Polycyclic aromatic compounds

Abstract

This invention provides a polycyclic aromatic compound. Specifically, it provides a polycyclic aromatic compound with a novel structure and an organic EL element using the same. By fabricating a polycyclic aromatic compound with a novel structure obtained by linking multiple aromatic rings with boron, nitrogen, and oxygen atoms, the options for materials used in organic devices, such as materials for organic EL elements, are increased. Furthermore, by using the polycyclic aromatic compound with the novel structure as a material for organic EL elements, organic EL elements with excellent luminous efficiency and device lifetime are provided.

Description

[0001] This application is a divisional application of the application filed on October 18, 2019, with application number 201980083651.2 and invention title "Polycyclic Aromatic Compounds". Technical Field

[0002] This invention relates to polycyclic aromatic compounds, organic electroluminescent elements using the same, organic field-effect transistors and organic thin-film solar cells, as well as display devices and lighting devices. It should be noted that in this specification, "organic electroluminescent element" is sometimes referred to as "organic EL element" or simply "element". Background Technology

[0003] Previously, display devices using electroluminescent elements have been extensively studied due to their ability to achieve energy savings and thinner designs. Consequently, organic electroluminescent elements formed from organic materials have been actively researched due to their ease of lightweighting and scaling. In particular, the development of organic materials with luminescent properties such as blue (one of the three primary colors of light) and organic materials with charge transport capabilities such as holes and electrons (potentially becoming semiconductors or superconductors) has been actively pursued, with both high-molecular-weight and low-molecular-weight compounds being studied to date.

[0004] Organic EL devices have the following structure: they include a pair of electrodes comprising an anode and a cathode, and one or more layers disposed between the pair of electrodes and containing organic compounds. Layers containing organic compounds include light-emitting layers, charge transport / injection layers for transporting or injecting charges such as holes and electrons, and various organic materials suitable for these layers have been developed.

[0005] As materials for luminescent layers, compounds such as benzo[a]fluorene compounds have been developed (International Publication No. 2004 / 061047). Furthermore, as hole transport materials, compounds such as triphenylamine compounds have been developed (Japanese Patent Application Publication No. 2001-172232). Additionally, as electron transport materials, compounds such as anthracene compounds have been developed (Japanese Patent Application Publication No. 2005-170911).

[0006] In addition, in recent years, materials derived from modified triphenylamine derivatives have been reported as materials used in organic EL elements and organic thin-film solar cells (International Publication No. 2012 / 118164). This material is characterized by improving its planarity by linking the aromatic rings constituting the triphenylamine to each other, using the practically applicable N,N'-diphenyl-N,N'-bis(3-methylphenyl)-1,1'-biphenyl-4,4'-diamine (TPD) as a reference. This document evaluates the charge transport properties of, for example, NO-linked compounds (Compound 1 on page 63), but does not describe methods for manufacturing materials other than NO-linked compounds. Furthermore, the overall electronic state of the compound differs depending on the elements to be linked; therefore, the properties obtained from materials other than NO-linked compounds are still unknown. Examples of such compounds can also be found (International Publication No. 2011 / 107186). For example, compounds with conjugated structures having high energy (T1) of triplet excitons are advantageous as materials for blue emitting layers because they can emit phosphorescence at shorter wavelengths. Furthermore, novel conjugated structures with high T1 are also needed as electron transport materials and hole transport materials for holding the emitting layer.

[0007] The host material of organic EL devices is typically a molecule composed of multiple existing aromatic rings, such as benzene or carbazole, linked by single bonds, phosphorus atoms, and silicon atoms. This is because linking multiple conjugated aromatic rings with smaller structures ensures the large HOMO-LUMO gap (band gap Eg) required for the host material. Furthermore, the host material of organic EL devices obtained using phosphorescent or thermally activated delayed fluorescence materials also requires a high triplet excitation energy (Eg). T However, by localizing the SOMO1 and SOMO2 orbitals of the triplet excited state (T1) through the connection of donor or acceptor aromatic rings and substituents, the exchange interaction between the two orbitals is reduced, thereby increasing the triplet excitation energy (E). T However, the redox stability of the small aromatic rings in conjugated systems is insufficient, and the lifetime of components using molecules obtained by linking existing aromatic rings as host materials is inadequate. On the other hand, polycyclic aromatic compounds with extended π-conjugated systems generally exhibit excellent redox stability, but their HOMO-LUMO gap (band gap Eg) and triplet excitation energy (E) are relatively high. T The low efficiency makes it unsuitable for use as the main material.

[0008] Existing technical documents

[0009] Patent documents

[0010] Patent Document 1: International Publication No. 2004 / 061047

[0011] Patent Document 2: Japanese Patent Application Publication No. 2001-172232

[0012] Patent Document 3: Japanese Patent Application Publication No. 2005-170911

[0013] Patent Document 4: International Publication No. 2012 / 118164

[0014] Patent Document 5: International Publication No. 2011 / 107186

[0015] Patent Document 6: International Publication No. 2015 / 102118 Summary of the Invention

[0016] The problem the invention aims to solve

[0017] As mentioned above, various materials have been developed for use in organic EL devices, but to increase the options for materials used in organic EL devices, it is desirable to develop materials formed from compounds different from those previously used. In particular, the properties of organic ELs obtained from materials other than the NO-linked system compounds reported in Patent Documents 1-4, or their manufacturing methods, are still unknown.

[0018] Furthermore, Patent Document 6 reports boron-containing polycyclic aromatic compounds and organic EL devices using them. Consequently, in order to improve device characteristics, there is a search for materials for the light-emitting layer, especially doped materials, that can improve luminous efficiency and device lifetime.

[0019] Solution for solving the problem

[0020] In order to solve the above-mentioned problems, the inventors conducted in-depth research and discovered that by configuring a layer containing a polycyclic aromatic compound with a novel structure between a pair of electrodes to form an organic EL element, an excellent organic EL element can be obtained, thereby completing the present invention. That is, the present invention provides materials for organic devices, such as polycyclic aromatic compounds and materials for organic EL elements containing polycyclic aromatic compounds.

[0021] It should be noted that in this specification, chemical structures and substituents are sometimes expressed in terms of the number of carbon atoms. However, when a chemical structure is substituted with a substituent, or when a substituent is further substituted with another substituent, the number of carbon atoms refers to the individual carbon atoms of the chemical structure and the substituent, not the total number of carbon atoms of the chemical structure and the substituent, or the total number of carbon atoms of the substituents. For example, "a substituent B with a carbon atom number of Y that is replaced by a substituent A with a carbon atom number of X" means that "a substituent B with a carbon atom number of Y" is replaced by "a substituent A with a carbon atom number of X". The number of carbon atoms Y is not the total number of carbon atoms of substituent A and substituent B. Furthermore, for example, "a substituent B with a carbon atom number of Y that is replaced by a substituent A" means that "a substituent B with a carbon atom number of Y" is replaced by "a substituent A (of any number of carbon atoms)". The number of carbon atoms Y is not the total number of carbon atoms of substituent A and substituent B.

[0022] Item 1.

[0023] A polycyclic aromatic compound is represented by the following general formula (1).

[0024]

[0025] (In the above formula (1),

[0026] Rings A, B, and C are each independently an aromatic or heteroaromatic ring, and at least one hydrogen atom in these rings may be substituted.

[0027] Y 1 Each can be independently B, P, P=O, P=S, Al, Ga, As, Si-R, or Ge-R, where R in Si-R and Ge-R is aryl, alkyl, or cycloalkyl.

[0028] X 1 Each is independently N or CR, where R in the aforementioned CR is an optionally substituted aryl, optionally substituted alkyl, or optionally substituted cycloalkyl.

[0029] X 2 Each of these can be independently >O, >NR, >C(-R)2, >S, or >Se, where R in >NR is an optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkyl, or optionally substituted cycloalkyl, and R in >C(-R)2 is hydrogen, optionally substituted aryl, optionally substituted alkyl, or optionally substituted cycloalkyl. Furthermore, R in >NR and / or >C(-R)2 can optionally be bonded to the aforementioned A and / or C rings via a linking group or a single bond.

[0030] X 1 When the value is N, some or all of two adjacent A rings can be bonded together by single bonds.

[0031] n is an integer greater than or equal to 1, and

[0032] At least one hydrogen atom in the compound shown in formula (1) may optionally be substituted with a deuterium, cyano, or halogen.

[0033] Item 2.

[0034] According to the polycyclic aromatic compound of claim 1, wherein rings A, B, and C are each independently an aromatic or heteroaromatic ring, and at least one hydrogen atom of these rings is optionally substituted or unsubstituted with an aryl group, a substituted or unsubstituted heteroaromatic group, a substituted or unsubstituted diarylamino group, a substituted or unsubstituted diheteroarylamino group, a substituted or unsubstituted arylheteroarylamino group, a substituted or unsubstituted diarylboroyl group (the two aryl groups are optionally bonded by a single bond or a linking group), a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, or a substituted silyl group.

[0035] Y 1 Each can be independently B, P, P=O, P=S, Al, Ga, As, Si-R, or Ge-R, where R in Si-R and Ge-R is aryl, alkyl, or cycloalkyl.

[0036] X 1 Each is independently N or CR, where R in the aforementioned CR is an optionally substituted aryl, optionally substituted alkyl, or optionally substituted cycloalkyl.

[0037] X 2 Each of these can be independently >O, >NR, >C(-R)2, >S, or >Se. In the aforementioned >NR, R is optionally an aryl group substituted with an alkyl or cycloalkyl group, a heteroaryl group substituted with an alkyl or cycloalkyl group, an alkyl or cycloalkyl group, and in the aforementioned >C(-R)2, R is hydrogen, an aryl group substituted with an alkyl or cycloalkyl group, an alkyl or cycloalkyl group. Furthermore, in the aforementioned >NR and / or the aforementioned >C(-R)2, R is optionally bonded to the aforementioned A ring and / or C ring via -O-, -S-, -C(-R)2-, -Si(-R)2-, or a single bond. In the aforementioned -C(-R)2- or -Si(-R)2-, R is hydrogen, an alkyl group, or a cycloalkyl group.

[0038] X 1 When the value is N, all adjacent A rings can be bonded to each other arbitrarily using single bonds.

[0039] n is an integer from 1 to 5, and

[0040] At least one hydrogen atom in the compound shown in formula (1) may be optionally replaced by deuterium, cyano or halogen.

[0041] Item 3.

[0042] The polycyclic aromatic compounds according to item 1 are represented by the following general formula (2).

[0043]

[0044] (In the above formula (2),

[0045] R a Each of these groups is independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (the two aryl groups are optionally bonded by a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, or alkyldicycloalkylsilyl, wherein at least one hydrogen atom is optionally substituted with an aryl, heteroaryl, alkyl, or cycloalkyl group.

[0046] R b Each of these groups is independently hydrogen, aryl, heteroaryl, diarylamino, diherylamino, arylherylamino, diarylboryl (the two aryl groups are optionally bonded by a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, or alkyldicycloalkylsilyl, wherein at least one hydrogen atom is optionally substituted with an aryl, heteroaryl, alkyl, or cycloalkyl group, and

[0047] R c Each of these groups is independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (the two aryl groups are optionally bonded by a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, or alkyldicycloalkylsilyl, wherein at least one hydrogen atom is optionally substituted with an aryl, heteroaryl, alkyl, or cycloalkyl group.

[0048] In addition, R a R b and R c The adjacent groups may optionally be bonded to each other and together with ring a, ring b, or ring c to form an aromatic ring or heteroaromatic ring, wherein at least one hydrogen atom of the formed ring may optionally be replaced by an aryl, heteroaryl, diarylamino, diherylamino, arylherylamino, diarylboryl (the two aryl groups may optionally be bonded by a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, or alkyldicycloalkylsilyl, wherein at least one hydrogen atom of these substituents may optionally be replaced by an aryl, heteroaryl, alkyl, or cycloalkyl.

[0049] Y 1Each can be independently B, P, P=O, P=S, Al, Ga, As, Si-R, or Ge-R, where R in Si-R and Ge-R is an aryl group with 6 to 12 carbon atoms, an alkyl group with 1 to 6 carbon atoms, or a cycloalkyl group with 3 to 14 carbon atoms.

[0050] X 1 Each can be independently N or CR, where R in CR is an aryl group with 6 to 12 carbon atoms, an alkyl group with 1 to 6 carbon atoms, or a cycloalkyl group with 3 to 14 carbon atoms.

[0051] X 2 Each is independently >O, >NR, >C(-R)2, >S, or >Se, where R in >NR is an aryl group with 6 to 12 carbon atoms, a heteroaryl group with 2 to 15 carbon atoms, an alkyl group with 1 to 6 carbon atoms, or a cycloalkyl group with 3 to 14 carbon atoms, and at least one hydrogen atom of the aryl or heteroaryl group is optionally substituted with an alkyl group with 1 to 6 carbon atoms or a cycloalkyl group with 3 to 14 carbon atoms, and R in >C(-R)2 is hydrogen, an aryl group with 6 to 12 carbon atoms, or an alkyl group with 1 to 6 carbon atoms. The aryl group is an alkyl group or a cycloalkyl group having 3 to 14 carbon atoms, wherein at least one hydrogen atom of the aryl group is optionally substituted with an alkyl group having 1 to 6 carbon atoms or a cycloalkyl group having 3 to 14 carbon atoms. Furthermore, the R in the aforementioned >NR and / or the aforementioned >C(-R)2 is optionally bonded to the aforementioned a ring and / or c ring via -O-, -S-, -C(-R)2-, -Si(-R)2- or a single bond, wherein the R in the aforementioned -C(-R)2- is hydrogen, an alkyl group having 1 to 6 carbon atoms, or a cycloalkyl group having 3 to 14 carbon atoms.

[0052] X 1 When the value is N, all adjacent a-rings can be bonded to each other arbitrarily using single bonds.

[0053] n is an integer from 1 to 3, and

[0054] In the compound shown in formula (2), at least one hydrogen atom may be optionally substituted with a deuterium, cyano, or halogen.

[0055] Item 4.

[0056] According to the polycyclic aromatic compound described in item 3, wherein R a Each of the following groups is independently hydrogen, an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, a diarylamino group (wherein the aryl group is an aryl group having 6 to 12 carbon atoms), a diarylboryl group (wherein the aryl group is an aryl group having 6 to 12 carbon atoms, and the two aryl groups are optionally bonded by a single bond or a linking group), an alkyl group having 1 to 24 carbon atoms, or a cycloalkyl group having 3 to 24 carbon atoms, wherein at least one hydrogen atom of these aryl or heteroaryl groups is optionally substituted by an alkyl group having 1 to 6 carbon atoms or a cycloalkyl group having 3 to 14 carbon atoms.

[0057] Rb Each of the following groups is independently hydrogen, an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, a diarylamino group (wherein the aryl group is an aryl group having 6 to 12 carbon atoms), a diarylboroyl group (wherein the aryl group is an aryl group having 6 to 12 carbon atoms, and the two aryl groups are optionally bonded by a single bond or a linking group), an alkyl group having 1 to 24 carbon atoms, or a cycloalkyl group having 3 to 24 carbon atoms, wherein at least one hydrogen atom of these aryl or heteroaryl groups is optionally substituted by an alkyl group having 1 to 6 carbon atoms or a cycloalkyl group having 3 to 14 carbon atoms, and

[0058] R c Each of the following groups is independently hydrogen, an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, a diarylamino group (wherein the aryl group is an aryl group having 6 to 12 carbon atoms), a diarylboryl group (wherein the aryl group is an aryl group having 6 to 12 carbon atoms, and the two aryl groups are optionally bonded by a single bond or a linking group), an alkyl group having 1 to 24 carbon atoms, or a cycloalkyl group having 3 to 24 carbon atoms, wherein at least one hydrogen atom of these aryl or heteroaryl groups is optionally substituted by an alkyl group having 1 to 6 carbon atoms or a cycloalkyl group having 3 to 14 carbon atoms.

[0059] In addition, R a R b and R c The adjacent groups may optionally be bonded to each other and, together with ring a, ring b, or ring c, form an aromatic ring with 9 to 16 carbon atoms or a heteroaromatic ring with 6 to 15 carbon atoms. At least one hydrogen atom of the formed ring may optionally be replaced by an aryl group with 6 to 30 carbon atoms, a heteroaromatic group with 2 to 30 carbon atoms, a diarylamino group (wherein the aryl group is an aryl group with 6 to 12 carbon atoms), a diarylboryl group (wherein the aryl group is an aryl group with 6 to 12 carbon atoms, and the two aryl groups may optionally be bonded by a single bond or a linking group), an alkyl group with 1 to 24 carbon atoms, or a cycloalkyl group with 3 to 24 carbon atoms. At least one hydrogen atom of these aryl or heteroaromatic groups may optionally be replaced by an alkyl group with 1 to 6 carbon atoms or a cycloalkyl group with 3 to 14 carbon atoms.

[0060] Y 1 Each can be independently B, P, P=O, P=S, or Si-R, where R in the aforementioned Si-R is an aryl group with 6 to 10 carbon atoms, an alkyl group with 1 to 5 carbon atoms, or a cycloalkyl group with 5 to 10 carbon atoms.

[0061] X 1 Each can be independently N or CR, where R in CR is an aryl group with 6 to 10 carbon atoms, an alkyl group with 1 to 5 carbon atoms, or a cycloalkyl group with 5 to 10 carbon atoms.

[0062] X 2Each is independently >O, >NR, >C(-R)2, or >S, wherein the R in >NR is an aryl group with 6 to 10 carbon atoms, an alkyl group with 1 to 5 carbon atoms, or a cycloalkyl group with 5 to 10 carbon atoms, and at least one hydrogen atom of the aryl group is optionally substituted with an alkyl group with 1 to 5 carbon atoms or a cycloalkyl group with 5 to 10 carbon atoms; and the R in >C(-R)2 is hydrogen, an aryl group with 6 to 10 carbon atoms, an alkyl group with 1 to 5 carbon atoms, or a cycloalkyl group with 5 to 10 carbon atoms, and at least one hydrogen atom of the aryl group is optionally substituted with an alkyl group with 1 to 5 carbon atoms or a cycloalkyl group with 5 to 10 carbon atoms.

[0063] n is an integer from 1 to 3, and

[0064] At least one hydrogen atom in the compound shown in formula (2) may be optionally replaced by deuterium, cyano or halogen.

[0065] Item 5.

[0066] According to the polycyclic aromatic compound described in item 3, wherein R a Each of the following groups is independently hydrogen, an aryl group having 6 to 16 carbon atoms, a heteroaryl group having 2 to 20 carbon atoms, a diarylamino group (wherein the aryl group is an aryl group having 6 to 10 carbon atoms), a diarylboryl group (wherein the aryl group is an aryl group having 6 to 10 carbon atoms, and the two aryl groups are optionally bonded by a single bond or a linking group), an alkyl group having 1 to 12 carbon atoms, or a cycloalkyl group having 3 to 16 carbon atoms, wherein at least one hydrogen atom of these aryl or heteroaryl groups is optionally substituted by an alkyl group having 1 to 6 carbon atoms or a cycloalkyl group having 3 to 14 carbon atoms.

[0067] R b Each of the following groups is independently hydrogen, an aryl group having 6 to 16 carbon atoms, a heteroaryl group having 2 to 20 carbon atoms, a diarylamino group (wherein the aryl group is an aryl group having 6 to 10 carbon atoms), a diarylboroyl group (wherein the aryl group is an aryl group having 6 to 10 carbon atoms, and the two aryl groups are optionally bonded by a single bond or a linking group), an alkyl group having 1 to 12 carbon atoms, or a cycloalkyl group having 3 to 16 carbon atoms, wherein at least one hydrogen atom of these aryl or heteroaryl groups is optionally substituted by an alkyl group having 1 to 6 carbon atoms or a cycloalkyl group having 3 to 14 carbon atoms, and

[0068] R c Each of the following groups is independently hydrogen, an aryl group having 6 to 16 carbon atoms, a heteroaryl group having 2 to 20 carbon atoms, a diarylamino group (wherein the aryl group is an aryl group having 6 to 10 carbon atoms), a diarylboryl group (wherein the aryl group is an aryl group having 6 to 10 carbon atoms, and the two aryl groups are optionally bonded by a single bond or a linking group), an alkyl group having 1 to 12 carbon atoms, or a cycloalkyl group having 3 to 16 carbon atoms, wherein at least one hydrogen atom of these aryl or heteroaryl groups is optionally substituted by an alkyl group having 1 to 6 carbon atoms or a cycloalkyl group having 3 to 14 carbon atoms.

[0069] Y1 Each can be independently represented as B, P, P=O, or P=S.

[0070] X 1 Let N be the number of ...

[0071] X 2 Each is independently >O, >NR, or >C(-R)2, where R in >NR is an aryl group with 6 to 10 carbon atoms, an alkyl group with 1 to 5 carbon atoms, or a cycloalkyl group with 5 to 10 carbon atoms, and at least one hydrogen atom of the aryl group is optionally substituted with an alkyl group with 1 to 5 carbon atoms or a cycloalkyl group with 5 to 10 carbon atoms; and R in >C(-R)2 is hydrogen, an aryl group with 6 to 10 carbon atoms, an alkyl group with 1 to 5 carbon atoms, or a cycloalkyl group with 5 to 10 carbon atoms, and at least one hydrogen atom of the aryl group is optionally substituted with an alkyl group with 1 to 5 carbon atoms or a cycloalkyl group with 5 to 10 carbon atoms.

[0072] n is an integer from 1 to 3, and

[0073] At least one hydrogen atom in the compound shown in formula (2) may be optionally replaced by deuterium, cyano or halogen.

[0074] Item 6.

[0075] According to the polycyclic aromatic compound described in item 3, wherein R a Each of the following groups is independently hydrogen, an aryl group having 6 to 16 carbon atoms, a heteroaryl group having 2 to 20 carbon atoms, a diarylamino group (wherein the aryl group is an aryl group having 6 to 10 carbon atoms), a diarylboryl group (wherein the aryl group is an aryl group having 6 to 10 carbon atoms, and the two aryl groups are optionally bonded by a single bond or a linking group), an alkyl group having 1 to 12 carbon atoms, or a cycloalkyl group having 3 to 16 carbon atoms, wherein at least one hydrogen atom of these aryl or heteroaryl groups is optionally substituted by an alkyl group having 1 to 5 carbon atoms or a cycloalkyl group having 5 to 10 carbon atoms.

[0076] R b Each of the following groups is independently hydrogen, an aryl group having 6 to 16 carbon atoms, a heteroaryl group having 2 to 20 carbon atoms, a diarylamino group (wherein the aryl group is an aryl group having 6 to 10 carbon atoms), a diarylboroyl group (wherein the aryl group is an aryl group having 6 to 10 carbon atoms, and the two aryl groups are optionally bonded by a single bond or a linking group), an alkyl group having 1 to 12 carbon atoms, or a cycloalkyl group having 3 to 16 carbon atoms, wherein at least one hydrogen atom of these aryl or heteroaryl groups is optionally substituted by an alkyl group having 1 to 5 carbon atoms or a cycloalkyl group having 5 to 10 carbon atoms, and

[0077] R cEach of the following groups is independently hydrogen, an aryl group having 6 to 16 carbon atoms, a heteroaryl group having 2 to 20 carbon atoms, a diarylamino group (wherein the aryl group is an aryl group having 6 to 10 carbon atoms), a diarylboryl group (wherein the aryl group is an aryl group having 6 to 10 carbon atoms, and the two aryl groups are optionally bonded by a single bond or a linking group), an alkyl group having 1 to 12 carbon atoms, or a cycloalkyl group having 3 to 16 carbon atoms, wherein at least one hydrogen atom of these aryl or heteroaryl groups is optionally substituted by an alkyl group having 1 to 5 carbon atoms or a cycloalkyl group having 5 to 10 carbon atoms.

[0078] Y 1 For B,

[0079] X 1 Let N be the number of ...

[0080] X 2 Each is independently >O or >NR, where R in >NR is an aryl group with 6 to 10 carbon atoms, an alkyl group with 1 to 5 carbon atoms, or a cycloalkyl group with 5 to 10 carbon atoms, and at least one hydrogen atom of the aryl group is optionally substituted with an alkyl group with 1 to 5 carbon atoms or a cycloalkyl group with 5 to 10 carbon atoms.

[0081] n is 1 or 2, and

[0082] At least one hydrogen atom in the compound shown in formula (2) may be optionally replaced by deuterium, cyano or halogen.

[0083] Item 7.

[0084] The polycyclic aromatic compound according to item 1 is represented by any of the following structural formulas.

[0085]

[0086] (In the above structural formulas, "Me" represents a methyl group.)

[0087] Item 8.

[0088] A reactive compound obtained by substituting a polycyclic aromatic compound, as described in any one of claims 1 to 7, with a reactive substituent.

[0089] Item 9.

[0090] A polymeric compound or a polymeric crosslinker, wherein the polymeric compound is obtained by polymerizing the reactive compound described in item 8 as a monomer, and the polymeric crosslinker is obtained by further crosslinking the polymeric compound.

[0091] Item 10.

[0092] A side-chain polymer compound or a side-chain polymer crosslinker, wherein the side-chain polymer compound is obtained by substituting the reactive compound described in item 8 onto the main chain polymer, and the side-chain polymer crosslinker is obtained by further crosslinking the side-chain polymer compound.

[0093] Item 11.

[0094] An organic device material comprising any one of claims 1 to 7.

[0095] Item 12.

[0096] An organic device material comprising the reactive compound described in item 8.

[0097] Item 13.

[0098] An organic device material comprising the polymer compound or polymer crosslinker described in item 9.

[0099] Item 14.

[0100] An organic device material comprising the side-group type polymer compound or side-group type polymer crosslinker as described in item 10.

[0101] Item 15.

[0102] The organic device material according to any one of claims 11 to 14, wherein the aforementioned organic device material is an organic electroluminescent element material, an organic field-effect transistor material, or an organic thin-film solar cell material.

[0103] Item 16.

[0104] According to item 15, the organic device material is a light-emitting layer material.

[0105] Item 17.

[0106] An ink composition comprising any one of claims 1 to 7, a polycyclic aromatic compound, and an organic solvent.

[0107] Item 18.

[0108] An ink composition comprising the reactive compound described in item 8 and an organic solvent.

[0109] Item 19.

[0110] An ink composition comprising a main-chain polymer, the reactive compound described in item 8, and an organic solvent.

[0111] Item 20.

[0112] An ink composition comprising the polymeric compound or polymeric crosslinker described in item 9, and comprising an organic solvent.

[0113] Item 21.

[0114] An ink composition comprising the side-group type polymer compound or side-group type polymer crosslinker as described in item 10, and comprising an organic solvent.

[0115] Item 22.

[0116] An organic electroluminescent element comprising: a pair of electrodes including an anode and a cathode, and an organic layer disposed between the pair of electrodes, said organic layer containing any one of claims 1 to 7, a reactive compound as described in claim 8, a polymer compound or polymer crosslinker as described in claim 9, or a side-chain polymer compound or side-chain polymer crosslinker as described in claim 10.

[0117] Item 23.

[0118] According to item 22, the organic electroluminescent element is wherein the aforementioned organic layer is a light-emitting layer.

[0119] Item 24.

[0120] According to the organic electroluminescent element of item 23, the aforementioned light-emitting layer comprises a host and includes the aforementioned polycyclic aromatic compound, reactive compound, polymer compound, polymer crosslinker, side-group type polymer compound or side-group type polymer crosslinker as a dopant.

[0121] Item 25.

[0122] According to the organic electroluminescent element of item 24, the aforementioned main body is anthracene compound, fluorene compound or dibenzo[a]pyrene compound.

[0123] Item 26.

[0124] The organic electroluminescent element according to any one of claims 23 to 25 has an electron transport layer and / or an electron injection layer disposed between the aforementioned cathode and the aforementioned light-emitting layer, wherein 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 derivatives, anthracene derivatives, benzo[a]fluorene derivatives, phosphine oxide derivatives, pyrimidine derivatives, carbazole derivatives, triazine derivatives, benzimidazole derivatives, phenanthrene derivatives, and hydroxyquinoline metal complexes.

[0125] Item 27.

[0126] According to the organic electroluminescent element of claim 26, the aforementioned electron transport layer and / or electron injection layer further comprises 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.

[0127] Item 28.

[0128] The organic electroluminescent element according to any one of claims 23 to 27, wherein at least one of the hole injection layer, hole transport layer, light emission layer, electron transport layer and electron injection layer comprises: a polymeric compound obtained by polymerizing a low-molecular-weight compound capable of forming each layer as a monomer, or a polymeric cross-linked compound obtained by further cross-linking the polymeric compound, or a side-chain type polymeric compound obtained by reacting a low-molecular-weight compound capable of forming each layer with a main-chain type polymer, or a side-chain type polymeric cross-linked compound obtained by further cross-linking the side-chain type polymeric compound.

[0129] Item 29.

[0130] A display device or lighting device comprising the organic electroluminescent element described in any one of claims 22 to 28.

[0131] The effects of the invention

[0132] According to a preferred embodiment of the present invention, a polycyclic aromatic compound with a novel structure can be provided that can be used as a material for organic devices such as organic EL elements, thereby providing excellent organic devices such as organic EL elements.

[0133] Specifically, the inventors have discovered that polycyclic aromatic compounds (basic skeleton parts) obtained by connecting aromatic rings with heteroelements such as boron, phosphorus, oxygen, nitrogen, and sulfur possess large HOMO-LUMO gaps (band gap Eg of thin films) and high triplet excitation energies (E0). TThe reason for this is believed to be that, due to the low aromaticity of the six-membered ring containing the heteroelement, the reduction of the HOMO-LUMO gap associated with the expansion of the conjugated system is suppressed; the SOMO1 and SOMO2 of the triplet excited state (T1) are localized due to the electronic perturbation of the heteroelement. Furthermore, the polycyclic aromatic compound (basic skeleton part) containing the heteroelement described in this invention exhibits a smaller exchange interaction between the two orbitals due to the localization of SOMO1 and SOMO2 in the triplet excited state (T1). Therefore, the energy difference between the triplet excited state (T1) and the singlet excited state (S1) is small, exhibiting thermally activated delayed fluorescence, thus making it useful as a fluorescent material for organic EL elements. In addition, it possesses a high triplet excitation energy (E0). T These materials are also useful as electron transport layers and hole transport layers in phosphorescent organic EL devices and organic EL devices utilizing thermally activated delayed fluorescence. Furthermore, the energies of HOMO and LUMO can be arbitrarily changed by introducing substituents into these polycyclic aromatic compounds (basic skeleton parts), thus allowing for optimization of ionization potential and electron affinity based on the surrounding materials.

[0134] Based on the characteristics of this basic framework, the compounds of the present invention can be expected to have lower melting points and sublimation temperatures by introducing cycloalkyl groups. This means that in sublimation purification, which is almost indispensable for the purification of materials for organic devices such as organic EL elements requiring high purity, purification can be carried out at lower temperatures, thus avoiding thermal decomposition of the material. Furthermore, this is also true in vacuum evaporation processes, which are effective means for manufacturing organic devices such as organic EL elements. Since the process can be carried out at lower temperatures, thermal decomposition of the material can be avoided, resulting in high-performance applications in organic devices. In addition, by introducing cycloalkyl groups, its solubility in organic solvents is improved, thus it can also be applied to the fabrication of elements utilizing coating processes. However, the present invention is not particularly limited to these principles. Attached Figure Description

[0135] Figure 1 This is a schematic cross-sectional view showing the organic EL element described in this embodiment.

[0136] Figure 2 This is the absorption spectrum of compound (1-230).

[0137] Figure 3 This is the fluorescence spectrum of compound (1-230).

[0138] Figure 4 It is a decay curve (5.8~40 nsec) used to measure the delayed fluorescence lifetime of compound (1-230).

[0139] Figure 5It is a decay curve (6.0~25μsec) used to measure the delayed fluorescence lifetime of compounds (1-230).

[0140] Figure 6 The comparison is of the absorption, fluorescence, and phosphorescence spectra of compound 1.

[0141] Figure 7 This is a decay curve (100~250 μsec) used to measure and compare the delayed fluorescence lifetime of compound 1. Detailed Implementation

[0142] 1. Polycyclic aromatic compounds

[0143] This application pertains to polycyclic aromatic compounds represented by the following general formula (1), preferably polycyclic aromatic compounds represented by the following general formula (2). It should be noted that the definitions of the symbols in the following formulas are the same as those above unless otherwise specified.

[0144]

[0145] In general formula (1), rings A, B, and C are each independently an aromatic or heteroaromatic ring, wherein at least one hydrogen atom of these rings is optionally substituted with a substituent. The substituent is preferably a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaromatic, a substituted or unsubstituted diarylamino, a substituted or unsubstituted diheteroaromatic, a substituted or unsubstituted arylheteroaromatic (an amino group having an aryl and a heteroaromatic), a substituted or unsubstituted diarylboroyl (two aryl groups optionally bonded by 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. Wherein, the two X... 2 When the value is >NR, substituents other than substituted silyl groups are preferred. Examples of substituents that include these groups include aryl, heteroaryl, alkyl, or cycloalkyl groups. Furthermore, the aforementioned aromatic or heteroaryl rings preferably have a group consisting of multiple Y groups. 1 X 1 and X 2 The general formula (1) consists of a central fused structure with a shared five- or six-membered ring.

[0146] Here, "a six-membered ring sharing a bond with the fused structure portion" refers to, for example, an a-ring (benzene ring (six-membered ring)) fused to the aforementioned fused structure portion as shown in the general formula (2) above. Furthermore, "an aromatic ring or heteroaromatic ring (as ring A) having the six-membered ring" means that ring A is formed solely by the six-membered ring, or that ring A is formed by further fused with other rings in a manner that includes the six-membered ring. In other words, "an aromatic ring or heteroaromatic ring (as ring A) having a six-membered ring" mentioned here refers to a six-membered ring constituting all or part of ring A fused to the aforementioned fused structure portion. The same explanation applies to "ring B (b-ring)," "ring C (c-ring)," or "five-membered ring."

[0147] In general formula (1), ring A (or ring B, ring C) corresponds to ring a and its multiple substituents R in general formula (2). a (or the b ring and its multiple substituents R) b c-ring and its multiple substituents R c That is, general formula (2) corresponds to the structure of choosing "A~C rings with six-membered rings" as the A~C rings of general formula (1). Based on this meaning, lowercase letters a~c are used to represent each ring of general formula (2).

[0148] In general formula (2), the substituents R of rings a, b, and c are... a R b and R c The adjacent groups may optionally be bonded to each other and together with ring a, ring b, or ring c to form an aromatic ring or heteroaromatic ring. At least one hydrogen atom of the formed ring may optionally be substituted with an aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (the two aryl groups may optionally be bonded by a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, or substituted silyl group, and at least one hydrogen atom of these may optionally be substituted with an aryl, heteroaryl, alkyl, or cycloalkyl group. Wherein, the two X groups... 2 When the value is >NR, the substituents are preferably other than the substituted silyl group. Therefore, the ring structure of the polycyclic aromatic compound represented by general formula (2) varies as shown in formulas (2-1) and (2-2) below, depending on the different bonding morphologies of the substituents on the a, b, and c rings. The A', B', and C' rings in each formula correspond to the A, B, and C rings of general formula (1). It should be noted that the definitions of the symbols in the following formulas are the same as those above unless otherwise specified.

[0149]

[0150] Regarding the A' ring, B' ring, and C' ring in the above equations (2-1) and (2-2), if we use general formula (2) to explain, it represents the substituent R. a R b and Rc The adjacent groups in the ring are bonded to each other and form aromatic or heteroaromatic rings with rings a, b, and c, respectively (or fused rings formed by fused other ring structures on rings a, b, or c). It should be noted that although not shown in the formula, there are compounds in which rings a, b, and c are all transformed into rings A', B', and C', respectively. Furthermore, from formulas (2-1) and (2-2) above, it can be seen that the R of ring a... a R with ring b b R of ring b b R with c ring c R of c ring c R with ring a a and R of different a rings a Each other (different b-rings of R) b R of different c-rings c (The groups that are adjacent to each other) do not meet the requirement of "adjacent groups to each other," meaning they do not bond. That is, "adjacent groups" refers to groups that are adjacent to each other on the same ring.

[0151] The compounds shown in formulas (2-1) and (2-2) above are, for example, compounds having an A' ring (or B' ring or C' ring) formed by fused benzene ring, indole ring, pyrrole ring, benzofuran ring or benzothiophene ring as a ring (or b ring or c ring), wherein the fused ring A' (or fused ring B' or fused ring C') formed is a naphthyl ring, carbazole ring, indole ring, dibenzofuran ring or dibenzothiophene ring, respectively.

[0152] Y in general formula (1) 1 The atoms bonded to the A, B, or C rings are B, P, P=O, P=S, Al, Ga, As, Si-R, or Ge-R, where R in Si-R and Ge-R is aryl, alkyl, or cycloalkyl. In the cases of P=O, P=S, Si-R, or Ge-R, the atoms bonded to the A, B, or C rings are P, Si, or Ge. 1 The preferred materials are B, P, P=O, P=S, or Si-R, with B being particularly preferred. This description is consistent with Y in general formula (2). 1 The same.

[0153] X in general formula (1) 1 Each is independently either N or CR, where R in CR is an optionally substituted aryl, optionally substituted alkyl, or optionally substituted cycloalkyl group. In the case of CR, the atoms bonded to rings A and B are C atoms. X 1 N is particularly preferred. This description is consistent with X in general formula (2). 1 The same.

[0154] X in general formula (1) 2Each is independently >O, >NR, >C(-R)2, >S, or >Se, where R in >NR is an optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkyl, optionally substituted cycloalkyl, or substituted silyl (wherein, the two X's are...). 2 When >NR, preferably a substituent other than a substituted silyl group), the R in the aforementioned >C(-R)2 is hydrogen, optionally substituted aryl, optionally substituted alkyl, optionally substituted cycloalkyl, or substituted silyl (wherein, the two X's are hydrogen, optionally substituted aryl, optionally substituted alkyl, optionally substituted cycloalkyl, or substituted silyl). 2 When the R is >NR, it is preferably a substituent other than a substituted silyl group. The R of the aforementioned >NR and / or the R of the aforementioned >C(-R)2 are optionally bonded to the aforementioned A ring and / or C ring via a linking group or a single bond. The linking group is preferably -O-, -S-, -C(-R)2-, or -Si(-R)2-. It should be noted that the R of the aforementioned "-C(-R)2-" or "-Si(-R)2-" is hydrogen, optionally a substituted aryl group, optionally a substituted alkyl group, optionally a substituted cycloalkyl group, or a substituted silyl group (wherein, the two X's are not substituted). 2 When the value is >NR, substituents other than the substituted silyl group are preferred. In particular, two X groups are preferred. 2 Compounds with >NR, two X 2 Compounds with >O, ​​and an X 2 For >NR and another X 2 For compounds with >O, ​​more preferably two X's 2 Compounds with >O, ​​and an X 2 For >NR and another X 2 For compounds with >O, ​​two X's are further preferred. 2 Compounds with >O. This description corresponds to X in general formula (2). 1 and X 2 The same.

[0155] Here, the provision in general formula (1) that “>NR’s R and / or >C(-R)2’s R are bonded to the aforementioned A ring and / or C ring by means of a linking group or a single bond” corresponds to the provision in general formula (2) that “>NR’s R and / or >C(-R)2’s R are bonded to the aforementioned a ring and / or c ring by means of -O-, -S-, -C(-R)2-, -Si(-R)2- or a single bond”.

[0156] This regulation can be represented by the following formula (2-3-1), having X 2 Compounds that incorporate the ring structure into the fused ring C' are represented. That is, for example, compounds having a benzene ring as the c ring in general formula (2) with X 2Compounds that enter through fusion with other rings to form a C' ring. The formed fused ring C' can be, for example, a phenoxazine ring, a phenothiazine ring, or an acridine ring.

[0157] Furthermore, the above provisions can also be expressed as shown in the following formula (2-3-2), with X 2 Compounds that incorporate the ring structure into the fused ring A' are represented. That is, for example, compounds having a benzene ring as the a ring in general formula (2) with X 2 Compounds that enter through fusion with other rings to form an A' ring. The formed fused ring A' can be, for example, a phenoxazine ring, a phenothiazine ring, or an acridine ring.

[0158] It should be noted that the definitions of the symbols in the following formulas are the same as those above unless otherwise specified.

[0159]

[0160] In general formula (1), X 1 When n is N, some or all of two adjacent A rings may be bonded to each other by means of a single bond. When bonding in this way, it is preferred that all two adjacent A rings are bonded to each other by means of a single bond. "Some or all" means that when n is 2 or more, there are 3 or more A rings, and two adjacent A rings have 2 or more locations with each other. Therefore, it is "some locations" or "all locations" among these multiple locations.

[0161] The following uses general formula (2) as an example to illustrate X. 1 Examples of structural formulas where, when N is present, some or all of two adjacent α-rings are bonded together by single bonds. The symbols in each structural formula are the same as defined above, except that R is omitted. b and R c A portion of R a .

[0162]

[0163] In general formula (1), n ​​is an integer greater than or equal to 1, an integer from 1 to 10, an integer from 1 to 5, an integer from 1 to 3, or 1 or 2, preferably 1 or 2, and particularly preferably 1. This description is the same as that for n in general formula (2).

[0164] In general formula (1), when n is 1, the following structures can be listed as examples. The symbols in each structure are the same as defined above. Furthermore, in the following examples, Y is shown... 1 For B and X 1 For N and X 2 For examples where the value is >0 or >NR, there are also other possible combinations. Furthermore, there are also examples where two adjacent A-rings are bonded to each other (or "all adjacent A-rings to each other" when n is 1) by a single bond.

[0165]

[0166] In general formula (1), when n is 2, the following structures can be listed as examples. The symbols in each structure are the same as defined above. Furthermore, in the following examples, Y is shown... 1 For B and X 1 For N and X 2 Examples of >O or >NR also exist, as do other possible combinations. Furthermore, there are also examples where some or all of two adjacent A-rings are bonded together by single bonds.

[0167]

[0168] In general formula (2), when n is 1, the following structures can be listed as examples. The symbols in each structural formula are the same as defined above, except that R is omitted. a R b and R c Substituents on R (phenyl in the formula) of >NR. Furthermore, in the following examples, Y is illustrated. 1 For B and X 1 For N and X 2 For examples of >O or >NR, there are also other possible combinations. In addition, there are also examples where two adjacent a-rings are bonded to each other (when n is 1, it is "all two adjacent a-rings to each other") by a single bond.

[0169]

[0170] The following examples illustrate the bonding of R (phenyl in the formula) to a c-ring (which may be an a-ring) in >NR. Single bonds or -O- are shown as linking groups used for bonding, but other options also exist.

[0171]

[0172] In general formula (2), when n is 2, the following structures can be listed as examples. The symbols in each structural formula are the same as defined above, except that R is omitted. a R b and R c Substituents on R (phenyl in the formula) of NR. Furthermore, in the following examples, Y is illustrated. 1 For B and X 1 For N and X 2 Examples of >O or >NR also exist, as do other possible combinations. Furthermore, there are also examples where some or all of two adjacent α-rings are bonded together by single bonds.

[0173]

[0174] The following examples illustrate the bonding of R (phenyl in the formula) to a c-ring (which may be an a-ring) in >NR. Single bonds or -O- are shown as linking groups used for bonding, but other options also exist.

[0175]

[0176] Regarding the "aromatic ring" in general formula (1), which serves as ring A, ring B, and ring C, examples include aromatic rings with 6 to 30 carbon atoms, preferably aromatic rings with 6 to 16 carbon atoms, more preferably aromatic rings with 6 to 12 carbon atoms, and particularly preferably aromatic rings with 6 to 10 carbon atoms. It should be noted that this "aromatic ring" corresponds to the "R" specified in general formula (2). a R b and R c "The adjacent groups in the ring are bonded to each other and form an aromatic ring together with the a ring, b ring or c ring". In addition, since the a ring (or the b ring, c ring) is already composed of a benzene ring with 6 carbon atoms, the total number of carbon atoms of the fused ring obtained by fusing it with the five-membered ring is 9, which becomes the lower limit of the number of carbon atoms.

[0177] Specific examples of "aromatic rings" include: benzene rings as monocyclic systems; biphenyl rings as bicyclic systems; naphthalene rings as fused bicyclic systems; terphenyl rings (m-terphenyl, o-terphenyl, p-terphenyl) as tricyclic systems; acenaphthene rings, fluorene rings, phenanthene rings, and phenanthrene rings as fused tricyclic systems; benzo[a]phenanthrene rings, pyrene rings, and tetraphenyl rings as fused tetracyclic systems; and perylene rings and pentaphenyl rings as fused pentacyclic systems.

[0178] Regarding the "heteroaromatic ring" in general formula (1), which serves as ring A, ring B, and ring C, examples include heteroaromatic rings with 2 to 30 carbon atoms, preferably heteroaromatic rings with 2 to 25 carbon atoms, more preferably heteroaromatic rings with 2 to 20 carbon atoms, even more preferably heteroaromatic rings with 2 to 15 carbon atoms, and particularly preferably heteroaromatic rings with 2 to 10 carbon atoms. Furthermore, examples of "heteroaromatic rings" include heterocycles containing 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen as cyclizing atoms in addition to carbon. It should be noted that this "heteroaromatic ring" corresponds to "R" specified in general formula (2). a R b and R c "The adjacent groups in the ring are bonded to each other and form a heteroaromatic ring together with the a ring, b ring or c ring". In addition, since the a ring (or the b ring, c ring) is already composed of a benzene ring with 6 carbon atoms, the total number of carbon atoms of the fused ring obtained by fusing the five-membered ring is 6, which becomes the lower limit of the number of carbon atoms.

[0179] Specific examples of "heteroaromatic rings" include, for example, pyrrole rings, oxazole rings, isoxazole rings, thiazole rings, isothiazole rings, imidazole rings, oxadiazole rings, thiadiazole rings, triazole rings, tetraazole 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, cyclophosphine rings, quinazolinite rings, quinoxaline rings, phthalazine rings, naphthidine rings, purine rings, pteridine rings, carbazole rings, acridine rings, and phenoxazine rings. Phenyrazine ring, phenothiazine ring, phenazine ring, dibenzo[b,e][1,4]nitrosilanehexacyclohexane ring, indene ring, furan ring, benzofuran ring, isobenzofuran ring, dibenzofuran ring, naphthobenzofuran ring, thiophene ring, benzothiophene ring, dibenzothiophene ring, naphthobenzothiophene ring, benzophosphane pentadiene ring, dibenzophosphane pentadiene ring, benzophosphane pentadiene oxide ring, dibenzophosphane pentadiene oxide ring, furazan ring, thiamethoxam ring, indolocarbazole ring, benzoindolocarbazole ring, and benzobenzoindolocarbazole ring, etc.

[0180] The above-mentioned "aromatic ring" or "heteroaromatic ring" may have at least one hydrogen atom optionally serving as a first substituent, and may be a substituted or unsubstituted "aryl", a substituted or unsubstituted "heteroaromatic", a substituted or unsubstituted "diarylamino", a substituted or unsubstituted "diheteroaromatic", a substituted or unsubstituted "arylheteroaromatic", a substituted or unsubstituted "diarylboroyl (the two aryl groups may optionally be bonded by a single bond or a linking group)", a substituted or unsubstituted "alkyl", or a substituted or unsubstituted group. The "cycloalkyl", substituted or unsubstituted "alkoxy", substituted or unsubstituted "aryloxy", or substituted silyl-substituted, can be listed as a monovalent group of the "aryl", "heteroaryl", "diarylamino", "diheteroarylamino", "aryl and heteroaryl of arylheteroarylamino", "diarylboryl", or "aryloxy" as the first substituent, which is a "aryl ring" or "heteroaryl ring" as described above.

[0181] Furthermore, the "alkyl" group used as the first substituent can be either straight-chain or branched, and examples include straight-chain alkyl groups with 1 to 24 carbon atoms or branched alkyl groups with 3 to 24 carbon atoms. Preferably, it is an alkyl group with 1 to 18 carbon atoms (branched alkyl groups with 3 to 18 carbon atoms), more preferably an alkyl group with 1 to 12 carbon atoms (branched alkyl groups with 3 to 12 carbon atoms), even more preferably an alkyl group with 1 to 6 carbon atoms (branched alkyl groups with 3 to 6 carbon atoms), and particularly preferably an alkyl group with 1 to 5 carbon atoms (branched alkyl groups with 3 to 5 carbon atoms).

[0182] Specific alkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, tert-pentyl (tert-pentylyl), n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, tert-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-pentadecanyl, n-hexadecyl, n-heptadecyl, n-octadecyl, n-eicosyl, etc.

[0183] In addition, examples include 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.

[0184] Furthermore, regarding "cycloalkyl" as the first substituent, examples include cycloalkyl with 3 to 24 carbon atoms, cycloalkyl with 3 to 20 carbon atoms, cycloalkyl with 3 to 16 carbon atoms, cycloalkyl with 3 to 14 carbon atoms, cycloalkyl with 3 to 12 carbon atoms, cycloalkyl with 5 to 10 carbon atoms, cycloalkyl with 5 to 8 carbon atoms, cycloalkyl with 5 to 6 carbon atoms, and cycloalkyl with 5 carbon atoms.

[0185] Specific examples of cycloalkyl groups include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, and their alkyl (especially methyl) substituted derivatives having 1 to 5 carbon atoms; norbornenyl, bicyclo[1.0.1]butyl, bicyclo[1.1.1]pentyl, bicyclo[2.0.1]pentyl, bicyclo[1.2.1]hexyl, bicyclo[3.0.1]hexyl, bicyclo[2.1.2]heptyl, bicyclo[2.2.2]octyl, adamantyl, diadamantyl, decahydronaphthyl, decahydroazyl, etc.

[0186] Furthermore, regarding the "alkoxy group" as the first substituent, examples include straight-chain alkoxy groups with 1 to 24 carbon atoms or branched-chain alkoxy groups with 3 to 24 carbon atoms. Preferably, it is an alkoxy group with 1 to 18 carbon atoms (branched-chain alkoxy groups with 3 to 18 carbon atoms), more preferably it is an alkoxy group with 1 to 12 carbon atoms (branched-chain alkoxy groups with 3 to 12 carbon atoms), even more preferably it is an alkoxy group with 1 to 6 carbon atoms (branched-chain alkoxy groups with 3 to 6 carbon atoms), and particularly preferably it is an alkoxy group with 1 to 5 carbon atoms (branched-chain alkoxy groups with 3 to 5 carbon atoms).

[0187] Specific alkoxy groups include methoxy, ethoxy, propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy, tert-pentyloxy, n-pentyloxy, isopentyloxy, neopentyloxy, tert-pentyloxy, n-hexyloxy, 1-methylpentyloxy, 4-methyl-2-pentyloxy, 3,3-dimethylbutoxy, 2-ethylbutoxy, n-heptyloxy, 1-methylhexyloxy, n-octyloxy, tert-octyloxy, and 1-methyl Heptyloxy, 2-ethylhexyloxy, 2-propylpentyloxy, n-nonyloxy, 2,2-dimethylheptyloxy, 2,6-dimethyl-4-heptyloxy, 3,5,5-trimethylhexyloxy, n-decyloxy, n-undecyloxy, 1-methyldecyloxy, n-dodecyloxy, n-tridecyloxy, 1-hexylheptyloxy, n-tetradecyloxy, n-pentadecanyloxy, n-hexadecyloxy, n-heptadecyloxy, n-octadecyloxy, n-eicosyloxy, etc.

[0188] Regarding "substituted silyl" as the first substituent, examples include triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, or alkyldicycloalkylsilyl.

[0189] As a "triarylsilyl group", it can be a group in which each of the three hydrogens of the silyl group is independently replaced by an aryl group, and as the aryl group, it can be a monovalent group of the aforementioned "aromatic ring". For substitution, the preferred aryl group is an aryl group with 6 to 10 carbon atoms, specifically phenyl, naphthyl, etc.

[0190] Specific examples of triarylsilyl compounds include triphenylsilyl, diphenylmonaphthylsilyl, monophenyldinaphthylsilyl, and trinaphthylsilyl.

[0191] As "trialkylsilyl", a group in which each of the three hydrogens of a silyl group is independently replaced by an alkyl group can be listed. This alkyl group can be referred to as "alkyl" in the first substituent above. For substitution, the preferred alkyl group is an alkyl group with 1 to 5 carbon atoms, specifically methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, tert-butyl, tert-amyl, etc.

[0192] Specific examples of trialkylsilyl groups include trimethylsilyl, triethylsilyl, tripropylsilyl, triisopropylsilyl, tributylsilyl, trisec-butylsilyl, tritert-butylsilyl, tritert-butylsilyl, tritert-pentylsilyl, ethyl dimethylsilyl, propyl dimethylsilyl, isopropyl dimethylsilyl, butyl dimethylsilyl, sec-butyl dimethylsilyl, tert-butyl dimethylsilyl, tert-pentyl dimethylsilyl, methyl diethylsilyl, propyl diethylsilyl, and isopropyl dimethylsilyl. Ethyl silane, butyl diethyl silane, sec-butyl diethyl silane, tert-butyl diethyl silane, tert-pentyl diethyl silane, methyl dipropyl silane, ethyl dipropyl silane, butyl dipropyl silane, sec-butyl dipropyl silane, tert-butyl dipropyl silane, tert-pentyl dipropyl silane, methyl diisopropyl silane, ethyl diisopropyl silane, butyl diisopropyl silane, sec-butyl diisopropyl silane, tert-butyl diisopropyl silane, tert-pentyl diisopropyl silane, etc.

[0193] As "tricycloalkylsilyl", it can be listed as a group in which each of the three hydrogens of the silyl group is independently replaced by a cycloalkyl group, which can be referred to as "cycloalkyl" in the first substituent above. For substitution, the preferred cycloalkyl group is a cycloalkyl group with 5 to 10 carbon atoms, specifically including cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, bicyclo[1.1.1]pentyl, bicyclo[2.0.1]pentyl, bicyclo[1.2.1]hexyl, bicyclo[3.0.1]hexyl, bicyclo[2.1.2]heptyl, bicyclo[2.2.2]octyl, adamantyl, decahydronaphthyl, decahydroazyl, etc.

[0194] Specific examples of tricycloalkylsilyl groups include tricyclopentylsilyl and tricyclohexylsilyl.

[0195] As specific examples of "dialkylcycloalkylsilyl" which is substituted with two alkyl groups and one cycloalkyl group, and "alkyldicycloalkylsilyl" which is substituted with one alkyl group and two cycloalkyl groups, examples of silyl groups substituted with groups selected from the specific alkyl and cycloalkyl groups mentioned above can be listed.

[0196] The description of “substituted silyl” is as described above, referring to the two X's in the polycyclic aromatic compounds represented by general formula (1) or general formula (2). 2 When the value is >NR, the substituent used to replace any hydrogen in the compound is preferably a substituent other than a substituted silyl group.

[0197] Furthermore, the "aryl" in "diarylboryl" as the first substituent can be referenced from the description of the aryl group above. Additionally, these two aryl groups are optionally bonded by a single bond or a linking group (e.g., >C(-R)2, >O, >S, or >NR). Here, R in >C(-R)2 and >NR is an aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, alkoxy, or aryloxy group (the above are the first substituents), which may optionally be further substituted with an aryl, heteroaryl, alkyl, or cycloalkyl group (the above are the second substituents). Specific examples of these groups can be referenced from the description of aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, alkoxy, or aryloxy groups as the above first substituents.

[0198] The first substituent, substituted or unsubstituted "aryl", substituted or unsubstituted "heteroaryl", substituted or unsubstituted "diarylamino", substituted or unsubstituted "diheteroarylamino", substituted or unsubstituted "arylheteroarylamino", substituted or unsubstituted "diarylboroyl (two aryl groups optionally bonded by a single bond or a linking group)", substituted or unsubstituted "alkyl", substituted or unsubstituted "cycloalkyl", substituted or unsubstituted "alkoxy", or substituted or unsubstituted "aryloxy" as described in the description of substitution or unsubstituent, wherein at least one hydrogen atom is optionally substituted by a second substituent. Examples of the second substituent include, for example, aryl, heteroaryl, alkyl, or cycloalkyl, specific examples of which can be referred to the description of the monovalent group of the "aromatic ring" or "heteroaromatic ring" above, or the "alkyl" or "cycloalkyl" as the first substituent. Furthermore, groups formed by replacing at least one hydrogen atom in the aryl or heteroaryl group as a second substituent with an aryl group such as phenyl (specifically, the groups described above), an alkyl group such as methyl (specifically, the groups described above), or a cycloalkyl group such as cyclohexyl (specifically, the groups described above) are also included in the aryl or heteroaryl group as a second substituent. As one example, when the second substituent is a carbazolyl group, a carbazolyl group in which at least one hydrogen atom at position 9 is replaced by an aryl group such as phenyl, an alkyl group such as methyl, or a cycloalkyl group such as cyclohexyl is also included in the heteroaryl group as a second substituent.

[0199] R as general formula (2) a R b and R c The aryl, heteroaryl, aryl of diarylamino, heteroaryl of diarylamino, aryl and heteroaryl of arylhexylamino, aryl and heteroaryl of diarylboryl, or aryloxy, can be listed as monovalent groups of the "aromatic ring" or "heteroaryl ring" described in general formula (1). Furthermore, as R a R b and R cThe alkyl, cycloalkyl, alkoxy, triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, or alkyldicycloalkylsilyl groups in the above general formula (1) can be referred to in the description of "alkyl", "cycloalkyl", "alkoxy", "triarylsilyl", "trialkylsilyl", "tricycloalkylsilyl", "dialkylcycloalkylsilyl", or "alkyldicycloalkylsilyl" as the first substituent. Furthermore, the same applies to aryl, heteroaryl, alkyl, or cycloalkyl groups as substituents on these groups. Additionally, for R... a R b and R c When the adjacent groups are bonded to each other and together with ring a, ring b or ring c to form an aromatic ring or heteroaromatic ring, the heteroaromatic groups, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryl groups are optionally bonded by a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl or alkyldicycloalkylsilyl, and the aryl, heteroaromatic, alkyl or cycloalkyl groups as further substituents are also the same.

[0200] R in general formula (2) a Among them, especially relative to Y bonded to the α ring. 1 For the R of the position a When the hydrogen is not used, but rather a halogen (especially chlorine), alkyl, cycloalkyl, aryl, heteroaryl, etc., it is preferred for synthesis. Furthermore, halogens can be used as a starting point to convert into R... a And the various substituents defined. In particular, in two X... 2 Compounds with >NR, two X 2 Compounds with >O, ​​and an X 2 For >NR and another X 2 In compounds with >O, ​​the R at the para position a In addition to chlorine, the following groups are preferred: R at the para position. a When the group is chlorine or smaller, especially when there are two X groups... 2 Compounds with a NR value are preferred.

[0201]

[0202]

[0203]

[0204] Specifically, the emission wavelength can be adjusted by the steric hindrance, electron-donating, and electron-withdrawing properties of the first substituent. Preferably, the substituent is a group represented by the following structural formula, more preferably methyl, tert-butyl, tert-pentyl, tert-octyl, phenyl, o-tolyl, p-tolyl, 2,4-xylyl, 2,5-xylyl, 2,6-xylyl, 2,4,6-trimethylyl, diphenylamino, di-p-tolylamino, bis(p-(tert-butyl)phenyl)amino, carbazole, 3,6-dimethylcarbazole, 3,6-di-tert-butylcarbazole, and phenoxy. Further preferably, it is methyl, tert-butyl, tert-pentyl, tert-octyl, phenyl, o-tolyl, 2,6-xylyl, 2,4,6-trimethylyl, diphenylamino, di-p-tolylamino, bis(p-(tert-butyl)phenyl)amino, carbazole, 3,6-dimethylcarbazole, and 3,6-di-tert-butylcarbazole. From the perspective of ease of synthesis, steric hindrance is preferred for selective synthesis. Specifically, tert-butyl, tert-pentyl, tert-octyl, o-tolyl, p-tolyl, 2,4-xylyl, 2,5-xylyl, 2,6-xylyl, 2,4,6-trimethylyl, di-p-tolylamino, bis(p-(tert-butyl)phenyl)amino, 3,6-dimethylcarbazole, and 3,6-di-tert-butylcarbazole are preferred.

[0205] In the following structural formulas, "Me" represents methyl, "tBu" represents tert-butyl, "tAm" represents tert-pentyl, and "tOct" represents tert-octyl.

[0206]

[0207]

[0208]

[0209]

[0210]

[0211] Y of general formula (1) 1 In Si-R and Ge-R, R is aryl, alkyl, or cycloalkyl, and the above-mentioned groups can be listed as such aryl, alkyl, or cycloalkyl groups. Particularly preferred are aryl groups with 6 to 10 carbon atoms (e.g., phenyl, naphthyl, etc.) and alkyl groups with 1 to 5 carbon atoms (e.g., methyl, ethyl, etc.). This description is consistent with Y in general formula (2). 1 The same.

[0212] X of general formula (1) 1In the CR, R is an aryl, alkyl, or cycloalkyl group optionally substituted with the second substituent described above. Examples of such aryl, alkyl, and cycloalkyl groups are listed above. Particularly preferred are aryl groups with 6 to 12 carbon atoms, aryl groups with 6 to 10 carbon atoms (e.g., phenyl, naphthyl, etc.), alkyl groups with 1 to 6 carbon atoms, alkyl groups with 1 to 5 carbon atoms (e.g., methyl, ethyl, etc.), and cycloalkyl groups with 3 to 16 carbon atoms (e.g., bicyclooctyl, adamantyl, etc.). This description is consistent with X in general formula (2). 1 The same.

[0213] X of general formula (1) 2 In the >NR formula, R is an aryl, heteroaryl, alkyl, or cycloalkyl group optionally substituted with the second substituent described above, wherein at least one hydrogen atom of the aryl or heteroaryl group is optionally substituted with, for example, an alkyl or cycloalkyl group. Examples of such aryl, heteroaryl, alkyl, or cycloalkyl groups include the groups described above. Particularly preferred are aryl groups with 6 to 10 carbon atoms (e.g., phenyl, naphthyl, etc.), heteroaryl groups with 2 to 15 carbon atoms (e.g., carbazolyl, etc.), alkyl groups with 1 to 5 carbon atoms (e.g., methyl, ethyl, etc.), and cycloalkyl groups with 3 to 16 carbon atoms (e.g., bicyclooctyl, adamantyl, etc.). This description is consistent with X in general formula (2). 2 The same.

[0214] X of general formula (1) 2 In the >C(-R)2, R is hydrogen, an aryl group, an alkyl group, or a cycloalkyl group optionally substituted with the second substituent described above, and at least one hydrogen atom of the aryl group is optionally substituted with, for example, an alkyl or cycloalkyl group. Examples of such aryl, alkyl, or cycloalkyl groups are listed above. Particularly preferred are aryl groups with 6 to 10 carbon atoms (e.g., phenyl, naphthyl, etc.), alkyl groups with 1 to 5 carbon atoms (e.g., methyl, ethyl, etc.), and cycloalkyl groups with 3 to 16 carbon atoms (e.g., bicyclooctyl, adamantyl, etc.). This description is consistent with X in general formula (2). 2 The same.

[0215] In general formula (1), the R in "-C(-R)2-" or "-Si(-R)2-" as the linking group is hydrogen, optionally substituted aryl, optionally substituted alkyl, optionally substituted cycloalkyl, or substituted silyl, preferably hydrogen, alkyl, or cycloalkyl. Examples of the above groups can be listed as the aryl, alkyl, cycloalkyl, or substituted silyl, and the substituents (second substituents) thereon. Alkyl groups having 1 to 5 carbon atoms (e.g., methyl, ethyl, etc.) are particularly preferred. This description is also the same as that for "-C(-R)2-" or "-Si(-R)2-" as the linking group in general formula (2).

[0216] Furthermore, all or part of the hydrogen in the chemical structure of the polycyclic aromatic compound represented by general formula (1) or (2) can be deuterium, cyano, or halogen. For example, in formula (1), ring A, ring B, ring C (rings A to C are aromatic or heteroaromatic rings), substituents on rings A to C, Y 1 When R (= aryl, heteroaryl, alkyl, cycloalkyl) is Si-R or Ge-R, X 1 When R is CR (= aryl, alkyl, cycloalkyl), X 2 When the R (=aryl, heteroaryl, alkyl, cycloalkyl) and the hydrogen in the linking group are >NR or >C(-R)2, they can be replaced by deuterium, cyano, or halogen. Examples of such substitutions include all or part of the hydrogens in the aryl or heteroaryl groups. The halogen is fluorine, chlorine, bromine, or iodine, preferably fluorine, chlorine, or bromine, and more preferably fluorine or chlorine.

[0217] Furthermore, the polycyclic aromatic compounds described in this invention can be used as materials for organic devices. Examples of organic devices include, for instance, organic electroluminescent elements, organic field-effect transistors, and organic thin-film solar cells. In particular, in organic electroluminescent elements, γ-ray dimethyl ether (γ) is preferably used as the dopant material for the light-emitting layer. 1 For B and X 1 For N and X 2 For compounds with >NR, Y 1 For B and X 1 For N and X 2 For compounds with >O, ​​Y 1 For B and X 1 For N and X 2 Compounds with >O and >NR; Y is preferably used as the host material for the luminescent layer. 1 For B and X 1 For N and X 2 For compounds with >NR and >O, Y 1 For B and X 1 For N and X 2 Compounds with >O; Y is preferred as an electron transport material. 1 For B and X 1 For N and X 2 For compounds with >O, ​​Y 1 For P=O, X 1 For N and X 2 Compounds with >O.

[0218] More specific examples of the polycyclic aromatic compounds of the present invention can be listed as compounds with the following structural formulas. It should be noted that in the following structural formulas, "Me" represents methyl, "Et" represents ethyl, "tBu" represents tert-butyl, "D" represents deuterium, "Ph" represents phenyl, "tAm" represents tert-amyl, and "CN" represents cyano.

[0219]

[0220]

[0221]

[0222]

[0223]

[0224]

[0225]

[0226]

[0227]

[0228]

[0229]

[0230]

[0231]

[0232]

[0233]

[0234]

[0235]

[0236]

[0237]

[0238]

[0239]

[0240]

[0241]

[0242]

[0243]

[0244]

[0245]

[0246]

[0247]

[0248]

[0249]

[0250]

[0251]

[0252]

[0253]

[0254]

[0255]

[0256]

[0257]

[0258]

[0259]

[0260]

[0261]

[0262]

[0263]

[0264]

[0265]

[0266]

[0267]

[0268]

[0269]

[0270]

[0271]

[0272]

[0273]

[0274]

[0275]

[0276]

[0277]

[0278]

[0279]

[0280]

[0281]

[0282]

[0283]

[0284]

[0285]

[0286]

[0287]

[0288]

[0289]

[0290]

[0291]

[0292]

[0293]

[0294]

[0295]

[0296]

[0297]

[0298]

[0299] The polycyclic aromatic compounds of general formula (1) described in this invention can be used as materials for organic devices, such as materials for organic electroluminescent elements, materials for organic field-effect transistors, or materials for organic thin-film solar cells, even if they are polymerized by using reactive compounds that have been substituted with reactive substituents on them as monomers (the aforementioned monomers used to obtain the polymeric compounds have polymerizable substituents), or polymeric crosslinked bodies obtained by further crosslinking the polymeric compounds (the aforementioned polymeric compounds used to obtain the polymeric crosslinked bodies have crosslinking substituents), or side-chain type polymeric compounds obtained by reacting a main-chain type polymer with the aforementioned reactive compounds (the aforementioned reactive compounds used to obtain the side-chain type polymeric compounds have reactive substituents), or side-chain type polymeric crosslinked bodies obtained by further crosslinking the side-chain type polymeric compounds (the aforementioned side-chain type polymeric compounds used to obtain the side-chain type polymeric crosslinked bodies have crosslinking substituents).

[0300] As for the aforementioned reactive substituents (including the aforementioned polymerizable substituents, the aforementioned crosslinking substituents, and reactive substituents for obtaining side-chain type polymers, hereinafter also simply referred to as "reactive substituents"), there are no particular limitations as long as they are substituents capable of increasing the molecular weight of the aforementioned polycyclic aromatic compounds, substituents capable of further crosslinking the polymer compounds obtained by such operation, and substituents capable of undergoing side-chain reactions with main-chain type polymers. Substituents with the following structures are preferred. * in each structural formula indicates a bonding position.

[0301]

[0302] L can be a single bond, -O-, -S-, >C=O, -OC(=O)-, alkylene group with 1 to 12 carbon atoms, oxoalkylene group with 1 to 12 carbon atoms, or polyoxoalkylene group with 1 to 12 carbon atoms. Among the above substituents, the groups shown in formula (XLS-1), formula (XLS-2), formula (XLS-3), formula (XLS-9), formula (XLS-10), or formula (XLS-17) are preferred, and the groups shown in formula (XLS-1), formula (XLS-3), or formula (XLS-17) are more preferred.

[0303] Detailed uses of such polymers, polymer crosslinkers, side-chain polymers, and side-chain polymer crosslinkers (hereinafter also referred to as "polymers and polymer crosslinkers") are described below.

[0304] 2. Methods for manufacturing polycyclic aromatic compounds

[0305] Polycyclic aromatic compounds represented by general formula (1) or formula (2) can be synthesized by applying, for example, the method disclosed in International Publication No. 2015 / 102118. That is, by synthesizing ring A (a ring) with ring B (b ring) and ring C (c ring) using X, as described below. 1 or X 2 The bonded intermediates, cyclized using the Tandem Hetero-Friedel-Crafts reaction (a series of aromatic electrophilic substitution reactions), can synthesize the desired polycyclic aromatic compounds. In the following route, X represents halogen or hydrogen, and the definitions of other symbols are the same as those above.

[0306]

[0307] The intermediates before cyclization in the above-mentioned routes can also be synthesized using the methods shown in International Publication No. 2015 / 102118, etc. That is, intermediates with desired substituents can be synthesized by appropriately combining Buchwald-Hartwig reaction, Suzuki coupling reaction, or etherification reaction based on nucleophilic substitution reaction, Ullmann reaction, etc.

[0308] The cyclization shown in the above route, based on the Tandem Hetero-Friedel-Crafts reaction, involves introducing Y atoms bonded to rings A (a), B (b), and C (c). 1 (e.g., boron B) reaction. First, using n-butyllithium, sec-butyllithium, or tert-butyllithium, etc., to react with X. 1 With X 2 The hydrogen atoms between them (X in the above route) are metallized in adjacent positions. Then, by adding Y... 1 Halides (such as boron trichloride, boron tribromide, etc.) are used for lithium-Y1 After metal exchange of (e.g., boron B), a Brønsted base such as N,N-diisopropylethylamine is added to induce a Tandem Bora-Friedel-Crafts reaction, yielding the target compound. Here, a Lewis acid such as aluminum trichloride can be added to promote the reaction.

[0309] In addition to the method of introducing lithium to the desired site (X in the above route) through ortho-metallization, lithium can also be introduced to the desired site by introducing halogens such as bromine atoms to the site where lithium is to be introduced, and by halogen-metal exchange.

[0310] Furthermore, the polycyclic aromatic compounds of the present invention also include structures in which at least some of the hydrogen atoms are replaced by deuterium, cyano, or halogen, and such compounds can be synthesized in the same manner as described above using raw materials that are deuterated, cyano-substituted, or halogenated (especially fluorinated or chlorinated) at the desired positions.

[0311] 3. Organic equipment

[0312] The polycyclic aromatic compounds described in this invention can be used as materials for organic devices. Examples of organic devices include organic electroluminescent elements, organic field-effect transistors, and organic thin-film solar cells.

[0313] 3-1. Organic electroluminescent elements

[0314] Hereinafter, the organic EL element of this embodiment will be described in detail with reference to the accompanying drawings. Figure 1 This is a schematic cross-sectional view showing the organic EL element of this embodiment.

[0315] <Structure of Organic Electroluminescent Element>

[0316] Figure 1 The organic EL element 100 shown includes: a substrate 101, an anode 102 disposed on the substrate 101, a hole injection layer 103 disposed on the anode 102, a hole transport layer 104 disposed on the hole injection layer 103, a light-emitting layer 105 disposed on the hole transport layer 104, an electron transport layer 106 disposed on the light-emitting layer 105, an electron injection layer 107 disposed on the electron transport layer 106, and a cathode 108 disposed on the electron injection layer 107.

[0317] It should be noted that the organic EL element 100 can also be manufactured in a reversed order, having, for example, a substrate 101, a cathode 108 disposed on the substrate 101, an electron injection layer 107 disposed on the cathode 108, an electron transport layer 106 disposed on the electron injection layer 107, a light-emitting layer 105 disposed on the electron transport layer 106, a hole transport layer 104 disposed on the light-emitting layer 105, a hole injection layer 103 disposed on the hole transport layer 104, and an anode 102 disposed on the hole injection layer 103.

[0318] Not all of the aforementioned layers are mandatory. The smallest structural unit is configured to include an anode 102, a light-emitting layer 105, and a cathode 108. The hole injection layer 103, hole transport layer 104, electron transport layer 106, and electron injection layer 107 are optional layers. Furthermore, each of the aforementioned layers can be composed of a single layer or multiple layers.

[0319] In addition to the aforementioned configuration of "substrate / anode / hole injection layer / hole transport layer / light-emitting layer / electron transport layer / electron injection layer / cathode", other configurations for forming organic EL devices include "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", and "substrate / anode / hole injection layer / hole transport layer / light-emitting layer / cathode". The configuration of "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 transport layer / cathode", "substrate / anode / light-emitting layer / electron injection layer / cathode".

[0320] <Substrate in Organic Electroluminescent Devices>

[0321] The substrate 101 serves as the support for the organic EL element 100 and can typically be made of quartz, glass, metal, plastic, etc. Depending on the purpose, the substrate 101 can be formed in the form of a plate, film, or sheet, and can be made of materials such as glass plates, metal plates, metal foils, plastic films, or plastic sheets. Glass plates and transparent synthetic resins such as polyester, polymethyl methacrylate, polycarbonate, and polysulfone are preferred. If a glass substrate is used, soda-lime glass or alkali-free glass can be used. Furthermore, the thickness is only required to maintain sufficient mechanical strength, for example, 0.2 mm or more. An upper limit for the thickness is, for example, 2 mm or less, preferably 1 mm or less. Regarding the glass material, fewer ions leached from the glass are preferable; therefore, alkali-free glass is preferred. Soda-lime glass with an insulating coating such as SiO2 is also commercially available and can be used. In addition, to improve gas barrier properties, a dense gas barrier film such as a silicon oxide film can be provided on at least one side of the substrate 101. In particular, when a plate, film or sheet made of synthetic resin with low gas barrier properties is used as the substrate 101, it is preferable to provide a gas barrier film.

[0322] <Anode in Organic Electroluminescent Devices>

[0323] The anode 102 functions to inject holes into the light-emitting layer 105. It should be noted that when a hole injection layer 103 and / or a hole transport layer 104 are provided between the anode 102 and the light-emitting layer 105, holes are injected into the light-emitting layer 105 by means of these layers.

[0324] Materials forming the anode 102 can include both inorganic and organic compounds. Inorganic compounds include, for example, metals (aluminum, gold, silver, nickel, palladium, chromium, etc.), metal oxides (oxides of indium, oxides of tin, indium-tin oxide (ITO), indium-zinc oxide (IZO), etc.), metal halides (copper iodide, etc.), copper sulfide, carbon black, ITO glass, Ness glass, etc. Organic compounds include, for example, conductive polymers such as poly(3-methylthiophene) and polythiophene, polypyrrole, and polyaniline. Furthermore, materials appropriately selected from those used as the anode of organic EL elements can be employed.

[0325] Regarding the resistance of the transparent electrode, there is no limitation as long as it can supply sufficient current for the light-emitting element to emit light. From the viewpoint of the power consumption of the light-emitting element, low resistance is preferred. For example, if an ITO substrate with a resistance of 300 Ω / □ or less is used as the element electrode, substrates with a resistance of around 10 Ω / □ are now available. Therefore, it is particularly desirable to use a low-resistance product, such as 100~5 Ω / □, preferably 50~5 Ω / □. The thickness of the ITO can be arbitrarily selected according to the resistance value, and it is usually used in the range of 50~300 nm.

[0326] Hole injection layer and hole transport layer in organic electroluminescent devices

[0327] Hole injection layer 103 efficiently injects holes moving from anode 102 into light-emitting layer 105 or hole transport layer 104. Hole transport layer 104 efficiently transports holes injected from anode 102 or holes injected from anode 102 via hole injection layer 103 to light-emitting layer 105. Hole injection layer 103 and hole transport layer 104 are formed by laminating or mixing one or more hole injection / transport materials, or by a mixture of hole injection / transport materials and polymer binders. Furthermore, inorganic salts such as ferric chloride (III) can be added to the hole injection / transport materials to form the layers.

[0328] As a hole injection / transport material, it is necessary to efficiently inject / transport holes from the positive electrode between electrodes under an applied electric field. Ideally, the hole injection efficiency should be high, and the injected holes should be transported efficiently. For this purpose, materials with low ionization potential and high hole mobility, as well as excellent stability, are preferred, and are less likely to generate impurities that would form traps during manufacturing and use.

[0329] As the material for forming the hole injection layer 103 and the hole transport layer 104, any compound can be selected from those conventionally used as charge transport materials for holes in photoconductive materials, and known compounds used in hole injection layers and hole transport layers of p-type semiconductors and organic EL devices. Specific examples include carbazole derivatives (N-phenylcarbazole, polyvinylcarbazole, etc.), bis(N-arylcarbazole) or bis(N-alkylcarbazole) and other biscarbazole derivatives; triarylamine derivatives (polymers with aromatic tertiary amino groups in the main chain or side chain, 1,1-bis(4-di-p-tolylaminophenyl)cyclohexane, N,N'-diphenyl-N,N'-di(3-methylphenyl)-4,4'-diaminobiphenyl, N,N'-diphenyl-N,N'-dinaphthyl-4,4'-diaminobiphenyl, N,N'-diphenyl-N,N'-di(3-methylphenyl)-4,4'-diphenyl-1,1'-diamine, N,N'-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, 4,4',4”-tris(3-methylphenyl(phenyl)amino)triphenylamine and other triphenylamine derivatives; star-shaped amine derivatives, etc.), violet derivatives, phthalocyanine derivatives (metal-free, copper phthalocyanine, etc.), dihydropyrazole derivatives, hydrazone compounds, benzofuran derivatives, thiophene derivatives, oxadiazole derivatives, quinoxaline derivatives (e.g., 1,4,5,8,9,12-hexaazabenzophenanthrene-2,3,6,7,10,11-hexacarboxynitrile, etc.), porphyrin derivatives and other heterocyclic compounds; polysilanes, etc. In polymer systems, polycarbonate, styrene derivatives, polyvinylcarbazole and polysilanes having the aforementioned monomers in their side chains are preferred, as long as they are compounds that can form a thin film necessary for the fabrication of the light-emitting element, can inject holes from the anode, and can transport holes, there are no particular limitations.

[0330] Furthermore, it is known that the conductivity of organic semiconductors is strongly affected by their doping. The matrix material of such organic semiconductors is composed of either electron-donating or electron-accepting compounds. For doping with electron-donating materials, strong electron-accepting compounds such as tetracyanoquinone dimethyl ether (TCNQ) or 2,3,5,6-tetrafluorotetracyano-1,4-benzoquinone dimethyl ether (F4TCNQ) are known (see, for example, “M. Pfeiffer, A. Beyer, T. Fritz, K. Leo, Appl. Phys. Lett., 73(22), 3202-3204 (1998)” and “J. Blochwitz, M. Pheiffer, T. Fritz, K. Leo, Appl. Phys. Lett., 73(6), 729-731 (1998)”). They generate so-called holes through electron migration processes in the electron-donating matrix material (hole-transporting material). The conductivity of the base material varies significantly depending on the number and mobility of holes. Examples of matrix materials with hole transport properties include benzidine derivatives (TPD, etc.), star-shaped amine derivatives (TDATA, etc.), and specific metal phthalocyanines (especially zinc phthalocyanines (ZnPc, etc.)) (Japanese Patent Application Publication No. 2005-167175).

[0331] The aforementioned hole injection layer materials and hole transport layer materials can also be used as hole layer materials in the following forms: polymeric compounds or their polymeric cross-links obtained by polymerizing reactive compounds obtained by substituting reactive substituents on them, or side-chain type polymeric compounds or their side-chain type polymeric cross-links obtained by reacting a main-chain type polymer with the aforementioned reactive compounds. The description of the reactive substituents in the polycyclic aromatic compounds shown in formula (1) can be cited as examples of such reactive substituents.

[0332] The applications of such polymers and polymer crosslinkers are detailed below.

[0333] <Emitting layer in organic electroluminescent devices>

[0334] The light-emitting layer 105 is a layer that emits light by recombination of holes injected from the anode 102 with electrons injected from the cathode 108 between electrodes to which an electric field is applied. As the material forming the light-emitting layer 105, any compound that is excited and emits light through the recombination of holes and electrons (a luminescent compound) is acceptable; preferably, it is a compound capable of forming a stable thin film shape and exhibiting high luminescence (fluorescence) efficiency in the solid state. In this invention, as the material for the light-emitting layer, a host material and, for example, a polycyclic aromatic compound of the above general formula (1) as a dopant material can be used.

[0335] The light-emitting layer can be a single layer or composed of multiple layers, formed from light-emitting layer materials (host material and dopant material). The host material and dopant material can each be one type or a combination of multiple types. The dopant material can be incorporated into the entire host material or contained in a specific area. Doping can be achieved through co-evaporation with the host material, or by pre-mixing the dopant with the host material and then simultaneously evaporating.

[0336] The amount of the main material varies depending on the type of main material, and can be determined based on its characteristics. The preferred amount of the main material is 50 to 99.999% by weight of the total material used in the light-emitting layer, more preferably 80 to 99.95% by weight, and even more preferably 90 to 99.9% by weight.

[0337] The amount of dopant varies depending on the type of dopant and can be determined based on its characteristics. The preferred amount of dopant is 0.001 to 50% by weight of the total material used in the luminescent layer, more preferably 0.05 to 20% by weight, and even more preferably 0.1 to 10% by weight. If it falls within the above range, it is preferable from the perspective of preventing concentration quenching, for example.

[0338] Examples of suitable main materials include fused-ring derivatives such as anthracene, pyrene, dibenzo[a]pyrene, or fluorene, which have long been known as luminescent agents; bis(styrene)-anthracene derivatives, styrene-phenylene derivatives, and other bis(styrene)-derived derivatives; tetraphenylbutadiene derivatives, cyclopentadiene derivatives, etc. Anthracene compounds, fluorene compounds, or dibenzo[a]pyrene compounds are particularly preferred.

[0339] <Anthracene compounds>

[0340] The anthracene compounds that are the main body are, for example, compounds represented by the following general formula (3).

[0341]

[0342] In equation (3),

[0343] X and Ar 4 Each independently consists of hydrogen, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted diarylamino, optionally substituted diheterarylamino, optionally substituted arylheterarylamino, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted alkenyl, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted arylthio, or optionally substituted silyl, all of X and Ar 4 They are not both hydrogen.

[0344] At least one hydrogen atom in the compound shown in formula (3) may be optionally substituted with a halogen, cyano, deuterium or optionally a heteroaryl group.

[0345] Furthermore, the structure shown in formula (3) can be used as a unit structure to form a polymer (preferably a dimer). In this case, examples of unit structures shown in formula (3) that are bonded to each other by means of X can be listed, such as single bonds, arylene groups (phenylene, biphenylene, and naphthylene, etc.) and heteroarylene groups (pyridine ring, dibenzofuran ring, dibenzothiophene ring, carbazole ring, benzocarbazole ring, and phenyl-substituted carbazole ring, etc., groups with divalent valence).

[0346] Details of the aforementioned aryl, heteroaryl, diarylamino, diarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio, or silyl groups are described in the preferred embodiments section below. Furthermore, as substituents thereon, aryl, heteroaryl, diarylamino, diarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio, or silyl groups are listed, and details of these are also described in the preferred embodiments section below.

[0347] The preferred embodiments of the above-described anthracene compounds are described below. The symbols in the following structures are defined in the same way as those defined above.

[0348]

[0349] In general formula (3), each X is independently a group represented by 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 the * position. Preferably, the two Xs are not simultaneously represented by formula (3-X3). More preferably, the two Xs are not simultaneously represented by formula (3-X2).

[0350] Furthermore, the structure shown in formula (3) can be used as a unit structure to form a polymer (preferably a dimer). In this case, examples of unit structures shown in formula (3) that are bonded to each other by means of X can be listed, such as single bonds, arylene groups (phenylene, biphenylene, and naphthylene, etc.) and heteroarylene groups (pyridine ring, dibenzofuran ring, dibenzothiophene ring, carbazole ring, benzocarbazole ring, and phenyl-substituted carbazole ring, etc., groups with divalent valence).

[0351] The naphthyl group in formulas (3-X1) and (3-X2) is optionally fused with one benzene ring. The fused structure is shown below.

[0352]

[0353] Ar 1 and Ar 2 Each group is independently hydrogen, phenyl, biphenyl, terphenyl, tetraphenyl, naphthyl, phenanthryl, fluorenyl, benzo[a]fluorenyl, hydroxyl, benzo[a]phenanthryl, pyrene, or a group represented by formula (A) above (including carbazole, benzo[a]carbazole, and phenyl-substituted carbazole). It should be noted that Ar 1 Or Ar 2 When the group is the one shown in formula (A), the group shown in formula (A) is bonded at its * position to the naphthalene ring in formula (3-X1) or formula (3-X2).

[0354] Ar 3 It can be phenyl, biphenyl, terphenyl, tetraphenyl, naphthyl, phenanthryl, fluorenyl, benzo[a]fluorenyl, hydroxyl, benzo[a]phenanthryl, pyrene, or a group represented by formula (A) above (including carbazole, benzo[a]carbazole, and phenyl-substituted carbazole). It should be noted that Ar 3 When the group is as shown in formula (A), the group shown in formula (A) is bonded at its * position to the single bond shown by the straight line in formula (3-X3). That is, the anthracene ring of formula (3) is directly bonded to the group shown in formula (A).

[0355] In addition, Ar 3 Ar can be optionally equipped with substituents. 3 At least one hydrogen atom may be further substituted by an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a phenanthryl group, a fluorenyl group, a phenyl group, a benzo[a]phenanthryl group, a pyrene group, or a group represented by formula (A) above (including carbazole and phenyl-substituted carbazole groups). It should be noted that Ar 3 When the substituent is a group represented by formula (A), the group represented by formula (A) is coupled to Ar in formula (3-X3) at its * position. 3 Bonding.

[0356] Ar 4Each of the following is independently hydrogen, phenyl, biphenyl, terphenyl, naphthyl, alkyl group substituted with 1 to 4 carbon atoms (methyl, ethyl, tert-butyl, etc.) and / or cycloalkyl group substituted with 5 to 10 carbon atoms.

[0357] Alkyl groups with 1 to 4 carbon atoms that are substituted on the silyl group can be methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, tert-butyl, cyclobutyl, etc., and the three hydrogens in the silyl group are each independently replaced by these alkyl groups.

[0358] Specific examples of "silyl groups substituted with alkyl groups having 1 to 4 carbon atoms" include trimethylsilyl, triethylsilyl, tripropylsilyl, triisopropylsilyl, tributylsilyl, trisec-butylsilyl, tritert-butylsilyl, ethyldimethylsilyl, propyldimethylsilyl, isopropyldimethylsilyl, butyldimethylsilyl, sec-butyldimethylsilyl, tert-butyldimethylsilyl, and methyldiethylsilyl. Propyl diethylsilyl, isopropyl diethylsilyl, butyl diethylsilyl, sec-butyl diethylsilyl, tert-butyl diethylsilyl, methyl dipropylsilyl, ethyl dipropylsilyl, butyl dipropylsilyl, sec-butyl dipropylsilyl, tert-butyl dipropylsilyl, methyl diisopropylsilyl, ethyl diisopropylsilyl, butyl diisopropylsilyl, sec-butyl diisopropylsilyl, tert-butyl diisopropylsilyl, etc.

[0359] Examples of cycloalkyl groups with 5 to 10 carbon atoms substituted on the silyl group include cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, norbornenyl, bicyclo[1.1.1]pentyl, bicyclo[2.0.1]pentyl, bicyclo[1.2.1]hexyl, bicyclo[3.0.1]hexyl, bicyclo[2.1.2]heptyl, bicyclo[2.2.2]octyl, adamantyl, decahydronaphthyl, and decahydroazyl, etc., in which the three hydrogens in the silyl group are each independently substituted by these cycloalkyl groups.

[0360] Specific examples of "silyl groups substituted with cycloalkyl groups having 5 to 10 carbon atoms" include tricyclopentylsilyl and tricyclohexylsilyl.

[0361] As substituted silyl groups, there are also dialkylcycloalkylsilyl groups substituted with two alkyl groups and one cycloalkyl group, and alkyldicycloalkylsilyl groups substituted with one alkyl group and two cycloalkyl groups. Specific examples of substituted alkyl and cycloalkyl groups can be listed above.

[0362] Furthermore, the hydrogen in the chemical structure of the anthracene compound represented by general formula (3) may optionally be replaced by the group represented by formula (A) above. When replaced by the group represented by formula (A), the group represented by formula (A) replaces at least one hydrogen in the compound represented by formula (3) at its * position.

[0363] The group shown in formula (A) is one of the substituents that the anthracene compounds shown in formula (3) may have.

[0364]

[0365] In the above formula (A), Y is -O-, -S-, or >NR. 29 R 21 ~R 28 Each of the following is 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, hydroxyl or cyano, R 21 ~R 28 The adjacent groups can be selectively bonded to each other to form hydrocarbon rings, aromatic rings, or heteroaromatic rings, R 29 It can be hydrogen or an aryl group that is optionally substituted.

[0366] As R 21 ~R 28 The "alkyl" in "optionally substituted alkyl" can be either straight-chain or branched, and examples include straight-chain alkyl with 1 to 24 carbon atoms or branched alkyl with 3 to 24 carbon atoms. Preferably, it is an alkyl with 1 to 18 carbon atoms (branched alkyl with 3 to 18 carbon atoms), more preferably an alkyl with 1 to 12 carbon atoms (branched alkyl with 3 to 12 carbon atoms), even more preferably an alkyl with 1 to 6 carbon atoms (branched alkyl with 3 to 6 carbon atoms), and particularly preferably an alkyl with 1 to 4 carbon atoms (branched alkyl with 3 to 4 carbon atoms).

[0367] Specific examples of "alkyl groups" include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, tert-octyl, 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-pentadecanyl, n-hexadecyl, n-heptadecyl, n-octadecyl, n-eicosyl, etc.

[0368] As R 21 ~R 28 The "cycloalkyl group" in "optionally substituted cycloalkyl group" can be listed as cycloalkyl groups with 3 to 24 carbon atoms, cycloalkyl groups with 3 to 20 carbon atoms, cycloalkyl groups with 3 to 16 carbon atoms, cycloalkyl groups with 3 to 14 carbon atoms, cycloalkyl groups with 5 to 10 carbon atoms, cycloalkyl groups with 5 to 8 carbon atoms, cycloalkyl groups with 5 to 6 carbon atoms, cycloalkyl groups with 5 carbon atoms, etc.

[0369] Specific examples of "cycloalkyl" include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl and their alkyl (especially methyl) substituted derivatives with 1 to 4 carbon atoms; norbornenyl, bicyclo[1.0.1]butyl, bicyclo[1.1.1]pentyl, bicyclo[2.0.1]pentyl, bicyclo[1.2.1]hexyl, bicyclo[3.0.1]hexyl, bicyclo[2.1.2]heptyl, bicyclo[2.2.2]octyl, adamantyl, diadamantyl, decahydronaphthyl, decahydroazyl, etc.

[0370] As R 21 ~R 28 The "aryl" in "optionally substituted aryl" can be exemplified by, for example, aryl groups with 6 to 30 carbon atoms, preferably aryl groups with 6 to 16 carbon atoms, more preferably aryl groups with 6 to 12 carbon atoms, and particularly preferably aryl groups with 6 to 10 carbon atoms.

[0371] Specific examples of "aryl" groups include phenyl as a monocyclic compound; biphenyl as a bicyclic compound; naphthyl as a fused bicyclic compound; terphenyl (m-terphenyl, o-terphenyl, p-terphenyl) as a tricyclic compound; acenaphthene, fluorenyl, phenatenyl, and phenanthrene as fused tricyclic compounds; benzo[a]phenanthrene, pyrene, and benzo[a]tetraphenyl as fused tetracyclic compounds; and perylene and benzo[a]pentaphenyl as fused pentacyclic compounds.

[0372] As R 21 ~R 28The term "heteroaryl group" in "optionally substituted heteroaryl group" can include, for example, heteroaryl groups with 2 to 30 carbon atoms, preferably heteroaryl groups with 2 to 25 carbon atoms, more preferably heteroaryl groups with 2 to 20 carbon atoms, even more preferably heteroaryl groups with 2 to 15 carbon atoms, and particularly preferably heteroaryl groups with 2 to 10 carbon atoms. Furthermore, examples of heteroaryl groups include heterocycles containing 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen as cyclic atoms in addition to carbon.

[0373] Specific examples of "heteroaryl" groups include, for instance, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazole, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, pyrazolyl, pyridyl, pyrimidinyl, pyridazinyl, triazinyl, indoleyl, isoindoleyl, 1H-indazoleyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolinyl, isoquinolinyl, cenolinyl, quinazolinyl, quinoxolinyl, phthalazinyl, naphridinyl, purinyl, pteridinyl, carbazoleyl, acridineyl, phenoxthiazolyl, phenoxazinyl, and phenthiazolyl. Phenoazinyl, dibenzo[b,e][1,4]nitrosilanehexacyclohexyl, indene, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, naphthobenzofuranyl, thiophenyl, benzothiophenyl, isobenzothiophenyl, dibenzothiophenyl, naphthobenzothiophenyl, benzophosphanepentadienyl, dibenzophosphanepentadienyl, monovalent group of benzophosphanepentadienyl oxide ring, monovalent group of dibenzophosphanepentadienyl oxide ring, furazinyl, thianyl, indolocarbazoyl, benzoindolocarbazoyl and benzobenzoindolocarbazoyl, etc.

[0374] As R 21 ~R 28 The "alkoxy group" in "optionally substituted alkoxy group" can include, for example, straight-chain alkoxy groups with 1 to 24 carbon atoms or branched alkoxy groups with 3 to 24 carbon atoms. Preferably, it is an alkoxy group with 1 to 18 carbon atoms (branched alkoxy groups with 3 to 18 carbon atoms), more preferably an alkoxy group with 1 to 12 carbon atoms (branched alkoxy groups with 3 to 12 carbon atoms), even more preferably an alkoxy group with 1 to 6 carbon atoms (branched alkoxy groups with 3 to 6 carbon atoms), and particularly preferably an alkoxy group with 1 to 4 carbon atoms (branched alkoxy groups with 3 to 4 carbon atoms).

[0375] Specific examples of "alkoxy groups" include methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, sec-butoxy, tert-butoxy, pentoxy, hexoxy, heptoxy, and octoxy.

[0376] As R 21 ~R 28The "aryloxy group" in "optionally substituted aryloxy group" refers to a group in which the hydrogen of the -OH group is replaced by an aryl group, which can be referenced as R above. 21 ~R 28 The "aryl" in the text refers to the group that is described.

[0377] As R 21 ~R 28 The "arylthio" in "optionally substituted arylthio" refers to a group in which the hydrogen of the -SH group is replaced by an aryl group, which can be referenced as R above. 21 ~R 28 The "aryl" in the text refers to the group that is described.

[0378] As R 21 ~R 28 The term "trialkylsilyl" can be listed as a group in which each of the three hydrogens in the silyl group is independently replaced by an alkyl group, which can be referenced as R in the above context. 21 ~R 28 The "alkyl" in the text refers to the group group. For substitution, the preferred alkyl group is an alkyl group having 1 to 4 carbon atoms, specifically including methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, tert-butyl, cyclobutyl, etc.

[0379] Specific examples of "trialkylsilyl" include trimethylsilyl, triethylsilyl, tripropylsilyl, triisopropylsilyl, tributylsilyl, trisec-butylsilyl, tritert-butylsilyl, ethyldimethylsilyl, propyldimethylsilyl, isopropyldimethylsilyl, butyldimethylsilyl, sec-butyldimethylsilyl, tert-butyldimethylsilyl, methyldiethylsilyl, and propyldiethylsilyl. Silyl groups, including isopropyl diethylsilyl, butyl diethylsilyl, sec-butyl diethylsilyl, tert-butyl diethylsilyl, methyl dipropylsilyl, ethyl dipropylsilyl, butyl dipropylsilyl, sec-butyl dipropylsilyl, tert-butyl dipropylsilyl, methyl diisopropylsilyl, ethyl diisopropylsilyl, butyl diisopropylsilyl, sec-butyl diisopropylsilyl, tert-butyl diisopropylsilyl, etc.

[0380] As R 21 ~R 28 The term "tricycloalkylsilyl" can be used to list groups in which the three hydrogens of a silyl group are each independently replaced by a cycloalkyl group, which can be referenced as R in the above context. 21 ~R 28The term "cycloalkyl" refers to the group group described in the text. For substitution, the preferred cycloalkyl group is a cycloalkyl group with 5 to 10 carbon atoms. Specifically, examples include cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, bicyclo[1.1.1]pentyl, bicyclo[2.0.1]pentyl, bicyclo[1.2.1]hexyl, bicyclo[3.0.1]hexyl, bicyclo[2.1.2]heptyl, bicyclo[2.2.2]octyl, adamantyl, decahydronaphthyl, decahydroazyl, etc.

[0381] Specific examples of "tricycloalkylsilyl" include tricyclopentylsilyl and tricyclohexylsilyl.

[0382] As specific examples of dialkylcycloalkylsilyl substituted with two alkyl groups and one cycloalkyl group, and alkyldicycloalkylsilyl substituted with one alkyl group and two cycloalkyl groups, silyl substituted with groups selected from the specific alkyl and cycloalkyl groups mentioned above can be listed.

[0383] As R 21 ~R 28 The "substituted amino group" in "optionally substituted amino group" can include, for example, amino groups in which two hydrogens are substituted by an aryl or heteroaryl group. An amino group in which two hydrogens are substituted by an aryl group is a diaryl-substituted amino group, an amino group in which two hydrogens are substituted by a heteroaryl group is a dihexanel-substituted amino group, and an amino group in which both hydrogens are aryl-hexanel-substituted amino groups. The aryl or heteroaryl group can be referenced as R in the above description. 21 ~R 28 The groups described are "aryl" and "heteroaryl".

[0384] Specific examples of "substituted amino groups" include diphenylamino, dinaphthylamino, phenylnaphthylamino, dipyridylamino, phenylpyridylamino, naphthylpyridylamino, etc.

[0385] As R 21 ~R 28 The "halogens" mentioned include fluorine, chlorine, bromine, and iodine.

[0386] As R 21 ~R 28 Several of the groups described above may be optionally substituted, and examples of substituents include alkyl, cycloalkyl, aryl, or heteroaryl groups. These alkyl, cycloalkyl, aryl, or heteroaryl groups can be referenced as R in the above description. 21 ~R 28 The group indicated by "alkyl", "cycloalkyl", "aryl" or "heteroaryl".

[0387] As Y ">NR 29 R in " 29The aryl group can be hydrogen or optionally substituted, and can be cited as R above. 21 ~R 28 The "aryl" group is used to describe the group, and furthermore, as a substituent, it can be referred to as R. 21 ~R 28 The substituents on the group indicate the group.

[0388] R 21 ~R 28 The adjacent groups may optionally bond to each other to form a hydrocarbon ring, an aromatic ring, or a heteroaromatic ring. In the absence of a ring, it is a group represented by formula (A-1) below; in the case of a ring formation, groups represented by formulas (A-2) to (A-14) below can be listed as examples. Y and * in the formulas are the same as defined above. It should be noted that at least one hydrogen atom in any of the groups represented by formulas (A-1) to (A-14) may optionally be substituted with an alkyl, cycloalkyl, aryl, heteroaryl, alkoxy, aryloxy, arylthio, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, alkyldicycloalkylsilyl, diaryl-substituted amino, diheteroaryl-substituted amino, arylheteroaryl-substituted amino, halogen, hydroxyl, or cyano group.

[0389]

[0390] As rings formed by the bonding of adjacent groups, examples of hydrocarbon rings include cyclohexane rings, and examples of aromatic or heteroaromatic rings include those in the above R... 21 ~R 28 The ring structures described in “aryl” and “heteroaryl” are formed by fusion with one or two benzene rings in the above formula (A-1).

[0391] As the group represented by formula (A), examples include any of the groups represented by formulas (A-1) to (A-14) above, preferably any of the groups represented by formulas (A-1) to (A-5) and (A-12) to (A-14) above, more preferably any of the groups represented by formulas (A-1) to (A-4) above, even more preferably any of the groups represented by formulas (A-1), (A-3) and (A-4) above, and particularly preferably the group represented by formula (A-1) above.

[0392] The group shown in formula (A) is, as described above, associated with the naphthalene ring in formula (3-X1) or formula (3-X2), the single bond in formula (3-X3), or the Ar group in formula (3-X3) at the * position in formula (A). 3In addition, it substitutes at least one hydrogen in the compounds represented by formula (3), but in their bonding forms, it is preferably with the naphthalene ring in formula (3-X1) or formula (3-X2), the single bond in formula (3-X3), and / or the Ar in formula (3-X3). 3 The form of bonding.

[0393] Furthermore, the naphthalene ring in formula (3-X1) or formula (3-X2), the single bond in formula (3-X3), and the Ar in formula (3-X3) 3 The bonding positions in the structure of the group shown in formula (A), and the positions in the structure of the group shown in formula (A) that substitute for at least one hydrogen atom in the compound shown in formula (3) can be any positions in the structure of formula (A), for example, any of the two benzene rings in the structure of formula (A), or R in the structure of formula (A). 21 ~R 28 Arbitrary rings formed by the bonding of adjacent groups, and ">NR" as Y in the structure of formula (A). 29 R in " 29 Bonding can be performed at any position within the structure.

[0394] As the group represented by formula (A), the following groups can be listed as examples. Y and * in the formula are the same as defined above.

[0395]

[0396] Furthermore, all or part of the hydrogen in the chemical structure of the anthracene compounds shown in general formula (3) can be deuterium.

[0397] Specific examples of anthracene compounds include compounds represented by formulas (3-1) to (3-72) below. It should be noted that in the following structural formulas, "Me" represents methyl, "D" represents deuterium, and "tBu" represents tert-butyl.

[0398]

[0399]

[0400]

[0401]

[0402] The anthracene compounds shown in formula (3) can be obtained by using compounds with reactive groups at desired positions on the anthracene skeleton and by using compounds with reactive groups at desired positions on the X and Ar axes. 4Compounds with reactive groups in parts of the structure of formula (A) are used as starting materials and manufactured by applying Suzuki coupling, Negishi coupling, or other known coupling reactions. Examples of reactive groups in these reactive compounds include halogens and boric acids. For specific manufacturing methods, refer to, for example, the synthesis methods described in paragraphs

[0089] to

[0175] of International Publication No. 2014 / 141725.

[0403] <fluorene compounds>

[0404] The compound shown in general formula (4) essentially functions as the host.

[0405]

[0406] In the above formula (4),

[0407] R 1 ~R 10 Each of the following is independently hydrogen, aryl, heteroaryl (which may optionally be bonded to the fluorene skeleton in formula (4) by means of a linking group), diarylamino, diheterarylamino, arylheterarylamino, alkyl, cycloalkyl, alkenyl, alkoxy or aryloxy, wherein at least one hydrogen atom may optionally be substituted by aryl, heteroaryl, alkyl or cycloalkyl.

[0408] In addition, R 1 With R 2 R 2 With R 3 R 3 With R 4 R 5 With R 6 R 6 With R 7 R 7 With R 8 Or R 9 With R 10 Each ring can be independently and optionally bonded to form a fused ring or a spiro ring, wherein at least one hydrogen atom in the formed ring is optionally substituted with an aryl, heteroaryl (which is optionally bonded to the formed ring by means of a linking group), diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkenyl, alkoxy, or aryloxy group, wherein at least one hydrogen atom is optionally substituted with an aryl, heteroaryl, alkyl, or cycloalkyl group, and

[0409] At least one hydrogen atom in the compound shown in formula (4) may be optionally substituted with halogen, cyano or deuterium.

[0410] Details of each group in the definition of formula (4) above can be found in the description of polycyclic aromatic compounds in formula (1) above.

[0411] As R 1 ~R10 The alkenyl group in the text can be exemplified by alkenyl groups having 2 to 30 carbon atoms, preferably alkenyl groups having 2 to 20 carbon atoms, more preferably alkenyl groups having 2 to 10 carbon atoms, even more preferably alkenyl groups having 2 to 6 carbon atoms, and particularly preferably alkenyl groups having 2 to 4 carbon atoms. The alkenyl group is preferably 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.

[0412] It should be noted that, as specific examples of heteroaryl groups, monovalent groups can also be listed by removing any one hydrogen atom from compounds of the following formulas (4-Ar1), (4-Ar2), (4-Ar3), (4-Ar4), or (4-Ar5).

[0413]

[0414] In equations (4-Ar1) to (4-Ar5), Y 1 Each can be independently O, S, or NR, and R can be phenyl, biphenyl, naphthyl, anthracene, or hydrogen.

[0415] At least one hydrogen atom in the structures of the above formulas (4-Ar1) to (4-Ar5) may be optionally substituted with phenyl, biphenyl, naphthyl, anthraceneyl, phenanthryl, methyl, ethyl, propyl or butyl.

[0416] These heteroaryl groups can be selectively bonded to the fluorene skeleton in formula (4) above via a linking group. That is, the fluorene skeleton in formula (4) can be directly bonded to the above heteroaryl groups, or they can be bonded to each other via a linking group. Examples of such linking groups include phenylene, biphenylene, naphthylene, anthracene, methylene, ethylene, -OCH2CH2-, -CH2CH2O-, or -OCH2CH2O-.

[0417] Furthermore, R in equation (4) 1 With R 2 R 2 With R 3 R 3 With R 4 R 5 With R 6 R 6 With R 7 Or R 7 With R 8 Each independently chooses to bond to form a fused ring, R 9 With R 10 Optional bonding forms a helical ring. From R 1 ~R 8The formed fused ring is a ring fused with the benzene ring in formula (4), and is either an aliphatic ring or an aromatic ring. An aromatic ring is preferred; examples of structures including the benzene ring in formula (4) include naphthalene rings and phenanthrene rings. From R... 9 and R 10 The resulting helical ring is a ring that is helically bonded to the five-membered ring in formula (4), and is an aliphatic ring or an aromatic ring. It is preferably an aromatic ring, such as a fluorene ring.

[0418] The compound represented by general formula (4) is preferably a compound represented by formula (4-1), formula (4-2) or formula (4-3) respectively, which are compounds fused with R in general formula (4). 1 With R 2 Compounds formed by bonding of benzene rings, and compounds fused with R in general formula (4) 3 With R 4 Compounds formed by bonding of benzene rings, R in general formula (4) 1 ~R 8 Compounds that are not bonded.

[0419]

[0420] R in equations (4-1), (4-2), and (4-3) 1 ~R 10 The definition of R in equation (4) 1 ~R 10 Similarly, R in equations (4-1) and (4-2) 11 ~R 14 The definition is also the same as R in equation (4). 1 ~R 10 same.

[0421] The compound represented by general formula (4) is further preferably a compound represented by formula (4-1A), formula (4-2A) or formula (4-3A), wherein R in formula (4-1), formula (4-1) or formula (4-3) is respectively. 9 With R 10 Compounds that bond together to form a spirofluorene ring.

[0422]

[0423] R in equations (4-1A), (4-2A) and (4-3A) 2 ~R 7 The definition of R in equations (4-1), (4-2), and (4-3) is the same as that in equation (4-3). 2 ~R 7 Similarly, R in equations (4-1A) and (4-2A) 11 ~R 14The definition is also the same as R in equations (4-1) and (4-2). 11 ~R 14 same.

[0424] In addition, all or part of the hydrogen in the compound shown in formula (4) may be optionally replaced by halogen, cyano or deuterium.

[0425] <Dibenzo-p-methyl compounds>

[0426] The main dibenzo[a]cyclohexane compounds are, for example, compounds represented by the following general formula (5).

[0427]

[0428] In the above formula (5),

[0429] R 1 ~R 16 Each of the following is independently hydrogen, aryl, heteroaryl (which may optionally be bonded to the dibenzoxane skeleton of formula (5) above by means of a linking group), diarylamino, diheterarylamino, arylheterarylamino, alkyl, cycloalkyl, alkenyl, alkoxy or aryloxy, wherein at least one hydrogen atom may optionally be substituted by aryl, heteroaryl, alkyl or cycloalkyl.

[0430] In addition, R 1 ~R 16 The adjacent groups may optionally be bonded to each other to form a fused ring, wherein at least one hydrogen atom in the formed ring may optionally be substituted with an aryl, heteroaryl (which may optionally be bonded to the formed ring by means of a linking group), diarylamino, diheterarylamino, arylheterarylamino, alkyl, cycloalkyl, alkenyl, alkoxy, or aryloxy group, wherein at least one hydrogen atom may optionally be substituted with an aryl, heteroaryl, alkyl, or cycloalkyl group, and

[0431] At least one hydrogen atom in the compound shown in formula (5) may be optionally substituted with a halogen, a cyano group or a deuterium.

[0432] Details of each group in the definition of formula (5) above can be found in the description of polycyclic aromatic compounds in formula (1) above.

[0433] The alkenyl group defined in formula (5) above can be, for example, an alkenyl group with 2 to 30 carbon atoms, preferably an alkenyl group with 2 to 20 carbon atoms, more preferably an alkenyl group with 2 to 10 carbon atoms, even more preferably an alkenyl group with 2 to 6 carbon atoms, and particularly preferably an alkenyl group with 2 to 4 carbon atoms. Preferably, the alkenyl group is 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.

[0434] It should be noted that, as specific examples of heteroaryl groups, monovalent groups can also be listed by removing any one hydrogen atom from compounds of the following formulas (5-Ar1), (5-Ar2), (5-Ar3), (5-Ar4), or (5-Ar5).

[0435]

[0436] In equations (5-Ar1) to (5-Ar5), Y 1 Each can be independently O, S, or NR, and R can be phenyl, biphenyl, naphthyl, anthracene, or hydrogen.

[0437] At least one hydrogen atom in the structures of formulas (5-Ar1) to (5-Ar5) may be optionally substituted with phenyl, biphenyl, naphthyl, anthraceneyl, phenanthryl, methyl, ethyl, propyl or butyl.

[0438] These heteroaryl groups can optionally be bonded to the dibenzo[a]benzyl skeleton in formula (5) above via a linking group. That is, the dibenzo[a]benzyl skeleton in formula (5) can be directly bonded to the above heteroaryl groups, or they can be bonded to each other via a linking group. Examples of such linking groups include phenylene, biphenylene, naphthylene, anthraceneylene, methylene, ethylene, -OCH2CH2-, -CH2CH2O-, or -OCH2CH2O-.

[0439] The compound represented by general formula (5) is preferably R. 1 R 4 R 5 R 8 R 9 R 12 R 13 and R 16 It is hydrogen. In this case, R in equation (5) 2 R 3 R 6 R 7 R 10 R 11 R 14 and R 15 Each is preferably hydrogen, phenyl, biphenyl, naphthyl, anthracene, phenanthrene, 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 optionally be bonded to the dibenzoxane skeleton of the above formula (5) by means of phenylene, biphenylene, naphthylene, anthracene, methylene, ethylene, -OCH2CH2-, -CH2CH2O- or -OCH2CH2O-), methyl, ethyl, propyl or butyl.

[0440] The compound represented by general formula (5) is more preferably R. 1 R 2 R 4 R 5 R 7 R 8 R 9 R 10 R 12 R 13 R 15 and R 16 It is hydrogen. In this case, R in equation (5) 3 R 6 R 11 and R 14 At least one of them (preferably one or both, more preferably one) is a monovalent group having the structure of the above formula (5-Ar1), (5-Ar2), (5-Ar3), (5-Ar4) or (5-Ar5) by means of a single bond, phenylene, biphenylene, naphthylene, anthraceneylene, methylene, ethylene, -OCH2CH2-, -CH2CH2O- or -OCH2CH2O-.

[0441] In addition to at least one of the aforementioned (i.e., except for positions substituted with a monovalent group having the aforementioned structure), it is hydrogen, phenyl, biphenyl, naphthyl, anthracene, methyl, ethyl, propyl, or butyl, wherein at least one of the hydrogen atoms is optionally substituted by phenyl, biphenyl, naphthyl, anthracene, methyl, ethyl, propyl, or butyl.

[0442] Furthermore, R in equation (5) 2 R 3 R 6 R 7 R 10 R 11 R 14 and R 15 When the group is selected from the monovalent group having the structure shown in formulas (5-Ar1) to (5-Ar5), at least one hydrogen in the structure may optionally be R in formula (5). 1 ~R 16 A single bond is formed by the bonding of any two elements in the matrix.

[0443] Regarding the aforementioned materials for the light-emitting layer (both the host material and the dopant material), even if a polymeric compound or its polymeric cross-linked form is prepared by polymerizing a reactive compound on which reactive substituents have been substituted, or a side-chain type polymeric compound or its side-chain type polymeric cross-linked form is prepared by reacting a main-chain type polymer with the aforementioned reactive compound, it can still be used as a material for the light-emitting layer. As for the reactive substituents in this case, the description of the polycyclic aromatic compounds shown in formula (1) can be referenced.

[0444] Details regarding the uses of such polymers and polymer crosslinkers are described below.

[0445] <An Example of a Polymer Host Material>

[0446]

[0447] In formula (SPH-1),

[0448] Each MU is an independent divalent aromatic group, and each EC is an independent monovalent aromatic group. The two hydrogens in MU are replaced by EC or MU, and k is an integer from 2 to 50000.

[0449] More specifically,

[0450] Each of MU can be independently arylene, heteroarylene, diarylenearylamino, diarylenearylboryl, oxaborine diyl, or azaborine diyl.

[0451] EC can be independently hydrogen, aryl, heteroaryl, diarylamino, diherylamino, arylherylamino, or aryloxy.

[0452] At least one hydrogen atom in MU and EC may optionally be further substituted with aryl, heteroaryl, diarylamino, alkyl, or cycloalkyl groups.

[0453] k is an integer from 2 to 50000.

[0454] k is preferably an integer from 20 to 50,000, and more preferably an integer from 100 to 50,000.

[0455] In formula (SPH-1), at least one hydrogen in MU and EC is optionally substituted with an alkyl group having 1 to 24 carbon atoms, a cycloalkyl group having 3 to 24 carbon atoms, a halogen, or deuterium. Furthermore, any -CH2- in the aforementioned alkyl group is optionally substituted with -O- or -Si(CH3)2-. Any -CH2- in the aforementioned alkyl group other than the -CH2- directly connected to EC in formula (SPH-1) is optionally substituted with an aryl group having 6 to 24 carbon atoms. Any hydrogen in the aforementioned alkyl group is optionally substituted with fluorine.

[0456] As a MU, divalent groups can be listed, for example, those obtained by removing any two hydrogen atoms from any of the following compounds.

[0457]

[0458] More specifically, examples of divalent groups shown in any of the following structures can be listed. In these structures, MU is bonded to other MUs or ECs at the * position.

[0459]

[0460]

[0461]

[0462]

[0463]

[0464]

[0465]

[0466]

[0467]

[0468] Furthermore, EC can be exemplified by monovalent groups as shown in any of the following structures. In these, the EC is bonded to MU at the * position.

[0469]

[0470]

[0471] Regarding the compound represented by formula (SPH-1), from the viewpoint of solubility and coating film-forming properties, it is preferable that 10-100% of the total number of MUs (k) in the molecule has an alkyl group with 1-24 carbon atoms; more preferably, 30-100% of the total number of MUs (k) in the molecule has an alkyl group with 1-18 carbon atoms (branched alkyl group with 3-18 carbon atoms); and even more preferably, 50-100% of the total number of MUs (k) in the molecule has an alkyl group with 1-12 carbon atoms (branched alkyl group with 3-12 carbon atoms). On the other hand, from the viewpoint of in-plane orientation and charge transport, it is preferable that 10-100% of the total number of MUs (k) in the molecule has an alkyl group with 7-24 carbon atoms; more preferably, 30-100% of the total number of MUs (k) in the molecule has an alkyl group with 7-24 carbon atoms (branched alkyl group with 7-24 carbon atoms).

[0472] The detailed uses of this polymer compound and polymer crosslinker are described below.

[0473] <Electron injection layer and electron transport layer in organic electroluminescent devices>

[0474] The electron injection layer 107 efficiently injects electrons moving from the cathode 108 into the light-emitting layer 105 or the electron transport layer 106. The electron transport layer 106 efficiently transports electrons injected from the cathode 108 or electrons injected from the cathode 108 via the electron injection layer 107 to the light-emitting layer 105. The electron transport layer 106 and the electron injection layer 107 are formed by laminating or mixing one or more electron transport / injection materials, or by a mixture of electron transport / injection materials and a polymer binder.

[0475] The electron injection / transport layer is responsible for injecting and transporting electrons from the cathode. Ideally, it should have high electron injection efficiency and efficiently transport the injected electrons. Therefore, materials with high electron affinity and high electron mobility, resulting in excellent stability and low likelihood of generating trap-forming impurities during manufacturing and use, are preferred. However, considering the balance between hole and electron transport, even materials with lower electron transport capacity can improve luminous efficiency as effectively as materials with high electron transport capacity, provided that the primary function is to efficiently prevent holes from the anode from flowing to the cathode and recombinizing. Therefore, the electron injection / transport layer in this embodiment also includes the function of a layer that efficiently prevents hole movement.

[0476] As the material for forming the electron transport layer 106 or the electron injection layer 107 (electron transport material), it can be arbitrarily selected from compounds that have been conventionally used as electron conduction compounds in photoconductive materials, and well-known compounds used in the electron injection layer and electron transport layer of organic EL devices.

[0477] As materials used in the electron transport layer or electron injection layer, it is preferable to contain at least one selected from the following: compounds comprising an aromatic ring or heteroaromatic ring composed of one or more atoms selected from carbon, hydrogen, oxygen, sulfur, silicon, and phosphorus; pyrrole derivatives and their fused-ring derivatives; and metal complexes having electron-accepting nitrogen. Specifically, examples include fused-ring aromatic ring derivatives such as naphthalene and anthracene; styryl aromatic ring derivatives represented by 4,4'-bis(diphenylvinyl)biphenyl; quinone derivatives such as perylene ketone derivatives, coumarin derivatives, naphthalenedicarboximide derivatives, anthraquinone, and biphenylquinone; phosphorus oxide derivatives, carbazole derivatives, and indole derivatives. Examples of metal complexes having electron-accepting nitrogen include hydroxyazole complexes such as hydroxyphenyloxazole complexes; azomethine complexes, cycloheptatrienolone metal complexes, flavonol metal complexes, and benzoquinone metal complexes. These materials can be used alone or in combination with different materials.

[0478] In addition, specific examples of other electron-conducting compounds include pyridine derivatives, naphthalene derivatives, anthracene derivatives, phenanthrene-line derivatives, perylene ketone derivatives, coumarin derivatives, naphthalenedicarboximide derivatives, anthraquinone derivatives, biphenylquinone derivatives, diphenylquinone derivatives, perylene derivatives, oxadiazole derivatives (such as 1,3-bis[(4-tert-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 8-hydroxyquinoline derivatives, hydroxyquinoline-based metal complexes, quinoxaline derivatives, polymers of quinoxaline derivatives, benzo[a]azole compounds, gallium complexes, pyrazole derivatives, and perfluorinated phenylene derivatives. Biological derivatives, triazine derivatives, pyrazine derivatives, benzoquinoline derivatives (2,2'-bis(benzo[h]quinoline-2-yl)-9,9'-spirodifluorene, etc.), imidazopyridine derivatives, borane derivatives, benzimidazole derivatives (tris(N-phenylbenzimidazole-2-yl)benzene, etc.), benzoxazole derivatives, benzothiazole derivatives, quinoline derivatives, oligopyridine derivatives such as terpyridine, bipyridine derivatives, terpyridine derivatives (1,3-bis(4'-(2,2':6'2”-terpyridyl))benzene, naphthidine derivatives (bis(1-naphthyl)-4-(1,8-naphthidyl-2-yl)phenylphosphine oxide, etc.), aldehyde azo derivatives, carbazole derivatives, indole derivatives, phosphorus oxide derivatives, bisstyrene derivatives, etc.

[0479] In addition, metal complexes with electron-accepting nitrogen can also be used, such as hydroxyquinoline metal complexes, hydroxyphenyloxazole complexes and other hydroxyazole complexes; azomethine complexes, cycloheptatrienolone metal complexes, flavonol metal complexes and benzoquinoline metal complexes, etc.

[0480] The above materials can be used alone or in combination with different materials.

[0481] Among the above materials, borane derivatives, pyridine derivatives, fluoranthene derivatives, BO-based derivatives, anthracene derivatives, benzo[a]fluorene derivatives, phosphine oxide derivatives, pyrimidine derivatives, carbazole derivatives, triazine derivatives, benzimidazole derivatives, phenanthrene derivatives, and hydroxyquinoline-based metal complexes are preferred.

[0482] <Boronane derivatives>

[0483] Borane derivatives include, for example, compounds represented by the following general formula (ETM-1), details of which are disclosed in Japanese Patent Application Publication No. 2007-27587.

[0484]

[0485] In the above formula (ETM-1), R 11 and R12 Each of the following is independently a hydrogen, alkyl, cycloalkyl, optionally substituted aryl, substituted silyl, optionally substituted nitrogen-containing heterocycle, or cyano group, R 13 ~R 16 Each of the substituents can be an optionally substituted alkyl group, an optionally substituted cycloalkyl group, or an optionally substituted aryl group; X can be an optionally substituted aryl group; Y can be an optionally substituted aryl group with 16 or fewer carbon atoms, a substituted boryl group, or an optionally substituted carbazole group; and n can be an integer from 0 to 3. Furthermore, aryl, heteroaryl, alkyl, or cycloalkyl groups can be listed as substituents when "optionally substituted" or "substituted".

[0486] Among the compounds represented by the above general formula (ETM-1), the compounds represented by the following general formula (ETM-1-1) and the compounds represented by the following general formula (ETM-1-2) are preferred.

[0487]

[0488] In formula (ETM-1-1), R 11 and R 12 Each of the following is independently a hydrogen, alkyl, cycloalkyl, optionally substituted aryl, substituted silyl, optionally substituted nitrogen-containing heterocycle, or cyano group, R 13 ~R 16 Each is independently a optionally substituted alkyl, optionally substituted cycloalkyl, or optionally substituted aryl group, R 21 and R 22 Each of the following is independently a group consisting of at least one of hydrogen, alkyl, cycloalkyl, optionally substituted aryl, substituted silyl, optionally substituted nitrogen-containing heterocycle, or cyano: X 1 For arylene groups with 20 or fewer carbon atoms that are optionally substituted, n is an integer from 0 to 3, and m is an integer from 0 to 4. Furthermore, aryl, heteroaryl, alkyl, or cycloalkyl groups can be listed as substituents when "optionally substituted" or "substituted".

[0489]

[0490] In formula (ETM-1-2), R 11 and R 12 Each of the following is independently a hydrogen, alkyl, cycloalkyl, optionally substituted aryl, substituted silyl, optionally substituted nitrogen-containing heterocycle, or cyano group, R 13 ~R 16 Each of the following is independently a optionally substituted alkyl, optionally substituted cycloalkyl, or optionally substituted aryl group, X 1The substituent is an arylene group with 20 or fewer carbon atoms that are optionally substituted, and n is an integer from 0 to 3. Furthermore, aryl, heteroarylalkyl, or cycloalkyl groups can be listed as substituents when "optionally substituted" or "substituted".

[0491] As X 1 Specific examples can be listed as any of the divalent groups shown in formulas (X-1) to (X-9) below.

[0492]

[0493] (In each formula, R) a Each is independently an alkyl, cycloalkyl, or optionally substituted phenyl group.

[0494] Specific examples of this borane derivative include the following compounds.

[0495]

[0496] This borane derivative can be manufactured using known raw materials and known synthetic methods.

[0497] <Pyridine Derivatives>

[0498] The pyridine derivative is, for example, a compound represented by the following formula (ETM-2), preferably a compound represented by formula (ETM-2-1) or formula (ETM-2-2).

[0499]

[0500] φ is an n-valent aromatic ring (preferably an n-valent benzene ring, naphthalene ring, anthracene ring, fluorene ring, benzo[a]fluorene ring, phenaene ring, phenanthrene ring, or benzo[a]phenanthrene ring), and n is an integer from 1 to 4.

[0501] In the above formula (ETM-2-1), R 11 ~R 18 Each of them is independently hydrogen, alkyl (preferably alkyl with 1 to 24 carbon atoms), cycloalkyl (preferably cycloalkyl with 3 to 12 carbon atoms) or aryl (preferably aryl with 6 to 30 carbon atoms).

[0502] In the above formula (ETM-2-2), R 11 and R 12 Each is independently hydrogen, alkyl (preferably alkyl with 1 to 24 carbon atoms), cycloalkyl (preferably cycloalkyl with 3 to 12 carbon atoms), or aryl (preferably aryl with 6 to 30 carbon atoms), R 11 With R 12 Rings are formed by optional bonding.

[0503] In each formula, the "pyridine substituent" is any one of the following formulas (Py-1) to (Py-15), and each pyridine substituent is independently and optionally substituted by an alkyl group having 1 to 4 carbon atoms or a cycloalkyl group having 5 to 10 carbon atoms. In addition, the pyridine substituent is optionally bonded to the φ, anthracene ring or fluorene ring in each formula by means of a phenylene or naphthylene group.

[0504]

[0505] The pyridine substituents are any of the above formulas (Py-1) to (Py-15), and among these, they are preferably any of the following formulas (Py-21) to (Py-44).

[0506]

[0507] At least one hydrogen atom in each pyridine derivative may be optionally substituted with deuterium, and one of the two “pyridine substituents” in formulas (ETM-2-1) and (ETM-2-2) may be optionally substituted with an aryl group.

[0508] As R 11 ~R 18 The term "alkyl" can be either straight-chain or branched, and examples include straight-chain alkyl groups with 1 to 24 carbon atoms or branched alkyl groups with 3 to 24 carbon atoms. Preferred "alkyl" is an alkyl group with 1 to 18 carbon atoms (branched alkyl groups with 3 to 18 carbon atoms). More preferred "alkyl" is an alkyl group with 1 to 12 carbon atoms (branched alkyl groups with 3 to 12 carbon atoms). Further preferred "alkyl" is an alkyl group with 1 to 6 carbon atoms (branched alkyl groups with 3 to 6 carbon atoms). Particularly preferred "alkyl" is an alkyl group with 1 to 4 carbon atoms (branched alkyl groups with 3 to 4 carbon atoms).

[0509] Specific examples of "alkyl groups" include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, tert-octyl, 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-pentadecanyl, n-hexadecyl, n-heptadecyl, n-octadecyl, n-eicosyl, etc.

[0510] The description of the alkyl group described above can be used as an example of an alkyl group that has 1 to 4 carbon atoms and is substituted at a pyridine substituent.

[0511] As R11 ~R 18 The term "cycloalkyl" can be exemplified by, for example, cycloalkyl groups having 3 to 12 carbon atoms. Preferably, the "cycloalkyl" is a cycloalkyl group having 3 to 10 carbon atoms. More preferably, the "cycloalkyl" is a cycloalkyl group having 3 to 8 carbon atoms. Even more preferably, the "cycloalkyl" is a cycloalkyl group having 3 to 6 carbon atoms.

[0512] Specific examples of "cycloalkyl groups" include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclopentyl, cycloheptyl, methylcyclohexyl, cyclooctyl, or dimethylcyclohexyl.

[0513] For cycloalkyl groups with 5 to 10 carbon atoms substituted on pyridine substituents, the above description of cycloalkyl groups can be cited.

[0514] As R 11 ~R 18 The "aryl" in the text is preferably an aryl group with 6 to 30 carbon atoms, more preferably an aryl group with 6 to 18 carbon atoms, even more preferably an aryl group with 6 to 14 carbon atoms, and particularly preferably an aryl group with 6 to 12 carbon atoms.

[0515] Specific examples of "aryl groups with 6 to 30 carbon atoms" include phenyl as a monocyclic aryl group; (1-,2-)naphthyl as a fused bicyclic aryl group; acenaphthene-(1-,3-,4-,5-)yl, fluorene-(1-,2-,3-,4-,9-)yl, phenaten-(1-,2-)yl, and (1-,2-,3-,4-,9-)phenanthyl as fused tricyclic aryl groups; benzo[a]phenanthrene-(1-,2-)yl, pyrene-(1-,2-,4-)yl, and tetraphenyl-(1-,2-,5-)yl as fused tetracyclic aryl groups; and perylene-(1-,2-,3-)yl and pentaphenyl-(1-,2-,5-,6-)yl as fused pentacyclic aryl groups.

[0516] Preferred aryl groups with 6 to 30 carbon atoms include phenyl, naphthyl, phenanthryl, hydroxyl, or benzo[a]phenanthryl, and more preferably phenyl, 1-naphthyl, 2-naphthyl, or phenanthryl. Phenyl, 1-naphthyl, or 2-naphthyl are particularly preferred.

[0517] In the above formula (ETM-2-2), R 11 With R 12 The rings are formed by selective bonding, and the cyclobutane, cyclopentane, cyclopentene, cyclopentadiene, cyclohexane, fluorene, or indene are among the five-membered rings that are selectively helically bonded to the fluorene skeleton.

[0518] Specific examples of this pyridine derivative include the following compounds.

[0519]

[0520] The pyridine derivative can be produced using known raw materials and known synthesis methods.

[0521] <Fluoranthene derivative>

[0522] The fluoranthene derivative is, for example, a compound represented by the following general formula (ETM-3), and details are disclosed in International Publication No. 2010 / 134352.

[0523]

[0524] In the above formula (ETM-3), X 12 ~X 21 represents hydrogen, a halogen, a linear, branched or cyclic alkyl group, a linear, branched or cyclic alkoxy group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. Here, as the substituents when substituted, aryl groups, heteroaryl groups, alkyl groups or cycloalkyl groups can be cited, etc.

[0525] Specific examples of the fluoranthene derivative include, for example, the following compounds.

[0526]

[0527] <BO-based derivative>

[0528] The BO-based derivative is, for example, a polycyclic aromatic compound represented by the following formula (ETM-4) or a polymer of a polycyclic aromatic compound having a structure represented by the following formula (ETM-4) multiple times.

[0529]

[0530] R 1 ~R 11 Each independently represents hydrogen, an aryl group, a heteroaryl group, a diarylamino group, a diheteroarylamino group, an arylheteroarylamino group, a diarylboron group (two aryl groups are optionally bonded via a single bond or a linking group), an alkyl group, a cycloalkyl group, an alkoxy group or an aryloxy group, and at least one hydrogen in them is optionally substituted by an aryl group, a heteroaryl group, an alkyl group or a cycloalkyl group.

[0531] In addition, adjacent groups among R 1 ~R 11 are optionally bonded to each other and together with the a-ring, b-ring or c-ring form an aryl ring or a heteroaryl ring, and at least one hydrogen of the formed ring is optionally substituted by an aryl group, a heteroaryl group, a diarylamino group, a diheteroarylamino group, an arylheteroarylamino group, a diarylboron group (two aryl groups are optionally bonded via a single bond or a linking group), an alkyl group, a cycloalkyl group, an alkoxy group or an aryloxy group, and at least one hydrogen of them is optionally substituted by an aryl group, a heteroaryl group, an alkyl group or a cycloalkyl group.

[0532] Furthermore, at least one hydrogen atom in the compound or structure represented by formula (ETM-4) may optionally be substituted with a halogen or deuterium.

[0533] For an explanation of the substituents and cyclic morphology in formula (ETM-4), the explanation of the polycyclic aromatic compounds shown in the above general formula (1) can be referenced.

[0534] Specific examples of this BO-based derivative include the following compounds.

[0535]

[0536] This BO-based derivative can be manufactured using known raw materials and known synthetic methods.

[0537] <Anthracene derivatives>

[0538] One of the anthracene derivatives is, for example, a compound represented by the following formula (ETM-5-1).

[0539]

[0540] Ar can be either divalent benzene or naphthalene, and R can be either divalent. 1 ~R 4 Each of them is independently hydrogen, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, or an aryl group having 6 to 20 carbon atoms.

[0541] Ar can be independently selected from divalent benzene or naphthalene, and the two Ar can be the same or different. From the viewpoint of ease of synthesis of anthracene derivatives, the same Ar is preferred. Ar is bonded to pyridine to form a "site containing Ar and pyridine", which is bonded to anthracene in the form of a group shown, for example, any of the following formulas (Py-1) to (Py-12).

[0542]

[0543] Of these groups, those shown in any of formulas (Py-1) to (Py-9) are preferred, and those shown in any of formulas (Py-1) to (Py-6) are more preferred. The structures of the two "Ar- and pyridine-containing sites" bonded to anthracene can be the same or different; from the viewpoint of ease of synthesis of anthracene derivatives, identical structures are preferred. From the viewpoint of element characteristics, it is preferred that the structures of the two "Ar- and pyridine-containing sites" are the same or different.

[0544] Regarding R 1 ~R 4The alkyl group having 1 to 6 carbon atoms can be either straight-chain or branched. That is, it is a straight-chain alkyl group having 1 to 6 carbon atoms or a branched alkyl group having 3 to 6 carbon atoms. More preferably, it is an alkyl group having 1 to 4 carbon atoms (branched alkyl group having 3 to 4 carbon atoms). Specific examples include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, or 2-ethylbutyl, etc., preferably methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, or tert-butyl, more preferably methyl, ethyl, or tert-butyl.

[0545] As R 1 ~R 4 Specific examples of cycloalkyl groups with 3 to 6 carbon atoms include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclopentyl, cycloheptyl, methylcyclohexyl, cyclooctyl, or dimethylcyclohexyl.

[0546] For R 1 ~R 4 The aryl group having 6 to 20 carbon atoms is preferably an aryl group having 6 to 16 carbon atoms, more preferably an aryl group having 6 to 12 carbon atoms, and particularly preferably an aryl group having 6 to 10 carbon atoms.

[0547] Specific examples of "aryl groups with 6 to 20 carbon atoms" include: phenyl, (o, m, p)tolyl, (2,3-, 2,4-, 2,5-, 2,6-, 3,4-, 3,5-)xylyl, trimethylyl (2,4,6-trimethylphenyl), and (o, m, p)isopropylphenyl as monocyclic aryl groups; (2-, 3-, 4-)biphenyl as dicyclic aryl groups; (1-, 2-)naphthyl as fused dicyclic aryl groups; and terphenyl as tricyclic aryl groups (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, p-terphenyl-4'-yl, p-terphenyl-2'-yl, m-terphenyl-2'-yl, m-terphenyl-3'-yl, p-terphenyl-4'-yl, p-terphenyl-2'-yl, p-terphenyl-3'-yl, p-terphenyl-4 ... -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); anthracene-(1-,2-,9-)yl, acenaphthene-(1-,3-,4-,5-)yl, fluorene-(1-,2-,3-,4-,9-)yl, phenamen-(1-,2-)yl, (1-,2-,3-,4-,9-)phenanthrene-yl as fused tricyclic aryl groups; benzo[a]phenanthrene-(1-,2-)yl, pyrene-(1-,2-,4-)yl, benzo[a]tetraphenyl-(1-,2-,5-)yl as fused tetracyclic aryl groups; perylene-(1-,2-,3-)yl as fused pentacyclic aryl groups, etc.

[0548] The preferred "aryl group with 6 to 20 carbon atoms" is phenyl, biphenyl, terphenyl or naphthyl, more preferably phenyl, biphenyl, 1-naphthyl, 2-naphthyl or meta-terphenyl-5'-yl, even more preferably phenyl, biphenyl, 1-naphthyl or 2-naphthyl, and most preferably phenyl.

[0549] One of the anthracene derivatives is, for example, a compound represented by the following formula (ETM-5-2).

[0550]

[0551] Ar 1 Each can be a single bond, divalent benzene, naphthalene, anthracene, fluorene, or finasteride.

[0552] Ar 2 Each aryl group is independently composed of 6 to 20 carbon atoms, and the same description as "aryl group with 6 to 20 carbon atoms" in the above formula (ETM-5-1) can be used. Preferably, it is an aryl group with 6 to 16 carbon atoms, more preferably an aryl group with 6 to 12 carbon atoms, and particularly preferably an aryl group with 6 to 10 carbon atoms. Specific examples include phenyl, biphenyl, naphthyl, terphenyl, anthracene, acenaphthene, fluorenyl, phenanthyl, benzo[a]phenanthryl, pyrene, tetraphenyl, perylene, etc.

[0553] R 1 ~R 4 Each of the following can be independently hydrogen, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, or an aryl group having 6 to 20 carbon atoms, as described in the above formula (ETM-5-1).

[0554] Specific examples of these anthracene derivatives include the following compounds.

[0555]

[0556] These anthracene derivatives can be manufactured using known raw materials and known synthetic methods.

[0557] Benzo[a]fluorene derivatives

[0558] Benzo[a]fluorene derivatives are, for example, compounds represented by the following formula (ETM-6).

[0559]

[0560] Ar 1Each aryl group is independently composed of 6 to 20 carbon atoms, and the same description as "aryl group with 6 to 20 carbon atoms" in the above formula (ETM-5-1) can be used. Preferably, it is an aryl group with 6 to 16 carbon atoms, more preferably an aryl group with 6 to 12 carbon atoms, and particularly preferably an aryl group with 6 to 10 carbon atoms. Specific examples include phenyl, biphenyl, naphthyl, terphenyl, anthracene, acenaphthene, fluorenyl, phenanthyl, benzo[a]phenanthryl, pyrene, tetraphenyl, perylene, etc.

[0561] Ar 2 Each is independently hydrogen, alkyl (preferably alkyl with 1 to 24 carbon atoms), cycloalkyl (preferably cycloalkyl with 3 to 12 carbon atoms), or aryl (preferably aryl with 6 to 30 carbon atoms), and the two Ar... 2 Rings are formed by optional bonding.

[0562] As Ar 2 The term "alkyl" can be either straight-chain or branched, and examples include straight-chain alkyl groups with 1 to 24 carbon atoms or branched alkyl groups with 3 to 24 carbon atoms. Preferred "alkyl" is an alkyl group with 1 to 18 carbon atoms (branched alkyl groups with 3 to 18 carbon atoms). More preferred "alkyl" is an alkyl group with 1 to 12 carbon atoms (branched alkyl groups with 3 to 12 carbon atoms). Further preferred "alkyl" is an alkyl group with 1 to 6 carbon atoms (branched alkyl groups with 3 to 6 carbon atoms). Particularly preferred "alkyl" is an alkyl group with 1 to 4 carbon atoms (branched alkyl groups with 3 to 4 carbon atoms). Specific examples of "alkyl groups" include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, etc.

[0563] As Ar 2 The term "cycloalkyl" can be exemplified by, for example, cycloalkyl groups having 3 to 12 carbon atoms. Preferably, the "cycloalkyl" is a cycloalkyl group having 3 to 10 carbon atoms. More preferably, the "cycloalkyl" is a cycloalkyl group having 3 to 8 carbon atoms. Even more preferably, the "cycloalkyl" is a cycloalkyl group having 3 to 6 carbon atoms. Specific examples of "cycloalkyl" include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclopentyl, cycloheptyl, methylcyclohexyl, cyclooctyl, or dimethylcyclohexyl.

[0564] As Ar 2 The "aryl" in the text is preferably an aryl group with 6 to 30 carbon atoms, more preferably an aryl group with 6 to 18 carbon atoms, even more preferably an aryl group with 6 to 14 carbon atoms, and particularly preferably an aryl group with 6 to 12 carbon atoms.

[0565] Specific examples of "aryl groups with 6 to 30 carbon atoms" include phenyl, naphthyl, acenaphthel, fluorenyl, phenanthyl, benzophenanthryl, pyrene, tetraphenyl, peryl, pentaphenyl, etc.

[0566] Two Ar 2 The rings can be formed by selective bonding, resulting in the selective spirobonding of cyclobutane, cyclopentane, cyclopentene, cyclopentadiene, cyclohexane, fluorene, or indene on the five-membered ring of the fluorene skeleton.

[0567] Specific examples of this benzo[a]fluorene derivative include the following compounds.

[0568]

[0569] This benzo[a]fluorene derivative can be manufactured using known raw materials and known synthetic methods.

[0570] Phosphine oxide derivatives

[0571] Phosphine oxide derivatives are, for example, compounds represented by the following formula (ETM-7-1). Further details are described in International Publication No. 2013 / 079217.

[0572]

[0573] R 5 It can be a substituted or unsubstituted alkyl group with 1 to 20 carbon atoms, a cycloalkyl group with 3 to 20 carbon atoms, an aryl group with 6 to 20 carbon atoms, or a heteroaryl group with 5 to 20 carbon atoms.

[0574] R 6 CN, substituted or unsubstituted, alkyl with 1 to 20 carbon atoms, cycloalkyl with 3 to 20 carbon atoms, heteroalkyl with 1 to 20 carbon atoms, aryl with 6 to 20 carbon atoms, heteroaryl with 5 to 20 carbon atoms, alkoxy with 1 to 20 carbon atoms, or aryloxy with 6 to 20 carbon atoms.

[0575] R 7 and R 8 Each can be independently substituted or unsubstituted, with 6 to 20 carbon atoms as an aryl group or 5 to 20 carbon atoms as a heteroaryl group.

[0576] R 9 It is oxygen or sulfur.

[0577] j is 0 or 1, k is 0 or 1, r is an integer from 0 to 4, and q is an integer from 1 to 3.

[0578] Here, aryl, heteroaryl, alkyl, or cycloalkyl groups can be listed as substituents when they are substituted.

[0579] Phosphine oxide derivatives can be compounds, for example, those shown in the following formula (ETM-7-2).

[0580]

[0581] R 1 ~R 3 They can be the same or different, and are selected from hydrogen, alkyl, cycloalkyl, aralkyl, alkenyl, cycloalkenyl, alkoxy, alkylthio, cycloalkylthio, aryl ether, aryl thioether, aryl, heterocyclic, halogen, cyano, aldehyde, carbonyl, carboxyl, amino, nitro, silyl, and fused rings formed between adjacent substituents.

[0582] Ar 1 They can be the same or different, and can be aryl or heteroaryl. Ar 2 They can be the same or different, and can be aryl or heteroaryl. Among them, Ar... 1 and Ar 2 At least one of them has a substituent or a fused ring is formed between adjacent substituents. n is an integer from 0 to 3. When n is 0, there is no unsaturated structural part; when n is 3, there is no R. 1 .

[0583] Among these substituents, alkyl refers to saturated aliphatic hydrocarbon groups such as methyl, ethyl, propyl, and butyl, which can be unsubstituted or substituted. There are no particular limitations on the substituents used when substituted; examples include alkyl, aryl, and heterocyclic groups, which will be consistent throughout the following description. Furthermore, there is no particular limitation on the number of carbon atoms in the alkyl group; from the perspective of ease of acquisition and cost, it is generally in the range of 1 to 20.

[0584] In addition, cycloalkyl refers to saturated alicyclic hydrocarbon groups such as cyclopropyl, cyclohexyl, norbornyl, and adamantyl, which can be unsubstituted or substituted. The number of carbon atoms in the alkyl moiety is not particularly limited, and is usually in the range of 3 to 20.

[0585] Furthermore, aralkyl groups refer to aromatic hydrocarbon groups such as benzyl and phenylethyl derived from aliphatic hydrocarbons. Both aliphatic and aromatic hydrocarbons can be unsubstituted or substituted. The number of carbon atoms in the aliphatic moiety is not particularly limited, typically ranging from 1 to 20.

[0586] Furthermore, alkenyl groups refer to unsaturated aliphatic hydrocarbon groups containing double bonds, such as vinyl, allyl, and butadienyl, which can be unsubstituted or substituted. The number of carbon atoms in an alkenyl group is not particularly limited, typically ranging from 2 to 20.

[0587] In addition, cycloalkenyl refers to unsaturated alicyclic hydrocarbon groups containing double bonds, such as cyclopentenyl, cyclopentadienyl, and cyclohexenyl, which can be unsubstituted or substituted.

[0588] Furthermore, the alkynyl group refers to an unsaturated aliphatic hydrocarbon group containing a triple bond, such as the ethynyl group, which can be unsubstituted or substituted. The number of carbon atoms in the alkynyl group is not particularly limited, typically ranging from 2 to 20.

[0589] Furthermore, alkoxy groups refer to aliphatic hydrocarbon groups such as methoxy groups, which are linked by an ether bond. These aliphatic hydrocarbon groups can be unsubstituted or substituted. The number of carbon atoms in an alkoxy group is not particularly limited, but is typically in the range of 1 to 20.

[0590] Furthermore, alkylthio groups are groups formed by replacing the oxygen atom in the ether bond of an alkoxy group with a sulfur atom.

[0591] In addition, cycloalkylthio groups refer to groups in which the oxygen atom of the ether bond of a cycloalkoxy group is replaced by a sulfur atom.

[0592] Furthermore, aryl ether groups refer to aromatic hydrocarbon groups such as phenoxy groups, which are linked by an ether bond. These aromatic hydrocarbon groups can be unsubstituted or substituted. The number of carbon atoms in an aryl ether group is not particularly limited, but is typically in the range of 6 to 40.

[0593] Furthermore, aryl thioether group is a group formed by replacing the oxygen atom of the ether bond in an aryl ether group with a sulfur atom.

[0594] Furthermore, aryl refers to aromatic hydrocarbon groups such as phenyl, naphthyl, biphenyl, phenanthryl, terphenyl, and pyrene. Aryl groups can be unsubstituted or substituted. The number of carbon atoms in an aryl group is not particularly limited, typically ranging from 6 to 40.

[0595] Furthermore, heterocyclic groups refer to cyclic groups having atoms other than carbon, such as furanyl, thiophene, oxazolyl, pyridinyl, quinolinyl, and carbazoleyl. These groups can be unsubstituted or substituted. The number of carbon atoms in heterocyclic groups is not particularly limited, but is usually in the range of 2 to 30.

[0596] Halogens are represented by fluorine, chlorine, bromine, and iodine.

[0597] It can also be contained in groups formed by substituting aldehyde, carbonyl, or amino groups with aliphatic hydrocarbons, alicyclic hydrocarbons, aromatic hydrocarbons, heterocycles, etc.

[0598] In addition, aliphatic hydrocarbons, alicyclic hydrocarbons, aromatic hydrocarbons, and heterocyclic hydrocarbons can be either unsubstituted or substituted.

[0599] Silyl groups refer to silicon compound groups such as trimethylsilyl, which may be unsubstituted or substituted. The number of carbon atoms in a silyl group is not particularly limited, typically ranging from 3 to 20. Furthermore, the number of silicon atoms is usually 1 to 6.

[0600] Fused rings formed between adjacent substituents refer to, for example, in Ar... 1With R 2 Ar 1 With R 3 Ar 2 With R 2 Ar 2 With R 3 R 2 With R 3 Ar 1 with Ar 2 Conjugate or non-conjugate condensed rings formed between [elements]. Here, when n is 1, any two R [elements] are chosen. 1 These rings can form conjugated or non-conjugated fused rings. These fused rings can contain nitrogen, oxygen, and sulfur atoms in their internal structure, and can also be further fused with other rings.

[0601] Specific examples of this phosphine oxide derivative include the following compounds.

[0602]

[0603] This phosphine oxide derivative can be manufactured using known raw materials and known synthetic methods.

[0604] <Pyrimidine derivatives>

[0605] 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). Further details are described in International Publication No. 2011 / 021689.

[0606]

[0607] Ar is independently either an aryl group or a heteroaryl group that is optionally substituted. n is an integer from 1 to 4, preferably an integer from 1 to 3, and more preferably 2 or 3.

[0608] The "aryl group" that can be substituted can be exemplified by aryl groups with 6 to 30 carbon atoms, preferably aryl groups with 6 to 24 carbon atoms, more preferably aryl groups with 6 to 20 carbon atoms, and even more preferably aryl groups with 6 to 12 carbon atoms.

[0609] Specific examples of "aryl" include phenyl as a monocyclic aryl group; (2-, 3-, 4-)biphenyl as a dicyclic aryl group; (1-, 2-)naphthyl as a fused dicyclic aryl group; terphenyl as a tricyclic aryl group (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); and fused tricyclic aryl groups. Acenaphthene-(1-,3-,4-,5-)yl, fluorene-(1-,2-,3-,4-,9-)yl, phenaten-(1-,2-)yl, (1-,2-,3-,4-,9-)phenanthrene; tetraphenyl as a tetracyclic aryl group (5'-phenyl-m-terphenyl-2-yl, 5'-phenyl-m-terphenyl-3-yl, 5'-phenyl-m-terphenyl-4-yl, m-tetraphenyl); benzophenanthrene-(1-,2-)yl, pyrene-(1-,2-,4-)yl, benzotetraphenyl-(1-,2-,5-)yl as a fused tetracyclic aryl group; perylene-(1-,2-,3-)yl, benzopentaphenyl-(1-,2-,5-,6-)yl as a fused pentacyclic aryl group, etc.

[0610] The term "heteroaryl" as "optionally substituted heteroaryl" can be exemplified by heteroaryl groups having 2 to 30 carbon atoms, preferably heteroaryl groups having 2 to 25 carbon atoms, more preferably heteroaryl groups having 2 to 20 carbon atoms, even more preferably heteroaryl groups having 2 to 15 carbon atoms, and particularly preferably heteroaryl groups having 2 to 10 carbon atoms. Furthermore, heterocyclic rings containing 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen as cyclic atoms, in addition to carbon, can also be exemplified.

[0611] Specific heteroaryl groups include, for example, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazole, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, pyrazolyl, pyridyl, pyrimidinyl, pyridazinyl, triazinyl, indole, isindole, 1H-indazole, benzimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolinyl, isoquinolinyl, cenolinyl, quinazolinyl, quinoxolinyl, phthalazinyl, naphridinyl, purine, pteridinyl, carbazole, acridineyl, phenoxthiazolyl, phenoxazinyl, phenthiazolyl. Phenazinyl, dibenzo[b,e][1,4]nitrosilanehexacyclohexyl, indene, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, naphthobenzofuranyl, thiophenyl, benzothiophenyl, isobenzothiophenyl, dibenzothiophenyl, naphthobenzothiophenyl, benzophosphanepentadienyl, dibenzophosphanepentadienyl, monovalent group of benzophosphanepentadienyl oxide ring, monovalent group of dibenzophosphanepentadienyl oxide ring, furazinyl, thianyl, indolocarbazoyl, benzoindolocarbazoyl and benzobenzoindolocarbazoyl, etc.

[0612] Furthermore, at least one hydrogen atom of the aforementioned aryl and heteroaryl groups may optionally be substituted, for example, by the aforementioned aryl and heteroaryl groups.

[0613] Specific examples of this pyrimidine derivative include the following compounds.

[0614]

[0615] This pyrimidine derivative can be manufactured using known raw materials and known synthetic methods.

[0616] <Carbazole derivatives>

[0617] Carbazole derivatives are, for example, compounds represented by the following formula (ETM-9) or polymers thereof formed by bonding multiple compounds together by single bonds, etc. Details are set out in U.S. Publication No. 2014 / 0197386.

[0618]

[0619] Ar is independently an aryl group or a heteroaryl group that is optionally substituted. n is an integer from 0 to 4, preferably an integer from 0 to 3, and more preferably 0 or 1.

[0620] The "aryl group" that can be substituted can be exemplified by aryl groups with 6 to 30 carbon atoms, preferably aryl groups with 6 to 24 carbon atoms, more preferably aryl groups with 6 to 20 carbon atoms, and even more preferably aryl groups with 6 to 12 carbon atoms.

[0621] Specific examples of "aryl" include phenyl as a monocyclic aryl group; (2-, 3-, 4-)biphenyl as a dicyclic aryl group; (1-, 2-)naphthyl as a fused dicyclic aryl group; terphenyl as a tricyclic aryl group (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); and fused tricyclic aryl groups. Acenaphthene-(1-,3-,4-,5-)yl, fluorene-(1-,2-,3-,4-,9-)yl, phenaten-(1-,2-)yl, (1-,2-,3-,4-,9-)phenanthrene; tetraphenyl as a tetracyclic aryl group (5'-phenyl-m-terphenyl-2-yl, 5'-phenyl-m-terphenyl-3-yl, 5'-phenyl-m-terphenyl-4-yl, m-tetraphenyl); benzophenanthrene-(1-,2-)yl, pyrene-(1-,2-,4-)yl, benzotetraphenyl-(1-,2-,5-)yl as a fused tetracyclic aryl group; perylene-(1-,2-,3-)yl, benzopentaphenyl-(1-,2-,5-,6-)yl as a fused pentacyclic aryl group, etc.

[0622] The term "heteroaryl" as "optionally substituted heteroaryl" can be exemplified by heteroaryl groups having 2 to 30 carbon atoms, preferably heteroaryl groups having 2 to 25 carbon atoms, more preferably heteroaryl groups having 2 to 20 carbon atoms, even more preferably heteroaryl groups having 2 to 15 carbon atoms, and particularly preferably heteroaryl groups having 2 to 10 carbon atoms. Furthermore, heterocyclic rings containing 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen as cyclic atoms, in addition to carbon, can also be exemplified.

[0623] Specific heteroaryl groups include, for example, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazole, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, pyrazolyl, pyridyl, pyrimidinyl, pyridazinyl, triazinyl, indole, isindole, 1H-indazole, benzimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolinyl, isoquinolinyl, cenolinyl, quinazolinyl, quinoxolinyl, phthalazinyl, naphridinyl, purine, pteridinyl, carbazole, acridineyl, phenoxthiazolyl, phenoxazinyl, phenthiazolyl. Phenazinyl, dibenzo[b,e][1,4]nitrosilanehexacyclohexyl, indene, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, naphthobenzofuranyl, thiophenyl, benzothiophenyl, isobenzothiophenyl, dibenzothiophenyl, naphthobenzothiophenyl, benzophosphanepentadienyl, dibenzophosphanepentadienyl, monovalent group of benzophosphanepentadienyl oxide ring, monovalent group of dibenzophosphanepentadienyl oxide ring, furazinyl, thianyl, indolocarbazoyl, benzoindolocarbazoyl and benzobenzoindolocarbazoyl, etc.

[0624] Furthermore, at least one hydrogen atom in the aforementioned aryl and heteroaryl groups may optionally be substituted, for example, by the aforementioned aryl and heteroaryl groups.

[0625] Carbazole derivatives can be polymers formed by bonding multiple compounds of the above formula (ETM-9) via single bonds or other means. In this case, in addition to single bonds, they can also be bonded via aromatic rings (preferably polyvalent benzene rings, naphthyl rings, anthracene rings, fluorene rings, benzo[a]fluorene rings, finadene rings, phenanthrene rings, or benzo[a]phenanthrene rings).

[0626] Specific examples of this carbazole derivative include the following compounds.

[0627]

[0628] This carbazole derivative can be manufactured using known raw materials and known synthetic methods.

[0629] <Triazine derivatives>

[0630] Triazine derivatives are, for example, compounds represented by the following formula (ETM-10), preferably compounds represented by the following formula (ETM-10-1). Details are set out in U.S. Publication No. 2011 / 0156013.

[0631]

[0632] Ar is independently either an aryl group or a heteroaryl group that is optionally substituted. n is an integer from 1 to 3, preferably 2 or 3.

[0633] The "aryl group" that can be substituted can be exemplified by aryl groups with 6 to 30 carbon atoms, preferably aryl groups with 6 to 24 carbon atoms, more preferably aryl groups with 6 to 20 carbon atoms, and even more preferably aryl groups with 6 to 12 carbon atoms.

[0634] Specific examples of "aryl" include phenyl as a monocyclic aryl group; (2-, 3-, 4-)biphenyl as a dicyclic aryl group; (1-, 2-)naphthyl as a fused dicyclic aryl group; terphenyl as a tricyclic aryl group (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); and fused tricyclic aryl groups. Acenaphthene-(1-,3-,4-,5-)yl, fluorene-(1-,2-,3-,4-,9-)yl, phenaten-(1-,2-)yl, (1-,2-,3-,4-,9-)phenanthrene; tetraphenyl as a tetracyclic aryl group (5'-phenyl-m-terphenyl-2-yl, 5'-phenyl-m-terphenyl-3-yl, 5'-phenyl-m-terphenyl-4-yl, m-tetraphenyl); benzophenanthrene-(1-,2-)yl, pyrene-(1-,2-,4-)yl, benzotetraphenyl-(1-,2-,5-)yl as a fused tetracyclic aryl group; perylene-(1-,2-,3-)yl, benzopentaphenyl-(1-,2-,5-,6-)yl as a fused pentacyclic aryl group, etc.

[0635] The term "heteroaryl" as "optionally substituted heteroaryl" can be exemplified by heteroaryl groups having 2 to 30 carbon atoms, preferably heteroaryl groups having 2 to 25 carbon atoms, more preferably heteroaryl groups having 2 to 20 carbon atoms, even more preferably heteroaryl groups having 2 to 15 carbon atoms, and particularly preferably heteroaryl groups having 2 to 10 carbon atoms. Furthermore, heterocyclic rings containing 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen as cyclic atoms, in addition to carbon, can also be exemplified.

[0636] Specific heteroaryl groups include, for example, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazole, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, pyrazolyl, pyridyl, pyrimidinyl, pyridazinyl, triazinyl, indole, isindole, 1H-indazole, benzimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolinyl, isoquinolinyl, cenolinyl, quinazolinyl, quinoxolinyl, phthalazinyl, naphridinyl, purine, pteridinyl, carbazole, acridineyl, phenoxthiazolyl, phenoxazinyl, phenthiazolyl. Phenazinyl, dibenzo[b,e][1,4]nitrosilanehexacyclohexyl, indene, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, naphthobenzofuranyl, thiophenyl, benzothiophenyl, isobenzothiophenyl, dibenzothiophenyl, naphthobenzothiophenyl, benzophosphanepentadienyl, dibenzophosphanepentadienyl, monovalent group of benzophosphanepentadienyl oxide ring, monovalent group of dibenzophosphanepentadienyl oxide ring, furazinyl, thianyl, indolocarbazoyl, benzoindolocarbazoyl and benzobenzoindolocarbazoyl, etc.

[0637] Furthermore, at least one hydrogen atom in the aforementioned aryl and heteroaryl groups may optionally be substituted, for example, by the aforementioned aryl and heteroaryl groups.

[0638] Specific examples of this triazine derivative include the following compounds.

[0639]

[0640] This triazine derivative can be manufactured using known raw materials and known synthetic methods.

[0641] <benzimidazole derivatives>

[0642] Benzimidazole derivatives are, for example, compounds represented by the following formula (ETM-11).

[0643]

[0644] φ is an n-valent aromatic ring (preferably an n-valent benzene ring, naphthyl ring, anthracene ring, fluorene ring, benzo[a]fluorene ring, finadene ring, phenanthrene ring, or benzo[a]phenanthrene ring), n is an integer from 1 to 4, and "benzimidazole substituent" is a substituent obtained by replacing the pyridinyl group in the "pyridine substituent" in the above formulas (ETM-2), (ETM-2-1), and (ETM-2-2) with a benzimidazole group, wherein at least one hydrogen in the benzimidazole derivative is optionally substituted with deuterium.

[0645]

[0646] The R in the above benzimidazole group 11R can be hydrogen, an alkyl group having 1 to 24 carbon atoms, a cycloalkyl group having 3 to 12 carbon atoms, or an aryl group having 6 to 30 carbon atoms, and can be referenced from the above formulas (ETM-2-1) and (ETM-2-2). 11 Explanation.

[0647] φ is preferably further composed of anthracene ring or fluorene ring, and the structure therein can be described by referring to the above formula (ETM-2-1) or formula (ETM-2-2), where R in each formula 11 ~R 18 The descriptions in ETM-2-1 or ETM-2-2 above can be referenced. Furthermore, in ETM-2-1 or ETM-2-2 above, the description uses a configuration with two pyridine substituents. However, when replacing them with benzimidazole substituents, both pyridine substituents can be replaced with benzimidazole substituents (i.e., n=2), or either one pyridine substituent can be replaced with a benzimidazole substituent, and the other pyridine substituent can be replaced with R. 11 ~R 18 Perform a substitution (i.e., n=1). Furthermore, for example, R in the above equation (ETM-2-1) can also be... 11 ~R 18 At least one of them is replaced with a benzimidazole substituent, and the "pyridine substituent" is represented by R. 11 ~R 18 Perform the replacement.

[0648] Specific examples of this benzimidazole derivative include, for instance, 1-phenyl-2-(4-(10-phenylanthracene-9-yl)phenyl)-1H-benzi[d]imidazole, 2-(4-(10-(naphthyl-2-yl)anthracene-9-yl)phenyl)-1-phenyl-1H-benzi[d]imidazole, 2-(3-(10-(naphthyl-2-yl)anthracene-9-yl)phenyl)-1-phenyl-1H-benzi[d]imidazole, and 5-(10-(naphthyl-2-yl)anthracene-9-yl)-1,2-diphenyl-1H-benzi[d]imidazole. Imidazole, 1-(4-(10-(naphth-2-yl)anthracene-9-yl)phenyl)-2-phenyl-1H-benzo[d]imidazol, 2-(4-(9,10-bis(naphth-2-yl)anthracene-2-yl)phenyl)-1-phenyl-1H-benzo[d]imidazol, 1-(4-(9,10-bis(naphth-2-yl)anthracene-2-yl)phenyl)-2-phenyl-1H-benzo[d]imidazol, 5-(9,10-bis(naphth-2-yl)anthracene-2-yl)-1,2-diphenyl-1H-benzo[d]imidazol, etc.

[0649]

[0650] This benzimidazole derivative can be manufactured using known raw materials and known synthetic methods.

[0651] <Phenanthroline derivatives>

[0652] The phenanthrene derivatives are, for example, compounds represented by the following formula (ETM-12) or formula (ETM-12-1). Details are set forth in International Publication No. 2006 / 021982.

[0653]

[0654] φ is an n-valent aromatic ring (preferably an n-valent benzene ring, naphthalene ring, anthracene ring, fluorene ring, benzo[a]fluorene ring, phenaene ring, phenanthrene ring, or benzo[a]phenanthrene ring), and n is an integer from 1 to 4.

[0655] Various R 11 ~R 18 Each of them is independently hydrogen, alkyl (preferably alkyl with 1 to 24 carbon atoms), cycloalkyl (preferably cycloalkyl with 3 to 12 carbon atoms), or aryl (preferably aryl with 6 to 30 carbon atoms). Furthermore, in the above formula (ETM-12-1), R... 11 ~R 18 Any of the molecules in the ring can bond with φ, which is an aromatic ring.

[0656] At least one hydrogen atom in each phenanthrene derivative may be optionally substituted with deuterium.

[0657] As R 11 ~R 18 The alkyl, cycloalkyl, and aryl groups in the above formula (ETM-2) can be referred to as R. 11 ~R 18 The explanation is as follows. In addition to the examples mentioned above, φ can also be represented by the following structural formulas. It should be noted that R in the following structural formulas is independently hydrogen, methyl, ethyl, isopropyl, cyclohexyl, phenyl, 1-naphthyl, 2-naphthyl, biphenyl, or terphenyl.

[0658]

[0659] Specific examples of this phenanthrene derivative include, for example, 4,7-diphenyl-1,10-phenanthrene, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthrene, 9,10-bis(1,10-phenanthrene-2-yl)anthracene, 2,6-bis(1,10-phenanthrene-5-yl)pyridine, 1,3,5-tris(1,10-phenanthrene-5-yl)benzene, 9,9'-difluoro-bis(1,10-phenanthrene-5-yl), copper bath, 1,3-bis(2-phenyl-1,10-phenanthrene-9-yl)benzene, and compounds with the following structural formulas.

[0660]

[0661] This phenanthrene derivative can be manufactured using known raw materials and known synthetic methods.

[0662] Hydroxyquinoline metal complexes

[0663] Hydroxyquinoline metal complexes are, for example, compounds represented by the following general formula (ETM-13).

[0664]

[0665] In the formula, R 1 ~R 6 Each of them is independently hydrogen, fluorine, alkyl, cycloalkyl, aralkyl, alkenyl, cyano, alkoxy or aryl, M is Li, Al, Ga, Be or Zn, and n is an integer from 1 to 3.

[0666] Specific examples of hydroxyquinoline-based metal complexes include lithium 8-hydroxyquinoline, tris(8-hydroxyquinoline)aluminum, tris(4-methyl-8-hydroxyquinoline)aluminum, tris(5-methyl-8-hydroxyquinoline)aluminum, tris(3,4-dimethyl-8-hydroxyquinoline)aluminum, tris(4,5-dimethyl-8-hydroxyquinoline)aluminum, tris(4,6-dimethyl-8-hydroxyquinoline)aluminum, bis(2-methyl-8-hydroxyquinoline)(phenol)aluminum, bis(2-methyl-8-hydroxyquinoline)(2-methylphenol)aluminum, bis(2-methyl-8-hydroxyquinoline)(3-methylphenol)aluminum, and bis( 2-Methyl-8-hydroxyquinoline (4-methylphenol)aluminum, bis(2-methyl-8-hydroxyquinoline (2-phenylphenol)aluminum, bis(2-methyl-8-hydroxyquinoline (3-phenylphenol)aluminum, bis(2-methyl-8-hydroxyquinoline (4-phenylphenol)aluminum, bis(2-methyl-8-hydroxyquinoline (2,3-dimethylphenol)aluminum, bis(2-methyl-8-hydroxyquinoline (2,6-dimethylphenol)aluminum, bis(2-methyl-8-hydroxyquinoline (3,4-dimethylphenol)aluminum, bis(2-methyl-8-hydroxyquinoline (3,5-dimethylphenol)aluminum) Aluminum, bis(2-methyl-8-hydroxyquinoline)(3,5-di-tert-butylphenol)aluminum, bis(2-methyl-8-hydroxyquinoline)(2,6-diphenylphenol)aluminum, bis(2-methyl-8-hydroxyquinoline)(2,4,6-triphenylphenol)aluminum, bis(2-methyl-8-hydroxyquinoline)(2,4,6-trimethylphenol)aluminum, bis(2-methyl-8-hydroxyquinoline)(2,4,5,6-tetramethylphenol)aluminum, bis(2-methyl-8-hydroxyquinoline)(1-naphthol)aluminum, bis(2-methyl-8-hydroxyquinoline)(2-naphthol)aluminum, bis(2,4-dimethyl... bis(2,4-dimethyl-8-hydroxyquinoline)(2-phenylphenol)aluminum, bis(2,4-dimethyl-8-hydroxyquinoline)(3-phenylphenol)aluminum, bis(2,4-dimethyl-8-hydroxyquinoline)(4-phenylphenol)aluminum, bis(2,4-dimethyl-8-hydroxyquinoline)(3,5-dimethylphenol)aluminum, bis(2,4-dimethyl-8-hydroxyquinoline)(3,5-ditert-butylphenol)aluminum, bis(2-methyl-8-hydroxyquinoline)aluminum-μ-oxo-bis(2-methyl-8-hydroxyquinoline)aluminum, bis(2,4-dimethyl-8-hydroxyquinoline)aluminum-μ-oxo- ...4-Dimethyl-8-hydroxyquinoline)aluminum, bis(2-methyl-4-ethyl-8-hydroxyquinoline)aluminum-μ-oxo-bis(2-methyl-4-ethyl-8-hydroxyquinoline)aluminum, bis(2-methyl-4-methoxy-8-hydroxyquinoline)aluminum-μ-oxo-bis(2-methyl-4-methoxy-8-hydroxyquinoline)aluminum, bis(2-methyl-5-cyano-8-hydroxyquinoline)aluminum-μ-oxo-bis(2-methyl-5-cyano-8-hydroxyquinoline)aluminum, bis(2-methyl-5-trifluoromethyl-8-hydroxyquinoline)aluminum-μ-oxo-bis(2-methyl-5-trifluoromethyl-8-hydroxyquinoline)aluminum, bis(10-hydroxybenzo[h]quinoline)beryllium, etc.

[0667] This hydroxyquinoline-based metal complex can be manufactured using known raw materials and known synthetic methods.

[0668] <Thiazole derivatives and benzothiazole derivatives>

[0669] Thiazole derivatives are, for example, compounds represented by the following formula (ETM-14-1).

[0670]

[0671] Benzothiazole derivatives are, for example, compounds represented by the following formula (ETM-14-2).

[0672]

[0673] In each formula, φ is an n-valent aromatic ring (preferably an n-valent benzene ring, naphthyl ring, anthracene ring, fluorene ring, benzo[a]fluorene ring, finadene ring, phenanthrene ring, or benzo[a]phenanthrene ring), n is an integer from 1 to 4, "thiazole substituent" and "benzo[a]thiazole substituent" are substituents obtained by replacing the pyridinium group in the "pyridine substituent" in the above formulas (ETM-2), (ETM-2-1) and (ETM-2-2) with the following thiazole group and benzo[a]thiazole group, and at least one hydrogen in the thiazole derivative and benzo[a]thiazole derivative may optionally be substituted with deuterium.

[0674]

[0675] φ is preferably further composed of anthracene ring or fluorene ring, and the structure therein can be described by referring to the above formula (ETM-2-1) or formula (ETM-2-2), where R in each formula 11 ~R 18The descriptions in ETM-2-1 or ETM-2-2 above can be referenced. Furthermore, while ETM-2-1 or ETM-2-2 describes a configuration with two pyridine substituents, when these are replaced with thiazole substituents (or benzothiazole substituents), both pyridine substituents can be replaced with thiazole substituents (or benzothiazole substituents) (i.e., n=2), or either one pyridine substituent can be replaced with a thiazole substituent (or benzothiazole substituent), and the other pyridine substituent can be replaced with R. 11 ~R 18 Perform a substitution (i.e., n=1). Furthermore, for example, R in the above equation (ETM-2-1) can also be... 11 ~R 18 At least one of them is replaced with a thiazole-based substituent (or a benzothiazole-based substituent), and the "pyridine-based substituent" is represented by R. 11 ~R 18 Perform the replacement.

[0676] These thiazole derivatives or benzothiazole derivatives can be manufactured using known raw materials and known synthetic methods.

[0677] The electron transport layer or electron injection layer may further include a substance capable of reducing the material forming the electron transport layer or electron injection layer. This reducing substance can be any substance possessing a certain reducing property, and is suitably selected from at least one 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.

[0678] Preferred reducing agents include alkali metals such as Na (work function 2.36 eV), K (work function 2.28 eV), Rb (work function 2.16 eV), or Cs (work function 1.95 eV); and alkaline earth metals such as Ca (work function 2.9 eV), Sr (work function 2.0~2.5 eV), or Ba (work function 2.52 eV), with substances having a work function of 2.9 eV or less being particularly preferred. Among these, alkali metals such as K, Rb, or Cs are more preferred, Rb or Cs are even more preferred, and Cs is the most preferred. These alkali metals, in particular, have high reducing power, and by adding a small amount to the material forming the electron transport layer or electron injection layer, the luminous brightness and lifetime of organic EL devices can be improved. Furthermore, combinations of two or more alkali metals with a work function of 2.9 eV or less are preferred as reducing agents, particularly combinations containing Cs, such as Cs and Na, Cs and K, Cs and Rb, or combinations of Cs, Na, and K. By including Cs, the reducing ability can be efficiently utilized, and by adding it to the material forming the electron transport layer or electron injection layer, the luminous brightness and lifetime of the organic EL device can be improved.

[0679] The aforementioned electron injection layer materials and electron transport layer materials can also be used as electron layer materials in the following forms: polymeric compounds or their polymeric cross-links obtained by polymerizing reactive compounds obtained by substituting reactive substituents on them, or side-chain type polymeric compounds or their side-chain type polymeric cross-links obtained by reacting a main-chain type polymer with the aforementioned reactive compounds. The description of the reactive substituents in the polycyclic aromatic compounds shown in formula (1) can be cited as examples of such reactive substituents.

[0680] The applications of such polymers and polymer crosslinkers are detailed below.

[0681] Cathode in Organic Electroluminescent Devices

[0682] The cathode 108 injects electrons into the light-emitting layer 105 by means of the electron injection layer 107 and the electron transport layer 106.

[0683] The material forming the cathode 108 is not particularly limited as long as it can efficiently inject electrons into the organic layer, and the same material as the material forming the anode 102 can be used. Preferably, metals such as tin, indium, calcium, aluminum, silver, copper, nickel, chromium, gold, platinum, iron, zinc, lithium, sodium, potassium, cesium, and magnesium, or alloys thereof (magnesium-silver alloys, magnesium-indium alloys, lithium fluoride / aluminum and other aluminum-lithium alloys, etc.) are preferred. To improve the electron injection efficiency and thus enhance the 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, methods such as doping the organic layer with trace amounts of lithium, cesium, and magnesium and using a highly stable electrode are known. Other dopants can also be used, such as inorganic salts like lithium fluoride, cesium fluoride, lithium oxide, and cesium oxide. However, they are not limited to these.

[0684] Furthermore, to protect the electrodes, preferred examples include stacking metals such as platinum, gold, silver, copper, iron, tin, aluminum, and indium, or alloys using these metals, as well as inorganic materials such as silicon dioxide, titanium dioxide, and silicon nitride, polyvinyl alcohol, vinyl chloride, and hydrocarbon polymers. These electrodes can be fabricated using methods such as resistance heating, electron beam evaporation, sputtering, ion plating, and coating; there are no particular limitations as long as conductivity can be achieved.

[0685] <Adhesives that can be used in each layer>

[0686] The materials used in the hole injection layer, hole transport layer, light emission layer, electron transport layer, and electron injection layer can be formed individually or dispersed in solvent-soluble resins such as polyvinyl chloride, polycarbonate, polystyrene, poly(N-vinylcarbazole), polymethyl methacrylate, polybutyl methacrylate, polyester, polysulfone, polyphenylene ether, polybutadiene, hydrocarbon resins, ketone resins, phenoxy resins, polyamide, ethyl cellulose, vinyl acetate resin, ABS resin, polyurethane resin, phenolic resin, xylene resin, petroleum resin, urea resin, melamine resin, unsaturated polyester resin, alkyd resin, epoxy resin, and silicone resin, etc., which are used as polymer binders.

[0687] <Methods for fabricating organic electroluminescent elements>

[0688] The layers constituting an organic electroluminescent (EL) element can be formed by depositing thin films of the materials to be composed of each layer using methods such as vapor deposition, resistance heating vapor deposition, electron beam vapor deposition, sputtering, molecular lamination, printing, spin coating, casting, and coating. The thickness of each layer formed in this way is not particularly limited and can be appropriately set according to the properties of the material, typically ranging from 2 nm to 5000 nm. Film thickness can usually be measured using a quartz oscillating film thickness measuring device. When using vapor deposition for thin film formation, the deposition conditions vary depending on the type of material, the target crystal structure of the film, and the association structure. Preferred deposition conditions are typically a boat heating temperature of +50 to +400°C and a vacuum degree of 10... -6 ~10 -3 The following parameters should be appropriately set: Pa, evaporation rate (0.01~50 nm / s), substrate temperature (-150~+300℃), and film thickness (2 nm~5 μm).

[0689] When applying a DC voltage to the organic EL element obtained through this operation, simply apply the voltage with the anode set to + and the cathode set to -. If a voltage of approximately 2 to 40V is applied, light emission can be observed from the transparent or semi-transparent electrode side (anode or cathode, and both sides). Furthermore, this organic EL element also emits light when pulsed current or alternating current is applied. It should be noted that the waveform of the applied alternating current can be arbitrary.

[0690] Next, as an example of a method for fabricating an organic EL device, a method for fabricating an organic EL device comprising an anode / hole injection layer / hole transport layer / light-emitting layer / electron transport layer / electron injection layer / cathode formed of a host material and a doped material will be described.

[0691] <Evaporation method>

[0692] After fabricating an anode by forming a thin film of anode material on a suitable substrate using methods such as vapor deposition, a hole injection layer and a hole transport layer are formed on the anode. A host material and a dopant material are then co-deposited on the anode to form a thin film, creating a light-emitting layer. An electron transport layer and an electron injection layer are then formed on the light-emitting layer. Finally, a cathode is fabricated by forming a thin film containing a cathode material using methods such as vapor deposition, thereby obtaining the target organic EL device. It should be noted that in the fabrication of the above-mentioned organic EL device, the fabrication order can be reversed, and the device can be fabricated in the order of cathode, electron injection layer, electron transport layer, light-emitting layer, hole transport layer, hole injection layer, and anode.

[0693] <Wet film formation method>

[0694] The wet film-forming method is carried out by preparing a low-molecular-weight compound that can form each organic layer of an organic EL element as a liquid organic layer-forming composition. When a suitable organic solvent for dissolving the low-molecular-weight compound is unavailable, the organic layer-forming composition can also be prepared from a polymeric compound, which is a reactive compound obtained by substituting reactive substituents onto the low-molecular-weight compound and polymerizing it together with other monomers and main-chain polymers that have solubility properties.

[0695] Generally, wet film formation involves a coating process of applying an organic layer forming composition onto a substrate and a drying process of removing the solvent from the applied organic layer forming composition. When the aforementioned polymeric compound has crosslinking substituents (also referred to as a crosslinked polymeric compound), it undergoes further crosslinking during the drying process to form a crosslinked polymer. Depending on the coating process, methods using a spin coater are called spin coating, methods using a slot coater are called slot coating, methods using printing plates are called gravure, offset, reverse offset, or flexographic printing, methods using an inkjet printer are called inkjet printing, and methods that spray in a mist are called spraying. Drying processes include air drying, heating, and vacuum drying. The drying process can be performed once or multiple times using different methods and conditions. Furthermore, for example, firing under reduced pressure, different methods can be used in combination.

[0696] Wet film deposition refers to film deposition methods that use solutions, such as some printing methods (inkjet printing), spin coating, casting, and coating processes. Unlike vacuum evaporation, wet film deposition does not require expensive vacuum evaporation equipment and can form films under atmospheric pressure. Furthermore, wet film deposition enables large-area, continuous production, which helps reduce manufacturing costs.

[0697] On the other hand, wet deposition methods are sometimes difficult to laminate compared to vacuum evaporation. When using wet deposition methods to fabricate laminated films, it is necessary to prevent the lower layers from dissolving due to the composition of the upper layers, and to use compositions with controlled solubility, crosslinking of the lower layers, and orthogonal solvents (immiscible solvents). However, even with these techniques, it is sometimes difficult to use wet deposition methods for coating the entire film.

[0698] Therefore, the following method is usually adopted: only a few layers are fabricated using wet deposition, and the rest are fabricated using vacuum evaporation to create organic EL devices.

[0699] For example, the following shows some steps for fabricating organic EL elements using a wet film deposition method.

[0700] (Step 1) Film formation of the anode based on vacuum evaporation

[0701] (Step 2) Film formation based on wet film formation method of a composition for forming a hole injection layer containing a material for the hole injection layer.

[0702] (Step 3) Film formation based on wet film formation method of a composition for forming a hole transport layer containing a material for the hole transport layer.

[0703] (Step 4) Film formation based on wet film formation method of the composition for forming a light-emitting layer containing host material and doped material

[0704] (Step 5) Electron transport layer film formation based on vacuum evaporation method

[0705] (Step 6) Electron injection layer film formation based on vacuum evaporation method

[0706] (Step 7) Film formation of the cathode based on vacuum evaporation

[0707] This process yields an organic EL device composed of an anode / hole injection layer / hole transport layer / light-emitting layer containing host and doped materials / electron transport layer / electron injection layer / cathode.

[0708] Of course, by using means to prevent the dissolution of the underlying light-emitting layer or by using means to form a film from the cathode side in the opposite manner to the above steps, it is possible to produce a layer-forming composition containing materials for an electron transport layer and materials for an electron injection layer, and to form them into films by a wet film-forming method.

[0709] Other film-forming methods

[0710] In the film formation of organic layer forming compositions, laser heating deposition (LITI) can be used. LITI refers to a method of heating and vaporizing a compound attached to a substrate using a laser. The material coated onto the substrate can be an organic layer forming composition.

[0711] <Optional Process>

[0712] Appropriate treatment, cleaning, and drying processes can be added before and after each step of the film formation process. Examples of treatment processes include exposure treatment, plasma surface treatment, ultrasonic treatment, ozone treatment, cleaning treatment using appropriate solvents, and heat treatment. Furthermore, a series of processes for making a bank can also be listed.

[0713] The dike can be constructed using photolithography. Positive and negative resist materials can be used as dike materials for photolithography. Additionally, patternable printing methods such as inkjet printing, gravure printing, reverse printing, and screen printing can also be used. In these cases, permanent resist materials can also be employed.

[0714] Materials used in dikes include, but are not limited to, polysaccharides and their derivatives, homopolymers and copolymers of hydroxyl-containing olefinic monomers, biopolymers, polyacrylamide compounds, polyesters, polystyrene, polyimide, polyamide-imide, polyether-imide, polysulfone, polyphenylene oxide, polyphenylene ether, polyurethane, epoxy (meth)acrylate, melamine (meth)acrylate, polyolefins, cyclic polyolefins, acrylonitrile-butadiene-styrene copolymer (ABS), silicone resins, polyvinyl chloride, chlorinated polyethylene, chlorinated polypropylene, polyacetate, polynorbornene, synthetic rubber, polyvinylidene fluoride, polytetrafluoroethylene, polyhexafluoropropylene and other fluorinated polymers, copolymers of fluoroolefins and hydrogen olefins, and fluorocarbon polymers.

[0715] <Organic layer-forming compositions used in wet film-forming methods>

[0716] The composition for forming organic layers is obtained by dissolving low-molecular-weight compounds capable of forming organic EL elements in an organic solvent, or by polymerizing such low-molecular-weight compounds into high-molecular-weight compounds. For example, the composition for forming a light-emitting layer contains: at least one polycyclic aromatic compound (or its polymer) 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 the host material of the light-emitting layer. The third component functions as a solvent for dissolving the first and second components in the composition, and provides a smooth and uniform surface shape during coating due to the controlled evaporation rate of the third component itself.

[0717] <Organic solvents>

[0718] 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, film formation properties, the presence or absence of coating defects, surface roughness, and smoothness can be controlled and improved. Furthermore, when forming a film using an inkjet printer, the stability of the meniscus in the inkjet head's pinholes can be controlled, thus controlling / improving ejection performance. Moreover, by controlling the film drying rate and the orientation of derivative molecules, the electrical properties, luminescent properties, efficiency, and lifetime of organic EL elements having an organic layer obtained from this composition for forming an organic layer can be improved.

[0719] (1) Properties of organic solvents

[0720] At least one organic solvent has a boiling point of 130°C to 300°C, more preferably 140°C to 270°C, and even more preferably 150°C to 250°C. A boiling point higher than 130°C is preferred from the viewpoint of inkjet ejection performance. Furthermore, a boiling point lower than 300°C is preferred from the viewpoint of coating defects, surface roughness, residual solvent, and smoothness. From the viewpoint of good inkjet ejection performance, film formation, smoothness, and low residual solvent, the organic solvent is more preferably composed of two or more organic solvents. On the other hand, depending on the circumstances, considering factors such as transportability, a solid composition can be prepared by removing the solvent from the organic layer forming composition.

[0721] Furthermore, the organic solvent is particularly preferably composed of a good solvent (GS) and a poor solvent (PS) for at least one solute, and the boiling point (BP) of the good solvent (GS) is... GS () lower than the boiling point (BP) of lean solvent (PS) PS ).

[0722] By adding a high-boiling-point lean solvent, the low-boiling-point good solvent will evaporate first during film formation, increasing the concentration of the components and the lean solvent in the composition, thus promoting rapid film formation. This results in a coating film with fewer defects, lower surface roughness, and higher smoothness.

[0723] Difference in solubility (S) GS -S PS The content is preferably 1% or more, more preferably 3% or more, and even more preferably 5% or more. The difference in boiling points (BP) PS -BP GS The temperature is preferably 10°C or higher, more preferably 30°C or higher, and even more preferably 50°C or higher.

[0724] After film formation, the organic solvent is removed from the coating through drying processes such as vacuum, reduced pressure, and heating. When heating, from the viewpoint of improving film formation properties, it is preferable to perform heating at a temperature below the glass transition temperature (Tg) of at least one solute +30°C. Furthermore, from the viewpoint of reducing residual solvent, it is preferable to perform heating at a temperature above the glass transition temperature (Tg) of at least one solute -30°C. Even if the heating temperature is below the boiling point of the organic solvent, the organic solvent will be sufficiently removed due to the thin film. In addition, multiple drying processes can be performed at different temperatures, or multiple drying methods can be used in combination.

[0725] (2) Specific examples of organic solvents

[0726] Organic solvents used in compositions for forming organic layers include alkylbenzene solvents, phenyl ether solvents, alkyl ether solvents, cyclic ketone solvents, aliphatic ketone solvents, monocyclic ketone solvents, solvents with a diester skeleton, and fluorinated solvents. Specific examples include pentanol, hexanol, heptanol, octanol, nonanol, decanol, undecaneol, dodecaneol, tetradecaneol, hexane-2-ol, heptane-2-ol, octane-2-ol, decane-2-ol, dodecane-2-ol, cyclohexanol, α-terpineol, β-terpineol, γ-terpineol, δ-terpineol, terpineol (mixtures), ethylene glycol monomethyl ether acetate, propylene glycol monomethyl ether acetate, diethylene glycol dimethyl ether, dipropylene glycol dimethyl ether, and so on. Ethylene 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-dimethylpyridine, 2-fluorom-xylene, 3-fluoroo-xylene, 2-chlorotrifluoride, cumene, toluene, 2-chloro-6-fluorotoluene, 2-fluoroanisole, anisole, 2,3-dimethylpyrazine, bromobenzene, 4-fluoroanisole, 3-fluoroanisole 3-Trifluoromethyl anisole, mesitylene, 1,2,4-trimethylbenzene, tert-butylbenzene, 2-methyl anisole, phenethyl ether, benzodioxane, 4-methyl anisole, sec-butylbenzene, 3-methyl anisole, 4-fluoro-3-methyl anisole, cymene, 1,2,3-trimethylbenzene, 1,2-dichlorobenzene, 2-fluorobenzonitrile, 4-fluoroveratrol, 2,6-dimethyl anisole, n-butylbenzene, 3-fluorobenzonitrile, naphthane (decahydronaphthalene), neopentylbenzene, 2,5-dimethyl anisole, 2,4-dimethyl anisole, benzonitrile, 3,5-dimethyl anisole, diphenyl ether, 1-fluoro-3,5-dimethoxybenzene, methyl benzoate, isopentylbenzene, 3,4-dimethyl anisole, o-tolyl The solvents include, but are not limited to, nitriles, n-pentylbenzene, veratrine ether, 1,2,3,4-tetrahydronaphthalene, ethyl benzoate, n-hexylbenzene, propyl benzoate, cyclohexylbenzene, 1-methylnaphthalene, butyl benzoate, 2-methylbiphenyl, 3-phenoxytoluene, 2,2'-bitoluene, 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)benzenebenzylbutyl ether, benzylpentyl ether, benzylhexyl ether, benzylheptyl ether, benzyloctyl ether, etc. Furthermore, one or a mixture of solvents may be used.

[0727] <Optional Ingredients>

[0728] The composition for forming organic layers may contain optional components without impairing its properties. Examples of optional components include binders and surfactants.

[0729] (1) Adhesive

[0730] The composition for forming an organic layer may contain a binder. The binder forms a film during film formation and bonds the resulting film to a substrate. Furthermore, the composition for forming an organic layer also functions to dissolve, disperse, and bind other components.

[0731] Examples of binders used in compositions for forming organic layers include, but are not limited to, acrylic resins, polyethylene terephthalate, ethylene-vinyl acetate copolymer, ethylene-vinyl alcohol copolymer, acrylonitrile-ethylene-styrene copolymer (AES) resin, ionomers, chlorinated polyethers, diallyl phthalate resin, unsaturated polyester resins, polyethylene, polypropylene, polyvinyl chloride, polyvinylidene chloride, polystyrene, polyvinyl acetate, Teflon, acrylonitrile-butadiene-styrene copolymer (ABS) resin, acrylonitrile-styrene copolymer (AS) resin, phenolic resins, epoxy resins, melamine resins, urea resins, alkyd resins, polyurethanes, and copolymers of the above resins and polymers.

[0732] The adhesive used in the composition for forming organic layers can be a single type or a mixture of multiple types.

[0733] (2) Surfactants

[0734] For example, to control the film surface uniformity, solvent affinity, and liquid repellency of the organic layer forming composition, the organic layer forming composition may contain a surfactant. Surfactants are classified as ionic and nonionic based on the structure of their hydrophilic groups, and further classified as alkyl, silicon, and fluorine based on the structure of their hydrophobic groups. Furthermore, they are classified according to their molecular structure as monomolecular systems with small molecular weights and simple structures, and polymeric systems with large molecular weights and side chains or branches. Additionally, they are classified according to their composition as single systems or mixed systems containing two or more surfactants and a substrate. All types of surfactants can be used as surfactants in this organic layer forming composition.

[0735] Examples of surfactants include Polyflow No. 45, Polyflow KL-245, Polyflow No. 75, Polyflow No. 90, Polyflow No. 95 (trade name, manufactured by Kyoei Chemical Industry 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 name, BYK-Chemie). (Made by Japan Company); KP-341, KP-358, KP-368, KF-96-50CS, KF-50-100CS (trade name, made by Shin-Etsu Chemical Co., Ltd.); Surflon SC-101, Surflon KH-40 (trade name, made by SEIMI CHEMICAL); FTERGENT 222F, FTERGENT 251, FTX-218 (trade name, made by NEOS); EFTOP EF-351, EFTOP EF-352, EFTOP EF-601, EFTOP EF-801, EFTOP EF-802 (trade name, made by Mitsubishi Materials Corporation); Megafac F-470, Megafac F-471, Megafac F-475, Megafac R-08, Megafac F-477, Megafac F-479, Megafac F-553, Megafac F-554 (trade name, manufactured by DIC); fluoroalkylbenzene sulfonates, fluoroalkyl carboxylates, fluoroalkyl polyoxyethylene ethers, fluoroalkyl ammonium iodide, fluoroalkyl betaine, fluoroalkyl sulfonates, diglycerol tetra(fluoroalkyl polyoxyethylene ether), fluoroalkyl trimethylammonium salt, fluoroalkyl aminosulfonates, polyoxyethylene nonylphenyl ether, polyoxyethylene octylphenyl ether, polyoxyethylene alkyl ether, polyoxyethylene laurate, polyoxyethylene oleate, polyoxyethylene stearate, polyoxyethylene laurylamine, sorbitol laurate, sorbitol palmitate, sorbitol stearate, sorbitol oleate, sorbitol fatty acid ester, polyoxyethylene sorbitol laurate, polyoxyethylene sorbitol palmitate, polyoxyethylene sorbitol stearate, polyoxyethylene sorbitol oleate, polyoxyethylene naphthyl ether, alkylbenzene sulfonates, and alkyl diphenyl ether disulfonates.

[0736] In addition, one surfactant can be used, or two or more surfactants can be used in combination.

[0737] Composition and properties of compositions for organic layer formation

[0738] The content of each component in the organic layer forming composition can be determined by considering the good solubility, storage stability, and film-forming properties of each component in the organic layer forming composition, the high quality of the coating obtained from the organic layer forming composition, the good ejectibility when using inkjet printing, and the good electrical properties, luminescence properties, efficiency, and lifespan of the organic EL element with the organic layer made using the composition. For example, in the case of a light-emitting layer forming composition, it is preferable that the first component is 0.0001 wt% to 2.0 wt% of the total weight of the light-emitting layer forming composition, the second component is 0.0999 wt% to 8.0 wt% of the total weight of the light-emitting layer forming composition, and the third component is 90.0 wt% to 99.9 wt% of the total weight of the light-emitting layer forming composition.

[0739] More preferably, the first component accounts for 0.005% to 1.0% of the total weight of the composition for forming the light-emitting layer, the second component accounts for 0.095% to 4.0% of the total weight of the composition for forming the light-emitting layer, and the third component accounts for 95.0% to 99.9% of the total weight of the composition for forming the light-emitting layer. Even more preferably, the first component accounts for 0.05% to 0.5% of the total weight of the composition for forming the light-emitting layer, the second component accounts for 0.25% to 2.5% of the total weight of the composition for forming the light-emitting layer, and the third component accounts for 97.0% to 99.7% of the total weight of the composition for forming the light-emitting layer.

[0740] The composition for forming an organic layer can be manufactured by appropriately selecting the above-mentioned components and subjecting them to stirring, mixing, heating, cooling, dissolving, dispersing, etc., using known methods. Furthermore, after preparation, appropriate selection and treatment such as filtration, degassing (also known as degassing), ion exchange treatment, and inactive gas replacement / sealing treatment can also be performed.

[0741] Regarding the viscosity of the composition for forming the organic layer, a high viscosity allows for good film formation and good ejectibility when using inkjet printing. On the other hand, a low viscosity facilitates the fabrication of thin films. Therefore, the viscosity of this composition for forming the organic layer at 25°C is preferably 0.3 to 3 mPa·s, more preferably 1 to 3 mPa·s. In this invention, the viscosity is a value measured using a conical plate type rotational viscometer (cone-plate type).

[0742] A low surface tension in the composition for forming the organic layer results in a coating with good film-forming properties and no defects. Conversely, a high surface tension results in good inkjet ejection properties. Therefore, regarding the viscosity of this composition for forming the organic layer, the surface tension at 25°C is preferably 20-40 mN / m, more preferably 20-30 mN / m. In this invention, the surface tension is a value measured using the pendant drop method.

[0743] <Cross-linked polymers: Compounds represented by the general formula (XLP-1)>

[0744] Next, the case where the above-mentioned polymeric compounds have cross-linking substituents will be described. Such cross-linking polymeric compounds are, for example, compounds represented by the following general formula (XLP-1).

[0745]

[0746] In formula (XLP-1),

[0747] MUx, ECx and k are the same as the definitions of MU, EC and k in the above formula (SPH-1), wherein the compound shown in formula (XLP-1) has at least one crosslinking substituent (XLS), preferably the content of the monovalent or divalent aromatic compound having the crosslinking substituent is 0.1 to 80% by weight in the molecule.

[0748] The content of the monovalent or divalent aromatic compound having crosslinking substituents is preferably 0.5 to 50% by weight, more preferably 1 to 20% by weight.

[0749] As a crosslinking substituent (XLS), there is no particular limitation as long as it is a group capable of further crosslinking the above-mentioned polymer compound, but substituents with the following structures are preferred. * in each structural formula indicates a bonding position.

[0750]

[0751] L can be a single bond, -O-, -S-, >C=O, -OC(=O)-, alkylene group with 1 to 12 carbon atoms, oxoalkylene group with 1 to 12 carbon atoms, or polyoxoalkylene group with 1 to 12 carbon atoms. Among the above substituents, the groups shown in formula (XLS-1), formula (XLS-2), formula (XLS-3), formula (XLS-9), formula (XLS-10), or formula (XLS-17) are preferred, and the groups shown in formula (XLS-1), formula (XLS-3), or formula (XLS-17) are more preferred.

[0752] Examples of divalent aromatic compounds having crosslinking substituents include compounds having the following partial structures.

[0753]

[0754]

[0755]

[0756]

[0757] <Methods for manufacturing polymers and cross-linked polymers>

[0758] The manufacturing methods for polymeric compounds and cross-linked polymeric compounds will be described using compounds represented by formula (SPH-1) and (XLP-1) as examples. These compounds can be synthesized by appropriately combining known manufacturing methods.

[0759] Solvents used in the reaction can include aromatic solvents, saturated / unsaturated hydrocarbon solvents, alcohol solvents, ether solvents, etc. Examples include dimethoxyethane, 2-(2-methoxyethoxy)ethane, and 2-(2-ethoxyethoxy)ethane.

[0760] Furthermore, the reaction can be carried out through a two-phase system. When conducting the reaction through a two-phase system, a phase transfer catalyst such as a quaternary ammonium salt can be added as needed.

[0761] Compounds of formula (SPH-1) and (XLP-1) can be synthesized in a single stage or through multiple stages. Furthermore, they can be synthesized via co-polymerization, where all starting materials are added to the reaction vessel before the reaction begins; via dropwise polymerization, where starting materials are added dropwise to the reaction vessel; or via precipitation polymerization, where the product precipitates as the reaction proceeds. These methods can be appropriately combined. For example, when synthesizing compounds of formula (SPH-1) in a single stage, the target compound is obtained by reacting with monomer units (MU) and end-capping units (EC) added to the reaction vessel. Furthermore, when synthesizing compounds of general formula (SPH-1) through multiple stages, the target compound is obtained by polymerizing monomer units (MU) to the target molecular weight and then adding end-capping units (EC) to allow the reaction. By adding different types of monomer units (MU) and reacting them in multiple stages, polymers with concentration gradients for the monomer unit structures can be produced. Additionally, the target polymer can be obtained through a post-reaction after preparing a precursor polymer.

[0762] Furthermore, by selecting the polymerizable groups of the monomer unit (MU), the primary structure of the polymer can be controlled. For example, as shown in synthetic routes 1 to 3, polymers with random primary structures (synthetic route 1) and polymers with regular primary structures (synthetic routes 2 and 3) can be synthesized, and appropriate combinations can be used depending on the target material. Moreover, if monomer units with three or more polymerizable groups are used, hyperbranched polymers and dendrimers can be synthesized.

[0763]

[0764] As the single unit that can be used in this invention, it can be specified according to Japanese Patent Application Publication No. 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, and International Publication No. 2015 / 1458. The method described in Japanese Patent Application Publication No. 71, Japanese Patent Application Publication No. 2010-215886, Japanese Patent Application Publication No. 2008-106241, Japanese Patent Application Publication No. 2010-215886, International Publication No. 2016 / 031639, Japanese Patent Application Publication No. 2011-174062, International Publication No. 2016 / 031639, International Publication No. 2016 / 031639, and International Publication No. 2002 / 045184 is used to synthesize the substance.

[0765] Furthermore, for specific polymer synthesis steps, please refer to Japanese Patent Application Publication No. 2012-036388, International Publication No. 2015 / 008851, Japanese Patent Application Publication No. 2012-36381, Japanese Patent Application Publication No. 2012-144722, International Publication No. 2015 / 194448, International Publication No. 2013 / 146806, International Publication No. 2015 / 145871, and other international publications. The method described in Japanese Patent Application Publication No. 2016 / 031639, International Publication No. 2016 / 125560, International Publication No. 2016 / 031639, International Publication No. 2016 / 125560, International Publication No. 2015 / 145871, International Publication No. 2011 / 049241, and Japanese Patent Application Publication No. 2012-144722 is used to synthesize the material.

[0766] <Examples of applications of organic electroluminescent elements>

[0767] Furthermore, the present invention can also be applied to display devices equipped with organic EL elements or lighting devices equipped with organic EL elements.

[0768] Display devices or lighting devices equipped with organic EL elements can be manufactured by known methods such as connecting the organic EL element of this embodiment to a known driving device, and can be driven by known driving methods such as DC driving, pulse driving, and AC driving.

[0769] Examples of display devices include panel displays such as color flat panel displays and flexible displays such as flexible color organic electroluminescent (EL) displays (see, for example, Japanese Patent Application Publication No. 10-335066, Japanese Patent Application Publication No. 2003-321546, and Japanese Patent Application Publication No. 2004-281086). Furthermore, examples of display methods include matrix and / or segmented displays. It should be noted that matrix displays and segmented displays can coexist on the same panel.

[0770] In a matrix, pixels for display are arranged two-dimensionally in a grid, mosaic, or similar pattern, and text and images are displayed through the collection of pixels. The shape and size of the pixels are determined according to the application. For example, in the image and text display of personal computers, monitors, and televisions, quadrilateral pixels with a single side of less than 300μm are typically used. Furthermore, in the case of large displays such as display panels, pixels with a single side on the order of mm are used. In the case of monochrome display, simply arranging pixels of the same color is sufficient; in the case of color display, red, green, and blue pixels are arranged and displayed. In this case, typically, there are triangular and striped types. Furthermore, the driving method for this matrix can be either a line-driven method or an active matrix. Line-driven methods have the advantage of simple structure, but considering the operating characteristics, active matrices are sometimes superior; therefore, their use also needs to be differentiated according to the application.

[0771] In the segmented mode (type), a pattern is formed to display predetermined information, and the defined area is illuminated. Examples include the time and temperature displays in digital clocks and thermometers; the operating status displays in audio equipment and induction cookers; and the panel displays in automobiles.

[0772] Examples of lighting devices include indoor lighting and backlights for liquid crystal displays (see, for example, Japanese Patent Application Publication Nos. 2003-257621, 2003-277741, and 2004-119211). Backlights are primarily used to improve the visibility of non-emissive display devices and are used in liquid crystal displays, clocks, audio equipment, automotive panels, display boards, and signs. In particular, for liquid crystal displays, especially for personal computers where thinness is a key issue, the backlight using the light-emitting element of this embodiment is thin and lightweight, considering that conventional methods are difficult to make thin due to their use of fluorescent lamps and light guide plates.

[0773] Furthermore, research is actively underway to apply color-conversion-based color enhancement technologies to liquid crystal displays (LCDs), organic EL displays, and lighting. Color conversion refers to the conversion (wavelength conversion) of light emitted from a light source into longer wavelengths, such as converting blue light into green and red light. By thinning a composition with this wavelength conversion function and combining it with, for example, a blue light source, the three primary colors of blue, green, and red can be extracted from the blue light source, i.e., white light can be extracted. By using a white light source combining this blue light source and a thin film with wavelength conversion function as a light source unit, and combining a liquid crystal driving section with a color filter, a full-color display can be fabricated. Alternatively, without a liquid crystal driving section, it can be used directly as a white light source, such as for LED lighting. In addition, by using a blue organic EL element as a light source and combining it with a thin film that converts light into green and red, a full-color organic EL display without a metal mask can be fabricated. Furthermore, by using a blue micro-LED as a light source and combining it with a thin film that converts light into green and red, a low-cost full-color micro-LED display can be fabricated.

[0774] The polycyclic aromatic compounds represented by the above general formula (1) are useful as fluorescent materials that provide high-purity blue or green emission by excitation light, and can also be used as materials with this wavelength conversion function. Specifically, the polycyclic aromatic compounds of formula (1) can be used, for example, as wavelength conversion materials that convert light with wavelengths of 300 nm to 449 nm into blue emission with a narrow half-width (below 25 nm, and further below 20 nm) having a maximum value in the range of 450 nm to 500 nm. In addition, they can be used, for example, as wavelength conversion materials that convert light with wavelengths of 300 nm to 499 nm into green emission with a narrow half-width (below 25 nm, and further below 20 nm) having a maximum value in the range of 500 nm to 570 nm.

[0775] The composition with wavelength conversion function may include, in addition to the polycyclic aromatic compound of formula (1), an adhesive resin, other additives, and a solvent. As the adhesive resin, for example, the resin described in paragraphs

[0173] to

[0176] of International Publication No. 2016 / 190283 may be used. As other additives, compounds described in paragraphs

[0177] to

[0181] of International Publication No. 2016 / 190283 may be used. Furthermore, as the solvent, any solvent suitable for dissolving these materials may be used.

[0776] The wavelength conversion film includes a wavelength conversion layer formed by curing a composition having wavelength conversion function. A known thin film forming method can be used as a method for forming the wavelength conversion layer from the composition. The wavelength conversion film may contain only a wavelength conversion layer formed from a composition containing a polycyclic aromatic compound of formula (1), or it may contain other wavelength conversion layers (e.g., wavelength conversion layers that convert blue light into green light and red light; wavelength conversion layers that convert blue light and green light into red light). Furthermore, the wavelength conversion film may also include a substrate layer and a barrier layer for preventing the color conversion layer from deteriorating due to oxygen, moisture, or heat.

[0777] 3-2. Other organic equipment

[0778] In addition to being used in the aforementioned organic electroluminescent elements, the polycyclic aromatic compounds described in this invention can also be used to fabricate organic field-effect transistors or organic thin-film solar cells.

[0779] An organic field-effect transistor (FET) is a transistor that controls current using an electric field generated by an input voltage. In addition to active and drain electrodes, it also has a gate electrode. When a voltage is applied to the gate electrode, an electric field is generated, which can arbitrarily block the flow of electrons (or holes) between the source and drain electrodes to control the current. FETs are easier to miniaturize than simple transistors (bipolar transistors) and are frequently used as components in integrated circuits and other similar devices.

[0780] Regarding the structure of organic field-effect transistors, the active electrode and drain electrode are typically disposed in contact with an organic semiconductor active layer formed using the polycyclic aromatic compound described in this invention, and then a gate electrode is disposed sandwiched between an insulating layer (dielectric layer) in contact with the organic semiconductor active layer. Examples of such device structures include the following.

[0781] (1) Substrate / Gate electrode / Insulator layer / Source electrode-Drain electrode / Organic semiconductor active layer

[0782] (2) Substrate / Gate electrode / Insulator layer / Organic semiconductor active layer / Source electrode-Drain electrode

[0783] (3) Substrate / Organic semiconductor active layer / Source electrode-Drain electrode / Insulator layer / Gate electrode

[0784] (4) Substrate / Source electrode-Drain electrode / Organic semiconductor active layer / Insulator layer / Gate electrode

[0785] Organic field-effect transistors constructed in this way can be used as pixel driving switching elements in active matrix driven liquid crystal displays and organic electroluminescent displays.

[0786] Organic thin-film solar cells have 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 stacked 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 compounds described in this invention can be used as materials for the hole transport layer, p-type semiconductor layer, n-type semiconductor layer, and electron transport layer, depending on their physical properties. The polycyclic aromatic compounds described in this invention can function as hole transport materials and electron transport materials in organic thin-film solar cells. In addition to the above, organic thin-film solar cells may also appropriately include hole blocking layers, electron blocking layers, electron injection layers, hole injection layers, smoothing layers, etc. In organic thin-film solar cells, known materials used in organic thin-film solar cells can be appropriately selected and combined.

[0787] Example

[0788] The present invention will be described in more detail below through examples, but the invention is not limited thereto. First, examples of the synthesis of polycyclic aromatic compounds will be described below.

[0789] Synthesis example (1)

[0790] Synthesis of compound (1-230): 7,10-bis(trimethylyl)-2,15,18-trimethyl-5,12-dioxa-8b-aza-16b,19b-diboronanthro[1,9-ab]benzo[j]perylene

[0791]

[0792] Under a nitrogen atmosphere, a 500 mL flask containing 1-bromo-3-chloro-5-fluorobenzene (compound IA, 14.7 g, 70 mmol), p-cresol (compound IB, 7.95 g, 74 mmol), potassium carbonate (14.5 g, 105 mmol), and N-methylpyrrolidone (NMP) was heated to 150 °C and stirred for 15 hours. The reaction solution was cooled to room temperature, filtered through a short column of Florisil (eluent: toluene), and extracted with hydrochloric acid and toluene to give 1-bromo-3-chloro-5-(p-tolyloxy)benzene (compound IC) (18.4 g, yield 88%).

[0793]

[0794] The structure of the obtained compound was confirmed by NMR determination.

[0795] 1 H-NMR (400MHz, CDCl3): δ=2.35 (s, 3H), 6.86-6.98 (m, 4H), 7.13-7.18 (m, 3H).

[0796] Under a nitrogen atmosphere, a flask containing compound IC (13.1 g, 44 mmol), p-toluidine (compound ID, 2.15 g, 20 mmol), Pd2(dba)3 (0.187 g, 0.20 mmol), tri-tert-butylphosphonium tetrafluoroborate (0.134 g, 0.46 mmol), tBuONa (4.77 g, 50 mmol), and toluene (120 mL) was stirred at 100 °C for 20 hours. The reaction solution was cooled to room temperature, filtered through a short column of Florisil (eluent: toluene), and washed with hexane to give 3-chloro-N-(3-chloro-5-(p-tolyloxy)phenyl)-N-(p-tolyl)-5-(p-tolyloxy)aniline (compound IE) (7.55 g, 70% yield).

[0797]

[0798] The structure of the obtained compound was confirmed by NMR determination.

[0799] 1 H-NMR (400MHz, CDCl3): δ = 2.32 (s, 6H), 2.33 (s, 3H), 6.49 (t, 2H), 6.61 (t, 2H), 6.68 (t, 2H), 6.89 (d, 4H), 7.01 (d, 2H), 7.11-7.14 (m, 6H).

[0800] Under a nitrogen atmosphere, a flask containing compound IE (1.89 g, 3.5 mmol), trimethylbenzylboronic acid (compound IF, 2.86 g, 17 mmol), Pd2(dba)3 (0.294 g, 0.32 mmol), SPhos (0.288 g, 0.70 mmol), tBuOK (1.63 g, 15 mmol), and tBuOH (21 mL) was heated to 80 °C and stirred for 24 hours. The reaction solution was cooled to room temperature and extracted with water and toluene. The solvent was then distilled off to obtain the crude product. The crude product was washed with methanol to obtain 2',4',6'-trimethyl-N-(p-tolyl)-5-(p-tolyloxy)-N-(2',4',6'-trimethyl-5-(p-tolyloxy)-[1,1'-biphenyl]-3-yl)-[1,1'-biphenyl]-3-amine (compound IG) (2.18 g, yield 88%).

[0801]

[0802] The structure of the obtained compound was confirmed by NMR determination.

[0803] 1 H-NMR (400MHz, CDCl3): δ = 1.98 (s, 12H), 2.26 (s, 6H), 2.27 (s, 3H), 2.29 (s, 6H) , 6.29 (s, 2H), 6.57 (s, 2H), 6.78 (t, 2H), 6.84 (s, 4H), 6.89 (d, 4H), 7.06 (t, 8H).

[0804] A Schrank flask containing compound IG (0.214 g, 0.30 mmol), boron triiodide (0.943 g, 2.4 mmol), and 1,2,4-trichlorobenzene (3.0 mL) was heated to 120 °C and stirred for 38 hours. The reaction solution was cooled to room temperature, and phosphate buffer (pH 7) was added to the reaction mixture. The aqueous layer was separated and extracted with dichloromethane. The reaction solution was then distilled off to obtain the crude product. The crude product was purified by silica gel column chromatography (eluent: hexane, toluene) to give compound (1-230) (30.0 mg, yield 14%).

[0805]

[0806] The structure of the obtained compound was confirmed by NMR determination.

[0807] 1H-NMR (400MHz, CDCl3): δ = 1.83 (s, 6H), 1.86 (s, 6H), 2.34 (s, 6H), 2.58 (s, 6H), 2.74 (s, 3H), 6. 84 (s,2H), 6.94 (s,2H), 6.99 (s,2H), 7.46-7.55 (m,4H), 7.63 (s,2H), 8.38 (s,2H), 8.76 (s,2H).

[0808] 11 B-NMR (160MHz, CDCl3): δ=41.3.

[0809] Synthesis example (2)

[0810] Synthesis of compounds (1-28): 7,10-bis(trimethylyl)-2,15,18-trimethyl-5,12-bis-p-methyl-5,12H-dihydro-5,8b,12-triaza-16b,19b-diborane[1,9-ab]benzo[j]perylene

[0811]

[0812] Under a nitrogen atmosphere, a flask containing 1,3-dibromo-5-chlorobenzene (compound IH, 5.41 g, 20 mmol), di-p-toluidine (compound II, 3.95 g, 20 mmol), Pd2(dba)3 (0.183 mg, 0.2 mmol), BINAP (0.249 mg, 0.4 mmol), tBuONa (2.12 g, 22 mmol), and toluene (100 mL) was heated to 80 °C and stirred for 40 hours. The reaction solution was cooled to room temperature and filtered through a short column packed with Florisil (eluent: toluene), followed by filtration through a short column packed with silica gel (eluent: hexane), thereby yielding 3-bromo-5-chloro-N,N-di(p-toluyl)amine (compound IJ) (7.29 g, yield 50%).

[0813]

[0814] The structure of the obtained compound was confirmed by NMR determination.

[0815] 1 H-NMR (400MHz, CDCl3): δ=2.33 (s, 6H), 6.82 (s, 1H), 6.94-7.00 (m, 5H), 7.10-7.12 (s, 4H).

[0816] Under a nitrogen atmosphere, a flask containing compound IJ (3.39 g, 8.8 mmol), p-toluidine (compound ID, 0.429 g, 4.0 mmol), Pd2(dba)3 (36.7 mg, 0.03 mmol), SPhos (32.8 mg, 0.08 mmol), tBuONa (1.15 g, 12 mmol), and toluene (15 mL) was heated to 90 °C and stirred for 12 hours. The reaction solution was cooled to room temperature, filtered through a short column packed with Florisil (eluent: toluene), and washed with methanol to obtain 5-chloro-N 1 -(3-chloro-5-bis(p-tolylaminophenyl))-N 1 N 3 N 3 - Tri-p-tolylphenyl-1,3-diamine (compound IK) (2.76 g, yield 96%).

[0817]

[0818] The structure of the obtained compound was confirmed by NMR determination.

[0819] 1 H-NMR (500MHz, CDCl3): δ = 2.27 (s, 15H), 6.45 (s, 2H), 6.47 (s, 2H), 6.53 (s, 2H), 6.90-6.92 (m, 10H), 7.03-7.05 (m, 10H).

[0820] Under a nitrogen atmosphere, a flask containing compound IK (2.88 g, 4.0 mmol), trimethylbenzylboronic acid (compound IF, 3.28 g, 20 mmol), Pd2(dba)3 (0.330 g, 0.36 mmol), SPhos (0.345 g, 0.84 mmol), tBuOK (2.69 g, 24 mmol), and tBuOH (40 mL) was heated to 80 °C and stirred for 24 hours. The reaction solution was cooled to room temperature and extracted with water and toluene. The solvent was then distilled off to obtain the crude product. The crude product was washed with methanol to obtain N. 3 -(5-(di-p-tolylamino)-2',4',6'-trimethyl-[1,1'-biphenyl]-3-yl)-2',4',6'-trimethyl-N 3 N 5 N 5 -Tri-p-tolyl-[1,1'-biphenyl]-3-amine (compound IM) (2.94 g, yield 83%).

[0821]

[0822] The structure of the obtained compound was confirmed by NMR determination.

[0823] 1 H-NMR (400MHz, CDCl3): δ = 1.98 (s, 12H), 2.26 (s, 6H), 2.27 (s, 3H), 2.29 (s, 6H) , 6.29 (s, 2H), 6.57 (s, 2H), 6.78 (t, 2H), 6,84 (s, 4H), 6.89 (d, 4H), 7.06 (t, 8H).

[0824] A Schrank flask containing compound IM (180.3 mg, 0.20 mmol), boron triiodide (0.627 g, 1.6 mmol), and 1,2,4-trichlorobenzene (2.0 mL) was heated to 150 °C and stirred for 20 hours. The reaction solution was cooled to room temperature, and phosphate buffer (pH 7) was added to the reaction mixture. The aqueous layer was separated and extracted with dichloromethane. The reaction solution was then distilled off to obtain the crude product. The crude product was purified using preparative thin-layer chromatography (PTLC) (developing solvent: hexane / toluene = 3 / 1 (volume ratio)) and gel permeation chromatography (GPC) (eluting buffer: 1,2-dichloroethane) to give compounds (1-28) (3.21 mg, yield 2%).

[0825]

[0826] The structure of the obtained compound was confirmed by NMR determination.

[0827] 1 H-NMR (400MHz, CDCl3): δ = 1.72 (m, 12H), 2.24 (s, 6H), 2.48 (s, 6H), 2.68 (s, 6H), 3.03 (s, 3H), 6. 39 (s, 2H), 6.47 (m, 4H), 6.99 (d, 2H), 7.28 (m, 6H), 7.39-7.40 (m, 6H), 9.17 (s, 2H), 9.51 (s, 2H).

[0828] 11 B-NMR (160MHz, CDCl3): δ=39.2

[0829] It should be noted that, based on further verification, the structure of compound (1-28) may have two adjacent benzene rings (equivalent to ring a in formula (2)) bonded together by a single bond, as shown in formula (1-28').

[0830]

[0831] Synthesis example (3)

[0832] Synthesis of compound (1-232): 7,10-bis(trimethylyl)-18-methyl-3,14-di-o-tolyl-5,12-dioxa-8b-aza-16b,19b-diboronanthro[1,9-ab]benzo[j]perylene

[0833]

[0834] A Schrank flask containing 2',4',6'-trimethyl-5-((2'-methyl-[1,1'-biphenyl]-3-yl)oxy)-N-(p-tolyl)-N-(2',4',6'-trimethyl-5-((2'-methyl-[1,1'-biphenyl]-3-yl)oxy)-[1,1'-biphenyl]-3-amine (compound IN, 1.98 g, 2.3 mmol), boron triiodide (7.05 g, 18 mmol), and 1,2,4-trichlorobenzene (20 mL) was heated to 150 °C and stirred for 40 hours. The reaction solution was cooled to room temperature, and phosphate buffer (pH 7) was added to the reaction mixture. The aqueous layer was separated and extracted with dichloromethane. The reaction solution was then distilled off to obtain the crude product. The crude product was purified using a short silica gel column (eluent: hexane, toluene), and the residue was washed twice with acetonitrile. Subsequently, the residue was washed with preparative GPC (eluent: dichloroethane), a silica gel column (eluent: hexane / toluene = 5 / 1 (volume ratio)), and acetonitrile to obtain compound (1-232) (58.0 mg, yield 3%).

[0835]

[0836] The structure of the obtained compound was confirmed by NMR determination.

[0837] 1 H-NMR (400MHz, CDCl3): δ = 1.85 (s, 6H), 1.88 (s, 6H), 2.35 (s, 6H), 2.41 (s, 6H), 2.75 (s, 3H), 6.86 (s, 2 H), 6.95 (s,2H), 7.03 (s,2H), 7.31-7.44 (m,10H), 7.57 (s,2H), 7.68 (s,2H), 8.65 (d,2H), 8.82 (s,2H).

[0838] 11 B-NMR (160MHz, CDCl3): δ=39.4.

[0839] Synthesis example (4)

[0840] Compound (1-2023): 3,15-bis(3,5-dimethylphenyl)-1,17-bis(trimethylyl)-5,9,13-trimethyl-3,15-dihydro-3,7c 2 Synthesis of ,15-triaza-7b,10b-diborontribenzo[a,l,op]fluorenzo[2,1,9,8,7-defghi]tetrabenzene

[0841]

[0842] Will contain N 3 -(3,5-dimethylphenyl)-N 5 -(5-((3,5-dimethylphenyl)(m-tolyl)amino)-2',4',6'-trimethyl-[1,1'-biphenyl]-3-yl)-2',4',6'-trimethyl-N 3 -(m-Tolyl)-N 5 A Schrank flask containing 0.274 g (0.29 mmol) of (p-tolyl)-[1,1'-biphenyl]-3,5-diamine, 0.470 g (1.2 mmol) of boron triiodide, and 3.0 mL of 1,2,4-trichlorobenzene was heated to 150 °C and stirred for 20 hours. The reaction solution was cooled to room temperature, and phosphate buffer (pH 7) was added to the reaction mixture. The aqueous layer was separated and extracted with dichloromethane. The reaction solution was then distilled off to give the crude product. The crude product was washed with acetonitrile, dichloroethane, toluene, and octane to give compound (1-2023) (11.0 mg, yield 4%).

[0843]

[0844] The structure of the obtained compound was confirmed by NMR and mass spectrometry.

[0845] 1 H-NMR (400MHz, CDCl3): δ = 1.74 (s, 12H), 2.24 (s, 6H), 2.39 (s, 12H), 2.44 (s, 6H), 2.99 (s, 3H), 6.39 (s,2H), 6.48 (s,4H), 6.89 (s,2H), 7.01 (s,4H), 7.14 (s,2H), 7.29 (d,2H), 9.25 (d,2H), 9.47 (s,2H).

[0846] LOWMS (MALDI-TOF / MS) m / z [M] ＋ calcd for C 67 H 59 B2N3 927.49; observed 927.73

[0847] By appropriately changing the compounds of the raw materials and using the method based on the above-described synthesis example, other polycyclic aromatic compounds of the present invention can be synthesized.

[0848] Next, the evaluation of the basic physical properties of the compounds of the present invention and the fabrication and evaluation of organic EL elements using the compounds of the present invention will be described.

[0849] <Evaluation of basic physical properties>

[0850] Sample preparation

[0851] When evaluating the absorption and luminescence properties (fluorescence and phosphorescence) of compounds, there are cases where the compound is dissolved in a solvent and evaluated in the solvent, and cases where the evaluation is performed in a thin film state. Furthermore, when evaluating in a thin film state, depending on how the compound is used in the organic EL element, there are cases where the compound is evaluated simply by thinning it into a thin film, and cases where the compound is dispersed in a suitable matrix material and then thinned into a thin film for evaluation.

[0852] Commercially available PMMA (polymethyl methacrylate) or similar materials can be used as the matrix material. Thin film samples dispersed in PMMA can be prepared, for example, by dissolving PMMA and the compound being evaluated in toluene, and then forming a thin film on a transparent quartz substrate (10 mm × 10 mm) using spin coating.

[0853] Furthermore, the following describes the method for preparing thin film samples when the matrix material is the main material. A transparent quartz support substrate (10mm × 10mm × 1.0mm) is fixed to the substrate support of a commercially available vapor deposition apparatus (manufactured by Choshu Sangyo Co., Ltd.), and a molybdenum vapor deposition boat containing the main material and a molybdenum vapor deposition boat containing the dopant material are mounted. Next, the vacuum chamber is reduced to 5 × 10⁻⁵ mm. -4 In the process described above, a vapor deposition boat containing the host material and a vapor deposition boat containing the dopant material are heated simultaneously to perform vapor deposition in a manner that achieves an appropriate film thickness, thus forming a mixed thin film of the host material and the dopant material. The vapor deposition rate is controlled according to a set weight ratio of the host material to the dopant material.

[0854] Evaluation of absorption and luminescence properties

[0855] Absorption spectra were measured using a UV-Vis-NIR spectrophotometer (Shimadzu Corporation, UV-2600). Fluorescence or phosphorescence spectra were measured using a spectrofluorescence spectrophotometer (Hitachi, F-7000).

[0856] For fluorescence spectroscopy measurements, photoluminescence was measured at room temperature using an appropriate excitation wavelength. For phosphorescence spectroscopy measurements, the accompanying cooling unit was used, and the samples were immersed in liquid nitrogen (at 77 K). An optical chopper was used to adjust the delay time from excitation light irradiation to the start of the measurement for phosphorescence spectrum observation. The samples were excited using an appropriate excitation wavelength, and photoluminescence was measured.

[0857] In addition, fluorescence quantum yield (PLQY) was determined using an absolute PL quantum yield measuring device (Hamamatsu Photonics, C9920-02G).

[0858] Evaluation of fluorescence lifetime (delayed fluorescence)

[0859] Fluorescence lifetime was measured at 300K using a fluorescence lifetime measuring apparatus (Hamamatsu Photonics, C11367-01). The components with fast and slow fluorescence lifetimes were determined at the maximum emission wavelength measured using an appropriate excitation wavelength. In the fluorescence lifetime measurement of typical organic EL materials emitting fluorescence at room temperature, the slow component involving the phosphorescent triplet component is hardly observed due to the thermal inactivation of the triplet component. When a slow component is observed in the compound being evaluated, it indicates that the triplet energy, representing a long excitation lifetime, has shifted to the singlet energy due to thermal activation and is observed as delayed fluorescence.

[0860] Calculation of bandgap (Eg)

[0861] The long wavelength end A (nm) of the absorption spectrum obtained by the aforementioned method is calculated using Eg = 1240 / A.

[0862] E S E T Calculation of ΔEST

[0863] Singlet excitation energy (E S The maximum emission wavelength B (nm) of the fluorescence spectrum is obtained through E S =1240 / B for calculation. Furthermore, the triplet excitation energy (E) T The maximum emission wavelength C (nm) of the phosphorescence spectrum is obtained through E T =1240 / C for calculation.

[0864] ΔEST utilizes E S With E T Energy difference ΔEST=E S -E TΔEST can also be defined using methods described, for example, in "Purely organic electroluminescent material realizing 100% conversion from electricity to light", H. Kaji, H. Suzuki, T. Fukushima, K. Shizu, K. Katsuaki, S. Kubo, T. Komino, H. Oiwa, F. Suzuki, A. Wakamiya, Y. Murata, C. Adachi, Nat. Commun. 2015, 6, 8476.

[0865] Evaluation of the basic physical properties of compounds (1-230)

[0866]

[0867] [Absorption and luminescence properties of dilute solutions]

[0868] The measured results show that a light-emitting light with an absorption peak wavelength of 482 nm, a fluorescence peak wavelength of 503 nm, a fluorescence peak half-width of 33 nm, and a PLQY of over 99% (sky blue to green with a narrow half-width) can be obtained. Figure 2 and Figure 3 ).

[0869] [Delayed fluorescence lifetime in dilute solutions]

[0870] The delayed fluorescence lifetime of compound (1-230) in toluene solution was measured. The fluorescence lifetime tau(prompt) was calculated based on the decay curve from 5.0 to 40 nsec and found to be 6.4 nsec. Figure 4 Furthermore, the delayed fluorescence lifetime tau (Delay) calculated from the decay curves of 6.0–25 μsec was 7.7 μsec. Figure 5 Therefore, using the methods described in J. Am. Chem. Soc. 2014, 136, 18070-18081 and Nat. Commun. 2015, 6, 8476, ΔEST was estimated to be 0.14 eV.

[0871] In summary, compounds (1-230) have a narrow half-width, can achieve high PLQY, and have small ΔEST and small tau (delay), thus they can be expected to be used as thermally activated delayed fluorescence materials.

[0872] Evaluation of the basic physical properties of compound (1-232)

[0873]

[0874] [Absorption and luminescence properties of dilute solutions]

[0875] The measured results show that the light emitted is sky blue to green with a narrow half-width, an absorption peak wavelength of 482 nm, a fluorescence peak wavelength of 504 nm, a fluorescence peak half-width of 31 nm, and a PLQY of 94%.

[0876] [Delayed fluorescence lifetime in dilute solutions]

[0877] The delayed fluorescence lifetime of compound (1-232) in toluene solution was measured. The fluorescence lifetime tau(prompt) was calculated from the decay curves of 4.6–40 nsec and found to be 5.7 nsec. Furthermore, the delayed fluorescence lifetime tau(Delay) was calculated from the decay curves of 5.8–6.6 μsec and found to be 1.8 μsec. Therefore, using the methods described in J. Am. Chem. Soc. 2014, 136, 18070–18081 and Nat. Commun. 2015, 6, 8476, ΔEST was estimated to be 0.11 eV.

[0878] In summary, compounds (1-232) have a narrow half-width, can achieve high PLQY, and have small ΔEST and small tau (delay), thus they can be expected to be used as thermally activated delayed fluorescence materials.

[0879] Evaluation of the basic physical properties of compound 1

[0880] The basic properties of the compound of formula (1-401) disclosed in International Publication No. 2015 / 102118 were evaluated as comparative compound 1.

[0881]

[0882] [Absorption and luminescence properties of the dispersible membrane]

[0883] The measured results show that a deep blue luminescent material with a narrow half-width at half-maximum (WWHM) was obtained, with an absorption peak wavelength of 439 nm, a fluorescence peak wavelength of 456 nm, a phosphorescence peak wavelength of 492 nm, a fluorescence peak WWHM of 36 nm, and a PLQY of 86%. Figure 6 Furthermore, based on the fluorescence peak wavelength and phosphorescence peak wavelength, ΔEST was calculated to be 0.20 eV.

[0884] [Delayed fluorescence lifetime of the dispersion film]

[0885] The delayed fluorescence lifetime was measured by preparing a thin film by dispersing comparative compound 1 at a concentration of 1% by weight in PMMA. The delayed fluorescence lifetime tau (Delay) was calculated from the decay curves of 100–250 μsec and found to be 94 μsec. Figure 7 ).

[0886] In summary, compound 1 exhibits an extremely high tau (delay), making it an undesirable luminescent material for organic EL elements utilizing TADF. Furthermore, its ΔEST is relatively small; therefore, while it is possible to exhibit TADF through improved element configuration, this is expected to result in elements with high roll-off and poor performance.

[0887] The following is a summary of the evaluation results of the basic physical properties.

[0888] [Table 1]

[0889]

[0890] <Evaluation of Organic EL Components>

[0891] As described above, the compounds of the present invention have sufficiently good PLQY and very small tau (delay), narrow half-width and emit deep blue light, and are therefore suitable as dopants for organic EL elements utilizing the TADF mechanism.

[0892] Evaluation items and evaluation methods

[0893] The evaluation parameters include driving voltage (V), emission wavelength (nm), CIE chromaticity (x,y), external quantum efficiency (%), maximum wavelength of emission spectrum (nm), half-width (nm), and roll-off. These evaluation parameters can be set using values ​​at appropriate luminance levels.

[0894] The quantum efficiency of a light-emitting element (LED) includes internal quantum efficiency and external quantum efficiency. Internal quantum efficiency represents the proportion of external energy injected into the LED's emissive layer in the form of electrons (or holes) that is purely converted into photons. On the other hand, external quantum efficiency is calculated based on the amount of photons released to the outside of the LED. Some photons generated in the emissive layer are absorbed internally by the LED or continuously reflected and are not released to the outside. Therefore, external quantum efficiency is lower than internal quantum efficiency.

[0895] The methods for measuring spectral radiance (emission spectrum) and external quantum efficiency are as follows. The element emits light by applying a voltage using an Advantest voltage / current generator R6144. The spectral radiance in the visible light region is measured using a TOPCON SR-3AR spectral radiance meter from a direction perpendicular to the emitting surface. Assuming the emitting surface is a perfectly diffused surface, the number of photons at each wavelength is obtained by dividing the measured spectral radiance value of each wavelength component by the wavelength energy and multiplying by π. The total number of photons emitted from the element is then accumulated across the entire observed wavelength region. The number of carriers injected into the element is obtained by dividing the applied current value by the elementary charge, and the external quantum efficiency is obtained by dividing the total number of photons emitted from the element by the number of carriers injected into the element. Furthermore, the half-maximum width (WWHM) of the emission spectrum is calculated as the width between wavelengths with the maximum emission wavelength as the center and its intensity reaching approximately 50%.

[0896] Attenuation refers to the phenomenon that efficiency decreases as voltage is applied to a component; a low efficiency is preferred. In TADF components, a large tau (delay) from dopants or auxiliary dopants results in greater attenuation, while a small tau (delay) results in less attenuation. As a method for comparing and evaluating the degree of attenuation, the efficiency at any two points of brightness or current density can be compared. High efficiency with low attenuation is preferred.

[0897] (1) Vapor-deposited organic EL element

[0898] Organic EL elements were fabricated, and current density, luminance, chromaticity, and external quantum efficiency were measured by applying voltage. Four configurations—A (Table 2), B (Table 3), C (Table 4), and D (Table 5)—were selected for evaluation as the fabricated organic EL elements. Configurations A through D are all suitable for thermally activated delayed fluorescence materials. Configuration A, as shown in the literature (Adv. Mater. 2016, 28, 2777-2781), is a configuration that promises high efficiency. Configuration B, as shown in the literature (Scientific Reports, 6, 2016, 22463), is a configuration that promises relatively high efficiency and long-term driving stability. Configuration C, as shown in the literature (Thin Solid Films, 619, 2016, 120-124), is a configuration using a different host material than Configuration A. Configuration D is a long-lifespan component configuration presented as publication number S4-2 at the 26th regular session of the Organic EL Symposium held on June 21 and 22, 2018. The application of the compounds of this invention is not limited to these configurations, and the film thickness and constituent materials of each layer can be appropriately varied according to the basic physical properties of the compounds of this invention.

[0899] [Table 2]

[0900] (The composition of organic EL elements A)

[0901]

[0902] In Table 2, “NPD” stands for N,N'-diphenyl-N,N'-dinathyl-4,4'-diaminobiphenyl, “TcTa” stands for 4,4',4”-tris(N-carbazolyl)triphenylamine, “mCP” stands for 1,3-bis(N-carbazolyl)benzene, “mCBP” stands for 3,3'-bis(N-carbazolyl)-1,1'-biphenyl, and “TSPO1” stands for diphenyl-[4-(triphenylsilyl)phenyl]phosphine oxide. The chemical structures are shown below.

[0903]

[0904] <Example A1>

[0905] <Component A: Components doped with compound (1-230)>

[0906] A 26mm × 28mm × 0.7mm glass substrate (manufactured by Optoscience) was obtained by sputtering an ITO film to a thickness of 200nm and grinding it to 50nm as a transparent support substrate. This transparent support substrate was fixed to the substrate holder of a commercially available vapor deposition apparatus (manufactured by Choshu Sangyo Co., Ltd.), and tantalum vapor deposition boats containing NPD, TcTa, mCP, mCBP, compound (1-230), and TSPO1, respectively, and aluminum nitride vapor deposition boats containing LiF and aluminum, respectively.

[0907] The following layers are sequentially formed on the ITO film of the transparent support substrate. The vacuum chamber is depressurized to 5 × 10⁻⁶. -4First, NPD is heated and deposited at a thickness of 40 nm. Next, TcTa is heated and deposited at a thickness of 15 nm to form a two-layer hole layer. Then, mCP is heated and deposited at a thickness of 15 nm to form an electron blocking layer. Next, mCBP and compound (1-230) are simultaneously heated and deposited at a thickness of 20 nm to form a light-emitting layer. The deposition rate is adjusted to a weight ratio of approximately 99:1 for mCBP to compound (1-230). Next, TSPO1 is heated and deposited at a thickness of 40 nm to form an electron transport layer. The deposition rate for each layer is 0.01–1 nm / s. Subsequently, LiF is heated and deposited at a thickness of 1 nm at a deposition rate of 0.01–0.1 nm / s. Finally, aluminum is heated and deposited at a thickness of 100 nm to form a cathode, thus obtaining an organic EL device. At this point, the evaporation rate of aluminum is adjusted to 1~10 nm / second.

[0908] Using an ITO electrode as the anode and an aluminum electrode as the cathode, a DC voltage was applied to measure brightness, chromaticity, and external quantum efficiency.

[0909] <Example A2>

[0910] <Component A: Components doped with compounds (1-28)>

[0911] Organic EL elements were obtained by replacing compounds (1-230) in Example A1 with compounds (1-28) in the same manner as in Example A1.

[0912] [Table 3]

[0913] (Composition of organic EL elements B)

[0914]

[0915] In Table 3, “HAT-CN” represents 1,4,5,8,9,12-hexaazabenzophenanthrene hexacarboxynitrile, “Tris-PCz” represents 9,9',9”-triphenyl-9H,9H',9H”-3,3',6',3”-tricarbazole, “T2T” represents 2,4,6-tris[[1,1'-biphenyl]-3-yl]-1,3,5-triazine, and “BPy-TP2” represents 2,7-bis([2,2'-bipyridin]-5-yl)benzophenanthrene. The chemical structures are shown below.

[0916]

[0917] <Example B1>

[0918] <Component B: Elements using compounds (1-230) as dopants>

[0919] A 26mm × 28mm × 0.7mm glass substrate (OPTOSCIENCE Corporation) obtained by sputtering ITO film to 50nm was used as a transparent support substrate. This transparent support substrate was fixed to the substrate support of a commercially available vapor deposition apparatus (Choshu Sangyo Corporation), and tantalum vapor deposition crucibles containing HAT-CN, Tris-PCz, mCBP, compound (1-230), T2T, and BPy-TP2, respectively, and aluminum nitride vapor deposition crucibles containing LiF and aluminum, respectively, were installed.

[0920] The following layers are sequentially formed on the ITO film of the transparent support substrate. The vacuum chamber is depressurized to 2.0 × 10⁻⁶. -4 First, HAT-CN was heated and vapor-deposited to a thickness of 10 nm. Next, Tris-PCz was heated and vapor-deposited to a thickness of 30 nm, thus forming a two-layer hole layer. Then, mCBP and compound (1-230) were simultaneously heated and vapor-deposited to a thickness of 30 nm to form a light-emitting layer. The deposition rate was adjusted to a weight ratio of approximately 90:10 for mCBP to compound (1-230). Next, T2T was heated and vapor-deposited to a thickness of 10 nm. Then, BPy-TP2 was vapor-deposited to a thickness of 30 nm to form a two-layer electron transport layer. The deposition rate for each layer was 0.01–1 nm / s. Subsequently, LiF is heated and vapor-deposited at a thickness of 1 nm and a vapor deposition rate of 0.01~0.1 nm / s. Then, aluminum is heated and vapor-deposited at a thickness of 100 nm and a vapor deposition rate of 0.1~2 nm / s to form a cathode, thereby obtaining an organic EL device.

[0921] <Example B2>

[0922] <Component B: Elements doped with compounds (1-28)>

[0923] Organic EL elements were obtained by replacing compounds (1-230) in Example B1 with compounds (1-28) in the same manner as in Example B1.

[0924] [Table 4]

[0925] (The composition of organic EL elements C)

[0926]

[0927] In Table 4, "2CzBN" represents 3,4-bis(9H-carbazol-9-yl)benzonitrile. The chemical structure is shown below.

[0928]

[0929] <Example C1>

[0930] <Composition C: Elements using compounds (1-230) as dopants>

[0931] A 26mm × 28mm × 0.7mm glass substrate (OPTOSCIENCE Corporation) obtained by grinding ITO film formed by sputtering to 50nm was used as a transparent support substrate. This transparent support substrate was fixed to the substrate holder of a commercially available vapor deposition apparatus (Choshu Sangyo Corporation), and tantalum vapor deposition crucibles containing HAT-CN, Tris-PCz, mCP, 2CzBN, compound (1-230), and BPy-TP2, and aluminum nitride vapor deposition crucibles containing LiF and aluminum were installed.

[0932] The following layers are sequentially formed on the ITO film of the transparent support substrate. The vacuum chamber is depressurized to 2.0 × 10⁻⁶. -4 First, HAT-CN was heated and deposited at a thickness of 10 nm. Next, Tris-PCz was heated and deposited at a thickness of 25 nm. Then, mCP was heated and deposited at a thickness of 10 nm, thus forming a three-layer hole layer. Next, 2CzBN and compound (1-230) were simultaneously heated and deposited at a thickness of 30 nm to form a light-emitting layer. The deposition rate was adjusted to a weight ratio of approximately 90:10 for 2CzBN to compound (1-230). Next, 2CzBN was heated and deposited at a thickness of 10 nm. Then, BPy-TP2 was deposited at a thickness of 40 nm to form a two-layer electron transport layer. The deposition rate for each layer was 0.01–1 nm / s. Subsequently, LiF is heated and vapor-deposited at a thickness of 1 nm and a vapor deposition rate of 0.01~0.1 nm / s. Then, aluminum is heated and vapor-deposited at a thickness of 100 nm and a vapor deposition rate of 0.1~2 nm / s to form a cathode, thereby obtaining an organic EL device.

[0933] <Example C2>

[0934] <Composition C: Components doped with compounds (1-28)>

[0935] Organic EL elements were obtained by replacing compounds (1-230) in Example C1 with compounds (1-28) in the same manner as in Example C1.

[0936] [Table 5]

[0937] (The composition of organic EL elements D)

[0938]

[0939] In Table 5, “SF3-TRZ” is 2-(9,9'-spirodifluorene-3-yl)-4,6-diphenylpyrimidine, and “Liq” is lithium 8-hydroxyquinoline. The chemical structures are shown below.

[0940]

[0941] <Example D1>

[0942] <Construction D: Elements using compounds (1-230) as dopants>

[0943] A 26mm × 28mm × 0.7mm glass substrate (OPTOSCIENCE Corporation) obtained by sputtering ITO film to 50nm was used as a transparent support substrate. This transparent support substrate was fixed to the substrate support of a commercially available vapor deposition apparatus (Choshu Sangyo Corporation), and tantalum vapor deposition crucibles containing HAT-CN, Tris-PCz, mCBP, compound (1-230), SF3-TRZ, and Liq, and aluminum nitride vapor deposition crucibles containing aluminum were installed.

[0944] The following layers are sequentially formed on the ITO film of the transparent support substrate. The vacuum chamber is depressurized to 2.0 × 10⁻⁶. -4 First, HAT-CN was heated and vapor-deposited to a thickness of 10 nm. Next, Tris-PCz was heated and vapor-deposited to a thickness of 30 nm, thus forming a two-layer hole layer. Then, mCBP was heated and vapor-deposited to a thickness of 5 nm, thus forming an electron blocking layer. Next, mCBP and compound (1-230) were simultaneously heated and vapor-deposited to a thickness of 30 nm to form a light-emitting layer. The vapor deposition rate was adjusted to a weight ratio of approximately 90:10 for mCBP to compound (1-230). Next, SF3-TRZ was heated and vapor-deposited to a thickness of 10 nm, thus forming a hole blocking layer. Next, SF3-TRZ and Liq were simultaneously heated and vapor-deposited to a thickness of 50 nm to form an electron transport layer. The vapor deposition rate was adjusted to a weight ratio of approximately 70:30 for SF3-TRZ to Liq. The vapor deposition rate for each layer was 0.01–1 nm / s. Subsequently, Liq is heated and vapor-deposited at a rate of 0.01~0.1 nm / s to achieve a film thickness of 2 nm. Then, aluminum is heated and vapor-deposited at a rate of 0.1~2 nm / s to achieve a film thickness of 100 nm to form a cathode, thereby obtaining an organic EL device.

[0945] <Example D2>

[0946] <Composition D: Components doped with compounds (1-28)>

[0947] Organic EL elements were obtained by replacing compounds (1-230) in Example D1 with compounds (1-28) in the same manner as in Example D1.

[0948] (2) Coated organic EL element

[0949] Next, an organic EL element obtained by coating to form an organic layer will be described.

[0950] <Synthesis of the host polymer: SPH-101>

[0951] SPH-101 was synthesized according to the method described in International Publication No. 2015 / 008851. A copolymer with M2 or M3 bonded to M1 was obtained, and the molar ratio of each unit was estimated to be 50:26:24 based on the feed ratio.

[0952]

[0953] <Synthesis of a Polymer Hole Transport Compound: XLP-101>

[0954] XLP-101 was synthesized according to the method described in Japanese Patent Application Publication No. 2018-61028. A copolymer with M2 or M3 bonded to the side of M7 was obtained, and the molar ratio of each unit was estimated to be 40:10:50 based on the feed ratio.

[0955]

[0956] <Examples T1~T9>

[0957] Prepare a coating solution for the materials that form each layer, and fabricate a coated organic EL element.

[0958] <Fabrication of Organic EL Components in Examples T1~T3>

[0959] The material composition of each layer in the organic EL element is shown in Table 6.

[0960] [Table 6]

[0961]

[0962] The structure of “ET” in Table 6 is shown below.

[0963]

[0964] <Preparation of composition (1) for forming light-emitting layer>

[0965] The composition (1) for forming a light-emitting layer is prepared by stirring the following components until a homogeneous solution is formed. The prepared composition for forming a light-emitting layer is spin-coated on a glass substrate and heated and dried under reduced pressure, whereby a coating film without film defects and excellent smoothness is obtained.

[0966] Compound (A) 0.04% by weight

[0967] SPH-101 1.96% by weight

[0968] Xylene 69.00% by weight

[0969] Decalin 29.00% by weight

[0970] It should be noted that Compound (A) is a polycyclic aromatic compound represented by General Formula (1), a polymer compound obtained by polymerizing the polycyclic aromatic compound as a monomer (i.e., the monomer has a reactive substituent), or a polymer crosslinked body obtained by further crosslinking the polymer compound. The polymer compound for obtaining the polymer crosslinked body has a crosslinkable substituent.

[0971] <PEDOT:PSS solution>

[0972] A commercially available PEDOT:PSS solution (Clevios (TM) P VP AI4083, an aqueous dispersion of PEDOT:PSS, manufactured by Heraeus Holdings) is used.

[0973]

[0974] <Preparation of OTPD solution>

[0975] OTPD (LT-N159, manufactured by Luminescence Technology Corp) and IK-2 (a photo cationic polymerization initiator, manufactured by SAN-APRO) are dissolved in toluene to prepare an OTPD solution with an OTPD concentration of 0.7% by weight and an IK-2 concentration of 0.007% by weight.

[0976]

[0977] <Preparation of XLP-101 solution>

[0978] XLP-101 is dissolved in xylene at a concentration of 0.6% by weight to prepare a 0.7% by weight XLP-101 solution.

[0979] <Preparation of PCz solution>

[0980] A 0.7% by weight PCz solution was prepared by dissolving PCz (polyvinylcarbazole) in dichlorobenzene.

[0981]

[0982] <Example T1>

[0983] A PEDOT:PSS solution was spin-coated onto a glass substrate with ITO deposited to a thickness of 150 nm, and then calcined on a hot plate at 200 °C for 1 hour to form a 40 nm thick PEDOT:PSS film (hole injection layer). Next, an OTPD solution was spin-coated, and after drying on a hot plate at 80 °C for 10 minutes, the film was exposed using an exposure machine at 100 mJ / cm². 2 The film is exposed to the specified exposure intensity and fired on a heating plate at 100°C for 1 hour to form an OTPD film (hole transport layer) with a thickness of 30 nm that is insoluble in the solution. Next, the light-emitting layer forming composition (1) is spin-coated and fired on a heating plate at 120°C for 1 hour to form a light-emitting layer with a thickness of 20 nm.

[0984] The fabricated multilayer film was fixed onto the substrate support of a commercially available vapor deposition apparatus (manufactured by Showa Vacuum Corporation). Molybdenum vapor deposition boats containing ET, LiF, and aluminum were then mounted. The vacuum chamber was reduced to 5 × 10⁻⁶. -4 After Pa, ET is heated and deposited at a thickness of 30 nm to form an electron transport layer. The deposition rate for forming the electron transport layer is set to 1 nm / s. Then, LiF is heated and deposited at a thickness of 1 nm at a deposition rate of 0.01~0.1 nm / s. Next, aluminum is heated and deposited at a thickness of 100 nm to form the cathode. This process yields an organic EL device.

[0985] <Example T2>

[0986] Organic EL elements were obtained using the same method as in Example T1. It should be noted that the hole transport layer was formed by spin-coating an XLP-101 solution and then firing it on a hot plate at 200°C for 1 hour to obtain a film with a thickness of 30 nm.

[0987] <Example T3>

[0988] Organic EL devices were obtained using the same method as in Example T1. It should be noted that the hole transport layer was formed by spin-coating a PCz solution and then firing it on a hot plate at 120°C for 1 hour to obtain a film with a thickness of 30 nm.

[0989] <Fabrication of Organic EL Components in Examples T4-T6>

[0990] The material composition of each layer in the organic EL element is shown in Table 7.

[0991] [Table 7]

[0992]

[0993] <Preparation of compositions (2) to (4) for forming the light-emitting layer>

[0994] The composition (2) for forming a light-emitting layer is prepared by stirring the following components until a homogeneous solution is formed.

[0995] Compound (A) 0.02% by weight

[0996] mCBP 1.98% by weight

[0997] Toluene 98.00% by weight

[0998] The composition (3) for forming the light-emitting layer is prepared by stirring the following components until a homogeneous solution is formed.

[0999] Compound (A) 0.02% by weight

[1000] SPH-101 1.98% by weight

[1001] Xylene 98.00% by weight

[1002] The composition (4) for forming the light-emitting layer is prepared by stirring the following components until a homogeneous solution is formed.

[1003] Compound (A) 0.02% by weight

[1004] DOBNA 1.98% by weight

[1005] Toluene 98.00% by weight

[1006] In Table 7, “mCBP” stands for 3,3'-bis(N-carbazolyl)-1,1'-biphenyl, “DOBNA” stands for 3,11-di-o-tolyl-5,9-dioxa-13b-boronanaphen[3,2,1-de]anthracene, and “TSPO1” stands for diphenyl[4-(triphenylsilyl)phenyl]phosphine oxide. The chemical structures are shown below.

[1007]

[1008] <Example T4>

[1009] After spin-coating an ND-3202 (manufactured by Nissan Chemical Industries, Ltd.) solution onto a glass substrate with an ITO film thickness of 45 nm, the substrate was heated at 50 °C for 3 minutes under atmospheric atmosphere, and then heated at 230 °C for 15 minutes to form an ND-3202 film (hole injection layer) with a thickness of 50 nm. Next, an XLP-101 solution was spin-coated, and the substrate was heated at 200 °C for 30 minutes under a nitrogen atmosphere to form an XLP-101 film (hole transport layer) with a thickness of 20 nm. Next, a light-emitting layer forming composition (2) was spin-coated, and the substrate was heated at 130 °C for 10 minutes under a nitrogen atmosphere to form a light-emitting layer with a thickness of 20 nm.

[1010] The fabricated multilayer film was fixed onto the substrate support of a commercially available vapor deposition apparatus (manufactured by Showa Vacuum Corporation). Molybdenum vapor deposition boats containing TSPO1, LiF, and aluminum were mounted. The vacuum chamber was reduced to 5 × 10⁻⁶. -4 After Pa, TSPO1 is heated and deposited at a thickness of 30 nm to form an electron transport layer. The deposition rate for forming the electron transport layer is set to 1 nm / s. Next, LiF is heated and deposited at a thickness of 1 nm at a deposition rate of 0.01~0.1 nm / s. Then, aluminum is heated and deposited at a thickness of 100 nm to form the cathode. This process is repeated to obtain an organic EL device.

[1011] <Examples T5 and T6>

[1012] Organic EL elements are obtained using the same method as in Example T4, with the composition (3) or (4) for forming the light-emitting layer.

[1013] <Fabrication of Organic EL Components in Examples T7-T9>

[1014] The material composition of each layer in the organic EL element is shown in Table 8.

[1015] [Table 8]

[1016]

[1017] <Preparation of compositions (5) to (7) for forming the light-emitting layer>

[1018] The composition (5) for forming the light-emitting layer is prepared by stirring the following components until a homogeneous solution is formed.

[1019] Compound (A) 0.02% by weight

[1020] 2PXZ-TAZ 0.18% by weight

[1021] mCBP 1.80% by weight

[1022] Toluene 98.00% by weight

[1023] The composition (6) for forming a light-emitting layer is prepared by stirring the following components until a homogeneous solution is formed.

[1024] Compound (A) 0.02% by weight

[1025] 2PXZ-TAZ 0.18% by weight

[1026] SPH-101 1.80% by weight

[1027] Xylene 98.00% by weight

[1028] The composition (7) for forming the light-emitting layer is prepared by stirring the following components until a homogeneous solution is formed.

[1029] Compound (A) 0.02% by weight

[1030] 2PXZ-TAZ 0.18% by weight

[1031] DOBNA 1.80% by weight

[1032] Toluene 98.00% by weight

[1033] In Table 8, “2PXZ-TAZ” is 10,10'-((4-phenyl-4H-1,2,4-triazol-3,5-diyl)bis(4,1-phenyl))bis(10H-phenoxazine). The chemical structure is shown below.

[1034]

[1035] <Example T7>

[1036] After spin-coating an ND-3202 (manufactured by Nissan Chemical Industries, Ltd.) solution onto a glass substrate with an ITO film thickness of 45 nm, the substrate was heated at 50 °C for 3 minutes under atmospheric atmosphere, and then heated at 230 °C for 15 minutes to form an ND-3202 film (hole injection layer) with a thickness of 50 nm. Next, an XLP-101 solution was spin-coated, and the substrate was heated at 200 °C for 30 minutes under a nitrogen atmosphere to form an XLP-101 film (hole transport layer) with a thickness of 20 nm. Next, a light-emitting layer forming composition (5) was spin-coated, and the substrate was heated at 130 °C for 10 minutes under a nitrogen atmosphere to form a light-emitting layer with a thickness of 20 nm.

[1037] The fabricated multilayer film was fixed onto the substrate support of a commercially available vapor deposition apparatus (manufactured by Showa Vacuum Corporation). Molybdenum vapor deposition boats containing TSPO1, LiF, and aluminum were mounted. The vacuum chamber was reduced to 5 × 10⁻⁶.-4 After Pa, TSPO1 is heated and deposited at a thickness of 30 nm to form an electron transport layer. The deposition rate for forming the electron transport layer is set to 1 nm / s. Next, LiF is heated and deposited at a thickness of 1 nm at a deposition rate of 0.01~0.1 nm / s. Then, aluminum is heated and deposited at a thickness of 100 nm to form the cathode. This process yields an organic EL device.

[1038] <Examples T8 and T9>

[1039] Organic EL elements were obtained using the same method as in Example T7, with the composition (6) or (7) for forming the light-emitting layer.

[1040] Industrial availability

[1041] In this invention, by providing polycyclic aromatic compounds with novel structures, the options for materials used in organic devices, such as materials for organic EL elements, can be increased. Furthermore, by using polycyclic aromatic compounds with novel structures as materials for, for example, organic electroluminescent elements, it is possible to provide excellent organic devices such as organic EL elements, display devices equipped with them, and lighting devices equipped with them.

[1042] Industrial availability

[1043] 100 Organic electroluminescent elements

[1044] 101 substrate

[1045] 102 Anode

[1046] 103 Hole Injection Layer

[1047] 104 Hole Transport Layer

[1048] 105 Emissive Layer

[1049] 106 Electron Transport Layer

[1050] 107 Electron Injection Layer

[1051] 108 cathode

Claims

1. A polycyclic aromatic compound, represented by the following general formula (1), In the above formula (1), Rings A, B, and C are each independently an aromatic or heteroaromatic ring, and at least one hydrogen atom in these rings may be substituted. Y 1 Each of these can be independently B, P, P=O, P=S, Al, Ga, As, Si-R, or Ge-R, wherein the R in Si-R and Ge-R is aryl, alkyl, or cycloalkyl. X 1 Each is independently N or CR, where R in CR is an optionally substituted aryl, optionally substituted alkyl, or optionally substituted cycloalkyl. X 2 Each of the following is independently >O, >NR, >C(-R)2, >S, or >Se, wherein the R in >NR is an optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkyl, or optionally substituted cycloalkyl, and the R in >C(-R)2 is hydrogen, optionally substituted aryl, optionally substituted alkyl, or optionally substituted cycloalkyl, and the R in >NR and / or >C(-R)2 is optionally bonded to the A ring and / or C ring by means of a linking group or a single bond. X 1 When the value is N, some or all of two adjacent A rings can be bonded together by single bonds. n is an integer greater than or equal to 1, and At least one hydrogen atom in the compound shown in formula (1) may be optionally replaced by deuterium, cyano or halogen.

2. The polycyclic aromatic compound according to claim 1, wherein, Rings A, B, and C are each independently an aromatic or heteroaromatic ring, wherein at least one hydrogen atom of these rings is optionally substituted or unsubstituted with an aryl group, a substituted or unsubstituted heteroaromatic group, a substituted or unsubstituted diarylamino group, a substituted or unsubstituted diheteroarylamino group, a substituted or unsubstituted arylheteroarylamino group, a substituted or unsubstituted diarylboryl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, or a substituted silyl group, wherein the two aryl groups in the diarylboryl group are optionally bonded by a single bond or a linking group. Y 1 Each of these can be independently B, P, P=O, P=S, Al, Ga, As, Si-R, or Ge-R, wherein the R in Si-R and Ge-R is aryl, alkyl, or cycloalkyl. X 1 Each is independently N or CR, where R in CR is an optionally substituted aryl, optionally substituted alkyl, or optionally substituted cycloalkyl. X 2 Each of the following is independently >O, >NR, >C(-R)2, >S, or >Se, wherein the R in >NR is an aryl group optionally substituted with an alkyl or cycloalkyl group, a heteroaryl group optionally substituted with an alkyl or cycloalkyl group, an alkyl or cycloalkyl group, and the R in >NR and / or >C(-R)2 is hydrogen, an aryl group optionally substituted with an alkyl or cycloalkyl group, an alkyl or cycloalkyl group, and the R in >NR and / or >C(-R)2 is optionally bonded to the A ring and / or C ring via -O-, -S-, -C(-R)2-, -Si(-R)2-, or a single bond, and the R in -C(-R)2- or -Si(-R)2- is hydrogen, an alkyl or cycloalkyl group. X 1 When the value is N, all adjacent A rings can be bonded to each other arbitrarily using single bonds. n is an integer from 1 to 5, and At least one hydrogen atom in the compound shown in formula (1) may be optionally replaced by deuterium, cyano or halogen.

3. The polycyclic aromatic compound according to claim 1, represented by the following general formula (2), In the above formula (2), R a Each of these elements is independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl, alkyl, cycloalkyl, alkoxy, aryloxy, triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, or alkyldicycloalkylsilyl, wherein at least one hydrogen atom is optionally substituted with an aryl, heteroaryl, alkyl, or cycloalkyl group, wherein... The two aryl groups in the diarylboronyl group are optionally bonded by single bonds or linking groups. R b Each of the following groups is independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl, alkyl, cycloalkyl, alkoxy, aryloxy, triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, or alkyldicycloalkylsilyl, wherein at least one hydrogen atom is optionally substituted with an aryl, heteroaryl, alkyl, or cycloalkyl group, wherein the two aryl groups in the diarylboryl group are optionally bonded by a single bond or a linking group, and R c Each of the following groups is independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl, alkyl, cycloalkyl, alkoxy, aryloxy, triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, or alkyldicycloalkylsilyl, wherein at least one hydrogen atom is optionally substituted with an aryl, heteroaryl, alkyl, or cycloalkyl group, wherein the two aryl groups in the diarylboryl group are optionally bonded by a single bond or a linking group. Furthermore, R a R b and R c The adjacent groups may optionally be bonded to each other and together with ring a, ring b, or ring c to form an aromatic ring or heteroaromatic ring. At least one hydrogen atom of the formed ring may optionally be substituted with an aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl, alkyl, cycloalkyl, alkoxy, aryloxy, triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, or alkyldicycloalkylsilyl. At least one hydrogen atom of these substituents may optionally be substituted with an aryl, heteroaryl, alkyl, or cycloalkyl group. The two aryl groups in the diarylboryl group may optionally be bonded by a single bond or a linking group. Y 1 Each of these can be independently B, P, P=O, P=S, Al, Ga, As, Si-R, or Ge-R, wherein the R in Si-R and Ge-R is an aryl group with 6 to 12 carbon atoms, an alkyl group with 1 to 6 carbon atoms, or a cycloalkyl group with 3 to 14 carbon atoms. X 1 Each is independently N or CR, wherein the R in CR is an aryl group having 6 to 12 carbon atoms, an alkyl group having 1 to 6 carbon atoms, or a cycloalkyl group having 3 to 14 carbon atoms. X 2 Each of the following is independently >O, >NR, >C(-R)2, >S, or >Se, wherein the R in >NR is an aryl group with 6 to 12 carbon atoms, a heteroaryl group with 2 to 15 carbon atoms, an alkyl group with 1 to 6 carbon atoms, or a cycloalkyl group with 3 to 14 carbon atoms, and at least one hydrogen atom of the aryl or heteroaryl group is optionally substituted with an alkyl group with 1 to 6 carbon atoms or a cycloalkyl group with 3 to 14 carbon atoms, and the R in >C(-R)2 is hydrogen, an aryl group with 6 to 12 carbon atoms, or a group with 1 to 6 carbon atoms. The aryl group is an alkyl group or a cycloalkyl group having 3 to 14 carbon atoms, wherein at least one hydrogen atom of the aryl group is optionally substituted with an alkyl group having 1 to 6 carbon atoms or a cycloalkyl group having 3 to 14 carbon atoms, and the R of the >NR and / or the >C(-R)2 is optionally bonded to the a ring and / or the c ring by means of -O-, -S-, -C(-R)2-, -Si(-R)2- or a single bond, wherein the R of the -C(-R)2- is hydrogen, an alkyl group having 1 to 6 carbon atoms, or a cycloalkyl group having 3 to 14 carbon atoms. X 1 When the value is N, all adjacent a-rings can be bonded to each other arbitrarily using single bonds. n is an integer from 1 to 3, and At least one hydrogen atom in the compound shown in formula (2) may be optionally replaced by deuterium, cyano or halogen.

4. The polycyclic aromatic compound according to claim 3, wherein, R a Each of the following groups is independently hydrogen, an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, a diarylamino group, a diarylboryl group, an alkyl group having 1 to 24 carbon atoms, or a cycloalkyl group having 3 to 24 carbon atoms. At least one hydrogen atom in these aryl or heteroaryl groups is optionally substituted with an alkyl group having 1 to 6 carbon atoms or a cycloalkyl group having 3 to 14 carbon atoms. The aryl group in the diarylamino group is an aryl group having 6 to 12 carbon atoms, and the aryl group in the diarylboryl group is optionally bonded by a single bond or a linking group. R b Each of the following groups is independently hydrogen, an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, a diarylamino group, a diarylboryl group, an alkyl group having 1 to 24 carbon atoms, or a cycloalkyl group having 3 to 24 carbon atoms. At least one hydrogen atom of these aryl or heteroaryl groups is optionally substituted with an alkyl group having 1 to 6 carbon atoms or a cycloalkyl group having 3 to 14 carbon atoms. The aryl group in the diarylamino group is an aryl group having 6 to 12 carbon atoms, and the aryl group in the diarylboryl group is an aryl group having 6 to 12 carbon atoms. The two aryl groups in the diarylboryl group are optionally bonded by a single bond or a linking group. R c Each of the following groups is independently hydrogen, an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, a diarylamino group, a diarylboryl group, an alkyl group having 1 to 24 carbon atoms, or a cycloalkyl group having 3 to 24 carbon atoms. At least one hydrogen atom in these aryl or heteroaryl groups is optionally substituted with an alkyl group having 1 to 6 carbon atoms or a cycloalkyl group having 3 to 14 carbon atoms. The aryl group in the diarylamino group is an aryl group having 6 to 12 carbon atoms, and the aryl group in the diarylboryl group is optionally bonded by a single bond or a linking group. Furthermore, R a R b and R c The adjacent groups may optionally bond to each other and, together with ring a, ring b, or ring c, form an aromatic ring with 9 to 16 carbon atoms or a heteroaromatic ring with 6 to 15 carbon atoms. At least one hydrogen atom in the formed ring may optionally be substituted by an aryl group with 6 to 30 carbon atoms, a heteroaromatic group with 2 to 30 carbon atoms, a diarylamino group, a diarylboryl group, an alkyl group with 1 to 24 carbon atoms, or a cycloalkyl group with 3 to 24 carbon atoms. At least one hydrogen atom in these aryl or heteroaromatic groups may optionally be substituted by an alkyl group with 1 to 6 carbon atoms or a cycloalkyl group with 3 to 14 carbon atoms. The aryl group in the diarylamino group is an aryl group with 6 to 12 carbon atoms, and the aryl group in the diarylboryl group is an aryl group with 6 to 12 carbon atoms. The two aryl groups in the diarylboryl group may optionally be bonded by a single bond or a linking group. Y 1 Each can be independently B, P, P=O, P=S, or Si-R, wherein the R in Si-R is an aryl group with 6 to 10 carbon atoms, an alkyl group with 1 to 5 carbon atoms, or a cycloalkyl group with 5 to 10 carbon atoms. X 1 Each is independently N or CR, wherein the R in CR is an aryl group having 6 to 10 carbon atoms, an alkyl group having 1 to 5 carbon atoms, or a cycloalkyl group having 5 to 10 carbon atoms. X 2 Each is independently >O, >NR, >C(-R)2, or >S, wherein the R in >NR is an aryl group with 6 to 10 carbon atoms, an alkyl group with 1 to 5 carbon atoms, or a cycloalkyl group with 5 to 10 carbon atoms, and at least one hydrogen atom of the aryl group is optionally substituted with an alkyl group with 1 to 5 carbon atoms or a cycloalkyl group with 5 to 10 carbon atoms; wherein the R in >C(-R)2 is hydrogen, an aryl group with 6 to 10 carbon atoms, an alkyl group with 1 to 5 carbon atoms, or a cycloalkyl group with 5 to 10 carbon atoms, and at least one hydrogen atom of the aryl group is optionally substituted with an alkyl group with 1 to 5 carbon atoms or a cycloalkyl group with 5 to 10 carbon atoms. n is an integer from 1 to 3, and At least one hydrogen atom in the compound shown in formula (2) may be optionally replaced by deuterium, cyano or halogen.

5. The polycyclic aromatic compound according to claim 3, wherein, R a Each of the following groups is independently hydrogen, an aryl group having 6 to 16 carbon atoms, a heteroaryl group having 2 to 20 carbon atoms, a diarylamino group, a diarylboryl group, an alkyl group having 1 to 12 carbon atoms, or a cycloalkyl group having 3 to 16 carbon atoms. At least one hydrogen atom in these aryl or heteroaryl groups is optionally substituted with an alkyl group having 1 to 6 carbon atoms or a cycloalkyl group having 3 to 14 carbon atoms. The aryl group in the diarylamino group is an aryl group having 6 to 10 carbon atoms, and the aryl group in the diarylboryl group is optionally bonded by a single bond or a linking group. R b Each of the following groups is independently hydrogen, an aryl group having 6 to 16 carbon atoms, a heteroaryl group having 2 to 20 carbon atoms, a diarylamino group, a diarylboryl group, an alkyl group having 1 to 12 carbon atoms, or a cycloalkyl group having 3 to 16 carbon atoms. At least one hydrogen atom of these aryl or heteroaryl groups is optionally substituted with an alkyl group having 1 to 6 carbon atoms or a cycloalkyl group having 3 to 14 carbon atoms. The aryl group in the diarylamino group is an aryl group having 6 to 10 carbon atoms, and the aryl group in the diarylboryl group is an aryl group having 6 to 10 carbon atoms. The two aryl groups in the diarylboryl group are optionally bonded by a single bond or a linking group. R c Each of the following groups is independently hydrogen, an aryl group having 6 to 16 carbon atoms, a heteroaryl group having 2 to 20 carbon atoms, a diarylamino group, a diarylboryl group, an alkyl group having 1 to 12 carbon atoms, or a cycloalkyl group having 3 to 16 carbon atoms. At least one hydrogen atom in these aryl or heteroaryl groups is optionally substituted with an alkyl group having 1 to 6 carbon atoms or a cycloalkyl group having 3 to 14 carbon atoms. The aryl group in the diarylamino group is an aryl group having 6 to 10 carbon atoms, and the aryl group in the diarylboryl group is optionally bonded by a single bond or a linking group. Y 1 Each can be independently represented as B, P, P=O, or P=S. X 1 Let N be the number of ... X 2 Each is independently >O, >NR, or >C(-R)2, wherein the R in >NR is an aryl group with 6 to 10 carbon atoms, an alkyl group with 1 to 5 carbon atoms, or a cycloalkyl group with 5 to 10 carbon atoms, and at least one hydrogen atom of the aryl group is optionally substituted with an alkyl group with 1 to 5 carbon atoms or a cycloalkyl group with 5 to 10 carbon atoms; wherein the R in >C(-R)2 is hydrogen, an aryl group with 6 to 10 carbon atoms, an alkyl group with 1 to 5 carbon atoms, or a cycloalkyl group with 5 to 10 carbon atoms, and at least one hydrogen atom of the aryl group is optionally substituted with an alkyl group with 1 to 5 carbon atoms or a cycloalkyl group with 5 to 10 carbon atoms. n is an integer from 1 to 3, and At least one hydrogen atom in the compound shown in formula (2) may be optionally replaced by deuterium, cyano or halogen.

6. The polycyclic aromatic compound according to claim 3, wherein, R a Each of the following groups is independently hydrogen, an aryl group having 6 to 16 carbon atoms, a heteroaryl group having 2 to 20 carbon atoms, a diarylamino group, a diarylboryl group, an alkyl group having 1 to 12 carbon atoms, or a cycloalkyl group having 3 to 16 carbon atoms. At least one hydrogen atom in these aryl or heteroaryl groups is optionally substituted with an alkyl group having 1 to 5 carbon atoms or a cycloalkyl group having 5 to 10 carbon atoms. The aryl group in the diarylamino group is an aryl group having 6 to 10 carbon atoms, and the aryl group in the diarylboryl group is optionally bonded by a single bond or a linking group. R b Each of the following groups is independently hydrogen, an aryl group having 6 to 16 carbon atoms, a heteroaryl group having 2 to 20 carbon atoms, a diarylamino group, a diarylboryl group, an alkyl group having 1 to 12 carbon atoms, or a cycloalkyl group having 3 to 16 carbon atoms. At least one hydrogen atom of these aryl or heteroaryl groups is optionally substituted with an alkyl group having 1 to 5 carbon atoms or a cycloalkyl group having 5 to 10 carbon atoms. The aryl group in the diarylamino group is aryl with 6 to 10 carbon atoms, the aryl group in the diarylboryl group is aryl with 6 to 10 carbon atoms, and the two aryl groups in the diarylboryl group are optionally bonded by a single bond or a linking group. R c Each of the following groups is independently hydrogen, an aryl group having 6 to 16 carbon atoms, a heteroaryl group having 2 to 20 carbon atoms, a diarylamino group, a diarylboryl group, an alkyl group having 1 to 12 carbon atoms, or a cycloalkyl group having 3 to 16 carbon atoms. At least one hydrogen atom in these aryl or heteroaryl groups is optionally substituted with an alkyl group having 1 to 5 carbon atoms or a cycloalkyl group having 5 to 10 carbon atoms. The aryl group in the diarylamino group is an aryl group having 6 to 10 carbon atoms, and the aryl group in the diarylboryl group is optionally bonded by a single bond or a linking group. Y 1 For B, X 1 Let N be the number of ... X 2 Each is independently >O or >NR, wherein the R in >NR is an aryl group having 6 to 10 carbon atoms, an alkyl group having 1 to 5 carbon atoms, or a cycloalkyl group having 5 to 10 carbon atoms, and at least one hydrogen atom of the aryl group is optionally substituted with an alkyl group having 1 to 5 carbon atoms or a cycloalkyl group having 5 to 10 carbon atoms. n is 1 or 2, and At least one hydrogen atom in the compound shown in formula (2) may be optionally replaced by deuterium, cyano or halogen.

7. The polycyclic aromatic compound according to claim 1, wherein it is represented by any of the following structural formulas, In the above structural formulas, "Me" represents methyl.

8. A reactive compound obtained by substituting a reactive substituent onto a polycyclic aromatic compound according to any one of claims 1 to 7.

9. A polymer compound or polymer crosslinker, wherein, The polymer compound is obtained by polymerizing the reactive compound of claim 8 as a monomer, and the polymer crosslinker is obtained by further crosslinking the polymer compound.

10. A side-group type polymer compound or a side-group type polymer crosslinker, wherein, The side-chain type polymer compound is obtained by substituting the reactive compound of claim 8 onto the main chain polymer, and the side-chain type polymer crosslinker is obtained by further crosslinking the side-chain type polymer compound.

11. A material for organic devices, comprising any one of the polycyclic aromatic compounds according to claims 1 to 7.

12. A material for an organic device comprising the reactive compound of claim 8.

13. A material for organic equipment, comprising the polymer compound or polymer crosslinker as described in claim 9.

14. A material for organic devices, comprising the side-chain type polymer compound or side-chain type polymer crosslinker as described in claim 10.

15. The material for organic equipment according to any one of claims 11 to 14, wherein, The materials used in the organic devices are materials for organic electroluminescent elements, materials for organic field-effect transistors, or materials for organic thin-film solar cells.

16. The material for organic equipment according to claim 15, wherein, The material used in the organic electroluminescent element is the material used for the light-emitting layer.

17. An ink composition comprising the polycyclic aromatic compound of any one of claims 1 to 7 and an organic solvent.

18. An ink composition comprising the reactive compound of claim 8 and an organic solvent.

19. An ink composition comprising a main-chain polymer, the reactive compound of claim 8, and an organic solvent.

20. An ink composition comprising the polymeric compound or polymeric crosslinker of claim 9, and comprising an organic solvent.

21. An ink composition comprising the side-chain type polymer compound or side-chain type polymer crosslinker of claim 10, and comprising an organic solvent.

22. An organic electroluminescent element comprising: a pair of electrodes including an anode and a cathode, and an organic layer disposed between the pair of electrodes. The organic layer contains any one of the polycyclic aromatic compounds of claims 1 to 7, the reactive compound of claim 8, the polymer compound or polymer crosslinker of claim 9, or the side-chain polymer compound or side-chain polymer crosslinker of claim 10.

23. The organic electroluminescent element according to claim 22, wherein, The organic layer is a light-emitting layer.

24. The organic electroluminescent element according to claim 23, wherein, The light-emitting layer comprises a host and includes, as dopants, the polycyclic aromatic compound, reactive compound, polymer compound, polymer crosslinker, side-group type polymer compound, or side-group type polymer crosslinker.

25. The organic electroluminescent element according to claim 24, wherein, The main component is anthracene compounds, fluorene compounds, or dibenzo[a]benzene compounds.

26. The organic electroluminescent element according to any one of claims 23 to 25, comprising an electron transport layer and / or an electron injection layer disposed between the cathode and the light-emitting layer, wherein 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 derivatives, anthracene derivatives, benzo[a]fluorene derivatives, phosphine oxide derivatives, pyrimidine derivatives, carbazole derivatives, triazine derivatives, benzimidazole derivatives, phenanthrene derivatives, and hydroxyquinoline metal complexes.

27. The organic electroluminescent element according to claim 26, wherein, The electron transport layer and / or electron injection layer further contain 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.

28. The organic electroluminescent element according to any one of claims 23 to 27, wherein, At least one of the hole injection layer, hole transport layer, light emission layer, electron transport layer, and electron injection layer comprises: a polymeric compound obtained by polymerizing a low-molecular-weight compound capable of forming each layer as a monomer, or a polymeric cross-linked compound obtained by further cross-linking the polymeric compound, or a side-chain type polymeric compound obtained by reacting a low-molecular-weight compound capable of forming each layer with a main-chain type polymer, or a side-chain type polymeric cross-linked compound obtained by further cross-linking the side-chain type polymeric compound.

29. A display device or lighting device comprising an organic electroluminescent element according to any one of claims 22 to 28.

Images