Amino-substituted polycyclic aromatic compound

Abstract

To provide a novel amino-substituted polycyclic aromatic compound and an organic EL device using the same.SOLUTION: Introduction of specific amino groups and specific substituents (Ra group and Rb group) into a polycyclic aromatic compound in which multiple aromatic rings are linked by a boron atom and an oxygen atom, etc. provides more choices of organic device materials such as an organic EL device material. In addition, use of such a novel amino-substituted polycyclic aromatic compound as the organic EL device material provides, for example, an organic EL device having excellent luminous efficiency and device life.SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to an amino-substituted polycyclic aromatic compound and a multimer thereof (hereinafter collectively referred to as "polycyclic aromatic compound"). and organic electroluminescent devices, organic field-effect transistors, and The present invention relates to an organic thin-film solar cell, a display device, and a lighting device. "Organic electroluminescent device" is sometimes written as "organic EL device" or simply "device." do. [Background technology]

[0002] Conventionally, display devices using electroluminescent light-emitting elements have been developed to be energy-efficient and thin. Various researches have been conducted, and organic electroluminescent devices made of organic materials are easy to make lighter and larger. In particular, the luminescence properties of blue, one of the three primary colors of light, have been actively investigated. Development of organic materials with charge transport capabilities (holes, electrons, etc.) (potential to become semiconductors or superconductors) Regarding the development of organic materials with the potential for It has been actively researched to date.

[0003] The organic EL element comprises a pair of electrodes consisting of an anode and a cathode, and a light-emitting element disposed between the pair of electrodes. The layer containing the organic compound has a structure consisting of one or more layers. The layers include a light-emitting layer and a charge transport / injection layer that transports or injects charges such as holes and electrons. However, a variety of organic materials suitable for these layers have been developed.

[0004] As a material for the light-emitting layer, for example, benzofluorene-based compounds have been developed (International (Publication No. 2004 / 061047) Examples of hole transport materials include triphenylamine. Compounds based on ZnO have been developed (Japanese Patent Application Laid-Open No. 2001-172232). For example, anthracene-based compounds have been developed (Japanese Patent Laid-Open Publication No. 2005-170911).

[0005] In recent years, triphenylamine has been used as a material for organic EL elements and organic thin-film solar cells. Materials that have been improved from amine derivatives have also been reported (WO 2012 / 118164). The starting material was N,N'-diphenyl-N,N'-bis(3-methylphenyl) )-1,1'-biphenyl-4,4'-diamine (TPD) as a reference A material characterized by enhanced planarity due to the linking of aromatic rings that make up the amine In this paper, for example, the charge transport properties of NO-linked compounds (compound 1 on page 63) are evaluated. However, there is no description of a method for producing materials other than NO-linked compounds. In addition, since the electronic state of the entire compound differs depending on the linked elements, there are many compounds other than NO-linked compounds. The properties that can be obtained from other materials are also unknown. For example, the triplet exciton energy (T1) is large. Compounds with a wider conjugated structure can emit phosphorescence at shorter wavelengths, resulting in blue light. It is useful as a material for the light-emitting layer. It is also useful as an electron transport material or hole transport material sandwiching the light-emitting layer. Therefore, compounds with novel conjugated structures having large T1 are desired.

[0006] The host material for organic EL devices generally contains existing aromatic rings such as benzene and carbazole. It is a molecule that is connected by multiple single bonds or phosphorus or silicon atoms. This is a relatively small conjugated system. By connecting many aromatic rings, the large HOMO-LUMO gap required for the host material can be obtained. This is because the band gap (Eg in the thin film) is guaranteed. The host materials for organic EL devices using thermally activated delayed fluorescent materials have high triplet excitation energy. Ghee (E T ) is also required, but the molecule must have a donor or acceptor aromatic ring or substituent. By linking, SOMO1 and SOMO2 in the triplet excited state (T1) are localized, By reducing the exchange interaction between the two orbitals, the triplet excitation energy (E T ) to improve However, the small aromatic rings in the conjugated system do not have sufficient redox stability. However, existing devices using molecules formed by linking aromatic rings as host materials do not have sufficient life spans. On the other hand, polycyclic aromatic compounds with extended π-conjugated systems generally have excellent redox stability. However, the HOMO-LUMO gap (band gap Eg in thin films) and triplet excitation Electromotive force (E T ) has been considered unsuitable as a host material. [Prior art documents] [Patent documents]

[0007] [Patent Document 1] International Publication No. 2004 / 061047 [Patent Document 2] Japanese Patent Application Laid-Open No. 2001-172232 [Patent Document 3] Japanese Patent Application Laid-Open No. 2005-170911 [Patent Document 4] International Publication No. 2012 / 118164 [Patent Document 5] International Publication No. 2011 / 107186 [Patent Document 6] International Publication No. 2015 / 102118 Summary of the Invention [Problem to be solved by the invention]

[0008] As mentioned above, various materials have been developed for use in organic EL devices. However, in order to increase the options for materials for organic EL devices, In particular, development of new materials other than the NO-linked compounds reported in Patent Documents 1 to 4 is desired. The organic EL characteristics obtained from these devices and their manufacturing methods are not yet known.

[0009] In addition, Patent Document 6 discloses a polycyclic aromatic compound containing boron and an organic EL device using the same. It has been reported that the luminous efficiency and the life span of the device can be improved further to further improve the device characteristics. There is a demand for light-emitting layer materials, particularly dopant materials, that can achieve this. [Means for solving the problem]

[0010] As a result of extensive research to solve the above problems, the present inventors have found that a specific amino group is introduced into the polymer. A layer containing a polycyclic aromatic compound is disposed between a pair of electrodes to form, for example, an organic EL device. The present inventors have found that an excellent organic EL device can be obtained by using the above method, and have completed the present invention. Furthermore, as a result of extensive research into solving the above problems, the present inventors have found that the amino group and specific A layer containing a polycyclic aromatic compound having substituents (Ra groups and Rb groups) introduced at specific positions By disposing the organic EL element between a pair of electrodes, for example, an excellent organic EL element can be obtained. The present invention was completed based on the discovery that a child can be obtained. That is, the present invention relates to the following amino-substituted polycyclic aromatic compounds or multimers thereof, The present invention relates to a material for organic EL devices containing the following amino-substituted polycyclic aromatic compounds or their multimers: We provide materials for organic devices such as silicon dioxide.

[0011] In this specification, chemical structures and substituents may be expressed by the number of carbon atoms. When a substituent is substituted, or when a substituent is further substituted, the number of carbon atoms is It means the total number of carbon atoms in the chemical structure and the substituents, or the number of carbon atoms in the substituents. It does not mean the total number of carbon atoms of the substituents. For example, "substituted with substituent A having carbon number X" "Substituent B with carbon number Y" refers to "substituent B with carbon number Y" with "substituent A with carbon number X". The carbon number Y is not the total number of carbon atoms of the substituent A and the substituent B. For example, "substituent B having Y carbon atoms substituted with substituent A" means "substituent B having Y carbon atoms" The number of carbon atoms Y is the number of substituents A and It is not the total number of carbon atoms of the substituents B and C.

[0012] Section 1. A polycyclic aromatic compound represented by the following general formula (1), or a compound having a structure represented by the following general formula (1): A polymer of polycyclic aromatic compounds with multiple structures. [ka] (In the above formula (1), Ring A, ring B and ring C are each independently an aryl ring or a heteroaryl ring. At least one hydrogen atom in these rings may be substituted, At least one hydrogen atom in at least one of the rings B and C is represented by the formula (Am) In the above formula (Am), Ar1 and Ar2 are each substituted with a group represented by each independently represents an aryl or heteroaryl, and the aryl or heteroaryl At least one hydrogen atom in Ar may be substituted, and Ar and Ar are each a single bond. Alternatively, the group represented by the formula (Am) may be bonded via a linking group, and the group represented by the formula (Am) may be bonded via a linking group. replacing hydrogen in the ring or C ring, Ring B and ring C may be bonded via a linking group; Y 1 is B, P, P=O, P=S, Al, Ga, As, Si-R or Ge-R wherein R in the Si—R and Ge—R is aryl, alkyl, or cycloalkyl; , X 1 and X 2 are independently >O, >NR, >Si(-R)2, >C(- R)2, >S or >Se, and R of the >NR is optionally substituted aryl. (excluding amino groups as substituents), optionally substituted heteroaryl, substituted and the >Si is an optionally substituted alkyl or an optionally substituted cycloalkyl. R in (-R)2 is an optionally substituted aryl, an optionally substituted heteroaryl, aryl, optionally substituted alkyl or optionally substituted cycloalkyl; R in the above >C(-R)2 is hydrogen, an optionally substituted aryl, an optionally substituted optionally substituted heteroaryl, optionally substituted alkyl or optionally substituted cycloaryl and at least one of >NR, >Si(—R)2 and >C(—R)2 is alkyl. In the other case, R is a linking group or a single bond to at least one of the A ring, the B ring and the C ring. and In the compound or structure represented by formula (1), the A ring, the B ring, the C ring, the aryl and the heterocyclic ring are At least one of the heteroaryls may be fused with at least one cycloalkane. Preferably, at least one hydrogen atom in the cycloalkane may be substituted, and the At least one -CH2- in the cycloalkane may be replaced with -O-; and, At least one hydrogen atom in the compound or structure represented by formula (1) can be replaced by a deuterium atom, a sialic acid atom, or a hydroxyl group. It may be substituted with methyl or halogen.

[0013] Section 2. Item 1. The polycyclic aromatic compound according to item 1, which is represented by the following general formula (1A), or the polycyclic aromatic compound according to item 1, which is represented by the following general formula (1 Item 2. A multimer of the polycyclic aromatic compound according to Item 1, having a plurality of structures represented by A). [ka] (In the above formula (1A), Ring A, ring B and ring C are each independently an aryl ring or a heteroaryl ring. At least one hydrogen atom in these rings may be substituted, At least one hydrogen atom in at least one of the rings B and C is represented by the formula (Am) In the above formula (Am), Ar1 is biphenylyl. Ar2 is aryl (excluding biphenylyl) or heteroaryl, At least one hydrogen atom in the phenylyl, aryl or heteroaryl is alkyl or or cycloalkyl, and the group represented by the above formula (Am) is Substitutes for hydrogen in ring B or ring C, Ring B and ring C may be bonded via a linking group; Y 1 is B, P, P=O, P=S, Al, Ga, As, Si-R or Ge-R wherein R in the Si—R and Ge—R is aryl, alkyl, or cycloalkyl; , X 1 and X 2 are independently >O, >NR, >Si(-R)2, >C(- R)2, >S or >Se, and R of the >NR is optionally substituted aryl. (excluding amino groups as substituents), optionally substituted heteroaryl, substituted and the >Si is an optionally substituted alkyl or an optionally substituted cycloalkyl. R in (-R)2 is an optionally substituted aryl, an optionally substituted heteroaryl, aryl, optionally substituted alkyl or optionally substituted cycloalkyl; R in the above >C(-R)2 is hydrogen, an optionally substituted aryl, an optionally substituted optionally substituted heteroaryl, optionally substituted alkyl or optionally substituted cycloaryl and at least one of >NR, >Si(—R)2 and >C(—R)2 is alkyl. In the other case, R is a linking group or a single bond to at least one of the A ring, the B ring and the C ring. and In the compound or structure represented by formula (1A), the A ring, the B ring, the C ring, the aryl and At least one of the heteroaryls is fused to at least one cycloalkane. At least one hydrogen atom in the cycloalkane may be substituted. At least one -CH2- in the cycloalkane may be replaced with -O-. ,and, At least one hydrogen atom in the compound or structure represented by formula (1A) may be replaced by a deuterium atom, a silyl atom, or a methyl group. may be substituted with an anion or halogen.

[0014] Section 3. In the above formula (1A), Ring A, ring B and ring C are each independently an aryl ring or a heteroaryl ring. At least one hydrogen atom in these rings is replaced by a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino, substituted or is an unsubstituted diheteroarylamino, a substituted or unsubstituted arylheteroarylamino, Substituted or unsubstituted diarylboryl (two aryls are connected via a single bond or a linking group) may be bonded to each other), substituted or unsubstituted alkyl, substituted or unsubstituted cyclohexane substituted or unsubstituted alkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, Alternatively, these rings may be substituted with substituted silyl, and these rings may be substituted with Y 1 , X 1 and X 2 a 5- or 6-membered ring sharing a bond with the central fused bicyclic structure of the above formula (1A) and At least one hydrogen atom in at least one of the rings B and C is represented by the formula (Am) and is substituted with a group represented by The B and C rings are >O, >NR, >Si(-R)2, >C(-R)2, >S or and R in the >NR and >Si(-R)2 may be bonded via >Se. aryl, aryl, aryls ... heteroaryl, alkyl or cycloalkyl optionally substituted with alkyl or cycloalkyl; R in the >C(—R)2 is hydrogen, alkyl or cycloalkyl. substituted with aryl, alkyl or cycloalkyl, optionally substituted with aryl; may be heteroaryl, alkyl, or cycloalkyl, and may also be >NR, > R in at least one of Si(-R)2 and >C(-R)2 is -O-, -S-, -C(-R)2- or a single bond to at least one of the rings B and C R in the -C(-R)2- may be hydrogen, alkyl or cycloalkyl. can be, Y 1 is B, P, P=O, P=S, Al, Ga, As, Si-R or Ge-R wherein R in the Si—R and Ge—R is aryl, alkyl, or cycloalkyl; , X 1 and X 2 are independently >O, >NR, >Si(-R)2, >C(- R in the above >NR and >Si(-R)2 is aryl, alkyl, or cycloalkyl, each of which may be independently substituted with alkyl or cycloalkyl; heteroaryl, alkyl or cycloalkyl optionally substituted with aryl or cycloalkyl; R in the >C(—R)2 is hydrogen, alkyl or cycloalkyl. substituted with aryl, alkyl or cycloalkyl, and the above-mentioned >NR, >S R in at least one of i(-R)2 and >C(-R)2 is -O-, -S-, - and at least one of the rings A, B and C via C(—R)2— or a single bond. R in the -C(-R)2- may be hydrogen, alkyl or cycloalkyl. It is In the compound or structure represented by formula (1A), the A ring, the B ring, the C ring, the aryl and At least one of the heteroaryls is fused to at least one cycloalkane. At least one hydrogen atom in the cycloalkane may be substituted. At least one -CH2- in the cycloalkane may be replaced with -O-. , In the case of a polymer, a dimer or a polymer having two or three structures represented by general formula (1A) is a trimer, and At least one hydrogen atom in the compound or structure represented by formula (1A) may be replaced by a deuterium atom, a silyl atom, or a methyl group. optionally substituted with an anion or halogen; Item 2. The polycyclic aromatic compound or a multimer thereof according to Item 2.

[0015] Section 4. Item 2. The polycyclic aromatic compound according to item 2, which is represented by the following general formula (2A): [ka] (In the above formula (2A), In the a ring, the b ring, and the c ring, any "-C(-R)=" (where R is the formula (2A) R in 1 ~R 11 ) may be replaced with "-N=", and any "-C(-R )=C(-R)- (where R is R in formula (2A) 1 ~R 11 ) is "-N(-R )-", "-O-", or "-S-", and the "-N(-R) R in - is aryl, alkyl, or cycloalkyl; R 1 ~R 11 are each independently hydrogen, aryl, heteroaryl, diaryla amino, diheteroarylamino, arylheteroarylamino, diarylboryl (2 the two aryls may be bonded via a single bond or a linking group), alkyl, cycloalkenyl, alkyl, alkoxy, aryloxy, triarylsilyl, trialkylsilyl, tri Cycloalkylsilyl, dialkylcycloalkylsilyl or alkyldicycloalkyl and aryl, aryl, aryl, heteroaryl, or aryl. may be substituted with alkyl or cycloalkyl, and R 1 ~R 11 Next to my house The adjacent groups are bonded to form an aryl or heteroaryl ring together with the a, b or c ring. At least one hydrogen atom in the formed ring may be selected from the group consisting of aryl, heterocyclic, Diaryl, diarylamino, diheteroarylamino, arylheteroarylamino Diarylboryl (two aryls may be bonded via a single bond or a linking group) (ii), alkyl, cycloalkyl, alkoxy, aryloxy, triarylsilyl, Trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl or may be substituted with alkyldicycloalkylsilyl, and at least One hydrogen is replaced by aryl, heteroaryl, alkyl, or cycloalkyl. It's okay to be there, R 4 ~R 11 At least one of the groups is a group represented by the above formula (Am), and / or in the aryl ring or heteroaryl ring formed together with the ring b or ring c. at least one hydrogen atom of the formula (Am) is substituted with a group represented by the formula (Am), R 7 and R 8 are bonded to form >O, >NR, >Si(-R)2, >C(-R)2, > R in the above >NR and >Si(-R)2 may be S or >Se, each independently being an aryl having 6 to 12 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, or a aryl having 1 carbon atom R in the above >C(-R)2 is an alkyl having 3 to 6 carbon atoms or a cycloalkyl having 3 to 14 carbon atoms. is hydrogen, aryl having 6 to 12 carbon atoms, heteroaryl having 2 to 15 carbon atoms, and the above-mentioned >NR, >Si R in at least one of (-R)2 and >C(-R)2 is -O-, -S-, -C (-R)2- or a single bond to at least one of the rings b and c; R in the -C(-R)2- may be alkyl having 1 to 6 carbon atoms or alkyl having 3 to 14 carbon atoms. is a cycloalkyl of Y 1 is B, P, P=O, P=S, Al, Ga, As, Si-R or Ge-R R in the Si—R and Ge—R is an aryl having 6 to 12 carbon atoms, an aryl having 1 to 6 carbon atoms, alkyl or cycloalkyl having 3 to 14 carbon atoms; X 1 and X 2 are independently >O, >NR, >Si(-R)2, >C(- R in the above >NR and >Si(-R)2 is aryl having 6 to 12 carbon atoms, heteroaryl having 2 to 15 carbon atoms, and R in the above >C(-R)2 is an alkyl having 3 to 14 carbon atoms or a cycloalkyl having 3 to 14 carbon atoms. , hydrogen, aryl having 6 to 12 carbon atoms, heteroaryl having 2 to 15 carbon atoms, alkyl or cycloalkyl having 3 to 14 carbon atoms, and R in at least one of -R)2 and >C(-R)2 is -O-, -S-, -C( -R)2- or a single bond to at least one of the ring a, ring b, and ring c R in the -C(-R)2- may be alkyl having 1 to 6 carbon atoms or alkyl having 3 to 6 carbon atoms. 14 cycloalkyl, In the compound represented by formula (2A), the ring a, the ring b, the ring c, and the formed At least one of the ring, the aryl and the heteroaryl has 3 to 24 carbon atoms, It may be condensed with at least one cycloalkane, At least one hydrogen atom is an aryl having 6 to 30 carbon atoms, a heteroaryl having 2 to 30 carbon atoms, or , and may be substituted with alkyl having 1 to 24 carbon atoms or cycloalkyl having 3 to 24 carbon atoms. Preferably, at least one -CH2- in the cycloalkane is replaced with -O-. It is also possible to At least one hydrogen atom in the compound of formula (2A) is deuterium, cyano, or may be substituted with halogen.

[0016] Section 5. In the above formula (2A), In the a ring, the b ring, and the c ring, any "-C(-R)=" (where R is the formula (2A) R in 1 ~R 11 ) may be replaced with "-N=", and any "-C(-R )=C(-R)- (where R is R in formula (2A) 1 ~R 11 ) is "-N(-R )-", "-O-", or "-S-", and the "-N(-R) R in "-" is an aryl having 6 to 12 carbon atoms, an alkyl having 1 to 6 carbon atoms, or an alkyl having 3 to 1 carbon atoms. 4 cycloalkyl, R 1 ~R 11 are each independently hydrogen, an aryl having 6 to 30 carbon atoms, an aryl having 2 to 3 carbon atoms, 0 heteroaryl, diarylamino (where aryl has 6 to 12 carbon atoms) , diarylboryl (where aryl is an aryl having 6 to 12 carbon atoms, and two aryls alkyl having 1 to 24 carbon atoms, Cycloalkyl and triarylsilyl with 3 to 24 prime numbers (where aryl has 6 to 12 carbon atoms) aryl), or trialkylsilyl (wherein alkyl has 1 to 6 carbon atoms) and R 1 ~R 11 Adjacent groups among these are bonded to form ring a, ring b, or ring c. Both of them form an aryl ring having 9 to 16 carbon atoms or a heteroaryl ring having 6 to 15 carbon atoms. At least one hydrogen atom in the formed ring may be substituted by an aryl having 6 to 10 carbon atoms, Alkyl having 1 to 12 carbon atoms, cycloalkyl having 3 to 16 carbon atoms, triarylsilyl (or (Aryl is aryl having 6 to 12 carbon atoms), or trialkylsilyl (but alkyl may be substituted with alkyl having 1 to 5 carbon atoms, R 4 ~R 11 At least one of the groups is a group represented by the above formula (Am), and / or in the aryl ring or heteroaryl ring formed together with the ring b or ring c. At least one hydrogen atom of the formula (Am) is substituted with a group represented by the formula (Am In the formula, Ar1 is biphenylyl, and Ar2 is an aryl having 6 to 30 carbon atoms (provided that biphenylyl is excluded) or heteroaryl having 2 to 30 carbon atoms, and the biphenylyl At least one hydrogen atom in the aryl or heteroaryl is replaced by an aryl having 1 to 24 carbon atoms. may be substituted with alkyl or cycloalkyl having 3 to 24 carbon atoms; R 7 and R 8 are bonded to form >O, >NR, >C(-R)2 or >S R in the above >NR may be an aryl having 6 to 10 carbon atoms, an alkyl having 1 to 5 carbon atoms, or is a cycloalkyl having 5 to 10 carbon atoms, and R in the >C(-R)2 is hydrogen, aryl having 1 to 10 carbon atoms, alkyl having 1 to 5 carbon atoms, or cycloalkyl having 5 to 10 carbon atoms; the law of nature, Y 1 is B, P, P=O, P=S or Si-R, and R of the Si-R is the number of carbon atoms 6-10 aryl, 1-5 carbon alkyl, or 5-10 carbon cycloalkyl can be, X 1 and X 2 are each independently >O, >NR, >C(-R)2 or >S R in the >NR is an aryl having 6 to 10 carbon atoms, an alkyl having 1 to 5 carbon atoms, or R in the >C(-R)2 is hydrogen, cycloalkyl having 6 to 10 carbon atoms, aryl having 1 to 5 carbon atoms, or cycloalkyl having 5 to 10 carbon atoms; , In the compound represented by formula (2A), the ring a, the ring b, the ring c, and the formed At least one of the ring, the aryl and the heteroaryl has 3 to 20 carbon atoms, It may be condensed with at least one cycloalkane, At least one hydrogen atom is an aryl having 6 to 16 carbon atoms, a heteroaryl having 2 to 22 carbon atoms, or , and may be substituted with alkyl having 1 to 12 carbon atoms or cycloalkyl having 3 to 16 carbon atoms. Well, and At least one hydrogen atom in the compound of formula (2A) is deuterium, cyano, or optionally substituted with halogen; Item 4. The polycyclic aromatic compound according to item 4.

[0017] Section 6. In the above formula (2A), In the a ring, the b ring, and the c ring, any "-C(-R)=" (where R is the formula (2A) R in 1 ~R 11) may be replaced with "-N=", and any "-C(-R )=C(-R)- (where R is R in formula (2A) 1 ~R 11 ) is "-N(-R )-", "-O-", or "-S-", and the "-N(-R) R in "-" is an aryl having 6 to 10 carbon atoms, an alkyl having 1 to 5 carbon atoms, or an alkyl having 5 to 1 carbon atoms. 0 cycloalkyl, R 1 ~R 11 are each independently hydrogen, an aryl having 6 to 16 carbon atoms, an aryl having 2 to 2 carbon atoms, 0 heteroaryl, diarylamino (where aryl is aryl having 6 to 10 carbon atoms) , alkyl having 1 to 12 carbon atoms or cycloalkyl having 3 to 16 carbon atoms; R 5 and R 10 At least one of the above is a group represented by the formula (Am), In m), Ar1 is biphenylyl, and Ar2 is an aryl having 6 to 16 carbon atoms (only (excluding biphenylyl) or heteroaryl having 2 to 20 carbon atoms, At least one hydrogen atom in the alkyl, aryl or heteroaryl is an alkyl group having 1 to 12 carbon atoms. may be substituted with alkyl or cycloalkyl having 3 to 16 carbon atoms, R 7 and R 8 may be bonded to form >O, >NR or >C(-R)2. R in the above >NR is an aryl having 6 to 10 carbon atoms, an alkyl having 1 to 5 carbon atoms, or a carbon atom. R in the >C(-R)2 is hydrogen, cycloalkyl having 6 to 10 carbon atoms. aryl, alkyl having 1 to 5 carbon atoms, or cycloalkyl having 5 to 10 carbon atoms; Y 1 is B, P, P=O or P=S, X 1and X 2 are each independently >O, >NR, or >C(-R)2; R in the above >NR is an aryl having 6 to 10 carbon atoms, an alkyl having 1 to 5 carbon atoms, or R in the >C(-R)2 is hydrogen, a cycloalkyl having 6 to 10 carbon atoms, aryl, alkyl having 1 to 5 carbon atoms, or cycloalkyl having 5 to 10 carbon atoms; In the compound represented by formula (2A), the ring a, the ring b, the ring c, and the At least one of the aryls having 6 to 10 carbon atoms as R in NR is an aryl having 3 to 16 carbon atoms. may be condensed with at least one cycloalkane, At least one hydrogen atom is an alkyl group having 1 to 6 carbon atoms or a cycloalkyl group having 3 to 14 carbon atoms. and At least one hydrogen atom in the compound of formula (2A) is deuterium, cyano, or optionally substituted with halogen; Item 4. The polycyclic aromatic compound according to item 4.

[0018] Section 7. In the above formula (2A), R 1 ~R 11 are each independently hydrogen, an aryl having 6 to 16 carbon atoms, a diaryla amino (wherein aryl is aryl having 6 to 10 carbon atoms), alkyl having 1 to 12 carbon atoms or is a cycloalkyl having 3 to 16 carbon atoms; R 5 and R 10 At least one of the above is a group represented by the formula (Am), In m), Ar1 is biphenylyl, and Ar2 is an aryl having 6 to 16 carbon atoms (only (excluding biphenylyl) or heteroaryl having 2 to 20 carbon atoms, At least one hydrogen atom in the alkyl, aryl or heteroaryl is an alkyl group having 1 to 12 carbon atoms. may be substituted with alkyl or cycloalkyl having 3 to 16 carbon atoms, Y 1 is B, X 1 and X 2 are both >NR, or X 1 is >NR and X 2 HA>O and R in the >NR is an aryl having 6 to 10 carbon atoms, an alkyl having 1 to 5 carbon atoms, or is a cycloalkyl having 5 to 10 carbon atoms, In the compound represented by formula (2A), the ring a, the ring b, the ring c, and the At least one of the aryls having 6 to 10 carbon atoms as R in NR is an aryl having 3 to 14 carbon atoms. It may be condensed with a cycloalkane, and at least one of the cycloalkane The hydrogen may be substituted with alkyl having 1 to 5 carbon atoms, and At least one hydrogen atom in the compound represented by formula (2A) is deuterium or halogen. optionally substituted, Item 4. The polycyclic aromatic compound according to item 4.

[0019] Section 8. Item 1, wherein the polycyclic aromatic compound is represented by the following general formula (2B): Item 2. A multimer of the polycyclic aromatic compound according to Item 1, having a plurality of structures represented by the formula (B). [ka] (In the above formula (2B), Any "-C(-H)=" in the a, b, and c rings is replaced with "-N=". It is okay to have R 21 ~R 30 are each independently hydrogen, aryl, heteroaryl, or diaryl Amino, diheteroarylamino, arylheteroarylamino, diarylboryl ( two aryls may be bonded via a single bond or a linking group), alkyl, cyclo Alkyl, alkoxy, aryloxy, triarylsilyl, trialkylsilyl, triarylsilyl Cycloalkylsilyl, dialkylcycloalkylsilyl or alkyldicycloalkylsilyl alkylsilyl, in which at least one hydrogen atom is an aryl, heteroaryl, or , optionally substituted with alkyl or cycloalkyl; R 21 ~R 30 Adjacent groups among these may be bonded to form an aryl ring or ring b together with the d or e ring. or heteroaryl ring, and at least one hydrogen atom in the ring formed The element is an aryl, heteroaryl, diarylamino, diheteroarylamino, aryl arylheteroarylamino, diarylboryl (two aryls are connected via a single bond or a linking group) alkyl, cycloalkyl, alkoxy, aryloxy, Triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylsilyl may be substituted with alkyldicycloalkylsilyl or alkyldicycloalkylsilyl, At least one hydrogen atom in the above is aryl, heteroaryl, alkyl, or cycloalkyl. may be substituted with alkyl, R 25 and R 26 are bonded to form >O, >NR, >Si(-R)2, >C(-R)2 , >S or >Se, and R in the >NR and >Si(—R)2 may be each independently represents an aryl having 6 to 12 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, or a carbon alkyl having 1 to 6 carbon atoms or cycloalkyl having 3 to 14 carbon atoms, At least one hydrogen atom is an aryl having 6 to 12 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, or a carbon atom. It may be substituted with alkyl having 1 to 6 prime numbers or cycloalkyl having 3 to 14 carbon atoms, R in the above >C(-R)2 is hydrogen, aryl having 6 to 12 carbon atoms, heteroaryl having 2 to 15 carbon atoms. aryl, alkyl having 1 to 6 carbon atoms, or cycloalkyl having 3 to 14 carbon atoms, At least one hydrogen atom in these groups is preferably an aryl group having 6 to 12 carbon atoms, a heterocyclic group having 2 to 15 carbon atoms, or aryl, alkyl having 1 to 6 carbon atoms, or cycloalkyl having 3 to 14 carbon atoms. It is okay to Ra is an aryl, heteroaryl, alkyl, cycloalkyl, alkoxy, or aryl group. Silyloxy, triarylsilyl, trialkylsilyl, tricycloalkylsilyl, diarylsilyl alkylcycloalkylsilyl or alkyldicycloalkylsilyl, At least one hydrogen atom in the may be substituted with methyl; Rb is hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino. Aryl, heteroaryl, amino, diarylboryl (two aryls are single bond or (which may be bonded via a linking group), alkyl, cycloalkyl, alkoxy, aryl Silyloxy, triarylsilyl, trialkylsilyl, tricycloalkylsilyl, diarylsilyl alkylcycloalkylsilyl or alkyldicycloalkylsilyl, At least one hydrogen atom in the may be substituted with methyl; Y 1 is B, P, P=O, P=S, Al, Ga, As, Si-R or Ge-R R in the Si—R and Ge—R is an aryl having 6 to 12 carbon atoms, an aryl having 1 to 6 carbon atoms, alkyl or cycloalkyl having 3 to 14 carbon atoms; X 1 and X 2 are independently >O, >NR, >Si(-R)2, >C(- R in the above >NR and >Si(-R)2 is aryl having 6 to 12 carbon atoms, heteroaryl having 2 to 15 carbon atoms, and 6 alkyl or cycloalkyl having 3 to 14 carbon atoms, One hydrogen atom can be used in aryls with 6 to 12 carbon atoms, heteroaryls with 2 to 15 carbon atoms, and aryls with 1 carbon atom. may be substituted with alkyl having 1 to 6 carbon atoms or cycloalkyl having 3 to 14 carbon atoms, R in C(-R)2 is hydrogen, 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; At least one hydrogen atom in the alkyl group is an aryl group having 6 to 12 carbon atoms, a heteroaryl group having 2 to 15 carbon atoms, or substituted with alkyl having 1 to 6 carbon atoms or cycloalkyl having 3 to 14 carbon atoms. and at least one of >NR, >Si(—R)2 and >C(—R)2 may be In the formula, R is -O-, -S-, -C(-R)2- or a single bond, and the ring a and the ring b are connected to each other. and c ring, and R of said -C(-R)2- may be bonded to at least one ring of alkyl having 1 to 6 prime numbers or cycloalkyl having 3 to 14 carbon atoms; In the compound or structure represented by formula (2B), the ring a, the ring b, the ring c, At least one of the d ring, the e ring, the formed ring, the aryl and the heteroaryl Each of the cycloalkanes may be condensed with at least one cycloalkane having 3 to 24 carbon atoms. At least one hydrogen atom in the cycloalkane is an aryl having 6 to 30 carbon atoms, Heteroaryl having 2 to 30 carbon atoms, alkyl having 1 to 24 carbon atoms, or cycloalkyl having 3 to 24 carbon atoms. and at least one - in the cycloalkane may be substituted with cycloalkyl. CH2- may be replaced by -O-, and At least one hydrogen atom in the compound or structure represented by formula (2B) may be replaced by a deuterium atom, a silyl atom, or a methyl group. may be substituted with an anion or halogen.

[0020] Section 9. In the above formula (2B), Any "-C(-H)=" in the a, b, and c rings is replaced with "-N=". It is okay to have R 21 ~R 30 are each independently hydrogen, an aryl having 6 to 30 carbon atoms, an aryl having 2 to 30 carbon atoms, 30 heteroaryl, diarylamino (where aryl is aryl having 6 to 12 carbon atoms) ), diarylboryl (where aryl is an aryl with 6 to 12 carbon atoms, and two aryls alkyl having 1 to 24 carbon atoms, Cycloalkyl and triarylsilyl having 3 to 24 carbon atoms (wherein aryl has 6 to 1 carbon atoms) 2 aryl), or trialkylsilyl (wherein alkyl has 1 to 6 carbon atoms) ) and R 21 ~R 30 Adjacent groups among these are bonded to each other and together with the d ring or e ring, have 9 to 1 carbon atoms. 6 aryl ring or heteroaryl ring having 6 to 15 carbon atoms, At least one hydrogen atom in the ring is selected from the group consisting of aryl having 6 to 30 carbon atoms, aryl having 2 to 30 carbon atoms, Heteroaryl, diarylamino (wherein aryl has 6 to 12 carbon atoms), Arylboryl (where aryl is an aryl with 6 to 12 carbon atoms, and two aryls are may be bonded via a single bond or a linking group), alkyl having 1 to 24 carbon atoms, Cycloalkyl with 3 to 24 carbon atoms, triarylsilyl (wherein aryl is an alkyl group with 6 to 12 carbon atoms) silyl), or trialkylsilyl (wherein alkyl has 1 to 6 carbon atoms). It may be replaced, R 25 and R 26 are bonded to form >O, >NR, or >C(-R)2. R in the >NR may each independently represent an 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 At least one hydrogen atom in these is an aryl having 6 to 12 carbon atoms, heteroaryl having 2 to 15 carbon atoms, alkyl having 1 to 6 carbon atoms, or cycloaryl having 3 to 14 carbon atoms R in the above >C(-R)2 may be substituted with hydrogen, alkyl having 6 to 12 carbon atoms. C2-C15 heteroaryl, C1-C6 alkyl or C3-C1 4 cycloalkyl, and at least one hydrogen atom in these is a cycloalkyl having 6 to 12 carbon atoms. Aryl, heteroaryl having 2 to 15 carbon atoms, alkyl having 1 to 6 carbon atoms or alkyl having 3 to 15 carbon atoms optionally substituted with cycloalkyl; Ra is an aryl having 6 to 30 carbon atoms, an alkyl having 1 to 24 carbon atoms, a silyl having 3 to 24 carbon atoms, chloroalkyl, triarylsilyl (wherein aryl has 6 to 12 carbon atoms), or or trialkylsilyl (wherein alkyl has 1 to 6 carbon atoms), At least one hydrogen atom in the alkyl group is an alkyl group having 1 to 24 carbon atoms or an alkyl group having 3 to 24 carbon atoms. optionally substituted with cycloalkyl; Rb is hydrogen, aryl having 6 to 30 carbon atoms, diarylamino (wherein aryl is carbon aryl having 6 to 12 carbon atoms), diarylboryl (aryl having 6 to 12 carbon atoms) two aryls may be bonded via a single bond or a linking group), Alkyl having 1 to 24 carbon atoms, cycloalkyl having 3 to 24 carbon atoms, triarylsilyl (but aryl having 6 to 12 carbon atoms), or trialkylsilyl (where alkyl has 6 to 12 carbon atoms) and at least one hydrogen atom in the aryl is an alkyl group having 1 to 6 carbon atoms. may be substituted with alkyl having 1 to 24 carbon atoms or cycloalkyl having 3 to 24 carbon atoms, Y 1 is B, P, P=O, P=S or Si-R, and R of the Si-R is the number of carbon atoms 6-10 aryl, 1-5 carbon alkyl, or 5-10 carbon cycloalkyl can be, X 1 and X 2 are each independently >O, >NR, >C(-R)2, or >S and R in the >NR is an aryl having 6 to 10 carbon atoms, an alkyl having 1 to 5 carbon atoms, or is a cycloalkyl having 5 to 10 carbon atoms, and at least one hydrogen atom in the cycloalkyl is a carbon atom. Aryl having 6 to 10 prime numbers, alkyl having 1 to 5 carbon atoms, or cycloalkyl having 5 to 10 carbon atoms R in the above >C(-R)2 may be substituted with hydrogen, an aryl having 6 to 10 carbon atoms, or alkyl having 1 to 5 carbon atoms or cycloalkyl having 5 to 10 carbon atoms; At least one hydrogen atom in the alkyl group is selected from the group consisting of aryl having 6 to 10 carbon atoms, alkyl having 1 to 5 carbon atoms, and alkyl having 1 to 5 carbon atoms. may be substituted with a cycloalkyl having 5 to 10 carbon atoms, In the compound or structure represented by formula (2B), the ring a, the ring b, the ring c, At least one of the d ring, the e ring, the formed ring, the aryl and the heteroaryl Each of the cycloalkanes may be condensed with at least one cycloalkane having 3 to 20 carbon atoms. At least one hydrogen atom in the cycloalkane is an aryl having 6 to 16 carbon atoms, Heteroaryl having 2 to 22 carbon atoms, alkyl having 1 to 12 carbon atoms, or cycloalkyl having 3 to 16 carbon atoms. may be substituted with chloroalkyl, and At least one hydrogen atom in the compound or structure represented by formula (2B) may be replaced by a deuterium atom, a silyl atom, or a methyl group. optionally substituted with an anion or halogen; Item 9. The polycyclic aromatic compound or a multimer thereof according to Item 8.

[0021] Section 10. In the above formula (2B), Any "-C(-H)=" in the a, b, and c rings is replaced with "-N=". It is okay to have R 21 ~R 30 are each independently hydrogen, an aryl having 6 to 16 carbon atoms, or a diaryl Amino (where aryl is aryl with 6 to 10 carbon atoms), diarylboryl (where aryl The aryl is an aryl having 6 to 10 carbon atoms, and two aryls are connected via a single bond or a linking group. may be bonded), alkyl having 1 to 12 carbon atoms or cycloalkyl having 3 to 16 carbon atoms It is Ra is an aryl having 6 to 30 carbon atoms, an alkyl having 1 to 24 carbon atoms, a silyl having 3 to 24 carbon atoms, At least one hydrogen atom in the aryl is substituted by an aryl having 1 to 24 carbon atoms. may be substituted by alkyl or cycloalkyl having 3 to 24 carbon atoms, Rb is hydrogen, aryl having 6 to 30 carbon atoms, diarylamino (wherein aryl is carbon aryl having 6 to 12 carbon atoms), diarylboryl (aryl having 6 to 12 carbon atoms) two aryls may be bonded via a single bond or a linking group), alkyl having 1 to 24 carbon atoms or cycloalkyl having 3 to 24 carbon atoms, At least one hydrogen atom is alkyl having 1 to 24 carbon atoms or cycloalkyl having 3 to 24 carbon atoms. may be replaced by kill, Y 1 is B, P, P=O or P=S, X 1 and X 2 are each independently >O or >NR, and R in the >NR is an aryl having 6 to 10 carbon atoms, an alkyl having 1 to 5 carbon atoms, or a cycloalkyl having 5 to 10 carbon atoms. alkyl, in which at least one hydrogen atom is an aryl having 6 to 10 carbon atoms; It may be substituted with alkyl having 1 to 5 carbon atoms or cycloalkyl having 5 to 10 carbon atoms. , In the compound or structure represented by formula (2B), the ring a, the ring b, the ring c, The ring d, the ring e, and the aryl having 6 to 10 carbon atoms as R in the >NR are At least one of the cycloalkanes may be condensed with at least one cycloalkane having 3 to 16 carbon atoms. Preferably, at least one hydrogen atom in the cycloalkane is an alkyl or alkyl group having 1 to 6 carbon atoms. may be substituted with a cycloalkyl having 3 to 14 carbon atoms, and At least one hydrogen atom in the compound or structure represented by formula (2B) may be replaced by a deuterium atom, a silyl atom, or a methyl group. optionally substituted with an anion or halogen; Item 9. The polycyclic aromatic compound or a multimer thereof according to Item 8.

[0022] Section 11. Cycloalkane-fused diarylamino groups, cycloalkane-fused carba substituted with a benzocarbazolyl group or a benzocarbazolyl group fused with a cycloalkane, 11. The polycyclic aromatic compound or a multimer thereof according to any one of 1 to 10.

[0023] Section 12. R in the above formula (2A) 2 Or, Rb in the above formula (2B) is a cycloalkane. a fused diarylamino group or a carbazolyl group fused with a cycloalkane Item 11. The polycyclic aromatic compound according to any one of Items 4 to 10.

[0024] Section 13. The cycloalkane according to item 11 or 12 is a cycloalkane having 3 to 20 carbon atoms. Polycyclic aromatic compounds.

[0025] Section 14. 14. The polycyclic aromatic compound or compound according to any one of Items 1 to 13, wherein the halogen is fluorine. is its polymer.

[0026] Section 15. Item 1. A polycyclic aromatic compound according to item 1, represented by the following structural formula: [ka]

[0027] Section 16. Item 1. The polycyclic aromatic compound according to item 1, which is represented by any one of the following structural formulas: [ka] [ka] [ka] In the above structural formula, "Me" is a methyl group, "tBu" is a t-butyl group, and "tAm" is a t-amino group. The mil group, "D" is deuterium.

[0028] Section 17. The polycyclic aromatic compound or its multimer according to any one of Items 1 to 16 has a reactive substituent. Substituted, reactive compounds.

[0029] Section 18. Item 17. A polymer compound obtained by polymerizing the reactive compound described in Item 17 as a monomer, or and a crosslinked polymer obtained by further crosslinking the polymer compound.

[0030] Section 19. A pendant polymer compound in which the reactive compound described in item 17 is substituted on a main chain polymer. or a pendant-type crosslinked polymer obtained by further crosslinking the pendant-type polymer compound. .

[0031] Section 20. Item 17. An organic compound containing a polycyclic aromatic compound or a multimer thereof according to any one of Items 1 to 16. Materials for devices.

[0032] Section 21. Item 18. A material for an organic device, comprising the reactive compound according to item 17.

[0033] Section 22. Item 19. A material for an organic device, comprising the polymer compound or crosslinked polymer according to item 18.

[0034] Section 23. Item 19. A method for manufacturing a pharmaceutical composition comprising a pendant polymer compound or a pendant polymer crosslinked body according to Item 19. Materials for organic devices.

[0035] Section 24. The organic device material is a material for an organic electroluminescent element, a material for an organic field effect transistor, or the like. 24. The organic device according to any one of items 20 to 23, which is a material for a solar cell or a thin film solar cell. Materials for use.

[0036] Section 25. Item 25. The organic electroluminescent element material according to Item 24, wherein the organic electroluminescent element material is a light-emitting layer material. material.

[0037] Section 26. Item 17. A method for producing a polycyclic aromatic compound or a multimer thereof according to any one of Items 1 to 16, comprising the steps of: An ink composition comprising:

[0038] Section 27. Item 18. An ink composition comprising the reactive compound according to item 17 and an organic solvent.

[0039] Section 28. Item 18. An ink composition comprising a main chain polymer, the reactive compound according to item 17, and an organic solvent. .

[0040] Section 29. Item 19. An ink composition comprising the polymer compound or crosslinked polymer according to item 18 and an organic solvent. thing.

[0041] Section 30. Item 19. A pendant polymer compound or a pendant polymer crosslinked body according to item 19, and an organic and a solvent.

[0042] Section 31. A pair of electrodes consisting of an anode and a cathode, and a device according to any one of items 1 to 16, disposed between the pair of electrodes Item 16. A polycyclic aromatic compound or a polymer thereof according to Item 15, a reactive compound according to Item 16, Item 18. A polymer compound or a crosslinked polymer according to Item 19. and an organic layer containing a pendant polymer compound or a pendant polymer crosslinked body. Electroluminescent device.

[0043] Section 32. Item 32. The organic electroluminescent device according to item 31, wherein the organic layer is a light-emitting layer.

[0044] Section 33. The light-emitting layer comprises a host, the polycyclic aromatic compound as a dopant, a polymer thereof, a reaction product thereof, and a fluorine-containing compound. reactive compounds, polymer compounds, crosslinked polymers, pendant polymer compounds or pendant polymer compounds Item 33. The organic electroluminescent device according to item 32, comprising a crosslinked polymer.

[0045] Section 34. The host is an anthracene-based compound, a fluorene-based compound, or a dibenzochrysene-based compound. Item 34. The organic electroluminescent device according to item 33, wherein the compound is a compound.

[0046] Section 35. At least one of an electron transport layer and an electron injection layer disposed between the cathode and the light-emitting layer At least one of the electron transport layer and the electron injection layer is a borane derivative, a pyridinium derivative, fluoranthene derivatives, BO derivatives, anthracene derivatives, benzofluorane derivatives thylene derivatives, phosphine oxide derivatives, pyrimidine derivatives, carbazole derivatives, Triazine derivatives, benzimidazole derivatives, phenanthroline derivatives, quinolinols Metal complexes, thiazole derivatives, benzothiazole derivatives, silole derivatives and azolines Any one of items 32 to 34, containing at least one selected from the group consisting of derivatives thereof The organic electroluminescent device is described.

[0047] Section 36. At least one of the electron transport layer and the electron injection layer further comprises an alkali metal, Alkali earth metals, rare earth metals, alkali metal oxides, alkali metal halides, alkali metals Alkaline earth metal oxides, alkaline earth metal halides, rare earth metal oxides, rare earth Halides of alkali metals, organic complexes of alkali metals, organic complexes of alkaline earth metals and dilute Item 35, containing at least one selected from the group consisting of organic complexes of earth metals. Organic electroluminescent device.

[0048] Section 37. At least one of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer The two layers are polymer compounds made by polymerizing low molecular weight compounds that can form each layer as monomers. Or, a polymer crosslinked body obtained by further crosslinking the polymer compound, or a polymer crosslinked body formed by forming each layer A pendant polymer compound obtained by reacting a low molecular weight compound with a main chain polymer, or Item 3 includes a pendant-type crosslinked polymer obtained by further crosslinking the pendant-type polymer compound. 37. The organic electroluminescent device according to any one of 1 to 36.

[0049] Section 38. A display device or a lighting device comprising the organic electroluminescent device according to any one of items 31 to 37. . [Effects of the Invention]

[0050] According to a preferred embodiment of the present invention, the present invention is directed to a material for an organic device, such as a material for an organic EL element. It is possible to provide novel amino-substituted polycyclic aromatic compounds that can be used as By using the amino-substituted polycyclic aromatic compounds, we have been able to provide excellent organic devices such as organic electroluminescence (EL) elements. It can be provided.

[0051] Specifically, the present inventors have proposed a method for converting an aromatic ring into a heteroatom such as boron, phosphorus, oxygen, nitrogen, or sulfur. Polycyclic aromatic compounds (basic skeleton parts) linked by atoms have a large HOMO-LUMO gap (Band gap in thin films Eg) and high triplet excitation energy (E T ) This is because the six-membered ring containing a heteroatom has low aromaticity, and as the conjugated system expands, The decrease in the HOMO-LUMO gap due to the electronic perturbation of the heteroatom is suppressed. This is due to the localization of SOMO1 and SOMO2 in the triplet excited state (T1). In addition, the polycyclic aromatic compound containing a hetero element according to the present invention (basic The backbone part) is responsible for the localization of SOMO1 and SOMO2 in the triplet excited state (T1). As a result, the exchange interaction between the two orbitals becomes smaller, and the triplet excited state (T1) and the singlet excited state The energy difference between the two states (S1) is small, and the compound exhibits thermally activated delayed fluorescence. It is also useful as a fluorescent material for devices using activated delayed fluorescence. Term excitation energy (E T ) materials utilize phosphorescent organic EL elements and thermally activated delayed fluorescence These polycyclic aromatic compounds are also useful as electron transport layers and hole transport layers in organic EL devices. Aromatic compounds (basic skeleton part) have the following characteristics: the HOMO and LUMO energies change with the introduction of substituents. Since the ionization potential and electron affinity can be adjusted according to the surrounding materials, It is possible to optimize it.

[0052] In addition to the characteristics of the basic skeleton portion, the compounds of the present invention (for example, the compounds represented by the above-mentioned formula (1A)) The compound of formula (2A) can improve the external quantum efficiency by introducing a specific amino group. This can be done. Furthermore, in addition to the characteristics of such a basic skeleton portion, the compounds of the present invention (for example, the compounds of the above-mentioned formula Compound (2B) can be made by introducing an amino group, Ra group, and Rb group at specific positions. The quantum efficiency and device life can be improved.

[0053] In addition to the above properties, the compound of the present invention has the following properties: The light is suppressed, and the device life and luminous efficiency can be expected to improve. These are important characteristics of devices, and the use of the compound of the present application is expected to have an effect of improving the characteristics of the device. It is also expected that the melting point and sublimation temperature will decrease. This means that high purity is required. In the sublimation purification, which is almost essential as a purification method for materials for organic devices such as organic EL elements, This means that the material can be purified at a relatively low temperature, preventing thermal decomposition of the material. This is also a promising method for producing organic devices such as organic EL elements using vacuum deposition. The same is true for the process, which can be carried out at relatively low temperatures, allowing for the thermal decomposition of materials. This can avoid the problems associated with the polycyclic organic compound, resulting in high-performance organic devices. Many polymers of aromatic compounds have high sublimation temperatures due to factors such as molecular weight and high planarity. Therefore, the reduction in the sublimation temperature by condensing the cycloalkane is more effective. The condensation of cycloalkanes improves the solubility in organic solvents, making it possible to use coating processes. However, the present invention is not limited to these principles. It is not going to be. [Brief explanation of the drawings]

[0054] [Figure 1] 1 is a schematic cross-sectional view showing an organic EL element according to an embodiment of the present invention. DETAILED DESCRIPTION OF THE INVENTION

[0055] 1. Amino-substituted polycyclic aromatic compounds and their multimers The present invention relates to a polycyclic aromatic compound represented by the following general formula (1), or It is a polymer of a polycyclic aromatic compound having a plurality of structures represented by the following formula: [ka] (In the above formula (1), Ring A, ring B and ring C are each independently an aryl ring or a heteroaryl ring. At least one hydrogen atom in these rings may be substituted, At least one hydrogen atom in at least one of the rings B and C is represented by the formula (Am) In the above formula (Am), Ar1 and Ar2 are each substituted with a group represented by each independently represents an aryl or heteroaryl, and the aryl or heteroaryl At least one hydrogen atom in Ar may be substituted, and Ar and Ar are each a single bond. Alternatively, the group represented by the formula (Am) may be bonded via a linking group, and the group represented by the formula (Am) may be bonded via a linking group. replacing hydrogen in the ring or C ring, Ring B and ring C may be bonded via a linking group; Y 1 is B, P, P=O, P=S, Al, Ga, As, Si-R or Ge-R wherein R in the Si—R and Ge—R is aryl, alkyl, or cycloalkyl; , X 1 and X 2 are independently >O, >NR, >Si(-R)2, >C(- R)2, >S or >Se, and R of the >NR is optionally substituted aryl. (excluding amino groups as substituents), optionally substituted heteroaryl, substituted and the >Si is an optionally substituted alkyl or an optionally substituted cycloalkyl. R in (-R)2 is an optionally substituted aryl, an optionally substituted heteroaryl, aryl, optionally substituted alkyl or optionally substituted cycloalkyl; R in the above >C(-R)2 is hydrogen, an optionally substituted aryl, an optionally substituted optionally substituted heteroaryl, optionally substituted alkyl or optionally substituted cycloaryl and at least one of >NR, >Si(—R)2 and >C(—R)2 is alkyl. In the other case, R is a linking group or a single bond to at least one of the A ring, the B ring and the C ring. and In the compound or structure represented by formula (1), the A ring, the B ring, the C ring, the aryl and the heterocyclic ring are At least one of the heteroaryls may be fused with at least one cycloalkane. Preferably, at least one hydrogen atom in the cycloalkane may be substituted, and the At least one -CH2- in the cycloalkane may be replaced with -O-; and, At least one hydrogen atom in the compound or structure represented by formula (1) can be replaced by a deuterium atom, a sialic acid atom, or a hydroxyl group. It may be substituted with methyl or halogen.

[0056] The explanation of the above formula (1) can be made by citing the explanation of formula (1A) given below. Regarding "aryl" and "heteroaryl" as Ar1 and Ar2, The description of the first substituent in formula (2B) below can be cited, and the aryl and Examples of the "substituents" for the heteroaryl and heteroaryl include aryl, heteroaryl, diaryl, and diaryl. Arylamino, diheteroarylamino, arylheteroarylamino, diarylbo aryl (two aryls may be bonded via a single bond or a linking group), alkyl, Cycloalkyl, alkoxy, aryloxy, trialkylsilyl, tricycloalkoxy alkylsilyl, dialkylcycloalkylsilyl, alkyldicycloalkylsilyl, etc. The details of these "substituents" will be described later in the section on the first substituent in formula (2B). In addition, Ar1 and Ar2 may be bonded via a single bond or a linking group. The bonding mode will be described later with reference to R in formula (2B). 25 and R 26 is combined The explanation for this case can be cited.

[0057] 1-1. Type A amino-substituted polycyclic aromatic compounds and their multimers In particular, the present invention relates to a polycyclic aromatic compound represented by the following general formula (1A), or A polymer of a polycyclic aromatic compound having a plurality of structures represented by formula (1A), At least one hydrogen atom in at least one ring is a group represented by the following formula (Am): Preferably, the polycyclic aromatic compound is represented by the following general formula (2A): A polymer of a polycyclic aromatic compound having a plurality of structures represented by the following general formula (2A), R 4 ~R 11 At least one of the following is a group represented by the following formula (Am), and / or b An aryl or heteroaryl ring formed together with the ring or ring (details will be explained later) ) at least one hydrogen atom is substituted with a group represented by the following formula (Am): [ka] In each structural formula, "A" to "C" and "a" to "c" respectively represent rings or The symbols represent the ring structure represented by a benzene ring, and the other symbols are the same as defined above. do.

[0058] In the general formula (1A), the ring A, the ring B and the ring C are each independently an aryl ring or is a heteroaryl ring, and at least one hydrogen atom in the ring is replaced with a substituent. The substituent may be a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino, substituted or unsubstituted diheteroaryl, substituted or unsubstituted arylheteroarylamino (aryl and substituted or unsubstituted diarylboryl (two amino groups with heteroaryl) The alkyl may be bonded via a single bond or a linking group, and a substituted or unsubstituted alkyl alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted Preferably, these groups have a substituent, such as aryloxy or substituted silyl. The substituents, if any, may be aryl, heteroaryl, alkyl or cycloalkyl. The aryl ring or heteroaryl ring may be Y 1 , X 1 and X 2 A 5-membered or 6-membered ring sharing a bond with the central fused 2-ring structure of general formula (1A) It is preferred that the ring has a membered ring.

[0059] Here, the "fused bicyclic structure" refers to the Y 1 , X 1 and X 2 It also means a structure in which two saturated hydrocarbon rings are fused together. The "six-membered ring sharing a bond with the ring structure" refers to, for example, the fused ring shown in the general formula (2A) above. It means a ring (a benzene ring (6-membered ring)) fused to a two-ring structure. The phrase "an aryl ring or heteroaryl ring has this six-membered ring" means that the A ring is formed by this six-membered ring alone. is formed, or other rings are fused to this six-membered ring so as to include this six-membered ring. In other words, the "six-membered ring (A The term "aryl or heteroaryl ring (which is a ring)" refers to a ring that constitutes all or part of ring A. The term "B ring (b ring)" and "C ring" refer to a 6-membered ring fused to the fused bicyclic structure. The same explanation applies to "(c-ring)" and "5-membered ring."

[0060] The ring A (or ring B or ring C) in the general formula (1A) is the same as the ring a in the general formula (2A). The substituent R 1 ~R 3 (or ring b and its substituent R 8 ~R 11 , c ring and its substituent R 4 ~ R 7 That is, general formula (2A) corresponds to "6" as rings A to C of general formula (1A). In this sense, each of the rings A to C having a ring structure of general formula (2A) corresponds to the selected structure. Rings are represented by lowercase letters a to c.

[0061] In the general formula (2A), the substituents R 1 ~R 11 adjacent groups among They bond together to form an aryl or heteroaryl ring together with ring a, ring b, or ring c. At least one hydrogen atom in the formed ring may be replaced by an aryl, heteroaryl, or aryl, diarylamino, diheteroarylamino, arylheteroarylamino, di arylboryl (two aryls may be bonded via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, triarylsilyl, triaryl alkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl or alkyl and at least one of these may be substituted with a dicycloalkylsilyl. The element may be substituted with aryl, heteroaryl, alkyl, or cycloalkyl. Therefore, the polycyclic aromatic compound represented by the general formula (2A) is a compound having rings a, b and c. Depending on the mutual bonding form of the substituents in As shown, the ring structures constituting the compounds vary. Ring A', ring B' and ring C' in each formula correspond to the A ring, the B ring, and the C ring in general formula (1A), respectively.

[0062] [ka]

[0063] The rings A', B' and C' in the formula (2A-1) and (2A-2) are represented by the general formula As explained in (2A), the substituent R 1 ~R 11 Adjacent groups in indicates an aryl or heteroaryl ring formed together with rings a, b, and c (ring a) (It can also be said that the ring b or ring c is a fused ring formed by fusing another ring structure to the ring b or ring c.) However, there are compounds in which the a, b and c rings have all been changed to A', B' and C' rings. As can be seen from the above formulas (2A-1) and (2A-2), for example, , b-ring R 8 and R in c-ring 7 , b-ring R 11 and a-ring R 1, R of ring c 4 and a-ring R 3 etc. They do not fall under the category of "adjacent groups" and are not bonded to each other unless otherwise specified. That is, "adjacent groups" means groups that are adjacent on the same ring.

[0064] The compounds represented by the above formula (2A-1) or (2A-2) can be prepared by, for example, forming an a ring (or a b ring) or Benzene ring, indole ring, pyrrole ring, benzophenone ring, A' ring (or B' ring or C' ring) formed by condensation of an orchid ring or a benzothiophene ring ring), and the resulting fused ring A' (or fused ring B' or fused ring Ring C') is a naphthalene ring, a carbazole ring, an indole ring, a dibenzofuran ring or or a dibenzothiophene ring.

[0065] Y in general formula (1A) 1 is B, P, P=O, P=S, Al, Ga, As, Si- R or Ge—R, wherein R of the Si—R and Ge—R is aryl, alkyl, or In the case of P=O, P=S, Si-R or Ge-R, the A ring, B The atom bonding to the ring or C ring is P, Si or Ge. 1 is B, P, P=O, P =S or Si-R is preferred, and B is particularly preferred. Y 1 But it's the same.

[0066] X in general formula (1A) 1 and X 2 are independently >O, >NR, and >S i(-R)2, >C(-R)2, >S or >Se, and R in the >NR is substituted. optionally substituted aryl (excluding amino groups as substituents); Heteroaryl, optionally substituted alkyl or optionally substituted cycloalkenyl R of the >Si(—R)2 is an optionally substituted aryl, a substituted optionally substituted heteroaryl, optionally substituted alkyl or optionally substituted R in the >C(—R)2 is hydrogen, an optionally substituted aryl, or aryl, optionally substituted heteroaryl, optionally substituted alkyl or substituted and >NR, >Si(-R)2 and >C(- R in at least one of the rings A, B and C is connected to the ring A by a linking group or a single bond. The linking group may be -O-, -S- or -C(-R)2- is preferred. In addition, R in the above "-C(-R)2-" is hydrogen, alkyl or cycloalkyl. This explanation applies to X in general formula (2A). 1 and X 2 But the same That is correct.

[0067] Here, in the general formula (1A), “the above-mentioned >NR, >Si(—R)2 and >C(—R In at least one of the above 2, R is a linking group or a single bond to the ring A, ring B and ring C. In general formula (2A), the definition of "bonded to at least one ring of the above >NR , R in at least one of >Si(-R)2 and >C(-R)2 is -O-, -S at least one of the ring a, ring b and ring c is connected by -, -C(-R)2- or a single bond; This corresponds to the provision that "is bonded to a ring of the formula (I)."

[0068] This provision is expressed by the following formula (2A-3-1), X1 or X 2 is fused ring B' and fused It can be expressed as a compound having a ring structure incorporated into ring C'. That is, for example, the general formula (2 A) X for the b-ring (or c-ring) of the benzene ring 1 (or X 2 ) It is a compound having ring B' (or ring C') formed by condensing other rings in such a way that The fused ring B' (or fused ring C') formed is, for example, a phenoxazine ring, a phenoxazine ring, or a phenoxazine ring. It is a thiazine ring or an acridine ring.

[0069] In addition, the above-mentioned provision is based on X represented by the following formula (2A-3-2) or (2A-3-3). 1 oh Call X 2 At least one of the ring structures is incorporated into the fused ring A'. That is, for example, X can be used for the benzene ring which is the a ring in the general formula (2A). 1 (Ma or X 2 , or X 1 and X 2 ) and other rings are condensed to form A The fused ring A' formed is, for example, a phenoxazine ring, a phenoxazine ring, or a phenoxazine ring. It is an ethynyl ring or an acridine ring.

[0070] [ka]

[0071] Furthermore, ring B and ring C may be bonded via a linking group. Examples of the linking group include , >O, >NR, >Si(-R)2, >C(-R)2, >S or >Se. R in the >NR and >Si(—R) 2 may each independently be substituted. aryl, optionally substituted heteroaryl, optionally substituted alkyl, or or optionally substituted cycloalkyl, and R in the >C(—R)2 is hydrogen, a substituent, or optionally substituted aryl, optionally substituted heteroaryl, optionally substituted The above-mentioned >NR is an optionally substituted alkyl or an optionally substituted cycloalkyl. R in at least one of >Si(-R)2 and >C(-R)2 is a linking group or a single bond. It may be bonded to at least one of the rings B and C by a bond, and as a linking group is preferably -O-, -S- or -C(-R)2-. " R is hydrogen, alkyl or cycloalkyl. This explanation is applicable to the general formula (2A). The same applies to the linking group connecting the b ring and the c ring.

[0072] Here, in the general formula (1A), “the above-mentioned >NR, >Si(—R)2 and >C(—R R in at least one of the groups (-O-, -S-, or -C(-R)2-) is a linking group (such as -O-, -S-, or -C(-R)2-). ) or is bonded to at least one of the rings B and C by a single bond." In the general formula (2A), the definition is "a few of the above-mentioned >NR, >Si(-R)2 and >C(-R)2" At least one R is connected to the preceding group by -O-, -S-, -C(-R)2- or a single bond. This corresponds to the provision that "the ring b is bonded to at least one of the rings b and c."

[0073] For details of the form in which ring B and ring C are bonded via a linking group, see the above-mentioned X 1 or X 2 Using equations (2A-3-1), (2A-3-2) and (2A-3-3) for The explanation can be cited.

[0074] The positions at which the ring B and the ring C are bonded are not particularly limited, but may be any of the positions described in the general formula (2A). Then, R 7 and R 8 are bonded, for example, >O, >NR, >Si(-R)2, >C(- R)2, >S or >Se. This form is preferred. 1 and (part of) the c-algebra and R 7 and R 8 This corresponds to the structure in which a six-membered ring is formed from the binding site of and (part of) the b ring. Also, Y 1 and one side of the benzene ring, which is the c-ring, and R 7 and R 8 and the binding site of b It can also be said that a six-membered ring is formed by being surrounded by one side of the benzene ring.

[0075] X 1 and X 2 and specific examples of the linking group connecting the B ring and the C ring include >O, In >NR, >Si(-R)2, >C(-R)2, >S or >Se, >O, >N -R, >C(-R)2 or >S is preferred, and >O, >NR or >C(-R)2 is more preferred. More preferred is >O or >NR, particularly preferred.

[0076] In formula (2A), any "-C(-R)=" (where R is R in formula (2A) 1 ~R 11 ) may be replaced with "-N=". [ka] As shown above, for example, "-C(-R 5 )=" is replaced with "-N=" Thus, the c ring, which is represented as a benzene ring in formula (2A), can be Pyridine ring, pyrimidine ring, pyridazine ring, pyrazine ring, and other nitrogen-containing heteroaryls In addition, when there is an adjacent group on the c ring (R 6 Oh BiR 7 ) are bonded to form a heteroaryl ring together with ring c (in the above formula, quinoline ring) ), and the formed ring may be further substituted (represented by n Rs) as described above. As stated above. In addition, there are the following variations: [ka] If other parts are replaced with "-N=" or if the a or b ring changes, It's the same even if there is one.

[0077] In formula (2A), any of "-C(-R)=C(-R)" in ring a, ring b, and ring c - (where R is R in formula (2A) 1 ~R 11 ) are "-N(-R)-", "-O The R in the "-N(-R)-" may be replaced with "-" or "-S-" and The substituents are aryl, alkyl, or cycloalkyl. This will be summarized later. [ka] As shown above, for example, "-C(-R 7 )=C(-R 6 )-" It may be replaced with "-N(-R)-", "-O-", or "-S-", like this The ring c shown as a benzene ring in formula (2A) is an R-substituted pyrrole ring or furan ring. , thiophene ring, or other nitrogen-, oxygen-, or sulfur-containing heteroaryl ring. When there is an adjacent group on the c ring (R 4 and R 5 ) these results The heteroaryl ring (indole ring, benzofuran ring, etc.) is bonded to the c ring together with the R-substituted ring, or benzothiophene ring), and the ring formed may be further substituted. (denoted by n R's) is as described above. In addition, there are the following variations: [ka] If other parts are replaced with "-N(-R)-", "-O-", or "-S-", The same applies when the a or b ring is changed.

[0078] In addition, the above formulas (2A-1), (2A-2), (2A-3-1), and (2A-3-2) ), and in the explanation of formula (2A-3-3), the a ring, the b ring, and the c ring are considered as benzene rings. As explained above, the rings a to c are nitrogen-containing heteroaryl rings (six- or five-membered rings) or oxygen-containing heteroaryl rings. The same applies to the case where the ring is changed to a carbon-sulfur heteroaryl ring (five-membered ring).

[0079] Examples of the "aryl ring" which is ring A, ring B and ring C in general formula (1A) include carbon An aryl ring having 6 to 30 carbon atoms is preferred, an aryl ring having 6 to 16 carbon atoms is preferred, and an aryl ring having 6 to 16 carbon atoms is preferred. An aryl ring having from 1 to 12 carbon atoms is more preferred, and an aryl ring having from 6 to 10 carbon atoms is particularly preferred. The "aryl ring" is defined as "R 1 ~R 11 Adjacent of "An aryl ring formed by bonding the groups together with ring a, ring b, or ring c" and Since the a ring (or b ring, c ring) is already composed of a benzene ring with 6 carbon atoms, The minimum carbon number is 9, which is the total number of carbon atoms in the fused ring formed by condensing the five-membered ring.

[0080] Specific examples of the "aryl ring" include a monocyclic benzene ring and a bicyclic biphenyl ring. ring, a fused bicyclic ring, a naphthalene ring, a tricyclic ring, a terphenyl ring (m-terphenyl, o-Terphenyl, p-Terphenyl), fused tricyclic ring system, acenaphthylene ring, fluoro phenylene ring, phenalene ring, phenanthrene ring, triphenylene ring which is a fused tetracyclic ring system, pyrene ring, naphthacene ring, and fused five-ring system perylene ring and pentacene ring.

[0081] Examples of the "heteroaryl ring" which is ring A, ring B and ring C in general formula (1A) include: and heteroaryl rings having 2 to 30 carbon atoms, and heteroaryl rings having 2 to 25 carbon atoms. A heteroaryl ring having 2 to 20 carbon atoms is preferred, and a heteroaryl ring having 2 to 15 carbon atoms is more preferred. An aryl ring is more preferred, and a heteroaryl ring having 2 to 10 carbon atoms is particularly preferred. Examples of "heteroaryl ring" include rings containing oxygen, sulfur, and Examples include heterocycles containing 1 to 5 heteroatoms selected from nitrogen. The "heteroaryl ring" in the formula (2A) is defined as "R 1 ~R 11 Adjacent of The heteroaryl ring formed by bonding these groups together with the ring a, ring b or ring c corresponds to , and because the a ring (or b ring, c ring) is already composed of a benzene ring with 6 carbon atoms, The lower limit of the carbon number is 6, which is the total carbon number of the fused ring formed by condensing this with a 5-membered ring.

[0082] Specific examples of the "heteroaryl ring" include a pyrrole ring, an oxazole ring, an isoaryl ring, and an aryl ring. Oxazole ring, thiazole ring, isothiazole ring, imidazole ring, oxadiazole ring, a thiadiazole ring, a triazole ring, a tetrazole ring, a pyrazole ring, a pyridine ring, Pyrimidine ring, pyridazine ring, pyrazine ring, triazine ring, indole ring, isoindole 1H-indazole ring, 1H-indazole ring, benzimidazole ring, benzoxazole ring, benzothiazole ring, Azole ring, 1H-benzotriazole ring, quinoline ring, isoquinoline ring, cinnoline ring , quinazoline ring, quinoxaline ring, phthalazine ring, naphthyridine ring, purine ring, pteridin ring ring, carbazole ring, acridine ring, phenoxathiin ring, phenoxazine ring, phenon Thiazine ring, phenazine ring, phenazasiline ring, indolizine ring, furan ring, benzofura benzofuran ring, isobenzofuran ring, dibenzofuran ring, thiophene ring, benzothiophene ring, dibenzofuran ring, Benzothiophene ring, furazan ring, thianthrene ring, indolocarbazole ring, benzoyl Indolocarbazole ring, benzobenzoindolocarbazole ring, naphthobenzofuran ring, etc. Examples include:

[0083] At least one hydrogen atom in the above "aryl ring" or "heteroaryl ring" is The substituents of 1 are substituted or unsubstituted "aryl" and substituted or unsubstituted "hetero aryl", substituted or unsubstituted "diarylamino", substituted or unsubstituted "dihe substituted or unsubstituted "arylheteroarylamino"; substituted or unsubstituted "arylheteroarylamino"; Or unsubstituted "diarylboryl" (two aryls are bonded via a single bond or a linking group). "substituted or unsubstituted "alkyl", "substituted or unsubstituted "silyl", "substituted or unsubstituted "alkyl", "substituted or unsubstituted "alkyl", "substituted or unsubstituted "silyl ... "chloroalkyl", substituted or unsubstituted "alkoxy", substituted or unsubstituted "aryl" The first substituent may be substituted with "silyl" or a substituted "silyl". "aryl" and "heteroaryl" as examples, and "diheteroaryl" as examples. the heteroaryl of "arylheteroarylamino" and the aryl of "arylheteroarylamino" Heteroaryl, aryl in "diarylboryl", and aryl in "aryloxy" Examples of the aryl ring include the monovalent group of the "aryl ring" or "heteroaryl ring" described above.

[0084] The "alkyl" as the first substituent may be either a straight chain or a branched chain. For example, a linear alkyl having 1 to 24 carbon atoms or a branched alkyl having 3 to 24 carbon atoms can be mentioned. Alkyl having 1 to 18 carbon atoms (branched alkyl having 3 to 18 carbon atoms) is preferred, Alkyl having 1 to 12 prime numbers (branched alkyl having 3 to 12 carbon atoms) is more preferred, Alkyl having 1 to 8 carbon atoms (branched alkyl having 3 to 8 carbon atoms) is more preferred, and alkyl having 1 to 6 carbon atoms is more preferred. Alkyl (branched alkyl having 3 to 6 carbon atoms) is particularly preferred, and alkyl (branched alkyl having 1 to 5 carbon atoms) is particularly preferred. Branched alkyl having 3 to 5 prime numbers is most preferred.

[0085] Specific examples of alkyl include methyl, ethyl, n-propyl, isopropyl, and n-butyl. butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl , t-pentyl (t-amyl), n-hexyl, 1-methylpentyl, 3,3-dimethyl Butyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, t-octyl butyl (1,1,3,3-tetramethylbutyl), 1-methylheptyl, 2-ethylhexyl Cyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 2,6-dimethyl 4-heptyl, 3,5,5-trimethylhexyl, n-decyl, n-undecyl, 1 -Methyldecyl, n-dodecyl, n-tridecyl, 1-hexylheptyl, n-tetradecyl sil, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, n -Eicosyl, etc. 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 ethylhexyl, 1-ethyl-1,3-dimethylbutyl, 1,1,2,2-tetramethylpropyl propyl, 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- Propyl-1-methylbutyl, 1,1-dimethylhexyl, and the like are also included.

[0086] The "cycloalkyl" as the first substituent is a cycloalkyl having 3 to 24 carbon atoms. cycloalkyl having 3 to 20 carbon atoms, cycloalkyl having 3 to 16 carbon atoms, cycloalkyl having 3 to 14 cycloalkyl, cycloalkyl having 5 to 10 carbon atoms, cycloalkyl having 5 to 8 carbon atoms cycloalkyl having 5 to 6 carbon atoms, cycloalkyl having 5 carbon atoms, and the like.

[0087] Specific cycloalkyl groups include cyclopropyl, cyclobutyl, cyclopentyl, Cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, and and alkyl (especially methyl) substituted derivatives of these having 1 to 5 carbon atoms, norbornenyl, bicyclo [1.0.1]butyl, bicyclo[1.1.1]pentyl, bicyclo[2.0.1]pentyl ethyl, bicyclo[1.2.1]hexyl, bicyclo[3.0.1]hexyl, bicyclo[ 2.1.2]heptyl, bicyclo[2.2.2]octyl, adamantyl, diamantyl , decahydronaphthalenyl, decahydroazulenyl, and the like.

[0088] Furthermore, the "alkoxy" as the first substituent includes, for example, straight chain or alkyl groups having 1 to 24 carbon atoms. or branched alkoxy having 3 to 24 carbon atoms. Branched alkoxy having 3 to 18 carbon atoms) is preferred, and alkoxy having 1 to 12 carbon atoms (carbon Alkoxy having 3 to 12 carbon atoms) is more preferred, and alkoxy having 1 to 6 carbon atoms (branched alkoxy having 3 to 12 carbon atoms) is more preferred. Alkoxy having 1 to 5 carbon atoms (branched alkoxy having 3 to 6 carbon atoms) is more preferred, and alkoxy having 1 to 5 carbon atoms (branched alkoxy having 3 to 6 carbon atoms) is more preferred. Particularly preferred are branched alkoxy groups having up to 5 carbon atoms.

[0089] Specific alkoxy includes methoxy, ethoxy, propoxy, isopropoxy, n -butoxy, isobutoxy, s-butoxy, t-butoxy, t-amyloxy, n-pentoxy t-pentyloxy, isopentyloxy, neopentyloxy, t-pentyloxy, n-hexyloxy Siloxy, 1-methylpentyloxy, 4-methyl-2-pentyloxy, 3,3-di Methylbutoxy, 2-ethylbutoxy, n-heptyloxy, 1-methylhexyloxy , n-octyloxy, t-octyloxy, 1-methylheptyloxy, 2-ethylheptyloxy xyloxy, 2-propylpentyloxy, n-nonyloxy, 2,2-dimethylheptyloxy Hexyloxy, 2,6-dimethyl-4-heptyloxy, 3,5,5-trimethylhexyl Oxy, n-decyloxy, n-undecyloxy, 1-methyldecyloxy, n-dode Cyloxy, n-tridecyloxy, 1-hexylheptyloxy, n-tetradecyloxy Oxy, n-pentadecyloxy, n-hexadecyloxy, n-heptadecyloxy, n -octadecyloxy, n-eicosyloxy, and the like.

[0090] The "substituted silyl" as the first substituent includes, for example, aryl, alkyl and and silyl substituted with at least one of cycloalkyl, triarylsilyl ... trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl or Examples include alkyldicycloalkylsilyl.

[0091] "Triarylsilyl" refers to a silyl group in which the three hydrogen atoms are independently aryl. The aryl may be substituted with an aryl, and the aryl may be the same as the "aryl" in the first substituent. The group described as "aromatic group" can be cited. Specific examples of "triarylsilyl" include triphenylsilyl and diphenylmononasilyl. Examples of the silyl group include dinaphthylsilyl, monophenyldinaphthylsilyl, and trinaphthylsilyl.

[0092] "Trialkylsilyl" refers to a silyl group in which the three hydrogen atoms are independently alkyl. The alkyl may be substituted with the alkyl group described above in the first substituent. The alkyl group preferably used for substitution is a carbonyl group. Alkyl having 1 to 5 prime numbers, specifically methyl, ethyl, propyl, i-propyl, Examples include butyl, sec-butyl, t-butyl, and t-amyl.

[0093] Specific examples of trialkylsilyl include trimethylsilyl, triethylsilyl, and triplylsilyl. Iodopropylsilyl, tri-i-propylsilyl, tributylsilyl, tri-sec-butylsilyl , tri-t-butylsilyl, tri-t-amylsilyl, ethyldimethylsilyl, propyldimethylsilyl Isopropylsilyl, i-propyldimethylsilyl, butyldimethylsilyl, sec-butyldimethylsilyl t-butyldimethylsilyl, t-amyldimethylsilyl, methyldiethylsilyl silyl, propyldiethylsilyl, i-propyldiethylsilyl, butyldiethylsilyl, sec-Butyldiethylsilyl, t-Butyldiethylsilyl, t-Amyldiethylsilyl , methyldipropylsilyl, ethyldipropylsilyl, butyldipropylsilyl, sec -Butyldipropylsilyl, t-Butyldipropylsilyl, t-Amyldipropylsilyl , methyldi-i-propylsilyl, ethyldi-i-propylsilyl, butyldi-i-propylsilyl sec-butyldi-i-propylsilyl, t-butyldi-i-propylsilyl, t-butyldi-i-propylsilyl Examples include methyldi-i-propylsilyl.

[0094] "Tricycloalkylsilyl" refers to a silyl group in which the three hydrogen atoms are independently Examples of the cycloalkyl substituted group include a group substituted with cycloalkyl, and the cycloalkyl is the same as the first substituent described above. The group described as "cycloalkyl" in the substituent can be cited. The most preferred cycloalkyl is a cycloalkyl having 5 to 10 carbon atoms, specifically cycloalkyl. cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclo Decyl, bicyclo[1.1.1]pentyl, bicyclo[2.0.1]pentyl, bicyclo [1.2.1]hexyl, bicyclo[3.0.1]hexyl, bicyclo[2.1.2]hexyl butyl, bicyclo[2.2.2]octyl, adamantyl, decahydronaphthalenyl, decahydronaphthalenyl Examples include hydroazulenyl.

[0095] Specific examples of tricycloalkylsilyl include tricyclopentylsilyl, tricyclo hexylsilyl, etc.

[0096] Dialkylcycloalkylsilyl, which is substituted with two alkyls and one cycloalkyl, , alkyldicycloalkylsilyl substituted with one alkyl and two cycloalkyl groups Specific examples include groups selected from the specific alkyl and cycloalkyl groups listed above. An example is Cyril, which has been replaced by

[0097] The "aryl" in the "diarylboryl" of the first substituent is the aryl group described above. The two aryls can be linked by a single bond or a linking group (e.g., >C( -R), >O, >S or >NR), where R in R)2 and >NR is aryl, heteroaryl, diarylamino, alkyl , cycloalkyl, alkoxy, or aryloxy (all of which are first substituents), The first substituent may further include aryl, heteroaryl, alkyl, or cycloalkyl (the above). , second substituent) may be substituted, and specific examples of these groups include the above-mentioned first substituent Aryl, heteroaryl, diarylamino, alkyl, cycloalkyl as groups; The descriptions of alkoxy or aryloxy can be cited.

[0098] The first substituent is a substituted or unsubstituted "aryl", a substituted or unsubstituted "heteroaryl", "Diaryl", substituted or unsubstituted "diarylamino", substituted or unsubstituted " "diheteroarylamino", substituted or unsubstituted "arylheteroarylamino", Substituted or unsubstituted "diarylboryl (two aryls are connected via a single bond or a linking group) "substituted or unsubstituted "alkyl", "substituted or unsubstituted "Cycloalkyl", substituted or unsubstituted "alkoxy", substituted or unsubstituted "a "Silyloxy" or "substituted silyl" refers to substituted or unsubstituted silyl. At least one hydrogen atom in each of these groups may be substituted with a second substituent. The second substituent may be, for example, an aryl, heteroaryl, alkyl, or cycloalkyl. Specific examples thereof include the above-mentioned "aryl ring" or "heteroaryl ring." " monovalent radical, and description of "alkyl" or "cycloalkyl" as the first substituent In addition, the aryl and heteroaryl as the second substituent include the following: At least one hydrogen atom in each of them is an aryl group such as phenyl (specific examples are the groups mentioned above). ), alkyl such as methyl (specific examples are the groups mentioned above), or cycloalkyl such as cyclohexyl. The structures substituted with alkyl (examples of which are given above) also have aryl or heteroaryl groups as second substituents. For example, when the second substituent is a carbazolyl group, At least one hydrogen atom at the 9-position is an aryl such as phenyl, an alkyl such as methyl Alternatively, a carbazolyl group substituted with a cycloalkyl such as cyclohexyl may also be used as the second substituent. The heteroaryl is included in the heteroaryl.

[0099] R in general formula (2A) 1 ~R 11 Aryl, heteroaryl, diarylamino in aryl, diheteroarylamino, heteroaryl, arylheteroarylamino aryl and heteroaryl in the aryl group, aryl in the diarylboryl group, or aryl in the aryloxy group The ring may be an "aryl ring" or a "heteroaryl ring" as described in the general formula (1A). Also, R 1 ~R 11 Alkyl, cycloalkyl, and alkoxy groups in The koxy or substituted silyl includes the first substituent in the above description of the general formula (1A). The term "alkyl", "cycloalkyl", "alkoxy" or "substituted silyl" as Further, aryl, heteroaryl and the like may be used as substituents for these groups. The same applies to aryl, alkyl, or cycloalkyl. 1 ~R 11 Adjacent The groups bond to each other to form an aryl or heteroaryl ring together with the a, b or c ring. When the ring is formed, the substituents on these rings, such as heteroaryl, diarylamino, diheteroaryl, Heteroarylamino, arylheteroarylamino, diarylboryl (two aryl alkyl, cycloalkyl, alkyl, alkyl- ... alkoxy, aryloxy or substituted silyl, and a further substituent aryl, The same applies to heteroaryl, alkyl, or cycloalkyl.

[0100] Specifically, the steric hindrance, electron donating property, and electron withdrawing property of the first substituent structure cause the emission of light. The wavelength can be adjusted, and the group is preferably represented by the following structural formula, and more preferably is methyl, t-butyl, t-amyl, t-octyl, phenyl, o-tolyl, p-tolyl xylyl, 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-dimethylcarbazolyl, 3,6-di-t-butylcarbazolyl and phenoxy, more preferably methyl, t-butyl, t-amyl, t-o Octyl, phenyl, o-tolyl, 2,6-xylyl, 2,4,6-mesityl, diphenyl Amino, di-p-tolylamino, bis(p-(t-butyl)phenyl)amino, carbazo aryl, 3,6-dimethylcarbazolyl and 3,6-di-t-butylcarbazolyl From the viewpoint of ease of synthesis, a larger steric hindrance is preferable for selective synthesis. Specifically, t-butyl, t-amyl, t-octyl, o-tolyl, p-tolyl, 2,4- Xylyl, 2,5-xylyl, 2,6-xylyl, 2,4,6-mesityl, di-p-trimethyl arylamino, bis(p-(t-butyl)phenyl)amino, 3,6-dimethylcarbazolyl and 3,6-di-t-butylcarbazolyl are preferred.

[0101] In the following structural formula, "Me" is methyl, "tBu" is t-butyl, and "tAm" is t- amyl, "tOct" represents t-octyl, and * represents the bond position. [ka] [ka] [ka] [ka] [ka]

[0102] In the general formula (2A), any "-C(-R)=C(-R)-" (where R is a group represented by the formula (2A ) in R 1 ~R 11 R in "-N(-R)-" which may be substituted by aryl, alkyl, or cycloalkyl, but the aryl, alkyl, or cycloalkyl Examples of the aryl group include those described above. In particular, aryl groups having 6 to 10 carbon atoms (e.g., phenyl, naphthyl) are preferred. alkyl having 1 to 5 carbon atoms or 1 to 4 carbon atoms (e.g., methyl, ethyl, etc.) Cycloalkyl having 5 to 10 carbon atoms (preferably cyclohexyl or adamantyl) is preferred. stomach.

[0103] Y in general formula (1A) 1 In the above, R in Si-R and Ge-R is aryl, alkyl or or cycloalkyl, but the aryl, alkyl or cycloalkyl is any of the above. In particular, aryl groups having 6 to 10 carbon atoms (e.g., phenyl, naphthyl, etc.) are mentioned. ), alkyl having 1 to 5 carbon atoms (e.g., methyl, ethyl, etc.) or cycloalkyl having 5 to 10 carbon atoms. The preferred alkyl groups are cyclohexyl and adamantyl. Y in (2A) 1 But it's the same.

[0104] X in general formula (1A) 1 and X 2In the above, R in NR, and rings B and C are R in >NR as a linking group may be substituted with the second substituent described above. , aryl, heteroaryl, alkyl, or cycloalkyl (provided that X 1 Oh and X 2 In the above formula, the aryl as R in NR is not substituted with an amino group), At least one hydrogen atom in the alkyl, heteroaryl, alkyl, or cycloalkyl is, for example, The aryl, heteroaryl, and heteroaryl groups may be substituted, for example, by alkyl or cycloalkyl. The alkyl, cycloalkyl and cycloalkyl groups include those described above. 10 aryl (e.g., phenyl, naphthyl, etc.), heteroaryl having 2 to 15 carbon atoms ( For example, carbazolyl, dibenzofuranyl, dibenzothiophenyl, etc.), carbon number 1 to 5 alkyl (e.g., methyl, ethyl, etc.) or cycloalkyl (preferably having 5 to 10 carbon atoms) Preferred are phenyl, naphthyl, carbazolyl, etc. , dibenzofuranyl or dibenzothiophenyl are more preferred, and dibenzofuranyl or More preferably, dibenzothiophenyl is used. Also, dibenzofuranyl or dibenzothio It is particularly preferred that the phenyl is substituted with a second substituent, specifically the second substituent Examples of the substituents include t-butyl, phenyl, and d5-phenyl. It is preferable that the substituent is at the para position of the nitrogen atom or sulfur atom. This applies to compounds such as the compound (1-3838) shown below. X in 2A) 1 and X 2 The same is true for the linking group connecting the b ring and the c ring. . [ka]

[0105] X in general formula (1A) 1 and X 2 In the above, R in Si(-R)2, and B ring and R in >Si(-R)2 as a linking group connecting the C ring and the C ring is substituted with the second substituent described above. aryl, heteroaryl, alkyl or cycloalkyl, optionally At least one of the aryl, heteroaryl, alkyl, or cycloalkyl The hydrogen atom of the aryl group may be substituted with, for example, alkyl or cycloalkyl. Heteroaryl, alkyl or cycloalkyl include the groups mentioned above. Aryl with 6 to 10 carbon atoms (e.g., phenyl, naphthyl, etc.), heterocyclic with 2 to 15 carbon atoms Aryl (e.g., carbazolyl), alkyl having 1 to 5 carbon atoms (e.g., methyl, ethyl) etc.) or cycloalkyl having 5 to 10 carbon atoms (preferably cyclohexyl or adamantyl). This explanation is based on the general formula (2A) where X 1 and X 2 But b-ring and The same applies to the linking group connecting the rings c.

[0106] X in general formula (1A) 1 and X 2 R in >C(-R)2 in the ring B and R in >C(-R)2 as a linking group connecting the C rings is substituted with hydrogen or the second substituent described above. optionally substituted aryl, heteroaryl, alkyl or cycloalkyl; At least one hydrogen atom in the aryl or heteroaryl may be, for example, an alkyl or The aryl, heteroaryl, alkyl or cycloalkyl may be substituted. Examples of cycloalkyl include the groups mentioned above. In particular, aryl having 6 to 10 carbon atoms (e.g., phenyl, naphthyl, etc.), heteroaryl having 2 to 15 carbon atoms (e.g., carbazolyl etc.), alkyl having 1 to 5 carbon atoms (e.g., methyl, ethyl, etc.) or alkyl having 5 to 10 carbon atoms Cycloalkyl (preferably cyclohexyl or adamantyl) is preferred. X in general formula (2A) 1 and X 2 The same applies to the linking group connecting the b ring and the c ring. That is correct.

[0107] In general formula (1A), X 1 and X 2 and a bond connecting ring b and ring c Examples of the linking group when the group is bonded to at least one of the rings A, B and C include Examples include -O-, -S-, -C(-R)2-, and single bonds. R in (-R)2- is hydrogen, alkyl or cycloalkyl, but the alkyl or cycloalkyl Examples of the cycloalkyl include the groups described above. In particular, alkyl having 1 to 5 carbon atoms (e.g., methyl, ethyl, etc.) or cycloalkyl (preferably cyclohexyl) having 5 to 10 carbon atoms This explanation is based on the linking group " in general formula (2A). The same is true for "-C(-R)2-".

[0108] The present invention also provides a polycyclic aromatic compound having a plurality of unit structures represented by general formula (1A). A polymer of the above, preferably a polycyclic aromatic compound having a plurality of unit structures represented by general formula (2A). The polymer is preferably a dimer to a hexamer, more preferably a dimer to a trimer, and more preferably a dimer. The polymer is particularly preferred if it has a plurality of the above unit structures in one compound. For example, the unit structure may be a single bond, an alkylene group having 1 to 3 carbon atoms, a phenylene group, In addition to the form in which multiple units are bonded together with a linking group such as a naphthylene group (linked polymer), the above unit structure Any ring (A ring, B ring or C ring, a ring, b ring or c ring) contained in The unit may be a ring-covalent polymer (a ring-covalent polymer). Any rings (ring A, ring B or ring C, ring a, ring b or ring c) contained in the structure are fused together The polymers may be bonded in such a manner (ring-fused polymers), but may also be ring-covalent polymers and Ring-fused multimers are preferred, and ring-covalent multimers are more preferred.

[0109] Examples of such multimers include those represented by the following formula (2A-4), formula (2A-4-1), and formula ( 2A-4-2), formula (2A-5-1) to formula (2A-5-4) or formula (2A-6) The multimeric compound represented by the following formula (2A-4) is a multimeric compound represented by the general formula As explained in (2A), a plurality of compounds of the general formula (2 A polymeric compound (ring-covalent polymer) having a unit structure represented by A) in one compound. The multimeric compound represented by the following formula (2A-4-1) is a compound represented by the general formula (2A). In this case, two units represented by the general formula (2A) are connected together so as to share the benzene ring, which is the a-ring. It is a polymeric compound (ring-covalent polymer) having a coordinate structure in one compound. The polymer compound represented by (2A-4-2) is an a-ring compound as explained in the general formula (2A). Three unit structures represented by general formula (2A) are combined into one compound so as to share a benzene ring. The compound is a polymeric compound (ring-covalent polymer) having the following formula (2A-5-1): The multimeric compound represented by any one of formulas (2A-5-1) to (2A-5-4) can be described by general formula (2A). For example, a plurality of compounds represented by the general formula (2A) are connected together so as to share a benzene ring, which is the b-ring (or c-ring). It is a polymeric compound (ring-covalent polymer) having a unit structure represented by the following formula in one compound. The multimeric compound represented by the following formula (2A-6) can be explained using the general formula (2A), for example: For example, a benzene ring, which is the b-ring (or a-ring, c-ring) of a certain unit structure, and a b-ring ( or a ring, c ring) are condensed with a benzene ring, It is a polymeric compound (a ring-fused polymer) having the unit structure shown in the figure in one compound.

[0110] [ka]

[0111] The multimeric compound is represented by formula (2A-4), formula (2A-4-1) or formula (2A-4-2). The polymerized form expressed by the formula (2A-5-1) to the formula (2A-5-4) or the formula ( 2A-6) and a polymerized form represented by the formula (2A -5-1) to Formula (2A-5-4), and a polymerized form represented by any one of Formula (2A-6) and a polymer in which the polymerized form represented by the formula (2A-4) and the formula (2A-4-1) or the polymerized form represented by formula (2A-4-2) and the polymerized form represented by formula (2A-5-1 ) to Formula (2A-5-4) and a polymerized form represented by Formula (2A-6). The polymer may be a combination of a polymerized form of the hydroxylase and a polymerized form of the hydroxylase.

[0112] Also, the polycyclic aromatic compounds represented by the general formula (1A) or (2A) and their multimers All or some of the hydrogen atoms in the chemical structure may be deuterium, cyano, or halogen. For example, in formula (1A), ring A, ring B, and ring C (rings A to C are aryl rings or heterocyclic rings) are aryl ring), substituents on rings A to C, Y 1 R when is Si-R or Ge-R (= alkyl, cycloalkyl, aryl), and X 1 and X 2 >NR, > C(-R)2 or >Si(-R)2, where R (= alkyl, cycloalkyl, alkyl) In the case of aryl, hydrogen may be replaced by deuterium, cyano, or halogen. In addition, all or some of the hydrogen atoms in the aryl or heteroaryl may be replaced by deuterium, cyano, or halo. The halogen is fluorine, chlorine, bromine or iodine. Preferably, it is fluorine, chlorine or bromine, more preferably fluorine or chlorine.

[0113] Furthermore, the polycyclic aromatic compound and its multimer according to the present invention can be used as a material for an organic device. Examples of organic devices that can be used include organic electroluminescent devices, organic field effect devices, and the like. Examples include transistors and organic thin-film solar cells. In particular, organic electroluminescent devices In the case of the dopant material of the light-emitting layer, Y 1 is B, X 1 and X 2 Compounds where is >NR Things, Y 1 is B, X 1 >O,X 2 Compounds where Y is >NR 1 is B, X 1 and X 2 but As a host material of the light-emitting layer, a compound in which Y 1is B, X 1 >O,X 2 Compounds where Y is >NR 1 is B, X 1 and X 2 Compounds in which is >O are preferred, As a child transport material, Y 1 is B, X 1 and X 2 Compounds where Y is >O 1 P=O,X 1 and X 2 Compounds in which is >O are preferably used.

[0114] Also, the polycyclic aromatic compounds represented by the general formula (1A) or (2A) and their multimers At least one of the aromatic and heteroaromatic rings in the chemical structure has at least one cycloalkyl group. It may be condensed with an alkane.

[0115] For example, aryl and heteroaryl rings that are rings A, B, C, a, b, and c. Aryl groups (aryl, diaryl) as the first and second substituents on the aryl ring, rings A to C arylamino, arylheteroarylamino, diarylboryl or aryloxy aryl group moiety in the amino or heteroaryl portion in arylheteroarylamino), from ring a to ring c The aryl group (as above) and heteroaryl group (as above) as the first and second substituents of Same as above), Y 1 Aryl groups as R in Si—R and Ge—R (similar to above) ), and X 1 and X 2 >NR, >Si(-R)2 and >C(-R)2 Among the aryl group (same as above) and heteroaryl group (same as above) as R in At least one may be fused with at least one cycloalkane.

[0116] Preferably, the aryl rings are ring A, ring B, ring C, ring a, ring b and ring c, and hetero rings. Aryl group (aryl, diaryla) as the first substituent on the aryl ring, ring A to ring C the aryl group in amino, diarylboryl, or aryloxy) and heteroaryl Aryl group (heteroaryl moiety in heteroaryl or diheteroarylamino) , an aryl group (similar to above) and a heteroaryl as the first substituent on rings a to c groups (as above), and X 1 and X 2 >NR, >Si(-R)2 and >Aryl groups (as above) and heteroaryl groups (as above) as R in C(-R)2 At least one of the (similar) is condensed with at least one cycloalkane good.

[0117] More preferably, the aryl rings are ring A, ring B, ring C, ring a, ring b and ring c, and ring A to ring C are An aryl group as the first substituent on the C ring (aryl in aryl or diarylamino) aryl group portion) and heteroaryl group (heteroaryl portion of heteroaryl) , an aryl group (similar to above) and a heteroaryl as the first substituent on rings a to c groups (as above), and X 1 and X 2 >NR, >Si(-R)2 and At least one of the aryl groups (similar to above) as R in C(-R)2 is at least It may be condensed with at least one cycloalkane.

[0118] More preferably, the aryl rings are ring A, ring B, ring C, ring a, ring b and ring c. An aryl group as the first substituent on the C ring (in aryl or diarylamino aryl group portion), aryl group as the first substituent on rings a to c (same as above), etc. Also, X 1 and X 2 R in >NR, >Si(-R)2 and >C(-R)2 At least one of the aryl groups (as above) is substituted with at least one cycloalkyl group. It may be condensed with a leucane.

[0119] "Cycloalkane" includes cycloalkanes with 3 to 24 carbon atoms, cycloalkanes with 3 to 20 carbon atoms, Cycloalkanes, cycloalkanes with 3 to 16 carbon atoms, cycloalkanes with 3 to 14 carbon atoms, Cycloalkanes with prime numbers 5-10, cycloalkanes with carbon numbers 5-8, cycloalkanes with carbon numbers 5-6 Examples include alkanes and cycloalkanes with five carbon atoms.

[0120] Specific cycloalkanes include cyclopropane, cyclobutane, cyclopentane, Cyclohexane, cycloheptane, cyclooctane, cyclononane, cyclodecane, nor Bornene, bicyclo[1.0.1]butane, bicyclo[1.1.1]pentane, bicyclo [2.0.1]pentane, bicyclo[1.2.1]hexane, bicyclo[3.0.1]hexane Hexane, bicyclo[2.1.2]heptane, bicyclo[2.2.2]octane, adaman naphthalene, diamantane, decahydronaphthalene and decahydroazulene, and alkyl (especially methyl) substituted derivatives having 1 to 5 carbon atoms, halogen (especially fluorine) substituted derivatives, and and deuterium-substituted derivatives.

[0121] Among these, for example, the carbon atom at the α-position of cycloalkane (aromatic In cycloalkanes fused to aromatic or heteroaromatic rings, the carbon atom adjacent to the fused site is A structure in which at least one hydrogen atom at the α-position carbon is substituted is preferred, and A structure in which two hydrogen atoms are replaced at the α-position carbon atom is more preferable, and a total of four hydrogen atoms at the two α-position carbon atoms are The substituent is preferably an alkyl group having 1 to 5 carbon atoms. Examples include aryl (especially methyl) substituted compounds, halogen (especially fluorine) substituted compounds, and deuterium substituted compounds. can be done. [ka]

[0122] The number of cycloalkanes fused to one aromatic ring or heteroaromatic ring is preferably 1 to 3. Preferably, one or two rings are preferable, and one ring is even more preferable. For example, one benzene ring Examples of phenyl groups fused with one or more cycloalkanes are shown below. In the above, * indicates a benzene ring included in the skeletal structure of the compound. In the case of a phenyl group, it means a bond substituted on the skeleton structure of the compound. The condensed cycloalkanes shown in formula (Cy-1-4) and formula (Cy-2-4) are The fused ring (group) may be an aromatic ring other than a benzene ring (phenyl group) or Even if the condensed cycloalkane is a cyclopentane or heteroaromatic ring, The same applies to cycloalkanes other than cyclohexane. [ka]

[0123] At least one -CH2- in the cycloalkane may be replaced with -O- However, when multiple -CH2- are replaced with -O-, adjacent -CH2- are replaced with -O-. It is not substituted. For example, a cycloalkane fused to one benzene ring (phenyl group) Examples of the structure in which one or more -CH2- groups are replaced with -O- are shown below. In the above, * indicates a benzene ring included in the skeletal structure of the compound. In the case of a phenyl group, it means a bond substituted on the skeleton structure of the compound. The condensed ring (group) is an aromatic ring or heteroaromatic ring other than a benzene ring (phenyl group). Even in the case of a ring, the condensed cycloalkane is cyclopentane or cyclohexane or The same applies to other cycloalkanes. [ka]

[0124] At least one hydrogen atom in the cycloalkane may be substituted, and this substituent and Examples of such groups include aryl, heteroaryl, diarylamino, and diheteroarylamino. Aryl, heteroaryl, amino, diarylboryl (two aryls are single bond or (which may be bonded via a linking group), alkyl, cycloalkyl, alkoxy, aryl Examples of the silyl group include aryloxy, substituted silyl, deuterium, cyano, and halogen. The explanation of the first substituent mentioned above can be cited. Among these substituents, alkyl (e.g., alkyl having 1 to 6 carbon atoms), cycloalkyl (e.g., cycloalkyl having 3 to 14 carbon atoms), Preferred are cycloalkyl, halogen (e.g., fluorine), and deuterium. When the ring is substituted, it may be substituted to form a spiro structure, for example, one benzene ring ( Examples of spiro structures formed in cycloalkanes fused to a phenyl group are shown below. In the structural formula, * indicates a benzene ring included in the skeletal structure of the compound. In the case of a phenyl group, it means a bond substituted in the skeleton structure of the compound. Taste. [ka]

[0125] Other forms of cycloalkane condensation include polycyclic cycloalkanes represented by general formula (1A) or (2A): The aromatic ring compounds and their multimers are, for example, diaryla condensed with cycloalkanes. an amino group (fused to the aryl moiety), a carbazolyl group (fused to the cycloalkane moiety) fused to the benzene ring portion of the Examples of "diarylamino groups" include those substituted with a benzene ring moiety (condensed with the benzene ring moiety). Examples of the first substituent include the groups explained above as the "first substituent."

[0126] Further specific examples include polycyclic aromatic compounds represented by general formula (2A) and R in its multimer 2 However, diarylamino groups fused with cycloalkanes (this carbazolyl group (fused to the aryl moiety) or cycloalkane-fused carbazolyl group (fused to the benzene ring) Examples include condensation into a moiety.

[0127] As an example, a polycyclic aromatic compound represented by the following general formula (2A-Cy) or Examples include a multimer of a polycyclic aromatic compound having a plurality of structures represented by the general formula (2A-Cy). In the following structural formula, Cy represents a cycloalkane, and n represents independently 1 to 3 (preferably 1). ) and "=(Cy)n" is an arbitrary structure in which n cycloalkanes are condensed. (In the structural formula below, n cycloalkanes are fused to the benzene ring (phenyl group). The definition of each symbol in the structural formula is the same as the definition of each symbol in general formula (2A). The meaning is the same as that of the b ring, the c ring, and the aryl ring formed together with the b ring or the c ring. At least one ring of the heteroaryl ring is substituted with a group represented by formula (Am) described below. [ka]

[0128] Specifically, compounds represented by the following formulas can be mentioned: "Cy" in the following formulas represents cycloaliphatic alkyl groups. Each n is independently 0 to the maximum condensable number (however, all n's are 0). n is preferably 0 to 2 (but all n's are not 0), more preferably Preferably, it is 1, and "=(Cy)n" is any structure in which n cycloalkanes are condensed. For example, in the following formula "2A-Cy-(1)", the benzene rings may be fused at any position. (n cycloalkanes are condensed at the position of "O" in the following structural formula.) "Ph" represents a phenoxy group, "Me" represents a methyl group, and each compound has the first and second substituents described above. and a second substituent, and at least one of the rings corresponding to the b ring and the c ring Another ring is substituted with the formula (Am) described below.

[0129] [ka]

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[0143] The polycyclic aromatic compound or its multimer represented by the general formula (1A) has a small number of B rings and C rings. At least one hydrogen atom in at least one ring is substituted with a group represented by the following formula (Am): In addition, the polycyclic aromatic compound represented by general formula (2A) or a multimer thereof is R 4 ~R 11 At least one of the following is a group represented by the following formula (Am), and / or b At least one of the aryl or heteroaryl rings formed together with the ring or ring c Another hydrogen atom is substituted with a group represented by the following formula (Am): [ka]

[0144] In formula (Am), Ar1 is biphenylyl, Ar2 is aryl (provided that biphenylyl (excluding biphenylyl, aryl or heteroaryl) At least one hydrogen atom in the alkyl group may be replaced by alkyl or cycloalkyl. The group represented by the above formula (Am) is, in *, in the ring B or ring C of the general formula (1A). hydrogen in the ring b or ring c in the general formula (2A), an aryl ring or a heterocyclic ring formed together with the ring b or ring c in the general formula (2A), It replaces hydrogen in the heteroaryl ring.

[0145] These aryl, heteroaryl, alkyl and cycloalkyl include those represented by the general formula Aryl, heteroaryl, alkyl and cycloalkyl as the first substituent in (1A) The description of the alkyl group can be cited.

[0146] Specific examples of Ar2 include phenyl, naphthyl, dibenzofuranyl, and dibenzothio. Phenyl, carbazolyl (N is substituted with alkyl or phenyl having 1 to 5 carbon atoms) These groups may be alkyl groups having 1 to 5 carbon atoms. alkyl (e.g., methyl, ethyl, etc.) or cycloalkyl having 5 to 10 carbon atoms (preferably It may be substituted with cyclohexyl or adamantyl.

[0147] The bonding position of the group represented by formula (Am) is preferably the same as that of R 5 Oh BiR 10 At least one position of.

[0148] Further specific examples of the amino-substituted polycyclic aromatic compounds of the present invention include those represented by the following structural formulas: In the structural formula below, "D" represents deuterium and "Me" represents a methyl group. "tBu" indicates a t-butyl group, "tAm" indicates a t-amyl group, and "Hex" indicates a hexyl group. vinegar.

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[0335] 1-2. Type B amino-substituted polycyclic aromatic compounds and their multimers In particular, the present invention relates to a polycyclic aromatic compound represented by the following general formula (2B), or It is a polymer of a polycyclic aromatic compound having a plurality of structures represented by formula (2B), and a specific b-ring An amino group is substituted at the position, and Ra and Rb groups are present at specific positions on the c and a rings, respectively. It is being replaced. [ka] In the structural formula above and the following structural formulas, "a" to "e" represent benzyl groups. The symbols represent the ring structure represented by Zene ring, and the other symbols are the same as defined above.

[0336] In the above formula (2B), R 21 ~R 30 are each independently hydrogen, aryl, or heteroaryl. aryl, diarylamino, diheteroarylamino, arylheteroarylamino, Diarylboryl (the two aryls may be bonded via a single bond or a linking group) , alkyl, cycloalkyl, alkoxy, aryloxy, triarylsilyl, tri Alkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl or a and alkyldicycloalkylsilyl (the above are the first substituents), and at least One hydrogen is replaced by aryl, heteroaryl, alkyl, or cycloalkyl. (These are referred to as second substituents.) Details of each of these groups will be described later.

[0337] In the above formula (2B), the substituents R 21 ~R 30 Adjacent groups of They may be bonded together with ring d or ring e to form an aryl or heteroaryl ring. At least one hydrogen atom in the formed ring is selected from aryl, heteroaryl, diaryl, arylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryls may be bonded via a single bond or a linking group), alkyl, cyclohexyl, alkyl, alkoxy, aryloxy, triarylsilyl, trialkylsilyl, Tricycloalkylsilyl, dialkylcycloalkylsilyl or alkyldicycloalkylsilyl and optionally substituted with alkylsilyl (these are referred to as first substituents), One hydrogen is replaced by aryl, heteroaryl, alkyl, or cycloalkyl. These groups and the aryl and heteroaryl rings may also be present (these are referred to as second substituents). Details will be provided below.

[0338] In the above formula (2B), the substituent R 21 ~R 30 Adjacent groups in The aryl or heteroaryl ring formed together with the d and e rings may be a benzene ring. These rings can also be considered fused rings formed by condensing other ring structures to the d or e ring shown in the figure. For example, a benzene ring, which is a d-ring (or e-ring), can be used as a ring structure. A benzophenone ring, an indole ring, a pyrrole ring, a benzofuran ring, or a benzothiophene ring is fused to the The resulting rings are naphthalene, carbazole, indole, and dibenzofuran. or dibenzothiophene ring. 25 and the e-ring R 26 is "next door" In other words, "adjacent groups" does not refer to groups adjacent to each other on the same ring. means.

[0339] In the above formula (2B), R 25 and R 26 are bonded to form >O, >NR, >Si(-R) 2, >C(-R)2, >S or >Se. As a result, the d and e rings The amino group having at least N(amino) is formed by bonding the d ring and the e ring together. A heteroaryl having N) derived from the >NR and >Si groups is formed. R in (-R)2 is independently an aryl having 6 to 12 carbon atoms, a hexacyclic alkyl group having 2 to 15 carbon atoms, or cycloalkyl having 3 to 14 carbon atoms, cycloaryl having 1 to 6 carbon atoms, or The above-mentioned first substituents), at least one hydrogen atom in these is an aryl group having 6 to 12 carbon atoms. C2-15 heteroaryl, C1-6 alkyl or C3-14 alkyl The R in >C(—R)2 may be substituted with cycloalkyl (the second substituent). is hydrogen, aryl having 6 to 12 carbon atoms, heteroaryl having 2 to 15 carbon atoms, or a cycloalkyl having 3 to 14 carbon atoms (these are the first substituents), At least one hydrogen atom in Substituted with aryl, alkyl having 1 to 6 carbon atoms, or cycloalkyl having 3 to 14 carbon atoms (These are referred to as second substituents.) Details of each of these groups will be described later.

[0340] In the above formula (2B), Ra is an aryl, heteroaryl, alkyl, cycloalkyl, Alkoxy, aryloxy, triarylsilyl, trialkylsilyl, tricycloa alkylsilyl, dialkylcycloalkylsilyl or alkyldicycloalkylsilyl (these are the first substituents), and at least one hydrogen atom in these is selected from the group consisting of aryl, hetero, The second substituent may be substituted with aryl, alkyl, or cycloalkyl. The first substituents include alkyl, triarylsilyl, trialkylsilyl, and silyl. Chloalkyl is preferred, and alkyl and cycloalkyl are more preferred. Specific preferred groups include adamantyl, t-butyl and t-amyl. The details of each group will be described later.

[0341] In the above formula (2B), Rb is hydrogen, aryl, heteroaryl, diarylamino, diaryl Heteroarylamino, arylheteroarylamino, diarylboryl (two aryl alkyl, cycloalkyl, Alkoxy, aryloxy, triarylsilyl, trialkylsilyl, tricycloa alkylsilyl, dialkylcycloalkylsilyl or alkyldicycloalkylsilyl (these are the first substituents), and at least one hydrogen atom in these is selected from the group consisting of aryl, hetero, The second substituent may be substituted with aryl, alkyl, or cycloalkyl. The first substituent is preferably alkyl or cycloalkyl. Specific examples of the first substituent include: Preferred examples of the radicals are hydrogen, methyl, adamantyl, t-butyl and t-amyl. Each of these groups will be described in detail below.

[0342] In the above formula (2B), Y 1 is B, P, P=O, P=S, Al, Ga, As, Si-R or or Ge—R, wherein R in the Si—R and Ge—R is aryl, alkyl, or cyclohexyl. The details of each of these groups will be described later. In the case of O, P=S, Si-R, or Ge-R, the atom bonding to the a-ring, b-ring, or c-ring is P, Si or Ge. 1 is preferably B, P, P=O, P=S or Si-R. Of these, B, P, P═O or P═S is more preferred, and B is particularly preferred.

[0343] In the above formula (2B), X 1 and X 2 are independently >O, >NR, >Si( -R), >C(-R), >S or >Se, and the >NR and >Si(-R R in 2) is independently an 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 (all of the above, First substituent), at least one hydrogen atom in these is aryl having 6 to 12 carbon atoms, Heteroaryl with 2 to 15 prime numbers, alkyl with 1 to 6 carbon atoms, or cycloalkyl with 3 to 14 carbon atoms The R in the above >C(-R)2 may be substituted with a hydrogen atom. aryl having 6 to 12 carbon atoms, heteroaryl having 2 to 15 carbon atoms, aryl having 1 to 6 carbon atoms alkyl or cycloalkyl having 3 to 14 carbon atoms (these are the first substituents), At least one hydrogen atom in the alkyl group is an aryl group having 6 to 12 carbon atoms, a heteroaryl group having 2 to 15 carbon atoms, or may be substituted with alkyl having 1 to 6 carbon atoms or cycloalkyl having 3 to 14 carbon atoms. (These are the second substituents.) The details of each of these groups will be described later. R in at least one of R, >Si(-R)2 and >C(-R)2 is -O-, - At least one of the rings a, b and c is connected by S-, -C(-R)2- or a single bond. R in the -C(-R)2- may be alkyl or alkyl having 1 to 6 carbon atoms. is a cycloalkyl having 3 to 14 carbon atoms (these are the first substituents). This will also be discussed later.

[0344] Here, "at least one of the above-mentioned >NR, >Si(—R)2 and >C(—R)2" In the formula, R is -O-, -S-, -C(-R)2- or a single bond, and the ring a, the ring b and the ring The provision that "bonds to at least one of rings a and c" means that the ring represented by the following formula (2B-3-1) X 1 or X 2 is a compound having a ring structure in which That is, for example, the benzyl ring b (or c) in the general formula (2B) can be expressed as For the ring, X 1 (or X 2 ) and another ring is condensed to form b' The compound has a ring (or ring c'). The resulting fused ring b' (or fused ring c') is, for example, a phenoxazine ring, a phenothiazine ring, or an acridine ring. In formula (2B-3-1), the amino group and Ra group shown in formula (2B) are omitted, but b The substitution position of the amino group in ring ' is shown in ring b of formula (2B) in ring b'. The substitution position of the Ra group in the c' ring is the same as that of the group of formula (2 The substitution position is the same as that shown in ring c of B).

[0345] [ka]

[0346] In addition, "at least one of the above-mentioned >NR, >Si(—R)2 and >C(—R)2 R in the formula (I) is -O-, -S-, -C(-R)2- or a single bond, and the ring a, the ring b and the ring The provision that "bonds to at least one ring of ring c" is applicable to the above formula (2B-3-2) and formula (2 B-3-3) is represented by X 1 and X 2 At least one of the following is incorporated into the fused ring a' It can also be expressed as a compound having a ring structure. For example, the a ring in general formula (2B) For a given benzene ring, X 1 (or X 2 , or X 1 Oyo X 2 ) to capture It is a compound having a ring a' formed by condensing another ring. is, for example, a phenoxazine ring, a phenothiazine ring, or an acridine ring. "Am" in formula (2B-3-2) and formula (2B-3-3) means the amino group shown in formula (2B). In addition, in formula (2B-3-2) and formula (2B-3-3), The Rb group in the a' ring is omitted, but the substitution position of the Rb group in the a' ring is The substitution positions are the same as those shown in the a-ring of (2B).

[0347] In formula (2B), any "-C(-H)=" in ring a, ring b, and ring c may be replaced with "-N The partial structures of each ring are shown below. "Am" in the structural formula is It is an amino group shown in formula (2B). [ka] [ka] [ka]

[0348] In the above formula (2B), R 21 ~R 30 Adjacent groups of the rings bond to form the d or e ring. Examples of the "aryl ring" formed together with the above include aryl rings having 9 to 30 carbon atoms. An aryl ring having 9 to 20 carbon atoms is preferable, and an aryl ring having 9 to 16 carbon atoms is more preferable. An aryl ring having 9 to 12 carbon atoms is more preferred, and an aryl ring having 9 to 10 carbon atoms is particularly preferred. Since the d-ring or e-ring is already composed of a benzene ring having 6 carbon atoms, The minimum carbon number is 9, which is the total number of carbon atoms in the fused ring formed by condensing a 5-membered ring to the fused ring.

[0349] Specific examples of the "aryl ring" include a bicyclic ring, a biphenyl ring, a fused bicyclic ring, and a naphthyl ring. Terphenyl ring, tricyclic terphenyl ring (m-terphenyl, o-terphenyl, p-terphenyl) phenyl), fused tricyclic rings such as acenaphthylene ring, fluorene ring, phenalene ring, Phenanthrene ring, fused tetracyclic triphenylene ring, pyrene ring, naphthacene ring, fused pentacyclic ring Examples of ring systems include perylene ring and pentacene ring.

[0350] In the above formula (2B), R 21 ~R 30 Adjacent groups of the rings bond to form the d or e ring. Examples of the "heteroaryl ring" formed together with A heteroaryl ring having 6 to 25 carbon atoms is preferred, and a heteroaryl ring having 6 to 20 carbon atoms is also preferred. A heteroaryl ring is more preferred, and a heteroaryl ring having 6 to 15 carbon atoms is even more preferred. Heteroaryl rings having 6 to 10 carbon atoms are particularly preferred. For example, the ring may contain a heteroatom selected from oxygen, sulfur, and nitrogen in addition to carbon as a ring-constituting atom. Examples include heterocyclic rings containing 1 to 5 carbon atoms. Since it is composed of a Zene ring, the total number of carbon atoms in the fused ring with a 5-membered ring fused to it is 6, which is the minimum carbon number. It becomes a prime number.

[0351] Specific examples of the "heteroaryl ring" include an indole ring, an isoindole ring, 1H-indazole ring, benzimidazole ring, benzoxazole ring, benzothiazo benzotriazole ring, quinoline ring, isoquinoline ring, cinnoline ring, quinolin ring, Zoline ring, quinoxaline ring, phthalazine ring, naphthyridine ring, carbazole ring, acrididine ring phenoxathiin ring, phenoxazine ring, phenothiazine ring, phenazine ring, phenazine ring Nazacillin ring, benzofuran ring, isobenzofuran ring, dibenzofuran ring, benzothiophene Phenylene ring, dibenzothiophene ring, thianthrene ring, indolocarbazole ring, benzoin dolocarbazole ring, benzobenzoindolocarbazole ring, naphthobenzofuran ring, etc. Examples include:

[0352] The "aryl" (first substituent) is, for example, an aryl having 6 to 30 carbon atoms, An aryl having 6 to 20 carbon atoms is preferred, an aryl having 6 to 16 carbon atoms is more preferred, and an aryl having 6 to 1 carbon atoms is more preferred. The aryl having 2 carbon atoms is more preferred, and the aryl having 6 to 10 carbon atoms is particularly preferred.

[0353] Specific examples of the aryl include phenyl, which is a monocyclic ring, biphenylyl, which is a bicyclic ring, and fused aryl. The bicyclic ring system is naphthyl, the tricyclic ring system is terphenylyl (m-terphenylyl, o-terphenylyl), p-terphenylyl), fused tricyclic ring systems, acenaphthylenyl, fluorenyl , phenalenyl, phenanthrenyl, fused tetracyclic ring systems triphenylenyl, pyrenyl, na Examples include phthalocenyl, and fused pentacyclic ring systems such as perylenyl and pentacenyl.

[0354] The "heteroaryl" (first substituent) is, for example, a heteroaryl having 2 to 30 carbon atoms. Heteroaryl having 2 to 25 carbon atoms is preferable, and heteroaryl having 2 to 20 carbon atoms is more preferable. Heteroaryl having 2 to 15 carbon atoms is more preferred, and heteroaryl having 2 to 10 carbon atoms is even more preferred. In addition, heteroaryl is particularly preferred. and heterocyclic rings each containing 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen. do.

[0355] Specific examples of heteroaryl include pyrrolyl, oxazolyl, and isoxazolyl. thiazolyl, isothiazolyl, imidazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, pyrazolyl, pyridinyl, pyrimidinyl, pyridazinyl, Pyrazinyl, triazinyl, indolyl, isoindolyl, 1H-indazolyl, benzo Imidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, Quinolinyl, isoquinolinyl, cinnolinyl, quinazolinyl, quinoxalinyl, phthalazinyl naphthyridinyl, purinyl, pteridinyl, carbazolyl, acridinyl, phenoxy Sathiinyl, phenoxazinyl, phenothiazinyl, phenazinyl, phenazasilinyl, Indolizinyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, Naphthobenzofuranyl, thiophenyl, benzothiophenyl, dibenzothiophenyl, Benzothiophenyl, benzophosphoryl, dibenzophosphoryl, benzophospho Monovalent radicals of dibenzophosphole oxide rings, monovalent radicals of dibenzophosphole oxide rings, furazanyl, thiazol-1, Indolocarbazolyl, benzindolocarbazolyl and benzobenzoyl Examples include benzoxazole and benzoxazole.

[0356] "Diarylamino", "Diheteroarylamino", "Arylheteroarylamino" The aryl and heteroaryl groups in "diarylboryl" and "diarylboryl" (the first substituents) The above description of "aryl" or "heteroaryl" can be used as the term. can.

[0357] The two aryls in "diarylboryl" may be a single bond or a linking group (e.g., > may be bonded via a C(-R), >O, >S or >NR), where >C R in (-R)2 and >NR is aryl, heteroaryl, diarylamino, aryl alkyl, cycloalkyl, alkoxy, or aryloxy (each of which is a first substituent); The first substituent may further include aryl, heteroaryl, alkyl, or cycloalkyl ( The above-mentioned second substituents may be substituted, and specific examples of these groups include the above-mentioned first The description of aryl, heteroaryl, diarylamino or aryloxy as substituents For clarity, please refer to the description of alkyl, cycloalkyl, or alkoxy as the first substituent below. Can be used.

[0358] The "alkyl" (first substituent) may be either a straight chain or a branched chain, and examples thereof include: Examples include linear alkyl groups having 1 to 24 carbon atoms and branched alkyl groups having 3 to 24 carbon atoms. Alkyl having 1 to 18 prime numbers (branched alkyl having 3 to 18 carbon atoms) is preferred, Alkyl having 2 (branched alkyl having 3 to 12 carbon atoms) is more preferred, and alkyl having 1 to 8 carbon atoms is more preferred. alkyl (branched alkyl having 3 to 8 carbon atoms) is more preferred, and alkyl (branched alkyl having 1 to 6 carbon atoms) is more preferred. Branched alkyl having 3 to 6 carbon atoms is particularly preferred, and alkyl having 1 to 5 carbon atoms (branched alkyl having 3 to 5 carbon atoms) is particularly preferred. branched alkyl) is most preferred.

[0359] Specific examples of alkyl include methyl, ethyl, n-propyl, isopropyl, and n-butyl. butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl , t-pentyl (t-amyl), n-hexyl, 1-methylpentyl, 3,3-dimethyl Butyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, t-octyl butyl (1,1,3,3-tetramethylbutyl), 1-methylheptyl, 2-ethylhexyl Cyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 2,6-dimethyl 4-heptyl, 3,5,5-trimethylhexyl, n-decyl, n-undecyl, 1 -Methyldecyl, n-dodecyl, n-tridecyl, 1-hexylheptyl, n-tetradecyl sil, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, n -Eicosyl, etc. 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 ethylhexyl, 1-ethyl-1,3-dimethylbutyl, 1,1,2,2-tetramethylpropyl propyl, 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- Propyl-1-methylbutyl, 1,1-dimethylhexyl, and the like are also included.

[0360] The "cycloalkyl" (first substituent) includes cycloalkyl having 3 to 24 carbon atoms, cycloalkyl having 3 to 20 carbon atoms, cycloalkyl having 3 to 16 carbon atoms, cycloalkyl having 3 to 14 carbon atoms Cycloalkyl having 5 to 10 carbon atoms, cycloalkyl having 5 to 8 carbon atoms, Examples include cycloalkyl having 5 to 6 carbon atoms and cycloalkyl having 5 carbon atoms.

[0361] Specific cycloalkyl groups include cyclopropyl, cyclobutyl, cyclopentyl, Cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, and and alkyl (especially methyl) substituted derivatives of these having 1 to 5 carbon atoms, norbornenyl, bicyclo [1.0.1]butyl, bicyclo[1.1.1]pentyl, bicyclo[2.0.1]pentyl ethyl, bicyclo[1.2.1]hexyl, bicyclo[3.0.1]hexyl, bicyclo[ 2.1.2]heptyl, bicyclo[2.2.2]octyl, adamantyl, diamantyl , decahydronaphthalenyl, decahydroazulenyl, and the like.

[0362] Examples of the "alkoxy" (first substituent) include linear or linear alkoxy groups having 1 to 24 carbon atoms. Examples include branched alkoxy with 3 to 24 carbon atoms. alkoxy having 1 to 12 carbon atoms (branched alkoxy having 3 to 18 carbon atoms) is preferred, Alkoxy having 1 to 6 carbon atoms (branched alkoxy having 3 to 6 carbon atoms) is more preferred, Alkoxy having 1 to 5 carbon atoms (branched alkoxy having 3 to 5 carbon atoms) is more preferred, Particularly preferred are alkoxy groups.

[0363] Specific alkoxy includes methoxy, ethoxy, propoxy, isopropoxy, n -butoxy, isobutoxy, s-butoxy, t-butoxy, t-amyloxy, n-pentoxy t-pentyloxy, isopentyloxy, neopentyloxy, t-pentyloxy, n-hexyloxy Siloxy, 1-methylpentyloxy, 4-methyl-2-pentyloxy, 3,3-di Methylbutoxy, 2-ethylbutoxy, n-heptyloxy, 1-methylhexyloxy , n-octyloxy, t-octyloxy, 1-methylheptyloxy, 2-ethylheptyloxy xyloxy, 2-propylpentyloxy, n-nonyloxy, 2,2-dimethylheptyloxy Hexyloxy, 2,6-dimethyl-4-heptyloxy, 3,5,5-trimethylhexyl Oxy, n-decyloxy, n-undecyloxy, 1-methyldecyloxy, n-dode Cyloxy, n-tridecyloxy, 1-hexylheptyloxy, n-tetradecyloxy Oxy, n-pentadecyloxy, n-hexadecyloxy, n-heptadecyloxy, n -octadecyloxy, n-eicosyloxy, and the like.

[0364] The aryl in "aryloxy" (first substituent) is the same as the above-mentioned "aryl". The explanation can be cited.

[0365] For "triarylsilyl" (first substituent), three hydrogen atoms in the silyl group are Each of these groups is independently substituted with an aryl, and the aryl is the first substituent described above. The groups described as "aryl" in the above can be cited. The aryl is an aryl having 6 to 10 carbon atoms, specifically, phenyl and naphthyl. Specific examples of triarylsilyl include triphenylsilyl and diphenylsilyl. Mononaphthylsilyl, monophenyldinaphthylsilyl, trinaphthylsilyl, etc. It can be given.

[0366] For "trialkylsilyl" (first substituent), the three hydrogen atoms in the silyl group are Each of these groups is independently substituted with an alkyl group, and the alkyl group is the same as the first substituent described above. The groups described as "alkyl" in the above can be cited. The alkyl is an alkyl having 1 to 5 carbon atoms, specifically, methyl, ethyl, propyl, i -propyl, butyl, sec-butyl, t-butyl, t-amyl, and the like.

[0367] Specific examples of trialkylsilyl include trimethylsilyl, triethylsilyl, and triplylsilyl. Iodopropylsilyl, tri-i-propylsilyl, tributylsilyl, tri-sec-butylsilyl , tri-t-butylsilyl, tri-t-amylsilyl, ethyldimethylsilyl, propyldimethylsilyl Isopropylsilyl, i-propyldimethylsilyl, butyldimethylsilyl, sec-butyldimethylsilyl t-butyldimethylsilyl, t-amyldimethylsilyl, methyldiethylsilyl silyl, propyldiethylsilyl, i-propyldiethylsilyl, butyldiethylsilyl, sec-Butyldiethylsilyl, t-Butyldiethylsilyl, t-Amyldiethylsilyl , methyldipropylsilyl, ethyldipropylsilyl, butyldipropylsilyl, sec -Butyldipropylsilyl, t-Butyldipropylsilyl, t-Amyldipropylsilyl , methyldi-i-propylsilyl, ethyldi-i-propylsilyl, butyldi-i-propylsilyl sec-butyldi-i-propylsilyl, t-butyldi-i-propylsilyl, t-butyldi-i-propylsilyl Examples include methyldi-i-propylsilyl.

[0368] "Tricycloalkylsilyl" (first substituent) is a silyl group with three hydrogen atoms. and the cycloalkyl is a group in which each of the above is independently substituted with cycloalkyl. The group described as "cycloalkyl" in the first substituent described above can be cited. The cycloalkyl to be substituted is preferably a cycloalkyl having 5 to 10 carbon atoms. Specifically, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclo Nonyl, cyclodecyl, bicyclo[1.1.1]pentyl, bicyclo[2.0.1]pentyl ethyl, bicyclo[1.2.1]hexyl, bicyclo[3.0.1]hexyl, bicyclo[ 2.1.2]heptyl, bicyclo[2.2.2]octyl, adamantyl, decahydronaphthalene Examples include phthalenyl and decahydroazulenyl.

[0369] Specific examples of tricycloalkylsilyl include tricyclopentylsilyl, tricyclo hexylsilyl, etc.

[0370] "Dialkylcycloalkylsilyl" is a compound substituted with two alkyls and one cycloalkyl. " (first substituent) and "alkyldicycloalkyl" substituted with one alkyl and two cycloalkyls. Specific examples of the "chloroalkylsilyl" (first substituent) include the specific alkyl and cycloalkylsilyl groups mentioned above. and silyl substituted with a group selected from cycloalkyl.

[0371] For details of the second substituents, the explanation of the first substituents can be cited.

[0372] Specifically, the steric hindrance, electron donating property and electron The wavelength of emitted light can be adjusted by the attraction, and the group is preferably represented by the following structural formula: More preferably, it is methyl, t-butyl, t-amyl, t-octyl, 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-dimethylcarbazolyl, 3,6-di-t-butyl and methyl, t-butyl, t-butylcarbazolyl, and phenoxy. -Amyl, t-octyl, phenyl, o-tolyl, 2,6-xylyl, 2,4,6-methy butyl, diphenylamino, di-p-tolylamino, bis(p-(t-butyl)phenyl) Amino, carbazolyl, 3,6-dimethylcarbazolyl and 3,6-di-t-butylcarbazolyl From the viewpoint of ease of synthesis, the greater the steric hindrance, the more selective the synthesis. Specifically, t-butyl, t-amyl, t-octyl, o-tolyl, p- Tolyl, 2,4-xylyl, 2,5-xylyl, 2,6-xylyl, 2,4,6-mesityl di-p-tolylamino, bis(p-(t-butyl)phenyl)amino, 3,6-dimethylamino Tylcarbazolyl and 3,6-di-t-butylcarbazolyl are preferred.

[0373] In the following structural formula, "Me" is methyl, "tBu" is t-butyl, and "tAm" is t- amyl, "tOct" represents t-octyl, and * represents the bond position. [ka] [ka] [ka] [ka] [ka]

[0374] Y in formula (2B) 1 In the above, R in Si-R and Ge-R is aryl, alkyl or is a cycloalkyl, but is particularly an aryl having 6 to 10 carbon atoms (e.g., phenyl, naphthyl) etc.), alkyl having 1 to 5 carbon atoms (e.g., methyl, ethyl, etc.) or alkyl having 5 to 10 carbon atoms Cycloalkyl (preferably cyclohexyl or adamantyl) is preferred.

[0375] X in formula (2B) 1 and X 2 As >NR R, as well as R25 and R 26 R in the linking group >NR formed by bonding is aryl, heteroaryl, alkyl or cycloalkyl (the above, the first substituent), which are aryl, heteroaryl It may be substituted with alkyl or cycloalkyl (these are referred to as second substituents), As the first and second substituents, particularly aryl having 6 to 10 carbon atoms (e.g., phenyl) is preferred. phenyl, naphthyl, etc.), heteroaryl having 2 to 15 carbon atoms (e.g., carbazolyl, diphenyl, naphthyl, etc.), benzofuranyl, dibenzothiophenyl, etc.), alkyl having 1 to 5 carbon atoms (e.g., methyl , ethyl, etc.) or cycloalkyl having 5 to 10 carbon atoms (preferably cyclohexyl or aryl). damantyl), and phenyl, naphthyl, carbazolyl, dibenzofuranyl or Dibenzothiophenyl is more preferred, and dibenzofuranyl or dibenzothiophenyl is Further, dibenzofuranyl or dibenzothiophenyl is more preferred as the second substituent. It is particularly preferred that the second substituent is t-butyl, phenyl, or the like. These substituents are substituted with oxygen or sulfur atoms. The substitution is preferably at the la position.

[0376] X in formula (2B) 1 and X 2 R in Si(-R)2 as well as R 25 Oh BiR 26 The R in the linking group Si(-R)2 formed by bonding is aryl, heteroaryl, aryl, alkyl, or cycloalkyl (these are the first substituents), which are , heteroaryl, alkyl, or cycloalkyl (the above 2 substituents), and as these (first and second substituents), alkyl groups having 6 to 10 carbon atoms are particularly preferred. aryl (e.g., phenyl, naphthyl, etc.), heteroaryl having 2 to 15 carbon atoms (e.g., carboxyl group, rubazolyl, etc.), alkyl having 1 to 5 carbon atoms (e.g., methyl, ethyl, etc.) or Cycloalkyl having 5 to 10 carbon atoms (preferably cyclohexyl or adamantyl) is preferred.

[0377] X in formula (2B) 1 and X 2 R in C(-R)2 as well as R 25 and R 26 R in the linking group >C(-R)2 formed by bonding is aryl, heteroaryl, aryl, alkyl, or cycloalkyl (these are the first substituents), The second substituent may be substituted with aryl, alkyl, or cycloalkyl. Substituents), and these (first and second substituents) are particularly aryl groups having 6 to 10 carbon atoms. aryl (e.g., phenyl, naphthyl, etc.), heteroaryl (e.g., carbamates) having 2 to 15 carbon atoms alkyl having 1 to 5 carbon atoms (e.g., methyl, ethyl, etc.) or alkyl having 5 to 5 carbon atoms (e.g., methyl, ethyl, etc.) Cycloalkyl (preferably cyclohexyl or adamantyl) is preferred.

[0378] In formula (2B), X 1 and X 2 is bonded to at least one of ring a, ring b and ring c In this case, the linking group may be, for example, -O-, -S-, -C(-R)2- or a single bond. Among these, R in "-C(-R)2-" is hydrogen, alkyl or cycloalkyl. alkyl, especially alkyl having 1 to 5 carbon atoms (e.g., methyl, ethyl, etc.) or Cycloalkyl having 5 to 10 carbon atoms (preferably cyclohexyl or adamantyl) is preferred.

[0379] The present invention also provides a polycyclic aromatic compound having a plurality of unit structures represented by general formula (2B): The multimer is preferably a dimer to a hexamer, more preferably a dimer to a trimer, and more preferably a dimer. The polymer is particularly preferably in the form of a compound having a plurality of the above unit structures. For example, the unit structure is preferably a single bond, an alkylene group having 1 to 3 carbon atoms, a phenylene group, a naphthalene group, or the like. In addition to the form in which multiple units are bonded together with linking groups such as butylene groups (linked polymers), Any ring (a, b or c) contained in the ring is shared by multiple unit structures. It may be a ring-sharing type polymer, or any ring ( a ring, b ring, or c ring) are bonded together in a condensed state (condensed ring type polymer). However, ring-sharing type multimers and ring-condensed type multimers are preferred, and ring-sharing type multimers are more preferred. preferable.

[0380] Examples of such multimers include those represented by the following formula (2B-4), formula (2B-4-1), or The multimeric compound represented by the following formula (2B-4) or formula (2B-5) is also included. The polymer compound represented by general formula (2B) is an a-ring benzoate. The unit structures represented by the two general formulas (2B) are combined into one compound by sharing the Zene ring. It is a polymeric compound (ring-covalent polymer) having the following formula (2B-6): The polymeric compound can be explained by the general formula (2B), for example, by the benzoate which is the a-ring of a certain unit structure. The benzene ring is fused with the benzene ring, which is the a-ring of a certain unit structure, to form two general formulas ( 2B) in one compound (a ring-fused polymer) be.

[0381] [ka] In addition, "Am" in the above structural formula is the amino group shown in formula (2B).

[0382] The polymeric compound is a polymerized form represented by formula (2B-4) or formula (2B-4-1). and the polymerized form represented by formula (2B-6).

[0383] In addition, the water in the chemical structure of the polycyclic aromatic compound represented by the general formula (2B) and its multimer The atoms may be deuterium, cyano, or halogen in whole or in part. For example, In (2B), the rings a to e, the substituents on these rings, Y 1 is Si-R or Ge- R (=aryl, alkyl, cycloalkyl) when R, and X 1 and X 2 When R is >NR, >C(-R)2 or >Si(-R)2, R (=aryl, hydroxyl) hydrogen in the alkyl, cycloalkyl, cyclohexane ... Among these, all or one of the aryls and heteroaryls can be substituted. In one embodiment, hydrogen atoms in the group are substituted with deuterium, cyano, or halogen. fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, more preferably or fluorine or chlorine.

[0384] Furthermore, the polycyclic aromatic compound and its multimer according to the present invention can be used as a material for an organic device. Examples of organic devices that can be used include organic electroluminescent devices, organic field effect devices, and the like. Examples include transistors and organic thin-film solar cells. In particular, organic electroluminescent devices In the case of the dopant material of the light-emitting layer, Y 1 is B, X 1 and X 2 Compounds where is >NR Things, Y 1 is B, X 1 >O,X 2 Compounds where Y is >NR 1 is B, X 1 and X 2 but As a host material of the light-emitting layer, a compound in which Y 1 is B, X 1 >O,X 2 Compounds where Y is >NR 1 is B, X 1 and X 2 Compounds in which is >O are preferred, As a child transport material, Y 1 is B, X 1 and X 2 Compounds where Y is >O 1 P=O,X 1 and X 2 Compounds in which is >O are preferably used.

[0385] In addition, the aromatic compounds in the chemical structure of the polycyclic aromatic compounds represented by the general formula (2B) and their multimers At least one of the aromatic and heteroaromatic rings is fused with at least one cycloalkane. It may be done.

[0386] For example, aryl rings and heteroaryl rings which are rings a to e, first and second bonds to these rings and an aryl group (aryl, diarylamino, arylheteroa) as the second substituent. the aryl group moiety in arylamino, diarylboryl, or aryloxy) and Heteroaryl groups (heteroaryl, diheteroarylamino or arylheteroaryl) heteroaryl moiety in aryl amino), Y 1 where R is the Si-R and Ge-R All aryl groups, and X 1 and X 2 >NR, >Si(-R)2 and > Aryl and heteroaryl groups as the first and second substituents for R in C(-R)2 At least one of the aryl groups is fused with at least one cycloalkane Good too.

[0387] Preferably, the aryl and heteroaryl rings are rings a to e, and the second rings to these rings are 1. An aryl group (aryl, diarylamino, diarylboryl or the aryl group in aryloxy) and heteroaryl groups (heteroaryl or the heteroaryl moiety in diheteroarylamino), and X 1 and X 2 Yes As the first substituent for R in >NR, >Si(-R)2 and >C(-R)2 At least one of the aryl and heteroaryl groups has at least one cycloalkyl group. It may be condensed with an alkane.

[0388] More preferred are aryl rings a to e, and aryl groups as the first substituents on these rings. Aryl groups (aryl groups in aryl or diarylamino) and heteroaryl groups a heteroaryl group (heteroaryl moiety in heteroaryl), and X 1 and X 2 Yes As the first substituent for R in >NR, >Si(-R)2 and >C(-R)2 At least one of the aryl groups is fused with at least one cycloalkane. That's fine.

[0389] More preferably, the aryl rings are rings a to e, and the first substituents on these rings are an aryl group (the aryl group portion of an aryl or diarylamino group), and X 1 and X 2 The first step for R in >NR, >Si(-R)2 and >C(-R)2 is At least one of the aryl groups as a substituent is substituted with at least one cycloalkane. It may be condensed with an alkyl group.

[0390] "Cycloalkane" includes cycloalkanes with 3 to 24 carbon atoms, cycloalkanes with 3 to 20 carbon atoms, Cycloalkanes, cycloalkanes with 3 to 16 carbon atoms, cycloalkanes with 3 to 14 carbon atoms, Cycloalkanes with prime numbers 5-10, cycloalkanes with carbon numbers 5-8, cycloalkanes with carbon numbers 5-6 Examples include alkanes and cycloalkanes with five carbon atoms.

[0391] Specific cycloalkanes include cyclopropane, cyclobutane, cyclopentane, Cyclohexane, cycloheptane, cyclooctane, cyclononane, cyclodecane, nor Bornene, bicyclo[1.0.1]butane, bicyclo[1.1.1]pentane, bicyclo [2.0.1]pentane, bicyclo[1.2.1]hexane, bicyclo[3.0.1]hexane Hexane, bicyclo[2.1.2]heptane, bicyclo[2.2.2]octane, adaman naphthalene, diamantane, decahydronaphthalene and decahydroazulene, and alkyl (especially methyl) substituted derivatives having 1 to 5 carbon atoms, halogen (especially fluorine) substituted derivatives, and and deuterium-substituted derivatives.

[0392] Among these, for example, the carbon atom at the α-position of cycloalkane (aromatic In cycloalkanes fused to aromatic or heteroaromatic rings, the carbon atom adjacent to the fused site is A structure in which at least one hydrogen atom at the α-position carbon is substituted is preferred, and A structure in which two hydrogen atoms are replaced at the α-position carbon atom is more preferable, and a total of four hydrogen atoms at the two α-position carbon atoms are The substituent is preferably an alkyl group having 1 to 5 carbon atoms. Examples include aryl (especially methyl) substituted compounds, halogen (especially fluorine) substituted compounds, and deuterium substituted compounds. can be done. [ka] In the above structural formula, "Am" is the amino group shown in formula (2B), and "Me" is It is a methyl group.

[0393] The number of cycloalkanes fused to one aromatic ring or heteroaromatic ring is preferably 1 to 3. Preferably, one or two rings are preferable, and one ring is even more preferable. For example, one benzene ring Examples of phenyl groups fused with one or more cycloalkanes are shown below. In the above, * indicates a benzene ring included in the skeletal structure of the compound. In the case of a phenyl group, it means a bond substituted on the skeleton structure of the compound. The condensed cycloalkanes shown in formula (Cy-1-4) and formula (Cy-2-4) are The fused ring (group) may be an aromatic ring other than a benzene ring (phenyl group) or Even if the condensed cycloalkane is a cyclopentane or heteroaromatic ring, The same applies to cycloalkanes other than cyclohexane. [ka]

[0394] At least one -CH2- in the cycloalkane may be replaced with -O- However, when multiple -CH2- are replaced with -O-, adjacent -CH2- are replaced with -O-. It is not substituted. For example, a cycloalkane fused to one benzene ring (phenyl group) Examples of the structure in which one or more -CH2- groups in the formula are replaced with -O- are shown below. In the above, * indicates a benzene ring included in the skeletal structure of the compound. In the case of a phenyl group, it means a bond substituted on the skeleton structure of the compound. The condensed ring (group) is an aromatic ring or heteroaromatic ring other than a benzene ring (phenyl group). Even in the case of a ring, the condensed cycloalkane is cyclopentane or cyclohexane or The same applies to other cycloalkanes. [ka]

[0395] At least one hydrogen atom in the cycloalkane may be substituted, and this substituent and Examples of such groups include aryl, heteroaryl, diarylamino, and diheteroarylamino. Aryl, heteroaryl, amino, diarylboryl (two aryls are single bond or (which may be bonded via a linking group), alkyl, cycloalkyl, alkoxy, aryl Examples of the silyl group include aryloxy, substituted silyl, deuterium, cyano, and halogen. The explanation of the first substituent can be cited. Among these substituents, alkyl ( For example, alkyl having 1 to 6 carbon atoms), cycloalkyl (for example, cycloalkyl having 3 to 14 carbon atoms), Preferred are cycloalkyl, halogen (e.g., fluorine), and deuterium. When substituted, it may be a substitution form forming a spiro structure, for example, one benzene ring ( Examples of spiro structures formed in cycloalkanes fused to a phenyl group are shown below. In the formula, * indicates a benzene ring included in the skeletal structure of the compound. In the case of a phenyl group, it means a bond that substitutes for the skeletal structure of the compound. do. [ka]

[0396] Another form of cycloalkane condensation is a polycyclic aromatic compound represented by general formula (2B): and polymers thereof, for example, diarylamino groups fused with cycloalkanes (this aryl group), carbazolyl group fused with cycloalkane (this benzene ring part) benzocarbazolyl group (fused to the benzene ring) or fused to a cycloalkane Examples of the "diarylamino group" include those substituted with a "diarylamino group" as described above in "First Examples of the substituent include the groups described above.

[0397] Further specific examples include polycyclic aromatic compounds represented by general formula (2B) and In the polymer, Rb is a diarylamino group fused with a cycloalkane (this aryl carbazolyl group (fused to the aryl moiety) or cycloalkane-fused carbazolyl group (fused to the benzene ring) Examples include condensation into a moiety.

[0398] As an example, a polycyclic aromatic compound represented by the following general formula (2B-Cy) or a polycyclic aromatic compound thereof In the following structural formula, "Am" represents an amino group shown in formula (2B), and "Cy" represents an amino group shown in formula (2B). " is a cycloalkane, each n is independently an integer of 1 to 3 (preferably 1), and "= "(Cy)n" means that n cycloalkanes are condensed at any position of the structure to be condensed. (In the structural formula below, n cycloalkanes are condensed to a benzene ring (phenyl group).) The definition of each symbol in the structural formula is the same as the definition of each symbol in general formula (2B). [ka]

[0399] Specifically, compounds represented by the following formulas can be mentioned: "Cy" in the following formulas represents cycloaliphatic alkyl groups. Each n is independently 0 to the maximum condensable number (however, all n's are 0). n is preferably 0 to 2 (but all n's are not 0), more preferably Preferably, it is 1, and "=(Cy)n" is any structure in which n cycloalkanes are condensed. For example, in the following formula "2B-Cy-(11)", each benzene ring can be fused at any position. (n cycloalkanes are condensed at any position).

[0400] [ka] [ka] [ka]

[0401] The compounds represented by each structural formula are substituted with the first and second substituents described above. In addition, examples of the above structural formula include those in which "B" in the above structural formula is P, P=O, The structural formulas where P=S, Al, Ga, As, Si-R or Ge-R are changed are also shown. It should be understood that in the examples of the above structural formulas, "O" in the above structural formulas is replaced with ">N-Ph The structural formula was changed to "Ph=(Cy)n" (the "Ph=(Cy)n" is a condensed cycloalkane It should be understood that the above structural formula also includes an optionally substituted phenyl group. In the above structural formula, "B" can be P, P=O, P=S, Al, Ga, As, Si-R or or Ge-R, and change "O" in the above structural formula to ">N-Ph=(Cy)n". The modified structural formula (the "Ph=(Cy)n" is a phenyl group which may be condensed with a cycloalkane. It should be understood that the aryl group is also shown.

[0402] Further specific examples of the amino-substituted polycyclic aromatic compounds of the present invention include those represented by the following structural formulas: In the structural formula below, "Me" represents a methyl group, and "tBu" represents a t -butyl group, "tAm" represents t-amyl group, and "Hex" represents hexyl group.

[0403] [ka]

[0404] [ka]

[0405] [ka]

[0406] [ka]

[0407]

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[0408]

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[0409]

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[0410]

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[0411]

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[0412]

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[0413]

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[0414]

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[0415]

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[0416]

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[0417]

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[0418]

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[0419]

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[0420]

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[0421]

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[0422]

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[0423]

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[0424]

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[0425]

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[0426]

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[0427]

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[0428]

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[0429]

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[0430]

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[0431]

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[0445]

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[0447]

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[0448]

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[0460] 1-3. Explanation common to compounds of general formula (1), type A and type B The polycyclic compound represented by general formula (1), formula (1A), formula (2A) or formula (2B) according to the present invention Aromatic compounds and their polymers are reactive compounds substituted with reactive substituents. A polymer compound polymerized as a monomer (the monomer for obtaining this polymer compound is having a polymerizable substituent), or a crosslinked polymer obtained by further crosslinking the polymer compound ( The polymer compound for obtaining this crosslinked polymer has a crosslinkable substituent, or A pendant polymer compound (this pendant) is obtained by reacting a chain polymer with the reactive compound. The reactive compound for obtaining the polymer compound has a reactive substituent, or The pendant polymer compound is further crosslinked to form a pendant polymer crosslinked body (this pendant polymer The pendant polymer compound for obtaining the pendant polymer crosslinked product has a crosslinkable substituent. ) as a material for organic devices, for example, a material for organic electroluminescent devices, an organic field effect transistor, It can be used as a material for a transistor or a material for an organic thin-film solar cell.

[0461] The reactive substituents described above (the polymerizable substituent, the crosslinkable substituent, and the pendant type (including reactive substituents for obtaining polymers, hereinafter also referred to simply as "reactive substituents") is a substituent capable of increasing the molecular weight of the polycyclic aromatic compound or its multimer, The resulting polymer compound can be further crosslinked by adding a substituent, or by adding a pendant group to the main chain polymer. There is no particular limitation as long as the substituent is compatible with the group, but examples thereof include alkenyl groups, alkynyl groups, cycloalkenyl groups, and the like. unsaturated alkyl groups (e.g., cyclobutenyl groups), at least one Groups where one -CH2- is replaced by -O- (e.g., epoxy group), condensed cycloalkanes Examples of unsaturated compounds include cyclobutenes (e.g., condensed cyclobutenes), and the following substituents are preferred: * in each structural formula indicates the bond position. [ka]

[0462] L's each independently represent a single bond, -O-, -S-, >C=O, -OC(=O)-, Alkylene having 1 to 12 carbon atoms, oxyalkylene having 1 to 12 carbon atoms, and Among the above substituents, the polyoxyalkylenes represented by the formula (XLS-1), the formula (XLS- 2), Formula (XLS-3), Formula (XLS-9), Formula (XLS-10) or Formula (XLS-1 A group represented by formula (XLS-1), formula (XLS-3) or formula (XLS-7) is preferred, The group represented by 17) is more preferred.

[0463] Such polymer compounds, crosslinked polymers, pendant polymer compounds and pendant polymer compounds Details of the use of the polymer crosslinked body (hereinafter also referred to simply as "polymer compound and polymer crosslinked body") The details will be described later.

[0464] 2. Method for producing amino-substituted polycyclic aromatic compounds and their multimers Polycyclic aromatic compounds represented by general formula (1), formula (1A), formula (2A) or formula (2B) And its multimers are basically composed of A ring (a ring), B ring (b ring) and C ring (c ring) and the bonding group (X 1 or X 2 (a group containing After that, ring A (ring a), ring B (ring b) and ring C (ring c) are bonded to each other by a bonding group (Y 1 containing a group The final product can be produced by combining the two (second reaction). For etherification reactions, general reactions such as nucleophilic substitution reactions and Ullmann reactions can be used. For amination reactions, general reactions such as the Buchwald-Hartwig reaction can be used. In the second reaction, a tandem hetero-Friedel-Crafts reaction (successive aromatic electrophiles) In addition, at some point in these reaction steps, a specific amine Using raw materials substituted with amino groups or adding a process to substitute with specific amino groups Thus, compounds of the present invention can be prepared in which a desired position is substituted with a specific amino group.

[0465] The second reaction is as shown in the following schemes (1) and (2), which converts the A ring (a ring) and the B ring (b ring) and Y bonding the C ring (c ring) 1 is a reaction that introduces Y 1 is a boron atom, X 1 and X 2 The case where X is an oxygen atom is shown below. First, 1 and X 2 The hydrogen atoms between n- Orthometalation with butyllithium, sec-butyllithium, or t-butyllithium Next, boron trichloride or boron tribromide is added to carry out lithium-boron metal exchange. Then, by adding a Bronsted base such as N,N-diisopropylethylamine, The target product can be obtained by a tandem boron-Friedel-Crafts reaction. In some cases, a Lewis acid such as aluminum trichloride may be added to promote the reaction. The structures in the above schemes (1) and (2), and the subsequent schemes (3) to (28) The symbols in the formulas are defined as above.

[0466] [ka] [ka]

[0467] The above schemes (1) and (2) are based on polycyclic aromatic rings represented by general formulas (1A) and (2A). The present invention mainly shows methods for producing aromatic compounds, but for their multimers, it is also possible to produce compounds with multiple A rings (a rings), It can be produced using an intermediate having a B ring (b ring) and a C ring (c ring). Details are explained in the following schemes (3) to (5). The target substance can be obtained by doubling or tripling the amount of the reagent.

[0468] [ka] [ka] [ka]

[0469] In the above scheme, lithium was introduced to the desired position by orthometalation. As shown in the following schemes (6) and (7), a bromine atom or the like is introduced at the desired position for lithium introduction. However, lithium can also be introduced into the desired position by halogen-metal exchange.

[0470] [ka] [ka]

[0471] The method for producing the multimer described in Scheme (3) can also be carried out in the same manner as in Scheme (6) and Scheme (7). and (7) introducing halogen atoms such as bromine atoms or chlorine atoms into the desired position of lithium. Lithium can also be introduced into the desired position by halogen-metal exchange (see below). Schemes (8), (9) and (10) are given below.

[0472] [ka] [ka] [ka]

[0473] This method allows the target compound to be obtained even in cases where ortho-metallation is not possible due to the influence of substituents. It is useful to be able to synthesize

[0474] By appropriately selecting the synthesis method described above and the raw materials used, the desired position can be specifically substituted with an amino group and having a substituent at a desired position, Y 1 is a boron atom, X 1 and X 2 but It is possible to synthesize polycyclic aromatic compounds containing oxygen atoms and their polymers.

[0475] Next, as an example, Y 1 is a boron atom, X 1 and X 2 When is a nitrogen atom, the following scheme ( 11) and (12). X 1 and X 2 As in the case where X is an oxygen atom, first 1 and X 2 The hydrogen atom between the two is orthometalated with n-butyllithium or the like. After adding borane, etc., and carrying out lithium-boron metal exchange, N,N-diisopropylethyl Addition of a Bronsted base such as an amine can induce a tandem boron-Friedel-Crafts reaction. In this case, aluminum trichloride or the like is used to promote the reaction, and the target product can be obtained. Lewis acid may be added. Also, at some point in these reaction steps, By using modified raw materials or adding a step of substituting specific amino groups, the desired Compounds of the invention can be prepared in which specific positions are substituted with amino groups.

[0476] [ka] [ka]

[0477] Also, Y 1 is a boron atom, X 1 and X 2 For the multimer in which is a nitrogen atom, As shown in schemes (6) and (7), bromine atoms, chlorine atoms, etc. are introduced at the desired position for lithium introduction. The halogen is introduced, and lithium is introduced into the desired position by halogen-metal exchange. (Schemes (13), (14) and (15) below).

[0478] [ka] [ka] [ka]

[0479] Next, as an example, Y 1is a phosphorus sulfide, a phosphorus oxide, or a phosphorus atom, and X 1 oh Call X 2 The cases where is an oxygen atom are shown in the following schemes (16) to (19). First of all, X 1 and X 2 The hydrogen atom between the two is orthometalated with n-butyllithium or the like. Then, add phosphorus trichloride and sulfur in that order, and finally add a Lewis acid such as aluminum trichloride and N By adding a Bronsted base such as N-diisopropylethylamine, tandem holosilane can be obtained. Sphagnum Friedel-Crafts reaction, Y 1 It is possible to obtain a compound in which the The obtained phosphorus sulfide compound can be treated with m-chloroperbenzoic acid (m-CPBA). By processing Y 1 is a phosphorus oxide, and By processing with Y 1 In addition, compounds in which the atom is a phosphorus atom can be obtained. At some point in the reaction process, a raw material substituted with a specific amino group is used, or a compound substituted with a specific amino group is used. By adding a step of substituting a specific amino group at a desired position, it is possible to obtain the compound of the present invention in which the desired position is substituted with a specific amino group. The compound can be prepared.

[0480] [ka] [ka] [ka] [ka]

[0481] Also, Y 1 is phosphorus sulfide, X1 and X 2 For the polymers where is an oxygen atom, As shown in the above schemes (6) and (7), a bromine atom or a chlorine atom is introduced at the desired position for lithium introduction. Lithium can also be introduced into the desired position by halogen-metal exchange. This can be achieved by the following schemes (20), (21) and (22). Y 1 is phosphorus sulfide, X 1 and X 2 The polymer when is an oxygen atom is also m-Chloroperbenzoic acid (m-CPBA) can be prepared as shown in schemes (18) and (19). By processing with Y 1 is a phosphorus oxide, and By processing with fins, Y 1 is a phosphorus atom.

[0482] [ka] [ka] [ka]

[0483] Here, Y 1 is B, P, P=O or P=S, and X 1 and X 2 is O or N Although an example of R is given, by changing the raw materials appropriately, it can be Y. 1 However, Al, Ga, As, Si -R or Ge-R, or X 1 and X 2 Compounds where is S can also be synthesized. do.

[0484] Specific examples of solvents used in the above reactions include t-butylbenzene and xylene.

[0485] In addition, in the general formula (2A), the substituents R 1 ~R 11 Adjacent The groups bond to each other to form an aryl or heteroaryl ring together with the a, b or c ring. At least one hydrogen atom in the formed ring may be substituted with an aryl or heterocyclic group. Therefore, the polycyclic aromatic ring represented by the general formula (2A) may be substituted with aryl. The compound can be substituted by the following scheme depending on the mutual bonding forms of the substituents in the a, b and c rings: As shown in formulas (2A-1) and (2A-2) of formulas (23) and (24), compounds These compounds are shown in the following schemes (23) and (24). The compounds can be synthesized by applying the synthetic methods shown in the above schemes (1) to (19) to the intermediates shown in the above schemes (1) to (19). In addition, if a raw material substituted with a specific amino group is used in any of these reaction steps, By adding a step of substituting a specific amino group, the desired position can be converted to a specific amino group. Compounds of the invention can be prepared that are substituted with amino groups.

[0486] [ka] [ka]

[0487] The rings A', B' and C' in the formula (2A-1) and (2A-2) are each independently a substituent. R 1 ~R 11 Adjacent groups of the The aryl or heteroaryl ring formed (other ring structures in ring a, ring b or ring c) Although not shown in the formula, the a-ring, b-ring and There are also compounds in which all of the rings A', B', and C' have been changed to rings A', B', and C'.

[0488] In addition, in the general formula (2A), "the above-mentioned >NR, >Si(-R)2 and >C(-R) R in at least one of the groups 2 is -O-, -S-, -C(-R)2- or a single bond. and bonded to at least one of the ring a, ring b and ring c" is defined as follows: X represented by formula (2A-3-1) in scheme (25) 1 or X 2 is fused ring B' and fused Compounds having a ring structure incorporated into ring C', and compounds of formula (2A-3-2) and formula (2A-3-3 ) is represented by X 1 or X 2 is expressed as a compound having a ring structure incorporated into fused ring A' These compounds can be synthesized by converting the intermediate shown in the following scheme (25) into the above scheme (1). )~(19) can be applied to the synthesis of these compounds. At some point in the reaction process, raw materials substituted with specific amino groups are used, or By adding a step of substituted with a specific amino group at a desired position, the compound of the present invention can be obtained. A mixture can be produced.

[0489] [ka]

[0490] In addition, in the synthesis methods of the above schemes (1) to (17) and (20) to (25), trichloride Before adding boron or boron tribromide, etc., 1 and X 2The hydrogen atom (or halogen atom) between ) by orthometalation with butyllithium, etc., to obtain tandem hetero-Friedel-Crafts The example of the reaction is shown, but without orthometalation using butyllithium etc., The reaction can also be promoted by adding boron, boron tribromide, or the like.

[0491] Also, Y 1 When the compound is phosphorus-based, X 1 and X 2 (In the formula below, O) hydrogen atoms between n-butyllithium and sec-butyllithium Alternatively, orthometalation with t-butyllithium or the like is carried out, followed by the addition of bis(diethylamino)chloroform. After adding sphingosine and carrying out lithium-phosphorus metal exchange, Lewis acid such as aluminum trichloride was added. By adding an acid, a tandem phosphatase Friedel-Crafts reaction can be carried out to obtain the desired product. This reaction method is also described in WO 2010 / 104047 (e.g., page 27). In addition, in some of these reaction steps, raw materials substituted with specific amino groups are By using a specific amino group or by adding a step of substituting a specific amino group, the desired position can be specified. Compounds of the invention can be prepared which are substituted with an amino group of the formula:

[0492] [ka] [ka]

[0493] In the above schemes (26) and (27), orthometalates such as butyllithium are also used. By using 2 or 3 times the molar amount of the methylation reagent relative to the molar amount of intermediate 1, a polymeric compound can be obtained. In addition, a bromine atom can be added in advance to the position where a metal such as lithium is to be introduced. By introducing halogen atoms such as atoms or chlorine atoms, the desired position can be achieved by halogen-metal exchange. Metal can be introduced to

[0494] In addition, compounds condensed with cycloalkanes can be treated in the same manner as the introduction of the amino group described above. In addition, in some reaction steps in each scheme, a cycloalkane-condensed raw material is used, or By adding a step of condensing cycloalkanes, the desired position can be condensed with cycloalkanes. The compound can be prepared by the method described above.

[0495] In addition, the polycyclic aromatic compounds represented by the general formula (2A-Cy) can be synthesized by the following scheme: As shown in (28), a cycloalkane-fused intermediate is synthesized and then cyclized. Polycyclic aromatic compounds fused with cycloalkanes at desired positions can be synthesized. 8), X represents halogen or hydrogen, and the definitions of other symbols are the same as those of the symbols in general formula (2A). is the same as the definition of

[0496] [ka]

[0497] The intermediate before cyclization in scheme (28) can also be synthesized by the method shown in scheme (1) etc. This can be achieved by the Buchwald-Hartwig reaction and Suzuki coupling. Reactions such as nucleophilic substitution reactions and etherification reactions by Ullmann reaction are also included. By combining these reactions, intermediates with desired substituents can be synthesized. In the above, commercially available products can be used as raw materials for the cycloalkane condensed precursor. .

[0498] Compounds of general formula (2A-Cy) having a cycloalkane-fused diphenylamino group can also be synthesized by the following method: The amino acid is reacted with trihalogenated anilines in the Buchwald-Hartwig reaction. After introducing a cycloalkane-condensed diphenylamino group by a polymerization reaction, X 1 , X 2 When NR, amination reactions such as the Buchwald-Hartwig reaction occur. Te, X 1 , X 2 When is O, etherification with phenol gives the intermediate (M- 3) and then react with a metalating reagent such as butyllithium to form the trans After metallization, the reaction is carried out with a boron halide such as boron tribromide, followed by diethyl iodide. Tandem volatilization by the action of a Bronsted base such as isopropylamine The compound of general formula (2A-Cy) can be synthesized by the Del-Crafts reaction. These reactions can also be applied to other cycloalkane-fused compounds.

[0499] The orthometalation reagents used in the above schemes (1) to (28) include methyl Al such as lithium, n-butyllithium, sec-butyllithium, and t-butyllithium Lithium, Lithium diisopropylamide, Lithium tetramethylpiperidide, Lithium Organic alkaline compounds such as ammonium hexamethyldisilazide and potassium hexamethyldisilazide Examples of the dispersion include alkali metals such as sodium dispersed in an organic solvent.

[0500] The metal-Y used in the above schemes (1) to (28)1 As a metal exchange reagent for , Y 1 trifluoride, Y 1 trichloride, Y 1 tribromide, Y 1 Y triiodide etc. 1 of Halides, such as CIPN(NEt2)2 1 Aminated halides of Y 1 Al Koxylate, Y 1 and aryloxy compounds of the above.

[0501] The Bronsted bases used in the above schemes (1) to (28) include N,N -Diisopropylethylamine, Triethylamine, 2,2,6,6-Tetramethylpiperidine Lysine, 1,2,2,6,6-pentamethylpiperidine, N,N-dimethylaniline, N ,N-dimethyltoluidine, 2,6-lutidine, sodium tetraphenylborate, tetraphenylborate Potassium triphenylborate, triphenylborane, tetraphenylsilane, Ar4BNa , Ar4BK, Ar3B, Ar4Si (where Ar is aryl such as phenyl). It can be obtained.

[0502] The Lewis acids used in the above schemes (1) to (28) include AlCl3, AlBr3 , AlF3, BF3·OEt2, BCl3, BBr3, GaCl3, GaBr3, InC l3, InBr3, In(OTf)3, SnCl4, SnBr4, AgOTf, ScCl 3, Sc(OTf)3, ZnCl2, ZnBr2, Zn(OTf)2, MgCl2, Mg Br2, Mg(OTf)2, LiOTf, NaOTf, KOTf, Me3SiOTf, C u(OTf)2, CuCl2, YCl3, Y(OTf)3, TiCl4, TiBr4, Z Examples include ZrCl4, ZrBr4, FeCl3, FeBr3, CoCl3, and CoBr3. can be.

[0503] In the above schemes (1) to (28), the promotion of the tandem hetero-Friedel-Crafts reaction For this purpose, a Bronsted base or Lewis acid may be used, provided that Y 1 trifluoride , Y 1 trichloride, Y 1 tribromide, Y 1 Y triiodide etc. 1 Using halides of In this case, hydrogen fluoride, hydrogen chloride, hydrogen bromide, and iodide are produced as the aromatic electrophilic substitution reaction proceeds. Since acids such as hydrogen fluoride are generated, it is effective to use a Bronsted base to capture the acid. On the other hand, Y 1 Aminated halides of Y 1 When an alkoxylated product of As the aromatic electrophilic substitution reaction progresses, amines and alcohols are produced, so in many cases, It is not necessary to use a Bronsted base, but the amino and alkoxy groups have low leaving ability. Therefore, the use of a Lewis acid that promotes the elimination is effective.

[0504] In addition, in the polycyclic aromatic compound and its multimer of the present invention, at least some of the hydrogen atoms are replaced with heavy water. Compounds substituted with fluorine or chlorine, or compounds substituted with cyano or halogens Such compounds may be deuterated, cyanated, fluorinated or Alternatively, chlorinated raw materials can be used to synthesize the compound in the same manner as above.

[0505] The polycyclic aromatic compound represented by the general formula (2B) and its multimer can be prepared, for example, from the compound disclosed in International Publication No. 2004 / 002264. It can be synthesized by applying the method disclosed in Publication No. 15 / 102118. That is, as shown in the following scheme (29), an Am group (an amino group represented by formula (2B)), Ra The intermediate having the Rb group and the Rb group was synthesized and used in a tandem hetero-Friedel-Crafts reaction. The desired polycyclic aromatic compounds and In the following scheme, X represents a halogen or hydrogen, and other symbols The definitions of the symbols are the same as those given above. [ka]

[0506] The intermediate before cyclization in the above scheme (29) can also be prepared by the method described in WO 2015 / 102118. It can be synthesized by the method shown in Buchwald-Hartwig et al. by ig reaction, Suzuki coupling reaction, nucleophilic substitution reaction, Ullmann reaction, etc. By appropriately combining etherification reactions, intermediates with desired substituents can be synthesized. It is possible.

[0507] The tandem hetero-Friedel-Crafts cyclization shown in the above scheme (29) is Y connecting ring a, ring b, and ring c 1 (boron) is introduced. First, X 1 Oh and X 2 The hydrogen atom between n-butyllithium, sec-butyllithium or t-butyl Orthometalation with lithium etc. Then, Y 1 Add the trichloride or tribromide of lithium After metal exchange of ammonium-boron, the bromine-containing amines such as N,N-diisopropylethylamine were Adding a base to the aryl group allows for a tandem boron-Friedel-Crafts reaction to yield the desired product. Here, a Lewis acid such as aluminum trichloride is added to promote the reaction. Good too.

[0508] In addition to the method of introducing lithium into the desired position by orthometalation, A halogen atom such as a bromine atom can be introduced into the desired position, and the desired compound can be obtained by halogen-metal exchange. Lithium can be introduced at any desired location.

[0509] In addition, in the polycyclic aromatic compound and its multimer of the present invention, at least some of the hydrogen atoms are replaced with heavy water. Compounds substituted with fluorine or chlorine, or compounds substituted with cyano or halogens Such compounds may be deuterated, cyanated, fluorinated or Alternatively, chlorinated raw materials can be used to synthesize the compound in the same manner as above.

[0510] In the synthesis of the polycyclic aromatic compound of formula (2B) and its multimer, the compound of formula (2B) may be synthesized by the method described above. The explanations for the synthesis of the compounds of formula (1A) and formula (2A) can be referred to.

[0511] 3. Organic Devices The amino-substituted polycyclic aromatic compound according to the present invention can be used as a material for organic devices. Examples of organic devices include organic electroluminescent devices and organic field effect transistors. Alternatively, organic thin-film solar cells may be used.

[0512] 3-1. Organic electroluminescent device The organic EL element according to this embodiment will be described in detail below with reference to the drawings. 1 is a schematic cross-sectional view showing an organic EL element according to an embodiment of the present invention.

[0513] <Structure of organic electroluminescent device> The organic EL device 100 shown in FIG. 1 comprises a substrate 101 and an anode provided on the substrate 101. 102, a hole injection layer 103 provided on the anode 102, and a a hole transport layer 104 formed on the hole transport layer 104; a light emitting layer 105 formed on the hole transport layer 104; An electron transport layer 106 is provided on the layer 105, and an electron transport layer 108 is provided on the electron transport layer 106. The device has an injection layer 107 and a cathode 108 provided on the electron injection layer 107 .

[0514] The organic EL element 100 can be fabricated in the reverse order, for example, by fabricating the substrate 101 and the substrate 102. a cathode 108 provided on the cathode 108; an electron injection layer 107 provided on the cathode 108; An electron transport layer 106 provided on the injection layer 107, and a 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 thereon, and an anode 102 provided on the hole injection layer 103; The configuration may also include the following.

[0515] Not all of the above layers are necessary, but the minimum structural unit is the anode 102 and the light-emitting layer. The cathode 108 is made up of a hole injection layer 103, a hole transport layer 104, an electron The transport layer 106 and the electron injection layer 107 are layers that are optionally provided. Each of them may consist of a single layer or multiple layers.

[0516] The organic EL element may be configured as a layer structure of the above-mentioned "substrate / anode / hole injection layer / hole In addition to the "transport layer / light-emitting layer / electron transport layer / electron injection layer / cathode" configuration, there is also the "substrate / anode / cathode" configuration. Hole transport layer / light-emitting layer / electron transport layer / electron injection layer / cathode," "Substrate / anode / hole injection layer / light-emitting layer" layer / electron transport layer / electron injection layer / cathode," "substrate / anode / hole injection layer / hole transport layer / light-emitting layer" / electron injection layer / cathode", "substrate / anode / hole injection layer / hole transport layer / light-emitting layer / electron transport layer / cathode", "substrate / anode / light-emitting layer / electron transport layer / electron injection layer / cathode", "substrate / anode / hole transport layer / light-emitting layer / electron injection layer / cathode," "substrate / anode / hole transport layer / light-emitting layer / electron transport layer / cathode", "substrate / anode / hole injection layer / light-emitting layer / electron injection layer / cathode", "substrate / anode / positive electrode hole injection layer / light-emitting layer / electron transport layer / cathode", "substrate / anode / light-emitting layer / electron transport layer / cathode", The structure may be "substrate / anode / light-emitting layer / electron injection layer / cathode."

[0517] <Substrate in organic electroluminescent device> The substrate 101 is a support for the organic EL element 100 and is usually made of quartz, glass, metal, or plastic. The substrate 101 may be in the form of a plate, a film, or a sheet depending on the purpose. For example, glass plates, metal plates, metal foils, plastic films, plastics, etc. Among them, glass plates, polyester, polymethacrylate, etc. are used. A plate made of a transparent synthetic resin such as polyethylene, polycarbonate, or polysulfone is preferred. For glass substrates, soda lime glass or alkali-free glass is used. It is sufficient that the thickness is sufficient to maintain mechanical strength, so for example, 0.2 mm or more is sufficient. The upper limit of the thickness is, for example, 2 mm or less, preferably 1 mm or less. As for the material, it is better to have less ions dissolved from the glass, so alkali-free glass is preferred. is preferred, but soda lime glass coated with a barrier coating such as SiO2 is also commercially available. In addition, the substrate 101 is provided with a material for enhancing the gas barrier property. A gas barrier film such as a dense silicon oxide film may be provided on at least one side of the substrate. When a synthetic resin plate, film, or sheet with low barrier properties is used as the substrate 101 It is preferable to provide a gas barrier film on the surface of the substrate.

[0518] <Anode in organic electroluminescent device> The anode 102 serves to inject holes into the light-emitting layer 105. At least one layer of a hole injection layer 103 and a hole transport layer 104 is provided between the layer 105 and the hole injection layer 103. When the organic layer 104 is provided with the organic EL element, holes are injected into the light-emitting layer 105 via the organic EL element.

[0519] Materials for forming 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), etc.), metal halides (copper iodide, etc.), Examples include copper sulfide, carbon black, ITO glass, and Nesa glass. Examples of such polythiophenes include poly(3-methylthiophene), polypyrrole, Examples include conductive polymers such as polyaniline. The material can be appropriately selected from those currently used.

[0520] The resistance of the transparent electrode is not limited as long as it can supply a sufficient current for the light emitting element to emit light. However, from the viewpoint of power consumption of the light emitting element, low resistance is desirable. For example, 300Ω / ITO substrates with a resistance of 10Ω / □ or less can function as device electrodes, but currently, substrates with a resistance of about 10Ω / □ are required. Therefore, for example, 100 to 5Ω / □, preferably 50 to 5Ω / □ It is especially desirable to use a low resistance product. The thickness of the ITO can be selected arbitrarily according to the resistance value. Although it is possible to increase the thickness, it is usually used in the range of 50 to 300 nm.

[0521] <Hole injection layer and hole transport layer in organic electroluminescent device> The hole injection layer 103 efficiently injects holes moving from the anode 102 into the light emitting layer 105. The hole transport layer 104 serves to inject electrons from the anode 102 into the hole transport layer 104. The injected holes or holes injected from the anode 102 through the hole injection layer 103 are efficiently The hole injection layer 103 and the hole transport layer 104 serve to transport electrons to the light-emitting layer 105. , respectively, one or more kinds of hole injection and transport materials are laminated or mixed, or hole injection and It is formed by a mixture of a transport material and a polymer binder. Also, iron chloride is used as the hole injection / transport material. An inorganic salt such as (III) may be added to form a layer.

[0522] As a hole injection / transport material, it efficiently transports holes from the positive electrode between electrodes with an applied electric field. It is necessary to have good hole injection and transport efficiency, and to have high hole injection efficiency and efficient transport of injected holes. To achieve this, it is necessary to have a small ionization potential and a high hole mobility. It is large and has excellent stability, making it difficult for impurities to be trapped during manufacturing and use. It is preferable that the material is a non-ionic surfactant.

[0523] The hole injection layer 103 and the hole transport layer 104 are made of a photoconductive material. Compounds that have been conventionally used as charge transport materials for holes, p-type semiconductors, organic EL devices, Any compound can be selected from known compounds used in the hole injection layer and hole transport layer of the polymer. Specific examples thereof include carbazole derivatives (N-phenylcarbazole, carbazole, polyvinylcarbazole, etc.), bis(N-arylcarbazole) or Biscarbazole derivatives such as bis(N-alkylcarbazole), triarylamine Derivatives (polymers with aromatic tertiary amino groups 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'-dinaphtho N,N'-diphenyl-4,4'-diphenyl-1,1'-diamine, N 4 ,N 4 ’ -diphenyl-N 4 ,N 4’ -bis(9-phenyl-9H-carbazol-3-yl) -[1,1'-biphenyl]-4,4'-diamine, N 4 ,N 4 ,N 4’ ,N 4’ -Tet La[1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4,4'-dia amine, 4,4',4"-tris(3-methylphenyl(phenyl)amino)triphenyl amines, triphenylamine derivatives, starburst amine derivatives, etc.), stilbe Phthalocyanine derivatives (metal-free, copper phthalocyanine, etc.), pyrazoline derivatives , hydrazone compounds, benzofuran derivatives, thiophene derivatives, oxadiazole derivatives quinoxaline derivatives (e.g., 1,4,5,8,9,12-hexaazatriphenylene benzophenone-2,3,6,7,10,11-hexacarbonitrile, porphyrin derivatives, etc. In the polymer system, the polymer having the above-mentioned monomer in the side chain is Preferred are polycarbonates, styrene derivatives, polyvinylcarbazole and polysilane. However, it is necessary to form a thin film necessary for manufacturing a light-emitting element, and it is also necessary to inject holes from the anode. There is no particular limitation as long as the compound can transport the

[0524] It is also known that the conductivity of organic semiconductors is strongly affected by their doping. Such organic semiconductor matrix materials are compounds with good electron donating properties, or , and is composed of compounds with good electron-accepting properties. For doping with electron-donating substances, Tetracyanoquinone dimethane (TCNQ) or 2,3,5,6-tetrafluorotetrafluoroethane 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 the document "J. Blochwitz, M. Pheiffer, T. Fritz, K. Leo, Appl. Phys. Lett., 73(6), 729-731(1998)). These are electron-donating base materials (hole-transporting materials) ) generates so-called holes by an electron transfer process. The conductivity of the base material changes considerably depending on the Examples of the oxidizing agent include benzidine derivatives (such as TPD) or starburst amine. derivatives (such as TDATA), or certain metal phthalocyanines (especially zinc phthalocyanines) ZnPc and the like) are known (Japanese Patent Laid-Open Publication No. 2005-167175).

[0525] The above-mentioned hole injection layer material and hole transport layer material are substituted with reactive substituents. Polymer compounds obtained by polymerizing reactive compounds as monomers, or polymer crosslinked compounds thereof or a pendant-type polymer compound obtained by reacting a main-chain polymer with the reactive compound. or its pendant polymer crosslinked product can also be used as a hole layer material. In this case, the reactive substituent is a group represented by the above formula (1), formula (1A), formula (2A) or formula ( The explanation for the polycyclic aromatic compound represented by 2B) can be cited. The uses of such polymer compounds and crosslinked polymers will be described in detail below.

[0526] <Light-emitting layer in organic electroluminescent device> The light-emitting layer 105 reacts with holes injected from the anode 102 between the electrodes to which an electric field is applied. The layer emits light by recombining with the electrons injected from the cathode 108. The material for forming 105 is a compound that emits light when excited by the recombination of holes and electrons. Any substance (luminescent compound) can be used, and it can be formed into a stable thin film shape and can be used in a solid state. In the present invention, the material for the light-emitting layer is preferably a compound that exhibits strong luminescence (fluorescence) efficiency in the light-emitting state. As a material, a host material and, for example, the above-mentioned formula (1) or formula (1A) as a dopant material and a polycyclic aromatic compound represented by formula (2A) or formula (2B) can be used.

[0527] The light-emitting layer may be a single layer or a multi-layer. The host material and the dopant material are The dopant material may be one kind or a combination of two or more kinds. It may be contained entirely or partially in the stock material. The doping method can be a co-evaporation method with the host material. Alternatively, the material may be mixed with the catalyst material in advance and then vapor-deposited simultaneously.

[0528] The amount of the host material used varies depending on the type of host material, and should be adjusted to suit the properties of the host material. The amount of the host material to be used is preferably 50 to 100% of the total amount of the materials for the light-emitting layer. 99.999% by weight, more preferably 80 to 99.95% by weight, and even more preferably The content is preferably 90 to 99.9% by weight.

[0529] The amount of dopant material used varies depending on the type of dopant material. The amount of dopant used should preferably be determined according to the characteristics of the light-emitting layer material. It is 0.001 to 50% by weight of the total, more preferably 0.05 to 20% by weight, and even more preferably It is more preferably 0.1 to 10% by weight. Within the above range, for example, concentration quenching phenomenon can be prevented. In addition, from the viewpoint of durability, it is preferable to use hydrogen atoms of the dopant material. is also preferably partially or fully deuterated.

[0530] The host materials used were anthracene, pyrene, and dibenzyl benzoate, which have long been known as light emitters. fused ring derivatives such as benzochrysene or fluorene, bisstyryl anthracene derivatives, Bisstyryl derivatives such as distyrylbenzene derivatives, tetraphenylbutadiene derivatives , cyclopentadiene derivatives, etc. In particular, anthracene compounds, fluorene compounds, etc. From the viewpoint of durability, phosphazene-based compounds and dibenzochrysene-based compounds are preferred. It is also preferable that some or all of the hydrogen atoms in the material are deuterated. Alternatively, a host compound in which all hydrogen atoms are deuterated and a compound in which some or all hydrogen atoms are deuterated are used. It is also preferable to form the light-emitting layer by combining a hydrogenated dopant compound.

[0531] <Anthracene compounds> The anthracene compound as the host is, for example, a compound represented by the following general formula (3): be. [ka]

[0532] In formula (3), X and Ar 4 are each independently hydrogen, an optionally substituted aryl, a substituted optionally substituted heteroaryl, optionally substituted diarylamino, substituted optionally substituted diheteroarylamino, optionally substituted arylheteroarylamino , optionally substituted alkyl, optionally substituted cycloalkyl, substituted optionally substituted alkenyl, optionally substituted alkoxy, optionally substituted aryl oxy, optionally substituted arylthio, or optionally substituted silyl; All X and Ar 4 cannot simultaneously become hydrogen, At least one hydrogen atom in the compound represented by formula (3) is replaced by a halogen atom, a cyano atom, or a deuterium atom. Or it may be substituted by an optionally substituted heteroaryl.

[0533] Furthermore, a polymer (preferably a dimer) is formed using the structure represented by formula (3) as a unit structure. In this case, for example, the unit structures represented by formula (3) may be bonded to each other via X. X may be a single bond, arylene (phenylene, biphenylene, and naphthylene), ethylene, etc.) and heteroarylene (pyridine ring, dibenzofuran ring, dibenzothiophene ring, etc.) phenyl ring, carbazole ring, benzocarbazole ring, and phenyl-substituted carbazole ring. (a group having a divalent bond) and the like.

[0534] The above aryl, heteroaryl, diarylamino, diheteroarylamino, aryl heteroarylamino, alkyl, cycloalkyl, alkenyl, alkoxy, aryl Details of aryloxy, arylthio, and silyl will be explained in the preferred embodiments section below. In addition, the substituents on these include aryl, heteroaryl, diarylamino, diheteroaryl, and the like. arylamino, arylheteroarylamino, alkyl, cycloalkyl, alkoxy aryl, alkoxy, aryloxy, arylthio, or silyl, and the like. The details of the above will also be explained in the preferred embodiments section below.

[0535] Preferred embodiments of the above anthracene-based compounds are described below. The definition is the same as above. [ka]

[0536] In the general formula (3), each X independently represents the above formula (3-X1), formula (3-X2), or A group represented by formula (3-X3), and the group represented by formula (3-X1), formula (3-X2) or formula (3-X The group represented by (3) is bonded to the anthracene ring of formula (3) at *. Preferably, two The Xs are not simultaneously a group represented by the formula (3-X3). At the same time, it does not become a group represented by formula (3-X2).

[0537] Furthermore, a polymer (preferably a dimer) is formed using the structure represented by formula (3) as a unit structure. In this case, for example, the unit structures represented by formula (3) may be bonded to each other via X. X may be a single bond, arylene (phenylene, biphenylene, and naphthylene), ethylene, etc.) and heteroarylene (pyridine ring, dibenzofuran ring, dibenzothiophene ring, etc.) phenyl ring, carbazole ring, benzocarbazole ring, and phenyl-substituted carbazole ring. (a group having a divalent bond) and the like.

[0538] The naphthylene moieties in formula (3-X1) and formula (3-X2) are fused with one benzene ring. The resulting condensed structure is as follows: [ka]

[0539] Ar 1 and Ar 2 are each independently hydrogen, phenyl, biphenylyl, terphenyl phenylyl, quaterphenylyl, naphthyl, phenanthryl, fluorenyl, benzofluorene phenylenyl, chrysenyl, triphenylenyl, pyrenylyl, or a group represented by the above formula (A) groups (including carbazolyl groups, benzocarbazolyl groups, and phenyl-substituted carbazolyl groups) In addition, Ar 1 or Ar 2 is a group represented by formula (A), The group bonded to the naphthalene ring in formula (3-X1) or formula (3-X2) at * do.

[0540] Ar 3 is phenyl, biphenylyl, terphenylyl, quaterphenylyl, naphthyl , phenanthryl, fluorenyl, benzofluorenyl, chrysenyl, triphenylenyl , pyrenylyl, or a group represented by the above formula (A) (carbazolyl group, benzocarbazolyl group) (This also includes phenyl-substituted carbazolyl groups and phenyl-substituted carbazolyl groups.) 3 is expressed by formula (A) In the case where the group represented by formula (A) is a group represented by formula (3-X3), the group represented by formula (A) is a group represented by formula (3-X3) at the *. That is, the anthracene ring of formula (3) is bonded to a single bond represented by formula (A). The group is directly bonded.

[0541] Also, Ar 3 may have a substituent, and Ar 3 At least one hydrogen atom in In addition, alkyl having 1 to 4 carbon atoms, cycloalkyl having 5 to 10 carbon atoms, phenyl, biphenyl fluorenyl, chrysenyl, triphenylyl, naphthyl, phenanthryl, fluorenyl, chrysenyl, triphenyl pyrenyl, pyrenyl, or a group represented by the above formula (A) (carbazolyl group and phenyl group) The Ar may be substituted with a phenyl-substituted carbazolyl group. 3 The substituents of is a group represented by formula (A), the group represented by formula (A) is represented by the formula (3- X3) in Ar 3 and combine.

[0542] Ar 4 are each independently hydrogen, phenyl, biphenylyl, terphenylyl, naphthyl, alkyl, or alkyl having 1 to 4 carbon atoms (methyl, ethyl, t-butyl, etc.) and / or The silyl group is preferably silyl substituted with cycloalkyl having 5 to 10 carbon atoms.

[0543] The alkyl having 1 to 4 carbon atoms to be substituted on the silyl is methyl, ethyl, propyl, i-propyl Examples of silyl include butyl, sec-butyl, t-butyl, and cyclobutyl. Three hydrogen atoms are independently substituted with these alkyl groups.

[0544] Specific examples of "silyl substituted with alkyl having 1 to 4 carbon atoms" include trimethylsilyl. silyl, triethylsilyl, tripropylsilyl, tri-i-propylsilyl, tributylsilyl silyl, tri-sec-butylsilyl, tri-t-butylsilyl, ethyldimethylsilyl, proton propyldimethylsilyl, i-propyldimethylsilyl, butyldimethylsilyl, sec-butyl t-butyldimethylsilyl, methyldiethylsilyl, propyldiethylsilyl Isopropylsilyl, i-propyldiethylsilyl, butyldiethylsilyl, sec-butyldiethylsilyl t-butyldiethylsilyl, methyldipropylsilyl, ethyldipropylsilyl butyldipropylsilyl, sec-butyldipropylsilyl, t-butyldipropyl methyldi-i-propylsilyl, ethyldi-i-propylsilyl, butyldi-i-propylsilyl sec-butyldi-i-propylsilyl, t-butyldi-i-propylsilyl Examples include:

[0545] The cycloalkyl having 5 to 10 carbon atoms that substitutes for the silyl is cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, norbornenyl, Bicyclo[1.1.1]pentyl, bicyclo[2.0.1]pentyl, bicyclo[1.2 .1]hexyl, bicyclo[3.0.1]hexyl, bicyclo[2.1.2]heptyl, Bicyclo[2.2.2]octyl, adamantyl, decahydronaphthalenyl, decahydro azulenyl, and the three hydrogens in the silyl are independently It is substituted with cycloalkyl.

[0546] Specific examples of "silyl substituted with cycloalkyl having 5 to 10 carbon atoms" include trimethylsilyl, trimethylsilyl, and cycloalkyl. Examples include cyclopentylsilyl and tricyclohexylsilyl.

[0547] Substituted silyls include di-substituted silyls with two alkyls and one cycloalkyl. Alkylcycloalkylsilyl and alkyl substituted with one alkyl and two cycloalkyl There is also alkyldicycloalkylsilyl, and specific examples of substituted alkyl and cycloalkyl are Examples of the group include the groups mentioned above.

[0548] In addition, hydrogen atoms in the chemical structure of the anthracene compound represented by the general formula (3) are represented by the formula (A When it is substituted with a group represented by formula (A), it may be substituted with a group represented by formula The group represented by (A) is at least one of the groups represented by * in the compound represented by formula (3). Replaces hydrogen with

[0549] The group represented by formula (A) is a substituent that the anthracene compound represented by formula (3) may have. It is one of the following. [ka]

[0550] In the above formula (A), Y is —O—, —S—, or >NR29 and R 21 ~R 28 Haso each independently represents hydrogen, optionally substituted alkyl, optionally substituted cycloalkyl, alkyl, optionally substituted aryl, optionally substituted heteroaryl, substituted optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted Arylthio, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkyi alkylsilyl, alkyldicycloalkylsilyl, optionally substituted amino, halogen , hydroxy or cyano, and R 21 ~R 28 Adjacent groups are bonded to each other and form carbon atoms. may form a hydrogen ring, an aryl ring, or a heteroaryl ring, and R 29 is hydrogen or is an optionally substituted aryl.

[0551] R 21 ~R 28 The "alkyl" in the "optionally substituted alkyl" is It may be either a straight chain or a branched chain, and may be, for example, a straight chain alkyl or a carbon Examples include branched alkyls having 3 to 24 carbon atoms. alkyl having 1 to 12 carbon atoms (branched alkyl having 3 to 12 carbon atoms) is preferred, alkyl) is more preferred, and alkyl having 1 to 6 carbon atoms (branched alkyl having 3 to 6 carbon atoms) is More preferred is alkyl having 1 to 4 carbon atoms (branched alkyl having 3 to 4 carbon atoms). It's nice.

[0552] Specific examples of "alkyl" include methyl, ethyl, n-propyl, isopropyl, n- Butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl t-pentyl (t-amyl), n-hexyl, 1-methylpentyl, 3,3-dimethyl butyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, t -Octyl (1,1,3,3-tetramethylbutyl), 1-methylheptyl, 2-ethyl Hexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 2,6-di Methyl-4-heptyl, 3,5,5-trimethylhexyl, n-decyl, n-undecyl , 1-methyldecyl, n-dodecyl, n-tridecyl, 1-hexylheptyl, n-tetradecyl Ladecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl , n-eicosyl, etc.

[0553] R 21 ~R 28 "Cycloalkyl" of "optionally substituted cycloalkyl" in " includes cycloalkyl having 3 to 24 carbon atoms, cycloalkyl having 3 to 20 carbon atoms, Cycloalkyl having 3 to 16 carbon atoms, cycloalkyl having 3 to 14 carbon atoms, cycloalkyl having 5 to 10 carbon atoms cycloalkyl having 5 to 8 carbon atoms, cycloalkyl having 5 to 6 carbon atoms, cycloalkyl having 5 carbon atoms Examples include cycloalkyl of the following.

[0554] Specific examples of "cycloalkyl" include cyclopropyl, cyclobutyl, and cyclopentyl. cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, and alkyl (especially methyl) substituted derivatives of these having 1 to 4 carbon atoms, norbornenyl, bis(methyl) chloro[1.0.1]butyl, bicyclo[1.1.1]pentyl, bicyclo[2.0.1] Pentyl, bicyclo[1.2.1]hexyl, bicyclo[3.0.1]hexyl, bicyclo Bicyclo[2.1.2]heptyl, bicyclo[2.2.2]octyl, adamantyl, diamantyl Examples include decahydronaphthalenyl, decahydroazulenyl, and the like.

[0555] R 21 ~R 28 The "aryl" in the "optionally substituted aryl" is For example, aryl having 6 to 30 carbon atoms is mentioned, and aryl having 6 to 16 carbon atoms is preferred. An aryl having 6 to 12 carbon atoms is more preferred, and an aryl having 6 to 10 carbon atoms is particularly preferred.

[0556] Specific examples of "aryl" include phenyl, which is a monocyclic ring, biphenylyl, which is a bicyclic ring, The fused bicyclic ring system naphthyl, the tricyclic ring system terphenylyl (m-terphenylyl, o-terphenylyl), p-Terphenylyl), fused tricyclic ring systems, acenaphthylenyl, fluorenyl, phenylenyl, phenalenyl, phenanthrenyl, fused tetracyclic ring systems triphenylenyl, pyrenyl , naphthacenyl, and fused five-ring systems such as perylenyl and pentacenyl.

[0557] R 21 ~R 28 "Heteroaryl" of "optionally substituted heteroaryl" in Examples of the heteroaryl include heteroaryls having 2 to 30 carbon atoms, and heteroaryls having 2 to 25 carbon atoms. Heteroaryl having 2 to 20 carbon atoms is preferred, and heteroaryl having 2 to 20 carbon atoms is more preferred. Heteroaryl having 15 carbon atoms is more preferred, and heteroaryl having 2 to 10 carbon atoms is particularly preferred. In addition, heteroaryl includes, for example, ring-constituting atoms other than carbon, such as oxygen, sulfur, and and heterocycles containing 1 to 5 heteroatoms selected from nitrogen and the like.

[0558] Specific examples of "heteroaryl" include pyrrolyl, oxazolyl, and isoxa. Zolyl, thiazolyl, isothiazolyl, imidazolyl, oxadiazolyl, thiadiazolyl aryl, triazolyl, tetrazolyl, pyrazolyl, pyridyl, pyrimidinyl, pyridazinyl , pyrazinyl, triazinyl, indolyl, isoindolyl, 1H-indazolyl, benzoyl Zoimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, Quinolyl, isoquinolyl, cinnolyl, quinazolyl, quinoxalinyl, phthalazinyl, na Phthyridinyl, purinyl, pteridinyl, carbazolyl, acridinyl, phenoxathiyl furyl, phenoxazinyl, phenothiazinyl, phenazinyl, indolizinyl, furyl, Benzofuranyl, isobenzofuranyl, dibenzofuranyl, thienyl, benzo[b]thienoyl nyl, dibenzothienyl, furazanyl, oxadiazolyl, thianthrenyl, naphthobenyl Examples include zofranil and naphthobenzothienyl.

[0559] R 21 ~R 28 As the "alkoxy" in "optionally substituted alkoxy" in Examples of the alkoxy include linear alkoxy having 1 to 24 carbon atoms and branched alkoxy having 3 to 24 carbon atoms. Alkoxy having 1 to 18 carbon atoms (branched alkoxy having 3 to 18 carbon atoms) is preferred. Alkoxy having 1 to 12 carbon atoms (branched alkoxy having 3 to 12 carbon atoms) is more preferred. alkoxy having 1 to 6 carbon atoms (branched alkoxy having 3 to 6 carbon atoms) is more preferred, Alkoxy having 1 to 4 carbon atoms (branched alkoxy having 3 to 4 carbon atoms) is particularly preferred.

[0560] Specific examples of "alkoxy" include methoxy, ethoxy, propoxy, and isopropoxy. , butoxy, isobutoxy, s-butoxy, t-butoxy, pentyloxy, hexyloxy Examples include oxy, heptyloxy, and octyloxy.

[0561] R 21 ~R 28 "Aryloxy" in "optionally substituted aryloxy" " is a group in which the hydrogen of the -OH group is substituted with an aryl, and this aryl is as defined above. R 21 ~R 28 The group described as "aryl" in the above formula can be used.

[0562] R 21 ~R 28 and the "arylthio" in the "optionally substituted arylthio" The hydrogen atom of the -SH group is replaced with an aryl group, and the aryl group is the same as the above-mentioned R 2 1 ~R 28 The group described as "aryl" in the above formula can be used.

[0563] R 21 ~R 28 The "trialkylsilyl" in the silyl group is a group consisting of three water atoms. and the alkyl is a group in which each atom is independently substituted with an alkyl group. 2 1 ~R 28 The groups described as "alkyl" in the above can be cited. The most preferred alkyl is alkyl having 1 to 4 carbon atoms, specifically methyl, ethyl, Examples include propyl, i-propyl, butyl, sec-butyl, t-butyl, and cyclobutyl. can be done.

[0564] Specific examples of "trialkylsilyl" include trimethylsilyl, triethylsilyl, trimethylsilyl, and trimethylsilyl. Tripropylsilyl, tri-i-propylsilyl, tributylsilyl, tri-sec-butylsilyl silyl, tri-t-butylsilyl, ethyldimethylsilyl, propyldimethylsilyl, i-propyl propyldimethylsilyl, butyldimethylsilyl, sec-butyldimethylsilyl, t-butyldimethylsilyl methyldiethylsilyl, methyldiethylsilyl, propyldiethylsilyl, i-propyldi Ethylsilyl, butyldiethylsilyl, sec-butyldiethylsilyl, t-butyldiethylsilyl methyldipropylsilyl, ethyldipropylsilyl, butyldipropylsilyl sec-butyldipropylsilyl, t-butyldipropylsilyl, methyldi-i-propyl Pyridilyl, ethyldi-i-propylsilyl, butyldi-i-propylsilyl, sec-butyl Examples include butyldi-i-propylsilyl and t-butyldi-i-propylsilyl.

[0565] R 21 ~R 28 The "tricycloalkylsilyl" in the above context refers to a silyl group with 3 and a group in which two hydrogen atoms are independently substituted with cycloalkyl. Kill is the R mentioned above. 21 ~R 28 The group described as "cycloalkyl" in The cycloalkyl to be substituted is preferably a cycloalkyl having 5 to 10 carbon atoms. Specifically, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl Cyclonyl, cyclononyl, cyclodecyl, bicyclo[1.1.1]pentyl, bicyclo[2.0 .1]pentyl, bicyclo[1.2.1]hexyl, bicyclo[3.0.1]hexyl, Bicyclo[2.1.2]heptyl, bicyclo[2.2.2]octyl, adamantyl, de Examples include decahydronaphthalenyl and decahydroazulenyl.

[0566] Specific examples of "tricycloalkylsilyl" include tricyclopentylsilyl, tricyclopentylsilyl, and tricyclopentylsilyl. Examples include cyclohexylsilyl.

[0567] Dialkylcycloalkylsilyl, which is substituted with two alkyls and one cycloalkyl, , alkyldicycloalkylsilyl substituted with one alkyl and two cycloalkyl groups Specific examples include groups selected from the specific alkyl and cycloalkyl groups listed above. An example is Cyril, which has been replaced by

[0568] R 21 ~R 28 The "substituted amino" in the "optionally substituted amino" Examples of such groups include amino groups in which two hydrogen atoms are replaced by aryl or heteroaryl groups. An amino in which two hydrogen atoms are replaced by aryl atoms is called a diaryl-substituted amino. is a heteroaryl-substituted amino, and two hydrogen atoms are is aryl and heteroaryl substituted amino; is arylheteroaryl substituted amino; The aryl and heteroaryl are the same as those described above. 21 ~R 28 "Aryl" in Reference may be made to groups described as "heteroaryl".

[0569] Specific examples of "substituted amino" include diphenylamino, dinaphthylamino, phenylamino, and the like. Nylnaphthylamino, dipyridylamino, phenylpyridylamino, naphthylpyridyl Examples include mino.

[0570] R 21 ~R 28The "halogens" in this document include fluorine, chlorine, bromine, and iodine. can be.

[0571] R 21 ~R 28 Some of the groups described as may be substituted as described above. In this case, the substituents are alkyl, cycloalkyl, aryl, or heteroaryl. The alkyl, cycloalkyl, aryl or heteroaryl may be any of the above. TA R 21 ~R 28 "Alkyl," "cycloalkyl," "aryl," or "hexaalkyl" in Reference can be made to the group described as "heteroaryl."

[0572] Y as 'NR' 29 "R" 29 is hydrogen or an optionally substituted aryl The aryl is the same as R 21 ~R 28 The term "aryl" is used in The groups described above can be cited, and the substituents thereof include R 21 ~R 28 Substituents for The groups described above can be cited.

[0573] R 21 ~R 28 Adjacent groups among them are bonded to each other to form a hydrocarbon ring, an aryl ring, or a heterocyclic ring. The case where no ring is formed is represented by the following formula (A-1): When a ring is formed, it is, for example, a group represented by any one of the following formulae (A-2) to (A-14): The group represented by any one of formulas (A-1) to (A-14) is exemplified. At least one hydrogen atom in the group is alkyl, cycloalkyl, aryl, or heteroaryl. alkyl, alkoxy, aryloxy, arylthio, trialkylsilyl, tricycloalkenyl alkylsilyl, dialkylcycloalkylsilyl, alkyldicycloalkylsilyl, di Aryl-substituted amino, diheteroaryl-substituted amino, arylheteroaryl-substituted amino , halogen, hydroxy or cyano. Y and * in the formula are as defined above. is the same definition as [ka]

[0574] Examples of rings formed by bonding adjacent groups to each other include hydrocarbon rings such as cyclohexane. The aryl and heteroaryl rings include the above-mentioned R 21 ~R 28 To These rings are the ring structures described in "aryl" and "heteroaryl" above. It is formed so as to be fused with one or two benzene rings in formula (A-1).

[0575] The group represented by formula (A) is, for example, any one of the above formulae (A-1) to (A-14). and the groups represented by the above formulae (A-1) to (A-5) and (A-12) to (A-6) are exemplified. A-14) is preferred, and a group represented by any one of the above formulas (A-1) to (A-4) is preferred. The groups represented by the above formula (A-1), formula (A-3) and formula (A-4) are more preferred. A group represented by any one of the following formulas is more preferred, and a group represented by the above formula (A-1) is particularly preferred. stomach.

[0576] The group represented by formula (A) is a group represented by formula (3-X1) or formula (3-X 2), the naphthalene ring in formula (3-X3), the single bond in formula (3-X3), Ar in formula (3-X3) 3 Combined with In addition, the substitution of at least one hydrogen atom in the compound represented by formula (3) is as described above. Among these bonding forms, the naphthyl group in formula (3-X1) or formula (3-X2) is The talene ring, the single bond in formula (3-X3), and Ar in formula (3-X3) 3 At least one of The form in which it is bound to is preferred.

[0577] In addition, in the structure of the group represented by formula (A), Phthalene ring, single bond in formula (3-X3), Ar in formula (3-X3) 3 The position where In addition, in the structure of the group represented by formula (A), at least one The position at which the two hydrogen atoms are substituted may be any position in the structure of formula (A), for example, Either of the two benzene rings in the structure of formula (A) or R 21 ~R 28 of Any of the rings formed by bonding adjacent groups to each other, or Y in the structure of formula (A) Te no ">NR 29 "R" 29 The bond can be at any position within the

[0578] Examples of the group represented by formula (A) include the following groups: This is the same definition as above. [ka] [ka]

[0579] In addition, all of the hydrogen atoms in the chemical structure of the anthracene compound represented by the general formula (3) are Alternatively, a portion of the hydrogen may be deuterium.

[0580] Specific examples of the anthracene-based compound include compounds of the following formula (3-1) to formula (3-1 42) In the following structural formula, "Me" represents methyl. "tBu" represents a t-butyl group, "D" represents a deuterium group, and "tBu" represents a t-butyl group.

[0581] [ka]

[0582] [ka]

[0583] [ka]

[0584] [ka]

[0585] [ka]

[0586] [ka]

[0587] [ka]

[0588] The anthracene compound represented by formula (3) has a reactive group at a desired position on the anthracene skeleton. a compound having X, Ar groups; 4 and a structure having a reactive group in a partial structure such as the structure of formula (A) Starting from the compound, Suzuki coupling, Negishi coupling, and other known coupling These reactive compounds can be produced by applying a ring-pulling reaction. Examples of the suitable organic compounds include halogens and boronic acids. The synthesis methods in paragraphs

[0089] to

[0175] of Publication No. 2014 / 141725 can be referred to.

[0589] <Fluorene-based compounds> The compound represented by the general formula (4) basically functions as a host. [ka]

[0590] In the above formula (4), R 1 From R 10 are each independently hydrogen, aryl, heteroaryl (the heteroaryl The alkyl may be bonded to the fluorene skeleton in the above formula (4) via a linking group), Diarylamino, diheteroarylamino, arylheteroarylamino, alkyl , cycloalkyl, alkenyl, alkoxy or aryloxy, At least one hydrogen atom is an aryl, heteroaryl, alkyl, or cycloalkyl. may be substituted, Also, R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 5 and R 6 , R 6 and R 7 , R 7 and R 8 Ma or R 9 and R 10 may each independently bond to form a fused ring or a spiro ring. At least one hydrogen atom in the formed ring is substituted with an aryl, heteroaryl (the heteroaryl the diarylamino group may be bonded to the formed ring via a linking group; No, diheteroarylamino, arylheteroarylamino, alkyl, cycloalkyl may be substituted with aryl, alkenyl, alkoxy or aryloxy; At least one hydrogen atom in the formula (I) is aryl, heteroaryl, alkyl, or cycloalkyl. and At least one hydrogen atom in the compound represented by formula (4) is halogen, cyano or heavy It may be substituted with hydrogen.

[0591] The details of each group in the definition of the above formula (4) are as described above in the formulas (1), (1A), and (2 The explanation for the polycyclic aromatic compound of formula (2A) or formula (2B) can be cited.

[0592] R 1 From R 10 The alkenyl in the formula (I) is, for example, an alkenyl having 2 to 30 carbon atoms. Alkenyl having 2 to 20 carbon atoms is preferable, and alkenyl having 2 to 10 carbon atoms is more preferable. Alkenyl having 2 to 6 carbon atoms is preferable, and alkenyl having 2 to 4 carbon atoms is particularly preferable. Preferred alkenyls are vinyl, 1-propenyl, 2-propenyl, 1-butene, nyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl , 4-pentenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl , or 5-hexenyl.

[0593] Specific examples of heteroaryl include the following formulae (4-Ar1), (4-Ar2), and (4-Ar3), (4-Ar4) or (4-Ar5) Monovalent groups represented by excluding atom(s) are also included. [ka] In formulas (4-Ar1) to (4-Ar5), Y 1 are each independently O, S or NR, where R is phenyl, biphenylyl, naphthyl, anthracenyl, or hydrogen. the law of nature, At least one hydrogen atom in the structures of the above formulas (4-Ar1) to (4-Ar5) is a hydrogen atom. Phenyl, biphenylyl, naphthyl, anthracenyl, phenanthrenyl, methyl, ethyl , propyl, or butyl.

[0594] These heteroaryls are linked to the fluorene skeleton in the above formula (4) via a linking group. That is, the fluorene skeleton in formula (4) and the heteroaryl and may be bonded directly or via a linking group. Examples include phenylene, biphenylene, naphthylene, anthracenylene, methylene, and ethylene. -OCH2CH2-, -CH2CH2O-, or -OCH2CH2O-, etc. It can be given.

[0595] Furthermore, R in equation (4) 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 5 and R 6 , R 6 and R 7 Ma or R 7 and R 8 are each independently bonded to form a fused ring, R 9 and R 10are bonded to form a spiro ring R 1 From R 8 The fused ring formed by The ring fused to the Zene ring is an aliphatic ring or an aromatic ring. Preferably, it is an aromatic ring. The structure containing the benzene ring in formula (4) includes a naphthalene ring and a phenanthrene ring. Examples include: R 9 and R 10 The spiro ring formed by The spiro-bonded ring is an aliphatic ring or an aromatic ring, preferably an aromatic ring; An example is a fluorene ring.

[0596] The compound represented by the general formula (4) is preferably a compound represented by the following formula (4-1), formula (4-2) or are compounds represented by formula (4-3), and in general formula (4), R 1 and R 2 but A compound in which a benzene ring formed by bonding is condensed, in general formula (4), R 3 and R 4 Conclusion a compound in which a benzene ring formed by bonding is condensed, and in general formula (4), R 1 From R 8 Noi All of them are unbound compounds. [ka]

[0597] R in formula (4-1), formula (4-2) and formula (4-3) 1 From R 10 The definition of is given by the formula ( 4) The corresponding R 1 From R 10 is the same as Equation (4-1) and Equation (4-2). R in 11 From R 14 The definition of R in equation (4)1 From R 10 is the same as

[0598] The compound represented by the general formula (4) is more preferably a compound represented by the following formula (4-1A), 2A) or (4-3A), and the compounds are represented by formula (4-1), formula (4 -2) or in formula (4-3), R 9 and R 10 are bonded to form a spiro-fluorene ring It is a compound that has been [ka]

[0599] R in formula (4-1A), formula (4-2A) and formula (4-3A) 2 From R 7 The definition of In formula (4-1), formula (4-2) and formula (4-3), the corresponding R 2 From R 7 Same as In formula (4-1A) and formula (4-2A), R 11 From R 14 The definition of formula (4- 1) and R in formula (4-2) 11 From R 14 is the same as

[0600] In addition, all or part of the hydrogen atoms in the compound represented by formula (4) may be replaced by halogen, chlorine, or the like. It may be substituted with anhydrous or deuterium.

[0601] Specific examples of the fluorene-based compound include compounds represented by the following formulae (4-4) to (4-22): ) In the structural formula below, "Me" represents a methyl group. Shows. [ka]

[0602] <Dibenzochrysene compounds> The dibenzochrysene compound as the host is, for example, a compound represented by the following general formula (5): It is a thing. [ka]

[0603] In the above formula (5), R 1 From R 16 are each independently hydrogen, aryl, heteroaryl (the heteroaryl The alkyl may be bonded to the dibenzochrysene skeleton in the above formula (5) via a linking group. (ii), diarylamino, diheteroarylamino, arylheteroarylamino, a alkyl, cycloalkyl, alkenyl, alkoxy or aryloxy; At least one hydrogen atom in may be replaced by kill, Also, R 1 From R 16 adjacent groups may be bonded to each other to form a fused ring, At least one hydrogen atom in the formed ring is substituted with an aryl, heteroaryl (the heteroaryl the aryl may be bonded to the formed ring via a linking group), diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, It may be substituted with alkenyl, alkoxy or aryloxy, At least one hydrogen is replaced by an aryl, heteroaryl, alkyl, or cycloalkyl. may be replaced, and At least one hydrogen atom in the compound represented by formula (5) is halogen, cyano or heavy It may be substituted with hydrogen.

[0604] The details of each group in the definition of the above formula (5) are as described above in the formulas (1), (1A), and (2). The explanation for the polycyclic aromatic compound of formula (2A) or formula (2B) can be cited.

[0605] The alkenyl in the definition of the above formula (5) is, for example, an alkenyl having 2 to 30 carbon atoms. Alkenyl having 2 to 20 carbon atoms is preferred, and alkenyl having 2 to 10 carbon atoms is also preferred. More preferably, alkenyl having 2 to 6 carbon atoms is further preferred, and alkenyl having 2 to 4 carbon atoms is further preferred. is particularly preferred. Preferred alkenyls include vinyl, 1-propenyl, 2-propenyl, 1 -butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl thenyl, 4-pentenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl hexenyl, or 5-hexenyl.

[0606] Specific examples of heteroaryl include those represented by the following formulae (5-Ar1), (5-Ar2), and (5-Ar3). (5-Ar3), (5-Ar4) or (5-Ar5) Monovalent groups represented by excluding atom(s) are also included. [ka] In formula (5-Ar1) to formula (5-Ar5), Y 1 are each independently O, S or NR, where R is phenyl, biphenylyl, naphthyl, anthracenyl, or hydrogen. the law of nature, At least one hydrogen atom in the structures of the above formulas (5-Ar1) to (5-Ar5) is a hydrogen atom. Phenyl, biphenylyl, naphthyl, anthracenyl, phenanthrenyl, methyl, ethyl , propyl, or butyl.

[0607] These heteroaryls can be linked to the dibenzochrysene in the above formula (5) via a linking group. That is, the dibenzochrysene skeleton in formula (5) may be bonded to the above-mentioned skeleton. The heteroaryl may be directly bonded to the heteroaryl, or may be bonded to the heteroaryl via a linking group. Examples of the linking group include phenylene, biphenylene, naphthylene, anthracenylene, methyl Stylene, ethylene, -OCH2CH2-, -CH2CH2O-, or -OCH2CH Examples include 2O-.

[0608] The compound represented by general formula (5) is preferably R 1 , R 4 , R 5 , R 8 , R 9 , R 1 2 , R 13 and R 16 is hydrogen. In this case, R in formula (5) 2 , R 3 , R 6 , R 7 , R 10 , R 11 , R 14 and R 15 are each independently hydrogen, phenyl, biphenyl, phenylyl, naphthyl, anthracenyl, phenanthrenyl, the above formula (5-Ar1), formula (5 -Ar2), formula (5-Ar3), formula (5-Ar4) or formula (5-Ar5) (The monovalent group having the structure is phenylene, biphenylene, naphthylene, Anthracenylene, methylene, ethylene, -OCH2CH2-, -CH2CH2O-, or Or, it is bonded to the dibenzochrysene skeleton in the above formula (5) via -OCH2CH2O-. Preferably, the alkyl group is methyl, ethyl, propyl, or butyl. .

[0609] The compound represented by general formula (5) is more preferably R 1 , R 2 , R 4 , R 5 , R 7 , R 8 , R 9 , R 10 , R 12 , R 13 , R 15 and R 16 is hydrogen. In this case, the formula (5)R 3 , R 6 , R 11 and R 14 At least one (preferably one or two) of and more preferably one) is a single bond, phenylene, biphenylene, naphthylene, anthylene, Racenylene, methylene, ethylene, -OCH2CH2-, -CH2CH2O-, or The above formula (5-Ar1), formula (5-Ar2), formula (5-A r3), a monovalent group having a structure of formula (5-Ar4) or formula (5-Ar5), Other than the at least one (i.e., other than the position substituted by the monovalent group having the structure) is hydrogen, phenyl, biphenylyl, naphthyl, anthracenyl, methyl, ethyl, propyl At least one hydrogen atom in these groups is phenyl, biphenyl, or butyl, substituted with phenyl, naphthyl, anthracenyl, methyl, ethyl, propyl, or butyl; It may be replaced.

[0610] Furthermore, R in equation (5) 2 , R 3 , R 6 , R 7 , R 10 , R 11 , R 14 and R 15 and A monovalent group having a structure represented by formula (5-Ar5) is selected from the above formula (5-Ar1). When selected, at least one hydrogen atom in the structure is R 1 From R 1 6 may be bonded to any one of the following to form a single bond.

[0611] Specific examples of the dibenzochrysene-based compound include compounds represented by the following formulas (5-1) to (5 -39) In addition, "tBu" in the following structural formula is This represents a t-butyl group. [ka]

[0612] [ka]

[0613] The above-mentioned materials for the light-emitting layer (host material and dopant material) may have reactive substituents. A polymer compound obtained by polymerizing a reactive compound substituted with , as a monomer, or a polymer compound obtained by polymerizing the polymer A molecular crosslinked body or a pendant polymer obtained by reacting a main chain polymer with the reactive compound. The compound or its pendant polymer crosslinked product can also be used as a material for the light-emitting layer. In this case, the reactive substituent may be any of the above formulas (1), (1A), (2A) and (3A). Alternatively, the explanation for the polycyclic aromatic compound represented by formula (2B) can be cited. The uses of such polymer compounds and crosslinked polymers will be described in detail below.

[0614] <Example of polymer host material> [ka]

[0615] In formula (SPH-1), Each MU is independently a bivalent group represented by removing any two hydrogen atoms from an aromatic compound. The groups EC are each independently represented by removing any one hydrogen atom from an aromatic compound. It is a monovalent group, and two hydrogen atoms in MU are replaced with EC or MU, and k is 2 to 50,000. is an integer.

[0616] More specifically, Each MU independently represents an arylene, heteroarylene, or diarylylenearyl group. amino, diarylylenearylboryl, oxaborine-diyl, azaborine-diyl , EC independently represents hydrogen, aryl, heteroaryl, diarylamino, diaryl, heteroarylamino, arylheteroarylamino or aryloxy; At least one hydrogen in MU and EC may further be aryl, heteroaryl, optionally substituted with diarylamino, alkyl and cycloalkyl; k is an integer from 2 to 50,000. k is preferably an integer of 20 to 50,000, and is preferably an integer of 100 to 50,000. It is more preferable that

[0617] At least one hydrogen atom in MU and EC in formula (SPH-1) is a hydrogen atom having 1 to 2 carbon atoms. 4 alkyl, cycloalkyl having 3 to 24 carbon atoms, substituted with halogen or deuterium Any -CH2- in the alkyl may be -O- or -Si(CH 3) may be substituted with 2-, and the alkyl may be directly substituted with EC in formula (SPH-1). Any -CH2- except the bonding -CH2- is replaced with an arylene having 6 to 24 carbon atoms. Any hydrogen in the alkyl may be substituted with fluorine.

[0618] For example, MU can be expressed by removing any two hydrogen atoms from any of the following compounds: Examples of such divalent groups include: [ka]

[0619] More specifically, divalent groups represented by any of the following structures are included: In this case, MU binds to another MU or EC at *.

[0620] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka]

[0621] Examples of EC include monovalent groups represented by any of the following structures: In these, EC binds to MU at *.

[0622] [ka] [ka]

[0623] The compound represented by formula (SPH-1) has the following structure in the molecule from the viewpoint of solubility and coating film-forming property. It is preferred that 10 to 100% of the total number of MUs (k) have alkyl groups having 1 to 24 carbon atoms. Of the total number of MUs in the molecule (k), 30-100% are alkyl (carbon number 1-18). It is more preferable that the total number of MU in the molecule (k) is 3 to 18. 50-100% of MU is alkyl with 1-12 carbon atoms (branched alkyl with 3-12 carbon atoms) On the other hand, from the viewpoint of in-plane orientation and charge transport, it is more preferable that the molecular 10-100% of the total number of MUs (k) in the Preferably, 30 to 100% of the total number of MUs (k) in the molecule are alkyl groups having 7 to 24 carbon atoms. It is more preferable that the alkyl group has a branched chain having 7 to 24 carbon atoms.

[0624] The uses of such polymer compounds and crosslinked polymers will be described in detail below.

[0625] <Electron injection layer and electron transport layer in organic electroluminescent device> The electron injection layer 107 efficiently injects electrons moving from the cathode 108 into the light-emitting layer 105. The electron transport layer 106 serves to inject electrons from the cathode 108 into the electron transport layer 106. The injected electrons or the electrons injected from the cathode 108 through the electron injection layer 107 are efficiently The electron transport layer 106 and the electron injection layer 107 serve to transport electrons to the light-emitting layer 105. , respectively, one or more kinds of electron transporting and injecting materials are laminated or mixed, or electron transporting and It is formed by a mixture of an injectable material and a polymeric binder.

[0626] The electron injection and transport layer is responsible for injecting electrons from the cathode and transporting them further. It is desirable that the layer has high electron injection efficiency and efficiently transports the injected electrons. To achieve this, the electron affinity must be large, the electron mobility must be large, and the stability must be excellent. It is preferable that the material be one that is unlikely to generate impurities that act as traps during production and use. However, when considering the balance of hole and electron transport, the holes from the anode do not recombine and When the electron transport ability is the main function of the cathode, the electron transport ability is the main function of the cathode. Even if the electron transport capacity is not so high, the effect of improving the luminous efficiency is equivalent to that of a material with a high electron transport capacity. 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.

[0627] The material (electron transport material) for forming the electron transport layer 106 or the electron injection layer 107 is: Compounds that have been conventionally used as electron transport compounds in photoconductive materials, organic EL devices The compound is arbitrarily selected from known compounds used in the electron injection layer and electron transport layer. You can be there.

[0628] The materials used for the electron transport layer or the electron injection layer include carbon, hydrogen, oxygen, sulfur, ketone, and the like. Aromatic or heteroaromatic rings composed of one or more atoms selected from among silicon and phosphorus Compounds consisting of a ring, pyrrole derivatives and their fused ring derivatives, and compounds having an electron-accepting nitrogen It is preferable that the metal complex contains at least one selected from the metal complexes Condensed ring aromatic derivatives such as phthalene and anthracene, 4,4'-bis(diphenylene) Styryl aromatic ring derivatives, represented by (thenyl)biphenyl, perinone derivatives, coumarin 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 an electron-accepting nitrogen include hydroxyphenyloxazole complexes. Hydroxyazole complexes, azomethine complexes, tropolone metal complexes, flavonols, etc. These materials can be used alone. However, it is acceptable to use a mixture of different materials.

[0629] Specific examples of other electron transport compounds include pyridine derivatives, naphthalene derivatives, and ammonium salts. Thracene 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 )1,3,4-oxadiazolyl]phenylene, etc.), thiophene derivatives, triazoles Derivatives (e.g., N-naphthyl-2,5-diphenyl-1,3,4-triazole), thiazides Azole derivatives, metal complexes of oxine derivatives, quinolinol metal complexes, quinoxaline derivatives Conductors, polymers of quinoxaline derivatives, benzazole compounds, gallium complexes, pyrazoles perfluorinated phenylene derivatives, triazine derivatives, pyrazine derivatives, benzophenone derivatives, benzoquinoline derivative (2,2'-bis(benzo[h]quinolin-2-yl)-9,9'-s pyrobifluorene, etc.), imidazopyridine derivatives, borane derivatives, benzimidazole Derivatives (such as tris(N-phenylbenzimidazol-2-yl)benzene), benzo Oxazole derivatives, benzothiazole derivatives, quinoline derivatives, terpyridines, etc. Polypyridine derivatives, bipyridine derivatives, terpyridine derivatives (1,3-bis(4'-( 2,2':6',2"-terpyridinyl))benzene, etc.), naphthyridine derivatives (bis (1-Naphthyl)-4-(1,8-naphthyridin-2-yl)phenylphosphine oxa ides, aldazine derivatives, carbazole derivatives, indole derivatives, phosphorus oxides Examples of the styryl derivatives include styryl derivatives and bisstyryl derivatives.

[0630] Metal complexes having an electron-accepting nitrogen atom can also be used, for example, quinolinol-based Metal complexes, hydroxyazole complexes such as hydroxyphenyloxazole complexes, azomes tin complexes, tropolone metal complexes, flavonol metal complexes, and benzoquinoline metal complexes. Examples include:

[0631] The above-mentioned materials may be used alone or in combination with other materials.

[0632] Among the above-mentioned materials, borane derivatives, pyridine derivatives, fluoranthene derivatives, BO derivatives, anthracene derivatives, benzofluorene derivatives, phosphine oxide derivatives , pyrimidine derivatives, carbazole derivatives, triazine derivatives, benzimidazole derivatives The compounds, phenanthroline derivatives, and quinolinol-based metal complexes are preferred.

[0633] <Borane derivatives> The borane derivative is, for example, a compound represented by the following general formula (ETM-1), and in detail This is disclosed in Japanese Patent Application Laid-Open No. 2007-27587. [ka] In the above formula (ETM-1), R 11 and R 12 are each independently hydrogen, alkyl, , cycloalkyl, optionally substituted aryl, substituted silyl, substituted or cyano, and R 13 ~R 16 teeth, each independently represents an optionally substituted alkyl, an optionally substituted cycloalkyl, X is an optionally substituted aryl or an optionally substituted aryl; Y is an optionally substituted aryl having 16 or less carbon atoms, a substituted boron n is independently 0; The integers are 0 to 3. In addition, the substitutions for "optionally substituted" and "substituted" are Substituents include aryl, heteroaryl, alkyl, and cycloalkyl. can be.

[0634] Among the compounds represented by the above general formula (ETM-1), the compound represented by the following general formula (ETM-1-1) and compounds represented by the following general formula (ETM-1-2) are preferred. [ka] In formula (ETM-1-1), R 11 and R 12 are each independently hydrogen, alkyl, , cycloalkyl, optionally substituted aryl, substituted silyl, substituted or cyano, and R 13 ~R 16 teeth, each independently represents an optionally substituted alkyl, an optionally substituted cycloalkyl, aryl, or optionally substituted aryl; R 21 and R 22 are independent of each other Examples of the alkyl group include hydrogen, alkyl, cycloalkyl, optionally substituted aryl, substituted at least one of silyl, an optionally substituted nitrogen-containing heterocycle, or cyano; , X 1 represents an optionally substituted arylene having 20 or less carbon atoms, and each n is independently and m are each independently an integer of 0 to 4. In the case of "optionally substituted" or "substituted", the substituents include aryl, hydroxyl, hydroxypropyl ... Examples include cycloaryl, alkyl, and cycloalkyl. [ka] In formula (ETM-1-2), R 11 and R 12 are each independently hydrogen, alkyl, , cycloalkyl, optionally substituted aryl, substituted silyl, substituted or cyano, and R 13 ~R 16 teeth, each independently represents an optionally substituted alkyl, an optionally substituted cycloalkyl, X is an alkyl group or an optionally substituted aryl group; 1 is the number of carbon atoms that may be substituted It is an arylene having 20 or less n's, and each n is independently an integer of 0 to 3. In the case of "optionally substituted" or "substituted", the substituents include aryl , heteroaryl, alkyl, or cycloalkyl.

[0635] X 1 Specific examples of the compound include those represented by any one of the following formulas (X-1) to (X-9). In each structural formula, * indicates the bonding position. [ka] (In each formula, R a are each independently an alkyl group, a cycloalkyl group, or a substituted It is a phenyl group that may be

[0636] Specific examples of the borane derivative include the following compounds: [ka]

[0637] This borane derivative can be produced using known raw materials and known synthesis methods.

[0638] <Pyridine derivatives> The pyridine derivative is, for example, a compound represented by the following formula (ETM-2), and preferably The compound is represented by formula (ETM-2-1) or formula (ETM-2-2). [ka]

[0639] φ is an n-valent aryl ring (preferably an n-valent benzene ring, naphthalene ring, anthracene ring, ring, fluorene ring, benzofluorene ring, phenalene ring, phenanthrene ring or trifluorene ring phenylene ring), and n is an integer of 1 to 4.

[0640] In the above formula (ETM-2-1), R 11 ~R 18are each independently hydrogen, alkyl (preferably alkyl having 1 to 24 carbon atoms), cycloalkyl (preferably alkyl having 3 to 4 carbon atoms), cycloalkyl having 6 to 12 carbon atoms) or aryl (preferably aryl having 6 to 30 carbon atoms). do.

[0641] In the above formula (ETM-2-2), R 11 and R 12 are each independently hydrogen , alkyl (preferably alkyl having 1 to 24 carbon atoms), cycloalkyl (preferably cycloalkyl having 3 to 12 carbon atoms) or aryl (preferably aryl having 6 to 30 carbon atoms) and R 11 and R 12 may be bonded to form a ring.

[0642] In each formula, the "pyridine-based substituent" is any one of the following formulae (Py-1) to (Py-15): The pyridine-based substituents are each independently an alkyl group having 1 to 4 carbon atoms or a carbon atom. The pyridine-based substituent may be substituted with a cycloalkyl having 5 to 10 carbon atoms. In each formula, the φ is bonded to an anthracene ring or a fluorene ring via an ethylene group or a naphthylene group. In each structural formula, * indicates the bonding position.

[0643] [ka]

[0644] The pyridine-based substituent is any one of the above formulas (Py-1) to (Py-15). Among these, any one of the following formulas (Py-21) to (Py-44) is preferred. * in each structural formula indicates the bond position. [ka]

[0645] At least one hydrogen atom in each pyridine derivative may be replaced by deuterium. In addition, the two "pyridine-based compounds" in the above formula (ETM-2-1) and formula (ETM-2-2) One of the "substituents" may be replaced by an aryl.

[0646] R 11 ~R 18 The "alkyl" in the formula (I) may be either a straight chain or a branched chain. For example, a linear alkyl having 1 to 24 carbon atoms or a branched alkyl having 3 to 24 carbon atoms can be mentioned. Preferred "alkyl" is alkyl having 1 to 18 carbon atoms (branched alkyl having 3 to 18 carbon atoms). More preferred "alkyl" is alkyl having 1 to 12 carbon atoms (alkyl having 3 to 12 carbon atoms). A more preferred "alkyl" is an alkyl having 1 to 6 carbon atoms. Particularly preferred "alkyl" is a branched alkyl having 1 to 6 carbon atoms. 4 alkyl (branched alkyl having 3 to 4 carbon atoms).

[0647] Specific examples of "alkyl" include methyl, ethyl, n-propyl, isopropyl, n- Butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl t-pentyl (t-amyl), n-hexyl, 1-methylpentyl, 3,3-dimethyl butyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, t -Octyl (1,1,3,3-tetramethylbutyl), 1-methylheptyl, 2-ethyl Hexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 2,6-di Methyl-4-heptyl, 3,5,5-trimethylhexyl, n-decyl, n-undecyl , 1-methyldecyl, n-dodecyl, n-tridecyl, 1-hexylheptyl, n-tetradecyl Ladecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl , n-eicosyl, etc. 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 ethylhexyl, 1-ethyl-1,3-dimethylbutyl, 1,1,2,2-tetramethylpropyl propyl, 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- Propyl-1-methylbutyl, 1,1-dimethylhexyl, and the like are also included.

[0648] The alkyl having 1 to 4 carbon atoms that is substituted on the pyridine-based substituent is the same as the alkyl described above. It can be cited.

[0649] R 11 ~R 18 The "cycloalkyl" in the above formula includes, for example, cycloalkyl having 3 to 12 carbon atoms. Preferred "cycloalkyl" is a cycloalkyl having 3 to 10 carbon atoms. A more preferred "cycloalkyl" is a cycloalkyl having 3 to 8 carbon atoms. More preferred "cycloalkyl" is cycloalkyl having 3 to 6 carbon atoms. Specific examples of "cycloalkyl" include cyclopropyl, cyclobutyl, and cyclopentyl. cyclohexyl, methylcyclopentyl, cycloheptyl, methylcyclohexyl, Examples include cyclooctyl and dimethylcyclohexyl.

[0650] R 11 ~R 18 As for the "aryl" in the above, preferred aryl is an aryl having 6 to 30 carbon atoms. Aryl is more preferably an aryl having 6 to 18 carbon atoms, and even more preferably Preferably, it is an aryl having 6 to 14 carbon atoms, and particularly preferably an aryl having 6 to 12 carbon atoms. do.

[0651] Specific examples of "aryl having 6 to 30 carbon atoms" include monocyclic aryl such as phenyl, condensed aryl, and the like. (1-,2-)naphthyl is a fused bicyclic aryl; acenaphthyl is a fused tricyclic aryl; ethylene-(1-, 3-, 4-, 5-)yl, fluorene-(1-, 2-, 3-, 4-, 9 -)yl, phenalen-(1-,2-)yl, (1-,2-,3-,4-,9-)phenalen triphenylene-(1-,2-)yl, pyrene-( 1-, 2-, 4-)yl, naphthacene-(1-, 2-, 5-)yl, fused pentacyclic aryl Perylene-(1-, 2-, 3-)yl, pentacene-(1-, 2-, 5-, 6-) Examples include Iru.

[0652] Preferred examples of the "aryl having 6 to 30 carbon atoms" include phenyl, naphthyl, phenanthryl, and chlorine. phenyl, 1-naphthyl, and the like are preferred. Particularly preferred are phenyl, 1-naphthyl and phenanthryl. Examples include 2-naphthyl and 2-naphthyl.

[0653] R in the above formula (ETM-2-2) 11 and R 12 Even if they bond to form a ring, As a result, the five-membered ring of the fluorene skeleton is often cyclobutane, cyclopentane, cyclopentane, Pentene, cyclopentadiene, cyclohexane, fluorene, or indene are spin It may be bonded to the

[0654] Specific examples of the pyridine derivative include the following compounds: [ka]

[0655] This pyridine derivative can be produced using known raw materials and known synthesis methods.

[0656] <Fluoranthene derivatives> The fluoranthene derivative is, for example, a compound represented by the following general formula (ETM-3): Details are disclosed in International Publication No. 2010 / 134352. [ka]

[0657] In the above formula (ETM-3), X 12 ~X 21 is hydrogen, halogen, straight chain, branched or cyclic alkyl, straight-chain, branched or cyclic alkoxy, substituted or unsubstituted aryl, or or substituted or unsubstituted heteroaryl. Examples of the aryl group include aryl, heteroaryl, alkyl, and cycloalkyl. .

[0658] Specific examples of this fluoranthene derivative include, for example, the following compounds. [Chemical formula]

[0659] <BO - based derivative> The BO - based derivative is, for example, a polycyclic aromatic compound represented by the following formula (ETM - 4), or a multimer of a polycyclic aromatic compound having a plurality of structures represented by the following formula (ETM - 4). [Chemical formula]

[0660] R 1 ~R 11 are each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkoxy or aryloxy, and at least one hydrogen in these may be substituted with aryl, heteroaryl, alkyl or cycloalkyl.

[0661] Also, adjacent groups among R 1 ~R 11 may combine with each other to form an aryl ring or a heteroaryl ring together with the a - ring, b - ring or c - ring, and at least one hydrogen in the formed ring may be substituted with aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkoxy or aryloxy, and at least one hydrogen in these may be substituted with aryl, heteroaryl, alkyl or cycloalkyl. [[ID=�0]]

[0662] ​​​​​​​​In addition, at least one hydrogen atom in the compound or structure represented by formula (ETM-4) It may be substituted with halogen or deuterium.

[0663] The substituents and ring formation forms in formula (ETM-4) are explained in the above formula (1), formula (1A), (2A) or (2B) This can be done.

[0664] Specific examples of the BO derivative include the following compounds: [ka]

[0665] This BO derivative can be produced using known raw materials and known synthesis methods.

[0666] <Anthracene derivatives> One of the anthracene derivatives is, for example, a compound represented by the following formula (ETM-5-1): do. [ka]

[0667] Ar are each independently a divalent benzene or naphthalene; R 1 ~R 4 teeth, Each independently represents hydrogen, alkyl having 1 to 6 carbon atoms, cycloalkyl having 3 to 6 carbon atoms, or or an aryl having 6 to 20 carbon atoms.

[0668] Ar may be independently selected from divalent benzene or naphthalene. The two Ar groups may be different or the same, but the synthesis of anthracene derivatives From the viewpoint of easiness, it is preferable that they are the same. Ar is bonded to pyridine, and and a pyridine moiety" is formed, and this moiety is, for example, represented by the following formula (Py-1) to formula ( Py-12) is bonded to anthracene. * indicates the bond position.

[0669] [ka]

[0670] Among these groups, the group represented by any one of the above formulas (Py-1) to (Py-9) A group represented by any one of the above formulae (Py-1) to (Py-6) is more preferred. The two "Ar and pyridine moieties" that bind to anthracene have the same structure. However, from the viewpoint of ease of synthesis of the anthracene derivative, it is preferable to use the same However, from the viewpoint of device characteristics, it is preferable that the two "Ar and pyrimidine" structures are the same. The structures of the "sin-containing moieties" may be the same or different.

[0671] R 1 ~R 4 The alkyl group having 1 to 6 carbon atoms can be either a straight chain or a branched chain. That is, it is a linear alkyl having 1 to 6 carbon atoms or a branched alkyl having 3 to 6 carbon atoms. More preferably, it is an alkyl having 1 to 4 carbon atoms (branched alkyl having 3 to 4 carbon atoms). Specific examples include methyl, ethyl, n-propyl, isopropyl, n-butyl, and isobutyl. butyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl t-amyl, n-hexyl, 1-methylpentyl, 3,3-dimethylbutyl, or or 2-ethylbutyl, and methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, or t-butyl is preferred, and methyl, ethyl, Or t-butyl is more preferred.

[0672] R 1 ~R 4 Specific examples of the cycloalkyl having 3 to 6 carbon atoms include cyclopropyl , cyclobutyl, cyclopentyl, cyclohexyl, methylcyclopentyl, cycloheptyl Examples include cyclohexyl, methylcyclohexyl, cyclooctyl, and dimethylcyclohexyl. can be done.

[0673] R 1 ~R 4 For aryls having 6 to 20 carbon atoms, aryls having 6 to 16 carbon atoms is preferred, aryl having 6 to 12 carbon atoms is more preferred, and aryl having 6 to 10 carbon atoms is particularly preferred. Preferred.

[0674] Specific examples of "aryl having 6 to 20 carbon atoms" include monocyclic aryl such as phenyl, ( o-,m-,p-)tolyl, (2,3-,2,4-,2,5-,2,6-,3,4-,3 ,5-)xylyl, mesityl (2,4,6-trimethylphenyl), (o-, m-, p- ) cumenyl, bicyclic aryl (2-, 3-, 4-) biphenylyl, fused bicyclic aryl (1-,2-)naphthyl, a tricyclic aryl; terphenylyl (m-terphenyl); 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-terphenyl-2-yl, m-terphenyl-3-yl, m-terpheny o-terphenyl-4-yl, o-terphenyl-2-yl, o-terphenyl-3-yl, o-terfenyl p-terphenyl-4-yl, p-terphenyl-2-yl, p-terphenyl-3-yl, ... phenyl-4-yl), fused tricyclic aryl anthracene-(1-, 2-, 9-phenyl-4-yl), -)yl, acenaphthylene-(1-,3-,4-,5-)yl, fluorene-(1-,2 -,3-,4-,9-)yl, phenalen-(1-,2-)yl, (1-,2-,3-, 4-, 9-)phenanthryl, fused tetracyclic aryl triphenylene-(1-, 2- )yl, pyrene-(1-, 2-, 4-)yl, tetracene-(1-, 2-, 5-)yl, Examples include perylene-(1-, 2-, 3-)yl, which is a fused pentacyclic aryl.

[0675] Preferred "aryl having 6 to 20 carbon atoms" are phenyl, biphenylyl, and terphenylyl. or naphthyl, more preferably phenyl, biphenylyl, 1-naphthyl, 2- naphthyl or m-terphenyl-5'-yl, more preferably phenyl, biphenyl It is preferably phenylyl, 1-naphthyl or 2-naphthyl, and most preferably phenyl.

[0676] One of the anthracene derivatives is, for example, a compound represented by the following formula (ETM-5-2): do. [ka]

[0677] Ar 1 are each independently a single bond, a divalent benzene, a divalent naphthalene, an anthracene, fluorene or phenalene.

[0678] Ar 2 are each independently an aryl having 6 to 20 carbon atoms, and The same explanation as for "aryl having 6 to 20 carbon atoms" in -1) can be cited. An aryl having 6 to 16 carbon atoms is preferred, an aryl having 6 to 12 carbon atoms is more preferred, and an aryl having 6 to 16 carbon atoms is more preferred. Particularly preferred is an aryl having a carbon number of 10 or less. Specific examples include phenyl, biphenylyl, and naphthyl. , terphenylyl, anthracenyl, acenaphthylenyl, fluorenyl, phenalenyl, Examples include phenanthryl, triphenylenyl, pyrenyl, tetracenyl, and perylenyl. can be.

[0679] R 1 ~R 4 are each independently hydrogen, alkyl having 1 to 6 carbon atoms, is a cycloalkyl or an aryl having 6 to 20 carbon atoms, and in the above formula (ETM-5-1), The explanations given can be cited.

[0680] Specific examples of these anthracene derivatives include the following compounds: [ka]

[0681] These anthracene derivatives can be produced using known raw materials and known synthesis methods. Cut.

[0682] <Benzofluorene derivatives> The benzofluorene derivative is, for example, a compound represented by the following formula (ETM-6). [ka]

[0683] Ar 1 are each independently an aryl having 6 to 20 carbon atoms, and The same explanation as for "aryl having 6 to 20 carbon atoms" in -1) can be cited. An aryl having 6 to 16 carbon atoms is preferred, an aryl having 6 to 12 carbon atoms is more preferred, and an aryl having 6 to 16 carbon atoms is more preferred. Particularly preferred is an aryl having a carbon number of 10 or less. Specific examples include phenyl, biphenylyl, and naphthyl. , terphenylyl, anthracenyl, acenaphthylenyl, fluorenyl, phenalenyl, Examples include phenanthryl, triphenylenyl, pyrenyl, tetracenyl, and perylenyl. can be.

[0684] Ar 2 are each independently hydrogen, alkyl (preferably alkyl having 1 to 24 carbon atoms), ), cycloalkyl (preferably cycloalkyl having 3 to 12 carbon atoms) or aryl (preferably Preferably, it is an aryl having 6 to 30 carbon atoms, and two Ar 2 are bonded to form a ring Good too.

[0685] Ar 2 The "alkyl" in the above may be either a straight chain or a branched chain, for example, Examples include linear alkyl having 1 to 24 carbon atoms and branched alkyl having 3 to 24 carbon atoms. The preferred "alkyl" is alkyl having 1 to 18 carbon atoms (branched alkyl having 3 to 18 carbon atoms). More preferred "alkyl" is alkyl having 1 to 12 carbon atoms (e.g., alkyl having 3 to 12 carbon atoms). A more preferred "alkyl" is an alkyl having 1 to 6 carbon atoms (a branched alkyl). Particularly preferred "alkyl" is alkyl having 1 to 4 carbon atoms. alkyl (branched alkyl with 3 to 4 carbon atoms). Specific examples of "alkyl" include methyl , ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl t-pentyl, n-pentyl, isopentyl, neopentyl, t-pentyl (t-amyl), n- Hexyl, 1-methylpentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl Examples include ethyl and 1-methylhexyl.

[0686] Ar 2 The "cycloalkyl" in the above formula includes, for example, cycloalkyl having 3 to 12 carbon atoms. Preferred "cycloalkyl" is a cycloalkyl having 3 to 10 carbon atoms. More preferred "cycloalkyl" is cycloalkyl having 3 to 8 carbon atoms. Preferred "cycloalkyl" is cycloalkyl having 3 to 6 carbon atoms. Examples of "cycloalkyl" include cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl. methylcyclopentyl, cycloheptyl, methylcyclohexyl, cyclooctyl or or dimethylcyclohexyl.

[0687] Ar 2 As for the "aryl" in the above, preferred aryl is an aryl having 6 to 30 carbon atoms. The aryl is more preferably an aryl having 6 to 18 carbon atoms, and further preferably an aryl having 6 to 18 carbon atoms. It is an aryl having 6 to 14 carbon atoms, and particularly preferably an aryl having 6 to 12 carbon atoms.

[0688] Specific examples of "aryl having 6 to 30 carbon atoms" include phenyl, naphthyl, and acenaphthyl. nyl, fluorenyl, phenalenyl, phenanthryl, triphenylenyl, pyrenyl, na Examples include phthalocenyl, perylenyl, and pentacenyl.

[0689] Two Ar 2 may be bonded to form a ring, resulting in a five-membered ring of the fluorene skeleton. These include cyclobutane, cyclopentane, cyclopentene, cyclopentadiene, and cyclohexene. The oxane, fluorene, or indene may be spiro-linked.

[0690] Specific examples of the benzofluorene derivative include the following compounds: [ka]

[0691] This benzofluorene derivative can be produced using known raw materials and known synthesis methods. Cut.

[0692] <Phosphine oxide derivatives> The phosphine oxide derivative is, for example, a compound represented by the following formula (ETM-7-1): The details are also described in International Publication No. 2013 / 079217. [ka] R 5 is a substituted or unsubstituted alkyl having 1 to 20 carbon atoms, a cycloalkyl having 3 to 16 carbon atoms, alkyl, aryl having 6 to 20 carbon atoms, or heteroaryl having 5 to 20 carbon atoms; R 6 is CN, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, silyl having 3 to 16 carbon atoms chloroalkyl, heteroalkyl having 1 to 20 carbon atoms, aryl having 6 to 20 carbon atoms, aryl having 5 carbon atoms Heteroaryl with up to 20 carbon atoms, alkoxy with 1 to 20 carbon atoms, or aryl with 6 to 20 carbon atoms It is oxy, R 7 and R 8 are each independently a substituted or unsubstituted aryl group having 6 to 20 carbon atoms. aryl or heteroaryl having 5 to 20 carbon atoms, R 9 is oxygen or sulfur, j is 0 or 1, k is 0 or 1, r is an integer of 0 to 4, and q is an integer of 1 to 3. is an integer. In the case where the group is substituted, the substituent may be an aryl, a heteroaryl, an alkyl, or the like. Or cycloalkyl, etc.

[0693] The phosphine oxide derivative is, for example, a compound represented by the following formula (ETM-7-2): Good too. [ka]

[0694] R 1 ~R 3 may be the same or different and are hydrogen, an alkyl group, a cycloalkyl group, Aralkyl groups, alkenyl groups, cycloalkenyl groups, alkynyl groups, alkoxy groups, alkoxy groups, alkylthio group, cycloalkylthio group, aryl ether group, aryl thioether group, aryl Aryl group, heterocyclic group, halogen, cyano group, aldehyde group, carbonyl group, carboxyl Among the fused rings formed between the substituted groups, amino groups, nitro groups, silyl groups, and adjacent substituents, are selected.

[0695] Ar 1 may be the same or different and are arylene or heteroarylene groups. Ar 2 may be the same or different and are aryl or heteroaryl groups However, Ar 1 and Ar 2 At least one of the groups has a substituent, or the adjacent groups A condensed ring is formed between the substituted and unsaturated groups. n is an integer of 0 to 3. When n is 0, the unsaturated group is When n is 3, R 1 does not exist.

[0696] Among these substituents, the alkyl group includes, for example, a methyl group, an ethyl group, a propyl group, a bromine group, and the like. refers to a saturated aliphatic hydrocarbon group, such as a methyl group, which may be unsubstituted or substituted. If substituted, the substituent is not particularly limited, and examples thereof include alkyl groups and aryl groups. , heterocyclic groups, etc., which are also included in the following description. The number of carbon atoms in the group is not particularly limited, but is usually in the range of 1 to 20 in terms of availability and cost. It is an enclosure.

[0697] The cycloalkyl group includes, for example, cyclopropyl, cyclohexyl, norbornyl, It refers to saturated alicyclic hydrocarbon groups such as benzoyl, benzoyl, and adamantyl, which can be unsubstituted or substituted. The number of carbon atoms in the alkyl group is not particularly limited, but is usually in the range of 3 to 20. be.

[0698] The aralkyl group is an aliphatic hydrocarbon group such as a benzyl group or a phenylethyl group. It indicates an aromatic hydrocarbon group mediated by a substituent, and both aliphatic and aromatic hydrocarbons are unsubstituted. The number of carbon atoms in the aliphatic moiety is not particularly limited, but it is usually 1. The range is ~20.

[0699] The alkenyl group is a double bonded group such as a vinyl group, an allyl group, or a butadienyl group. represents an unsaturated aliphatic hydrocarbon group containing a bond, 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.

[0700] The cycloalkenyl group includes, for example, a cyclopentenyl group, a cyclopentadienyl group, and the like. It refers to an unsaturated alicyclic hydrocarbon group containing a double bond, such as a cyclohexene group or a cyclohexene group. It doesn't matter if it's a substitution or a replacement.

[0701] The alkynyl group is an unsaturated aliphatic group containing a triple bond, such as an acetylenyl group. represents a hydrocarbon group, which may be unsubstituted or substituted. The number is not particularly limited, but is usually in the range of 2 to 20.

[0702] The alkoxy group is an aliphatic carbonized group via an ether bond, such as a methoxy group. 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 is usually in the range of 1-20.

[0703] An alkylthio group is a group in which the oxygen atom of the ether bond of an alkoxy group is replaced with a sulfur atom. It is a group that has been

[0704] 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.

[0705] The aryl ether group is an aromatic group formed via an ether bond, such as a phenoxy group. The aromatic hydrocarbon group may be unsubstituted or substituted. The number of carbon atoms in the aryl ether group is not particularly limited, but is usually in the range of 6 to 40.

[0706] In addition, an aryl thioether group is a group in which the oxygen atom of the ether bond of the aryl ether group is It is a group substituted with a sulfur atom.

[0707] The aryl group includes, for example, a phenyl group, a naphthyl group, a biphenyl group, a phenanthrene group, and the like. The aryl group refers to an aromatic hydrocarbon group such as an alkyl group, a terphenyl group, or a pyrenyl group. The number of carbon atoms in the aryl group is not particularly limited, but is usually , ranging from 6 to 40.

[0708] The heterocyclic group includes, for example, a furanyl group, a thiophenyl group, an oxazolyl group, a pyridinyl group, and the like. a cyclic structural group having atoms other than carbon, such as a quinolinyl group, a carbazolyl group, The heterocyclic group may be unsubstituted or substituted. The number of carbon atoms in the heterocyclic group is not particularly limited. , usually in the range of 2 to 30.

[0709] Halogen refers to fluorine, chlorine, bromine, and iodine.

[0710] Aldehyde groups, carbonyl groups, and amino groups are used in aliphatic hydrocarbons, alicyclic hydrocarbons, and aromatic hydrocarbons. It may also include groups substituted with aromatic hydrocarbons, heterocycles, etc.

[0711] In addition, aliphatic hydrocarbons, alicyclic hydrocarbons, aromatic hydrocarbons, and heterocyclic rings may be unsubstituted or substituted. It doesn't matter if it's broken.

[0712] The silyl group refers to a silicon compound group such as a trimethylsilyl group, which is an unsubstituted silyl group. The number of carbon atoms in the silyl group is not particularly limited, but is usually 3. The silicon number is usually in the range of 1 to 20.

[0713] 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 Ar2 Conjugates formed between etc. or It is a non-conjugated fused ring. Here, when n is 1, two R 1 Conjugate or non-conjugate condensation These fused rings may contain nitrogen, oxygen, or sulfur atoms in the ring structure. Alternatively, it may be condensed with another ring.

[0714] Specific examples of the phosphine oxide derivative include the following compounds: . [ka]

[0715] This phosphine oxide derivative can be produced using known raw materials and known synthesis methods. can be done.

[0716] <Pyrimidine derivatives> The pyrimidine derivative is, for example, a compound represented by the following formula (ETM-8), and is preferably is a compound 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]

[0717] Ar each independently represents an optionally substituted aryl or an optionally substituted n is an integer of 1 to 4, preferably an integer of 1 to 3, More preferably, it is 2 or 3.

[0718] The "aryl" in the "optionally substituted aryl" includes, for example, an aryl having 6 to 30 carbon atoms. The aryl having 6 to 24 carbon atoms is preferable, and the aryl having 6 to 24 carbon atoms is more preferable. The aryl group preferably has from 1 to 20 carbon atoms, and more preferably has from 6 to 12 carbon atoms.

[0719] Specific examples of "aryl" include phenyl, which is a monocyclic aryl, and phenyl, which is a bicyclic aryl. (2-, 3-, 4-) biphenylyl, fused bicyclic aryl, (1-, 2-) naphthyl tricyclic aryl terphenylyl (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 p-terphenyl-2-yl, p-terphenyl-3-yl, p-terphenyl-4-yl), fused triphenyl Aryl ring systems, such as acenaphthylene-(1-, 3-, 4-, 5-)yl, fluorene- (1-,2-,3-,4-,9-)yl, phenalen-(1-,2-)yl, (1-,2 -, 3-, 4-, 9-)phenanthryl, tetracyclic aryl quaterphenylyl (5 '-Phenyl-m-terphenyl-2-yl, 5'-phenyl-m-terphenyl-3- yl, 5'-phenyl-m-terphenyl-4-yl, m-quaterphenylyl), condensed Tetracyclic aryls such as triphenylen-(1-,2-)yl and pyrene-(1-,2-,4 -)yl, naphthacene-(1-, 2-, 5-)yl, and perylene, a fused pentacyclic aryl. -(1-, 2-, 3-)yl, pentacene-(1-, 2-, 5-, 6-)yl, etc. can be done.

[0720] The "heteroaryl" in "optionally substituted heteroaryl" includes, for example, carbonyl groups. Heteroaryl having 2 to 30 carbon atoms is exemplified, and heteroaryl having 2 to 25 carbon atoms is preferred. Heteroaryl having 2 to 20 carbon atoms is more preferred, and heteroaryl having 2 to 15 carbon atoms is preferred. Heteroaryl having 2 to 10 carbon atoms is more preferred, and heteroaryl having 2 to 10 carbon atoms is particularly preferred. Examples of the ring-constituting atom include a hetero atom selected from oxygen, sulfur, and nitrogen in addition to carbon. Examples include heterocycles containing 1 to 5 aryl atoms.

[0721] Specific examples of heteroaryl include furyl, thienyl, pyrrolyl, and oxazolidinyl. isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, pyrazolyl, oxazolyl thiadiazolyl, furazanyl, thiadiazolyl, triazolyl, tetrazolyl, pyridyl, Pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, benzofuranyl, isobenzo Furanyl, benzo[b]thienyl, indolyl, isoindolyl, 1H-indazolyl, Benzimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl quinolyl, isoquinolyl, cinnolyl, quinazolyl, quinoxalinyl, phthalazinyl , naphthyridinyl, purinyl, pteridinyl, carbazolyl, acridinyl, fenoxa dinyl, phenothiazinyl, phenazinyl, phenoxathiinyl, thianthrenyl, in Examples include dolizinyl.

[0722] The aryl and heteroaryl may be substituted, and may each be, for example, any of the above. The aryl and heteroaryl may be substituted.

[0723] Specific examples of the pyrimidine derivative include the following compounds: [ka]

[0724] This pyrimidine derivative can be produced using known raw materials and known synthesis methods.

[0725] <Carbazole derivatives> The carbazole derivative is, for example, a compound represented by the following formula (ETM-9), or It is a polymer formed by multiple bonds such as single bonds. Details are described in U.S. Patent Publication No. 2014 / 0197386. It has been done. [ka]

[0726] Ar each independently represents an optionally substituted aryl or an optionally substituted Each n is independently an integer of 0 to 4, preferably It is an integer of 0 to 3, and more preferably 0 or 1.

[0727] The "aryl" in the "optionally substituted aryl" includes, for example, an aryl having 6 to 30 carbon atoms. The aryl having 6 to 24 carbon atoms is preferable, and the aryl having 6 to 24 carbon atoms is more preferable. The aryl group preferably has from 1 to 20 carbon atoms, and more preferably has from 6 to 12 carbon atoms.

[0728] Specific examples of "aryl" include phenyl, which is a monocyclic aryl, and phenyl, which is a bicyclic aryl. (2-, 3-, 4-) biphenylyl, fused bicyclic aryl, (1-, 2-) naphthyl tricyclic aryl terphenylyl (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 p-terphenyl-2-yl, p-terphenyl-3-yl, p-terphenyl-4-yl), fused triphenyl Aryl ring systems, such as acenaphthylene-(1-, 3-, 4-, 5-)yl, fluorene- (1-,2-,3-,4-,9-)yl, phenalen-(1-,2-)yl, (1-,2 -, 3-, 4-, 9-)phenanthryl, tetracyclic aryl quaterphenylyl (5 '-Phenyl-m-terphenyl-2-yl, 5'-phenyl-m-terphenyl-3- yl, 5'-phenyl-m-terphenyl-4-yl, m-quaterphenylyl), condensed Tetracyclic aryls such as triphenylen-(1-,2-)yl and pyrene-(1-,2-,4 -)yl, naphthacene-(1-, 2-, 5-)yl, and perylene, a fused pentacyclic aryl. -(1-, 2-, 3-)yl, pentacene-(1-, 2-, 5-, 6-)yl, etc. can be done.

[0729] The "heteroaryl" in "optionally substituted heteroaryl" includes, for example, carbonyl groups. Heteroaryl having 2 to 30 carbon atoms is exemplified, and heteroaryl having 2 to 25 carbon atoms is preferred. Heteroaryl having 2 to 20 carbon atoms is more preferred, and heteroaryl having 2 to 15 carbon atoms is preferred. Heteroaryl having 2 to 10 carbon atoms is more preferred, and heteroaryl having 2 to 10 carbon atoms is particularly preferred. Examples of the ring-constituting atom include a hetero atom selected from oxygen, sulfur, and nitrogen in addition to carbon. Examples include heterocycles containing 1 to 5 aryl atoms.

[0730] Specific examples of heteroaryl include furyl, thienyl, pyrrolyl, and oxazolidinyl. isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, pyrazolyl, oxazolyl thiadiazolyl, furazanyl, thiadiazolyl, triazolyl, tetrazolyl, pyridyl, Pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, benzofuranyl, isobenzo Furanyl, benzo[b]thienyl, indolyl, isoindolyl, 1H-indazolyl, Benzimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl quinolyl, isoquinolyl, cinnolyl, quinazolyl, quinoxalinyl, phthalazinyl , naphthyridinyl, purinyl, pteridinyl, carbazolyl, acridinyl, fenoxa dinyl, phenothiazinyl, phenazinyl, phenoxathiinyl, thianthrenyl, in Examples include dolizinyl.

[0731] The aryl and heteroaryl may be substituted, and may each be, for example, any of the above. The aryl and heteroaryl may be substituted.

[0732] The carbazole derivative is a compound represented by the above formula (ETM-9) that is bonded by multiple bonds such as single bonds. In this case, in addition to the single bond, an aryl ring (preferably a polyvalent Benzene ring, naphthalene ring, anthracene ring, fluorene ring, benzofluorene ring, phen The rings may be bonded together via a naphthylene ring, a naphthylene ring, a phenanthrene ring, or a triphenylene ring).

[0733] Specific examples of the carbazole derivative include the following compounds: [ka]

[0734] This carbazole derivative can be produced using known raw materials and known synthesis methods. .

[0735] <Triazine derivatives> The triazine derivative is, for example, a compound represented by the following formula (ETM-10), and is preferably The compound is represented by the following formula (ETM-10-1). This is described in Publication No. 6013. [ka]

[0736] Ar each independently represents an optionally substituted aryl or an optionally substituted n is an integer of 1 to 3, preferably 2 or 3.

[0737] The "aryl" in the "optionally substituted aryl" includes, for example, an aryl having 6 to 30 carbon atoms. The aryl having 6 to 24 carbon atoms is preferable, and the aryl having 6 to 24 carbon atoms is more preferable. The aryl group preferably has from 1 to 20 carbon atoms, and more preferably has from 6 to 12 carbon atoms.

[0738] Specific examples of "aryl" include phenyl, which is a monocyclic aryl, and phenyl, which is a bicyclic aryl. (2-, 3-, 4-) biphenylyl, fused bicyclic aryl, (1-, 2-) naphthyl tricyclic aryl terphenylyl (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 p-terphenyl-2-yl, p-terphenyl-3-yl, p-terphenyl-4-yl), fused triphenyl Aryl ring systems, such as acenaphthylene-(1-, 3-, 4-, 5-)yl, fluorene- (1-,2-,3-,4-,9-)yl, phenalen-(1-,2-)yl, (1-,2 -, 3-, 4-, 9-)phenanthryl, tetracyclic aryl quaterphenylyl (5 '-Phenyl-m-terphenyl-2-yl, 5'-phenyl-m-terphenyl-3- yl, 5'-phenyl-m-terphenyl-4-yl, m-quaterphenylyl), condensed Tetracyclic aryls such as triphenylen-(1-,2-)yl and pyrene-(1-,2-,4 -)yl, naphthacene-(1-, 2-, 5-)yl, and perylene, a fused pentacyclic aryl. -(1-, 2-, 3-)yl, pentacene-(1-, 2-, 5-, 6-)yl, etc. can be done.

[0739] The "heteroaryl" in "optionally substituted heteroaryl" includes, for example, carbonyl groups. Heteroaryl having 2 to 30 carbon atoms is exemplified, and heteroaryl having 2 to 25 carbon atoms is preferred. Heteroaryl having 2 to 20 carbon atoms is more preferred, and heteroaryl having 2 to 15 carbon atoms is preferred. Heteroaryl having 2 to 10 carbon atoms is more preferred, and heteroaryl having 2 to 10 carbon atoms is particularly preferred. Examples of the ring-constituting atom include a hetero atom selected from oxygen, sulfur, and nitrogen in addition to carbon. Examples include heterocycles containing 1 to 5 aryl atoms.

[0740] Specific examples of heteroaryl include furyl, thienyl, pyrrolyl, and oxazolidinyl. isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, pyrazolyl, oxazolyl thiadiazolyl, furazanyl, thiadiazolyl, triazolyl, tetrazolyl, pyridyl, Pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, benzofuranyl, isobenzo Furanyl, benzo[b]thienyl, indolyl, isoindolyl, 1H-indazolyl, Benzimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl quinolyl, isoquinolyl, cinnolyl, quinazolyl, quinoxalinyl, phthalazinyl , naphthyridinyl, purinyl, pteridinyl, carbazolyl, acridinyl, fenoxa dinyl, phenothiazinyl, phenazinyl, phenoxathiinyl, thianthrenyl, in Examples include dolizinyl.

[0741] The aryl and heteroaryl may be substituted, and may each be, for example, any of the above. The aryl and heteroaryl may be substituted.

[0742] Specific examples of the triazine derivative include the following compounds: [ka]

[0743] This triazine derivative can be produced using known raw materials and known synthesis methods.

[0744] <Benzimidazole derivatives> The benzimidazole derivative is, for example, a compound represented by the following formula (ETM-11): . [ka]

[0745] φ is an n-valent aryl ring (preferably an n-valent benzene ring, naphthalene ring, anthracene ring, ring, fluorene ring, benzofluorene ring, phenalene ring, phenanthrene ring or trifluorene ring a phenylene ring), n is an integer of 1 to 4, and the "benzimidazole-based substituent" is The "pyriferous" in formula (ETM-2), formula (ETM-2-1) and formula (ETM-2-2) It is a substituent in which the pyridyl group in the "pyridyl-based substituent" is replaced with a benzimidazole group, At least one hydrogen atom in the benzimidazole derivative may be replaced by deuterium. In the structural formula below, * indicates the bond position. [ka]

[0746] R in the benzimidazole group 11 is hydrogen, alkyl with 1 to 24 carbon atoms, carbon cycloalkyl having 3 to 12 carbon atoms or aryl having 6 to 30 carbon atoms, 2-1) and R in Equation (ETM-2-2) 11 The explanation can be cited.

[0747] φ is preferably an anthracene ring or a fluorene ring, and in this case, The structure can be explained by referring to the explanation of the above formula (ETM-2-1) or formula (ETM-2-2). R in each formula 11 ~R 18 is the above formula (ETM-2-1) or formula (ETM-2-2) The explanation in the above formula (ETM-2-1) or formula (ETM- 2-2) is explained as a form in which two pyridine-based substituents are bonded, but these are When replacing both pyridine-based substituents with benzimidazole-based substituents, It may be replaced by an azole-based substituent (i.e., n=2), or any one of the pyridine-based substituents. The substituent is replaced with a benzimidazole-based substituent and the other pyridine-based substituent is replaced with R 11 ~R 1 8 (i.e., n=1). Furthermore, for example, in the above formula (ETM-2-1), R in 11 ~R 18 At least one of the groups is replaced with a benzimidazole-based substituent to form a "pi Lysine-based substituents" R 11 ~R 18 may be replaced with .

[0748] Specific examples of the benzimidazole derivative include 1-phenyl-2-(4-( 10-Phenylanthracen-9-yl)phenyl)-1H-benzo[d]imidazole , 2-(4-(10-(naphthalen-2-yl)anthracen-9-yl)phenyl)- 1-phenyl-1H-benzo[d]imidazole, 2-(3-(10-(naphthalene-2 -yl)anthracen-9-yl)phenyl)-1-phenyl-1H-benzo[d]imide dazole, 5-(10-(naphthalen-2-yl)anthracen-9-yl)-1,2- Diphenyl-1H-benzo[d]imidazole, 1-(4-(10-(naphthalene-2- (yl)anthracen-9-yl)phenyl)-2-phenyl-1H-benzo[d]imida 2-(4-(9,10-di(naphthalen-2-yl)anthracen-2-yl)azole phenyl)-1-phenyl-1H-benzo[d]imidazole, 1-(4-(9,10- Di(naphthalen-2-yl)anthracen-2-yl)phenyl)-2-phenyl-1H -benzo[d]imidazole, 5-(9,10-di(naphthalen-2-yl)anthracene) (2-phenyl-1H-benzo[d]imidazole) do. [ka]

[0749] This benzimidazole derivative can be produced using known raw materials and known synthesis methods. can.

[0750] <Phenanthroline derivatives> The phenanthroline derivative is, for example, a compound represented by the following formula (ETM-12) or the formula (ETM-12- 1), the details of which are described in WO 2006 / 021982. [ka]

[0751] φ is an n-valent aryl ring (preferably an n-valent benzene ring, naphthalene ring, anthracene ring, ring, fluorene ring, benzofluorene ring, phenalene ring, phenanthrene ring or trifluorene ring phenylene ring), and n is an integer of 1 to 4.

[0752] R in each formula 11 ~R 18 are each independently hydrogen, alkyl (preferably having 1 to 10 carbon atoms), 24 alkyl), cycloalkyl (preferably cycloalkyl having 3 to 12 carbon atoms) or is an aryl (preferably an aryl having 6 to 30 carbon atoms). 2-1) R 11 ~R 18 Either of these bonds to φ, an aryl ring.

[0753] At least one hydrogen atom in each phenanthroline derivative is replaced with a deuterium atom. good.

[0754] R 11 ~R 18The alkyl, cycloalkyl and aryl in the formula ( R in ETM-2 11 ~R 18 The explanation of the above can be cited. In addition to the above examples, the following structural formulas are also available. In the structural formulas below, R represents Independently, hydrogen, methyl, ethyl, isopropyl, cyclohexyl, phenyl, 1-naphthyl, The aryl group is 2-naphthyl, biphenylyl, or terphenylyl. * indicates the bond position. [ka]

[0755] Specific examples of the phenanthroline derivative include 4,7-diphenyl-1,10 -phenanthroline, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline Phosphorus, 9,10-di(1,10-phenanthrolin-2-yl)anthracene, 2,6- Di(1,10-phenanthrolin-5-yl)pyridine, 1,3,5-tri(1,10- phenanthrolin-5-yl)benzene, 9,9'-difluoro-bi(1,10-phenanthroline-5-yl)benzene 1,3-bis(2-phenyl-1,10-furan-5-yl) phenanthroline-9-yl)benzene and compounds represented by the following structural formula: [ka]

[0756] This phenanthroline derivative can be produced using known raw materials and known synthesis methods. Cut.

[0757] <Quinolinol-based metal complexes> The quinolinol metal complex is, for example, a compound represented by the following general formula (ETM-13): do. [ka] In the formula, R 1 ~R 6 are each independently hydrogen, fluorine, alkyl, cycloalkyl, aralkyl, alkenyl, cyano, alkoxy, or aryl; M is Li, Al, It is Ga, Be or Zn, and n is an integer of 1 to 3.

[0758] Specific examples of quinolinol-based metal complexes include 8-quinolinol lithium and tris(8- Tris(4-methyl-8-quinolinolato)aluminum, Tris(4-methyl-8-quinolinolato)aluminum aluminum, tris(5-methyl-8-quinolinolato)aluminum, tris(3,4-dimethyl Tris(4,5-dimethyl-8-quinolinolate)aluminum, tris(4,5-dimethyl-8-quinolinolate)aluminum tris(4,6-dimethyl-8-quinolinolato)aluminum, tris(4,6-dimethyl-8-quinolinolato)aluminum, Bis(2-methyl-8-quinolinolato)(phenolato)aluminum, bis(2-methyl Bis(2-methyl-8-quinolinolato)(2-methylphenolato)aluminum -8-quinolinolato)(3-methylphenolato)aluminum, bis(2-methyl- 8-quinolinolato)(4-methylphenolato)aluminum, bis(2-methyl-8 -quinolinolato)(2-phenylphenolato)aluminum, bis(2-methyl-8 -quinolinolato)(3-phenylphenolato)aluminum, bis(2-methyl-8 -quinolinolato)(4-phenylphenolato)aluminum, bis(2-methyl-8 -quinolinolato)(2,3-dimethylphenolato)aluminum, bis(2-methyl -8-quinolinolato)(2,6-dimethylphenolato)aluminum, bis(2-methyl- bis(2-methyl-8-quinolinolato)(3,4-dimethylphenolato)aluminum -methyl-8-quinolinolato)(3,5-dimethylphenolato)aluminum, bis (2-methyl-8-quinolinolate)(3,5-di-t-butylphenolate)aluminium ammonium, bis(2-methyl-8-quinolinolato)(2,6-diphenylphenolato)a Aluminum, bis(2-methyl-8-quinolinolato)(2,4,6-triphenylphenyl) Aluminum bis(2-methyl-8-quinolinolate)(2,4,6-trimethyl-8-quinolinolate) Methylphenolate)aluminum, bis(2-methyl-8-quinolinolate)(2,4 ,5,6-tetramethylphenolate)aluminum, bis(2-methyl-8-quinolinol) bis(2-methyl-8-quinolinolate)(1-naphtholate)aluminum, bis(2-methyl-8-quinolinolate) (2-naphtholato)aluminum, bis(2,4-dimethyl-8-quinolinolato)( 2-phenylphenolate)aluminum, bis(2,4-dimethyl-8-quinolinol) bis(2,4-dimethyl-8-quinolinyl)aluminum(triphenylphenolate) bis(2,4-dimethyl-8-)(4-phenylphenolate)aluminum Quinolinolato)(3,5-dimethylphenolato)aluminum, bis(2,4-dimethylphenolato)aluminum (3,5-di-t-butylphenolate)aluminum, bis(methyl-8-quinolinolato) Bis(2-methyl-8-quinolinolato)aluminum-μ-oxo-bis(2-methyl- 8-quinolinolato)aluminum, bis(2,4-dimethyl-8-quinolinolato)aluminum Aluminum-μ-oxo-bis(2,4-dimethyl-8-quinolinolato)aluminum , bis(2-methyl-4-ethyl-8-quinolinolato)aluminum-μ-oxo-bi Bis(2-methyl-4-ethyl-8-quinolinolato)aluminum, Bis(2-methyl- 4-Methoxy-8-quinolinolato)aluminum-μ-oxo-bis(2-methyl-4 -Methoxy-8-quinolinolato)aluminum, bis(2-methyl-5-cyano-8- Quinolinolato)aluminum-μ-oxo-bis(2-methyl-5-cyano-8-quino Aluminum linoleate, bis(2-methyl-5-trifluoromethyl-8-quinolinol) bis(2-methyl-5-trifluoromethyl-8-methyl-2-oxo-2-methyl-5-trifluoromethyl-4-methyl-2-methyl-2-oxo ... Quinolinolate)aluminum, Bis(10-hydroxybenzo[h]quinoline)beryl Examples include Umu.

[0759] This quinolinol-based metal complex can be produced using known raw materials and known synthesis methods. Cut.

[0760] <Thiazole Derivatives and Benzothiazole Derivatives> The thiazole derivative is, for example, a compound represented by the following formula (ETM-14-1). [ka] The benzothiazole derivative is, for example, a compound represented by the following formula (ETM-14-2): do. [ka]

[0761] In each formula, φ represents an n-valent aryl ring (preferably an n-valent benzene ring, naphthalene ring, a helical ring, a fluorene ring, a benzofluorene ring, a phenalene ring, a phenanthrene ring, or triphenylene ring), and n is an integer of 1 to 4. The "zothiazole-based substituent" is a group represented by the above formula (ETM-2), formula (ETM-2-1) and formula (E The pyridyl group in the "pyridine-based substituent" in TM-2-2) is the following thiazole group or It is a substituent substituted for the benzothiazole group, and is used in thiazole derivatives and benzothiazo At least one hydrogen atom in the aryl derivative may be substituted with a deuterium atom. The * in the figure indicates the bond position. [ka]

[0762] φ is preferably an anthracene ring or a fluorene ring, and in this case, The structure can be explained by referring to the explanation of the above formula (ETM-2-1) or formula (ETM-2-2). R in each formula 11 ~R 18 is the above formula (ETM-2-1) or formula (ETM-2-2) The explanation in the above formula (ETM-2-1) or formula (ETM- 2-2) is explained as a form in which two pyridine-based substituents are bonded, but these are When replacing with an azole-based substituent (or a benzothiazole-based substituent), both pyridines Even if the thiazole-based substituent is replaced with a thiazole-based substituent (or a benzothiazole-based substituen...

Claims

1. A polycyclic aromatic compound represented by the following general formula (1), or a structure represented by the following general formula (1): A polymer of polycyclic aromatic compounds with multiple structures. 【Chemistry 1】 (In the above formula (1), Ring A, ring B and ring C are each independently an aryl ring or a heteroaryl ring. At least one hydrogen atom in these rings may be substituted. At least one hydrogen atom in at least one of the rings B and C is represented by the above formula (Am). In the above formula (Am), Ar is substituted with a group represented by １ and Ar ２ Is that Each independently is an aryl or heteroaryl, At least one hydrogen atom in Ar may be substituted. １ and Ar ２ is a single bond Alternatively, the group represented by the formula (Am) may be bonded via a linking group. replacing hydrogen in the ring or C ring, Ring B and ring C may be bonded via a linking group; Y １ is B, P, P=O, P=S, Al, Ga, As, Si-R or Ge-R R of the Si—R and Ge—R is aryl, alkyl or cycloalkyl. 、 X １ and X ２ are each independently >O, >N-R, >Si(-R) ２ , > C (- R) ２ , >S or >Se, and R of the >N-R is an optionally substituted aryl. (excluding amino groups as substituents), optionally substituted heteroaryl, and the >Si is an optionally substituted alkyl or an optionally substituted cycloalkyl. (-R) ２ R is an optionally substituted aryl, an optionally substituted heteroaryl, aryl, optionally substituted alkyl or optionally substituted cycloalkyl; Above>C(-R) ２ R is hydrogen, optionally substituted aryl, optionally substituted Heteroaryl, optionally substituted alkyl or optionally substituted cycloalkyl and the above-mentioned >N-R, >Si(-R) ２ and >C(-R) ２ At least R in the other embodiment is a linking group or a single bond to at least one of the A ring, the B ring and the C ring. and In the compound or structure represented by formula (1), the A ring, the B ring, the C ring, the aryl and the heterocyclic ring are At least one of the heteroaryls may be fused to at least one cycloalkane. At least one hydrogen atom in the cycloalkane may be substituted. At least one -CH in the cycloalkane ２ - may be replaced by -O-; and, At least one hydrogen atom in the compound or structure represented by formula (1) is deuterium, sialic acid, or aryl. may be substituted with aryl or halogen.

2. The polycyclic aromatic compound according to claim 1, which is represented by the following general formula (1A): A multimer of the polycyclic aromatic compound according to claim 1 having a plurality of structures represented by (1A). 【Chemistry 2】 (In the above formula (1A), Ring A, ring B and ring C are each independently an aryl ring or a heteroaryl ring. At least one hydrogen atom in these rings may be substituted. At least one hydrogen atom in at least one of the rings B and C is represented by the above formula (Am). In the above formula (Am), Ar is substituted with a group represented by １ is biphenylyl , Ar ２ is aryl (except biphenylyl) or heteroaryl, and the biphenyl is At least one hydrogen in the phenylyl, aryl or heteroaryl is an alkyl or or cycloalkyl, and the group represented by the above formula (Am) may be Substituting for hydrogen in ring B or ring C; Ring B and ring C may be bonded via a linking group; Y １ is B, P, P=O, P=S, Al, Ga, As, Si-R or Ge-R R of the Si—R and Ge—R is aryl, alkyl or cycloalkyl. 、 X １ and X ２ are each independently >O, >N-R, >Si(-R) ２ , > C (- R) ２ , >S or >Se, and R of the >N-R is an optionally substituted aryl. (excluding amino groups as substituents), optionally substituted heteroaryl, and the >Si is an optionally substituted alkyl or an optionally substituted cycloalkyl. (-R) ２ R is an optionally substituted aryl, an optionally substituted heteroaryl, aryl, optionally substituted alkyl or optionally substituted cycloalkyl; Above>C(-R) ２ R is hydrogen, optionally substituted aryl, optionally substituted Heteroaryl, optionally substituted alkyl or optionally substituted cycloalkyl and the above-mentioned >N-R, >Si(-R) ２ and >C(-R) ２ At least R in the other embodiment is a linking group or a single bond to at least one of the A ring, the B ring and the C ring. and In the compound or structure represented by formula (1A), the A ring, the B ring, the C ring, the aryl and At least one of the heteroaryls is fused to at least one cycloalkane. At least one hydrogen atom in the cycloalkane may be substituted. At least one -CH in the cycloalkane ２ - may be replaced by -O- ,and, At least one hydrogen atom in the compound or structure represented by formula (1A) is replaced by a deuterium atom, a silyl atom, or a cyclohexane atom. may be substituted with an anion or halogen.

3. In the above formula (1A), Ring A, ring B and ring C are each independently an aryl ring or a heteroaryl ring. At least one hydrogen atom in these rings is replaced by a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino, substituted or is an unsubstituted diheteroarylamino, a substituted or unsubstituted arylheteroarylamino Substituted or unsubstituted diarylboryl (two aryls are connected via a single bond or a linking group) may be bonded to one another), substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl aryloxy, substituted or unsubstituted aryloxy, Alternatively, these rings may be substituted with substituted silyl, and these rings may be substituted with Y １ , X １ and X ２ A 5- or 6-membered ring sharing a bond with the central fused bicyclic structure of the above formula (1A) having At least one hydrogen atom in at least one of the rings B and C is represented by the above formula (Am). is substituted with a group represented by The B and C rings are >O, >N-R, >Si(-R) ２ , >C(-R) ２ , > S or >Se may be bonded through the >N-R and >Si(-R) ２ The R in aryl, aryls ... Heteroaryl, alkyl or cycloalkyl optionally substituted; chloroalkyl, and the >C(-R) ２ R is hydrogen, alkyl or cycloalkyl. substituted with aryl, alkyl or cycloalkyl, and the above-mentioned >N-R, > Si(-R) ２ and >C(-R) ２ At least one of R is -O-, -S-, -C(-R) ２ or a single bond to at least one of the rings B and C; The -C(-R) ２ R in - is hydrogen, alkyl or cycloalkyl. can be, Y １ is B, P, P=O, P=S, Al, Ga, As, Si-R or Ge-R R of the Si—R and Ge—R is aryl, alkyl or cycloalkyl. 、 X １ and X ２ are each independently >O, >N-R, >Si(-R) ２ , > C (- R) ２ , >S or >Se, and the >N-R and >Si(-R) ２ The R in each aryl, alkyl, or cycloalkyl, each of which may be substituted with alkyl or cycloalkyl; Heteroaryl, alkyl or cycloalkyl optionally substituted. is alkyl, and the >C(-R) ２ R is hydrogen, alkyl or cycloalkyl aryl, alkyl or cycloalkyl, Heteroaryl, alkyl or cycloalkyl are also suitable, and the above >N-R, >S i(-R) ２ and >C(-R) ２ At least one of R is -O-, -S-, - C(-R) ２ or a single bond to at least one of the rings A, B and C; may be bonded, and the -C(-R) ２ R in - is hydrogen, alkyl or cycloalkyl. It is In the compound or structure represented by formula (1A), the A ring, the B ring, the C ring, the aryl and At least one of the heteroaryls is fused to at least one cycloalkane. At least one hydrogen atom in the cycloalkane may be substituted. At least one -CH in the cycloalkane ２ - may be replaced by -O- 、 In the case of a polymer, a dimer having two or three structures represented by the general formula (1A) or is a trimer, and At least one hydrogen atom in the compound or structure represented by formula (1A) is replaced by a deuterium atom, a silyl atom, or a cyclohexane atom. may be substituted with an anion or halogen; The polycyclic aromatic compound or a multimer thereof according to claim 2.

4. The polycyclic aromatic compound according to claim 2, which is represented by the following general formula (2A): 【Chemistry 3】 (In the above formula (2A), In the a ring, the b ring, and the c ring, any "-C(-R)=" (wherein R is represented by the formula (2A) R in １ ~R １１ ) may be replaced with "-N=", and any "-C(-R )=C(-R)- (where R is R in formula (2A) １ ~R １１ (-N(-R )-", "-O-", or "-S-", and the "-N(-R) R in -" is aryl, alkyl, or cycloalkyl; R １ ~R １１ are each independently hydrogen, aryl, heteroaryl, diaryla amino, diheteroarylamino, arylheteroarylamino, diarylboryl (2 the aryl may be bonded via a single bond or a linking group, alkyl, cycloalkyl alkyl, alkoxy, aryloxy, triarylsilyl, trialkylsilyl, triaryl ... Cycloalkylsilyl, dialkylcycloalkylsilyl or alkyldicycloalkyl and aryl, aryl, heteroaryl, may be substituted with alkyl or cycloalkyl; １ ~R １１ Next to my house Adjacent groups are bonded to each other to form an aryl or heteroaryl ring together with the a, b or c ring. At least one hydrogen atom in the ring formed may be selected from the group consisting of aryl, heterocyclic, Diaryl, diarylamino, diheteroarylamino, arylheteroarylamino Diarylboryl (two aryls may be bonded via a single bond or a linking group) (ii), alkyl, cycloalkyl, alkoxy, aryloxy, triarylsilyl, Trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl or may be substituted with alkyldicycloalkylsilyl, and at least One hydrogen is replaced by aryl, heteroaryl, alkyl, or cycloalkyl. It's okay to be there, R ４ ~R １１ At least one of the groups represented by formula (Am) is a group represented by formula (Am) above, and / or in an aryl ring or heteroaryl ring formed together with the ring b or ring c At least one hydrogen atom of the formula (Am) is substituted with a group represented by the formula (Am), R ７ and R ８ is bonded to >O, >N-R, >Si(-R) ２ , >C(-R) ２ , > S or >Se, and the >N-R and >Si(-R) ２ The R in each independently being an aryl having 6 to 12 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, is an alkyl having 3 to 6 carbon atoms or a cycloalkyl having 3 to 14 carbon atoms, ２ R is hydrogen, an aryl having 6 to 12 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, or cycloalkyl having 3 to 14 carbon atoms, and the above-mentioned >N-R, >Si (-R) ２ and >C(-R) ２ At least one of R is -O-, -S-, -C (-R) ２ or a single bond is bonded to at least one of the rings b and c; The -C(-R) ２ - R is an alkyl group having 1 to 6 carbon atoms or an alkyl group having 3 to 14 carbon atoms. is a cycloalkyl of Y １ is B, P, P=O, P=S, Al, Ga, As, Si-R or Ge-R R in the Si-R and Ge-R is an aryl having 6 to 12 carbon atoms, an aryl having 1 to 6 carbon atoms, alkyl or cycloalkyl having 3 to 14 carbon atoms; X １ and X ２ are each independently >O, >N-R, >Si(-R) ２ , > C (- R) ２ , >S or >Se, and the >N-R and >Si(-R) ２ The R in each each independently being an aryl having 6 to 12 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, 6 alkyl or cycloalkyl having 3 to 14 carbon atoms, and the >C(-R) ２ The R in , hydrogen, aryl having 6 to 12 carbon atoms, heteroaryl having 2 to 15 carbon atoms, alkyl or cycloalkyl having 3 to 14 carbon atoms, and the above-mentioned >N-R, >Si( -R) ２ and >C(-R) ２ At least one of R is -O-, -S-, -C( -R) ２ or bonded to at least one of the ring a, ring b and ring c via a single bond; The -C(-R) ２ R in - is an alkyl group having 1 to 6 carbon atoms or cycloalkyl of 14; In the compound represented by formula (2A), the ring a, the ring b, the ring c, and the formed At least one of the ring, the aryl and the heteroaryl has 3 to 24 carbon atoms. It may be condensed with at least one cycloalkane, At least one hydrogen atom is an aryl having 6 to 30 carbon atoms or a heteroaryl having 2 to 30 carbon atoms. , and may be substituted with alkyl having 1 to 24 carbon atoms or cycloalkyl having 3 to 24 carbon atoms. Preferably, at least one -CH in the cycloalkane ２ - is replaced by -O- And, At least one hydrogen atom in the compound represented by formula (2A) is deuterium, cyano or It may be substituted with halogen.

5. In the above formula (2A), In the a ring, the b ring, and the c ring, any "-C(-R)=" (wherein R is represented by the formula (2A) Inside R １ ~R １１ ) may be replaced with "-N=", and any "-C(-R )=C(-R)- (where R is R in formula (2A) １ ~R １１ (-N(-R The "-N(-R)-" may be replaced with "-O-" or "-S-" and the "-N(-R)-" may be replaced with "-N(-R)-" or "-O-" or "-S-". R in "-" is an aryl having 6 to 12 carbon atoms, an alkyl having 1 to 6 carbon atoms, or a cyclic group having 3 to 1 4 cycloalkyl; R １ ~R １１ each independently represents a hydrogen atom, an aryl group having 6 to 30 carbon atoms, 0 heteroaryl, diarylamino (wherein aryl is an aryl having 6 to 12 carbon atoms) , diarylboryl (wherein the aryl is an aryl having 6 to 12 carbon atoms, and two aryls may be bonded via a single bond or a linking group), alkyl having 1 to 24 carbon atoms, Cycloalkyl with 3 to 24 prime numbers, triarylsilyl (wherein aryl has 6 to 12 carbon atoms) aryl), or trialkylsilyl (wherein the alkyl has 1 to 6 carbon atoms) and R １ ~R １１ adjacent groups are bonded to ring a, ring b, or ring c. Together they form an aryl ring having 9 to 16 carbon atoms or a heteroaryl ring having 6 to 15 carbon atoms. At least one hydrogen atom in the formed ring may be an aryl having 6 to 10 carbon atoms, Alkyl having 1 to 12 carbon atoms, cycloalkyl having 3 to 16 carbon atoms, triarylsilyl (or (Aryl is an aryl having 6 to 12 carbon atoms), or trialkylsilyl (wherein alkyl is may be substituted with alkyl having 1 to 5 carbon atoms; R ４ ~R １１ At least one of the groups represented by formula (Am) is a group represented by formula (Am) above, and / or in an aryl ring or heteroaryl ring formed together with the ring b or ring c At least one hydrogen atom of the formula (Am) is substituted with a group represented by the formula (Am ) in which Ar １ is biphenylyl, Ar ２ is an aryl having 6 to 30 carbon atoms (where biphenylyl) or heteroaryl having 2 to 30 carbon atoms, At least one hydrogen atom in the aryl or heteroaryl is an aryl having 1 to 24 carbon atoms. cycloalkyl or cycloalkyl having 3 to 24 carbon atoms; R ７ and R ８ are bonded together, >O, >N-R, >C(-R) ２ Or > S R in the >N--R may be an aryl having 6 to 10 carbon atoms, an alkyl having 1 to 5 carbon atoms, or is a cycloalkyl having 5 to 10 carbon atoms, and the >C(-R) ２ R is hydrogen, carbon number 6 aryl having 1 to 10 carbon atoms, alkyl having 1 to 5 carbon atoms, or cycloalkyl having 5 to 10 carbon atoms; the law of nature, Y １ is B, P, P=O, P=S or Si-R, R of the Si-R is the number of carbon atoms 6 to 10 aryl, 1 to 5 carbon alkyl, or 5 to 10 carbon cycloalkyl can be, X １ and X ２ are each independently >O, >N-R, >C(-R) ２ Or > S R of the >N-R is an aryl having 6 to 10 carbon atoms, an alkyl having 1 to 5 carbon atoms, or is a cycloalkyl having 5 to 10 carbon atoms, and the >C(-R) ２ R is hydrogen, carbon number 6- 10 aryl, alkyl having 1 to 5 carbon atoms, or cycloalkyl having 5 to 10 carbon atoms; 、 In the compound represented by formula (2A), the ring a, the ring b, the ring c, and the formed At least one of the ring, the aryl and the heteroaryl has 3 to 20 carbon atoms. It may be condensed with at least one cycloalkane, At least one hydrogen atom is an aryl having 6 to 16 carbon atoms or a heteroaryl having 2 to 22 carbon atoms. , and may be substituted with alkyl having 1 to 12 carbon atoms or cycloalkyl having 3 to 16 carbon atoms. Well, and At least one hydrogen atom in the compound represented by formula (2A) is deuterium, cyano or optionally substituted with halogen; The polycyclic aromatic compound according to claim 4.

6. In the above formula (2A), In the a ring, the b ring, and the c ring, any "-C(-R)=" (wherein R is represented by the formula (2A) Inside R １ ~R １１ ) may be replaced with "-N=", and any "-C(-R )=C(-R)- (where R is R in formula (2A) １ ~R １１ (-N(-R )-", "-O-", or "-S-", and the "-N(-R) R in "-" is an aryl having 6 to 10 carbon atoms, an alkyl having 1 to 5 carbon atoms, or a cyclic group having 5 to 1 0 cycloalkyl; R １ ~R １１ are each independently hydrogen, an aryl having 6 to 16 carbon atoms, 0 heteroaryl, diarylamino (wherein aryl is an aryl having 6 to 10 carbon atoms) , alkyl having 1 to 12 carbon atoms or cycloalkyl having 3 to 16 carbon atoms; R ５ and R １０ At least one of the above is a group represented by the formula (Am), m) In the above, Ar １ is biphenylyl, Ar ２ Aryl (only aryl with 6 to 16 carbon atoms) (excluding biphenylyl) or heteroaryl having 2 to 20 carbon atoms, At least one hydrogen atom in the aryl, aryl or heteroaryl is an aryl having 1 to 12 carbon atoms. may be substituted by alkyl or cycloalkyl having 3 to 16 carbon atoms; R ７ and R ８ is bonded to >O, >N-R or >C(-R) ２ It is fine if it is R in the >N-R is an aryl having 6 to 10 carbon atoms, an alkyl having 1 to 5 carbon atoms, or a is a cycloalkyl having a number of 5 to 10, and the >C(-R) ２ R is hydrogen, 6 to 10 carbon atoms aryl, alkyl having 1 to 5 carbon atoms, or cycloalkyl having 5 to 10 carbon atoms; Y １ is B, P, P=O or P=S, X １ and X ２ are each independently >O, >N-R or >C(-R) ２ and R in the above >N-R is an aryl having 6 to 10 carbon atoms, an alkyl having 1 to 5 carbon atoms, or 5 to 10, and the >C(-R) ２ R is hydrogen, a compound having 6 to 10 carbon atoms aryl, alkyl having 1 to 5 carbon atoms, or cycloalkyl having 5 to 10 carbon atoms; In the compound represented by formula (2A), the ring a, the ring b, the ring c, and the At least one of the aryls having 6 to 10 carbon atoms as R in N-R is an aryl having 3 to 16 carbon atoms. may be condensed with at least one cycloalkane, At least one hydrogen atom is an alkyl group having 1 to 6 carbon atoms or a cycloalkyl group having 3 to 14 carbon atoms. and At least one hydrogen atom in the compound represented by formula (2A) is deuterium, cyano or optionally substituted with halogen; The polycyclic aromatic compound according to claim 4.

7. In the above formula (2A), R １ ~R １１ are each independently hydrogen, an aryl having 6 to 16 carbon atoms, a diaryla amino (wherein aryl is aryl having 6 to 10 carbon atoms), alkyl having 1 to 12 carbon atoms, or is a cycloalkyl having 3 to 16 carbon atoms; R ５ and R １０ At least one of the above is a group represented by the formula (Am), m) In the above, Ar １ is biphenylyl, Ar ２ Aryl having 6 to 16 carbon atoms (only (excluding biphenylyl) or heteroaryl having 2 to 20 carbon atoms, At least one hydrogen atom in the aryl, aryl or heteroaryl is an aryl having 1 to 12 carbon atoms. may be substituted by alkyl or cycloalkyl having 3 to 16 carbon atoms; Y １ is B, X １ and X ２ are both >N-R, or X １ is >N-R and X ２ Ha>O R of the >N-R is an aryl having 6 to 10 carbon atoms, an alkyl having 1 to 5 carbon atoms, or is a cycloalkyl having 5 to 10 carbon atoms; In the compound represented by formula (2A), the ring a, the ring b, the ring c, and the At least one of the aryls having 6 to 10 carbon atoms as R in N-R is an aryl having 3 to 14 carbon atoms. It may be condensed with a cycloalkane, and at least one of the cycloalkanes The hydrogen may be substituted with an alkyl having 1 to 5 carbon atoms; and At least one hydrogen atom in the compound represented by formula (2A) is deuterium or halogen. optionally substituted, The polycyclic aromatic compound according to claim 4.

8. The polycyclic aromatic compound according to claim 1, which is represented by the following general formula (2B): A multimer of the polycyclic aromatic compound according to claim 1 having a plurality of structures represented by (2B). 【Chemistry 4】 (In the above formula (2B), Any "-C(-H)=" in the a, b, and c rings is replaced with "-N=". It is okay to have R ２１ ~R ３０ each independently represents hydrogen, aryl, heteroaryl, or diaryl Amino, diheteroarylamino, arylheteroarylamino, diarylboryl ( Two aryls may be bonded via a single bond or a linking group), alkyl, cyclo Alkyl, alkoxy, aryloxy, triarylsilyl, trialkylsilyl, triarylsilyl Tricycloalkylsilyl, dialkylcycloalkylsilyl or alkyldicycloalkylsilyl and xylsilyl, in which at least one hydrogen is an aryl, heteroaryl, , optionally substituted with alkyl or cycloalkyl; R ２１ ~R ３０ Adjacent groups among these may be bonded to each other to form an aryl ring together with the d or e ring. or heteroaryl ring, and at least one of the hydrogen atoms in the ring formed may be hydrogen or heteroaryl. The element is an aryl, heteroaryl, diarylamino, diheteroarylamino, aryl arylheteroarylamino, diarylboryl (two aryls are connected via a single bond or a linking group) may be bonded to each other), alkyl, cycloalkyl, alkoxy, aryloxy, Triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylsilyl may be substituted with alkyldicycloalkylsilyl or alkyldicycloalkylsilyl, At least one hydrogen atom in each of the groups is an aryl, heteroaryl, alkyl, or cycloalkyl group. may be substituted with alkyl, R ２５ and R ２６ is bonded to >O, >N-R, >Si(-R) ２ , >C(-R) ２ , >S or >Se, and the >N-R and >Si(-R) ２ The R in each independently represents an 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, At least one hydrogen atom is an aryl having 6 to 12 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, It may be substituted by alkyl having 1 to 6 prime numbers or cycloalkyl having 3 to 14 carbon atoms, Above>C(-R) ２ R is hydrogen, an aryl having 6 to 12 carbon atoms, a heterocyclic group having 2 to 15 carbon atoms, aryl, alkyl having 1 to 6 carbon atoms, or cycloalkyl having 3 to 14 carbon atoms; At least one hydrogen atom in these groups is an aryl group having 6 to 12 carbon atoms, a heterocyclic group having 2 to 15 carbon atoms, or aryl, alkyl having 1 to 6 carbon atoms, or cycloalkyl having 3 to 14 carbon atoms; It is okay to Ra is an aryl, heteroaryl, alkyl, cycloalkyl, alkoxy, aryl, silyl, triarylsilyl, trialkylsilyl, tricycloalkylsilyl, diarylsilyl, alkylcycloalkylsilyl or alkyldicycloalkylsilyl. At least one hydrogen atom in the alkyl group is an aryl, heteroaryl, alkyl, or cycloalkyl group. may be substituted with Rb is hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino. No, arylheteroarylamino, diarylboryl (two aryls are single bond or may be bonded via a linking group), alkyl, cycloalkyl, alkoxy, aryl silyl, triarylsilyl, trialkylsilyl, tricycloalkylsilyl, diarylsilyl, alkylcycloalkylsilyl or alkyldicycloalkylsilyl. At least one hydrogen atom in the alkyl group is an aryl, heteroaryl, alkyl, or cycloalkyl group. may be substituted with Y １ is B, P, P=O, P=S, Al, Ga, As, Si-R or Ge-R R in the Si-R and Ge-R is an aryl having 6 to 12 carbon atoms, an aryl having 1 to 6 carbon atoms, alkyl or cycloalkyl having 3 to 14 carbon atoms; X １ and X ２ are each independently >O, >N-R, >Si(-R) ２ , > C (- R) ２ , >S or >Se, and the >N-R and >Si(-R) ２ The R in each each independently being an aryl having 6 to 12 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, 6 alkyl or cycloalkyl having 3 to 14 carbon atoms, One hydrogen atom is an aryl having 6 to 12 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, or may be substituted with an alkyl having 1 to 6 carbon atoms or a cycloalkyl having 3 to 14 carbon atoms; C(-R) ２ R is hydrogen, an aryl having 6 to 12 carbon atoms, or a heteroaryl having 2 to 15 carbon atoms. alkyl having 1 to 6 carbon atoms or cycloalkyl having 3 to 14 carbon atoms; At least one hydrogen atom in the formula (I) is an aryl group having 6 to 12 carbon atoms, a heteroaryl group having 2 to 15 carbon atoms, or substituted with alkyl, alkyl having 1 to 6 carbon atoms, or cycloalkyl having 3 to 14 carbon atoms. Also, the above-mentioned >N-R, >Si(-R) ２ and >C(-R) ２ At least one of In the formula, R is -O-, -S-, -C(-R) ２ or a single bond, and ring c may be bonded to at least one ring, and said -C(-R) ２ The R in - is charcoal is an alkyl group having 1 to 6 prime numbers or a cycloalkyl group having 3 to 14 carbon atoms; In the compound or structure represented by formula (2B), At least one of the d ring, the e ring, the formed ring, the aryl and the heteroaryl One of the cycloalkanes may be condensed with at least one cycloalkane having 3 to 24 carbon atoms. At least one hydrogen atom in the cycloalkane is an aryl having 6 to 30 carbon atoms, Heteroaryl having 2 to 30 carbon atoms, alkyl having 1 to 24 carbon atoms, or cycloalkyl having 3 to 24 carbon atoms. At least one of the cycloalkanes may be substituted with - CH ２ - may be replaced by -O-, and At least one hydrogen atom in the compound or structure represented by formula (2B) is deuterium, silyl may be substituted with an anion or halogen.

9. In the above formula (2B), Any "-C(-H)=" in the a, b, and c rings is replaced with "-N=". It is okay to have R ２１ ~R ３０ each independently represents a hydrogen atom, an aryl group having 6 to 30 carbon atoms, 30 heteroaryl, diarylamino (wherein aryl is an aryl having 6 to 12 carbon atoms) ), diarylboryl (wherein the aryl is an aryl having 6 to 12 carbon atoms, and two aryls the alkyl group may be bonded via a single bond or a linking group), an alkyl group having 1 to 24 carbon atoms, Cycloalkyl having 3 to 24 carbon atoms, triarylsilyl (wherein aryl has 6 to 1 carbon atoms) 2 aryl), or trialkylsilyl (wherein the alkyl has 1 to 6 carbon atoms) ) and R ２１ ~R ３０ Adjacent groups among these are bonded to each other to form a ring having 9 to 1 carbon atoms together with the d ring or the e ring. 6 aryl ring or 6 to 15 carbon heteroaryl ring may be formed. At least one hydrogen atom in the ring is an aryl having 6 to 30 carbon atoms, Heteroaryl, diarylamino (wherein aryl has 6 to 12 carbon atoms), Arylboryl (wherein the aryl is an aryl having 6 to 12 carbon atoms, and the two aryls are may be bonded via a single bond or a linking group), alkyl having 1 to 24 carbon atoms, Cycloalkyl having 3 to 24 carbon atoms, triarylsilyl (wherein aryl is an alkyl group having 6 to 12 carbon atoms) silyl), or trialkylsilyl (wherein alkyl has 1 to 6 carbon atoms). It may be replaced, R ２５ and R ２６ is bonded to >O, >N-R, or >C(-R) ２ , and R in the >N-R may each independently be an 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. At least one hydrogen atom in these is an 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. The >C(-R) may be substituted with alkyl. ２ R is hydrogen, aryl with 6 to 12 carbon atoms aryl, heteroaryl having 2 to 15 carbon atoms, alkyl having 1 to 6 carbon atoms or alkyl having 3 to 1 carbon atoms 4 cycloalkyl, in which at least one hydrogen is a cycloalkyl having 6 to 12 carbon atoms. Aryl, heteroaryl having 2 to 15 carbon atoms, alkyl having 1 to 6 carbon atoms or alkyl having 3 to 6 carbon atoms. 14, optionally substituted with cycloalkyl; Ra is an aryl group having 6 to 30 carbon atoms, an alkyl group having 1 to 24 carbon atoms, a silyl group having 3 to 24 carbon atoms, chloroalkyl, triarylsilyl (wherein aryl has 6 to 12 carbon atoms), or or trialkylsilyl (wherein alkyl has 1 to 6 carbon atoms), At least one hydrogen atom in the alkyl group is selected from the group consisting of alkyl having 1 to 24 carbon atoms and alkyl having 3 to 24 carbon atoms. optionally substituted with cycloalkyl; Rb is hydrogen, aryl having 6 to 30 carbon atoms, diarylamino (wherein aryl is a carbon atom). aryl having 6 to 12 carbon atoms), diarylboryl (aryl having 6 to 12 carbon atoms) wherein the two aryls may be bonded via a single bond or a linking group), Alkyl having 1 to 24 carbon atoms, cycloalkyl having 3 to 24 carbon atoms, triarylsilyl (wherein aryl is aryl having 6 to 12 carbon atoms), or trialkylsilyl (wherein alkyl is At least one hydrogen atom in the aryl is an alkyl group having 1 to 6 carbon atoms. may be substituted by alkyl having 3 to 24 carbon atoms or cycloalkyl having 3 to 24 carbon atoms; Y １ is B, P, P=O, P=S or Si-R, R of the Si-R is the number of carbon atoms 6 to 10 aryl, 1 to 5 carbon alkyl, or 5 to 10 carbon cycloalkyl can be, X １ and X ２ are each independently >O, >N-R, >C(-R) ２ , or >S R in the >N-R is an aryl having 6 to 10 carbon atoms, an alkyl having 1 to 5 carbon atoms, or is a cycloalkyl having 5 to 10 carbon atoms, in which at least one hydrogen is Aryl having 6 to 10 prime numbers, alkyl having 1 to 5 carbon atoms, or cycloalkyl having 5 to 10 carbon atoms. may be substituted with the >C(-R) ２ R is hydrogen, aryl group having 6 to 10 carbon atoms. alkyl having 1 to 5 carbon atoms or cycloalkyl having 5 to 10 carbon atoms; At least one hydrogen atom in the alkyl group is an aryl group having 6 to 10 carbon atoms, an alkyl group having 1 to 5 carbon atoms, or may be substituted with a cycloalkyl having 5 to 10 carbon atoms; In the compound or structure represented by formula (2B), At least one of the d ring, the e ring, the formed ring, the aryl and the heteroaryl Each of the two may be condensed with at least one cycloalkane having 3 to 20 carbon atoms. At least one hydrogen atom in the cycloalkane is an aryl having 6 to 16 carbon atoms, Heteroaryl having 2 to 22 carbon atoms, alkyl having 1 to 12 carbon atoms, or cycloalkyl having 3 to 16 carbon atoms. may be substituted with chloroalkyl, and At least one hydrogen atom in the compound or structure represented by formula (2B) is deuterium, silyl may be substituted with an anion or halogen; The polycyclic aromatic compound or a multimer thereof according to claim 8.

10. In the above formula (2B), Any "-C(-H)=" in the a, b, and c rings is replaced with "-N=". It is okay to have R ２１ ~R ３０ each independently represents hydrogen, an aryl having 6 to 16 carbon atoms, or a diaryl Amino (where aryl is aryl with 6 to 10 carbon atoms), diarylboryl (where aryl The aryl is an aryl having 6 to 10 carbon atoms, and two aryls are connected via a single bond or a linking group. may be bonded to each other), alkyl having 1 to 12 carbon atoms or cycloalkyl having 3 to 16 carbon atoms It is Ra is an aryl group having 6 to 30 carbon atoms, an alkyl group having 1 to 24 carbon atoms, a silyl group having 3 to 24 carbon atoms, At least one hydrogen atom in the aryl is an aryl having 1 to 24 carbon atoms. may be substituted by alkyl or cycloalkyl having 3 to 24 carbon atoms; Rb is hydrogen, aryl having 6 to 30 carbon atoms, diarylamino (wherein aryl is a carbon atom). aryl having 6 to 12 carbon atoms), diarylboryl (aryl having 6 to 12 carbon atoms) wherein the two aryls may be bonded via a single bond or a linking group), alkyl having 1 to 24 carbon atoms or cycloalkyl having 3 to 24 carbon atoms, At least one hydrogen atom is an alkyl group having 1 to 24 carbon atoms or a cycloalkyl group having 3 to 24 carbon atoms. may be replaced by kill, Y １ is B, P, P=O or P=S, X １ and X ２ are each independently >O or >N-R, and R of the >N-R is an aryl having 6 to 10 carbon atoms, an alkyl having 1 to 5 carbon atoms, or a cycloalkyl having 5 to 10 carbon atoms. alkyl, in which at least one hydrogen is an aryl having 6 to 10 carbon atoms; It may be substituted with alkyl having 1 to 5 carbon atoms or cycloalkyl having 5 to 10 carbon atoms. 、 In the compound or structure represented by formula (2B), The ring d, the ring e, and the R of the >N-R are each an aryl having 6 to 10 carbon atoms. At least one of the cycloalkanes may be condensed with at least one cycloalkane having 3 to 16 carbon atoms. Preferably, at least one hydrogen in the cycloalkane is an alkyl or aryl group having 1 to 6 carbon atoms. may be substituted with a cycloalkyl having 3 to 14 carbon atoms, and At least one hydrogen atom in the compound or structure represented by formula (2B) is deuterium, silyl may be substituted with an anion or halogen; The polycyclic aromatic compound or a multimer thereof according to claim 8.

11. Diarylamino groups fused with cycloalkanes, carba groups fused with cycloalkanes substituted with a benzocarbazolyl group or a benzocarbazolyl group fused with a cycloalkane; 11. The polycyclic aromatic compound or a multimer thereof according to any one of claims 1 to 10.

12. R in the above formula (2A) ２ Or, Rb in the above formula (2B) is a cycloalkane. a diarylamino group fused with a cycloalkane or a carbazolyl group fused with a cycloalkane. The polycyclic aromatic compound according to any one of claims 4 to 10.

13. The cycloalkane is a cycloalkane having 3 to 20 carbon atoms.

2. The polycyclic aromatic compound according to claim 1 .

14. The polycyclic aromatic compound according to any one of claims 1 to 13, wherein the halogen is fluorine. Or a polymer thereof.

15. The polycyclic aromatic compound according to claim 1, which is represented by the following structural formula: 【Chemistry 5】

16. The polycyclic aromatic compound according to claim 1 , which is represented by any one of the following structural formulas: 【Chemistry 6】 【Chemistry 7】 【Chemistry 8】 In the above structural formula, "Me" is a methyl group, "tBu" is a t-butyl group, and "tAm" is a t-amino group. A mil radical, "D" is deuterium.

17. The polycyclic aromatic compound or its multimer according to any one of claims 1 to 16 is provided with a reactive substituent. Group-substituted, reactive compounds.

18. A polymer compound obtained by polymerizing the reactive compound according to claim 17 as a monomer, or Or, a polymer crosslinked body obtained by further crosslinking the polymer compound.

19. A pendant-type polymer in which the reactive compound according to claim 17 is substituted on the main chain polymer. or a pendant polymer crosslinked by further crosslinking said pendant polymer compound. Bridge body.

20. A composition comprising the polycyclic aromatic compound or a multimer thereof according to any one of claims 1 to 16. Materials for organic devices.

21. A material for an organic device, comprising the reactive compound according to claim 17.

22. A material for an organic device, comprising the polymer compound or crosslinked polymer according to claim 18. Fee.

23. A polymer comprising the pendant polymer compound or the pendant polymer crosslinked body according to claim 19. A material for organic devices.

24. The organic device material is a material for an organic electroluminescent element, a material for an organic field effect transistor, The organic degassing device according to any one of claims 20 to 23, which is a material for an organic thin-film solar cell. Material for vices.

25. The organic device according to claim 24, wherein the material for an organic electroluminescent device is a material for a light-emitting layer. Materials for use.

26. A polycyclic aromatic compound or a multimer thereof according to any one of claims 1 to 16 and an organic solvent An ink composition comprising:

27. An ink composition comprising the reactive compound according to claim 17 and an organic solvent.

28. An ink composition comprising a main chain polymer, the reactive compound according to claim 17, and an organic solvent. Composition.

29. An ink comprising the polymer compound or crosslinked polymer according to claim 18 and an organic solvent. composition.

30. A pendant type polymer compound or a pendant type crosslinked polymer according to claim 19, and an organic solvent.

31. A pair of electrodes consisting of an anode and a cathode, and a liquid crystal display device according to any one of claims 1 to 16, which is disposed between the pair of electrodes. A polycyclic aromatic compound or a multimer thereof according to any one of claims 1 to 17, A compound, a polymer compound or a crosslinked polymer according to claim 18, or claim 19. The organic compound containing the pendant polymer compound or the pendant polymer crosslinked body described in and a layer.

32. 32. The organic electroluminescent device according to claim 31, wherein the organic layer is a light-emitting layer.

33. The light-emitting layer comprises a host, the polycyclic aromatic compound as a dopant, a polymer thereof, a reaction product thereof, and a fluorine-containing compound. Reactive compounds, polymer compounds, crosslinked polymers, pendant polymer compounds or pendant The organic electroluminescent device according to claim 32 , further comprising a crosslinked polymer.

34. The host is an anthracene compound, a fluorene compound, or a dibenzochrysene compound. The organic electroluminescent device according to claim 33, which is a compound.

35. At least one of an electron transport layer and an electron injection layer disposed between the cathode and the light emitting layer At least one of the electron transport layer and the electron injection layer is a borane derivative, a pyridinium derivative, fluoranthene derivatives, BO derivatives, anthracene derivatives, benzofluorane derivatives, phenylene derivatives, phosphine oxide derivatives, pyrimidine derivatives, carbazole derivatives, threonine derivatives, Riazine derivatives, benzimidazole derivatives, phenanthroline derivatives, quinolinols Metal complexes, thiazole derivatives, benzothiazole derivatives, silole derivatives and azolines Any one of claims 32 to 34, comprising at least one selected from the group consisting of derivatives.

1. An organic electroluminescent device according to any one of claims 1 to 9.

36. At least one of the electron transport layer and the electron injection layer further comprises an alkali metal, Alkali earth metals, rare earth metals, alkali metal oxides, alkali metal halides, Alkaline earth metal oxides, alkaline earth metal halides, rare earth metal oxides, rare earth halide of alkali metals, organic complexes of alkali metals, organic complexes of alkaline earth metals and dilute 36. The method according to claim 35, further comprising the step of: The organic electroluminescent device according to claim 1 .

37. At least one of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer The layers are made of polymeric compounds that are polymerized using low molecular weight compounds as monomers that can form each layer. Or, a polymer crosslinked body obtained by further crosslinking the polymer compound, or a polymer A pendant polymer compound obtained by reacting a low molecular weight compound obtained with a main chain polymer, or The present invention also provides a pendant-type crosslinked polymer obtained by further crosslinking the pendant-type polymer compound. Item 37. An organic electroluminescent device according to any one of items 31 to 36.

38. A display device or lighting device comprising the organic electroluminescent device according to any one of claims 31 to 37. Device.

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