Polycyclic aromatic compounds

Abstract

This polycyclic aromatic compound which has a structure that is composed of one or more structural units represented by formula (1) is useful as an organic device material for organic EL elements and the like. In the formula, Z represents N or C-R11 (wherein R11 represents a hydrogen atom or a substituent); ring C represents a ring that is represented by formula (C); ZC represents N or C-RC (wherein RC represents a hydrogen atom or a substituent); Xc represents >S; Y1 represents B; one of X1 and X2 represents >N-LCY-RCY, and the other represents >N-GA or >N-GB; LCY represents a substituted or unsubstituted arylene group; RCY represents a substituted or unsubstituted cycloalkyl group; GA and GB respectively represent a group represented by formula (GA) and a group represented by formula (GB); Zg represents N or C-Rg (wherein Rg represents a hydrogen atom or a substituent); A represents >O; aryl rings or heteroaryl rings in the structure may be fused by a cycloalkane; and at least one hydrogen atom in the structure may be substituted by a cyano group, a halogen atom or a deuterium atom.

Description

[Technical Field]

[0001] This invention relates to polycyclic aromatic compounds. In particular, this invention relates to polycyclic aromatic compounds containing nitrogen and boron. This invention also relates to materials for organic devices, organic electroluminescent devices, and display devices and lighting devices containing the above-mentioned polycyclic aromatic compounds. [Background technology]

[0002] Conventionally, display devices using electroluminescent light-emitting elements have been studied extensively due to their potential for power saving and miniaturization. Furthermore, organic electroluminescent elements made from organic materials have been actively investigated because they are easily made lighter and larger. In particular, the development of organic materials with luminescence properties such as blue, one of the three primary colors of light, and the development of organic materials with charge transport capabilities (potentially becoming semiconductors or superconductors) have been actively researched, regardless of whether they are polymer compounds or low molecular weight compounds.

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

[0004] Among these, Patent Documents 1 to 5 disclose that polycyclic aromatic compounds containing boron are useful as materials for organic electroluminescent devices and the like. It has been reported that organic electroluminescent devices containing these polycyclic aromatic compounds have good external quantum efficiency. Patent Documents 2 and 3 disclose structures in which heterocyclic compounds such as benzothiophene are condensed. Patent Documents 4 and 5 disclose structures having cycloalkyl groups as substituents. [Prior art documents] [Patent Documents]

[0005] [Patent Document 1] International Publication No. 2015 / 102118 [Patent Document 2] International Publication No. 2020 / 111830 [Patent Document 3] International Publication No. 2020 / 251049 [Patent Document 4] International Publication No. 2018 / 216990 [Patent Document 5] International Publication No. 2019 / 198699 [Overview of the project] [Problems that the invention aims to solve]

[0006] As mentioned above, various materials have been developed for use in organic EL devices, but in order to increase the range of materials available for organic EL devices, there is a need for the development of materials composed of compounds different from those used in conventional devices. The object of this invention is to provide novel compounds useful as materials for organic devices such as organic light-emitting diodes (OLEDs). [Means for solving the problem]

[0007] The present inventors diligently studied to solve the above problems and succeeded in producing polycyclic aromatic compounds that provide high luminescence efficiency by combining specific fused ring structures and substituents in the structures of compounds described in Patent Documents 1 to 5. Furthermore, they discovered that an excellent organic EL element can be obtained by arranging a layer containing this polycyclic aromatic compound between a pair of electrodes to construct an organic EL element, thus completing the present invention. In other words, the present invention provides the following polycyclic aromatic compounds, and further, materials for organic devices containing the following polycyclic aromatic compounds.

[0008] The present invention specifically has the following configuration.

[0009] <1> A polycyclic aromatic compound having a structure consisting of one or more structural units represented by the following formula (1); [ka]

[0010] In formula (1), Each Z is independent of N or CR. 11 Thereafter, Z=Z may be >O, >NR, >C(-R)2, >Si(-R)2, >S, or >Se, and the R in >NR, >C(-R)2, and >Si(-R)2 are each independently hydrogen, a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted alkyl, or a substituted or unsubstituted cycloalkyl, and the two Rs in >C(-R)2 and >Si(-R)2 may or may not be bonded to each other to form a ring. R 11 Each of these is independently hydrogen, a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted diarylamino, a substituted or unsubstituted diheteroarylamino, a substituted or unsubstituted arylheteroarylamino, a substituted or unsubstituted diarylboryl, a substituted or unsubstituted alkyl, a substituted or unsubstituted cycloalkyl, a substituted or unsubstituted alkenyl, a substituted or unsubstituted alkoxy, a substituted or unsubstituted aryloxy, a substituted or unsubstituted arylthio, or a substituted silyl. The two aryls in the diarylamino are either not bonded to each other or are bonded via a linking group, the two heteroaryls in the diheteroarylamino are either not bonded to each other or are bonded via a linking group, the aryl and heteroaryls in the arylheteroarylamino are either not bonded to each other or are bonded via a linking group, and the two aryls in the diarylboryl are either not bonded to each other or are bonded via a single bond or a linking group. Two adjacent R 11The atoms are bonded to each other to form or not form an aryl ring or heteroaryl ring, and at least one hydrogen atom of the formed aryl ring and heteroaryl ring is either substituted or unsubstituted with a substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino, substituted or unsubstituted diheteroarylamino, substituted or unsubstituted arylheteroarylamino, substituted or unsubstituted diarylboryl, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted arylthio, or substituted silyl, and the two aryl atoms of the diarylamino are either not bonded to each other or are bonded via a linking group, the two heteroaryl atoms of the diheteroarylamino are either not bonded to each other or are bonded via a linking group, the aryl and heteroaryl atoms of the arylheteroarylamino are either not bonded to each other or are bonded via a linking group, and the two aryl atoms of the diarylboryl are either not bonded to each other or are bonded via a single bond or a linking group. A C ring is a ring represented by formula (C), In formula (C), X c >O, >NR, >C(-R)2, >Si(-R)2, >S, or >Se, where R in >NR, >C(-R)2, and >Si(-R)2 is independently hydrogen, a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted alkyl, or a substituted or unsubstituted cycloalkyl, and the two Rs in >C(-R)2 and >Si(-R)2 are bonded to each other to form a ring, or are not bonded to each other. Z C Each of these can be independently N or CR C And R CEach of these is independently hydrogen, a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted diarylamino, a substituted or unsubstituted diheteroarylamino, a substituted or unsubstituted arylheteroarylamino, a substituted or unsubstituted diarylboryl, a substituted or unsubstituted alkyl, a substituted or unsubstituted cycloalkyl, a substituted or unsubstituted alkenyl, a substituted or unsubstituted alkoxy, a substituted or unsubstituted aryloxy, a substituted or unsubstituted arylthio, or a substituted silyl, wherein the two aryls of the diarylamino are not bonded to each other or are bonded via a linking group, the two heteroaryls of the diheteroarylamino are not bonded to each other or are bonded via a linking group, the aryl and heteroaryl of the arylheteroarylamino are not bonded to each other or are bonded via a linking group, and the two aryls of the diarylboryl are not bonded to each other or are bonded via a single bond or a linking group. Two adjacent R C These atoms may bond to each other to form an aryl ring or a heteroaryl ring, and at least one hydrogen atom of the formed aryl ring and heteroaryl ring is substituted or unsubstituted with a substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino, substituted or unsubstituted diheteroarylamino, substituted or unsubstituted arylheteroarylamino, substituted or unsubstituted diarylboryl, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, or substituted or unsubstituted arylthio, and the two aryl atoms of the diarylamino are not bonded to each other or are bonded via a linking group, the two heteroaryl atoms of the diheteroarylamino are not bonded to each other or are bonded via a linking group, the aryl and heteroaryl atoms of the arylheteroarylamino are not bonded to each other or are bonded via a linking group, and the two aryl atoms of the diarylboryl are not bonded to each other or are bonded via a single bond or a linking group. However, for any two consecutive Zs C one of them is a carbon atom bonded to Y 1 and the other is a carbon atom bonded to X 2 ; Y 1 is B, P, P=O, P=S, Al, Ga, As, Si-R, or Ge-R, where R in the Si-R and Ge-R is substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl; X 1 and one of X 2 is >N-L CY -R CY and the other is >N-GA or >N-GB, L CY is substituted or unsubstituted alkylene, substituted or unsubstituted cycloalkylene, substituted or unsubstituted arylene, or substituted or unsubstituted heteroarylene, and R in the >N-L CY -R CY is substituted or unsubstituted cycloalkyl, GA is a group represented by formula (GA), and GB is a group represented by formula (GB); CY In formula (GA) and formula (GB),

[0011]

Chemical formula

[0012] In formula (GA) and formula (GB), Z g is independently N or C-R g respectively, and R gEach of these is independently hydrogen, a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted diarylamino, a substituted or unsubstituted diheteroarylamino, a substituted or unsubstituted arylheteroarylamino, a substituted or unsubstituted diarylboryl, a substituted or unsubstituted alkyl, a substituted or unsubstituted cycloalkyl, a substituted or unsubstituted alkenyl, a substituted or unsubstituted alkoxy, a substituted or unsubstituted aryloxy, a substituted or unsubstituted arylthio, or a substituted silyl, wherein the two aryls of the diarylamino are not bonded to each other or are bonded via a linking group, the two heteroaryls of the diheteroarylamino are not bonded to each other or are bonded via a linking group, the aryl and heteroaryl of the arylheteroarylamino are not bonded to each other or are bonded via a linking group, and the two aryls of the diarylboryl are not bonded to each other or are bonded via a single bond or a linking group. Two adjacent R g These atoms may bond to each other to form an aryl ring or a heteroaryl ring, and at least one hydrogen atom of the formed aryl ring and heteroaryl ring is substituted or unsubstituted with a substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino, substituted or unsubstituted diheteroarylamino, substituted or unsubstituted arylheteroarylamino, substituted or unsubstituted diarylboryl, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, or substituted or unsubstituted arylthio, and the two aryl atoms of the diarylamino are not bonded to each other or are bonded via a linking group, the two heteroaryl atoms of the diheteroarylamino are not bonded to each other or are bonded via a linking group, the aryl and heteroaryl atoms of the arylheteroarylamino are not bonded to each other or are bonded via a linking group, and the two aryl atoms of the diarylboryl are not bonded to each other or are bonded via a single bond or a linking group. However, any one of the Z in each formula g is a carbon atom bonded to N; A is >O, >NR, >Si(-R)2, >S, or >Se, where the R in >NR and >Si(-R)2 are independently hydrogen, a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted alkyl, or a substituted or unsubstituted cycloalkyl, and the two Rs in >Si(-R)2 are bonded to each other to form a ring or not; In the aforementioned structure, at least one of the aryl ring or heteroaryl ring is condensed with or uncondensed with at least one cycloalkane, at least one hydrogen in the cycloalkane may be substituted, and at least one -CH2- in the cycloalkane may be substituted with or unsubstituted with -O-; In the above structure, at least one hydrogen atom is either substituted with cyano, halogen, or deuterium, or it is not substituted.

[0013] <2> The structural unit represented by formula (1) is represented by formulas (1a), (1b), (1c), (1d), (1e), (1f), (1g), or (1h), <1> Polycyclic aromatic compounds as described above; [ka]

[0014] [ka]

[0015] In equations (1a), (1b), (1c), (1d), (1e), (1f), (1g), and (1h), Each Z is independent of N or CR. 11Thereafter, where Z=Z may be >O, >NR, >C(-R)2, >Si(-R)2, >S, or >Se, and the R in >NR, >C(-R)2, and >Si(-R)2 are each independently hydrogen, a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted alkyl, or a substituted or unsubstituted cycloalkyl, and the two Rs in >C(-R)2 and >Si(-R)2 may or may not be bonded to each other to form a ring. R 11 Each of these is independently hydrogen, a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted diarylamino, a substituted or unsubstituted diheteroarylamino, a substituted or unsubstituted arylheteroarylamino, a substituted or unsubstituted diarylboryl, a substituted or unsubstituted alkyl, a substituted or unsubstituted cycloalkyl, a substituted or unsubstituted alkenyl, a substituted or unsubstituted alkoxy, a substituted or unsubstituted aryloxy, a substituted or unsubstituted arylthio, or a substituted silyl. The two aryls in the diarylamino are either not bonded to each other or are bonded via a linking group, the two heteroaryls in the diheteroarylamino are either not bonded to each other or are bonded via a linking group, the aryl and heteroaryls in the arylheteroarylamino are either not bonded to each other or are bonded via a linking group, and the two aryls in the diarylboryl are either not bonded to each other or are bonded via a single bond or a linking group. Two adjacent R 11The atoms are bonded to each other to form or not form an aryl ring or heteroaryl ring, and at least one hydrogen atom of the formed aryl ring and heteroaryl ring is either substituted or unsubstituted with a substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino, substituted or unsubstituted diheteroarylamino, substituted or unsubstituted arylheteroarylamino, substituted or unsubstituted diarylboryl, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted arylthio, or substituted silyl, and the two aryl atoms of the diarylamino are either not bonded to each other or are bonded via a linking group, the two heteroaryl atoms of the diheteroarylamino are either not bonded to each other or are bonded via a linking group, the aryl and heteroaryl atoms of the arylheteroarylamino are either not bonded to each other or are bonded via a linking group, and the two aryl atoms of the diarylboryl are either not bonded to each other or are bonded via a single bond or a linking group. X c >O, >NR, >C(-R)2, >Si(-R)2, >S, or >Se, where R in >NR, >C(-R)2, and >Si(-R)2 is independently hydrogen, a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted alkyl, or a substituted or unsubstituted cycloalkyl, and the two Rs in >C(-R)2 and >Si(-R)2 are bonded to each other to form a ring, or are not bonded to each other. Z C Each of these can be independently N or CR C And R CEach of these is independently hydrogen, a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted diarylamino, a substituted or unsubstituted diheteroarylamino, a substituted or unsubstituted arylheteroarylamino, a substituted or unsubstituted diarylboryl, a substituted or unsubstituted alkyl, a substituted or unsubstituted cycloalkyl, a substituted or unsubstituted alkenyl, a substituted or unsubstituted alkoxy, a substituted or unsubstituted aryloxy, a substituted or unsubstituted arylthio, or a substituted silyl, wherein the two aryls of the diarylamino are not bonded to each other or are bonded via a linking group, the two heteroaryls of the diheteroarylamino are not bonded to each other or are bonded via a linking group, the aryl and heteroaryl of the arylheteroarylamino are not bonded to each other or are bonded via a linking group, and the two aryls of the diarylboryl are not bonded to each other or are bonded via a single bond or a linking group. Two adjacent R C These atoms may bond to each other to form an aryl ring or a heteroaryl ring, and at least one hydrogen atom of the formed aryl ring and heteroaryl ring is substituted or unsubstituted with a substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino, substituted or unsubstituted diheteroarylamino, substituted or unsubstituted arylheteroarylamino, substituted or unsubstituted diarylboryl, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, or substituted or unsubstituted arylthio, and the two aryl atoms of the diarylamino are not bonded to each other or are bonded via a linking group, the two heteroaryl atoms of the diheteroarylamino are not bonded to each other or are bonded via a linking group, the aryl and heteroaryl atoms of the arylheteroarylamino are not bonded to each other or are bonded via a linking group, and the two aryl atoms of the diarylboryl are not bonded to each other or are bonded via a single bond or a linking group. Y 1 is B, P, P=O, P=S, Al, Ga, As, Si-R, or Ge-R, where R in Si-R and Ge-R is a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted alkyl, or a substituted or unsubstituted cycloalkyl; X 1 and X 2 Either one of them is >NL CY -R CY The other is >N-GA or >N-GB, >NL CY -R CY L CY is a substituted or unsubstituted alkylene, a substituted or unsubstituted cycloalkylene, a substituted or unsubstituted arylene, or a substituted or unsubstituted heteroarylene, and the above >NL CY -R CY R CY These are substituted or unsubstituted cycloalkyl groups. GA is a group represented by formula (GA), and GB is a group represented by formula (GB), ; In the aforementioned structure, at least one of the aryl ring or heteroaryl ring is condensed with or uncondensed with at least one cycloalkane, at least one hydrogen in the cycloalkane may be substituted, and at least one -CH2- in the cycloalkane may be substituted with or unsubstituted with -O-; In the above structure, at least one hydrogen atom is either substituted with cyano, halogen, or deuterium, or it is not substituted.

[0016] <3> The structural unit represented by formula (1) is represented by formula (1a), <2> The polycyclic aromatic compounds described above. <4> L CY R is substituted or unsubstituted 1,4-phenylene, substituted or unsubstituted 4,4'-biphenylene, or substituted or unsubstituted 4,4''-terphenylene, CYis an unsubstituted 1-adamantyl, <1> ~ <3> A polycyclic aromatic compound as described in any of the following. <5> X 1 and X 2 Either one of them is >N-GA, <1> ~ <4> A polycyclic aromatic compound as described in any of the following.

[0017] <6> The following formula is used: <5> Polycyclic aromatic compounds as described above; [ka]

[0018] [ka] In the formula, Me is methyl, tBu is t-butyl, and D is deuterium.

[0019] <7> X 1 and X 2 If either one of them is >N-GB, <1> ~ <4> A polycyclic aromatic compound as described in any of the following. <8> The following formula is used: <7> Polycyclic aromatic compounds as described above; [ka]

[0020] [ka]

[0021] [ka]

[0022] [ka]

[0023] [ka] In the formula, Me is methyl, tBu is t-butyl, and D is deuterium.

[0024] <9> <1> ~ <8> A material for organic devices containing a polycyclic aromatic compound as described in any of the above. <10> It includes a pair of electrodes consisting of an anode and a cathode, and a light-emitting layer disposed between the pair of electrodes, wherein the light-emitting layer <1> ~ <8> An organic electroluminescent element containing a polycyclic aromatic compound as described in any of the above. <11> The light-emitting layer comprises a host and the polycyclic aromatic compound as a dopant. <10> Organic electroluminescent device as described above. <12> The host is an anthracene compound, a fluorene compound, or a dibenzochrysene compound. <11> Organic electroluminescent device as described above. <13> <10> ~ <12> A display device or lighting device equipped with an organic electroluminescent element as described in any of the above. [Effects of the Invention]

[0025] The present invention provides novel polycyclic aromatic compounds useful as materials for organic devices such as organic electroluminescent devices. The polycyclic aromatic compounds of the present invention can be used in the manufacture of organic devices such as organic electroluminescent devices. [Brief explanation of the drawing]

[0026] [Figure 1] This is a schematic cross-sectional view showing an example of an organic field light-emitting device. [Figure 2] This is an energy level diagram showing the energy relationships between the host, assisting dopant, and emitting dopant of a TAF device using a common fluorescent dopant. [Figure 3] This is an energy level diagram showing an example of the energy relationship between the host, assisting dopant, and emitting dopant in an organic electroluminescent device according to one aspect of the present invention. [Modes for carrying out the invention]

[0027] The present invention will be described in detail below. The following descriptions of constituent elements may be based on representative embodiments or specific examples, but the present invention is not limited to such embodiments. In this specification, numerical ranges expressed using "~" mean a range that includes the numbers written before and after "~" as the lower and upper limits. Also, in this specification, "hydrogen" in the description of structural formulas means "hydrogen atom (H)". In this specification, organic electroluminescent elements may be referred to as organic EL elements.

[0028] In this specification, chemical structures and substituents are sometimes expressed in terms of carbon number. However, when a substituent is substituted into a chemical structure, or when a substituent is further substituted into another substituent, the carbon number refers to the carbon number of the chemical structure and the substituent itself, and does not refer to the total carbon number of the chemical structure and substituent, or the total carbon number of the substituents. For example, "substituent B with carbon number Y substituted by substituent A with carbon number X" means that "substituent A with carbon number X" is substituted into "substituent B with carbon number Y," and carbon number Y is not the total carbon number of substituent A and substituent B. Also, for example, "substituent B with carbon number Y substituted by substituent A" means that "substituent A (without carbon number limitation)" is substituted into "substituent B with carbon number Y," and carbon number Y is not the total carbon number of substituent A and substituent B.

[0029] The chemical structural formulas described herein (including general formulas drawn using the Markush structure formula, as shown in formula (1) below) are planar structural formulas, and therefore, in reality, various isomeric structures such as enantioisomers, diastereoisomers, and rotational isomers may exist. In this specification, unless otherwise specified, the compounds described may have any isomeric structure conceivable from their planar structural formula, or they may be mixtures of possible isomers in any proportion.

[0030] This specification describes numerous structural formulas of aromatic compounds. While aromatic compounds are described using combinations of double and single bonds, in reality, due to π-electron resonance, even a single substance can have multiple equivalent resonance structures where double and single bonds alternate. This specification describes only one resonance structure per substance; however, unless otherwise specified, it is assumed that other organically equivalent resonance structures are also included. This is referenced later in notations such as "Z=Z". For example, regarding "Z=Z" in formula (1) described later, an example is shown below. However, this is not limited to this; it naturally applies not only to the single resonance structure described, but also to other possible equivalent resonance structures.

[0031] [ka]

[0032] In this specification, we use two expressions: "may be" and "not be, or have been," but both expressions have the same meaning.

[0033] In this specification, the term "adjacent" refers to adjacent elements within the same ring, unless otherwise specified.

[0034] In this specification, substituents may be substituted with further substituents. (Substituents may be described as “substituted or unsubstituted”). This means that at least one hydrogen of the substituent ("first substituent" or “first substituent") is substituted with or unsubstituted with a further substituent ("second substituent" or “second substituent"). The first substituent (first substituent) and the second substituent (second substituent) can be described in the specification, respectively.

[0035] <1. Polycyclic aromatic compounds> The polycyclic aromatic compounds of the present invention are polycyclic aromatic compounds having a structure consisting of one or more structural units represented by formula (1). The polycyclic aromatic compounds of the present invention have high luminescence quantum yield (PLQY), a narrow emission half-width, and excellent color purity.

[0036] [ka]

[0037] In equation (1), in ring A and ring B, Z is independently either N or CR. 11 Either Z=Z is independently >O, >NR, >C(-R)2, >Si(-R)2, >S, or >Se, and the R in >NR, >C(-R)2, and >Si(-R)2 is independently hydrogen, a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted alkyl, or a substituted or unsubstituted cycloalkyl, and the two Rs in >C(-R)2 and >Si(-R)2 are bonded to each other to form a ring or not. Here, the aryl, heteroaryl, alkyl, and cycloalkyl groups are referred to as first substituents. These groups are described as "substituted or unsubstituted," but if at least one hydrogen is substituted, aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl groups are preferred. These aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, and substituted silyl groups are referred to as second substituents.

[0038] CR 11 R 11Each of these groups is independently a hydrogen atom, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl 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 alkenyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted arylthio group, or a substituted silyl group. Here, the aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio, and substituted silyl groups are referred to as first substituents. Although these groups are described as "substituted or unsubstituted," aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl groups are preferred when at least one hydrogen atom is substituted. These aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, and substituted silyl groups are referred to as second substituents.

[0039] R 11 Preferred elements include hydrogen, substituted or unsubstituted aryls, substituted or unsubstituted heteroaryls, substituted or unsubstituted diarylaminos, substituted or unsubstituted alkyls, substituted or unsubstituted cycloalkyls, or substituted silyls.

[0040] Next, we will explain the statement that "each Z=Z is independently >O, >NR, >C(-R)2, >Si(-R)2, >S, or >Se". For example, in ring A in equation (1), rings obtained by replacing "Z=Z" with >O, ​​>NR, >C(-R)2, >Si(-R)2, >S, or >Se include cyclopentadiene rings, pyrrole rings, furan rings, and thiophene rings. In ring A, for example, one Z=Z is >NR, >O, >S, or >C(-R)2, and the remaining Z is CR 11For example, if one Z=Z is >NR, >O, >S, >C(-R)2, and the remaining Z is CR 11 And, as will be described later, adjacent R 11 Here are some examples where a benzene ring is formed. However, the forms that ring A and other elements can take are not limited to the examples below.

[0041] [ka]

[0042] As described above, aromatic compounds have organically equivalent resonance structures, so any possible resonance structure may be used as the basis. Note that the R in >NR, >C(-R)2, and >Si(-R)2, where Z=Z, are independently hydrogen, a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted alkyl, or a substituted or unsubstituted cycloalkyl. The two Rs in >C(-R)2 and >Si(-R)2 are either bonded to each other to form a ring or not. These groups are described as "substituted or unsubstituted," but when at least one hydrogen is substituted, aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl groups are preferred. For details regarding the first and second substituents, and the terms used herein and their preferred ranges, please refer to the specification.

[0043] Note that each Z is independent and all are CR. 11 It is preferable that this is the case. Also, Y on the benzene ring 1 R becomes the parametric position 11 is a hydrogen or non-hydrogen substituent, and other R 11 It is preferable that is hydrogen. In the B ring, Y is on the benzene ring. 1 R becomes the parametric position 11 is a substituent other than hydrogen, and other R 11It is more preferable that is hydrogen. As for the substituent in this case, the preferred substituents described later as the first substituent include, for example, tertiary alkyl (t-butyl or t-amyl, etc.) represented by formula (tR), cycloalkyl, diarylamino or arylheteroarylamino which may be substituted with tertiary alkyl or alkyl represented by formula (tR). In ring A, Y on the benzene ring. 1 R becomes the parametric position 11 is hydrogen or alkyl (such as methyl or t-butyl), and other R 11 It is more preferable that it be hydrogen.

[0044] Two adjacent R 11 These groups may bond to each other to form an aryl ring or a heteroaryl ring. At least one hydrogen of the formed aryl ring and heteroaryl ring is substituted or unsubstituted with a substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino, substituted or unsubstituted diheteroarylamino, substituted or unsubstituted arylheteroarylamino, substituted or unsubstituted diarylboryl, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted arylthio, or substituted silyl, or unsubstituted. If substituted, the substituent is preferably a substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, or substituted silyl. Although these groups are described as "substituted or unsubstituted," if at least one hydrogen is substituted, aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl is preferred. With regard to the first and second substituents, and to the terms and preferred ranges used herein, refer to the description in the specification. The aryl ring formed is preferably a benzene ring, naphthalene ring, indene ring, or cyclopentadiene ring, and the heteroaryl ring formed is preferably a thiophene ring, pyrrole ring, furan ring, benzothiophene ring, benzofuran ring, or indole ring.

[0045] In equation (1), the C ring is a ring structure represented by equation (C). In equation (C), any two consecutive Z C One side is Y 1 The carbon that bonds with X 2 This is a carbon that is bonded to it. This is two consecutive Z atoms on either of the c1 rings, as shown below. C Y 1 and X 2 It may bond with any of the following, and also with two consecutive Z of any of the c2 rings. C Y 1 and X 2 This means that it may be combined with any of the following. A preferred form is shown below. In formulas (1a), (1b), (1c), (1d), (1e), (1f), (1g), and (1h), Z c Each of them is independent and all are CR 11 A form in which this is preferred is also preferred in formulas (1c), (1d), (1e), (1f), (1g), and (1h), where the Z of the c2 ring is c Each of them is independent and all are CR c And, as will be described later, adjacent R c A form in which these elements form bonds with each other to form an aryl ring (preferably a benzene ring) is also preferred. Furthermore, in formulas (1a), (1b), (1c), (1d), (1e), (1f), (1g), and (1h), formulas (1a) and (1b) are preferred, with formula (1a) being the most preferred. For explanations of each symbol and term, please refer to the description in this specification later.

[0046] [ka]

[0047] In formula (1), Xc The group is >O, >NR, >C(-R)2, >Si(-R)2, >S, or >Se, where the R in >NR, >C(-R)2, and >Si(-R)2 is independently hydrogen, a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted alkyl, or a substituted or unsubstituted cycloalkyl, and the two Rs in >C(-R)2 and >Si(-R)2 are bonded to each other to form a ring or not. The two Rs in >C(-R)2 and >Si(-R)2 are bonded to each other to form a ring or not. These groups are described as "substituted or unsubstituted," but if at least one hydrogen is substituted, aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl groups are preferred. For the first and second substituents, and for the terms used herein and their preferred ranges, refer to the description in the specification.

[0048] In formula (1), Z C Each of these can be independently N or CR C And R C Each of these is independently hydrogen, a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted diarylamino, a substituted or unsubstituted diheteroarylamino, a substituted or unsubstituted arylheteroarylamino, a substituted or unsubstituted diarylboryl, a substituted or unsubstituted alkyl, a substituted or unsubstituted cycloalkyl, a substituted or unsubstituted alkenyl, a substituted or unsubstituted alkoxy, a substituted or unsubstituted aryloxy, a substituted or unsubstituted arylthio, or a substituted silyl. These groups are described as "substituted or unsubstituted," but when at least one hydrogen is substituted, aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl groups are preferred. For details regarding these first and second substituents, and for the terms used herein and their preferred ranges, please refer to the specification.

[0049] Two adjacent Rs C may be bonded to each other to form an aryl ring or a heteroaryl ring. At least one hydrogen of the formed aryl ring and heteroaryl ring is substituted or unsubstituted by aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio, or substituted silyl, or is unsubstituted. When substituted, the substituent is preferably aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl. Although these groups are described as "substituted or unsubstituted", when at least one hydrogen is substituted, aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl is preferred. The aryl ring formed is preferably a benzene ring, naphthalene ring, indene ring, or cyclopentadiene ring, and the heteroaryl ring formed is preferably a thiophene ring, pyrrole ring, furan ring, benzothiophene ring, benzofuran ring, or indole ring, with the benzene ring being most preferred. Regarding this first substituent and the second substituent, and regarding the terms used herein and their preferred ranges, reference can be made to the description in the specification.

[0050] In formula (1c), formula (1d), formula (1e), formula (1f), formula (1g) and formula (1h), Z of the c2 ring C are all independently N or C-R C and adjacent C-R CIt is preferable that they form a bond with each other to form an aryl ring or a heteroaryl ring (preferably an aryl ring, more preferably a benzene ring). This preferred form is shown below. Regarding the definitions of the symbols in Formula (1c-2), Formula (1d-2), Formula (1e-2), Formula (1f-2), Formula (1g-2) and Formula (1h-2), and their preferred ranges, reference can be made to the descriptions of Formula (1c), Formula (1d), Formula (1e), Formula (1f), Formula (1g) and Formula (1h).

[0051] [Chemical Formula]

[0052] In Formula (1) and its preferred form, Y 1 is, independently of each other, B, P, P=O, P=S, Al, Ga, As, Si-R, or Ge-R, B or P=O is preferred, and B is most preferred. R in the Si-R and Ge-R is aryl having 6 to 12 carbon atoms, alkyl having 1 to 6 carbon atoms, or cycloalkyl having 3 to 14 carbon atoms. R in Si-R and Ge-R in Formula (1) 1 is aryl, alkyl or cycloalkyl, and examples of this aryl, alkyl or cycloalkyl include the groups described above. Particularly, aryl having 6 to 10 carbon atoms (such as phenyl, naphthyl, etc.), alkyl having 1 to 5 carbon atoms (such as methyl, ethyl, etc.) or cycloalkyl having 5 to 10 carbon atoms (preferably cyclohexyl or adamantyl) are preferred.

[0053] In Formula (1), one of X 1 and X 2 is >N-L CY -R CY and the other is >N-GA or >N-GB.

[0054] In >N-L CY -R CY for L CYThe group is a substituted or unsubstituted alkylene, a substituted or unsubstituted cycloalkylene, a substituted or unsubstituted arylene, or a substituted or unsubstituted heteroarylene, preferably a substituted or unsubstituted arylene or a substituted or unsubstituted heteroarylene, more preferably a substituted or unsubstituted phenylene, a substituted or unsubstituted naphthylene, a substituted or unsubstituted biphenylylene, a substituted or unsubstituted terphenylylene, a substituted or unsubstituted fluorenylene, or a substituted or unsubstituted dibenzofuranylene, and even more preferably a substituted or unsubstituted 1,4-phenylene, a substituted or unsubstituted 4,4'-biphenylene, or a substituted or unsubstituted 4,4''-terphenylene. Groups in which any one of these divalent groups is replaced by naphthylene are also preferred. These groups are described as "substituted or unsubstituted," but when at least one hydrogen is substituted, aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl groups are preferred. Aryl and alkyl groups (particularly methyl, or tR as described below) are more preferred. These may be further substituted with aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl groups. For details regarding these first and second substituents, and the terms and their preferred ranges used herein, please refer to the specification. When we say "substituted or unsubstituted," the substituents are particularly preferably alkyl or alkyl-substituted aryl groups, and more preferably methyl or methyl-substituted phenyl groups.

[0055] >NL CY -R CY In R CY This is a substituted or unsubstituted cycloalkyl group, with substituted or unsubstituted adamantyl being preferred, and unsubstituted adamantyl being most preferred. In all cases, 1-adamantyl is preferred. >NL CY -R CY The specific form is shown in equations (CY-1) to (CY-13) below. In equations (CY-1) to (CY-13), L CYAt least one hydrogen atom in the portion corresponding to the above is either substituted or unsubstituted according to the above description. In formulas (CY-1) to (CY-10), formulas (CY-1), (CY-7), (CY-8), or (CY-9) are preferred, and formulas (CY-1) or (CY-7) are more preferred.

[0056] [ka]

[0057] GA is a group represented by formula (GA), and GB is a group represented by formula (GB). [ka] An example of equation (GB) is given by equation (GB') below.

[0058] [ka]

[0059] In each formula, Z g Each of these can be independently N or CR g The CR g R g Each of these groups is independently a hydrogen, a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted diarylamino, a substituted or unsubstituted diheteroarylamino, a substituted or unsubstituted arylheteroarylamino, a substituted or unsubstituted diarylboryl, a substituted or unsubstituted alkyl, a substituted or unsubstituted cycloalkyl, a substituted or unsubstituted alkenyl, a substituted or unsubstituted alkoxy, a substituted or unsubstituted aryloxy, a substituted or unsubstituted arylthio, or a substituted silyl. Although these groups are described as "substituted or unsubstituted," aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl groups are preferred when at least one hydrogen is substituted. gThe R is preferably an aryl or alkyl (particularly a tR as described later), and most preferably an alkyl (particularly a tR as described later). For the terms used herein and their preferred ranges, please refer to the specification. In formulas (GA) and (GB), respectively, 0 to 3 R a is a substituent other than hydrogen, and other R a It is preferably hydrogen, and 0 to 2 R a is a substituent other than hydrogen, and other R a It is more preferably hydrogen, and 0 to 1 R a is a substituent other than hydrogen, and other R a It is even more preferable that it be hydrogen.

[0060] In each equation, two adjacent R g These groups may bond to each other to form an aryl ring or a heteroaryl ring, where at least one hydrogen of the formed aryl and heteroaryl rings is substituted or unsubstituted with a substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino, substituted or unsubstituted diheteroarylamino, substituted or unsubstituted arylheteroarylamino, substituted or unsubstituted diarylboryl, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, or substituted or unsubstituted arylthio, or unsubstituted. Although these groups are described as "substituted or unsubstituted," when at least one hydrogen is substituted, aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl groups are preferred. For the terms described herein and their preferred ranges, refer to the description in the specification.

[0061] Also, any one of Z g X 1 or X 2 It is a carbon atom bonded to N. The bond is located on either the g1 or g2 ring.

[0062] A is >O, >NR, >Si(-R)2, >S, or >Se, where the R in >NR and >Si(-R)2 is independently hydrogen, a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted alkyl, or a substituted or unsubstituted cycloalkyl, and the two Rs in >Si(-R)2 are bonded to each other to form a ring or not. Although these groups are described as "substituted or unsubstituted," aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl groups are preferred when at least one hydrogen is substituted. For the terms described herein and their preferred ranges, refer to the description in the specification, but A is preferably >O, >NR, or >S, more preferably >O or >NR, and even more preferably >O.

[0063] Regarding the specific form of formula (GA), examples include any of the following formulas (GA-1) to (GA-52). However, it is not limited to these examples. In the following formulas, * represents X. 1 Or X 2 This represents the bond position with N in N-GA. At least one hydrogen in formulas (GA-1) to (GA-52) is substituted or unsubstituted according to the above description. Among formulas (GA-1) to (GA-52), formulas (GA-1), (GA-4), (GA-5), (GA-6), (GA-7), (GA-8), (GA-9), (GA-10), (GA-11), (GA-12), or (GA-13) are preferred, formulas (GA-1), (GA-5), (GA-10), or (GA-11) are more preferred, and formulas (GA-1) or (GA-5) are most preferred.

[0064] [ka]

[0065] [ka]

[0066] Regarding the specific form of equation (GB), examples include any of the following equations (GB-1) to (GB-14). However, it is not limited to these examples. In the following equations, * represents X. 1 Or X 2 This represents the bond position with N in N-GB. At least one hydrogen in equations (GB-1) to (GB-14) is either substituted or unsubstituted according to the above description. Of formulas (GB-1) to (GB-14), formulas (GB-1), (GB-2), (GB-3), (GB-6), (GB-7), (GB-8), (GB-9), (GB-10), (GB-12), (GB-13), or (GB-14) are preferred, formulas (GB-1), (GB-3), (GB-5), (GB-6), (GB-7), (GB-10), (GB-13), or (GB-14) are more preferred, and formulas (GB-1), (GB-3), (GB-6), (GB-13), or (GB-14) are most preferred.

[0067] [ka]

[0068] The polycyclic aromatic compound of the present invention is a polycyclic aromatic compound having a structure consisting of one or more structural units represented by formula (1) and its preferred form. Examples of polycyclic aromatic compounds having a structure consisting of one of the above structural units include the polycyclic aromatic compound represented by the formula described above as the structural unit represented by formula (1). Examples of polycyclic aromatic compounds having a structure consisting of two or more structural units represented by formula (1) include compounds corresponding to the polymer of the polycyclic aromatic compound represented by the formula described above as the structural unit represented by formula (1). The polymer is preferably a 2-6 mer, more preferably a 2-3 mer, and particularly preferably a dimer. The polymer may be in a form in which a single compound has multiple of the above unit structures, and may be in a form in which any ring (A ring, B ring, or C ring) included in the above structural unit is shared among multiple unit structures, or may be in a form in which any rings (A ring, B ring, or C ring) included in the above unit structures are condensed together. Furthermore, the above unit structure may also be in a form in which multiple linking groups such as single bonds and alkylenes, phenylenes, and naphthylenes having 1 to 3 carbon atoms are bonded together. Of these, a form in which the rings are shared is preferred.

[0069] A polycyclic aromatic compound having a structure consisting of one or more structural units represented by formula (1), and at least one selected from the group consisting of an aryl ring and a heteroaryl ring in a preferred form thereof, is either not fused with or is fused with at least one cycloalkane.

[0070] The cycloalkane can be any cycloalkane having 3 to 24 carbon atoms. In this case, at least one hydrogen atom in the cycloalkane may be substituted with an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, an alkyl group having 1 to 24 carbon atoms, or a cycloalkyl group having 3 to 24 carbon atoms. At least one -CH2- in the cycloalkane may be substituted with -O-, but a cycloalkane in which all atoms are -CH2- is preferred.

[0071] When a structure consisting of one or more structural units represented by formula (1) is condensed with at least one cycloalkane, it is preferable that the at least one cycloalkane is a cycloalkane having 3 to 20 carbon atoms, wherein at least one hydrogen atom in the cycloalkane may be substituted with an aryl group having 6 to 16 carbon atoms, a heteroaryl group having 2 to 22 carbon atoms, an alkyl group having 1 to 12 carbon atoms, or a cycloalkyl group having 3 to 16 carbon atoms.

[0072] Examples of "cycloalkanes" include cycloalkanes with 3 to 24 carbon atoms, cycloalkanes with 3 to 20 carbon atoms, cycloalkanes with 3 to 16 carbon atoms, cycloalkanes with 3 to 14 carbon atoms, cycloalkanes with 5 to 10 carbon atoms, cycloalkanes with 5 to 8 carbon atoms, cycloalkanes with 5 to 6 carbon atoms, and cycloalkanes with 6 carbon atoms.

[0073] Specific examples of cycloalkanes include cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctane, cyclononane, cyclodecane, norbornene, bicyclo[1.1.0]butane, bicyclo[1.1.1]pentane, bicyclo[2.1.0]pentane, bicyclo[2.1.1]hexane, bicyclo[3.1.0]hexane, bicyclo[2.2.1]heptane, bicyclo[2.2.2]octane, adamantane, diamantane, decahydronaphthalene, and decahydroazulene, as well as alkyl (especially methyl), halogen (especially fluorine), and deuterium-substituted compounds of these compounds having 1 to 5 carbon atoms.

[0074] Among these, for example, as shown in the following structural formula, a structure in which at least one hydrogen at the α-position carbon of cycloalkane (in the cycloalkyl condensed to an aryl ring or heteroaryl ring, the carbon at the position adjacent to the carbon of the condensation site, corresponding to the benzylic position) is substituted is preferred, a structure in which two hydrogens at the α-position carbon are substituted is more preferred, and a structure in which a total of four hydrogens at two α-position carbons are substituted is even more preferred. This is to protect chemically active sites and improve the durability of the compound. Examples of this substituent include an alkyl (especially methyl) substituent having 1 to 5 carbon atoms, a halogen (especially fluorine) substituent, and a deuterium substituent. In particular, it is preferred that a partial structure represented by the following formula (Z-11) is bonded to adjacent carbon atoms in the aryl ring or heteroaryl ring.

[0075]

Chemical formula

[0076] The number of cycloalkanes condensed to one aryl ring or heteroaryl ring is preferably 1 to 3, more preferably 1 or 2, and even more preferably 1. For example, examples of one or more cycloalkanes condensed to one benzene ring (phenyl) are shown below. * represents the bonding position, and that position may be any carbon that constitutes the benzene ring and does not constitute the cycloalkane. Cycloalkanes condensed in the same way as in formula (Cy-1-4) and formula (Cy-2-4) may be condensed. Even when the condensed ring (group) is another aryl ring or heteroaryl ring other than the benzene ring (phenyl), or when the condensed cycloalkane is a cycloalkane other than cyclopentane or cyclohexane, the same applies.

[0077]

Chemical formula

[0078] At least one -CH2- in a cycloalkane may be substituted with -O-. For example, the following shows a cycloalkane condensed to a single benzene ring (phenyl) in which one or more -CH2- groups are substituted with -O-. The same applies when the condensed ring (group) is an aromatic ring or heteroaromatic ring other than a benzene ring (phenyl), or when the condensed cycloalkane is a cycloalkane other than cyclopentane or cyclohexane.

[0079] [ka]

[0080] At least one hydrogen atom in the cycloalkane may be substituted, and examples of such substituents include aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl, alkyl, cycloalkyl, alkoxy, aryloxy, substituted silyl, deuterium, cyano, or halogen, the details of which can be found by referring to the description of the first substituent in this specification. Among these substituents, alkyl (e.g., alkyls having 1 to 6 carbon atoms), cycloalkyl (e.g., cycloalkyls having 3 to 14 carbon atoms), halogen (e.g., fluorine), and deuterium are preferred. Furthermore, when a cycloalkyl is substituted, the substitution may form a spiro structure, an example of which is shown below.

[0081] [ka]

[0082] One form of cycloalkane condensation is the condensation of the A, B, and C rings of a polycyclic aromatic compound having a structure consisting of one or more structural units represented by formula (1) with a cycloalkane.

[0083] Other forms of cycloalkane condensation include polycyclic aromatic compounds having a structure consisting of one or more structural units represented by formula (1), and in a preferred form thereof, X 1 or X 2 Either one of the following >NL CY -R CY L CY A form that includes a ring condensed with a cycloalkane, and also X 1 or X 2 Examples include forms containing a ring condensed with a cycloalkane on either >N-GA (GA) or >N-GB (GB), as well as having a diarylamino condensed with a cycloalkane, a carbazolyl condensed with a cycloalkane (condensed on this benzene ring), or a benzocarbazolyl condensed with a cycloalkane (condensed on this benzene ring). For diarylaminos, the group described above as the "first substituent" is an example.

[0084] A polycyclic aromatic compound having a structure consisting of one or more structural units represented by formula (1), and a preferred form thereof. The cycloalkane condensation described above is preferably condensed on the A ring, B ring, or C ring, and more preferably condensed on the B ring or C ring. A form in which both the B ring and C ring are condensed is also preferred.

[0085] Furthermore, by introducing a cycloalkane structure to the polycyclic aromatic compound of the present invention, a decrease in melting point and sublimation temperature can be expected. This means that in sublimation purification, which is almost indispensable as a purification method for organic devices such as organic EL elements that require high purity, purification can be performed at a relatively low temperature, thus avoiding thermal decomposition of the material. The same applies to the vacuum deposition process, which is a powerful means of fabricating organic devices such as organic EL elements, as the process can be carried out at a relatively low temperature, thus avoiding thermal decomposition of the material and resulting in the acquisition of high-performance organic devices. In addition, since the solubility in organic solvents is improved by introducing a cycloalkane structure, it can also be applied to the fabrication of elements using a coating process. However, the present invention is not particularly limited to these principles. For this reason, it is preferable that the above-mentioned cycloalkane condensation is introduced in polycyclic aromatic compounds having a structure consisting of one or more structural units represented by formula (1), and in the preferred form thereof.

[0086] In a structure consisting of one or more structural units represented by formula (1) and its preferred forms, all or part of the hydrogen atoms are substituted with deuterium, cyanosides, or halogens, or are not substituted.

[0087] For example, in a structure consisting of a structural unit represented by formula (1) and one or more preferred forms thereof, the structure includes an A ring, a B ring, a C ring, substituents on the A-C rings, and Y 1 When R is Si-R or Ge-R, R (=alkyl, cycloalkyl, aryl), and X 1 and X 2 one of >NL CY -R CY L CY Or R CY , or X 1 and X 2In one of the >N-GA or >N-GB, the hydrogen in the GA or GB can be substituted with deuterium, cyanopropyl alcohol, or halogen, with a notable example being that all or some of the hydrogens in the aryl or heteroaryl are substituted with deuterium, cyanopropyl alcohol, or halogen. The halogen is fluorine, chlorine, bromine, or iodine, preferably fluorine, chlorine, or bromine, more preferably fluorine or chlorine, and even more preferably fluorine. The form in which hydrogen is replaced with deuterium is particularly preferred for improving the stability of the compound. It is preferable that one hydrogen is replaced with deuterium, more preferably that multiple hydrogens are replaced with deuterium, even more preferably that all hydrogens in the aromatic moiety are replaced with deuterium, and most preferably that all hydrogens are replaced with deuterium.

[0088] Examples of "aryl rings" include aryl rings having 6 to 30 carbon atoms, with aryl rings having 6 to 16 carbon atoms being preferred, aryl rings having 6 to 12 carbon atoms being more preferred, and aryl rings having 6 to 10 carbon atoms being particularly preferred.

[0089] Specific examples of "aryl rings" include the monocyclic benzene ring, the bicyclic biphenyl ring, the condensed bicyclic naphthalene ring and indene ring, the tricyclic terphenyl ring (m-terphenyl, o-terphenyl, p-terphenyl), the condensed tricyclic acenaphthylene ring, fluorene ring, phenalene ring, phenanthrene ring, and anthracene ring, the condensed tetracyclic triphenylene ring, pyrene ring, naphthalene ring, and chrysene ring, and the condensed pentacyclic perylene ring and pentacene ring. Furthermore, the fluorene ring, benzofluorene ring, and indene ring also include structures in which a fluorene ring, benzofluorene ring, and cyclopentane ring are spiro-linked, respectively. Furthermore, the fluorene ring, benzofluorene ring, and indene ring also include those in which two of the two hydrogen atoms of the methylene group are replaced by alkyl groups such as methyl as the first substituent described later, resulting in the dimethylfluorene ring, dimethylbenzofluorene ring, and dimethylindene ring, respectively.

[0090] Examples of "heteroaryl rings" include heteroaryl rings having 2 to 30 carbon atoms, with heteroaryl rings having 2 to 25 carbon atoms being preferred, heteroaryl rings having 2 to 20 carbon atoms being more preferred, heteroaryl rings having 2 to 15 carbon atoms being even more preferred, and heteroaryl rings having 2 to 10 carbon atoms being particularly preferred. Examples of "heteroaryl rings" include heterocycles containing 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen in addition to carbon as ring constituent atoms.

[0091] Specific "heteroaryl rings" include, for example, pyrrole ring, oxazole ring, isoxazole ring, thiazole ring, isothiazole ring, imidazole ring, oxadiazole ring, thiadiazole ring, triazole ring, tetrazole ring, pyrazole ring, pyridine ring, pyrimidine ring, pyridazine ring, pyrazine ring, triazine ring, indole ring, isoindole ring, 1H-indazole ring, benzimidazole ring, benzoxazole ring, benzothiazole ring, 1H-benzotriazole ring, quinoline ring, isoquinoline ring, cinnoline ring, quinazoline ring, quinoxaline ring, phthalazine ring, naphthyridine ring, purine ring, pteridine ring, carbazole ring, carboline ring, acridine ring, phenoxathiin ring, phenoxazine ring, phenothiazine ring, phenazine ring, phenazasiline ring, indolizine ring, furan ring, benzofuran ring, isobenzofuran ring, dibenzofuran ring, thiophene ring, benzothiophene ring, dibenzothiophene ring, furazan ring, thianthrene ring, indolocarbazole ring, benzindolocarbazole ring, benzobenzindolocarbazole ring, naphthobenzofuran ring, dioxin ring, dihydroacridine ring, xanthene ring, thioxanthene ring, dibenzodioxin ring, etc. Further, in the dihydroacridine ring, xanthene ring, thioxanthene ring, two of the two hydrogens of methylene are each substituted with an alkyl such as methyl as the first substituent described later, and dimethyldihydroacridine ring, dimethylxanthene ring, dimethylthioxanthene ring, etc. are also preferred. Also, bipyridine ring, phenylpyridine ring, pyridylphenyl ring which are bicyclic systems, and terpyridyl ring, bispyridylphenyl ring, pyridylbiphenyl ring which are tricyclic systems are also mentioned as "heteroaryl rings". Further, the "heteroaryl ring" shall also include a pyran ring.

[0092] Further, the following formula (BO) is also included in the heteroaryl ring.

Chemical formula

[0093] At least one hydrogen atom in the above-mentioned "aryl ring" or "heteroaryl ring" may be substituted with a first substituent, which is a substituted or unsubstituted "aryl", a substituted or unsubstituted "heteroaryl", a substituted or unsubstituted "diarylamino", a substituted or unsubstituted "diheteroarylamino", a substituted or unsubstituted "arylheteroarylamino", a substituted or unsubstituted "diarylboryl", a substituted or unsubstituted "alkyl", a substituted or unsubstituted "alkenyl", a substituted or unsubstituted "cycloalkyl", a substituted or unsubstituted "alkoxy", a substituted or unsubstituted "aryloxy", or a substituted or unsubstituted "arylthio", or a substituted "silyl".

[0094] Specifically, "aryl" refers to a monovalent group obtained by removing one hydrogen atom from the aforementioned "aryl ring." Examples include aryls with 6 to 30 carbon atoms, with aryls with 6 to 24 carbon atoms being preferred, aryls with 6 to 20 carbon atoms being more preferred, aryls with 6 to 16 carbon atoms being even more preferred, aryls with 6 to 12 carbon atoms being particularly preferred, and aryls with 6 to 10 carbon atoms being most preferred.

[0095] Furthermore, "heteroaryl" refers to a monovalent group obtained by removing one hydrogen atom from the "heteroaryl ring" described above. Examples include heteroaryls having 2 to 30 carbon atoms, with heteroaryls having 2 to 25 carbon atoms being preferred, heteroaryls having 2 to 20 carbon atoms being more preferred, heteroaryls having 2 to 15 carbon atoms being even more preferred, and heteroaryls having 2 to 10 carbon atoms being particularly preferred. Examples of heteroaryls include heterocycles containing 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen in addition to carbon as ring constituent atoms.

[0096] The aryl and heteroaryl in "substituted or unsubstituted diarylamino," "substituted or unsubstituted diheteroarylamino," and "substituted or unsubstituted arylheteroarylamino" as first substituents can be referenced from the "aryl" and "heteroaryl" described above, along with their preferred ranges.

[0097] In diarylaminos, the two aryls are either not bonded to each other or are bonded via a linking group. In diheteroarylaminos, the two heteroaryls are either not bonded to each other or are bonded via a linking group. In arylheteroarylaminos, the aryl and heteroaryl are either not bonded to each other or are bonded via a linking group. That is, wherever "diarylamino," "diheteroarylamino," or "arylheteroarylamino" is used in this specification, unless otherwise specified, it is assumed that the following explanations are added: "The two aryls in the diarylamino are either not bonded to each other or are bonded via a linking group," "The two heteroaryls in the diheteroarylamino are either not bonded to each other or are bonded via a linking group," and "The aryl and heteroaryl in the arylheteroarylamino are either not bonded to each other or are bonded via a linking group," respectively.

[0098] The above statement, "not bonded to each other, or bonded via a linking group," means that, as shown below, for example, the two phenyl groups in diphenylamino may be bonded together by a linking group. This explanation also applies to diheteroarylaminos and arylheteroarylaminos, which are formed with aryl or heteroaryl groups.

[0099] [ka]

[0100] Specifically, the linking groups are >O and >NR. X ,>C(-R X )2, >Si(-R X )2, >S, >CO, >CS, >SO, >SO2, and >Se are listed, R XEach of these is independently alkyl, cycloalkyl, aryl, or heteroaryl, and these may be substituted with alkyl, cycloalkyl, aryl, or heteroaryl, and also >C(-R X )2, >Si(-R X )2 in each of the two R X This is a single bond or a linking group X Y They may be joined to each other via X to form a ring. Y For example, >O, >NR Y ,>C(-R Y )2, >Si(-R Y )2, >S, >CO, >CS, >SO, >SO2, and >Se are listed, R Y Each of these is independently an alkyl, cycloalkyl, aryl, or heteroaryl, and these may be substituted with alkyl, cycloalkyl, aryl, or heteroaryl. However, X Y >C(-R Y )2 and >Si(-R Y )In the case of 2, two R Y They do not bond to form further rings. Furthermore, alkenylenes can also be given as linking groups. Any hydrogen atom of the alkenylene can independently form R 2X It may also be replaced with R 2X Each of these is independently an alkyl, cycloalkyl, substituted silyl, aryl, and heteroaryl, which may be substituted with alkyl, cycloalkyl, substituted silyl, or aryl.

[0101] Furthermore, the "alkyl" as the first substituent may be either linear or branched, for example, a linear alkyl having 1 to 24 carbon atoms or a branched alkyl having 3 to 24 carbon atoms. A C1 to 18 alkyl (a branched alkyl having 3 to 18 carbon atoms) is preferred, a C1 to 12 alkyl (a branched alkyl having 3 to 12 carbon atoms) is more preferred, a C1 to 8 alkyl (a branched alkyl having 3 to 8 carbon atoms) is even more preferred, a C1 to 6 alkyl (a branched alkyl having 3 to 6 carbon atoms) is particularly preferred, and a C1 to 5 alkyl (a branched alkyl having 3 to 5 carbon atoms) is most preferred.

[0102] Specific alkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl(t-amyl), n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, and t-octyl(1,1,3,3-tetramethylbutyl) Examples include 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 2,6-dimethyl-4-heptyl, 3,5,5-trimethylhexyl, n-decyl, n-undecyl, 1-methyldecyl, n-dodecyl, n-tridecyl, 1-hexylheptyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, and n-eicosyl. Other 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, and 1,1-dimethylhexyl.

[0103] As substituents containing the above-mentioned "alkyl," the tertiary-alkyl represented by the following formula (tR) is one of the particularly preferred substituents to the aryl or heteroaryl rings in the A, B, and C rings. This is because such bulky substituents increase the intermolecular distance, thereby improving the quantum emission yield (PLQY). Furthermore, substituents in which the tertiary-alkyl represented by formula (tR) is substituted as a second substituent are also preferred. Specifically, examples include diarylamino substituted with the tertiary-alkyl represented by (tR), carbazolyl (preferably N-carbazol) substituted with the tertiary-alkyl represented by (tR), or benzocarbazol (preferably N-benzocarbazol) substituted with the tertiary-alkyl represented by (tR). For "diarylamino," the group described below as the "first substituent" is an example. Examples of substitutions of the (tR) group on diarylamino, carbazolyl, and benzocarbazolyl groups include cases where some or all of the hydrogen atoms in the aryl or benzene ring of these groups are substituted with the (tR) group.

[0104] [ka]

[0105] In the formula (tR), R a , R b , and R c Each of these is an alkyl group having 1 to 24 carbon atoms, and any -CH2- in the alkyl group may be substituted with -O-, and the group represented by formula (tR) is substituted with at least one hydrogen in the structure containing the structural unit represented by formula (1) in *.

[0106] R a , R b and R cThe "alkyl group having 1 to 24 carbon atoms" can be either linear or branched. Examples include linear alkyl groups having 1 to 24 carbon atoms or branched alkyl groups having 3 to 24 carbon atoms, alkyl groups having 1 to 18 carbon atoms (branched alkyl groups having 3 to 18 carbon atoms), alkyl groups having 1 to 12 carbon atoms (branched alkyl groups having 3 to 12 carbon atoms), alkyl groups having 1 to 6 carbon atoms (branched alkyl groups having 3 to 6 carbon atoms), and alkyl groups having 1 to 4 carbon atoms (branched alkyl groups having 3 to 4 carbon atoms).

[0107] In equation (tR) of equation (1), R a , R b , and R c The total number of carbon atoms is preferably 3 to 20, and particularly preferably 3 to 10.

[0108] R a , R b , and R c Specific alkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl, n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, t-octyl, 1-methylheptyl, 2 Examples include -ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 2,6-dimethyl-4-heptyl, 3,5,5-trimethylhexyl, n-decyl, n-undecyl, 1-methyldecyl, n-dodecyl, n-tridecyl, 1-hexylheptyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, and n-eicosyl.

[0109] Examples of groups represented by formula (tR) include t-butyl, t-amyl, 1-ethyl-1-methylpropyl, 1,1-diethylpropyl, 1,1-dimethylbutyl, 1-ethyl-1-methylbutyl, 1,1,3,3-tetramethylbutyl, 1,1,4-trimethylpentyl, 1,1,2-trimethylpropyl, 1,1-dimethyloctyl, 1,1-dimethylpentyl, 1,1-dimethylheptyl, 1,1,5-trimethylhexyl, 1-ethyl- Examples include 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, and 1,1-dimethylhexyl. Of these, t-butyl and t-amyl are preferred.

[0110] Examples of "cycloalkyl" as the first substituent include cycloalkyl groups with 3 to 24 carbon atoms, 3 to 20 carbon atoms, 3 to 16 carbon atoms, 3 to 14 carbon atoms, 5 to 10 carbon atoms, 5 to 8 carbon atoms, 5 to 6 carbon atoms, and 5 carbon atoms. As specified herein, cyclohexyl includes monocyclic cyclohexyl groups as well as polycyclic groups such as adamantyl, as will be listed later.

[0111] Specific examples of cycloalkyls include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, norbornel, bicyclo[1.1.0]butyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.0]pentyl, bicyclo[2.1.1]hexyl, bicyclo[3.1.0]hexyl, bicyclo[2.2.1]heptyl, bicyclo[2.2.2]octyl, adamantyl, diamantyl, decahydronaphthalenyl, decahydroazlenyl, and alkyl (especially methyl) substituted derivatives of these compounds having 1 to 5 carbon atoms.

[0112] Examples of the first substituent, "alkenyl," include linear alkenyls with 2 to 24 carbon atoms or branched alkenyls with 4 to 24 carbon atoms. Alkenyls with 2 to 18 carbon atoms are preferred, alkenyls with 2 to 12 carbon atoms are more preferred, alkenyls with 2 to 6 carbon atoms are even more preferred, and alkenyls with 2 to 4 carbon atoms are particularly preferred. Specific examples of "alkenyls" include vinyl, allyl, and butadienyl.

[0113] As the first substituent, "alkoxy" can be, for example, a linear alkoxy having 1 to 24 carbon atoms or a branched alkoxy having 3 to 24 carbon atoms. An alkoxy having 1 to 18 carbon atoms (a branched alkoxy having 3 to 18 carbon atoms) is preferred, an alkoxy having 1 to 12 carbon atoms (a branched alkoxy having 3 to 12 carbon atoms) is more preferred, an alkoxy having 1 to 6 carbon atoms (a branched alkoxy having 3 to 6 carbon atoms) is even more preferred, and an alkoxy having 1 to 5 carbon atoms (a branched alkoxy having 3 to 5 carbon atoms) is particularly preferred.

[0114] Specific examples of alkoxys include methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, s-butoxy, t-butoxy, t-amyloxy, pentyloxy, hexyloxy, heptyloxy, and octyloxy.

[0115] The first substituent, "aryloxy," is a group in which the hydrogen of the -OH group is substituted with an aryl group, and the aryl group and its preferred range can be referenced from those described above.

[0116] The first substituent, "arylthio," is a group in which the hydrogen of the -SH group is substituted with an aryl group, and the aryl group and its preferred range can be referenced from those described above.

[0117] Furthermore, as the first substituent, a "substituted silyl" can be a silyl substituted with three substituents selected from the group consisting of alkyl, cycloalkyl, and aryl. Examples include trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, alkyldicycloalkylsilyl, triarylsilyl, dialkylarylsilyl, and alkyldiarylsilyl.

[0118] "Trialkylsilyl" refers to a group in which each of the three hydrogen atoms in the silyl group is independently substituted with an alkyl group. The alkyl group and its preferred range can be described by referring to the group described as "alkyl" in the first substituent above. Preferred alkyl groups for substitution are C1-C5 alkyl groups, specifically methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, t-butyl, and t-amyl.

[0119] Specific examples of trialkylsilyls include trimethylsilyl, triethylsilyl, tripropylsilyl, triisopropylsilyl, tributylsilyl, trisec-butylsilyl, trit-butylsilyl, trit-amylsilyl, ethyldimethylsilyl, propyldimethylsilyl, isopropyldimethylsilyl, butyldimethylsilyl, sec-butyldimethylsilyl, t-butyldimethylsilyl, t-amyldimethylsilyl, methyldiethylsilyl, propyldiethylsilyl, isopropyldiethylsilyl, butyldiethylsilyl, sec-butyldiethylsilyl, t-butyldiethylsilyl, t-amyldiethylsilyl, methyldipropylsilyl, ethyldipropylsilyl, t-amyldipropylsilyl, methyldiisopropylsilyl, ethyldiisopropylsilyl, butyldiisopropylsilyl, sec-butyldiisopropylsilyl, t-butyldiisopropylsilyl, t-amyldiisopropylsilyl, and t-amyldiisopropylsilyl.

[0120] "Tricycloalkylsilyl" refers to a group in which each of the three hydrogen atoms in the silyl group is independently substituted with a cycloalkyl group. The cycloalkyl group and its preferred range can be described by referring to the group described as "cycloalkyl" in the first substituent above. Preferred cycloalkyl groups for substitution are cycloalkyl groups having 5 to 10 carbon atoms, specifically including cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.0]pentyl, bicyclo[2.1.1]hexyl, bicyclo[3.1.0]hexyl, bicyclo[2.2.1]heptyl, bicyclo[2.2.2]octyl, adamantyl, decahydronaphthalenyl, and decahydroazlenyl.

[0121] Specific examples of tricycloalkylsilyls include tricyclopentylsilyl and tricyclohexylsilyl.

[0122] Specific examples of dialkylcycloalkylsilyls substituted with two alkyl groups and one cycloalkyl group, and alkyldicycloalkylsilyls substituted with one alkyl group and two cycloalkyl groups, include silyls substituted with groups selected from the specific alkyl and cycloalkyl groups mentioned above.

[0123] Specific examples of dialkylarylsilyls, alkyldiarylsilyls, and triarylsilyls, which are substituted with two alkyl groups and one aryl group, respectively, include silyls substituted with groups selected from the specific alkyl and aryl groups mentioned above. A particularly specific example of a triarylsilyl is triphenylsilyl.

[0124] Furthermore, the description of aryl in the first substituent "diarylboryl" and its preferred range can be referenced from the description of aryl above. In addition, these two aryls may be linked by a single bond or by a linking group. Examples of linking groups include >C(-R)2, >O, >S, and >NR. Here, R in >C(-R)2 and >NR is aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, alkoxy, or aryloxy (all of the above are first substituents), and the first substituent may be further substituted with aryl, heteroaryl, alkyl, or cycloalkyl (all of the above are second substituents). Specific examples of these groups can be referenced from the description of aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, alkoxy, or aryloxy as first substituents above. When "diarylboryl" is simply described in this specification, unless otherwise specified, it is assumed that the description "the two aryls of the diarylboryl are either not linked to each other or are linked by a single bond or by a linking group" is added.

[0125] As described, the first substituent (first substituent) is a substituted or unsubstituted "aryl", substituted or unsubstituted "heteroaryl", substituted or unsubstituted "diarylamino", substituted or unsubstituted "diheteroarylamino", substituted or unsubstituted "arylheteroarylamino", substituted or unsubstituted "diarylboryl", substituted or unsubstituted "alkyl", substituted or unsubstituted "cycloalkyl", substituted or unsubstituted "alkenyl", substituted or unsubstituted "alkoxy", substituted or unsubstituted "aryloxy", substituted or unsubstituted "arylthio", or substituted "silyl", and as described, at least one hydrogen in them may be substituted with the second substituent (second substituent). Unless otherwise specified, the second substituent is preferably an aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl. Specific examples can be found in the descriptions of "aryl," "heteroaryl," "diarylamino," "alkyl," "cycloalkyl," or "substituted silyl" as the first substituent. Furthermore, aryl and heteroaryl structures as the second substituent also include those in which at least one hydrogen is substituted with an aryl group such as phenyl (specific examples are the groups mentioned above), an alkyl group such as methyl or t-butyl (specific examples are the groups mentioned above), or a cycloalkyl group such as cyclohexyl (specific examples are the groups mentioned above). For example, in the case of a carbazolyl as the second substituent, a carbazolyl in which at least one hydrogen at the 9-position is substituted with an aryl group such as phenyl, an alkyl group such as methyl, or a cycloalkyl group such as cyclohexyl is also included as a heteroaryl structure as the second substituent. This description can also be applied to other descriptions of the first and second substituents in this specification.

[0126] The emission wavelength can be adjusted by the steric hindrance, electron-donating, and electron-withdrawing properties of the structure of the first substituent. Preferably, the group is represented by the following structural formula, and more preferably, methyl, t-butyl, t-amyl, t-octyl, neopentyl, adamantyl, phenyl, o-tolyl, p-tolyl, 2,4-xylyl, 2,5-xylyl, 2,6-xylyl, 2,4,6-mesityl, diphenylamino, di-p-tolylamino, bis(p-(t-butyl)phenyl)amino, carbazolyl, 3,6-dimethylcarbazolyl, 3,6- The compounds are di-t-butylcarbazol and phenoxy, and more preferably methyl, t-butyl, t-amyl, t-octyl, neopentyl, adamantyl, phenyl, o-tolyl, 2,6-xylyl, 2,4,6-mesityl, diphenylamino, di-p-tolylamino, bis(p-(t-butyl)phenyl)amino, carbazolyl, 3,6-dimethylcarbazolyl, and 3,6-di-t-butylcarbazolyl. From the viewpoint of ease of synthesis, greater steric hindrance is preferable for selective synthesis, and specifically, t-butyl, t-amyl, t-octyl, adamantyl, o-tolyl, p-tolyl, 2,4-xylyl, 2,5-xylyl, 2,6-xylyl, 2,4,6-mesityl, di-p-tolylamino, bis(p-(t-butyl)phenyl)amino, 3,6-dimethylcarbazolyl, and 3,6-di-t-butylcarbazolyl are preferred.

[0127] In the structural formula below, "Me" represents methyl, "tBu" represents t-butyl, "tAm" represents t-amyl, "tOct" represents t-octyl, and * represents the bond position. [ka]

[0128] [ka]

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[0139] Polycyclic aromatic compounds having a structure consisting of one or more structural units represented by formula (1) and its preferred forms are preferably structures containing at least one tert-alkyl (such as t-butyl or t-amyl), neopentyl, or adamantyl represented by formula (tR), and preferably contain a tert-alkyl (such as t-butyl or t-amyl) represented by formula (tR). This is because such bulky substituents increase the intermolecular distance, thereby improving the luminescence quantum yield (PLQY). Diarylaminos are also preferred substituents. Furthermore, diarylaminos substituted with the group of formula (tR), carbazolyls (preferably N-carbazol) substituted with the group of formula (tR), or benzocarbazols (preferably N-benzocarbazol) substituted with the group of formula (tR) are also preferred. Examples of substitutions of the (tR) group on diarylamino, carbazolyl, and benzocarbazolyl groups include cases where some or all of the hydrogen atoms in the aryl or benzene ring of these groups are substituted with the (tR) group.

[0140] Further specific examples of the polycyclic aromatic compound represented by formula (1) of the present invention include the following compounds. In the following structural formula, "Me" represents methyl, "tBu" represents t-butyl, "tAm" represents t-amyl, and "D" represents deuterium. Note that the following structure is just one example.

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[0188] The polycyclic aromatic compounds of the present invention can be produced by the following procedure.

[0189] <Method for producing polycyclic aromatic compounds> A structure having one or more structural units represented by formula (1) or formula (2) basically consists of an A ring (a ring), a B ring (b ring), and a C ring (c ring) bonded together by a bonding group (X 1 Ya X 2 An intermediate is produced by bonding the rings with a group containing (Y) (first reaction), and then the A ring (a ring), B ring (b ring), and C ring (c ring) are bonded with a group containing (Y) 1 The final product can be produced by bonding with a group containing (second reaction). In the first reaction, for example, if it is an etherification reaction, general reactions such as nucleophilic substitution reactions and Ullmann reactions can be used, and if it is an amination reaction, general reactions such as the Buchwald-Hartwig reaction can be used. In the second reaction, a tandem hetero-Friedel-Crafts reaction (sequential aromatic electrophilic substitution reaction, the same applies below) can be used. By using a starting material having the desired fused ring at some point in the reaction process, or by adding a ring condensation step, the compound can be produced in a fused ring in which at least one ring selected from the group consisting of rings A, B, and C is composed of two or more rings selected from the group consisting of a monocyclic aryl ring, a monocyclic heteroaryl ring, and a cyclopentadiene ring.

[0190] <Manufacturing method via intermediate-1> The polycyclic aromatic compounds of the present invention can be produced by a manufacturing method comprising the following steps. For details of each step, please refer to International Publication No. 2015 / 102118.

[0191] Using an organic alkali compound, X in intermediate 1 below 1 and X 2 The reaction step involves metallizing the halogen atoms (Hal) between them, and Y 1 Halides of Y1 Amination halogens, Y 1 Alkoxy compounds and Y 1 Using a reagent selected from the group consisting of aryl oxyides, the metal and Y 1 A reaction step to exchange and, using a Brønsted base, a continuous aromatic electrophilic substitution reaction is carried out, resulting in the Y 1 The reaction, which includes a reaction step to bond the B ring and the C ring, is described below.

[0192] [ka]

[0193] Examples of metallating reagents used in the halogen-metal exchange reaction in the scheme described above include alkyllithium compounds such as methyllithium, n-butyllithium, sec-butyllithium, and t-butyllithium; isopropylmagnesium chloride; isopropylmagnesium bromide; phenylmagnesium chloride; phenylmagnesium bromide; and lithium chloride complexes of isopropylmagnesium chloride, known as turbogrignard reagents.

[0194] In addition to the reagents mentioned above, other organic alkali compounds used as metalling reagents in the orthometal exchange reaction in the scheme described above include lithium diisopropylamide, lithium tetramethylpiperidide, lithium hexamethyldisilazide, potassium hexamethyldisilazide, lithium tetramethylpiperidinylmagnesium chloride-lithium chloride complex, and lithium tri-n-butylmagnesate.

[0195] Furthermore, when alkyllithium is used as a metalling reagent, additives that can accelerate the reaction include N,N,N',N'-tetramethylethylenediamine, 1,4-diazabicyclo[2.2.2]octane, and N,N-dimethylpropylene urea.

[0196] Furthermore, Lewis acids used in the schemes described above include AlCl3, AlBr3, AlF3, BF3·OEt2, BCl3, BBr3, GaCl3, GaBr3, InCl3, InBr3, In(OTf)3, SnCl4, SnBr4, AgOTf, ScCl3, Sc(OTf)3, ZnCl2, ZnBr2, Zn(OTf)2, MgCl2, MgBr2, Mg(OTf)2, LiOTf, NaOTf, KOTf, Me3SiOTf, Cu(OTf)2, CuCl2, YCl3, Y(OTf)3, TiCl4, TiBr4, ZrCl4, ZrBr4, FeCl3, FeBr3, CoCl3, and CoBr3. These Lewis acids can also be used in a similar manner when supported on a solid.

[0197] Furthermore, examples of Brønsted acids used in the schemes described above include p-toluenesulfonic acid, methanesulfonic acid, trifluoromethanesulfonic acid, fluorosulfonic acid, carborane acid, trifluoroacetic acid, (trifluoromethanesulfonyl)imide, tris(trifluoromethanesulfonyl)methane, hydrogen chloride, hydrogen bromide, and hydrogen fluoride. Examples of solid Brønsted acids include Amberlist (trade name: Dow Chemical), Nafion (trade name: DuPont), zeolite, and TeikaCure (trade name: Teika Corporation).

[0198] Furthermore, amines that may be added to the schemes described above include diisopropylethylamine, triethylamine, tributylamine, 1,4-diazabicyclo[2.2.2]octane, N,N-dimethyl-p-toluidine, N,N-dimethylaniline, pyridine, 2,6-lutidine, and 2,6-di-t-butylamine.

[0199] Furthermore, solvents used in the schemes described above include o-dichlorobenzene, chlorobenzene, toluene, benzene, methylene chloride, chloroform, dichloroethylene, benzotrifluoride, decalin, cyclohexane, hexane, heptane, 1,2,4-trimethylbenzene, xylene, diphenyl ether, anisole, cyclopentyl methyl ether, tetrahydrofuran, dioxane, and methyl-t-butyl ether.

[0200] Here, Y 1 However, although an example of B was described, by appropriately changing the raw materials, Y can be produced. 1 However, compounds with P, P=O, P=S, Al, Ga, As, Si-R, or Ge-R can also be synthesized.

[0201] In the above scheme, a Brønsted base or Lewis acid may be used to accelerate the tandem hetero-Friedel-Crafts reaction. However, Y 1 trifluoride, Y 1 trichloride, Y 1 Tribromide of Y 1 Y such as triiodide 1 When using halides, as the aromatic electrophilic substitution reaction progresses, acids such as hydrogen fluoride, hydrogen chloride, hydrogen bromide, and hydrogen iodide are generated, so the use of a Brønsted base to capture the acids is effective. On the other hand, Y 1 Amination halogens, Y 1 When using alkoxy compounds, amines and alcohols are produced as the aromatic electrophilic substitution reaction progresses, so in many cases, it is not necessary to use a Brønsted base. However, because the leaving ability of aminos and alkoxys is low, the use of a Lewis acid to promote their elimination is effective.

[0202] Furthermore, the polycyclic aromatic compounds of the present invention also include compounds in which at least some hydrogen atoms are substituted with deuterium or cyano compounds, and compounds in which they are substituted with halogens such as fluorine or chlorine. Such compounds can be synthesized in the same manner as described above by using raw materials in which the desired positions have been deuterated, cyanated, fluorinated, or chlorinated.

[0203] <2. Organic Devices> The polycyclic aromatic compounds of the present invention can be used as materials for organic devices. Examples of organic devices include organic field-light-emitting devices, organic field-effect transistors, and organic thin-film solar cells.

[0204] The polycyclic aromatic compounds and their polymers according to the present invention can be used as materials for organic devices. Examples of organic devices include organic field-light-emitting devices, organic field-effect transistors, and organic thin-film solar cells, but organic field-light-emitting devices are preferred. The polycyclic aromatic compounds and their polymers according to the present invention are preferably organic field-light-emitting materials, more preferably materials for light-emitting layers (light-emitting materials), and most preferably dopant materials for light-emitting layers.

[0205] <2-1. Organic electroluminescent element> <2-1-1. Structure of an organic electroluminescent element> Figure 1 is a schematic cross-sectional view showing an example of an organic EL element. The organic EL element 100 shown in Figure 1 comprises a substrate 101, an anode 102 provided on the substrate 101, a hole injection layer 103 provided on the anode 102, a hole transport layer 104 provided on the hole injection layer 103, a light-emitting layer 105 provided on the hole transport layer 104, an electron transport layer 106 provided on the light-emitting layer 105, an electron injection layer 107 provided on the electron transport layer 106, and a cathode 108 provided on the electron injection layer 107.

[0206] The organic EL element 100 may also be configured by reversing the manufacturing order, for example, by having a substrate 101, a cathode 108 provided on the substrate 101, an electron injection layer 107 provided on the cathode 108, an electron transport layer 106 provided on the electron injection layer 107, an emissive layer 105 provided on the electron transport layer 106, a hole transport layer 104 provided on the emissive layer 105, a hole injection layer 103 provided on the hole transport layer 104, and an anode 102 provided on the hole injection layer 103.

[0207] Not all of the above layers are necessarily required; the minimum configuration unit consists of an anode 102, a light-emitting layer 105, and a cathode 108, and 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 above layers may consist of a single layer or multiple layers.

[0208] In addition to the above-mentioned "substrate / anode / hole injection layer / hole transport layer / emissive layer / electron transport layer / electron injection layer / cathode" configurations, other configurations of layers constituting an organic EL element include "substrate / anode / hole transport layer / emissive layer / electron transport layer / electron injection layer / cathode", "substrate / anode / hole injection layer / emissive layer / electron transport layer / electron injection layer / cathode", "substrate / anode / hole injection layer / hole transport layer / emissive layer / electron injection layer / cathode", and "substrate / anode / hole injection layer / hole transport layer / emissive layer / electron transport The configuration may also be "transport layer / cathode", "substrate / anodode / emissive layer / electron transport layer / electron injection layer / cathode", "substrate / anodode / hole transport layer / emissive layer / electron injection layer / cathode", "substrate / anodode / hole transport layer / emissive layer / electron transport layer / cathode", "substrate / anodode / hole injection layer / emissive layer / electron injection layer / cathode", "substrate / anodode / hole injection layer / emissive layer / electron transport layer / cathode", "substrate / anodode / emissive layer / electron transport layer / cathode", or "substrate / anodode / emissive layer / electron injection layer / cathode".

[0209] <2-1-2. Light-emitting layer in organic electroluminescent devices> The polycyclic aromatic compounds of the present invention are preferably used as materials for forming one or more organic layers in an organic electroluminescent device, and more preferably as materials for forming a light-emitting layer. The light-emitting layer 105 is a layer that emits light by recombining holes injected from the anode 102 and electrons injected from the cathode 108 between electrodes to which an electric field is applied. The material for forming the light-emitting layer 105 can be any compound that emits light when excited by the recombination of holes and electrons (luminescent compound), and it is preferable that it can form a stable thin film shape and exhibits strong luminescence (fluorescence) efficiency in the solid state. The polycyclic aromatic compounds of the present invention can be used as materials for the light-emitting layer, may be used as dopant materials, or may be used as host materials, but it is preferable to use them as materials for the light-emitting layer, and more preferably as dopant materials.

[0210] While there are instances where assisting dopants and emitting dopants are used in combination as dopants, in this specification, when simply referred to as "dopant," it refers to a luminescent dopant used alone.

[0211] The light-emitting layer may consist of a single layer or multiple layers, each formed from a light-emitting layer material (host material, dopant material). The host material and dopant material may each be of one type or a combination of multiple types. The dopant material may be contained throughout the host material or partially contained within it. As for the doping method, it can be formed by co-deposition with the host material, but it may also be mixed with the host material beforehand and then deposited simultaneously.

[0212] <Dopant Materials> The polycyclic aromatic compounds of the present invention can be preferably used as dopant materials. Examples of dopant materials other than the polycyclic aromatic compounds of the present invention are shown below. It is also preferable to use the following dopant materials in combination with the polycyclic aromatic compounds of the present invention. In the following structural formulas, "Me" represents methyl, "tBu" represents t-butyl, and "D" represents deuterium.

[0213] [ka]

[0214] [ka]

[0215] [ka]

[0216] [ka]

[0217] The amount of host material used varies depending on the type of host material and should be determined according to the characteristics of that host material. The guideline for the amount of host material used is preferably 50 to 99.999% by mass of the total material for the light-emitting layer, more preferably 80 to 99.95% by mass, and even more preferably 90 to 99.9% by mass.

[0218] The amount of dopant material used varies depending on the type of dopant material and should be determined according to the characteristics of that dopant material. A guideline for the amount of dopant used is preferably 0.001 to 50% by mass of the total material for the light-emitting layer, more preferably 0.05 to 20% by mass, and even more preferably 0.1 to 10% by mass. Within this range, for example, it is preferable in that it can prevent density quenching.

[0219] <Host Materials> Examples of host materials include condensed ring derivatives such as anthracene, pyrene, dibenzochrycene, or fluorene, which have been known as luminescent materials for some time; bisstyryl derivatives such as bisstyrylanthracene derivatives and distyrylbenzene derivatives; tetraphenylbutadiene derivatives; cyclopentadiene derivatives; fluorene derivatives; and benzofluorene derivatives.

[0220] Furthermore, as the host material, for example, a compound represented by any of the following formulas (H1), (H2), and (H3) can be used. [ka]

[0221] In formulas (H1), (H2), and (H3), L 1The compounds are arylenes having 6 to 24 carbon atoms, heteroarylenes having 2 to 24 carbon atoms, heteroarylene-arylenes having 6 to 24 carbon atoms, and arylene-heteroarylene-arylenes having 6 to 24 carbon atoms, with arylenes having 6 to 16 carbon atoms being preferred, arylenes having 6 to 12 carbon atoms being more preferred, and arylenes having 6 to 10 carbon atoms being particularly preferred. Specifically, examples include divalent groups such as benzene rings, biphenyl rings, terphenyl rings, and fluorene rings. As for heteroarylenes, heteroarylenes having 2 to 24 carbon atoms are preferred, heteroarylenes having 2 to 20 carbon atoms are more preferred, heteroarylenes having 2 to 15 carbon atoms are even more preferred, and heteroarylenes having 2 to 10 carbon atoms are particularly preferred. Specifically, pyrrole ring, oxazole ring, isoxazole ring, thiazole ring, isothiazole ring, imidazole ring, oxadiazole ring, thiadiazole ring, triazole ring, tetrazole ring, pyrazole ring, pyridine ring, pyrimidine ring, pyridazine ring, pyrazine ring, triazine ring, indole ring, isoindole ring, 1H-indazole ring, and Examples of divalent groups include the nzoimidazole ring, benzoxazole ring, benzothiazole ring, 1H-benzotriazole ring, quinoline ring, isoquinoline ring, sinnoline ring, quinazoline ring, quinoxaline ring, phthalazine ring, naphthyridine ring, purine ring, pteridine ring, carbazole ring, acridine ring, phenoxatiin ring, phenoxazine ring, phenothiazine ring, phenazine ring, indoridine ring, furan ring, benzofuran ring, isobenzofuran ring, dibenzofuran ring, thiophene ring, benzothiophene ring, dibenzothiophene ring, furazan ring, oxadiazole ring, and thianthlene ring. At least one hydrogen atom in each of the compounds represented by the above formulas may be substituted with an alkyl, cyano, halogen, or deuterium atom having 1 to 6 carbon atoms.

[0222] Preferred specific examples include compounds represented by any of the structural formulas listed below. In the structural formulas listed below, at least one hydrogen atom may be substituted with a halogen, cyano, a C1-C4 alkyl group (e.g., methyl or t-butyl), phenyl, or naphthyl.

[0223] [ka]

[0224] [ka]

[0225] [ka]

[0226] [ka]

[0227] <Anthracene compounds> Examples of anthracene compounds that can serve as hosts include the compound represented by formula (3-H) and the compound represented by formula (3-H2). [ka]

[0228] In formula (3-H), X and Ar 4 Each is independently hydrogen, a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted diarylamino, an optionally substituted diheteroarylamino, a substituted or unsubstituted arylheteroarylamino, a substituted or unsubstituted alkyl, an optionally substituted cycloalkyl, a substituted or unsubstituted alkenyl, a substituted or unsubstituted alkoxy, a substituted or unsubstituted aryloxy, a substituted or unsubstituted arylthio, or a substituted silyl, and all X and Ar 4 They cannot become hydrogen at the same time. In the compound represented by formula (3-H), at least one hydrogen atom is substituted with a halogen, cyano, deuterium, or an optionally substituted heteroaryl, or is unsubstituted.

[0229] Furthermore, a polymer (preferably a dimer) may be formed using the structure represented by formula (3-H) as the unit structure. In this case, for example, the unit structures represented by formula (3-H) may be bonded together via X, and X may be a single bond, arylene (phenylene, biphenylene, naphthylene, etc.), and heteroarylene (pyridine ring, dibenzofuran ring, dibenzothiophene ring, carbazole ring, benzocarbazole ring, and phenyl-substituted carbazole ring, etc., which are groups having a divalent bond value).

[0230] Details of each group in the compound represented by formula (3-H) can be found by referring to the explanation in formula (1) above, and will be further explained in the section on preferred embodiments below.

[0231] Preferred embodiments of the above anthracene compound are described below. The definitions of the symbols in the following structures are the same as those described above. [ka]

[0232] In formula (3-H), each X is independently a group represented by formula (3-X1), formula (3-X2), or formula (3-X3), and the groups represented by formula (3-X1), formula (3-X2), or formula (3-X3) bond to the anthracene ring of formula (3-H) at *. Preferably, two Xs do not simultaneously become the group represented by formula (3-X3). More preferably, two Xs do not simultaneously become the group represented by formula (3-X2).

[0233] Furthermore, a polymer (preferably a dimer) may be formed using the structure represented by formula (3-H) as the unit structure. In this case, for example, the unit structures represented by formula (3-H) may be bonded together via X, and X may be a single bond, arylene (phenylene, biphenylene, naphthylene, etc.), and heteroarylene (pyridine ring, dibenzofuran ring, dibenzothiophene ring, carbazole ring, benzocarbazole ring, and phenyl-substituted carbazole ring, etc., which are groups having a divalent bond value).

[0234] The naphthylene moieties in formulas (3-X1) and (3-X2) may be condensed with a single benzene ring. The resulting structure is as follows: [ka]

[0235] Ar 1 and Ar 2 Each of these is independently hydrogen, phenyl, biphenylyl, terphenylyl, quaterphenylyl, naphthyl, phenanthryl, fluorenyl, benzofluorenyl, crisenyl, triphenylenyl, pyrenyl, or a group represented by formula (A) (including carbazolyl, benzocarbazolyl, and phenyl-substituted carbazolyl). 1 or Ar 2 If the group is represented by formula (A), then the group represented by formula (A) is bonded to the naphthalene ring in formula (3-X1) or formula (3-X2) at its *.

[0236] Ar 3 This refers to phenyl, biphenylyl, terphenylyl, quaterphenylyl, naphthyl, phenanthryl, fluorenyl, benzofluorenyl, crisenyl, triphenylenyl, pyrenyl, or a group represented by formula (A) (including carbazolyl, benzocarbazolyl, and phenyl-substituted carbazolyl). Note that Ar 3 If the group is represented by formula (A), then the group represented by formula (A) bonds with the single bond represented by the line in formula (3-X3) at its *. That is, the anthracene ring of formula (3-H) and the group represented by formula (A) bond directly.

[0237] Also, Ar 3 It may have substituents, Ar 3At least one hydrogen in may be further substituted with an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, a phenyl group, a biphenylyl group, a terphenylyl group, a naphthyl group, a phenanthryl group, a fluorenyl group, a crisenyl group, a triphenylenyl group, a pyrenyl group, or a group represented by formula (A) (including carbazolyl and phenyl-substituted carbazolyl groups). Note that Ar 3 If the substituent on is the group represented by formula (A), then the group represented by formula (A) is the Ar in formula (3-X3) in its * 3 It combines with it.

[0238] Ar 4 These are silyls that are independently substituted with hydrogen, phenyl, biphenylyl, terphenylyl, naphthyl, or C1-C4 alkyl (methyl, ethyl, t-butyl, etc.) and / or C5-C10 cycloalkyl.

[0239] Examples of alkyl groups with 1 to 4 carbon atoms that can substitute for silyls include methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, t-butyl, and cyclobutyl, with each of the three hydrogen atoms in the silyl molecule being independently substituted by one of these alkyl groups.

[0240] Specific examples of "silyls substituted with alkyl groups having 1 to 4 carbon atoms" include trimethylsilyl, triethylsilyl, tripropylsilyl, triisopropylsilyl, tributylsilyl, trisec-butylsilyl, trit-butylsilyl, ethyldimethylsilyl, propyldimethylsilyl, isopropyldimethylsilyl, butyldimethylsilyl, sec-butyldimethylsilyl, t-butyldimethylsilyl, methyldiethylsilyl, propyldiethylsilyl, isopropyldiethylsilyl, butyldiethylsilyl, sec-butyldiethylsilyl, t-butyldiethylsilyl, methyldipropylsilyl, ethyldipropylsilyl, butyldipropylsilyl, sec-butyldipropylsilyl, t-butyldipropylsilyl, methyldiisopropylsilyl, ethyldiisopropylsilyl, butyldiisopropylsilyl, sec-butyldiisopropylsilyl, and t-butyldiisopropylsilyl.

[0241] Examples of cycloalkyl groups with 5 to 10 carbon atoms that can substitute for silyl include cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, norborneyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.0]pentyl, bicyclo[2.1.1]hexyl, bicyclo[3.1.0]hexyl, bicyclo[2.2.1]heptyl, bicyclo[2.2.2]octyl, adamantyl, decahydronaphthalenyl, and decahydroazlenyl, where the three hydrogen atoms in the silyl are each independently substituted by one of these cycloalkyl groups.

[0242] Specific examples of "silyls substituted with cycloalkyl groups having 5 to 10 carbon atoms" include tricyclopentylsilyl and tricyclohexylsilyl.

[0243] Substituted silyls include dialkylcycloalkylsilyls, which are substituted with two alkyl groups and one cycloalkyl group, and alkyldicycloalkylsilyls, which are substituted with one alkyl group and two cycloalkyl groups. The groups mentioned above are specific examples of the alkyl and cycloalkyl groups to be substituted.

[0244] Furthermore, the hydrogen atoms in the chemical structure of the anthracene compound represented by formula (3-H) may be substituted with the group represented by formula (A). When substituted with the group represented by formula (A), the group represented by formula (A) substitutes for at least one hydrogen atom in the compound represented by formula (3-H) at that *.

[0245] The group represented by formula (A) is one of the substituents that the anthracene compound represented by formula (3-H) may have. [ka]

[0246] In equation (A), Y is -O-, -S-, or >NR 29 And R 21 ~R 28 Each is independently hydrogen, an optionally substituted alkyl, an optionally substituted cycloalkyl, an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted alkoxy, an optionally substituted aryloxy, an optionally substituted arylthio, a trialkylsilyl, a tricycloalkylsilyl, a dialkylcycloalkylsilyl, an alkyldicycloalkylsilyl, an optionally substituted amino, a halogen, a hydroxyl, or a cyano, and R 21 ~R 28 Among these, adjacent groups may be bonded to each other to form a hydrocarbon ring, an aryl ring, or a heteroaryl ring, R 29 is hydrogen or an aryl that may be substituted. In equation (A), Y is preferably -O-.

[0247] R 21 ~R 28In the "alkyl which may be substituted" part, the "alkyl" can be either linear or branched, for example, a linear alkyl having 1 to 24 carbon atoms or a branched alkyl having 3 to 24 carbon atoms. A alkyl having 1 to 18 carbon atoms (a branched alkyl having 3 to 18 carbon atoms) is preferred, a alkyl having 1 to 12 carbon atoms (a branched alkyl having 3 to 12 carbon atoms) is more preferred, a alkyl having 1 to 6 carbon atoms (a branched alkyl having 3 to 6 carbon atoms) is even more preferred, and a alkyl having 1 to 4 carbon atoms (a branched alkyl having 3 to 4 carbon atoms) is particularly preferred.

[0248] Specific examples of "alkyl" include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl, n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, t-octyl, 1-methylheptyl, Examples include 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 2,6-dimethyl-4-heptyl, 3,5,5-trimethylhexyl, n-decyl, n-undecyl, 1-methyldecyl, n-dodecyl, n-tridecyl, 1-hexylheptyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, and n-eicosyl.

[0249] R 21 ~R 28 Examples of "cycloalkyl" in "may be substituted" include cycloalkyls with 3 to 24 carbon atoms, cycloalkyls with 3 to 20 carbon atoms, cycloalkyls with 3 to 16 carbon atoms, cycloalkyls with 3 to 14 carbon atoms, cycloalkyls with 5 to 10 carbon atoms, cycloalkyls with 5 to 8 carbon atoms, cycloalkyls with 5 to 6 carbon atoms, and cycloalkyls with 5 carbon atoms.

[0250] Specific examples of "cycloalkyl" include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, and their alkyl (especially methyl) substituted derivatives having 1 to 4 carbon atoms, as well as norbornel, bicyclo[1.1.0]butyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.0]pentyl, bicyclo[2.1.1]hexyl, bicyclo[3.1.0]hexyl, bicyclo[2.2.1]heptyl, bicyclo[2.2.2]octyl, adamantyl, diamantyl, decahydronaphthalenyl, and decahydroazlenyl.

[0251] R 21 ~R 28 In the "aryl that may be substituted" in this expression, examples of "aryl" include aryls having 6 to 30 carbon atoms, preferably aryls having 6 to 16 carbon atoms, more preferably aryls having 6 to 12 carbon atoms, and particularly preferably aryls having 6 to 10 carbon atoms.

[0252] Specific examples of "aryl" include monocyclic phenyl, bicyclic biphenylyl, condensed bicyclic naphthyl, tricyclic terpheniryl (m-terpheniryl, o-terpheniryl, p-terpheniryl), condensed tricyclic acenaphthirenyl, fluorenyl, phenalenyl, phenantrenyl, tetracyclic triphenylenyl, pyrenyl, naphthacenyl, and condensed pentacyclic perilenyl, pentacenyl, etc.

[0253] R 21 ~R 28 In the "heteroaryl that may be substituted" in this context, examples of "heteroaryl" include heteroaryls having 2 to 30 carbon atoms, with heteroaryls having 2 to 25 carbon atoms being preferred, heteroaryls having 2 to 20 carbon atoms being more preferred, heteroaryls having 2 to 15 carbon atoms being even more preferred, and heteroaryls having 2 to 10 carbon atoms being particularly preferred. Examples of heteroaryls include heterocycles containing 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen in addition to carbon as ring constituent atoms.

[0254] Specific examples of "heteroaryls" include pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, pyrazolyl, pyridyl, pyrimidinyl, pyridadinyl, pyrazinyl, triazinyl, indolyl, isoindolyl, 1H-indazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolyl, isoxyl Examples include noryl, cinnoryl, quinazolyl, quinoxalinyl, phthalazinyl, naphthilidinyl, prinyl, pteridinyl, carbazolyl, acridinyl, phenoxathiinyl, phenoxadinyl, phenothiazinyl, phenadinyl, indolidinyl, furyl, benzofuranil, isobenzofuranil, dibenzofuranil, thienyl, benzo[b]thienyl, dibenzothienyl, flazanil, thiantrenil, naphtobenzofuranil, and naphtobenzothienyl.

[0255] R 21 ~R 28 In the "alkoxy that may be substituted" in the formula, examples of "alkoxy" include linear alkoxys with 1 to 24 carbon atoms or branched alkoxys with 3 to 24 carbon atoms. Alkoxys with 1 to 18 carbon atoms (branched alkoxys with 3 to 18 carbon atoms) are preferred, alkoxys with 1 to 12 carbon atoms (branched alkoxys with 3 to 12 carbon atoms) are more preferred, alkoxys with 1 to 6 carbon atoms (branched alkoxys with 3 to 6 carbon atoms) are even more preferred, and alkoxys with 1 to 4 carbon atoms (branched alkoxys with 3 to 4 carbon atoms) are particularly preferred.

[0256] Specific examples of "alkoxys" include methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, s-butoxy, t-butoxy, pentyloxy, hexyloxy, heptyloxy, and octyloxy.

[0257] R 21 ~R 28In the context of "arlyoxy which may be substituted," the "aryloxy" refers to a group in which the hydrogen of the -OH group is substituted with an aryl group, and this aryl is the same as the R mentioned above. 21 ~R 28 We can cite the base described as "aryl" in this context.

[0258] R 21 ~R 28 In the context of "arylthio which may be substituted", the "arylthio" refers to a group in which the hydrogen of the -SH group is substituted with an aryl group, and this aryl is the same as the R mentioned above. 21 ~R 28 We can cite the base described as "aryl" in this context.

[0259] R 21 ~R 28 In this context, "trialkylsilyl" refers to a group in which the three hydrogen atoms of the silyl group are each independently substituted with alkyl groups, and this alkyl group is the R mentioned above. 21 ~R 28 The group described as "alkyl" in the above can be referenced. Preferred alkyl groups for substitution are alkyl groups having 1 to 4 carbon atoms, specifically including methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, t-butyl, and cyclobutyl.

[0260] Specific examples of "trialkylsilyls" include trimethylsilyl, triethylsilyl, tripropylsilyl, triisopropylsilyl, tributylsilyl, trisec-butylsilyl, trit-butylsilyl, ethyldimethylsilyl, propyldimethylsilyl, isopropyldimethylsilyl, butyldimethylsilyl, sec-butyldimethylsilyl, t-butyldimethylsilyl, methyldiethylsilyl, propyldiethylsilyl, isopropyldiethylsilyl, butyldiethylsilyl, sec-butyldiethylsilyl, t-butyldiethylsilyl, methyldipropylsilyl, ethyldipropylsilyl, butyldipropylsilyl, sec-butyldipropylsilyl, t-butyldipropylsilyl, methyldiisopropylsilyl, ethyldiisopropylsilyl, butyldiisopropylsilyl, sec-butyldiisopropylsilyl, and t-butyldiisopropylsilyl.

[0261] R 21 ~R 28 In this context, "tricycloalkylsilyl" refers to a group in which the three hydrogen atoms of the silyl group are each independently substituted with a cycloalkyl group, and this cycloalkyl group is the R mentioned above. 21 ~R 28 The group described as "cycloalkyl" in the above can be cited. Preferred cycloalkyls for substitution are cycloalkyls having 5 to 10 carbon atoms, specifically including cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.0]pentyl, bicyclo[2.1.1]hexyl, bicyclo[3.1.0]hexyl, bicyclo[2.2.1]heptyl, bicyclo[2.2.2]octyl, adamantyl, decahydronaphthalenyl, decahydroazlenyl, and the like.

[0262] Specific examples of "tricycloalkylsilyls" include tricyclopentylsilyl and tricyclohexylsilyl.

[0263] Specific examples of dialkylcycloalkylsilyls substituted with two alkyl groups and one cycloalkyl group, and alkyldicycloalkylsilyls substituted with one alkyl group and two cycloalkyl groups, include silyls substituted with groups selected from the specific alkyl and cycloalkyl groups mentioned above.

[0264] R 21 ~R 28 In the context of "aminos that may be substituted," examples of "substituted aminos" include aminos in which two hydrogens are substituted with aryl or heteroaryl groups. Aminos in which two hydrogens are substituted with aryl groups are diaryl-substituted aminos (the two aryls may not be bonded to each other or may be bonded via a linking group), aminos in which two hydrogens are substituted with heteroaryl groups are diheteroaryl-substituted aminos, and aminos in which two hydrogens are substituted with aryl and heteroaryl groups are arylheteroaryl-substituted aminos. These aryl and heteroaryl groups are the same as those mentioned above in R 21 ~R 28 The bases described as "aryl" and "heteroaryl" in the above can be cited.

[0265] Specific examples of "substituted amino acids" include diphenylamino, dinaphthylamino, phenylnaphthylamino, dipyridylamino, phenylpyridylamino, and naphthylpyridylamino.

[0266] R 21 ~R 28 Examples of "halogens" in this context include fluorine, chlorine, bromine, and iodine.

[0267] R 21 ~R 28 Some of the groups described above may be substituted as described above, and examples of substituents in this case include alkyl, cycloalkyl, aryl, or heteroaryl groups. These alkyl, cycloalkyl, aryl, or heteroaryl groups are the R groups described above. 21 ~R 28The groups described as "alkyl," "cycloalkyl," "aryl," or "heteroaryl" in the above context can be referenced.

[0268] Y as ">NR" 29 R in " 29 is hydrogen or an aryl that may be substituted, and this aryl is as described above R 21 ~R 28 The group described as "aryl" in the above can be cited, and its substituent is R 21 ~R 28 The groups described as substituents on can be cited.

[0269] R 21 ~R 28 Adjacent groups may bond to each other to form a hydrocarbon ring, an aryl ring, or a heteroaryl ring. The group that does not form a ring is represented by formula (A-1) below, while the group that does form a ring is represented by formulas (A-2) to (A-14) below, for example. At least one hydrogen in any of the groups represented by formulas (A-1) to (A-14) may be substituted with alkyl, cycloalkyl, aryl, heteroaryl, alkoxy, aryloxy, arylthio, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, alkyldicycloalkylsilyl, diaryl (the two aryls may not be bonded to each other or may be bonded via a linking group)-substituted amino, diheteroaryl-substituted amino, arylheteroaryl-substituted amino, halogen, hydroxyl, or cyano.

[0270] [ka]

[0271] Examples of rings formed by the bonding of adjacent groups include the cyclohexane ring in the case of hydrocarbon rings, and the aforementioned R in the case of aryl rings and heteroaryl rings. 21 ~R 28Examples include the ring structures described as "aryl" and "heteroaryl" in formula (A-1), where these rings are formed to condense with one or two benzene rings.

[0272] The group represented by formula (A) is a group obtained by removing one hydrogen atom from any position in formula (A), where * indicates the position. In other words, the group represented by formula (A) may have any position as its bonded position. For example, either carbon atom on the two benzene rings in the structure of formula (A), or R in the structure of formula (A). 21 ~R 28 Among them, any atom on a ring formed by the bonding of adjacent groups to each other, or as Y in the structure of formula (A), ">NR 29 R in " 29 Any position in the middle, or ">NR 29 N(R) in " 29 It can be a group that directly bonds with (which forms a bonding site). The same applies to the group represented by any of formulas (A-1) to (A-14).

[0273] Examples of the group represented by formula (A) include any of the groups represented by formulas (A-1) to (A-14), with groups represented by any of formulas (A-1) to (A-5) and formulas (A-12) to (A-14) being preferred, groups represented by any of formulas (A-1) to (A-4) being more preferred, groups represented by any of formulas (A-1), (A-3), and (A-4) being even more preferred, and the group represented by formula (A-1) being particularly preferred.

[0274] Examples of groups represented by formula (A) include the following. The definitions of Y and * in the formula are the same as above. [ka]

[0275] [ka]

[0276] In the compound represented by formula (3-H), the group represented by formula (A) is 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 A form in which it is combined with one of the following is preferred.

[0277] Furthermore, all or part of the hydrogen atoms in the chemical structure of the anthracene compound represented by formula (3-H) may be deuterium.

[0278] The anthracene compound used as a host may be, for example, a compound represented by the following formula (3-H2). [ka]

[0279] In formula (3-H2), Ar c R is an optionally substituted aryl or optionally substituted heteroaryl, c is hydrogen, alkyl, or cycloalkyl, and Ar 11 Ar 12 Ar 13 Ar 14 Ar 15 Ar 16 Ar 17 , and Ar 18 Each of these is independently a hydrogen, an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted diarylamino, an optionally substituted diheteroarylamino, an optionally substituted arylheteroarylamino, an optionally substituted alkyl, an optionally substituted cycloalkyl, an optionally substituted alkenyl, an optionally substituted alkoxy, an optionally substituted aryloxy, an optionally substituted arylthio, or an optionally substituted silyl, wherein at least one hydrogen in the compound represented by formula (1) may be substituted with a halogen, a cyano, or a deuterium.

[0280] The definitions of "optionally substituted aryl," "optionally substituted heteroaryl," "optionally substituted diarylamino," "optionally substituted diheteroarylamino," "optionally substituted arylheteroarylamino," "optionally substituted alkyl," "optionally substituted cycloalkyl," "optionally substituted alkenyl," "optionally substituted alkoxy," "optionally substituted aryloxy," "optionally substituted arylthio," or "optionally substituted silyl" in formula (3-H) are the same as those in formula (3-H) above, and the explanation in formula (1) can be referenced.

[0281] The "aryl group that may be substituted" is preferably a group represented by any of the following formulas (3-H2-X1) to (3-H2-X8).

[0282] [ka]

[0283] In equations (3-H2-X1) to (3-H2-X8), * indicates the bond position. In equations (3-H2-X1) to (3-H2-X3), Ar 21 Ar 22 , and Ar 23 Each of these is independently hydrogen, phenyl, biphenylyl, terphenylyl, quaterphenylyl, naphthyl, phenanthryl, fluorenyl, benzofluorenyl, crisenyl, triphenylenyl, pyrenyl, anthracenyl, or a group represented by formula (A). In the explanation of formula (3-H2), the group represented by formula (A) is the same as that explained for the anthracene compound represented by formula (3-H).

[0284] In equations (3-H2-X4) to (3-H2-X8), Ar 24 Ar 25 Ar 26 Ar 27 Ar 28 Ar 29 , and Ar30 Each of these is independently hydrogen, phenyl, biphenylyl, terphenylyl, naphthyl, phenanthryl, fluorenyl, crisenyl, triphenylenyl, pyrenyl, or a group represented by formula (A). In addition, one or more hydrogens in each of the groups represented by formulas (3-H2-X1) to (3-H2-X8) may be substituted with an alkyl group having 1 to 6 carbon atoms (preferably methyl or t-butyl).

[0285] Furthermore, preferred examples of "optionally substituted aryls" include terpheniryl (in particular m-terphenyl-5'-yl), which may be substituted with one or more substituents selected from the group consisting of phenyl, biphenylyl, terphenylyl, naphthyl, phenanthryl, fluorenyl, crisenyl, triphenylenyl, pyrenyl, and the group represented by formula (A).

[0286] Examples of "optionally substituted heteroaryls" include the group represented by formula (A). Other specific examples of "optionally substituted aryls" and "optionally substituted heteroaryls" include dibenzofuryl, naphthobenzofuryl, and phenyl-substituted dibenzofuryl.

[0287] At least one hydrogen atom in the compound represented by formula (1) may be substituted with a halogen, cyano, or deuterium. Examples of halogens in this case include fluorine, chlorine, bromine, and iodine. Compounds in which all hydrogen atoms in the compound represented by formula (3-H2) are substituted with deuterium are particularly preferred.

[0288] In formula (3-H2), R c The element is hydrogen, alkyl, or cycloalkyl, preferably hydrogen, methyl, or t-butyl, and more preferably hydrogen. In formula (3-H2), Ar 11 ~Ar 18Preferably, at least two of the substituents are optionally substituted aryl or optionally substituted heteroaryl. That is, the anthracene compound represented by formula (3-H2) preferably has a structure in which at least three substituents selected from the group consisting of optionally substituted aryl and optionally substituted heteroaryl are bonded to the anthracene ring.

[0289] Anthracene compounds represented by formula (3-H2) are Ar 11 ~Ar 18 It is more preferable that two of the substituents are optionally substituted aryl or optionally substituted heteroaryl, and the other six substituents are hydrogen, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted alkenyl, or optionally substituted alkoxy. In other words, it is more preferable that the anthracene compound represented by formula (3-H2) has a structure in which three substituents selected from the group consisting of optionally substituted aryl and optionally substituted heteroaryl are bonded to the anthracene ring.

[0290] Anthracene compounds represented by formula (3-H2) are Ar 11 ~Ar 18 It is more preferable that any two of the elements are optionally substituted aryl or optionally substituted heteroaryl, and the other six are hydrogen, methyl, or t-butyl.

[0291] Furthermore, in equation (3-H2), R c is hydrogen and Ar 11 ~Ar 18 It is preferable that any six of them are hydrogen.

[0292] The anthracene compound represented by formula (3-H2) is preferably an anthracene compound represented by the following formulas: (3-H2-A), (3-H2-B), (3-H2-C), (3-H2-D), or (3-H2-E). [ka]

[0293] In formulas (3-H2-A), (3-H2-B), (3-H2-C), (3-H2-D), or (3-H2-E), Ar c ', Ar 11 ', Ar 12 ', Ar 13 ', Ar 14 ', Ar 15 ', Ar 17 ', and Ar 18 Each of the following groups is independently phenyl, biphenylyl, terphenylyl, quaterphenylyl, naphthyl, phenanthryl, fluorenyl, benzofluorenyl, crisenyl, triphenylenyl, pyrenyl, or a group represented by formula (A), and at least one hydrogen in these groups may be substituted with phenyl, biphenylyl, terphenylyl, quaterphenylyl, naphthyl, phenanthryl, fluorenyl, benzofluorenyl, crisenyl, triphenylenyl, pyrenyl, or a group represented by formula (A). Here, when both the hydrogen of the methylene group in fluorenyl and benzofluorenyl are substituted with phenyl, these phenyl groups may be bonded to each other by single bonds. c ', Ar 11 ', Ar 12 ', Ar 13 ', Ar 14 ', Ar 15 ', Ar 17 ', and Ar 18 The carbon atoms of the anthracene ring that are not bonded may have methyl or t-butyl atoms bonded to them instead of hydrogen atoms.

[0294] Ar c ', Ar 11 ', Ar 12 ', Ar 13 ', Ar 14 ', Ar 15 ', Ar 17 ', and Ar 18 When each of these is a substituted or unsubstituted phenyl or a substituted or unsubstituted naphthyl, it is preferable that the group is represented by any of the above formulas (3-H2-X1) to (3-H2-X7).

[0295] Ar c ', Ar 11 ', Ar 12 ', Ar 13 ', Ar 14 ', Ar 15 ', Ar 17 ', and Ar 18 Each of the groups is more preferably independently phenyl, biphenylyl (especially biphenyl-2-yl or biphenyl-4-yl), terphenylyl (especially m-terphenyl-5'-yl), naphthyl, phenanthryl, fluorenyl, or any of the above formulas (A-1) to (A-4), in which case at least one hydrogen in these groups may be substituted with phenyl, biphenylyl, naphthyl, phenanthryl, fluorenyl, or any of the above formulas (A-1) to (A-4).

[0296] Furthermore, at least one hydrogen atom in the compounds represented by formulas (3-H2-A), (3-H2-B), (3-H2-C), (3-H2-D), or (3-H2-E) may be substituted with a halogen, cyano, or deuterium. The deuterated form is preferred, and a form in which the entire anthracene ring is deuterated, or a form in which all hydrogen atoms are deuterated, is preferred.

[0297] Particularly preferred anthracene compounds represented by the formula (3-H2) include the anthracene compounds represented by the following formula (3-H2-Aa). [ka]

[0298] In formula (3-H2-Aa), Ar c ', Ar 14 ', and Ar 15Each of the following groups is independently phenyl, biphenylyl, terphenylyl, naphthyl, phenanthryl, fluorenyl, benzofluorenyl, crisenyl, triphenylenyl, pyrenyl, or any of the above formulas (A-1) to (A-11), and at least one hydrogen in these groups may be substituted with phenyl, biphenylyl, terphenylyl, naphthyl, phenanthryl, fluorenyl, benzofluorenyl, crisenyl, triphenylenyl, pyrenyl, or any of the above formulas (A-1) to (A-11). Here, when both the hydrogen of the methylene group in fluorenyl and benzofluorenyl are substituted with phenyl, these phenyl groups may be bonded to each other by single bonds. Also, Ar c ', Ar 14 ', and Ar 15 Carbon atoms on an anthracene ring that are not bonded to a ' group may be substituted with methyl or t-butyl instead of hydrogen. At least one hydrogen in the compound represented by formula (3-H2-Aa) may be substituted with a halogen or cyano, and at least one hydrogen in the compound represented by formula (3-H2-Aa) may be substituted with deuterium.

[0299] In formula (3-H2-Aa), Ar c ', Ar 14 ', and Ar 15 Each of the groups is preferably independently phenyl, biphenylyl, terphenylyl, naphthyl, phenanthryl, fluorenyl, or any of the groups represented by formulas (A-1) to (A-4) above, and at least one hydrogen in these groups may be substituted with phenyl, naphthyl, phenanthryl, fluorenyl, or any of the groups represented by formulas (A-1) to (A-4).

[0300] In the compound represented by formula (3-H2-Aa), at least the carbon at position 10 of the anthracene ring (Ar cIt is preferable that the hydrogen bonded to the carbon atom to which the ' is attached (with the carbon atom at position 9) is substituted with deuterium. That is, the compound represented by formula (3-H2-Aa) is preferably the compound represented by the following formula (3-H2-Ab). In formula (3-H2-Ab), D is deuterium, and Ar c ', Ar 14 ', and Ar 15 ' is the same as the definition in formula (3-H2-Aa). In formula (3-H2-Ab), D indicates that at least this position is deuterium, and one or more of the other hydrogens in formula (3-H2-Ab) may also be deuterium, and it is also preferable that all of the hydrogens in formula (3-H2-Ab) are deuterium.

[0301] [ka]

[0302] Specific examples of anthracene compounds include, for example, the compounds represented by formulas (3-131-Y) to (3-182-Y), (3-183-N), (3-184-Y) to (3-284-Y), and (3-500) to (3-557), and (3-600) to (3-605), and (3-606-Y) to (3-626-Y). The hydrogen atoms in these formulas may be partially or entirely substituted with deuterium, but particularly preferred forms of deuterium substitution are listed individually. In the formulas, Y represents -O-, -S-, >NR. 29 (R 29 (This is the same definition as above) or >C(-R 30 )2(R 30 R may be either an aryl or alkyl group that is linked, 29 For example, phenyl, R 30 For example, methyl. The formula numbering is as follows: for example, if Y is O, formula (3-131-Y) becomes formula (3-131-O), and Y is -S- or >NR. 29 In these cases, the equations are (3-131-S) or (3-131-N), respectively.

[0303]

change

[0304]

change

[0305]

change

[0306]

change

[0307]

change

[0308]

change

[0309]

change

[0310]

change

[0311]

change

[0312]

change

[0313]

change

[0314] [ka]

[0315] [ka]

[0316] [ka]

[0317] [ka]

[0318] [ka]

[0319] [ka]

[0320] [ka]

[0321] [ka]

[0322] [ka] In the above formula, D is deuterium.

[0323] Among these compounds, formulas (3-131-Y)~(3-134-Y), formula (3-138-Y), formula (3-140-Y)~(3-143-Y), formula (3-150-Y), formula (3-153-Y)~(3-156-Y), formula (3-166-Y), formula (3-168-Y), formula (3-173-Y), formula (3-177-Y), formula (3-180-Y)~(3-183-N), formula (3-185-Y), formula (3-190-Y), formula (3-223-Y), formula (3-241- Compounds represented by formulas (Y), (3-250-Y), (3-252-Y) to (3-254-Y), (3-270-Y) to (3-284-Y), (3-501), (3-507), (3-508), (3-509), (3-513), (3-514), (3-519), (3-521), (3-538) to (3-547), or (3-600) to (3-605), and (3-606-Y) to (3-626-Y) are preferred. Furthermore, Y is -O- or >NR 29 It is preferable that it is -O-, and more preferably that it is deuterium-substituted. The deuterium substitution form is also preferred.

[0324] The above anthracene compounds include compounds having a reactive group at a desired position on the anthracene skeleton, and anthracene compounds represented by formula (3-H), where X and Ar 4 The compounds can be produced by applying Suzuki coupling, Negishi coupling, or other known coupling reactions, using compounds having reactive groups in substructures such as the structure of formula (A) as starting materials. Examples of reactive groups in these reactive compounds include halogens and boronic acids. For specific production methods, refer to the synthesis methods in paragraphs

[0089] to

[0175] of International Publication No. 2014 / 141725, for example.

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

[0326] In formula (4-H), R 1 From R 10 Each of these is independently a hydrogen, aryl, heteroaryl (the heteroaryl may be bonded to the fluorene skeleton in formula (4-H) via a linking group), diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkenyl, alkoxy, or aryloxy, and at least one hydrogen in these may be substituted with an aryl, heteroaryl, alkyl, or cycloalkyl, and R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 5 and R 6 , R 6 and R 7 , R 7 and R 8 or R 9 and R 10 Each of these may be independently bonded to form a fused ring or spiro ring, and at least one hydrogen in the formed ring may be substituted with an aryl, heteroaryl (the heteroaryl may be bonded to the formed ring via a linking group), diarylamino), diheteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkenyl, alkoxy, or aryloxy, and at least one hydrogen in these may be substituted with an aryl, heteroaryl, alkyl, or cycloalkyl, and at least one hydrogen in the compound represented by formula (4-H) may be substituted with a halogen, cyano, or deuterium.

[0327] For details of each group in the definition of formula (4-H), refer to the explanation for the polycyclic aromatic compound of formula (1) described above.

[0328] R 1 From R 10Examples of alkenyls include alkenyls having 2 to 30 carbon atoms, with alkenyls having 2 to 20 carbon atoms being preferred, alkenyls having 2 to 10 carbon atoms being more preferred, alkenyls having 2 to 6 carbon atoms being even more preferred, and alkenyls having 2 to 4 carbon atoms being particularly preferred. Preferred alkenyls are vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, or 5-hexenyl.

[0329] Furthermore, as specific examples of heteroaryls, monovalent groups can also be given, which are represented by removing any one hydrogen atom from the compounds of the following formulas: (4-Ar1), (4-Ar2), (4-Ar3), (4-Ar4), or (4-Ar5).

[0330] [ka]

[0331] In equations (4-Ar1) to (4-Ar5), Y 1 Each of these is independently O, S, or NR, where R is phenyl, biphenylyl, naphthyl, anthracenyl, or hydrogen, and at least one hydrogen in the structures of formulas (4-Ar1) to (4-Ar5) may be substituted with phenyl, biphenylyl, naphthyl, anthracenyl, phenantrenyl, methyl, ethyl, propyl, or butyl.

[0332] These heteroaryls may be bonded to the fluorene skeleton in formula (4-H) via linking groups. That is, the fluorene skeleton in formula (4-H) and the heteroaryls may not only be directly bonded, but may also be bonded to each other via linking groups. Examples of such linking groups include phenylene, biphenylene, naphthylene, anthracenylene, methylene, ethylene, -OCH2CH2-, -CH2CH2O-, or -OCH2CH2O-.

[0333] Also, R in equation (4-H) 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 5 and R 6 , R 6 and R 7 or R 7 and R 8 Each of them independently bonds to form a fused ring, R 9 and R 10 They may be bonded together to form a spiro ring. 1 From R 8 The condensed ring formed by this process is a ring that condenses with the benzene ring in formula (4-H), and is either an aliphatic or aromatic ring. Preferably, it is an aromatic ring, and examples of structures including the benzene ring in formula (4-H) include naphthalene rings and phenanthrene rings. 9 and R 10 The spiro ring formed by this process is a ring that spirobonds to the 5-membered ring in formula (4-H), and is either an aliphatic or aromatic ring. Preferably, it is an aromatic ring, such as a fluorene ring.

[0334] The compound represented by formula (4-H) is preferably a compound represented by the following formulas (4-H-1), (4-H-2), or (4-H-3), where in each case R in formula (4-H) 1 and R 2 A compound in which a benzene ring formed by the bonding of R is condensed, in formula (4-H). 3 and R 4 A compound in which a benzene ring formed by the bonding of R is condensed, in formula (4-H). 1 From R 8 It is a compound in which none of the following are bonded.

[0335] [ka]

[0336] R in equations (4-H-1), (4-H-2), and (4-H-3) 1 From R10 The definition of is the corresponding R in equation (4-H). 1 From R 10 This is the same as R in equations (4-H-1) and (4-H-2). 11 From R 14 The definition of R in equation (4-H) is also 1 From R 10 It is the same as this.

[0337] The compound represented by formula (4-H) is more preferably the compound represented by the following formulas (4-H-1A), (4-H-2A), or (4-H-3A), where R is present in formulas (4-H-1), (4-H-1), or (4-H-3), respectively. 9 and R 10 This is a compound in which a spirofluorene ring is formed by the bonding of two molecules.

[0338] [ka]

[0339] R in equations (4-H-1A), (4-H-2A), and (4-H-3A) 2 From R 7 The definition of corresponds to R in equations (4-1), (4-2), and (4-3). 2 From R 7 This is the same as R in equations (4-H-1A) and (4-H-2A). 11 From R 14 The definition of R in equations (4-1) and (4-2) is also 11 From R 14 It is the same as this.

[0340] Furthermore, in the compound represented by formula (4-H), all or part of the hydrogen atoms may be substituted with halogens, cyanosides, or deuterium.

[0341] A more specific example of a fluorene compound as a host in the present invention is the compound represented by the following structural formula. Note that "Me" indicates methyl. [ka]

[0342] <Dibenzocricene compounds> Dibenzochrysene compounds used as hosts are, for example, compounds represented by the following formula (5-H). [ka]

[0343] In formula (5-H), R 1 From R 16 Each of these is independently a hydrogen, aryl, heteroaryl (the heteroaryl may be bonded to the dibenzochrysene skeleton in formula (5-H) via a linking group), diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkenyl, alkoxy, or aryloxy, wherein at least one hydrogen in these may be substituted with an aryl, heteroaryl, alkyl, or cycloalkyl, and R 1 From R 16 Adjacent groups may bond to each other to form a fused ring, and at least one hydrogen in the formed ring may be substituted with an aryl, heteroaryl (the heteroaryl may be bonded to the formed ring via a linking group), diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkenyl, alkoxy, or aryloxy, and at least one hydrogen in these may be substituted with an aryl, heteroaryl, alkyl, or cycloalkyl, and at least one hydrogen in the compound represented by formula (5-H) may be substituted with a halogen, cyano, or deuterium.

[0344] For details of each group in the definition of formula (5-H), refer to the explanation for the polycyclic aromatic compound of formula (1) described above.

[0345] Examples of alkenyls in the definition of formula (5-H) include alkenyls having 2 to 30 carbon atoms, with alkenyls having 2 to 20 carbon atoms being preferred, alkenyls having 2 to 10 carbon atoms being more preferred, alkenyls having 2 to 6 carbon atoms being even more preferred, and alkenyls having 2 to 4 carbon atoms being particularly preferred. Preferred alkenyls are vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, or 5-hexenyl.

[0346] Furthermore, as specific examples of heteroaryls, monovalent groups can also be represented by removing any one hydrogen atom from the compounds of the following formulas: (5-Ar1), (5-Ar2), (5-Ar3), (5-Ar4), or (5-Ar5).

[0347] [ka]

[0348] In equations (5-Ar1) to (5-Ar5), Y 1 Each of these is independently O, S, or NR, where R is phenyl, biphenylyl, naphthyl, anthracenyl, or hydrogen, and at least one hydrogen in the structures of formulas (5-Ar1) to (5-Ar5) may be substituted with phenyl, biphenylyl, naphthyl, anthracenyl, phenantrenyl, methyl, ethyl, propyl, or butyl.

[0349] These heteroaryls may be bonded to the dibenzochrysene skeleton in formula (5-H) via a linking group. That is, the dibenzochrysene skeleton in formula (5-H) and the heteroaryls may not only be directly bonded, but may also be bonded to each other via a linking group. Examples of such linking groups include phenylene, biphenylene, naphthylene, anthracenylene, methylene, ethylene, -OCH2CH2-, -CH2CH2O-, or -OCH2CH2O-.

[0350] The compound represented by formula (5-H) is preferably R 1 , R 4 , R 5 , R 8 , R 9 , R 12 , R 13 and R 16 is hydrogen. In this case, R in equation (5-H) 2 , R 3 , R 6 , R 7 , R 10 , R 11 , R 14 and R 15 Preferably, each of these is independently hydrogen, phenyl, biphenylyl, naphthyl, anthracenyl, phenantrenyl, a monovalent group having the structure of formula (5-Ar1), formula (5-Ar2), formula (5-Ar3), formula (5-Ar4), or formula (5-Ar5) (the monovalent group having this structure may be bonded to the dibenzochrysene skeleton in formula (5-H) via phenylene, biphenylene, naphthylene, anthracenylene, methylene, ethylene, -OCH2CH2-, -CH2CH2O-, or -OCH2CH2O-), methyl, ethyl, propyl, or butyl.

[0351] The compound represented by formula (5-H) is more preferably R 1 , R 2 , R 4 , R 5 , R 7 , R 8 , R 9 , R 10 , R 12 , R 13 , R 15 and R 16 is hydrogen. In this case, R in equation (5-H) 3 , R 6 , R 11 and R 14At least one (preferably one or two, more preferably one) of the groups is a monovalent group having the structure of formula (5-Ar1), formula (5-Ar2), formula (5-Ar3), formula (5-Ar4), or formula (5-Ar5) via a single bond, phenylene, biphenylene, naphthylene, anthracenylene, methylene, ethylene, -OCH2CH2-, -CH2CH2O-, or -OCH2CH2O-, and the other groups (i.e., the positions other than those substituted by the monovalent group having the aforementioned structure) are hydrogen, phenyl, biphenylyl, naphthyl, anthracenyl, methyl, ethyl, propyl, or butyl, wherein at least one hydrogen in these groups may be substituted with phenyl, biphenylyl, naphthyl, anthracenyl, methyl, ethyl, propyl, or butyl.

[0352] Also, R in equation (5-H) 2 , R 3 , R 6 , R 7 , R 10 , R 11 , R 14 and R 15 If a monovalent group having a structure represented by formulas (5-Ar1) to (5-Ar5) is selected, then at least one hydrogen in that structure is R in formula (5-H). 1 From R 16 It may also bond with either of them to form a single bond.

[0353] A more specific example of a dibenzochrysene compound as a host in the present invention is the compound represented by the following structural formula. Note that "tBu" represents t-butyl. [ka]

[0354] [ka]

[0355] The above-mentioned materials for the light-emitting layer (host material and dopant material) can also be used as materials for the light-emitting layer as polymer compounds obtained by polymerizing reactive compounds in which reactive substituents are substituted as monomers, or as polymer crosslinks thereof, or as pendant-type polymer compounds obtained by reacting a main-chain polymer with the reactive compound, or as pendant-type polymer crosslinks thereof. In this case, the explanation for the polycyclic aromatic compound represented by formula (1) can be referred to for the reactive substituent.

[0356] <Emitting layer containing assisting dopant and emitting dopant> The light-emitting layer in an organic electroluminescent device may include a host compound as a first component, an assisting dopant (compound) as a second component, and an emitting dopant (compound) as a third component. The polycyclic aromatic compound of the present invention may also be used as the emitting dopant. A thermally activated delayed phosphor can be used as the assisting dopant (compound).

[0357] In the following explanation, an organic electroluminescent device that uses a thermally activated delayed phosphor as an assisting dopant may be referred to as a "TAF device" (TADF Assisting Fluorescence device). In a TAF device, the "host compound" refers to a compound whose lowest excitation singlet energy level, determined from the short-wavelength shoulder of the fluorescence spectrum peak, is higher than that of the thermally activated delayed phosphor as the second component and the emitting dopant as the third component.

[0358] A "thermally activated delayed phosphor" refers to a compound that absorbs thermal energy to undergo reverse intersystem crossing from the lowest excited triplet state to the lowest excited singlet state, and then radiatively deactivates from that lowest excited singlet state to emit delayed fluorescence. However, "thermally activated delayed fluorescence" also includes compounds that undergo a higher-order triplet state during the excitation process from the lowest excited triplet state to the lowest excited singlet state. For example, there is a paper by Monkman et al. from the University of Durham (NATURE COMMUNICATIONS, 7:13680, DOI: 10.1038 / ncomms13680), a paper by Hosokai et al. from the National Institute of Advanced Industrial Science and Technology (Hosokai et al., Sci. Adv. 2017;3: e1603282), a paper by Sato et al. from Kyoto University (Scientific Reports, 7:4820, DOI:10.1038 / s41598-017-05007-7), and a conference presentation by Sato et al. from Kyoto University (The 98th Annual Meeting of the Chemical Society of Japan, Presentation No.: 2I4-15, Mechanism of High-Efficiency Luminescence in Organic Electroluminescence Using DABNA as a Luminescent Molecule, Graduate School of Engineering, Kyoto University). In this invention, a target compound is determined to be a "thermally activated delayed phosphor" if a slow fluorescence component is observed when the fluorescence lifetime of a sample containing the target compound is measured at 300 K. Here, a slow fluorescence component refers to one with a fluorescence lifetime of 0.1 μsec or more. Fluorescence lifetime can be measured, for example, using a fluorescence lifetime analyzer (Hamamatsu Photonics, C11367-01).

[0359] The polycyclic aromatic compounds of the present invention can function as emitting dopants, and the "thermally activated delayed phosphor" can function as an assisting dopant that assists the luminescence of the polycyclic aromatic compounds of the present invention.

[0360] Figure 2 shows the energy level diagram of the light-emitting layer of a TAF device using a common fluorescent dopant as the emitting dopant (ED). In the figure, the energy level of the host ground state is E(1,G), the lowest excited singlet energy level obtained from the short-wavelength shoulder of the host fluorescence spectrum is E(1,S,Sh), the lowest excited triplet energy level obtained from the short-wavelength shoulder of the host phosphorescence spectrum is E(1,T,Sh), the energy level of the second component, the assisting dopant, ground state is E(2,G), the lowest excited singlet energy level obtained from the short-wavelength shoulder of the second component, the assisting dopant, is E(2,S,Sh), and the phosphorescence of the second component, the assisting dopant... Let E(2,T,Sh) be the lowest excited triplet energy level determined from the short-wavelength shoulder of the spectrum, E(3,G) be the ground state energy level of the third component, the emitting dopant, E(3,S,Sh) be the lowest excited singlet energy level determined from the short-wavelength shoulder of the fluorescence spectrum of the third component, the emitting dopant, and E(3,T,Sh) be the lowest excited triplet energy level determined from the short-wavelength shoulder of the phosphorescence spectrum of the third component, the emitting dopant. Let h+ represent holes, e- represent electrons, and FRET (Fluorescence Resonance Energy Transfer) be the fluorescence resonance energy transfer. In a TAF device, when a general fluorescent dopant is used as the emitting dopant (ED), the energy upconverted by the assisting dopant is transferred to the lowest excited singlet energy level E(3,S,Sh) of the emitting dopant and emits light. However, some of the lowest excited triplet energy E(2,T,Sh) on the assisting dopant moves to the lowest excited triplet energy level E(3,T,Sh) of the emitting dopant, or intersystem crossing occurs on the emitting dopant from the lowest excited singlet energy level E(3,S,Sh) to the lowest excited triplet energy level E(3,T,Sh), followed by thermal deactivation to the ground state E(3,G). Due to this pathway, some energy is not used for emission, resulting in wasted energy.

[0361] In contrast, the organic electroluminescent device of this embodiment can efficiently utilize the energy transferred from the assisting dopant to the emitting dopant for light emission, thereby achieving high luminescence efficiency. This is presumed to be due to the following light emission mechanism.

[0362] Figure 3 shows the preferred energy relationships in the organic electroluminescent device of this embodiment. In the organic electroluminescent device of this embodiment, the compound having a boron atom as the emitting dopant has a high lowest excited triplet energy level E(3,T,Sh). Therefore, even if the excited singlet energy upconverted by the assisting dopant undergoes intersystem crossing to the lowest excited triplet energy level E(3,T,Sh) in the emitting dopant, it is either upconverted on the emitting dopant or recovered to the lowest excited triplet energy level E(2,T,Sh) on the assisting dopant (thermally activated delayed phosphor). Thus, the generated excitation energy can be used for light emission without waste. Furthermore, by separating the upconversion and light emission functions into two types of molecules, each suited to its respective role, the residence time of high energy is reduced, and the burden on the compound is expected to decrease.

[0363] In this embodiment, known host compounds can be used, for example, compounds having at least one of a carbazole ring and a furan ring, and among these, it is preferable to use a compound in which at least one of furanil and carbazolyl is bonded to at least one of arylene and heteroarylene. Specific examples include mCP and mCBP.

[0364] The lowest excited triplet energy level E(1,T,Sh), determined from the short-wavelength shoulder of the phosphorescence spectrum of the host compound, is preferably higher than the lowest excited triplet energy levels E(2,T,Sh) and E(3,T,Sh) of the emitter or assisting dopant having the highest lowest excited triplet energy level in the light-emitting layer, from the viewpoint of promoting TADF generation in the light-emitting layer without inhibiting it. Specifically, the lowest excited triplet energy level E(1,T,Sh) of the host compound is preferably 0.01 eV or higher, more preferably 0.03 eV or higher, and even more preferably 0.1 eV or higher, compared to E(2,T,Sh) and E(3,T,Sh). Furthermore, a TADF-active compound may be used as the host compound.

[0365] For example, the host compound can be a compound represented by any of the above formulas (H1), (H2), and (H3).

[0366] <Thermally activated delayed phosphors (assisting dopants)> The thermally activated delay phosphor (TADF compound) used in TAF elements is preferably a donor-acceptor type thermally activated delay phosphor (DA-type TADF compound) designed to enable efficient reverse intersystem crossing by localizing the HOMO (Highest Occupied Molecular Orbital) and LUMO (Lowest Unoccupied Molecular Orbital) within the molecule using an electron-donating substituent called a donor and an electron-accepting substituent called an acceptor. Hereinafter, "electron-donating substituent" (donor) refers to substituents and substructures in which the HOMO orbital is localized within the thermally activated delay phosphor molecule, and "electron-accepting substituent" (acceptor) refers to substituents and substructures in which the LUMO orbital is localized within the thermally activated delay phosphor molecule.

[0367] Generally, thermally activated delayed phosphors using donors and acceptors exhibit large spin-orbit coupling (SOC) due to their structure, and small exchange interaction between the HOMO and LUMO, resulting in a small ΔE(ST) and thus very fast reverse intersystem crossing velocities. On the other hand, thermally activated delayed phosphors using donors and acceptors exhibit large structural relaxation in the excited state (in some molecules, the stable structure differs between the ground state and the excited state; therefore, when a conversion from the ground state to the excited state occurs due to an external stimulus, the structure subsequently changes to the stable structure in the excited state), resulting in a broad emission spectrum. Therefore, using them as luminescent materials may reduce color purity.

[0368] As a thermally activated delayed phosphor in a TAF element, for example, a compound in which the donor and acceptor are directly or via a spacer can be used. As the electron-donating group (donor structure) and electron-accepting group (acceptor structure) used in the thermally activated delayed phosphor of the present invention, for example, the structures described in Chemistry of Materials, 2017, 29, 1946-1963 can be used. Examples of donor structures include carbazole, dimethylcarbazole, di-tert-butylcarbazole, dimethoxycarbazole, tetramethylcarbazole, benzofluorocarbazole, benzothienocarbazole, phenyldihydroindocarbazole, phenylbicarbazole, bicarbazole, tercarbazole, diphenylcarbazolylamine, tetraphenylcarbazolyldiamine, phenoxazine, dihydrophenazine, phenothiazine, dimethyldihydroacridine, diphenylamine, bis(tert-butylphenyl)amine, N1-(4-(diphenylamino)phenyl)-N4,N4-diphenylbenzene-1,4-diamine, dimethyltetraphenyldihydroacridinediamine, tetramethyl-dihydroindenoacridine, and diphenyl-dihydrodibenzoazacillin.Acceptor structures include sulfonyldibenzene, benzophenone, phenylenbis(phenylmethanone), benzonitrile, isonicotinonitrile, phthalonitrile, isophthalonitrile, paraphthalonitrile, benzenetricarbonitride, triazole, oxazole, thiadiazole, benzothiazole, benzobis(thiazole), benzoxazole, benzobis(oxazole), quinoline, benzimidazole, dibenzoquinoxaline, heptazphenalene, thioxanthone Examples include oxides, dimethylanthracenone, anthracendione, 5H-cyclopenta[1,2-b:5,4-b']dipyridine, fluo-orange carbonitride, triephenyltriazine, pyrazine dicarbonitride, pyrimidine, phenylpyrimidine, methylpyrimidine, pyridine dicarbonitride, dibenzoquinoxaline dicarbonitride, bis(phenylsulfonyl)benzene, dimethylthioxanthene dioxide, thianthurene tetraoxide, and tris(dimethylphenyl)borane. In particular, compounds having thermally activated delayed fluorescence in TAF elements are preferably compounds having at least one selected from carbazole, phenoxazine, acridine, triazine, pyrimidine, pyrazine, thioxanthene, benzonitrile, phthalonitrile, isophthalonitrile, diphenylsulfone, triazole, oxadiazole, thiadiazole, and benzophenone as a substructure.

[0369] The compound used as the second component of the light-emitting layer in a TAF element is preferably a thermally activated delayed phosphor whose emission spectrum overlaps at least partially with the absorption peak of the emitting dopant. Below, examples of compounds that can be used as the second component (thermally activated delayed phosphor) of the light-emitting layer in a TAF element are given. However, the compounds that can be used as thermally activated delayed phosphors in a TAF element are not limited to the following example compounds. In the following formula, Me represents methyl, tBu represents t-butyl, and the dashed line represents the bond position.

[0370] [ka]

[0371] [ka]

[0372] [ka]

[0373] [ka]

[0374] [ka]

[0375] Furthermore, as a thermally activated delayed phosphor, a compound represented by any of the following formulas (AD1), (AD2), and (AD3) can also be used. [ka]

[0376] In the above formulas (AD1), (AD2), and (AD3), M is independently a single bond, -O-, >N-Ar, or >CAr2, and is preferably a single bond, -O-, or >N-Ar from the viewpoint of the depth of the HOMO of the formed substructure and the height of the lowest excited singlet energy level and the lowest excited triplet energy level. J is a spacer structure that separates the donor substructure and the acceptor substructure, and is independently an arylene having 6 to 18 carbon atoms, and is preferably an arylene having 6 to 12 carbon atoms from the viewpoint of the magnitude of conjugation that leaches from the donor substructure and the acceptor substructure. More specifically, phenylene, methylphenylene, and dimethylphenylene are examples. Q is independently =C(-H)- or =N-, and is preferably =N- from the viewpoint of the shallowness of the LUMO of the formed substructure and the height of the lowest excited singlet energy level and the lowest excited triplet energy level. Ar is independently hydrogen, a C6-C24 aryl, a C2-C24 heteroaryl, a C1-C12 alkyl, or a C3-C18 cycloalkyl, and is preferably hydrogen, a C6-C12 aryl, a C2-C14 heteroaryl, a C1-C4 alkyl, or a C6-C10 cycloalkyl, more preferably hydrogen, phenyl, tolyl, xylyl, mesityl, biphenyl, pyridyl, bipyridyl, triazyl, carbazolyl, dimethylcarbazol, ditert-butylcarbazol, benzimidazole, or phenylbenzimidazole, and even more preferably hydrogen, phenyl, or carbazolyl. m is 1 or 2. n is an integer less than or equal to (6-m), and is preferably an integer from 4 to (6-m) from the viewpoint of steric hindrance. Furthermore, at least one hydrogen atom in each of the above formulas may be substituted with a halogen or deuterium.

[0377] More specifically, the compounds used as the second component in this embodiment are preferably 4CzBN, 4CzBN-Ph, 5CzBN, 3Cz2DPhCzBN, 4CzIPN, 2PXZ-TAZ, Cz-TRZ3, BDPCC-TPTA, MA-TA, PA-TA, FA-TA, PXZ-TRZ, DMAC-TRZ, BCzT, DCzTrz, DDCzTRz, spiroAC-TRZ, Ac-HPM, Ac-PPM, Ac-MPM, TCzTrz, TmCzTrz, and DCzmCzTrz.

[0378] The compound used as the second component in this embodiment may be a donor-acceptor type TADF compound represented by DA, in which one donor D and one acceptor A are directly bonded or bonded via a linking group. However, it is preferable that the compound has a structure represented by the following formula (DAD1), in which multiple donor Ds are directly bonded or bonded via linking groups to one acceptor A, as this results in better characteristics of the organic electroluminescent element. (D 1 -L 1 )nA 1 (DAD1) Formula (DAD1) includes compounds represented by the following formula (DAD2). D 2 -L 2 -A 2 -L 3 -D 3 (DAD2) In equations (DAD1) and (DAD2), D 1 , D 2 and D 3 Each of these independently represents a donor group. The donor structure described above can be used as the donor group. A 1 and A 2 Each of these independently represents an acceptor group. The above acceptor structure can be used as the acceptor group. 1 , L 2 and L 3Each of these independently represents a single bond or a conjugated linkage group. The conjugated linkage group is a spacer structure that separates the donor group and the acceptor group, and is preferably an arylene having 6 to 18 carbon atoms, and more preferably an arylene having 6 to 12 carbon atoms. 1 , L 2 and L 3 It is even more preferable that each of them be independently phenylene, methylphenylene, or dimethylphenylene. In formula (DAD1), n ​​is 2 or more, and A 1 n represents an integer less than or equal to the maximum number of substitutions possible. n can be selected, for example, from 2 to 10 or from 2 to 6. When n is 2, the compound is represented by formula (DAD2). n D 1 They may be the same or different, and n L 1 These may be the same or different. Preferred specific examples of the compounds represented by formulas (DAD1) and (DAD2) include 2PXZ-TAZ and the following compounds, but the second component that can be used in the present invention is not limited to these compounds.

[0379] [ka]

[0380] In this embodiment, the light-emitting layer may consist of a single layer or multiple layers. Furthermore, the host compound, the thermally activated delayed phosphor, and the polycyclic aromatic compound of the present invention may be contained in the same layer, or at least one component may be contained in multiple layers. The host compound, thermally activated delayed phosphor, and polycyclic aromatic compound of the present invention contained in the light-emitting layer may each be one type or a combination of multiple types. The assisting dopant and the emitting dopant may be contained entirely or partially in the host compound as a matrix. The light-emitting layer doped with the assisting dopant and the emitting dopant can be formed by a ternary co-evaporation method of depositing the host compound, assisting dopant and emitting dopant, a method of pre-mixing the host compound, assisting dopant and emitting dopant and then simultaneously depositing them, or a wet deposition method in which a light-emitting layer forming composition (paint) prepared by dissolving the host compound, assisting dopant and emitting dopant in an organic solvent is applied.

[0381] The amount of host compound used varies depending on the type of host compound and should be determined according to the characteristics of that host compound. A guideline for the amount of host compound used is preferably 40 to 99.999% by mass of the total material for the light-emitting layer, more preferably 50 to 99.99% by mass, and even more preferably 60 to 99.9% by mass. Within this range, for example, efficient charge transport and efficient energy transfer to the dopant are preferable.

[0382] The amount of assisting dopant (thermally activated delayed phosphor) used varies depending on the type of assisting dopant and should be determined according to the characteristics of that assisting dopant. The guideline for the amount of assisting dopant used is preferably 1 to 60% by mass of the total material for the light-emitting layer, more preferably 2 to 50% by mass, and even more preferably 5 to 30% by mass. Within this range, for example, it is preferable in that energy can be efficiently transferred to the emitting dopant.

[0383] The amount of emitting dopant (a compound containing boron atoms) used varies depending on the type of emitting dopant and should be determined according to the characteristics of that emitting dopant. A guideline for the amount of emitting dopant used is preferably 0.001 to 30% by mass of the total material for the light-emitting layer, more preferably 0.01 to 20% by mass, and even more preferably 0.1 to 10% by mass. Within this range, for example, it is preferable in that it can prevent density quenching.

[0384] A lower concentration of the emitting dopant is preferable in that it can prevent concentration quenching. A higher concentration of the assisting dopant is preferable in terms of the efficiency of the thermally activated delayed fluorescence mechanism. Furthermore, in terms of the efficiency of the thermally activated delayed fluorescence mechanism of the assisting dopant, a lower concentration of the emitting dopant compared to the assisting dopant is preferable.

[0385] <2-1-3. Substrates in Organic Electroluminescent Devices> The substrate 101 is a support for the organic EL element 100, and is typically made of quartz, glass, metal, or plastic. The substrate 101 is formed in the form of a plate, film, or sheet depending on the purpose, and can be made of glass, metal, metal foil, plastic film, or plastic sheet, for example. Among these, glass plates and transparent synthetic resin plates such as polyester, polymethacrylate, polycarbonate, or polysulfone are preferred. If a glass substrate is used, soda-lime glass or alkali-free glass can be used, and the thickness only needs to be sufficient to maintain mechanical strength, for example, 0.2 mm or more is sufficient. The upper limit of the thickness is, for example, 2 mm or less, preferably 1 mm or less. Regarding the glass material, alkali-free glass is preferred because it is better to have fewer ions eluted from the glass, but soda-lime glass with a barrier coating such as SiO2 is also commercially available and can be used. Furthermore, to enhance the gas barrier properties, the substrate 101 may be provided with a gas barrier film, such as a dense silicon oxide film, on at least one side. It is particularly preferable to provide a gas barrier film when using a synthetic resin plate, film, or sheet with low gas barrier properties as the substrate 101.

[0386] <2-1-4. Anode in an Organic Electroluminescent Device> The anode 102 plays the role of injecting holes into the light-emitting layer 105. If either the hole injection layer 103 or the transport layer 104 is provided between the anode 102 and the light-emitting layer 105, the holes will be injected into the light-emitting layer 105 via these layers.

[0387] Materials for forming the anode 102 include inorganic compounds and organic compounds. Examples of inorganic compounds include metals (aluminum, gold, silver, nickel, palladium, chromium, etc.), metal oxides (indium oxide, tin oxide, indium-tin oxide (ITO), indium-zinc oxide (IZO), etc.), metal halides (copper iodide, etc.), copper sulfide, carbon black, ITO glass, and NESA glass. Examples of organic compounds include polythiophenes such as poly(3-methylthiophene), conductive polymers such as polypyrrole and polyaniline. In addition, other materials used as anodes in organic EL elements can be appropriately selected and used.

[0388] The resistance of the transparent electrode is not limited as long as it can supply sufficient current for the light-emitting element to emit light, but from the viewpoint of the power consumption of the light-emitting element, low resistance is desirable. For example, an ITO substrate with a resistance of 300 Ω / □ or less will function as an element electrode, but since substrates of about 10 Ω / □ are now available, it is particularly desirable to use a low-resistance product of, for example, 100 to 5 Ω / □, preferably 50 to 5 Ω / □. The thickness of the ITO can be arbitrarily selected according to the resistance value, but it is usually used between 50 and 300 nm.

[0389] <2-1-5. Hole injection layer and hole transport layer in organic electroluminescent devices> The hole injection layer 103 plays the role of efficiently injecting holes moving from the anode 102 into the light-emitting layer 105 or the hole transport layer 104. The hole transport layer 104 plays the role of efficiently transporting holes injected from the anode 102 or holes injected from the anode 102 via the hole injection layer 103 to the light-emitting layer 105. The hole injection layer 103 and the hole transport layer 104 are each formed by laminating and mixing one or more types of hole injection / transport materials, or by a mixture of hole injection / transport materials and a polymer binder. Alternatively, an inorganic salt such as iron(III) chloride may be added to the hole injection / transport material to form a layer.

[0390] For hole-injecting and transporting materials, it is necessary to efficiently inject and transport holes from the positive electrode between electrodes under an applied electric field. Therefore, it is desirable to have high hole injection efficiency and efficient transport of the injected holes. To achieve this, it is preferable to have a low ionization potential, high hole mobility, excellent stability, and a material that does not easily generate trapping impurities during manufacturing and use.

[0391] As the material for forming the hole injection layer 103 and the hole transport layer 104, any compound can be selected from among compounds conventionally used as charge transport materials for holes in photoconductive materials, p-type semiconductors, and known compounds used in hole injection layers and hole transport layers of organic EL devices. Specific examples include carbazole derivatives (N-phenylcarbazole, polyvinylcarbazole, etc.), biscarbazole derivatives such as bis(N-arylcarbazole) or bis(N-alkylcarbazole), triarylamine derivatives (4,4',4”-tris(N-carbazol)triphenylamine, polymers having aromatic tertiary amino acids in the main chain or side chain, 1,1-bis(4-di-p-tolylaminophenyl)cyclohexane, N,N'-diphenyl-N,N'-di(3-methylphenyl)-4,4'-diaminobiphenyl, N,N'-diphenyl-N,N'-dinaphthyl-4,4'-diaminobiphenyl, N,N'-diphenyl-N,N'-di(3-methylphenyl)-4,4'-diphenyl-1,1'-diamine, N,N'-dinaphthyl-N,N'-diphenyl-4,4'-diphenyl-1,1'-diamine, N 4 ,N 4’ -diphenyl-N 4 ,N 4’ -Bis(9-phenyl-9H-carbazole-3-yl)-[1,1'-biphenyl]-4,4'-diamine, N 4 ,N 4 ,N 4’ ,N 4’Triphenylamine derivatives such as -tetra[1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4,4'-diamine, 4,4',4”-tris(3-methylphenyl(phenyl)amino)triphenylamine, starburstamine derivatives, etc., stilbene derivatives, phthalocyanine derivatives (metal-free, copper phthalocyanine, etc.), pyrazoline derivatives, hydrazone compounds, benzofuran derivatives and thiophene derivatives, oxadiazole derivatives, quinoxaline derivatives Examples include conductors (e.g., 1,4,5,8,9,12-hexaazatriphenylene-2,3,6,7,10,11-hexacarbonitrine), heterocyclic compounds such as porphyrin derivatives, and polysilanes. Among polymer systems, polycarbonates, styrene derivatives, polyvinylcarbazoles, and polysilanes having the monomers in their side chains are preferred, but the compound is not particularly limited as long as it can form a thin film necessary for fabricating a light-emitting device, allow holes to be injected from the anode, and transport holes.

[0392] Furthermore, the conductivity of organic semiconductors is known to be strongly influenced by doping. Such organic semiconductor matrix materials are composed of compounds with good electron-donating properties or compounds with good electron-accepting properties. Strong electron acceptors such as tetracyanoquinone dimethane (TCNQ) or 2,3,5,6-tetrafluorotetracyano-1,4-benzoquinone dimethane (F4TCNQ) are known for doping with electron-donating substances (see, for example, "M. Pfeiffer, A. Beyer, T. Fritz, K. Leo, Appl. Phys. Lett., 73(22), 3202-3204 (1998)" and "J. Blochwitz, M. Pfeiffer, T. Fritz, K. Leo, Appl. Phys. Lett., 73(6), 729-731 (1998)"). These generate so-called holes through an electron transfer process in the electron-donating base material (hole transporter). The conductivity of the base material changes considerably depending on the number and mobility of holes. Examples of matrix materials having hole transport properties include benzidine derivatives (such as TPD) or starburst amine derivatives (such as TDATA), or certain metal phthalocyanines (especially zinc phthalocyanine (ZnPc)) (Japanese Patent Publication No. 2005-167175). The polycyclic aromatic compounds of the present invention may be used as materials for forming hole injection layers or hole transport layers.

[0393] <2-1-6. Electron blocking layer in organic electroluminescent devices> An electron blocking layer may be provided between the hole injection / transport layer and the light-emitting layer to prevent the diffusion of electrons from the light-emitting layer. For forming the electron blocking layer, any compound represented by one of the above formulas (H1), (H2), and (H3) can be used. The polycyclic aromatic compounds of the present invention may also be used as materials for forming electron blocking layers.

[0394] <2-1-7. Electron injection layer and electron transport layer in organic electroluminescent devices> The electron injection layer 107 plays the role of efficiently injecting electrons moving from the cathode 108 into the light-emitting layer 105 or the electron transport layer 106. The electron transport layer 106 plays the role of efficiently transporting 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 each formed by laminating and mixing one or more types of electron transport / injection materials, or by a mixture of electron transport / injection materials and a polymer binder.

[0395] The electron injection and transport layer is responsible for injecting electrons from the cathode and transporting them. It is desirable for this layer to have high electron injection efficiency and to efficiently transport the injected electrons. To achieve this, it is preferable for the material to have high electron affinity, high electron mobility, excellent stability, and to be a material that does not easily generate trapping impurities during manufacturing and use. However, when considering the balance between hole and electron transport, if the main role is to efficiently prevent holes from the anode from flowing to the cathode side without recombining, then even if the electron transport capacity is not very high, the effect of improving luminescence efficiency will be equivalent to that of a material with high electron transport capacity. Therefore, the electron injection and transport layer in this embodiment may also include the function of a layer that can efficiently prevent the movement of holes.

[0396] The material used to form the electron transport layer 106 or electron injection layer 107 (electron transport material) can be arbitrarily selected from compounds conventionally used as electron transfer compounds in photoconductive materials, and known compounds used in the electron injection layer and electron transport layer of organic EL elements.

[0397] The materials used in the electron transport layer or electron injection layer preferably contain at least one selected from compounds consisting of aromatic rings or heteroaromatic rings composed of one or more atoms selected from carbon, hydrogen, oxygen, sulfur, silicon, and phosphorus, pyrrole derivatives and their 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(diphenylethenyl)biphenyl, perinone derivatives, coumarin derivatives, naphthalimide derivatives, quinone derivatives such as anthraquinone and diphenoquinone, phosphine oxide derivatives, arylnitrile derivatives, and indole derivatives. Examples of metal complexes having electron-accepting nitrogen include hydroxyazole complexes such as hydroxyphenyloxazole complexes, azomethine complexes, tropolone metal complexes, flavonol metal complexes, and benzoquinoline metal complexes. These materials can be used individually or in combination with different materials.

[0398] Furthermore, specific examples of other electron transfer compounds include pyridine derivatives, naphthalene derivatives, fluorantene derivatives, BO derivatives, anthracene derivatives, phenanthroline derivatives, perinone derivatives, coumarin derivatives, naphthalimide derivatives, anthraquinone derivatives, diphenoquinone derivatives, diphenylquinone derivatives, perylene derivatives, oxadiazole derivatives (such as 1,3-bis[(4-t-butylphenyl)1,3,4-oxadiazolyl]phenylene), thiophene derivatives, triazole derivatives (such as N-naphthyl-2,5-diphenyl-1,3,4-triazole), thiadiazole derivatives, metal complexes of oxine derivatives, quinolinol-based metal complexes, quinoxaline derivatives, polymers of quinoxaline derivatives, benzazole compounds, gallium complexes, pyrazole derivatives, perfluorinated phenylene derivatives, triazine derivatives, pyrazine derivatives, and benzoquinone derivatives. Examples include phosphorus derivatives (such as 2,2'-bis(benzo[h]quinoline-2-yl)-9,9'-spirobifluorene), imidazopyridine derivatives, borane derivatives, benzimidazole derivatives (such as tris(N-phenylbenzimidazole-2-yl)benzene), benzoxazole derivatives, thiazole derivatives, benzothiazole derivatives, quinoline derivatives, oligopyridine derivatives such as terpyridine, bipyridine derivatives, terpyridine derivatives (such as 1,3-bis(2,2':6',2”-terpyridine-4'-yl)benzene), naphthyridine derivatives (such as bis(1-naphthyl)-4-(1,8-naphthyridine-2-yl)phenylphosphine oxide), aldazine derivatives, pyrimidine derivatives, arylnitrile derivatives, indole derivatives, phosphine oxide derivatives, bisstyryl derivatives, silole derivatives, and azoline derivatives.

[0399] Furthermore, metal complexes containing electron-accepting nitrogen can also be used, such as quinolinol-based metal complexes, hydroxyazole complexes such as hydroxyphenyl oxazole complexes, azomethine complexes, tropolone metal complexes, flavonol metal complexes, and benzoquinoline metal complexes.

[0400] The materials mentioned above can be used individually, but they can also be used in combination with other materials.

[0401] Among the materials mentioned above, borane derivatives, pyridine derivatives, fluorantene derivatives, BO derivatives, anthracene derivatives, benzofluorene derivatives, phosphine oxide derivatives, pyrimidine derivatives, arylnitrile derivatives, triazine derivatives, benzimidazole derivatives, phenanthroline derivatives, quinolinol-based metal complexes, thiazole derivatives, benzothiazole derivatives, silole derivatives, and azoline derivatives are preferred.

[0402] The polycyclic aromatic compounds of the present invention may be used as materials for forming electron injection layers or electron transport layers.

[0403] The electron transport layer or electron injection layer may further contain a substance capable of reducing the material forming the electron transport layer or electron injection layer. This reducing substance can be any substance having a certain reducing property; for example, at least one selected from the group consisting of alkali metals, alkaline earth metals, rare earth metals, alkali metal oxides, alkali metal halides, alkaline earth metal oxides, alkaline earth metal halides, rare earth metal oxides, rare earth metal halides, alkali metal organic complexes, alkaline earth metal organic complexes, and rare earth metal organic complexes can be suitably used.

[0404] Preferred reducing substances include alkali metals such as Na (work function 2.36 eV), K (2.28 eV), Rb (2.16 eV), or Cs (1.95 eV), and alkaline earth metals such as Ca (2.9 eV), Sr (2.0-2.5 eV), or Ba (2.52 eV), with substances having a work function of 2.9 eV or less being particularly preferred. Of these, alkali metals K, Rb, or Cs are more preferred reducing substances, Rb or Cs are even more preferred, and Cs is the most preferred. These alkali metals have particularly high reducing ability, and their addition in relatively small amounts to materials forming electron transport layers or electron injection layers can improve the luminescence brightness and extend the lifespan of organic EL devices. Furthermore, combinations of two or more alkali metals are also preferred as reducing substances with a work function of 2.9 eV or less, and combinations including Cs, such as Cs and Na, Cs and K, Cs and Rb, or Cs, Na, and K, are particularly preferred. By including Cs, the reducing ability can be efficiently exhibited, and by adding it to the material forming the electron transport layer or electron injection layer, improvements in luminescence brightness and extended lifespan can be achieved in organic EL devices.

[0405] <2-1-8. Cathode in Organic Electroluminescent Devices> The cathode 108 plays the role of injecting electrons into the light-emitting layer 105 via the electron injection layer 107 and the electron transport layer 106.

[0406] The material forming the cathode 108 is not particularly limited as long as it can efficiently inject electrons into the organic layer, but the same material as the material forming the anode 102 can be used. Among these, metals such as tin, indium, calcium, aluminum, silver, copper, nickel, chromium, gold, platinum, iron, zinc, lithium, sodium, potassium, cesium, and magnesium, or their alloys (such as magnesium-silver alloys, magnesium-indium alloys, and aluminum-lithium alloys such as lithium fluoride / aluminum), are preferred. To increase electron injection efficiency and improve device characteristics, alloys containing lithium, sodium, potassium, cesium, calcium, magnesium, or these low work function metals are effective. However, these low work function metals are generally unstable in the atmosphere. To improve this, for example, a method is known in which the organic layer is doped with trace amounts of lithium, cesium, or magnesium to use electrodes with high stability. Other dopants that can be used include inorganic salts such as lithium fluoride, cesium fluoride, lithium oxide, and cesium oxide. However, they are not limited to these.

[0407] Furthermore, for electrode protection, it is preferable to laminate metals such as platinum, gold, silver, copper, iron, tin, aluminum, and indium, or alloys using these metals, as well as inorganic materials such as silica, titania, and silicon nitride, polyvinyl alcohol, vinyl chloride, and hydrocarbon polymer compounds. The method for fabricating these electrodes is not particularly limited as long as conductivity can be achieved, such as resistance heating, electron beam deposition, sputtering, ion plating, and coating.

[0408] <2-1-9. Binding agents that may be used in each layer> The materials used in the hole injection layer, hole transport layer, light emission layer, electron transport layer, and electron injection layer described above can form each layer individually, but they can also be dispersed in solvent-soluble resins such as polyvinyl chloride, polycarbonate, polystyrene, poly(N-vinylcarbazole), polymethyl methacrylate, polybutyl methacrylate, polyester, polysulfone, polyphenylene oxide, polybutadiene, hydrocarbon resins, ketone resins, phenoxy resins, polyamides, ethylcellulose, vinyl acetate resins, ABS resins, and polyurethane resins, or in curable resins such as phenolic resins, xylene resins, petroleum resins, urea resins, melamine resins, unsaturated polyester resins, alkyd resins, epoxy resins, and silicone resins as polymer binders.

[0409] <2-1-10. Method for fabricating organic electroluminescent devices> Each layer constituting an organic EL element can be formed by thinning the material to be composed of each layer using methods such as vapor deposition, resistance heating deposition, electron beam deposition, sputtering, molecular stacking, printing, inkjet, spin coating or casting, or coating. There are no particular limitations on the thickness of each layer formed in this way, and it can be set appropriately according to the properties of the material, but it is usually in the range of 2 nm to 5000 nm. The thickness can usually be measured with a quartz crystal oscillating film thickness analyzer. When thinning using vapor deposition, the deposition conditions vary depending on the type of material, the desired crystal structure and association structure of the film, etc. Generally, the deposition conditions are a boat heating temperature of +50 to +400°C and a vacuum of 10°C. -6 ~10 -3 It is preferable to appropriately set the Pa, deposition rate to 0.01 to 50 nm / second, substrate temperature to -150 to +300°C, and film thickness to 2 nm to 5 μm.

[0410] Next, as an example of a method for fabricating an organic EL element, we will describe a method for fabricating an organic EL element consisting of an anode, a hole injection layer, a hole transport layer, an emissive layer made of host material and dopant material, an electron transport layer, an electron injection layer, and a cathode. An anode is fabricated by forming a thin film of anode material on a suitable substrate by vapor deposition or the like, and then thin films of a hole injection layer and a hole transport layer are formed on this anode. A thin film of host material and dopant material is co-deposited on this to form an emissive layer, and then an electron transport layer and an electron injection layer are formed on this emissive layer. Furthermore, a thin film made of cathode material is formed by vapor deposition or the like to form the cathode, thereby obtaining the desired organic EL element. In addition, in the fabrication of the organic EL element described above, it is also possible to reverse the fabrication order and fabricate the cathode, electron injection layer, electron transport layer, emissive layer, hole transport layer, hole injection layer, and anode in that order.

[0411] When applying a DC voltage to the organic EL element obtained in this way, the voltage should be applied with the anode as + and the cathode as -. When 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, or both). Furthermore, this organic EL element will also emit light when a pulsed current or alternating current is applied. The waveform of the applied AC current can be arbitrary.

[0412] <2-1-11. Application Examples of Organic Electroluminescent Devices> Organic EL elements can also be applied to display devices or lighting equipment. A display device or lighting device equipped with an organic EL element can be manufactured by known methods, such as connecting the organic EL element to a known driving device, and can be driven using known driving methods such as DC driving, pulse driving, or AC driving as appropriate.

[0413] 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 Publication No. 10-335066, Japanese Patent Publication No. 2003-321546, and Japanese Patent Publication No. 2004-281086). Examples of display methods include either matrix or segment displays. Matrix and segment displays may coexist on the same panel.

[0414] In a matrix display, pixels for display are arranged two-dimensionally, such as in a grid or mosaic pattern, and characters or images are displayed using a collection of pixels. The shape and size of the pixels are determined by the application. For example, for displaying images and characters on personal computers, monitors, and televisions, square pixels with sides of 300 μm or less are usually used, while for large displays such as display panels, pixels with sides on the order of millimeters are used. For monochrome displays, pixels of the same color can be arranged, but for color displays, red, green, and blue pixels are arranged side by side. In this case, there are typically delta type and stripe type displays. The matrix can be driven by either a line-sequential drive method or an active matrix. Line-sequential drive has the advantage of a simpler structure, but considering the operating characteristics, the active matrix may be superior in some cases, so it is necessary to choose the appropriate method depending on the application.

[0415] In segment-based displays, a pattern is formed to display predetermined information, and a designated area is illuminated. Examples include time and temperature displays in digital clocks and thermometers, operating status displays in audio equipment and induction cooktops, and panel displays in automobiles.

[0416] Examples of lighting devices include lighting devices such as indoor lighting and backlights for liquid crystal displays (see, for example, Japanese Patent Publication No. 2003-257621, Japanese Patent Publication No. 2003-277741, and Japanese Patent Publication No. 2004-119211). Backlights are mainly used to improve the visibility of non-self-illuminating display devices and are used in liquid crystal displays, clocks, audio equipment, automobile panels, display boards, and signs. In particular, for liquid crystal displays, especially backlights for personal computers where miniaturization is a challenge, conventional methods using fluorescent lamps or light guide plates make miniaturization difficult. Therefore, backlights using organic EL elements are characterized by their thinness and light weight.

[0417] <2-2. Other Organic Devices> The polycyclic aromatic compounds according to the present invention can be used not only in the organic field-light-emitting device described above, but also in the fabrication of organic field-effect transistors or organic thin-film solar cells.

[0418] An organic field-effect transistor (OCT) is a type of transistor that controls current using an electric field generated by a voltage input. In addition to source and drain electrodes, it has a gate electrode. When a voltage is applied to the gate electrode, an electric field is generated, allowing the current to be controlled by arbitrarily blocking the flow of electrons (or holes) between the source and drain electrodes. Compared to simple transistors (bipolar transistors), OTCs are easier to miniaturize and are frequently used as components in integrated circuits.

[0419] The structure of an organic field-effect transistor typically includes a source electrode and a drain electrode in contact with an organic semiconductor active layer formed using the polycyclic aromatic compound according to the present invention, and a gate electrode further separated by an insulating layer (dielectric layer) in contact with the organic semiconductor active layer. Examples of such device structures include the following: (1) Substrate / Gate electrode / Insulator layer / Source electrode / Drain electrode / Organic semiconductor active layer (2) Substrate / Gate electrode / Insulator layer / Organic semiconductor active layer / Source electrode / Drain electrode (3) Substrate / Organic semiconductor active layer / Source electrode / Drain electrode / Insulator layer / Gate electrode (4) Substrate / Source electrode / Drain electrode / Organic semiconductor active layer / Insulator layer / Gate electrode Organic field-effect transistors configured in this way can be applied as pixel driving switching elements in active-matrix driven liquid crystal displays and organic electroluminescent displays.

[0420] 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 compound according to the present invention can be used as a material for the hole transport layer, p-type semiconductor layer, n-type semiconductor layer, and electron transport layer, depending on its physical properties. The polycyclic aromatic compound according to the present invention can function as a hole transport material or an electron transport material in organic thin-film solar cells. In addition to the above, organic thin-film solar cells may appropriately include a hole blocking layer, an electron blocking layer, an electron injection layer, a hole injection layer, a smoothing layer, etc. Organic thin-film solar cells can be appropriately selected and combined with known materials used in organic thin-film solar cells.

[0421] <3. Wavelength conversion materials> The polycyclic aromatic compounds of the present invention can be used as wavelength conversion materials. Currently, there is much research into applying multi-color technology using color conversion methods to liquid crystal displays, organic EL displays, and lighting. Color conversion refers to the conversion of light emitted from a light source to longer wavelength light, for example, converting ultraviolet light or blue light into green light or red light. By creating a film of a wavelength conversion material with this color conversion function and combining it with, for example, a blue light source, it becomes possible to extract the three primary colors of blue, green, and red from the blue light source, i.e., to extract white light. By using such a white light source, which combines a blue light source with a wavelength conversion film with color conversion function, as a light source unit and combining it with a liquid crystal drive unit and a color filter, it becomes possible to manufacture a full-color display. Furthermore, if the liquid crystal drive unit is not required, it can be used as a white light source as is, and can be applied as a white light source for LED lighting, for example. In addition, by using a blue organic EL element as a light source and combining it with a wavelength conversion film that converts blue light into green and red light, it becomes possible to manufacture a full-color organic EL display without using a metal mask. Furthermore, by using a blue microLED as a light source in combination with a wavelength conversion film that converts blue light into green and red light, it becomes possible to create low-cost full-color microLED displays.

[0422] The polycyclic aromatic compounds of the present invention can be used as wavelength conversion materials. Using a wavelength conversion material containing the polycyclic aromatic compounds of the present invention, light from light sources and light-emitting elements that generate ultraviolet light or shorter wavelength blue light can be converted into blue or green light with high color purity suitable for use in display devices (display devices using organic EL elements or liquid crystal displays). The color to be converted can be adjusted by appropriately selecting substituents on the polycyclic aromatic compounds of the present invention, binder resins used in the wavelength conversion composition described later, etc. The wavelength conversion material can be prepared as a wavelength conversion composition containing the polycyclic aromatic compounds of the present invention. Alternatively, a wavelength conversion film may be formed using this wavelength conversion composition.

[0423] The wavelength conversion composition may contain, in addition to the polycyclic aromatic compound of the present invention, a binder resin, other additives, and a solvent. As the binder resin, for example, those described in paragraphs 0173-0176 of International Effect 2016 / 190283 can be used. As the other additive, compounds described in paragraphs 0177-0181 of International Effect 2016 / 190283 can be used. As the solvent, refer to the description of solvents included in the above-mentioned light-emitting layer forming composition.

[0424] The wavelength conversion film includes a wavelength conversion layer formed by curing a wavelength conversion composition. Known film formation methods can be used as a method for producing the wavelength conversion layer from the wavelength conversion composition. The wavelength conversion film may consist solely of a wavelength conversion layer formed from a composition containing the polycyclic aromatic compound of the present invention, or it may include other wavelength conversion layers (for example, a wavelength conversion layer that converts blue light to green or red light, or a wavelength conversion layer that converts blue or green light to red light). Furthermore, the wavelength conversion film may include a substrate layer and a barrier layer to prevent degradation of the color conversion layer due to oxygen, moisture, or heat. [Examples]

[0425] The present invention will be described in more detail below with reference to examples, but the present invention is not limited to these examples. In the description of the examples, Me represents methyl, Et represents ethyl, i Pr stands for isopropyl, and tBu stands for t-butyl.

[0426] Synthesis example (1): Synthesis of compound (1-1) [ka]

[0427] Under a nitrogen atmosphere, intermediate (X-1) (47.0 g), 1-t-butyl-3,4,5-trichlorobenzene (23.8 g), dichlorobis[di-t-butyl(4-dimethylaminophenyl)phosphino]palladium(II) (Pd-132) (0.909 g) as a palladium catalyst, sodium t-butoxide (NaOtBu, 14.4 g), and toluene (500 ml) were placed in a flask and heated at 120°C for 5 hours. After the reaction was complete, water and ethyl acetate were added to the reaction mixture and stirred, and the organic layer was separated and washed with water. Subsequently, the organic layer was concentrated, and the resulting crude product was purified using a silica gel short-pass column (eluent: heptane) to obtain 48.2 g of intermediate (X-2). [ka]

[0428] Under a nitrogen atmosphere, intermediate (X-2) (33.5 g), intermediate (X-3) (20.8 g), palladium catalyst Pd-132 (0.719 g), NaOtBu (7.21 g), and toluene (300 ml) were placed in a flask and heated at 120°C for 3 hours. After the reaction was complete, water and ethyl acetate were added to the reaction mixture and stirred, and the organic layer was separated and washed with water. The organic layer was then concentrated, and the resulting crude product was purified using a silica gel short-pass column (eluent: toluene / heptane = 1 / 9 (volume ratio)) to obtain 48.2 g of intermediate (X-4). [ka]

[0429] Intermediate (X-4) (10.5g) and tert-butylbenzene ( t In a flask containing 100 ml of Bu-benzene, a 1.60 M tert-butyllithium pentane solution is prepared at 0°C under a nitrogen atmosphere. tBuLi (12.5 ml) was added. After the dropwise addition was complete, the temperature was raised to 70°C and stirred for 0.5 hours, then components with a lower boiling point than tert-butylbenzene were removed by vacuum distillation. The mixture was cooled to -50°C, boron tribromide (2.06 g) was added, and the temperature was raised to room temperature and stirred for 0.5 hours. Then, it was cooled again to 0°C and N,N-diisopropylethylamine (EtN i Add Pr2 (1.29 g), stir at room temperature until the exothermic reaction subsides, then raise the temperature to 100°C and heat and stir for 1 hour. Cool the reaction mixture to room temperature, add aqueous sodium acetate solution cooled in an ice bath, then ethyl acetate, and separate the layers. After concentrating the organic layer, purify it using a silica gel short-pass column (eluent: chlorobenzene). Recrystallization of the resulting crude product from toluene yielded 6.90 g of compound (1-1). [ka]

[0430] The structure of the compound obtained by NMR measurement was confirmed. 1 H-NMR(CDCl3): 8.59(d, 1H), 7.86(d, 1H), 7.72-7.68(m, 3H), 7.64(dd, 1H), 7.45(dd, 2H) ), 7.37(dd, 2H), 7.34(d, 1H), 6.95(t, 1H), 6.88(d, 2H), 6.75(d, 1H), 6. 56 (d, 1H), 6.24 (d, 1H), 6.17 (d, 1H), 2.19 (s, 3H), 2.08 (d, 6H), 1.86 (s, 6H), 1.49(s, 9H), 1.46(s, 9H), 1.06(d, 9H), 1.02(s, 9H), 0.88(s, 18H).

[0431] Synthesis Example (2): Synthesis of Compounds (1-10) Compound (1-10) was obtained using the same procedure as in Synthesis Example 1, except that compound (X-4) was changed to compound (X-4-10). MS confirmed the target compound (1-10) with m / z(M+H) = 1009.69. [ka]

[0432] Synthesis Example (3): Synthesis of Compounds (1-35) Compound (1-35) was obtained using the same procedure as in Synthesis Example 1, except that compound (X-4) was changed to compound (X-4-35). MS confirmed the target compound (1-35) with m / z(M+H) = 1077.77. [ka]

[0433] Synthesis Example (4): Synthesis of Compounds (1-142) Compound (1-142) was obtained using the same procedure as in Synthesis Example 1, except that compound (X-4) was changed to compound (X-4-142). MS confirmed the target compound (1-142) with m / z(M+H) = 925.55. [ka]

[0434] Synthesis Example (5): Synthesis of Compounds (1-155) Compound (1-155) was obtained using the same procedure as in Synthesis Example 1, except that compound (X-4) was changed to compound (X-4-155). MS confirmed the target compound (1-155) with m / z(M+H) = 883.47. [ka]

[0435] Synthesis Example (6): Synthesis of Compounds (1-166) Compound (1-166) was obtained using the same procedure as in Synthesis Example 1, except that compound (X-4) was changed to compound (X-4-166). MS confirmed the target compound (1-166) with m / z(M+H) = 937.55. [ka]

[0436] Synthesis Example (7): Synthesis of Compounds (1-180) Compound (1-180) was obtained using the same procedure as in Synthesis Example 1, except that compound (X-4) was changed to compound (X-4-180). MS confirmed the target compound (1-180) with m / z(M+H) = 897.50. [ka]

[0437] Synthesis Example (8): Synthesis of Compounds (1-220) Compound (1-220) was obtained using the same procedure as in Synthesis Example 1, except that compound (X-4) was changed to compound (X-4-220). MS confirmed the target compound (1-220) with m / z(M+H) = 1185.82. [ka]

[0438] Synthesis Example (9): Synthesis of Compounds (1-230) Compound (1-230) was obtained using the same procedure as in Synthesis Example 1, except that compound (X-4) was changed to compound (X-4-230). MS confirmed the target compound (1-230) with m / z(M+H) = 1129.76. [ka]

[0439] Synthesis Example (10): Synthesis of Compound (1-237) Compound (1-237) was obtained using the same procedure as in Synthesis Example 1, except that compound (X-4) was changed to compound (X-4-237). MS confirmed the target compound (1-237) with m / z(M+H) = 1041.63. [ka]

[0440] Synthesis Example (11): Synthesis of Compounds (1-239) Compound (1-239) was obtained using the same procedure as in Synthesis Example 1, except that compound (X-4) was changed to compound (X-4-239). MS confirmed the target compound (1-239) with m / z(M+H) = 1055.65. [ka]

[0441] Synthesis Example (12): Synthesis of Compounds (1-240) Compound (1-240) was obtained using the same procedure as in Synthesis Example 1, except that compound (X-4) was changed to compound (X-4-240). MS confirmed the target compound (1-240) with m / z(M+H) = 1013.60. [ka]

[0442] Synthesis Example (13): Synthesis of Compounds (1-245) Compound (1-245) was obtained using the same procedure as in Synthesis Example 1, except that compound (X-4) was changed to compound (X-4-245). MS confirmed the target compound (1-245) with m / z(M+H) = 1261.85. [ka]

[0443] Synthesis Example (14): Synthesis of Compounds (1-246) Compound (1-246) was obtained using the same procedure as in Synthesis Example 1, except that compound (X-4) was changed to compound (X-4-246). MS confirmed the target compound (1-246) with m / z(M+H) = 1205.79. [ka]

[0444] Synthesis Example (15): Synthesis of Compounds (1-248) Compound (1-248) was obtained using the same procedure as in Synthesis Example 1, except that compound (X-4) was changed to compound (X-4-248). MS confirmed the target compound (1-248) with m / z(M+H) = 1207.80. [ka]

[0445] Synthesis Example (16): Synthesis of Compounds (1-249) Compound (1-249) was obtained using the same procedure as in Synthesis Example 1, except that compound (X-4) was changed to compound (X-4-249). MS confirmed the target compound (1-249) with m / z(M+H) = 1153.76. [ka]

[0446] Synthesis Example (17): Synthesis of Compounds (1-250) Compound (1-250) was obtained using the same procedure as in Synthesis Example 1, except that compound (X-4) was changed to compound (X-4-250). MS confirmed the target compound (1-250) with m / z(M+H) = 1179.77. [ka]

[0447] Synthesis Example (18): Synthesis of Compounds (1-251) Compound (1-251) was obtained using the same procedure as in Synthesis Example 1, except that compound (X-4) was changed to compound (X-4-251). MS confirmed the target compound (1-251) with m / z(M+H) = 1165.76. [ka]

[0448] Synthesis Example (19): Synthesis of Compounds (1-252) Compound (1-252) was obtained using the same procedure as in Synthesis Example 1, except that compound (X-4) was changed to compound (X-4-252). MS confirmed the target compound (1-252) with m / z(M+H) = 1111.71. [ka]

[0449] Synthesis Example (20): Synthesis of Compounds (1-253) Compound (1-253) was obtained using the same procedure as in Synthesis Example 1, except that compound (X-4) was changed to compound (X-4-253). MS confirmed the target compound (1-253) with m / z(M+H) = 1125.73. [ka]

[0450] Synthesis Example (21): Synthesis of Compounds (1-255) Compound (1-255) was obtained using the same procedure as in Synthesis Example 1, except that compound (X-4) was changed to compound (X-4-255). MS confirmed the target compound (1-255) with m / z(M+H) = 1189.76. [ka]

[0451] Synthesis Example (22): Synthesis of Compounds (1-257) Compound (1-257) was obtained using the same procedure as in Synthesis Example 1, except that compound (X-4) was changed to compound (X-4-257). MS confirmed the target compound (1-257) with m / z(M+H) = 1172.87. [ka]

[0452] Synthesis Example (23): Synthesis of Compounds (1-258) Compound (1-258) was obtained using the same procedure as in Synthesis Example 1, except that compound (X-4) was changed to compound (X-4-258). MS confirmed the target compound (1-258) with m / z(M+H) = 1041.63. [ka]

[0453] Synthesis Example (24): Synthesis of Compounds (1-262) Compound (1-262) was obtained using the same procedure as in Synthesis Example 1, except that compound (X-4) was changed to compound (X-4-262). MS confirmed the target compound (1-262) with m / z(M+H) = 1149.73. [ka]

[0454] Synthesis Example (25): Synthesis of Compounds (1-263) Compound (1-263) was obtained using the same procedure as in Synthesis Example 1, except that compound (X-4) was changed to compound (X-4-263). MS confirmed the target compound (1-263) with m / z(M+H) = 1107.68. [ka]

[0455] Synthesis Example (26): Synthesis of Compounds (1-265) Compound (1-265) was obtained using the same procedure as in Synthesis Example 1, except that compound (X-4) was changed to compound (X-4-265). MS confirmed the target compound (1-265) with m / z(M+H) = 1337.88. [ka]

[0456] Synthesis Example (27): Synthesis of Compounds (1-267) Compound (1-267) was obtained using the same procedure as in Synthesis Example 1, except that compound (X-4) was changed to compound (X-4-267). MS confirmed the target compound (1-267) with m / z(M+H) = 1318.98. [ka]

[0457] Synthesis Example (28): Synthesis of Compounds (1-269) Compound (1-269) was obtained using the same procedure as in Synthesis Example 1, except that compound (X-4) was changed to compound (X-4-269). MS confirmed the target compound (1-269) with m / z(M+H) = 1091.79. [ka]

[0458] Synthesis Example (29): Synthesis of Compounds (1-272) Compound (1-272) was obtained using the same procedure as in Synthesis Example 1, except that compound (X-4) was changed to compound (X-4-272). MS confirmed the target compound (1-272) with m / z(M+H) = 1015.67. [ka]

[0459] Synthesis Example (30): Synthesis of Compounds (1-282) Compound (1-282) was obtained using the same procedure as in Synthesis Example 1, except that compound (X-4) was changed to compound (X-4-282). MS confirmed the target compound (1-282) with m / z(M+H) = 1059.73. [ka]

[0460] Synthesis Example (31): Synthesis of Compounds (1-285) Compound (1-285) was obtained using the same procedure as in Synthesis Example 1, except that compound (X-4) was changed to compound (X-4-285). MS confirmed the target compound (1-285) with m / z(M+H) = 1061.75. [ka]

[0461] Synthesis Example (32): Synthesis of Compound (1-287) Compound (1-287) was obtained using the same procedure as in Synthesis Example 1, except that compound (X-4) was changed to compound (X-4-287). MS confirmed the target compound (1-287) with m / z(M+H) = 1135.76. [ka]

[0462] Synthesis Example (33): Synthesis of Compounds (1-296) Compound (1-296) was obtained using the same procedure as in Synthesis Example 1, except that compound (X-4) was changed to compound (X-4-296). MS confirmed the target compound (1-296) with m / z(M+H) = 1079.70. [ka]

[0463] Synthesis Example (34): Synthesis of Compound (1-297) Compound (1-297) was obtained using the same procedure as in Synthesis Example 1, except that compound (X-4) was changed to compound (X-4-297). MS confirmed the target compound (1-297) with m / z(M+H) = 1133.75. [ka]

[0464] Synthesis Example (35): Synthesis of Compounds (1-298) Compound (1-298) was obtained using the same procedure as in Synthesis Example 1, except that compound (X-4) was changed to compound (X-4-298). MS confirmed the target compound (1-298) with m / z(M+H) = 1025.65. [ka]

[0465] Synthesis Example (36): Synthesis of Compound (1-303) Compound (1-303) was obtained using the same procedure as in Synthesis Example 1, except that compound (X-4) was changed to compound (X-4-303). MS confirmed the target compound (1-303) with m / z(M+H) = 1075.81. [ka]

[0466] Synthesis Example (37): Synthesis of Compound (1-305) Compound (1-305) was obtained using the same procedure as in Synthesis Example 1, except that compound (X-4) was changed to compound (X-4-305). MS confirmed the target compound (1-305) with m / z(M+H) = 1083.73. [ka]

[0467] Synthesis Example (38): Synthesis of Compounds (1-308) Compound (1-308) was obtained using the same procedure as in Synthesis Example 1, except that compound (X-4) was changed to compound (X-4-308). MS confirmed the target compound (1-308) with m / z(M+H) = 1135.76. [ka]

[0468] Synthesis Example (39): Synthesis of Compounds (1-312) Compound (1-312) was obtained using the same procedure as in Synthesis Example 1, except that compound (X-4) was changed to compound (X-4-312). MS confirmed the target compound (1-312) with m / z(M+H) = 971.61. [ka]

[0469] Synthesis Example (40): Synthesis of Compounds (1-314) Compound (1-314) was obtained using the same procedure as in Synthesis Example 1, except that compound (X-4) was changed to compound (X-4-314). MS confirmed the target compound (1-314) with m / z(M+H) = 1211.80. [ka]

[0470] Synthesis Example (41): Synthesis of Compounds (1-316) Compound (1-316) was obtained using the same procedure as in Synthesis Example 1, except that compound (X-4) was changed to compound (X-4-316). MS confirmed the target compound (1-316) with m / z(M+H) = 1027.67. [ka]

[0471] Synthesis Example (42): Synthesis of Compounds (1-319) Compound (1-319) was obtained using the same procedure as in Synthesis Example 1, except that compound (X-4) was changed to compound (X-4-319). MS confirmed the target compound (1-319) with m / z(M+H) = 1117.72. [ka]

[0472] Synthesis Example (43): Synthesis of Compounds (1-320) Compound (1-320) was obtained using the same procedure as in Synthesis Example 1, except that compound (X-4) was changed to compound (X-4-320). MS confirmed the target compound (1-320) with m / z(M+H) = 1081.72. [ka]

[0473] Synthesis Example (44): Synthesis of Compounds (1-325) Compound (1-325) was obtained using the same procedure as in Synthesis Example 1, except that compound (X-4) was changed to compound (X-4-325). MS confirmed the target compound (1-325) with m / z(M+H) = 1245.87. [ka]

[0474] Synthesis Example (45): Synthesis of Compound (1-331) Compound (1-331) was obtained using the same procedure as in Synthesis Example 1, except that compound (X-4) was changed to compound (X-4-331). MS confirmed the target compound (1-331) with m / z(M+H) = 1191.83. [ka]

[0475] Synthesis Example (46): Synthesis of Compound (1-333) Compound (1-333) was obtained using the same procedure as in Synthesis Example 1, except that compound (X-4) was changed to compound (X-4-333). MS confirmed the target compound (1-333) with m / z(M+H) = 1265.84. [ka]

[0476] Synthesis Example (47): Synthesis of Compounds (1-339) Compound (1-339) was obtained using the same procedure as in Synthesis Example 1, except that compound (X-4) was changed to compound (X-4-339). MS confirmed the target compound (1-339) with m / z(M+H) = 1098.60. [ka]

[0477] Synthesis Example (48): Synthesis of Compounds (1-340) Compound (1-340) was obtained using the same procedure as in Synthesis Example 1, except that compound (X-4) was changed to compound (X-4-340). MS confirmed the target compound (1-340) with m / z(M+H) = 1318.81. [ka]

[0478] Synthesis Example (49): Synthesis of Compounds (1-345) Compound (1-345) was obtained using the same procedure as in Synthesis Example 1, except that compound (X-4) was changed to compound (X-4-345). MS confirmed the target compound (1-345) with m / z(M+H) = 1284.74. [ka]

[0479] Synthesis Example (50): Synthesis of Compounds (1-349) Compound (1-349) was obtained using the same procedure as in Synthesis Example 1, except that compound (X-4) was changed to compound (X-4-349). MS confirmed the target compound (1-349) with m / z(M+H) = 1312.77. [ka]

[0480] Synthesis Example (51): Synthesis of Compounds (1-353) Compound (1-353) was obtained using the same procedure as in Synthesis Example 1, except that compound (X-4) was changed to compound (X-4-353). MS confirmed the target compound (1-353) with m / z(M+H) = 1074.65. [ka]

[0481] Synthesis Example (52): Synthesis of Compounds (1-362) Compound (1-362) was obtained using the same procedure as in Synthesis Example 1, except that compound (X-4) was changed to compound (X-4-362). MS confirmed the target compound (1-362) with m / z(M+H) = 1296.79. [ka]

[0482] Synthesis Example (53): Synthesis of Compounds (1-367) Compound (1-367) was obtained using the same procedure as in Synthesis Example 1, except that compound (X-4) was changed to compound (X-4-367). MS confirmed the target compound (1-367) with m / z(M+H) = 1248.79. [ka]

[0483] Synthesis Example (54): Synthesis of Compound (1-374) Compound (1-374) was obtained using the same procedure as in Synthesis Example 1, except that compound (X-4) was changed to compound (X-4-374). MS confirmed the target compound (1-374) with m / z(M+H) = 963.58. [ka]

[0484] Synthesis Example (55): Synthesis of Compounds (1-384) Compound (1-384) was obtained using the same procedure as in Synthesis Example 1, except that compound (X-4) was changed to compound (X-4-384). MS confirmed the target compound (1-384) with m / z(M+H) = 1151.74. [ka]

[0485] Synthesis Example (56): Synthesis of Compound (1-387) Compound (1-387) was obtained using the same procedure as in Synthesis Example 1, except that compound (X-4) was changed to compound (X-4-387). MS confirmed the target compound (1-387) with m / z(M+H) = 1151.74. [ka]

[0486] Synthesis Example (57): Synthesis of Compounds (1-398) Compound (1-398) was obtained using the same procedure as in Synthesis Example 1, except that compound (X-4) was changed to compound (X-4-398). MS confirmed the target compound (1-398) with m / z(M+H) = 1183.76. [ka]

[0487] Synthesis Example (58): Synthesis of Compound (1-401) Compound (1-401) was obtained using the same procedure as in Synthesis Example 1, except that compound (X-4) was changed to compound (X-4-401). MS confirmed the target compound (1-401) with m / z(M+H) = 1217.84. [ka]

[0488] Synthesis Example (59): Synthesis of Compound (1-407) Compound (1-407) was obtained using the same procedure as in Synthesis Example 1, except that compound (X-4) was changed to compound (X-4-407). MS confirmed the target compound (1-407) with m / z(M+H) = 991.62. [ka]

[0489] Synthesis Example (60): Synthesis of Compounds (1-412) Compound (1-412) was obtained using the same procedure as in Synthesis Example 1, except that compound (X-4) was changed to compound (X-4-412). MS confirmed the target compound (1-412) with m / z(M+H) = 1097.69. [ka]

[0490] Synthesis Example (61): Synthesis of Compounds (1-416) Compound (1-416) was obtained using the same procedure as in Synthesis Example 1, except that compound (X-4) was changed to compound (X-4-416). MS confirmed the target compound (1-416) with m / z(M+H) = 1179.77. [ka]

[0491] Synthesis Example (62): Synthesis of Compounds (1-419) Compound (1-419) was obtained using the same procedure as in Synthesis Example 1, except that compound (X-4) was changed to compound (X-4-419). MS confirmed the target compound (1-419) with m / z(M+H) = 1179.77. [ka]

[0492] Synthesis Example (63): Synthesis of Compound (1-426) Compound (1-426) was obtained using the same procedure as in Synthesis Example 1, except that compound (X-4) was changed to compound (X-4-426). MS confirmed the target compound (1-426) with m / z(M+H) = 1032.34. [ka]

[0493] Synthesis Example (64): Synthesis of Compound (1-432) Compound (1-432) was obtained using the same procedure as in Synthesis Example 1, except that compound (X-4) was changed to compound (X-4-432). MS confirmed the target compound (1-432) with m / z(M+H) = 1005.69. [ka]

[0494] Synthesis Example (65): Synthesis of Compound (1-439) Compound (1-422) was obtained using the same procedure as in Synthesis Example 1, except that compound (X-4) was changed to compound (X-4-439). MS confirmed the target compound (1-439) with m / z(M+H) = 1135.76. [ka]

[0495] Synthesis Example (66): Synthesis of Compound (1-442) Compound (1-442) was obtained using the same procedure as in Synthesis Example 1, except that compound (X-4) was changed to compound (X-4-442). MS confirmed the target compound (1-442) with m / z(M+H) = 1239.83. [ka]

[0496] Synthesis Example (67): Synthesis of Compound (1-444) Compound (1-444) was obtained using the same procedure as in Synthesis Example 1, except that compound (X-4) was changed to compound (X-4-444). MS confirmed the target compound (1-444) with m / z(M+H) = 1188.74. [ka]

[0497] Synthesis Example (68): Synthesis of Compounds (1-449) Compound (1-449) was obtained using the same procedure as in Synthesis Example 1, except that compound (X-4) was changed to compound (X-4-449). MS confirmed the target compound (1-449) with m / z(M+H) = 1284.74. [ka]

[0498] Synthesis Example (69): Synthesis of Compound (1-452) Compound (1-452) was obtained using the same procedure as in Synthesis Example 1, except that compound (X-4) was changed to compound (X-4-452). MS confirmed the target compound (1-452) with m / z(M+H) = 1416.83. [ka]

[0499] Synthesis Example (70): Synthesis of Compounds (1-455) Compound (1-455) was obtained using the same procedure as in Synthesis Example 1, except that compound (X-4) was changed to compound (X-4-455). MS confirmed the target compound (1-455) with m / z(M+H) = 1226.81. [ka]

[0500] Synthesis Example (71): Synthesis of Compounds (1-461) Compound (1-461) was obtained using the same procedure as in Synthesis Example 1, except that compound (X-4) was changed to compound (X-4-461). MS confirmed the target compound (1-461) with m / z(M+H) = 1194.74. [ka]

[0501] Synthesis Example (72): Synthesis of Compounds (1-462) Compound (1-462) was obtained using the same procedure as in Synthesis Example 1, except that compound (X-4) was changed to compound (X-4-462). MS confirmed the target compound (1-462) with m / z(M+H) = 1152.66. [ka]

[0502] Synthesis Example (73): Synthesis of Compound (1-472) Compound (1-472) was obtained using the same procedure as in Synthesis Example 1, except that compound (X-4) was changed to compound (X-4-472). MS confirmed the target compound (1-472) with m / z(M+H) = 1353.03. [ka]

[0503] Synthesis Example (74): Synthesis of Compound (1-473) Compound (1-473) was obtained using the same procedure as in Synthesis Example 1, except that compound (X-4) was changed to compound (X-4-473). MS confirmed the target compound (1-473) with m / z(M+H) = 1330.99. [ka]

[0504] Synthesis Example (75): Synthesis of Compounds (1-474) Compound (1-474) was obtained using the same procedure as in Synthesis Example 1, except that compound (X-4) was changed to compound (X-4-474). MS confirmed the target compound (1-474) with m / z(M+H) = 999.55. [ka]

[0505] The structure of the compound obtained by NMR measurement was confirmed. 1 H-NMR(CDCl3): 8.73(s, 1H), 8.40(s, 1H), 8.10(dd, 1H), 7.90(s, 1H), 7.82(s, 1H), 7.76-7.74(m, 4H), 7.41-7.48(m, 9H), 6.76(s, 1H), 6.33- 6.30(m, 3H), 2.23(s, 3H), 2.10(s, 6H), 1.89(s, 6H), 1.69-1.66(m, 4H), 1.37(s, 6H), 1.12(s, 9H), 0.98(s, 6H), 0.89(s, 9H).

[0506] Synthesis Example (76): Synthesis of Compounds (1-489) Compound (1-489) was obtained using the same procedure as in Synthesis Example 1, except that compound (X-4) was changed to compound (X-4-489). MS confirmed the target compound (1-489) with m / z(M+H) = 1110.56. [ka]

[0507] Synthesis Example (77): Synthesis of Compounds (1-498) Compound (1-498) was obtained using the same procedure as in Synthesis Example 1, except that compound (X-4) was changed to compound (X-4-498). MS confirmed the target compound (1-498) with m / z(M+H) = 1094.58. [ka]

[0508] Synthesis Example (78): Synthesis of Compounds (1-509) Compound (1-509) was obtained using the same procedure as in Synthesis Example 1, except that compound (X-4) was changed to compound (X-4-509). MS confirmed the target compound (1-509) with m / z(M+H) = 1021.53. [ka]

[0509] Synthesis Example (79): Synthesis of Compound (1-522) Compound (1-522) was obtained using the same procedure as in Synthesis Example 1, except that compound (X-4) was changed to compound (X-4-522). MS confirmed the target compound (1-522) with m / z(M+H) = 1133.66. [ka]

[0510] Synthesis Example (80): Synthesis of Compound (1-527) Compound (1-527) was obtained using the same procedure as in Synthesis Example 1, except that compound (X-4) was changed to compound (X-4-527). MS confirmed the target compound (1-527) with m / z(M+H) = 1186.59. [ka]

[0511] Synthesis Example (81): Synthesis of Compounds (1-542) Compound (1-542) was obtained using the same procedure as in Synthesis Example 1, except that compound (X-4) was changed to compound (X-4-542). MS confirmed the target compound (1-542) with m / z(M+H) = 1170.61. [ka]

[0512] Synthesis Example (82): Synthesis of Compound (1-547) Compound (1-547) was obtained using the same procedure as in Synthesis Example 1, except that compound (X-4) was changed to compound (X-4-547). MS confirmed the target compound (1-547) with m / z(M+H) = 1189.68. [ka]

[0513] Synthesis Example (83): Synthesis of Compounds (1-552) Compound (1-552) was obtained using the same procedure as in Synthesis Example 1, except that compound (X-4) was changed to compound (X-4-552). MS confirmed the target compound (1-552) with m / z(M+H) = 1171.73. [ka]

[0514] Synthesis Example (84): Synthesis of Compounds (1-569) Compound (1-569) was obtained using the same procedure as in Synthesis Example 1, except that compound (X-4) was changed to compound (X-4-569). MS confirmed the target compound (1-569) with m / z(M+H) = 1212.64. [ka]

[0515] Synthesis Example (85): Synthesis of Compound (1-573) Compound (1-573) was obtained using the same procedure as in Synthesis Example 1, except that compound (X-4) was changed to compound (X-4-573). MS confirmed the target compound (1-573) with m / z(M+H) = 1068.51. [ka]

[0516] Synthesis Example (86): Synthesis of Compounds (1-582) Compound (1-582) was obtained using the same procedure as in Synthesis Example 1, except that compound (X-4) was changed to compound (X-4-582). MS confirmed the target compound (1-582) with m / z(M+H) = 1206.71. [ka]

[0517] Synthesis Example (87): Synthesis of Compounds (1-584) Compound (1-584) was obtained using the same procedure as in Synthesis Example 1, except that compound (X-4) was changed to compound (X-4-584). MS confirmed the target compound (1-584) with m / z(M+H) = 1049.56. [ka]

[0518] Synthesis Example (88): Synthesis of Compounds (1-589) Compound (1-589) was obtained using the same procedure as in Synthesis Example 1, except that compound (X-4) was changed to compound (X-4-589). MS confirmed the target compound (1-589) with m / z(M+H) = 1186.59. [ka]

[0519] Synthesis Example (89): Synthesis of Compounds (1-600) Compound (1-600) was obtained using the same procedure as in Synthesis Example 1, except that compound (X-4) was changed to compound (X-4-600). MS confirmed the target compound (1-600) with m / z(M+H) = 1170.61. [ka]

[0520] Synthesis Example (90): Synthesis of Compound (1-607) Compound (1-607) was obtained using the same procedure as in Synthesis Example 1, except that compound (X-4) was changed to compound (X-4-607). MS confirmed the target compound (1-607) with m / z(M+H) = 1144.51. [ka]

[0521] Synthesis Example (91): Synthesis of Compound (1-614) Compound (1-614) was obtained using the same procedure as in Synthesis Example 1, except that compound (X-4) was changed to compound (X-4-614). MS confirmed the target compound (1-614) with m / z(M+H) = 1216.51. [ka]

[0522] Synthesis Example (92): Synthesis of Compound (1-619) Compound (1-619) was obtained using the same procedure as in Synthesis Example 1, except that compound (X-4) was changed to compound (X-4-619). MS confirmed the target compound (1-619) with m / z(M+H) = 1128.53. [ka]

[0523] Synthesis Example (93): Synthesis of Compound (1-627) Compound (1-627) was obtained using the same procedure as in Synthesis Example 1, except that compound (X-4) was changed to compound (X-4-627). MS confirmed the target compound (1-627) with m / z(M+H) = 1179.73. [ka]

[0524] Synthesis Example (94): Synthesis of Compound (1-633) Compound (1-633) was obtained using the same procedure as in Synthesis Example 1, except that compound (X-4) was changed to compound (X-4-633). MS confirmed the target compound (1-633) with m / z(M+H) = 1081.72. [ka]

[0525] Synthesis Example (95): Synthesis of Compound (1-638) Compound (1-638) was obtained using the same procedure as in Synthesis Example 1, except that compound (X-4) was changed to compound (X-4-638). MS confirmed the target compound (1-638) with m / z(M+H) = 1211.80. [ka]

[0526] Synthesis Example (96): Synthesis of Compounds (1-640) Compound (1-640) was obtained using the same procedure as in Synthesis Example 1, except that compound (X-4) was changed to compound (X-4-640). MS confirmed the target compound (1-640) with m / z(M+H) = 1027.67. [ka]

[0527] Synthesis Example (97): Synthesis of Compound (1-642) Compound (1-642) was obtained using the same procedure as in Synthesis Example 1, except that compound (X-4) was changed to compound (X-4-642). MS confirmed the target compound (1-642) with m / z(M+H) = 1157.75. [ka]

[0528] Synthesis Example (98): Synthesis of Compound (1-644) Compound (1-644) was obtained using the same procedure as in Synthesis Example 1, except that compound (X-4) was changed to compound (X-4-644). MS confirmed the target compound (1-644) with m / z(M+H) = 1097.69. [ka]

[0529] Synthesis Example (99): Synthesis of Compound (1-646) Compound (1-646) was obtained using the same procedure as in Synthesis Example 1, except that compound (X-4) was changed to compound (X-4-646). MS confirmed the target compound (1-646) with m / z(M+H) = 1117.66. [ka]

[0530] By appropriately changing the raw material compounds, other compounds of the present invention can be synthesized by a method similar to the synthesis example described above.

[0531] <<Methods for Evaluating the Basic Physical Properties of Compounds>> <Preparing the sample> When evaluating the absorption and luminescence properties (fluorescence and phosphorescence) of a compound under evaluation, the compound may be evaluated in a solvent after dissolving it, or in a thin film state. Furthermore, when evaluating in a thin film state, depending on how the compound is used in an organic EL device, the compound may be evaluated as a thin film, or the compound may be dispersed in an appropriate matrix material and then evaluated as a thin film. Here, a thin film obtained by vapor-depositing only the compound under evaluation is called a "single film," and a thin film obtained by applying and drying a coating solution containing the compound under evaluation and a matrix material is called a "coated film."

[0532] Commercially available materials such as PMMA (polymethyl methacrylate) can be used as the matrix material. In this example, the PMMA and the compound to be evaluated are dissolved in toluene, and then a thin film is formed on a transparent quartz support substrate (10 mm x 10 mm) by spin coating to prepare the sample.

[0533] Furthermore, thin film samples where the matrix material is a host compound are prepared as follows: A transparent quartz support substrate (10 mm × 10 mm × 1.0 mm) is fixed to the substrate holder of a commercially available deposition apparatus (manufactured by Choshu Sangyo Co., Ltd.), a molybdenum deposition boat containing the host compound and a molybdenum deposition boat containing the dopant material are attached, and then the vacuum chamber is set to 5 × 10 -4 The pressure was reduced to Pa. Next, the deposition boat containing the host compound and the deposition boat containing the dopant material were heated simultaneously, and the host compound and dopant material were co-deposited to an appropriate film thickness to form a mixed thin film (sample) of the host compound and dopant material. Here, the deposition rate was controlled according to the set mass ratio of the host compound and dopant material.

[0534] <Evaluation of absorption and emission properties> The absorption spectrum of the sample will be measured using a UV-Vis-Near-Infrared spectrophotometer (Shimadzu Corporation, UV-2600). The fluorescence spectrum or phosphorescence spectrum of the sample will be measured using a spectrofluorometer (Hitachi High-Tech Corporation, F-7000).

[0535] For fluorescence spectrum measurement, the sample is excited at an appropriate excitation wavelength at room temperature and photoluminescence is measured. For phosphorescence spectrum measurement, the sample is immersed in liquid nitrogen (temperature 77K) using the attached cooling unit and measured. To observe the phosphorescence spectrum, an optical chopper was used to adjust the delay time from excitation light irradiation to the start of measurement. The sample is excited at an appropriate excitation wavelength and photoluminescence is measured.

[0536] Furthermore, the fluorescence quantum yield (PLQY) is measured using an absolute PL quantum yield analyzer (Hamamatsu Photonics K.K., C9920-02G).

[0537] Next, we will describe the evaluation of the basic physical properties of the polycyclic aromatic compound of the present invention.

[0538] <Evaluation of fluorescence lifetime (delayed fluorescence)> The fluorescence lifetime was measured at 300K using a fluorescence lifetime analyzer (Hamamatsu Photonics K.K., C11367-01). Specifically, both the fast-emission and slow-emission components of the fluorescence lifetime were observed at the maximum emission wavelength measured with an appropriate excitation wavelength. In typical room-temperature fluorescence lifetime measurements of organic EL materials that emit fluorescence, the slow-emission component involving the phosphorescent triplet component is rarely observed due to thermal deactivation of the triplet component. If a slow-emission component is observed in the compound under evaluation, it indicates that the triplet energy with a long excitation lifetime was shifted to the singlet energy due to thermal activation and observed as delayed fluorescence.

[0539] <Calculation of Energy Gap (Eg)> The long-wavelength end A (nm) of the absorption spectrum obtained by the method described above is used to calculate Eg = 1240 / A.

[0540] <Measurement of ionization potential (Ip)> A transparent support substrate (28mm x 26mm x 0.7mm) coated with ITO (indium tin oxide) is fixed to the substrate holder of a commercially available deposition apparatus (manufactured by Choshu Sangyo Co., Ltd.), and a molybdenum deposition boat containing the target compound is attached. Then, the vacuum chamber is set to 5 x 10 -4 The pressure is reduced to Pa. Next, the deposition boat is heated to evaporate the target compound, forming a single film (Neat film) of the target compound.

[0541] The obtained individual films are used as samples, and the ionization potential of the target compound is measured using a photoelectron spectrometer (Sumitomo Heavy Industries, Ltd. PYS-201).

[0542] <Calculation of electron affinity (Ea)> The electron affinity can be estimated from the difference between the ionization potential measured by the method described above and the energy gap calculated by the method described above.

[0543] <Measurement of the lowest excited singlet energy level E(S,Sh) and the lowest excited triplet energy level E(T,Sh)> For a single film of the target compound formed on a glass substrate, the fluorescence spectrum is observed at 77K using the second absorption peak from the long wavelength side of the absorption spectrum as the excitation light, and the lowest excited singlet energy level E(S,Sh) is determined from the short-wavelength shoulder of the peak of the fluorescence spectrum. Also, for a single film of the target compound formed on a glass substrate, the phosphorescence spectrum is observed at 77K using the second absorption peak from the long wavelength side of the absorption spectrum as the excitation light, and the lowest excited triplet energy level E(T,Sh) is determined from the short-wavelength shoulder of the peak of the phosphorescence spectrum.

[0544] <<Fabrication and Evaluation of Organic Light-Emitting Diodes>> Next, we will describe the fabrication and evaluation of organic EL elements using the polycyclic aromatic compounds of the present invention. The compounds of the present invention have an appropriate energy gap (Eg) and a high lowest excitation triplet energy (E T Because it is characterized by a small ΔEST, it is expected to be applied to light-emitting layers and charge transport layers, and is particularly expected to be applied to light-emitting layers.

[0545] <Organic EL element configuration> Organic EL elements were manufactured using the polycyclic aromatic compound of the present invention. [Component Configuration A] Table 1 below shows the material composition of each layer in the organic EL element of Example 1. [Table 1]

[0546] The chemical structures of "HI", "HAT-CN", "HT-1", "HT-2", "BH", "ET-1", "ET-2", "Liq", "Comparative Compound (1)" described in Chinese Publication No. 112961175, "Comparative Compound (2)" described in International Publication No. 2020-022751, "Comparative Compound (3)" described in International Publication No. 2020-251049, "Comparative Compound (4)" described in International Publication No. 2020-251049, and "Comparative Compound (5)" described in International Publication No. 2020-251049 are shown below in Tables 1 and 2.

[0547] [ka]

[0548] [ka]

[0549] (Example 1) A 26mm x 28mm x 0.7mm glass substrate (manufactured by OptoScience Co., Ltd.), which had been polished to 150nm by sputtering an ITO film to a thickness of 180nm, was used as the transparent support substrate. This transparent support substrate was fixed to the substrate holder of a commercially available deposition apparatus (manufactured by Showa Vacuum Co., Ltd.), and molybdenum deposition boats containing HI, HAT-CN, HT-1, HT-2, BH, compound (1-1), ET-1, and ET-2, respectively, and aluminum nitride deposition boats containing Liq, LiF, and aluminum, respectively, were attached.

[0550] The following layers are sequentially formed on the ITO film of the transparent support substrate. The vacuum chamber is 5 × 10 -4 The pressure was reduced to Pa. First, HI was heated and deposited to a thickness of 40 nm. Next, HAT-CN was heated and deposited to a thickness of 5 nm. Then, HT-1 was heated and deposited to a thickness of 45 nm. Next, HT-2 was heated and deposited to a thickness of 10 nm to form a hole layer consisting of four layers. Next, BH and compound (1-1) were heated simultaneously and deposited to a thickness of 25 nm to form an emissive layer. The deposition rate was adjusted so that the mass ratio of BH to compound (1-1) was approximately 97:3. Furthermore, ET-1 was heated and deposited to a thickness of 5 nm. Next, ET-2 and Liq were heated simultaneously and deposited to a thickness of 25 nm to form a two-layer electron layer. The deposition rate was adjusted so that the mass ratio of ET-2 to Liq was approximately 50:50. The deposition rate for each layer was 0.01 to 1 nm / second. Subsequently, LiF was heated and deposited at a deposition rate of 0.01 to 0.1 nm / second to achieve a film thickness of 1 nm. Then, aluminum was heated and deposited to a film thickness of 100 nm to form a cathode, thereby obtaining an organic EL device.

[0551] (Examples 2-99, Comparative Examples 1-5) Organic EL devices for Examples 2-99 and Comparative Examples 1-5 were obtained in the same manner as in Example 1, except that the compounds listed in Table 2 were used instead of compound (1-1).

[0552] <Evaluation items and evaluation methods> The evaluation items include driving voltage (V), emission wavelength (nm), CIE chromaticity (x,y), external quantum efficiency (%), maximum wavelength (nm) and full width at half maximum (nm) of the emission spectrum. These evaluation items are, for example, 1000 cd / m². 2 The value at the time of emission can be used.

[0553] The quantum efficiency of a light-emitting device has two components: internal quantum efficiency and external quantum efficiency. Internal quantum efficiency indicates the proportion of external energy injected into the light-emitting layer of the device as electrons (or holes) that is purely converted into photons. External quantum efficiency, on the other hand, is calculated based on the amount of these photons emitted to the outside of the device. Since some of the photons generated in the light-emitting layer are absorbed or reflected within the device and not emitted to the outside, the external quantum efficiency is lower than the internal quantum efficiency.

[0554] The measurement method for spectral radiance (emission spectrum) and external quantum efficiency is as follows: Using an Advantest R6144 voltage / current generator, the device's radiance was 1000 cd / m². 2 A voltage is applied to cause the element to emit light. A TOPCON SR-3AR spectroradiometer is used to measure the spectral radiance in the visible light region from a direction perpendicular to the light-emitting surface. Assuming the light-emitting surface is a perfectly diffusive 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. Next, the number of photons is integrated across the entire observed wavelength range to obtain the total number of photons emitted from the element. 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. The full width at half maximum of the emission spectrum is determined as the width between the wavelengths above and below the maximum emission wavelength where the intensity is 50%.

[0555] For the organic EL elements of Examples 1 to 7, a DC voltage was applied with the ITO electrode as the anode and the LiF / aluminum electrode as the cathode, resulting in a reading of 1000 cd / m². 2 The characteristics during light emission were measured. The results are shown in Table 2.

[0556] [Table 2] JPEG0007850913000253.jpg255162JPEG0007850913000254.jpg174170 [Industrial applicability]

[0557] The polycyclic aromatic compounds of the present invention are useful as materials for organic devices, particularly as materials for light-emitting layers in organic electroluminescent devices. By using the polycyclic aromatic compounds of the present invention as dopants for light-emitting layers, organic electroluminescent devices with low voltage and high efficiency light emission can be obtained. [Explanation of symbols]

[0558] 100 Organic Electroluminescent Devices 101 circuit board 102 Anode 103 Hole injection layer 104 Hole transport layer 105 Light-emitting layer 106 Electron transport layer 107 Electron injection layer 108 Cathode

Claims

1. A polycyclic aromatic compound having a structure represented by the following formula (1a); 【Chemistry 1】 In formula (1a), Each Z is independently C-R 11, R １１ Each of these is independently hydrogen, a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted diarylamino, a substituted or unsubstituted diheteroarylamino, a substituted or unsubstituted arylheteroarylamino, a substituted or unsubstituted diarylboryl, a substituted or unsubstituted alkyl, a substituted or unsubstituted cycloalkyl, a substituted or unsubstituted alkenyl, a substituted or unsubstituted alkoxy, a substituted or unsubstituted aryloxy, a substituted or unsubstituted arylthio, or a substituted silyl. Two adjacent R １１ These elements are bonded to each other to form or not form a benzene ring, naphthalene ring, indene ring, cyclopentadiene ring, thiophene ring, pyrrole ring, furan ring, benzothiophene ring, benzofuran ring, or indole ring, and at least one hydrogen atom of the formed ring is either unsubstituted or substituted with a substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino, substituted or unsubstituted diheteroarylamino, substituted or unsubstituted arylheteroarylamino, substituted or unsubstituted diarylboryl, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted arylthio, or substituted silyl. X c is >O, >N-R, >C(-R)2, or >S, where the R in >N-R and >C(-R)2 are independently hydrogen, a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted alkyl, or a substituted or unsubstituted cycloalkyl, and the two Rs in >C(-R)2 are bonded to each other to form a ring, or not. Z Ｃ Each of them is independently C-R C, and R Ｃ Each of these is independently hydrogen, a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted diarylamino, a substituted or unsubstituted diheteroarylamino, a substituted or unsubstituted arylheteroarylamino, a substituted or unsubstituted diarylboryl, a substituted or unsubstituted alkyl, a substituted or unsubstituted cycloalkyl, a substituted or unsubstituted alkenyl, a substituted or unsubstituted alkoxy, a substituted or unsubstituted aryloxy, a substituted or unsubstituted arylthio, or a substituted silyl. Two adjacent R Ｃ These may bond to each other to form a benzene ring, naphthalene ring, indene ring, cyclopentadiene ring, thiophene ring, pyrrole ring, furan ring, benzothiophene ring, benzofuran ring, or indole ring, wherein at least one hydrogen atom of the formed ring is substituted or unsubstituted with a substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino, substituted or unsubstituted diheteroarylamino, substituted or unsubstituted arylheteroarylamino, substituted or unsubstituted diarylboryl, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, or substituted or unsubstituted arylthio, or unsubstituted. Y1 is B; X １ and X ２ either one of them is > N - L ＣＹ - R ＣＹ and the other one is > N - GA or > N - GB, LCY is a group in which one phenylene in any of the divalent groups of phenylene, biphenylylene, terphenylylene, fluorenylene, dibenzofuranylene, or any of the divalent groups thereof is replaced by naphthylene, and at least one hydrogen of the phenylene, naphthylene, biphenylylene, terphenylylene, fluorenylene, and dibenzofuranylene may be substituted with an aryl or alkyl group, and the >N-L ＣＹ -R ＣＹ R ＣＹ These are substituted or unsubstituted cycloalkyl groups. GA is a group represented by formula (GA), and GB is a group represented by formula (GB); 【Chemistry 2】 In formulas (GA) and (GB), Z ｇ Each of these is independently C-R g, and R ｇ Each of these is independently hydrogen, aryl, or alkyl, and at least one hydrogen of the aryl may be substituted with an alkyl. However, any one Z in each equation ｇ is the carbon atom bonded to N; A is >O, >N-R, or >S, where R in >N-R is independently hydrogen, a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted alkyl, or a substituted or unsubstituted cycloalkyl; In the above structure, at least one of the aryl ring or heteroaryl ring is condensed with at least one carbon 3 to 24 cycloalkane, or is not condensed, and at least one hydrogen in the cycloalkane may be substituted with an alkyl group, and at least one -CH group in the cycloalkane ２ - is either substituted with -O- or not, and; In the above structure, at least one hydrogen atom is substituted with cyano, halogen, or deuterium, or is not substituted. The substituents used when referring to a compound as substituted or unsubstituted are selected from aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, and substituted silyl compounds. The substituted silyls are all silyls substituted with three substituents selected from the group consisting of alkyl, cycloalkyl, and aryl atoms. The aryls are all aryls having 6 to 30 carbon atoms, the heteroaryls are all heteroaryls having 2 to 30 carbon atoms, the alkyls are all alkyls having 1 to 24 carbon atoms, and the cycloalkyls are all cycloalkyls having 3 to 24 carbon atoms.

2. L ＣＹ The polycyclic aromatic compound according to claim 1, wherein is substituted or unsubstituted 1,4-phenylene, substituted or unsubstituted 4,4'-biphenylene, or substituted or unsubstituted 4,4''-terphenylene.

3. The polycyclic aromatic compound according to Claim 1, wherein N-L CY-R CY is represented by any of the following formulas (CY-4) to (CY-13); 【Transformation 3】 During the ceremony, RCY is a substituted or unsubstituted cycloalkyl group, where R is H. At least one hydrogen atom in the portion corresponding to LCY may be substituted with an aryl or alkyl group.

4. The polycyclic aromatic compound according to claim 3, wherein >N-LCY-RCY is represented by any of formulas (CY-7), (CY-8), or (CY-9), and at least one hydrogen in the portion corresponding to LCY may be substituted with an aryl or alkyl group.

5. The polycyclic aromatic compound according to any one of claims 1 to 4, wherein RCY is unsubstituted 1-adamantyl.

6. X １ and X ２ The polycyclic aromatic compound according to any one of claims 1 to 5, wherein either of the members is >N-GA, and GA is a group represented by any one of the following formulas: (GA-4), (GA-5), (GA-6), (GA-7), (GA-8), (GA-9), (GA-10), (GA-11), (GA-12), or (GA-13); 【Chemistry 4】 In the formula, A is >O, >N-R, or >S, where R in >N-R is independently hydrogen, a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted alkyl, or a substituted or unsubstituted cycloalkyl. At least one hydrogen atom in the formula may be substituted with an alkyl group.

7. A polycyclic aromatic compound according to claim 1, represented by any of the following formulas; 【Transformation 5】 【Transformation 6】 【Transformation 7】 【Transformation 8】 【Chemistry 9】 【Chemistry 10】 【Chemistry 11】 In the formula, Me is methyl, tBu is t-butyl, and D is deuterium.

8. Formula (1-509), Formula (1-527), Formula (1-542), Formula (1-251), Formula (1-252), Formula (1-253), Formula (1-257), Formula (1-589), Formula (1-600), Formula (1-607), (1-627), Formula (1-522), Formula (1- 547), formula (1-552), formula (1-584), formula (1-255), formula (1-614), formula (1-2455), formula (1-246), formula (1-248), formula (1-249), formula (1-250), formula (1-265), formula (1-267), formula (1-26) 9) The polycyclic aromatic compound according to claim 7, represented by any one of the following: formula (1-287), formula (1-303), formula (1-319), formula (1-345), formula (1-349), formula (1-362), formula (1-384), formula (1-387), formula (1-401), formula (1-416), formula (1-419), formula (1-439), formula (1-449), formula (1-452), formula (1-461), formula (1-472), formula (1-473), formula (1-638), formula (1-642), formula (1-646), and formula (1-442).

9. A material for organic devices containing a polycyclic aromatic compound according to any one of claims 1 to 8.

10. An organic electroluminescent element comprising a pair of electrodes consisting of an anode and a cathode, and a light-emitting layer disposed between the pair of electrodes, wherein the light-emitting layer contains a polycyclic aromatic compound according to any one of claims 1 to 8.

11. The organic electroluminescent element according to claim 10, wherein the light-emitting layer comprises a host and the polycyclic aromatic compound as a dopant.

12. The organic electroluminescent element according to claim 11, wherein the host is an anthracene compound, a fluorene compound, or a dibenzochrysene compound.

13. A display device or lighting device comprising an organic electroluminescent element according to any one of claims 10 to 12.

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