Polycyclic aromatic compound

Abstract

[Problem] To provide a novel polycyclic aromatic compound, and an organic EL element that uses the same. [Solution] A polycyclic aromatic compound represented by general formula (1A) or general formula (1B) increases options for organic device materials. In addition, using this novel material to fabricate, for example, an organic EL element provides a superior element. A moiety [φ1]n is a moiety obtained by linking a total of n unitary structures of at least one type selected from formula (φ1-m1), formula (φ1-m2), formula (φ1-p1), and formula (φ1-p2). n is an integer equal to or greater than 1. B1 rings, B2 rings, and C rings are aryl rings or heteroaryl rings that may be substituted. Ra is hydrogen or a substituent. Y is B or the like. X1 > N-R or the like. X2 is N or the like. Adjacent C rings may be bonded by single bonds or the like. The polycyclic aromatic compound may be condensed with a cycloalkane, and may be substituted by deuterium or the like.

Description

Technical Field

[0001] The present invention relates to a polycyclic aromatic compound, an organic electroluminescent device, an organic field effect transistor, an organic thin film solar cell, a wavelength conversion filter using the same, and a display device and a lighting device. In this specification, the "organic electroluminescent device" may be referred to as an "organic EL device" or simply an "element".

Background Art

[0002] Conventionally, display devices using light-emitting elements that emit light by an electric field have been variously studied because they can save power and be made thinner. Further, organic electroluminescent devices made of organic materials have been actively studied because they can be easily made lighter and larger. In particular, regarding the development of organic materials having light-emitting characteristics such as blue, which is one of the three primary colors of light, and the development of organic materials having charge transport capabilities (capable of becoming semiconductors or superconductors) such as holes and electrons, both high molecular compounds and low molecular compounds have been actively studied so far.

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

[0004] As materials for the light-emitting layer, for example, benzofluorene-based compounds have been developed (International Publication No. 2004 / 061047). Further, as hole transport materials, for example, triphenylamine-based compounds have been developed (Japanese Patent Application Laid-Open No. 2001-172232). Further, as electron transport materials, for example, anthracene-based compounds have been developed (Japanese Patent Application Laid-Open No. 2005-170911).

[0005] In recent years, materials obtained by improving triphenylamine derivatives have also been reported as materials for use in organic EL elements and organic thin-film solar cells (International Publication No. WO2012 / 118164). This material is based on N,N'-diphenyl-N,N'-bis(3-methylphenyl)-1,1'-biphenyl-4,4'-diamine (TPD), which has already been put into practical use, and is characterized by enhancing the planarity while arranging nitrogen at the center of the ring structure by linking aromatic rings constituting triphenylamine to each other. In this document, for example, the charge transport properties of an NO linking system compound (Compound 1 on page 63) are evaluated, but the manufacturing method of materials other than the NO linking system compound is not described. Also, since the electronic state of the entire compound differs if the linking element is different, the properties obtained from materials other than the NO linking system compound are still unknown. Examples of such compounds can also be found in other documents (International Publication No. WO2011 / 107186). For example, a compound having a conjugated structure with a large triplet exciton energy (T1) can emit phosphorescence with a shorter wavelength, and thus is useful as a material for a blue light-emitting layer. Also, there is a demand for a compound having a novel conjugated structure with a large T1 as an electron transport material or a hole transport material sandwiching the light-emitting layer.

[0006] The host material of an organic EL element is generally a molecule in which a plurality of existing aromatic rings such as benzene and carbazole are linked by single bonds or phosphorus atoms or silicon atoms. This is because by linking a large number of aromatic rings with a relatively small conjugated system, a large HOMO-LUMO gap (band gap Eg in a thin film), which is required for the host material, is ensured. Furthermore, for the host material of an organic EL element using a phosphorescent material or a thermally activated delayed fluorescence material, a high triplet excitation energy (E T ) is also required. However, by linking a donor or acceptor-type aromatic ring or substituent to the molecule, SOMO1 and SOMO2 in the triplet excited state (T1) are localized, and the exchange interaction between both orbitals is reduced, thereby obtaining a triplet excitation energy (E Tit becomes possible to improve. However, small aromatic rings with a conjugated system do not have sufficient redox stability, and devices using molecules obtained by connecting existing aromatic rings as host materials do not have sufficient lifetimes. On the other hand, polycyclic aromatic compounds having an extended π-conjugated system generally have excellent redox stability, but the HOMO-LUMO gap (band gap Eg in thin films) and triplet excitation energy (E T ) are low, so they have been considered unsuitable as host materials.

[0007] In recent years, compounds in which a plurality of aromatic rings are condensed with boron or the like as a central atom have also been reported (International Publication No. 2015 / 102118). In this document, evaluation of an organic EL device using a compound in which the plurality of aromatic rings are condensed as a dopant material for a light-emitting layer has been carried out.

Prior Art Documents

Patent Documents

[0008]

Patent Document 1

Patent Document 2

Patent Document 3

Patent Document 4

Patent Document 5

Patent Document 6

Summary of the Invention

Problems to be Solved by the Invention

[0009] As reported in Patent Documents 1 to 5, various materials have been developed as materials used in organic EL elements. However, in order to increase the options for materials for organic EL elements, the development of materials composed of compounds different from the conventional ones is desired. In particular, it is beneficial to explore organic EL characteristics obtained from materials other than NO-linked compounds in which nitrogen is arranged at the center of the ring structure and their manufacturing methods.

[0010] Further, Patent Document 6 reports a polycyclic aromatic compound containing boron and an organic EL element using the same. However, a very large number of compounds are disclosed in the document. In order to further improve the element characteristics, it is beneficial to explore materials for the light-emitting layer, particularly dopant materials, etc., that can improve organic EL characteristics such as luminous efficiency and element lifetime.

[0011] In addition, as a method for forming the organic layers constituting the organic EL element, at present, in addition to the vacuum evaporation method, a wet film-forming method is also used. Therefore, in particular, the development of ink materials for wet film formation for forming a hole injection layer, a hole transport layer, and a light-emitting layer is being actively carried out, and it is also beneficial to explore such ink materials.

Means for Solving the Problems

[0012] As a result of intensive studies to solve the above problems, the present inventors have found that by disposing a layer containing a polycyclic aromatic compound having a novel structure between a pair of electrodes to form, for example, an organic EL element, an excellent organic EL element can be obtained, and the present invention has been completed. That is, the present invention provides the following polycyclic aromatic compounds, and further organic device materials such as materials for organic EL elements containing the following polycyclic aromatic compounds.

[0013] In this specification, the chemical structure and substituents may be represented by the number of carbon atoms. However, when a substituent is substituted on a chemical structure, or when a further substituent is substituted on a substituent, the number of carbon atoms means the number of carbon atoms of each of the chemical structure and the substituent, and does not mean the total number of carbon atoms of the chemical structure and the substituent, or the total number of carbon atoms of the substituent and the substituent. For example, "substituent B having Y carbon atoms substituted with substituent A having X carbon atoms" means that "substituent A having X carbon atoms" substitutes "substituent B having Y carbon atoms", and Y is not the total number of carbon atoms of substituent A and substituent B. Another example, "substituent B having Y carbon atoms substituted with substituent A" means that "(substituent A without carbon number limitation)" substitutes "substituent B having Y carbon atoms", and Y is not the total number of carbon atoms of substituent A and substituent B.

[0014] Item 1. A polycyclic aromatic compound represented by the following general formula (1A) or general formula (1B).

Chemical formula

Chemical formula

[0015] Item 2. The part of [[φ1]n] is a part formed by linking a total of n units selected from the group consisting of the unit structure represented by the above formula (φ1-m1), the unit structure represented by the above formula (φ1-m2), the unit structure represented by the above formula (φ1-p1), and the unit structure represented by the above formula (φ1-p2). n is an integer from 1 to 5. The B1 ring, B2 ring, and C ring are each independently an aryl ring or a heteroaryl ring, and at least one hydrogen in these rings may be substituted with substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino, substituted or unsubstituted diheteroarylamino, substituted or unsubstituted arylheteroarylamino, substituted or unsubstituted diarylboril (the two aryls may be bonded via a single bond or a linking group), substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, or substituted silyl. R a are each independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino, substituted or unsubstituted diheteroarylamino, substituted or unsubstituted arylheteroarylamino, substituted or unsubstituted diarylboril (the two aryls may be bonded via a single bond or a linking group), substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, or substituted silyl. In the a ring, "-C(-R a )=" may be replaced with "-N=". Y is, independently of each other, B, P, P=O, P=S, Al, Ga, As, Si-R, or Ge-R, where R of Si-R and R of Ge-R are aryl, heteroaryl, alkyl, or cycloalkyl, X 1 is, independently of each other, >N-R, >O, >S, >C(-R)2, >Si(-R)2, or >Se, where R of >N-R, R of >C(-R)2, and R of >Si(-R)2 are, independently of each other, aryl optionally substituted with alkyl or cycloalkyl, heteroaryl optionally substituted with alkyl or cycloalkyl, alkyl, or cycloalkyl, Also, for the X 1 as >C(-R)2, the two Rs and as >Si(-R)2, the two Rs may each be independently linked by a single bond, -CH=CH-, -CR=CR-, -C≡C-, -N(-R)-, -O-, -S-, -C(-R)2-, -Si(-R)2-, or -Se-, where R of -CR=CR-, R of -N(-R)-, R of -C(-R)2-, and R of -Si(-R)2- are, independently of each other, hydrogen, aryl, heteroaryl, alkyl, alkenyl, alkynyl, or cycloalkyl, at least one hydrogen in said R may be substituted with alkyl or cycloalkyl, and two adjacent Rs may form a ring, optionally forming cycloalkylene, arylene, or heteroarylene, Also, for the X 1At least one of R in >N-R, R in >C(-R)2, and R in >Si(-R)2 may be bonded to at least one of the B1 ring, B2 ring, C ring, and a ring by a single bond, -CH=CH-, -CR=CR-, -C≡C-, -N(-R)-, -O-, -S-, -C(-R)2-, -Si(-R)2-, or -Se-. R in -CR=CR-, R in -N(-R)-, R in -C(-R)2-, and R in -Si(-R)2- are each independently hydrogen, aryl, heteroaryl, alkyl, alkenyl, alkynyl, or cycloalkyl. At least one hydrogen in the R may be substituted with alkyl or cycloalkyl. Two adjacent Rs may form a ring and may form cycloalkylene, arylene, or heteroarylene. X 2 is each independently N or C-R. R in the C-R is each independently aryl optionally substituted with alkyl or cycloalkyl, heteroaryl optionally substituted with alkyl or cycloalkyl, alkyl, or cycloalkyl. X 2 When X is N, adjacent C rings in the above formula (1A), formula (φ1-m1), and formula (φ1-m2) may each independently be bonded by a single bond, -CH=CH-, -CR=CR-, -C≡C-, -N(-R)-, -O-, -S-, -C(-R)2-, -Si(-R)2-, or -Se-. R in -CR=CR-, R in -N(-R)-, R in -C(-R)2-, and R in -Si(-R)2- are each independently hydrogen, aryl, heteroaryl, alkyl, alkenyl, alkynyl, or cycloalkyl. At least one hydrogen in the R may be substituted with alkyl or cycloalkyl. Two adjacent Rs may form a ring and may form cycloalkylene, arylene, or heteroarylene. In the compound represented by the above formula (1A) or formula (1B), at least one of the B1 ring, B2 ring, C ring, aryl, and heteroaryl may be condensed with at least one cycloalkane, at least one hydrogen in the cycloalkane may be substituted, and at least one -CH2- in the cycloalkane may be substituted with -O-. At least one hydrogen in the compound represented by the above formula (1A) or formula (1B) may be substituted with deuterium, cyano, or halogen. The polycyclic aromatic compound according to item 1.

[0016] Item 3. The polycyclic aromatic compound according to item 1, which is represented by the following general formula (2A) or general formula (2B). [Chemical formula] [Chemical formula] The part of [φ2]n is a part composed of a total of n linked units selected from the group consisting of the unit structure represented by the above formula (φ2-m1), the unit structure represented by the above formula (φ2-m2), the unit structure represented by the above formula (φ2-p1), and the unit structure represented by the above formula (φ2-p2). n is an integer from 1 to 3. R a 、R b 、and R c are each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboril (the two aryls may be bonded via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, or alkyldicycloalkylsilyl. The R a 、R b 、and R cAt least one hydrogen in may be substituted with aryl, heteroaryl, alkyl, or cycloalkyl, and R b and R c Among them, adjacent groups may be bonded to form an aryl ring or a heteroaryl ring together with the b1 ring and the c ring, and at least one hydrogen in the formed ring may be substituted with aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboril (the two aryls may be bonded via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, or alkyldicycloalkylsilyl, and at least one hydrogen in these substituents may be substituted with aryl, heteroaryl, alkyl, or cycloalkyl, In the a ring, "-C(-R a )=" may be replaced with "-N=". In the b1 ring and the c ring, any "-C(-R)=" (where R is R b or R c ) may be replaced with "-N=", and any "-C(-R)=C(-R)-" (where R is R b or R c ) may be replaced with "-N(-R)-", "-O-", "-S-", "-C(-R)2-", "-Si(-R)2-", or "-Se-", and the R in "-N(-R)-", the R in "-C(-R)2-", and the R in "-Si(-R)2-" are aryl, heteroaryl, alkyl, or cycloalkyl, In the b2 ring, any "-C(-R b )=" may be replaced with "-N=", and one "-C(-R b )=" is a single bond, and the other "-C(-R b)=」 may be replaced by 「-N(-R)-」, 「-O-」, 「-S-」, 「-C(-R)2-」, 「-Si(-R)2-」, or 「-Se-」, where R in 「-N(-R)-」, R in 「-C(-R)2-」, and R in 「-Si(-R)2-」 are aryl, heteroaryl, alkyl, or cycloalkyl, Y is independently B, P, P=O, P=S, Al, Ga, As, Si-R, or Ge-R, where R in Si-R and R in Ge-R are aryl, heteroaryl, alkyl, or cycloalkyl, X 1 is independently >N-R, >O, >S, >C(-R)2, >Si(-R)2, or >Se, where R in >N-R, R in >C(-R)2, and R in >Si(-R)2 are independently aryl having 6 to 12 carbon atoms which may be substituted with alkyl having 1 to 6 carbon atoms or cycloalkyl having 3 to 14 carbon atoms, heteroaryl having 2 to 15 carbon atoms which may be substituted with alkyl having 1 to 6 carbon atoms or cycloalkyl having 3 to 14 carbon atoms, alkyl having 1 to 6 carbon atoms, or cycloalkyl having 3 to 14 carbon atoms, Also, for X 1 the two Rs in >C(-R)2 and the two Rs in >Si(-R)2 as X may be independently bonded by a single bond, -CH=CH-, -CR=CR-, -C≡C-, -N(-R)-, -O-, -S-, -C(-R)2-, -Si(-R)2-, or -Se-, where R in -CR=CR-, R in -N(-R)-, R in -C(-R)2-, and R in -Si(-R)2- are independently hydrogen, aryl having 6 to 12 carbon atoms, heteroaryl having 2 to 15 carbon atoms, alkyl having 1 to 6 carbon atoms, alkenyl having 1 to 6 carbon atoms, alkynyl having 1 to 6 carbon atoms, or cycloalkyl having 3 to 14 carbon atoms, and at least one hydrogen in the R may be substituted with alkyl having 1 to 6 carbon atoms or cycloalkyl having 3 to 14 carbon atoms, and two adjacent Rs may form a ring, forming cycloalkylene having 3 to 14 carbon atoms, arylene having 6 to 12 carbon atoms, or heteroarylene having 2 to 15 carbon atoms, Also, for the X1 At least one of R in >N-R, R in >C(-R)2, and R in >Si(-R)2 may be bonded to at least one of the a-ring, b1-ring, b2-ring, and c-ring by a single bond, -CH=CH-, -CR=CR-, -C≡C-, -N(-R)-, -O-, -S-, -C(-R)2-, -Si(-R)2-, or -Se-. R in -CR=CR-, R in -N(-R)-, R in -C(-R)2-, and R in -Si(-R)2- are each independently hydrogen, aryl having 6 to 12 carbon atoms, heteroaryl having 2 to 15 carbon atoms, alkyl having 1 to 6 carbon atoms, alkenyl having 1 to 6 carbon atoms, alkynyl having 1 to 6 carbon atoms, or cycloalkyl having 3 to 14 carbon atoms. At least one hydrogen in the R may be substituted with alkyl having 1 to 6 carbon atoms or cycloalkyl having 3 to 14 carbon atoms. Two adjacent Rs may form a ring and may form cycloalkylene having 3 to 14 carbon atoms, arylene having 6 to 12 carbon atoms, or heteroarylene having 2 to 15 carbon atoms. X 2 are each independently N or C-R. R in the C-R is each independently 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. X 2 When X is N, adjacent Rs in adjacent c-rings in the above formula (2A), formula (φ2-m1), and formula (φ2-m2) cThe groups may be combined to form a single bond, -CH=CH-, -CR=CR-, -C≡C-, -N(-R)-, -O-, -S-, -C(-R)2-, -Si(-R)2-, or -Se-, where R in -CR=CR-, R in -N(-R)-, R in -C(-R)2-, and R in -Si(-R)2- are each independently hydrogen, aryl having 6 to 12 carbon atoms, heteroaryl having 2 to 15 carbon atoms, alkyl having 1 to 6 carbon atoms, alkenyl having 1 to 6 carbon atoms, alkynyl having 1 to 6 carbon atoms, or cycloalkyl having 3 to 14 carbon atoms, and at least one hydrogen in the R may be substituted with alkyl having 1 to 6 carbon atoms or cycloalkyl having 3 to 14 carbon atoms. Two adjacent Rs may form a ring, which may form cycloalkylene having 3 to 14 carbon atoms, arylene having 6 to 12 carbon atoms, or heteroarylene having 2 to 15 carbon atoms. In the compound represented by the above formula (2A) or formula (2B), at least one of the b1 ring, the c ring, the formed ring, the aryl, and the heteroaryl may be condensed with at least one cycloalkane having 3 to 24 carbon atoms, and at least one hydrogen in the cycloalkane may be substituted with 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 -CH2- in the cycloalkane may be substituted with -O-. At least one hydrogen in the compound represented by the above formula (2A) or formula (2B) may be substituted with deuterium, cyano, or halogen.

[0017] Item 4. The part of [[φ2]n] is a part composed of a total of n linked units selected from the group consisting of the unit structure represented by the above formula (φ2-m1), the unit structure represented by the above formula (φ2-m2), the unit structure represented by the above formula (φ2-p1), and the unit structure represented by the above formula (φ2-p2). n is an integer from 1 to 3. R a 、R b 、and R cis, independently, hydrogen, an aryl having 6 to 30 carbon atoms, a heteroaryl having 2 to 30 carbon atoms, a diarylamino (wherein aryl is an aryl having 6 to 12 carbon atoms), a diarylboranyl (wherein aryl is an aryl having 6 to 12 carbon atoms and the two aryls may be bonded via a single bond or a linking group), an alkyl having 1 to 24 carbon atoms, or a cycloalkyl having 3 to 24 carbon atoms, and the R a , R b , and at least one hydrogen in R c may be substituted with an aryl having 6 to 12 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, an alkyl having 1 to 6 carbon atoms, or a cycloalkyl having 3 to 14 carbon atoms. Further, adjacent groups among R b and R c may be bonded to each other to form, together with the b1 ring and the c ring, an aryl ring having 9 to 16 carbon atoms or a heteroaryl ring having 6 to 15 carbon atoms. At least one hydrogen in the formed ring may be substituted with an aryl having 6 to 30 carbon atoms, a heteroaryl having 2 to 30 carbon atoms, a diarylamino (wherein aryl is an aryl having 6 to 12 carbon atoms), a diarylboranyl (wherein aryl is an aryl having 6 to 12 carbon atoms and the two aryls may be bonded via a single bond or a linking group), an alkyl having 1 to 24 carbon atoms, or a cycloalkyl having 3 to 24 carbon atoms. At least one hydrogen in these substituents may be substituted with an aryl having 6 to 12 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, an alkyl having 1 to 6 carbon atoms, or a cycloalkyl having 3 to 14 carbon atoms. In the a ring, “-C(-R a )=” may be replaced with “-N=”. In the b1 ring and the c ring, any “-C(-R)=” (where R is R b or R c ) may be replaced with “-N=”. Any “-C(-R)=C(-R)-” (where R is R b or R c(wherein) may be replaced by “-N(-R)-”, “-O-”, “-S-”, “-C(-R)2-”, “-Si(-R)2-”, or “-Se-”, and R in said “-N(-R)-”, R in “-C(-R)2-”, and R in “-Si(-R)2-” are 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, In the b2 ring, any “-C(-R b )=” may be replaced by “-N=”, and also, one “-C(-R b )=” is a single bond, and the other “-C(-R b )=” may be replaced by “-N(-R)-”, “-O-”, “-S-”, “-C(-R)2-”, “-Si(-R)2-”, or “-Se-”, and R in said “-N(-R)-”, R in “-C(-R)2-”, and R in “-Si(-R)2-” are 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, Y is independently B, P, P=O, P=S, Al, Ga, As, Si-R, or Ge-R, and R in said Si-R and R in Ge-R are 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, X 1 is independently >N-R, >O, >S, >C(-R)2, >Si(-R)2, or >Se, and R in said >N-R, R in >C(-R)2, and R in >Si(-R)2 are independently aryl having 6 to 10 carbon atoms which may be substituted by alkyl having 1 to 5 carbon atoms or cycloalkyl having 5 to 10 carbon atoms, heteroaryl having 2 to 10 carbon atoms which may be substituted by alkyl having 1 to 5 carbon atoms or cycloalkyl having 5 to 10 carbon atoms, alkyl having 1 to 5 carbon atoms, or cycloalkyl having 5 to 10 carbon atoms, Also, said X 1As for the two Rs of >C(-R)2 and the two Rs of >Si(-R)2, each independently may be bonded by a single bond, -CH=CH-, -CR=CR-, -C≡C-, -N(-R)-, -O-, -S-, -C(-R)2-, -Si(-R)2-, or -Se-. The Rs of -CR=CR-, -N(-R)-, -C(-R)2-, and -Si(-R)2- are each independently hydrogen, aryl having 6 to 10 carbon atoms, heteroaryl having 2 to 10 carbon atoms, alkyl having 1 to 5 carbon atoms, alkenyl having 1 to 5 carbon atoms, alkynyl having 1 to 5 carbon atoms, or cycloalkyl having 5 to 10 carbon atoms. At least one hydrogen in the R may be substituted with alkyl having 1 to 5 carbon atoms or cycloalkyl having 5 to 10 carbon atoms. Two adjacent Rs may form a ring and may form cycloalkylene having 5 to 10 carbon atoms, arylene having 6 to 10 carbon atoms, or heteroarylene having 2 to 10 carbon atoms. Also, the said X 1 At least one of the Rs of >N-R, the R of >C(-R)2, and the R of >Si(-R)2 may be bonded to at least one of the a-ring, b1-ring, b2-ring, and c-ring by a single bond, -CH=CH-, -CR=CR-, -C≡C-, -N(-R)-, -O-, -S-, -C(-R)2-, -Si(-R)2-, or -Se-. The Rs of -CR=CR-, -N(-R)-, -C(-R)2-, and -Si(-R)2- are each independently hydrogen, aryl having 6 to 10 carbon atoms, heteroaryl having 2 to 10 carbon atoms, alkyl having 1 to 5 carbon atoms, alkenyl having 1 to 5 carbon atoms, alkynyl having 1 to 5 carbon atoms, or cycloalkyl having 5 to 10 carbon atoms. At least one hydrogen in the R may be substituted with alkyl having 1 to 5 carbon atoms or cycloalkyl having 5 to 10 carbon atoms. Two adjacent Rs may form a ring and may form cycloalkylene having 5 to 10 carbon atoms, arylene having 6 to 10 carbon atoms, or heteroarylene having 2 to 10 carbon atoms. X 2is independently N or C-R, where R of the C-R is independently aryl having 6 to 10 carbon atoms, heteroaryl having 2 to 10 carbon atoms, alkyl having 1 to 5 carbon atoms, or cycloalkyl having 5 to 10 carbon atoms, X 2 When X is N, adjacent Rs in all adjacent c rings in the above formula (2A), formula (φ2-m1), and formula (φ2-m2) c may be bonded to each other to form a single bond, -CH=CH-, -CR=CR-, -C≡C-, -N(-R)-, -O-, -S-, -C(-R)2-, -Si(-R)2-, or -Se-, where R of -CR=CR-, R of -N(-R)-, R of -C(-R)2-, and R of -Si(-R)2- are independently hydrogen, aryl having 6 to 10 carbon atoms, heteroaryl having 2 to 10 carbon atoms, alkyl having 1 to 5 carbon atoms, alkenyl having 1 to 5 carbon atoms, alkynyl having 1 to 5 carbon atoms, or cycloalkyl having 5 to 10 carbon atoms, and at least one hydrogen in the R may be substituted with alkyl having 1 to 5 carbon atoms or cycloalkyl having 5 to 10 carbon atoms, and two adjacent Rs may form a ring to form cycloalkylene having 5 to 10 carbon atoms, arylene having 6 to 10 carbon atoms, or heteroarylene having 2 to 10 carbon atoms, In the compound represented by the above formula (2A) or formula (2B), at least one of the b1 ring, the c ring, the formed ring, the aryl, and the heteroaryl may be condensed with at least one cycloalkane having 3 to 20 carbon atoms, and at least one hydrogen in the cycloalkane may be substituted with aryl having 6 to 16 carbon atoms, heteroaryl having 2 to 15 carbon atoms, alkyl having 1 to 12 carbon atoms, or cycloalkyl having 3 to 16 carbon atoms, At least one hydrogen in the compound represented by the above formula (2A) or formula (2B) may be substituted with deuterium, cyano, or halogen, The polycyclic aromatic compound according to item 3.

[0018] Item 5. In the part of [φ2]n in the above formula (2A), it is a part formed by connecting a total of n units selected from the group consisting of the unit structure represented by the above formula (φ2-m1) and the unit structure represented by the above formula (φ2-m2). In the part of [φ2]n in the above formula (2B), it is a part formed by connecting a total of n units selected from the group consisting of the unit structure represented by the above formula (φ2-p1) and the unit structure represented by the above formula (φ2-p2). n is an integer from 1 to 3. R a 、R b 、and R c are each independently hydrogen, aryl having 6 to 16 carbon atoms, heteroaryl having 2 to 20 carbon atoms, diarylamino (where aryl is aryl having 6 to 10 carbon atoms), diarylboryl (where aryl is aryl having 6 to 10 carbon atoms, and the two aryls may be bonded via a single bond or a linking group), alkyl having 1 to 12 carbon atoms, or cycloalkyl having 3 to 16 carbon atoms. At least one hydrogen in the said R a 、R b 、and R c may be substituted with aryl having 6 to 10 carbon atoms, heteroaryl having 2 to 10 carbon atoms, alkyl having 1 to 5 carbon atoms, or cycloalkyl having 5 to 10 carbon atoms. In the a ring, "-C(-R a )=" may be replaced with "-N=". In the b1 ring and the c ring, any "-C(-R)=" (where R is R b or R c ) may be replaced with "-N=", and any "-C(-R)=C(-R)-" (where R is R b or R c ) may be replaced with "-N(-R)-", "-O-", "-S-", or "-C(-R)2-". The R in the said "-N(-R)-" and the R in the "-C(-R)2-" are aryl having 6 to 10 carbon atoms, heteroaryl having 2 to 10 carbon atoms, alkyl having 1 to 5 carbon atoms, or cycloalkyl having 5 to 10 carbon atoms. In the b2 ring, any “-C(-R b )=” may be replaced by “-N=”, and also, one “-C(-R b )=” is a single bond, and the other “-C(-R b )=” may be replaced by “-N(-R)-”, “-O-”, “-S-”, or “-C(-R)2-”. The R of the “-N(-R)-” and the R of the “-C(-R)2-” are each independently aryl having 6 to 10 carbon atoms, heteroaryl having 2 to 10 carbon atoms, alkyl having 1 to 5 carbon atoms, or cycloalkyl having 5 to 10 carbon atoms. Y is each independently B, P, P=O, or P=S. X 1 is each independently >N-R, >O, >S, or >C(-R)2. The R of the >N-R and the R of the >C(-R)2 are each independently aryl having 6 to 10 carbon atoms which may be substituted by alkyl having 1 to 5 carbon atoms, heteroaryl having 2 to 10 carbon atoms which may be substituted by alkyl having 1 to 5 carbon atoms, alkyl having 1 to 5 carbon atoms, or cycloalkyl having 5 to 10 carbon atoms. Also, the two Rs of >C(-R)2 and the two Rs of >Si(-R)2 as the X 1 may be bonded to each other independently by a single bond, -CH=CH-, -CR=CR-, -N(-R)-, -O-, -S-, or -C(-R)2-. The R of the -CR=CR-, the R of the -N(-R)-, and the R of the -C(-R)2- are each independently hydrogen, aryl having 6 to 10 carbon atoms, heteroaryl having 2 to 10 carbon atoms, alkyl having 1 to 5 carbon atoms, alkenyl having 1 to 5 carbon atoms, alkynyl having 1 to 5 carbon atoms, or cycloalkyl having 5 to 10 carbon atoms. Two adjacent Rs may form a ring, and may form cycloalkylene having 5 to 10 carbon atoms, arylene having 6 to 10 carbon atoms, or heteroarylene having 2 to 10 carbon atoms. Also, the X 1At least one of R in >N-R, R in >C(-R)2, and R in >Si(-R)2 may be bonded to at least one of the a ring, b1 ring, b2 ring, and c ring by a single bond, -CH=CH-, -CR=CR-, -N(-R)-, -O-, -S-, or -C(-R)2-. R in -CR=CR-, R in -N(-R)-, and R in -C(-R)2- are each independently hydrogen, aryl having 6 to 10 carbon atoms, heteroaryl having 2 to 10 carbon atoms, alkyl having 1 to 5 carbon atoms, alkenyl having 1 to 5 carbon atoms, alkynyl having 1 to 5 carbon atoms, or cycloalkyl having 5 to 10 carbon atoms. Two adjacent Rs may form a ring and may form cycloalkylene having 5 to 10 carbon atoms, arylene having 6 to 10 carbon atoms, or heteroarylene having 2 to 10 carbon atoms. X 2 is N, In all adjacent Rs in adjacent c rings in the above formula (2A), formula (φ2-m1), and formula (φ2-m2), c they may be bonded to each other to form a single bond, -CH=CH-, -CR=CR-, -N(-R)-, -O-, -S-, or -C(-R)2-. R in -CR=CR-, R in -N(-R)-, and R in -C(-R)2- are each independently aryl having 6 to 10 carbon atoms, heteroaryl having 2 to 10 carbon atoms, alkyl having 1 to 5 carbon atoms, alkenyl having 1 to 5 carbon atoms, alkynyl having 1 to 5 carbon atoms, or cycloalkyl having 5 to 10 carbon atoms. Two adjacent Rs may form a ring and may form cycloalkylene having 5 to 10 carbon atoms, arylene having 6 to 10 carbon atoms, or heteroarylene having 2 to 10 carbon atoms. In the compound represented by the above formula (2A) or formula (2B), at least one of the b1 ring, the c ring, the aryl, and the heteroaryl may be condensed with at least one cycloalkane having 3 to 16 carbon atoms, and at least one hydrogen in the cycloalkane may be substituted with aryl having 6 to 10 carbon atoms, heteroaryl having 2 to 10 carbon atoms, alkyl having 1 to 5 carbon atoms, or cycloalkyl having 5 to 10 carbon atoms. At least one hydrogen in the compound represented by the above formula (2A) or formula (2B) may be substituted with deuterium, cyano, or halogen. The polycyclic aromatic compound according to Item 3.

[0019] Item 6. The part of [φ2]n in the above formula (2A) is a part composed of a total of n linked units selected from the group consisting of the unit structure represented by the above formula (φ2-m1) and the unit structure represented by the above formula (φ2-m2). The part of [φ2]n in the above formula (2B) is a part composed of a total of n linked units selected from the group consisting of the unit structure represented by the above formula (φ2-p1) and the unit structure represented by the above formula (φ2-p2). n is 1 or 2. R a R b and R c are each independently hydrogen, aryl having 6 to 16 carbon atoms, heteroaryl having 2 to 20 carbon atoms, diarylamino (where aryl is aryl having 6 to 10 carbon atoms), diarylboryl (where aryl is aryl having 6 to 10 carbon atoms and the two aryls may be bonded via a single bond or a linking group), alkyl having 1 to 12 carbon atoms, or cycloalkyl having 3 to 16 carbon atoms, and at least one hydrogen in the R a R b and R c may be substituted with alkyl having 1 to 5 carbon atoms or cycloalkyl having 5 to 10 carbon atoms. In the a ring, "-C(-R a )=" may be replaced with "-N=". In the b1 ring and the c ring, any "-C(-R)=" (where R is R b or R c ) may be replaced with "-N=", and any "-C(-R)=C(-R)-" (where R is R b or R c(wherein) may be replaced by “-N(-R)-”, “-O-”, or “-S-”, and R in the “-N(-R)-” is aryl having 6 to 10 carbon atoms, heteroaryl having 2 to 10 carbon atoms, alkyl having 1 to 5 carbon atoms, or cycloalkyl having 5 to 10 carbon atoms, In the b2 ring, any “-C(-R b )=” may be replaced by “-N=”, and one of “-C(-R b )=” is a single bond, and the other “-C(-R b )=” may be replaced by “-N(-R)-”, “-O-”, or “-S-”, and R in the “-N(-R)-” is aryl having 6 to 10 carbon atoms, heteroaryl having 2 to 10 carbon atoms, alkyl having 1 to 5 carbon atoms, or cycloalkyl having 5 to 10 carbon atoms, Y is independently B, X 1 is independently >N-R or >O, and R in the >N-R is independently aryl having 6 to 10 carbon atoms which may be substituted by alkyl having 1 to 5 carbon atoms, alkyl having 1 to 5 carbon atoms, or cycloalkyl having 5 to 10 carbon atoms, Further, R in the >N-R as the X 1 may be bonded to at least one of the a ring, b1 ring, b2 ring, and c ring by a single bond, X 2 is N, In all adjacent c rings in the above formula (2A), formula (φ2-m1), and formula (φ2-m2), adjacent R c to each other may be bonded to form a single bond, In the compound represented by the above formula (2A) or formula (2B), at least one of the b1 ring, the c ring, and aryl having 6 to 10 carbon atoms as R in the >N-R may be condensed with cycloalkane having 3 to 14 carbon atoms, and at least one hydrogen in the cycloalkane may be substituted by alkyl having 1 to 5 carbon atoms, At least one hydrogen in the compound represented by the above formula (2A) or formula (2B) may be substituted by deuterium, cyano, or halogen, The polycyclic aromatic compound described in item 3.

[0020] Item 7. The polycyclic aromatic compound described in item 1, represented by the following structural formula. [Chemical formula] (In the structural formula, "Me" represents a methyl group.)

[0021] Item 8. The polycyclic aromatic compound described in item 1, represented by any of the following structural formulas. [Chemical formula] [Chemical formula] (In the structural formula, "Me" represents a methyl group and "tBu" represents a t-butyl group.)

[0022] Item 9. The polycyclic aromatic compound described in item 1, represented by any of the following structural formulas. [Chemical formula] (In the structural formula, "Me" represents a methyl group and "tBu" represents a t-butyl group.)

[0023] Item 10. A reactive compound in which a reactive substituent is substituted on the polycyclic aromatic compound described in any of items 1 to 9.

[0024] Item 11. A polymer compound obtained by polymerizing the reactive compound described in item 10 as a monomer, or a polymer crosslinked body obtained by further crosslinking the polymer compound.

[0025] Item 12. A pendant polymer compound obtained by substituting the main-chain polymer with the reactive compound described in item 10, or a pendant polymer crosslinked body obtained by further crosslinking the pendant polymer compound.

[0026] Item 13. A material for an organic device containing a polycyclic aromatic compound described in any one of Items 1 to 9.

[0027] Item 14. A material for an organic device containing a reactive compound described in Item 10.

[0028] Item 15. A material for an organic device containing a polymer compound or a polymer crosslinked body described in Item 11.

[0029] Item 16. A material for an organic device containing a pendant-type polymer compound or a pendant-type polymer crosslinked body described in Item 12.

[0030] Item 17. The material for an organic device according to any one of Items 13 to 16, wherein the material for an organic device is a material for an organic electroluminescent element, a material for an organic field effect transistor, a material for an organic thin film solar cell, or a material for a wavelength conversion filter.

[0031] Item 18. The material for an organic device according to Item 17, wherein the material for an organic electroluminescent element is a material for a light emitting layer.

[0032] Item 19. An ink composition containing a polycyclic aromatic compound described in any one of Items 1 to 9 and an organic solvent.

[0033] Item 20. An ink composition containing a reactive compound described in Item 10 and an organic solvent.

[0034] Item 21. An ink composition containing a main chain type polymer, a reactive compound described in Item 10, and an organic solvent.

[0035] Item 22. An ink composition containing a polymer compound or a polymer crosslinked body described in Item 11 and an organic solvent.

[0036] Item 23. An ink composition comprising the pendant-type polymer compound or pendant-type polymer crosslinked body described in Item 12 and an organic solvent.

[0037] Item 24. An organic electroluminescent device having a pair of electrodes composed of an anode and a cathode, and an organic layer disposed between the pair of electrodes and containing the polycyclic aromatic compound described in any one of Items 1 to 9, the reactive compound described in Item 10, the polymer compound or polymer crosslinked body described in Item 11, or the pendant-type polymer compound or pendant-type polymer crosslinked body described in Item 12.

[0038] Item 25. The organic electroluminescent device according to Item 24, wherein the organic layer is a light-emitting layer.

[0039] Item 26. The organic electroluminescent device according to Item 25, wherein the light-emitting layer contains a host and the polycyclic aromatic compound, reactive compound, polymer compound, polymer crosslinked body, pendant-type polymer compound or pendant-type polymer crosslinked body as a dopant.

[0040] Item 27. The organic electroluminescent device according to Item 26, wherein the host is an anthracene-based compound, a fluorene-based compound or a dibenzocrisene-based compound.

[0041] Item 28. having at least one layer of an electron transport layer and an electron injection layer disposed between the cathode and the light-emitting layer, and at least one of the electron transport layer and the electron injection layer contains at least one selected from the group consisting of borane derivatives, pyridine derivatives, fluoranthene derivatives, BO-based derivatives, anthracene derivatives, benzofluorene derivatives, phosphine oxide derivatives, pyrimidine derivatives, carbazole derivatives, triazine derivatives, benzimidazole derivatives, phenanthroline derivatives, quinolinol-based metal complexes, thiazole derivatives, benzothiazole derivatives, silole derivatives and azoline derivatives, the organic electroluminescent device according to any one of items 25 to 27.

[0042] Item 29. The organic electroluminescent device according to item 28, wherein at least one layer of the electron transport layer and the electron injection layer further contains at least one selected from the group consisting of alkali metals, alkaline earth metals, rare earth metals, oxides of alkali metals, halides of alkali metals, oxides of alkaline earth metals, halides of alkaline earth metals, oxides of rare earth metals, halides of rare earth metals, organic complexes of alkali metals, organic complexes of alkaline earth metals and organic complexes of rare earth metals.

[0043] Item 30. The organic electroluminescent device according to any one of items 24 to 29, wherein at least one layer of the hole injection layer, the hole transport layer, the light-emitting layer, the electron transport layer and the electron injection layer is a polymer compound obtained by polymerizing a low molecular compound capable of forming each layer as a monomer, or a polymer crosslinked body obtained by further crosslinking the polymer compound, or a pendant polymer compound obtained by reacting a low molecular compound capable of forming each layer with a main chain type polymer, or a pendant polymer crosslinked body obtained by further crosslinking the pendant polymer compound.

[0044] Item 31. A display device or a lighting device including the organic electroluminescent device according to any one of items 24 to 30.

[0045] Item 32. A wavelength conversion filter comprising the material for a wavelength conversion filter described in item 17.

Advantages of the Invention

[0046] According to a preferred embodiment of the present invention, it is possible to provide a polycyclic aromatic compound having a novel structure that can be used as a material for an organic device such as a material for an organic EL element, and by using this polycyclic aromatic compound, it is possible to provide an excellent organic device such as an organic EL element.

[0047] Specifically, the present inventors have found that a polycyclic aromatic compound in which aromatic rings are linked by hetero elements such as boron, phosphorus, oxygen, nitrogen, and sulfur has a large HOMO-LUMO gap or a small HOMO-LUMO gap (band gap Eg in a thin film) depending on the method of linking the hetero elements. This is presumably because a 6-membered ring containing a hetero element has low aromaticity, which suppresses or promotes the reduction of the HOMO-LUMO gap associated with the extension of the conjugated system and the localization or delocalization of each orbital. These polycyclic aromatic compounds have a robust skeleton in which 5-membered rings or 6-membered rings are condensed or linked, so that the half-width of the fluorescence emission peak is narrow, and high-color-purity emission can be obtained when used as an emitter of an organic EL element. In addition, by selecting the method of linking the hetero elements, thermally activated delayed fluorescence is exhibited, and high efficiency can be obtained when used as an emitter of an organic EL element. Furthermore, by introducing substituents, the energies of HOMO and LUMO can be arbitrarily moved, so that it is possible to optimize the ionization potential and electron affinity according to the surrounding materials. However, the present invention is not particularly limited to these principles.

Brief Description of the Drawings

[0048]

Figure 1

Figure 2

Figure 3

Figure 4

Figure 5

Embodiments for Carrying Out the Invention

[0049] 1. Polycyclic aromatic compound <Description of the overall structure of the compound> The invention of the present application is a polycyclic aromatic compound represented by the following general formula (1A) or general formula (1B). In addition, the definitions of the symbols in each structural formula are the same as those described above, and further, the definitions of the symbols in all the structural formulas shown after this paragraph are also the same as those described above.

Chemical formula

Chemical formula

[0050] Further, the invention of the present application is preferably a polycyclic aromatic compound represented by the following general formula (2A) or general formula (2B). In addition, the definitions of the symbols in each structural formula are the same as those described above, and further, the definitions of the symbols in all the structural formulas shown after this paragraph are also the same as those described above.

Chemical formula

Chemical formula

[0051] The above n is an integer of 1 or more, and an integer of 1 to 5, an integer of 1 to 3, 1 or 2 is preferable. Further, when dissolved in a solution and used as an ink composition for coating, n is preferably an integer of 1 to 20, an integer of 2 to 7, or an integer of 3 to 5.

[0052] <Description of the unit structure constituting the compound> The above polycyclic aromatic compound is a compound in which at least one unit structure of the meta-type unit structure and the para-type unit structure shown below is condensed and linked so that (n + 1) (where n is an integer of 1 or more) share the B1 ring or the b1 ring. The ring part formed by condensing so as to share the B1 ring is represented by the B2 ring in the above formulas (φ1-m1), (φ1-m2), (φ1-p1) and (φ1-p2), and the ring part formed by condensing so as to share the b1 ring is represented by the b2 ring in the above formulas (φ2-m1), (φ2-m2), (φ2-p1) and (φ2-p2). [Chemical formula]

[0053] The meta-type unit structure has a structure in which two Ys are located at the meta-position of the a ring, and the para-type unit structure has a structure in which two Ys are located at the para-position of the a ring. Both unit structures contain two condensed bicyclic structures. The condensed bicyclic structure means a structure in which two 6-membered saturated hydrocarbon rings are condensed in the meta-type unit structure (a decahydronaphthalene-type structure composed of Y, X 1 and X 2 ), and the two condensed bicyclic structures are arranged (condensed) around the a ring so as to be condensed with each other. Further, in the para-type unit structure, a structure in which two 6-membered saturated hydrocarbon rings are condensed (Y and two Xs 1It refers to a decahydronaphthalene-type structure composed of..., and two condensed bicyclic structures are arranged (condensed) around the a-ring so as to be located at the para-position of the a-ring.

[0054] <Description of the connection form of the unit structure> The polycyclic aromatic compound of the above formula (1A) contains at least one meta-type unit structure 1 as the unit structure φ1, and the other unit structures φ1 may be only the meta-type unit structure 1, only the para-type unit structure 1, or a mixture of the meta-type unit structure 1 and the para-type unit structure 1. However, a preferred form is a compound in which a total of (n + 1) meta-type unit structures 1 are linked as the unit structure φ1.

[0055] The polycyclic aromatic compound of the above formula (1B) contains at least one para-type unit structure 1 as the unit structure φ1, and the other unit structures φ1 may be only the para-type unit structure 1, only the meta-type unit structure 1, or a mixture of the para-type unit structure 1 and the meta-type unit structure 1. However, a preferred form is a compound in which a total of (n + 1) para-type unit structures 1 are linked as the unit structure φ1.

[0056] The polycyclic aromatic compound of the above formula (2A) contains at least one meta-type unit structure 2 as the unit structure φ2, and the other unit structures φ2 may be only the meta-type unit structure 2, only the para-type unit structure 2, or a mixture of the meta-type unit structure 2 and the para-type unit structure 2. However, a preferred form is a compound in which a total of (n + 1) meta-type unit structures 2 are linked as the unit structure φ2.

[0057] The polycyclic aromatic compound of the above formula (2B) contains at least one para-type unit structure 2 as the unit structure φ2, and the other unit structures φ2 may be only the para-type unit structure 2, only the meta-type unit structure 2, or a mixture of the para-type unit structure 2 and the meta-type unit structure 2. However, a preferred form is a compound in which a total of (n + 1) para-type unit structures 2 are linked as the unit structure φ2.

[0058] As the forms when each unit structure is connected, there are two types of the meta-type unit structure 1, namely the form of the above formula (φ1-m1) and the form of the above formula (φ1-m2) (the vertically inverted form), and there are two types of the para-type unit structure 1, namely the form of the above formula (φ1-p1) and the form of the above formula (φ1-p2) (the vertically inverted form), and there are two types of the meta-type unit structure 2, namely the form of the above formula (φ2-m1) and the form of the above formula (φ2-m2) (the vertically inverted form), and there are two types of the para-type unit structure 2, namely the form of the above formula (φ2-p1) and the form of the above formula (φ2-p2) (the vertically inverted form).

[0059] Regarding the polycyclic aromatic compound of the above formula (1A), formula (1B), formula (2A) or formula (2B), the vertically inverted forms may be mixed and connected, but a compound connected only in the non-vertically inverted form is preferred.

[0060] In formula (1A), as φ1, a form in which at least one selected from the group consisting of formula (φ1-m1) and formula (φ1-m2) is selected in total by n is preferred, and a form in which only n formula (φ1-m1) are selected is more preferred. In formula (1B), as φ1, a form in which at least one selected from the group consisting of formula (φ1-p1) and formula (φ1-p2) is selected in total by n is preferred, and a form in which only n formula (φ1-p1) are selected is more preferred. In formula (2A), as φ2, a form in which at least one selected from the group consisting of formula (φ2-m1) and formula (φ2-m2) is selected in total by n is preferred, and a form in which only n formula (φ2-m1) are selected is more preferred. In formula (2B), as φ2, a form in which at least one selected from the group consisting of formula (φ2-p1) and formula (φ2-p2) is selected in total by n is preferred, and a form in which only n formula (φ2-p1) are selected is more preferred.

[0061] In the B1 ring and b1 ring in the above-mentioned meta-type unit structure and para-type unit structure, they are condensed at one position in the condensed bicyclic structure. However, as described above, when the unit structures are condensed and linked so as to share the B1 ring or b1 ring, the B1 ring and b1 ring are deformed into a structure condensed at two positions in the condensed bicyclic structure (a structure sandwiched between two condensed bicyclic structures). Therefore, as shown in the above formula (φ1-m1), formula (φ1-m2), formula (φ1-p1), formula (φ1-p2), formula (φ2-m1), formula (φ2-m2), formula (φ2-p1), and formula (φ2-p2), the notations are changed to B2 ring and b2 ring, respectively. Note that the notations of the B1 ring and b1 ring not involved in the linkage are left unchanged.

[0062] <Description of each part of the compound and the unit structure> Next, each part of the compound and the unit structure will be described. As described above, since the polycyclic aromatic compound of formula (1A), formula (1B), formula (2A), or formula (2B) is a compound formed by repeatedly linking the above-mentioned meta-type unit structure and para-type unit structure, the description of each part of the compound and the description of each part of the unit structure (the above-mentioned meta-type unit structure, para-type unit structure, unit structure of formula (φ1-m1), formula (φ1-m2), formula (φ1-p1), formula (φ1-p2), formula (φ2-m1), formula (φ2-m2), formula (φ2-p1), or formula (φ2-p2)) are basically the same. However, as described above, the B1 ring and b1 ring whose structures are deformed when the unit structures are linked, and the B2 ring and b2 ring after their deformation will be separately described as necessary.

[0063] <Description of the ring structure and its substituents> In each formula, the B1 ring, the B2 ring, and the C ring are each independently an aryl ring or a heteroaryl ring, and at least one hydrogen in these rings may be substituted with a substituent. This substituent is preferably a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted diarylamino, a substituted or unsubstituted diheteroarylamino, a substituted or unsubstituted arylheteroarylamino (an amino group having an aryl and a heteroaryl), a substituted or unsubstituted diarylboril (two aryls may be bonded via a single bond or a linking group), a substituted or unsubstituted alkyl, a substituted or unsubstituted cycloalkyl, a substituted or unsubstituted alkoxy, a substituted or unsubstituted aryloxy, or a substituted silyl. Examples of the substituent when these groups have a substituent include aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboril (two aryls may be bonded via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, or substituted silyl. The details of the rings and substituents listed here will be summarized and described later.

[0064] R in each formula ais hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino, substituted or unsubstituted diheteroarylamino, substituted or unsubstituted arylheteroarylamino (an amino group having aryl and heteroaryl), substituted or unsubstituted diarylboril (two aryls may be bonded via a single bond or a linking group), substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, or substituted silyl. When these groups have substituents, examples of the substituents include aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboril (two aryls may be bonded via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, or substituted silyl. Details of the rings and substituents listed here will be summarized and described later.

[0065] R in each formula b and R c Specific examples of, and more specific examples of R a are each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboril (two aryls may be bonded via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, or alkyldicycloalkylsilyl, and at least one hydrogen in the R a , R b , and R c may be substituted with aryl, heteroaryl, alkyl, or cycloalkyl. Details of the substituents listed here will be summarized and described later.

[0066] The aryl ring or heteroaryl ring as the B1 ring, B2 ring, and C ring preferably has a 5-membered ring or 6-membered ring that shares a bond with the above-described fused bicyclic structure. Here, the "6-membered ring sharing a bond with the condensed bicyclic structure" means, for example, the b1 ring, b2 ring, and c ring (benzene ring (6-membered ring)) fused to the condensed bicyclic structure as shown by formula (2A), formula (2B), and their unit structural formulas. Also, "an aryl ring or heteroaryl ring (which are the B1 ring, B2 ring, and C ring) has this 6-membered ring" means that the B1 ring, B2 ring, and C ring are formed only by this 6-membered ring, or the B1 ring, B2 ring, and C ring are formed to include this 6-membered ring by further fusing other rings or the like to this 6-membered ring. In other words, the "aryl ring or heteroaryl ring (which are the B1 ring, B2 ring, and C ring) having a 6-membered ring" referred to here means that the 6-membered ring constituting all or part of the B1 ring, B2 ring, and C ring is fused to the condensed bicyclic structure. The same explanation applies to the "5-membered ring".

[0067] The B1 ring, B2 ring, and C ring respectively correspond to the b1 ring and its substituent R b , the b2 ring and its substituent R b and the c ring and its substituent R c That is, formula (2A), formula (2B), and their unit structural formulas respectively correspond to the structures in which the B1 ring, B2 ring, and C ring as the B1 ring, B2 ring, and C ring of formula (1A), formula (1B), and their unit structural formulas are selected as "the B1 ring, B2 ring, and C ring having a 6-membered ring (which is a benzene ring)". In that sense, the rings in formula (2A), formula (2B), and their unit structural formulas are represented by the lowercase letters "b1", "b2", and "c".

[0068] <Description of the change in the ring structure due to the bond between substituents> The substituents R b and R cAmong them, adjacent groups may combine to form an aryl ring or a heteroaryl ring together with the b1 ring or the c ring, and at least one hydrogen in the formed ring may be substituted with aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (the two aryls may be bonded via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, or alkyldicycloalkylsilyl, and at least one hydrogen in these substituents may be substituted with aryl, heteroaryl, alkyl, or cycloalkyl. Details of the rings and substituents listed here will be described later in summary.

[0069] Therefore, depending on the mutual bonding form of the substituents in the b1 ring and the c ring, the polycyclic aromatic compound of formula (2A) or formula (2B) has a changing ring structure as shown in the following formulas (2A-fr1) to (2A-fr7) and formulas (2B-fr1) to (2B-fr7). The B1' ring and the C' ring in each formula correspond to the B1 ring and the C ring in formula (1A) and formula (1B), respectively. The display of φ1 and the B1 ring on the right side in each formula is omitted. In addition, the structural changes of the c ring represented by the following formulas also apply to its unit structural formula, but since there are no adjacent groups in the b2 ring in the unit structural formula, no new ring is formed.

[0070]

Chemical formula

Chemical formula

Chemical formula

[0071]

Chemical formula

[0072] In the above formulas (2A-fr1) to (2A-fr7) and formulas (2B-fr1) to (2B-fr7), the B1' ring and the C' ring, as described in formulas (2A) and (2B), have a plurality of substituents R b and R c where adjacent groups among them are bonded to form an aryl ring or a heteroaryl ring together with the b1 ring and the c ring respectively (it can also be said to be a condensed ring formed by condensing another ring structure to the b1 ring or the c ring). Also, as can be seen from the above formulas, for example, Rb of the b1 ring and R c of the c ring, and R c of different c rings do not fall under "adjacent groups" and basically do not bond to each other. That is, "adjacent groups" means groups adjacent on the same ring.

[0073] The above formulas (2A-fr1) to (2A-fr7) and formulas (2B-fr1) to (2B-fr7) have a B1' ring or a C' ring formed by condensing, for example, a benzene ring, an indole ring, a pyrrole ring, a benzofuran ring, or a benzothiophene ring, etc. to the benzene ring which is the b1 ring or the c ring, and the formed condensed ring B1' or condensed ring C' is, respectively, a naphthalene ring, a carbazole ring, an indole ring, a dibenzofuran ring, or a dibenzothiophene ring, etc.

[0074] For example, more specific examples of formulas (2A-fr1) to (2A-fr3) and formulas (2B-fr1) to (2B-fr3) are shown below. [Chemistry] [Chemistry]

[0075] The above formula (2A-fr1-ex) is a specific example of formula (2A-fr1), where two adjacent Rs in the b1 ring of formula (2A) b are bonded to form an aryl ring (naphthalene ring) represented by B1' together with the b1 ring (benzene ring). The formed aryl ring has a 6-membered ring (benzene ring b1) that shares a bond with the above-described condensed bicyclic structure. In addition, any substituent on the aryl ring B1' (B1 ring of formula (1A)) is represented by n Rs in addition to R b , and the upper limit of n is the maximum number that can be substituted.

[0076] The above formulas (2A-fr2-ex) and (2A-fr3-ex) are specific examples of formulas (2A-fr2) and (2A-fr3), respectively, where two adjacent Rs in the c ring of formula (2A) c are bonded to form a heteroaryl ring (carbazole ring and dibenzofuran ring, respectively) represented by C' together with the c ring (benzene ring). The formed heteroaryl ring has a 6-membered ring (benzene ring c) that shares a bond with the above-described condensed bicyclic structure. In addition, any substituent on the heteroaryl ring C' (C ring of formula (1A)) is represented by n Rs in addition to R c , and the upper limit of n is the maximum number that can be substituted.

[0077] The above formula (2B-fr1-ex) is a specific example of formula (2B-fr1), where two adjacent Rs in the b1 ring of formula (2B) b are bonded to form an aryl ring (naphthalene ring) represented by B1' together with the b1 ring (benzene ring). The formed aryl ring has a 6-membered ring (benzene ring b1) that shares a bond with the above-described condensed bicyclic structure. In addition, any substituent on the aryl ring B1' (B1 ring of formula (1B)) is represented by n Rs in addition to R b , and the upper limit of n is the maximum number that can be substituted.

[0078] The above formulas (2B-fr2-ex) and (2B-fr3-ex) are specific examples of formulas (2B-fr2) and (2B-fr3), respectively, where two adjacent Rs in the c ring of formula (2B) cThey are combined to form a heteroaryl ring (a carbazole ring and a dibenzofuran ring, respectively, represented by C’) together with the c ring (benzene ring). The formed heteroaryl ring has a 6-membered ring (benzene ring c) that shares a bond with the above-described condensed bicyclic structure. Note that any substituent on the heteroaryl ring C’ (the C ring in formula (1B)) is represented by R c In addition to this, there are n Rs, and the upper limit of n is the maximum number that can be substituted.

[0079] In the above description, formulas (2A) and (2B) were used, but this description can be similarly applied to their partial structural formulas. Further, the above description can be similarly applied to any form other than the specific examples described above.

[0080] An example in which the ring structure constituting the compound changes will be described more specifically. In this description, the formula representing the entire compound of formulas (2A) and (2B) above, and the formulas representing the partial structures of formula (φ2-m1), formula (φ2-m2), formula (φ2-p1), and formula (φ2-p2) are simplified (the substituents R a 、R b and R c are made invisible but actually exist), and are represented by the following overall formula (Y2X3-A), overall formula (Y2X4-B), partial formula (φ2-Y2X3-m1), partial formula (φ2-Y2X3-m2), partial formula (φ2-Y2X4-p1), and partial formula (φ2-Y2X4-p2), respectively.

Chemical formula

[0081] For example, the case where a 5-membered ring structure is condensed to the b1 ring in the overall formula (Y2X3-A) is shown below.

Chemical formula

[0082] Here, Q is independently >N-R, >O, >S, >C(-R)2, >Si(-R)2, or >Se, where R in >N-R, R in >C(-R)2, and R in >Si(-R)2 are each independently an optionally substituted aryl or an optionally substituted heteroaryl, and the same applies hereinafter. Details of the substituents listed here will be summarized and described later. When Q is X 1 at the meta position with respect to it, the TADF property tends to be high. Also, in order to shorten the emission wavelength, it is preferable that Q is >O. Further, when Q is >S, >Si(-R)2, or >Se, which is a heavier atom than a B atom, a C atom, an N atom, and an O atom, the TADF property tends to be high due to the heavy atom effect.

[0083] When Q is >O, the b1 ring is a dibenzofuran ring, and this case is shown below.

Chemical formula

[0084] Also, regarding the partial structure φ2, a 5-membered ring structure can be similarly condensed. For example, the case where a 5-membered ring structure is condensed to the c ring in the partial formula (φ2-Y2X3-m1) is shown below.

Chemical formula

[0085] When Q is >O, the c ring is a dibenzofuran ring, and this case is shown below.

Chemical formula

[0086] <Description of the central element Y in the compound> In each formula, Y is B, P, P=O, P=S, Al, Ga, As, Si-R, or Ge-R, and R in the Si-R and Ge-R is aryl, heteroaryl, alkyl, or cycloalkyl. In the case of P=O, P=S, Si-R, or Ge-R, the atoms bonding to the a ring, B1 ring (b1 ring), B2 ring (b2 ring), and C ring (c ring) are P, Si, or Ge. Y is preferably B, P, P=O, P=S, or Si-R, more preferably B, P, P=O, or P=S, and particularly preferably B. Details of the substituents listed here will be summarized and described later.

[0087] Next, examples of Y will be further specifically described using the overall formula and partial formulas described above.

[0088] By arranging Y in the meta positions to each other, the multiple resonance effect is enhanced, and there is a tendency to obtain high TADF properties and emission with a narrow half-width. When Y is P, P=O, or P=S, there is a tendency to obtain emission with a shorter wavelength and a large ΔEST, and when Y is B, there is a tendency to obtain emission with a longer wavelength and a small ΔEST. [Chemical formula]

[0089] By arranging Y in the para positions to each other, the multiple resonance effect is weakened, and there is a tendency to obtain a large ΔEST and emission with a narrow half-width. When Y is P, P=O, and P=S, there is a tendency to obtain emission with a shorter wavelength and a large ΔEST, and when Y is B, there is a tendency to obtain emission with a longer wavelength and a small ΔEST. [Chemical formula]

[0090] Also, the partial structure φ2 can be considered in the same way. [Chemical formula] [Chemical formula]

Chem.

[0091] <Linking element X in the compound 1 and X 2 description> X in each formula 1 is, independently of each other, >N-R, >O, >S, >C(-R)2, >Si(-R)2, or >Se, where R in >N-R, R in >C(-R)2, and R in >Si(-R)2 are, independently of each other, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkyl, or optionally substituted cycloalkyl. X 1 From the viewpoint of stability, >N-R, >O, >S, or >C(-R)2 is preferable, and >N-R or >O is more preferable. From the viewpoint of short-wavelength emission, >N-R, >O, or >C(-R)2 is preferable, and >O or >C(-R)2 is more preferable. X in each formula 2 is, independently of each other, N or C-R, where R in C-R is, independently of each other, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkyl, or optionally substituted cycloalkyl. X 2 is preferably N. Details of the substituents listed here will be described later in a summary.

[0092] Next, examples of X 1 and X 2 will be further specifically described using the overall formula and partial formulas described above.

[0093] By arranging X in the meta - position with respect to each other, the multiple resonance effect is enhanced, and there is a tendency to obtain a small ΔEST. On the other hand, by arranging X in the para - position with respect to each other, the multiple resonance effect is weakened, and there is a tendency to obtain a large ΔEST. When Y is P, P = O, and P = S, emission at a shorter wavelength and a large ΔEST are obtained, and when Y is B, emission at a longer wavelength and a small ΔEST are obtained. Further, since X in the polycyclic aromatic compound of the present invention is always arranged in the meta - position or para - position, it has a robust skeleton and tends to emit light with a narrow half - value width.

Chemical formula

[0094] Also, the partial structure φ2 can be considered in the same way.

Chemical formula

[0095]

Chemical formula

[0096] Also, the said X 1For >C(-R)2, the two Rs and for >Si(-R)2, the two Rs may each independently be bonded by a single bond or a linking group. Examples of such a linking group include -CH2-CH2-, -CHR-CHR-, -CR2-CR2-, -CH=CH-, -CR=CR-, -C≡C-, -N(-R)-, -O-, -S-, -C(-R)2-, -Si(-R)2-, or -Se-. For example, the following structures are included. Note that the Rs in -CHR-CHR-, -CR2-CR2-, -CR=CR-, -N(-R)-, -C(-R)2-, and -Si(-R)2- are each independently hydrogen, aryl, heteroaryl, alkyl, alkenyl, alkynyl, or cycloalkyl, and at least one hydrogen in the R may be substituted with alkyl or cycloalkyl. Also, two adjacent Rs may form a ring and may form cycloalkylene, arylene, and heteroarylene. Details of the substituents listed here will be described later in summary. [Chemical Formula]

[0097] Among these, a single bond, -CR=CR-, -N(-R)-, -O-, -S-, -C(-R)2-, -Si(-R)2-, and -Se- as linking groups are preferred, a single bond, -CR=CR-, -N(-R)-, -O-, -S-, and -C(-R)2- as linking groups are more preferred, a single bond, -CR=CR-, -N(-R)-, -O-, and -S- as linking groups are even more preferred, and a single bond is most preferred.

[0098] The position where two Rs are bonded by a single bond or a linking group is not particularly limited as long as it is a bondable position, but it is preferably bonded at the most adjacent position. For example, when the two Rs are phenyl groups, it is preferably bonded between the ortho (2-position) positions with reference to the bonding position (1-position) of "C" or "Si" in the phenyl group (refer to the above structural formula).

[0099] <X1 <Description of the change in the ring structure due to the bond between the ring and [X]] X 1 Among R of >N-R, R of >C(-R)2, and R of >Si(-R)2, at least one may be bonded to at least one of the B1 ring (b1 ring), B2 ring (b2 ring), C ring (c ring), and a ring in each formula by a single bond or a linking group. X that can be involved in the bonding 1 As such, >N-R and >C(-R)2 are preferred, and >N-R is more preferred. As the ring to be bonded, the B1 ring (b1 ring) and the C ring (c ring) are preferred. Examples of the linking group for bonding R and the ring include -CH2-CH2-, -CHR-CHR-, -CR2-CR2-, -CH=CH-, -CR=CR-, -C≡C-, -N(-R)-, -O-, -S-, -C(-R)2-, -Si(-R)2-, and -Se-. Among them, -CR=CR-, -N(-R)-, -O-, -S-, and -C(-R)2- are preferred, and -CR=CR-, -N(-R)-, -O-, and -S- are more preferred. In the case of the above-mentioned "-CHR-CHR-", "-CR2-CR2-", "-CR=CR-", "-N(-R)-", "-C(-R)2-", and "-Si(-R)2-", each R is independently hydrogen, aryl, heteroaryl, alkyl, alkenyl, alkynyl, or cycloalkyl, and at least one hydrogen in the R may be substituted with alkyl or cycloalkyl. Also, two adjacent Rs may form a ring to form cycloalkylene, arylene, or heteroarylene. Details of the substituents listed here will be summarized and described later.

[0100] In Formula (1A) and Formula (1B), "the X 1 Among R of >N-R, R of >C(-R)2, and R of >Si(-R)2 as such, at least one is bonded to at least one of the B1 ring, B2 ring, C ring, and a ring by a single bond or a linking group" and the provision in Formula (2A) and Formula (2B) is "the X 1At least one of R in >N-R, R in >C(-R)2, and R in >Si(-R)2 is bonded to at least one of the a-ring, b1-ring, b2-ring, and c-ring by a single bond, -CH=CH-, -CR=CR-, -C≡C-, -N(-R)-, -O-, -S-, -C(-R)2-, -Si(-R)2-, or -Se-. This corresponds to the regulation of "

[0101] This regulation can be expressed, for example, by the following structural formula which is a combination of formula (2A) and φ2 as formula (φ2-m1) (n = 1). Note that the substituents R a , R b and R c are not shown but actually exist.

Chemical Structure

[0102] This regulation can be expressed, for example, by the following structural formula which is a combination of formula (2B) and φ2 as formula (φ2-p1) (n = 1). Note that the substituents R a , R b and R c are not shown but actually exist.

Chemical formula

[0103] Note that the description of the above specific examples can be similarly applied to all forms other than these specific examples.

[0104] <Description of the form in which adjacent C rings or c rings are bonded to each other> In the above formula (1A), formula (φ1-m1), and formula (φ1-m2), adjacent C rings may be bonded to each other independently by a single bond or a linking group. Further, in the above formula (2A), formula (φ2-m1), and formula (φ2-m2), adjacent R's in adjacent c rings (X that links two c rings c to the ortho position of R 2 with respect to c ) may be bonded to each other independently by a single bond or a linking group. Such a bond is preferably when X between two C rings or two c rings 2 is N. When bonding, it is preferable that all of the adjacent C rings or c rings are bonded to each other.

[0105] Examples of the linking group include -CH2-CH2-, -CHR-CHR-, -CR2-CR2-, -CH=CH-, -CR=CR-, -C≡C-, -N(-R)-, -O-, -S-, -C(-R)2-, -Si(-R)2-, and -Se-. Among them, -CR=CR-, -N(-R)-, -O-, -S-, and -C(-R)2- are preferable, and -CR=CR-, -N(-R)-, -O-, and -S- are more preferable. In the above, R in "-CHR-CHR-", "-CR2-CR2-", "-CR=CR-", "-N(-R)-", "-C(-R)2-", and "-Si(-R)2-" is independently hydrogen, aryl, heteroaryl, alkyl, alkenyl, alkynyl, or cycloalkyl, and at least one hydrogen in the R may be substituted with alkyl or cycloalkyl. Further, two adjacent R's may form a ring, and may form cycloalkylene, arylene, and heteroarylene. Details of the substituents listed here will be described together later.

[0106] Next, examples of the bonding between adjacent C rings or c rings will be further specifically described using the overall formulas and partial formulas described above.

[0107] As the group connecting the two rings, from the viewpoint of high TADF property, a single bond, >O and >C(-R)2 are preferable, and a single bond is more preferable.

[0108]

Chemical formula

[0109] Also, the partial structure φ2 can be considered in the same way.

Chemical formula

[0110]

Chemical formula

[0111] <Description of the structural changes of the a ring, b1 ring, c ring, and b2 ring>

[0112] In the previous explanations, the a-ring, b1-ring, c-ring, and b2-ring were described as benzene rings. Hereinafter, examples will be described in which the a-ring, b1-ring, c-ring, and b2-ring are structurally changed to a 5-membered or 6-membered aryl ring or heteroaryl ring that is not a benzene ring. Note that the previous explanations are similarly understood even when these rings undergo the following structural changes.

[0113] <Structural change of the a ring> In the a-ring, "-C(-R a )=" may be replaced by "-N=", and it may be a pyridine ring. The a-ring having "-C(-R a )=" is included only in Formula (1A), Formula (φ1-m1), Formula (φ1-m2), Formula (2A), Formula (φ2-m1), and Formula (φ2-m2), and is not included in Formula (1B), Formula (φ1-p1), Formula (φ1-p2), Formula (2B), Formula (φ2-p1), and Formula (φ2-p2). Note that the following structural diagrams are diagrams showing only a part of the a-ring and its peripheral structure.

Chemical formula

[0114] <Structural changes of the b1 ring and c ring> In the b1 ring and the c ring, any "-C(-R)=" (where R is R b or R c ) may be replaced by "-N=".

Chemical formula

[0115] In addition, there are also the following modification examples.

Chemical formula

[0116] The same applies when other positions are replaced by "-N=" or when the b1 ring changes.

[0117] Also, in the b1 ring and the c ring, any "-C(-R)=C(-R)-" (where R is R b or R cIt may be replaced by "-N(-R)-", "-O-", "-S-", "-C(-R)2-", "-Si(-R)2-", or "-Se-", and R in the "-N(-R)-", R in the "-C(-R)2-", and R in the "-Si(-R)2-" are aryl, heteroaryl, alkyl, or cycloalkyl. Details of the substituents listed here will be summarized and described later.

Chemical formula

[0118] In addition, there are also the following modification examples.

Chemical formula

[0119] The same applies when other positions are replaced by "-N(-R)-", "-O-", "-S-", "-C(-R)2-", "-Si(-R)2-", or "-Se-", or when the b1-ring changes.

[0120] The two Rs in the "-C(-R)2-" and the two Rs in the "-Si(-R)2-" may each independently be bonded by a single bond or a linking group. Examples of such a linking group include -CH2-CH2-, -CHR-CHR-, -CR2-CR2-, -CH=CH-, -CR=CR-, -C≡C-, -N(-R)-, -O-, -S-, -C(-R)2-, -Si(-R)2-, or -Se-. For example, the following structures are included. Note that the Rs in -CHR-CHR-, -CR2-CR2-, -CR=CR-, -N(-R)-, -C(-R)2-, and -Si(-R)2- are each independently hydrogen, aryl, heteroaryl, alkyl, alkenyl, alkynyl, or cycloalkyl, and at least one hydrogen in the R may be substituted with alkyl or cycloalkyl. Also, two adjacent Rs may form a ring to form cycloalkylene, arylene, and heteroarylene. Details of the substituents listed here will be described later in summary.

Chemical formula

[0121] Among these, a single bond, -CR=CR-, -N(-R)-, -O-, -S-, -C(-R)2-, -Si(-R)2-, and -Se- as linking groups are preferred, a single bond, -CR=CR-, -N(-R)-, -O-, -S-, and -C(-R)2- as linking groups are more preferred, a single bond, -CR=CR-, -N(-R)-, -O-, and -S- as linking groups are even more preferred, and a single bond is most preferred.

[0122] The position where two Rs are bonded by a single bond or a linking group is not particularly limited as long as it is a bondable position, but it is preferably bonded at the most adjacent position. For example, when the two Rs are phenyl groups, it is preferable to bond the ortho (2-position) positions with reference to the bonding position (1-position) of "C" or "Si" in the phenyl group (refer to the above structural formula).

[0123] <Structural change of the b2 ring> In the b2 ring, any "-C(-R b )=" may be replaced by "-N=". The following structural diagrams only extract a part of the b2 ring and its peripheral structure.

Chemical formula

[0124] Also, in the b2 ring, one "-C(-R b )=" is a single bond, and the other "-C(-R b )=" may be replaced by "-N(-R)-", "-O-", "-S-", "-C(-R)2-", "-Si(-R)2-", or "-Se-". The R in "-N(-R)-", the R in "-C(-R)2-", and the R in "-Si(-R)2-" are aryl, heteroaryl, alkyl, or cycloalkyl. The details of the substituents listed here will be summarized and described later. The other "-C(-R b )=" is preferably replaced by "-N(-R)-", "-O-", "-S-", or "-C(-R)2-", and more preferably replaced by "-N(-R)-", "-O-", or "-S-". The following structural diagrams only extract a part of the b2 ring and its peripheral structure.

Chemical formula

[0125] One "-C(-R b )=" and the other "-C(-R b )=" being reversed is the same.

[0126] The two Rs of the "-C(-R)2-" and the two Rs of the "-Si(-R)2-" may each independently be bonded by a single bond or a linking group. Examples of this linking group include -CH2-CH2-, -CHR-CHR-, -CR2-CR2-, -CH=CH-, -CR=CR-, -C≡C-, -N(-R)-, -O-, -S-, -C(-R)2-, -Si(-R)2-, or -Se-. For example, the following structures may be mentioned. Here, the R in -CHR-CHR-, the R in -CR2-CR2-, the R in -CR=CR-, the R in -N(-R)-, the R in -C(-R)2-, and the R in -Si(-R)2- are each independently hydrogen, aryl, heteroaryl, alkyl, alkenyl, alkynyl, or cycloalkyl, and at least one hydrogen in the R may be substituted with alkyl or cycloalkyl. Also, two adjacent Rs may form a ring and may form cycloalkylene, arylene, and heteroarylene. The details of the substituents listed here will be described later in summary. [Chemical formula]

[0127] Among these, a single bond, -CR=CR-, -N(-R)-, -O-, -S-, -C(-R)2-, -Si(-R)2-, and -Se- as the linking group are preferred, a single bond, -CR=CR-, -N(-R)-, -O-, -S-, and -C(-R)2- as the linking group are more preferred, a single bond, -CR=CR-, -N(-R)-, -O-, and -S- as the linking group are even more preferred, and a single bond is most preferred.

[0128] The position where two Rs are bonded by a single bond or a linking group is not particularly limited as long as it is a bondable position, but it is preferably bonded at the most adjacent position. For example, when the two Rs are phenyl groups, it is preferably bonded between the ortho (2-position) positions with reference to the bonding position (1-position) of "C" or "Si" in the phenyl group (refer to the above structural formula).

[0129] <Description of the specific structural changes of the a ring, b1 ring, c ring, and b2 ring> Next, an example in which the a-ring, b1-ring, c-ring, and b2-ring undergo structural changes will be further specifically described using the overall formula and partial formulas described above.

[0130] When the a-ring, b1-ring, c-ring, and b2-ring form a nitrogen (N)-containing aromatic ring, X in each formula 1 or X 2 when N is in the ortho or para position with respect to it, the multiple resonance effect is enhanced, and there is a tendency to obtain emission at a shorter wavelength and a smaller ΔEST. When N is in the meta position with respect to X in each formula 1 or X 2 the multiple resonance effect is weakened, and there is a tendency to obtain emission at a longer wavelength and a larger ΔEST. However, these apply when it is a 6-membered ring. For example, the case where the carbon atoms of the a-ring, b1-ring, and c-ring in the overall formula (Y2X3-A) are substituted with N is shown below.

Chemical formula

[0131] Also, the b2-ring in the partial structure φ2 can be considered in the same way.

[0132] The b1-ring, c-ring, and b2-ring can be structurally changed to a 5-membered or 6-membered aryl ring or heteroaryl ring that is not a benzene ring. For example, in the overall formula (Y2X3-A), the case where the b1-ring and c-ring are substituted with a 5-membered ring structure having a benzene ring is shown below.

Chemical formula

[0133] Here, Q is, independently of each other, >N-R, >O, >S, >C(-R)2, >Si(-R)2, or >Se, and R of >N-R, R of >C(-R)2, and R of >Si(-R)2 are each independently an optionally substituted aryl or an optionally substituted heteroaryl, and the same applies hereinafter. The details of the substituents listed here will be summarized and described later. From the perspective of stability, >C(-R)2, >S, or >N-R is preferred for Q, and >S is more preferred. Also, when having a 5-membered ring structure, the TADF property becomes lower.

[0134] More specifically, when Q is >S, the b1 ring and the c ring become benzothiophene rings.

Chemical formula

[0135] Also, the partial structure φ2 can be considered in the same way. For example, in the partial formula (φ2-Y2X3-m1), the case where the c ring is replaced by a 5-membered ring structure having a benzene ring is shown below.

Chemical formula

[0136] More specifically, when Q is >S, the c ring becomes a benzothiophene ring.

Chemical formula

[0137] <Specific description of the ring and substituents> Next, the details of the rings and substituents (including the second substituents that further substitute the first substituent) listed in the previous explanations will be summarized and explained.

[0138] The "aryl ring" is, for example, an aryl ring having 6 to 30 carbon atoms, preferably an aryl ring having 6 to 20 carbon atoms, an aryl ring having 6 to 16 carbon atoms, an aryl ring having 6 to 12 carbon atoms, or an aryl ring having 6 to 10 carbon atoms, etc. Note that the "aryl ring" as the B1 ring and the C ring in formula (1A) and formula (1B) is the "R" defined in formula (2A) and formula (2B) b and R cThis corresponds to an "aryl ring" formed by the linkage of adjacent groups among them together with the b1 ring and the c ring. Regarding this "formed aryl ring", since the b1 ring or the c ring is already composed of a benzene ring having 6 carbon atoms, the total number of carbon atoms of the condensed ring in which the smallest 5-membered ring is condensed to this benzene ring is 9, which is the lower limit of the number of carbon atoms.

[0139] Specific "aryl rings" include, for example, a benzene ring which is a monocyclic system, a naphthalene ring which is a condensed bicyclic system, an acenaphthylene ring, a fluorene ring, a phenalene ring, or a phenanthrene ring, an anthracene ring which are condensed tricyclic systems, a triphenylene ring, a pyrene ring, or a naphthacene ring which are condensed tetracyclic systems, or a perylene ring or a pentacene ring which are condensed pentacyclic systems.

[0140] The "heteroaryl ring" is, for example, a heteroaryl ring having 2 to 30 carbon atoms, preferably a heteroaryl ring having 2 to 25 carbon atoms, a heteroaryl ring having 2 to 20 carbon atoms, a heteroaryl ring having 2 to 15 carbon atoms, or a heteroaryl ring having 2 to 10 carbon atoms. Further, the "heteroaryl ring" is, for example, a heterocyclic ring containing 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen in addition to carbon as ring-constituting atoms. Note that the "heteroaryl ring" as the B1 ring and the C ring in the formula (1A) and the formula (1B) corresponds to a "heteroaryl ring" formed by the linkage of adjacent groups among "R" b and R c together with the b1 ring and the c ring. Regarding this "formed aryl ring", since the b1 ring or the c ring is already composed of a benzene ring having 6 carbon atoms, the total number of carbon atoms of the condensed ring in which the smallest 5-membered ring is condensed to this benzene ring is 6, which is the lower limit of the number of carbon atoms. However, since the b1 ring and the c ring which are this benzene ring may be changed to a nitrogen-containing heteroaryl ring (6-membered ring or 5-membered ring) or an oxygen- and sulfur-containing heteroaryl ring (5-membered ring) as described above, in this case, the lower limit of the number of carbon atoms changes accordingly.

[0141] Specific "heteroaryl rings" include, for example, pyrrole rings, oxazole rings, isoxazole rings, thiazole rings, isothiazole rings, imidazole rings, oxadiazole rings, thiadiazole rings, triazole rings, tetrazole rings, pyrazole rings, pyridine rings, pyrimidine rings, pyridazine rings, pyrazine rings, triazine rings, indole rings, isoindole rings, 1H-indazole rings, benzimidazole rings, benzoxazole rings, benzothiazole rings, 1H-benzotriazole rings, quinoline rings, isoquinoline rings, cinnoline rings, quinazoline rings, quinoxaline rings, phenanthroline rings, phthalazine rings, naphthyridine rings, purine rings, pteridine rings, carbazole rings, acridine rings, phenoxathiine rings, phenoxazine rings, phenothiazine rings, phenazine rings, phenazasiline rings, indolizine rings, furan rings, benzofuran rings, isobenzofuran rings, dibenzofuran rings, naphthobenzofuran rings, thiophene rings, benzothiophene rings, isobenzothiophene rings, dibenzothiophene rings, naphthobenzothiophene rings, benzophosphole rings, dibenzophosphole rings, benzophosphole oxide rings, dibenzophosphole oxide rings, furazan rings, thianthrene rings, indolocarbazole rings, benzoindolocarbazole rings, benzobenzoindolocarbazole rings, imidazoline rings, or oxazoline rings, etc.

[0142] "Aryl" is, for example, aryl having 6 to 30 carbon atoms, preferably aryl having 6 to 20 carbon atoms, aryl having 6 to 16 carbon atoms, aryl having 6 to 12 carbon atoms, or aryl having 6 to 10 carbon atoms, etc.

[0143] Specific "aryl" includes, for example, phenyl which is a monocyclic system, biphenylyl (2-biphenylyl, 3-biphenylyl, or 4-biphenylyl) which is a bicyclic system, naphthyl (1-naphthyl or 2-naphthyl) which is a condensed bicyclic system, terphenylyl (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-terphenyl-4-yl, o-terphenyl-2-yl, o-terphenyl-3-yl, o-terphenyl-4-yl, p-terphenyl-2-yl, p-terphenyl-3-yl, or p-terphenyl-4-yl) which is a tricyclic system, acenaphthylen-(1-, 3-, 4-, or 5-)yl, fluorene-(1-, 2-, 3-, 4-, or 9-)yl, phenalen-(1- or 2-)yl, or phenanthren-(1-, 2-, 3-, 4-, or 9-)yl which are condensed tricyclic systems, quarterphenyl (5'-phenyl-m-terphenyl-2-yl, 5'-phenyl-m-terphenyl-3-yl, 5'-phenyl-m-terphenyl-4-yl, or m-quarterphenyl) which is a tetracyclic system, triphenylene-(1- or 2-)yl, pyrene-(1-, 2-, or 4-)yl, or naphthacene-(1-, 2-, or 5-)yl which are condensed tetracyclic systems, or perylene-(1-, 2-, or 3-)yl, or pentacene-(1-, 2-, 5-, or 6-)yl which are condensed pentacyclic systems, etc.

[0144] Note that the aryl as the second substituent, i.e., the aryl as the substituent (the second substituent) that further substitutes the substituent (the first substituent), also includes a structure in which at least one hydrogen in the aryl is substituted with an aryl such as phenyl (specific examples are the groups described above), an alkyl such as methyl (specific examples are the groups described later), or a cycloalkyl such as cyclohexyl or adamantyl (specific examples are the groups described later). As an example, when the second substituent is a fluorenyl group, at least one hydrogen at the 9-position thereof is a fluorenyl group substituted with an aryl such as phenyl, an alkyl such as methyl, or a cycloalkyl such as cyclohexyl or adamantyl, and such a group is also included in the aryl as the second substituent.

[0145] "Arylene" is, for example, an arylene having 6 to 30 carbon atoms, preferably an arylene having 6 to 20 carbon atoms, an arylene having 6 to 16 carbon atoms, an arylene having 6 to 12 carbon atoms, or an arylene having 6 to 10 carbon atoms. Specific examples of "arylene" include, for example, a structure obtained by removing one hydrogen from the above-described "aryl" (monovalent group) to form a divalent group.

[0146] "Heteroaryl" is, for example, a heteroaryl having 2 to 30 carbon atoms, preferably a heteroaryl having 2 to 25 carbon atoms, a heteroaryl having 2 to 20 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, or a heteroaryl having 2 to 10 carbon atoms. Further, "heteroaryl" is a monovalent group such as a heterocyclic ring containing 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen in addition to carbon as ring-constituting atoms.

[0147] Specific "heteroaryl" includes, for example, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, pyrazolyl, pyridinyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, indolyl, isoindolyl, 1H-indazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolinyl, isoquinolinyl, cinnolinyl, quinazolinyl, quinoxalinyl, phenanthrolinyl, phthalazinyl, naphthyridinyl, purinyl, pteridinyl, carbazolyl, acridinyl, phenoxathiinyl, phenoxazinyl, phenothiazinyl, phenazinyl, phenazasilinyl, indolizinyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, naphthobenzofuranyl, thiophenyl, benzothiophenyl, isobenzothiophenyl, dibenzothiophenyl, naphthobenzothiophenyl, benzophospholyl, dibenzophospholyl, a monovalent group of a benzophosphole oxide ring, a monovalent group of a dibenzophosphole oxide ring, phthalazinyl, thianthrenyl, indolocarbazolyl, benzindolocarbazolyl, benzobenzindolocarbazolyl, imidazolinyl, oxazolinyl, or dibenzosilacyclopentadienyl, etc.

[0148] Note that the heteroaryl as the second substituent, i.e., the heteroaryl as the substituent (the second substituent) that further substitutes the substituent (the first substituent), also includes a structure in which at least one hydrogen in the heteroaryl is substituted with an aryl such as phenyl (specific examples are the groups described above), an alkyl such as methyl (specific examples are the groups described later), or a cycloalkyl such as cyclohexyl or adamantyl (specific examples are the groups described later). As an example, when the second substituent is a carbazolyl group, a carbazolyl group in which at least one hydrogen at the 9-position is substituted with an aryl such as phenyl, an alkyl such as methyl, or a cycloalkyl such as cyclohexyl or adamantyl, etc., is also included in the heteroaryl as the second substituent.

[0149] "Heteroarylene" is, for example, heteroarylene having 2 to 30 carbon atoms, preferably heteroarylene having 2 to 25 carbon atoms, heteroarylene having 2 to 20 carbon atoms, heteroarylene having 2 to 15 carbon atoms, or heteroarylene having 2 to 10 carbon atoms, etc. Further, "heteroarylene" is a divalent group such as a heterocyclic ring containing 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen in addition to carbon as ring-constituting atoms, for example. Specific examples of "heteroarylene" include, for example, a structure in which one hydrogen is removed from the above-described "heteroaryl" (monovalent group) to form a divalent group.

[0150] "Diarylamino" is an amino group substituted with two aryls, and for the details of this aryl, the description of "aryl" above can be cited. "Diheteroarylamino" is an amino group substituted with two heteroaryls, and for the details of this heteroaryl, the description of "heteroaryl" above can be cited. "Arylheteroarylamino" is an amino group substituted with an aryl and a heteroaryl, and for the details of this aryl and heteroaryl, the descriptions of "aryl" and "heteroaryl" above can be cited.

[0151] "Diarylborolyl" is a borolyl group substituted by two aryls, and for the details of this aryl, the description of "aryl" mentioned above can be cited. Further, these two aryls may be bonded via a single bond or a linking group (for example, -CH2-CH2-, -CHR-CHR-, -CR2-CR2-, -CH=CH-, -CR=CR-, -C≡C-, >N-R, >O, >S, >C(-R)2, >Si(-R)2, or >Se). Here, R in -CHR-CHR-, R in -CR2-CR2-, R in -CR=CR-, R in >N-R, R in >C(-R)2, and R in >Si(-R) is aryl, heteroaryl, diarylamino, alkyl, alkenyl, alkynyl, cycloalkyl, alkoxy, or aryloxy, and at least one hydrogen in the said R may be further substituted by aryl, heteroaryl, alkyl, alkenyl, alkynyl, or cycloalkyl. Also, two adjacent Rs may form a ring, and may form cycloalkylene, arylene, and heteroarylene. For the details of the substituents listed here, the descriptions of "aryl", "arylene", "heteroaryl", "heteroarylene", and "diarylamino" mentioned above, as well as the descriptions of "alkyl", "alkenyl", "alkynyl", "cycloalkyl", "cycloalkylene", "alkoxy", and "aryloxy" to be described later can be cited.

[0152] "Alkyl" may be either straight-chain or branched-chain, for example, straight-chain alkyl having 1 to 24 carbon atoms or branched-chain alkyl having 3 to 24 carbon atoms, preferably alkyl having 1 to 18 carbon atoms (branched-chain alkyl having 3 to 18 carbon atoms), alkyl having 1 to 12 carbon atoms (branched-chain alkyl having 3 to 12 carbon atoms), alkyl having 1 to 6 carbon atoms (branched-chain alkyl having 3 to 6 carbon atoms), alkyl having 1 to 5 carbon atoms (branched-chain alkyl having 3 to 5 carbon atoms), alkyl having 1 to 4 carbon atoms (branched-chain alkyl having 3 to 4 carbon atoms), and the like.

[0153] Specific "alkyl" includes, for example, methyl, ethyl, n-propyl, isopropyl, 1-ethyl-1-methylpropyl, 1,1-diethylpropyl, 1,1,2-trimethylpropyl, 1,1,2,2-tetramethylpropyl, 1-ethyl-1,2,2-trimethylpropyl, n-butyl, isobutyl, s-butyl, t-butyl, 2-ethylbutyl, 1,1-dimethylbutyl, 3,3-dimethylbutyl, 1,1-diethylbutyl, 1-ethyl-1-methylbutyl, 1-propyl-1-methylbutyl, 1,1,3-trimethylbutyl, 1-ethyl-1,3-dimethylbutyl, n-pentyl, isopentyl, neopentyl, t-pentyl (t-amyl), 1-methylpentyl, 2-propylpentyl, 1,1-dimethylpentyl, 1-ethyl-1-methylpentyl, 1-propyl-1-methylpentyl, 1-butyl-1-methylpentyl, 1,1,4-trimethylpentyl, n-hexyl, 1-methylhexyl, 2-ethylhexyl, 1,1-dimethylhexyl, 1-ethyl-1-methylhexyl, 1,1,5-trimethylhexyl, 3,5,5-trimethylhexyl, n-heptyl, 1-methylheptyl, 1-hexylheptyl, 1,1-dimethylheptyl, 2,2-dimethylheptyl, 2,6-dimethyl-4-heptyl, n-octyl, t-octyl (1,1,3,3-tetramethylbutyl), 1,1-dimethyloctyl, n-nonyl, n-decyl, 1-methyldecyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, or n-eicosyl, etc.

[0154] Regarding "alkenyl", the above description of "alkyl" can be referred to. It is a group in which the C-C single bond in the structure of "alkyl" is replaced by a C=C double bond, including not only a group in which one single bond is replaced by a double bond but also a group in which two or more single bonds are replaced by double bonds (also called alkadien-yl or alkanetriene-yl).

[0155] Regarding "alkynyl", the description of "alkyl" mentioned above can be referred to. It is a group in which the C-C single bond in the structure of "alkyl" is replaced by a C≡C triple bond, and it includes not only a group in which only one single bond is replaced by a triple bond but also a group in which two or more single bonds are replaced by triple bonds (also called alkadiyn-yl or alkanetriyn-yl).

[0156] "Cycloalkyl" is, for example, cycloalkyl having 3 to 24 carbon atoms, preferably cycloalkyl having 3 to 20 carbon atoms, cycloalkyl having 3 to 16 carbon atoms, cycloalkyl having 3 to 14 carbon atoms, cycloalkyl having 3 to 12 carbon atoms, cycloalkyl having 5 to 10 carbon atoms, cycloalkyl having 5 to 8 carbon atoms, cycloalkyl having 5 to 6 carbon atoms, or cycloalkyl having 5 carbon atoms, etc.

[0157] Specific "cycloalkyl" includes, for example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, or their C1-C5 or C1-C4 alkyl (especially methyl) substitution products, norbornenyl, bicyclo[1.1.0]butyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.0]pentyl, bicyclo[2.1.1]hexyl, bicyclo[3.1.0]hexyl, bicyclo[2.2.1]heptyl, bicyclo[2.2.2]octyl, adamantyl, diamantyl, decahydronaphthalenyl, or decahydroazulenyl, etc.

[0158] "Cycloalkylene" is, for example, cycloalkylene having 3 to 24 carbon atoms, preferably cycloalkylene having 3 to 20 carbon atoms, cycloalkylene having 3 to 16 carbon atoms, cycloalkylene having 3 to 14 carbon atoms, cycloalkylene having 3 to 12 carbon atoms, cycloalkylene having 5 to 10 carbon atoms, cycloalkylene having 5 to 8 carbon atoms, cycloalkylene having 5 to 6 carbon atoms, or cycloalkylene having 5 carbon atoms, etc. Specific "cycloalkylene" includes, for example, the structure obtained by removing one hydrogen from the above-mentioned "cycloalkyl" (monovalent group) to form a divalent group.

[0159] "Alkoxy" may be either linear or branched, for example, linear alkoxy having 1 to 24 carbon atoms or branched alkoxy having 3 to 24 carbon atoms, preferably alkoxy having 1 to 18 carbon atoms (branched alkoxy having 3 to 18 carbon atoms), alkoxy having 1 to 12 carbon atoms (branched alkoxy having 3 to 12 carbon atoms), alkoxy having 1 to 6 carbon atoms (branched alkoxy having 3 to 6 carbon atoms), alkoxy having 1 to 5 carbon atoms (branched alkoxy having 3 to 5 carbon atoms), alkoxy having 1 to 4 carbon atoms (branched alkoxy having 3 to 4 carbon atoms), and the like.

[0160] Specific "alkoxy" includes, for example, methoxy, ethoxy, n-propoxy, isopropoxy, 1-ethyl-1-methylpropoxy, 1,1-diethylpropoxy, 1,1,2-trimethylpropoxy, 1,1,2,2-tetramethylpropoxy, 1-ethyl-1,2,2-trimethylpropoxy, n-butoxy, isobutoxy, s-butoxy, t-butoxy, 2-ethylbutoxy, 1,1-dimethylbutoxy, 3,3-dimethylbutoxy, 1,1-diethylbutoxy, 1-ethyl-1-methylbutoxy, 1-propyl-1-methylbutoxy, 1,1,3-trimethylbutoxy, 1-ethyl-1,3-dimethylbutoxy, n-pentyloxy, isopentyloxy, neopentyloxy, t-pentyloxy (t-amyloxy), 1-methylpentyloxy, 2-propylpentyloxy, 1,1-dimethylpentyloxy, 1-ethyl-1-methylpentyloxy, 1-propyl-1-methylpentyloxy, 1-butyl-1-methylpentyloxy, 1,1,4-trimethylpentyloxy, n-hexyloxy, 1-methylhexyloxy, 2-ethylhexyloxy, 1,1-dimethylhexyloxy, 1-ethyl-1-methylhexyloxy, 1,1,5-trimethylhexyloxy, 3,5,5-trimethylhexyloxy, n-heptyloxy, 1-methylheptyloxy, 1-hexylheptyloxy, 1,1-dimethylheptyloxy, 2,2-dimethylheptyloxy, 2,6-dimethyl-4-heptyloxy, n-octyloxy, t-octyloxy (1,1,3,3-tetramethylbutyloxy), 1,1-dimethyloctyloxy, n-nonyloxy, n-decyloxy, 1-methyldecyloxy, n-undecyloxy, n-dodecyloxy, n-tridecyloxy, n-tetradecyloxy, n-pentadecyloxy, n-hexadecyloxy, n-heptadecyloxy, n-octadecyloxy, or n-eicosyloxy, etc.

[0161] "Aryloxy" is a group represented by "Ar-O- (Ar is an aryl group)", and for the details of this aryl, the description of "aryl" mentioned above can be cited.

[0162] "Replacement silyl" is, for example, a silyl substituted with at least one of aryl, alkyl, and cycloalkyl, and preferably is triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, or alkyldicycloalkylsilyl.

[0163] "Triarylsilyl" is a silyl group substituted with three aryls, and for details of this aryl, the description of "aryl" mentioned above can be cited. Specific "triarylsilyl" is, for example, triphenylsilyl, diphenylmononaphthylsilyl, monophenyldinaphthylsilyl, or trinaphthylsilyl, etc.

[0164] "Trialkylsilyl" is a silyl group substituted with three alkyls, and for details of this alkyl, the description of "alkyl" mentioned above can be cited. Specific "trialkylsilyl" is, for example, trimethylsilyl, triethylsilyl, tri-n-propylsilyl, triisopropylsilyl, tri-n-butylsilyl, triisobutylsilyl, tri-s-butylsilyl, tri-t-butylsilyl, ethyldimethylsilyl, n-propyldimethylsilyl, isopropyldimethylsilyl, n-butyldimethylsilyl, isobutyldimethylsilyl, s-butyldimethylsilyl, t-butyldimethylsilyl, methyldiethylsilyl, n-propyldiethylsilyl, isopropyldiethylsilyl, n-butyldiethylsilyl, s-butyldiethylsilyl, t-butyldiethylsilyl, methyldi-n-propylsilyl, ethyldi-n-propylsilyl, n-butyldi-n-propylsilyl, s-butyldi-n-propylsilyl, t-butyldi-n-propylsilyl, methyldiisopropylsilyl, ethyldiisopropylsilyl, n-butyldiisopropylsilyl, s-butyldiisopropylsilyl, or t-butyldiisopropylsilyl, etc.

[0165] "Tricycloalkylsilyl" is a silyl group substituted with three cycloalkyls, and for the details of this cycloalkyl, the description of "cycloalkyl" mentioned above can be cited. Specific examples of "tricycloalkylsilyl" include, for example, tricyclopentylsilyl or tricyclohexylsilyl.

[0166] "Dialkylcycloalkylsilyl" is a silyl group substituted with two alkyls and one cycloalkyl, and for the details of this alkyl and cycloalkyl, the descriptions of "alkyl" and "cycloalkyl" mentioned above can be cited.

[0167] "Alkyldicycloalkylsilyl" is a silyl group substituted with one alkyl and two cycloalkyls, and for the details of this alkyl and cycloalkyl, the descriptions of "alkyl" and "cycloalkyl" mentioned above can be cited.

[0168] The substituents (including the first substituent and the second substituent) can adjust the emission wavelength by selecting the substituents because the steric hindrance, electron-donating property, and electron-withdrawing property of their structures affect the emission wavelength of the polycyclic aromatic compound. Preferably, it is a group represented by the following structural formula, more preferably methyl, t-butyl, bicyclooctyl, cyclohexyl, adamantyl, 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, diphenylboranyl, dimesitylboranyl, dibenzooxaborininyl, phenyldibenzodiborininyl, carbazolyl, 3,6-dimethylcarbazolyl, 3,6-di-t-butylcarbazolyl, and phenoxy, and even more preferably methyl, t-butyl, phenyl, o-tolyl, 2,6-xylyl, 2,4,6-mesityl, diphenylamino, di-p-tolylamino, bis(p-(t-butyl)phenyl)amino, carbazolyl, 3,6-dimethylcarbazolyl, and 3,6-di-t-butylcarbazolyl. From the perspective of ease of synthesis, a larger steric hindrance is preferred for selective synthesis. Specifically, t-butyl, 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-dimethylcarbazolyl, and 3,6-di-t-butylcarbazolyl are preferred.

[0169] In the following structural formula, "Me" represents methyl, "tBu" represents t-butyl, "tAm" represents t-amyl, "tOct" represents t-octyl, and * represents the bonding position.

Chemical formula

Chemical formula

Chemical formula

Chemical formula

[0170] <Description of cycloalkane condensation> Further, at least one of the aromatic ring and the heteroaromatic ring in the chemical structure of the polycyclic aromatic compound of the present invention may be condensed with at least one cycloalkane.

[0171] For example, aryl and heteroaryl rings such as B1 ring, B2 ring, C ring, b1 ring, and c ring, aryl groups (aryl group moieties in aryl, diarylamino, arylheteroaryl amino, diarylboril, aryloxy or triarylsilyl) and heteroaryl groups (heteroaryl moieties in heteroaryl, diheteroaryl amino or arylheteroaryl amino) as the first and second substituents on these rings, aryl or heteroaryl rings formed by bonding adjacent substituents in the b1 ring and c ring, aryl groups (the same as above) and heteroaryl groups (the same as above) as the first and second substituents on the a ring and b2 ring, X 1 At least one of the aryl or heteroaryl groups as R of >N-R, R of >C(-R)2, and R of >Si(-R)2 may be condensed with at least one cycloalkane.

[0172] Preferably, aryl and heteroaryl rings such as B1 ring, B2 ring, C ring, b1 ring, and c ring, aryl groups (aryl group moieties in aryl, diarylamino, diarylboril or aryloxy) and heteroaryl groups (heteroaryl moieties in heteroaryl or diheteroaryl amino) as the first substituents on these rings, aryl or heteroaryl rings formed by bonding adjacent substituents in the b1 ring and c ring, aryl groups (the same as above) and heteroaryl groups (the same as above) as the first substituents on the a ring and b2 ring, X 1 At least one of the aryl or heteroaryl groups as R of >N-R, R of >C(-R)2, and R of >Si(-R)2 may be condensed with at least one cycloalkane.

[0173] More preferably, aryl rings which are B1 ring, B2 ring, C ring, b1 ring, and c ring, aryl groups as the first substituents on these rings (aryl group moieties in aryl or diarylamino) and heteroaryl groups (heteroaryl moieties in heteroaryl), an aryl ring formed by bonding adjacent substituents on b1 ring and c ring, aryl groups as the first substituents on a ring and b2 ring (the same as above) and heteroaryl groups (the same as above), X 1 Of the aryl groups as R in >N-R which is 1 , at least one may be condensed with at least one cycloalkane.

[0174] Even more preferably, aryl rings which are B1 ring, B2 ring, C ring, b1 ring, and c ring, aryl groups as the first substituents on these rings (aryl group moieties in aryl or diarylamino), aryl groups as the first substituents on a ring and b2 ring (the same as above), X 1 Of the aryl groups as R in >N-R which is 1 , at least one may be condensed with at least one cycloalkane.

[0175] Examples of the "cycloalkane" include cycloalkanes having 3 to 24 carbon atoms, cycloalkanes having 3 to 20 carbon atoms, cycloalkanes having 3 to 16 carbon atoms, cycloalkanes having 3 to 14 carbon atoms, cycloalkanes having 5 to 10 carbon atoms, cycloalkanes having 5 to 8 carbon atoms, cycloalkanes having 5 to 6 carbon atoms, cycloalkanes having 5 carbon atoms, and the like.

[0176] Specific cycloalkanes include cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctane, cyclononane, cyclodecane, norbornene, bicyclo[1.1.0]butane, bicyclo[1.1.1]pentane, bicyclo[2.1.0]pentane, bicyclo[2.1.1]hexane, bicyclo[3.1.0]hexane, bicyclo[2.2.1]heptane, bicyclo[2.2.2]octane, adamantane, diamantane, decahydronaphthalene and decahydroazulene, and their C1-C5 alkyl (especially methyl) substituents, halogen (especially fluorine) substituents, deuterium substituents, etc.

[0177] Among these, for example, a structure in which at least one hydrogen at the α-position carbon of the cycloalkane (in the cycloalkyl condensed to an aromatic ring or a heteroaromatic ring, the carbon at the position adjacent to the carbon at the condensation site) is substituted, as shown in the following structural formula, is preferable, a structure in which two hydrogens at the α-position carbon are substituted is more preferable, and a structure in which a total of four hydrogens at two α-position carbons are substituted is even more preferable. Examples of this substituent include C1-C5 alkyl (especially methyl) substituents, halogen (especially fluorine) substituents, deuterium substituents, etc.

Chemical formula

[0178] The number of cycloalkanes fused to one aromatic ring or heteroaromatic ring is preferably 1 to 3, more preferably 1 or 2, and even more preferably 1. For example, examples of one or more cycloalkanes fused to one benzene ring (phenyl group) are shown below. In each structural formula, * means a benzene ring contained in the skeletal structure of the compound when it is a benzene ring, and means a bond substituting the skeletal structure of the compound when it is a phenyl group. Cycloalkanes fused to each other may be fused as in formula (Cy-1-4) and formula (Cy-2-4). Even when the ring (group) to be fused is another aromatic ring or heteroaromatic ring other than the benzene ring (phenyl group), or when the cycloalkane to be fused is a cycloalkane other than cyclopentane or cyclohexane, the same applies.

Chem.

[0179] At least one -CH2- in the cycloalkane may be substituted with -O-. However, when a plurality of -CH2- are substituted with -O-, adjacent -CH2- are not substituted with -O-. For example, examples of one or more -CH2- in a cycloalkane fused to one benzene ring (phenyl group) substituted with -O- are shown below. In each structural formula, * means a benzene ring contained in the skeletal structure of the compound when it is a benzene ring, and means a bond substituting the skeletal structure of the compound when it is a phenyl group. Even when the ring (group) to be fused is another aromatic ring or heteroaromatic ring other than the benzene ring (phenyl group), or when the cycloalkane to be fused is a cycloalkane other than cyclopentane or cyclohexane, the same applies.

Chem.

[0180] At least one hydrogen in the cycloalkane may be substituted, and examples of such substituents include aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (the two aryls may be bonded via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, substituted silyl, deuterium, cyano or halogen. Details of these can cite the description of the first substituent mentioned above. Among these substituents, alkyl (for example, alkyl having 1 to 6 carbon atoms), cycloalkyl (for example, cycloalkyl having 3 to 14 carbon atoms), halogen (for example, fluorine) and deuterium are preferable. When cycloalkyl substitutes, it may be in a substitution form that forms a spiro structure. For example, an example in which a spiro structure is formed in a cycloalkane condensed to one benzene ring (phenyl group) is shown below. * in each structural formula means a benzene ring contained in the skeletal structure of the compound when it is a benzene ring, and means a bond substituting the skeletal structure of the compound when it is a phenyl group. [Chemical formula]

[0181] As other forms of cycloalkane condensation, polycyclic aromatic compounds represented by formula (1A), formula (1B), formula (2A), or formula (2B) are, for example, diarylamino groups condensed with cycloalkanes (condensed to this aryl group part), carbazolyl groups condensed with cycloalkanes (condensed to this benzene ring part) or benzocarbazolyl groups condensed with cycloalkanes (condensed to this benzene ring part) substituted examples. Examples of the "diarylamino group" include the groups described as the above-mentioned "first substituent".

[0182] Furthermore, as more specific examples, R in the polycyclic aromatic compound represented by formula (1A) or formula (2A) aExamples include a diarylamino group condensed with a cycloalkane (condensed to this aryl group moiety) or a carbazolyl group condensed with a cycloalkane (condensed to this benzene ring moiety).

[0183] <Explanation of substitution by deuterium, cyano, or halogen> At least one hydrogen in the polycyclic aromatic compound of the present invention may be substituted with deuterium, cyano, or halogen. Halogen is fluorine, chlorine, bromine, or iodine, with fluorine, chlorine, or bromine being preferred, and fluorine or chlorine being more preferred.

[0184] <Explanation of specific examples of the polycyclic aromatic compound of the present invention> More specific examples of the polycyclic aromatic compound include compounds represented by the following structural formulas. In the following structural formulas, "Me" represents a methyl group and "tBu" represents a t-butyl group.

[0185]

Chemical formula

[0186]

Chemical formula

[0187]

Chemical formula

[0188]

Chemical formula

[0189]

Chemical formula

[0190]

Chemical formula

[0191]

Chem.

[0192]

Chem.

[0193]

Chem.

[0194]

Chem.

[0195]

Chem.

[0196]

Chem.

[0197]

Chem.

[0198]

Chem.

[0199]

Chem.

[0200]

Chem.

[0201]

Chem.

[0202]

Chem.

[0203]

Chem.

[0204]

Chem.

[0205]

Chem.

[0206]

Chem.

[0207]

Chem.

[0208]

Chem.

[0209]

Chem.

[0210]

Chem.

[0211]

Chem.

[0212]

Chem.

[0213]

Chem.

[0214]

Chem.

[0215]

Chem.

[0216]

Chem.

[0217]

Chem.

[0218]

Chem.

[0219]

Chem.

[0220]

Chem.

[0221] <Explanation of the Polymerization of Polycyclic Aromatic Compounds> The polycyclic aromatic compound represented by the above general formula (1A) or general formula (1B) can also be used as a polymer compound obtained by polymerizing a reactive compound having a reactive substituent as a monomer (the monomer for obtaining this polymer compound has a polymerizable substituent), or a polymer crosslinked product obtained by further crosslinking the polymer compound (the polymer compound for obtaining this polymer crosslinked product has a crosslinkable substituent), or a pendant polymer compound obtained by reacting a main chain polymer with the reactive compound (the reactive compound for obtaining this pendant polymer compound has a reactive substituent), or a pendant polymer crosslinked product obtained by further crosslinking the pendant polymer compound (the pendant polymer compound for obtaining this pendant polymer crosslinked product has a crosslinkable substituent) as a material for organic devices, for example, a material for organic electroluminescent elements, a material for organic field effect transistors, a material for organic thin film solar cells, or a wavelength conversion filter.

[0222] The above-mentioned reactive substituents (including the polymerizable substituent, the crosslinkable substituent, and the reactive substituent for obtaining a pendant polymer, hereinafter simply referred to as "reactive substituents") are not particularly limited as long as they are substituents capable of polymerizing the above polycyclic aromatic compound, substituents capable of further crosslinking the polymer compound thus obtained, and substituents capable of pendent reaction with the main chain polymer, but substituents having the following structures are preferred. * in each structural formula indicates the bonding position.

Chemical formula

[0223] L is, independently of each other, a single bond, -O-, -S-, >C=O, -O-C(=O)-, alkylene having 1 to 12 carbon atoms, oxyalkylene having 1 to 12 carbon atoms, and polyoxyalkylene having 1 to 12 carbon atoms. Among the above substituents, groups represented by formula (XLS-1), formula (XLS-2), formula (XLS-3), formula (XLS-9), formula (XLS-10) or formula (XLS-17) are preferred, and groups represented by formula (XLS-1), formula (XLS-3) or formula (XLS-17) are more preferred.

[0224] Such a polymer compound, polymer crosslinked body, pendant-type polymer compound, and pendant-type polymer crosslinked body may contain, as a repeating unit, at least one selected from substituted or unsubstituted triarylamine, substituted or unsubstituted fluorene, substituted or unsubstituted anthracene, substituted or unsubstituted tetracene, substituted or unsubstituted triazine, substituted or unsubstituted carbazole, substituted or unsubstituted tetraphenylsilane, substituted or unsubstituted spirofluorene, substituted or unsubstituted triphenylphosphine, substituted or unsubstituted dibenzothiophene, and substituted or unsubstituted dibenzofuran, in addition to the repeating unit of the polycyclic aromatic compound represented by formula (1A) or formula (1B). Examples of the substituents in these repeating units include aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (the two aryls may be bonded via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, or alkyldicycloalkylsilyl. Regarding the "aryl" of triarylamine and the details of these substituents, the description in the polycyclic aromatic compound represented by formula (1A) or formula (1B) can be cited.

[0225] Details of the uses of such a polymer compound, polymer crosslinked body, pendant-type polymer compound, and pendant-type polymer crosslinked body (hereinafter, also simply referred to as "polymer compound and polymer crosslinked body") will be described later.

[0226] 2. Method for producing polycyclic aromatic compound Basically, the polycyclic aromatic compound of the present invention first has an a ring, and a B1 ring (b1 ring), a B2 ring (b2 ring), and a C ring (c ring) connected by a linking group (X 1 or X 2By bonding with a group containing a group), an intermediate is produced (first reaction), and then, by bonding the a-ring, B1-ring (b1-ring), B2-ring (b2-ring), and C-ring (c-ring) with a bonding group (a group containing Y), the final product can be produced (second reaction). The production method described in International Publication No. 2015 / 102118 can be referred to.

[0227] In the first reaction, for example, in the case of an etherification reaction, general reactions such as a nucleophilic substitution reaction and an Ullmann reaction can be used, and in the case of an amination reaction, a general reaction such as a Buchwald-Hartwig reaction can be used. Also, in the second reaction, a tandem hetero Friedel-Crafts reaction (a continuous aromatic electrophilic substitution reaction, the same hereinafter) can be used.

[0228] The second reaction is a reaction for introducing Y that bonds the a-ring, B1-ring (b1-ring), B2-ring (b2-ring), and C-ring (c-ring) as shown in the following schemes (1) and (2). First, X 1 and X 2 The hydrogen atom between them is orthometalated with n-butyllithium, sec-butyllithium, t-butyllithium, etc. Next, a halide of Y such as boron trichloride or boron tribromide is added, and after performing a metal exchange of lithium-boron, a Bronsted base such as N,N-diisopropylethylamine is added to cause a tandem borofriedel-crafts reaction to obtain the target product. In the second reaction, a Lewis acid such as aluminum trichloride may be added to accelerate the reaction. In the following schemes (1) and (2), as well as in each structural formula in the subsequent schemes, the definitions of the symbols are the same as the above-described definitions.

[0229]

Chem.

Chem.

[0230] In the above scheme (1), the unit structure φ1 is not illustrated. However, since the compounds of the present invention are compounds formed by repeatedly linking the above-described "meta-type unit structure" and "para-type unit structure", similar reactions occur in all unit structures, and the compounds of the present invention can be produced. The above scheme (2) is a method for producing a compound having a representative structure. In formula (1A), it shows a method for producing a compound in which n (n = 1) unit structures of formula (φ1-m1) are selected as φ1.

[0231] In the above scheme, lithium was introduced to the desired position by orthometalation. However, as in the following scheme (3), a bromine atom or the like can be introduced to the position where lithium is to be introduced, and lithium can also be introduced to the desired position by halogen-metal exchange. According to this method, it is useful because the target product can be produced even in cases where orthometalation cannot be carried out due to the influence of substituents.

Chemical Formula

[0232] The above schemes (1) to (3) are representative production methods where Y is boron (B) or the like.

[0233] Next, as an example, the cases where Y is phosphorus sulfide, phosphorus oxide, or a phosphorus atom are shown in the following schemes (4) and (5). Similar to before, first, the hydrogen atom between X 1 and X 2 is orthometalated with n-butyllithium or the like. Then, phosphorus trichloride and sulfur are added in this order, and finally, a Lewis acid such as aluminum trichloride and a Brønsted base such as N,N-diisopropylethylamine are added to cause a tandem phospha-Friedel-Crafts reaction to obtain a compound where Y is phosphorus sulfide. Further, by treating the obtained phosphorus sulfide compound with m-chloroperbenzoic acid (m-CPBA), a compound where Y is phosphorus oxide can be obtained, and by treating it with triethylphosphine, a compound where Y is a phosphorus atom can be obtained.

[0234] [Chemistry] [Chemistry]

[0235] In the above scheme, mainly examples where Y is B, P, P=O or P=S are described. However, by appropriately changing the raw materials, other compounds can also be produced.

[0236] In the above scheme, before adding the halide of Y such as boron trichloride or boron tribromide, the hydrogen atom (or halogen atom) between X 1 and X 2 is orthometalated with butyllithium or the like to give an example of a tandem hetero Friedel-Crafts reaction. However, the reaction can also proceed by adding a halide of Y such as boron trichloride or boron tribromide without performing orthometalation using butyllithium or the like.

[0237] Examples of the solvent used in the above scheme include t-butylbenzene and xylene.

[0238] Examples of the orthometalation reagent used in the above scheme include alkyllithiums such as methyllithium, n-butyllithium, sec-butyllithium, t-butyllithium, organic alkali compounds such as lithium diisopropylamide, lithium tetramethylpiperidide, lithium hexamethyldisilazide, potassium hexamethyldisilazide, and dispersed alkali metals such as dispersed Na in an organic solvent.

[0239] Examples of the metal-Y metal exchange reagent used in the above scheme include halides of Y such as trifluoride of Y, trichloride of Y, tribromide of Y, triiodide of Y, amino halides of Y such as CIPN(NEt2)2, alkoxides of Y, aryloxides of Y, and the like.

[0240] Examples of the Bronsted base used in the above scheme include N,N - diisopropylethylamine, triethylamine, 2,2,6,6 - tetramethylpiperidine, 1,2,2,6,6 - pentamethylpiperidine, N,N - dimethylaniline, N,N - dimethyltoluidine, 2,6 - lutidine, sodium tetraphenylborate, potassium tetraphenylborate, triphenylborane, tetraphenylsilane, Ar4BNa, Ar4BK, Ar3B, Ar4Si (where Ar is an aryl such as phenyl), and the like.

[0241] Examples of the Lewis acid used in the above scheme include AlCl3, AlBr3, AlF3, BF3·OEt2, BCl3, BBr3, GaCl3, GaBr3, InCl3, InBr3, In(OTf)3, SnCl4, SnBr4, AgOTf, ScCl3, Sc(OTf)3, ZnCl2, ZnBr2, Zn(OTf)2, MgCl2, MgBr2, Mg(OTf)2, LiOTf, NaOTf, KOTf, Me3SiOTf, Cu(OTf)2, CuCl2, YCl3, Y(OTf)3, TiCl4, TiBr4, ZrCl4, ZrBr4, FeCl3, FeBr3, CoCl3, CoBr3, and the like.

[0242] In the above scheme, a Bronsted base or a Lewis acid may be used to promote the tandem hetero - Friedel - Crafts reaction. However, when using halides of Y such as trifluoride of Y, trichloride of Y, tribromide of Y, and triiodide of Y, acids such as hydrogen fluoride, hydrogen chloride, hydrogen bromide, and hydrogen iodide are generated as the aromatic electrophilic substitution reaction proceeds. Therefore, the use of a Bronsted base to capture the acid is effective. On the other hand, when using aminated halides of Y or alkoxides of Y, amines and alcohols are generated as the aromatic electrophilic substitution reaction proceeds. In many cases, it is not necessary to use a Bronsted base. However, since the leaving ability of the amino group and the alkoxy group is low, the use of a Lewis acid to promote the elimination is effective.

[0243] In addition, the polycyclic aromatic compounds of the present invention also include compounds in which at least some of the hydrogens are substituted with deuterium, cyano, or halogen. Such compounds can be produced in the same manner as described above by using halogenated raw materials such as deuterated, cyanated, fluorinated, or chlorinated raw materials at desired positions.

[0244] 3. Organic device In the chemical structural formulas exemplified hereinafter, "Me" represents a methyl group and "tBu" represents a t-butyl group. The polycyclic aromatic compounds according to the present invention can be used as materials for organic devices. Examples of the organic devices include organic electroluminescent elements, organic field effect transistors, organic thin film solar cells, or wavelength conversion filters.

[0245] 3-1. Organic electroluminescent element The polycyclic aromatic compounds according to the present invention can be used, for example, as materials for organic electroluminescent elements. Hereinafter, the organic EL element according to the present embodiment will be described in detail with reference to the drawings. FIG. 1 is a schematic cross-sectional view showing the organic EL element according to the present embodiment.

[0246] <Structure of Organic Electroluminescent Element> The organic EL element 100 shown in FIG. 1 includes a substrate 101, an anode 102 provided on the substrate 101, a hole injection layer 103 provided on the anode 102, a hole transport layer 104 provided on the hole injection layer 103, a light emitting layer 105 provided on the hole transport layer 104, an electron transport layer 106 provided on the light emitting layer 105, an electron injection layer 107 provided on the electron transport layer 106, and a cathode 108 provided on the electron injection layer 107.

[0247] Note that the organic EL element 100 may have a structure in which the manufacturing order is reversed. For example, it may include a substrate 101, a cathode 108 provided on the substrate 101, an electron injection layer 107 provided on the cathode 108, an electron transport layer 106 provided on the electron injection layer 107, a light-emitting layer 105 provided on the electron transport layer 106, a hole transport layer 104 provided on the light-emitting layer 105, a hole injection layer 103 provided on the hole transport layer 104, and an anode 102 provided on the hole injection layer 103.

[0248] Not all of the above layers are essential. With a minimum structural unit consisting of an anode 102, a light-emitting layer 105, and a cathode 108, the hole injection layer 103, the hole transport layer 104, the electron transport layer 106, and the electron injection layer 107 are layers that can be optionally provided. Also, each of the above layers may consist of a single layer or a plurality of layers.

[0249] As modes of the layers constituting the organic EL element, in addition to the above-described "substrate / anode / hole injection layer / hole transport layer / light-emitting layer / electron transport layer / electron injection layer / cathode" configuration mode, there are also "substrate / anode / hole transport layer / light-emitting layer / electron transport layer / electron injection layer / cathode", "substrate / anode / hole injection layer / light-emitting 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 / hole injection layer / light-emitting layer / electron transport layer / cathode", "substrate / anode / light-emitting layer / electron transport layer / cathode", "substrate / anode / light-emitting layer / electron injection layer / cathode" configuration modes.

[0250] <Substrate in the organic electroluminescent element> The substrate 101 is a support for the organic EL element 100, and usually, quartz, glass, metal, plastic, etc. are used. The substrate 101 is formed in a plate shape, film shape, or sheet shape according to the purpose, and for example, a glass plate, metal plate, metal foil, plastic film, plastic sheet, etc. are used. Among these, a glass plate and a plate made of a transparent synthetic resin such as polyester, polymethacrylate, polycarbonate, or polysulfone are preferable. In the case of a glass substrate, soda-lime glass, alkali-free glass, etc. are used, and the thickness only needs to be sufficient to maintain mechanical strength, so for example, 0.2 mm or more is sufficient. The upper limit value of the thickness is, for example, 2 mm or less, preferably 1 mm or less. Regarding the glass material, since it is better that there are fewer eluted ions from the glass, alkali-free glass is more preferable, but soda-lime glass with a barrier coat such as SiO2 is also commercially available, so this can be used. Further, in order to enhance 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 101. In particular, when a plate, film, or sheet made of a synthetic resin with low gas barrier property is used as the substrate 101, it is preferable to provide a gas barrier film.

[0251] <Anode in an organic electroluminescent element> The anode 102 serves to inject holes into the light-emitting layer 105. When at least one layer of a hole injection layer 103 and a hole transport layer 104 is provided between the anode 102 and the light-emitting layer 105, holes are injected into the light-emitting layer 105 through these layers.

[0252] Examples of materials for forming the anode 102 include inorganic compounds and organic compounds. Examples of inorganic compounds include metals (such as aluminum, gold, silver, nickel, palladium, chromium, etc.), metal oxides (such as indium oxide, tin oxide, indium-tin oxide (ITO), indium-zinc oxide (IZO), etc.), metal halides (such as copper iodide, etc.), copper sulfide, carbon black, ITO glass, Nesa glass, etc. Examples of organic compounds include polythiophenes such as poly(3-methylthiophene), and conductive polymers such as polypyrrole and polyaniline. In addition, it can be appropriately selected and used from substances used as anodes of organic EL elements.

[0253] The resistance of the transparent electrode is not limited as long as sufficient current for the light emission of the light-emitting element can be supplied, but it is desirable to have a low resistance from the viewpoint of the power consumption of the light-emitting element. For example, an ITO substrate with a resistance of 300 Ω / sq or less can function as an element electrode, but currently substrates with a resistance of about 10 Ω / sq can also be supplied. Therefore, it is particularly desirable to use low-resistance products with a resistance of, for example, 100 to 5 Ω / sq, preferably 50 to 5 Ω / sq. The thickness of the ITO can be arbitrarily selected according to the resistance value, but it is usually used in the range of 50 to 300 nm.

[0254] <Hole injection layer and hole transport layer in organic electroluminescent device> The hole injection layer 103 serves to efficiently inject holes moving from the anode 102 into the light-emitting layer 105 or the hole transport layer 104. The hole transport layer 104 serves to efficiently transport holes injected from the anode 102 or holes injected from the anode 102 through the hole injection layer 103 to the light-emitting layer 105. The hole injection layer 103 and the hole transport layer 104 are each formed by laminating or mixing one or more hole injection / transport materials, or by a mixture of a hole injection / transport material and a polymer binder. In addition, an inorganic salt such as iron(III) chloride may be added to the hole injection / transport material to form a layer.

[0255] As a hole injection / transporting material, it is necessary to efficiently inject / transport holes from the anode between electrodes to which an electric field is applied, and it is desirable that the hole injection efficiency is high and the injected holes are efficiently transported. For this purpose, it is preferable that the material has a small ionization potential, a large hole mobility, excellent stability, and is less likely to generate trap impurities during production and use.

[0256] As a material for forming the hole injection layer 103 and the hole transport layer 104, a polycyclic aromatic compound represented by the above general formula (1A) or general formula (1B) can be used. In addition, in a photoconductive material, an arbitrary compound can be selected and used from compounds conventionally used as hole charge transport materials, p-type semiconductors, and known compounds used in the hole injection layer and the hole transport layer of an organic EL element.

[0257] Specific examples thereof include carbazole derivatives (N-phenylcarbazole, polyvinylcarbazole, etc.), biscarbazole derivatives such as bis(N-arylcarbazole) or bis(N-alkylcarbazole), triarylamine derivatives (polymers having an aromatic tertiary amino group 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'-dinaphthyl-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’-Tetra[1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4,4'-diamine, triphenylamine derivatives such as 4,4',4''-tris(3-methylphenyl(phenyl)amino)triphenylamine, starburst amine derivatives, etc.), stilbene derivatives, phthalocyanine derivatives (metal-free, copper phthalocyanine, etc.), pyrazoline derivatives, hydrazone-based compounds, benzofuran derivatives and thiophene derivatives, oxadiazole derivatives, quinoxaline derivatives (e.g., 1,4,5,8,9,12-hexaazatriphenylene-2,3,6,7,10,11-hexacarbonitrile, etc.), heterocyclic compounds such as porphyrin derivatives, polysilane, etc. In the polymer system, polycarbonate, styrene derivatives, polyvinylcarbazole, and polysilane having the above monomers in the side chain are preferred, but it is not particularly limited as long as it can form a thin film necessary for the production of the light-emitting element, can inject holes from the anode, and can further transport holes.

[0258] Also, it is known that the conductivity of organic semiconductors is strongly affected by their doping. Such organic semiconductor matrix materials are composed of compounds with good electron-donating properties or compounds with good electron-accepting properties. For doping with electron-donating substances, strong electron acceptors such as tetracyanoquinodimethane (TCNQ) or 2,3,5,6-tetrafluorotetracyano-1,4-benzoquinodimethane (F4TCNQ) are known (for example, see the literature "M. Pfeiffer, A. Beyer, T. Fritz, K. Leo, Appl. Phys. Lett., 73(22), 3202 - 3204(1998)" and the literature "J. Blochwitz, M. Pheiffer, T. Fritz, K. Leo, Appl. Phys. Lett., 73(6), 729 - 731(1998)"). These generate so-called holes by the electron transfer process in electron-donating base materials (hole transport materials). The conductivity of the base material changes significantly depending on the number and mobility of the holes. As matrix materials having hole transport characteristics, for example, benzidine derivatives (such as TPD) or starburst amine derivatives (such as TDATA), or specific metal phthalocyanines (especially zinc phthalocyanine (ZnPc), etc.) are known (Japanese Patent Laid-Open No. 2005-167175).

[0259] The above-described hole injection layer materials and hole transport layer materials can also be used as hole layer materials in the form of polymer compounds obtained by polymerizing a reactive compound having a reactive substituent substituted thereon as a monomer, or polymer cross-linked bodies thereof, or pendant polymer compounds obtained by reacting a main chain polymer with the reactive compound, or pendant polymer cross-linked bodies thereof. As the reactive substituent in this case, the description of the polycyclic aromatic compound represented by formula (1A) or formula (1B) can be cited. Details of the uses of such polymer compounds and polymer cross-linked bodies will be described later.

[0260] <The light-emitting layer in the organic electroluminescent device> The light-emitting layer 105 is a layer that emits light by recombining holes injected from the anode 102 and electrons injected from the cathode 108 between electrodes to which an electric field is applied. As the material for forming the light-emitting layer 105, a polycyclic aromatic compound represented by the above general formula (1A) or general formula (1B) can be used. Also, any compound (luminescent compound) that is excited by the recombination of holes and electrons to emit light is acceptable, and it is preferable that the compound can form a stable thin film shape and exhibits strong light emission (fluorescence) efficiency in the solid state.

[0261] The light-emitting layer may be either a single layer or a plurality of layers, and each is formed of a material for the light-emitting layer (host material, dopant material). The host material and the dopant material may each be of one type or a combination of a plurality of types. Also, a material for the hole transport layer or a material for the electron transport layer may be mixed with the host material, or a combination thereof may be used. The dopant material may be contained in the whole host material or partially, and either is acceptable. As the doping method, it can be formed by co-evaporation with the host material, but it may also be co-evaporated after being premixed with the host material, or formed into a film by a wet film-forming method after being premixed with the host material together with an organic solvent.

[0262] The amount of the host material used varies depending on the type of the host material, and it may be determined according to the characteristics of the host material. The standard amount of the host material used is preferably 50 to 99.999% by weight of the total material for the light-emitting layer, more preferably 80 to 99.95% by weight, and still more preferably 90 to 99.9% by weight.

[0263] The amount of the dopant material used varies depending on the type of the dopant material, and it may be determined according to the characteristics of the dopant material. The standard amount of the dopant used is preferably 0.001 to 50% by weight, more preferably 0.05 to 20% by weight, and still more preferably 0.1 to 10% by weight of the total material for the light-emitting layer. If it is within the above range, for example, it is preferable in that the concentration quenching phenomenon can be prevented. Further, from the viewpoint of durability, it is also preferable that some or all of the hydrogen atoms of the dopant material are deuterated.

[0264] On the other hand, in an organic EL element using a thermally activated delayed fluorescence dopant material, it is preferable that the amount of the dopant material used is low in terms of preventing the concentration quenching phenomenon, but it is preferable that the amount of the dopant material used is high from the viewpoint of the efficiency of the thermally activated delayed fluorescence mechanism. Furthermore, in an organic EL element using a thermally activated delayed fluorescence assist dopant material, from the viewpoint of the efficiency of the thermally activated delayed fluorescence mechanism of the assist dopant material, it is preferable that the amount of the dopant material used is lower than the amount of the assist dopant material used.

[0265] When the assist dopant material is used, the standard amounts of the host material, the assist dopant material, and the dopant material are 40 to 99.999% by weight, 59 to 1% by weight, and 20 to 0.001% by weight, respectively, of the total material for the light-emitting layer, preferably 60 to 99.99% by weight, 39 to 5% by weight, and 10 to 0.01% by weight, respectively, and more preferably 70 to 99.95% by weight, 29 to 10% by weight, and 5 to 0.05% by weight. The polycyclic aromatic compound represented by the above general formula (1A) or general formula (1B) can also be used as the assist dopant material.

[0266] Examples of the host material include condensed ring derivatives such as anthracene, pyrene, dibenzocrisene, or fluorene, which have been known as light emitters, bisstyryl derivatives such as bisstyrylanthracene derivatives and distyrylbenzene derivatives, tetraphenylbutadiene derivatives, cyclopentadiene derivatives, etc. In particular, anthracene-based compounds, fluorene-based compounds, or dibenzocrisene-based compounds are preferred. Further, from the viewpoint of durability, it is also preferable that some or all of the hydrogen atoms of the host material are deuterated. Furthermore, it is also preferable to form the light-emitting layer by combining a host compound in which some or all of the hydrogen atoms are deuterated and a dopant compound in which some or all of the hydrogen atoms are deuterated.

[0267] <Anthracene-based compound> The anthracene-based compound as the host is, for example, a compound represented by the following general formula (3). [Chemical formula]

[0268] In formula (3), X and Ar 4 are each independently hydrogen, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted diarylamino, optionally substituted diheteroarylamino, optionally substituted arylheteroarylamino, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted alkenyl, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted arylthio, or optionally substituted silyl, and all X and Ar 4 do not simultaneously become hydrogen, and at least one hydrogen in the compound represented by formula (3) may be substituted with halogen, cyano, deuterium, or optionally substituted heteroaryl.

[0269] In addition, a multimer (preferably a dimer) may be formed using the structure represented by formula (3) as a unit structure. In this case, for example, a form in which the unit structures represented by formula (3) are bonded to each other via X can be mentioned. Examples of X include a single bond, arylene (such as phenylene, biphenylene, and naphthylene), and heteroarylene (a group having a divalent valence such as a pyridine ring, a dibenzofuran ring, a dibenzothiophene ring, a carbazole ring, a benzocarbazole ring, and a phenyl-substituted carbazole ring).

[0270] Details of the above aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio, or silyl will be described in the column of preferred embodiments below. In addition, examples of substituents for these groups include aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio, or silyl, and details of these will also be described in the column of preferred embodiments below.

[0271] Preferred embodiments of the above anthracene-based compound will be described below. The definitions of the symbols in the following structures are the same as those described above.

Chemical formula

[0272] In general formula (3), X is, independently of each other, a group represented by the above formula (3-X1), formula (3-X2), or formula (3-X3), and the group represented by formula (3-X1), formula (3-X2), or formula (3-X3) is bonded to the anthracene ring of formula (3) at *. Preferably, two X's do not simultaneously become a group represented by formula (3-X3). More preferably, two X's do not simultaneously become a group represented by formula (3-X2) either.

[0273] In addition, a multimer (preferably a dimer) may be formed using the structure represented by formula (3) as a unit structure. In this case, for example, a form in which the unit structures represented by formula (3) are bonded to each other via X can be mentioned. Examples of X include a single bond, arylene (such as phenylene, biphenylene, and naphthylene), and heteroarylene (a group having a divalent valence such as a pyridine ring, a dibenzofuran ring, a dibenzothiophene ring, a carbazole ring, a benzocarbazole ring, and a phenyl-substituted carbazole ring).

[0274] The naphthylene moieties in formula (3-X1) and formula (3-X2) may be condensed with one benzene ring. The structure condensed in this way is as follows.

Chemical formula

[0275] Ar 1 and Ar 2 are each independently hydrogen, phenyl, biphenylyl, terphenylyl, quaterphenylyl, naphthyl, phenanthryl, fluorenyl, benzofluorenyl, chrysenyl, triphenylenyl, pyrenylyl, or a group represented by the above formula (A) (including a carbazolyl group, a benzocarbazolyl group, and a phenyl-substituted carbazolyl group). When Ar 1 or Ar 2 is a group represented by formula (A), the group represented by formula (A) is bonded to the naphthalene ring in formula (3-X1) or formula (3-X2) at its *.

[0276] Ar 3 is phenyl, biphenylyl, terphenylyl, quaterphenylyl, naphthyl, phenanthryl, fluorenyl, benzofluorenyl, chrysenyl, triphenylenyl, pyrenylyl, or a group represented by the above formula (A) (including a carbazolyl group, a benzocarbazolyl group, and a phenyl-substituted carbazolyl group). When Ar 3When the group is represented by the formula (A), the group represented by the formula (A) is bonded to the single bond represented by the straight line in the formula (3-X3) at the *. That is, the anthracene ring of the formula (3) is directly bonded to the group represented by the formula (A).

[0277] Also, Ar 3 may have a substituent, and Ar 3 at least one hydrogen in may be further substituted with an alkyl having 1 to 4 carbon atoms, a cycloalkyl having 5 to 10 carbon atoms, phenyl, biphenylyl, terphenylyl, naphthyl, phenanthryl, fluorenyl, chrysenyl, triphenylenyl, pyrenyl, or a group represented by the above formula (A) (including a carbazolyl group and a phenyl-substituted carbazolyl group). Note that when the substituent that Ar 3 has is a group represented by the formula (A), the group represented by the formula (A) is bonded to Ar in the formula (3-X3) at the *. 3 and binds.

[0278] Ar 4 are each independently hydrogen, phenyl, biphenylyl, terphenylyl, naphthyl, or a silyl substituted with an alkyl having 1 to 4 carbon atoms (such as methyl, ethyl, t-butyl, etc.) and / or a cycloalkyl having 5 to 10 carbon atoms.

[0279] Examples of the alkyl having 1 to 4 carbon atoms that substitutes for silyl include methyl, ethyl, propyl, i-propyl, butyl, sec-butyl, t-butyl, cyclobutyl, etc., and the three hydrogens in silyl are each independently substituted with these alkyls.

[0280] Specific "silyl substituted with an alkyl having 1 to 4 carbon atoms" includes trimethylsilyl, triethylsilyl, tripropylsilyl, tri-i-propylsilyl, tributylsilyl, tri-sec-butylsilyl, tri-t-butylsilyl, ethyldimethylsilyl, propyldimethylsilyl, i-propyldimethylsilyl, butyldimethylsilyl, sec-butyldimethylsilyl, t-butyldimethylsilyl, methyldiethylsilyl, propyldiethylsilyl, i-propyldiethylsilyl, butyldiethylsilyl, sec-butyldiethylsilyl, t-butyldiethylsilyl, methyldipropylsilyl, ethyldipropylsilyl, butyldipropylsilyl, sec-butyldipropylsilyl, t-butyldipropylsilyl, methyldi-i-propylsilyl, ethyldi-i-propylsilyl, butyldi-i-propylsilyl, sec-butyldi-i-propylsilyl, t-butyldi-i-propylsilyl, and the like.

[0281] The cycloalkyl having 5 to 10 carbon atoms that substitutes for silyl includes cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, norbornenyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.0]pentyl, bicyclo[2.1.1]hexyl, bicyclo[3.1.0]hexyl, bicyclo[2.2.1]heptyl, bicyclo[2.2.2]octyl, adamantyl, decahydronaphthalenyl, decahydroazulenyl, and the like, and the three hydrogens in silyl are each independently substituted with these cycloalkyls.

[0282] Specific "silyl substituted with a cycloalkyl having 5 to 10 carbon atoms" includes tricyclopentylsilyl, tricyclohexylsilyl, and the like.

[0283] The substituted silyl also includes dialkylcycloalkylsilyl substituted with two alkyls and one cycloalkyl, and alkyldicycloalkylsilyl substituted with one alkyl and two cycloalkyls. Specific examples of the alkyl and cycloalkyl for substitution include the groups described above.

[0284] Further, the hydrogen in the chemical structure of the anthracene-based compound represented by the general formula (3) may be substituted with the group represented by the above formula (A). When substituted with the group represented by the formula (A), the group represented by the formula (A) substitutes at least one hydrogen in the compound represented by the formula (3) therein.

[0285] The group represented by the formula (A) is one of the substituents that the anthracene-based compound represented by the formula (3) may have. [Chemical formula]

[0286] In the above formula (A), Y is -O-, -S- or >N-R 29 wherein, R 21 ~R 28 are each independently hydrogen, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted arylthio, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, alkyldicycloalkylsilyl, optionally substituted amino, halogen, hydroxy or cyano, and among R 21 ~R 28 adjacent groups may be bonded to each other to form a hydrocarbon ring, an aryl ring or a heteroaryl ring, and R 29 is hydrogen or optionally substituted aryl.

[0287] R 21 ~R 28In the case of "alkyl which may be substituted", the "alkyl" may be either straight-chain or branched-chain, and examples thereof include straight-chain alkyl having 1 to 24 carbon atoms or branched-chain alkyl having 3 to 24 carbon atoms. Alkyl having 1 to 18 carbon atoms (branched-chain alkyl having 3 to 18 carbon atoms) is preferred, alkyl having 1 to 12 carbon atoms (branched-chain alkyl having 3 to 12 carbon atoms) is more preferred, alkyl having 1 to 6 carbon atoms (branched-chain alkyl having 3 to 6 carbon atoms) is still more preferred, and alkyl having 1 to 4 carbon atoms (branched-chain alkyl having 3 to 4 carbon atoms) is particularly preferred.

[0288] 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-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, t-octyl (1,1,3,3-tetramethylbutyl), 1-methylheptyl, 2-ethylhexyl, 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, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, n-eicosyl, and the like.

[0289] R 21 ~R 28 In the case of "cycloalkyl which may be substituted", the "cycloalkyl" 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, and the like.

[0290] Specific examples of the "cycloalkyl" include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, and their C1-C4 alkyl (especially methyl) substituents, norbornenyl, bicyclo[1.1.0]butyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.0]pentyl, bicyclo[2.1.1]hexyl, bicyclo[3.1.0]hexyl, bicyclo[2.2.1]heptyl, bicyclo[2.2.2]octyl, adamantyl, diamantyl, decahydronaphthalenyl, decahydroazulenyl, and the like.

[0291] R 21 ~R 28 Examples of the "aryl" in the "optionally substituted aryl" in R~R include aryl having 6 to 30 carbon atoms, preferably aryl having 6 to 16 carbon atoms, more preferably aryl having 6 to 12 carbon atoms, and particularly preferably aryl having 6 to 10 carbon atoms.

[0292] Specific examples of the "aryl" include phenyl which is a monocyclic system, biphenylyl which is a bicyclic system, naphthyl which is a condensed bicyclic system, terphenyl (m-terphenyl, o-terphenyl, p-terphenyl) which is a tricyclic system, acenaphthylenyl, fluorenyl, phenalenyl, phenanthrenyl which are condensed tricyclic systems, triphenylenyl, pyrenyl, naphthacenyl which are condensed tetracyclic systems, perylenyl, pentacenyl which are condensed pentacyclic systems, and the like.

[0293] R 21 ~R 28 Examples of the "heteroaryl" in the "optionally substituted heteroaryl" in R~R include heteroaryl having 2 to 30 carbon atoms, preferably heteroaryl having 2 to 25 carbon atoms, more preferably heteroaryl having 2 to 20 carbon atoms, still more preferably heteroaryl having 2 to 15 carbon atoms, and particularly preferably heteroaryl having 2 to 10 carbon atoms. Further, examples of the heteroaryl include heterocycles containing 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen in addition to carbon as ring-constituting atoms.

[0294] Specific examples of the "heteroaryl" include, for example, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, pyrazolyl, pyridinyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, indolyl, isoindolyl, 1H-indazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolinyl, isoquinolinyl, cinnolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, naphthyridinyl, purinyl, pteridinyl, carbazolyl, acridinyl, phenoxathiinyl, phenoxazinyl, phenothiazinyl, phenazinyl, phenazasilinyl, indolizinyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, naphthobenzofuranyl, thiophenyl, benzothiophenyl, dibenzothiophenyl, naphthobenzothiophenyl, benzophosphoryl, dibenzophosphoryl, a monovalent group of a benzophosphole oxide ring, a monovalent group of a dibenzophosphole oxide ring, phthalazinyl, thianthrenyl, indolocarbazolyl, benzoindolocarbazolyl, and benzo-benzoindolocarbazolyl, and the like.

[0295] R 21 ~R 28 Examples of the "alkoxy" in the "optionally substituted alkoxy" in R~R include linear alkoxy having 1 to 24 carbon atoms or 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 even more preferred, and alkoxy having 1 to 4 carbon atoms (branched alkoxy having 3 to 4 carbon atoms) is particularly preferred.

[0296] Specific "alkoxy" groups include methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, s-butoxy, t-butoxy, pentyloxy, hexyloxy, heptyloxy, octyloxy, and the like.

[0297] R 21 ~R 28 The "aryloxy" in the "optionally substituted aryloxy" in R 21 ~R 28 is a group in which the hydrogen of the -OH group is substituted with an aryl, and this aryl can cite the groups described as "aryl" in R

[0298] R 21 ~R 28 The "arylthio" in the "optionally substituted arylthio" in R 21 ~R 28 is a group in which the hydrogen of the -SH group is substituted with an aryl, and this aryl can cite the groups described as "aryl" in R

[0299] R 21 ~R 28 The "trialkylsilyl" in R 21 ~R 28 refers to a group in which the three hydrogens in the silyl group are each independently substituted with an alkyl, and this alkyl can cite the groups described as "alkyl" in R

[0300] Specific examples of the "trialkylsilyl" group include trimethylsilyl, triethylsilyl, tripropylsilyl, tri-i-propylsilyl, tributylsilyl, tri-sec-butylsilyl, tri-t-butylsilyl, ethyldimethylsilyl, propyldimethylsilyl, i-propyldimethylsilyl, butyldimethylsilyl, sec-butyldimethylsilyl, t-butyldimethylsilyl, methyldiethylsilyl, propyldiethylsilyl, i-propyldiethylsilyl, butyldiethylsilyl, sec-butyldiethylsilyl, t-butyldiethylsilyl, methyldipropylsilyl, ethyldipropylsilyl, butyldipropylsilyl, sec-butyldipropylsilyl, t-butyldipropylsilyl, methyldi-i-propylsilyl, ethyldi-i-propylsilyl, butyldi-i-propylsilyl, sec-butyldi-i-propylsilyl, t-butyldi-i-propylsilyl, and the like.

[0301] R 21 ~R 28 Examples of the "tricycloalkylsilyl" group in 21 ~ 28 include groups in which the three hydrogens in the silyl group are each independently substituted with a cycloalkyl group, and this cycloalkyl group can be cited as the group described as the "cycloalkyl" group in 21 ~ 28 . Preferred cycloalkyl groups for substitution are cycloalkyl groups having 5 to 10 carbon atoms, specifically, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.0]pentyl, bicyclo[2.1.1]hexyl, bicyclo[3.1.0]hexyl, bicyclo[2.2.1]heptyl, bicyclo[2.2.2]octyl, adamantyl, decahydronaphthalenyl, decahydroazulenyl, and the like. 21 ~R 28 Examples of the "tricycloalkylsilyl" group include tricyclopentylsilyl, tricyclohexylsilyl, and the like.

[0302]

[0303] ​Specific examples of a dialkylcycloalkylsilyl substituted with two alkyls and one cycloalkyl and an alkyldicycloalkylsilyl substituted with one alkyl and two cycloalkyls include silyls substituted with groups selected from the specific alkyls and cycloalkyls described above.

[0304] R 21 ~R 28 Examples of the "substituted amino" in the "optionally substituted amino" in R 21 ~R 28 include, for example, amino groups in which two hydrogens are substituted with aryl or heteroaryl. An amino in which two hydrogens are substituted with aryl is a diaryl-substituted amino, an amino in which two hydrogens are substituted with heteroaryl is a diheteroaryl-substituted amino, and an amino in which two hydrogens are substituted with aryl and heteroaryl is an arylheteroaryl-substituted amino. This aryl or heteroaryl can cite the groups described as "aryl" or "heteroaryl" in R

[0305] Specific examples of the "substituted amino" include diphenylamino, dinaphthylamino, phenylnaphthylamino, dipyridylamino, phenylpyridylamino, naphthylpyridylamino, and the like.

[0306] R 21 ~R 28 Examples of the "halogen" in R

[0307] R 21 ~R 28 Among the groups described as R 21 ~R 28 some may be optionally substituted as described above, and examples of the substituents in this case include alkyl, cycloalkyl, aryl, or heteroaryl. This alkyl, cycloalkyl, aryl, or heteroaryl can cite the groups described as "alkyl", "cycloalkyl", "aryl", or "heteroaryl" in R

[0308] As Y, ">N-R 29 " in R 29 is hydrogen or an aryl which may be substituted. As this aryl, the groups described as "aryl" in R 21 ~R 28 can be cited, and as its substituents, the groups described as substituents for R 21 ~R 28 can be cited.

[0309] R 21 ~R 28 Among them, adjacent groups may be bonded to each other to form a hydrocarbon ring, an aryl ring or a heteroaryl ring. The case where no ring is formed is a group represented by the following formula (A-1), and the case where a ring is formed includes, for example, groups represented by any of the following formulas (A-2) to (A-14). In addition, at least one hydrogen in the group represented by any of the formulas (A-1) to (A-14) may be substituted with alkyl, cycloalkyl, aryl, heteroaryl, alkoxy, aryloxy, arylthio, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, alkyldicycloalkylsilyl, diaryl-substituted amino, diheteroaryl-substituted amino, arylheteroaryl-substituted amino, halogen, hydroxy or cyano. * in each structural formula represents a bonding position, and Y has the same definition as above.

Chemical formula

[0310] Examples of the ring formed by adjacent groups bonding to each other include a cyclohexane ring in the case of a hydrocarbon ring, and the ring structures described as "aryl" and "heteroaryl" in R 21 ~R 28 can be cited in the above. These rings are formed so as to be condensed with one or two benzene rings in the above formula (A-1).

[0311] Examples of the group represented by the formula (A) include groups represented by any of the above formulas (A-1) to (A-14), with groups represented by any of the above formulas (A-1) to (A-5) and formulas (A-12) to (A-14) being preferred, groups represented by any of the above formulas (A-1) to (A-4) being more preferred, groups represented by any of the above formulas (A-1), (A-3) and (A-4) being even more preferred, and the group represented by the above formula (A-1) being particularly preferred.

[0312] The group represented by the formula (A) binds at the * in the formula (A) to the naphthalene ring in the formula (3-X1) or formula (3-X2), the single bond in the formula (3-X3), or Ar in the formula (3-X3), and replaces at least one hydrogen in the compound represented by the formula (3). As described above, among these bonding forms, the form of binding to at least one of the naphthalene ring in the formula (3-X1) or formula (3-X2), the single bond in the formula (3-X3), and Ar in the formula (3-X3) is preferred. 3 Also, among the bonding forms of the group represented by the formula (A), the position where the naphthalene ring in the formula (3-X1) or formula (3-X2), the single bond in the formula (3-X3), or Ar in the formula (3-X3) binds, and the position where it replaces at least one hydrogen in the compound represented by the formula (3) can be any position in the structure of the formula (A). For example, it can be either of the two benzene rings in the structure of the formula (A), any ring formed by adjacent groups among R to R binding to each other in the structure of the formula (A), or any position in R in ">N-R" as Y in the structure of the formula (A). 3

[0313] In addition, in the structure of the group represented by the formula (A), the position where the naphthalene ring in the formula (3-X1) or formula (3-X2), the single bond in the formula (3-X3), or Ar in the formula (3-X3) binds, and the position where it replaces at least one hydrogen in the compound represented by the formula (3) can be any position in the structure of the formula (A). For example, it can be either of the two benzene rings in the structure of the formula (A), any ring formed by adjacent groups among R to R binding to each other in the structure of the formula (A), or any position in R in ">N-R" as Y in the structure of the formula (A). 3 Examples of the group represented by the formula (A) include the following groups. Y and * in the formula have the same definitions as above. 21 ~R 28 Among them, any ring formed by adjacent groups binding to each other, or any position in R in ">N-R" as Y in the structure of the formula (A). 29 29

[0314] Examples of the group represented by the formula (A) include the following groups. Y and * in the formula have the same definitions as above.

Chemical formula

[0315] In addition, in the chemical structure of the anthracene-based compound represented by the general formula (3), all or part of the hydrogen may be deuterium.

[0316] Specific examples of the anthracene-based compound include, for example, compounds represented by any of the following formulas (3-1) to (3-142). In the following structural formulas, "Me" represents a methyl group, "D" represents deuterium, and "tBu" represents a t-butyl group.

[0317] [Chemical formula]

[0318] [Chemical formula]

[0319] [Chemical formula]

[0320] [Chemical formula]

[0321] [Chemical formula]

[0322] [Chemical formula]

[0323] [Chemical formula]

[0324] The anthracene-based compound represented by formula (3) is a compound having a reactive group at a desired position of the anthracene skeleton, and X, Ar 4 and a compound having a reactive group in a partial structure such as the structure of formula (A) as starting materials, and can be produced by applying Suzuki coupling, Negishi coupling, and other known coupling reactions. Examples of the reactive groups of these reactive compounds include halogen and boronic acid. As a specific production method, for example, the synthesis methods in paragraphs

[0089] to

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

[0325] <Fluorene-based compound> The compound represented by general formula (4) basically functions as a host.

Chemical formula

[0326] In the above formula (4), R 1 to R 10 are each independently hydrogen, aryl, heteroaryl (the heteroaryl 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, and at least one hydrogen in the R 1 to R 10 may be substituted with aryl, heteroaryl, alkyl or cycloalkyl, 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 or R 9 and R 10They may each independently combine to form a condensed ring or a spiro ring, and at least one hydrogen in the formed ring may be substituted with aryl, heteroaryl (the heteroaryl may be bonded to the formed ring via a linking group), diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkenyl, alkoxy or aryloxy, and at least one hydrogen in these substituents may be substituted with aryl, heteroaryl, alkyl or cycloalkyl, and At least one hydrogen in the compound represented by formula (4) may be substituted with halogen, cyano or deuterium.

[0327] Details of each group in the definition of the above formula (4) can cite the description in the polycyclic aromatic compound represented by the above formula (1A) or formula (1B).

[0328] R 1 From R 10 Examples of the alkenyl in R

[0329] Specific examples of heteroaryl also include monovalent groups represented by removing any one hydrogen atom from the compounds of the following formula (4-Ar1), formula (4-Ar2), formula (4-Ar3), formula (4-Ar4) or formula (4-Ar5).

Chemical formula

[0330] These heteroaryls may be bonded to the fluorene skeleton in Formula (4) via a linking group. That is, not only can the fluorene skeleton in Formula (4) and the above heteroaryl be directly bonded, but they may also be bonded via a linking group therebetween. Examples of such a linking group include phenylene, biphenylene, naphthylene, anthracenylene, methylene, ethylene, -OCH2CH2-, -CH2CH2O-, or -OCH2CH2O-.

[0331] Also, R in Formula (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 or R 7 and R 8 may each independently combine to form a fused ring, and R 9 and R 10 may combine to form a spiro ring. The fused ring formed by R 1 to R 8 is a ring fused to the benzene ring in Formula (4), and is an aliphatic ring or an aromatic ring. Preferably it is an aromatic ring, and examples of the structure including the benzene ring in Formula (4) include a naphthalene ring and a phenanthrene ring. The spiro ring formed by R 9 and R 10 is a ring spiro-bonded to the 5-membered ring in Formula (4), and is an aliphatic ring or an aromatic ring. Preferably it is an aromatic ring, and examples include a fluorene ring.

[0332] The compound represented by the general formula (4) is preferably a compound represented by the following formula (4-1), formula (4-2) or formula (4-3), and in each case, in the general formula (4), R 1 and R 2 are combined to form a condensed compound having a benzene ring, in the general formula (4), R 3 and R 4 are combined to form a condensed compound having a benzene ring, in the general formula (4), a compound in which none of R 1 to R 8 is bonded. [Chemical formula]

[0333] The definitions of R 1 to R 10 in the formula (4-1), formula (4-2) and formula (4-3) are the same as the corresponding R 1 to R 10 in the formula (4), and the definitions of R 11 to R 14 in the formula (4-1) and formula (4-2) are also the same as the corresponding R 1 to R 10 in the formula (4).

[0334] The compound represented by the general formula (4) is more preferably a compound represented by the following formula (4-1A), formula (4-2A) or formula (4-3A), and in each case, in the formula (4-1), formula (4-1) or formula (4-3), R 9 and R 10 are combined to form a spiro-fluorene ring. [Chemical formula]

[0335] The definitions of R 2 to R 7 in the formula (4-1A), formula (4-2A) and formula (4-3A) are the same as the corresponding R 2 to R 7is the same as that in Formula (4-1A) and Formula (4-2A), and the definition of R from R in Formula (4-1A) and Formula (4-2A) is also the same as that of R from R in Formula (4-1) and Formula (4-2). 11 to R 14 is also the same as that of R from R in Formula (4-1) and Formula (4-2). 11 to R 14 is the same as that in Formula (4-1) and Formula (4-2).

[0336] In addition, in the compound represented by Formula (4), all or part of the hydrogen may be substituted with halogen, cyano or deuterium.

[0337] Specific examples of the fluorene-based compound include, for example, compounds represented by any of the following Formulas (4-4) to (4-22). In the following structural formulas, "Me" represents a methyl group.

Chemical formula

[0338] <Dibenzocrisene-based compound> The dibenzocrisene-based compound as a host is, for example, a compound represented by the following general formula (5).

Chemical formula

[0339] In the above formula (5), R 1 to R 16 are each independently hydrogen, aryl, heteroaryl (the heteroaryl may be bonded to the dibenzocrisene skeleton in the above formula (5) via a linking group), diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkenyl, alkoxy or aryloxy, and at least one hydrogen in the R 1 to R 16 may be substituted with aryl, heteroaryl, alkyl or cycloalkyl, and also, R 1 to R 16Among them, adjacent groups may be bonded to form a condensed ring, and at least one hydrogen in the formed ring may be substituted with aryl, heteroaryl (the heteroaryl may be bonded to the formed ring via a linking group), diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkenyl, alkoxy or aryloxy, and at least one hydrogen in these substituents may be substituted with aryl, heteroaryl, alkyl or cycloalkyl, and At least one hydrogen in the compound represented by the formula (5) may be substituted with halogen, cyano or deuterium.

[0340] Details of each group in the definition of the above formula (5) can cite the description in the polycyclic aromatic compound represented by the above formula (1A) or formula (1B).

[0341] Examples of the alkenyl in the definition of the above formula (5) include alkenyl having 2 to 30 carbon atoms, preferably alkenyl having 2 to 20 carbon atoms, more preferably alkenyl having 2 to 10 carbon atoms, still more preferably alkenyl having 2 to 6 carbon atoms, and particularly preferably alkenyl having 2 to 4 carbon atoms. Preferred alkenyls are vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, or 5-hexenyl.

[0342] Specific examples of the heteroaryl also include monovalent groups represented by removing any one hydrogen atom from the compounds of the following formula (5-Ar1), formula (5-Ar2), formula (5-Ar3), formula (5-Ar4) or formula (5-Ar5).

Chemical formula

[0343] These heteroaryls may be bonded to the dibenzocrisene skeleton in formula (5) via a linking group. That is, not only can the dibenzocrisene skeleton in formula (5) and the above heteroaryl be directly bonded, but they may also be bonded via a linking group therebetween. Examples of this linking group include phenylene, biphenylene, naphthylene, anthracenylene, methylene, ethylene, -OCH2CH2-, -CH2CH2O-, or -OCH2CH2O-.

[0344] The compound represented by general formula (5) preferably has R 1 、R 4 、R 5 、R 8 、R 9 、R 12 、R 13 and R 16 being hydrogen. In this case, R 2 、R 3 、R 6 、R 7 、R 10 、R 11 、R 14 and R 15Each is independently hydrogen, phenyl, biphenylyl, naphthyl, anthracenyl, phenanthrenyl, a monovalent group having the structure of the above formula (5-Ar1), formula (5-Ar2), formula (5-Ar3), formula (5-Ar4) or formula (5-Ar5) (the monovalent group having the structure may be connected to the dibenzocrisene skeleton in the above formula (5) via phenylene, biphenylene, naphthylene, anthracenylene, methylene, ethylene, -OCH2CH2-, -CH2CH2O-, or -OCH2CH2O-), methyl, ethyl, propyl, or butyl is preferable.

[0345] The compound represented by the 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, R 3 、R 6 、R 11 and R 14 at least one (preferably one or two, more preferably one) of is a single bond, phenylene, biphenylene, naphthylene, anthracenylene, methylene, ethylene, -OCH2CH2-, -CH2CH2O-, or a monovalent group having the structure of the above formula (5-Ar1), formula (5-Ar2), formula (5-Ar3), formula (5-Ar4) or formula (5-Ar5) via -OCH2CH2O-, Other than the at least one (that is, other than the position substituted with the monovalent group having the structure) is hydrogen, phenyl, biphenylyl, naphthyl, anthracenyl, methyl, ethyl, propyl, or butyl, and at least one hydrogen in these groups may be substituted with phenyl, biphenylyl, naphthyl, anthracenyl, methyl, ethyl, propyl, or butyl.

[0346] Also, R in the formula (5)2 , R 3 , R 6 , R 7 , R 10 , R 11 , R 14 and R 15 As, when a monovalent group having a structure represented by the above formula (5-Ar1) to formula (5-Ar5) is selected, at least one hydrogen in the structure may be bonded to any of R 1 from R 16 to form a single bond.

[0347] Specific examples of the dibenzocrisene-based compound include, for example, compounds represented by any of the following formulas (5-1) to (5-39). In the following structural formulas, "tBu" represents a t-butyl group.

Chemical formula

[0348]

Chemical formula

[0349] The above-described materials for the light-emitting layer (host material and dopant material) can also be used as a light-emitting layer material in the form of a polymer compound obtained by polymerizing a reactive compound having a reactive substituent as a monomer, or a polymer crosslinked body thereof, or a pendant polymer compound obtained by reacting a main-chain polymer with the reactive compound, or a pendant polymer crosslinked body thereof. As the reactive substituent in this case, the description of the polycyclic aromatic compound represented by the formula (1A) or formula (1B) can be cited. Details of the uses of such polymer compounds and polymer crosslinked bodies will be described later.

[0350] <An example of a polymer host material>

Chemical formula

[0351] In formula (SPH-1), MU is a divalent group each independently represented by removing any two hydrogen atoms from an aromatic compound, and EC is a monovalent group each independently represented by removing any one hydrogen atom from an aromatic compound. Two hydrogens in MU are substituted with EC or MU, and k is an integer from 2 to 50,000.

[0352] More specifically, MU is each independently arylene, heteroarylene, diarylene arylamino, diarylene arylboryl, oxaborin-diyl, or azaborin-diyl, EC is each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, or aryloxy, At least one hydrogen in MU and EC may be further substituted with aryl, heteroaryl, diarylamino, alkyl, and cycloalkyl, k is an integer from 2 to 50,000. k is preferably an integer from 20 to 50,000, and more preferably an integer from 100 to 50,000.

[0353] At least one hydrogen in MU and EC in formula (SPH-1) may be substituted with alkyl having 1 to 24 carbon atoms, cycloalkyl having 3 to 24 carbon atoms, halogen, or deuterium. Further, any -CH2- in the alkyl may be substituted with -O- or -Si(CH3)2-. Any -CH2- in the alkyl excluding the -CH2- directly bonded to EC in formula (SPH-1) may be substituted with arylene having 6 to 24 carbon atoms. Any hydrogen in the alkyl may be substituted with fluorine.

[0354] Examples of MU include a divalent group represented by removing any two hydrogen atoms from any of the following compounds.

Chemical formula

[0355] More specifically, divalent groups represented by any of the following structures can be mentioned. In these, MU is bonded to another MU or EC at *.

Chemical formula

Chemical formula

Chemical formula

Chemical formula

Chemical formula

Chemical formula

Chemical formula

Chemical formula

Chemical formula

[0356] Also, as EC, monovalent groups represented by any of the following structures can be mentioned. In these, EC is bonded to MU at *.

[0357]

Chemical formula

Chemical formula

[0358] From the viewpoints of solubility and coatability to form a film, it is preferable that 10 to 100% of the total number (k) of MUs in the molecule have an alkyl group having 1 to 24 carbon atoms, more preferably 30 to 100% of the total number (k) of MUs in the molecule have an alkyl group having 1 to 18 carbon atoms (a branched alkyl group having 3 to 18 carbon atoms), and still more preferably 50 to 100% of the total number (k) of MUs in the molecule have an alkyl group having 1 to 12 carbon atoms (a branched alkyl group having 3 to 12 carbon atoms). On the other hand, from the viewpoints of in-plane orientation and charge transport, it is preferable that 10 to 100% of the total number (k) of MUs in the molecule have an alkyl group having 7 to 24 carbon atoms, and more preferably 30 to 100% of the total number (k) of MUs in the molecule have an alkyl group having 7 to 24 carbon atoms (a branched alkyl group having 7 to 24 carbon atoms).

[0359] Details of the uses of such polymer compounds and polymer crosslinked bodies will be described later.

[0360] <Electron injection layer, electron transport layer in organic electroluminescent device> The electron injection layer 107 serves to efficiently inject electrons moving from the cathode 108 into the light emitting layer 105 or the electron transport layer 106. The electron transport layer 106 serves to efficiently transport electrons injected from the cathode 108 or electrons injected from the cathode 108 through the electron injection layer 107 to the light emitting layer 105. The electron transport layer 106 and the electron injection layer 107 are each formed by laminating and mixing one or two or more kinds of electron transport / injection materials, or by a mixture of an electron transport / injection material and a polymer binder.

[0361] The electron injection / transport layer is a layer that controls the injection of electrons from the cathode and further transports the electrons. It is desirable that the electron injection efficiency is high and the injected electrons can be transported efficiently. For this purpose, it is preferable that the material has a large electron affinity, a large electron mobility, excellent stability, and is less likely to generate trap impurities during manufacturing and use. However, when considering the transport balance between holes and electrons, if it mainly plays a role in efficiently preventing holes from the anode from flowing to the cathode without recombination, even if the electron transport ability is not so high, the effect of improving the light emission efficiency is equivalent to that of a material with a high electron transport ability. Therefore, the electron injection / transport layer in this embodiment may also include the function of a layer that can efficiently block the movement of holes.

[0362] As the material (electron transport material) for forming the electron transport layer 106 or the electron injection layer 107, a polycyclic aromatic compound represented by the above general formula (1A) or general formula (1B) can be used. Also, it can be arbitrarily selected and used from compounds conventionally used as electron transfer compounds in photoconductive materials and known compounds used in the electron injection layer and electron transport layer of organic EL elements.

[0363] As materials used for the electron transport layer or the electron injection layer, it is preferable to contain at least one selected from compounds composed of aromatic rings or heteroaromatic rings composed of one or more atoms selected from carbon, hydrogen, oxygen, sulfur, silicon, and phosphorus, pyrrole derivatives and their condensed ring derivatives, and metal complexes having electron-accepting nitrogen. Specifically, condensed ring aromatic ring derivatives such as naphthalene and anthracene, styryl aromatic ring derivatives typified by 4,4'-bis(diphenylethenyl)biphenyl, perinone derivatives, coumarin derivatives, naphthalimide derivatives, quinone derivatives such as anthraquinone and diphenoquinone, phosphorus oxide derivatives, carbazole derivatives, and indole derivatives can be mentioned. Examples of the metal complex having electron-accepting nitrogen include hydroxyazole complexes such as hydroxyphenyloxazole complexes, azomethine complexes, tropolone metal complexes, flavonol metal complexes, and benzoquinoline metal complexes. These materials can be used alone or in combination with different materials.

[0364] In addition, specific examples of other electron transfer compounds include pyridine derivatives, naphthalene derivatives, anthracene derivatives, phenanthroline derivatives, perinone derivatives, coumarin derivatives, naphthalimide derivatives, anthraquinone derivatives, diphenoquinone derivatives, diphenylquinone derivatives, perylene derivatives, oxadiazole derivatives (such as 1,3-bis[(4-t-butylphenyl)1,3,4-oxadiazolyl]phenylene), thiophene derivatives, triazole derivatives (such as N-naphthyl-2,5-diphenyl-1,3,4-triazole), thiadiazole derivatives, metal complexes of oxine derivatives, quinolinol-based metal complexes, quinoxaline derivatives, polymers of quinoxaline derivatives, benzazole compounds, gallium complexes, pyrazole derivatives, perfluorinated phenylene derivatives, triazine derivatives, pyrazine derivatives, benzoquinoline derivatives (such as 2,2’-bis(benzo[h]quinolin-2-yl)-9,9’-spirobifluorene), imidazopyridine derivatives, borane derivatives, benzimidazole derivatives (such as tris(N-phenylbenzimidazol-2-yl)benzene), benzoxazole derivatives, benzothiazole derivatives, quinoline derivatives, oligopyridine derivatives such as terpyridine, bipyridine derivatives, terpyridine derivatives (such as 1,3-bis(4’-(2,2’:6’2”-terpyridinyl))benzene), naphthyridine derivatives (such as bis(1-naphthyl)-4-(1,8-naphthyridin-2-yl)phenylphosphine oxide), aldazine derivatives, carbazole derivatives, indole derivatives, phosphine oxide derivatives, bisstyryl derivatives, and the like.

[0365] In addition, metal complexes having electron-accepting nitrogen can also be used, for example, hydroxyazole complexes such as quinolinol-based metal complexes and hydroxyphenyloxazole complexes, azomethine complexes, tropolone metal complexes, flavonol metal complexes, and benzoquinoline metal complexes.

[0366] The above-described materials can be used alone or can be mixed and used with different materials.

[0367] Among the above-described materials, borane derivatives, pyridine derivatives, fluoranthene derivatives, BO-based derivatives, anthracene derivatives, benzofluorene derivatives, phosphine oxide derivatives, pyrimidine derivatives, carbazole derivatives, triazine derivatives, benzimidazole derivatives, phenanthroline derivatives, and quinolinol-based metal complexes are preferred.

[0368] <Borane derivative> The borane derivative is, for example, a compound represented by the following general formula (ETM-1), and specifically, it is disclosed in JP-A-2007-27587. [Chemical formula] In the above formula (ETM-1), R 11 and R 12 are each independently at least one of hydrogen, alkyl, cycloalkyl, optionally substituted aryl, substituted silyl, optionally substituted nitrogen-containing heterocycle, or cyano, and R 13 ~R 16 are each independently optionally substituted alkyl, optionally substituted cycloalkyl or optionally substituted aryl, X is optionally substituted arylene, Y is optionally substituted aryl having 16 or less carbon atoms, substituted boryl, or optionally substituted carbazolyl, and n is each independently an integer of 0 to 3. Further, examples of the substituent in the case of "optionally substituted" or "substituted" include aryl, heteroaryl, alkyl, or cycloalkyl.

[0369] Among the compounds represented by the above general formula (ETM-1), compounds represented by the following general formula (ETM-1-1) and compounds represented by the following general formula (ETM-1-2) are preferred. [Chemical formula] In formula (ETM-1-1), R 11 and R 12is independently at least one of hydrogen, alkyl, cycloalkyl, optionally substituted aryl, substituted silyl, optionally substituted nitrogen-containing heterocycle, or cyano, and R 13 ~R 16 is independently optionally substituted alkyl, optionally substituted cycloalkyl or optionally substituted aryl, and R 21 and R 22 are independently at least one of hydrogen, alkyl, cycloalkyl, optionally substituted aryl, substituted silyl, optionally substituted nitrogen-containing heterocycle, or cyano, and X 1 is optionally substituted arylene having 20 or less carbon atoms, n is independently an integer of 0 to 3, and m is independently an integer of 0 to 4. Further, examples of the substituent in the case of "optionally substituted" or "substituted" include aryl, heteroaryl, alkyl, or cycloalkyl. [Chemical formula] In formula (ETM-1-2), R 11 and R 12 are independently at least one of hydrogen, alkyl, cycloalkyl, optionally substituted aryl, substituted silyl, optionally substituted nitrogen-containing heterocycle, or cyano, and R 13 ~R 16 are independently optionally substituted alkyl, optionally substituted cycloalkyl or optionally substituted aryl, and X 1 is optionally substituted arylene having 20 or less carbon atoms, and n is independently an integer of 0 to 3. Further, examples of the substituent in the case of "optionally substituted" or "substituted" include aryl, heteroaryl, alkyl, or cycloalkyl.

[0370] X 1Specific examples thereof include divalent groups represented by any of the following formulas (X-1) to (X-9). * in each structural formula represents a bonding position. [Chemical formula] (In each formula, R a is independently an alkyl group, a cycloalkyl group, or an optionally substituted phenyl group.)

[0371] Specific examples of this borane derivative include, for example, the following compounds. [Chemical formula]

[0372] This borane derivative can be produced using known raw materials and known synthesis methods.

[0373] [Pyridine derivative] The pyridine derivative is, for example, a compound represented by the following formula (ETM-2), and preferably a compound represented by formula (ETM-2-1) or formula (ETM-2-2). [Chemical formula]

[0374] φ is an n-valent aryl ring (preferably an n-valent benzene ring, naphthalene ring, anthracene ring, fluorene ring, benzofluorene ring, phenalene ring, phenanthrene ring, or triphenylene ring), and n is an integer from 1 to 4.

[0375] In the above formula (ETM-2-1), R 11 ~R 18 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).

[0376] In the above formula (ETM-2-2), R11 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 combine to form a ring.

[0377] In each formula, the "pyridine-based substituent" is any one of the following formulas (Py-1) to (Py-15), and the pyridine-based substituents may each independently be substituted with alkyl having 1 to 4 carbon atoms or cycloalkyl having 5 to 10 carbon atoms. Further, the pyridine-based substituent may be bonded to φ, an anthracene ring or a fluorene ring in each formula via a phenylene group or a naphthylene group. * in each structural formula represents the bonding position.

Chemical formula

[0378] The pyridine-based substituent is any one of the above formulas (Py-1) to (Py-15), and among these, it is preferably any one of the following formulas (Py-21) to (Py-44). * in each structural formula represents the bonding position.

Chemical formula

[0379] At least one hydrogen in each pyridine derivative may be substituted with deuterium, and one of the two "pyridine-based substituents" in the above formulas (ETM-2-1) and (ETM-2-2) may be replaced with aryl.

[0380] R 11 ~R 18The "alkyl" herein may be either straight-chain or branched-chain, and examples thereof include straight-chain alkyl having 1 to 24 carbon atoms or branched-chain alkyl having 3 to 24 carbon atoms. Preferred "alkyl" is alkyl having 1 to 18 carbon atoms (branched-chain alkyl having 3 to 18 carbon atoms). More preferred "alkyl" is alkyl having 1 to 12 carbon atoms (branched-chain alkyl having 3 to 12 carbon atoms). Further preferred "alkyl" is alkyl having 1 to 6 carbon atoms (branched-chain alkyl having 3 to 6 carbon atoms). Particularly preferred "alkyl" is alkyl having 1 to 4 carbon atoms (branched-chain alkyl having 3 to 4 carbon atoms).

[0381] 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-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, t-octyl (1,1,3,3-tetramethylbutyl), 1-methylheptyl, 2-ethylhexyl, 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, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, n-eicosyl, and the like. In addition, 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-methylhexyl, 1-ethyl-1,3-dimethylbutyl, 1,1,2,2-tetramethylpropyl, 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, etc. can be mentioned.

[0382] As the alkyl having 1 to 4 carbon atoms substituting the pyridine-based substituent, the description of the above alkyl can be cited.

[0383] R 11 ~R 18 Examples of the "cycloalkyl" in R~R include cycloalkyl having 3 to 12 carbon atoms. Preferred "cycloalkyl" is cycloalkyl having 3 to 10 carbon atoms. More preferred "cycloalkyl" is cycloalkyl having 3 to 8 carbon atoms. Even more preferred "cycloalkyl" is cycloalkyl having 3 to 6 carbon atoms. Specific examples of the "cycloalkyl" include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclopentyl, cycloheptyl, methylcyclohexyl, cyclooctyl or dimethylcyclohexyl, etc.

[0384] As the cycloalkyl having 5 to 10 carbon atoms substituting the pyridine-based substituent, the description of the above cycloalkyl can be cited.

[0385] R 11 ~R 18As the "aryl" in the formula, preferred aryl groups have 6 to 30 carbon atoms, more preferred aryl groups have 6 to 18 carbon atoms, still more preferred aryl groups have 6 to 14 carbon atoms, and particularly preferred aryl groups have 6 to 12 carbon atoms.

[0386] Specific examples of the "aryl group having 6 to 30 carbon atoms" include phenyl which is a monocyclic aryl group, (1-, 2-) naphthyl which is a condensed bicyclic aryl group, acenaphthylen-(1-, 3-, 4-, 5-)yl, fluorene-(1-, 2-, 3-, 4-, 9-)yl, phenalen-(1-, 2-)yl, (1-, 2-, 3-, 4-, 9-)phenanthryl which are condensed tricyclic aryl groups, triphenylene-(1-, 2-)yl, pyrene-(1-, 2-, 4-)yl, naphthacene-(1-, 2-, 5-)yl which are condensed tetracyclic aryl groups, perylene-(1-, 2-, 3-)yl, pentacene-(1-, 2-, 5-, 6-)yl which are condensed pentacyclic aryl groups, and the like.

[0387] Preferred "aryl groups having 6 to 30 carbon atoms" include phenyl, naphthyl, phenanthryl, chrysenyl or triphenylenyl, etc., more preferably phenyl, 1-naphthyl, 2-naphthyl or phenanthryl, and particularly preferably phenyl, 1-naphthyl or 2-naphthyl.

[0388] R in the above formula (ETM-2-2) 11 and R 12 may combine to form a ring. As a result, a cyclobutane, cyclopentane, cyclopentene, cyclopentadiene, cyclohexane, fluorene or indene, etc. may be spiro-bonded to the 5-membered ring of the fluorene skeleton.

[0389] Specific examples of this pyridine derivative include, for example, the following compounds.

Chemical formula

[0390] This pyridine derivative can be produced using known raw materials and known synthesis methods.

[0391] <Fluoranthene derivative> The fluoranthene derivative is, for example, a compound represented by the following general formula (ETM-3), and is specifically disclosed in International Publication No. 2010 / 134352. [Chemical formula]

[0392] In the above formula (ETM-3), X 12 ~X 21 represents hydrogen, halogen, linear, branched or cyclic alkyl, linear, branched or cyclic alkoxy, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl. Here, examples of the substituent when it is substituted include aryl, heteroaryl, alkyl or cycloalkyl.

[0393] Specific examples of this fluoranthene derivative include, for example, the following compounds. [Chemical formula]

[0394] <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]

[0395] R 1 ~R 11are each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboril (the two aryls may be bonded via a single bond or a linking group), alkyl, cycloalkyl, alkoxy or aryloxy, and the R 1 ~R 11 at least one hydrogen in may be optionally substituted with aryl, heteroaryl, alkyl or cycloalkyl.

[0396] Also, R 1 ~R 11 adjacent groups among 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 optionally substituted with aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboril (the two aryls may be bonded via a single bond or a linking group), alkyl, cycloalkyl, alkoxy or aryloxy, and at least one hydrogen in these substituents may be optionally substituted with aryl, heteroaryl, alkyl or cycloalkyl.

[0397] Also, at least one hydrogen in the compound or structure represented by formula (ETM-4) may be optionally substituted with halogen or deuterium.

[0398] Regarding the substituents, ring formation forms in formula (ETM-4), and the description of the multimer formed by combining a plurality of the structures of formula (ETM-4), the description in International Publication No. 2015 / 102118 or the description of the polycyclic aromatic compound represented by the above formula (1A) or formula (1B) can be cited.

[0399] Specific examples of this BO-based derivative include, for example, the following compounds.

Chemical formula

[0400] This BO-based derivative can be produced using known raw materials and known synthesis methods.

[0401] <Anthracene derivative> One of the anthracene derivatives is, for example, a compound represented by the following formula (ETM-5-1). [Chemical formula]

[0402] Ar is, independently of each other, divalent benzene or naphthalene, and R 1 ~R 4 is, independently of each other, hydrogen, alkyl having 1 to 6 carbon atoms, cycloalkyl having 3 to 6 carbon atoms, or aryl having 6 to 20 carbon atoms.

[0403] Ar can be appropriately selected independently of each other from divalent benzene or naphthalene, and the two Ars may be different or the same, but from the viewpoint of the ease of synthesis of the anthracene derivative, it is preferably the same. Ar is bonded to pyridine to form a "site consisting of Ar and pyridine", and this site is bonded to anthracene as a group represented by, for example, any of the following formulas (Py-1) to (Py-12). * in each structural formula represents the bonding position. [Chemical formula]

[0404] Among these groups, a group represented by any of the above formulas (Py-1) to (Py-9) is preferable, and a group represented by any of the above formulas (Py-1) to (Py-6) is more preferable. The two "sites consisting of Ar and pyridine" bonded to anthracene may have the same or different structures, but from the viewpoint of the ease of synthesis of the anthracene derivative, it is preferably the same structure. However, from the viewpoint of device characteristics, it is preferable that the structures of the two "sites consisting of Ar and pyridine" are the same or different.

[0405] R 1 ~R 4 For the alkyl group having 1 to 6 carbon atoms in R, either a straight-chain or a branched-chain may be used. That is, it is a straight-chain alkyl group having 1 to 6 carbon atoms or a branched-chain alkyl group having 3 to 6 carbon atoms. More preferably, it is an alkyl group having 1 to 4 carbon atoms (a branched-chain alkyl group having 3 to 4 carbon atoms). Specific examples 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-dimethylbutyl, or 2-ethylbutyl, etc. Among them, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, or t-butyl are preferred, and methyl, ethyl, or t-butyl are more preferred.

[0406] R 1 ~R 4 Specific examples of the cycloalkyl group having 3 to 6 carbon atoms in R include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclopentyl, cycloheptyl, methylcyclohexyl, cyclooctyl, or dimethylcyclohexyl, etc.

[0407] R 1 ~R 4 For the aryl group having 6 to 20 carbon atoms in R, an aryl group having 6 to 16 carbon atoms is preferred, an aryl group having 6 to 12 carbon atoms is more preferred, and an aryl group having 6 to 10 carbon atoms is particularly preferred.

[0408] Specific examples of "aryl having 6 to 20 carbon atoms" include phenyl, which is a monocyclic aryl, (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; (2-, 3-, 4-) biphenylyl, which is a bicyclic aryl; (1-, 2-) naphthyl, which is a condensed bicyclic aryl; terphenylyl (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-terphenyl-4-yl, o-terphenyl-2-yl, o-terphenyl-3-yl, o-terphenyl-4-yl, p-terphenyl-2-yl, p-terphenyl-3-yl, p-terphenyl-4-yl), which is a tricyclic aryl; anthracen-(1-, 2-, 9-) yl, acenaphthylen-(1-, 3-, 4-, 5-) yl, fluorene-(1-, 2-, 3-, 4-, 9-) yl, phenalen-(1-, 2-) yl, (1-, 2-, 3-, 4-, 9-) phenanthryl, which are condensed tricyclic aryls; triphenylene-(1-, 2-) yl, pyrene-(1-, 2-, 4-) yl, tetracen-(1-, 2-, 5-) yl, which are condensed tetracyclic aryls; perylene-(1-, 2-, 3-) yl, which is a condensed pentacyclic aryl, and the like.

[0409] Preferred "aryl having 6 to 20 carbon atoms" is phenyl, biphenylyl, terphenylyl or naphthyl; more preferred is phenyl, biphenylyl, 1-naphthyl, 2-naphthyl or m-terphenyl-5'-yl; still more preferred is phenyl, biphenylyl, 1-naphthyl or 2-naphthyl; and most preferred is phenyl.

[0410] One of the anthracene derivatives is, for example, a compound represented by the following formula (ETM-5-2).

Chemical formula

[0411] Ar 1 is, independently of one another, a single bond, divalent benzene, naphthalene, anthracene, fluorene, or phenalene.

[0412] Ar 2 is, independently of one another, aryl having 6 to 20 carbon atoms, and the same description as "aryl having 6 to 20 carbon atoms" in the above formula (ETM-5-1) can be cited. Aryl 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. Specific examples include phenyl, biphenylyl, naphthyl, terphenylyl, anthracenyl, acenaphthylenyl, fluorenyl, phenalenyl, phenanthryl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, etc.

[0413] R 1 ~R 4 is, independently of one another, hydrogen, alkyl having 1 to 6 carbon atoms, cycloalkyl having 3 to 6 carbon atoms or aryl having 6 to 20 carbon atoms, and the description in the above formula (ETM-5-1) can be cited.

[0414] Specific examples of these anthracene derivatives include, for example, the following compounds.

Chemical formula

[0415] These anthracene derivatives can be produced using known raw materials and known synthesis methods.

[0416] <Benzofluorene derivative> The benzofluorene derivative is, for example, a compound represented by the following formula (ETM-6).

Chemical formula

[0417] Ar 1is, independently of each other, aryl having 6 to 20 carbon atoms, and the same description as "aryl having 6 to 20 carbon atoms" in the above formula (ETM-5-1) can be cited. Aryl 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. Specific examples include phenyl, biphenylyl, naphthyl, terphenylyl, anthracenyl, acenaphthylenyl, fluorenyl, phenalenyl, phenanthryl, triphenylenyl, pyrenyl, tetracenyl, perylenyl and the like.

[0418] Ar 2 is, independently of each other, 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 two Ars 2 may be bonded to form a ring.

[0419] Ar 2 The "alkyl" in Ar may be either linear or branched, and examples include linear alkyl having 1 to 24 carbon atoms or branched alkyl having 3 to 24 carbon atoms. 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 (branched alkyl having 3 to 12 carbon atoms). Even more preferred "alkyl" is alkyl having 1 to 6 carbon atoms (branched alkyl having 3 to 6 carbon atoms). Particularly preferred "alkyl" is alkyl having 1 to 4 carbon atoms (branched alkyl having 3 to 4 carbon atoms). Specific "alkyl" includes 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-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl and the like.

[0420] Ar 2Examples of the "cycloalkyl" herein include cycloalkyls having 3 to 12 carbon atoms. Preferred "cycloalkyl" is cycloalkyl having 3 to 10 carbon atoms. More preferred "cycloalkyl" is cycloalkyl having 3 to 8 carbon atoms. Even more preferred "cycloalkyl" is cycloalkyl having 3 to 6 carbon atoms. Specific examples of the "cycloalkyl" include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclopentyl, cycloheptyl, methylcyclohexyl, cyclooctyl or dimethylcyclohexyl, etc.

[0421] Ar 2 Examples of the "aryl" herein, preferred aryl is aryl having 6 to 30 carbon atoms, more preferred aryl is aryl having 6 to 18 carbon atoms, even more preferably aryl having 6 to 14 carbon atoms, and particularly preferably aryl having 6 to 12 carbon atoms.

[0422] Specific examples of the "aryl having 6 to 30 carbon atoms" include phenyl, naphthyl, acenaphthylenyl, fluorenyl, phenalenyl, phenanthryl, triphenylenyl, pyrenyl, naphthacenyl, perylenyl, pentacenyl, etc.

[0423] Two Ars 2 may be bonded to form a ring. As a result, cyclobutane, cyclopentane, cyclopentene, cyclopentadiene, cyclohexane, fluorene or indene, etc. may be spiro-bonded to the 5-membered ring of the fluorene skeleton.

[0424] Specific examples of this benzofluorene derivative include, for example, the following compounds.

Chemical formula

[0425] This benzofluorene derivative can be produced using known raw materials and known synthesis methods.

[0426] <Phosphine Oxide Derivative> The phosphine oxide derivative is, for example, a compound represented by the following formula (ETM-7-1). Details are also described in International Publication No. 2013 / 079217.

Chemical formula

[0427] The phosphine oxide derivative may also be, for example, a compound represented by the following formula (ETM-7-2).

Chemical formula

[0428] R 1 ~R 3may be the same or different, and is selected from hydrogen, an alkyl group, a cycloalkyl group, an aralkyl group, an alkenyl group, a cycloalkenyl group, an alkynyl group, an alkoxy group, an alkylthio group, a cycloalkylthio group, an aryl ether group, an arylthioether group, an aryl group, a heterocyclic group, a halogen, a cyano group, an aldehyde group, a carbonyl group, a carboxyl group, an amino group, a nitro group, a silyl group, and a condensed ring formed between adjacent substituents.

[0429] Ar 1 may be the same or different, and is an arylene group or a heteroarylene group. Ar 2 may be the same or different, and is an aryl group or a heteroaryl group. However, Ar 1 and Ar 2 at least one of them has a substituent or forms a condensed ring with an adjacent substituent. n is an integer from 0 to 3. When n is 0, there is no unsaturated structure portion. When n is 3, R 1 does not exist.

[0430] Among these substituents, the alkyl group represents, for example, a saturated aliphatic hydrocarbon group such as a methyl group, an ethyl group, a propyl group, or a butyl group, which may be unsubstituted or substituted. There are no particular restrictions on the substituents when it is substituted. For example, an alkyl group, an aryl group, a heterocyclic group, etc. can be mentioned. This point is also common to the following descriptions. Also, the number of carbon atoms of the alkyl group is not particularly limited, but usually ranges from 1 to 20 from the viewpoints of availability and cost.

[0431] Also, the cycloalkyl group represents, for example, a saturated alicyclic hydrocarbon group such as cyclopropyl, cyclohexyl, norbornyl, or adamantyl, which may be unsubstituted or substituted. The number of carbon atoms in the alkyl group portion is not particularly limited, but usually ranges from 3 to 20.

[0432] In addition, an aralkyl group refers to, for example, an aromatic hydrocarbon group via an aliphatic hydrocarbon such as a benzyl group or a phenylethyl group, and both the aliphatic hydrocarbon and the aromatic hydrocarbon may be unsubstituted or substituted. The number of carbon atoms in the aliphatic part is not particularly limited, but is usually in the range of 1 to 20.

[0433] In addition, an alkenyl group refers to, for example, an unsaturated aliphatic hydrocarbon group containing a double bond such as a vinyl group, an allyl group, or a butadienyl group, 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.

[0434] In addition, a cycloalkenyl group refers to, for example, an unsaturated alicyclic hydrocarbon group containing a double bond such as a cyclopentenyl group, a cyclopentadienyl group, or a cyclohexenyl group, which may be unsubstituted or substituted.

[0435] In addition, an alkynyl group refers to, for example, an unsaturated aliphatic hydrocarbon group containing a triple bond such as an ethynyl group, which may be unsubstituted or substituted. The number of carbon atoms in the alkynyl group is not particularly limited, but is usually in the range of 2 to 20.

[0436] In addition, an alkoxy group refers to, for example, an aliphatic hydrocarbon group via an ether bond such as a methoxy group, and the aliphatic hydrocarbon group may be unsubstituted or substituted. The number of carbon atoms in the alkoxy group is not particularly limited, but is usually in the range of 1 to 20.

[0437] In addition, an alkylthio group is a group in which the oxygen atom of the ether bond of an alkoxy group is replaced by a sulfur atom.

[0438] In addition, a cycloalkylthio group is a group in which the oxygen atom of the ether bond of a cycloalkoxy group is replaced by a sulfur atom.

[0439] The aryl ether group refers to, for example, an aromatic hydrocarbon group via an ether bond such as a phenoxy group, and 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.

[0440] The aryl thioether group is a group in which the oxygen atom of the ether bond of the aryl ether group is substituted with a sulfur atom.

[0441] The aryl group refers to, for example, aromatic hydrocarbon groups such as a phenyl group, a naphthyl group, a biphenyl group, a phenanthryl group, a terphenyl group, and a pyrenyl group. The aryl group may be unsubstituted or substituted. The number of carbon atoms in the aryl group is not particularly limited, but is usually in the range of 6 to 40.

[0442] The heterocyclic group refers to, for example, a cyclic structural group having an atom other than carbon such as a furanyl group, a thiophenyl group, an oxazolyl group, a pyridyl group, a quinolinyl group, and a carbazolyl group, and this may be unsubstituted or substituted. The number of carbon atoms in the heterocyclic group is not particularly limited, but is usually in the range of 2 to 30.

[0443] Halogen refers to fluorine, chlorine, bromine, and iodine.

[0444] The aldehyde group, carbonyl group, and amino group can also include groups substituted with an aliphatic hydrocarbon, alicyclic hydrocarbon, aromatic hydrocarbon, heterocycle, etc.

[0445] The aliphatic hydrocarbon, alicyclic hydrocarbon, aromatic hydrocarbon, and heterocycle may be unsubstituted or substituted.

[0446] The silyl group refers to, for example, a silicon compound group such as a trimethylsilyl group, and this may be unsubstituted or substituted. The number of carbon atoms in the silyl group is not particularly limited, but is usually in the range of 3 to 20. Also, the number of silicon atoms is usually 1 to 6.

[0447] The condensed ring formed between adjacent substituents is, for example, Ar 1 and R 2 , Ar 1 and R 3 , Ar 2 and R 2 , Ar 2 and R 3 , R 2 and R 3 , Ar 1 and Ar 2 etc. It is a conjugated or non-conjugated condensed ring formed therebetween. Here, when n is 1, two R 1 may form a conjugated or non-conjugated condensed ring with each other. These condensed rings may contain nitrogen, oxygen, or sulfur atoms in the ring structure, and may further condense with another ring.

[0448] Specific examples of this phosphine oxide derivative include, for example, the following compounds.

Chemical formula

[0449] This phosphine oxide derivative can be produced using known raw materials and known synthesis methods.

[0450] <Pyrimidine derivative> The pyrimidine derivative is, for example, a compound represented by the following formula (ETM-8), preferably a compound represented by the following formula (ETM-8-1). Details are also described in International Publication No. WO2011 / 021689.

Chemical formula

[0451] Ar is each independently optionally substituted aryl or optionally substituted heteroaryl. n is an integer from 1 to 4, preferably an integer from 1 to 3, more preferably 2 or 3.

[0452] Examples of the "aryl" in "aryl which may be substituted" include aryl having 6 to 30 carbon atoms, preferably aryl having 6 to 24 carbon atoms, more preferably aryl having 6 to 20 carbon atoms, and even more preferably aryl having 6 to 12 carbon atoms.

[0453] Specific examples of "aryl" include phenyl which is a monocyclic aryl, (2-, 3-, 4-) biphenylyl which is a bicyclic aryl, (1-, 2-) naphthyl which is a condensed bicyclic aryl, 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-terphenyl-4-yl, o-terphenyl-2-yl, o-terphenyl-3-yl, o-terphenyl-4-yl, p-terphenyl-2-yl, p-terphenyl-3-yl, p-terphenyl-4-yl) which is a tricyclic aryl, acenaphthylene-(1-, 3-, 4-, 5-)yl, fluorene-(1-, 2-, 3-, 4-, 9-)yl, phenalene-(1-, 2-)yl, (1-, 2-, 3-, 4-, 9-)phenanthryl which are condensed tricyclic aryls, quaterphenyl (5'-phenyl-m-terphenyl-2-yl, 5'-phenyl-m-terphenyl-3-yl, 5'-phenyl-m-terphenyl-4-yl, m-quaterphenyl) which is a tetracyclic aryl, triphenylene-(1-, 2-)yl, pyrene-(1-, 2-, 4-)yl, naphthacene-(1-, 2-, 5-)yl which are condensed tetracyclic aryls, perylene-(1-, 2-, 3-)yl, pentacene-(1-, 2-, 5-, 6-)yl which are condensed pentacyclic aryls, and the like.

[0454] Examples of the "heteroaryl" in the "optionally substituted heteroaryl" include heteroaryls having 2 to 30 carbon atoms, preferably heteroaryls having 2 to 25 carbon atoms, more preferably heteroaryls having 2 to 20 carbon atoms, still more preferably heteroaryls having 2 to 15 carbon atoms, and particularly preferably heteroaryls having 2 to 10 carbon atoms. Further examples of the heteroaryl include heterocyclic rings containing 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen in addition to carbon as ring-constituting atoms.

[0455] Specific examples of the heteroaryl include, for example, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, pyrazolyl, pyridinyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, indolyl, isoindolyl, 1H-indazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolinyl, isoquinolinyl, cinnolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, naphthyridinyl, purinyl, pteridinyl, carbazolyl, acridinyl, phenoxathiinyl, phenoxazinyl, phenothiazinyl, phenazinyl, phenazasilinyl, indolizinyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, naphthobenzofuranyl, thiophenyl, benzothiophenyl, dibenzothiophenyl, naphthobenzothiophenyl, benzophosphoryl, dibenzophosphoryl, a monovalent group of a benzophosphole oxide ring, a monovalent group of a dibenzophosphole oxide ring, phthalazinyl, thianthrenyl, indolocarbazolyl, benzoindolocarbazolyl, and benzobenzoindolocarbazolyl.

[0456] Further, at least one hydrogen in the above aryl and heteroaryl may be substituted, and each may be substituted, for example, with the above aryl or heteroaryl.

[0457] Specific examples of this pyrimidine derivative include, for example, the following compounds. [Chem.]

[0458] This pyrimidine derivative can be produced using known raw materials and known synthesis methods.

[0459] [Carbazole derivative] The carbazole derivative is, for example, a compound represented by the following formula (ETM-9), or a multimer in which a plurality of them are bonded by a single bond or the like. Details are described in US Patent Publication No. 2014 / 0197386. [Chem.]

[0460] Ar is each independently an aryl which may be substituted, or a heteroaryl which may be substituted. n is each independently an integer of 0 to 4, preferably an integer of 0 to 3, more preferably 0 or 1.

[0461] Examples of the "aryl" in the "aryl which may be substituted" include aryls having 6 to 30 carbon atoms, preferably aryls having 6 to 24 carbon atoms, more preferably aryls having 6 to 20 carbon atoms, and still more preferably aryls having 6 to 12 carbon atoms.

[0462] Specific "aryl" includes phenyl which is a monocyclic aryl, (2-, 3-, 4-) biphenylyl which is a bicyclic aryl, (1-, 2-) naphthyl which is a condensed bicyclic aryl, 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-terphenyl-4-yl, o-terphenyl-2-yl, o-terphenyl-3-yl, o-terphenyl-4-yl, p-terphenyl-2-yl, p-terphenyl-3-yl, p-terphenyl-4-yl) which is a tricyclic aryl, condensed tricyclic aryls such as acenaphthylene-(1-, 3-, 4-, 5-)yl, fluorene-(1-, 2-, 3-, 4-, 9-)yl, phenalene-(1-, 2-)yl, (1-, 2-, 3-, 4-, 9-)phenanthryl, quarterphenyl (5'-phenyl-m-terphenyl-2-yl, 5'-phenyl-m-terphenyl-3-yl, 5'-phenyl-m-terphenyl-4-yl, m-quarterphenyl) which is a tetracyclic aryl, condensed tetracyclic aryls such as triphenylene-(1-, 2-)yl, pyrene-(1-, 2-, 4-)yl, naphthacene-(1-, 2-, 5-)yl, condensed pentacyclic aryls such as perylene-(1-, 2-, 3-)yl, pentacene-(1-, 2-, 5-, 6-)yl, etc.

[0463] Examples of the "heteroaryl" in "optionally substituted heteroaryl" include heteroaryl having 2 to 30 carbon atoms, preferably heteroaryl having 2 to 25 carbon atoms, more preferably heteroaryl having 2 to 20 carbon atoms, still more preferably heteroaryl having 2 to 15 carbon atoms, and particularly preferably heteroaryl having 2 to 10 carbon atoms. Further, examples of the heteroaryl include heterocycles containing 1 to 5 heteroatoms selected from oxygen, sulfur and nitrogen in addition to carbon as ring-constituting atoms.

[0464] Specific heteroaryl groups include, for example, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, pyrazolyl, pyridinyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, indolyl, isoindolyl, 1H-indazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolinyl, isoquinolinyl, cinnolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, naphthyridinyl, purinyl, pteridinyl, carbazolyl, acridinyl, phenoxathiinyl, phenoxazinyl, phenothiazinyl, phenazinyl, phenazasilinyl, indolizinyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, naphthobenzofuranyl, thiophenyl, benzothiophenyl, dibenzothiophenyl, naphthobenzothiophenyl, benzophosphoryl, dibenzophosphoryl, a monovalent group of a benzophosphole oxide ring, a monovalent group of a dibenzophosphole oxide ring, phthalazinyl, thianthrenyl, indolocarbazolyl, benzoindolocarbazolyl, and benzobenzoindolocarbazolyl, etc.

[0465] Also, at least one hydrogen in the above aryl and heteroaryl groups may be substituted, and each may be substituted, for example, with the above aryl or heteroaryl groups.

[0466] The carbazole derivative may be a multimer in which the compound represented by the above formula (ETM-9) is bonded through a plurality of single bonds or the like. In this case, in addition to the single bond, it may be bonded through an aryl ring (preferably a polyvalent benzene ring, naphthalene ring, anthracene ring, fluorene ring, benzofluorene ring, phenalene ring, phenanthrene ring or triphenylene ring).

[0467] Specific examples of this carbazole derivative include, for example, the following compounds.

Chemical formula

[0468] This carbazole derivative can be produced using known raw materials and known synthesis methods.

[0469] <Triazine derivative> The triazine derivative is, for example, a compound represented by the following formula (ETM-10), preferably a compound represented by the following formula (ETM-10-1). Details are described in US Patent Publication No. 2011 / 0156013. [Chemical formula]

[0470] Ar is each independently optionally substituted aryl or optionally substituted heteroaryl. n is an integer from 1 to 3, preferably 2 or 3.

[0471] Examples of the "aryl" in the "optionally substituted aryl" include aryl having 6 to 30 carbon atoms, preferably aryl having 6 to 24 carbon atoms, more preferably aryl having 6 to 20 carbon atoms, and still more preferably aryl having 6 to 12 carbon atoms.

[0472] Specific "aryl" includes phenyl which is a monocyclic aryl, (2-, 3-, 4-) biphenylyl which is a bicyclic aryl, (1-, 2-) naphthyl which is a condensed bicyclic aryl, 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-terphenyl-4-yl, o-terphenyl-2-yl, o-terphenyl-3-yl, o-terphenyl-4-yl, p-terphenyl-2-yl, p-terphenyl-3-yl, p-terphenyl-4-yl) which is a tricyclic aryl, acenaphthylene-(1-, 3-, 4-, 5-)yl, fluorene-(1-, 2-, 3-, 4-, 9-)yl, phenalene-(1-, 2-)yl, (1-, 2-, 3-, 4-, 9-)phenanthryl which are condensed tricyclic aryls, quarterphenyl (5'-phenyl-m-terphenyl-2-yl, 5'-phenyl-m-terphenyl-3-yl, 5'-phenyl-m-terphenyl-4-yl, m-quarterphenyl) which is a tetracyclic aryl, triphenylene-(1-, 2-)yl, pyrene-(1-, 2-, 4-)yl, naphthacene-(1-, 2-, 5-)yl which are condensed tetracyclic aryls, perylene-(1-, 2-, 3-)yl, pentacene-(1-, 2-, 5-, 6-)yl which are condensed pentacyclic aryls, and the like.

[0473] Examples of the "heteroaryl" in "optionally substituted heteroaryl" include heteroaryl having 2 to 30 carbon atoms, preferably heteroaryl having 2 to 25 carbon atoms, more preferably heteroaryl having 2 to 20 carbon atoms, still more preferably heteroaryl having 2 to 15 carbon atoms, and particularly preferably heteroaryl having 2 to 10 carbon atoms. Further, examples of the heteroaryl include heterocycles containing 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen in addition to carbon as ring-constituting atoms.

[0474] Specific heteroaryl groups include, for example, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, pyrazolyl, pyridinyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, indolyl, isoindolyl, 1H - indazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, 1H - benzotriazolyl, quinolinyl, isoquinolinyl, cinnolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, naphthyridinyl, purinyl, pteridinyl, carbazolyl, acridinyl, phenoxathiinyl, phenoxazinyl, phenothiazinyl, phenazinyl, phenazasilinyl, indolizinyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, naphthobenzofuranyl, thiophenyl, benzothiophenyl, dibenzothiophenyl, naphthobenzothiophenyl, benzophosphoryl, dibenzophosphoryl, monovalent groups of benzophosphole oxide ring, monovalent groups of dibenzophosphole oxide ring, phthalazinyl, thianthrenyl, indolocarbazolyl, benzoindolocarbazolyl, and benzobenzoindolocarbazolyl, etc.

[0475] Also, at least one hydrogen in the above - mentioned aryl and heteroaryl may be substituted, and each may be substituted, for example, by the above - mentioned aryl or heteroaryl.

[0476] Specific examples of this triazine derivative include, for example, the following compounds.

Chemical formula

[0477] This triazine derivative can be produced using known raw materials and known synthetic methods.

[0478] <Benzimidazole derivative> The benzimidazole derivative is, for example, a compound represented by the following formula (ETM - 11). [Chemistry]

[0479] φ is an n-valent aryl ring (preferably an n-valent benzene ring, naphthalene ring, anthracene ring, fluorene ring, benzofluorene ring, phenalene ring, phenanthrene ring or triphenylene ring), n is an integer from 1 to 4, and the "benzimidazole-based substituent" is a substituent in which the pyridyl group in the "pyridine-based substituent" in the above formula (ETM-2), formula (ETM-2-1) and formula (ETM-2-2) is replaced by a benzimidazole group. At least one hydrogen in the benzimidazole derivative may be replaced by deuterium. * in the following structural formula represents the bonding position. [Chemistry]

[0480] R in the above benzimidazole group 11 is hydrogen, alkyl having 1 to 24 carbon atoms, cycloalkyl having 3 to 12 carbon atoms or aryl having 6 to 30 carbon atoms, and the description of R in the above formula (ETM-2-1) and formula (ETM-2-2) can be cited. 11

[0481] φ is preferably further an anthracene ring or a fluorene ring. In this case, the structure can cite the description in the above formula (ETM-2-1) or formula (ETM-2-2), and R in each formula 11 ~R 18 can cite the description in the above formula (ETM-2-1) or formula (ETM-2-2). Also, in the above formula (ETM-2-1) or formula (ETM-2-2), it is described in the form where two pyridine-based substituents are bonded. When replacing these with benzimidazole-based substituents, both pyridine-based substituents may be replaced by benzimidazole-based substituents (i.e., n = 2), or either one of the pyridine-based substituents may be replaced by a benzimidazole-based substituent and the other pyridine-based substituent may be R 11 ~R 18It may be replaced (i.e., n = 1). Further, for example, R in the above formula (ETM-2-1) 11 ~R 18 At least one of them may be replaced with a benzimidazole-based substituent to make the "pyridine-based substituent" R 11 ~R 18 It may be replaced.

[0482] Specific examples of this benzimidazole derivative include, for example, 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-(naphthalen-2-yl)anthracen-9-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole, 5-(10-(naphthalen-2-yl)anthracen-9-yl)-1,2-diphenyl-1H-benzo[d]imidazole, 1-(4-(10-(naphthalen-2-yl)anthracen-9-yl)phenyl)-2-phenyl-1H-benzo[d]imidazole, 2-(4-(9,10-di(naphthalen-2-yl)anthracen-2-yl)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)anthracen-2-yl)-1,2-diphenyl-1H-benzo[d]imidazole, etc.

Chemical formula

[0483] This benzimidazole derivative can be produced using known raw materials and known synthesis methods.

[0484] <Phenanthroline derivative> The phenanthroline derivative is a compound represented by, for example, the following formula (ETM-12) or formula (ETM-12-1). Details are described in International Publication No. 2006 / 021982. [Chemical formula]

[0485] φ is an n-valent aryl ring (preferably an n-valent benzene ring, naphthalene ring, anthracene ring, fluorene ring, benzofluorene ring, phenalene ring, phenanthrene ring or triphenylene ring), and n is an integer from 1 to 4.

[0486] In each formula, R 11 ~R 18 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). Further, in the above formula (ETM-12-1), one of R 11 ~R 18 is bonded to φ which is an aryl ring.

[0487] At least one hydrogen in each phenanthroline derivative may be substituted with deuterium.

[0488] R 11 ~R 18 For alkyl, cycloalkyl and aryl in R 11 ~R 18 in the above formula (ETM-2), the description can be cited. Further, in addition to the above examples, φ includes, for example, the following structural formulas. In the following structural formulas, each R is independently hydrogen, methyl, ethyl, isopropyl, cyclohexyl, phenyl, 1-naphthyl, 2-naphthyl, biphenylyl or terphenylyl. Further, * in each structural formula represents the bonding position. [Chemical formula]

[0489] Specific examples of this phenanthroline derivative include, for example, 4,7-diphenyl-1,10-phenanthroline, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline, 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-bis(1,10-phenanthrolin-5-yl), bathocuproine, 1,3-bis(2-phenyl-1,10-phenanthrolin-9-yl)benzene, and compounds represented by the following structural formula.

Chemical formula

[0490] This phenanthroline derivative can be produced using known raw materials and known synthesis methods.

[0491] <Quinolinol-based metal complex> The quinolinol-based metal complex is, for example, a compound represented by the following general formula (ETM-13).

Chemical formula

[0492] Specific examples of the quinolinol-based metal complex include lithium 8-quinolinolate, tris(8-quinolinolato)aluminum, tris(4-methyl-8-quinolinolato)aluminum, tris(5-methyl-8-quinolinolato)aluminum, tris(3,4-dimethyl-8-quinolinolato)aluminum, tris(4,5-dimethyl-8-quinolinolato)aluminum, tris(4,6-dimethyl-8-quinolinolato)aluminum, bis(2-methyl-8-quinolinolato)(phenolato)aluminum, bis(2-methyl-8-quinolinolato)(2-methylphenolato)aluminum, bis(2-methyl-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-8-quinolinolato)(3,4-dimethylphenolato)aluminum, bis(2-methyl-8-quinolinolato)(3,5-dimethylphenolato)aluminum, bis(2-methyl-8-quinolinolato)(3,5-di-t-butylphenolato)aluminum, bis(2-methyl-8-quinolinolato)(2,6-diphenylphenolato)aluminum, bis(2-methyl-8-quinolinolato)(2,4,6-triphenylphenolato)aluminum, bis(2-methyl-8-quinolinolato)(2,4,6-trimethylphenolato)aluminum, bis(2-methyl-8-quinolinolato)(2,4,5,6-tetramethylphenolato)aluminum, bis(2-methyl-8-quinolinolato)(1-naphtholato)aluminum, bis(2-methyl-8-quinolinolato)(2-naphtholato)aluminum, bis(2,4-dimethyl-8-quinolinolato)(2-phenylphenolato)aluminum, bis(2,(4-Dimethyl-8-quinolinolate)(3-phenylphenolate)aluminum, bis(2,4-dimethyl-8-quinolinolate)(4-phenylphenolate)aluminum, bis(2,4-dimethyl-8-quinolinolate)(3,5-dimethylphenolate)aluminum, bis(2,4-dimethyl-8-quinolinolate)(3,5-di-t-butylphenolate)aluminum, bis(2-methyl-8-quinolinolate)aluminum-μ-oxo-bis(2-methyl-8-quinolinolate)aluminum, bis(2,4-dimethyl-8-quinolinolate)aluminum-μ-oxo-bis(2,4-dimethyl-8-quinolinolate)aluminum, bis(2-methyl-4-ethyl-8-quinolinolate)aluminum-μ-oxo-bis(2-methyl-4-ethyl-8-quinolinolate)aluminum, bis(2-methyl-4-methoxy-8-quinolinolate)aluminum-μ-oxo-bis(2-methyl-4-methoxy-8-quinolinolate)aluminum, bis(2-methyl-5-cyano-8-quinolinolate)aluminum-μ-oxo-bis(2-methyl-5-cyano-8-quinolinolate)aluminum, bis(2-methyl-5-trifluoromethyl-8-quinolinolate)aluminum-μ-oxo-bis(2-methyl-5-trifluoromethyl-8-quinolinolate)aluminum, bis(10-hydroxybenzo[h]quinoline)beryllium, etc. can be mentioned.,

[0493] This quinolinol-based metal complex can be produced using known raw materials and known synthesis methods.

[0494] <Thiazole derivatives and benzothiazole derivatives> The thiazole derivative is, for example, a compound represented by the following formula (ETM-14-1). [Chemical formula] The benzothiazole derivative is, for example, a compound represented by the following formula (ETM-14-2). [Chemical formula]

[0495] Each φ is an n-valent aryl ring (preferably an n-valent benzene ring, naphthalene ring, anthracene ring, fluorene ring, benzofluorene ring, phenalene ring, phenanthrene ring or triphenylene ring), n is an integer from 1 to 4, and the "thiazole-based substituent" and "benzothiazole-based substituent" are substituents in which the pyridyl group among the "pyridine-based substituents" in the above formula (ETM-2), formula (ETM-2-1) and formula (ETM-2-2) is replaced by the following thiazole group or benzothiazole group, and at least one hydrogen in the thiazole derivative and benzothiazole derivative may be replaced by deuterium. * in the following structural formula represents the bonding position.

Chemical formula

[0496] φ is more preferably an anthracene ring or a fluorene ring. In this case, the structure can be cited from the description in the above formula (ETM-2-1) or formula (ETM-2-2), and R 11 ~R 18 in each formula can be cited from the description in the above formula (ETM-2-1) or formula (ETM-2-2). Also, in the above formula (ETM-2-1) or formula (ETM-2-2), the two pyridine-based substituents are described in a combined form. When replacing them with thiazole-based substituents (or benzothiazole-based substituents), both pyridine-based substituents may be replaced by thiazole-based substituents (or benzothiazole-based substituents) (i.e., n = 2), or any one of the pyridine-based substituents may be replaced by a thiazole-based substituent (or benzothiazole-based substituent) and the other pyridine-based substituent may be replaced by R 11 ~R 18 (i.e., n = 1). Further, for example, at least one of R 11 ~R 18 in the above formula (ETM-2-1) is replaced by a thiazole-based substituent (or benzothiazole-based substituent) to replace the "pyridine-based substituent" with R 11 ~R 18 may also be possible.

[0497] These thiazole derivatives or benzothiazole derivatives can be produced using known raw materials and known synthesis methods.

[0498] The electron transport layer or the electron injection layer may further contain a substance capable of reducing the material forming the electron transport layer or the electron injection layer. As long as this reducing substance has a certain reducing property, various substances can be used. For example, it is preferably at least one selected from the group consisting of alkali metals, alkaline earth metals, rare earth metals, oxides of alkali metals, halides of alkali metals, oxides of alkaline earth metals, halides of alkaline earth metals, oxides of rare earth metals, halides of rare earth metals, organic complexes of alkali metals, organic complexes of alkaline earth metals, and organic complexes of rare earth metals.

[0499] Preferred reducing substances include alkali metals such as Na (work function 2.36 eV), K (2.28 eV), Rb (2.16 eV), or Cs (1.95 eV), and alkaline earth metals such as Ca (2.9 eV), Sr (2.0 - 2.5 eV), or Ba (2.52 eV). Substances with a work function of 2.9 eV or less are particularly preferred. Among these, more preferred reducing substances are alkali metals of K, Rb, or Cs, even more preferably Rb or Cs, and most preferably Cs. These alkali metals have particularly high reducing ability, and by adding a relatively small amount to the material forming the electron transport layer or the electron injection layer, an improvement in the emission luminance and an extension of the lifetime in the organic EL element can be achieved. Also, as reducing substances with a work function of 2.9 eV or less, combinations of two or more of these alkali metals are also preferred, particularly combinations containing Cs, such as combinations of Cs and Na, Cs and K, Cs and Rb, or Cs and Na and K. By containing Cs, the reducing ability can be efficiently exerted, and by adding it to the material forming the electron transport layer or the electron injection layer, an improvement in the emission luminance and an extension of the lifetime in the organic EL element can be achieved.

[0500] The above-described materials for the electron injection layer and the electron transport layer can also be used as electron layer materials in the form of a polymer compound obtained by polymerizing a reactive compound having a reactive substituent as a monomer, or a polymer crosslinked body thereof, or a pendant-type polymer compound obtained by reacting a main-chain polymer with the reactive compound, or a pendant-type polymer crosslinked body thereof. As the reactive substituent in this case, the description of the polycyclic aromatic compound represented by the formula (1A) or the formula (1B) can be cited. Details of the uses of such polymer compounds and polymer crosslinked bodies will be described later.

[0501] <Cathode in the organic electroluminescent element> The cathode 108 serves to inject electrons into the light-emitting layer 105 via the electron injection layer 107 and the electron transport layer 106.

[0502] The material for forming the cathode 108 is not particularly limited as long as it can efficiently inject electrons into the organic layer, and the same materials as those for forming the anode 102 can be used. Among them, metals such as tin, indium, calcium, aluminum, silver, copper, nickel, chromium, gold, platinum, iron, zinc, lithium, sodium, potassium, cesium, and magnesium, or their alloys (such as magnesium-silver alloy, magnesium-indium alloy, aluminum-lithium alloy such as lithium fluoride / aluminum, etc.) are preferable. In order to improve the electron injection efficiency and device characteristics, lithium, sodium, potassium, cesium, calcium, magnesium, or alloys containing these low work function metals are effective. However, these low work function metals are generally unstable in the atmosphere. To improve this point, for example, a method of doping a trace amount of lithium, cesium, or magnesium into the organic layer and using a highly stable electrode is known. Other dopants can also be used, such as inorganic salts such as lithium fluoride, cesium fluoride, lithium oxide, and cesium oxide. However, it is not limited to these.

[0503] Furthermore, for electrode protection, it is preferable to laminate metals such as platinum, gold, silver, copper, iron, tin, aluminum, and indium, or alloys using these metals, and inorganic substances such as silica, titania, and silicon nitride, polyvinyl alcohol, vinyl chloride, hydrocarbon-based polymer compounds, etc. The manufacturing methods of these electrodes are not particularly limited as long as conduction can be achieved, such as resistance heating, electron beam evaporation, sputtering, ion plating, and coating.

[0504] <Binder that may be used in each layer> The materials used for the above hole injection layer, hole transport layer, light-emitting layer, electron transport layer, and electron injection layer can form each layer alone, but can also be used by dispersing them in solvent-soluble resins such as polyvinyl chloride, polycarbonate, polystyrene, poly(N-vinylcarbazole), polymethyl methacrylate, polybutyl methacrylate, polyester, polysulfone, polyphenylene oxide, polybutadiene, hydrocarbon resin, ketone resin, phenoxy resin, polyamide, ethyl cellulose, vinyl acetate resin, ABS resin, polyurethane resin, etc., or curable resins such as phenol resin, xylene resin, petroleum resin, urea resin, melamine resin, unsaturated polyester resin, alkyd resin, epoxy resin, silicone resin, etc.

[0505] <Manufacturing method of organic electroluminescent element> Each layer constituting the organic EL element can be formed by making a thin film of the material to constitute each layer by methods such as evaporation method, resistance heating evaporation, electron beam evaporation, sputtering, molecular lamination method, printing method, spin coating method, casting method, coating method, etc. There is no particular limitation on the film thickness of each layer formed in this way, and it can be appropriately set according to the properties of the material, but it is usually in the range of 2 nm to 5000 nm. The film thickness can usually be measured with a crystal oscillator type film thickness measuring device, etc. When thinning by the evaporation method, the evaporation conditions vary depending on the type of material, the intended crystal structure and association structure of the film, etc. The evaporation conditions are generally boat heating temperature +50 to +400 °C, vacuum degree 10 -6 ~10-3 It is preferably appropriately set within the range of Pa, deposition rate of 0.01 to 50 nm / second, substrate temperature of -150 to +300 °C, and film thickness of 2 nm to 5 μm.

[0506] When applying a DC voltage to the organic EL element thus obtained, it may be applied with the anode as + and the cathode as - polarities. When applying a voltage of about 2 to 40 V, light emission can be observed from the transparent or semi-transparent electrode side (anode or cathode, and both). In addition, this organic EL element also emits light when a pulsed current or an alternating current is applied. The waveform of the alternating current to be applied may be arbitrary.

[0507] Next, as an example of a method for manufacturing an organic EL element, a method for manufacturing an organic EL element composed of an anode / hole injection layer / hole transport layer / light-emitting layer composed of a host material and a dopant material / electron transport layer / electron injection layer / cathode will be described.

[0508] <Evaporation method> After forming an anode by forming a thin film of an anode material on a suitable substrate by an evaporation method or the like, thin films of a hole injection layer and a hole transport layer are formed on this anode. A thin film is formed by co-evaporating a host material and a dopant material thereon to form a light-emitting layer. An electron transport layer and an electron injection layer are formed on this light-emitting layer, and a thin film made of a cathode material is further formed by an evaporation method or the like to form a cathode, whereby the target organic EL element is obtained. In the production of the above-described organic EL element, it is also possible to reverse the production order and produce in the order of cathode, electron injection layer, electron transport layer, light-emitting layer, hole transport layer, hole injection layer, and anode.

[0509] <Wet film formation method> The wet film formation method is carried out by preparing a low molecular compound capable of forming each organic layer of the organic EL element as a liquid composition for forming an organic layer and using this. When there is no suitable organic solvent for dissolving this low molecular compound, an organic layer forming composition may be prepared from a polymer compound polymerized with another monomer or a main chain type polymer having a solubility function as a reactive compound in which a reactive substituent is substituted for the low molecular compound.

[0510] The wet film-forming method generally forms a coating film through a coating process of applying a composition for forming an organic layer on a substrate and a drying process of removing a solvent from the applied composition for forming an organic layer. When the above polymer compound has a crosslinkable substituent (this is also referred to as a crosslinkable polymer compound), further crosslinking occurs during this drying process to form a polymer crosslinked body. Depending on the difference in the coating process, the method using a spin coater is called the spin coating method, the method using a slit coater is called the slit coating method, the method using a plate is called gravure, offset, reverse offset, flexographic printing method, the method using an inkjet printer is called the inkjet method, and the method of spraying in a mist is called the spray method. For the drying process, there are methods such as air drying, heating, and vacuum drying. The drying process may be performed only once, or may be performed multiple times using different methods and conditions. Also, for example, different methods may be used in combination, such as firing under reduced pressure.

[0511] The wet film-forming method is a film-forming method using a solution, for example, some printing methods (inkjet method), spin coating method, casting method, coating method, etc. Different from the vacuum evaporation method, the wet film-forming method does not require the use of an expensive vacuum evaporation device and can form a film under atmospheric pressure. In addition, the wet film-forming method enables large-area formation and continuous production, leading to a reduction in manufacturing costs.

[0512] On the other hand, when compared with the vacuum evaporation method, the wet film-forming method may be difficult to laminate. When producing a laminated film using the wet film-forming method, it is necessary to prevent the dissolution of the lower layer by the upper layer composition, and compositions with controlled solubility, crosslinking of the lower layer, and orthogonal solvents (solvents that do not dissolve in each other) are used. However, even when using these techniques, it may be difficult to use the wet film-forming method for coating all films.

[0513] Therefore, generally, a method is adopted in which only some layers are formed by the wet film-forming method and the rest are formed by the vacuum evaporation method to fabricate an organic EL element.

[0514] For example, the procedure for manufacturing an organic EL device by partially applying a wet film formation method is shown below. (Step 1) Film formation by vacuum evaporation method of the anode (Step 2) Film formation by wet film formation method of the composition for forming a hole injection layer containing a hole injection layer material (Step 3) Film formation by wet film formation method of the composition for forming a hole transport layer containing a hole transport layer material (Step 4) Film formation by wet film formation method of the composition for forming a light-emitting layer containing a host material and a dopant material (Step 5) Film formation by vacuum evaporation method of the electron transport layer (Step 6) Film formation by vacuum evaporation method of the electron injection layer (Step 7) Film formation by vacuum evaporation method of the cathode By going through this procedure, an organic EL device composed of anode / hole injection layer / hole transport layer / light-emitting layer composed of host material and dopant material / electron transport layer / electron injection layer / cathode can be obtained. Of course, by using means to prevent dissolution of the lower light-emitting layer, or by using means such as film formation from the cathode side contrary to the above procedure, a composition for forming a layer containing an electron transport layer material or an electron injection layer material can be prepared and deposited by the wet film formation method.

[0515] <Other film formation methods> For film formation of the composition for forming an organic layer, laser-induced thermal imaging (LITI) can be used. LITI is a method of laser-heated evaporation of a compound attached to a substrate, and the composition for forming an organic layer can be used as the material applied to the substrate.

[0516] <Optional steps> Before and after each step of film formation, appropriate treatment steps, washing steps, and drying steps may be appropriately inserted. Examples of treatment steps include exposure treatment, plasma surface treatment, ultrasonic treatment, ozone treatment, washing treatment using an appropriate solvent, and heat treatment, etc. Furthermore, a series of steps for fabricating a bank are also included.

[0517] Photolithography technology can be used to fabricate the bank. As bank materials that can be used in photolithography, positive resist materials and negative resist materials can be used. Also, patternable printing methods such as inkjet printing, gravure offset printing, reverse offset printing, and screen printing can be used. In that case, permanent resist materials can also be used.

[0518] Examples of materials used for the bank include, but are not limited to, polysaccharides and their derivatives, homopolymers and copolymers of ethylenic monomers having hydroxyl groups, biopolymer compounds, polyacryloyl compounds, polyesters, polystyrenes, polyimides, polyamide-imides, polyether-imides, polysulfides, polysulfones, polyphenylenes, polyphenyl ethers, polyurethanes, epoxy (meth) acrylates, melamine (meth) acrylates, polyolefins, cyclic polyolefins, acrylonitrile-butadiene-styrene copolymer polymers (ABS), silicone resins, polyvinyl chlorides, chlorinated polyethylenes, chlorinated polypropylenes, polyacetates, polynorbornenes, synthetic rubbers, fluoropolymers such as polyvinylidene fluoride, polytetrafluoroethylene, and polyhexafluoropropylene, copolymer polymers of fluoroolefin-hydrocarbon olefin, and fluorocarbon polymers.

[0519] <Composition for forming an organic layer used in the wet film forming method> The composition for forming an organic layer is obtained by dissolving a low-molecular compound capable of forming each organic layer of an organic EL element or a high-molecular compound obtained by polymerizing the low-molecular compound in an organic solvent. For example, the composition for forming a light-emitting layer contains at least one polycyclic aromatic compound (or its high-molecular compound) as a dopant material as a first component, at least one host material as a second component, and at least one organic solvent as a third component. The first component functions as a dopant component of the light-emitting layer obtained from the composition, and the second component functions as a host component of the light-emitting layer. The third component functions as a solvent for dissolving the first component and the second component in the composition, and gives a smooth and uniform surface shape by the controlled evaporation rate of the third component itself during coating.

[0520] <organic solvent> The composition for forming an organic layer contains at least one organic solvent. By controlling the evaporation rate of the organic solvent during film formation, the film-forming property, the presence or absence of defects in the coating film, the surface roughness, and the smoothness can be controlled and improved. Further, during film formation using the inkjet method, the meniscus stability at the pinholes of the inkjet head can be controlled, and the ejection property can be controlled and improved. In addition, by controlling the drying rate of the film and the orientation of the derivative molecules, the electrical characteristics, light-emitting characteristics, efficiency, and lifetime of the organic EL element having an organic layer obtained from the composition for forming an organic layer can be improved.

[0521] (1) Physical properties of the organic solvent The boiling point of at least one organic solvent is 130°C to 300°C, more preferably 140°C to 270°C, and even more preferably 150°C to 250°C. When the boiling point is higher than 130°C, it is preferable from the viewpoint of the ejection property of the inkjet. Also, when the boiling point is lower than 300°C, it is preferable from the viewpoints of coating film defects, surface roughness, residual solvent, and smoothness. The organic solvent preferably has a configuration containing two or more organic solvents from the viewpoints of good inkjet ejection property, film-forming property, smoothness, and low residual solvent. On the other hand, in some cases, considering transportability and the like, a composition in a solid state may be obtained by removing the solvent from the composition for forming an organic layer.

[0522] Furthermore, the organic solvent contains a good solvent (GS) and a poor solvent (PS) for at least one of the solutes, and the boiling point (BP GS ) of the good solvent (GS) is lower than the boiling point (BP PS ) of the poor solvent (PS), and the configuration is particularly preferable. By adding a high-boiling poor solvent, the low-boiling good solvent volatilizes first during film formation, increasing the concentration of the inclusions and the concentration of the poor solvent in the composition and promoting rapid film formation. As a result, a coating film with few defects, a small surface roughness, and high smoothness can be obtained.

[0523] The solubility difference (S GS -S PS ) is preferably 1% or more, more preferably 3% or more, and even more preferably 5% or more. The boiling point difference (BP PS -BP GS ) is preferably 10°C or more, more preferably 30°C or more, and even more preferably 50°C or more.

[0524] The organic solvent is removed from the coating film by a drying process such as vacuum, reduced pressure, or heating after film formation. When heating is performed, from the viewpoint of improving coating film formability, it is preferably performed at a temperature of at least one kind of glass transition temperature (Tg) of the solute + 30°C or lower. Also, from the viewpoint of reducing the residual solvent, it is preferably heated at a temperature of at least one kind of glass transition point (Tg) of the solute - 30°C or higher. Even if the heating temperature is lower than the boiling point of the organic solvent, the organic solvent is sufficiently removed because the film is thin. Also, drying may be performed multiple times at different temperatures, or multiple drying methods may be used in combination.

[0525] (2) Specific examples of the organic solvent Examples of the organic solvent used in the composition for forming the organic layer include alkylbenzene solvents, phenyl ether solvents, alkyl ether solvents, cyclic ketone solvents, aliphatic ketone solvents, monocyclic ketone solvents, solvents having a diester skeleton, and fluorine-containing solvents. Specific examples include pentanol, hexanol, heptanol, octanol, nonanol, decanol, undecanol, dodecanol, tetradecanol, hexan-2-ol, heptan-2-ol, octan-2-ol, decan-2-ol, dodecan-2-ol, cyclohexanol, α-terpineol, β-terpineol, γ-terpineol, δ-terpineol, terpineol (mixture), ethylene glycol monomethyl ether acetate, propylene glycol monomethyl ether acetate, diethylene glycol dimethyl ether, dipropylene glycol dimethyl ether, diethylene glycol ethyl methyl ether, diethylene glycol isopropyl methyl ether, dipropylene glycol monomethyl ether, diethylene glycol diethyl ether, diethylene glycol monomethyl ether, diethylene glycol butyl methyl ether, tripropylene glycol dimethyl ether, triethylene glycol dimethyl ether, diethylene glycol monobutyl ether, ethylene glycol monophenyl ether, triethylene glycol monomethyl ether, diethylene glycol dibutyl ether, triethylene glycol butyl methyl ether, polyethylene glycol dimethyl ether, tetraethylene glycol dimethyl ether, p-xylene, m-xylene, o-xylene, 2,6-lutidine, 2-fluoro-m-xylene, 3-fluoro-o-xylene, 2-chlorobenzotrifluoride, cumene, toluene, 2-chloro-6-fluorotoluene, 2-fluoroanisole, anisole, 2,3-dimethylpyrazine, bromobenzene, 4-fluoroanisole, 3-fluoroanisole, 3-trifluoromethylanisole, mesitylene, 1,2,4-trimethylbenzene, t-butylbenzene, 2-methylanisole, phenetole, benzodioxole, 4-methylanisole, s-butylbenzene, 3-methylanisole, 4-fluoro-3-methylanisole, cymene, 1,2,3-trimethylbenzene, 1,2-dichlorobenzene, 2-fluorobenzonitrile, 4-fluoroveratrole, 2,6-dimethylanisole, n-butylbenzene, 3-fluorobenzonitrile, decalin (decalin), neopentylbenzene, 2,5-dimethylanisole, 2,4-dimethylanisole, benzonitrile, 3,5-dimethylanisole, diphenyl ether, 1-fluoro-3,5-dimethoxybenzene, methyl benzoate, isopentylbenzene, 3,4-dimethylanisole, o-tolunitrile, n-amylbenzene, veratrole, 1,2,3,4-tetrahydronaphthalene, ethyl benzoate, n-hexylbenzene, propyl benzoate, cyclohexylbenzene, 1-methylnaphthalene, butyl benzoate, 2-methylbiphenyl, 3-phenoxytoluene, 2,2'-bipyridyl, dodecylbenzene, dipentylbenzene, tetramethylbenzene, trimethoxybenzene, trimethoxytoluene, 2,3-dihydrobenzofuran, 1-methyl-4-(propoxymethyl)benzene, 1-methyl-4-(butyloxymethyl)benzene, 1-methyl-4-(pentyloxymethyl)benzene, 1-methyl-4-(hexyloxymethyl)benzene, 1-methyl-4-(heptyloxymethyl)benzene benzyl butyl ether, benzyl pentyl ether, benzyl hexyl ether, benzyl heptyl ether, benzyl octyl ether and the like, but are not limited thereto. Further, the solvent may be used singly or in combination.,

[0526] <Optional component> The composition for forming an organic layer may contain an optional component as long as its properties are not impaired. Examples of the optional component include a binder and a surfactant and the like.,

[0527] (1) Binder The composition for forming an organic layer may contain a binder. The binder forms a film during film formation and bonds the obtained film to the substrate. Further, it serves to dissolve, disperse and bind other components in the composition for forming an organic layer.,

[0528] Examples of the binder used in the composition for forming the organic layer include, but are not limited to, acrylic resin, polyethylene terephthalate, ethylene-vinyl acetate copolymer, ethylene-vinyl alcohol copolymer, acrylonitrile-ethylene-styrene copolymer (AES) resin, ionomer, chlorinated polyether, diallyl phthalate resin, unsaturated polyester resin, polyethylene, polypropylene, polyvinyl chloride, polyvinylidene chloride, polystyrene, polyvinyl acetate, Teflon, acrylonitrile-butadiene-styrene copolymer (ABS) resin, acrylonitrile-styrene copolymer (AS) resin, phenol resin, epoxy resin, melamine resin, urea resin, alkyd resin, polyurethane, and copolymers of the above resins and polymers.

[0529] The binder used in the composition for forming the organic layer may be only one type or a mixture of multiple types.

[0530] (2) Surfactant The composition for forming the organic layer may contain a surfactant, for example, for controlling the film surface uniformity of the composition for forming the organic layer, the hydrophilicity of the film surface, and the liquid repellency. Surfactants are classified into ionic and non-ionic types based on the structure of the hydrophilic group, and further classified into alkyl-based, silicon-based, and fluorine-based types based on the structure of the hydrophobic group. Also, from the molecular structure, it is classified into a single molecular system having a relatively small molecular weight and a simple structure and a polymer system having a large molecular weight and side chains or branches. Also, from the composition, it is classified into a single system and a mixed system in which two or more surfactants and a substrate are mixed. As the surfactant that can be used in the composition for forming the organic layer, all types of surfactants can be used.

[0531] Examples of surfactants include Polyflow No. 45, Polyflow KL-245, Polyflow No. 75, Polyflow No. 90, Polyflow No. 95 (trade names, manufactured by Kyoeisha Chemical Co., Ltd.), Disperbyk 161, Disperbyk 162, Disperbyk 163, Disperbyk 164, Disperbyk 166, Disperbyk 170, Disperbyk 180, Disperbyk 181, Disperbyk 182, BYK 300, BYK 306, BYK 310, BYK 320, BYK 330, BYK 342, BYK 344, BYK 346 (trade names, manufactured by BYK-Chemie Japan Co., Ltd.), KP-341, KP-358, KP-368, KF-96-50CS, KF-50-100CS (trade names, manufactured by Shin-Etsu Chemical Co., Ltd.), Surflon SC-101, Surflon KH-40 (trade names, manufactured by Seimi Chemical Co., Ltd.), Ftergent 222F, Ftergent 251, FTX-218 (trade names, manufactured by Neos Co., Ltd.), EFTOP EF-351, EFTOP EF-352, EFTOP EF-601, EFTOP EF-801, EFTOPEF-802 (trade name, manufactured by Mitsubishi Materials Corporation), Mega Fac F-470, Mega Fac F-471, Mega Fac F-475, Mega Fac R-08, Mega Fac F-477, Mega Fac F-479, Mega Fac F-553, Mega Fac F-554 (trade name, manufactured by DIC Corporation), fluoroalkylbenzenesulfonate, fluoroalkylcarboxylate, fluoroalkylpolyoxyethylene ether, fluoroalkylammonium iodide, fluoroalkylbetaine, fluoroalkylsulfonate, diglycerin tetrakis(fluoroalkylpolyoxyethylene ether), fluoroalkyltrimethylammonium salt, fluoroalkylaminosulfonate, polyoxyethylene nonylphenyl ether, polyoxyethylene octylphenyl ether, polyoxyethylene alkyl ether, polyoxyethylene laurate, polyoxyethylene oleate, polyoxyethylene stearate, polyoxyethylene laurylamine, sorbitan laurate, sorbitan palmitate, sorbitan stearate, sorbitan oleate, sorbitan fatty acid ester, polyoxyethylene sorbitan laurate, polyoxyethylene sorbitan palmitate, polyoxyethylene sorbitan stearate, polyoxyethylene sorbitan oleate, polyoxyethylene naphthyl ether, alkylbenzenesulfonate, and alkyldiphenyl ether disulfonate can be mentioned.

[0532] Also, the surfactant may be used alone or in combination of two or more.

[0533] <Composition and Physical Properties of Composition for Forming Organic Layer> The content of each component in the composition for forming an organic layer is determined in consideration of the good solubility, storage stability, and film-forming property of each component in the composition for forming an organic layer, the good film quality of the coating film obtained from the composition for forming an organic layer, the good ejection property when the inkjet method is used, and the good electrical characteristics, light-emitting characteristics, efficiency, and lifespan of the organic EL element having the organic layer produced using the composition. For example, in the case of the composition for forming a light-emitting layer, the first component is 0.0001 wt% to 2.0 wt% based on the total weight of the composition for forming a light-emitting layer, the second component is 0.0999 wt% to 8.0 wt% based on the total weight of the composition for forming a light-emitting layer, and the third component is 90.0 wt% to 99.9 wt% based on the total weight of the composition for forming a light-emitting layer, which is preferable.

[0534] More preferably, the first component is 0.005 wt% to 1.0 wt% based on the total weight of the composition for forming a light-emitting layer, the second component is 0.095 wt% to 4.0 wt% based on the total weight of the composition for forming a light-emitting layer, and the third component is 95.0 wt% to 99.9 wt% based on the total weight of the composition for forming a light-emitting layer. Even more preferably, the first component is 0.05 wt% to 0.5 wt% based on the total weight of the composition for forming a light-emitting layer, the second component is 0.25 wt% to 2.5 wt% based on the total weight of the composition for forming a light-emitting layer, and the third component is 97.0 wt% to 99.7 wt% based on the total weight of the composition for forming a light-emitting layer.

[0535] The composition for forming an organic layer can be produced by appropriately selecting known methods such as stirring, mixing, heating, cooling, dissolving, and dispersing for the above-described components. Further, after preparation, filtration, degassing (also referred to as degas), ion exchange treatment, and inert gas substitution / encapsulation treatment, etc. can be appropriately selected and carried out.

[0536] As for the viscosity of the composition for forming an organic layer, a higher viscosity provides better film-forming properties and better ejection properties when using the inkjet method. On the other hand, a lower viscosity makes it easier to form a thin film. Therefore, the viscosity of the composition for forming an organic layer preferably has a viscosity at 25 °C of 0.3 to 3 mPa·s, more preferably 1 to 3 mPa·s. In the present invention, the viscosity is a value measured using a cone and plate type rotational viscometer (cone plate type).

[0537] As for the surface tension of the composition for forming an organic layer, a lower surface tension provides better film-forming properties and a coating film without defects. On the other hand, a higher surface tension provides better inkjet ejection properties. Therefore, the viscosity of the composition for forming an organic layer preferably has a surface tension at 25 °C of 20 to 40 mN / m, more preferably 20 to 30 mN / m. In the present invention, the surface tension is a value measured using the sessile drop method.

[0538] <Crosslinkable polymer compound: A compound represented by the general formula (XLP-1)> Next, the case where the above-described polymer compound has a crosslinkable substituent will be described. Such a crosslinkable polymer compound is, for example, a compound represented by the following general formula (XLP-1). [Chemical formula] In formula (XLP-1), MUx, ECx and k have the same definitions as MU, EC and k in the above formula (SPH-1), provided that the compound represented by formula (XLP-1) has at least one crosslinkable substituent (XLS), and preferably the content of the monovalent or divalent aromatic compound having a crosslinkable substituent is 0.1 to 80% by weight in the molecule.

[0539] The content of the monovalent or divalent aromatic compound having a crosslinkable substituent is preferably 0.5 to 50% by weight, more preferably 1 to 20% by weight.

[0540] The crosslinkable substituent (XLS) is not particularly limited as long as it is a group capable of further crosslinking the above-described polymer compound, but substituents having the following structures are preferred. * in each structural formula indicates the bonding position.

Chemical formula

[0541] L is, independently of each other, a single bond, -O-, -S-, >C=O, -O-C(=O)-, alkylene having 1 to 12 carbon atoms, oxyalkylene having 1 to 12 carbon atoms, and polyoxyalkylene having 1 to 12 carbon atoms. Among the above substituents, groups represented by formula (XLS-1), formula (XLS-2), formula (XLS-3), formula (XLS-9), formula (XLS-10), or formula (XLS-17) are preferred, and groups represented by formula (XLS-1), formula (XLS-3), or formula (XLS-17) are more preferred.

[0542] Examples of the divalent aromatic compound having a crosslinkable substituent include compounds having the following partial structures. * in the following structural formula represents the bonding position.

Chemical formula

Chemical formula

Chemical formula

Chemical formula

[0543] <Manufacturing methods of polymer compounds and crosslinkable polymer compounds> Regarding the manufacturing methods of polymer compounds and crosslinkable polymer compounds, the compounds represented by formula (SPH-1) and formula (XLP-1) described above will be described as examples. These compounds can be synthesized by appropriately combining known manufacturing methods.

[0544] Examples of the solvent used in the reaction include aromatic solvents, saturated / unsaturated hydrocarbon solvents, alcohol solvents, ether solvents, etc., such as dimethoxyethane, 2-(2-methoxyethoxy)ethane, 2-(2-ethoxyethoxy)ethane, and the like.

[0545] Also, the reaction may be carried out in a two-phase system. When carrying out the reaction in a two-phase system, a phase transfer catalyst such as a quaternary ammonium salt may be added as necessary.

[0546] When producing the compound of formula (SPH-1) and the compound of (XLP-1), it may be produced in one step or through multiple steps. Also, it may be carried out by a batch polymerization method in which all the raw materials are put into the reaction vessel and then the reaction is started, or by a dropwise polymerization method in which the raw materials are added dropwise to the reaction vessel, or by a precipitation polymerization method in which the product precipitates as the reaction proceeds, and these can be combined appropriately for synthesis. For example, when synthesizing the compound represented by formula (SPH-1) in one step, the target product is obtained by carrying out the reaction with the monomer unit (MU) and the end cap unit (EC) added to the reaction vessel. Also, when synthesizing the compound represented by the general formula (SPH-1) in multiple steps, the target product is obtained by polymerizing the monomer unit (MU) to the desired molecular weight and then adding the end cap unit (EC) and reacting. By adding different types of monomer units (MU) in multiple steps and carrying out the reaction, a polymer having a concentration gradient in the structure of the monomer unit can be produced. Also, after preparing the precursor polymer, the target polymer can be obtained by subsequent reaction.

[0547] Also, by selecting the polymerizable group of the monomer unit (MU), the primary structure of the polymer can be controlled. For example, as shown in Synthesis Schemes 1 to 3, it is possible to synthesize a polymer having a random primary structure (Synthesis Scheme 1), a polymer having a regular primary structure (Synthesis Schemes 2 and 3), etc., and these can be used in appropriate combinations according to the target product. Furthermore, by using a monomer unit having three or more polymerizable groups, hyperbranched polymers and dendrimers can be synthesized.

Chem.

[0548] As the monomer units that can be used in the present invention, they can be synthesized according to the methods described in JP-A-2010-189630, International Publication No. 2012 / 086671, International Publication No. 2013 / 191088, International Publication No. 2002 / 045184, International Publication No. 2011 / 049241, International Publication No. 2013 / 146806, International Publication No. 2005 / 049546, International Publication No. 2015 / 145871, JP-A-2010-215886, JP-A-2008-106241, JP-A-2010-215886, International Publication No. 2016 / 031639, JP-A-2011-174062, International Publication No. 2016 / 031639, International Publication No. 2016 / 031639, International Publication No. 2002 / 045184.

[0549] Regarding the specific polymer synthesis procedures, they can be synthesized according to the methods described in JP-A-2012-036388, International Publication No. 2015 / 008851, JP-A-2012-36381, JP-A-2012-144722, International Publication No. 2015 / 194448, International Publication No. 2013 / 146806, International Publication No. 2015 / 145871, International Publication No. 2016 / 031639, International Publication No. 2016 / 125560, International Publication No. 2016 / 031639, International Publication No. 2016 / 031639, International Publication No. 2016 / 125560, International Publication No. 2015 / 145871, International Publication No. 2011 / 049241, JP-A-2012-144722.

[0550] <Application Examples of Organic Electroluminescent Devices> In addition, the present invention can also be applied to a display device including an organic EL element or an illumination device including an organic EL element. A display device or lighting device including an organic EL element can be manufactured by a known method such as connecting the organic EL element according to the present embodiment and a known driving device, and can be driven by appropriately using a known driving method such as direct current driving, pulse driving, or alternating current driving.

[0551] Examples of the display device include panel displays such as color flat panel displays, and flexible displays such as flexible color organic electroluminescence (EL) displays (see, for example, Japanese Patent Application Laid-Open No. 10-335066, Japanese Patent Application Laid-Open No. 2003-321546, Japanese Patent Application Laid-Open No. 2004-281086, etc.). Further, examples of the display method of the display include a matrix and / or segment method. Note that matrix display and segment display may coexist in the same panel.

[0552] In a matrix, pixels for display are two-dimensionally arranged in a grid pattern or a mosaic pattern, and characters and images are displayed by a set of pixels. The shape and size of the pixels are determined by the application. For example, for image and character display of a personal computer, monitor, or television, square pixels with a side length of usually 300 μm or less are used. In the case of a large display such as a display panel, pixels with a side length on the order of mm are used. In the case of monochrome display, pixels of the same color may be arranged. In the case of color display, red, green, and blue pixels are arranged for display. In this case, typically, there are a delta type and a stripe type. As the driving method of this matrix, either a line sequential driving method or an active matrix may be used. The line sequential driving has the advantage of a simple structure, but considering the operating characteristics, the active matrix may be superior in some cases, so it is necessary to use them appropriately depending on the application.

[0553] In the segment method (type), a pattern is formed to display predetermined information, and light is emitted from a determined area. For example, time and temperature display in a digital clock or thermometer, operation state display in an audio device or electromagnetic cooker, and panel display of an automobile are included.

[0554] Examples of the lighting device include lighting devices such as indoor lighting, and backlights for liquid crystal display devices (see, for example, JP-A-2003-257621, JP-A-2003-277741, JP-A-2004-119211, etc.). The backlight is mainly used for the purpose of improving the visibility of a display device that does not emit light by itself, and is used for liquid crystal display devices, watches, audio devices, automotive panels, display boards, and signs. In particular, as a backlight for a personal computer application where thinning is an issue, especially for a liquid crystal display device, considering that it is difficult to thin the conventional method because it consists of a fluorescent lamp and a light guide plate, the backlight using the light-emitting element according to the present embodiment is characterized by being thin and lightweight.

[0555] 3-2. Other organic devices The polycyclic aromatic compound according to the present invention can be used for the production of organic field effect transistors, organic thin film solar cells, wavelength conversion filters, etc., in addition to the above-described organic electroluminescent elements.

[0556] An organic field effect transistor is a transistor that controls current by an electric field generated by a voltage input, and a gate electrode is provided in addition to a source electrode and a drain electrode. When a voltage is applied to the gate electrode, an electric field is generated, and it is a transistor that can arbitrarily block the flow of electrons (or holes) flowing between the source electrode and the drain electrode to control the current. The field effect transistor is easier to miniaturize than a simple transistor (bipolar transistor) and is often used as an element for constructing an integrated circuit or the like.

[0557] The structure of the organic field effect transistor usually has a source electrode and a drain electrode provided in contact with an organic semiconductor active layer formed using the polycyclic aromatic compound according to the present invention, and a gate electrode may be provided with an insulating layer (dielectric layer) in contact with the organic semiconductor active layer interposed therebetween. Examples of the element structure include the following structures. (1) Substrate / gate electrode / insulator layer / source electrode and drain electrode / organic semiconductor active layer (2) Substrate / gate electrode / insulator layer / organic semiconductor active layer / source electrode and drain electrode (3) Substrate / organic semiconductor active layer / source electrode and drain electrode / insulator layer / gate electrode (4) Substrate / source electrode and drain electrode / organic semiconductor active layer / insulator layer / gate electrode The organic field effect transistor configured as described above can be applied as a pixel driving switching element for a liquid crystal display or an organic electroluminescence display using an active matrix driving method, etc.

[0558] The organic thin film solar cell has a structure in which an anode such as ITO, a hole transport layer, a photoelectric conversion layer, an electron transport layer, and a cathode are laminated on a transparent substrate such as glass. The photoelectric conversion layer has a p-type semiconductor layer on the anode side and an n-type semiconductor layer on the cathode side. The polycyclic aromatic compound according to the present invention can be used as a material for the hole transport layer, the p-type semiconductor layer, the n-type semiconductor layer, and the electron transport layer according to its physical properties. The polycyclic aromatic compound according to the present invention can function as a hole transport material or an electron transport material in an organic thin film solar cell. The organic thin film solar cell may appropriately include a hole blocking layer, an electron blocking layer, an electron injection layer, a hole injection layer, a smoothing layer, etc. in addition to the above. Known materials used for organic thin film solar cells can be appropriately selected and combined for use in the organic thin film solar cell.

[0559] Quantum dots with a narrow emission half-width are used as the phosphor of a wavelength conversion filter for the purpose of widening the color gamut of a display. On the other hand, there are problems such as instability against oxidation, high aggregability due to being nanoparticles, and the metal used being regulated as a pollutant. The polycyclic aromatic compound according to the present invention can be used as the phosphor of a wavelength conversion filter. As the matrix for dispersing this polycyclic aromatic compound, a polymer material having high transparency, low water vapor permeability, low oxygen permeability, and high thermal stability is preferable. Examples thereof include (meth)acrylic polymers such as polymethyl (meth)acrylate and cycloolefin polymers such as Zeonex.

Example

[0560] Hereinafter, the present invention will be described more specifically by way of examples, but the present invention is not limited thereto. First, a synthesis example of a polycyclic aromatic compound will be described below.

[0561] Synthesis Example (1) Compound (1A-92): 8,10,12,14-tetrakis(3,5-dimethylphenyl)-1,6,16,21,22,28-hexamethyl-3a 2 ,3b,8,10,12,14,18b,18c 2 ,24b,25b-decahydro-3a 2 ,8,10,12,14,18c 2 -hexaaza-3b,18b,24b,25b-tetraboraindeno[4’,3’,2’,1’:3,4,5]phenanthro[2,1,10,9-g1h1i1j1]inden o[4’,3’,2’,1’:3,4,5]phenanthro[2,1,10,9-yza1b1]nonacene synthesis

Chemical formula

[0562] Under a nitrogen atmosphere, N 1 ,N 3-Bis(3,5-dimethylphenyl)benzene-1,3-diamine (0.158 g, 0.50 mmol), 3-chloro-5-(4,5-dimethyl-9H-carbazol-9-yl)-N-(3,5-dimethylphenyl)-N-(m-tolyl)aniline (0.541 g, 1.1 mmol), Pd2(dba)3 (22.9 mg, 0.025 mmol), 2-dicyclohexylphosphino-2’,6’-dimethoxybiphenyl (SPhos: 20.5 mg, 0.050 mmol), NaOtBu (0.144 g, 1.5 mmol) and a flask containing o-xylene (2.5 ml) were heated to 110 °C and stirred for 16 h. The reaction solution was cooled to room temperature and filtered using a Florisil short path column (eluent: toluene / heptane = 1 / 10 (volume ratio)), and then the obtained crude product was purified by reprecipitation using hexane and dichloromethane to obtain N 1 ,N 1 ’-(1,3-phenylene)bis(5-(4,5-dimethyl-9H-carbazol-9-yl)-N 1 ,N 3 -bis(3,5-dimethylphenyl)-N 3 -(m-tolyl)benzene-1,3-diamine) as a white solid (0.474 g, yield 74%).

Chemical Structure

[0563] The structure of the compound obtained by NMR measurement was confirmed. 1 1H-NMR (400 MHz, CDCl3): δ = 2.09 (s, 12H), 2.16 (s, 12H), 2.20 (s, 6H), 2.98 (s, 12H), 6.50 (s, 2H), 6.56 (s, 2H), 6.60 (s, 2H), 6.62 - 6.64 (m, 6H), 6.69 - 6.72 (m, 6H), 6.75 (d, 2H) 6.79 (s, 2H), 6.86 - 6.88 (m, 3H), 6.91 (s, 2H), 6.96 (d, 4H), 7.02 (t, 2H), 7.09 (t, 1H), 7.19 - 7.20 (m, 8H).

[0564] N 1,N 1 ’-(1,3-phenylene)bis(5-(4,5-dimethyl-9H-carbazol-9-yl)-N 1 ,N 3 -bis(3,5-dimethylphenyl)-N 3 -(m-tolyl)benzene-1,3-diamine) (0.127 g, 0.10 mmol) and o-dichlorobenzene (1.0 ml) were placed in a flask. Under a nitrogen atmosphere at room temperature, boron tribromide (0.15 ml, 1.6 mmol) was added. After the addition was complete, the mixture was heated to 200 °C and stirred for 20 hours. The reaction solution was cooled to room temperature, and hydrogen bromide in the reaction solution was distilled off under reduced pressure. Dichloromethane (500 ml) was added to dilute the reaction solution, and then a phosphate buffer solution (pH = 7, 100 ml) was added at room temperature. The aqueous layer was extracted three times with dichloromethane, and then the solvent was distilled off under reduced pressure. The obtained crude product was washed with toluene to obtain Compound (1A-92) as a yellow solid (34.6 mg, yield 27%). [Chemical formula]

[0565] The structure of the compound obtained by NMR measurement was confirmed. 1 H-NMR (500 MHz, (CDCl2)2): δ = 2.26 (s, 12H), 2.34 (s, 12H), 2.39 (s, 6H), 3.34 (s, 6H), 3.45 (s, 6H), 5.48 (s, 1H), 6.07 (s, 2H), 6.64 (s, 4H), 6.77 (s, 2H), 6.84 (s, 4H), 6.97 (s, 2H), 7.06 (s, 2H), 7.19 (d, 2H), 7.64 (d, 2H), 7.87 (d, 2H), 9.01 - 9.05 (m, 4H), 9.49 (d, 2H), 10.9 (s, 1H).

[0566] Synthesis Example (2) Compound (1A-142): 8,10,12,14-tetrakis(3,5-di-t-butylphenyl)-6,16-di-t-butyl-1,21,22,28-tetramethyl-3a 2 ,3b,8,10,12,14,18b,18c 2, 24b, 25b - Decahydro - 3a 2 , 8, 10, 12, 14, 18c 2 - Hexaaza - 3b, 18b, 24b, 25b - Tetraboraindeno[4’, 3’, 2’, 1’:3, 4, 5]phenanthro[2, 1, 10, 9 - g1h1i1j1]indenol[4’, 3’, 2’, 1’:3, 4, 5]phenanthro[2, 1, 10, 9 - yza1b1]nonacene synthesis

Chem.

[0567] N 1 , N 1’ -(1, 3 - Phenylene)bis(5 - (4, 5 - dimethyl - 9H - carbazol - 9 - yl)-N 1 , N 3 - Bis(3, 5 - di - t - butylphenyl)-N 3 -(3 - (t - butyl)phenyl)benzene - 1, 3 - diamine)(0.171 g, 0.10 mmol) and o - dichlorobenzene (1.0 ml) were placed in a flask. Under a nitrogen atmosphere at room temperature, boron tribromide (0.15 ml, 1.6 mmol) was added. After the addition was complete, the mixture was heated to 200 °C and stirred for 20 hours. The reaction solution was cooled to room temperature, and hydrogen bromide in the reaction solution was distilled off under reduced pressure. Acetonitrile (15 ml) and triethylamine (1.0 ml) were added to the reaction solution, and after ultrasonic cleaning, suction filtration was performed. The obtained crude product was purified by a silica gel column (eluent: hexane / dichloromethane = 7 / 3) and washed with acetonitrile to obtain compound (1A - 142) as a yellow solid (50.9 mg, yield 29%).

Chem.

[0568] The structure of the compound obtained by NMR measurement was confirmed. 1H-NMR (400 MHz, CDCl3): δ = 1.12 (s, 18H), 1.15 (s, 36H), 1.30 (s, 36H), 3.18 (s, 6H), 3.29 (s, 6H), 5.94 (s, 2H), 6.04 (s, 2H), 6.24 (s, 1H), 6.93 (s, 4H), 7.01 (s, 4H), 7.22 (s, 2H), 7.32 (d, 2H), 7.43 (d, 2H), 7.52 (s, 2H), 7.60 (d, 2H), 8.86 (d, 2H), 8.97 (d, 2H), 9.31 (d, 2H), 10.8 (s, 1H).

[0569] Synthesis Example (3) Synthesis of Compound (1A-149)

Chemical Structure

[0570] To a flask containing Compound (Int-1A-149) (0.10 g) and o-dichlorobenzene (1.0 ml), boron tribromide (0.20 ml) was added at room temperature under a nitrogen atmosphere. After completion of the dropwise addition, the mixture was heated to 200 °C and stirred for 20 hours. The reaction solution was cooled to room temperature, and hydrogen bromide in the reaction solution was distilled off under reduced pressure. Acetonitrile (15 ml) and triethylamine (1.0 ml) were added to the reaction solution, and after ultrasonic cleaning, suction filtration was performed. The obtained crude product was purified by silica gel column (eluent: toluene) and washed with acetonitrile to obtain Compound (1A-149) as a yellow solid (10 mg). The target compound, Compound (1A-149), was confirmed by MALDI-MS at m / z = 2493.56.

Chemical Structure

[0571] Synthesis Example (4) Synthesis of Compound (1A-151)

Chemical Structure

[0572] To a flask containing compound (Int-1A-151) (0.10 g) and o-dichlorobenzene (1.0 ml), boron tribromide (0.20 ml) was added at room temperature under a nitrogen atmosphere. After completion of the addition dropwise, the mixture was heated to 200 °C and stirred for 20 hours. The reaction solution was cooled to room temperature, and hydrogen bromide in the reaction solution was distilled off under reduced pressure. Acetonitrile (15 ml) and triethylamine (1.0 ml) were added to the reaction solution, ultrasonic cleaning was performed, and then suction filtration was carried out. The obtained crude product was purified by a silica gel column (eluent: toluene) and washed with acetonitrile to obtain compound (1A-151) as a yellow solid (4 mg). The target compound (1A-151) was confirmed by MALDI-MS at m / z = 3260.01. [Chemical formula]

[0573] Synthesis Example (5) Synthesis of Compound (1A-195) [Chemical formula]

[0574] To a flask containing compound (Int-1A-195) (0.175 g, 0.10 mmol) and o-dichlorobenzene (1.0 ml), boron tribromide (0.15 ml, 1.6 mmol) was added at room temperature under a nitrogen atmosphere. After completion of the addition dropwise, the mixture was heated to 200 °C and stirred for 20 hours. The reaction solution was cooled to room temperature, and hydrogen bromide in the reaction solution was distilled off under reduced pressure. Dichloromethane (500 ml) was added to dilute the reaction solution, and then a phosphate buffer solution (pH = 7, 100 ml) was added at room temperature. The aqueous layer was extracted three times with dichloromethane, and then the solvent was distilled off under reduced pressure. The obtained crude product was purified by a silica gel column (eluent: hexane / toluene = 2 / 1) to obtain compound (1A-195) as a yellow solid (76.8 mg, yield 43%). [...

Claims

**Claim 1**: A polycyclic aromatic compound represented by the following general formula (2A). [Chemical Formula 3] 【Chemical Formula 4】 The part of "[φ2]n" is a part formed by linking a total of n units selected from the group consisting of the unit structure represented by the above formula (φ2 - m1) and the unit structure represented by the above formula (φ2 - m2). n is an integer from 1 to 3. Each Ra is independently hydrogen or alkyl having 1 to 4 carbon atoms. Rb and Rc are each independently hydrogen, aryl having 6 to 10 carbon atoms, diarylamino (wherein aryl is aryl having 6 to 10 carbon atoms), or alkyl having 1 to 12 carbon atoms, and at least one hydrogen in the Rb and Rc may be substituted with alkyl having 1 to 4 carbon atoms. Y is B. X １ is >N-R, and R in the >N-R is each independently an aryl having 6 to 10 carbon atoms which may be substituted with an alkyl having 1 to 4 carbon atoms, X ２ is N, In the above formula (2A), formula (φ2-m1), and formula (φ2-m2), adjacent Rs in adjacent c rings ｃ at least one pair of which are combined to form a single bond or an arylene having 6 to 10 carbon atoms, At least one hydrogen in the compound represented by the above formula (2A) may be substituted with deuterium, cyano, or halogen. **Claim 2** The polycyclic aromatic compound according to Claim 1, represented by the following structural formula. 【Chemical Formula 5】 ("Me" in the structural formula represents a methyl group.) **Claim 3** The polycyclic aromatic compound according to Claim 1, represented by any of the following structural formulas. 【Chemical Formula 6】 【Chemical Formula 7】 ("Me" in the structural formula represents a methyl group, and "tBu" represents a t-butyl group.) **Claim 4** The polycyclic aromatic compound according to Claim 1, represented by any of the following structural formulas. 【Chemical 8】 ("Me" in the structural formula represents a methyl group, and "tBu" represents a t-butyl group.) **Claim 5** A material for an organic device, containing the polycyclic aromatic compound according to any of Claims 1 to 4. **Claim 6** The material for an organic device according to Claim 5, wherein the material for an organic device is a material for an organic electroluminescent element, a material for an organic field effect transistor, a material for an organic thin film solar cell, or a material for a wavelength conversion filter. **Claim 7** The material for an organic device according to Claim 6, wherein the material for an organic electroluminescent element is a material for a light emitting layer. **Claim 8** An ink composition containing the polycyclic aromatic compound according to any of Claims 1 to 4 and an organic solvent. **Claim 9** An organic electroluminescent element having a pair of electrodes consisting of an anode and a cathode, and an organic layer disposed between the pair of electrodes and containing the polycyclic aromatic compound according to any of Claims 1 to 4. **Claim 10** The organic electroluminescent element according to Claim 9, wherein the organic layer is a light emitting layer. **Claim 11** The organic electroluminescent device according to claim 10, wherein the light-emitting layer contains a host and the polycyclic aromatic compound as a dopant.

12. The organic electroluminescent device according to claim 11, wherein the host is an anthracene-based compound, a fluorene-based compound, or a dibenzocrisene-based compound.

13. The organic electroluminescent device according to any one of claims 10 to 12, having at least one layer of an electron transport layer and an electron injection layer disposed between the cathode and the light-emitting layer, and at least one of the electron transport layer and the electron injection layer contains at least one selected from the group consisting of a borane derivative, a pyridine derivative, a fluoranthene derivative, a BO-based derivative, an anthracene derivative, a benzofluorene derivative, a phosphine oxide derivative, a pyrimidine derivative, a carbazole derivative, a triazine derivative, a benzimidazole derivative, a phenanthroline derivative, a quinolinol-based metal complex, a thiazole derivative, a benzothiazole derivative, a silole derivative, and an azoline derivative.

14. The organic electroluminescent device according to claim 13, wherein at least one layer of the electron transport layer and the electron injection layer further contains at least one selected from the group consisting of an alkali metal, an alkaline earth metal, a rare earth metal, an oxide of an alkali metal, a halide of an alkali metal, an oxide of an alkaline earth metal, a halide of an alkaline earth metal, an oxide of a rare earth metal, a halide of a rare earth metal, an organic complex of an alkali metal, an organic complex of an alkaline earth metal, and an organic complex of a rare earth metal.

15. A display device or a lighting device including the organic electroluminescent device according to any one of claims 9 to 14.

16. A wavelength conversion filter including the material for a wavelength conversion filter according to claim 6.

Images