KR-20260068026-A - AMINO-SUBSTITUTED POLYCYCLIC AROMATIC COMPOUNDS

Abstract

The present invention aims to provide a novel amino-substituted polycyclic aromatic compound and an organic EL device using the same. According to the present invention, in order to solve the above problem, by introducing a specific amino group or a specific substituent (Ra group and Rb group) into a polycyclic aromatic compound in which a plurality of aromatic rings are connected with boron atoms and oxygen atoms, etc., the options for materials for organic devices, such as materials for organic EL devices, can be increased. In addition, by using such a novel amino-substituted polycyclic aromatic compound as a material for organic EL devices, for example, an organic EL device with excellent luminous efficiency and device lifespan can be provided.

Inventors

• 하타케야마 타쿠지
• 바바 다이스케
• 고바야시 다카히로
• 오모리 히데후미
• 시렌 가즈시

Assignees

• 가꼬우 호징 관세이 가쿠잉
• 에스케이머티리얼즈제이엔씨 주식회사

Dates

Publication Date

20260513

Application Date

20260407

Priority Date

20190607

Claims (20)

1. Polycyclic aromatic compounds represented by the following general formula (1): (Among the above formula (1), Ring A, ring B, and ring C are each independently an aryl ring having 6 to 16 carbon atoms, or a heteroaryl ring having 2 to 15 carbon atoms containing nitrogen, oxygen, or sulfur as a heteroelement, and at least one hydrogen in these rings is an aryl having 6 to 16 carbon atoms, a heteroaryl having 2 to 15 carbon atoms containing nitrogen, oxygen, or sulfur as a heteroelement, a diarylamino, a diheteroarylamino, an arylheteroarylamino, an alkyl having 1 to 6 carbon atoms, a cycloalkyl having 3 to 14 carbon atoms, an alkoxy having 1 to 6 carbon atoms, an aryloxy having 6 to 16 carbon atoms, a triarylsilyl (wherein the aryl is an aryl having 6 to 16 carbon atoms), a trialkylsilyl (wherein the alkyl is an alkyl having 1 to 6 carbon atoms), a tricycloalkylsilyl (wherein the cycloalkyl is a cycloalkyl having 3 to 14 carbon atoms). It may be substituted with a dialkylcycloalkylsilyl (where the alkyl is an alkyl having 1 to 6 carbon atoms and the cycloalkyl is a cycloalkyl having 3 to 14 carbon atoms) or an alkyldicycloalkylsilyl (where the alkyl is an alkyl having 1 to 6 carbon atoms and the cycloalkyl is a cycloalkyl having 3 to 14 carbon atoms), and the aryl in the above diarylamino and arylheteroarylamino is an aryl having 6 to 16 carbon atoms, and the heteroaryl in the above diheteroarylamino and arylheteroarylamino is a heteroaryl having 2 to 15 carbon atoms containing nitrogen, oxygen, or sulfur as a heteroelement, and at least one hydrogen in these is an aryl having 6 to 16 carbon atoms, a heteroaryl having 2 to 15 carbon atoms containing nitrogen, oxygen, or sulfur as a heteroelement, an alkyl having 1 to 6 carbon atoms, or a cycloalkyl having 3 to 14 carbon atoms. It may be further substituted, At least one hydrogen in at least one of the B ring and the C ring is substituted with a group represented by the formula (Am), wherein in the formula (Am), Ar 1 and Ar 2 are each independently an aryl having 6 to 16 carbon atoms, at least one of Ar 1 and Ar 2 is a naphthyl, and at least one hydrogen in the aryl or naphthyl is an aryl having 6 to 16 carbon atoms, a heteroaryl having 2 to 15 carbon atoms containing nitrogen, oxygen, or sulfur as a heteroelement, a diarylamino, a diheteroarylamino, an arylheteroarylamino, an alkyl having 1 to 6 carbon atoms, a cycloalkyl having 3 to 14 carbon atoms, an alkoxy having 1 to 6 carbon atoms, an aryloxy having 6 to 16 carbon atoms, a triarylsilyl (wherein the aryl is an aryl having 6 to 16 carbon atoms), or a trialkylsilyl (wherein the alkyl is an alkyl having 1 to 6 carbon atoms). It may be substituted with tricycloalkylsilyl (wherein the cycloalkyl is a cycloalkyl having 3 to 14 carbon atoms), dialkylcycloalkylsilyl (wherein the alkyl is an alkyl having 1 to 6 carbon atoms and the cycloalkyl is a cycloalkyl having 3 to 14 carbon atoms), or alkyldicycloalkylsilyl (wherein the alkyl is an alkyl having 1 to 6 carbon atoms and the cycloalkyl is a cycloalkyl having 3 to 14 carbon atoms), wherein the aryl in the above diarylamino and arylheteroarylamino is an aryl having 6 to 16 carbon atoms, and the heteroaryl in the above diheteroarylamino and arylheteroarylamino is a heteroaryl having 2 to 15 carbon atoms containing nitrogen, oxygen, or sulfur as a heteroelement, and at least one hydrogen in these is an aryl having 6 to 16 carbon atoms, or a heteroelement having 2 to 15 carbon atoms containing nitrogen, oxygen, or sulfur as a heteroelement. It may be further substituted with a heteroaryl, an alkyl group having 1 to 6 carbon atoms, or a cycloalkyl group having 3 to 14 carbon atoms, and the group represented by the above formula (Am) substitutes for a hydrogen in the B ring or C ring in *, and Y 1 is B, and X1 and X2 are >NR, and R of the >NR is, respectively, an aryl having 6 to 16 carbon atoms, a heteroaryl having 2 to 15 carbon atoms containing nitrogen, oxygen, or sulfur as a heteroatom, an aryl having 6 to 16 carbon atoms that may be substituted with an alkyl having 1 to 6 carbon atoms or a cycloalkyl having 3 to 14 carbon atoms (excluding an amino group as a substituent), or an aryl having 6 to 16 carbon atoms, a heteroaryl having 2 to 15 carbon atoms containing nitrogen, oxygen, or sulfur as a heteroatom, or a heteroaryl having 2 to 15 carbon atoms containing nitrogen, oxygen, or sulfur as a heteroatom that may be substituted with an alkyl having 1 to 6 carbon atoms or a cycloalkyl having 3 to 14 carbon atoms, and R in at least one of the >NRs is -O-, -S-, -C(-R) 2- , or the A ring, B ring and by means of a single bond It may be bonded to at least one ring among the C rings, and R of the -C(-R) 2- is hydrogen, an alkyl having 1 to 6 carbon atoms, or a cycloalkyl having 3 to 14 carbon atoms. In the compound or structure represented by formula (1), at least one of the A ring, B ring, C ring, aryl, and heteroaryl may be condensed into at least one cycloalkane having 3 to 16 carbon atoms, and at least one hydrogen in the cycloalkane may be substituted with an aryl having 6 to 16 carbon atoms, a heteroaryl having 2 to 15 carbon atoms containing nitrogen, oxygen, or sulfur as a heteroelement, an alkyl having 1 to 6 carbon atoms, or a cycloalkyl having 3 to 14 carbon atoms, and at least one -CH₂- in the cycloalkane may be substituted with -O-. At least one hydrogen in the compound or structure represented by formula (1) may be substituted with deuterium, cyano, or halogen, and However, at least one of the following conditions (A) to (C) is satisfied: (A) In at least one of the above >NRs as X 1 and X 2 , R is a phenyl whose 2nd position is substituted with an aryl having 6 to 16 carbon atoms, an alkyl having 1 to 6 carbon atoms, or a cycloalkyl having 3 to 14 carbon atoms, and at least one hydrogen in these may be further substituted with an alkyl having 1 to 6 carbon atoms. (B) R in at least one of the above >NRs as X 1 and X 2 is a heteroaryl having 2 to 15 carbon atoms containing nitrogen, oxygen, or sulfur as a heteroelement, and at least one hydrogen in the said heteroaryl may be substituted with an aryl having 6 to 16 carbon atoms, a heteroaryl having 2 to 15 carbon atoms containing nitrogen, oxygen, or sulfur as a heteroelement, an alkyl having 1 to 6 carbon atoms, or a cycloalkyl having 3 to 14 carbon atoms. (C) At least one of the B ring and the C ring is a condensed ring of five and six members containing nitrogen, oxygen, or sulfur as a heteroelement, and shares a bond with the condensed two-ring structure in the center of Formula (1) composed of Y1 , X1 , and X2 in the five-membered ring.)
2. In paragraph 1, Polycyclic aromatic compounds represented by the following general formula (2B); (Among the above formula (2B), In the rings a, b, and c, any "-C(-H)=" may be substituted with "-N=", and R 21 to R 30 are each independently hydrogen, an aryl having 6 to 12 carbon atoms, a heteroaryl having 2 to 15 carbon atoms containing nitrogen, oxygen, or sulfur as a heteroatom, diarylamino, diheteroarylamino, arylheteroarylamino, an alkyl having 1 to 5 carbon atoms, a cycloalkyl having 5 to 10 carbon atoms, an alkoxy having 1 to 5 carbon atoms, an aryloxy having 6 to 12 carbon atoms, a triarylsilyl (where the aryl is an aryl having 6 to 12 carbon atoms), a trialkylsilyl (where the alkyl is an alkyl having 1 to 5 carbon atoms), a tricycloalkylsilyl (where the cycloalkyl is a cycloalkyl having 5 to 10 carbon atoms), a dialkylcycloalkylsilyl (where the alkyl is an alkyl having 1 to 5 carbon atoms and the cycloalkyl is a cycloalkyl having 5 to 10 carbon atoms), or an alkyldicycloalkylsilyl (where the alkyl is a number of carbon atoms (1 to 5 alkyl, and the cycloalkyl is a cycloalkyl having 5 to 10 carbon atoms), wherein the aryl in the diarylamino and arylheteroarylamino is an aryl having 6 to 12 carbon atoms, and the heteroaryl in the diheteroarylamino and arylheteroarylamino is a heteroaryl having 2 to 15 carbon atoms containing nitrogen, oxygen, or sulfur as a heteroelement, and at least one hydrogen in these may be substituted with an aryl having 6 to 12 carbon atoms, a heteroaryl having 2 to 15 carbon atoms containing nitrogen, oxygen, or sulfur as a heteroelement, an alkyl having 1 to 5 carbon atoms, or a cycloalkyl having 5 to 10 carbon atoms. Adjacent groups among R21 to R25 are bonded to form a naphthalene ring together with a d-ring, and at least one hydrogen in the formed naphthalene ring is an aryl having 6 to 12 carbon atoms, a heteroaryl having 2 to 15 carbon atoms containing nitrogen, oxygen, or sulfur as a heteroelement, a diarylamino, a diheteroarylamino, an arylheteroarylamino, an alkyl having 1 to 5 carbon atoms, a cycloalkyl having 5 to 10 carbon atoms, an alkoxy having 1 to 5 carbon atoms, an aryloxy having 6 to 12 carbon atoms, a triarylsilyl (wherein the aryl is an aryl having 6 to 12 carbon atoms), a trialkylsilyl (wherein the alkyl is an alkyl having 1 to 5 carbon atoms), a tricycloalkylsilyl (wherein the cycloalkyl is a cycloalkyl having 5 to 10 carbon atoms), or a dialkylcycloalkylsilyl (wherein the alkyl is an alkyl having 1 to 5 carbon atoms, and the cycloalkyl is a It may be substituted with a cycloalkyl having 5 to 10 carbon atoms), or an alkyl dicycloalkylsilyl (wherein the alkyl is an alkyl having 1 to 5 carbon atoms and the cycloalkyl is a cycloalkyl having 5 to 10 carbon atoms), and the aryl in the diarylamino and arylheteroarylamino is an aryl having 6 to 12 carbon atoms, and the heteroaryl in the diheteroarylamino and arylheteroarylamino is a heteroaryl having 2 to 15 carbon atoms containing nitrogen, oxygen, or sulfur as a heteroelement, and at least one hydrogen therein may be further substituted with an aryl having 6 to 12 carbon atoms, a heteroaryl having 2 to 15 carbon atoms containing nitrogen, oxygen, or sulfur as a heteroelement, an alkyl having 1 to 5 carbon atoms, or a cycloalkyl having 5 to 10 carbon atoms. Ra is an aryl having 6 to 12 carbon atoms, a heteroaryl having 2 to 15 carbon atoms containing nitrogen, oxygen, or sulfur as a heteroatom, an alkyl having 1 to 5 carbon atoms, a cycloalkyl having 5 to 10 carbon atoms, an alkoxy having 1 to 5 carbon atoms, an aryloxy having 6 to 12 carbon atoms, a triarylsilyl (wherein the aryl is an aryl having 6 to 12 carbon atoms), a trialkylsilyl (wherein the alkyl is an alkyl having 1 to 5 carbon atoms), a tricycloalkylsilyl (wherein the cycloalkyl is a cycloalkyl having 5 to 10 carbon atoms), a dialkylcycloalkylsilyl (wherein the alkyl is an alkyl having 1 to 5 carbon atoms and the cycloalkyl is a cycloalkyl having 5 to 10 carbon atoms), or an alkyldicycloalkylsilyl (wherein the alkyl is an alkyl having 1 to 5 carbon atoms and the cycloalkyl is a cycloalkyl having 5 to 10 carbon atoms), and at least one of these Hydrogen may be substituted with an aryl having 6 to 12 carbon atoms, a heteroaryl having 2 to 15 carbon atoms containing nitrogen, oxygen, or sulfur as a heteroatom, an alkyl having 1 to 5 carbon atoms, or a cycloalkyl having 5 to 10 carbon atoms, and Rb is hydrogen, an aryl having 6 to 12 carbon atoms, a heteroaryl having 2 to 15 carbon atoms containing nitrogen, oxygen, or sulfur as a heteroelement, a diarylamino, a diheteroarylamino, an arylheteroarylamino, an alkyl having 1 to 5 carbon atoms, a cycloalkyl having 5 to 10 carbon atoms, an alkoxy having 1 to 5 carbon atoms, an aryloxy having 6 to 12 carbon atoms, a triarylsilyl (where the aryl is an aryl having 6 to 12 carbon atoms), a trialkylsilyl (where the alkyl is an alkyl having 1 to 5 carbon atoms), a tricycloalkylsilyl (where the cycloalkyl is a cycloalkyl having 5 to 10 carbon atoms), a dialkylcycloalkylsilyl (where the alkyl is an alkyl having 1 to 5 carbon atoms and the cycloalkyl is a cycloalkyl having 5 to 10 carbon atoms), or an alkyldicycloalkylsilyl (where the alkyl is an alkyl having 1 to 5 carbon atoms, and The cycloalkyl is a cycloalkyl having 5 to 10 carbon atoms, and the aryl in the diarylamino and arylheteroarylamino is an aryl having 6 to 12 carbon atoms, and the heteroaryl in the diheteroarylamino and arylheteroarylamino is a heteroaryl having 2 to 15 carbon atoms containing nitrogen, oxygen, or sulfur as a heteroelement, and at least one hydrogen in these may be substituted with an aryl having 6 to 12 carbon atoms, a heteroaryl having 2 to 15 carbon atoms containing nitrogen, oxygen, or sulfur as a heteroelement, an alkyl having 1 to 5 carbon atoms, or a cycloalkyl having 5 to 10 carbon atoms. Y 1 is B, and X1 and X2 are >NR, wherein R of the >NR is independently an aryl having 6 to 12 carbon atoms, or a heteroaryl having 2 to 15 carbon atoms containing nitrogen, oxygen, or sulfur as a heteroatom, and at least one hydrogen therein may be substituted with an aryl having 6 to 12 carbon atoms, a heteroaryl having 2 to 15 carbon atoms containing nitrogen, oxygen, or sulfur as a heteroatom, an alkyl having 1 to 5 carbon atoms, or a cycloalkyl having 5 to 10 carbon atoms; furthermore, R in at least one of the >NR may be bonded to at least one of the a-, b-, and c- rings by means of -O-, -S-, -C(-R) 2- , or a single bond, and R of the -C(-R) 2- is an alkyl having 1 to 5 carbon atoms or a cycloalkyl having 5 to 10 carbon atoms. In the compound or structure represented by formula (2B), at least one of the a-ring, the b-ring, the c-ring, the d-ring, the e-ring, the formed naphthalene ring, the aryl, and the heteroaryl may be condensed into at least one cycloalkane having 3 to 16 carbon atoms, and at least one hydrogen in the cycloalkane may be substituted with an aryl having 6 to 12 carbon atoms, a heteroaryl having 2 to 15 carbon atoms containing nitrogen, oxygen, or sulfur as a heteroelement, an alkyl having 1 to 5 carbon atoms, or a cycloalkyl having 5 to 10 carbon atoms, and at least one -CH₂- in the cycloalkane may be substituted with -O-. At least one hydrogen in the compound or structure represented by formula (2B) may be substituted with deuterium, cyano, or halogen, and Provided that at least one of the following conditions (A') and (B') is satisfied: (A') In at least one of the above >NRs as X 1 and X 2 , R is a phenyl whose 2nd position is substituted with an aryl having 6 to 12 carbon atoms, an alkyl having 1 to 5 carbon atoms, or a cycloalkyl having 5 to 10 carbon atoms, and at least one hydrogen in these may be further substituted with an alkyl having 1 to 5 carbon atoms. (B') In at least one of the above >NRs as X 1 and X 2 , R is a C2 to C5 heteroaryl containing nitrogen, oxygen, or sulfur as a heteroelement, and at least one hydrogen in the said heteroaryl may be substituted with an C6 to C12 aryl, a C2 to C5 heteroaryl containing nitrogen, oxygen, or sulfur as a heteroelement, an C1 to C5 alkyl, or a C5 to C10 cycloalkyl.)
3. In paragraph 2, Among the above formula (2B), In the rings a, b, and c, any "-C(-H)=" may be substituted with "-N=", and R 21 to R 30 are each independently hydrogen, an aryl having 6 to 10 carbon atoms, a heteroaryl having 2 to 10 carbon atoms containing nitrogen, oxygen, or sulfur as a heteroatom, a diarylamino (where aryl is an aryl having 6 to 10 carbon atoms), an alkyl having 1 to 5 carbon atoms, a cycloalkyl having 5 to 10 carbon atoms, or a trialkylsilyl (where alkyl is an alkyl having 1 to 5 carbon atoms), and Adjacent groups among R21 to R25 are bonded to form a naphthalene ring together with a d-ring, and at least one hydrogen in the formed naphthalene ring may be substituted with an aryl having 6 to 10 carbon atoms, a heteroaryl having 2 to 10 carbon atoms containing nitrogen, oxygen, or sulfur as a heteroatom, a diarylamino (where the aryl is an aryl having 6 to 10 carbon atoms), an alkyl having 1 to 5 carbon atoms, a cycloalkyl having 5 to 10 carbon atoms, a triarylsilyl (where the aryl is an aryl having 6 to 10 carbon atoms), or a trialkylsilyl (where the alkyl is an alkyl having 1 to 5 carbon atoms). Ra is an aryl having 6 to 10 carbon atoms, an alkyl having 1 to 5 carbon atoms, a cycloalkyl having 5 to 10 carbon atoms, a triarylsilyl (where the aryl is an aryl having 6 to 10 carbon atoms), or a trialkylsilyl (where the alkyl is an alkyl having 1 to 5 carbon atoms), and at least one hydrogen in the aryl may be substituted with an alkyl having 1 to 5 carbon atoms or a cycloalkyl having 5 to 10 carbon atoms. Rb is hydrogen, an aryl having 6 to 10 carbon atoms, a diarylamino (where aryl is an aryl having 6 to 10 carbon atoms), an alkyl having 1 to 5 carbon atoms, a cycloalkyl having 5 to 10 carbon atoms, a triarylsilyl (where aryl is an aryl having 6 to 10 carbon atoms), or a trialkylsilyl (where alkyl is an alkyl having 1 to 5 carbon atoms), and at least one hydrogen in the aryl may be substituted with an alkyl having 1 to 5 carbon atoms or a cycloalkyl having 5 to 10 carbon atoms. Y 1 is B, and X1 and X2 are >NR, and R of the >NR is, respectively, an aryl having 6 to 10 carbon atoms, or a heteroaryl having 2 to 10 carbon atoms comprising nitrogen, oxygen, or sulfur as a heteroatom, and at least one hydrogen therein may be substituted with an aryl having 6 to 10 carbon atoms, an alkyl having 1 to 5 carbon atoms, or a cycloalkyl having 5 to 10 carbon atoms. In the compound or structure represented by formula (2B), at least one of the a-ring, the b-ring, the c-ring, the d-ring, the e-ring, the formed naphthalene ring, the aryl, and the heteroaryl may be condensed into at least one cycloalkane having 3 to 14 carbon atoms, and at least one hydrogen in the cycloalkane may be substituted with an aryl having 6 to 10 carbon atoms, a heteroaryl having 2 to 10 carbon atoms containing nitrogen, oxygen, or sulfur as a heteroelement, an alkyl having 1 to 5 carbon atoms, or a cycloalkyl having 5 to 10 carbon atoms. At least one hydrogen in the compound or structure represented by formula (2B) may be substituted with deuterium, cyano, or halogen, and However, a polycyclic aromatic compound satisfying at least one of the following conditions (A) and (B): (A") In at least one of the above >NRs as X 1 and X 2 , R is a phenyl whose 2nd position is substituted with an aryl having 6 to 10 carbon atoms, an alkyl having 1 to 5 carbon atoms, or a cycloalkyl having 5 to 10 carbon atoms, and at least one hydrogen in these may be further substituted with an alkyl having 1 to 5 carbon atoms. (B) In at least one of the above >NRs as X 1 and X 2 , R is a C2 to C10 heteroaryl comprising nitrogen, oxygen, or sulfur as a heteroelement, and at least one hydrogen in the said heteroaryl may be substituted with an C6 to C10 aryl, a C1 to C5 alkyl, or a C5 to C10 cycloalkyl.)
4. In paragraph 1, The above condition (A) is a polycyclic aromatic compound, which is as follows: (A) R in at least one of the above >NRs as X 1 and X 2 is 2-biphenylyl which may be substituted with an aryl having 6 to 10 carbon atoms, an alkyl having 1 to 5 carbon atoms, or a cycloalkyl having 5 to 10 carbon atoms.
5. In paragraph 1, A polycyclic aromatic compound substituted with a diarylamino group condensed with a cycloalkane having 3 to 14 carbon atoms (where the aryl is an aryl having 6 to 10 carbon atoms), a carbazolyl group condensed with a cycloalkane having 3 to 14 carbon atoms, or a benzocarbazolyl group condensed with a cycloalkane having 3 to 14 carbon atoms.
6. In paragraph 2, Rb in the above formula (2B) is a polycyclic aromatic compound, which is a diarylamino group condensed with a cycloalkane having 5 to 6 carbon atoms (where aryl is an aryl having 6 to 10 carbon atoms) or a carbazolyl group condensed with a cycloalkane having 5 to 6 carbon atoms.
7. In paragraph 5, The above cycloalkanes are polycyclic aromatic compounds, which are cycloalkanes having 5 to 6 carbon atoms.
8. In paragraph 1, The above halogen is a polycyclic aromatic compound, which is fluorine.
9. Polycyclic aromatic compounds represented by any one of the following structural formulas: In the above structural formula, “Me” is a methyl group, “tBu” is a tert-butyl group, and “tAm” is tert-amyl group, "D" is deuterium, and "HEX" is a hexyl group.
10. A material for an organic device containing a polycyclic aromatic compound described in any one of claims 1 to 9.
11. In Paragraph 10, The above organic device material is an organic device material, wherein the organic device material is a material for an organic field-effect light-emitting diode, a material for an organic field-effect transistor, or a material for an organic thin-film solar cell.
12. In Paragraph 11, An organic device material in which the above-mentioned organic field light-emitting diode material is a material for a light-emitting layer.
13. An organic electroluminescent device comprising a pair of electrodes consisting of an anode and a cathode, and an organic layer disposed between the pair of electrodes and containing a polycyclic aromatic compound described in any one of claims 1 to 9.
14. In Paragraph 13, An organic field light-emitting device in which the above organic layer is a light-emitting layer.
15. In Paragraph 14, An organic electroluminescent device comprising the above-mentioned light-emitting layer, the host, and the above-mentioned polycyclic aromatic compound as a dopant.
16. In paragraph 15, An organic electroluminescent device in which the host is an anthracene compound, a fluorene compound, or a dibenzochrycene compound.
17. In Paragraph 14, An organic electroluminescent device having at least one of an electron transport layer and 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 a boran derivative, a pyridine derivative, a fluoranthene derivative, a BO-based derivative, anthracene derivative, a benzofluorene derivative, a phosphine oxide derivative, a pyrimidine derivative, a carbazole derivative, a triazine derivative, a benzimidazole derivative, a phenanthroline derivative, a quinolinol-based metal complex, a thiazole derivative, a benzothiazole derivative, a silol derivative, and an azoline derivative.
18. In Paragraph 17, An organic electroluminescent device comprising, wherein at least one layer among the electron transport layer and the electron injection layer further comprises at least one selected from the group consisting of an alkali metal, an alkaline earth metal, a rare earth metal, an oxide of an alkali metal, a halide of an alkali metal, an oxide of an alkaline earth metal, a halide of an alkaline earth metal, an oxide of a rare earth metal, a halide of a rare earth metal, an organic complex of an alkaline earth metal, an organic complex of an alkaline earth metal, and an organic complex of a rare earth metal.
19. A display device equipped with an organic field light-emitting element as described in paragraph 13.
20. A lighting device equipped with an organic field light-emitting element as described in paragraph 13.

Description

Amino-substituted polycyclic aromatic compounds The present invention relates to amino-substituted polycyclic aromatic compounds and their polymers (hereinafter collectively referred to as “polycyclic aromatic compounds”), organic field-effect light-emitting diodes, organic field-effect transistors, and organic thin-film solar cells using the same, as well as display devices and lighting devices. Additionally, in this specification, “organic field-effect light-emitting diodes” may be referred to as “organic EL devices” or simply “devices.” Conventionally, display devices using electroluminescent light-emitting elements have been extensively studied because they allow for low power consumption and thinness. Additionally, organic electroluminescent elements made of organic materials have been actively explored because they facilitate lightweighting and large-scale production. In particular, the development of organic materials with light-emitting properties such as blue, one of the three primary colors of light, and the development of organic materials equipped with charge transport capabilities such as holes and electrons (which have the potential to become semiconductors or superconductors) have been actively studied so far, regardless of whether they are polymer compounds or low-molecular-weight compounds. An organic EL device has a structure comprising a pair of electrodes consisting of a positive electrode and a negative electrode, and one or more layers containing an organic compound disposed between the pair of electrodes. The layers containing the organic compound include a light-emitting layer or a charge transport/injection layer that transports or injects charges such as holes and electrons, but various organic materials suitable for these layers have been developed. As materials for the emissive layer, for example, benzofluorene-based compounds have been developed (International Publication No. 2004/061047). In addition, as hole transport materials, for example, triphenylamine-based compounds have been developed (Japanese Patent Publication No. 2001-172232). In addition, as electron transport materials, for example, anthracene-based compounds have been developed (Japanese Patent Publication No. 2005-170911). In addition, recently, materials modified from triphenylamine derivatives have been reported for use in organic EL devices or organic thin-film solar cells (International Publication No. 2012/118164). This material is characterized by enhanced planarity through the linking of the aromatic rings constituting triphenylamine, based on N,N'-diphenyl-N,N'-bis(3-methylphenyl)-1,1'-biphenyl-4,4'-diamine (TPD), which is already commercialized. In this document, for example, the charge transport properties of NO-linked compounds (Compound 1 on page 63) are evaluated; however, the manufacturing method for materials other than NO-linked compounds is not described, and furthermore, since the electronic state of the entire compound differs depending on the linked elements, the properties obtained from materials other than NO-linked compounds are not yet known. Examples of such compounds are found elsewhere (International Publication No. 2011/107186). For example, compounds having a conjugate structure with a large triplet exciton energy (T1) can emit phosphorescence of a shorter wavelength, making them useful as materials for blue light-emitting layers. In addition, compounds having a novel conjugate structure with a large T1 are also required as electron transport materials or hole transport materials that bind the light-emitting layer. The host material for organic EL devices is generally a molecule in which conventional aromatic rings, such as benzene or carbazole, are linked by single bonds or multiple connections of phosphorus or silicon atoms. This is because the large HOMO-LUMO gap (band gap Eg in thin films) required for the host material is ensured by linking multiple aromatic rings with relatively small conjugation systems. Furthermore, while a high triplet excitation energy ( ET ) is required for host materials of organic EL devices using phosphorescent materials or thermally activated delayed fluorescent materials, it is possible to improve the triplet excitation energy ( ET ) by linking donor or acceptor aromatic rings or substituents to the molecule, thereby localizing SOMO1 and SOMO2 in the triplet excited state (T1) and reducing the exchange interaction between the two orbitals. However, aromatic rings with small conjugation systems do not have sufficient redox stability, and devices using molecules with connected conventional aromatic rings as host materials do not have sufficient lifespan. Meanwhile, polycyclic aromatic compounds having an extended π-conjugation system have generally been considered unsuitable as host materials because, although they have excellent redox stability, their HOMO-LUMO gap (band gap Eg in thin films) and triplet excitation energy ( ET ) are low. FIG. 1 is a sc