Polycyclic aromatic compounds

Abstract

This invention provides novel polycyclic aromatic compounds and organic EL devices using the same. [Solution] For example, the compound (1A-18) shown below is presented. TIFF2026113508000231.tif53170 By fabricating organic EL devices using novel polycyclic aromatic compounds, for example, as dopant materials, we can provide organic EL devices with a narrow full width at half maximum of the emission spectrum and excellent color purity, as well as organic EL devices with superior quantum efficiency and device lifetime.

Description

[Technical Field]

[0001] This invention relates to polycyclic aromatic compounds, organic field-emitting elements using the same, and organic field-effect transients. Organic devices such as solar cells, organic thin-film solar cells, and wavelength conversion filters, as well as display devices. This relates to a lighting and illumination device. In this specification, "organic electroluminescent device" is referred to as "organic E It is sometimes referred to as an "L element" or simply as an "element." [Background technology]

[0002] Conventionally, display devices using electroluminescent light-emitting elements have been able to reduce power consumption and make them thinner. Various studies have been conducted, and furthermore, organic electroluminescent devices made of organic materials are easily made lighter and larger. For this reason, it has been actively studied. In particular, light emission such as blue and green, which are one of the three primary colors of light. Development of organic materials with specific properties, and charge transport capabilities such as holes and electrons (semiconductors and superconductors). Regarding the development of organic materials that possess the potential to become polymer compounds, low molecular weight compounds Regardless, these have been actively researched to date.

[0003] An organic EL element consists of a pair of electrodes, an anode and a cathode, and an electrode placed between the pair of electrodes. The structure consists of one or more layers containing an organic compound. These include light-emitting layers and charge transport / injection layers that transport or inject charges such as holes and electrons. However, various organic materials suitable for these layers have been developed.

[0004] Currently, materials used for the light-emitting layer include fluorescent materials, phosphorescent materials, and thermally activated delayed fluorescence (TADF) materials. Three types of materials are used. For example, in fluorescent materials, benzofluorene compounds are being developed. It has been published (International Publication No. 2004 / 061047), and in phosphorescent materials, noble gold having a polydentate ligand Complexes of this group have been developed (Japanese Patent Publication No. 2014-239225).

[0005] Furthermore, in recent years, improved materials derived from azavorin have also been reported (International Publication No. 2015 / 1 (Publication No. 02118). It has a single peak with a narrow emission width at half maximum and a singlet energy (S 1 ) and three Multiplet energy (T 1 The energy difference (ΔS) 1 T 1 Compounds having a small conjugated structure Because it offers high color purity and high efficiency due to thermally activated delayed fluorescence (TADF), it is suitable for blue and It is useful as a material for green light-emitting layers. Also useful as an electron transport material or hole transport material sandwiching the light-emitting layer. Even if the triplet energy (T 1 There is a need for compounds with novel conjugated structures that have a large ) ru.

[0006] However, fluorescent materials have the problem of low luminescence efficiency, while phosphorescent materials and TADF materials have the problem of low luminescence. Although it has high light efficiency, it has the problem of having a wide half-width in its emission spectrum and low color purity of emission. Furthermore, phosphorescent materials have the problem of being expensive because they contain precious metals (Nature Vol.4). 92 13 December 2012, Applied Physics Letters 75, 4 (1999)). [Prior art documents] [Patent Documents]

[0007] [Patent Document 1] International Publication No. 2004 / 061047 [Patent Document 2] Japanese Patent Publication No. 2014-239225 [Patent Document 3] International Publication No. 2015 / 102118 [Non-patent literature]

[0008] [Non-Patent Document 1] Nature Vol.492 13 December 2012 [Non-Patent Document 2] Applied Physics Letters 75, 4 (1999) [Overview of the Initiative] [Problems that the invention aims to solve]

[0009] As mentioned above, various materials have been developed for use in organic EL elements. However, in order to increase the options for materials for organic EL elements, a compound different from conventional ones is used. The development of materials is desired. In addition, Patent Document 3 describes a polycyclic aromatic compound containing boron and Organic EL elements using this have been reported, but in order to further improve the element characteristics, color purity, Light-emitting layer materials, particularly dopant materials, that can improve luminous efficiency and device lifespan. This is in demand. Also, as shown in Non-Patent Documents 1 and 2, thermally activated delayed fluorescence materials and In phosphorescent materials that utilize the heavy atom effect, the emission spectrum has a wide half-width and color purity. There was a problem in terms of improving the degree.

[0010] Furthermore, in addition to the vacuum deposition method, there are currently other methods for forming the organic layer that constitutes an organic EL element. Since the film deposition method is also used, in particular, the hole injection layer, hole transport layer, and light-emitting layer are formed. Active development is underway to create wet film-forming ink materials, and these ink materials are being used to mimic... Searching is also beneficial. [Means for solving the problem]

[0011] The present inventors have diligently studied to solve the above problems and have found a novel polycyclic aromatic compound We have succeeded in manufacturing it, and furthermore, the singlet and triplet energies required for thermally activated delayed fluorescence We found that this compound is effective as a material with small differences. And, for example, A polycyclic aromatic compound is used as the dopant material, and a compound with a larger triplet energy than it is used The process involves constructing an organic EL element by placing a light-emitting layer, which uses a compound as a host material, between a pair of electrodes. This led to the discovery that a superior thermally activated delayed fluorescence type organic EL element can be obtained, thus completing the present invention. I made them do it.

[0012] In this specification, chemical structures and substituents may be represented by the number of carbon atoms, but in the case of chemical structures... The number of carbon atoms in cases where a substitution group is substituted, or where a substituent is further substituted, is determined by the chemical formula. This refers to the number of carbon atoms in the chemical structure and each substituent, as well as the total number of carbon atoms in the chemical structure and substituents. This does not mean the total number of carbon atoms in the substituents. For example, "substituted with substituent A having X carbon atoms." A substituent B with a carbon number of Y is a substituent A with a carbon number of X on a substituent B with a carbon number of Y. This means substitution, and the number of carbon atoms Y is not the total number of carbon atoms of substituents A and B. For example, "substituent B with carbon number Y substituted with substituent A" means "substituent B with carbon number Y". This means that substituent A (without carbon number restrictions) is substituted, and the carbon number Y is equal to substituent A. This is not the total number of carbon atoms in substituent B.

[0013] Section 1. A polycyclic aromatic compound represented by the following general formula (1A) or general formula (1B). [ka] In the above formula (1A) or formula (1B), R a is hydrogen or a substituent, and "-C(-R a )=" in the a-ring may be replaced by "-N=", and ring B, ring C, ring D, ring E, ring F, and ring G are each independently an aryl ring or a heteroaryl ring, and at least one hydrogen in these rings may be substituted, and Y 1 , Y 2 , and Y 3 are each independently >B-, >P-, >P(=O)-, > P(=S)-, >Al-, >Ga-, >As-, >C(-R)-, >Si(-R)-, or >Ge(-R)-, where the R of >C(-R)-, the R of >Si(-R)-, and the R of >Ge(-R)- are each independently an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted alkyl, or an optionally substituted cycloalkyl, and X 1 and X 2 are each independently >N-R, >O, >S, >C(-R)2, >S i(-R)2, or >Se, where the R of >N-R, the R of >C(-R)2, and the R of >Si(-R)2 are each independently hydrogen, an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted alkyl, or an optionally substituted cycloalkyl, and at least one of the two Rs of >C(-R)2 and the two Rs of >Si(-R )2 may be bonded by a single bond or a linking group, and , X 1 as the R of >N-R, the R of >C(-R)2, or the R of >Si(-R)2 is They may be bonded to at least one of the a-ring and B-ring by a single bond or a linking group. X 2 The R in >NR, R in >C(-R)2, or R in >Si(-R)2 are They may be bonded to at least one of the α ring and the E ring by a single bond or a linking group. The C and D rings, the G and B rings, and the F and E rings are each independent of each other. They may be bonded by a bond or a linking group. However, in formula (1A) above, the CD bond between the C ring and the D ring, and X 1 As >NR R (where R is the substituted aryl or heteroar) (Limited to the cycloalkyl group which may be substituted) and X of the B ring 1 B knot Combined, X 2 >NR's R (where R is the aryl which may be substituted, the A heteroaryl or cycloalkyl group which may be substituted. (limited to) and X of the E ring 2 One or two of the three bonds with the E bond It exists, Furthermore, in formula (1B) above, the CD bond between the C and D rings and the GB bond between the G and B rings are represented. And, of the three bonds between the F ring and the FE bond of the E ring, one or two bonds are It exists, In the compound represented by formula (1A) or formula (1B) above, the B ring, C ring, D ring, E ring At least one of the F ring, G ring, aryl, and heteroaryl is at least one It may be condensed with a cycloalkane, and at least one of the cycloalkanes Hydrogen may be substituted, and at least one -CH2- in the cycloalkane It may also be substituted with -O-, At least one hydrogen in the compound represented by the above formula (1A) or formula (1B) is It may be substituted with deuterium, cyanopropyl alcohol, or halogen.

[0014] Section 2. In the above formula (1A) or formula (1B), R a These are hydrogen, optionally substituted aryls, and optionally substituted heteroaryls. , optionally substituted diarylamino, optionally substituted diheteroarylamino , optionally substituted aryl heteroarylamino, optionally substituted diaryl aryl boryl (the two aryls may be linked by a single bond or a linking group), substituted Optional alkyl groups, optional cycloalkyl groups, optional substituted groups The alkoxy, optionally substituted aryloxy, or substituted silyl, In ring a, "-C(-R a )=" can be replaced with "-N=". Rings B, C, D, E, F, and G are each independently an aryl ring or It is a heteroaryl ring, and at least one hydrogen in these rings is substituted. A good aryl, a heteroaryl that may be substituted, a diaryl that may be substituted Diheteroarylamino, optionally substituted diheteroarylamino, optionally substituted arylamino A heteroarylamino, or possibly substituted diarylboryl (the two aryls are single). Alkyl, which may be bonded (or bonded via a linking group), may be substituted, substituted Optionally substituted cycloalkyls, optionally substituted alkoxys, even if substituted It may be substituted with a good aryloxy or substituted silyl. Y 1 , Y 2, and Y 3 are each independently >B-, >P-, >P(=O)-, > P(=S)-, >Al-, >Ga-, >As-, >C(-R)-, >Si(-R)-, or >Ge(-R)-, where R of >C(-R)-, R of >Si(-R)-, and R of >Ge(-R)- are each independently aryl, heteroaryl, alkyl, or cycloalkyl, and at least one hydrogen in said R may be substituted with alkyl or cycloalkyl, X 1 and X 2 are each independently >N-R, >O, >S, >C(-R)2, >S i(-R)2, or >Se, where R of >N-R, R of >C(-R)2, and > R of >Si(-R)2 are each independently hydrogen, aryl, heteroaryl, alkyl , or cycloalkyl, and at least one hydrogen in said R may be substituted with alkyl or cycloalkyl, and at least one of the two Rs of >C(-R)2 and > the two Rs of >Si(-R)2 may be bonded by a single bond, -CH=CH-, -CR= CR-, -C≡C-, -N(-R)-, -O-, -S-, -C(-R)2-, -Si(- R)2-, or -Se-, and R of -CR=CR-, -N( -R)-, -C(-R)2-, and -Si(-R)2- are each independently hydrogen, aryl, heteroaryl, alkyl, alkenyl, alkynyl, or cyclo alkyl, and at least one hydrogen in said R may be substituted with alkyl or cyclo alkyl, and also, two adjacent Rs may form a ring, forming cycloal kylene, arylene, or heteroarylene, X 1 The R in >NR, R in >C(-R)2, or R in >Si(-R)2 are , single bond, -CH=CH-, -CR=CR-, -C≡C-, -N(-R)-, -O-, - S-, -C(-R)2-, -Si(-R)2-, or -Se-, the a-ring and B-ring It may be combined with at least one of X 2 The above >NR's R, >C(-R) In 2, R, or in >Si(-R)2, R represents a single bond, -CH=CH-, -CR=CR-, - C≡C-, -N(-R)-, -O-, -S-, -C(-R)2-, -Si(-R)2-, Alternatively, it may be bonded to at least one of the α ring and the E ring by -Se-, and the - CR = R in CR-, R in -N(-R)-, R in -C(-R)2-, and -Si(-R) R in 2- can be independently hydrogen, aryl, heteroaryl, alkyl, or alkeni. R is alkynyl or cycloalkyl, and at least one hydrogen in R is They may be substituted with alkyl or cycloalkyl groups, and two adjacent R groups may be substituted with each other. These form rings, forming cycloalkylenes, arylenes, and heteroarylenes. Often, The C and D rings, the G and B rings, and the F and E rings are each independent of each other. Bond, -CH=CH-, -CR=CR-, -C≡C-, -N(-R)-, -O-, -S- They may be bonded by -C(-R)2-, -Si(-R)2-, or -Se-. The R in -CR=CR-, the R in -N(-R)-, the R in -C(-R)2-, and -Si( In -R)2-, R can be independently hydrogen, aryl, heteroaryl, alkyl, or Lukenyl, alkynyl, or cycloalkyl, and at least one of the R The hydrogen atoms may be substituted with alkyl or cycloalkyl groups, and two adjacent hydrogen atoms may be substituted with alkyl or cycloalkyl groups. R atoms form rings, creating cycloalkylenes, arylenes, and heteroarylenes. It's fine to do so, However, in formula (1A) above, the CD bond between the C ring and the D ring, and X 1 As >NR R (This R may be substituted with the alkyl or cycloalkyl group) (Limited to the heteroaryl or cycloalkyl compounds) and X of the B ring 1 B bond and , X 2 >NR's R (where R is substituted with the alkyl or cycloalkyl) (This may be limited to the aryl, heteroaryl, or cycloalkyl compounds.) and X of the E ring 2 Of the three bonds with the E bond, one or two bonds are present. And, Furthermore, in formula (1B) above, the CD bond between the C and D rings and the GB bond between the G and B rings are represented. And, of the three bonds between the F ring and the FE bond of the E ring, one or two bonds are It exists, In the compound represented by formula (1A) or formula (1B) above, the B ring, C ring, D ring, E ring At least one of the F ring, G ring, aryl, and heteroaryl is at least one It may be condensed with a cycloalkane, and at least one of the cycloalkanes Hydrogen may be substituted, and at least one -CH2- in the cycloalkane It may also be substituted with -O-, At least one hydrogen in the compound represented by the above formula (1A) or formula (1B) is It may be substituted with deuterium, cyano, or halogen. A polycyclic aromatic compound as described in item 1.

[0015] Section 3. Polycyclic aromaticization as described in item 1, represented by the following general formula (2A) or the following general formula (2B). Compound. [ka] In the above formula (2A) or formula (2B), R a hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamine No, aryl heteroarylamino, diarylboryl (the two aryls are single-bonded or Alkyl, cycloalkyl, alkoxy, and aryl groups (which may be linked by linking groups) Oxy, triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dial The R is a chlorocycloalkylsilyl or alkyldicycloalkylsilyl, and a to At least one hydrogen in is aryl, heteroaryl, alkyl, or cycloaryl It is also acceptable if it is replaced with Lukil. In ring a, "-C(-R a )=" can be replaced with "-N=". R b , R c , R d , R e , R f , and R g These are, independently, hydrogen, aryl, Heteroaryl, diarylamino, diheteroarylamino, arylheteroaryl Amino, diarylboryl (the two aryl groups may be linked by a single bond or a linking group) (Good), alkyl, cycloalkyl, alkoxy, aryloxy, triarylsilyl , trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, or alkyldicycloalkylsilyl, and the Rb , R c , R d , R e , R f ,oh Call R g At least one hydrogen in is aryl, heteroaryl, alkyl, and R may be substituted with a cycloalkyl group, and also R b , R c , R d , R e , R f , oyo biR g Among these, adjacent groups bond together to form a b-ring, c-ring, d-ring, e-ring, f-ring, and so on. The γ ring may also form an aryl ring or a heteroaryl ring, and the formed At least one hydrogen in the ring is aryl, heteroaryl, diarylamino, or di Heteroarylamino, arylheteroarylamino, diarylboryl (two aryl (The groups may be linked by single bonds or linking groups), alkyl, cycloalkyl, A Lucoxy, aryloxy, triarylsilyl, trialkylsilyl, tricycloal Killsilyl, dialkylcycloalkylsilyl, or alkyldicycloalkylsilyl They may be substituted with, and at least one hydrogen in these substituents is aryl, They may be substituted with heteroaryl, alkyl, or cycloalkyl groups. In rings b, c, d, e, f, and g, any "-C(-R)=" (this Here R is R b , R c , R d , R e , R f , or R g (is replaced by "-N=") It is also fine to have any "-C(-R)=C(-R)-" (where R is R b , R c , R d , R e , R f , or R g (is) "-N(-R)-", "-O-", "-S-" Replaced by "-C(-R)2-", "-Si(-R)2-", or "-Se-" It may also include R in "-N(-R)-", R in "-C(-R)2-", and "-Si The R in "(-R)2-" represents hydrogen, aryl, heteroaryl, alkyl, or cycloaryl It is a kill, and at least one hydrogen in R is alkyl or cycloalkyl. Substitutions may occur, such as the two Rs in "-C(-R)2-" and "-Si(-R )2-" has at least one single bond between the two Rs, -CH=CH-, -CR=CR- , -C≡C-, -N(-R)-, -O-, -S-, -C(-R)2-, -Si(-R)2 - or -Se- may be bonded by -CR=CR- R, -N(-R) -R, -C(-R)2-, and -Si(-R)2- are each independent of each other. Hydrogen, aryl, heteroaryl, alkyl, alkenyl, alkynyl, or cyclo It is a lucyl, and at least one hydrogen in R is alkyl or cycloalkyl. It may be substituted with, and two adjacent Rs may form a ring, resulting in a cycloalkylene. They may form arylene or heteroarylene. Y 1 , Y 2 , and Y 3 These are, independently, >B-, >P-, >P(=O)-, > P(=S)-, >Al-, >Ga-, >As-, >C(-R)-, >Si(-R)-, or is >Ge(-R)-, and R in >C(-R)-, R in >Si(-R)-, and >The R in Ge(-R)- can be aryl, heteroaryl, alkyl, or or is a cycloalkyl group, and at least one hydrogen atom in R is alkyl or It may also be substituted with a cycloalkyl group. X 1 and X 2 These are >NR, >O, >S, >C(-R)2, and >S, respectively, independently. i(-R)2, or >Se, where R of >NR, R of >C(-R)2, and > In Si(-R)2, R can be independently hydrogen, aryl, heteroaryl, or alkyl. , or cycloalkyl, where at least one hydrogen in R is alkyl or The cycloalkyl group may be substituted with the two R groups of the >C(-R)2 and > At least one of the two R groups in Si(-R)2 is a single bond, -CH=CH-, -CR= CR-, -C≡C-, -N(-R)-, -O-, -S-, -C(-R)2-, -Si(- R)2- or -Se- may be bonded, and the R, -N( The R in -R)-, the R in -C(-R)2-, and the R in -Si(-R)2- are independent of each other. And hydrogen, aryl, heteroaryl, alkyl, alkenyl, alkynyl, or cy It is a chloroalkyl group, and at least one hydrogen atom in R is alkyl or cycloalkyl. It may be substituted with R, and two adjacent Rs may form a ring, cycloal They may form chilenes, arylenes, or heteroarylenes. X 1 The R in >NR, R in >C(-R)2, or R in >Si(-R)2 are , single bond, -CH=CH-, -CR=CR-, -C≡C-, -N(-R)-, -O-, - S-, -C(-R)2-, -Si(-R)2-, or -Se-, the a-ring and b-ring It may be combined with at least one of X 2 The above >NR's R, >C(-R) In 2, R, or in >Si(-R)2, R represents a single bond, -CH=CH-, -CR=CR-, - C≡C-, -N(-R)-, -O-, -S-, -C(-R)2-, -Si(-R)2-, Alternatively, it may be bonded to at least one of the a-ring and e-ring by -Se-, and the - CR = R in CR-, R in -N(-R)-, R in -C(-R)2-, and -Si(-R) R in 2- can be independently hydrogen, aryl, heteroaryl, alkyl, or alkeni. R is alkynyl or cycloalkyl, and at least one hydrogen in R is They may be substituted with alkyl or cycloalkyl groups, and two adjacent R groups may be substituted with each other. These form rings, forming cycloalkylenes, arylenes, and heteroarylenes. Often, The c and d rings, the g and b rings, and the f and e rings are each independent of each other. Bond, -CH=CH-, -CR=CR-, -C≡C-, -N(-R)-, -O-, -S- They may be bonded by -C(-R)2-, -Si(-R)2-, or -Se-. The R in -CR=CR-, the R in -N(-R)-, the R in -C(-R)2-, and -Si( In -R)2-, R can be independently hydrogen, aryl, heteroaryl, alkyl, or Lukenyl, alkynyl, or cycloalkyl, and at least one of the R The hydrogen atoms may be substituted with alkyl or cycloalkyl groups, and two adjacent hydrogen atoms may be substituted with alkyl or cycloalkyl groups. R atoms form rings, creating cycloalkylenes, arylenes, and heteroarylenes. It's fine to do so, However, in formula (2A) above, the cd bond of the c ring and the d ring, and X 1As >NR R (This R may be substituted with the alkyl or cycloalkyl group) (Limited to the heteroaryl or cycloalkyl compounds) and X of the b ring 1 b bond and , X 2 >NR's R (where R is substituted with the alkyl or cycloalkyl) (This may be limited to the aryl, heteroaryl, or cycloalkyl compounds.) and X of the e ring 2 Of the three bonds with the e bond, one or two bonds are present. And, Furthermore, in formula (2B) above, the cd bond between the c and d rings and the gb bond between the g and b rings are represented. And, of the three bonds between the f-ring and the fe bond of the e-ring, one or two of the bonds are It exists, In the compound represented by the above formula (2A) or formula (2B), the b ring, the c ring, and The d ring, the e ring, the f ring, the g ring, the ring on which the above is formed, the aryl, and the At least one heteroaryl is at least one cycloalkane having 3 to 24 carbon atoms. They may be condensed in such a way, and at least one hydrogen in the cycloalkane is carbon number aryls with 6-30 carbon atoms, heteroaryls with 2-30 carbon atoms, alkyls with 1-24 carbon atoms, Alternatively, it may be substituted with a cycloalkyl group having 3 to 24 carbon atoms, and the cycloalkane may be substituted with a cycloalkyl group having 3 to 24 carbon atoms. At least one of the -CH2- molecules may be substituted with -O-. At least one hydrogen in the compound represented by the above formula (2A) or formula (2B) is It may be substituted with deuterium, cyanopropyl alcohol, or halogen.

[0016] Section 4. In the above formula (2A) or formula (2B), Ra is hydrogen, aryl having 6 to 30 carbon atoms, heteroaryl having 2 to 30 carbon atoms, diaryl -lamino (where aryl is aryl having 6 to 12 carbon atoms), diarylboranyl (where aryl is aryl having 6 to 12 carbon atoms, and the two aryls may be bonded by a single bond or a linking group ), alkyl having 1 to 24 carbon atoms, or cycloalkyl having 3 to 24 carbon atoms, and at least one hydrogen in said R may be substituted with aryl having 6 to 12 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, alkyl having 1 to 6 carbon atoms, or cycloalkyl having 3 to 14 carbon atoms, and "-C(-R )=" in the a ring may be replaced by "-N=", R a ), R R b ), R c ), R d ), R e ), R f ), and R g are each independently hydrogen, aryl having 6 to 30 carbon atoms, heteroaryl having 2 to 30 carbon atoms, diarylamino (where aryl is aryl having 6 to 12 carbon atoms), diarylboranyl (where aryl is aryl having 6 to 12 carbon atoms and the two aryls may be bonded by a single bond or a linking group), alkyl having 1 to 24 carbon atoms, or cycloalkyl having 3 to 24 carbon atoms, and at least one hydrogen in said R [[ID=4l]]), R b ), R c ), R d ), R e ), R f ), and R g may be substituted with aryl having 6 to 12 carbon atoms,<{ heteroaryl having 2 to 15 carbon atoms, alkyl having 1 to 6 carbon atoms, or cycloalkyl having 3 to 14 carbon atoms, and also, R ), R b ), R c ), Rd , R e , R f , and R g among the adjacent groups are combined to form an aryl ring having 9 to 16 carbon atoms or a heteroaryl ring having 6 to 15 carbon atoms together with the b-ring, c-ring, d-ring, e-ring, f -ring, and g-ring, and at least one hydrogen in the formed ring is an aryl having 6 to 30 carbon atoms, a heteroaryl having 2 to 30 carbon atoms, diarylamino (where the aryl is an aryl having 6 to 12 carbon atoms), diarylboryl (where the aryl is an aryl having 6 to 12 carbon atoms and the two aryls may be bonded by a single bond or a linking group), an alkyl having 1 to 24 carbon atoms, or a cycloalkyl having 3 to 24 carbon atoms, and may be substituted, and at least one hydrogen in these substituents is an aryl having 6 to 12 carbon atoms, a carbon heteroaryl having 2 to 15 carbon atoms, an alkyl having 1 to 6 carbon atoms, or a cycloalkyl having 3 to 14 carbon atoms, and may be substituted, In the b-ring, c-ring, d-ring, e-ring, f-ring, and g-ring, any “-C(−R)=” (where R is R , R , R , R , R here) may be replaced by “-N=”, and any “-C(−R)=C(−R)-” (where R is R[[ID=3l]] b , R c , R d , R e , R f , or R g here) may be replaced by “-N(−R)-”, “-O-”, “-S-” , “-C(−R)2-”, “-Si(−R)2-”, or “-Se-”. b , R c , R d , R e , R f , or R g here), and may be replaced by “-N(−R)-”, “-O-”, “-S-”, “-C(−R)2-”, “-Si(−R)2-”, or “-Se-”. It may also include R in "-N(-R)-", R in "-C(-R)2-", and "-Si In "(-R)2-", R stands for hydrogen, aryl atoms with 6-12 carbon atoms, and heteroaryl atoms with 2-15 carbon atoms. The R is an alkyl group having 1 to 6 carbon atoms, or a cycloalkyl group having 3 to 14 carbon atoms. At least one hydrogen atom in is an alkyl group having 1 to 6 carbon atoms or a cyclic group having 3 to 14 carbon atoms. It may also be substituted with a ralkyl group, and the two Rs of "-C(-R)2-" and At least one of the two Rs in "-Si(-R)2-" is a single bond, -CH=CH-, - CR=CR-, -C≡C-, -N(-R)-, -O-, -S-, -C(-R)2-, -S It may be bonded by i(-R)2- or -Se-, and the R in -CR=CR- R in -N(-R)-, R in -C(-R)2-, and R in -Si(-R)2- are each These independently include hydrogen, aryl atoms with 6 to 12 carbon atoms, heteroaryl atoms with 2 to 15 carbon atoms, and carbon atoms. Alkyls with 1 to 6 carbon atoms, alkenyls with 1 to 6 carbon atoms, alkynyls with 1 to 6 carbon atoms, or carbon It is a cycloalkyl group with prime numbers 3 to 14, and at least one hydrogen atom in R is a carbon number They may be substituted with 1-6 alkyl groups or 3-14 cycloalkyl groups, Two adjacent R atoms form a ring, forming cycloalkylenes with 3 to 14 carbon atoms, and cycloalkylenes with 6 to 14 carbon atoms. They may form 12-carat arylenes, or heteroarylenes with 2 to 15 carbon atoms. Y 1 , Y 2 , and Y 3 These are, independently, >B-, >P-, >P(=O)-, > P(=S)-, >Al-, >Ga-, >As-, >C(-R)-, >Si(-R)-, or is >Ge(-R)-, and R in >C(-R)-, R in >Si(-R)-, and The R in Ge(-R)- is independently an aryl group with 6 to 12 carbon atoms and a group with 2 to 1 carbon atoms. 5 heteroaryls, C1-C6 alkyls, or C3-C4 cycloalkyls And at least one hydrogen in R is an alkyl group having 1 to 6 carbon atoms or a carbon number It may also be substituted with 3 to 14 cycloalkyl groups. X 1 and X 2 These are >NR, >O, >S, >C(-R)2, and >S, respectively, independently. i(-R)2, or >Se, where R of >NR, R of >C(-R)2, and > In Si(-R)2, the R atoms are, independently, hydrogen, an aryl atom with 6 to 12 carbon atoms, and an aryl atom with 2 carbon atoms. ~15 heteroaryls, 1-6 C1 alkyls, or 3-14 C1 cycloaryls It is a kill, and at least one hydrogen in R is an alkyl or carbon having 1 to 6 carbon atoms. It may also be substituted with cycloalkyl groups with prime numbers between 3 and 14. X 1 The R in >NR, R in >C(-R)2, or R in >Si(-R)2 are , single bond, -CH=CH-, -CR=CR-, -C≡C-, -N(-R)-, -O-, - S-, -C(-R)2-, -Si(-R)2-, or -Se-, the a-ring and b-ring It may be combined with at least one of X 2 The above >NR's R, >C(-R) In 2, R, or in >Si(-R)2, R represents a single bond, -CH=CH-, -CR=CR-, - C≡C-, -N(-R)-, -O-, -S-, -C(-R)2-, -Si(-R)2-, Alternatively, it may be bonded to at least one of the a-ring and e-ring by -Se-, and the - CR = R in CR-, R in -N(-R)-, R in -C(-R)2-, and -Si(-R) The R in 2- are, independently, hydrogen, aryl atoms with 6 to 12 carbon atoms, and helium atoms with 2 to 15 carbon atoms. Teloaryl, alkyl with 1-6 carbon atoms, alkenyl with 1-6 carbon atoms, a Lukinyl, or a cycloalkyl with 3 to 14 carbon atoms, and at least one of the R atoms One hydrogen atom is substituted with an alkyl group having 1 to 6 carbon atoms or a cycloalkyl group having 3 to 14 carbon atoms. It is also fine if two adjacent Rs form a ring, and cycloal groups with 3 to 14 carbon atoms are formed. Forms chilenne, arylene with 6-12 carbon atoms, or heteroarylene with 2-15 carbon atoms. Even if you do, The c and d rings, the g and b rings, and the f and e rings are each independent of each other. Bond, -CH=CH-, -CR=CR-, -C≡C-, -N(-R)-, -O-, -S- They may be bonded by -C(-R)2-, -Si(-R)2-, or -Se-. The R in -CR=CR-, the R in -N(-R)-, the R in -C(-R)2-, and -Si( In -R)2-, R represents, independently, hydrogen, an aryl group with 6 to 12 carbon atoms, and an aryl group with 2 to 1 carbon atoms. 5 heteroaryls, C1-C6 alkyls, C1-C6 alkenyls, C1- 6 alkynyl or cycloalkyl with 3 to 14 carbon atoms, and at least one of the R atoms. Each hydrogen atom is placed in an alkyl group with 1 to 6 carbon atoms or a cycloalkyl group with 3 to 14 carbon atoms. They may be replaced, and two adjacent Rs may form a ring, with 3 to 14 carbon atoms. Roalkylenes, arylenes with 6-12 carbon atoms, or heteroarylenes with 2-15 carbon atoms. It may also form a structure, However, in formula (2A) above, the cd bond of the c ring and the d ring, and X 1 As >NR R (where R is an alkyl group having 1 to 6 carbon atoms or a cycloalkyl group having 3 to 14 carbon atoms) The aryl atoms having 6 to 12 carbon atoms and the heteroaryl atoms having 2 to 15 carbon atoms may be substituted. (Limited to cycloalkyl groups having 3 to 14 carbon atoms) and X of the b ring 1 b bond and, X 2 >NR's R (this R is the alkyl with 1 to 6 carbon atoms or 3 to 1 carbon atoms) The aryl group having 6 to 12 carbon atoms, which may be substituted with cycloalkyl groups, and the carbon (Limited to heteroaryls with 2 to 15 carbon atoms, or cycloalkyls with 3 to 14 carbon atoms) X 2 Of the three bonds with the e bond, one or two bonds are present. the law of nature, Furthermore, in formula (2B) above, the cd bond between the c and d rings and the gb bond between the g and b rings are represented. And, of the three bonds between the f-ring and the fe bond of the e-ring, one or two of the bonds are It exists, In the compound represented by the above formula (2A) or formula (2B), the b ring, the c ring, and The d ring, the e ring, the f ring, the g ring, the ring on which the above is formed, the aryl, and the At least one heteroaryl is at least one cycloalkane having 3 to 24 carbon atoms. They may be condensed in such a way, and at least one hydrogen in the cycloalkane is carbon number aryls with 6-16 carbon atoms, heteroaryls with 2-15 carbon atoms, alkyls with 1-12 carbon atoms, Alternatively, it may be substituted with a cycloalkyl group having 3 to 16 carbon atoms. At least one hydrogen in the compound represented by the above formula (2A) or formula (2B) is It may be substituted with deuterium, cyano, or halogen. Polycyclic aromatic compounds as described in item 3.

[0017] Section 5. In the above formula (2A) or formula (2B), R a These include hydrogen, aryl atoms with 6 to 16 carbon atoms, heteroaryl atoms with 2 to 20 carbon atoms, and diaryl atoms. arylamino (however, aryl refers to aryl with 6 to 10 carbon atoms), diarylboryl (however Aryls are aryl compounds with 6 to 10 carbon atoms, and two aryls are linked by a single bond or a linking group. (May be bonded together), alkyl groups with 1 to 12 carbon atoms, or cycloa groups with 3 to 16 carbon atoms It is Lukil, and the R a At least one hydrogen atom in the compound is an aryl atom with 6 to 10 carbon atoms. Heteroaryls with 2 to 10 carbon atoms, alkyls with 1 to 5 carbon atoms, or sylions with 5 to 10 carbon atoms It may also be substituted with a chloroalkyl group. In ring a, "-C(-R a )=" can be replaced with "-N=". R b , R c , R d , R e , R f , and R g These are, independently, hydrogen, carbon atoms with 6 carbon atoms... 16 aryls, heteroaryls with 2-20 carbon atoms, diarylaminos (however aryl) (aryls with 6-10 carbon atoms), diarylboryls (where aryls have 6-10 carbon atoms) (It is an aryl compound, and the two aryl compounds may be linked by a single bond or a linking group), carbon The R is an alkyl group with prime numbers 1 to 12, or a cycloalkyl group with 3 to 16 carbon atoms. b , R c , R d , R e , R f , and R g At least one hydrogen atom in is a carbon atom with 6 to 10 carbon atoms. Aryl, heteroaryl with 2 to 10 carbon atoms, alkyl with 1 to 5 carbon atoms, or 5 carbon atoms It may be substituted with ~10 cycloalkyl groups, and R b , Rc , R d , R e , R f , and R g Adjacent groups bond together to form rings b, c, d, e, and f, respectively. Along with the ring and the γ ring, there are aryl rings with 9 to 16 carbon atoms or heteroaryl rings with 6 to 15 carbon atoms. A ring may be formed, and at least one hydrogen in the formed ring has six carbon atoms. ~16 aryls, heteroaryls with 2-20 carbon atoms, diarylaminos (however, aryl (aryl is an aryl with 6 to 10 carbon atoms), diarylboryl (however, aryl is an aryl with 6 to 10 carbon atoms) (The aryl group is such that the two aryl groups may be linked by a single bond or a linking group.) Even if substituted with alkyl groups having 1 to 12 carbon atoms, or cycloalkyl groups having 3 to 16 carbon atoms Often, at least one hydrogen atom in these substituents is an aryl or carbon atom having 6 to 10 carbon atoms. Heteroaryls with 2 to 10 prime numbers, alkyls with 1 to 5 carbon atoms, or sicqs with 5 to 10 carbon atoms It may also be substituted with a r-alkyl group. In rings b, c, d, e, f, and g, any "-C(-R)=" (this Here R is R b , R c , R d , R e , R f , or R g (is replaced by "-N=") It's fine if you keep it, Y 1 , Y 2 , and Y 3 These are, independently, >B-, >P-, >P(=O)-, and And >P(=S)-, X 1 and X 2 These are, independently, >NR, >O, >S, or >C(-R)2 Thus, R in >NR and R in >C(-R)2 are, independently, hydrogen and carbon. Aryls with 6 to 10 carbon atoms, heteroaryls with 2 to 10 carbon atoms, alkyls with 1 to 5 carbon atoms, or is a cycloalkyl group having 5 to 10 carbon atoms, and at least one hydrogen atom in R is It may also be substituted with an alkyl group having 1 to 5 carbon atoms or a cycloalkyl group having 5 to 10 carbon atoms. , X 1 As for the R in >NR or >C(-R)2, the R is a single bond, -N(-R)- The β ring may be bonded by -O-, -S-, or -C(-R)2-, X 2 and In the above, R in >NR or R in >C(-R)2 is a single bond, -N(-R)-, -O- The e ring may be bonded by -S- or -C(-R)2-, and the -N(-R The R in -C(-R)2- and the R in -C(-R)2- are, independently, hydrogen and a carbon atom with 6 to 10 carbon atoms. Rheel, heteroaryl with 2-10 carbon atoms, alkyl with 1-5 carbon atoms, or with 5 carbon atoms It is a cycloalkyl group of 10, and at least one hydrogen atom in R is a carbon atom with 1 to 5 carbon atoms. They may be substituted with alkyl or cycloalkyl groups having 5 to 10 carbon atoms. The c and d rings, the g and b rings, and the f and e rings are each independent of each other. Even if they are bonded by -N(-R)-, -O-, -S-, or -C(-R)2- Often, the R in -N(-R)- and the R in -C(-R)2- are, independently of each other, hydrogen. aryl compounds with 6 to 10 carbon atoms, heteroaryl compounds with 2 to 10 carbon atoms, and alkyl compounds with 1 to 5 carbon atoms. R, or a cycloalkyl group having 5 to 10 carbon atoms, wherein at least one water molecule in R The element is substituted with an alkyl group having 1 to 5 carbon atoms or a cycloalkyl group having 5 to 10 carbon atoms. Often, However, in formula (2A) above, the cd bond of the c ring and the d ring, and X 1 As >NR R (where R is an alkyl group having 1 to 5 carbon atoms or a cycloalkyl group having 5 to 10 carbon atoms) (Limited to the aforementioned aryls having 6 to 10 carbon atoms, which may be replaced) and the X of the b ring 1 b bond and , X 2 >NR's R (this R is the alkyl or C1-C5 alkyl or C5- (Limited to the aryls having 6 to 10 carbon atoms, which may be substituted with 10 cycloalkyl groups.) and X of the e ring 2 Of the three bonds with the e bond, one or two bonds are present. And, Furthermore, in formula (2B) above, the cd bond between the c and d rings and the gb bond between the g and b rings are represented. And, of the three bonds between the f-ring and the fe bond of the e-ring, one or two of the bonds are It exists, In the compound represented by the above formula (2A) or formula (2B), the b ring, the c ring, and The d ring, the e ring, the f ring, the g ring, the ring on which the above is formed, the aryl, and the At least one heteroaryl is a cycloalkane having 3 to 16 carbon atoms. They may be condensed in such a way, and at least one hydrogen in the cycloalkane is carbon number aryl groups with 6-10 carbon atoms, heteroaryl groups with 2-10 carbon atoms, alkyl groups with 1-5 carbon atoms, It may also be substituted with a cycloalkyl group having 5 to 10 carbon atoms. At least one hydrogen in the compound represented by the above formula (2A) or formula (2B) is It may be substituted with deuterium, cyano, or halogen. Polycyclic aromatic compounds as described in item 3.

[0018] Section 6. In the above formula (2A) or formula (2B), R a These include hydrogen, aryl atoms with 6 to 16 carbon atoms, heteroaryl atoms with 2 to 20 carbon atoms, and diaryl atoms. arylamino (however, aryl refers to aryl with 6 to 10 carbon atoms), diarylboryl (however Aryls are aryl compounds with 6 to 10 carbon atoms, and two aryls are linked by a single bond or a linking group. (May be bonded together), alkyl groups with 1 to 12 carbon atoms, or cycloa groups with 3 to 16 carbon atoms It is Lukil, and the R a At least one hydrogen in is an alkyl group having 1 to 5 carbon atoms. It may also be substituted with a cycloalkyl group having 5 to 10 carbon atoms. R b , R c , R d , R e , R f , and R g These are, independently, hydrogen, carbon atoms with 6 carbon atoms... 16 aryls, heteroaryls with 2-20 carbon atoms, diarylaminos (however aryl) (aryls with 6-10 carbon atoms), diarylboryls (where aryls have 6-10 carbon atoms) (It is an aryl compound, and the two aryl compounds may be linked by a single bond or a linking group), carbon The R is an alkyl group with prime numbers 1 to 12, or a cycloalkyl group with 3 to 16 carbon atoms. b , R c , R d , R e , R f , and R g At least one hydrogen in is a carbon atom with 1 to 5 carbon atoms. It may be substituted with lucyl or a cycloalkyl group having 5 to 10 carbon atoms. Y 1 , Y 2 , and Y 3 It is >B-, X 1 and X 2 >NR, where R in >NR is hydrogen, carbon atoms with 6 to 10 carbon atoms. Rheel, heteroaryl with 2-10 carbon atoms, alkyl with 1-5 carbon atoms, or with 5 carbon atoms It is a cycloalkyl group of 10, and at least one hydrogen atom in R is a carbon atom with 1 to 5 carbon atoms. It may also be substituted with alkyl groups. X 1 In the aforementioned >NR, R may be bonded to the b ring by a single bond, X 2 and In the aforementioned >NR, R may be bonded to the e ring by a single bond. The c and d rings, the g and b rings, and the f and e rings are each independent of each other. They may be bonded together, However, in formula (2A) above, the cd bond of the c ring and the d ring, and X 1 As >NR R (This R is a C6-C10 alkyl which may be substituted with the C1-C5 alkyl) (Limited to reels) and X of ring b 1 b bond and X 2 >NR's R (this R is the aforementioned (Limited to aryl atoms with 6 to 10 carbon atoms, which may be substituted with alkyl atoms with 1 to 5 carbon atoms.) X 2 Of the three bonds with the e bond, one or two bonds are present. the law of nature, Furthermore, in formula (2B) above, the cd bond between the c and d rings and the gb bond between the g and b rings are represented. And, of the three bonds between the f-ring and the fe bond of the e-ring, one or two of the bonds are It exists, In the compound represented by the above formula (2A) or formula (2B), the b ring, the c ring, and The d ring, the e ring, the f ring, the g ring, the aryl, and the heteroaryl Even if at least one is condensed with at least one cycloalkane having 3 to 14 carbon atoms Often, at least one hydrogen atom in the cycloalkane is an alkyl group having 1 to 5 carbon atoms. Even if it is replaced, At least one hydrogen in the compound represented by the above formula (2A) or formula (2B) is It may be substituted with deuterium, cyano, or halogen. Polycyclic aromatic compounds as described in item 3.

[0019] Section 7. A polycyclic aromatic compound as described in item 3, represented by one of the following structural formulas. [ka] In each formula, R is independently a hydrogen atom, an aryl atom with 6 to 16 carbon atoms, and a heteroatomic atom with 2 to 20 carbon atoms. Aryl, diarylamino (where aryl refers to aryl with 6 to 10 carbon atoms), diary Luboryl (however, aryl is an aryl with 6 to 10 carbon atoms, and the two aryls are single-bonded) (or may be bonded by a linking group), C1-C12 alkyl, or C3 It is a cycloalkyl group of ~16 atoms, and at least one hydrogen atom in R has 1 to 5 carbon atoms. It may be substituted with an alkyl group or a cycloalkyl group having 5 to 10 carbon atoms. Each of o is an independent integer between 1 and 3. p are independent integers from 1 to 4. Each q is an independent integer between 1 and 5. In each of the above formulas, at least one hydrogen atom is deuterium, cyano, or It may be substituted with a halogen.

[0020] Section 8. A polycyclic aromatic compound as described in item 1, represented by one of the following structural formulas. [ka] [ka] [ka]

[0021] Section 9. A reactive polycyclic aromatic compound, as described in any of items 1 to 8, is substituted with a reactive substituent. Compound.

[0022] Section 10. A polymer compound obtained by polymerizing the reactive compound described in item 9 as a monomer, or A polymer crosslinked material obtained by further crosslinking the polymer compound in question.

[0023] Section 11. A pendant-type polymer compound obtained by substituting the reactive compound described in item 9 into the main chain polymer, Alternatively, a pendant-type polymer crosslinked material obtained by further crosslinking the said pendant-type polymer compound.

[0024] Section 12. A material for organic devices containing a polycyclic aromatic compound as described in any of items 1 to 8.

[0025] Section 13. A material for organic devices containing the reactive compounds described in item 9.

[0026] Section 14. Materials for organic devices containing the polymer compounds or polymer crosslinks described in item 10.

[0027] Section 15. Contains the pendant-type polymer compound or pendant-type polymer crosslinked material described in item 11. Materials for organic devices.

[0028] Section 16. The aforementioned organic device material is an organic electroluminescent device material, an organic field-effect transistor material Materials, materials for organic thin-film solar cells, or materials for wavelength conversion filters, as specified in items 12-15. Materials for organic devices, as described below.

[0029] Section 17. The material for the organic electroluminescent device is a material for the light-emitting layer, as described in item 16. material.

[0030] Section 18. An ink composition comprising a polycyclic aromatic compound as described in any of items 1 to 8 and an organic solvent. .

[0031] Section 19. An ink composition comprising the reactive compound described in item 9 and an organic solvent.

[0032] Section 20. An ink composition comprising a main-chain polymer, a reactive compound as described in item 9, and an organic solvent.

[0033] Section 21. An ink composition comprising a polymer compound or polymer crosslinker as described in item 10 and an organic solvent. thing.

[0034] Section 22. The pendant-type polymer compound or pendant-type polymer crosslinker described in item 11, and organic An ink composition comprising a solvent.

[0035] Section 23. A pair of electrodes consisting of an anode and a cathode, and a device placed between the pair of electrodes, any of items 1 to 8. Polycyclic aromatic compounds as described in item 9, reactive compounds as described in item 9, polymers as described in item 10 A compound or a polymer crosslinked material, or a pendant-type polymer compound as described in item 11. An organic field light-emitting element having an organic layer containing a pendant-type polymer crosslinker.

[0036] Section 24. The organic electroluminescent element described in item 23, wherein the organic layer is a light-emitting layer.

[0037] Section 25. The light-emitting layer comprises a host, the polycyclic aromatic compound as a dopant, and a reactive compound. Polymer compounds, polymer crosslinks, pendant-type polymer compounds, or pendant-type polymer crosslinks An organic electroluminescent element as described in item 24, including a body.

[0038] Section 26. The aforementioned light-emitting layer further comprises a compound represented by the following general formula (H1) and a compound represented by the following general formula (H2). The compound that is subjected to the following general formula (H3), the compound represented by the following general formula (H4) Compounds containing the following formula, compounds represented by the following general formula (H5), compounds represented by the following general formula (H6) The item contains at least one selected from the group consisting of compounds and TADF materials. Organic electroluminescent device as described in 25. [ka] In the above general formula (H1), L 1 This is arylene with 6 to 30 carbon atoms or helium with 2 to 30 carbon atoms. It is teloarrine, In the above general formula (H2), L 2 and L 3 These are, independently, ants with 6 to 30 carbon atoms. It is a heteroaryl compound or a heteroaryl compound with 2 to 30 carbon atoms. In the above general formula (H3), MU independently represents any two hydrogen atoms from an aromatic compound. Except for the divalent group represented, EC independently takes any one water from the aromatic compound. It is a monovalent group represented by excluding elementary atoms, where the two hydrogen atoms in MU are substituted with EC or MU. Here, k is an integer between 2 and 50000. In the above general formula (H4), G is independently either =C(-H)- or =N-, and Note = C(-H)- where H is replaced by a substituent or a structure represented by other formulas (H4) Often, In the above general formula (H5), R 1 ~R 11 These are, independently, hydrogen, aryl, heteroaryl, and diarylia. Mino, diheteroarylamino, arylheteroarylamino, alkyl or cyclo It is alkyl, and the R 1 ~R 11 At least one hydrogen in is further aryl, It may be substituted with teloaryl, diarylamino, alkyl, or cycloalkyl. Ku, R 1 ~R 11 Adjacent groups among them bond together with the a, b, or c rings, forming an aryl group. They may form a ring or a heteroaryl ring, and at least one of the formed rings The hydrogen in aryl, heteroaryl, diarylamino, diheteroarylamino, and They may be substituted with a reel heteroarylamino, alkyl, or cycloalkyl group. At least one hydrogen atom in these substituents is further aryl, heteroaryl, or dia They may be substituted with reel-amino, alkyl, or cycloalkyl groups. In ring a, ring b, and ring c, any "-C(-R)=" (where R is R 1 ~R 1 1 The part "-N=" may be replaced with "-N=". In the above general formula (H6), R 1 ~R 16 These are, independently, hydrogen, aryl, heteroaryl, and diarylia. Mino, diheteroarylamino, arylheteroarylamino, alkyl or cyclo It is alkyl, and the R 1~R 16 At least one hydrogen in is further aryl, It may be substituted with teloaryl, diarylamino, alkyl, or cycloalkyl. Ku, R 1 ~R 16 Among them, adjacent groups bond together to form rings a, b, c, or d, forming a ring They may form a reel ring or a heteroaryl ring, and in the formed ring, Another hydrogen is aryl, heteroaryl, diarylamino, diheteroarylamino Even if substituted with aryl heteroarylamino, alkyl, or cycloalkyl Often, at least one hydrogen atom in these substituents is further aryl or heteroaryl. They may be substituted with diarylamino, alkyl, or cycloalkyl groups, and In each of the above formulas, at least one hydrogen atom in the compound or structure has 1 to 6 carbon atoms. Substituted with alkyl, cycloalkyl, cyano, halogen, or deuterium. It's okay if it's not allowed.

[0039] Section 27. At least one electron transport layer and electron injection layer disposed between the cathode and the light-emitting layer It has two layers, and at least one of the electron transport layer and the electron injection layer is a borane derivative, pyri Zin derivatives, fluorantene derivatives, BO derivatives, anthracene derivatives, benzofluor Len derivatives, phosphine oxide derivatives, pyrimidine derivatives, carbazole derivatives, Liazin derivatives, benzimidazole derivatives, phenanthroline derivatives, quinolinol derivatives Metal complexes, thiazole derivatives, benzothiazole derivatives, silole derivatives, and azolines A compound comprising at least one selected from the group consisting of derivatives, as specified in any of items 23 to 26. The organic electroluminescent device described.

[0040] Section 28. At least one of the electron transport layer and electron injection layer is further composed of alkali metals, etc. Alkali earth metals, rare earth metals, alkali metal oxides, alkali metal halides, Oxides of alkaline earth metals, halides of alkaline earth metals, oxides of rare earth metals, rare earth Metallic halides, alkali metal organic complexes, alkaline earth metal organic complexes and rare The description in item 27 contains at least one selected from the group consisting of organic complexes of earth metals. Organic electroluminescent element.

[0041] Section 29. At least one of the following: hole injection layer, hole transport layer, light emission layer, electron transport layer, and electron injection layer Each layer is a polymer compound formed by polymerizing low-molecular-weight compounds that can form each layer as monomers. Alternatively, a polymer crosslinked polymer obtained by further crosslinking the polymer compound, or forming each layer The resulting low molecular weight compound is reacted with a main chain polymer to form a pendant-type polymer compound, or Item 2 includes a pendant-type polymer crosslinked product obtained by further crosslinking the pendant-type polymer compound. An organic electroluminescent device as described in any of 3 to 28.

[0042] Section 30. Display device or lighting device equipped with an organic electroluminescent element as described in any of items 23 to 29 .

[0043] Section 31. A wavelength conversion filter comprising the wavelength conversion filter material described in item 16. [Effects of the Invention]

[0044] According to a preferred embodiment of the present invention, a novel polycyclic aromatic compound is used as, for example, a dopant material. By fabricating organic EL elements using this method, we were able to create an organic EL element with a narrow half-width of emission spectrum and excellent color purity. We can provide organic EL elements, and furthermore, organic EL elements with superior quantum efficiency and device lifespan. Furthermore, the novel polycyclic aromatic compounds of the present invention have a rigid structure, which also contributes to their development. The light spectrum is sharper, the emission spectrum has a narrower half-width, and the emission has high color purity. Many compounds give this effect.

[0045] Specifically, the inventors have found that the aromatic ring is a heterozygous compound of boron, phosphorus, oxygen, nitrogen, sulfur, etc. Polycyclic aromatic compounds linked by elements have a large HOMO-LUMO gap (in thin films). We found that it has a band gap (Eg) and a high triplet energy. This is because it is hetero Because the six-membered ring containing the element has low aromaticity, the HOMO-LUMO gap associated with the expansion of the conjugated system The decrease in the number of elements is suppressed, and the electronic perturbation of heteroatoms causes SOMO to enter a triplet excited state. This is thought to be caused by the localization of 1 and SOMO2.

[0046] Furthermore, the polycyclic aromatic compound containing the heteroatom according to the present invention is in a triplet excited state. The localization of SOMO1 and SOMO2 reduces the exchange interaction between the two orbitals. Therefore, the energy difference between the triplet excited state and the singlet excited state is small, and it exhibits thermally activated delayed fluorescence. Therefore, it is also useful as a fluorescent material for organic EL elements. Furthermore, it possesses a high triplet energy. The materials used include the electron transport layer of phosphorescent organic EL elements and organic EL elements that utilize thermally activated delayed fluorescence. They are also useful as hole transport layers. Furthermore, these polycyclic aromatic compounds are useful for introducing substituents. Therefore, because the energy of HOMO and LUMO can be moved arbitrarily, ionized potatoes It is possible to optimize the natural properties and electron affinity according to the surrounding materials. [Brief explanation of the drawing]

[0047]

Figure 1

[0048] 1. Polycyclic aromatic compound of the present invention <Description of the overall structure of the compound> The present invention relates to a polycyclic aromatic compound represented by the following general formula (1A) or general formula (1B). Preferably, a polycyclic aromatic compound represented by the following general formula (2A) or general formula (2B). In the above equations, "B" to "G" inside the circle are symbols indicating the ring structure represented by the circle. Therefore, "a" to "g" within the 6-membered aromatic ring are benzene rings or, in some cases, modified versions thereof. It is a ring (such as a 6-membered or 5-membered heteroaromatic ring), and the other signs are the same as in the definition above. Yes. Furthermore, the definition of the signs in all structural formulas shown from this paragraph onward is the same as the definition above. That is the case. [ka] [ka]

[0049] The compounds of the present invention are characterized by having one or two carbazole-like structures within the molecule. As explained below, in each formula, carbazole-like structures are formed at three locations. Furthermore, a carbazole-like structure is formed at one or two of the three locations. To use as a sign.

[0050] This carbazole-like structure, as will be described in detail later, in formula (1A), for example, the C ring and It is formed by the bonding of the D ring, containing "N", and also X 1 or X 2 In the case of NR It is formed when R is bonded to either a B ring or an E ring. Also, in formula (2A), for example The bond between the c ring and the d ring (R c and R d Formed by a combination with "N", and other , X 1 or X 2 In the case of NR, R is bonded to either the b ring or the e ring (R and R b Also is R e It is formed when it is bonded with (1B). Similarly, in formula (1B), the C ring and the D ring It is formed containing "N" through bonding, and also contains "N" through bonding of the G ring and B ring. It is formed by and also contains "N" through the bonding of the F ring and E ring. Also, formula ( 2B) Similarly, the bond between the c ring and the d ring (R c and R d (Combined with) It is formed including N, and also the bond between the g ring and the b ring (R g and R b (Combined with) It is formed including N, and also the bond between the f ring and the e ring (R f and R e (Combination with) results in "N" It is formed by including.

[0051] <Description of the ring structure and its substituents> R a is hydrogen or a substituent. This substituent may be an aryl substituent, which may be substituted. , optionally substituted heteroaryl, optionally substituted diarylamino, substituted Diheteroarylaminos which may be substituted, aryl heteroarylaminos which may be substituted Diarylboryl, which may be substituted (the two aryls are single-bonded or linked). (may be bonded by a group), may be substituted alkyl, may be substituted Cycloalkyl, optionally substituted alkoxy, optionally substituted aryl alkoxy Silyl or substituted silyl groups are preferred. If these groups have substituents, the substituents are: Examples include aryl, heteroaryl, alkyl, or cycloalkyl compounds. Details of the substituents listed above will be discussed in more detail later.

[0052] Rings B, C, D, E, F, and G are each independently an aryl ring or It is a heteroaryl ring, and at least one hydrogen in these rings is substituted with a substituent. This substituent may be an aryl which may be substituted, or even if substituted. A good heteroaryl, optionally substituted diarylamino, optionally substituted diarylamino heteroarylamino, optionally substituted arylheteroarylamino, substituted Diarylboryl (the two aryls are linked by a single bond or a linking group) (may be present), optionally substituted alkyl, optionally substituted cycloalkyl, substituted alkoxys, substituted aryloxys, or substituted syloxys Lyl is preferred. If these groups have substituents, possible substituents are aryl and hetero. Examples include aryl, alkyl, or cycloalkyl groups. Note that the rings and arrangements listed here are not representative of the rings and arrangements listed here. Details of the conversion mechanism will be explained in more detail later.

[0053] R b , R c , R d , R e , R f , and Rg These are, independently, hydrogen, aryl, Heteroaryl, diarylamino, diheteroarylamino, arylheteroaryl Amino, diarylboryl (the two aryl groups may be linked by a single bond or a linking group) (Good), alkyl, cycloalkyl, alkoxy, aryloxy, triarylsilyl , trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, or alkyldicycloalkylsilyl, and the R b , R c , R d , R e , R f ,oh Call R g At least one hydrogen in is aryl, heteroaryl, alkyl, and It may be substituted with a cycloalkyl group. For details on the substituents listed here, see below. These will be discussed in more detail later.

[0054] The aryl ring or heteroaryl ring in formulas (1A) and (1B) (i.e., The B-G rings are 5-membered or 6-membered rings that share bonds with the fused bicyclic structure contained in each formula. It is preferable to have it.

[0055] Here, "condensed biringle structure" means that in equation (1A), Y 1 , X 1 , and N are included in the composition The structure in which two saturated hydrocarbon rings are fused (the first fused biring structure on the left in the formula), and Y 2 , X 2 A structure in which two saturated hydrocarbon rings, including N, are condensed (right in the formula) This means the second condensed biring structure on the side. Similarly, in equation (1B), Y 1 and A structure in which two saturated hydrocarbon rings, each containing two nitrogen atoms, are condensed (the first on the left in the formula) (Condensed biringle structure) and Y 2 and two saturated hydrocarbon rings, each containing two nitrogen atoms, are condensed. The resulting structure (the second condensed biring structure on the right side of the formula) and Y 3 and consists of two Ns This refers to a structure in which two saturated hydrocarbon rings are fused together (the lower third fused biring structure in the formula). Although not shown in the figures for equations (2A) and (2B), a condensed biring structure exists in the same location. It exists.

[0056] Furthermore, "a 6-membered ring that shares a bond with a condensed biring structure" refers to, for example, formula (2A) or formula (2A). As shown in B), it refers to a b-ring (benzene ring (6-membered ring)) fused to a condensed bi-ring structure. Furthermore, "an aryl ring or heteroaryl ring (which is a B ring) has this 6-membered ring" means Either the B ring is formed by this 6-membered ring alone, or the 6-membered ring is included in this 6-membered ring. Furthermore, this means that other rings condense to form a B ring. In other words, here "An aryl ring or heteroaryl ring having a 6-membered ring (which is a B ring)" means a B ring This means that the six-membered ring constituting a part or portion of the structure is condensed into a condensed biring structure. (c ring),” “D ring (d ring),” “E ring (e ring),” “F ring (f ring),” “G ring (g ring). The same explanation applies to "5-membered ring" as well. ru.

[0057] The B ring, C ring, D ring, and E ring in equation (1A) correspond to the rings in equation (2A), respectively. b-ring and its substituent R b , the c ring and its substituent R c , the d-ring and its substituent R d , and the e-ring and so substituent R eThis corresponds to the following: Equation (2A) is the B-E ring of equation (1A) = "6 The selected structure corresponds to "rings B to E having a six-membered ring". "Having a six-membered ring" means As will be described later, for example, for a 6-membered ring b, its four substituents R b The neighbor of In this ring, adjacent groups bond together to form a ring, and another ring is further fused to the 6-membered b-ring. This is because it may correspond to ring B. In this sense, each ring in equation (1A) is capitalized. In contrast to the representation using B to E in equation (2A), each ring in equation (2A) is represented using lowercase b to e.

[0058] In equation (1B), the B ring, C ring, D ring, E ring, F ring, and G ring are, respectively, in equation (2 B) The b-ring and its substituent R b , the c ring and its substituent R c , the d-ring and its substituent R d , e The ring and its substituent R e , the f-ring and its substituent R f , and the g ring and its substituent R g It corresponds to. In other words, equation (2B) is a "B-ring to G-ring having a 6-membered ring" as the B-ring to G-ring of equation (1B). This corresponds to the selected structure. "Having" a 6-membered ring means, as will be explained later, for example, The b-ring is a 6-membered ring, and its four substituents R b Adjacent groups of these groups bond together to form a ring. In some cases, a B-ring is formed when another ring is fused to a 6-membered b-ring. Therefore. In this sense, each ring in equation (1B) is represented by uppercase B to G, whereas Then, each ring in equation (2B) was represented by a lowercase letter, b through g.

[0059] <Description of the change in the ring structure due to the bonding between substituents> The substituents R of the b, c, d, e, f, and g rings b , R c , Rd , R e , R f , and R g Adjacent groups bond together to form a b-ring, c-ring, d-ring, The e, f, and g rings may form an aryl ring or a heteroaryl ring together. Furthermore, at least one hydrogen in the formed ring is an aryl, heteroaryl, or diaryl compound. arylamino, diheteroarylamino, arylheteroarylamino, diarylboli (The two aryl groups may be linked by a single bond or a linking group), alkyl, cyk Roalkyl, alkoxy, aryloxy, triarylsilyl, trialkylsilyl, Tricycloalkylsilyl, dialkylcycloalkylsilyl, or alkyldicyclo They may be substituted with alkylsilyls, and at least one hydrogen in these substituents It may be substituted with aryl, heteroaryl, alkyl, or cycloalkyl compounds. The details of the rings and substituents listed here will be explained in more detail later.

[0060] Therefore, the polycyclic aromatic compounds of formula (2A) or formula (2B) are in the b-ring to g-ring. Depending on the bonding configuration of the substituents, for example, formulas (2A-fr) and (2B-fr) can be used. As shown in ), the ring structure constituting the compound changes. The B' ring and C' ring in the following formula are These correspond to the B ring and C ring in equations (1A) and (1B), respectively. Note that the d ring The ~g ring can also change in a similar manner. [ka]

[0061] The B' ring and C' ring in the above formulas (2A-fr) and (2B-fr) are the same as in formula (2A) And as explained by formula (2B), multiple substituents R b and R c Among adjacent units The aryl rings or heteroaryl rings formed by bonding with the b-ring and c-ring, respectively, are This is shown (it can also be described as a fused ring formed by the fusion of another ring structure with the b or c ring). Also, the above formula As can be seen from this, for example, the R of ring b b and the R of the c ring c , that is, substituents in different rings These two elements do not fall under the category of "adjacent elements," and therefore, they generally do not bond. "Adjacent groups" refers to groups adjacent to each other on the same ring.

[0062] Formulas (2A-fr) and (2B-fr) above represent a benzene ring which is either a b-ring or a c-ring. In contrast, for example, a benzene ring, an indole ring, a pyrrole ring, a benzofuran ring, or ben It has a B' or C' ring formed by the condensation of a zothiophene ring, etc., and the formed condensed ring B' or the fused ring C' is a naphthalene ring, a carbazole ring, an indole ring, and a di These include benzofuran rings or dibenzothiophene rings.

[0063] More specific examples of equations (2A-fr) and (2B-fr) are shown below. [ka]

[0064] The above equations (2A-fr-ex) and (2B-fr-ex) are equivalent to equation (2A-f r) and formula (2B-fr) are concrete examples, and in ring b of formulas (2A) and (2B) Two adjacent R b The aryl ring indicated by B' is formed by bonding with the b ring (benzene ring). A naphthalene ring is formed, and two adjacent R rings in the c ringc The two are joined together, forming a c ring (benz This is an example where an aryl ring (dibenzofuran ring) indicated by C' was formed along with the 'n' ring. The resulting aryl ring is a 6-membered ring (benzene ring b or c) It has aryl rings B' and C' (the B ring of formulas (1A) and (1B) and Any substituent on the C ring is R b and R c In addition, this has also been shown with n Rs, and the upper limit of n This is the maximum number of substitutions possible. Note that these explanations apply to all forms other than the specific examples mentioned above. For example, when the d-ring to g-ring changes, or when other aryl rings or heteroaryl rings are formed. The same applies to this as well.

[0065] <Description of the central element Y 1 ~Y 3 in the compound> Y 1 , Y 2 , and Y 3 These are, independently, >B-, >P-, >P(=O)-, > P(=S)-, >Al-, >Ga-, >As-, >C(-R)-, >Si(-R)-, or is >Ge(-R)-, and R in >C(-R)-, R in >Si(-R)-, and >The R in Ge(-R)- is an aryl that can be substituted, and even if substituted... A good heteroaryl, optionally substituted alkyl, or optionally substituted cycloalkyl It is Y 1 , Y 2 , and Y 3 For example, >B-, >P-, >P(=O)-, or >P(=S)- is preferred, and >B- is more preferred. Details of the substituents listed here are also provided. This will be discussed in more detail later.

[0066] <Description of the change in the ring structure due to the bonding between rings> In formulas (1A) and (1B), the C ring and D ring are single bonds or linking groups (these They may also be bonded by a bonding group (which is also called a bonding group). Also, the G ring in formula (1B) And the B ring, as well as the F ring and the E ring, each independently consists of a single bond or a linking group (these are They may also be bonded by a bonding group (collectively called a bonding group). The bond between the C ring and the D ring is called a CD bond. The bond between the G ring and the B ring is also called a GB bond, and the bond between the F ring and the E ring is also called an FE bond.

[0067] The linking groups include -CH2-CH2-, -CHR-CHR-, -CR2-CR2-, and - CH=CH-, -CR=CR-, -C≡C-, -N(-R)-, -O-, -S-, -C( -R)2-, -Si(-R)2-, or -Se- are examples. Note that -CHR- R in CHR-, R in -CR2-CR2-, R in -CR=CR-, R in -N(-R)-, - The R in C(-R)2- and the R in -Si(-R)2- are, independently of each other, hydrogen and ali. Alkyl, heteroaryl, alkyl, alkenyl, alkynyl, or cycloalkyl Furthermore, at least one hydrogen atom in R is substituted with an alkyl or cycloalkyl group. It may also be possible for two adjacent Rs to form a ring, such as cycloalkylene or allile. They may also form heteroarylenes. Details of the substituents listed here are not provided. This will be discussed in more detail later.

[0068] The bonding groups include single bonds, and the linking groups are -CR=CR-, -N(-R)-, and -O-. -S-, -C(-R)2-, -Si(-R)2-, and -Se- are preferred, single bonds, -CR=CR-, -N(-R)-, -O-, -S-, and -C(-R) as linking groups 2- is more preferred, and as single bonds, -CR=CR-, -N(-R)-, -O- as linking groups. , and -S- are even more preferred, and single bonds are most preferred.

[0069] The position where the two rings are bonded by the bonding group is not particularly limited as long as it is a position where bonding is possible. It is preferable that the bonds are formed at the most adjacent positions, for example, the bond positions of "N" in each ring ( It is preferable that the ortho (position 2) is bonded to the position of position 1) (Equation (1A) (See structural formula (1B)).

[0070] The c-ring and d-ring in equations (2A) and (2B) of the lower-level equations are also treated in the same way as in the higher-level equations. They may be bonded by single bonds or by linking groups (collectively also called bonding groups). Furthermore, the g-ring and b-ring, as well as the f-ring and e-ring, in equation (2B) of the lower-level equation are also in the upper-level equation. Similarly, each can be independently a single bond or a linking group (collectively also called a bonding group). They may be bonded by the following: the bond between the c and d rings is a cd bond, and the bond between the g and b rings is a cd bond. Gb bonds, and bonds between f-rings and e-rings are also called fe bonds. The type of linking group and bond position are determined by the higher-level formula. You can quote the explanation.

[0071] <Description of the carbazole-like structure (1)> As described above, the compound of the present invention has a C ring and a D ring (c ring and d ring), a G ring and The B ring (g ring and b ring), and the F ring and E ring (f ring and e ring) can be bonded together. In formulas (1A) and (2A), the first carbazole-like structure is as shown in formula (1B) and In formula (2B), the first, second, and third carbazole-like structures can be formed. In the structural formulas below, the dotted lines represent bonding groups (single bonds and linking groups). However, this does not apply to the compounds of the present invention. This is when one or two of the three carbazole-like structures that can be formed within the molecule are formed. It is characterized by having this feature. [ka] [ka]

[0072] The reason it's called a "carbazole-like structure" is, for example, as explained by formula (2A), the c-ring and d-ring The "N" bond is connected to the ortho (position 2) of the "N" atom via a single bond, with the bond position (position 1) being the reference point. This is because, in such cases, the carbazole structure, which is the most basic structure, is formed within the molecule. Furthermore, as mentioned above, there are other types of bonding groups besides single bonds, and the bonding positions between rings are also limited. It is not a target, and as will be explained elsewhere, each ring such as the c ring is bonded to adjacent substituents, etc. Because the ring structure changes further, structures other than carbazole are also formed. It is called a "carbazole-like structure" because it also forms structures similar to carbazole.

[0073] When a carbazole-like structure is formed, the binding group can be a single bond, and the linking group can be - CH2-CH2-, -CHR-CHR-, -CR2-CR2-, -CR=CR-, -N( -R)-, -O-, -S-, -C(-R)2-, -Si(-R)2-, and -Se- are Preferably, single bonds, linking groups -CR=CR-, -N(-R)-, -O-, -S-, -C(-R)2- is more preferred, and -CR=CR- and -N as single bonds and linking groups. (-R)-, -O-, and -S- are more preferred, with single bonds being the most preferred.

[0074] When a carbazole-like structure is formed, the position where the two rings are bonded by the binding group is While there are no particular limitations as long as the joints can be made, it is preferable to join them at the most adjacent positions. For example, the positions of the ortho (position 2) relative to the bond position (position 1) of "N" in each ring. It is preferable that they be bonded together (formulas (1A), (1B), (2A), and (2B) (See structural formula). When a carbazole-like structure is formed, the two rings that are joined are preferably both benzene rings. stomach.

[0075] <Description of the linking elements X 1 and X 2 in the compound> X in equations (1A) and (2A) 1 and X 2 These are, independently, >NR , >O, >S, >C(-R)2, >Si(-R)2, or >Se, and the >NR R in C(-R)2 and R in Si(-R)2 are, independently of each other, hydrogen. aryls which may be substituted, heteroaryls which may be substituted These are also alkyl groups, or cycloalkyl groups that may be substituted. (The following are listed below.) Details of the substituents will be discussed in more detail later.

[0076] X 1 and X 2 Preferably, >NR, >O, >S, or >C(-R)2 are used. >NR or >O is more preferred, and >NR is even more preferred. (Referring to the view of good TADF properties) From this perspective, >NR, >O, and >S are preferred, and more specifically, due to the multiple resonance effect From the viewpoint of orbital localization, >NR is preferred, and from the viewpoint of heavy atom effects, >S is preferred. Furthermore, from the viewpoint of emission wavelength, >O is preferred for short-wavelength emission, and for long-wavelength emission. >NR or >S is preferred.

[0077] >At least one of the two Rs in C(-R)2 and the two Rs in Si(-R)2 One may be bonded by a single bond or by a linking group (these are collectively also called a bonding group). The linking groups for this include -CH2-CH2-, -CHR-CHR-, and -CR2-CR2. -, -CH=CH-, -CR=CR-, -C≡C-, -N(-R)-, -O-, -S-, Examples include -C(-R)2-, -Si(-R)2-, or -Se-, and the following structure is an example. These are examples. Note that R in -CHR-CHR-, R in -CR2-CR2-, and -CR= R in CR-, R in -N(-R)-, R in -C(-R)2-, and R in -Si(-R)2- R can be any of the following, independently: hydrogen, aryl, heteroaryl, alkyl, alkenyl, and Lukinyl or cycloalkyl, wherein at least one hydrogen in R is a It may be substituted with kyl or cycloalkyl. Also, two adjacent Rs may form a ring. They may form cycloalkylenes, arylenes, and heteroarylenes. Details of the substituents listed here will be explained in more detail later. [ka]

[0078] The bonding groups include single bonds, and the linking groups are -CR=CR-, -N(-R)-, and -O-. -S-, -C(-R)2-, -Si(-R)2-, and -Se- are preferred, single bonds, -CR=CR-, -N(-R)-, -O-, -S-, and -C(-R) as linking groups 2- is more preferred, and as single bonds, -CR=CR-, -N(-R)-, -O- as linking groups. , and -S- are even more preferred, and single bonds are most preferred.

[0079] The positions where the two R groups bond via the bonding group are not particularly limited as long as they are bondable positions. It is preferable that the bonds are formed at the most adjacent positions, for example, when the two R groups are phenyl groups. The ortho (2nd position) is defined based on the bond position (1st position) of the "C" or "Si" in the phenyl group. It is preferable that the bonds are formed at the same positions (see the structural formula above).

[0080] <X 1 or X 2 <Description of the change in the ring structure due to the bonding between X and the ring> X in equations (1A) and (2A) 1 >NR's R, >C(-R)2's R , or >Si(-R)2, where R is a single bond or a linking group (these are collectively called a bonding group) (u) may be bonded to at least one of the a ring and the B ring (b ring). X in equations (1A) and (2A) 2 >NR's R, >C(-R)2's R , or >Si(-R)2, where R is a single bond or a linking group (these are collectively called a bonding group) (u) may be bonded to at least one of the a-ring and the E-ring (e-ring).

[0081] The linking groups include -CH2-CH2-, -CHR-CHR-, -CR2-CR2-, and - CH=CH-, -CR=CR-, -C≡C-, -N(-R)-, -O-, -S-, -C( -R)2-, -Si(-R)2-, and -Se- are examples. Note that -CHR- R in CHR-, R in -CR2-CR2-, R in -CR=CR-, R in -N(-R)-, - The R in C(-R)2- and the R in -Si(-R)2- are, independently of each other, hydrogen and ali. Alkyl, heteroaryl, alkyl, alkenyl, alkynyl, or cycloalkyl Furthermore, at least one hydrogen atom in R is substituted with an alkyl or cycloalkyl group. It may also be possible for two adjacent Rs to form a ring, such as cycloalkylene or allile. They may also form heteroarylenes. Details of the substituents listed here are not provided. This will be discussed in more detail later.

[0082] X involved in the binding 1 or X 2 As such, >NR and >C(-R)2 are preferred. NR is preferable.

[0083] The bonding groups include single bonds, and the linking groups are -CR=CR-, -N(-R)-, and -O-. -S-, -C(-R)2-, -Si(-R)2-, and -Se- are preferred, single bonds, -CR=CR-, -N(-R)-, -O-, -S-, and -C(-R) as linking groups 2- is more preferred, and as single bonds, -CR=CR-, -N(-R)-, -O- as linking groups. , and -S- are even more preferred, and single bonds are most preferred.

[0084] The rings that join together are, X 1 For X, the B ring (b ring) is preferred, 2 Regarding the E ring ( (E-ring) is preferable.

[0085] In the higher-level formula (1A), "R of >NR, R of >C(-R)2, or >Si In (-R)2, R is a single bond or linking group, with less than one bond between the a ring and the B ring (or E ring). The provision that "both are combined with one" is expressed in the subordinate formula (2A) as "the R of >NR, before Note: In C(-R)2, R, or in Si(-R)2, R represents a single bond, -CH=CH-, -C R=CR-, -C≡C-, -N(-R)-, -O-, -S-, -C(-R)2-, -Si (-R)2- or -Se-, at least one of the a-ring and b-ring (or e-ring) This corresponds to the provision that "is combined with".

[0086] This regulation can be represented, for example, by the following structural formula. Note that substituent R in the structural formula a , R b , R c , R d , and R e It was hidden, but it actually exists. [ka]

[0087] In the structural formula on the left, X 1 and X 2 The options are (>NR, >C(-R)2, and >Si (-R)2) is an example in which R is bonded to the b ring and the e ring, respectively, and the b ring (benzene X for rings (and e rings (benzene rings)) 1 or X 2 The other rings contract as if to incorporate them. This represents a compound having a B' ring and an E' ring formed by fusion. 'and fused ring E' is, for example, a phenoxazine ring, a phenothiazine ring, or a carbazole ring. , or an acridine ring, etc.

[0088] The central structural formula represents a more specific example of the structural formula on the left, X 1 and X 2 is > The R (phenyl group) in NR is bonded to the b ring (benzene ring) and e ring (benzene ring) by single bonds. This is an example where the carbazole rings B' and E', enclosed by dashed lines, are formed by bonding with the rhombic ring. ru.

[0089] The structural formula on the right represents a more specific example of the structural formula on the left, X 1 and X 2 >N The R (phenyl group) of -R is connected to the b ring (benzene ring) by the linking group -O- The phenoxazine ring B' enclosed by the dashed line is formed by bonding, and the e ring is formed by the linking group -S-. This is an example where a phenothiazine ring E', enclosed by a dashed line, is formed by bonding with a benzene ring.

[0090] X 1 and X 2 The options are (>NR, >C(-R)2, and >Si(-R)2). The positions where R is bonded to the ring (ring B, ring E, ring b and ring e) by a bonding group are: The location is not particularly limited, but it is preferable to connect at the most adjacent locations, for example. If R is a phenyl group, then the "X" in the ring to be bonded and the phenyl group. 1 " and "X 2 " It is preferable that the bonds are formed at the ortho (position 2) relative to the bond position (position 1). (See the structural formula above.)

[0091] Furthermore, the explanation of the specific examples above does not apply to any other forms, such as X 1 oh Call X 2 If either of them is bonded to the ring, if it is bonded to the a ring, if it is bonded to the other linking group This can also be applied in similar cases.

[0092] <Description of the carbazole-like structure (2)> In the compound of the present invention, as described above, X in formulas (1A) and (2A) 1 Oh biX 2 R can bond with adjacent rings, but of these bonding configurations, X 1 ">N" as -R of R (where R is the substituted aryl or substituted heterozygous aryl) (Limited to loaryl or the optionally substituted cycloalkyl) and "B ring" or The bond formed with the "b ring" (X 1 B bond or X 1 The second bond (also called a b bond) Carbazole-like structures are further, X 2 "R of NR" as ">NR" (this R is the substitution An aryl which may be substituted, a heteroaryl which may be substituted, or the substituted A bond formed between a cycloalkyl group (which may be cycloalkyl) and an "E ring" or "e ring". (X 2 E-joint or X 2 A third carbazole-like structure exists due to an e-bond (also called an e-bond). It is possible. [ka]

[0093] The R in NR, which can form a carbazole-like structure, may be substituted. A la is preferable. Furthermore, a single bond is preferred as the bonding group between R and the ring.

[0094] <Description of the number of carbazole-like structures> As described above, in formulas (1A) and (2A), the first carbazole-like structure is It is formed from a CD bond or cd bond, and the second structure is X 1 B bond or X 1 b knot It is formed from a combination, and the third structure is X 2 E-joint or X 2 Formed from an e bond Furthermore, in formulas (1B) and (2B), the first carbazole-like structure is CD-bound. Alternatively, it is formed from a cd bond, and the second structure is derived from a GB bond or gb bond. The third structure is formed, and the third structure is formed from an FE bond or fe bond. The compound of the present invention The substance is one or two of these three carbazole-like structures that can be formed within the molecule. It is characterized by the formation of a structure.

[0095] In formulas (1A) and (2A), if only the first carbazole-like structure exists... (1Cz isomer), if only the second carbazole-like structure exists (2Cz isomer), the first And if a second carbazole-like structure exists (12Cz isomer), the second and third carbazoles While a basol-like structure exists (23Cz isomer), there are also 1Cz, 12Cz, and The 23Cz isomer is preferred, the 1Cz and 12Cz isomers are more preferred, and the 1Cz isomer is even more preferred. preferable.

[0096] In equations (1B) and (2B), if only the first carbazole-like structure exists... (1Cz isomer), if the first and second carbazole-like structures exist, (12Cz isomer) However, the 1Cz isomer is preferred.

[0097] <Description of the structural changes of the a-ring, b~g rings> In the explanation so far, the a, b, c, d, e, f, and g rings have been described as benzene rings. As illustrated and explained above, below, rings a, b to g are not benzene rings, but are 5-membered rings. This section describes examples of structural changes to a six-membered aryl ring or heteroaryl ring. The explanation above should also be understood in the case where these rings undergo the following structural changes. It can be done.

[0098] <Structural change of the a-ring> In equations (1A) and (2A), the -C(-R) in the a ring a Replace )=" with "-N=". It may be replaced and form a pyridine ring. Note that the following structural diagram shows the a ring and its surrounding structure. This is a diagram showing only a portion of it. [ka]

[0099] <Structural changes of the b~g rings> In the b, c, d, e, f, and g rings in formulas (2A) and (2B) Any "-C(-R)=" (where R is R b , R c , R d , R e , R f , or R g in The part "-N=" may be replaced with "-N=". [ka] As shown above, for example, in the d-ring, "-C(-R d Replace the part that says ")=" with "-N=". They may be replaced, and in this way, the d rings that are represented as benzene rings in each formula are pyr For zinc rings, pyrimidine rings, pyridazine rings, pyrazine rings, and other nitrogen-containing heteroaryl rings It may change. Also, if there are adjacent groups on the d-ring (in the above formula, the remaining two) Adjacent R d These are bonded together to form a heteroaryl ring (quino in the above formula) along with the d ring. It forms a phosphorus ring, and the formed ring may be further substituted (indicated by n Rs). This is as stated above.

[0100] Other variations include the following: [ka]

[0101] X 1 , X 2 , or >N- bonded carbon at the ortho or para position "-C(- R d It is preferable that ")=" is replaced with "-N=".

[0102] If other parts are replaced with "-N=", or if there are b, c, e, or f rings other than d rings The same applies when the g ring changes.

[0103] In the b, c, d, e, f, and g rings in formulas (2A) and (2B) Any "-C(-R)=C(-R)-" (where R is R b , R c , R d , R e , R f , or R g (is) "-N(-R)-", "-O-", "-S-", "-C(-R) It may be replaced with "2-", "-Si(-R)2-", or "-Se-", as described above. The R in "-N(-R)-", the R in "-C(-R)2-", and the R in "-Si(-R)2-" R is hydrogen, aryl, heteroaryl, alkyl, or cycloalkyl, and Even if at least one hydrogen in R is substituted with an alkyl or cycloalkyl group Good. Details of the substituents listed here will be discussed later. [ka] As shown above, for example, in the d-ring, "-C(-R d )=C(-R d The part that says )-" "-N(-R)-", "-O-", "-S-", "-C(-R)2-", "-Si(-R )2-" or "-Se-" may be replaced in this way, and in each expression, benz The d-rings shown as n-rings include R-substituted pyrrole rings, furan rings, thiophene rings, and others. It may change into a nitrogen-containing oxygen-sulfur heteroaryl ring (5-membered ring) or an aryl ring (5-membered ring). i. Also, if there are adjacent groups on the d-ring (in the above formula, the remaining two adjacent R groups) d ) These are bonded together with the d ring to form a heteroaryl ring (in the above formula, the R-substituted ind- Forms rings such as benzofuran rings, benzothiophene rings, or aryl rings, As mentioned above, the resulting ring may be further substituted (shown by n Rs). be.

[0104] Other variations include the following: [ka]

[0105] Other parts are "-N(-R)-", "-O-", "-S-", and "-C(-R)2-". When replaced with "-Si(-R)2-" or "-Se-", or when a b-ring other than a d-ring is replaced The same applies when the c, e, f, and g rings are altered.

[0106] The two Rs in "-C(-R)2-" and the two Rs in "-Si(-R)2-" At least one of the elements is connected by a single bond or a linking group (collectively also called a bonding group) They may be bonded. Examples of these linking groups include -CH2-CH2-, -CHR-CHR-, -CR2-CR2-, -CH=CH-, -CR=CR-, -C≡C-, -N(-R)-, Examples include -O-, -S-, -C(-R)2-, -Si(-R)2-, or -Se-. For example, the following structure can be cited. Note that R in -CHR-CHR- and -CR2-CR2 -R, -CR=CR-R, -N(-R)-R, -C(-R)2-R, and -S In i(-R)2-, R can be independently hydrogen, aryl, heteroaryl, or alkyl. , alkenyl, alkynyl, or cycloalkyl, and at least 1 in R One hydrogen may be substituted with an alkyl or cycloalkyl group. Also, two adjacent hydrogens Two Rs form a ring, creating cycloalkylenes, arylenes, and heteroarylenes. It is acceptable if it is achieved. Details of the substituents listed here will be discussed in more detail later. [ka]

[0107] The bonding groups include single bonds, and the linking groups are -CR=CR-, -N(-R)-, and -O-. -S-, -C(-R)2-, -Si(-R)2-, and -Se- are preferred, single bonds, -CR=CR-, -N(-R)-, -O-, -S-, and -C(-R) as linking groups 2- is more preferred, and as single bonds, -CR=CR-, -N(-R)-, -O- as linking groups. , and -S- are even more preferred, and single bonds are most preferred.

[0108] The positions where the two R groups bond via the bonding group are not particularly limited as long as they are bondable positions. It is preferable that the bonds are formed at the most adjacent positions, for example, when the two R groups are phenyl groups. The ortho (2nd position) is defined based on the bond position (1st position) of the "C" or "Si" in the phenyl group. It is preferable that the bonds are formed at the same positions (see the structural formula above).

[0109] <Specific description of the ring and substituents> Next, regarding the rings and substituents listed in the explanation so far (the second substituent which is further substituted on the first substituent) Details (including the conversion mechanism) will be explained separately.

[0110] The "aryl ring" is, for example, an aryl ring having 6 to 30 carbon atoms, preferably having 6 carbon atoms. Aryl rings with ~20 carbon atoms, aryl rings with 6 to 16 carbon atoms, aryl rings with 6 to 12 carbon atoms, These include aryl rings with 6 to 10 carbon atoms. Note that the "aryl rings" as rings B to G in formulas (1A) and (1B) are, (2A) and formula (2B) "R b , R c , R d , R e , R f , and R g of The adjacent groups within the ring bond together to form the b, c, d, e, f, and g rings, respectively. This corresponds to "aryl ring formed together with", but this "formed aryl ring" is Since rings b to g are already composed of benzene rings with 6 carbon atoms, the most suitable ring for this benzene ring is... The lower limit for the number of carbon atoms in a fused ring, formed by the fusion of two small five-membered rings, is 9. However, as mentioned above, the benzene rings b-g are nitrogen-containing heteroaryl rings. Even if it changes into a (6-membered ring or 5-membered ring) or an oxygen-containing sulfur heteroaryl ring (5-membered ring), Therefore, in this case, the lower limit of the number of carbon atoms changes accordingly.

[0111] Specific examples of "aryl rings" include the monocyclic benzene ring and the condensed bicyclic naphthium ring. Talene rings, condensed tricyclic rings, acenaphthylene rings, fluorene rings, phenalene rings, or These are phenanthrene rings, anthracene rings, condensed tetracyclic systems, triphenylene rings, and pyrene rings. , or a naphthacene ring, or a condensed pentacyclic system such as a perylene ring or a pentacene ring. That's right.

[0112] The "heteroaryl ring" is, for example, a heteroaryl ring having 2 to 30 carbon atoms, and is preferably These are heteroaryl rings with 2 to 25 carbon atoms, heteroaryl rings with 2 to 20 carbon atoms, and carbon atoms with 2 carbon atoms. These include heteroaryl rings with approximately 15 carbon atoms, or heteroaryl rings with 2 to 10 carbon atoms. A "heteroaryl ring" is, for example, a ring composed of atoms other than carbon, such as oxygen, sulfur, and nitrogen. These include heterocycles containing 1 to 5 heteroatoms selected from a given set. Note that the "heteroaryl ring" in formulas (1A) and (1B) is the B-G ring. This is defined by "R" in equations (2A) and (2B). b , R c , R d , R e , R f , and R g Adjacent groups bond together to form a b-ring, c-ring, d-ring, e-ring, f-ring, and so on. This corresponds to "a heteroaryl ring formed together with a γ ring," but this "formed heteroaryl ring" Regarding the "benzene ring," since rings b to g are already composed of benzene rings with 6 carbon atoms, The lower limit for the number of carbon atoms in a fused ring, formed by the fusion of a minimum 5-membered ring with this benzene ring, is 6. However, as mentioned above, the benzene rings b-g are nitrogen-containing heteroaryl rings. Even if it changes into a (6-membered ring or 5-membered ring) or an oxygen-containing sulfur heteroaryl ring (5-membered ring), Therefore, in this case, the lower limit of the number of carbon atoms changes accordingly.

[0113] Specific examples of "heteroaryl rings" include pyrrole rings, oxazole rings, and isoxazole rings. Zole ring, thiazole ring, isothiazole ring, imidazole ring, oxadiazole ring, thi diazole ring, triazole ring, tetrazol ring, pyrazole ring, pyridine ring, pyrimi Zin ring, pyridazine ring, pyrazine ring, triazine ring, indole ring, isoindole ring, 1H-indazole ring, benzimidazole ring, benzoxazole ring, benzothiazo Lu ring, 1H-benzotriazole ring, quinoline ring, isoquinoline ring, synnoline ring, quinine ring Zoline ring, quinoxaline ring, phenanthroline ring, phthalazine ring, naphthyridine ring, pli Pteridine ring, carbazole ring, acridine ring, phenoxa Zinc ring, phenothiazine ring, phenazine ring, phenazacillin ring, indoridine ring, furan Ring, benzofuran ring, isobenzofuran ring, dibenzofuran ring, naphthobenzofuran ring, Thiophene ring, benzothiophene ring, isobenzothiophene ring, dibenzothiophene ring, Naphthobenzothiophene ring, benzophosphorus ring, dibenzophosphorus ring, benzophosphorus ring Dibenzophosphate ring, dibenzophosphate ring, furazan ring, thianthlene ring, India Locarbazole ring, benzoindocarbazole ring, benzobenzoindocarbazole These include rings, imidazoline rings, or oxazoline rings.

[0114] "Aryl" refers to, for example, an aryl with 6 to 30 carbon atoms, preferably with 6 to 2 carbon atoms. 0 aryl atoms, aryl atoms with 6 to 16 carbon atoms, aryl atoms with 6 to 12 carbon atoms, or 6 carbon atoms Examples include 10-10 reels.

[0115] Specific examples of "aryl" include monocyclic phenyl and bicyclic biphenyl. (2-biphenylyl, 3-biphenylyl, or 4-biphenylyl), a condensed bicyclic system. Naphthyl (1-naphthyl or 2-naphthyl), and the tricyclic terpheniryl (m- Terphenyl-2'-yl, m-terphenyl-4'-yl, m-terphenyl-5'- Il, o-terphenyl-3'-yl, o-terphenyl-4'-yl, p-terphenyl Ru-2'-yl, m-terphenyl-2-yl, m-terphenyl-3-yl, m-ter Phenyl-4-yl, o-terphenyl-2-yl, o-terphenyl-3-yl, o- Terphenyl-4-yl, p-terphenyl-2-yl, p-terphenyl-3-yl, Alternatively, p-terphenyl-4-yl), a condensed tricyclic system, acenaphthylene-(1-, 3-, 4-, or 5-) fluorine, fluorene-(1-, 2-, 3-, 4-, or 9 -)yl, phenalene-(1- or 2-)yl, phenanthrene-(1-, 2-, 3 -, 4-, or 9-)il, or anthracene-(1-, 2-, or 9-) 5'-phenyl-m-terphenyl-2-yl, a tetracyclic compound. , 5'-phenyl-m-terphenyl-3-yl, 5'-phenyl-m-terphenyl- 4-yl, or m-quaterphenyl), a condensed tetracyclic system, triphenylene-(1 - or 2-)yl, pyren-(1-, 2-, or 4-)yl, or naphthase n-(1-, 2-, or 5-)yl, or a condensed pentacyclic system, perylene-(1- , 2-, or 3-)il, or pentase-(1-, 2-, 5-, or 6- ) and so on.

[0116] Furthermore, an aryl molecule is used as the second substituent, i.e., the substituent (first substituent) is further substituted. The aryl substituent (second substituent) has at least one water molecule in the aryl The elements are aryl groups such as phenyl (specific examples are the groups mentioned above), and alkyl groups such as methyl (specific examples are...) (These are the groups described later), or cycloalkyl groups such as cyclohexyl or adamantyl. Structures substituted with the group described later are also included in the category of aryl as a second substituent. One example is when the second substituent is a fluorenyl group, at least at the 9-position. Each hydrogen atom is an aryl group such as phenyl, an alkyl group such as methyl, or a cyclohexagon. These include fluorenyl groups substituted with cycloalkyl groups such as syl or adamantyl. Such groups are also included in aryl groups as secondary substituents.

[0117] "Arylene" is, for example, arylene having 6 to 30 carbon atoms, preferably having 6 carbon atoms. Arylenes with up to 20 carbon atoms, arylenes with 6 to 16 carbon atoms, arylenes with 6 to 12 carbon atoms, These include arylenes with 6 to 10 carbon atoms. A specific example of "arirene" is, for instance, the "aryl" (monovalent group) mentioned above, which is used to form one water molecule. Examples include structures that use a divalent base after removing the element.

[0118] "Heteroaryl" is, for example, a heteroaryl with 2 to 30 carbon atoms, preferably, Heteroaryl compounds with 2 to 25 carbon atoms, heteroaryl compounds with 2 to 20 carbon atoms, and heteroaryl compounds with 2 to 15 carbon atoms. These include heteroaryls, or heteroaryls with 2 to 10 carbon atoms. A "reel" is, for example, a ring element selected from oxygen, sulfur, and nitrogen in addition to carbon. It is a monovalent group, such as a heterocycle, that contains 1 to 5 telo atoms.

[0119] Specific examples of "heteroaryls" include pyrrolyl, oxazolyl, and isoxa. Zolyl, thiazolyl, isothiazolyl, imidazolyl, oxadiazolyl, thiadiazolyl Triazolyl, tetrazolyl, pyrazolyl, pyridinyl, pyrimidinyl, pyridadinyl Lu, pyrazinyl, triazinyl, indolyl, isoindolyl, 1H-indazolyl, be Nzoimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl , quinolinyl, isoquinolinyl, cinnolinyl, quinazolinyl, quinoxalinyl, fena Ntorolinil, Phthalazinil, Naphthilidinil, Prinyl, Pteridinil, Carbazolyl , acridinyl, phenoxazinyl, phenoxazinyl, phenothiazinyl, phenadyl Nyl, phenazacylinyl, indolidinyl, furanyl, benzofuranyl, isobenzofuranyl Nyl, dibenzofuranil, naphthobenzofuranil, thiophenyl, benzothiophenyl, Isobenzothiophenyl, dibenzothiophenyl, naphthobenzothiophenyl, benzothiophenyl Suphoryl, dibenzophosphoryl, monovalent group of the benzophosphorus oxide ring, dibenzophosphorus Monovalent groups of the hol oxide ring, flazanyl, thianthrenyl, indrocarbazolyl, ve Nzoindocarbazolyl, benzobenzoindocarbazolyl, imidazolinyl, also Examples include oxazolinyl.

[0120] Furthermore, a heteroaryl as the second substituent, i.e., a substituent (first substituent) is also placed The heteroaryl as the substitution substituent (second substituent) has At least one hydrogen atom is present in aryl groups such as phenyl (specific examples are the groups mentioned above), methyl groups, etc. Alkyl groups (specific examples of which will be discussed later), or cyclohexyl or adamantyl groups, etc. Structures substituted with cycloalkyl groups (specific examples of which will be discussed later) also have heteros as the second substituent. It is included in the arrow. One example is when the second substituent is a carbazolyl group, at least at position 9. Each hydrogen atom is an aryl group such as phenyl, an alkyl group such as methyl, or a cyclohexagon. These include carbazolyl groups substituted with cycloalkyl groups such as syl or adamantyl. Such groups are also included in heteroaryls as secondary substituents.

[0121] "Heteroarylene" is, for example, a heteroarylene having 2 to 30 carbon atoms, preferably These are heteroarylenes with 2 to 25 carbon atoms, heteroarylenes with 2 to 20 carbon atoms, and heteroarylenes with 2 carbon atoms. These include heteroarylenes with ~15 carbon atoms, or heteroarylenes with 2 to 10 carbon atoms. "Heteroarylenes" are, for example, ring constituent atoms that include oxygen, sulfur, and nitrogen in addition to carbon. It is a divalent group, such as a heterocycle, containing 1 to 5 heteroatoms selected from the above. A specific example of "heteroarylene" is the "heteroaryl" (monovalent group) mentioned above. One example is a structure in which one hydrogen atom is removed to form a divalent group.

[0122] "Diarylamino" is an amino group in which two aryl groups are substituted, and this aryl group For further details, you can refer to the explanation of "Aryl" mentioned above. "Diheteroarylamino" is an amino group in which two heteroaryl groups are substituted, For details on heteroaryl compounds, refer to the explanation of "heteroaryl compounds" mentioned above. "Aryl heteroarylamino" is an amino acid substituted with aryl and heteroaryl. It is a no-group, and for details on this aryl and heteroaryl, see "aryl" above. And we can quote the explanation of "heteroaryl."

[0123] "Diarylboryl" is a boryl group in which two aryl groups are substituted, and this aryl For more details, refer to the explanation of "Aryl" above. Also, these two aryls are , single bonds or linking groups (e.g., -CH=CH-, -CR=CR-, -C≡C-, >N-) Bonded via R, >O, >S, >C(-R)2, >Si(-R)2, or >Se) It may be there. Here, the R of -CR=CR-, the R of >NR, the R of >C(-R)2, In the notation Si(-R)2, R can stand for aryl, heteroaryl, diarylamino, or alkyl. , alkenyl, alkynyl, cycloalkyl, alkoxy, or aryloxy Furthermore, at least one hydrogen atom in R may be an aryl, heteroaryl, or alkyl group. They may be substituted with alkenyl, alkynyl, or cycloalkyl compounds. Also, adjacent Two R groups form a ring, resulting in cycloalkylene, arylene, and heteroarylene. They may form an aryl substituent. For details on the substituents listed here, see the "aryl substituents" mentioned above. "Arylene", "heteroaryl", "heteroaryl", and "diaryl" Explanation of "amino," as well as "alkyl," "alkenyl," and "alkynyl" described later. "Cycloalkyl," "cycloalkylene," "alkoxy," and "aryloxy" You can quote the explanation from "[...]."

[0124] "Alkyl" can be either a straight chain or a branched chain, for example, a straight chain with 1 to 24 carbon atoms. A branched alkyl group having 3 to 24 carbon atoms, preferably with 1 to 18 carbon atoms. Alkyl (branched-chain alkyl with 3-18 carbon atoms), alkyl (with 1-12 carbon atoms) 2 branched-chain alkyl groups, C1-C6 alkyl groups (C3-C6 branched-chain alkyl groups), carbon Alkyl groups with 1 to 5 prime atoms (branched-chain alkyl groups with 3 to 5 carbon atoms), alkyl groups with 1 to 4 carbon atoms (carbon Examples include branched alkyl groups with prime numbers 3-4.

[0125] Specific examples of "alkyl" include methyl, ethyl, n-propyl, isopropyl, and 1 -Ethyl-1-methylpropyl, 1,1-diethylpropyl, 1,1,2-trimethylpropyl Ropil, 1,1,2,2-tetramethylpropyl, 1-ethyl-1,2,2-trimethyl Propyl, n-butyl, isobutyl, s-butyl, t-butyl, 2-ethylbutyl, 1, 1-dimethylbutyl, 3,3-dimethylbutyl, 1,1-diethylbutyl, 1-ethyl- 1-methylbutyl, 1-propyl-1-methylbutyl, 1,1,3-trimethylbutyl, 1-Ethyl-1,3-dimethylbutyl, n-pentyl, isopentyl, neopentyl, t -Pentyl(t-amyl), 1-methylpentyl, 2-propylpentyl, 1,1-dimethyl Tylpentyl, 1-ethyl-1-methylpentyl, 1-propyl-1-methylpentyl, 1-Butyl-1-methylpentyl, 1,1,4-trimethylpentyl, n-hexyl, 1 -methylhexyl, 2-ethylhexyl, 1,1-dimethylhexyl, 1-ethyl-1- Methylhexyl, 1,1,5-trimethylhexyl, 3,5,5-trimethylhexyl, n-heptyl, 1-methylheptyl, 1-hexylheptyl, 1,1-dimethylheptyl , 2,2-dimethylheptyl, 2,6-dimethyl-4-heptyl, n-octyl, t-octyl Ctyl (1,1,3,3-tetramethylbutyl), 1,1-dimethyloctyl, n-nonyl L, n-decyl, 1-methyldecyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-oc These include tadecyl or n-eicosyl.

[0126] Regarding "alkenyl," you can refer to the explanation of "alkyl" above. It is a group in which the CC single bond in the structure of "alkyl" is replaced with a C=C double bond, and there is not just one. A group in which two or more single bonds are replaced by double bonds (such as alkadiene-yl or alkantriene) This also includes (also known as -il).

[0127] Regarding "alkynyl," you can refer to the explanation of "alkyl" above. It is a group in which the single C≡C bond in the structure of "alkyl" is replaced with a triple C≡C bond, and there is not just one of them. Groups in which two or more single bonds are replaced by triple bonds (such as alkadiynes and alkantriynes) This also includes (also known as -il).

[0128] "Cycloalkyl" refers to, for example, a cycloalkyl group having 3 to 24 carbon atoms, preferably, Cycloalkyl groups with 3 to 20 carbon atoms, cycloalkyl groups with 3 to 16 carbon atoms, and groups with 3 to 14 carbon atoms. Cycloalkyl, cycloalkyl with 3 to 12 carbon atoms, cycloalkyl with 5 to 10 carbon atoms, Cycloalkyl groups with 5-8 carbon atoms, cycloalkyl groups with 5-6 carbon atoms, or cycloalkyl groups with 5 carbon atoms. Examples include rhalkyls.

[0129] Specific examples of "cycloalkyl" include cyclopropyl, cyclobutyl, and cyclopene. Cyclothyl, Cyclohexyl, Cycloheptyl, Cyclooctyl, Cyclononyl, Cyclodecyl or alkyl (especially methyl) substituted derivatives of these C1-C5 or C1-C4 compounds, nor Bornenyl, bicyclo[1.1.0]butyl, bicyclo[1.1.1]pentyl, bicyclo [2.1.0]pentyl, bicyclo[2.1.1]hexyl, bicyclo[3.1.0] Hexyl, bicyclo[2.2.1]heptyl, bicyclo[2.2.2]octyl, Adamantine These include ntyl, diamantyl, decahydronaphthalenyl, or decahydroazurenyl. ru.

[0130] "Cycloalkylene" is, for example, a cycloalkylene having 3 to 24 carbon atoms, preferably These are cycloalkylenes with 3 to 20 carbon atoms, cycloalkylenes with 3 to 16 carbon atoms, and cycloalkylenes with 3 carbon atoms. ~14 cycloalkylenes, cycloalkylenes with 3-12 carbon atoms, cycloalkylenes with 5-10 carbon atoms Roalkylene, cycloalkylene with 5-8 carbon atoms, cycloalkylene with 5-6 carbon atoms, Examples include cycloalkylenes with 5 carbon atoms. A specific example of "cycloalkylene" is the "cycloalkyl" (monovalent group) mentioned above. One example is a structure in which one hydrogen atom is removed to form a divalent group.

[0131] "Alkoxy" can be either a straight chain or a branched chain, for example, a straight chain with 1 to 24 carbon atoms. Alkoxy or branched alkoxy having 3 to 24 carbon atoms, preferably having 1 to 1 carbon atoms. 8 alkoxys (branched chain alkoxys with 3 to 18 carbon atoms), alkoxys with 1 to 12 carbon atoms ( Branched alkoxys with 3 to 12 carbon atoms, alkoxys with 1 to 6 carbon atoms (branched alkoxys with 3 to 6 carbon atoms) Alkoxy chains), alkoxys with 1-5 carbon atoms (branched alkoxys with 3-5 carbon atoms), carbon These include alkoxys with 1 to 4 carbon atoms (branched chain alkoxys with 3 to 4 carbon atoms), etc.

[0132] Specific examples of "alkoxy" include methoxy, ethoxy, n-propoxy, and isopropyl. Poxy, 1-ethyl-1-methylpropoxy, 1,1-diethylpropoxy, 1,1,2 -Trimethylpropoxy, 1,1,2,2-Tetramethylpropoxy, 1-Ethyl-1, 2,2-trimethylpropoxy, n-butoxy, isobutoxy, s-butoxy, t-butoxy Xy, 2-ethylbutoxy, 1,1-dimethylbutoxy, 3,3-dimethylbutoxy, 1 ,1-Diethylbutoxy, 1-Ethyl-1-methylbutoxy, 1-Propyl-1-methyl Butoxy, 1,1,3-trimethylbutoxy, 1-ethyl-1,3-dimethylbutoxy, n-pentyloxy, isopentyloxy, neopentyloxy, t-pentyloxy ( t-amyloxy), 1-methylpentyloxy, 2-propylpentyloxy, 1,1 -Dimethylpentyloxy, 1-ethyl-1-methylpentyloxy, 1-propyl-1 -Methylpentyloxy, 1-butyl-1-methylpentyloxy, 1,1,4-trimethyl Tylpentyloxy, n-hexyloxy, 1-methylhexyloxy, 2-ethylhexyl Siloxy, 1,1-dimethylhexyloxy, 1-ethyl-1-methylhexyloxy , 1,1,5-trimethylhexyloxy, 3,5,5-trimethylhexyloxy, n -heptyloxy, 1-methylheptyloxy, 1-hexylheptyloxy, 1,1- Dimethylheptyloxy, 2,2-dimethylheptyloxy, 2,6-dimethyl-4-dimethylheptyloxy Butyloxy, n-octyloxy, t-octyloxy(1,1,3,3-tetramethicone) 1,1-dimethyloctyloxy, n-nonyloxy, n-decyloxy Xy, 1-methyldecyloxy, n-undecyloxy, n-dodecyloxy, n-tri Decyloxy, n-tetradecyloxy, n-pentadecyloxy, n-hexadecyloxy Xy, n-heptadecyloxy, n-octadecyloxy, or n-eicosyloxy And so on.

[0133] "Aryloxy" is a group represented as "Ar-O- (Ar is an aryl group)", For details on the arrow, you can refer to the explanation of "arrow" above.

[0134] "Substituting silyl" is, for example, at least aryl, alkyl, and cycloalkyl. A silyl that is substituted with one, preferably a triarylsilyl or trialkylsilyl. , tricycloalkylsilyl, dialkylcycloalkylsilyl, or alkyldisic It is a roalkylsilyl compound.

[0135] "Triarylsilyl" is a silyl group substituted with three aryl groups, and this aryl For more details about "Aryl," you can refer to the explanation of "Aryl" mentioned above. Specific examples of "triarylsilyl" include triphenylsilyl and diphenylmonona. Examples include phthylsilyl, monophenyldinaphthylsilyl, or trinaphthylsilyl.

[0136] "Trialkylsilyl" is a silyl group substituted with three alkyl groups, and this alkyl For further details, you can refer to the explanation of "alkyl" mentioned above. Specific examples of "trialkylsilyl" include trimethylsilyl, triethylsilyl, Tri-n-propylsilyl, triisopropylsilyl, tri-n-butylsilyl, triisopropylsilyl butylsilyl, tri-s-butylsilyl, tri-t-butylsilyl, ethyldimethylsilyl, n -Propyldimethylsilyl, isopropyldimethylsilyl, n-butyldimethylsilyl, Isobutyldimethylsilyl, s-butyldimethylsilyl, t-butyldimethylsilyl, Isopropyl diethylsilyl, n-propyl diethylsilyl, isopropyl diethylsilyl, n- Butyldiethylsilyl, s-butyldiethylsilyl, t-butyldiethylsilyl, methyl Di-n-propylsilyl, ethyl di-n-propylsilyl, n-butyl di-n-propylsilyl s-butyldi-n-propylsilyl, t-butyldi-n-propylsilyl, methyl diisopropyl Ropyrsilyl, ethyldiisopropylsilyl, n-butyldiisopropylsilyl, s- These include t-butyldiisopropylsilyl or t-butyldiisopropylsilyl.

[0137] "Tricycloalkylsilyl" is a silyl group substituted with three cycloalkyl groups. For details on this cycloalkyl, you can refer to the explanation of "cycloalkyl" mentioned above. . A specific example of "tricycloalkylsilyl" is tricyclopentylsilyl or Examples include tricyclohexylsilyl.

[0138] "Dialkylcycloalkylsilyl" is a compound of two alkyl groups and one cycloalkyl group. These are silyl groups substituted with [a specific compound], and details of these alkyl and cycloalkyl groups are described above. You can quote the explanations of "alkyl" and "cycloalkyl" provided above.

[0139] "Alkyldicycloalkylsilyl" is a compound of one alkyl and two cycloalkyl These are silyl groups substituted with [a specific compound], and details of these alkyl and cycloalkyl groups are described above. You can quote the explanations of "alkyl" and "cycloalkyl" provided above.

[0140] Specifically, this involves the steric hindrance, electron-donating, and electron-withdrawing properties of the structures of the first and second substituents. The emission wavelength can be adjusted depending on the properties, and preferably the group is represented by the following structural formula. More preferably, methyl, t-butyl, t-amyl, t-octyl, neopentyl, ada Mantyl, phenyl, o-tolyl, p-tolyl, 2,4-xylyl, 2,5-xylyl, 2,6-Xylyl, 2,4,6-Mesityl, Diphenylamino, Di-p-Tolylamino, Bis(p-(t-butyl)phenyl)amino,carbazolyl, 3,6-dimethylcarbazol The most preferred are lyl, 3,6-di-t-butylcarbazolyl, and phenoxy, and more preferably lyl, 3,6-di-t-butylcarbazolyl, and phenoxy. Methyl, t-butyl, t-amyl, t-octyl, neopentyl, adamantyl, phen Nyl, o-tolyl, 2,6-xylyl, 2,4,6-mesityl, diphenylamino, di- p-Tolylamino, bis(p-(t-butyl)phenyl)amino, carbazolyl, 3,6 -dimethylcarbazolyl and 3,6-di-t-butylcarbazolyl. Easily synthesized. From this perspective, a greater steric hindrance is preferable for selective synthesis, specifically, t -Butyl, t-amyl, t-octyl, adamantyl, o-tril, p-tril, 2,4 -Xylyl, 2,5-Xylyl, 2,6-Xylyl, 2,4,6-Mesityl, Di-p-T Lylamino, bis(p-(t-butyl)phenyl)amino, 3,6-dimethylcarbazoli Lu and 3,6-di-t-butylcarbazol are preferred.

[0141] In the structural formula below, "Me" is methyl, "tBu" is t-butyl, and "tAm" is t- Amir, where "tOct" represents t-octyl, and * indicates the bond position. [ka]

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[0142] <Description of cycloalkane condensation> Furthermore, at least the aromatic ring and heteroaromatic ring in the chemical structure of the polycyclic aromatic compound of the present invention Each of them may be condensed with at least one cycloalkane.

[0143] For example, in a compound represented by formula (1A) or formula (1B), the B ring, C ring, D ring, E rings, F rings, G rings, aryls, and heteroaryls, represented by formula (2A) or formula (2B). In the compound, the b-ring, c-ring, d-ring, e-ring, f-ring, g-ring, the "formed ring", At least one of the aryl and heteroaryl is at least one cycloalkane It may be condensed.

[0144] "Cycloalkanes" include cycloalkanes with 3 to 24 carbon atoms and cycloalkanes with 3 to 20 carbon atoms. Chloalkanes, cycloalkanes with 3-16 carbon atoms, cycloalkanes with 3-14 carbon atoms, carbon Cycloalkanes with 5-10 prime numbers, cycloalkanes with 5-8 carbon atoms, cycloalkanes with 5-6 carbon atoms Examples include alkanes and cycloalkanes (which have 5 carbon atoms).

[0145] Specific examples of cycloalkanes include cyclopropane, cyclobutane, and cyclopentane. Cyclohexane, cycloheptane, cyclooctane, cyclononane, cyclodecane, nor Bornen, bicyclo[1.1.0]butane, bicyclo[1.1.1]pentane, bicyclo [2.1.0] Pentane, bicyclo[2.1.1] Hexane, bicyclo[3.1.0] Hexane Xane, bicyclo[2.2.1]heptane, bicyclo[2.2.2]octane, adamant Tan, diamantane, decahydronaphthalene and decahydroazulene, as well as this These alkyl (especially methyl) substituted compounds and halogen (especially fluorine) substituted compounds of carbon atoms 1 to 5. Examples include deuterium-substituted compounds.

[0146] Among these, for example, the α-carbon of cycloalkanes (aromatic) as shown in the structural formula below. In cycloalkyl groups that condense on a group ring or heteroaromatic ring, the carbon adjacent to the carbon at the condensation site A structure in which at least one hydrogen atom is substituted at the α-position carbon is preferred. A structure in which two hydrogens are substituted is more preferred, with a total of four at the two α-positions of the carbon. A structure in which hydrogen is substituted is even more preferred. Possible substituents include alkyl groups having 1 to 5 carbon atoms. Examples include halogen-substituted (especially methyl), halogen-substituted (especially fluorine), and deuterium-substituted compounds. It is possible. [ka]

[0147] The number of cycloalkanes fused to one aromatic or heteroaromatic ring is preferably 1 to 3. More preferably one or two, and even more preferably one. For example, one benzene ring. Examples of structures in which one or more cycloalkanes are condensed around a phenyl group are shown below. In this case, * represents a benzene ring, if it is a benzene ring, that is a benzene ring included in the skeletal structure of the compound. This means that, in the case of a phenyl group, it refers to a bond that substitutes into the skeletal structure of the compound. As shown in equations (Cy-1-4) and (Cy-2-4), condensed cycloalkanes Condensation may occur. The ring (group) to be condensed may be other aromatic rings other than a benzene ring (phenyl group). Or, even in the case of a heteroaromatic ring, if the condensing cycloalkane is cyclopentane or cyclo The same applies to other cycloalkanes besides chlorohexane. [ka]

[0148] In cycloalkanes, at least one -CH2- is likely to be substituted with an -O-. However, if multiple -CH2- groups are substituted with -O- groups, then adjacent -CH2- groups must be replaced with -O- groups. It will not be substituted. For example, a cycloalkalan condensed to one benzene ring (phenyl group) Examples of the substitution of one or more -CH2- groups with -O- groups in the following structure are shown below. In this case, * represents a benzene ring, if it is a benzene ring, that is a benzene ring included in the skeletal structure of the compound. This means that, in the case of a phenyl group, it refers to a bond that substitutes into the skeletal structure of the compound. The ring (group) being condensed is an aromatic ring or heteroaromatic ring other than a benzene ring (phenyl group). Even in the case of a ring, if the condensing cycloalkane is cyclopentane or cyclohexane The same applies to other cycloalkanes. [ka]

[0149] At least one hydrogen in the cycloalkane may be substituted, and this substituent and For example, aryl, heteroaryl, diarylamino, diheteroarylamino No, aryl heteroarylamino, diarylboryl (the two aryls are single-bonded or Alkyl, cycloalkyl, alkoxy, ally (may be linked via a linking group) Examples include oxy, substituted silyl, deuterium, cyano, or halogen; for further details, see above. The description of the first substituent mentioned above can be cited. Among these substituents, alkyl( For example, alkyl groups with 1 to 6 carbon atoms, cycloalkyl groups (for example, cycloalkyl groups with 3 to 14 carbon atoms) Preferred elements include chloroalkyl compounds, halogens (e.g., fluorine), and deuterium. When substitution occurs, it may be in a substitution form that forms a spiro structure, for example, one benzene ring (f Examples of spiro structures formed on cycloalkanes condensed with an enyl group are shown below. In the formula, * represents a benzene ring, if it is a benzene ring, and is a benzene ring included in the skeletal structure of the compound. This means that, in the case of a phenyl group, it refers to a bond that is substituted into the skeletal structure of the compound. ru. [ka]

[0150] Other forms of cycloalkane condensation include, for example, the polycyclic aromatic compound of the present invention being cycloalkane condensed Diarylamino group condensed with roalkane (condensation to this aryl group portion), cycloal A carbazolyl group condensed with a can (condensed onto this benzene ring) or a cycloalkane Examples include substitution with a condensed benzocarbazolyl group (condensed onto this benzene ring portion). The above explanation can be cited for the "diarylamino group".

[0151] Furthermore, as a more specific example, polycyclic aromatic compounds represented by formula (1A) or formula (2A) are also relevant. R in compounds a However, the diarylamino group condensed with a cycloalkane (this aryl Carbazolyl group (condensed to the base portion) or condensed with a cycloalkane (this benzene ring portion) An example of this is a condensation.

[0152] <Description of substitution with deuterium, cyano, or halogen> In the polycyclic aromatic compound of the present invention, at least one hydrogen is deuterium, cyano, or It may be substituted with a halogen. The halogen may be fluorine, chlorine, bromine, or iodine. Fluorine, chlorine, or bromine are preferred, and fluorine or chlorine are more preferred.

[0153] <Description of specific examples of the polycyclic aromatic compound of the present invention> For example, compounds represented by any of the following structural formulas are preferred. [ka] [ka] [ka] [ka] In each formula, R is independently a hydrogen atom, an aryl atom with 6 to 16 carbon atoms, and a heteroatomic atom with 2 to 20 carbon atoms. Aryl, diarylamino (where aryl refers to aryl with 6 to 10 carbon atoms), diary Luboryl (however, aryl is an aryl with 6 to 10 carbon atoms, and the two aryls are single-bonded) (or may be bonded by a linking group), C1-C12 alkyl, or C3 It is a cycloalkyl group of ~16 atoms, and at least one hydrogen atom in R has 1 to 5 carbon atoms. It may be substituted with an alkyl group or a cycloalkyl group having 5 to 10 carbon atoms. Each of o is an independent integer between 1 and 3. p are independent integers from 1 to 4. Each q is an independent integer between 1 and 5. In each of the above formulas, at least one hydrogen atom is deuterium, cyano, or It may be substituted with a halogen.

[0154] A more detailed explanation of R can be found in the explanation by Ariel et al. mentioned above. o, p, and q are preferably 1 or 2, more preferably 1, and even more preferably 0. stomach.

[0155] <Utilization as a thermally activated delayed fluorescence (TADF) material> The compounds of the present invention can also be used as TADF materials. In particular, formula (1B) and Compounds represented by formulas (1A) and (2A) are more favorable than compounds represented by formula (2B). This is preferable, and also, rings that share a bond with a fused bicyclic structure in the B-G ring or b-g ring. It is preferable that the ring is 6-membered, and more preferably that the ring, including the a-ring, is a 6-membered aryl ring. stomach. Furthermore, single bonds are preferred as the binding groups for forming carbazole-like structures (example) As shown in the structural formula below, if only the first carbazole-like structure exists (1Cz isomer), Preferably (structural formulas other than 1A-111, 1A-112, and 1A-214), carbazoles. Among similar structures, the para position is particularly important when considering the "N" bond position in the carbazole structure. It is preferable that an aryl ring, such as a phenyl group, is substituted at the para position of the c or d ring. (Structural formulas other than 1A-214, 1A-331, and 1A-702), X 1 and X 2 bond position Based on the position, diarylamino groups or carba groups are placed at the meta position (especially the meta position in the B-ring and E-ring). It is preferable that nitrogen-containing groups such as zolyl groups are substituted (1A-31, 1A-32, 1A-3 8. Structural formula of 1A-407). [ka] [ka]

[0156] <Description of specific examples of the polycyclic aromatic compound of the present invention> More specific examples of polycyclic aromatic compounds include compounds represented by the following structural formulas. It can be done. Note that in the structural formula below, "Me" is a methyl group, "tBu" is a t-butyl group, and "D" This indicates deuterium.

[0157] [ka]

[0158] [ka]

[0159] [ka]

[0160] [ka]

[0161] [ka]

[0162] [ka]

[0163] [ka]

[0164] [ka]

[0165] [ka]

[0166]

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[0167]

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[0168]

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[0169]

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[0170]

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[0171]

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[0172]

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[0173]

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[0174]

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[0175]

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[0176]

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[0177]

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[0178]

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[0179]

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[0180]

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[0181]

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[0182]

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[0183]

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[0184]

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[0185]

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[0186]

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[0187] [ka]

[0188] [ka]

[0189] [ka]

[0190] [ka]

[0191] [ka]

[0192] [ka]

[0193] [ka]

[0194] [ka]

[0195] [ka]

[0196] The polycyclic aromatic compounds according to the present invention are reactive compounds in which reactive substituents are substituted thereon. Polymerized polymer compound as a monomer (the monomer used to obtain this polymer compound) (having polymerizable substituents), or a polymer crosslinked by further crosslinking the polymer compound. (The polymer compound used to obtain this crosslinked polymer has a crosslinkable substituent), or A pendant-type polymer compound obtained by reacting a main-chain polymer with the reactive compound (this pendant The reactive compound for obtaining a polymer compound of the nucleotide type has a reactive substituent, or A pendant-type polymer crosslinked material obtained by further crosslinking the said pendant-type polymer compound (this pen The pendant-type polymer compound for obtaining a dant-type polymer crosslinked material has a crosslinkable substituent. Even if it is used, it is a material for organic devices, for example, a material for organic electroluminescent devices, an organic electroluminescent device It can be used as a material for transistors, a material for organic thin-film solar cells, or a wavelength conversion filter. Cut.

[0197] The above-mentioned reactive substituents (the polymerizable substituent, the crosslinkable substituent, and pendant type) (Includes reactive substituents for obtaining polymers, and hereafter also simply referred to as "reactive substituents") This refers to substituents that can increase the molecular weight of the above polycyclic aromatic compound, and polymers obtained in this way. substituents that can further crosslink the compound, and substituents that can undergo pendant reactions with the main chain polymer. While not particularly limited if available, substituents with the following structures are preferred. * in each structural formula indicates a bond position. This indicates. [ka]

[0198] L is independent of each other, a single bond, -O-, -S-, >C=O, -OC(=O)-, Alkylenes with 1 to 12 carbon atoms, oxyalkylenes with 1 to 12 carbon atoms, and C1-12 It is a polyoxyalkylene. Among the substituents above, formula (XLS-1), formula (XLS- 2) Formula (XLS-3), Formula (XLS-9), Formula (XLS-10), or Formula (XLS-1 7) The group represented by formula (XLS-1), formula (XLS-3), or formula (XLS- The group represented by 17) is more preferred.

[0199] Such polymer compounds, polymer crosslinks, pendant-type polymer compounds, and pendants The cross-linked polymer of type T can be substituted with other units in addition to the repeating units of the polycyclic aromatic compound according to the present invention. ku is an unsubstituted triarylamine, substituted or unsubstituted fluorene, substituted or unsubstituted fluorene. Substituted anthracene, substituted or unsubstituted tetracene, substituted or unsubstituted triazine , substituted or unsubstituted carbazoles, substituted or unsubstituted tetraphenylsilanes, Substituted or unsubstituted spirofluorene, substituted or unsubstituted triphenylphosphine, Substituted or unsubstituted dibenzothiophenes, and substituted or unsubstituted dibenzofurans. The compound may contain at least one selected from the group of compounds consisting of the above as a repeating unit.

[0200] Examples of substituents in these repeating units include aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diary Ruboryl (the two aryls may be linked by a single bond or via a linking group), Alky , cycloalkyl, alkoxy, aryloxy, triarylsilyl, trialkyl Silyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, or alkyl Examples include dicycloalkylsilyls. The "aryl" in triarylamine, and this Details of these substituents can be referenced from the description in the polycyclic aromatic compound according to the present invention. .

[0201] Such polymer compounds, polymer crosslinks, pendant-type polymer compounds and pendants Detailed information on the uses of cross-linked polymer compounds (hereinafter also simply referred to as "polymer compounds and cross-linked polymer compounds") Details will be discussed later.

[0202] 2. Method for producing a polycyclic aromatic compound according to the present invention The polycyclic aromatic compounds of the present invention basically consist of an a-ring and a B-ring to a G-ring or a b-ring to a g-ring. and a bonding group ("N" or X 1 or X 2 An intermediate is produced by bonding with a group containing ( (First reaction), then the a ring and the B ring to G ring or the b ring to g ring are bonded together by a Y group. 1 ~Y 3 of The final product can be produced by bonding with a (containing) group (second reaction). International publication. The manufacturing method described in Publication No. 2015 / 102118 can be used as a reference.

[0203] In the first reaction, for example, in the case of an etherification reaction, nucleophilic substitution reactions and Ullmann reactions are used. Common reactions can be used, and in the case of amination reactions, the Buchwald-Hartwig reaction is one example. A general reaction can be used. In addition, the second reaction is a tandem hetero-Friedel-Crafts reaction. A response (a series of electrophilic aromatic substitution reactions, the same applies hereafter) can be used.

[0204] The second reaction proceeds as shown in schemes (1) and (2) below, involving ring a and rings B to G. Y connects the b ring to the g ring. 1 ~Y 3 This is a reaction that introduces "N" and X. 1 and X 2 The hydrogen atoms between them, and the hydrogen atoms between "N"s, are called n-butyllithium, sec-butyllithium, and sec-butyllithium. Orthometallation is performed using lithium t-butyllithium or similar. Then, boron trichloride is added. Y such as boron tribromide 1 ~Y 3 Add the halide and perform lithium-boron metal exchange. After that, by adding a Brønsted base such as N,N-diisopropylethylamine, The target product can be obtained by carrying out a tandem Boraf Friedelcrafts reaction. Second reaction odor In order to accelerate the reaction, a Lewis acid such as aluminum trichloride may be added. In schemes (1) and (2), and in subsequent schemes, the signs in each structural formula are The definition is the same as the definition above.

[0205] [ka] [ka]

[0206] In the above scheme, lithium was introduced to the desired location by orthometallation, As shown in the scheme (3) below, introduce bromine atoms, etc., at the position where you want to introduce lithium, and then halogen Lithium can also be introduced to the desired position by metal replacement. This allows for the production of the target product even in cases where orthometalation is not possible due to the influence of substituents. It is useful. [ka]

[0207] The above schemes (1) to (3) are Y 1 ~Y 3 This is a typical manufacturing method for boron (B), etc. be.

[0208] Next, as an example, Y1 ~Y 3 The field where is phosphorus sulfide, phosphorus oxide, or phosphorus atom The combination is shown in schemes (4) and (5) below. As before, first "N" and X 1 Oh biX 2 The hydrogen atoms between them, or the hydrogen atoms between "N"s, are orthogonal with n-butyllithium, etc. Metallization is performed. Then, phosphorus trichloride and sulfur are added in that order, and finally aluminum trichloride, etc. By adding a Lewis acid and a Brønsted base such as N,N-diisopropylethylamine... Then, the tandem phosphine Friedelcrafts reaction is carried out, Y 1 ~Y 3 It is a phosphorus sulfide. A compound can be obtained. Furthermore, the obtained phosphorus sulfide compound can be obtained by m-chloroperbenzoation. By treating with fragrant acid (m-CPBA), Y 1 ~Y 3 To obtain a compound that is a phosphorus oxide, This can be done by treating with triethylphosphine. 1 ~Y 3 Compounds in which the atom is phosphorus You can obtain this.

[0209] [ka] [ka]

[0210] In the above scheme, Y 1 ~Y 3 However, examples such as B, P, P=O, or P=S are provided. However, by appropriately changing the raw materials, other compounds can also be manufactured.

[0211] In the above scheme, Y such as boron trichloride or boron tribromide 1 ~Y 3 Add the halogenated compound Before that, "N" and X 1 and X 2 Hydrogen atoms (or halogen atoms) between them, or the same "N" The process of orthometalizing the hydrogen atoms (or halogen atoms) between the atoms using butyllithium or similar materials. I have shown an example of a tandem hetero-Friedel-Crafts reaction, but using butyllithium, etc. Without performing orthometallation, Y such as boron trichloride and boron tribromide 1 ~Y 3 halogen The reaction can also be accelerated by adding chemical compounds.

[0212] Examples of solvents used in the above scheme include t-butylbenzene and xylene. .

[0213] The orthometalation reagents used in the above scheme are methyllithium and n-butyllithium. Alkyl lithium such as thium, sec-butyllithium, t-butyllithium, and lithium Diisopropylamide, Lithium tetramethylpiperidide, Lithium hexamethyldisyl Organic alkali compounds such as dido, potassium hexamethyldisilazide, and organic solvent dispersions such as Na. Examples include dispersed alkali metals.

[0214] The metal used in the above scheme - (Y 1 ~Y 3 As a metal exchange reagent, Y 1 ~Y 3 trifluoride, Y 1 ~Y 3 trichloride, Y 1 ~Y 3 Tribromide of Y 1 ~Y 3 triiodide Y such as 1 ~Y 3 Y halides such as CIPN(NEt2)2 1 ~Y 3Amination Halides, Y 1 ~Y 3 Alkoxy compounds of Y 1 ~Y 3 Examples include aryl oxy compounds. It can be done.

[0215] The Brønsted base used in the above scheme is N,N-diisopropylethyl Amine, triethylamine, 2,2,6,6-tetramethylpiperidine, 1,2,2,6 ,6-Pentamethylpiperidine, N,N-dimethylaniline, N,N-dimethyltoluidine N, 2,6-lutidine, sodium tetraphenylborate, potassium tetraphenylborate Mu, triphenylborane, tetraphenylsilane, Ar4BNa, Ar4BK, Ar3B Examples include Ar4Si (where Ar is an aryl group such as phenyl).

[0216] The Lewis acids used in the above scheme are AlCl3, AlBr3, AlF3, and BF3. 3·OEt2, BCl3, BBr3, GaCl3, GaBr3, InCl3, InBr3 , In(OTf)3, SnCl4, SnBr4, AgOTf, ScCl3, Sc(OTf )3, ZnCl2, ZnBr2, Zn(OTf)2, MgCl2, MgBr2, Mg(O Tf)2, LiOTf, NaOTf, KOTf, Me3SiOTf, Cu(OTf)2, CuCl2, YCl3, Y(OTf)3, TiCl4, TiBr4, ZrCl4, ZrB Examples include r4, FeCl3, FeBr3, CoCl3, and CoBr3.

[0217] In the above scheme, to facilitate the tandem hetero-Friedel-Crafts reaction, Brønste A Lewis base or Lewis acid may be used. However, Y 1 ~Y 3trifluoride, Y 1 ~Y 3 trichloride, Y 1 ~Y 3 Tribromide of Y 1 ~Y 3 Y such as triiodide 1 ~Y 3 No Haro When genamides are used, as the aromatic electrophilic substitution reaction progresses, hydrogen fluoride and hydrogen chloride are produced. Because acids such as hydrogen bromide and hydrogen iodide are produced, Brønsted bases are used to capture the acids. It is effective to use. On the other hand, Y 1 ~Y 3 Amination halogens, Y 1 ~Y 3 Alcoholic When cylides are used, amines and alcohols are produced as the aromatic electrophilic substitution reaction progresses. In many cases, it is not necessary to use Brønsted bases to achieve this, but amino groups and A Because the lucoxy group has low detachment ability, the use of a Lewis acid to promote its detachment is effective.

[0218] Furthermore, the polycyclic aromatic compounds of the present invention contain at least some hydrogen as deuterium, cyano, and This includes compounds that are substituted with halogens, but for such compounds, the desired position is By using halogenated raw materials such as deuterated, cyanated, fluorinated, or chlorinated raw materials It can be manufactured in the same manner as described above.

[0219] 3. Organic device In the chemical structural formulas shown below, "Me" represents a methyl group and "tBu" represents a t-butyl group. represent. The polycyclic aromatic compounds according to the present invention can be used as materials for organic devices. Examples of such devices include organic field-emitting diodes, organic field-effect transistors, and organic thin films. Examples include solar cells or wavelength conversion filters.

[0220] 3-1. Organic electroluminescent device The organic EL element according to this embodiment will be described in detail below with reference to the drawings. Figure 1 This is a schematic cross-sectional view showing an organic EL element according to this embodiment.

[0221] <Structure of Organic Field-Emitting Light> The organic EL element 100 shown in Figure 1 consists of a substrate 101 and an anode provided on the substrate 101. 102, a hole injection layer 103 provided on the anode 102, and a hole injection layer 103 provided on the hole injection layer 103 A hole transport layer 104 is provided, and a light-emitting layer 105 is provided on the hole transport layer 104, and light emission An electron transport layer 106 provided on top of layer 105, and an electron transport layer 106 provided on top of electron transport layer 106 It has an injection layer 107 and a cathode 108 provided on the electron injection layer 107.

[0222] Furthermore, the organic EL element 100 can be manufactured in the reverse order, for example, using substrate 101 and substrate 10 A cathode 108 provided on 1, an electron injection layer 107 provided on the cathode 108, and electron An electron transport layer 106 provided on top of the injection layer 107, and an electron transport layer 106 provided on top of the electron transport layer 106 A light-emitting layer 105, a hole transport layer 104 provided on the light-emitting layer 105, and a hole transport layer 104 A hole injection layer 103 provided on top of and an anode 102 provided on top of the hole injection layer 103 A configuration having the following characteristics is also possible.

[0223] Not all of the above layers are necessarily required; the minimum constituent unit consists of the anode 102 and the light-emitting layer. The structure consists of 105 and cathode 108, with a hole injection layer 103, a hole transport layer 104, and electron The transport layer 106 and the electron injection layer 107 are optional layers. Each layer may consist of a single layer or multiple layers.

[0224] The configuration of the layers constituting the organic EL element is as described above: "substrate / anodote / hole injection layer / hole In addition to the configuration of "transport layer / light-emitting layer / electron transport layer / electron injection layer / cathode", there is also "substrate / anode / positive Pore ​​transport layer / Emitting layer / Electron transport layer / Electron injection layer / Cathode, Substrate / Anode / Hole injection layer / Emitting Layer / Electron transport layer / Electron injection layer / Cathode, Substrate / Anode / Hole injection layer / Hole transport layer / Emitting layer / Electron injection layer / Cathode", "Substrate / Anode / Hole injection layer / Hole transport layer / Emitting layer / Electron transport layer / " Cathode, Substrate / Anode / Emitting Layer / Electron Transport Layer / Electron Injection Layer / Cathode, Substrate / Anode / Hole Transport layer / emissive layer / electron injection layer / cathode, substrate / anode / hole transport layer / emissive layer / electron transport layer / cathode", "substrate / anode / hole injection layer / emissive layer / electron injection layer / cathode", "substrate / anode / positive "Pore injection layer / light-emitting layer / electron transport layer / cathode", "Substrate / anode / light-emitting layer / electron transport layer / cathode", The configuration may also consist of "substrate / anode / light-emitting layer / electron injection layer / cathode".

[0225] <Substrates for organic electroluminescent devices> The substrate 101 is a support for the organic EL element 100, and is typically made of quartz, glass, metal, or plastic. Materials such as plastic are used. The substrate 101 can be in the form of a plate, film, or sheet depending on the purpose. Formed in a t shape, for example, glass plate, metal plate, metal foil, plastic film, plastic Sheets such as glass and polyester / polymetallic are used. A transparent synthetic resin sheet such as rilate, polycarbonate, or polysulfone is preferred. For lath substrates, soda-lime glass or alkali-free glass are used, and the thickness It only needs to be thick enough to maintain mechanical strength, for example, 0.2 mm or more. i. The upper limit of the thickness is, for example, 2 mm or less, preferably 1 mm or less. glass Regarding the material, it is better to use alkali-free glass as it has fewer ions leached from the glass. While this is preferable, soda-lime glass with a barrier coating such as SiO2 is also commercially available. Therefore, this can be used. In addition, the substrate 101 is designed to enhance gas barrier properties. Furthermore, a gas barrier film such as a dense silicon oxide film may be provided on at least one side, and in particular, gas When using a board, film, or sheet made of synthetic resin with low barrier properties as the substrate 101. It is preferable to provide a gas barrier film.

[0226] <Anode in an organic electroluminescent element> The anode 102 plays the role of injecting holes into the light-emitting layer 105. At least one of the following layers is provided between layer 105: a hole injection layer 103 and a hole transport layer 104. If these are present, holes will be injected into the light-emitting layer 105 via them.

[0227] Materials that can form the anode 102 include inorganic compounds and organic compounds. Examples of compounds include metals (aluminum, gold, silver, nickel, palladium, chromium). (etc.), metal oxides (indium oxide, tin oxide, indium-tin oxide (I TO), indium zinc oxide (IZO), metal halides (copper iodide, etc.), Examples include copper sulfide, carbon black, ITO glass, and NESA glass. Organic compounds and For example, polythiophenes such as poly(3-methylthiophene), polypyrrole, Examples include conductive polymers such as polyaniline. Other examples include those used as anodes in organic EL elements. It can be appropriately selected and used from among the substances currently in use.

[0228] The resistance of the transparent electrode is not limited, as long as it can supply enough current for the light-emitting element to emit light. However, from the standpoint of the power consumption of the light-emitting element, low resistance is desirable. For example, 300Ω / □The following ITO substrates will function as element electrodes, but currently, substrates with an impedance of approximately 10Ω / □ are available. Since it is also possible to supply such as, for example, 100~5Ω / □, preferably 50~5Ω / It is especially desirable to use low-resistance components marked with a square. The thickness of the ITO can be arbitrarily selected according to the resistance value. It can be used in a wider range, but it is usually used in the 50-300nm range.

[0229] <Hole injection layer and hole transport layer in organic electroluminescent devices> The hole injection layer 103 efficiently delivers holes moving from the anode 102 into the light-emitting layer 105. Alternatively, it plays the role of injecting into the hole transport layer 104. The hole transport layer 104 is from the anode 102 The injected holes or holes injected from the anode 102 through the hole injection layer 103 are efficiently The hole injection layer 103 and hole transport layer 104 play a role in transporting the holes to the light-emitting layer 105. Each involves laminating or mixing one or more types of hole injection / transport materials, or hole injection / transport materials. It is formed from a mixture of transport material and polymer binder. Additionally, iron chloride is used as the hole injection / transport material. (III) An inorganic salt may be added to form a layer.

[0230] As a hole-injecting and transporting material, it efficiently transports holes from the positive electrode between electrodes under an applied electric field. It is necessary to inject and transport the holes efficiently, and the hole injection efficiency is high, and the injected holes are transported efficiently. It is desirable to do so. For this to happen, the ionization potential must be small and the hole mobility must be It is large, highly stable, and less likely to generate trapping impurities during manufacturing and use. It is preferable that the material is a good substance. In the present invention, as the material for the hole injection layer and the hole transport layer The use of polycyclic aromatic compounds represented by the above general formula (1A) or general formula (1B) is possible. can.

[0231] The material used to form the hole injection layer 103 and the hole transport layer 104 is a photoconductive material. Compounds, p-type semiconductors, and organic EL elements have been conventionally used as charge transport materials for holes. Select any compound from among the known compounds used in the hole injection layer and hole transport layer of this child. They can be selected and used. Specific examples include carbazole derivatives (N-phenylacetate). Lubazole, polyvinylcarbazole, etc.), bis(N-arylcarbazole) or Biscarbazole derivatives such as bis(N-alkylcarbazole), triarylamines Derivatives (polymers having aromatic tertiary amino acids in the main chain or side chain, 1,1-bis(4-di- p-Tolylaminophenyl)cyclohexane, N,N'-diphenyl-N,N'-di(3 -methylphenyl)-4,4'-diaminobiphenyl,N,N'-diphenyl-N,N' -Dinaphthyl-4,4'-diaminobiphenyl, N,N'-diphenyl-N,N'-di( 3-methylphenyl)-4,4'-diphenyl-1,1'-diamine, N,N'-dinaph Tyl-N,N'-diphenyl-4,4'-diphenyl-1,1'-diamine, N 4 ,N 4 ’ -diphenyl-N 4 ,N 4’ -Bis(9-phenyl-9H-carbazole-3-yl) -[1,1'-biphenyl]-4,4'-diamine, N 4 ,N 4 ,N 4’ ,N 4’ -Teto Ra([1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4,4'-di Amine, 4,4',4”-tris(3-methylphenyl(phenyl)amino)triphen Triphenylamine derivatives such as sylamine, starburst amine derivatives, etc., still Ben derivatives, phthalocyanine derivatives (metal-free, copper phthalocyanine, etc.), pyrazoline derivatives Body, hydrazone compounds, benzofuran derivatives and thiophene derivatives, oxadiazole derivatives Conductors, quinoxaline derivatives (e.g., 1,4,5,8,9,12-hexaazatripheny (e.g., len-2,3,6,7,10,11-hexacarbonitride), porphyrin derivatives Examples include heterocyclic compounds and polysilanes. Polymer systems have the monomer in their side chains. Polycarbonate, styrene derivatives, polyvinylcarbazole, and polysilane are preferred. However, it is necessary to form a thin film required for the fabrication of a light-emitting element, and to be able to inject holes from the anode, and furthermore, The compound is not particularly limited as long as it can transport pores.

[0232] Furthermore, it is known that the conductivity of organic semiconductors is strongly affected by doping. Such organic semiconductor matrix materials are compounds with good electron-donating properties, or It is composed of compounds with good electron-accepting properties. For doping with electron-donating substances, Tetracyanoquinone dimethane (TCNQ) or 2,3,5,6-tetrafluorotetra Strong electron acceptors such as cyano-1,4-benzoquinone dimethane (F4TCNQ) are known. (For example, see the reference "M. Pfeiffer, A. Beyer, T. Fritz, K. Leo, Appl. Phys. Lett., 73(22), 32 02-3204(1998) and reference "J.Blochwitz, M.Pfeiffer, T.Fritz, K.Leo, Appl.Phys.Lett., See 73(6), 729-731(1998). These are electron-donating base materials (hole transport materials). The electron transfer process in ) generates so-called holes. The number and mobility of holes This significantly alters the conductivity of the base material. Examples of the compound include benzidine derivatives (such as TPD) or starburst amino acids. Derivatives of phosphates (such as TDATA), or certain metal phthalocyanines (especially zinc phthalocyanines). Anine (ZnPc, etc.) is known (Japanese Patent Publication No. 2005-167175).

[0233] The hole injection layer material and hole transport layer material described above are provided by substituting reactive substituents therein. A polymer compound obtained by polymerizing a reactive compound as a monomer, or a polymer crosslink thereof. A body, or a pendant-type polymer compound obtained by reacting a main-chain polymer with the reactive compound. Alternatively, it can be used as a material for the hole layer, either as a pendant-type polymer crosslinked material or as such. In this case, the reactive substituent is represented by the above general formula (1A) or general formula (1B). We can cite the explanation for polycyclic aromatic compounds. Details of the applications of such polymer compounds and polymer crosslinks will be described later.

[0234] <Emitting layer in organic electroluminescent element> The light-emitting layer 105 emits holes injected from the anode 102 between electrodes to which an electric field is applied. This is a light-emitting layer that emits light by recombining with electrons injected from cathode 10⁸. The material that forms 105 is a compound that emits light when excited by the recombination of holes and electrons. Any substance (luminescent compound) will suffice, and it must be able to form a stable thin film shape and be in a solid state. It is preferable that the compound exhibits strong luminescence (fluorescence) efficiency in its state. In the present invention, the material for the luminescent layer As materials, a host material and, for example, a dopant material of the above general formula (1A) or general A polycyclic aromatic compound represented by formula (1B) can be used.

[0235] The light-emitting layer can consist of a single layer or multiple layers, and each layer is made of a material for the light-emitting layer (phosphorus). It is formed from a host material and a dopant material. The host material and the dopant material are, respectively It can be one type or a combination of multiple types. The dopant material is H It may be included in the entire material or in part. As for the coating method, it can be formed by co-deposition with a host material, but The host material is pre-mixed with the host material and then simultaneously deposited, or the host material is pre-mixed with an organic solvent. The film may also be formed by a wet deposition method.

[0236] The amount of host material used varies depending on the type of host material, and should be adjusted according to the characteristics of that host material. You can decide based on that. The guideline for the amount of host material to use is preferably 50% of the total amount of material for the light-emitting layer. It is 99.999% by weight, more preferably 80-99.95% by weight, and even more preferably It is more accurately 90-99.9% by weight.

[0237] The amount of dopant material used varies depending on the type of dopant material. It should be determined according to the characteristics. The guideline for the amount of dopant material to use is preferably for the light-emitting layer. It is 0.001 to 50% by weight of the total material, more preferably 0.05 to 20% by weight. More preferably, it is 0.1 to 10% by weight. Within the above range, for example, density quenching It is preferable in that it can prevent the phenomenon. Also, from the viewpoint of durability, the hydrogen of the dopant material It is also preferable that some or all of the atoms are deuterated.

[0238] On the other hand, in organic field light-emitting devices using thermally activated delayed fluorescence dopant materials, the dopants While it is preferable to use a low concentration of the ant material in order to prevent the concentration quenching phenomenon, A higher concentration of dopant material is preferable in terms of the efficiency of the thermally activated delayed fluorescence mechanism. Furthermore, in organic electroluminescent devices using thermally activated delayed fluorescence-assisted dopant materials... In this regard, from the standpoint of the efficiency of the thermally activated delayed fluorescence mechanism of the assist dopant material, It is preferable that the amount of dopant material used is at a lower concentration compared to the amount of dopant material used.

[0239] When assist dopant material is used, the host material and assist dopant The approximate amounts of material and dopant material to be used are 40-99% of the total material for the light-emitting layer. The amounts are 0.999% by weight, 59-1% by weight, and 20-0.001% by weight, preferably so These are 60-99.99% by weight, 39-5% by weight, and 10-0.01% by weight, respectively. More preferably, 70-99.95% by weight, 29-10% by weight, and 5-0.05% by weight The compound represented by the above general formula (1A) or general formula (1B) and its polymerization The compound can also be used as an assist dopant material.

[0240] As host materials, anthracene and pyrene, which have long been known as luminescent materials, are used. Condensed ring derivatives, bis-styrylanthracene derivatives and distylylbenzene derivatives, etc. Styryl derivatives, tetraphenylbutadiene derivatives, cyclopentadiene derivatives, fluorine Examples include fluorene derivatives and benzofluorene derivatives.

[0241] The triplet energy of the host material does not inhibit but promotes the generation of TADF within the luminescent layer. From this perspective, the dopant or ase with the highest triplet energy within the luminescent layer It is preferable that the dopant energy is higher than that of the host material. Specifically, the host material The triplet energy is preferably 0.01 eV or higher, and more preferably 0.03 eV or higher. A voltage of 0.1 eV or higher is even more preferable. Furthermore, even if a TADF-active compound is used as the host material... good.

[0242] As host materials, for example, compounds represented by the following general formula (H1), the following general formula (H 2) Compounds represented by the following general formula (H3), compounds represented by the following general formula (H4) Compounds containing the structure shown, compounds represented by the following general formula (H5), and compounds represented by the following general formula (H6) Examples include compounds represented by the general formula (H1) and TADF materials. Preferably represented by the general formula (H1) It is a compound that can be found. [ka]

[0243] <Compounds represented by the general formula (H1)> [ka] In the above formula (H1), L 1 These are arylenes with 6 to 30 carbon atoms or heterozygotes with 2 to 30 carbon atoms. It is an arylene, preferably an arylene with 6 to 24 carbon atoms, and preferably an arylene with 6 to 16 carbon atoms. arylene is more preferred, arylene with 6 to 12 carbon atoms is even more preferred, and arylene with 6 to 10 carbon atoms is more preferred. Reylene is particularly preferred, and heteroarylene having 2 to 25 carbon atoms is also preferred. Heteroarylenes with 2 to 20 carbon atoms are more preferred, and heteroarylenes with 2 to 15 carbon atoms are even more preferred. Preferably, heteroarylenes having 2 to 10 carbon atoms are preferred. Specifically as arylenes Specifically, benzene rings, biphenyl rings, naphthalene rings, terphenyl rings, and acenaphthylene rings. fluorene ring, phenalene ring, phenanthrene ring, triphenylene ring, pyrene ring, naphth Examples of divalent groups include tacene rings, perylene rings, and pentacene rings. Also, hetero Specifically, reylenes include pyrrole rings, oxazole rings, isoxazole rings, and thiazo rings. Isothiazole ring, isothiazole ring, imidazole ring, oxadiazole ring, thiadiazole ring, Triazole ring, tetrazole ring, pyrazole ring, pyridine ring, pyrimidine ring, pyridadi H-ring, pyrazine ring, triazine ring, indole ring, isoindole ring, 1H-indazo 1H-ben ring, benzimidazole ring, benzoxazole ring, benzothiazole ring, 1H-ben Zotriazole ring, quinoline ring, isoquinoline ring, sinnoline ring, quinazoline ring, quinoki Sarin ring, phthalazine ring, naphthyridine ring, purine ring, pteridine ring, carbazole ring, Acridine ring, phenoxathiine ring, phenoxazine ring, phenothiazine ring, phenazine Ring, phenazacillin ring, indoridine ring, furan ring, benzofuran ring, isobenzofuran ring, dibenzofuran ring, thiophene ring, benzothiophene ring, dibenzothiophene ring, f Razan ring, thianthlene ring, indolocarbazole ring, benzoindolocarbazole ring, Examples of divalent groups include the benzobenzoindocarbazole ring and the naphthobenzofuran ring. It is possible. In the compound represented by formula (H1), at least one hydrogen atom is an alkyl group having 1 to 6 carbon atoms. It is substituted with cycloalkyl, cyano, halogen, or deuterium atoms having 3 to 14 carbon atoms. That's good too.

[0244] <Compounds represented by the general formula (H2)> [ka] In the above formula (H2), L 2 and L 3 These are, independently, aryl atoms with 6 to 30 carbon atoms. Alternatively, it is a heteroaryl with 2 to 30 carbon atoms. As for aryls, there are heteroaryls with 6 to 24 carbon atoms. A aryl is preferred, an aryl with 6 to 16 carbon atoms is more preferred, and an aryl with 6 to 12 carbon atoms is preferred. A more preferable aryl is a C6-C10 aryl, and a particularly preferable aryl is a C6-C10 aryl, specifically a benzene ring. Ring, biphenyl ring, naphthalene ring, terphenyl ring, acenaphthylene ring, fluorene ring, Phenalene ring, phenanthrene ring, triphenylene ring, pyrene ring, naphthacene ring, perile Examples include monovalent groups such as ¹ⁿ rings and pentacene rings. Heteroaryls include those with a carbon number Heteroaryls with 2 to 25 carbon atoms are preferred, and heteroaryls with 2 to 20 carbon atoms are more preferred. A heteroaryl with 2 to 15 carbon atoms is more preferred, and a heteroaryl with 2 to 10 carbon atoms is also preferred. Particularly preferred are pyrrole rings, oxazole rings, isoxazole rings, and thia rings. Zole ring, isothiazole ring, imidazole ring, oxadiazole ring, thiadiazole ring triazole ring, tetrazol ring, pyrazole ring, pyridine ring, pyrimidine ring, pyrida Zin ring, pyrazine ring, triazine ring, indole ring, isoindole ring, 1H-indazo Benzoid ring, benzimidazole ring, benzoxazole ring, benzothiazole ring, 1H-be Nzotriazole ring, quinoline ring, isoquinoline ring, sinnoline ring, quinazoline ring, quino Xaline ring, phthalazine ring, naphthyridine ring, purine ring, pteridine ring, carbazole ring , acridine ring, phenoxathiine ring, phenoxazine ring, phenothiazine ring, phenadyl phenazacillin ring, indoridine ring, furan ring, benzofuran ring, isobenzofuran ring benzo-ring, dibenzofuran ring, thiophene ring, benzothiophene ring, dibenzothiophene ring, Flazan ring, thianthlene ring, indolocarbazole ring, benzoindolocarbazole ring Examples of monovalent groups include the benzobenzoindocarbazole ring and the naphthobenzofuran ring. It can be done. At least one hydrogen atom in the compound represented by formula (H2) is an alkyl group having 1 to 6 carbon atoms. It is substituted with cycloalkyl, cyano, halogen, or deuterium atoms having 3 to 14 carbon atoms. That's good too.

[0245] <Compounds represented by the general formula (H3) (an example of a polymer host material)> [ka]

[0246] In equation (H3), Each MU is a divalent compound, independently represented by removing any two hydrogen atoms from an aromatic compound. Each of the bases, EC, is independently represented by removing any one hydrogen atom from an aromatic compound. It is a monovalent group, where two hydrogen atoms in MU are substituted with EC or MU, and k is 2 to 50000. It is an integer.

[0247] More specifically, MU is independently allirene, heteroarylene, and diarylene aryla It is mino, diarylenearylboryl, oxavorin-diyl, azavorin-diyl , ECs are, independently, hydrogen, aryl, heteroaryl, diarylamino, and di It is a heteroarylamino, arylheteroarylamino, or aryloxy, At least one hydrogen in MU and EC is further aryl, heteroaryl, They may be substituted with diarylamino, alkyl, and cycloalkyl groups. k is an integer between 2 and 50000. k is preferably an integer between 20 and 50000, and is an integer between 100 and 50000. It is preferable to do so.

[0248] In formula (H3), at least one hydrogen atom in MU and EC is a carbon atom with 1 to 24 carbon atoms. Lukyl, cycloalkyl with 3 to 24 carbon atoms, may be substituted with halogen or deuterium. Furthermore, any -CH2- in the alkyl group is either -O- or -Si(CH3)2 - may be substituted, and is directly linked to EC in formula (H3) in the alkyl group. Any -CH2- other than CH2- may be substituted with arylene having 6 to 24 carbon atoms. Any hydrogen atom in the alkyl group may be substituted with fluorine.

[0249] For example, remove any two hydrogen atoms from any of the following compounds and list them in the table. Examples of divalent groups include those that are converted to iontophoresis. [ka]

[0250] More specifically, divalent groups represented by one of the following structures are included. And MU combines with other MUs or ECs in *.

[0251] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka]

[0252] Furthermore, examples of ECs include monovalent groups represented by one of the following structures. In these cases, EC is coupled with MU at *.

[0253] [ka] [ka]

[0254] The compound represented by formula (H3) has a total MU content in the molecule, from the viewpoint of solubility and coating film-forming properties. Preferably, 10 to 100% of the number (k) of MU has an alkyl group with 1 to 24 carbon atoms. 30-100% of the total number of MU (k) in the molecule are alkyl groups with 1-18 carbon atoms (3 carbon atoms). It is more preferable to have ~18 branched alkyl groups, and the total number of MUs (k) in the molecule is 50 ~100% of MU contains alkyl groups with 1 to 12 carbon atoms (branched alkyl groups with 3 to 12 carbon atoms). It is even more preferable to do so. On the other hand, from the viewpoint of in-plane orientation and charge transport, M in the molecule It is preferable that 10-100% of the total number of U (k) have alkyl groups with 7-24 carbon atoms. Furthermore, 30-100% of the total number of MU (k) in the molecule are alkyl (carbon) with 7-24 carbon atoms. It is more preferable to have a number of branched alkyl groups (7 to 24).

[0255] <Compounds containing a structure represented by the general formula (H4)> The compound in question is a compound containing a structure represented by the following formula (H4), and multiple such structures are used. Preferably 1 to 5, more preferably 1 to 3, even more preferably 1 to 2, most preferably The term "ku" includes one element, and if it includes multiple elements, the structures are directly connected by single bonds or specific bonds. They are bonded at the substrate. [ka]

[0256] In the above general formula (H4), G is independently either "=C(-H)-" or "=N-". Yes, and the H in the above "=C(-H)-" is a substituent or a structure represented by other formulas (H4). It may have been replaced.

[0257] Compounds containing the structure represented by the general formula (H4) are, for example, described in International Publication No. 2012 / 153780. Compounds described in International Publication No. 2013 / 038650, etc., can be used, as described in the aforementioned literature. It can be manufactured according to the method.

[0258] Examples of substituents where H in G, "=C(-H)-", is substituted are as follows: These are examples, but they are not limited to these.

[0259] Examples of substituents called "aryl groups" include phenyl, tolyl, xylyl, and naphthyl. Lu, phenanthril, pyrenyl, crisenyl, benzo[c]phenanthril, benzo[g ]Crysenyl, benzoantryl, triphenylenyl, fluorenyl, 9,9-dimethyl Fluorenil, benzofluorenil, dibenzofluorenil, biphenylil, terphenil Examples include lyl, quaterphenylyl, fluoranthenyl, and preferably phenyl, bif Phenyl, terphenyl, quaterphenyl, naphthyl, triphenylenyl and Examples of substituted aryl groups include tolyl and xyl. Examples include lyl and 9,9-dimethylfluorenyl. As the specific examples show... The aryl group includes both condensed aryl groups and uncondensed aryl groups.

[0260] Specific examples of the substituent "heteroaryl group" include pyrrolyl, pyrazolyl, and pyrazi Nyl, pyrimidinyl, pyridazinyl, pyridyl, triazinyl, indolyl, isoindodinyl Lil, imidazolyl, benzimidazolyl, indazolyl, imidazo[1,2-a]pyl Dinyl, furyl, benzofuranil, isobenzofuranil, dibenzofuranil, azadiben Zofuranil, thiophenyl, benzothienyl, dibenzothienyl, azadibenzothienyl , quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, naphthilidinyl, carbazo Lyl, azacarbazolyl, phenanthrolinyl, acridinyl, phenanthrolinyl, f Enazinyl, phenothiazinyl, phenoxazinyl, oxazolyl, oxadiazolyl, Flazanyl, benzoxazolyl, thienyl, thiazolyl, thiadiazolyl, benzthia Examples include zolyl, triazolyl, tetrazolyl, and preferably dibenzofuranil, di Benzothienyl, carbazolyl, pyridyl, pyrimidinyl, triazinyl, azadibenzo Examples include furanyl and azadibenzothienyl. Nzothienyl, azadibenzofuranyl, or azadibenzothienyl are more preferred.

[0261] The substituent "substituted silyl group" is a substituted or unsubstituted trialkylsilyl group, substituted or or unsubstituted arylalkylsilyl groups, and substituted or unsubstituted triarylsilyl groups It is also preferable that the group be selected from a group consisting of groups.

[0262] Specific examples of substituted or unsubstituted trialkylsilyl groups include trimethylsilyl and Examples include triethylsilyl and substituted or unsubstituted arylalkylsilyl groups. Specific examples include diphenylmethylsilyl, ditylmethylsilyl, and phenylmethylsilyl Examples include triarylsilyl groups. Specific examples of substituted or unsubstituted triarylsilyl groups. Examples include triphenylsilyl and tritrilsilyl.

[0263] The substituent, "substituted phosphine oxide group," is a substituted or unsubstituted diaryl phosphine oxide group. It is also preferable that it be a diarylphosphine oxide group. Substituted or unsubstituted diarylphosphine oxide Specific examples of the 'do' group include diphenylphosphine oxide and ditrilphosphine oxide. Examples include "Do," etc.

[0264] Examples of substituted carboxyl groups include benzoyloxy. ru.

[0265] The linking groups that combine multiple structures represented by formula (H4) include the aforementioned aryl and hete groups. Examples include 2-4 valent, 2-3 valent, or 2 valent derivatives of roaryl.

[0266] Specific examples of compounds containing the structure represented by the general formula (H4) are shown below. [ka] [ka]

[0267] <Compounds represented by the general formula (H5)> [ka] In the above formula (H5), R 1 ~R 11 These are, independently, hydrogen, aryl, heteroaryl, and diarylia. Mino, diheteroarylamino, arylheteroarylamino, alkyl or cyclo Alkyl (the above are the first substituents), and the R 1 ~R 11 at least one hydrogen Furthermore, aryl, heteroaryl, diarylamino, alkyl, or cycloalkyl (The above may be substituted with the second substituent.) R 1 ~R 11 Adjacent groups among them bond together with the a, b, or c rings, forming an aryl group. They may form a ring or a heteroaryl ring, and at least one of the formed rings The hydrogen in aryl, heteroaryl, diarylamino, diheteroarylamino, and The first substituent is a reel heteroarylamino, alkyl, or cycloalkyl compound. They may be replaced, and at least one hydrogen in these substituents is further aryl, Heteroaryl, diarylamino, alkyl, or cycloalkyl (the above, the second substituent) ) may be replaced with, In ring a, ring b, and ring c, any "-C(-R)=" (where R is R 1 ~R 1 1 The part "-N=" may be replaced with "-N=". In the compound represented by formula (H5), at least one hydrogen atom is independently a It may be substituted with chlorogen or deuterium.

[0268] Any "-C(-R)=" in ring a, ring b, and ring c in equation (H5) (where R is R 1 ~R 11 (is) is replaced with "-N=", and pyridine ring, pyrimidine ring, pyrida It may be changed to a din ring, pyrazine ring, or other nitrogen-containing heteroaryl ring. For further details, refer to the explanations in the above general formulas (2A) and (2B).

[0269] Preferably, in the above formula (H5), R 1 ~R 11 These are, independently, hydrogen, aryl atoms with 6 to 30 carbon atoms, and aryl atoms with 2 to 3 carbon atoms. 0 heteroaryl and diarylamino (where aryl is an aryl with 6 to 12 carbon atoms) , an alkyl group having 1 to 12 carbon atoms or a cycloalkyl group having 3 to 16 carbon atoms, and the R 1 ~ R 11 At least one hydrogen in is further an aryl group with 6-30 carbon atoms, and a group with 2-3 carbon atoms. 0 heteroaryl and diarylamino (where aryl is an aryl with 6 to 12 carbon atoms) Even if substituted with alkyl groups having 1 to 12 carbon atoms or cycloalkyl groups having 3 to 16 carbon atoms often, R 1 ~R 11 Among them, adjacent groups bond together to form an a-ring, b-ring, or c-ring, resulting in a total of 9 carbon atoms. They may form an aryl ring with ~16 carbon atoms or a heteroaryl ring with 6 to 15 carbon atoms, At least one hydrogen in the formed ring is an aryl group with 6 to 30 carbon atoms, and a group with 2 to 3 carbon atoms. 0 heteroaryl and diarylamino (where aryl is an aryl with 6 to 12 carbon atoms) Even if substituted with alkyl groups having 1 to 12 carbon atoms or cycloalkyl groups having 3 to 16 carbon atoms Often, at least one hydrogen atom in these substituents is further an aryl group having 6 to 30 carbon atoms. heteroaryl and diarylamino compounds with 2 to 30 carbon atoms (whereas aryl compounds have 6 to 1 carbon atoms). (2 aryls), alkyls with 1 to 12 carbon atoms, or cycloalkyls with 3 to 16 carbon atoms. It may have been replaced.

[0270] More preferably, in the above formula (H5), R 1 ~R 11 These are, independently, hydrogen, aryl atoms with 6 to 16 carbon atoms, and aryl atoms with 2 to 1 carbon atoms. 5 heteroaryl and diarylamino (where aryl is an aryl with 6 to 10 carbon atoms) , an alkyl group having 1 to 6 carbon atoms or a cycloalkyl group having 3 to 14 carbon atoms, and the R 1 ~R 11 At least one hydrogen in is further an aryl group with 6-16 carbon atoms, and a group with 2-15 carbon atoms. heteroaryls, diarylaminos (where aryl is an aryl with 6 to 10 carbon atoms), It may also be substituted with alkyl groups having 1 to 6 carbon atoms or cycloalkyl groups having 3 to 14 carbon atoms. , R 1 ~R 11 Among them, adjacent groups bond together to form an a-ring, b-ring, or c-ring, resulting in a total of 9 carbon atoms. They may form an aryl ring with ~12 carbon atoms or a heteroaryl ring with 6 to 12 carbon atoms, At least one hydrogen in the formed ring is an aryl group with 6 to 16 carbon atoms, and a group with 2 to 1 carbon atoms. 5 heteroaryl and diarylamino (where aryl is an aryl with 6 to 10 carbon atoms) It may also be substituted with alkyl groups having 1 to 6 carbon atoms or cycloalkyl groups having 3 to 14 carbon atoms. Furthermore, at least one hydrogen atom in these substituents is further an aryl atom having 6 to 16 carbon atoms. Heteroaryl and diarylamino compounds with 2 to 15 carbon atoms (whereas aryl compounds have 6 to 10 carbon atoms) Substituted with an aryl, C1-C6 alkyl, or C3-C4 cycloalkyl group. It's okay if it's not allowed.

[0271] In the first and second substituents described above, aryl, heteroaryl, diarylar The "aryl" in mino, diheteroarylamino, and arylheteroarylamino Examples of "heteroaryls" include the following:

[0272] Specific examples of "aryl" include aryls with 6 to 30 carbon atoms. aryls with 6 to 24 carbon atoms are preferred, and aryls with 6 to 20 carbon atoms are more preferred, and aryls with 6 carbon atoms are preferred. ~16 aryls are more preferred, and aryls with 6 to 12 carbon atoms are particularly preferred. 6 to 10 aryl groups are most preferred. For example, monocyclic aryl groups such as phenyl and bicyclic aryl groups. The reel is (2-,3-,4-)biphenylyl, and the condensed bicyclic aryl is (1-,2 -) Naphthyl, a tricyclic aryl terpheniryl (m-terphenyl-2'-yl, m-terphenyl-4'-yl, m-terphenyl-5'-yl, o-terphenyl-3 '-yl, o-terphenyl-4'-yl, p-terphenyl-2'-yl, m-terf phenyl-2-yl, m-terphenyl-3-yl, m-terphenyl-4-yl, o-terphenyl o-terphenyl-2-yl, o-terphenyl-3-yl, o-terphenyl-4-yl, p -Terphenyl-2-yl, p-Terphenyl-3-yl, p-Terphenyl-4-yl ), a condensed tricyclic aryl, acenaphthylene-(1-,3-,4-,5-)yl, Luoren-(1-,2-,3-,4-,9-)yl, Phenalen-(1-,2-)yl, (1-,2-,3-,4-,9-)phenanthryl, a tetracyclic aryl quaterphenyl Nilyl(5'-phenyl-m-terphenyl-2-yl, 5'-phenyl-m-terphenyl) Nyl-3-yl, 5'-phenyl-m-terphenyl-4-yl, m-quaterphenyl (Lu) Triphenylene-(1-,2-)yl, pyrene-(1- ,2-,4-)yl, naphthasen-(1-,2-,5-)yl, condensed pentacyclic aryl Perylene-(1-,2-,3-)yl and pentasene-(1-,2-,5-,6-)yl These are some examples.

[0273] Specific examples of "heteroaryls" include heteroaryls with 2 to 30 carbon atoms. A heteroaryl with 2 to 25 carbon atoms is preferred, and a heteroaryl with 2 to 20 carbon atoms is preferred. More preferably, heteroaryls having 2 to 15 carbon atoms are even more preferred, and those having 2 to 10 carbon atoms are more preferably Heteroaryls are particularly preferred. For example, pyrrolyl, oxazolyl, isoxazolyl, Thiazolyl, isothiazolyl, imidazolyl, oxadiazolyl, thiadiazolyl, tri Azolyl, Tetrazolyl, Pyrazolyl, Pyridinyl, Pyrimidinyl, Pyridadinyl, Pyridazinyl Dinyl, triazinyl, indolyl, isoindolyl, 1H-indazolyl, benzimi Dazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinoli Nyl, Isoquinolinyl, Synnolinyl, Quinazolinyl, Quinoxalinyl, Phthalazinyl Naphthilidinyl, Purinyl, Pteridinyl, Carbazolyl, Acridinyl, Phenoxa Inyl, phenoxadinyl, phenothiazinyl, phenadinyl, phenazacylinyl, Inyl Doridinyl, Furanil, Benzofuranil, Isobenzofuranil, Dibenzofuranil, Naph Tobenzofuranil, thiophenyl, benzothiophenyl, isobenzothiophenyl, dibe Nzothiophenyl, naphthobenzothiophenyl, benzophosphoryl, dibenzophosphoryl , monovalent group of benzophosphole oxide ring, monovalent group of dibenzophosphole oxide ring, Flazanil, thianthrenil, indolocarbazol, benzoindocarbazol Examples include benzobenzoindocarbazolyl.

[0274] In the first and second substituents described above, "alkyl" refers to a straight chain and a branched chain. Either of these is acceptable, for example, a linear alkyl group with 1 to 24 carbon atoms or a branched alkyl group with 3 to 24 carbon atoms. Examples include alkyl chains, which are alkyl groups with 1 to 18 carbon atoms (branched-chain alkyl groups with 3 to 18 carbon atoms). C1-C12 alkyl groups are preferred, and C3-C12 branched alkyl groups are more preferred. Furthermore, alkyl groups having 1 to 6 carbon atoms (branched-chain alkyl groups having 3 to 6 carbon atoms) are more preferable. Alkyl groups with 1 to 5 prime numbers (branched-chain alkyl groups with 3 to 5 carbon atoms) and alkyl groups with 1 to 4 carbon atoms (carbon atoms) Branched alkyl groups with 3 to 4 prime numbers are particularly preferred, and methyl groups are most preferred. For example, methyl ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl til, n-pentyl, isopentyl, neopentyl, t-pentyl (t-amyl), n- Hexyl, 1-methylpentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-hept Tyl, 1-methylhexyl, n-octyl, t-octyl(1,1,3,3-tetramethyl (Butyl), 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n- Nyl, 2,2-dimethylheptyl, 2,6-dimethyl-4-heptyl, 3,5,5-tri Methylhexyl, n-decyl, n-undecyl, 1-methyldecyl, n-dodecyl, n- Tridecyl, 1-hexylheptyl, n-tetradecyl, n-pentadecyl, n-hexa Examples include decyl, n-heptadecyl, n-octadecyl, and n-eicosyl. For example, 1-ethyl-1-methylpropyl, 1,1-diethylpropyl, 1,1-dimethylpropyl 1,1,4-Trimethylpentyl, 1,1 ,2-trimethylpropyl, 1,1-dimethyloctyl, 1,1-dimethylpentyl, 1 ,1-dimethylheptyl, 1,1,5-trimethylhexyl, 1-ethyl-1-methylhexyl Xyl, 1-ethyl-1,3-dimethylbutyl, 1,1,2,2-tetramethylpropyl , 1-butyl-1-methylpentyl, 1,1-diethylbutyl, 1-ethyl-1-methyl Pentyl, 1,1,3-trimethylbutyl, 1-propyl-1-methylpentyl, 1,1 ,2-trimethylpropyl,1-ethyl-1,2,2-trimethylpropyl,1-prop Other examples include 1-methylbutyl and 1,1-dimethylhexyl.

[0275] In the first and second substituents described above, "cycloalkyl" refers to a group with 3 carbon atoms. 24-C14 cycloalkyl groups, C3-C12 cycloalkyl groups, C3-C16 cycloalkyl groups Kill, cycloalkyl groups with 3-14 carbon atoms, cycloalkyl groups with 5-10 carbon atoms, cycloalkyl groups with 5- 8-C12 cycloalkyl groups, 5-6 C12 cycloalkyl groups, 5-C12 cycloalkyl groups, etc. Examples include cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl. cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, and these carbon Alkyl (especially methyl) substituted compounds of numbers 1 to 4, bicyclo[1.1.0]butyl, bicyclo [1.1.1] Pentyl, bicyclo[2.1.0] Pentyl, bicyclo[2.1.1] He Xyl, bicyclo[3.1.0]hexyl, bicyclo[2.2.1]heptyl, bicyclo [2.2.2] Octyl, adamantyl, diamantyl, decahydronaphthalenyl, deca Examples include hydroazurenyl.

[0276] When the first substituent is aryl, the substitution position is R 1 , R 3 , R 4 , R 5 , R 10 and R 11 Preferably, R 1 and R 3 Substitution to R 5 and R 10 Substitution to R 4 oh Call R 11 Substitution to is more preferable, and the aryl group is preferably a phenyl group.

[0277] When the first substituent is a heteroaryl compound, the substitution site is R 1 , R 2 , R 3 , R4 , R 5 , R 6 , R 9 , R 10 and R 11 Preferably, R 1 Substitution to R 2 Substitution to R 3 Substitution to R 1 and R 3 Substitution to R 4 and R 11 Substitution to R 5 and R 10 to Replacement, R 6 and R 9 Substitution to is more preferable, and the heteroaryl group is preferably a carbazolyl group. This heteroaryl (e.g., carbazolyl) is placed at the above position via a phenylene group. It's okay to exchange it.

[0278] A specific example of a compound represented by formula (H5) is, for example, the compound represented by the following structural formula. Compounds are one example. Note that "Me" in the formula represents a methyl group.

[0279] [ka] [ka]

[0280] The compound represented by formula (H5) is formed by first bonding the a-c rings with a bonding group (-O-). An intermediate is produced (first reaction), and then the a-c rings are bonded with B (boron) to form the final product. The final product can be produced (second reaction). In the first reaction, for example, a nucleophilic substitution reaction or Common etherification reactions such as the Luman reaction can be used. In addition, in the second reaction, tandem The hetero-Friedel-Crafts reaction (a series of aromatic electrophilic substitution reactions) can be used. For details of the second reaction, please refer to the explanation in International Publication No. 2015 / 102118. It is possible.

[0281] <Compounds represented by the general formula (H6)> [ka] In the above formula (H6), R 1 ~R 16 These are, independently, hydrogen, aryl, heteroaryl, and diarylia. Mino, diheteroarylamino, arylheteroarylamino, alkyl or cyclo Alkyl (the above are the first substituents), and the R 1 ~R 16 at least one hydrogen Furthermore, aryl, heteroaryl, diarylamino, alkyl, or cycloalkyl (The above may be substituted with the second substituent.) R 1 ~R 16 Adjacent groups among them bond together to form rings a, b, c, or d. They may form an aryl ring or a heteroaryl ring, and at least in the formed ring Each hydrogen atom is aryl, heteroaryl, diarylamino, or diheteroaryl. Mino, arylheteroarylamino, alkyl, or cycloalkyl (all of the above are first substitutions) They may be substituted with a (group), and at least one hydrogen in these substituents is further a Reels, heteroaryls, diarylaminos, alkyls, or cycloalkyls (the above, the first It may also be substituted with two substituents. In the compound represented by formula (H6), at least one hydrogen atom is independently a It may be substituted with chlorogen or deuterium.

[0282] Preferably, in the above formula (H6), R 1 ~R 16 These are, independently, hydrogen, aryl atoms with 6 to 30 carbon atoms, and aryl atoms with 2 to 3 carbon atoms. 0 heteroaryl and diarylamino (where aryl is an aryl with 6 to 12 carbon atoms) , an alkyl group having 1 to 12 carbon atoms or a cycloalkyl group having 3 to 16 carbon atoms, and the R 1 ~ R 16 At least one hydrogen in is further an aryl group with 6-30 carbon atoms, and a group with 2-3 carbon atoms. 0 heteroaryl and diarylamino (where aryl is an aryl with 6 to 12 carbon atoms) Even if substituted with alkyl groups having 1 to 12 carbon atoms or cycloalkyl groups having 3 to 16 carbon atoms often, R 1 ~R 16 Adjacent groups among them bond together to form rings a, b, c, or d. Even if it forms an aryl ring with 9 to 16 carbon atoms or a heteroaryl ring with 6 to 15 carbon atoms Often, at least one hydrogen atom in the formed ring is an aryl or carbon atom with 6 to 30 carbon atoms. Heteroaryl and diarylamino compounds with 2 to 30 carbon atoms (where aryl is an a compound with 6 to 12 carbon atoms). (Reel), substituted with alkyl groups having 1 to 12 carbon atoms or cycloalkyl groups having 3 to 16 carbon atoms. It is also possible that at least one hydrogen atom in these substituents has 6 to 30 carbon atoms. Aryl, heteroaryls with 2-30 carbon atoms, diarylaminos (where aryl is carbon) aryl atoms (6-12 carbon atoms), alkyl atoms (1-12 carbon atoms), or cycloalkyl atoms (3-16 carbon atoms) It may be replaced with a kill.

[0283] More preferably, in the above formula (H6), R 1 ~R 16These are, independently, hydrogen, aryl atoms with 6 to 16 carbon atoms, and aryl atoms with 2 to 1 carbon atoms. 5 heteroaryl and diarylamino (where aryl is an aryl with 6 to 10 carbon atoms) , an alkyl group having 1 to 6 carbon atoms or a cycloalkyl group having 3 to 14 carbon atoms, and the R 1 ~R 16 At least one hydrogen in is further an aryl group with 6-16 carbon atoms, and a group with 2-15 carbon atoms. heteroaryls, diarylaminos (where aryl is an aryl with 6 to 10 carbon atoms), It may also be substituted with alkyl groups having 1 to 6 carbon atoms or cycloalkyl groups having 3 to 14 carbon atoms. , R 1 ~R 16 Adjacent groups among them bond together to form rings a, b, c, or d. Even if it forms an aryl ring with 9 to 12 carbon atoms or a heteroaryl ring with 6 to 12 carbon atoms Often, at least one hydrogen atom in the formed ring is an aryl or carbon atom with 6 to 16 carbon atoms. Heteroaryl and diarylamino compounds with 2 to 15 carbon atoms (where aryl is an a) (Reel), substituted with alkyl groups having 1 to 6 carbon atoms or cycloalkyl groups having 3 to 14 carbon atoms They may also be present, and at least one hydrogen in these substituents may further be a C6-C16 atom Riesl, heteroaryls with 2 to 15 carbon atoms, diarylaminos (where aryl refers to the number of carbon atoms) aryl (6-10 carbon atoms), alkyl (1-6 carbon atoms), or cycloalkyl (3-14 carbon atoms) It may be replaced with .

[0284] In the first and second substituents described above, aryl, heteroaryl, diarylar The "aryl" in mino, diheteroarylamino, and arylheteroarylamino Examples of "heteroaryls" include the following:

[0285] Specific examples of "aryl" include aryls with 6 to 30 carbon atoms. aryls with 6 to 24 carbon atoms are preferred, and aryls with 6 to 20 carbon atoms are more preferred, and aryls with 6 carbon atoms are preferred. ~16 aryls are more preferred, and aryls with 6 to 12 carbon atoms are particularly preferred. 6 to 10 aryl groups are most preferred. For example, monocyclic aryl groups such as phenyl and bicyclic aryl groups. The reel is (2-,3-,4-)biphenylyl, and the condensed bicyclic aryl is (1-,2 -) Naphthyl, a tricyclic aryl terpheniryl (m-terphenyl-2'-yl, m-terphenyl-4'-yl, m-terphenyl-5'-yl, o-terphenyl-3 '-yl, o-terphenyl-4'-yl, p-terphenyl-2'-yl, m-terf phenyl-2-yl, m-terphenyl-3-yl, m-terphenyl-4-yl, o-terphenyl o-terphenyl-2-yl, o-terphenyl-3-yl, o-terphenyl-4-yl, p -Terphenyl-2-yl, p-Terphenyl-3-yl, p-Terphenyl-4-yl ), a condensed tricyclic aryl, acenaphthylene-(1-,3-,4-,5-)yl, Luoren-(1-,2-,3-,4-,9-)yl, Phenalen-(1-,2-)yl, (1-,2-,3-,4-,9-)phenanthryl, a tetracyclic aryl quaterphenyl Nilyl(5'-phenyl-m-terphenyl-2-yl, 5'-phenyl-m-terphenyl) Nyl-3-yl, 5'-phenyl-m-terphenyl-4-yl, m-quaterphenyl (Lu) Triphenylene-(1-,2-)yl, pyrene-(1- ,2-,4-)yl, naphthasen-(1-,2-,5-)yl, condensed pentacyclic aryl Perylene-(1-,2-,3-)yl and pentasene-(1-,2-,5-,6-)yl These are some examples.

[0286] Specific examples of "heteroaryls" include heteroaryls with 2 to 30 carbon atoms. A heteroaryl with 2 to 25 carbon atoms is preferred, and a heteroaryl with 2 to 20 carbon atoms is preferred. More preferably, heteroaryls having 2 to 15 carbon atoms are even more preferred, and those having 2 to 10 carbon atoms are more preferably Heteroaryls are particularly preferred. For example, pyrrolyl, oxazolyl, isoxazolyl, Thiazolyl, isothiazolyl, imidazolyl, oxadiazolyl, thiadiazolyl, tri Azolyl, Tetrazolyl, Pyrazolyl, Pyridinyl, Pyrimidinyl, Pyridadinyl, Pyridazinyl Dinyl, triazinyl, indolyl, isoindolyl, 1H-indazolyl, benzimi Dazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinoli Nyl, Isoquinolinyl, Synnolinyl, Quinazolinyl, Quinoxalinyl, Phthalazinyl Naphthilidinyl, Purinyl, Pteridinyl, Carbazolyl, Acridinyl, Phenoxa Inyl, phenoxadinyl, phenothiazinyl, phenadinyl, phenazacylinyl, Inyl Doridinyl, Furanil, Benzofuranil, Isobenzofuranil, Dibenzofuranil, Naph Tobenzofuranil, thiophenyl, benzothiophenyl, isobenzothiophenyl, dibe Nzothiophenyl, naphthobenzothiophenyl, benzophosphoryl, dibenzophosphoryl , monovalent group of benzophosphole oxide ring, monovalent group of dibenzophosphole oxide ring, Flazanil, thianthrenil, indolocarbazol, benzoindocarbazol Examples include benzobenzoindocarbazolyl.

[0287] In the first and second substituents described above, "alkyl" refers to a straight chain and a branched chain. Either of these is acceptable, for example, a linear alkyl group with 1 to 24 carbon atoms or a branched alkyl group with 3 to 24 carbon atoms. Examples include alkyl chains, which are alkyl groups with 1 to 18 carbon atoms (branched-chain alkyl groups with 3 to 18 carbon atoms). C1-C12 alkyl groups are preferred, and C3-C12 branched alkyl groups are more preferred. Furthermore, alkyl groups having 1 to 6 carbon atoms (branched-chain alkyl groups having 3 to 6 carbon atoms) are more preferable. Alkyl groups with 1 to 5 prime numbers (branched-chain alkyl groups with 3 to 5 carbon atoms) and alkyl groups with 1 to 4 carbon atoms (carbon atoms) Branched alkyl groups with 3 to 4 prime numbers are particularly preferred, and methyl groups are most preferred. For example, methyl ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl til, n-pentyl, isopentyl, neopentyl, t-pentyl (t-amyl), n- Hexyl, 1-methylpentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-hept Tyl, 1-methylhexyl, n-octyl, t-octyl(1,1,3,3-tetramethyl (Butyl), 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n- Nyl, 2,2-dimethylheptyl, 2,6-dimethyl-4-heptyl, 3,5,5-tri Methylhexyl, n-decyl, n-undecyl, 1-methyldecyl, n-dodecyl, n- Tridecyl, 1-hexylheptyl, n-tetradecyl, n-pentadecyl, n-hexa Examples include decyl, n-heptadecyl, n-octadecyl, and n-eicosyl. For example, 1-ethyl-1-methylpropyl, 1,1-diethylpropyl, 1,1-dimethylpropyl 1,1,4-Trimethylpentyl, 1,1 ,2-trimethylpropyl, 1,1-dimethyloctyl, 1,1-dimethylpentyl, 1 ,1-dimethylheptyl, 1,1,5-trimethylhexyl, 1-ethyl-1-methylhexyl Xyl, 1-ethyl-1,3-dimethylbutyl, 1,1,2,2-tetramethylpropyl , 1-butyl-1-methylpentyl, 1,1-diethylbutyl, 1-ethyl-1-methyl Pentyl, 1,1,3-trimethylbutyl, 1-propyl-1-methylpentyl, 1,1 ,2-trimethylpropyl,1-ethyl-1,2,2-trimethylpropyl,1-prop Other examples include 1-methylbutyl and 1,1-dimethylhexyl.

[0288] In the first and second substituents described above, "cycloalkyl" refers to a group with 3 carbon atoms. 24-C14 cycloalkyl groups, C3-C12 cycloalkyl groups, C3-C16 cycloalkyl groups Kill, cycloalkyl groups with 3-14 carbon atoms, cycloalkyl groups with 5-10 carbon atoms, cycloalkyl groups with 5- 8-C12 cycloalkyl groups, 5-6 C12 cycloalkyl groups, 5-C12 cycloalkyl groups, etc. Examples include cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl. cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, and these carbon Alkyl (especially methyl) substituted compounds of numbers 1 to 4, bicyclo[1.1.0]butyl, bicyclo [1.1.1] Pentyl, bicyclo[2.1.0] Pentyl, bicyclo[2.1.1] He Xyl, bicyclo[3.1.0]hexyl, bicyclo[2.2.1]heptyl, bicyclo [2.2.2] Octyl, adamantyl, diamantyl, decahydronaphthalenyl, deca Examples include hydroazurenyl.

[0289] The compound represented by formula (H6) can be produced with reference to the description described in International Publication No. 2014 / 042197. It can be produced with reference to the description described in International Publication No. 2014 / 042197.

[0290] <TADF material> By reducing the energy difference between the singlet excited state and the triplet excited state, reverse energy transfer from the triplet excited state, which usually has a low transition probability, to the singlet excited state occurs with high efficiency. As a result, luminescence from the singlet state (thermally activated delayed fluorescence, TADF) is exhibited. In ordinary fluorescence emission, 75% of the triplet excitons generated by current excitation pass through the thermal deactivation path and thus cannot be taken as fluorescence. On the other hand, in TADF, all excitons can be used for fluorescence emission, and a highly efficient organic EL device can be realized. Examples of TADF materials that can be used for such purposes include compounds represented by the following general formula (H7),

[0291] or compounds having the following general formula (H7) as a partial structure. In formula (H7), ED is an electron-donating group, Ln is a linking group, EA is an electron-accepting

Chemical formula

[0292] TADF materials consist of electron-donating substituents called donors and electron-accepting substituents called acceptors. Localizing the intramolecular HOMO and LUMO using acceptive substituents enables efficient reverse intersystem interaction. Designed to cause a difference (reverse intersystem crossing), donor-acceptance It is preferable that the compound is a TA-type TADF compound (DA-type TADF compound).

[0293] Herein, in this specification, "electron-donating substituent" (donor) refers to a TADF compound. This refers to substituents and substructures in which LUMO orbitals are localized within a molecule, and is described as "electron-accepting." A substituent (acceptor) is a substituent in a TADF compound molecule where the HOMO orbital is localized. And this shall mean substructures.

[0294] Generally, TADF compounds using donors and acceptors have spin orbits due to their structure. The spin orbit coupling (SOC) is large, and the exchange between the HOMO and LUMO is... Because the function is small and ΔE(ST) is small, a very fast inverse interterm crossing velocity can be obtained. On the other hand, TADF compounds using donors and acceptors exhibit greater structural relaxation in the excited state. In some molecules, the stable structure differs between the ground state and the excited state, so external stimuli cause the ground state When a transformation from the bottom state to an excited state occurs, the structure then becomes a stable structure in the excited state. Because it gives a wide emission spectrum (which changes), using it as an emissive material reduces color purity. There is a possibility that it will happen.

[0295] If the color purity decreases due to the TADF material, a fluorescent compound can be added as another component to the light-emitting layer. Alternatively, it can be added to a layer adjacent to the luminescent layer. TADF material is an assisting dopant. As a dopant, the other components act as emitting dopants. Other components include the equivalent The absorption spectrum of the compound overlaps, at least partially, with the emission peak of the assisting dopant. Any compound will do.

[0296] Examples of donor and acceptor structures used in TADF materials include Ch The structure described in the Ministry of Materials, 2017, 29, 1946-1963 can be used. For example, sp 3 Examples include functional groups containing nitrogen, and more specifically, carbazo Dimethylcarbazole, di-butylcarbazole, dimethoxycarbazole, Tramethylcarbazole, benzofluorocarbazole, benzothienocarbazole, f Phenyldihydroindocarbazole, phenylbicarbazole, bicarbazole, tar Carbazole, diphenylcarbazolylamine, tetraphenylcarbazolyldiamine, Phenoxazine, dihydrophenazine, phenothiazine, dimethyldihydroacridine, Diphenylamine, (bis(t-butyl)phenyl)amine, ((diphenylamino)phenyl (Nyl)diphenylbenzenediamine, dimethyltetraphenyldihydroacridinediamine , tetramethyl-dihydro-indenoacridine and diphenyl-dihydrodibenzo Examples of groups derived from azacillin include sp. 2 nitrogen Aromatic rings containing elemental groups, CN-substituted aromatic rings, rings having ketones and cyano groups, more specifically , sulfonyl dibenzene, benzophenone, phenylenebis(phenylmethanone), ben Zonitrile, isonicotinonitrile, phthalonitrile, isophthalonitrile, paraphthalo Nitrile, triazole, oxazole, thiadiazole, benzothiazole, benzobi S (thiazole), benzoxazole, benzobis(oxazole), quinoline, ben Zoimidazole, dibenzoquinoxaline, heptazaphenalen, thioxanthondioxaline SID, dimethylanthracenone, anthracendione, pyridine, cycloheptavipyridin N, benzenetricarbonitride, full orange carbonitride, pyrazinedicarbonitride Ryl, pyridine dicarbonitrile, dibenzoquinoxaline dicarbonitrile, pyrimidine Phenylpyrimidine, methylpyrimidine, triazine, triphenyltriazine, bis (Phenylsulfonyl)benzene, Dimethylthioxanthenedioxide, Thianslente Examples of groups derived from traoxide and tris(dimethylphenyl)borane include Examples of Ln include single bonds and arylenes, and more specifically, fe Examples include nilenene, biphenylene, and naphthylene. Also, in all of these structures, water The element may be substituted with alkyl, cycloalkyl, and aryl. In particular, as a substructure Carbazole, phenoxazine, acridine, triazine, pyrimidine, pyrazine, Thioxanthene, benzonitrile, phthalonitrile, isophthalonitrile, diphenyl Select from rufon, triazole, oxadiazole, thiadiazole, and benzophenone. It is preferable that the compound has at least one of the selected compounds.

[0297] Compounds represented by general formula (H7) are, more specifically, those represented by the following general formulas (H7-1), ( It is a compound represented by either formula (H7-2) or formula (H7-3). [ka]

[0298] In the above general formulas (H7-1), (H7-2), and (H7-3), M is independently a single bond, -O-, >N-Ar, or >C(-Ar)2. , the depth of the HOMO of the substructure formed and the excited singlet energy levels and excited triplet From the viewpoint of energy level height, it is preferably a single bond, -O- or >N-Ar. , J is a spacer structure that separates the donor substructure from the acceptor substructure. Each is independently an arylene with 6 to 18 carbon atoms, and the donor substructure and accept From the perspective of the magnitude of conjugation leaching from the turbid substructure, arylenes with 6 to 12 carbon atoms are Preferably, and more specifically, phenylene, methylphenylene and dimethylphenylene Listed, Q is independently =C(-H)- or =N-, and the L of the substructure it forms The shallowness of the UMO and the height of the excited singlet energy level and excited triplet energy level From this perspective, preferably, =N- Ar is composed of hydrogen, aryl atoms with 6 to 24 carbon atoms, and heteropropyl atoms with 2 to 24 carbon atoms, each independently. Loaryl, alkyl with 1 to 12 carbon atoms, or cycloalkyl with 3 to 18 carbon atoms, The depth of the HOMO of the substructure formed and the excited singlet energy levels and excited triplet energy levels From the viewpoint of energy level height, preferably hydrogen, aryl atoms having 6 to 12 carbon atoms, carbon number 2-14 heteroaryl groups, 1-4 C1 alkyl groups, or 6-10 C1 cycloaryl groups Kill, and more preferably hydrogen, phenyl, tolyl, xylyl, mesityl, biphenyl L, pyridyl, bipyridyl, triazinyl, carbazolyl, dimethylcarbazolyl, di- These are t-butylcarbazol, benzimidazole, or phenylbenzimidazole. More preferably, hydrogen, phenyl, or carbazolyl, m is either 1 or 2. n is an integer between 2 and (6-m), and from the viewpoint of steric hindrance, preferably between 4 and (6-m) It is an integer of ). Furthermore, at least one hydrogen atom in each of the above formulas is a halogen or It may be substituted with deuterium.

[0299] Examples of compounds represented by formula (H7) include compounds represented by the following structure: Note that in the structural formula, * indicates a bond position, "Me" is a methyl group, and "tBu" is a t-butyl group. show.

[0300] [ka]

[0301] [ka]

[0302] [ka]

[0303] [ka]

[0304] [ka]

[0305] [ka]

[0306] [ka]

[0307] [ka]

[0308] [ka]

[0309] Among the specific compounds listed above, 4CzB is a particularly noteworthy example of a compound represented by the general formula (H7). N, 4CzBN-Ph, 5CzBN, 3Cz2DPhCzBN, 4CzIPN, 2PXZ -TAZ, Cz-TRZ3, BDPCC-TPTA, MA-TA, PA-TA, FA-T A, PXZ-TRZ, DMAC-TRZ, BCzT, DCzTrz, DDCzTrz, s piroAC-TRZ, Ac-HPM, Ac-PPM, Ac-MPM, TCzTrz, T mCzTrz and DCzmCzTrz are preferred.

[0310] Furthermore, the dopant material is represented by the above general formula (1A) or general formula (1B). In addition to polycyclic aromatic compounds, known compounds can be used, depending on the desired emission color. A variety of materials can be selected. Specifically, for example, phenanthrene, ant Spiren, pyrene, tetracene, pentacene, perylene, naphthopyrene, dibenzopyrene, Condensed ring derivatives such as rubrene and chrysene, benzoxazole derivatives, benzothiazo azole derivatives, benzimidazole derivatives, benzotriazole derivatives, oxazole derivatives Body, oxadiazole derivatives, thiazole derivatives, imidazole derivatives, thiadiazole Derivatives, triazole derivatives, pyrazoline derivatives, stilbene derivatives, thiophene derivatives tetraphenylbutadiene derivatives, cyclopentadiene derivatives, bistyryl anthracite Bistyryl derivatives such as sen derivatives and distyrylbenzene derivatives (Japanese Patent Publication No. 1-245087) (Report), Bistyryl arylene derivative (Japanese Patent Publication No. 2-247278), Diazindacene derivative Body, furan derivatives, benzofuran derivatives, phenylisobenzofuran, dimethylisobe Isobenzofuran, di(2-methylphenyl)isobenzofuran, di(2-trifluoromethyl Isobenzofuran derivatives such as phenyl)isobenzofuran and phenylisobenzofuran , dibenzofuran derivatives, 7-dialkylaminocoumarin derivatives, 7-piperidinocumarin 7-hydroxycoumarin derivatives, 7-methoxycoumarin derivatives, 7-acetoxide Cyclomarin derivatives, 3-benzothiazolylcoumarin derivatives, 3-benzimidazolylcoumarin Phosphorus derivatives, coumarin derivatives such as 3-benzoxazolylcoumarin derivatives, dicyanome Chilenpyran derivatives, dicyanomethylentiopyran derivatives, polymethine derivatives, cyanine Derivatives, oxobenzoanthracene derivatives, xanthene derivatives, rhodamine derivatives, flu Olethene derivatives, pyrylium derivatives, carbostyryl derivatives, acridine derivatives, oxy Sazine derivatives, phenylene oxide derivatives, quinacridone derivatives, quinazoline derivatives, Pyrrolopyridine derivatives, phlopyridine derivatives, 1,2,5-thiadiazolopyrene derivatives, Pyromethene derivatives, perinone derivatives, pyrrolopyrrole derivatives, squarylium derivatives, bi Olantron derivatives, phenazine derivatives, acridone derivatives, deazaflavin derivatives, f Examples include ruolene derivatives and benzofluorene derivatives.

[0311] Examples of dopant materials for each colored light include naphthalene and anthracite. Sen, phenanthrene, pyrene, triphenylene, perylene, fluorene, indene, ku Aromatic hydrocarbon compounds such as lysene and their derivatives, furan, pyrrole, thiophene, siloxane 9-Silafluorene, 9,9'-Spirobicilafluorene, Benzothiophene, Indole, dibenzothiophene, dibenzofuran, imidazopyridine, f Xenanthroline, pyrazine, naphthyridine, quinoxaline, pyrrolopyridine, thioxan Aromatic heterocyclic compounds such as tene and their derivatives, distylylbenzene derivatives, tetraphen Rubutadiene derivatives, stilbene derivatives, aldazine derivatives, coumarin derivatives, imidazo thiazole, thiadiazole, carbazole, oxazole, oxadiazole, Azole derivatives such as triazoles and their metal complexes and N,N'-diphenyl-N Representative example: N'-di(3-methylphenyl)-4,4'-diphenyl-1,1'-diamine Examples include aromatic amine derivatives.

[0312] Additionally, green to yellow dopant materials include coumarin derivatives, phthalimide derivatives, and naphth. Thalimide derivatives, perinone derivatives, pyrrolopyrrole derivatives, cyclopentadiene derivatives , acridone derivatives, quinacridone derivatives and naphthacene derivatives such as rubrene, etc. Furthermore, the compounds exemplified above as blue to blue-green dopant materials include aryl and helium. Introducing substituents that enable longer wavelengths, such as teloaryl, arylvinyl, amino, and cyano. The compound described above is also a suitable example.

[0313] Furthermore, as an orange-to-red dopant material, bis(diisopropylphenyl)perylene Naphthalimide derivatives such as tetracarboxylate imide, perinone derivatives, acetylacetate Rare earth complexes such as Eu complexes with ligands like benzoylacetone and phenanthroline. Body, 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4 H-pyran and its analogues, magnesium phthalocyanine, aluminum chlorophthalocyanine Metal phthalocyanine derivatives such as nin, rhodamine compounds, deazaflavin derivatives, bear Phosphorus derivatives, quinacridone derivatives, phenoxazine derivatives, oxazine derivatives, quinazori Derivatives of phenylalanide, pyrrolopyridine derivatives, squarylium derivatives, biolantron derivatives, phenylalanide derivatives Examples include nazine derivatives, phenoxazone derivatives, and thiadiazolopylene derivatives. Furthermore, the compounds exemplified above as blue to blue-green and green to yellow dopant materials include aryl compounds. , substituents that enable long-wavelength conversion such as heteroaryl, arylvinyl, amino, and cyano The introduced compound is also a suitable example.

[0314] Other dopants are listed in the June 2004 issue of Chemical Industry, page 13, and the list therein. Compounds can be appropriately selected and used from those listed in the references provided.

[0315] Among the dopant materials mentioned above, amines and perylene derivatives having a stilbene structure are particularly noteworthy. The derivative, borane derivative, aromatic amine derivative, coumarin derivative, pyrane derivative, or pyrene derivative A conductor is preferred.

[0316] Amines having a stilbene structure can be represented, for example, by the following formula. [ka] In the said formula, Ar 1 It is an m-valent group derived from aryls with 6 to 30 carbon atoms, Ar 2 Oh biAr 3 These are each independently aryl atoms with 6 to 30 carbon atoms, but Ar 1 ~Ar 3 few At least one has a stilbene structure, Ar 1 ~Ar 3 are aryl, heteroaryl, Alkyl, cycloalkyl, tri-substituted silyl (aryl, alkyl and cycloalkyl It may be substituted with a tri-substituted silyl (or cyano) or at least one of the following, and And m is an integer between 1 and 4.

[0317] Among amines having a stilbene structure, diaminostilbene, represented by the following formula, is more preferred. stomach. [ka] In the said formula, Ar 2 and Ar 3 These are each independently aryl atoms with 6 to 30 carbon atoms. Ar 2 and Ar 3 These include aryl, heteroaryl, alkyl, cycloalkyl, and tri Substituting silyls (trisubstituted with at least one aryl, alkyl, and cycloalkyl group) It may be substituted with a cyyl or cyano compound.

[0318] Specific examples of aryl compounds with 6 to 30 carbon atoms include phenyl, naphthyl, acenaphthirenyl, and flu. Olenyl, phenalenyl, phenantrenyl, anthril, fluoranthenyl, triphe Nirenyl, pyrenyl, crisenyl, naphthacenyl, perilenyl, stilbenyl, distyly Examples include fluorenyl, distyrylbiphenyl, and distyrylfluorenyl.

[0319] A specific example of an amine having a stilbene structure is N,N,N',N'-tetra(4-biphene). Niryl)-4,4'-diaminostilbene, N,N,N',N'-tetra(1-naphthyl) )-4,4'-diaminostilbene, N,N,N',N'-tetra(2-naphthyl)-4 ,4'-diaminostilbene,N,N'-di(2-naphthyl)-N,N'-diphenyl- 4,4'-diaminostilbene, N,N'-di(9-phenanthryl)-N,N'-diph phenyl-4,4'-diaminostilbene, 4,4'-bis[4”-bis(diphenylamylbene) [(no)styryl]-biphenyl, 1,4-bis[4'-bis(diphenylamino)styryl] ]-benzene, 2,7-bis[4'-bis(diphenylamino)styryl]-9,9-di Methylfluorene, 4,4'-bis(9-ethyl-3-carbazovinylene)-biphenyl Examples include 4,4'-bis(9-phenyl-3-carbazovinylene)-biphenyl. ru. Furthermore, stills described in Japanese Patent Publication No. 2003-347056 and Japanese Patent Publication No. 2001-307884, etc. Amines having a ben structure may also be used.

[0320] Examples of perylene derivatives include 3,10-bis(2,6-dimethylphenyl)peri Len, 3,10-bis(2,4,6-trimethylphenyl)perylene, 3,10-dife Nylperylene, 3,4-diphenylperylene, 2,5,8,11-tetra-t-butyl Lylene, 3,4,9,10-tetraphenylperylene, 3-(1'-pyrenyl)-8,1 1-Di(t-butyl)perylene, 3-(9'-anthryl)-8,11-Di(t-butyl) Examples include perylene and 3,3'-bis(8,11-di(t-butyl)perylenel). ru. Also, Japanese Patent Publication No. 11-97178, Japanese Patent Publication No. 2000-133457, Japanese Patent Publication No. 2000-26324, Japanese Patent Publication No. 2 Japanese Patent Publication No. 001-267079, Japanese Patent Publication No. 2001-267078, Japanese Patent Publication No. 2001-267076, Japanese Patent Publication No. 2000-34234 Perylene described in the Public Gazette, Japanese Patent Publication No. 2001-267075, and Japanese Patent Publication No. 2001-217077, etc. Derivatives may also be used.

[0321] Examples of borane derivatives include 1,8-diphenyl-10-(dimethylboryl) Anthracene, 9-phenyl-10-(dimethylboryl)anthracene, 4-(9'- Anthril) Dimethylborylnaphthalene, 4-(10'-phenyl-9'-anthryl) Dimethylborylnaphthalene, 9-(dimethylboryl)anthracene, 9-(4'-bi Phenylyl)-10-(dimethylboryl)anthracene, 9-(4'-(N-carbazol Examples include lyl(phenyl)-10-(dimethylboryl)anthracene. Furthermore, even if you use borane derivatives described in International Publication No. 2000 / 40586, etc. good.

[0322] Aromatic amine derivatives can be represented, for example, by the following formula. [ka] In the said formula, Ar 4 Ar is an n-valent group derived from aryl atoms with 6 to 30 carbon atoms, 5 Oh biAr 6 Each of these is an aryl group with 6 to 30 carbon atoms, and Ar 4 ~Ar 6 is, Alkyl, heteroaryl, alkyl, cycloalkyl, trisubstituted silyl (aryl, alkyl) Substituted with silyl (trisubstituted with at least one cycloalkyl or cycloalkyl) or cyano This may be the case, and n is an integer between 1 and 4.

[0323] In particular, Ar 4 anthracene, chrysene, fluorene, benzofluorene or pyrene It is a divalent group derived from Ar 5 and Ar 6 Each of them independently has 6 to 30 carbon atoms. It is a reel, Ar 4 ~Ar 6 These are aryl, heteroaryl, alkyl, and cycloalkyl Tri-substituted silyl(aryl, alkyl, and cycloalkyl) It may be substituted with a silyl (or cyano) and n is 2, aromatic Amine derivatives are more preferred.

[0324] Specific examples of aryl compounds with 6 to 30 carbon atoms include phenyl, naphthyl, acenaphthirenyl, and flu. Olenyl, phenalenyl, phenantrenyl, anthril, fluoranthenyl, triphe Examples include nirenyl, pyrenyl, crisenyl, naphthacenyl, perilenyl, and pentacenyl. It is possible.

[0325] As for aromatic amine derivatives, as for chrysene derivatives, for example, N,N,N',N'-the Traphenylchrysene-6,12-diamine, N,N,N',N'-tetra(p-tolyl ) Chrysene-6,12-diamine, N,N,N',N'-tetra(m-tolyl)chrysene -6,12-diamine, N,N,N',N'-tetrakis(4-isopropylphenyl) Chrysen-6,12-diamine, N,N,N',N'-tetra(naphthalene-2-yl) Chrysene-6,12-diamine, N,N'-diphenyl-N,N'-di(p-tolyl) Lysene-6,12-diamine, N,N'-diphenyl-N,N'-bis(4-ethylphenyl Nyl)chrysene-6,12-diamine, N,N'-diphenyl-N,N'-bis(4-) Sopropylphenyl)chrysene-6,12-diamine, N,N'-diphenyl-N,N' -Bis(4-t-butylphenyl)chrysene-6,12-diamine, N,N'-bis(4 -Isopropylphenyl)-N,N'-di(p-tolyl)chrysene-6,12-diamine These are some examples.

[0326] Furthermore, as a pyrene derivative, for example, N,N,N',N'-tetraphenylpyrene-1, 6-diamine, N,N,N',N'-tetra(p-tolyl)pyrene-1,6-diamine, N,N,N',N'-tetra(m-tolyl)pyrene-1,6-diamine, N,N,N', N'-Tetrakis(4-isopropylphenyl)pyrene-1,6-diamine, N,N,N ',N'-Tetrakis(3,4-dimethylphenyl)pyrene-1,6-diamine, N,N '-diphenyl-N,N'-di(p-tolyl)pyrene-1,6-diamine, N,N'-di Phenyl-N,N'-bis(4-ethylphenyl)pyrene-1,6-diamine, N,N' -Diphenyl-N,N'-bis(4-isopropylphenyl)pyrene-1,6-diamine N,N'-diphenyl-N,N'-bis(4-t-butylphenyl)pyrene-1,6- Diamine, N,N'-bis(4-isopropylphenyl)-N,N'-di(p-tolyl) Pyrene-1,6-diamine, N,N,N',N'-tetrakis(3,4-dimethylphenicol (Lu)-3,8-diphenylpyrene-1,6-diamine, N,N,N,N-tetraphenyl Pyrene-1,8-diamine, N,N'-bis(biphenyl-4-yl)-N,N'-diamine Phenylpyrene-1,8-diamine, N 1 ,N 6 -diphenyl-N 1 ,N 6 -Bis-(4- Examples include trimethylsilanylphenyl)-1H,8H-pyrene-1,6-diamine. It can be done.

[0327] Furthermore, anthracene-based compounds include, for example, N,N,N,N-tetraphenylanthracene. N-9,10-diamine, N,N,N',N'-tetra(p-tolyl)anthracene-9 ,10-diamine, N,N,N',N'-tetra(m-tolyl)anthracene-9,10 -Diamine, N,N,N',N'-Tetrakis(4-isopropylphenyl)anthrace N-9,10-diamine, N,N'-diphenyl-N,N'-di(p-tolyl)anthrate Sen-9,10-diamine, N,N'-diphenyl-N,N'-di(m-tolyl)ant Spiral-9,10-diamine, N,N'-diphenyl-N,N'-bis(4-ethylphenyl Nyl)anthracene-9,10-diamine, N,N'-diphenyl-N,N'-bis(4 -Isopropylphenyl)anthracene-9,10-diamine, N,N'-diphenyl- N,N'-Bis(4-t-butylphenyl)anthracene-9,10-diamine, N,N '-Bis(4-isopropylphenyl)-N,N'-di(p-tolyl)anthracene-9 ,10-diamine, 2,6-di-t-butyl-N,N,N',N'-tetra(p-tolyl Anthracene-9,10-diamine, 2,6-di-t-butyl-N,N'-diphenyl -N,N'-bis(4-isopropylphenyl)anthracene-9,10-diamine, 2 ,6-di-t-butyl-N,N'-bis(4-isopropylphenyl)-N,N'-di( p-Tolyl)anthracene-9,10-diamine,2,6-dicyclohexyl-N,N' -Bis(4-isopropylphenyl)-N,N'-di(p-tolyl)anthracene-9, 10-Diamine, 2,6-Dicyclohexyl-N,N'-Bis(4-Isopropylphenicol) (Lu)-N,N'-bis(4-t-butylphenyl)anthracene-9,10-diamine, 9,10-Bis(4-diphenylaminophenyl)anthracene, 9,10-Bis(4 -di(1-naphthylamino)phenyl)anthracene, 9,10-bis(4-di(2-na Phthylamino)phenyl)anthracene, 10-di-p-tolylamino-9-(4-di- p-Tolylamino-1-naphthyl)anthracene, 10-diphenylamino-9-(4- Diphenylamino-1-naphthyl)anthracene, 10-diphenylamino-9-(6- Examples include diphenylamino-2-naphthyl)anthracene.

[0328] In addition, there is [4-(4-diphenylaminophenyl)naphthalene-1-yl]- Diphenylamine, [6-(4-diphenylaminophenyl)naphthalene-2-yl] -Diphenylamine, 4,4'-bis[4-diphenylaminonaphthalene-1-yl]bi Phenyl, 4,4'-bis[6-diphenylaminonaphthalene-2-yl]biphenyl, 4,4"-Bis[4-diphenylaminonaphthalene-1-yl]-p-terphenyl, 4 ,4"-bis[6-diphenylaminonaphthalene-2-yl]-p-terphenyl etc. It can be listed. Alternatively, aromatic amine derivatives described in Japanese Patent Publication No. 2006-156888, etc., may be used.

[0329] Examples of coumarin derivatives include coumarin-6 and coumarin-334. Furthermore, Japanese Patent Publication No. 2004-43646, Japanese Patent Publication No. 2001-76876, and Japanese Patent Publication No. Hei 6-298758 Any of the coumarin derivatives described above may be used.

[0330] Examples of pyran derivatives include DCM and DCJTB, listed below. [ka] Also, Japanese Patent Publication No. 2005-126399, Japanese Patent Publication No. 2005-097283, Japanese Patent Publication No. 2002-234892, Japanese Patent Publication No. 2001-220577, Japanese Patent Publication No. 2001-081090, and Japanese Patent Publication No. 2001-052869, etc. The listed pyran derivatives may also be used.

[0331] The above-mentioned materials for the light-emitting layer (host material and dopant material) have reactive substituents added to them. A polymer compound obtained by polymerizing a reactive compound substituted with a monomer, or a polymer compound thereof. A molecular crosslinked polymer, or a pendant-type polymer obtained by reacting a main-chain polymer with the reactive compound. The compound, or its pendant-type polymer crosslinked form, can be used as a material for the light-emitting layer. This can be achieved. In this case, the reactive substituent is either the general formula (1A) or the general formula (1B) above. We can cite the explanation for polycyclic aromatic compounds represented by [formula]. Details of the applications of such polymer compounds and polymer crosslinks will be described later.

[0332] <Electron injection layer and electron transport layer in organic electroluminescent devices> The electron injection layer 107 efficiently directs electrons moving from the cathode 108 into the light-emitting layer 105. Alternatively, it plays the role of injecting into the electron transport layer 106. The electron transport layer 106 is from the cathode 108 The injected electrons or electrons injected from the cathode 108 through the electron injection layer 107 are efficiently The electron transport layer 106 and electron injection layer 107 play a role in transporting electrons to the light-emitting layer 105. Each involves laminating or mixing one or more types of electron transport / injection materials, or electron transport / injection materials. It is formed from a mixture of injection material and polymer binder.

[0333] The electron injection and transport layer is responsible for the injection of electrons from the cathode and the subsequent transport of electrons. It is desirable that the layer has high electron injection efficiency and efficiently transports the injected electrons. Therefore, it is necessary to have high electron affinity, high electron mobility, and excellent stability. It is preferable that the substance is one that is less likely to generate trapping impurities during manufacturing and use. However, when considering the balance of hole and electron transport, if holes from the anode do not recombine When the primary role is to efficiently prevent electrons from flowing to the cathode side, the electron transport capacity is Even if not extremely high, the effect of improving luminescence efficiency is equivalent to that of materials with high electron transport capabilities. Therefore, the electron injection / transport layer in this embodiment can efficiently block the movement of holes. The functions of the layer may also be included.

[0334] The material used to form the electron transport layer 106 or the electron injection layer 107 (electron transport material) is: Compounds that have been conventionally used as electron transfer compounds in photoconductive materials, organic EL elements From among known compounds used in the electron injection layer and electron transport layer, any one compound may be selected and used. It is possible. In this invention, the electron transport material is the above general formula (1A) or one A polycyclic aromatic compound represented by general formula (1B) can be used.

[0335] Materials used in electron transport layers or electron injection layers include carbon, hydrogen, oxygen, sulfur, and kerosene. Aromatic rings or heteroaromatic compounds composed of one or more atoms selected from inium and phosphorus. Compounds consisting of rings, pyrrole derivatives and their fused ring derivatives, and compounds having electron-accepting nitrogen It is preferable to include at least one selected from among the metal complexes. Specifically, Phthalene, anthracene and other condensed ring aromatic ring derivatives, 4,4'-bis(diphenyl) Styryl aromatic ring derivatives, such as tenyl biphenyl, perinone derivatives, and coumarins. Derivatives, naphthalimide derivatives, quinone derivatives such as anthraquinone and diphenoquinone, Examples include phosphorus oxide derivatives, carbazole derivatives, and indole derivatives. Examples of metal complexes having electron-accepting nitrogen include hydroxyphenyloxazole complexes. Hydroxyazole complexes, azomethine complexes, tropolone metal complexes, flavonols, etc. Examples include metal complexes and benzoquinoline metal complexes. These materials can be used individually. However, it is acceptable to use it mixed with other materials.

[0336] Furthermore, specific examples of other electron transfer compounds include pyridine derivatives, naphthalene derivatives, and ammonium compounds. Tracene derivatives, phenanthroline derivatives, perinone derivatives, coumarin derivatives, naphthalene Imide derivatives, anthraquinone derivatives, diphenoquinone derivatives, diphenylquinone derivatives , perylene derivatives, oxadiazole derivatives (1,3-bis[(4-t-butylphenyl (e.g., 1,3,4-oxadiazolyl]phenylene), thiophene derivatives, triazoles Derivatives (such as N-naphthyl-2,5-diphenyl-1,3,4-triazole), thiadi Azole derivatives, oxine derivative metal complexes, quinolinol-based metal complexes, quinoxaline derivatives Conductors, quinoxaline derivative polymers, benzazole compounds, gallium complexes, pyrazole phenylene derivatives, perfluorinated phenylene derivatives, triazine derivatives, pyrazine derivatives, benzyl derivatives Zoquinoline derivative (2,2'-bis(benzo[h]quinoline-2-yl)-9,9'-s Pyrobifluorene, imidazopyridine derivatives, borane derivatives, benzimidazole Derivatives (such as tris(N-phenylbenzimidazole-2-yl)benzene), benzo Oxazole derivatives, benzothiazole derivatives, quinoline derivatives, terpyridine, etc. Ligopyridine derivatives, bipyridine derivatives, terpyridine derivatives (1,3-bis(2,2' :6',2"-terpyridin-4'-yl)benzene, etc., naphthyridine derivatives (bis (1-Naphthyl)-4-(1,8-Naphthyridine-2-yl)phenylphosphine oxa (e.g., iodides), aldazine derivatives, carbazole derivatives, indole derivatives, phosphine derivatives Examples include kinase derivatives and bis-styryl derivatives.

[0337] Furthermore, metal complexes containing electron-accepting nitrogen can also be used, for example, quinolinol-based Metal complexes and hydroxyazole complexes such as hydroxyphenyloxazole complexes, azometh Tin complexes, tropolone metal complexes, flavonol metal complexes and benzoquinoline metal complexes These are some examples.

[0338] The materials mentioned above can be used individually, but they can also be used in combination with other materials.

[0339] Among the materials mentioned above, borane derivatives, pyridine derivatives, fluorantene derivatives, BO System derivatives, anthracene derivatives, benzofluorene derivatives, phosphine oxide derivatives Pyrimidine derivatives, carbazole derivatives, triazine derivatives, benzimidazole derivatives The isomer, phenanthroline derivatives, and quinolinol-based metal complexes are preferred.

[0340] <Bolan derivatives> Borane derivatives are compounds represented by the following general formula (ETM-1), for example, and in detail... This is disclosed in Japanese Patent Publication No. 2007-27587. [ka] In the above formula (ETM-1), R 11 and R 12 These are, independently, hydrogen and alkyl. cycloalkyl, optionally substituted aryl, substituted silyl, substituted It may be a nitrogen-containing heterocycle, or at least one cyano, and R 13 ~R 16 teeth, Each independently may be a substituted alkyl group or a substituted cycloalkyl group. X is an aryl or may be substituted, and X is an aryl or may be substituted. Y is an aryl with 16 or fewer carbon atoms, which may be substituted, or a substituted boryl. , or substituted carbazolyl, and n is independently 0~ It is an integer of 3. Also, substitutions in cases where "substitution is permitted" or "substitution has been performed". Examples of the groups include aryl, heteroaryl, alkyl, or cycloalkyl groups. ru.

[0341] Among the compounds represented by the above general formula (ETM-1), the following general formula (ETM-1-1) Compounds represented by the formula shown below or compounds represented by the general formula (ETM-1-2) are preferred. [ka] In formula (ETM-1-1), R 11 and R 12 These are, independently, hydrogen and alkyl. cycloalkyl, optionally substituted aryl, substituted silyl, substituted It may be a nitrogen-containing heterocycle, or at least one cyano, and R 13 ~R 16 teeth, Each independently may be a substituted alkyl group or a substituted cycloalkyl group. R is an aryl or may be substituted with R 21 and R 22 They are independent of each other. hydrogen, alkyl, cycloalkyl, optionally substituted aryl, substituted At least one of a silyl, an optionally substituted nitrogen-containing heterocycle, or a cyano, X 1 is an arylene with 20 or fewer carbon atoms, which may be substituted, and n is independently The integers are 0 to 3, and each of the integers m is independently an integer between 0 and 4. Substituents that may be replaced or are replaced include aryl and heteronucleotides. Examples include loaryl, alkyl, and cycloalkyl compounds. [ka] In formula (ETM-1-2), R 11 and R 12 These are, independently, hydrogen and alkyl. cycloalkyl, optionally substituted aryl, substituted silyl, substituted It may be a nitrogen-containing heterocycle, or at least one cyano, and R 13 ~R 16 teeth, Each independently may be a substituted alkyl group or a substituted cycloalkyl group. It is an aryl that may be replaced by X 1 This may be a carbon-2 substituted The numbers are all arrines less than or equal to 0, and each n is an independent integer between 0 and 3. Substituents that may be substituted or are substituted include aryl substituents. Examples include heteroaryl, alkyl, and cycloalkyl compounds.

[0342] X 1 A specific example of this is a 2 expressed by any of the following equations (X-1) to (X-9). The valence base is listed. The asterisk (*) in each structural formula indicates a bond position. [ka] (In each formula, R a Each is independently an alkyl group, a cycloalkyl group, or substituted. (It is a suitable phenyl group.)

[0343] Specific examples of these borane derivatives include the following compounds. [ka]

[0344] This borane derivative can be produced using known raw materials and known synthesis methods.

[0345] <Pyridine derivatives> The pyridine derivative is, for example, a compound represented by the following formula (ETM-2), and is preferably It is a compound represented by formula (ETM-2-1) or formula (ETM-2-2). [ka]

[0346] φ is an n-valent aryl ring (preferably an n-valent benzene ring, naphthalene ring, or anthracene ring). ring, fluorene ring, benzofluorene ring, phenalene ring, phenanthrene ring or truffle It is an énylene ring, and n is an integer from 1 to 4.

[0347] In the above formula (ETM-2-1), R 11 ~R 18 These are, independently, hydrogen and A Lukyl (preferably alkyl with 1 to 24 carbon atoms), cycloalkyl (preferably with 3 carbon atoms) (~12 cycloalkyls) or aryls (preferably aryls with 6 to 30 carbon atoms) ru.

[0348] In the above formula (ETM-2-2), R 11 and R 12 Each of them independently, hydrogen , alkyl (preferably alkyl with 1 to 24 carbon atoms), cycloalkyl (preferably carbon Cycloalkyls (3 to 12 carbon atoms) or aryls (preferably aryls with 6 to 30 carbon atoms) And R 11 and R 12 They may be joined together to form a ring.

[0349] In each formula, the "pyridine substituent" is one of the following: (Py-1) to (Py-15) The pyridine substituents are either C1-C4 alkyl groups or carbon groups. It may be substituted with cycloalkyl groups of 5 to 10. Also, pyridine substituents may be phenyl Bonding to the φ, anthracene ring, or fluorene ring in each formula via a ylene group or naphthylene group. They may be combined. * in each structural formula indicates a bond position.

[0350] [ka]

[0351] The pyridine substituent is one of the above formulas (Py-1) to (Py-15), however Among these, it is preferable that it be one of the following equations (Py-21) to (Py-44). The asterisk (*) in each structural formula indicates a bond position. [ka]

[0352] At least one hydrogen atom in each pyridine derivative may be substituted with deuterium, Furthermore, the two "pyridine-based" compounds in the above formulas (ETM-2-1) and (ETM-2-2) One of the substituents may be replaced with an aryl group.

[0353] R 11 ~R 18 In this context, "alkyl" can be either a straight chain or a branched chain. Examples include linear alkyl groups with 1 to 24 carbon atoms or branched alkyl groups with 3 to 24 carbon atoms. The preferred "alkyl" is an alkyl group with 1 to 18 carbon atoms (a branched-chain alkyl group with 3 to 18 carbon atoms). A more preferred "alkyl" is an alkyl group with 1 to 12 carbon atoms (3 to 12 carbon atoms). It is a branched alkyl group with 12 carbon atoms. A more preferred alkyl group is an alkyl group with 1 to 6 carbon atoms. It is a branched alkyl group (with 3 to 6 carbon atoms). Particularly preferred alkyl groups have 1 to 6 carbon atoms. It is a 4-C1 alkyl group (a branched alkyl group with 3 to 4 carbon atoms).

[0354] Specific examples of "alkyl" include methyl, ethyl, n-propyl, isopropyl, n- Butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopen Tyl, t-pentyl (t-amyl), n-hexyl, 1-methylpentyl, 4-methyl- 2-Pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methyl Hexyl, n-octyl, t-octyl (1,1,3,3-tetramethylbutyl), 1- Methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-di Methylheptyl, 2,6-dimethyl-4-heptyl, 3,5,5-trimethylhexyl, n-decyl, n-undecyl, 1-methyldecyl, n-dodecyl, n-tridecyl, 1- Hexylheptyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptyl Examples include tadecyl, n-octadecyl, and n-eicosyl. Also, for example, 1-ethyl-1-methylpropyl, 1,1-diethylpropyl, 1,1 -dimethylbutyl, 1-ethyl-1-methylbutyl, 1,1,4-trimethylpentyl, 1,1,2-trimethylpropyl, 1,1-dimethyloctyl, 1,1-dimethylpentyl 1,1-dimethylheptyl, 1,1,5-trimethylhexyl, 1-ethyl-1-methyl Tylhexyl, 1-ethyl-1,3-dimethylbutyl, 1,1,2,2-tetramethylbutyl Ropil, 1-butyl-1-methylpentyl, 1,1-diethylbutyl, 1-ethyl-1- Methylpentyl, 1,1,3-trimethylbutyl, 1-propyl-1-methylpentyl, 1,1,2-trimethylpropyl, 1-ethyl-1,2,2-trimethylpropyl, 1- Examples include propyl-1-methylbutyl and 1,1-dimethylhexyl.

[0355] For alkyl groups with 1 to 4 carbon atoms to be substituted for pyridine substituents, see the above explanation of alkyl groups. It can be quoted.

[0356] R 11 ~R 18 Examples of "cycloalkyl" in this context include cycloalkyl groups with 3 to 12 carbon atoms. Examples include cycloalkyl groups. Preferred "cycloalkyl" groups are cycloalkyl groups with 3 to 10 carbon atoms. It is a kill. A more preferred "cycloalkyl" is a cycloalkyl with 3 to 8 carbon atoms. A more preferred "cycloalkyl" is a cycloalkyl group having 3 to 6 carbon atoms. Specific examples of "cycloalkyl" include cyclopropyl, cyclobutyl, and cyclopentyl , cyclohexyl, methylcyclopentyl, cycloheptyl, methylcyclohexyl, Examples include cyclooctyl or dimethylcyclohexyl.

[0357] As for cycloalkyl groups with 5 to 10 carbon atoms to be substituted with pyridine substituents, the above cycloalkyl group We can quote Lukil's explanation.

[0358] R 11 ~R 18 In this context, preferred aryls are those with 6 to 30 carbon atoms. It is an aryl, and more preferably an aryl with 6 to 18 carbon atoms, and even more preferably More preferably, an aryl compound having 6 to 14 carbon atoms, and particularly preferably an aryl compound having 6 to 12 carbon atoms. ru.

[0359] Specific examples of "aryls with 6 to 30 carbon atoms" include monocyclic aryls such as phenyl and fuzzy aryls. (1-,2-)naphthyl is a bicyclic aryl compound, and asenaphthyl is a tricyclic aryl compound. Chilen-(1-,3-,4-,5-)yl, Fluorene-(1-,2-,3-,4-,9 -) yl, phenalene-(1-,2-) yl, (1-,2-,3-,4-,9-) phenalene Triphenylene-(1-,2-)yl, pyrene-( 1-,2-,4-)yl, naphthacene-(1-,2-,5-)yl, condensed pentacyclic aryl Perylene-(1-,2-,3-)yl, pentasene-(1-,2-,5-,6-) Examples include Il.

[0360] Preferred "aryls with 6 to 30 carbon atoms" include phenyl, naphthyl, phenanthryl, and cyanoacrylate. Examples include lysenyl or triphenylenyl, and more preferably phenyl, 1-naphthol. Examples include phenyl, 2-naphthyl, or phenanthryl, with phenyl, 1-naphthyl being particularly preferred. Phthyl or 2-naphthyl are examples.

[0361] In the above formula (ETM-2-2), R 11 and R 12 Even if they are bonded together to form a ring Often, as a result, the five-membered ring of the fluorene skeleton contains cyclobutane, cyclopentane, and cyclo Pentene, cyclopentadiene, cyclohexane, fluorene, or indene are among the stimulants. It is acceptable for them to be joined together.

[0362] Specific examples of pyridine derivatives include the following compounds. [ka]

[0363] This pyridine derivative can be produced using known raw materials and known synthesis methods.

[0364] <Fluoranthene derivative> The fluoranthene derivative is, for example, a compound represented by the following general formula (ETM-3), and is specifically disclosed in International Publication No. 2010 / 134352.

Chemical formula

[0365] In the above formula (ETM-3), X 12 ~X 21 each independently represents hydrogen, halogen, linear, branched or cyclic alkyl, linear, branched or cyclic alkoxy, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl. Here, when substituted, the substituents include aryl, heteroaryl, alkyl or cycloalkyl, etc. . <0004,900><00049,01><00049,02>Specific examples of this fluoranthene derivative include, for example, the following compounds. <00049,03><00049,04>

Chemical formula

Chemical formula

[0369] Also, R 1 ~R 11 Among them, adjacent groups bond together to form ring a, b, or c. They may form a reel ring or a heteroaryl ring, and in the formed ring, Another hydrogen atom is aryl, heteroaryl, diarylamino, and diheteroarylamino. aryl heteroarylamino, diarylboryl (the two aryls are single-bonded or linked) Alkyl, cycloalkyl, alkoxy, and aryl groups (which may be linked via a binder). They may be substituted with oxy or substituted silyl, and at least one of these substituents One hydrogen is substituted with an aryl, heteroaryl, alkyl, or cycloalkyl group. That's good too.

[0370] Furthermore, at least one hydrogen in the compound or structure represented by formula (ETM-4) It may be substituted with a halogen or deuterium.

[0371] The substituents and ring formation morphology in formula (ETM-4), and the structure of formula (ETM-4) are multiple. For an explanation of the polymers formed by the combination, see the general formula (1A) or general formula (1B) above. The description of the polycyclic aromatic compound can be cited.

[0372] Specific examples of these BO derivatives include the following compounds. [ka]

[0373] This BO derivative can be produced using known raw materials and known synthesis methods.

[0374] <Anthracene derivatives> One anthracene derivative is, for example, the compound represented by the following formula (ETM-5-1). ru. [ka]

[0375] Ar is independently either divalent benzene or naphthalene, and R 1 ~R 4 teeth, Each independently consists of hydrogen, a C1-C6 alkyl group, a C3-C6 cycloalkyl group, and These are aryl atoms with 6 to 20 carbon atoms.

[0376] Ar can be independently selected from divalent benzene or naphthalene as appropriate. The two Ar atoms may be different or the same, but the synthesis of anthracene derivatives From the standpoint of ease, it is preferable that they be the same. Ar combines with pyridine to form "Ar and It forms a "part consisting of bipyridine," and this part is, for example, the following formula (Py-1) ~ formula ( It is attached to anthracene as a group represented by one of the following in each structural formula: * indicates the connection position.

[0377] [ka]

[0378] Among these groups, the group represented by any of the above formulas (Py-1) to (Py-9) is Preferably, a group represented by any of the above formulas (Py-1) to (Py-6) is preferred. The two "Ar and pyridine moieties" that bind to anthracene have the same structure. They may be the same or different, but from the viewpoint of the ease of synthesis of anthracene derivatives, they are the same. It is preferable that the structure be the same. However, from the viewpoint of device characteristics, two "Ar and pyramidal" The structure of the "part consisting of din" is preferable whether it is the same or different.

[0379] R 1 ~R 4 For alkyl groups with 1 to 6 carbon atoms, both linear and branched chains are used. Good. That is, a linear alkyl group with 1 to 6 carbon atoms or a branched alkyl group with 3 to 6 carbon atoms. More preferably, an alkyl group having 1 to 4 carbon atoms (a branched alkyl group having 3 to 4 carbon atoms). Specific examples include methyl, ethyl, n-propyl, isopropyl, n-butyl, and isopropyl. butyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl Tyl(t-amyl), n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl, Examples include 3,3-dimethylbutyl or 2-ethylbutyl, and methyl, ethyl, n -Propyl, isopropyl, n-butyl, isobutyl, s-butyl, or t-butyl Preferably, methyl, ethyl, or t-butyl is preferred.

[0380] R 1 ~R 4 A specific example of a cycloalkyl group with 3 to 6 carbon atoms is cyclopropyl Cyclobutyl, cyclopentyl, cyclohexyl, methylcyclopentyl, cyclohexyl Examples include methylcyclohexyl, cyclooctyl, or dimethylcyclohexyl. It is possible.

[0381] R 1 ~R 4 Regarding aryls with 6 to 20 carbon atoms, the aryls with 6 to 16 carbon atoms are... A C6-C12 aryl is preferred, a C6-C10 aryl is particularly preferred. It is preferable.

[0382] Specific examples of "aryls with 6 to 20 carbon atoms" include monocyclic aryls such as phenyl, ( o-,m-,p-) trill, (2,3-,2,4-,2,5-,2,6-,3,4-,3 ,5-)xylyl, mesityl(2,4,6-trimethylphenyl), (o-,m-,p- )Cumenyl, a bicyclic aryl (2-,3-,4-)biphenylyl, a condensed bicyclic aryl (1-,2-)naphthyl is a aryl compound, and terpheniryl (m-terphthyl) is a tricyclic aryl compound. Enyl-2'-yl, m-terphenyl-4'-yl, m-terphenyl-5'-yl, o-terphenyl-3'-yl, o-terphenyl-4'-yl, p-terphenyl-2 '-yl, m-terphenyl-2-yl, m-terphenyl-3-yl, m-terphenyl Lu-4-yl, o-terphenyl-2-yl, o-terphenyl-3-yl, o-terf Phenyl-4-yl, p-terphenyl-2-yl, p-terphenyl-3-yl, p-terphenyl Anthracene-(1-,2-,9) is a condensed tricyclic aryl compound. -)yl, asenaphthylene-(1-,3-,4-,5-)yl, fluorene-(1-,2 -,3-,4-,9-)il, phenalene-(1-,2-)il, (1-,2-,3-, 4-,9-)phenanthryl, a condensed tetracyclic aryl triphenylene-(1-,2- )yl, pyren-(1-,2-,4-)yl, tetracene-(1-,2-,5-)yl, Examples include perylene-(1-,2-,3-)yl, a condensed pentacyclic aryl.

[0383] Preferred "aryl compounds with 6 to 20 carbon atoms" include phenyl, biphenylyl, and terphenylyl. or naphthyl, more preferably phenyl, biphenylyl, 1-naphthyl, 2- Naphthyl or m-terphenyl-5'-yl, more preferably phenyl, bian The material is phenylyl, 1-naphthyl, or 2-naphthyl, most preferably phenyl.

[0384] One anthracene derivative is, for example, the compound represented by the following formula (ETM-5-2). ru. [ka]

[0385] Ar 1 These are, independently, single bonds, divalent benzene, naphthalene, anthracene, It is either fluorene or phenalene.

[0386] Ar 2 Each of these is an aryl group with 6 to 20 carbon atoms, and the above formula (ETM-5 The same explanation as in -1) for "aryls with 6 to 20 carbon atoms" can be cited. aryls with 6 to 16 carbon atoms are preferred, aryls with 6 to 12 carbon atoms are more preferred, and aryls with 6 carbon atoms are preferred. Aryl compounds of ~10 are particularly preferred. Specific examples include phenyl, biphenylyl, and naphthyl. terpheniryl, anthracenyl, acenaphtyrenyl, fluorenyl, phenalenyl, Examples include phenanthryl, triphenylenyl, pyrenyl, tetracenyl, and perirenyl. It can be done.

[0387] R 1 ~R 4 These are, independently, hydrogen, alkyl groups with 1 to 6 carbon atoms, and alkyl groups with 3 to 6 carbon atoms. It is a chloroalkyl or an aryl with 6 to 20 carbon atoms, and in the above formula (ETM-5-1) You can quote the following explanation.

[0388] Specific examples of these anthracene derivatives include the following compounds: [ka]

[0389] These anthracene derivatives can be produced using known raw materials and known synthesis methods. Cut.

[0390] <Benzofluorene derivatives> Benzofluorene derivatives are compounds represented by the following formula (ETM-6), for example. [ka]

[0391] Ar 1 Each of these is an aryl group with 6 to 20 carbon atoms, and the above formula (ETM-5 The same explanation as in -1) for "aryls with 6 to 20 carbon atoms" can be cited. aryls with 6 to 16 carbon atoms are preferred, aryls with 6 to 12 carbon atoms are more preferred, and aryls with 6 carbon atoms are preferred. Aryl compounds of ~10 are particularly preferred. Specific examples include phenyl, biphenylyl, and naphthyl. terpheniryl, anthracenyl, acenaphtyrenyl, fluorenyl, phenalenyl, Examples include phenanthryl, triphenylenyl, pyrenyl, tetracenyl, and perirenyl. It can be done.

[0392] Ar 2 These are, independently, hydrogen and alkyl (preferably alkyl having 1 to 24 carbon atoms). ), cycloalkyl (preferably cycloalkyl with 3 to 12 carbon atoms) or aryl (preferably The most common aryl group has 6 to 30 carbon atoms, and consists of two Ar 2 They are joined together to form a ring. That's good too.

[0393] Ar 2 The "alkyl" in this context can be either a linear or branched chain, for example, Examples include linear alkyl groups with 1 to 24 carbon atoms or branched alkyl groups with 3 to 24 carbon atoms. The term "alkyl" refers to alkyl groups with 1 to 18 carbon atoms (branched-chain alkyl groups with 3 to 18 carbon atoms). Therefore, a more preferred "alkyl" is an alkyl group with 1 to 12 carbon atoms (a fraction of which has 3 to 12 carbon atoms). It is a branched alkyl group. A more preferred "alkyl" is an alkyl group with 1 to 6 carbon atoms (carbon It is a branched alkyl group with 3 to 6 carbon atoms. Particularly preferred alkyl groups are those with 1 to 4 carbon atoms. It is a branched alkyl group (with 3-4 carbon atoms). A specific example of "alkyl" is methyl. ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl til, n-pentyl, isopentyl, neopentyl, t-pentyl (t-amyl), n- Hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, Examples include 2-ethylbutyl, n-heptyl, and 1-methylhexyl.

[0394] Ar 2 In this context, "cycloalkyl" refers to, for example, cycloalkyl groups with 3 to 12 carbon atoms. Examples include: A preferred "cycloalkyl" is a cycloalkyl with 3 to 10 carbon atoms. A more preferred "cycloalkyl" is a cycloalkyl with 3 to 8 carbon atoms. Preferred "cycloalkyl" is a cycloalkyl with 3 to 6 carbon atoms. Examples of "roalkyl" include cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl Methylcyclopentyl, cycloheptyl, methylcyclohexyl, cyclooctyl Examples include dimethylcyclohexyl.

[0395] Ar 2 In this context, preferred aryls are those with 6 to 30 carbon atoms. A more preferred aryl is an aryl with 6 to 18 carbon atoms, and even more preferably a carbon aryl. The aryl group has 6 to 14 prime numbers, and is particularly preferably an aryl group with 6 to 12 carbon atoms.

[0396] Specific examples of "aryl compounds with 6 to 30 carbon atoms" include phenyl, naphthyl, and acenaphthyl Nyl, fluorenyl, phenalenyl, phenanthryl, triphenylenyl, pyrenyl, na Examples include phthalocenyl, perirenyl, and pentacenyl.

[0397] Two Ar 2 These may be bonded together to form a ring, resulting in a five-membered ring of the fluorene skeleton. It contains cyclobutane, cyclopentane, cyclopentene, cyclopentadiene, and cyclohexane. Xane, fluorene, or indene may be spirolinked to it.

[0398] Specific examples of these benzofluorene derivatives include the following compounds: [ka]

[0399] This benzofluorene derivative can be produced using known raw materials and known synthesis methods. Cut.

[0400] <Phosphine oxide derivatives> Phosphine oxide derivatives are compounds represented by the following formula (ETM-7-1), for example. Yes, it exists. Further details are also described in International Publication No. 2013 / 079217. [ka] R 5 These are substituted or unsubstituted alkyl groups with 1 to 20 carbon atoms, and cycloa groups with 3 to 20 carbon atoms. Lukyl is an aryl or heteroaryl with 6 to 20 carbon atoms. R 6 CN, substituted or unsubstituted alkyl groups with 1 to 20 carbon atoms, and 3 to 20 carbon atoms. Chloalkyl, heteroalkyl with 1-20 carbon atoms, aryl with 6-20 carbon atoms, 5 carbon atoms ~20 heteroaryls, alkoxys with 1-20 carbon atoms, or aryls with 6-20 carbon atoms. It is an oxy, R 7 and R 8 Each of these is independently a substituted or unsubstituted ally with 6 to 20 carbon atoms. It is a heteroaryl with 5 to 20 carbon atoms. R 9 It is oxygen or sulfur, j is 0 or 1, k is 0 or 1, r is an integer from 0 to 4, and q is an integer from 1 to 3 It is an integer. In this case, the substituents that are substituted are aryl, heteroaryl, and alkyl. Other examples include cycloalkyl groups.

[0401] Phosphine oxide derivatives are compounds represented by the following formula (ETM-7-2), for example. That's good too. [ka]

[0402] R 1 ~R 3 They may be the same or different, and include hydrogen, alkyl groups, cycloalkyl groups, Aralkyl group, alkenyl group, cycloalkenyl group, alkynyl group, alkoxy group, alkyl group Kilthio group, cycloalkylthio group, aryl ether group, arylthioether group, A Lille group, heterocyclic group, halogen, cyano group, aldehyde group, carbonyl group, carboxyl Among the condensed rings formed between the amino group, nitro group, silyl group, and adjacent substituents They were selected.

[0403] Ar 1 These may be the same or different, and are either an arylene group or a heteroarylene group. Ar 2 These may be the same or different, and are either an aryl group or a heteroaryl group. However, Ar 1 and Ar 2 At least one of them has a substituent, or adjacent A fused ring is formed between the substituent and the compound. n is an integer from 0 to 3, and when n is 0, it is unsaturated. There are no structural parts, and when n is 3, R 1 It does not exist.

[0404] Among these substituents, alkyl groups include, for example, methyl, ethyl, propyl, and b This group exhibits saturated aliphatic hydrocarbon groups such as til groups, and these can be unsubstituted or substituted. There are no particular restrictions on the substituents when substituted; for example, alkyl groups, aryl groups. Examples include heterocyclic groups, and this point is also common to the following description. Furthermore, alkyl groups are also included. The number of carbon atoms in the base is not particularly limited, but due to availability and cost considerations, it is usually in the range of 1 to 20. It is enclosed.

[0405] Furthermore, cycloalkyl groups include, for example, cyclopropyl, cyclohexyl, norbornyl. It exhibits saturated alicyclic hydrocarbon groups such as ru and adamantyl, which are either unsubstituted or substituted. That's fine. The number of carbon atoms in the alkyl group is not particularly limited, but is usually in the range of 3 to 20. be.

[0406] Furthermore, aralkyl groups are aliphatic carbonized groups such as benzyl groups and phenylethyl groups. It shows an aromatic hydrocarbon group via an element, and both aliphatic hydrocarbons and aromatic hydrocarbons are unsubstituted. However, substitution is acceptable. The number of carbon atoms in the aliphatic portion is not particularly limited, but is usually 1. The range is ~20.

[0407] Furthermore, alkenyl groups are double bonds such as vinyl groups, allyl groups, and butadienyl groups. This represents an unsaturated aliphatic hydrocarbon group containing a compound, which may be unsubstituted or substituted. The number of carbon atoms in the alkenyl group is not particularly limited, but is usually in the range of 2 to 20.

[0408] Furthermore, cycloalkenyl groups include, for example, cyclopentenyl and cyclopentadienyl groups. It shows an unsaturated alicyclic hydrocarbon group containing a double bond, such as a cyclohexene group, and this is ostagmoid. It doesn't matter whether it's a substitution or a replacement.

[0409] Furthermore, an alkynyl group is an unsaturated aliphatic group containing a triple bond, such as an acetylenyl group. This represents a hydrocarbon group, which may be unsubstituted or substituted. The carbon of the alkynyl group. The number is not particularly limited, but it is usually in the range of 2 to 20.

[0410] Furthermore, alkoxy groups are, for example, aliphatic carbon groups that undergo ether bonding. It represents a hydrogen group, and the aliphatic hydrocarbon group may be unsubstituted or substituted. The number of carbon atoms in the group is not particularly limited, but it is usually in the range of 1 to 20.

[0411] Furthermore, an alkylthio group is defined as a group in which the oxygen atom in the ether bond of an alkoxy group is replaced by a sulfur atom. It is the basis.

[0412] Furthermore, a cycloalkylthio group is a group in which the oxygen atom of the ether bond of a cycloalkoxy group is sulfur It is a group substituted with a yellow atom.

[0413] Furthermore, aryl ether groups are aromatic compounds that are linked to ether bonds, such as phenoxy groups. It represents a fragrant hydrocarbon group, and the aromatic hydrocarbon group may be unsubstituted or substituted. The number of carbon atoms in the reel ether group is not particularly limited, but is usually in the range of 6 to 40.

[0414] Furthermore, an arylthioether group is defined as the oxygen atom of the ether bond of an aryl ether group. It is a group substituted with a sulfur atom.

[0415] Furthermore, aryl groups include, for example, phenyl, naphthyl, biphenyl, and phenant groups. This refers to aromatic hydrocarbon groups such as lyl groups, terphenyl groups, and pyrenyl groups. Aryl groups are absent. Substitution or substituted is acceptable. The number of carbon atoms in the aryl group is not particularly limited, but usually The range is 6 to 40.

[0416] Furthermore, heterocyclic groups include, for example, furanyl groups, thiophenyl groups, oxazolyl groups, and pyridyl groups. It shows cyclic structural groups having atoms other than carbon, such as a quinolinyl group and a carbazolyl group. This can be unsubstituted or substituted. The number of carbon atoms in the heterocyclic group is not particularly limited. The range is usually between 20 and 30.

[0417] Halogens refer to fluorine, chlorine, bromine, and iodine.

[0418] Aldehyde groups, carbonyl groups, and amino groups include aliphatic hydrocarbons, alicyclic hydrocarbons, and aromatic compounds. Groups substituted with cyclic hydrocarbons, heterocyclic rings, etc., can also be included.

[0419] Furthermore, aliphatic hydrocarbons, alicyclic hydrocarbons, aromatic hydrocarbons, and heterocyclic hydrocarbons can be substituted even if they are unsubstituted. It's okay if it's included.

[0420] A silyl group refers to a silicon compound group such as a trimethylsilyl group, and this is an unassigned group. It can be either a substitution or a substitution. The number of carbon atoms in the silyl group is not particularly limited, but usually it is 3. The range is ~20. Also, the silicon number is usually between 1 and 6.

[0421] The fused ring formed between adjacent substituents is, for example, Ar 1 and R 2 Ar 1 and R 3 , A r 2 and R 2 Ar 2 and R 3 , R 2 and R 3 Ar 1 and Ar 2 Conjugation or It is a non-conjugated fused ring. Here, when n is 1, there are two R 1 Contraction of conjugate or non-conjugate terms between two entities. They may form fused rings. These fused rings contain nitrogen, oxygen, and sulfur atoms in their intraring structure. Alternatively, it may be fused with another ring.

[0422] Specific examples of these phosphine oxide derivatives include the following compounds: . [ka]

[0423] This phosphine oxide derivative is manufactured using known raw materials and known synthesis methods. It is possible.

[0424] <Pyrimidine derivatives> The pyrimidine derivative is, for example, a compound represented by the following formula (ETM-8), and is preferably This compound is represented by the following formula (ETM-8-1). For details, see International Publication No. 2011 / 021689. It is also stated in the official gazette. [ka]

[0425] Each Ar is an aryl that may be substituted, or may be substituted. It is a good heteroaryl. n is an integer from 1 to 4, preferably an integer from 1 to 3. More preferably, 2 or 3.

[0426] Examples of "aryls that may be substituted" include those with 6 to 30 carbon atoms. Examples include aryls, preferably aryls having 6 to 24 carbon atoms, more preferably aryls having 6 carbon atoms. ~20 aryl atoms, more preferably aryl atoms with 6 to 12 carbon atoms.

[0427] Specific examples of "aryl" include monocyclic aryls such as phenyl and bicyclic aryls. (2-,3-,4-)biphenylyl is a condensed bicyclic aryl (1-,2-)naphthyl The tricyclic aryl terpheniryl (m-terphenyl-2'-yl, m-terf) phenyl-4'-yl, m-terphenyl-5'-yl, o-terphenyl-3'-yl, o-terphenyl-4'-yl, p-terphenyl-2'-yl, m-terphenyl-2 -yl, m-terphenyl-3-yl, m-terphenyl-4-yl, o-terphenyl -2-yl, o-terphenyl-3-yl, o-terphenyl-4-yl, p-terphenyl (Nyl-2-yl, p-terphenyl-3-yl, p-terphenyl-4-yl), condensed tri The cyclic aryl is acenaphthylene-(1-,3-,4-,5-)yl, fluorene- (1-,2-,3-,4-,9-) yl, phenalene-(1-,2-) yl, (1-,2 -,3-,4-,9-)phenanthryl, tetracyclic aryl quaterpheniryl (5 '-phenyl-m-terphenyl-2-yl, 5'-phenyl-m-terphenyl-3- Il, 5'-phenyl-m-terphenyl-4-yl, m-quaterphenylyl), condensation The tetracyclic aryls are triphenylene-(1-,2-)yl and pyrene-(1-,2-,4 -)yl, naphthasen-(1-,2-,5-)yl, and perylene, a condensed pentacyclic aryl system. Examples include -(1-,2-,3-)il and pentase-(1-,2-,5-,6-)il. It is possible.

[0428] Examples of "heteroaryls that may be substituted" include carbon Examples include heteroaryl compounds with 2 to 30 prime numbers, with heteroaryl compounds having 2 to 25 carbon atoms being preferred. Heteroaryls having 2 to 20 carbon atoms are more preferred, and heteroaryls having 2 to 15 carbon atoms are preferred. More preferably, heteroaryls having 2 to 10 carbon atoms are particularly preferred. For example, the ring constituent atoms may be selected from oxygen, sulfur, and nitrogen in addition to carbon. Examples include heterocycles containing one to five ion atoms.

[0429] Specific heteroaryls include, for example, pyrrolyl, oxazolyl, and isoxazoli. Lu, thiazolyl, isothiazolyl, imidazolyl, oxadiazolyl, thiadiazolyl, Triazolyl, tetrazolyl, pyrazolyl, pyridinyl, pyrimidinyl, pyridadinyl, Pyrazinyl, triazinyl, indolyl, isoindolyl, 1H-indazolyl, benzo Imidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, ki Norinyl, Isoquinolinyl, Synnorinyl, Quinazolinyl, Quinoxalinyl, Phthalajini Lu, naphthilidinil, prinyl, pteridinil, carbazolyl, acridinil, phenoxy Satinyl, phenoxadinyl, phenothiazinyl, phenadinyl, phenazacylinyl, Indolidinyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, Naphthobenzofuranyl, thiophenyl, benzothiophenyl, dibenzothiophenyl, na Futobenzothiophenyl, benzophosphoryl, dibenzophosphoryl, benzophosphorus Monovalent group of an oxide ring, monovalent group of a dibenzophosphole oxide ring, fluzanyl, thiant Renyl, indolocarbazolyl, benzoindocarbazolyl, and benzobenzoindocarbazolyl. Examples include locarbazolil.

[0430] Furthermore, at least one hydrogen in the above aryl and heteroaryl is substituted. They may be present, and each may be substituted with, for example, the aryl or heteroaryl compounds mentioned above.

[0431] Specific examples of these pyrimidine derivatives include the following compounds. [ka]

[0432] This pyrimidine derivative can be produced using known raw materials and known synthesis methods.

[0433] <Carbazole derivatives> Carbazole derivatives include, for example, compounds represented by the following formula (ETM-9), or compounds that are... It is a polymer formed by multiple single bonds or other linkages. Further details are described in U.S. Public Publication No. 2014 / 0197386. It is being done. [ka]

[0434] Each Ar is an aryl that may be substituted, or may be substituted. It is a good heteroaryl. Each n is an independent integer between 0 and 4, preferably An integer between 0 and 3, more preferably 0 or 1.

[0435] Examples of "aryls that may be substituted" include those with 6 to 30 carbon atoms. Examples include aryls, preferably aryls having 6 to 24 carbon atoms, more preferably aryls having 6 carbon atoms. ~20 aryl atoms, more preferably aryl atoms with 6 to 12 carbon atoms.

[0436] Specific examples of "aryl" include monocyclic aryls such as phenyl and bicyclic aryls. (2-,3-,4-)biphenylyl is a condensed bicyclic aryl (1-,2-)naphthyl The tricyclic aryl terpheniryl (m-terphenyl-2'-yl, m-terf) phenyl-4'-yl, m-terphenyl-5'-yl, o-terphenyl-3'-yl, o-terphenyl-4'-yl, p-terphenyl-2'-yl, m-terphenyl-2 -yl, m-terphenyl-3-yl, m-terphenyl-4-yl, o-terphenyl -2-yl, o-terphenyl-3-yl, o-terphenyl-4-yl, p-terphenyl (Nyl-2-yl, p-terphenyl-3-yl, p-terphenyl-4-yl), condensed tri The cyclic aryl is acenaphthylene-(1-,3-,4-,5-)yl, fluorene- (1-,2-,3-,4-,9-) yl, phenalene-(1-,2-) yl, (1-,2 -,3-,4-,9-)phenanthryl, tetracyclic aryl quaterpheniryl (5 '-phenyl-m-terphenyl-2-yl, 5'-phenyl-m-terphenyl-3- Il, 5'-phenyl-m-terphenyl-4-yl, m-quaterphenylyl), condensation The tetracyclic aryls are triphenylene-(1-,2-)yl and pyrene-(1-,2-,4 -)yl, naphthasen-(1-,2-,5-)yl, and perylene, a condensed pentacyclic aryl system. Examples include -(1-,2-,3-)il and pentase-(1-,2-,5-,6-)il. It is possible.

[0437] Examples of "heteroaryls that may be substituted" include carbon Examples include heteroaryl compounds with 2 to 30 prime numbers, with heteroaryl compounds having 2 to 25 carbon atoms being preferred. Heteroaryls having 2 to 20 carbon atoms are more preferred, and heteroaryls having 2 to 15 carbon atoms are preferred. More preferably, heteroaryls having 2 to 10 carbon atoms are particularly preferred. For example, the ring constituent atoms may be selected from oxygen, sulfur, and nitrogen in addition to carbon. Examples include heterocycles containing one to five ion atoms.

[0438] Specific heteroaryls include, for example, pyrrolyl, oxazolyl, and isoxazoli. Lu, thiazolyl, isothiazolyl, imidazolyl, oxadiazolyl, thiadiazolyl, Triazolyl, tetrazolyl, pyrazolyl, pyridinyl, pyrimidinyl, pyridadinyl, Pyrazinyl, triazinyl, indolyl, isoindolyl, 1H-indazolyl, benzo Imidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, ki Norinyl, Isoquinolinyl, Synnorinyl, Quinazolinyl, Quinoxalinyl, Phthalajini Lu, naphthilidinil, prinyl, pteridinil, carbazolyl, acridinil, phenoxy Satinyl, phenoxadinyl, phenothiazinyl, phenadinyl, phenazacylinyl, Indolidinyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, Naphthobenzofuranyl, thiophenyl, benzothiophenyl, dibenzothiophenyl, na Futobenzothiophenyl, benzophosphoryl, dibenzophosphoryl, benzophosphorus Monovalent group of an oxide ring, monovalent group of a dibenzophosphole oxide ring, fluzanyl, thiant Renyl, indolocarbazolyl, benzoindocarbazolyl, and benzobenzoindocarbazolyl. Examples include locarbazolil.

[0439] Furthermore, at least one hydrogen in the above aryl and heteroaryl is substituted. They may be present, and each may be substituted with, for example, the aryl or heteroaryl compounds mentioned above.

[0440] Carbazole derivatives are compounds represented by the above formula (ETM-9) with multiple bonds such as single bonds. It may also be a combined polymer. In this case, in addition to single bonds, there may be an aryl ring (preferably a polyvalent one). Benzene ring, naphthalene ring, anthracene ring, fluorene ring, benzofluorene ring, phen They may be linked by a narene ring, a phenanthrene ring, or a triphenylene ring.

[0441] Specific examples of these carbazole derivatives include the following compounds. [ka]

[0442] This carbazole derivative can be produced using known raw materials and known synthesis methods. .

[0443] <Triadine derivatives> Triazine derivatives are, for example, compounds represented by the following formula (ETM-10), and are preferred. The compound is represented by the following formula (ETM-10-1). For details, see US Publication No. 2011 / 01560. It is described in Bulletin No. 13. [ka]

[0444] Each Ar is an aryl that may be substituted, or may be substituted. It is a good heteroaryl. n is an integer from 1 to 3, preferably 2 or 3.

[0445] Examples of "aryls that may be substituted" include those with 6 to 30 carbon atoms. Examples include aryls, preferably aryls having 6 to 24 carbon atoms, more preferably aryls having 6 carbon atoms. ~20 aryl atoms, more preferably aryl atoms with 6 to 12 carbon atoms.

[0446] Specific examples of "aryl" include monocyclic aryls such as phenyl and bicyclic aryls. (2-,3-,4-)biphenylyl is a condensed bicyclic aryl (1-,2-)naphthyl The tricyclic aryl terpheniryl (m-terphenyl-2'-yl, m-terf) phenyl-4'-yl, m-terphenyl-5'-yl, o-terphenyl-3'-yl, o-terphenyl-4'-yl, p-terphenyl-2'-yl, m-terphenyl-2 -yl, m-terphenyl-3-yl, m-terphenyl-4-yl, o-terphenyl -2-yl, o-terphenyl-3-yl, o-terphenyl-4-yl, p-terphenyl (Nyl-2-yl, p-terphenyl-3-yl, p-terphenyl-4-yl), condensed tri The cyclic aryl is acenaphthylene-(1-,3-,4-,5-)yl, fluorene- (1-,2-,3-,4-,9-) yl, phenalene-(1-,2-) yl, (1-,2 -,3-,4-,9-)phenanthryl, tetracyclic aryl quaterpheniryl (5 '-phenyl-m-terphenyl-2-yl, 5'-phenyl-m-terphenyl-3- Il, 5'-phenyl-m-terphenyl-4-yl, m-quaterphenylyl), condensation The tetracyclic aryls are triphenylene-(1-,2-)yl and pyrene-(1-,2-,4 -)yl, naphthasen-(1-,2-,5-)yl, and perylene, a condensed pentacyclic aryl system. Examples include -(1-,2-,3-)il and pentase-(1-,2-,5-,6-)il. It is possible.

[0447] Examples of "heteroaryls that may be substituted" include carbon Examples include heteroaryl compounds with 2 to 30 prime numbers, with heteroaryl compounds having 2 to 25 carbon atoms being preferred. Heteroaryls having 2 to 20 carbon atoms are more preferred, and heteroaryls having 2 to 15 carbon atoms are preferred. More preferably, heteroaryls having 2 to 10 carbon atoms are particularly preferred. For example, the ring constituent atoms may be selected from oxygen, sulfur, and nitrogen in addition to carbon. Examples include heterocycles containing one to five ion atoms.

[0448] Specific heteroaryls include, for example, pyrrolyl, oxazolyl, and isoxazoli. Lu, thiazolyl, isothiazolyl, imidazolyl, oxadiazolyl, thiadiazolyl, Triazolyl, tetrazolyl, pyrazolyl, pyridinyl, pyrimidinyl, pyridadinyl, Pyrazinyl, triazinyl, indolyl, isoindolyl, 1H-indazolyl, benzo Imidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, ki Norinyl, Isoquinolinyl, Synnorinyl, Quinazolinyl, Quinoxalinyl, Phthalajini Lu, naphthilidinil, prinyl, pteridinil, carbazolyl, acridinil, phenoxy Satinyl, phenoxadinyl, phenothiazinyl, phenadinyl, phenazacylinyl, Indolidinyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, Naphthobenzofuranyl, thiophenyl, benzothiophenyl, dibenzothiophenyl, na Futobenzothiophenyl, benzophosphoryl, dibenzophosphoryl, benzophosphorus Monovalent group of an oxide ring, monovalent group of a dibenzophosphole oxide ring, fluzanyl, thiant Renyl, indolocarbazolyl, benzoindocarbazolyl, and benzobenzoindocarbazolyl. Examples include locarbazolil.

[0449] Furthermore, at least one hydrogen in the above aryl and heteroaryl is substituted. They may be present, and each may be substituted with, for example, the aryl or heteroaryl compounds mentioned above.

[0450] Specific examples of these triazine derivatives include the following compounds. [ka]

[0451] This triazine derivative can be produced using known raw materials and known synthesis methods.

[0452] <Benzimidazole derivatives> Benzimidazole derivatives are compounds represented by the following formula (ETM-11), for example. . [ka]

[0453] φ is an n-valent aryl ring (preferably an n-valent benzene ring, naphthalene ring, or anthracene ring). ring, fluorene ring, benzofluorene ring, phenalene ring, phenanthrene ring or truffle It is an phenylene ring, where n is an integer from 1 to 4, and the "benzoimidazole substituent" is above The "peri" in notation (ETM-2), formula (ETM-2-1), and formula (ETM-2-2) A substituent in which the pyridyl group in the "zin-based substituent" is replaced by a benzimidazole group. In benzimidazole derivatives, at least one hydrogen atom may be substituted with deuterium. i. In the structural formulas below, * indicates a bond position. [ka]

[0454] R in the above benzimidazole group 11 It consists of hydrogen, alkyl groups with 1 to 24 carbon atoms, and carbon atoms. The above formula (ETM- 2-1) and R in equation (ETM-2-2) 11You can quote the explanation.

[0455] φ is further preferably an anthracene ring or a fluorene ring, in this case The structure can be described by referring to the explanation in the above formula (ETM-2-1) or formula (ETM-2-2). And in each equation, R 11 ~R 18 This is the above formula (ETM-2-1) or formula (ETM-2-2) The explanation can be cited. Also, the above formula (ETM-2-1) or formula (ETM- In 2-2), it is described as a form in which two pyridine substituents are bonded, but these are bent When replacing with zoimidazole substituents, replace both pyridine substituents with benzimidazole substituents. It may be replaced with a zole substituent (i.e., n=2), or any one of the pyridine substituents Replace one substitution group with a benzimidazole substituent and the other pyridine substituent with R 11 ~R 1 8 It may also be replaced with (i.e., n=1). Furthermore, for example, in the above equation (ETM-2-1) Okeru R 11 ~R 18 Replace at least one of the benzimidazole substituents to form "P "Lysine substituent" 11 ~R 18 You can replace it with this.

[0456] A specific example of this benzimidazole derivative is, for example, 1-phenyl-2-(4-( 10-phenylanthracene-9-yl)phenyl)-1H-benzo[d]imidazole , 2-(4-(10-(naphthalene-2-yl)anthracene-9-yl)phenyl)- 1-Phenyl-1H-benzo[d]imidazole, 2-(3-(10-(naphthalene-2 -yl)anthracene-9-yl)phenyl)-1-phenyl-1H-benzo[d]imi Dazole, 5-(10-(naphthalene-2-yl)anthracene-9-yl)-1,2- Diphenyl-1H-benzo[d]imidazole, 1-(4-(10-(naphthalene-2- Il)anthracene-9-yl)phenyl)-2-phenyl-1H-benzo[d]imida Zol, 2-(4-(9,10-di(naphthalene-2-yl)anthracene-2-yl) Phenyl)-1-phenyl-1H-benzo[d]imidazole, 1-(4-(9,10- Di(naphthalene-2-yl)anthracene-2-yl)phenyl)-2-phenyl-1H -Benzo[d]imidazole, 5-(9,10-di(naphthalene-2-yl)anthrace Examples include 1,2-diphenyl-1H-benzo[d]imidazole. ru. [ka]

[0457] This benzimidazole derivative can be produced using known raw materials and known synthesis methods. can.

[0458] <Phenanthroline derivatives> Phenanthroline derivatives include, for example, those of the following formula (ETM-12) or formula (ETM-12- It is the compound represented by 1). Details are described in International Publication No. 2006 / 021982. [ka]

[0459] φ is an n-valent aryl ring (preferably an n-valent benzene ring, naphthalene ring, or anthracene ring). ring, fluorene ring, benzofluorene ring, phenalene ring, phenanthrene ring or truffle It is an énylene ring, and n is an integer from 1 to 4.

[0460] R in each formula 11 ~R 18 These are, independently, hydrogen, alkyl (preferably with 1 carbon atom) 24 alkyl groups, cycloalkyl groups (preferably cycloalkyl groups with 3 to 12 carbon atoms), and is an aryl (preferably an aryl with 6 to 30 carbon atoms). Also, the above formula (ETM-1 In 2-1), R 11 ~R 18 One of these bonds with φ, which is an aryl ring.

[0461] Even if at least one hydrogen atom in each phenanthroline derivative is substituted with deuterium good.

[0462] R 11 ~R 18 The alkyl, cycloalkyl and aryl in the above formula ( R in ETM-2) 11 ~R 18 The explanation can be quoted. Also, φ is as described above. In addition to the examples above, the following structural formulas can be given as an example. Note that R in the following structural formulas represents each These are independently hydrogen, methyl, ethyl, isopropyl, cyclohexyl, phenyl, 1-na These are phthyl, 2-naphthyl, biphenylyl, or terphenylyl. Also, in each structural formula... * indicates the connection position. [ka]

[0463] A specific example of this phenanthroline derivative is, for example, 4,7-diphenyl-1,10 -Phenanthroline, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthrone Phosphorus, 9,10-di(1,10-phenanthroline-2-yl)anthracene, 2,6- Di(1,10-phenanthroline-5-yl)pyridine, 1,3,5-tri(1,10- Phenanthroline-5-yl)benzene, 9,9'-difluoro-bi(1,10-phen (Centroline-5-yl), basocproine, 1,3-bis(2-phenyl-1,10-f) Examples include phenanthroline-9-yl)benzene and compounds represented by the following structural formula. [ka]

[0464] This phenanthroline derivative can be produced using known raw materials and known synthesis methods. Cut.

[0465] <Quinolinol-based metal complexes> Quinolinol-based metal complexes are compounds represented by the following general formula (ETM-13), for example. ru. [ka] In the formula, R 1 ~R 6 These are, independently, hydrogen, fluorine, alkyl, cycloalkyl, It is aralkyl, alkenyl, cyano, alkoxy or aryl, and M is Li, Al, It is Ga, Be, or Zn, and n is an integer between 1 and 3.

[0466] Specific examples of quinolinol-based metal complexes include 8-quinolinol lithium and tris(8- Aluminum (4-methyl-8-quinolinolate), Tris(4-methyl-8-quinolinolate)aluminium Tris(5-methyl-8-quinolinolate)aluminum, Tris(3,4-dimethicone) (Lu-8-Quinolinolate) Aluminum, Tris(4,5-Dimethyl-8-Quinolinolate) Aluminum, Tris(4,6-dimethyl-8-quinolinolate)aluminum, S(2-methyl-8-quinolinolate)(phenolate)aluminum, bis(2-methyl) (Lu-8-Quinolinolate)(2-methylphenolate)aluminum, bis(2-methyl -8-Quinolinolate)(3-methylphenolate)aluminum, bis(2-methyl- 8-Quinolinolate)(4-Methylphenolate)Aluminum, Bis(2-Methyl-8 -Quinolinolate)(2-phenylphenolate)aluminum, bis(2-methyl-8 -Quinolinolate)(3-phenylphenolate)aluminum, bis(2-methyl-8 -Quinolinolate)(4-phenylphenolate)aluminum, bis(2-methyl-8 -Quinolinolate)(2,3-dimethylphenolate)aluminum, bis(2-methyl -8-Quinolinolate)(2,6-dimethylphenolate)aluminum, bis(2-Me (3,4-dimethylphenolate)aluminum, bis(2 -Methyl-8-quinolinolate)(3,5-dimethylphenolate)aluminum, bis (2-methyl-8-quinolinolate)(3,5-di-t-butylphenolate)aluminium Um, bis(2-methyl-8-quinolinolate)(2,6-diphenylphenolate) Luminium, bis(2-methyl-8-quinolinolate)(2,4,6-triphenylphenyl (Nolat) Aluminum, bis(2-methyl-8-quinolinolate)(2,4,6-tri Methylphenolate)aluminum, bis(2-methyl-8-quinolinolate)(2,4 ,5,6-tetramethylphenolate)aluminum, bis(2-methyl-8-quinolino (1-naphtholate)aluminum, bis(2-methyl-8-quinolinolate) (2-naphtholate)aluminum, bis(2,4-dimethyl-8-quinolinolate)( 2-Phenylphenolate)aluminum, bis(2,4-dimethyl-8-quinolinolate) (3-phenylphenolate)aluminum, bis(2,4-dimethyl-8-quinol) (4-phenylphenolate)aluminum, bis(2,4-dimethyl-8- (3,5-Dimethylphenolate) Aluminum, Bis(2,4-Dimethyl (3,5-di-t-butylphenolate)aluminum, butylphenolate S(2-methyl-8-quinolinolate)aluminum-μ-oxo-bis(2-methyl- 8-Quinolinolate)aluminum, bis(2,4-dimethyl-8-quinolinolate)a Luminium-μ-oxo-bis(2,4-dimethyl-8-quinolinolate)aluminum , bis(2-methyl-4-ethyl-8-quinolinolate)aluminum-μ-oxo-bi S(2-methyl-4-ethyl-8-quinolinolate)aluminum, bis(2-methyl- 4-Methoxy-8-Quinolinolate)aluminum-μ-oxo-bis(2-methyl-4 -Methoxy-8-Quinolinolate)aluminum, bis(2-methyl-5-cyano-8- (Quinolinolate) Aluminum-μ-oxo-bis(2-methyl-5-cyano-8-quino Linolate) Aluminum, bis(2-methyl-5-trifluoromethyl-8-quinoline (RAH) Aluminum-μ-oxo-bis(2-methyl-5-trifluoromethyl-8- (Quinoline) Aluminum, Bis(10-hydroxybenzo[h]quinoline) Beryl Examples include Um.

[0467] This quinolinol-based metal complex can be produced using known raw materials and known synthesis methods. Cut.

[0468] <Thiazole derivatives and benzothiazole derivatives> Thiazole derivatives are compounds represented by the following formula (ETM-14-1), for example. [ka] Benzothiazole derivatives are compounds represented by, for example, the following formula (ETM-14-2). ru. [ka]

[0469] In each formula, φ represents an n-valent aryl ring (preferably an n-valent benzene ring, naphthalene ring, or ant). Helical ring, fluorene ring, benzofluorene ring, phenalene ring, phenanthrene ring or It is a triphenylene ring, and n is an integer from 1 to 4, and it is a "thiazole substituent" or "ben The "zothiazole substituents" are the above formulas (ETM-2), (ETM-2-1), and (E In TM-2-2), the pyridyl group among the "pyridine substituents" is the thiazole group or A substituent that replaces the benzothiazole group, and is used in thiazole derivatives and benzothiazole At least one hydrogen atom in the derivative may be substituted with deuterium. (See structural formula below) The asterisk (*) inside indicates the connection point. [ka]

[0470] φ is further preferably an anthracene ring or a fluorene ring, in this case The structure can be described by referring to the explanation in the above formula (ETM-2-1) or formula (ETM-2-2). And in each equation, R 11 ~R 18This is the above formula (ETM-2-1) or formula (ETM-2-2) The explanation can be cited. Also, the above formula (ETM-2-1) or formula (ETM- In 2-2), it is described as a form in which two pyridine substituents are bonded, but these are When replacing with a zole substituent (or benzothiazole substituent), both pyri Even if you replace the din substituent with a thiazole substituent (or benzothiazole substituent) Okay (i.e., n=2), and replace any one of the pyridine substituents with a thiazole substituent ( (or a benzothiazole substituent) is replaced with the other pyridine substituent R 11 ~R 18 It may also be replaced with (i.e., n=1). Furthermore, for example, in the above equation (ETM-2-1) Keru R 11 ~R 18 At least one of them is a thiazole substituent (or benzothiazole substituent) Replace with a substituent to make a "pyridine substituent" R 11 ~R 18 You can replace it with this.

[0471] These thiazole derivatives or benzothiazole derivatives are synthesized using known raw materials and known synthesis methods. It can be manufactured using the law.

[0472] <Silole derivatives> Silole derivatives are compounds represented by the following formula (ETM-15), for example. Further details are available. It is described in Public Gazette No. 9-194487. [ka]

[0473] X and Y are independently alkyl, cycloalkyl, alkenyl, or alkynyl aryl, alkoxy, alkenyloxy, alkynyloxy, aryl, heteroaryl These may be substituted. For details of these bases, see the general formula (1A) above. And the explanation in general formula (1B), and further the explanation in formula (ETM-7-2) above, It can be used. Also, alkenyloxy and alkynyloxy can be used with alkoxy. The alkyl portion is replaced by an alkenyl or alkynyl group, and these alkynyl groups For details on Kenil and Alkinil, refer to the explanation in formula (ETM-7-2) above. can. Furthermore, X and Y combine to form a cycloalkyl ring (and a ring in which part of it is unsaturated). It may be formed, and the details of this cycloalkyl ring are shown in the above general formula (1A) and general formula (1 You can refer to the explanation of cycloalkyl in B).

[0474] R 1 ~R 4 These are, independently, hydrogen, halogen, alkyl, cycloalkyl, and ammonium compounds. Coxy, aryloxy, amino, alkylcarbonyl, arylcarbonyl, alkoxy Cicarbonyl, aryloxycarbonyl, azo group, alkylcarbonyloxy, aryl Alkac carbonyloxy, alkoxycarbonyloxy, aryloxycarbonyloxy, Sulfinyl, sulfonyl, sulfanyl, silyl, carbamoyl, aryl, hetero Aryl, alkenyl, alkynyl, nitro, formyl, nitroso, formyloxy, i Socyano, cyanate group, isocyanate group, thiocyanate group, isothiocyanate group , or cyano, these are alkyl, cycloalkyl, aryl, or halogen It may be substituted with a substituent, and may form a fused ring with an adjacent substituent.

[0475] R 1 ~R 4 In this context, halogens, alkyls, cycloalkyls, alkoxys, and arylo Details on xy, amino, aryl, heteroaryl, alkenyl, and alkynyl The explanations in general formulas (1A) and (1B) above can be cited.

[0476] R 1 ~R 4 In this context, alkylcarbonyl, arylcarbonyl, alkoxycarbonyl Lu, aryloxycarbonyl, alkylcarbonyloxy, arylcarbonyloxy , alkyl in alkoxycarbonyloxy and aryloxycarbonyloxy For details on aryls and alkoxys, please refer to the above general formulas (1A) and (1B). You can quote the explanation in [the relevant section].

[0477] As a silyl, it consists of a silyl group and at least one of the three hydrogen atoms of the silyl group. Examples of these groups independently include those substituted with aryl, alkyl, or cycloalkyl groups. Resubstituted silyls are preferred, including triarylsilyls, trialkylsilyls, and tricycloalkyls. Lucilyl, dialkylcycloalkylsilyl, and alkyldicycloalkylsilyl, etc. These can be listed. Details on aryl, alkyl, and cycloalkyl in these can be found below. The explanations in general formulas (1A) and (1B) above can be cited.

[0478] The fused ring formed between adjacent substituents is, for example, R 1 and R 2 , R 2 and R 3 , R 3 and R 4These are conjugated or unconjugated fused rings formed between such elements. These fused rings have an intraring structure. It may contain nitrogen, oxygen, and sulfur atoms, and may also be fused with other rings.

[0479] However, preferably, R 1 and R 4 If is a phenyl group, then X and Y are alkyl groups It is not phenyl. Also, preferably R 1 and R 4 If it is a thienyl group, X and Y is alkyl, R 2 and R 3 is alkyl, aryl, alkenyl or R 2 and R 3 It is a structure that does not simultaneously satisfy the condition of a cycloalkyl group that is bonded to form a ring. Also, preferably For more information, R 1 and R 4 If R is a silyl group, 2 , R 3 X and Y are independent of each other. And it is not hydrogen or an alkyl group having 1 to 6 carbon atoms. Also, preferably R 1 and R 2 In the case of a structure in which a benzene ring is fused, X and Y are not alkyl and phenyl.

[0480] These silole derivatives can be produced using known raw materials and known synthesis methods. .

[0481] <Azoline derivatives> Azoline derivatives are compounds represented by the following formula (ETM-16), for example. For further details, please refer to the national government. It is described in the International Publication No. 2017 / 014226. [ka]

[0482] In formula (ETM-16), φ is a group with an m-value derived from aromatic hydrocarbons with 6 to 40 carbon atoms or an aromatic group with 2 to 40 carbon atoms. It is an m-valent group derived from a heterocycle, and at least one hydrogen of φ is an alkyl group with 1 to 6 carbon atoms. aryl, cycloalkyl groups with 3 to 14 carbon atoms, aryl groups with 6 to 18 carbon atoms, or groups with 2 to 18 carbon atoms. It may also be substituted with a heteroaryl, Y is independently -O-, -S-, or >N-Ar, and Ar has 6 carbon atoms. 12 aryl or heteroaryl with 2 to 12 carbon atoms, and at least one Ar Hydrogen is found in alkyl groups with 1-4 carbon atoms, cycloalkyl groups with 5-10 carbon atoms, and acyclic groups with 6-12 carbon atoms. It may be substituted with a reel or a heteroaryl with 2 to 12 carbon atoms, R 1 ~R 5 haso Each is independently hydrogen, an alkyl group with 1 to 4 carbon atoms, or a cycloalkyl group with 5 to 10 carbon atoms. Yes, however, Ar in >N-Ar and R 1 ~R 5 one of the following This is the site that binds to L, L independently represents a divalent group represented by the following formula (L-1), and the following formula (L- Selected from the group consisting of divalent groups represented in 2), [ka] In formula (L-1), X 1 ~X 6 Each of them is independent of =CR 6 - or = N- and X 1 ~X 6 At least two of them are =CR 6 - and X 1 ~X 6 Two of the =CR 6 -R in 6 The φ or azoline ring is the site that binds to the ring, while the others are =CR.6 -ni Keru R 6 It is hydrogen, In formula (L-2), X 7 ~X 14 Each of them is independent of =CR 6 - or = N- and X 7 ~X 14 At least two of them are =CR 6 - and X 7 ~X 14 Two of the = CR 6 -R in 6 The φ or azoline ring is the site that binds to the ring, while the others are =CR. 6 -R in 6 It is hydrogen, At least one hydrogen atom of L is an alkyl group with 1 to 4 carbon atoms, or a cycloalkyl group with 5 to 10 carbon atoms. It is substituted with aryl atoms having 6 to 10 carbon atoms or heteroaryl atoms having 2 to 10 carbon atoms. Often, m is an integer from 1 to 4, and when m is from 2 to 4, the group formed by the azoline ring and L is They may be the same or different, and, In the compound represented by formula (ETM-16), at least one hydrogen atom is substituted with deuterium. It's okay to be there.

[0483] Specific azoline derivatives are those with the following general formula (ETM-16-1) or general formula (ETM- It is a compound represented by 16-2). [ka] In equations (ETM-16-1) and (ETM-16-2), φ is a group with an m-value derived from aromatic hydrocarbons with 6 to 40 carbon atoms or an aromatic group with 2 to 40 carbon atoms. It is an m-valent group derived from a heterocycle, and at least one hydrogen of φ is an alkyl group with 1 to 6 carbon atoms. aryl, cycloalkyl groups with 3 to 14 carbon atoms, aryl groups with 6 to 18 carbon atoms, or groups with 2 to 18 carbon atoms. It may also be substituted with a heteroaryl, In equation (ETM-16-1), Y is independently -O-, -S-, or >NA. r is a aryl or heteroaryl with 6-12 carbon atoms. Furthermore, at least one hydrogen atom of Ar is an alkyl group with 1 to 4 carbon atoms, or a cycloal group with 5 to 10 carbon atoms. Lukyl, substituted with aryls with 6 to 12 carbon atoms or heteroaryls with 2 to 12 carbon atoms. It's okay to be there, In formula (ETM-16-1), R 1 ~R 4 These are hydrogen and aluminum atoms with 1 to 4 carbon atoms, respectively, independently. It is a cycloalkyl group having 5 to 10 carbon atoms, however, R 1 and R 2 They are identical, Also R 3 and R 4 They are identical, In formula (ETM-16-2), R 1 ~R 5 These are hydrogen and aluminum atoms with 1 to 4 carbon atoms, respectively, independently. It is a cycloalkyl group having 5 to 10 carbon atoms, however, R 1 and R 2 They are identical, Also R 3 and R 4 They are identical, In equations (ETM-16-1) and (ETM-16-2), L independently represents a divalent group represented by the following formula (L-1), and the following formula (L- Selected from the group consisting of divalent groups represented in 2), [ka] In formula (L-1), X 1 ~X 6 Each of them is independent of =CR 6 - or = N- and X 1 ~X 6 At least two of them are =CR 6 - and X 1 ~X 6 Two of the =CR 6 -R in 6 The φ or azoline ring is the site that binds to the ring, while the others are =CR. 6 -ni Keru R 6 It is hydrogen, In formula (L-2), X 7 ~X 14 Each of them is independent of =CR 6 - or = N- and X 7 ~X 14 At least two of them are =CR 6 - and X 7 ~X 14 Two of the = CR 6 -R in 6 The φ or azoline ring is the site that binds to the ring, while the others are =CR. 6 -R in 6 It is hydrogen, At least one hydrogen atom of L is an alkyl group with 1 to 4 carbon atoms, or a cycloalkyl group with 5 to 10 carbon atoms. It is substituted with aryl atoms having 6 to 10 carbon atoms or heteroaryl atoms having 2 to 10 carbon atoms. Often, m is an integer from 1 to 4, and when m is from 2 to 4, the group formed by the azoline ring and L is They may be the same or different, and, At least one compound represented by formula (ETM-16-1) or formula (ETM-16-2) The other hydrogen atom may be replaced by deuterium.

[0484] Preferably, φ is a monovalent group represented by the following formulas (φ1-1) to (φ1-18), Divalent groups represented by equations (φ2-1) to (φ2-34), and below equations (φ3-1) to (φ3 -3) represents a trivalent group, and the following tetravalent group represented by formulas (φ4-1) to (φ4-2) Selected from the group consisting of the following groups, at least one hydrogen of φ is an alkyl or carbon group having 1 to 6 carbon atoms. Cycloalkyl groups with 3 to 14 prime numbers, aryl groups with 6 to 18 carbon atoms, or heteroalkyl groups with 2 to 18 carbon atoms. It may be substituted with a loaryl group. * in the structural formula below indicates a bond position. [ka] [ka] [ka] In the above formula, Z is >CR2, >N-Ar, >NL, -O- or -S-, and >C In R2, R is independently an alkyl group with 1 to 4 carbon atoms and a sic group with 5 to 10 carbon atoms. These are rhalkyl groups, aryl groups with 6 to 12 carbon atoms, or heteroaryl groups with 2 to 12 carbon atoms. R atoms may be bonded to each other to form a ring, and in >N-Ar, Ar has 6 to 12 carbon atoms. It is an aryl or heteroaryl with 2 to 12 carbon atoms, and L in >NL is the above one In general formula (ETM-16), formula (ETM-16-1), or general formula (ETM-16-2) It is L.

[0485] Preferably, L is benzene, naphthalene, pyridine, pyrazine, pyrimidine, pyrida Zin, triazine, quinoline, isoquinoline, naphthyridine, phthalazine, quinoxaline , a divalent ring group selected from the group consisting of quinazoline, sinnoline, and pteridine Yes, at least one hydrogen of L is an alkyl group with 1-4 carbon atoms, or a cycloa group with 5-10 carbon atoms. Lukyl, substituted with aryls having 6 to 10 carbon atoms or heteroaryls having 2 to 10 carbon atoms. It's okay to be there.

[0486] Preferably, Ar in >N-Ar as Y or Z is phenyl, naphthyl, phenyl Ridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, iso Quinolinyl, Naphthilidinyl, Phthalazinyl, Quinoxalinyl, Quinazolinyl, Sinnori Selected from the group consisting of nyl and pteridinyl, Ar in >N-Ar as Y At least one hydrogen atom is either an alkyl group with 1 to 4 carbon atoms, or a cycloalkyl group with 5 to 10 carbon atoms. Alternatively, it may be substituted with an aryl group having 6 to 10 carbon atoms.

[0487] Preferably, R 1 ~R 4 Each is independently hydrogen, an alkyl group with 1 to 4 carbon atoms, or carbon atoms. It is a cycloalkyl group of number 5 to 10, where R 1 and R 2 They are identical, R 3 and R 4 is the same It is one, and also R 1 ~R 4 Not all of them become hydrogen at the same time, and m is 1 or When m is 2, the group formed by the azoline ring and L is the same.

[0488] Specific examples of azoline derivatives include the following compounds. The "Me" in this example represents a methyl group. [ka] [ka]

[0489] More preferably, φ is given by the following formulas (φ2-1), (φ2-31), (φ2-32), Selected from the group consisting of divalent groups represented by formulas (φ2-33) and (φ2-34), At least one hydrogen atom of φ may be substituted with an aryl group having 6 to 18 carbon atoms, and each structure The asterisk (*) in the formula indicates the bonding position. [ka] L is benzene, pyridine, pyrazine, pyrimidine, pyridazine, and triazine. A divalent ring group selected from the following group, where at least one hydrogen of L has 1 to 4 carbon atoms. Alkyl, cycloalkyl with 5-10 carbon atoms, aryl or carbon number It may also be substituted with 2 to 14 heteroaryl compounds. In >N-Ar as Y, Ar is phenyl, pyridinyl, pyridinyl, pyrimidi Selected from the group consisting of nyl, pyridazinyl, and triazinyl, and at least one of the Ar The other hydrogen atom is an alkyl group with 1 to 4 carbon atoms, a cycloalkyl group with 5 to 10 carbon atoms, or a C5 hydrogen atom. It may also be replaced with aryl groups 6 to 10. R 1 ~R 4 Each is independently a hydrogen atom, an alkyl group with 1 to 4 carbon atoms, or a group with 5 to 10 carbon atoms. It is a cycloalkyl, however, R 1 and R 2 They are identical, R 3 and R 4 They are identical, Ta R 1 ~R 4 Not all of them will turn into hydrogen at the same time, and, m is 2, and the group formed by the azoline ring and L is the same.

[0490] Other specific examples of azoline derivatives include the following compounds. Note the structure. In the formula, "Me" represents a methyl group. [ka]

[0491] In the above formulas defining this azoline derivative, alkyl, cycloalkyl, aryl and For details on heteroaryls, see the general formulas (1A) and (1B) above. You can quote the explanation.

[0492] This azoline derivative can be produced using known raw materials and known synthesis methods.

[0493] The electron transport layer or electron injection layer further comprises the material forming the electron transport layer or electron injection layer. It may contain a substance that can reduce the material. This reducing substance is a substance that has a certain degree of reducing properties. Therefore, various substances are used, for example, alkali metals, alkaline earth metals, rare earth metals Groups, alkali metal oxides, alkali metal halides, alkaline earth metal oxides, Alkaline earth metal halides, rare earth metal oxides, rare earth metal halides, A Organic complexes of lucid metals, organic complexes of alkaline earth metals, and organic complexes of rare earth metals At least one selected from the group can be suitably used.

[0494] Preferred reducing substances include Na (work function 2.36 eV) and K (work function 2.28 eV). , alkali metals such as Rb (2.16 eV) or Cs (1.95 eV), and Ca ( (2.9eV), Sr (2.0-2.5eV), or Ba (2.52eV), etc. Examples include earth metals, with materials having a work function of 2.9 eV or less being particularly preferred. Of these, the more preferred reducing substances are alkali metals such as K, Rb, or Cs, and even more preferred These alkali metals are either Rb or Cs, with Cs being the most preferred. In particular, it has high reducing ability and is used as an additive in relatively small amounts to materials that form electron transport layers or electron injection layers. This will improve the luminescence brightness and extend the lifespan of organic EL elements. As reducing substances with a voltage of 2.9 eV or less, combinations of two or more of these alkali metals are also preferred. In particular, combinations containing Cs, for example, Cs and Na, Cs and K, Cs and Rb, Alternatively, a combination of Cs, Na, and K is preferred. Including Cs enhances the reducing ability. It can be efficiently exerted by adding it to the material forming the electron transport layer or electron injection layer. This will improve the luminescence brightness and extend the lifespan of organic EL elements.

[0495] The electron injection layer material and electron transport layer material described above are provided by substituting reactive substituents therein. A polymer compound obtained by polymerizing a reactive compound as a monomer, or a polymer crosslink thereof. A body, or a pendant-type polymer compound obtained by reacting a main-chain polymer with the reactive compound. Alternatively, it can be used as a material for electronic layers, either as a pendant-type polymer crosslinked material or as such. In this case, the reactive substituent is represented by the above general formula (1A) or general formula (1B). We can cite the explanation for polycyclic aromatic compounds. Details of the applications of such polymer compounds and polymer crosslinks will be described later.

[0496] <Cathode in an organic electroluminescent device> The cathode 108 transmits electrons to the light-emitting layer 105 via the electron injection layer 107 and the electron transport layer 106. It plays the role of injecting offspring.

[0497] Any material that can efficiently inject electrons into the organic layer can be used as the material for forming cathode 108. While not particularly limited, materials similar to those used to form the anode 102 can be used. However, tin, indium, calcium, aluminum, silver, copper, nickel, chromium, gold Platinum, iron, zinc, lithium, sodium, potassium, cesium, and magnesium, etc. The metal or alloys thereof (magnesium-silver alloy, magnesium-indium alloy, f Lithium oxide (such as aluminum-lithium alloys like aluminum) is preferred. To increase electron injection efficiency and improve device characteristics, lithium, sodium, potassium Alloys containing cesium, calcium, magnesium, or these low work function metals are effective. Yes, they exist. However, these low work function metals are generally unstable in the atmosphere. To improve this point, for example, trace amounts of lithium, cesium, and magnesium can be added to the organic layer. A method is known to use doping to create highly stable electrodes. Other dopants Examples include lithium fluoride, cesium fluoride, lithium oxide, and cesium oxide. Inorganic salts can also be used, however, they are not limited to these.

[0498] Furthermore, platinum, gold, silver, copper, iron, tin, aluminum, and indigo are used for electrode protection. Metals such as um, or alloys using these metals, as well as silica, titania, and silicon nitride. Inorganic materials such as ions, polyvinyl alcohol, vinyl chloride, hydrocarbon polymer compounds, etc. Layering is a preferred example. Methods for fabricating these electrodes include resistance heating and electronic heating. Beam deposition, sputtering, ion plating, and coating, etc., to remove electrical conductivity. If you can do that, there are no particular restrictions.

[0499] <Binding agents that may be used in each layer> Materials used in the above hole injection layer, hole transport layer, light emission layer, electron transport layer, and electron injection layer The material can form each layer ...

Claims

1. A polycyclic aromatic compound represented by the following general formula (1A) or general formula (1B). 【Chemistry 1】 In the above formula (1A) or formula (1B), R ａ is a hydrogen atom or substituent, and in the a-ring, "-C(-R ａ )=" is placed in place of "-N=". It's okay if they've been replaced. Rings B, C, D, E, F, and G are each independently an aryl ring or It is a heteroaryl ring, and even if at least one hydrogen in these rings is substituted often, Y １ , Y ２ , and Y ３ These are, independently of each other, >B-, >P-, >P(=O)-, > P(=S)-, >Al-, >Ga-, >As-, >C(-R)-, >Si(-R)-, or t is >Ge(-R)-, and R in >C(-R)-, R in >Si(-R)-, and > In Ge(-R)-, the R's are, independently, aryls that may be substituted, or even if substituted. A good heteroaryl, optionally substituted alkyl, or optionally substituted cycloalkyl It is X １ and X ２ These are, independently, >N-R, >O, >S, >C(-R) ２ ,>S i(−R) ２ or >Se, and R of the >N−R, >C(−R) ２ of R, and > Si(-R) ２ R is independently hydrogen, an optional aryl, or a substituted element. A heteroaryl which may be substituted, an alkyl which may be substituted, or a heteroaryl which may be substituted It may be a cycloalkyl, and the above >C(-R) ２ The two Rs and >Si(-R ) ２ At least one of the two R groups may be connected by a single bond or a linking group. 、 X １ The above >N-R's R, >C(-R) ２ R, or >Si(-R) ２ The R is They may be bonded to at least one of the a-ring and B-ring by a single bond or a linking group. X ２ The above >N-R's R, >C(-R) ２ R, or >Si(-R) ２ The R is They may be bonded to at least one of the α ring and the E ring by a single bond or a linking group. The C and D rings, the G and B rings, and the F and E rings are each independent of each other. They may be bonded by a bond or a linking group. However, in formula (1A) above, the CD bond of the C ring and the D ring, and X １ As for N-R R (where R is the optionally substituted aryl or the optionally substituted hetero (Limited to the cycloalkyl group which may be substituted) and X of the B ring １ B knot Combined, X ２ > R of N-R (where R is the substituted aryl, the A heteroaryl or cycloalkyl group which may be substituted. (limited to) and X of the E ring ２ One or two of the three bonds with the E bond It exists, Furthermore, in formula (1B) above, the CD bond between the C ring and the D ring, and the GB bond between the G ring and the B ring. And, of the three bonds between the F ring and the FE bond of the E ring, one or two bonds are It exists, In the compound represented by formula (1A) or formula (1B) above, the B ring, C ring, D ring, E ring At least one of the F ring, G ring, aryl, and heteroaryl is at least one It may be condensed with a cycloalkane, and at least one of the cycloalkanes Hydrogen may be substituted, and at least one -CH group in the cycloalkane ２ - It may also be substituted with -O-, At least one hydrogen in the compound represented by formula (1A) or formula (1B) above is It may be substituted with deuterium, cyanopropyl alcohol, or halogen.

2. In the above formula (1A) or formula (1B), R ａ These are hydrogen, optionally substituted aryls, and optionally substituted heteroaryls. , optionally substituted diarylamino, optionally substituted diheteroarylamino , optionally substituted aryl heteroarylamino, optionally substituted diaryl aryl boryl (the two aryls may be linked by a single bond or a linking group), substituted Optional alkyl groups, optional cycloalkyl groups, optional substituted groups Alkoxy, optionally substituted aryloxy, or substituted silyl, In ring a, "-C(-R ａ )=" may be replaced with "-N=". Rings B, C, D, E, F, and G are each independently an aryl ring or It is a heteroaryl ring, and at least one hydrogen in these rings is substituted. A good aryl, a heteroaryl that may be substituted, a diaryl that may be substituted Diheteroarylamino, optionally substituted diheteroarylamino, optionally substituted arylamino A heteroarylamino, optionally substituted diarylboryl (the two aryls are single Alkyl, which may be substituted, (possibly bonded via a bond or linking group) Optionally substituted cycloalkyls, optionally substituted alkoxys, even if substituted It may be substituted with a good aryloxy or substituted silyl. Y １ , Y ２ , and Y ３ These are, independently of each other, >B-, >P-, >P(=O)-, > P(=S)-, >Al-, >Ga-, >As-, >C(-R)-, >Si(-R)-, or t is >Ge(-R)-, and R in >C(-R)-, R in >Si(-R)-, and >The R in Ge(-R)- can be aryl, heteroaryl, alkyl, and or is a cycloalkyl group, and at least one hydrogen atom in R is alkyl or They may also be substituted with cycloalkyl groups. X １ and X ２ These are, independently, >N-R, >O, >S, >C(-R) ２ ,>S i(-R) ２ , or >Se, and R of >N-R, >C(-R) ２ R of, and > Si(-R) ２ R can be independently hydrogen, aryl, heteroaryl, or alkyl. , or cycloalkyl, wherein at least one hydrogen in R is alkyl or may be substituted with a cycloalkyl group, and the above >C(-R) ２ The two Rs and > Si(-R) ２ At least one of the two Rs is a single bond, -CH=CH-, -CR= CR-、-C≡C-、-N(-R)-、-O-、-S-、-C(-R) ２ -、-Si(- R) ２ - or -Se- may be bonded, and the R, -N of -CR=CR- -R)- of R, -C(-R) ２ -R and -Si(-R) ２ The R values ​​for each are independent. And hydrogen, aryl, heteroaryl, alkyl, alkenyl, alkynyl, or cy It is a chloroalkyl group, and at least one hydrogen atom in R is alkyl or cycloalkyl. It may be substituted with R, and two adjacent Rs may form a ring, cycloal They may form chilenes, arylenes, or heteroarylenes. X １ The above >N-R's R, >C(-R) ２ R, or >Si(-R) ２ The R is , single bond, -CH=CH-, -CR=CR-, -C≡C-, -N(-R)-, -O-, - S-, -C (-R) ２ -, -Si(-R) ２ - or -Se- indicates the a-ring and B-ring It may be combined with at least one of X ２ The above >N-R's R, >C(-R) ２ R, or >Si(-R) ２ R is a single bond, -CH=CH-, -CR=CR-, - C≡C-、-N(-R)-、-O-、-S-、-C(-R) ２ -、-Si(-R) ２ -、 Alternatively, it may be bonded to at least one of the a ring and the E ring by -Se-, and the - CR = CR- R, -N(-R)- R, -C(-R) ２ -R and -Si(-R) ２ The R in - can be independently hydrogen, aryl, heteroaryl, alkyl, or alkeni. R is alkynyl or cycloalkyl, and at least one hydrogen in R is They may be substituted with alkyl or cycloalkyl groups, and two adjacent R groups may be substituted with each other. These form rings, forming cycloalkylenes, arylenes, and heteroarylenes. Often, The C and D rings, the G and B rings, and the F and E rings are each independent of each other. Bond, -CH=CH-, -CR=CR-, -C≡C-, -N(-R)-, -O-, -S- , -C (-R) ２ -, -Si(-R) ２ They may be joined by - or -Se-, The R in -CR=CR-, the R in -N(-R)-, and -C(-R) ２ -R and -Si( -R) ２ The R in - is independently hydrogen, aryl, heteroaryl, alkyl, and aryl. Lukenyl, alkynyl, or cycloalkyl, and at least one of R The hydrogen atoms may be substituted with alkyl or cycloalkyl groups, and two adjacent hydrogen atoms may be substituted with alkyl or cycloalkyl groups. R atoms form rings, creating cycloalkylenes, arylenes, and heteroarylenes. It's fine to do so, However, in formula (1A) above, the CD bond of the C ring and the D ring, and X １ As for N-R R (This R may be substituted with the alkyl or cycloalkyl, the alkyl (Limited to the heteroaryl or cycloalkyl compounds) and X of the B ring １ B bond and , X ２ >N-R's R (where R is substituted with the alkyl or cycloalkyl group) (This may be limited to the aryl, heteroaryl, or cycloalkyl compounds.) and X of the E ring ２ Of the three bonds with the E bond, one or two bonds exist. And, Furthermore, in formula (1B) above, the CD bond between the C ring and the D ring, and the GB bond between the G ring and the B ring. And, of the three bonds between the F ring and the FE bond of the E ring, one or two bonds are It exists, In the compound represented by formula (1A) or formula (1B) above, the B ring, C ring, D ring, E ring At least one of the F ring, G ring, aryl, and heteroaryl is at least one It may be condensed with a cycloalkane, and at least one of the cycloalkanes Hydrogen may be substituted, and at least one -CH group in the cycloalkane ２ - It may also be substituted with -O-, At least one hydrogen in the compound represented by formula (1A) or formula (1B) above is It may be substituted with deuterium, cyano, or halogen. The polycyclic aromatic compound as described in claim 1.

3. A polycyclic fragrance according to claim 1, represented by the following general formula (2A) or the following general formula (2B). family compounds. 【Chemistry 2】 In the above formula (2A) or formula (2B), R ａ These are hydrogen, aryl, heteroaryl, diarylamino, and diheteroarylamino. No, aryl heteroarylamino, diarylboryl (the two aryls are single-bonded or Alkyl, cycloalkyl, alkoxy, and aryl groups (may be linked by a linking group) Oxy, triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dial The R is a chlorocycloalkylsilyl or alkyldicycloalkylsilyl. ａ to At least one hydrogen in is aryl, heteroaryl, alkyl, or cycloaryl It is also acceptable if it is replaced with Lukil. In ring a, "-C(-R ａ )=" may be replaced with "-N=". R ｂ , R ｃ , R ｄ , R ｅ , R ｆ , and R ｇ These are, independently, hydrogen, aryl, Heteroaryl, diarylamino, diheteroarylamino, arylheteroaryl Amino, diarylboryl (the two aryls may be linked by a single bond or a linking group) (Good), alkyl, cycloalkyl, alkoxy, aryloxy, triarylsilyl , trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, or alkyldicycloalkylsilyl, and the R ｂ , R ｃ , R ｄ , R ｅ , R ｆ ,oh Call R ｇ At least one hydrogen in is aryl, heteroaryl, alkyl, and R may be substituted with a cycloalkyl group, and also R ｂ , R ｃ , R ｄ , R ｅ , R ｆ , oyo biR ｇ Among these, adjacent groups bond together to form a b ring, c ring, d ring, e ring, f ring, and so on. The aryl ring or heteroaryl ring may be formed together with the γ ring, At least one hydrogen in the ring is aryl, heteroaryl, diarylamino, or di Heteroarylamino, arylheteroarylamino, diarylboryl (two aryl The groups may be linked by single bonds or linking groups), alkyl, cycloalkyl, and A Lucoxy, aryloxy, triarylsilyl, trialkylsilyl, tricycloal Killsilyl, dialkylcycloalkylsilyl, or alkyldicycloalkylsilyl They may be substituted with, and at least one hydrogen in these substituents is aryl, They may be substituted with heteroaryl, alkyl, or cycloalkyl groups. In rings b, c, d, e, f, and g, any "-C(-R)=" (this Here R is, R ｂ , R ｃ , R ｄ , R ｅ , R ｆ , or R ｇ (is replaced by "-N=") Alternatively, any "—C(—R)=C(—R)—" (where R is R ｂ , R ｃ , R ｄ , R ｅ , R ｆ , or R ｇ (is) "-N(-R)-", "-O-", "-S-" , "-C(-R) ２ -", "-Si(-R) ２ -", or "-Se-", is replaced by It may be present, and the R in the aforementioned "-N(-R)-" and "-C(-R)" ２ The R in "-" and "-Si (-R) ２ The R in "-" represents hydrogen, aryl, heteroaryl, alkyl, or cycloaryl It is a kill, and at least one hydrogen in R is alkyl or cycloalkyl. The above "-C(-R)" may be substituted. ２ The two R's of "-" and "-Si(-R)" ) ２ At least one of the two R's in -" is a single bond, -CH=CH-, -CR=CR- 、-C≡C-、-N(-R)-、-O-、-S-、-C(-R) ２ -、-Si(-R) ２ They may be bonded by - or -Se-, and the R, -N(-R) of -CR=CR- -R, -C(-R) ２ -R and -Si(-R) ２ The R values ​​in - are independent of each other. Hydrogen, aryl, heteroaryl, alkyl, alkenyl, alkynyl, or cyclo It is a lucyl, and at least one hydrogen in R is alkyl or cycloalkyl. It may be substituted with, and two adjacent Rs may form a ring, resulting in a cycloalkylene They may form arylene or heteroarylene. Y １ , Y ２ , and Y ３ These are, independently of each other, >B-, >P-, >P(=O)-, > P(=S)-, >Al-, >Ga-, >As-, >C(-R)-, >Si(-R)-, or t is >Ge(-R)-, and R in >C(-R)-, R in >Si(-R)-, and >The R in Ge(-R)- can be aryl, heteroaryl, alkyl, and or is a cycloalkyl group, and at least one hydrogen atom in R is alkyl or It may also be substituted with a cycloalkyl group. X １ and X ２ These are, independently, >N-R, >O, >S, >C(-R) ２ ,>S i(-R) ２ , or >Se, and R of >N-R, >C(-R) ２ R of, and > Si(-R) ２ R can be independently hydrogen, aryl, heteroaryl, or alkyl. , or cycloalkyl, wherein at least one hydrogen in R is alkyl or may be substituted with a cycloalkyl group, and the above >C(-R) ２ The two Rs and > Si(-R) ２ At least one of the two Rs is a single bond, -CH=CH-, -CR= CR-、-C≡C-、-N(-R)-、-O-、-S-、-C(-R) ２ -、-Si(- R) ２ - or -Se- may be bonded, and the R, -N of -CR=CR- -R)- of R, -C(-R) ２ -R and -Si(-R) ２ The R values ​​for each are independent. And hydrogen, aryl, heteroaryl, alkyl, alkenyl, alkynyl, or cy It is a chloroalkyl group, and at least one hydrogen atom in R is alkyl or cycloalkyl. It may be substituted with R, and two adjacent Rs may form a ring, cycloal They may form chilenes, arylenes, or heteroarylenes. X １ The above >N-R's R, >C(-R) ２ R, or >Si(-R) ２ The R is , single bond, -CH=CH-, -CR=CR-, -C≡C-, -N(-R)-, -O-, - S-, -C (-R) ２ -, -Si(-R) ２ - or -Se- indicates the a-ring and b-ring It may be combined with at least one of X ２ The above >N-R's R, >C(-R) ２ R, or >Si(-R) ２ R is a single bond, -CH=CH-, -CR=CR-, - C≡C-、-N(-R)-、-O-、-S-、-C(-R) ２ -、-Si(-R) ２ -、 Alternatively, it may be bonded to at least one of the a ring and the e ring by -Se-, and the - CR = CR- R, -N(-R)- R, -C(-R) ２ -R and -Si(-R) ２ The R in - can be independently hydrogen, aryl, heteroaryl, alkyl, or alkeni. R is alkynyl or cycloalkyl, and at least one hydrogen in R is They may be substituted with alkyl or cycloalkyl groups, and two adjacent R groups may be substituted with each other. These form rings, forming cycloalkylenes, arylenes, and heteroarylenes. Often, The c and d rings, the g and b rings, and the f and e rings are each independent of each other. Bond, -CH=CH-, -CR=CR-, -C≡C-, -N(-R)-, -O-, -S- , -C (-R) ２ -, -Si(-R) ２ They may be joined by - or -Se-, The R in -CR=CR-, the R in -N(-R)-, and -C(-R) ２ -R and -Si( -R) ２ The R in - is independently hydrogen, aryl, heteroaryl, alkyl, and aryl. Lukenyl, alkynyl, or cycloalkyl, and at least one of R The hydrogen atoms may be substituted with alkyl or cycloalkyl groups, and two adjacent hydrogen atoms may be substituted with alkyl or cycloalkyl groups. R atoms form rings, creating cycloalkylenes, arylenes, and heteroarylenes. It's fine to do so, However, in formula (2A) above, the cd bond of the c ring and the d ring, and X １ As for N-R R (This R may be substituted with the alkyl or cycloalkyl, the alkyl (Limited to the heteroaryl or cycloalkyl compounds) and X of the b ring １ b bond and , X ２ >N-R's R (where R is substituted with the alkyl or cycloalkyl group) (This may be limited to the aryl, heteroaryl, or cycloalkyl compounds.) and X of the e ring ２ Of the three bonds with the e bond, one or two bonds exist. And, Furthermore, in formula (2B) above, the cd bond between the c ring and the d ring, and the gb bond between the g ring and the b ring. And, of the three bonds between the f-ring and the fe-bond of the e-ring, one or two of the bonds are It exists, In the compound represented by formula (2A) or formula (2B) above, the b ring, the c ring, The d ring, the e ring, the f ring, the g ring, the ring on which the above is formed, the aryl, and the At least one of the heteroaryls is at least one cycloalkane having 3 to 24 carbon atoms. They may be condensed in such a way, and at least one hydrogen in the cycloalkane is carbon number aryls with 6 to 30 carbon atoms, heteroaryls with 2 to 30 carbon atoms, alkyls with 1 to 24 carbon atoms, Alternatively, it may be substituted with a cycloalkyl group having 3 to 24 carbon atoms, and the cycloalkane may be substituted with a cycloalkyl group having 3 to 24 carbon atoms. at least one -CH ２ The - can also be substituted with -O-. At least one hydrogen in the compound represented by formula (2A) or formula (2B) above is It may be substituted with deuterium, cyanopropyl alcohol, or halogen.

4. In the above formula (2A) or formula (2B), R ａ These include hydrogen, aryl atoms with 6 to 30 carbon atoms, heteroaryl atoms with 2 to 30 carbon atoms, and diaryl atoms. arylamino (where aryl has 6 to 12 carbon atoms), diarylboryl (however Aryls are aryl compounds with 6 to 12 carbon atoms, and two aryls are linked by a single bond or a linking group. (May be bonded together), alkyl groups having 1 to 24 carbon atoms, or cycloalkyl groups having 3 to 24 carbon atoms. It is Lukil, and the R ａ At least one hydrogen atom in is an aryl atom having 6 to 12 carbon atoms. Heteroaryl atoms with 2 to 15 carbon atoms, alkyl atoms with 1 to 6 carbon atoms, or cyanoacrylate atoms with 3 to 14 carbon atoms It may also be substituted with a chloroalkyl group. In ring a, "-C(-R ａ )=" may be replaced with "-N=". R ｂ , R ｃ , R ｄ , R ｅ , R ｆ , and R ｇ These are, independently, hydrogen, carbon atoms with 6 carbon atoms... 30 aryls, heteroaryls with 2 to 30 carbon atoms, diarylaminos (however aryl) (aryls with 6 to 12 carbon atoms), diarylboryls (where aryls have 6 to 12 carbon atoms) (It is an aryl compound, and the two aryl compounds may be linked by a single bond or a linking group), carbon The R is an alkyl group with 1 to 24 prime numbers, or a cycloalkyl group with 3 to 24 carbon atoms. ｂ , R ｃ , R ｄ , R ｅ , R ｆ , and R ｇ At least one hydrogen in is a carbon-6 to carbon-12 Aryl, heteroaryl with 2 to 15 carbon atoms, alkyl with 1 to 6 carbon atoms, or 3 carbon atoms It may be substituted with cycloalkyl groups up to 14, and also R ｂ , R ｃ , R ｄ , R ｅ , R ｆ , and R ｇ Among these, adjacent groups bond together to form a b ring, c ring, d ring, e ring, and f ring, respectively. Along with the ring and the γ ring, there are aryl rings with 9 to 16 carbon atoms or heteroaryl rings with 6 to 15 carbon atoms. A ring may be formed, and at least one hydrogen in the formed ring has six carbon atoms. ~30 aryls, heteroaryls with 2 to 30 carbon atoms, diarylaminos (however, aryl) (The aryl group has 6 to 12 carbon atoms), diarylboryl (where aryl has 6 to 12 carbon atoms) (These are aryl compounds, and the two aryl compounds may be linked by a single bond or a linking group.) Even if substituted with alkyl groups having 1 to 24 carbon atoms, or cycloalkyl groups having 3 to 24 carbon atoms Often, at least one hydrogen atom in these substituents is an aryl or carbon atom having 6 to 12 carbon atoms. Heteroaryls with 2 to 15 prime numbers, alkyls with 1 to 6 carbon atoms, or sic compounds with 3 to 14 carbon atoms. It may also be substituted with a r-alkyl group. In rings b, c, d, e, f, and g, any "-C(-R)=" (this Here R is, R ｂ , R ｃ , R ｄ , R ｅ , R ｆ , or R ｇ (is replaced by "-N=") It is also fine to have any "-C(-R) = C(-R)-" (where R is R ｂ , R ｃ , R ｄ , R ｅ , R ｆ , or R ｇ (is) "-N(-R)-", "-O-", "-S-" "-C (-R) ２ -”, “-Si(-R) ２ Replaced with "-" or "-Se-" It may be present, and the R in the aforementioned "-N(-R)-" and "-C(-R)" ２ The R in "-" and "-Si (-R) ２ The R in "-" represents hydrogen, aryl atoms with 6 to 12 carbon atoms, and heteroaryl atoms with 2 to 15 carbon atoms. R is an alkyl group having 1 to 6 carbon atoms, or a cycloalkyl group having 3 to 14 carbon atoms, and the R is an alkyl group having 1 to 6 carbon atoms. At least one hydrogen atom in is an alkyl group having 1 to 6 carbon atoms or a cyclic group having 3 to 14 carbon atoms. It may be substituted with a rhalkyl, and the "-C(-R)" ２ -" and the two R's and -Si(-R) ２ At least one of the two Rs in -" is a single bond, -CH=CH-, - CR=CR-、-C≡C-、-N(-R)-、-O-、-S-、-C(-R) ２ -、-S i(-R) ２ - or -Se- may be bonded, and the R of -CR=CR- -N(-R)-'s R, -C(-R) ２ -R and -Si(-R) ２ - The R is each These independently include hydrogen, aryl atoms with 6 to 12 carbon atoms, heteroaryl atoms with 2 to 15 carbon atoms, and carbon atoms. Alkyls with 1 to 6 carbon atoms, alkenyls with 1 to 6 carbon atoms, alkynyls with 1 to 6 carbon atoms, or carbon It is a cycloalkyl group with prime numbers 3 to 14, and at least one hydrogen atom in R is a carbon number They may be substituted with alkyl groups having 1 to 6 carbon atoms or cycloalkyl groups having 3 to 14 carbon atoms, Two adjacent R groups form a ring, forming cycloalkylenes with 3 to 14 carbon atoms, and cycloalkylenes with 6 to 14 carbon atoms. It may form 12 arylenes, or heteroarylenes with 2 to 15 carbon atoms. Y １ , Y ２ , and Y ３ These are, independently of each other, >B-, >P-, >P(=O)-, > P(=S)-, >Al-, >Ga-, >As-, >C(-R)-, >Si(-R)-, or t is >Ge(-R)-, and R in >C(-R)-, R in >Si(-R)-, and >The R in Ge(-R)- is independently an aryl group with 6 to 12 carbon atoms and a group with 2 to 1 carbon atoms. 5 heteroaryl groups, C1-C6 alkyl groups, or C3-C4 cycloalkyl groups In this R, at least one hydrogen atom is an alkyl group having 1 to 6 carbon atoms or a C1 It may also be substituted with 3 to 14 cycloalkyl groups. X １ and X ２ These are, independently, >N-R, >O, >S, >C(-R) ２ ,>S i(-R) ２ , or >Se, and R of >N-R, >C(-R) ２ R of, and > Si(-R) ２ R is independently hydrogen, aryl atoms with 6 to 12 carbon atoms, and aryl atoms with 2 carbon atoms. ~15 heteroaryls, 1-6 C1 alkyls, or 3-14 C1 cycloaryls It is a kill, and at least one hydrogen in R is an alkyl or carbon having 1 to 6 carbon atoms. It may also be substituted with cycloalkyl groups with prime numbers between 3 and 14. X １ The above >N-R's R, >C(-R) ２ R, or >Si(-R) ２ The R is , single bond, -CH=CH-, -CR=CR-, -C≡C-, -N(-R)-, -O-, - S-, -C (-R) ２ -, -Si(-R) ２ - or -Se- indicates the a-ring and b-ring It may be combined with at least one of X ２ The above >N-R's R, >C(-R) ２ R, or >Si(-R) ２ R is a single bond, -CH=CH-, -CR=CR-, - C≡C-、-N(-R)-、-O-、-S-、-C(-R) ２ -、-Si(-R) ２ -、 Alternatively, it may be bonded to at least one of the a ring and the e ring by -Se-, and the - CR = CR- R, -N(-R)- R, -C(-R) ２ -R and -Si(-R) ２ The R in - is independently hydrogen, aryl atoms with 6 to 12 carbon atoms, and helium atoms with 2 to 15 carbon atoms. Teloaryl, alkyl with 1 to 6 carbon atoms, alkenyl with 1 to 6 carbon atoms, a Lukinyl, or a cycloalkyl group having 3 to 14 carbon atoms, and at least one of the R atoms One hydrogen atom is substituted with an alkyl group having 1 to 6 carbon atoms or a cycloalkyl group having 3 to 14 carbon atoms. It is also possible for two adjacent Rs to form a ring, and a cycloal with 3 to 14 carbon atoms. Forms kylene, arylene with 6 to 12 carbon atoms, or heteroarylene with 2 to 15 carbon atoms. Even if you do, The c and d rings, the g and b rings, and the f and e rings are each independent of each other. Bond, -CH=CH-, -CR=CR-, -C≡C-, -N(-R)-, -O-, -S- , -C (-R) ２ -, -Si(-R) ２ They may be joined by - or -Se-, The R in -CR=CR-, the R in -N(-R)-, and -C(-R) ２ -R and -Si( -R) ２ The R in - represents, independently, hydrogen, aryl atoms with 6 to 12 carbon atoms, and aryl atoms with 2 to 1 carbon atoms. 5 heteroaryls, C1-C6 alkyls, C1-C6 alkenyls, C1- 6 alkynyl or cycloalkyl with 3 to 14 carbon atoms, and at least one of the R atoms. Each hydrogen atom is placed on an alkyl group with 1 to 6 carbon atoms or a cycloalkyl group with 3 to 14 carbon atoms. They may be replaced, and two adjacent Rs may form a ring, with 3 to 14 carbon atoms. Roalkylenes, arylenes with 6 to 12 carbon atoms, or heteroarylenes with 2 to 15 carbon atoms. It may also form a structure, However, in formula (2A) above, the cd bond of the c ring and the d ring, and X １ As for N-R R (where R is an alkyl group having 1 to 6 carbon atoms or a cycloalkyl group having 3 to 14 carbon atoms) The aryl atoms having 6 to 12 carbon atoms and the heteroaryl atoms having 2 to 15 carbon atoms may be substituted. (Limited to cycloalkyl groups having 3 to 14 carbon atoms) and X of the b ring １ b-bond and, X ２ >N-R's R (this R is the alkyl group having 1 to 6 carbon atoms or 3 to 1 carbon atoms) The aryl group having 6 to 12 carbon atoms, which may be substituted with cycloalkyl groups, and the carbon (Limited to heteroaryls with 2 to 15 carbon atoms, or cycloalkyls with 3 to 14 carbon atoms) X of the e-circle ２ Of the three bonds with the e bond, one or two bonds are present. the law of nature, Furthermore, in formula (2B) above, the cd bond between the c ring and the d ring, and the gb bond between the g ring and the b ring. And, of the three bonds between the f-ring and the fe-bond of the e-ring, one or two of the bonds are It exists, In the compound represented by formula (2A) or formula (2B) above, the b ring, the c ring, The d ring, the e ring, the f ring, the g ring, the ring on which the above is formed, the aryl, and the At least one of the heteroaryls is at least one cycloalkane having 3 to 24 carbon atoms. They may be condensed in such a way, and at least one hydrogen in the cycloalkane is carbon number aryl groups with 6 to 16 carbon atoms, heteroaryl groups with 2 to 15 carbon atoms, alkyl groups with 1 to 12 carbon atoms, Alternatively, it may be substituted with a cycloalkyl group having 3 to 16 carbon atoms. At least one hydrogen in the compound represented by formula (2A) or formula (2B) above is It may be substituted with deuterium, cyano, or halogen. The polycyclic aromatic compound as described in claim 3.

5. In the above formula (2A) or formula (2B), R ａ These include hydrogen, aryl atoms with 6 to 16 carbon atoms, heteroaryl atoms with 2 to 20 carbon atoms, and diaryl atoms. arylamino (whereas aryl has 6 to 10 carbon atoms), diarylboryl (however Aryls are aryl compounds with 6 to 10 carbon atoms, and two aryls are linked by a single bond or a linking group. (May be bonded together), alkyl groups having 1 to 12 carbon atoms, or cycloa groups having 3 to 16 carbon atoms It is Lukil, and the R ａ At least one hydrogen atom in is an aryl atom having 6 to 10 carbon atoms. Heteroaryls with 2 to 10 carbon atoms, alkyls with 1 to 5 carbon atoms, or sylions with 5 to 10 carbon atoms It may also be substituted with a chloroalkyl group. In ring a, "-C(-R ａ )=" may be replaced with "-N=". R ｂ , R ｃ , R ｄ , R ｅ , R ｆ , and R ｇ These are, independently, hydrogen, carbon atoms with 6 carbon atoms... 16 aryls, heteroaryls with 2 to 20 carbon atoms, diarylaminos (however aryl) (aryls with 6 to 10 carbon atoms), diarylboryls (where aryls have 6 to 10 carbon atoms) (It is an aryl compound, and the two aryl compounds may be linked by a single bond or a linking group), carbon The R is an alkyl group with prime numbers 1 to 12, or a cycloalkyl group with 3 to 16 carbon atoms. ｂ , R ｃ , R ｄ , R ｅ , R ｆ , and R ｇ At least one hydrogen in is a carbon-10 Aryl, heteroaryl with 2 to 10 carbon atoms, alkyl with 1 to 5 carbon atoms, or 5 carbon atoms It may be substituted with ~10 cycloalkyl groups, and R ｂ , R ｃ , R ｄ , R ｅ , R ｆ , and R ｇ Among these, adjacent groups bond together to form a b ring, c ring, d ring, e ring, and f ring, respectively. Along with the ring and the γ ring, there are aryl rings with 9 to 16 carbon atoms or heteroaryl rings with 6 to 15 carbon atoms. A ring may be formed, and at least one hydrogen in the formed ring has six carbon atoms. ~16 aryls, heteroaryls with 2 to 20 carbon atoms, diarylaminos (however, aryl) (aryl is an aryl with 6 to 10 carbon atoms), diarylboryl (however, aryl is an aryl with 6 to 10 carbon atoms) (These are aryl compounds, and the two aryl compounds may be linked by a single bond or a linking group.) Even if substituted with alkyl groups having 1 to 12 carbon atoms, or cycloalkyl groups having 3 to 16 carbon atoms Often, at least one hydrogen atom in these substituents is an aryl or carbon atom having 6 to 10 carbon atoms. Heteroaryls with 2 to 10 prime numbers, alkyls with 1 to 5 carbon atoms, or sic compounds with 5 to 10 carbon atoms. It may also be substituted with a r-alkyl group. In rings b, c, d, e, f, and g, any "-C(-R)=" (this Here R is, R ｂ , R ｃ , R ｄ , R ｅ , R ｆ , or R ｇ (is replaced by "-N=") It's fine if you keep it, Y １ , Y ２ , and Y ３ These are, independently, >B-, >P-, >P(=O)-, and Ta is > P (= S) -, X １ and X ２ These are, independently, >N-R, >O, >S, or >C(-R) ２ And the R and C(-R) of >N-R ２ R is independently hydrogen and carbon aryls with 6 to 10 carbon atoms, heteroaryls with 2 to 10 carbon atoms, alkyls with 1 to 5 carbon atoms, or is a cycloalkyl group having 5 to 10 carbon atoms, and at least one hydrogen atom in R is It may also be substituted with alkyl groups having 1 to 5 carbon atoms or cycloalkyl groups having 5 to 10 carbon atoms. 、 X １ The above >N-R's R or >C(-R) ２ R is a single bond, -N(-R)- -O-, -S-, or -C(-R) ２ - means that it may be bonded to the b ring, X ２ and The above >N-R's R or >C(-R) ２ R represents a single bond, -N(-R)-, -O- -S-, or -C(-R) ２ -Therefore, it may be bonded to the e ring, and the -N(-R ) - R and - C (-R) ２ The R in - represents hydrogen and carbon atoms with 6 to 10 carbon atoms, respectively, independently. Rheel, heteroaryl with 2 to 10 carbon atoms, alkyl with 1 to 5 carbon atoms, or with 5 carbon atoms It is a cycloalkyl group of 10, and at least one hydrogen atom in R is a carbon-1 to carbon-5 group. They may be substituted with alkyl or cycloalkyl groups having 5 to 10 carbon atoms. The c and d rings, the g and b rings, and the f and e rings are each independent of each other. Bonding, -N(-R)-, -O-, -S-, or -C(-R) ２ Even if they are joined by - Often, the R and -C(-R) of the aforementioned -N(-R) ２ The R in - is independently of hydrogen. aryl compounds with 6 to 10 carbon atoms, heteroaryl compounds with 2 to 10 carbon atoms, and alkyl compounds with 1 to 5 carbon atoms. R, or a cycloalkyl group having 5 to 10 carbon atoms, wherein at least one water molecule in R The element is substituted with an alkyl group having 1 to 5 carbon atoms or a cycloalkyl group having 5 to 10 carbon atoms. Often, However, in formula (2A) above, the cd bond of the c ring and the d ring, and X １ As for N-R R (where R is an alkyl group having 1 to 5 carbon atoms or a cycloalkyl group having 5 to 10 carbon atoms) (Limited to the aforementioned aryls having 6 to 10 carbon atoms, which may be replaced) and the X of the b ring １ b bond and , X ２ >N-R's R (this R is the alkyl or C1-C5 alkyl or C5- (Limited to the aryl atoms having 6 to 10 carbon atoms, which may be substituted with 10 cycloalkyl groups.) and X of the e ring ２ Of the three bonds with the e bond, one or two bonds exist. And, Furthermore, in formula (2B) above, the cd bond between the c ring and the d ring, and the gb bond between the g ring and the b ring. And, of the three bonds between the f-ring and the fe-bond of the e-ring, one or two of the bonds are It exists, In the compound represented by formula (2A) or formula (2B) above, the b ring, the c ring, The d ring, the e ring, the f ring, the g ring, the ring on which the above is formed, the aryl, and the At least one of the heteroaryls is at least one cycloalkane having 3 to 16 carbon atoms. They may be condensed in such a way, and at least one hydrogen in the cycloalkane is carbon number aryl groups with 6 to 10 carbon atoms, heteroaryl groups with 2 to 10 carbon atoms, alkyl groups with 1 to 5 carbon atoms, It may be substituted with a cycloalkyl group having 5 to 10 carbon atoms. At least one hydrogen in the compound represented by formula (2A) or formula (2B) above is It may be substituted with deuterium, cyano, or halogen. The polycyclic aromatic compound as described in claim 3.

6. In the above formula (2A) or formula (2B), R ａ These include hydrogen, aryl atoms with 6 to 16 carbon atoms, heteroaryl atoms with 2 to 20 carbon atoms, and diaryl atoms. arylamino (whereas aryl has 6 to 10 carbon atoms), diarylboryl (however Aryls are aryl compounds with 6 to 10 carbon atoms, and two aryls are linked by a single bond or a linking group. (May be bonded together), alkyl groups having 1 to 12 carbon atoms, or cycloa groups having 3 to 16 carbon atoms It is Lukil, and the R ａ At least one hydrogen in is an alkyl group having 1 to 5 carbon atoms. It may be substituted with a cycloalkyl group having 5 to 10 carbon atoms. R ｂ , R ｃ , R ｄ , R ｅ , R ｆ , and R ｇ These are, independently, hydrogen, carbon atoms with 6 carbon atoms... 16 aryls, heteroaryls with 2 to 20 carbon atoms, diarylaminos (however aryl) (aryls with 6 to 10 carbon atoms), diarylboryls (where aryls have 6 to 10 carbon atoms) (It is an aryl compound, and the two aryl compounds may be linked by a single bond or a linking group), carbon The R is an alkyl group with prime numbers 1 to 12, or a cycloalkyl group with 3 to 16 carbon atoms. ｂ , R ｃ , R ｄ , R ｅ , R ｆ , and R ｇ At least one hydrogen in is a carbon-1 to carbon-5 a It may be substituted with lucyl or a cycloalkyl group having 5 to 10 carbon atoms. Y １ , Y ２ , and Y ３ It is >B-, X １ and X ２ This is >N-R, where R in >N-R is hydrogen, and a carbon atom with 6 to 10 carbon atoms. Rheel, heteroaryl with 2 to 10 carbon atoms, alkyl with 1 to 5 carbon atoms, or with 5 carbon atoms It is a cycloalkyl group of 10, and at least one hydrogen atom in R is a carbon-1 to carbon-5 group. It may also be substituted with alkyl groups. X １ In the aforementioned >N-R, R may be bonded to the b ring by a single bond, X ２ and In the aforementioned >N-R, R may be bonded to the e ring by a single bond. The c and d rings, the g and b rings, and the f and e rings are each independent of each other. They may be bonded together, However, in formula (2A) above, the cd bond of the c ring and the d ring, and X １ As for N-R R (This R is a C6-C10 alkyl which may be substituted with the C1-C5 alkyl) (Limited to reels) and X of ring b １ b bond and X ２ > R of N-R (this R is the aforementioned (Limited to aryl atoms having 6 to 10 carbon atoms, which may be substituted with alkyl atoms having 1 to 5 carbon atoms) X of the e-circle ２ Of the three bonds with the e bond, one or two bonds are present. the law of nature, Furthermore, in formula (2B) above, the cd bond between the c ring and the d ring, and the gb bond between the g ring and the b ring. And, of the three bonds between the f-ring and the fe-bond of the e-ring, one or two of the bonds are It exists, In the compound represented by formula (2A) or formula (2B) above, the b ring, the c ring, The d ring, the e ring, the f ring, the g ring, the aryl, and the heteroaryl Even if at least one is condensed with at least one cycloalkane having 3 to 14 carbon atoms Often, at least one hydrogen atom in the cycloalkane is an alkyl group having 1 to 5 carbon atoms. Even if it is replaced, At least one hydrogen in the compound represented by formula (2A) or formula (2B) above is It may be substituted with deuterium, cyano, or halogen. The polycyclic aromatic compound as described in claim 3.

7. A polycyclic aromatic compound according to claim 3, represented by any of the following structural formulas. 【Transformation 3】 In each formula, R is independently a hydrogen atom, an aryl atom with 6 to 16 carbon atoms, or a heteroatomic atom with 2 to 20 carbon atoms. Aryl, diarylamino (where aryl has 6 to 10 carbon atoms), diary Luboryl (where aryl is an aryl with 6 to 10 carbon atoms, and the two aryls are single-bonded) (or may be bonded by a linking group), alkyl with 1 to 12 carbon atoms, or 3 carbon atoms It is a cycloalkyl group of ~16 atoms, and at least one hydrogen atom in R has 1 to 5 carbon atoms. It may be substituted with an alkyl group or a cycloalkyl group having 5 to 10 carbon atoms. Each of o is an independent integer between 1 and 3. p are independent integers from 1 to 4. Each q is an independent integer between 1 and 5. In each of the above formulas, at least one hydrogen atom is deuterium, cyano, or It may be substituted with a halogen.

8. A polycyclic aromatic compound according to claim 1, represented by any of the following structural formulas. 【Chemistry 4】 【Transformation 5】 【Transformation 6】

9. A polycyclic aromatic compound according to any one of claims 1 to 8 is substituted with a reactive substituent, sexual compound.

10. A polymer compound obtained by polymerizing the reactive compound described in claim 9 as a monomer, and This is a polymer crosslinked material obtained by further crosslinking the polymer compound in question.

11. A pendant-type polymer compound obtained by substituting the reactive compound described in claim 9 into the main chain polymer. A substance, or a pendant-type polymer compound further crosslinked. body.

12. A material for organic devices containing a polycyclic aromatic compound as described in any one of claims 1 to 8. 。

13. A material for an organic device containing the reactive compound described in claim 9.

14. A material for organic devices containing the polymer compound or polymer crosslinker described in claim 10. Fee.

15. The pendant-type polymer compound or pendant-type polymer crosslinked material described in claim 11 Materials for organic devices.

16. The aforementioned organic device material is an organic electroluminescent device material, an organic field-effect transistor material Claims 12 to 15 are materials, organic thin-film solar cell materials, or wavelength conversion filter materials. Organic device materials as described in any of the following.

17. The organic electroluminescent material is a material for the light-emitting layer, as described in claim 16. Materials for use.

18. An ink mixture comprising a polycyclic aromatic compound as described in any one of claims 1 to 8 and an organic solvent. Finished product.

19. An ink composition comprising the reactive compound described in claim 9 and an organic solvent.

20. An ink composition comprising a main-chain polymer, the reactive compound described in claim 9, and an organic solvent. thing.

21. An ink comprising the polymer compound or polymer crosslinker described in claim 10 and an organic solvent. composition.

22. A pendant-type polymer compound or pendant-type polymer crosslinked material as described in claim 11, An ink composition containing an organic solvent.

23. A pair of electrodes consisting of an anode and a cathode, and disposed between the pair of electrodes, according to claims 1 to 8. A polycyclic aromatic compound as described in either claim, a reactive compound as described in claim 9, or a compound as described in claim 10. The polymer compound or polymer crosslinked material to be placed on, or the pendant type described in claim 11. An organic electric field having an organic layer containing a polymer compound or a pendant-type polymer crosslinked material. Light-emitting element.

24. The organic electroluminescent element according to claim 23, wherein the organic layer is a light-emitting layer.

25. The light-emitting layer comprises a host, the polycyclic aromatic compound as a dopant, and a reactive compound. Polymer compounds, polymer crosslinks, pendant-type polymer compounds, or pendant-type polymer crosslinks An organic electroluminescent element according to claim 24, comprising a body.

26. The aforementioned light-emitting layer further comprises a compound represented by the following general formula (H1) and a compound represented by the following general formula (H2). Compounds that are subjected to the following general formula (H3), compounds represented by the following general formula (H4) Compounds containing the following formula, compounds represented by the following general formula (H5), compounds represented by the following general formula (H6) The product contains at least one selected from the group consisting of compounds and TADF materials. An organic electroluminescent element as described in item 25. 【Transformation 7】 In the above general formula (H1), L １ This is arylene with 6 to 30 carbon atoms or helium with 2 to 30 carbon atoms. It is teloarrine, In the above general formula (H2), L ２ and L ３ These are, independently, ants with 6 to 30 carbon atoms. It is a heteroaryl compound or a heteroaryl compound with 2 to 30 carbon atoms. In the above general formula (H3), MU independently comprises any two hydrogen atoms from an aromatic compound. The divalent groups represented by the parentheses, EC, each independently possess any one water molecule from the aromatic compound. It is a monovalent group represented by excluding elementary atoms, where two hydrogen atoms in MU are substituted with EC or MU. Here, k is an integer between 2 and 50000. In the above general formula (H4), G is independently either =C(-H)- or =N-, and Note = The H in C(-H)- is substituted with a substituent or a structure represented by other formulas (H4) Often, In the above general formula (H5), R １ ~R １１ These are, independently, hydrogen, aryl, heteroaryl, and diarylia. Mino, diheteroarylamino, arylheteroarylamino, alkyl or cyclo It is alkyl, and the R １ ~R １１ At least one hydrogen in is further aryl, he It may be substituted with teloaryl, diarylamino, alkyl, or cycloalkyl. Ku, R １ ~R １１ Adjacent groups among them bond together with the a, b, or c rings, forming an aryl group. They may form a ring or a heteroaryl ring, and at least one of the formed rings The hydrogen in aryl, heteroaryl, diarylamino, diheteroarylamino, and They may be substituted with a reel heteroarylamino, alkyl, or cycloalkyl group. At least one hydrogen atom in these substituents is further aryl, heteroaryl, or dia They may be substituted with reel-amino, alkyl, or cycloalkyl groups. In ring a, ring b, and ring c, any "-C(-R) =" (where R is R １ ~R １ １ The part "-N=" may be replaced with "-N=". In the above general formula (H6), R １ ~R １６ These are, independently, hydrogen, aryl, heteroaryl, and diarylia. Mino, diheteroarylamino, arylheteroarylamino, alkyl or cyclo It is alkyl, and the R １ ~R １６ At least one hydrogen in is further aryl, he It may be substituted with teloaryl, diarylamino, alkyl, or cycloalkyl. Ku, R １ ~R １６ Among them, adjacent groups bond together to form an a-ring, b-ring, c-ring, or d-ring. They may form a reel ring or a heteroaryl ring, and in the formed ring, Another hydrogen is aryl, heteroaryl, diarylamino, diheteroarylamino Even if substituted with aryl heteroarylamino, alkyl, or cycloalkyl Often, at least one hydrogen atom in these substituents is further aryl or heteroaryl. They may be substituted with diarylamino, alkyl, or cycloalkyl groups, and In each of the above formulas, at least one hydrogen atom in the compound or structure has 1 to 6 carbon atoms. Substituted with alkyl, cycloalkyl, cyano, halogen, or deuterium. It's okay if it's not allowed.

27. At least one electron transport layer and electron injection layer disposed between the cathode and the light-emitting layer It has two layers, and at least one of the electron transport layer and the electron injection layer is a borane derivative, pyri Zin derivatives, fluorantene derivatives, BO derivatives, anthracene derivatives, benzofluorine Len derivatives, phosphine oxide derivatives, pyrimidine derivatives, carbazole derivatives, Liazin derivatives, benzimidazole derivatives, phenanthroline derivatives, quinolinol derivatives Metal complexes, thiazole derivatives, benzothiazole derivatives, silole derivatives, and azolines Any of claims 23 to 26, containing at least one selected from the group consisting of derivatives Organic electroluminescent element described below.

28. At least one of the electron transport layer and electron injection layer is further made of alkali metal, Alkali earth metals, rare earth metals, alkali metal oxides, alkali metal halides, Oxides of alkaline earth metals, halides of alkaline earth metals, oxides of rare earth metals, rare earth Metallic halides, alkali metal organic complexes, alkaline earth metal organic complexes and rare Claim 27 contains at least one selected from the group consisting of organic complexes of earth metals. The organic electroluminescent device described.

29. At least one of the following: hole injection layer, hole transport layer, light emission layer, electron transport layer, and electron injection layer Each layer is a polymer compound formed by polymerizing low-molecular-weight compounds that can form each layer as monomers. Alternatively, a polymer crosslinked polymer obtained by further crosslinking the polymer compound, or forming each layer The resulting low molecular weight compound is reacted with a main chain polymer to form a pendant-type polymer compound, or A claim comprising a pendant-type polymer crosslinked material obtained by further crosslinking the pendant-type polymer compound. An organic electroluminescent element as described in any of items 23 to 28.

30. Display device or lighting equipped with an organic electroluminescent element as described in any one of claims 23 to 29 Device.

31. A wavelength conversion filter comprising the wavelength conversion filter material described in claim 16.

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