KR20230140136A - Polycyclic aromatic compound - Google Patents

Abstract

[Problem] To provide a new compound useful as an organic device material such as an organic EL device.
[Solution] A polycyclic aromatic compound having a structure consisting of one or two or more structural units represented by the following formula (1);

In formula (1), ring A, ring B, and ring C are optionally substituted aryl rings or optionally substituted heteroaryl rings; Y ¹ is B, P, P=O, P=S, Al, Ga, As, Si-R, or Ge-R; X ¹ and X ² are >O, >NR, >C(-R) ₂ , >Si(-R) ₂ , >S, or >Se, provided that at least one is Attribution >NR; At least one hydrogen in the above structure may be replaced with cyano, halogen, or deuterium.

Description

Polycyclic aromatic compound {POLYCYCLIC AROMATIC COMPOUND}

The present invention relates to polycyclic aromatic compounds. The present invention particularly relates to polycyclic aromatic compounds containing nitrogen and boron. The present invention also relates to materials for organic devices containing the polycyclic aromatic compound, organic electroluminescent elements, and display devices and lighting devices.

Conventionally, display devices using light-emitting elements that emit electroluminescence have been studied in various ways because they enable lower power consumption and thinner dimensions. Furthermore, organic electroluminescent elements made of organic materials have been actively studied because they can easily be made lighter or larger. . In particular, regarding the development of organic materials with luminescent properties such as blue, one of the three primary colors of light, and the development of organic materials with charge transport capabilities such as holes and electrons (with the potential to become semiconductors or superconductors), polymer compounds , regardless of low molecular weight compounds, have been actively studied so far.

An organic electroluminescent element has a structure consisting of a pair of electrodes consisting of an anode and a cathode, and one or more layers that are disposed between the pair of electrodes and contain an organic compound. Layers containing organic compounds include a light-emitting layer and a charge transport/injection layer that transports or injects charges such as holes and electrons, and various organic materials suitable for these layers are being developed.

Among them, Patent Document 1 discloses 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 this polycyclic aromatic compound have good external quantum efficiency. Patent Document 2 and Patent Document 3 disclose polycyclic aromatic compounds having a condensed cycloalkane structure. This structure has a low sublimation temperature due to the condensed cycloalkane structure, has high stability, and thus has the effect of obtaining an organic electroluminescent device with excellent efficiency and long life characteristics, and concentration quenching is suppressed by the condensed cycloalkyl structure. Effects can also be expected.

Patent Document 1: International Publication 2015/102118 Patent Document 2: International Publication 2020/017931 Patent Document 3: International Publication 2020/218079

As described above, a variety of materials are being developed as materials for use in organic EL devices. However, in order to increase the selection of materials for organic EL devices, the development of materials made of compounds different from conventional ones is expected to be developed.

The object of the present invention is to provide novel compounds useful as materials for organic devices such as organic EL elements.

The present inventors conducted intensive studies to solve the above problems and succeeded in producing a novel polycyclic aromatic compound with superior luminescent properties compared to the polycyclic aromatic compound having a similar structure to the compound described in Patent Document 1. That is, by combining a condensed cycloalkyl structure that has the effect of suppressing concentration quenching and a specific substitution structure, they succeeded in producing a polycyclic aromatic compound that provides high luminous efficiency, etc. Furthermore, it was discovered that an excellent organic EL device could be obtained by disposing a layer containing this polycyclic aromatic compound between a pair of electrodes to form an organic EL device, and the present invention was completed. That is, the present invention provides the following polycyclic aromatic compounds, and further materials for organic devices containing the following polycyclic aromatic compounds.

The present invention specifically has the following configuration.

<1>

A polycyclic aromatic compound having a structure consisting of one or two or more structural units represented by the following formula (1);

　

In equation (1),

Ring A, ring B, and ring C are each independently a substituted or unsubstituted aryl ring, or a substituted or unsubstituted heteroaryl ring;

Y ¹ is B, P, P=O, P=S, Al, Ga, As, Si-R, or Ge-R, and R of 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} _{_} Aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, or a monovalent group represented by the formula (G), wherein >C(-R) ₂ , and >Si (-R) ₂ R is each independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, and >C (- R) ₂ and the two R of the >Si(-R) ₂ may be combined with each other to form a ring, and among the R of the >NR, the >C(-R) ₂ and the >Si(-R) ₂ At least one R may be bonded to at least one of the A ring and the B ring, or to at least one of the A ring and the C ring through a single bond or a linking group,

However, at least one of X ¹ and X ² is >NR where R is a monovalent group represented by formula (G),

In equation (G),

L is a single bond, alkylene, cycloalkylene, arylene or heteroarylene, of which at least one hydrogen may be substituted, and the (G-A) ring and (G-B) ring are each independently substituted or unsubstituted. It is an aryl ring, or a substituted or unsubstituted heteroaryl ring;

X ³ and X ⁴ are each independently >O, >NR, >C(-R) ₂ , >Si(-R) ₂ , >S, or >Se, and ) ₂ , and the R of >Si(-R) ₂ is each independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl and the two R of the >C(-R) ₂ and the >Si(-R) ₂ may be combined with each other to form a ring, and the R of the >NR, the >C(-R) ₂ and the > At least one R of Si(-R) ₂ is a single bond with at least one of the (GA) ring and the (GB) ring, or a single bond with at least one of the (GA) ring and the (GB) ring, or through a linking group. It can be combined,

In the structure represented by formula (1), at least one of the aryl ring or heteroaryl ring may be condensed with at least one cycloalkane, and at least one hydrogen in the cycloalkane may be substituted, At least one -CH ₂ - in the cycloalkane may be substituted with -O-, and;

At least one hydrogen in the structure represented by formula (1) may be substituted with cyano, halogen, or deuterium.

<2>

The polycyclic aromatic compound described in <1>, wherein the structural unit represented by formula (1) is a structural unit represented by the following formula (2);

　

In equation (2),

Z in ring a, b, and c is each independently N or CR ¹¹ , and R ¹¹ of CR ¹¹ is each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, Arylheteroarylamino, diarylboryl, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio, or substituted silyl, where at least one hydrogen is aryl, heteroaryl, diarylamino, alkyl. , cycloalkyl, or substituted silyl;

The two aryls of the diarylamino are not bonded to each other or are bonded through a linking group, and the two heteroaryls of the diheteroarylamino are not bonded to each other or are bonded through a linking group, and the two heteroaryls of the arylheteroarylamino are not bonded to each other or are bonded through a linking group. Aryl and heteroaryl are not bonded to each other or are bonded to each other through a linking group, and the two aryls of the diarylboryl are not bonded to each other or are bonded to each other through a single bond or linking group;

Two adjacent R ¹¹ may be bonded to each other to form an aryl ring or heteroaryl ring, and the formed aryl ring and heteroaryl ring are respectively aryl, heteroaryl, diarylamino, diheteroarylamino, and arylheteroarylamino. , diarylboryl, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio, or substituted silyl, and at least one hydrogen in these is aryl, heteroaryl, diarylamino, alkyl. , cycloalkyl, or substituted silyl;

The two aryls of the diarylamino are not bonded to each other or are bonded through a linking group, and the two heteroaryls of the diheteroarylamino are not bonded to each other or are bonded through a linking group, and the two heteroaryls of the arylheteroarylamino are not bonded to each other or are bonded through a linking group. Aryl and heteroaryl are not bonded to each other or are bonded to each other through a linking group, and the two aryls of the diarylboryl are not bonded to each other or are bonded to each other through a single bond or linking group;

Z=Z may each independently be >O, >NR, >C(-R) ₂ , >Si(-R) ₂ , >S, or >Se, wherein the >NR and the >C(-R) ₂ and R of >Si(-R) ₂ is each independently hydrogen, aryl, heteroaryl, alkyl, or cycloalkyl, and at least one hydrogen therein is aryl, heteroaryl, diarylamino, alkyl, or cycloalkyl. may be further substituted with alkyl or substituted silyl, and the two R of >C(-R) ₂ and >Si(-R) ₂ may be bonded to each other to form a ring;

Y ¹ is B, or P=O,

_X ^{1 and} _{_} Alkyl, cycloalkyl, or a monovalent group represented by the formula (G-2), wherein at least one hydrogen is further substituted with aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl. R of >C(-R) ₂ and >Si(-R) ₂ may be hydrogen, aryl, heteroaryl, alkyl, or cycloalkyl, and at least one hydrogen thereof may be aryl, heteroaryl, or cycloalkyl. It may be further substituted with aryl, diarylamino, alkyl, cycloalkyl, or substituted silyl, and the two R of >C(-R) ₂ and >Si(-R) ₂ may be bonded to each other to form a ring. And at least one R among R of >NR, >C(-R) ₂ and R of >Si(-R) ₂ is -O-, -S-, -C(-R) ₂ - Alternatively, it may be bonded to one or two C of Z which is CR ¹¹ by a single bond, provided that at least one of X ¹ and X ² is a monovalent group where R is represented by the formula (G-2) > NR,

In formula (G-2),

Z ^G in the Ga ring and Gb ring is each independently N or CR ¹² , and R ¹² of CR ¹² is each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, or arylhetero. Arylamino, diarylboryl, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio, or substituted silyl, where at least one hydrogen is aryl, heteroaryl, diarylamino, alkyl, or cyclo. It may be substituted with alkyl or substituted silyl;

The two aryls of the diarylamino are not bonded to each other or are bonded through a linking group, and the two heteroaryls of the diheteroarylamino are not bonded to each other or are bonded through a linking group, and the two heteroaryls of the arylheteroarylamino are not bonded to each other or are bonded through a linking group. Aryl and heteroaryl are not bonded to each other or are bonded to each other through a linking group, and the two aryls of the diarylboryl are not bonded to each other or are bonded to each other through a single bond or linking group;

Two adjacent R ¹² may be bonded to each other to form an aryl ring or heteroaryl ring, and the formed aryl ring and heteroaryl ring are respectively aryl, heteroaryl, diarylamino, diheteroarylamino, and arylheteroaryl. It may be substituted with amino, diarylboryl, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio, or substituted silyl, and at least one hydrogen in these is aryl, heteroaryl, diarylamino, It may be substituted with alkyl, cycloalkyl, or substituted silyl;

The two aryls of the diarylamino are not bonded to each other or are bonded through a linking group, and the two heteroaryls of the diheteroarylamino are not bonded to each other or are bonded through a linking group, and the two heteroaryls of the arylheteroarylamino are not bonded to each other or are bonded through a linking group. Aryl and heteroaryl are not bonded to each other or are bonded to each other through a linking group, and the two aryls of the diarylboryl are not bonded to each other or are bonded to each other through a single bond or linking group;

Z ^G =Z ^G may each independently be >O, >NR, >C(-R) ₂ , >Si(-R) ₂ , >S, or >Se, and the >NR, the >C(-R ) ₂ and the R of >Si(-R) ₂ are each independently hydrogen, aryl, heteroaryl, substituted alkyl, or cycloalkyl, and at least one hydrogen in these is aryl, heteroaryl, diarylamino , may be substituted with alkyl, cycloalkyl, or substituted silyl, and the two R of >C(-R) ₂ and >Si(-R) ₂ may be bonded to each other to form a ring;

X ³ and X ⁴ are each independently >O, >NR, >C(-R) ₂ , >Si(-R) ₂ , >S, or >Se, and ) ₂ , and the >Si(-R) ₂ , R is each independently hydrogen, aryl, heteroaryl, alkyl, or cycloalkyl, and at least one hydrogen in these is aryl, heteroaryl, It may be substituted with diarylamino, alkyl, cycloalkyl, or substituted silyl, and the two R of >C(-R) ₂ and >Si(-R) ₂ may be bonded to each other to form a ring, and At least one R of the >NR, the >C(-R) ₂ and the >Si(-R) ₂ is -O-, -S-, -C(-R ¹⁴ ) ₂ - or a single bond may be bonded to one or two Cs in Z ^G which is CR ¹² , and R ¹⁴ of -C(-R ¹⁴ ) ₂ - is hydrogen, alkyl, or cycloalkyl,

L is a single bond, arylene or heteroarylene, and at least one hydrogen of the arylene and the heteroarylene may be substituted with aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl. ,

In the structure represented by formula (2), at least one of the aryl ring or heteroaryl ring may be condensed with at least one cycloalkane, and at least one hydrogen in the cycloalkane may be substituted, At least one -CH ₂ - in the cycloalkane may be substituted with -O-, and;

At least one hydrogen in the structure represented by formula (2) may be substituted with cyano, halogen, or deuterium.

<3>

In formula (2), Y ¹ is B, and in the above structure, at least one of the aryl ring or heteroaryl ring is condensed with at least one cycloalkane, and at least one hydrogen in the cycloalkane is may be substituted, and at least one -CH ₂ - in the cycloalkane may be substituted with -O-.

<4>

The polycyclic aromatic compound according to any one of <1> to <3>, which is represented by the following formula.

<5>

A material for an organic device containing the polycyclic aromatic compound according to any one of <1> to <4>.

<6>

Organic electroluminescence, 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 the polycyclic aromatic compound according to any one of <1> to <4>. device.

<7>

The organic electroluminescent device according to <6>, wherein the light-emitting layer includes a host and the polycyclic aromatic compound as a dopant.

<8>

The organic electroluminescent device according to <7>, wherein the host is an anthracene compound, a fluorene compound, or a dibenzochrysene compound.

<9>

A display device or lighting device including the organic electroluminescent element according to any one of <6> to <8>.

According to the present invention, a novel polycyclic aromatic compound useful as a material for organic devices such as organic electroluminescent elements is provided. The polycyclic aromatic compound of the present invention can be used in the production of organic devices such as organic electroluminescent elements.

1 is a schematic cross-sectional view showing an example of an organic electroluminescent device.
Figure 2 is an energy level diagram showing the energy relationship between the host, assisting dopant, and emitting dopant of a TAF device using a general fluorescent dopant.
Figure 3 is an energy level diagram showing an example of the energy relationship between the host, assisting dopant, and emitting dopant in the organic electroluminescent device of one embodiment of the present invention.

Below, the present invention will be described in detail. The description of the structural requirements described below may be based on representative embodiments or specific examples, but the present invention is not limited to such embodiments. In addition, in this specification, the numerical range indicated using “~” means a range that includes the numerical values written before and after “~” as the lower limit and upper limit. In addition, in this specification, “hydrogen” in the description of the structural formula means “hydrogen atom (H).” In this specification, the organic electroluminescent device is sometimes referred to as an organic EL device.

In this specification, the chemical structure or substituent is sometimes expressed by the number of carbon atoms. In the case where the chemical structure is substituted by a substituent or when the substituent is further substituted by a substituent, the number of carbon atoms refers to the number of carbon atoms in the chemical structure or each substituent. It does not mean the total carbon number of the structure and substituents, or the total carbon number of substituents and substituents. For example, “substituent B of carbon number Y substituted by substituent A of carbon number X” means that “substituent A of carbon number It is not the total number of carbons in B. Also, for example, “substituent B of carbon number Y substituted by substituent A” means that “substituent A (with no limitation on carbon number)” is substituted for “substituent B of carbon number Y”, and carbon number Y is substituent A and It is not the total carbon number of substituent B.

Since the chemical structural formula described in this specification (including general formulas drawn as Markush structural formulas such as formula (1) described later) is a planar structural formula, in reality, it is a variety of structural formulas such as enantio isomers, diastereo isomers, and rotational isomers. Isomer structures sometimes exist. In this specification, unless otherwise specified, the described compound may have any isomeric structure conceivable from its planar structural formula, or may be a mixture of possible isomers in any ratio.

<1. Polycyclic aromatic compounds>

The polycyclic aromatic compound of the present invention is a polycyclic aromatic compound having a structure consisting of one or two or more structural units represented by formula (1). The polycyclic aromatic compound of the present invention has a high luminescence quantum yield (PLQY), a narrow luminescence half width, and excellent color purity.

In formula (1), ring A, ring B, and ring C are each independently an optionally substituted aryl ring or optionally substituted heteroaryl ring.

The aryl ring or heteroaryl ring in ring A, ring B, and ring C is preferably bonded to either Y ¹ , X ¹ , or X ² in a 5-membered ring or a 6-membered ring. “It is bonded to Y ¹ and any one of X ^{1 and} It means that a ring is formed by further condensation. In other words, it means that the 5-membered ring or 6-membered ring constituting all or part of the ring is bonded to Y ¹ and any one of X ¹ and X ² . In the aryl ring or heteroaryl ring of ring A, ring B, and ring C, two or three consecutive ring atoms (carbon atoms) are directly bonded to Y ¹ and any one of X ¹ and X ² You can do it. That is, in the aryl ring or heteroaryl ring in ring B, two consecutive ring atoms (carbon atoms) of any pair are directly bonded to Y ¹ and X ¹ , and the aryl ring in ring C or In the heteroaryl ring, any two consecutive ring atoms ⁽ carbon atoms) are directly bonded to Y ¹ and Three consecutive ring atoms (carbon atoms) are directly bonded to Y ¹ , X ¹ and X ² .

Examples of the “aryl ring” in the A ring, B ring, or C ring of formula (1) include an aryl ring having 6 to 30 carbon atoms, with an aryl ring having 6 to 16 carbon atoms being preferable. An aryl ring with 6 to 12 carbon atoms is more preferable, and an aryl ring with 6 to 10 carbon atoms is particularly preferable.

Specific examples of “aryl rings” include monocyclic benzene rings, bicyclic biphenyl rings, condensed bicyclic naphthalene rings, indene rings, and tricyclic terphenyl rings (m-terphenyl, o-terphenyl, p-terphenyl). ), acenaphthylene ring, fluorene ring, phenalene ring, phenanthrene ring, anthracene ring, condensed 3-ring system, triphenylene ring, pyrene ring, naphthacene ring, chrysene ring, fused 5-ring system, perylene ring, Pentacene pills, etc. can be mentioned. Additionally, the fluorene ring, benzofluorene ring, and indene ring also include structures in which a fluorene ring, a benzofluorene ring, and a cyclopentane ring are spiro-bonded, respectively. In addition, in the fluorene ring, benzofluorene ring and indene ring, two of the two hydrogens of methylene are respectively substituted with alkyl such as methyl as the first substituent described later, resulting in dimethylfluorene ring, dimethylbenzofluorene ring and dimethyl. It also includes those made of denwan, etc.

Examples of the “heteroaryl ring” in ring A, ring B, or ring C of formula (1) include heteroaryl rings having 2 to 30 carbon atoms, and heteroaryl rings having 2 to 25 carbon atoms are preferable. A heteroaryl ring with 2 to 20 carbon atoms is more preferable, a heteroaryl ring with 2 to 15 carbon atoms is even more preferable, and a heteroaryl ring with 2 to 10 carbon atoms is particularly preferable. Examples of the “heteroaryl ring” include heterocycles containing 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen in addition to carbon as ring atoms.

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, benzoimidazole ring, benzoxazole ring, benzothiazole ring, 1H-benzotriazole ring, quinoline ring. , isoquinoline ring, cinnoline ring, quinazoline ring, quinoxaline ring, phthalazine ring, naphthridine ring, purine ring, pteridine ring, carbazole ring, carborine ring, acridine ring, phenoxathione ring, pe Noxanine ring, phenothiazine ring, phenazine ring, phenaxacillin ring, indolizine ring, furan ring, benzofuran ring, isobenzofuran ring, dibenzofuran ring, thiophene ring, benzothiophene ring, dibenzothiophene ring , furazane ring, thiantrene ring, indolocarbazole ring, benzoindolocarbazole ring, dibenzoindolocarbazole ring, naphthobenzofuran ring, dioxine ring, dihydroacridine ring, xanthene ring, thioxanthene ring. , dibenzodioxine ring, etc. In addition, two of the two hydrogens of the dihydroacridine ring, xanthene ring, thioxanthene ring, silver, and methylene are each replaced with an alkyl such as methyl as the first substituent described later to form dimethyldihydroacridine ring, dimethylxanthene ring, and dimethylthio. It is also preferable that it is a xanthene ring or the like. Additionally, dicyclic bipyridine rings, phenylpyridine rings, and pyridylphenyl rings, and tricyclic terpyridine rings, bispyridylphenyl rings, and pyridylbiphenyl rings, can also be cited as “heteroaryl rings.” In addition, “heteroaryl ring” shall also include pyran ring.

In addition, the following formula (BO) is also included in the heteroaryl ring.

　

At least one hydrogen in the “aryl ring” or “heteroaryl ring” is the first substituent, substituted or unsubstituted “aryl”, substituted or unsubstituted “heteroaryl”, or substituted or unsubstituted “. Diarylamino (two aryls may not be bonded to each other or may be bonded through a linking group)”, substituted or unsubstituted “diheteroarylamino (two heteroaryls may not be bonded to each other or may be bonded through a single bond or linking group)” may be bonded)”, substituted or unsubstituted “arylheteroarylamino (aryl and heteroaryl are not bonded to each other or are bonded through a linking group)”, substituted or unsubstituted “diarylboryl (two aryls)” may not be bonded to each other or may be bonded through a single bond or linking group)”, substituted or unsubstituted “alkyl”, substituted or unsubstituted “alkenyl”, substituted or unsubstituted “cycloalkyl”, substituted or It may be substituted with unsubstituted “alkoxy,” substituted or unsubstituted “aryloxy,” substituted or unsubstituted “arylthio,” or “substituted silyl.”

Specifically, “aryl” is a monovalent group with one hydrogen removed from the above-mentioned “aryl ring”, and examples include aryl with 6 to 30 carbon atoms, with aryl with 6 to 24 carbon atoms being preferred, and 6 carbon atoms. Aryl with -20 carbon atoms is more preferable, aryl with 6 to 16 carbon atoms is still more preferable, aryl with 6 to 12 carbon atoms is particularly preferable, and aryl with 6 to 10 carbon atoms is most preferable.

In addition, “heteroaryl” is a monovalent group obtained by removing one hydrogen from the above-mentioned “heteroaryl ring”, and examples include heteroaryl having 2 to 30 carbon atoms, with heteroaryl having 2 to 25 carbon atoms being preferable. Heteroaryl with 2 to 20 carbon atoms is more preferable, heteroaryl with 2 to 15 carbon atoms is even more preferable, and heteroaryl with 2 to 10 carbon atoms is particularly preferable. Examples of heteroaryl include heterocycles containing 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen in addition to carbon as ring atoms.

As the first substituent, “diarylamino which may be substituted (two aryls may be bonded through a linking group or may not be bonded)” and “diheteroarylamino which may be substituted (two heteroaryls may be bonded through a linking group)” aryl in each of “(may or may not be bonded through)” and “arylheteroarylamino which may be substituted (aryl and heteroaryl may or may not be bonded through a linking group)” As the or heteroaryl, those described above as “aryl” or “heteroaryl” can be cited.

Diarylamino as the first substituent (two aryls may be bonded through a linking group or may not be bonded), diheteroarylamino as the first substituent (two heteroaryls may be bonded through a linking group, bonding may not be bonded), and for arylheteroarylamino (aryl and heteroaryl may be bonded through a linking group or may not be bonded) as the first substituent, "may be bonded through a linking group or may not be bonded" The description “may be” indicates that, for example, two phenyl groups of a diphenylamino group form a bond as a linking group, as shown below. This description also applies to diheteroarylamino and arylheteroarylamino, formed from aryl or heteroaryl.

　　

_{The linking} ^{group specifically} includes _> O, ^> NR ^may _be mentioned, ^and R ^{R X} _in ( ^-R X ^Y includes >O, >NR ^Y , >C(-R ^Y ) ₂ , >Si(-R ^Y ) ₂ , >S, >CO, >CS, >SO, >SO ₂ , and >Se. and ^RY is each independently alkyl, cycloalkyl, aryl, or heteroaryl, and these may be substituted with alkyl, cycloalkyl, aryl, or heteroaryl. ^{However , in the} _{case where} Furthermore, alkenylene can also be mentioned as a linking group. Any hydrogen ^of the alkenylene may each independently be substituted with ^R It may be substituted.

Additionally, in this specification, when simply described as “diarylamino,” “diheteroarylamino,” or “arylheteroarylamino,” unless specifically limited, “two aryls may be bonded through a linking group,” respectively. “The two heteroaryls may be bonded through a linking group or may not be bonded,” and “The aryl and heteroaryl may be bonded through a linking group or not bonded.” The explanation has been added.

In addition, the "alkyl" as the first substituent may be either straight chain or branched chain, and examples include straight chain alkyl with 1 to 24 carbon atoms or branched chain alkyl with 3 to 24 carbon atoms. Alkyl with 1 to 18 carbon atoms (branched chain alkyl with 3 to 18 carbon atoms) is preferable, alkyl with 1 to 12 carbon atoms (branched chain alkyl with 3 to 12 carbon atoms) is more preferable, and alkyl with 1 to 8 carbon atoms (branched chain alkyl with 3 to 12 carbon atoms) is more preferable. Branched chain alkyl with ~8 carbon atoms) is more preferable, alkyl with 1 to 6 carbon atoms (branched chain alkyl with 3 to 6 carbon atoms) is particularly preferable, and alkyl with 1 to 5 carbon atoms (branched chain alkyl with 3 to 5 carbon atoms) is more preferable. This is most desirable.

Specific alkyl examples include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl (t-amyl), n. -hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, t-octyl (1,1,3 , 3-tetramethylbutyl), 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 2,6-dimethyl-4-heptyl, 3,5,5- Trimethylhexyl, n-decyl, n-undecyl, 1-methyldecyl, n-dodecyl, n-tridecyl, 1-hexylheptyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-hepta Decyl, n-octadecyl, n-eicosyl, etc. can be mentioned. Also, for example, 1-ethyl-1-methylpropyl, 1,1-diethylpropyl, 1,1-dimethylbutyl, 1-ethyl-1-methylbutyl, 1,1,4-trimethylpentyl, 1, 1,2-trimethylpropyl, 1,1-dimethyloctyl, 1,1-dimethylpentyl, 1,1-dimethylheptyl, 1,1,5-trimethylhexyl, 1-ethyl-1-methylhexyl, 1-ethyl- 1,3-dimethylbutyl, 1,1,2,2-tetramethylpropyl, 1-butyl-1-methylpentyl, 1,1-diethylbutyl, 1-ethyl-1-methylpentyl, 1,1,3 -Trimethylbutyl, 1-propyl-1-methylpentyl, 1,1,2-trimethylpropyl, 1-ethyl-1,2,2-trimethylpropyl, 1-propyl-1-methylbutyl, 1,1-dimethylhexyl etc. can also be mentioned.

As a substituent containing the above "alkyl", tertiary alkyl represented by the formula (tR) below is a particularly preferred substituent for the aryl ring or heteroaryl ring in the A ring, B ring, and C ring. It is one. This is because the distance between molecules increases due to such bulky substituents, thereby improving the luminescence quantum yield (PLQY). Additionally, a substituent in which the tertiary alkyl represented by the formula (tR) is substituted by another substituent as the second substituent is also preferable. Specifically, diarylamino substituted with tertiary alkyl represented by (tR) (two aryls may not be bonded to each other or may be bonded through a linking group), and diarylamino substituted with tertiary alkyl represented by (tR). and benzocarbazolyl (preferably N-benzocarbazolyl) substituted with carbazolyl (preferably N-carbazolyl) or tertiary alkyl represented by (tR). As for “diarylamino (two aryls may not be bonded to each other or may be bonded through a linking group)”, groups described below as “first substituents” can be mentioned. Substitution forms for the group of the formula (tR) for diarylamino (two aryls may not be bonded to each other or may be bonded through a linking group), carbazolyl, and benzocarbazolyl include the aryl ring in these groups, or Examples include where some or all of the hydrogen in the benzene ring is replaced with a group of the formula (tR).

　　

In formula (tR), R ^a , R ^b , and R ^c are each independently alkyl having 1 to 24 carbon atoms, and any -CH ₂ - in the alkyl may be substituted with -O-, and the formula ( The group represented by tR) is substituted for at least one hydrogen in the structure containing the structural unit represented by formula (1) in *.

The “alkyl having 1 to 24 carbon atoms” for R ^a , R ^b and R ^c may be either straight chain or branched chain, for example, straight chain alkyl having 1 to 24 carbon atoms or branched alkyl having 3 to 24 carbon atoms, Alkyl with 1 to 18 carbon atoms (branched chain alkyl with 3 to 18 carbon atoms), alkyl with 1 to 12 carbon atoms (branched chain alkyl with 3 to 12 carbon atoms), alkyl with 1 to 6 carbon atoms (branched chain alkyl with 3 to 6 carbon atoms) , alkyl with 1 to 4 carbon atoms (branched chain alkyl with 3 to 4 carbon atoms).

The total number of carbon atoms of R ^a , R ^b , and R ^c in formula (tR) of formula (1) is preferably 3 to 20 carbon atoms, and particularly preferably 3 to 10 carbon atoms.

Specific alkyls for R ^a , R ^b , and R ^c 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-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 2,6-dimethyl-4-heptyl, 3,5,5-trimethylhexyl, n-decyl, n -Undecyl, 1-methyldecyl, n-dodecyl, n-tridecyl, 1-hexylheptyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, n -Eicosil, etc. can be mentioned.

Examples of the group represented by the formula (tR) include t-butyl, t-amyl, 1-ethyl-1-methyl propyl, 1,1-diethylpropyl, 1,1-dimethylbutyl, and 1-ethyl-1. -Methyl butyl, 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-1-methylhexyl, 1-ethyl-1,3-dimethylbutyl, 1,1,2,2-tetramethylpropyl, 1-butyl- 1-Methylpentyl, 1,1-diethyl butyl, 1-ethyl-1-methylpentyl, 1,1,3-trimethylbutyl, 1-propyl-1-methylpentyl, 1,1,2-trimethylpropyl, 1 -Ethyl-1,2,2-trimethylpropyl, 1-propyl-1-methylbutyl, 1,1-dimethylhexyl, etc. Among these, t-butyl and t-amyl are preferred.

Additionally, “cycloalkyl” as the first substituent includes cycloalkyl with 3 to 24 carbon atoms, cycloalkyl with 3 to 20 carbon atoms, cycloalkyl with 3 to 16 carbon atoms, cycloalkyl with 3 to 14 carbon atoms, and cycloalkyl with 5 to 10 carbon atoms. , cycloalkyl with 5 to 8 carbon atoms, cycloalkyl with 5 to 6 carbon atoms, cycloalkyl with 5 carbon atoms, etc. As listed below, cyclohexyl in this specification includes monocyclic cyclohexyl and the like, as well as polycyclic ones such as adamantyl.

Specific cycloalkyl examples include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, bicyclo[1.1.0]butyl, bicyclo[1.1.1]pentyl, and bicyclo[. 2.1.0]pentyl, bicyclo[2.1.1]hexyl, bicyclo[3.1.0]hexyl, bicyclo[2.2.1]heptyl(norbornyl), bicyclo[2.2.2]octyl, adamantyl, Diamantyl, decahydronaphtharenyl, decahydroazulenyl, and alkyl (especially methyl) substituted products having 1 to 5 carbon atoms thereof.

Examples of “alkenyl” as the first substituent include straight-chain alkenyl with 2 to 24 carbon atoms or branched alkenyl with 4 to 24 carbon atoms. Alkenyl with 2 to 18 carbon atoms is preferable, alkenyl with 2 to 12 carbon atoms is more preferable, alkenyl with 2 to 6 carbon atoms is even more preferable, and alkenyl with 2 to 4 carbon atoms is especially preferable.

Specific examples of “alkenyl” include vinyl, allyl, butadienyl, and the like.

Moreover, examples of “alkoxy” as the first substituent include straight-chain alkoxy with 1 to 24 carbon atoms or branched chain alkoxy with 3 to 24 carbon atoms. Alkoxy with 1 to 18 carbon atoms (branched chain alkoxy with 3 to 18 carbon atoms) is preferable, alkoxy with 1 to 12 carbon atoms (branched chain alkoxy with 3 to 12 carbon atoms) is more preferable, and alkoxy with 1 to 6 carbon atoms (branched chain alkoxy with 3 to 12 carbon atoms) is more preferable. Branched-chain alkoxy with ~6 carbon atoms) is more preferable, and alkoxy with 1-5 carbon atoms (branched-chain alkoxy with 3-5 carbon atoms) is particularly preferable.

Specific alkoxy groups include methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, s-butoxy, t-butoxy, t-amyloxy, pentyloxy, hexyloxy, heptyloxy, octyloxy, etc. can be mentioned.

As “arylthio” as the first substituent, it is a group in which the hydrogen of the -SH group is substituted with aryl, and the above-described aryl can be cited.

Additionally, examples of “substituted silyl” as the first substituent include silyl substituted with three substituents selected from the group consisting of alkyl, cycloalkyl, and aryl. Examples include trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, alkyldicycloalkylsilyl, trialylsilyl, dialkylarylsilyl, and alkyldiarylsilyl.

Examples of “trialkylsilyl” include groups in which three hydrogens in silyl are each independently substituted with alkyl, and this alkyl can be cited as the group described as “alkyl” in the first substituent described above. Alkyl preferred for substitution is alkyl having 1 to 5 carbon atoms, and specific examples include methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, t-butyl, and t-amyl.

Specific trialkylsilyl includes trimethylsilyl, triethylsilyl, tripropylsilyl, triisopropylsilyl, tributylsilyl, trisec-butylsilyl, trit-butylsilyl, trit-amylsilyl, ethyldimethylsilyl, and propyldimethyl. Silyl, isopropyldimethylsilyl, butyldimethylsilyl, sec-butyldimethylsilyl, t-butyldimethylsilyl, t-amyldimethylsilyl, methyldiethylsilyl, propyldiethylsilyl, isopropyldiethylsilyl, butyldiethylsilyl, sec-butyldiethylsilyl, t-butyldiethylsilyl, t-amyldiethylsilyl, methyldipropylsilyl, ethyldipropylsilyl, butyldipropylsilyl, sec-butyldipropylsilyl, t-butyldipropylsilyl, t-amyldipropylsilyl, methylisopropylsilyl, ethyldiisopropylsilyl, butyldiisopropylsilyl, sec-butyldiisopropylsilyl, t-butyldiisopropylsilyl, t-amyldiisopropylsilyl, etc. You can.

“Tricycloalkylsilyl” includes groups in which three hydrogens in the silyl group are each independently substituted with cycloalkyl, and this cycloalkyl refers to the group described as “cycloalkyl” in the first substituent described above. You can. Cycloalkyl preferred for substitution is cycloalkyl having 5 to 10 carbon atoms, specifically cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, bicyclo[1.1.1]pentyl, and 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, decahydronaphtharenyl, Decahydroazulenyl, etc. can be mentioned.

Specific examples of tricycloalkylsilyl include tricyclopentylsilyl, tricyclohexylsilyl, and the like.

Specific examples of dialkylcycloalkylsilyl in which two alkyls and one cycloalkyl are substituted and alkyldicycloalkylsilyl in which one alkyl and two cycloalkyls are substituted are substituted with a group selected from the above-mentioned specific alkyl and cycloalkyl. Examples include silyl.

Specific examples of dialkylarylsilyl substituted with two alkyls and one aryl, alkyldiarylsilyl substituted with one alkyl and two aryls, and triarylsilyl substituted with three aryls include the specific alkyls and aryls described above. and silyl substituted with a group selected from . Specific examples of triarylsilyl include triphenylsilyl.

In addition, as "aryl" in "diarylboryl (two aryls are not bonded to each other or are bonded through a single bond or linking group)" of the first substituent, the above-mentioned description of aryl can be cited. Additionally, these two aryls may be linked through a single bond or a linking group (for example, >C(-R) ₂ , >O, >S, or >NR). Here, R of >C(-R) ₂ and >NR is aryl, heteroaryl, diarylamino (two aryls may not be bonded to each other or may be bonded through a linking group), alkyl, cycloalkyl, alkoxy, or It is aryloxy (above, first substituent), and the first substituent may be further substituted with aryl, heteroaryl, alkyl, or cycloalkyl (above, second substituent). Specific examples of these groups include the above-mentioned first substituent. The description of aryl, heteroaryl, diarylamino (two aryls may not be bonded to each other or may be bonded through a linking group), alkyl, cycloalkyl, alkoxy, or aryloxy may be cited.

The first substituent is substituted or unsubstituted “aryl”, substituted or unsubstituted “heteroaryl”, or substituted or unsubstituted “diarylamino (two aryls are not bonded to each other or are bonded through a linking group). ”, substituted or unsubstituted “diheteroarylamino (two heteroaryls are not bonded to each other or are bonded through a single bond or linking group)”, substituted or unsubstituted “arylheteroarylamino (aryl and heteroaryl) are not bonded to each other or are bonded through a single bond or linking group)”, substituted or unsubstituted “diarylboryl (two aryls are not bonded to each other or are bonded through a single bond or linking group)”, substituted or unsubstituted “alkyl”, substituted or unsubstituted “cycloalkyl”, substituted or unsubstituted “alkenyl”, substituted or unsubstituted “alkoxy”, substituted or unsubstituted “aryloxy”, substituted or unsubstituted. Substituted “arylthio” or substituted “silyl” may be substituted or unsubstituted, and at least one hydrogen therein may be substituted with a second substituent. The second substituent preferably includes aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl, and specific examples thereof include "aryl", "heteroaryl" as the first substituent, Reference may be made to the description of “diarylamino,” “alkyl,” “cycloalkyl,” or “substituted silyl.” In addition, for aryl and heteroaryl as the second substituent, at least one hydrogen thereof is aryl such as phenyl (specific examples are the groups described above), alkyl such as methyl or t-butyl (specific examples are the groups described above) ) or structures substituted with cycloalkyl such as cyclohexyl (specific examples are the groups described above) are also included in aryl or heteroaryl as the second substituent. As an example, when the second substituent is carbazolyl, carbazolyl in which at least one hydrogen at the 9th position is substituted with an aryl such as phenyl, an alkyl such as methyl, or a cycloalkyl such as cyclohexyl is also substituted for the second substituent. Included in heteroaryl as a substituent. This description can also be applied to descriptions of other first and second substituents in this specification.

The emission wavelength can be adjusted by the structural steric hindrance, electron donating, and electron withdrawing properties of the first substituent. Preferably, it is a group represented by the following structural formula, 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-di-t-butylcarbazolyl and phenoxy, 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, 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-butyl carbazolyl are preferred.

In the structural formula below, “Me” represents methyl, “tBu” represents t-butyl, “tAm” represents t-amyl, “tOct” represents t-octyl, and * represents the binding position.

　

　

Polycyclic aromatic compounds having a structure consisting of one or two or more structural units represented by formula (1) include tertiary alkyl (t-butyl or t-amyl, etc.), neo-alkyl, etc. represented by the above-mentioned formula (tR). It is preferable that the structure contains at least one pentyl or adamantyl, and it is preferable that it contains a tertiary alkyl (t-butyl or t-amyl, etc.) represented by the formula (tR). This is because the distance between molecules increases due to such bulky substituents, thereby improving the luminescence quantum yield (PLQY). Additionally, as a substituent, diarylamino (two aryls may not be bonded to each other or may be bonded through a linking group) is also preferable. Furthermore, diarylamino substituted with a group of the formula (tR) (the two aryls may not be bonded to each other or may be bonded through a linking group), carbazolyl substituted with a group of the formula (tR) (preferably, N- carbazolyl) or benzocarbazolyl substituted with a group of the formula (tR) (preferably N-benzocarbazolyl) is also preferred. Substitution forms for the group of the formula (tR) for diarylamino (two aryls may not be bonded to each other or may be bonded through a linking group), carbazolyl, and benzocarbazolyl include the aryl ring in these groups, or Examples include where some or all of the hydrogen in the benzene ring is replaced with a group of the formula (tR).

In formula (1), Y ¹ is each independently B, P, P=O, P=S, Al, Ga, As, Si-R, or Ge-R, and B or P=O is preferred. , B is most preferable. R in Si-R and Ge-R is aryl with 6 to 12 carbon atoms, alkyl with 1 to 6 carbon atoms, or cycloalkyl with 3 to 14 carbon atoms. R of Si-R and Ge-R in Y ¹ in formula (1) is aryl, alkyl, or cycloalkyl. Examples of the aryl, alkyl, or cycloalkyl include the groups described above. In particular, aryl with 6 to 10 carbon atoms (e.g. phenyl, naphthyl, etc.), alkyl with 1 to 5 carbon atoms (e.g. methyl, ethyl, etc.), or cycloalkyl with 5 to 10 carbon atoms (preferably cyclohexyl or adamantine). til) is preferable.

X ¹ and X ² in formula (1) are each independently >O, >NR, >Si(-R) ₂ , >C(-R) ₂ , >S, >Se, or R The monovalent group represented by (G) is >NR. In formula (2) described later, including the case where R is >NR, which is a monovalent group represented by formula (G-2), this type of >NR is referred to as >NG in this specification. Provided that at least one of X ¹ and X ² is >NG. When one of _X ¹ and X ² is >NG, ^the other X ¹ or It is more preferable that it is NR.

R of >NR where X ^{1 or} R of >Si(-R) ₂ of X ¹ and X ² is each independently hydrogen, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkyl, or optionally substituted cycloalkyl.

R of >Si(-R) ₂ and >C(-R) ₂ of X ¹ or X ² is each independently hydrogen, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkyl, Or it is cycloalkyl which may be substituted, and it is preferable that two R's are the same, and two R's may be combined to form a ring.

For aryl, heteroaryl, alkyl, and cycloalkyl at R of > ^NR , >Si(-R) ² _, or >C(-R) ₂ which is X 1 or You can refer to .

R of >NR where X ^{1 or} It is more desirable. As an example of cycloalkyl, the examples described later can be given. Here, as aryl, phenyl, biphenylyl (particularly 2-biphenylyl), and terphenylyl (particularly terphenyl-2'-yl) are preferable, and as heteroaryl, benzothienyl (2-benzo thienyl, 6-benzothienyl, etc.), benzofuranyl (2-benzofuranyl, 3-benzofuranyl, 5-benzofuranyl, etc.), dibenzofuranyl (2-dibenzofuranyl, 3-dibenzofuranyl) Benzofuranyl, 4-dibenzofuranyl, 5-dibenzofuranyl, etc.) are preferred. As the substituent, tertiary alkyl (particularly t-butyl) or cycloalkyl (particularly adamantyl) represented by the above formula (tR) is preferable. The number of substituents in aryl and heteroaryl is preferably 0 to 2, more preferably 1 or 2, and even more preferably 1. It is also preferable that the aryl ring in the aryl described above is condensed with an optionally substituted cycloalkane as described later. As specific cycloalkanes, those described later can be referred to.

Particularly preferable examples ^of R of >NR where X ¹ or ) can be mentioned. As 2-biphenyl which may be substituted, 2-biphenylyl substituted with 1 to 3 t-butyl is particularly preferable. As terphenyl-2'-yl which may be substituted, unsubstituted [1,1':3',1''-terphenyl]-2'-yl is particularly preferable. As aryl condensed with cycloalkane, the following are particularly preferable.

(Me represents methyl, tBu represents t-butyl, and * represents the binding site.)

When either X ^{1 or}

R in at least one of > ^NR , >Si(-R) ₂ and >C(-R) ₂ of X ¹ or and may be bonded to any one of the C rings. That is, R in at least ^one of >NR, >Si(-R) ₂ and >C(-R) ₂ of , R in at least one of >NR, >Si(-R) ₂ and >C(-R) ₂ of X ² may be bonded to either the A ring or the C ring by a linking group or a single bond. As the linking group, -O-, -S-, or -C(-R ¹³ ) ₂ - is preferred. R ¹³ in the above “-C(-R ¹³ ) ₂ -” is hydrogen, alkyl, or cycloalkyl. Examples of the alkyl or cycloalkyl include the groups described above as the first substituent, respectively. In particular, alkyl with 1 to 5 carbon atoms (for example, methyl, ethyl, etc.) or cycloalkyl with 5 to 10 carbon atoms (preferably cyclohexyl or adamantyl) is preferable.

This regulation can be expressed as ^a compound having a ring structure in which X ¹ or That is, for example, it is a compound having a B' ring (or C' ring) formed by condensing other rings by inserting X ¹ (or X ² ) into the B ring (or C ring), which is a benzene ring. The resulting condensed ring B' (or condensed ring C') is, for example, a carbazole ring, a phenoxazine ring, a phenothiazine ring, or an acridine ring.

In addition, the above regulation refers to a compound having a ring structure in which either X ^{1 or} can also be expressed. That is, for example, it is a compound having an A' ring formed by condensing the other ring by inserting either X ¹ or X ² into ring A, which is a benzene ring. The resulting condensed ring A' is, for example, a carbazole ring, a phenoxazine ring, a phenothiazine ring, or an acridine ring.

As an example, R of >N-R may be substituted cycloalkyl, and a form in which R is bonded to the A ring, B ring, or C ring by a single bond is also preferable. As cycloalkyl, optionally substituted cyclopentyl or optionally substituted cyclohexyl is preferable.

A particularly preferable example of the condensed ring formed as described above includes the structure represented by formula (A11). As described above, in this case, the two carbons substituted by the methyl group are asymmetric carbons, and the compound represented by formula (1) may include diastereomers and enantiomers, but the compound represented by formula (1) Any of these isomers may be used, and the possible isomers may be mixed in an arbitrary ratio.

In formula (A11), Me is methyl, and is bonded to one ring of the two rings to which X ¹ or X ² is bonded at two * positions and to the other ring at the ** positions. Examples of such structures include the structures of compounds represented by any of the formulas (1-17), (1-32), (1-56), and (1-72) described later.

By using the compound ^of the present invention, which has R >NR in the above preferable range as X ¹ or

^R in >Si(-R) ₂ that is X ¹ or . Here, the substituent when substituted includes the second substituent described above. Examples of the aryl, heteroaryl, alkyl, or cycloalkyl include the groups described above as the first substituent. In particular, aryl with 6 to 10 carbon atoms (e.g., phenyl, naphthyl, etc.), heteroaryl with 2 to 15 carbon atoms (e.g., carbazolyl, etc.), and alkyl with 1 to 5 carbon atoms (e.g., methyl, ethyl, etc.) Alternatively, cycloalkyl having 5 to 10 carbon atoms (preferably cyclohexyl or adamantyl) is preferred.

^R in >C(-R) ₂ that is X ¹ or . Here, the substituent when substituted includes the second substituent mentioned above. Examples of the aryl, heteroaryl, alkyl, or cycloalkyl include the groups described above as the first substituent. In particular, aryl with 6 to 10 carbon atoms (e.g., phenyl, naphthyl, etc.), heteroaryl with 2 to 15 carbon atoms (e.g., carbazolyl, etc.), and alkyl with 1 to 5 carbon atoms (e.g., methyl, ethyl, etc.) Alternatively, cycloalkyl having 5 to 10 carbon atoms (preferably cyclohexyl or adamantyl) is preferred.

Next, the group represented by formula (G) in formula (1) will be explained.

In formula (G), L is a single bond, alkylene, cycloalkylene, arylene, or heteroarylene. “Alkylene,” “cycloalkylene,” “arylene,” and “heteroarylene” include 2 excluding one hydrogen from “alkyl,” “cycloalkyl,” “aryl,” and “heteroaryl” in this specification. You can raise the flag of A. As L, a single bond, arylene, or heteroarylene is preferable, a single bond or arylene is preferable, and a single bond is most preferable. In addition, at least one hydrogen among “alkylene”, “cycloalkylene”, “arylene”, and “heteroarylene” may be substituted, but in this case, the substituent may be substituted or unsubstituted aryl, substituted or unsubstituted Heteroaryl, substituted or unsubstituted diarylamino (two aryls may not be bonded to each other or may be bonded through a linking group), substituted or unsubstituted diheteroarylamino (two heteroaryls may not bond to each other, or may be bonded through a single bond or a linking group), substituted or unsubstituted arylheteroarylamino (aryl and heteroaryl are not bonded to each other or are bonded through a linking group), substituted or unsubstituted diarylboryl (2 (two aryls may not be bonded to each other or may be bonded through a single bond or linking group), substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkenyl , substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted arylthio, or substituted silyl, but an unsubstituted form of L is also preferable. Regarding the second substituents for these first substituents, reference may be made to the above description.

In formula (G), the (G-A) ring and (G-B) ring are a substituted or unsubstituted aryl ring or a substituted or unsubstituted heteroaryl ring. For the preferable range and substituent, reference can be made to the description of the A ring, B ring, and C ring in formula (1) above, but a substituted or unsubstituted benzene ring is preferable.

In formula (G), X ³ and X ⁴ are each independently >O, >NR, >C(-R) ₂ , >Si(-R) ₂ , >S, or >Se, and R is hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, >C(-R) ₂ , and >Si(-R ) R in ₂ is each independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, >C(-R) ₂ and >The two R's of Si(-R) ₂ may be combined with each other to form a ring.

In addition, in formula (G), at least one R ^of >NR, >C(-R) ₂ and >Si(-R) ₂ as X ³ and ) may be bonded to at least one of the following through a linking group or single bond. As the linking group, -O-, -S-, or -C(-R ¹⁴ ) ₂ - is preferred. In addition, R ¹⁴ in the above “-C(-R ¹⁴ ) ₂ -” is hydrogen, alkyl, or cycloalkyl, and examples of the alkyl or cycloalkyl include the groups described above as the first substituent, respectively. In particular, alkyl with 1 to 5 carbon atoms (for example, methyl, ethyl, etc.) or cycloalkyl with 5 to 10 carbon atoms (preferably cyclohexyl or adamantyl) is preferable.

The polycyclic aromatic compound of the present invention is a polycyclic aromatic compound having a structure consisting of one or two or more structural units represented by formula (1) and formula (2) described later. As a polycyclic aromatic compound having a structure consisting of one of the above structural units, a polycyclic aromatic compound represented by the formula described above as the structural unit represented by formula (1) can be presented. Examples of the polycyclic aromatic compound having a structure consisting of two or more structural units represented by formula (1) include compounds corresponding to a multimer of the polycyclic aromatic compound represented by the formula described above as the structural unit represented by formula (1). can be mentioned. The polymer is preferably a 2 to 6-mer, more preferably a 2- to 3-mer, and especially preferably a dimer. The multimer may be in the form of having a plurality of the above unit structures in one compound, and may be a form in which any ring (A ring, B ring or C ring) included in the structural unit is shared and bonded to a plurality of unit structures. Additionally, any rings (A ring, B ring, or C ring) included in the unit structure may be condensed and bonded to each other. Additionally, the unit structure may be a single bond or a form in which multiple linking groups such as alkylene, phenylene, or naphthylene having 1 to 3 carbon atoms are bonded together. Among these, a form in which rings are shared and bonded together is preferable.

In a polycyclic aromatic compound having a structure consisting of one or two or more structural units represented by formula (1), at least one selected from the group consisting of an aryl ring and a heteroaryl ring is condensed with at least one cycloalkane. It is done. The same applies to the polycyclic aromatic compound represented by formula (2) described later, and the following explanation also applies to the polycyclic aromatic compound represented by formula (2).

The cycloalkane may be any cycloalkane having 3 to 24 carbon atoms. At this time, at least one hydrogen in the cycloalkane may be substituted with aryl with 6 to 30 carbon atoms, heteroaryl with 2 to 30 carbon atoms, alkyl with 1 to 24 carbon atoms, or cycloalkyl with 3 to 24 carbon atoms, and the corresponding At least one -CH ₂ - in the cycloalkane may be substituted with -O-, but cycloalkanes in which all -CH ₂ - are preferred are preferred.

When at least one selected from the group consisting of an aryl ring and a heteroaryl ring in a structure consisting of one or two or more structural units represented by formula (1) is condensed with at least one cycloalkane, at least one The cycloalkane is a cycloalkane with 3 to 20 carbon atoms, and at least one hydrogen in the cycloalkane is aryl with 6 to 16 carbon atoms, heteroaryl with 2 to 22 carbon atoms, alkyl with 1 to 12 carbon atoms, or 3 carbon atoms. It is preferable that it is a cycloalkane which may be substituted with cycloalkyl of ~16.

As “cycloalkane”, cycloalkane with 3 to 24 carbon atoms, cycloalkane with 3 to 20 carbon atoms, cycloalkane with 3 to 16 carbon atoms, cycloalkane with 3 to 14 carbon atoms, cycloalkane with 5 to 10 carbon atoms, cycloalkane with 5 to 8 carbon atoms. cycloalkanes, cycloalkanes with 5 to 6 carbon atoms, cycloalkanes with 6 carbon atoms, etc.

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

Among these, for example, as shown in the structural formula below, the α-position carbon of a cycloalkane (in cycloalkyl condensing to an aryl ring or heteroaryl ring, the carbon adjacent to the carbon of the condensation site, corresponds to the benzyl position) ), a structure in which at least one hydrogen is substituted is preferable, a structure in which two hydrogens in the α-position carbons are substituted is more preferable, and a total of four hydrogens in the two α-position carbons are substituted. This structure is more desirable. This is to protect the chemically active portion and improve the durability of the compound. Examples of this substituent include alkyl (especially methyl) substituents having 1 to 5 carbon atoms, halogen (especially fluorine) substituents, and deuterium substituents. In particular, it is preferable to have a structure in which a partial structure represented by the following formula (Z-11) is bonded to an adjacent carbon atom in the aryl ring or heteroaryl ring.

In formula (Z-11), Me represents methyl and * represents the binding site.

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, an example in which one or more cycloalkanes are condensed in one benzene ring (phenyl) is shown below. * represents the bonding position, and the position may be any of the carbons that constitute the benzene ring and do not constitute the cycloalkane. Cycloalkanes condensed as in formula (Cy-1-4) and (Cy-2-4) may be condensed. The same applies even if the ring (group) to be condensed is an aryl ring or heteroaryl ring other than a benzene ring (phenyl), and even if the cycloalkane to be condensed is a cycloalkane other than cyclopentane or cyclohexane.

　

At least one -CH ₂ - in the cycloalkane may be substituted with -O-. For example, an example in which one or more -CH ₂ - in a cycloalkane condensed to one benzene ring (phenyl) is replaced with -O- is shown below. This applies even if the ring (group) to be condensed is an aromatic ring or heteroaromatic ring other than the benzene ring (phenyl), and even if the cycloalkane to be condensed is a cycloalkane other than cyclopentane or cyclohexane.

At least one hydrogen in the cycloalkane may be substituted, and examples of this substituent include aryl, heteroaryl, diarylamino (two aryls are not bonded to each other or are bonded through a linking group), di. Heteroarylamino (two heteroaryls are not bonded to each other or are bonded through a single bond or linking group), arylheteroarylamino (aryl and heteroaryl are not bonded to each other or are bonded through a single bond or linking group) , diarylboryl ((two aryls are not bonded to each other or are bonded through a single bond or linking group), alkyl, cycloalkyl, alkoxy, aryloxy, substituted silyl, deuterium, cyano, or halogen, The details of these can be referred to the description of the above-mentioned first substituent.Among these substituents, alkyl (for example, alkyl with 1 to 6 carbon atoms), cycloalkyl (for example, cycloalkyl with 3 to 14 carbon atoms), Preferred are halogen (e.g. fluorine), deuterium, etc. In addition, when cycloalkyl is substituted, it may be in a form of substitution that forms a spiro structure, an example of which is shown below.

　

As a form of cycloalkane condensation, first, an aryl ring in each of ring A, ring B, and ring C in a polycyclic aromatic compound having a structure consisting of one or two or more structural units represented by formula (1). and heteroaryl rings, aryl rings and heteroaryl rings (a-ring, b-ring, and c-ring in formula (2)) described later, and forms in which the aryl ring and heteroaryl ring in the condensed ring are condensed with cycloalkane. there is.

Other forms of cycloalkane condensation include polycyclic aromatic compounds having a structure consisting of one or two or more structural units represented by formula (1), and polycyclic aromatic compounds represented by formula (2) described later, for example. , R is an aryl condensed with a cycloalkane >N-R, diarylamino condensed with a cycloalkane (two aryls may not be bonded to each other or may be bonded through a linking group, and are condensed at the aryl portion), condensed with a cycloalkane Examples include carbazolyl (condensed with this benzene ring portion) or benzocarbazolyl condensed with cycloalkane (condensed with this benzene ring portion). As for "diarylamino (two aryls may not be bonded to each other or may be bonded through a linking group)", the group described as the "first substituent" above can be mentioned.

In the polycyclic aromatic compound having a structure consisting of one or two or more structural units represented by formula (1), and the polycyclic aromatic compound represented by formula (2) described later, the above cycloalkane condensation is A ( A form condensed to the a) ring, B(b) ring, or C(c) ring is preferable, and a form condensed to the A(a) ring or B(b) ring is more preferable. Also, a form condensed on both the A(a) ring and the B(b) ring is also preferred.

Additionally, by introducing a cycloalkane structure into the polycyclic aromatic compound of the present invention, a decrease in melting point or sublimation temperature can be expected. This means that in sublimation purification, which is almost essential as a purification method for materials for organic devices such as organic EL elements that require high purity, thermal decomposition of the material can be avoided because purification can be done at a relatively low temperature. This also applies to the vacuum deposition process, which is a powerful means for manufacturing organic devices such as organic EL elements. Since the process can be performed at a relatively low temperature, thermal decomposition of the material can be avoided, and as a result, high-performance organic devices can be obtained. You can. In addition, since the solubility in organic solvents is improved by introducing a cycloalkane structure, it becomes possible to apply it to device manufacturing using a coating process. However, the present invention is not particularly limited to these principles. From this, in polycyclic aromatic compounds having a structure consisting of one or two or more structural units represented by formula (1), and polycyclic aromatic compounds represented by formula (2) described later, the above-mentioned cycloalkane condensation is introduced. It is desirable to be

All or part of the hydrogen in a structure consisting of one or two or more structural units represented by formula (1) may be deuterium, cyano, or halogen. The same applies to the polycyclic aromatic compound represented by formula (2) described later, and the following explanation also applies to the polycyclic aromatic compound represented by formula (2).

For example, in a structure consisting of one or two or more structural units represented by formula (1), ring A, ring B, ring C (rings A to C are aryl rings or heteroaryl rings), A to C Substituents on the ring, R (=alkyl, cycloalkyl, aryl) when Y ¹ is Si-R or Ge-R, and X ¹ and X ² are >NR, >C(-R) ₂ , or > When Si(-R) ₂ , the hydrogen in R (=alkyl, cycloalkyl, aryl) may be substituted with deuterium, cyano, or halogen, but among these, all or part of the hydrogen in aryl or heteroaryl Aspects in which is substituted with deuterium, cyano, or halogen can be mentioned. Halogen is fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine, or bromine, more preferably fluorine or chlorine, and fluorine is still more preferable. Furthermore, from the viewpoint of durability, it is preferable that all or part of the hydrogen in the structure consisting of one or two or more structural units represented by formula (1) is deuterated, and it is also preferable that all of the hydrogen is deuterated. do.

A preferable example of a polycyclic aromatic compound having a structure consisting of one or two or more structural units represented by formula (1) includes a polycyclic aromatic compound represented by the following formula (2). In addition, for the substituent in formula (2), the structure of the ring included, and the preferable range, each description of the corresponding formula (1) can be referred to.

In equation (2), Y ¹ is the same as Y ¹ in equation (1).

In formula (2), Z is each independently N or CR ¹¹ , and ¹¹ of CR ¹¹ is each independently hydrogen, aryl, heteroaryl, diarylamino (two aryls are not bonded to each other or are a linking group are bonded through), diheteroarylamino (two heteroaryls are not bonded to each other or are bonded through a linking group), arylheteroarylamino (aryl and heteroaryl are not bonded to each other or are bonded through a linking group) present), diarylboryl (two aryls are not bonded to each other or are bonded through a single bond or linking group), alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio, or substituted silyl. At least one hydrogen may be substituted with aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl. For details of the substituents listed here, reference may be made to the description of the first and second substituents above.

Two adjacent R ¹¹ may be bonded to each other to form an aryl ring or heteroaryl ring, and the formed aryl ring and heteroaryl ring are respectively aryl, heteroaryl, or diarylamino (two aryls are not bonded to each other, or are bonded through a linking group), diheteroarylamino (two heteroaryls are not bonded to each other or are bonded through a linking group), arylheteroarylamino (aryl and heteroaryl are not bonded to each other or are bonded through a linking group) is substituted with diarylboryl (two aryls are not bonded to each other or are bonded through a single bond or linking group), alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio, or substituted silyl. may be present, and at least one hydrogen in these may be substituted with aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl. For details of the substituents listed here, reference may be made to the description of the first and second substituents above.

In equation (2), Z=Z may each independently be >O, >NR, >C(-R) ₂ , >Si(-R) ₂ , >S, or >Se, >O, >NR , >C(-R) ₂ , or >S is more preferable. R of the >NR, the >C(-R) ₂ and the >Si(-R) ₂ is each independently hydrogen, aryl, heteroaryl, alkyl, or cycloalkyl, and at least one hydrogen in these is , aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl. Additionally, the two R's of >C(-R) ₂ and >Si(-R) ₂ may be bonded to each other to form a ring. In addition, for details of the substituents listed here, reference may be made to the description of the first and second substituents above.

In the b ring, c ring, etc., the ring obtained by replacing the position of “Z=Z” with >O, >NR, >C(-R) ₂ , >Si(-R) ₂ , >S, or >Se , cyclopentadiene ring, pyrrole ring, furan ring, thiophene ring, etc. When the remaining Zs are further adjacent, they are CR ¹¹ , and R ¹¹ combines to form a benzene ring, an indene ring, an indole ring, a benzofuran ring, or a benzothiophene ring can be formed. The formed ring may have a substituent. In b rings, etc., one Z=Z is >NR, >O, >S, >C(-R) ₂ and the remaining Z is CH, and one Z=Z is >NR, >O , >S, >C(-R) ₂ , the remaining Zs are adjacent, and all are CR ¹¹ , and an example in which these R ¹¹ are bonded to each other to form a benzene ring is shown below. However, the forms that the b ring, c ring, etc. can take are not limited to the following examples.

In addition, R ¹¹ of CR ¹¹ is bonded to form an aryl ring such as a cyclopentadiene ring, pyrrole ring, furan ring, thiophene ring, indene ring, indole ring, benzofuran ring, or benzothiophene ring, and heteroaryl ring. An example of forming is shown below.

In ^the above example, an example of the b ring bonded to Y ¹ and

X ¹ and X ² in equation (2) are each independently >O, >NR, >Si(-R) ₂ , >C(-R) ₂ , >S, >Se, or R The monovalent group represented by (G-2) is >NR (>NG). Provided that at least one of X ¹ and X ² is >NG. Regarding the specific ranges of >NR, >Si(-R) ₂ , and >C(-R) ₂ , the description regarding X ¹ and X ² in the above formula (1) can be referred to. When either _X ^{1 or} X ² is >NG, the other X ¹ or It is more preferable that it is NR.

In formula ( ¹ ) _, R in at least one of >NR, >Si(-R) ₂ and >C(-R) ² in And the above-mentioned statement that it may be bonded to at least one of the B rings, or at least one of the A rings and the C rings through a linking group or a single bond, in formula (2), "Also, R of the >NR , R in at least one of R of >C(-R) ₂ and >Si(-R) ₂ is -O-, -S-, -C(-R ¹³ ) ₂ - or a single bond. Accordingly, it is combined with one or two C in Z, which is CR ¹¹ , and corresponds to the stipulation of “. Specifically, the R may be bonded to C (carbon atom) in Z, which is the spatially closest CR ¹¹ in each ring shown below, and in formula ( ² ), >NR, >Si as R of (-R) ₂ or >C(-R) ₂ is connected to C (carbon atom) in Z, which is the spatially closest CR ¹¹ of at least one of the a ring and the b ring, through a linking group or a single bond. It may be bonded, and R of > ^NR , >Si(-R) ₂ or >C(-R) ₂ as It may be bonded to C (carbon atom) in Z, which is nearby CR ¹¹ . Regarding R ¹³ of “-C(-R ¹³ ) ₂ -” among these, the above description can be referred to.

In formula (2), the number of rings (monocycles) containing Z as N is 0 to 4, preferably 0 to 3, more preferably 0 to 2, and especially preferably 0 to 1. In each of the above formulas, it is also preferable that Z is all CR ¹¹ .

In formula (2), in the ring (monocycle) containing Z which is N, it is preferable that one or two of the plurality of Z's are N, and when two are N, the two N's are not adjacent to each other. desirable. When the 6-membered ring is a ring containing N and Z, a pyridine ring, a pyrimidine ring, a pyridazine ring, or a 1,2,3-triazine ring is preferable, and a pyridine ring or a pyrimidine ring is more preferable. When the 5-membered ring is a ring containing N and Z, a thiazole ring or an oxazole ring is preferable.

The group represented by formula (G-2) in formula (2) will be explained. In formula (G-2), Z ^G is N or CR ¹² , and R ¹² of CR ¹² is each independently hydrogen, aryl, heteroaryl, diarylamino (two aryls are not bonded to each other or have a linking group) are bonded through), diheteroarylamino (two heteroaryls are not bonded to each other or are bonded through a linking group), arylheteroarylamino (aryl and heteroaryl are not bonded to each other or are bonded through a linking group) ), diarylboryl (two aryls are not bonded to each other or are bonded through a single bond or linking group), alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio, or substituted silyl, and these are At least one hydrogen may be substituted with aryl, heteroaryl, aryl amino, alkyl, cycloalkyl, or substituted silyl. For details of the substituents listed here, reference may be made to the description of the first and second substituents above.

Two adjacent R ¹² may be bonded to each other to form an aryl ring or heteroaryl ring, and the formed aryl ring and heteroaryl ring are respectively aryl, heteroaryl, or diarylamino (two aryls are not bonded to each other, or are bonded through a linking group), diheteroarylamino (two heteroaryls are not bonded to each other or are bonded through a linking group), arylheteroarylamino (aryl and heteroaryl are not bonded to each other or are bonded through a linking group) is substituted with diarylboryl (two aryls are not bonded to each other or are bonded through a single bond or linking group), alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio, or substituted silyl. may be present, and at least one hydrogen in these may be substituted with aryl, heteroaryl, aryl amino, alkyl, cycloalkyl, or substituted silyl. For details of the substituents listed here, reference may be made to the description of the first and second substituents above.

In equation (G-2), Z ^G =Z ^G may each independently be >O, >NR, >C(-R) ₂ , >Si(-R) ₂ , >S, or >Se, > It is more preferable that it is O, >NR, >C(-R) ₂ , or >S. R of the >NR, the >C(-R) ₂ and the >Si(-R) ₂ is each independently hydrogen, aryl, heteroaryl, alkyl, or cycloalkyl, and at least one hydrogen in these is , aryl, heteroaryl, arylamino, alkyl, cycloalkyl, or substituted silyl. The two R's of >C(-R) ₂ and >Si(-R) ₂ may be bonded to each other to form a ring. Additionally, for details of the substituents listed here, reference may be made to the description of the first and second substituents above.

In formula (G-2), the positions of “Z ^G =Z ^G ” of the (Ga) ring and (Gb) ring are >O, >NR, >C(-R) ₂ , >Si(-R) ₂ , Regarding the ring obtained by substitution with >S or >Se, reference can be made to the description of “Z=Z” in the a ring and b ring in the above-mentioned formula (1). Also, regarding the specific form, the above description can be referred to by replacing Y ¹ and X ¹ with X ³ and X ⁴ .

-O-, -S-, -C(-R 14 for >NR, >Si(-R) ₂ and >C(-R) ₂ for X ³ and X ⁴ in formula (G- ² ) ) ₂ - Alternatively, it may be bonded to one or two of C in Z ^G of CR ¹² by a single bond. This means that in formula (G) in formula (1), at least one R of ">NR, >C(-R) ₂ and >Si(-R) ₂ is a (GA) ring by a linking group or a single bond. and (GB) may be combined with at least one of a linking group or a single bond.” Specifically, the R in the formula (G-2) is -O-, -S-, -C(-R ¹³ ) ₂ to C (carbon atom) of Z ^G , which is the spatially closest CR ¹² in each ring. - Alternatively, they may be bonded by a single bond. Among these, R ¹⁴ in “-C(-R ¹⁴ ) ₂ -” is hydrogen, alkyl, or cycloalkyl. Examples of the alkyl or cycloalkyl include the groups described above as the first substituent, respectively. In particular, alkyl with 1 to 5 carbon atoms (for example, methyl, ethyl, etc.) or cycloalkyl with 5 to 10 carbon atoms (preferably cyclohexyl or adamantyl) is preferable.

In formula (G-2), one bond of L, a divalent group, is connected to Z ^G (C (carbon atom) of CR ¹² which is Z ^G ) of any one of the (Ga) ring, The other binding hand is bonded to N (nitrogen atom) of >NG.

In formula (G-2), the number of rings (monocycles) containing Z as N is 0 to 4, preferably 0 to 3, more preferably 0 to 2, and especially preferably 0 to 1. do. In each of the above formulas, it is also preferable that all Zs are CR ^Z.

In the formula (G-2), in the ring (monocycle) containing Z that is N, it is preferable that one or two of the plurality of Zs are N, and when two are N, the two N are not adjacent to each other. It is desirable to have When the 6-membered ring is a ring containing N and Z, a pyridine ring, a pyrimidine ring, a pyridazine ring, or a 1,2,3-triazine ring is preferable, and a pyridine ring or a pyrimidine ring is more preferable. When the 5-membered ring is a ring containing N and Z, a thiazole ring or an oxazole ring is preferable.

Specifically, the group represented by formula (G-2) includes the forms described below as formulas (G-2-1) to (G-2-16). However, it is not limited to this example.

In formulas (G-2-1) ^to (G-2-16), R is >NR, >Si( ^-R ) ₂ and >C(-R) ₂ in You can refer to what is defined as. At least one hydrogen of these groups may be substituted with a substituent, and the description of the first and second substituents above can be referred to for the form of substitution.

Additional 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. Additionally, the following structure is an example.

　

The polycyclic aromatic compound of the present invention can be produced by the following procedure.

<Method for producing polycyclic aromatic compounds>

A polycyclic aromatic compound having a structure consisting of one or two or more structural units represented by formula (1) or formula (2) basically consists of first an A ring (a ring), a B ring (b ring), and An intermediate is prepared by linking the C ring (c ring) with ^a linking group (a group containing X ¹ or The final product can be prepared by linking the ring (c ring) with a linking group (group containing Y ¹ ) (second reaction). In the first reaction, for example, if it is an etherification reaction, general reactions such as nucleophilic substitution reaction and Ullman reaction can be used, and if it is an amination reaction, general reactions such as Birchwald-Hartwig reaction can be used. In addition, in the second reaction, a tandem hetero Friedel Crafts reaction (successive aromatic electron substitution reaction, hereinafter the same) can be used. Somewhere in the reaction process, by using a raw material having the desired condensed ring or adding a step to condense the ring, at least one ring selected from the group consisting of A ring, B ring, and C ring is a monocyclic aryl ring, A compound can be prepared from a condensed ring composed of two or more rings selected from the group consisting of a monocyclic heteroaryl ring and a cyclopentadiene ring.

<Production method via Intermediate-1>

The polycyclic aromatic compound of the present invention can be produced by a production method including the following steps. For each process below, refer to the description in International Publication No. 2015/102118.

A ^{reaction step} of ^metalizing the halogen atom (Hal) between X ^{1 and} A reaction step of exchanging the metal with Y ¹ using a reagent selected from the group consisting of an alkoxylate of and an aryloxy oxide of Y ¹ , and a continuous aromatic electron substitution reaction using a Bronsted base to obtain Y ¹ The reaction including the reaction step of combining ring B and ring C is recorded below.

　

The metalizing reagent used in the halogen-metal exchange reaction in the scheme explained so far includes alkyl lithium such as methyllithium, n-butyllithium, sec-butyllithium, and t-butyllithium, isopropylmagnesium chloride, and isobromide. Examples include propylmagnesium, phenylmagnesium chloride, phenylmagnesium bromide, and the lithium chloride complex of isopropylmagnesium chloride, known as a turbo Grignard reagent.

In addition, the metalizing reagents used in the ortho-metal exchange reaction in the scheme explained so far include, in addition to the above reagents, lithium diisopropylamide, lithium tetramethyl piperidide, lithium hexamethyl disilazide, and potassium hexamethylene. Organic alkali compounds such as methyldisilazide, lithium tetramethylpiperidinyl magnesium·lithium chloride complex, and lithium tri-n-butylmagnesate can be mentioned.

In addition, when using alkyl lithium as a metalizing reagent, additives that promote the reaction include N,N,N',N'-tetramethylethylenediamine, 1,4-diazabicyclo[2.2.2]octane, N , N-dimethylpropylene urea, etc.

In addition, the Lewis acids used in the schemes explained so far include AlCl ₃ , AlBr ₃ , AlF ₃ , BF ₃ ·OEt ₂ , BCl ₃ , BBr ₃ , GaCl 3 , GaBr ₃ , InCl _{3 ,} InBr ₃ , and In(OTf ) ₃ , SnCl ₄ , SnBr ₄ , AgOTf, ScCl ₃ , Sc(OTf) ₃ , ZnCl ₂ , ZnBr ₂ , Zn(OTf) ₂ , MgCl ₂ , MgBr ₂ , Mg(OTf) ₂ , LiOTf, NaOTf, KOTf, Me3SiOTf, Cu(OTf) ₂ , CuCl ₂ , YCl ₃ , Y(OTf) ₃ , TiCl ₄ , TiBr ₄ , ZrCl ₄ , ZrBr ₄ , FeCl 3, FeBr ₃ , CoCl _{3 ,} CoBr _3, etc. Additionally, these Lewis acids supported on solids can also be used in the same way.

In addition, the Bronsted acids used in the schemes explained so far include p-toluenesulfonic acid, methanesulfonic acid, trifluoromethanesulfonic acid, fluorosulfonic acid, carboranic acid, trifluoroacetic acid, (trifluoromethanesulfonyl) )imide, tris(trifluoromethanesulfonyl)methane, hydrogen chloride, hydrogen bromide, hydrogen fluoride, etc. Additionally, solid Bronsted acids include Amberlyst (brand name: Dow Chemical), Nafion (brand name: DuPont), Zeolite, and Teikacure (brand name: Teika Co., Ltd.).

Additionally, amines that may be added in the schemes explained so far include diisopropylethylamine, triethylamine, tributylamine, 1,4-diazabicyclo[2.2.2]octane, and N,N-dimethyl-p-. Toluidine, N,N-dimethyl aniline, pyridine, 2,6-lutidine, 2,6-di-t-butylamine, etc. can be mentioned.

In addition, solvents used in the schemes explained so far 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, methyl-t-butyl ether, etc.

Here, an example where Y ¹ is B is described, but by appropriately changing the raw materials, compounds where Y ¹ is P, P=O, P=S, Al, Ga, As, Si-R or Ge-R can also be synthesized. can do.

In the above scheme, a Bronsted base or Lewis acid may be used to promote the tandem hetero Friedel Crafts reaction. However, when a halide of Y ¹ such as trifluoride of Y 1 , trichloride of Y ¹ , tribromide of Y ^{1 or} triiodide of Y ¹ is used, as the aromatic electron substitution reaction progresses, fluoride Because acids such as hydrogen, hydrogen chloride, hydrogen bromide, and hydrogen iodide are produced, the use of a Brønsted base to capture the acid is effective. On the other hand, when an aminated halide of Y ¹ or an alkoxylate of Y ¹ is used, amines and alcohols are produced as the aromatic electron substitution reaction progresses, so in many cases, it is not necessary to use a Brønsted base. Since the detachment ability of amino or alkoxy is low, the use of a Lewis acid that promotes detachment is effective.

In addition, the polycyclic aromatic compound of the present invention also includes compounds in which at least some of the hydrogen atoms are substituted with deuterium or cyano, and compounds in which the hydrogen atoms are substituted with halogens such as fluorine or chlorine. In such compounds, the desired position is deuterated, It can be synthesized in the same manner as above by using cyaninated, fluorinated or chlorinated raw materials.

<2. Organic Device>

The polycyclic aromatic compound of the present invention can be used as a material for organic devices. Examples of organic devices include organic electroluminescent elements, organic field-effect transistors, and organic thin-film solar cells.

The polycyclic aromatic compound and its multimer according to the present invention can be used as a material for organic devices. Examples of organic devices include organic electroluminescent devices, organic field-effect transistors, and organic thin-film solar cells, but it is preferable that they are organic electroluminescent devices. The polycyclic aromatic compound and its multimer according to the present invention are preferably organic electroluminescent device materials, more preferably materials for a light-emitting layer (light-emitting material), and most preferably dopant materials for the light-emitting layer. In particular, in organic electroluminescent devices, as a dopant material for the light emitting layer, a polycyclic aromatic compound having a structure consisting of one or two or more structural units represented by formula (1) of the present invention or formula (2) described later. In this case, compounds ⁱⁿ which Y ¹ is B ^, Preferably, as the host material ^of the light-emitting ^{layer, a compound in which Y 1 is B} , one ^of A compound in which one of the ^two is >NG and the other is >O is more preferable, and as an electron transport material, a compound in which Y ¹ is B or P=O is preferably used.

<2-1. Organic electroluminescent device>

<2-1-1. Structure of organic electroluminescent device>

1 is a schematic cross-sectional view showing an example of an organic EL device.

The organic EL device 100 shown in FIG. 1 includes a substrate 101, an anode 102 provided on the substrate 101, a hole injection layer 103 provided on the anode 102, and a hole injection layer. A hole transport layer 104 provided on (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, and an electron provided on the electron transport layer 106. It has an injection layer 107 and a cathode 108 provided on the electron injection layer 107.

In addition, the organic EL element 100 reverses the manufacturing order, for example, a substrate 101, a cathode 108 provided on the substrate 101, and an electron injection layer provided on the cathode 108 ( 107), an electron transport layer 106 provided on the electron injection layer 107, a light emitting layer 105 provided on the electron transport layer 106, a hole transport layer 104 provided on the light emitting layer 105, and a hole transport layer. It may be configured to include a hole injection layer 103 provided on (104) and an anode 102 provided on the hole injection layer 103.

It is not necessary to have all of the above layers, and the minimum structural unit is composed of an anode 102, a light emitting layer 105, and a cathode 108, and a hole injection layer 103, a hole transport layer 104, and an electron transport layer 106. ), the electron injection layer 107 is a layer installed arbitrarily. In addition, each of the above layers may be composed of a single layer or may be composed of multiple layers.

As aspects of the layers constituting the organic EL element, in addition to the above-mentioned “substrate/anode/hole injection layer/hole transport layer/light emitting layer/electron transport layer/electron injection layer/cathode”, “substrate/anode/hole transport layer/light emitting layer” /electron transport layer/electron injection layer/cathode”, “substrate/anode/hole injection layer/light-emitting layer/electron transport layer/electron injection layer/cathode”, “substrate/anode/hole injection layer/hole transport layer/light-emitting layer/electron injection layer/ cathode”, “substrate/anode/hole injection layer/hole transport layer/light-emitting layer/electron transport layer/cathode”, “substrate/anode/light-emitting layer/electron transport layer/electron injection layer/cathode”, “substrate/anode/hole transport layer/light-emitting layer/ “Electron injection layer/cathode”, “substrate/anode/hole transport layer/light-emitting layer/electron transport layer/cathode”, “substrate/anode/hole injection layer/light-emitting layer/electron injection layer/cathode”, “substrate/anode/hole injection layer/ The configuration may be “light emitting layer/electron transport layer/cathode”, “substrate/anode/light emitting layer/electron transport layer/cathode”, or “substrate/anode/light emitting layer/electron injection layer/cathode”.

<2-1-2. Emitting layer in organic electroluminescent device>

The polycyclic aromatic compound of the present invention is preferably used as a material for forming one or more organic layers in an organic electroluminescent device, and is more preferably used as a material 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 forming the light-emitting layer 105 may be any compound (luminescent compound) that is excited and emits light by recombination of holes and electrons, and can form a stable thin film shape and have strong luminescence (fluorescence) efficiency in the solid state. It is preferable that it is a compound representing . The polycyclic aromatic compound of the present invention can be used as a material for an emitting layer, may be used as a dopant material, and may be used as a host material, but is preferably used as a material for an emitting layer, and is more preferably used as a dopant material. .

Additionally, as a dopant, there are examples where an assisting dopant and an emitting dopant are used in combination, but in this specification, when “dopant” is used, it refers to a light-emitting dopant used alone.

The light-emitting layer may be a single layer, may be composed of multiple layers, or may be either, and is formed of materials for the light-emitting layer (host material and dopant material), respectively. The host material and the dopant material may be of one type, a combination of multiple types, or any of them. The dopant material may be contained in the entire host material, may be contained partially, or may be any one. As a doping method, it can be formed by co-deposition with the host material, but may be deposited simultaneously after mixing with the host material in advance.

The amount of host material used varies depending on the type of host material, and can be determined according to the characteristics of the host material. The standard for the usage amount of the host material is preferably 50 to 99.999% by mass, more preferably 80 to 99.95% by mass, and still more preferably 90 to 99.9% by mass of the total light emitting layer material.

The amount of dopant material used varies depending on the type of dopant material, and can be determined according to the characteristics of the dopant material. The standard for the amount of dopant used is preferably 0.001 to 50 mass% of the total light emitting layer material, more preferably 0.05 to 20 mass%, and even more preferably 0.1 to 10 mass%. The above range is preferable because, for example, concentration quenching phenomenon can be prevented.

<Host material>

As host materials, condensed ring derivatives such as anthracene, pyrene, dibenzochrysene or fluorene, which were previously known as light emitters, bistyryl derivatives such as bistyryl anthracene derivatives and distyrylbenzene derivatives, tetraphenylbutadiene derivatives, and cyclo Pentadiene derivatives, fluorene derivatives, benzofluorene derivatives, etc. can be mentioned.

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

　

In formulas (H1), (H2) and (H3), L ¹ is arylene with 6 to 24 carbon atoms, heteroarylene with 2 to 24 carbon atoms, heteroarylene arylene with 6 to 24 carbon atoms, and arylene with 6 to 24 carbon atoms. Arylene is heteroarylene arylene, and arylene with 6 to 16 carbon atoms is preferable, arylene with 6 to 12 carbon atoms is more preferable, and arylene with 6 to 10 carbon atoms is particularly preferable, and specifically, benzene ring. , biphenyl ring, terphenyl ring, and fluorene ring. As heteroarylene, heteroarylene with 2 to 24 carbon atoms is preferable, heteroarylene with 2 to 20 carbon atoms is more preferable, heteroarylene with 2 to 15 carbon atoms is still more preferable, and heteroarylene with 2 to 10 carbon atoms is more preferable. Arylene is particularly preferable, and specifically, pyrrole ring, oxazole ring, isoxazole ring, thiazole ring, isothiazole ring, imidazole ring, oxadiazole ring, thiadiazole ring, triazole ring, tetrazole ring, pyrazole ring, and pyridine. Ring, pyrimidine ring, pyridazine ring, pyrazine ring, triazine ring, indole ring, isoindole ring, 1H-indazole ring, benzoimidazole ring, benzoxazole ring, benzothiazole ring, 1H-benzotriazole ring, quinoline ring, Isoquinoline ring, cinnoline ring, quinazoline ring, quinoxaline ring, phthalazine ring, naphthridine ring, purine ring, pteridine ring, carbazole ring, acridine ring, phenoxathione ring, phenoxazine ring, phenothia Zinc ring, phenazine ring, indolizine ring, furan ring, benzofuran ring, isobenzofuran ring, dibenzofuran ring, thiophene ring, benzothiophene ring, dibenzothiophene ring, furazane ring, oxadiazole ring and thiant Bivalent groups such as renwan can be mentioned. At least one hydrogen in the compound represented by each of the above formulas may be substituted with alkyl, cyano, halogen, or deuterium having 1 to 6 carbon atoms.

Preferred specific examples include compounds represented by any of the structural formulas listed below. In addition, in the structural formulas listed below, at least one hydrogen may be substituted with halogen, cyano, alkyl with 1 to 4 carbon atoms (for example, methyl or t-butyl), phenyl, or naphthyl.

　

　　

<Anthracene compound>

Examples of anthracene compounds as hosts include compounds represented by the formula (3-H) and compounds represented by the formula (3-H2).

In formula (3-H),

X and Ar ⁴ are each independently hydrogen, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted diarylamino (the two aryls may not be bonded to each other or may be bonded through a linking group) , diheteroarylamino which may be substituted (two heteroaryls may not be bonded to each other or may be bonded through a single bond or linking group), arylheteroarylamino which may be substituted (aryl and heteroaryl may not be bonded to each other or , may be bonded through a single bond or linking group), optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted alkenyl, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted It is arylthio or optionally substituted silyl, and all X and Ar ⁴ are never hydrogen at the same time,

At least one hydrogen in the compound represented by formula (3-H) may be substituted with halogen, cyano, deuterium, or optionally substituted heteroaryl.

Additionally, a multimer (preferably a duplex) may be formed using the structure represented by formula (3-H) as the unit structure. In this case, for example, a form is given in which the unit structures represented by the formula (3-H) are bonded to each other through and heteroarylene (a group in which pyridine ring, dibenzofuran ring, dibenzothiophene ring, carbazole ring, benzocarbazole ring, and phenyl substituted carbazole ring have a divalent bond value).

Details of each group in the compound represented by formula (3-H) can be cited from the description in formula (1) above, and are further explained in the preferred embodiments section below.

Preferred embodiments of the anthracene compound are described below. The definitions of symbols in the following structure are the same as the definitions described above.

In formula (3-H), The group represented by the formula (X2) or (3-X3) is bonded to the anthracene ring of the formula (3-H) in *. Preferably, two Xs do not become groups represented by the formula (3-X3) at the same time. More preferably, two Xs do not simultaneously become groups represented by the formula (3-X2).

Additionally, a multimer (preferably a duplex) may be formed using the structure represented by formula (3-H) as the unit structure. In this case, for example, there is a form in which the unit structures represented by formula (3-H) are bonded through and heteroarylene (a group in which pyridine ring, dibenzofuran ring, dibenzothiophene ring, carbazole ring, benzocarbazole ring, and phenyl substituted carbazole ring have a divalent bond value).

The naphthylene moiety in formulas (3-X1) and (3-X2) may be condensed with one benzene ring. The condensed structure in this way is as follows.

　

Ar ¹ and Ar ² are each independently hydrogen, phenyl, biphenylyl, terphenylyl, quarterphenylyl, naphthyl, phenanthryl, fluorenyl, benzofluorenyl, chrysenyl, triphenylenyl, p. Reniryl, or a group represented by formula (A) (including carbazolyl, benzocarbazolyl, and phenyl-substituted carbazolyl). In addition, when Ar ¹ or Ar ² is a group represented by formula (A), the group represented by formula (A) bonds to the naphthalene ring in formula (3-X1) or formula (3-X2) at *.

Ar ³ is phenyl, biphenylyl, terphenylyl, quarterphenylyl, naphthyl, phenanthryl, fluorenyl, benzofluorenyl, chrysenyl, triphenylenyl, pyrenylyl, or formula (A) (also includes carbazolyl, benzocarbazolyl and phenyl substituted carbazolyl). Additionally, when Ar ³ is a group represented by formula (A), the group represented by formula (A) is bonded at * to the single bond represented by the straight line in formula (3-X3). That is, the anthracene ring of formula (3-H) and the group represented by formula (A) are directly bonded.

Additionally, Ar ³ may have a substituent, and at least one hydrogen in Ar ³ is alkyl with 1 to 4 carbon atoms, cycloalkyl with 5 to 10 carbon atoms, phenyl, biphenylyl, terphenylyl, naphthyl, or phenene. It may be further substituted with tril, fluorenyl, chrysenyl, triphenylenyl, pyrenyl, or a group represented by formula (A) (including carbazolyl and phenyl-substituted carbazolyl). In addition, when the substituent of Ar ³ is a group represented by formula (A), the group represented by formula (A) bonds to Ar ³ in formula (3-X3) at *.

Ar ⁴ is each independently hydrogen, phenyl, biphenylyl, terphenylyl, naphthyl, or alkyl of 1 to 4 carbon atoms (methyl, ethyl, t-butyl, etc.) and/or cycloalkyl of 5 to 10 carbon atoms. It is silyl substituted with .

Alkyl having 1 to 4 carbon atoms substituted for silyl includes methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, t-butyl, cyclobutyl, etc., and each of the three hydrogens in silyl is independent. , these are substituted with alkyl.

Specific examples of “silyl substituted with alkyl having 1 to 4 carbon atoms” include trimethylsilyl, triethylsilyl, tripropylsilyl, triisopropylsilyl, tributylsilyl, trisec-butylsilyl, trit-butylsilyl, and ethyldimethyl. Silyl, propyldimethylsilyl, isopropyldimethylsilyl, butyldimethylsilyl, sec-butyldimethylsilyl, t-butyldimethylsilyl, methyldiethylsilyl, propyldiethylsilyl, isopropyldiethylsilyl, butyldiethylsilyl, sec- Butyldiethylsilyl, t-butyldiethylsilyl, methyldipropylsilyl, ethyldipropylsilyl, butyldipropylsilyl, sec-butyldipropylsilyl, t-butyldipropylsilyl, methylisopropylsilyl, ethyldiisopropyl Silyl, butyldiisopropylsilyl, sec-butyldiisopropylsilyl, t-butyldiisopropylsilyl, etc. can be mentioned.

Cycloalkyl having 5 to 10 carbon atoms substituted for silyl includes cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.0]pentyl, and bicycloalkyl. Cyclo[2.1.1]hexyl, bicyclo[3.1.0]hexyl, bicyclo[2.2.1]heptyl(norbornenyl), bicyclo[2.2.2]octyl, adamantyl, decahydronaphtharenyl, deca Examples include hydroazulenyl, and the three hydrogens in silyl are each independently substituted with these cycloalkyls.

Specific examples of “silyl substituted with cycloalkyl having 5 to 10 carbon atoms” include tricyclopentylsilyl, tricyclohexylsilyl, and the like.

Substituted silyl includes dialkylcycloalkylsilyl substituted with two alkyls and one cycloalkyl, and alkyldicycloalkylsilyl substituted with one alkyl and two cycloalkyls, and the substituted alkyl and cycloalkyl Specific examples include the groups described above.

Additionally, hydrogen in the chemical structure of the anthracene compound represented by formula (3-H) may be substituted with a group represented by formula (A). When substituted with a group represented by formula (A), the group represented by formula (A) is substituted for at least one hydrogen in the compound represented by formula (3-H) in its *.

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

In formula (A), Y is -O-, -S- or >NR ²⁹ , and R ²¹ to R ²⁸ are each independently hydrogen, optionally substituted alkyl, optionally substituted cycloalkyl, or optionally substituted aryl. , optionally substituted heteroaryl, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted arylthio, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, alkyldicycloalkylsilyl, substituted It may be amino, halogen, hydroxy or cyano, and the adjacent groups among R ²¹ to ^{R 28} may be bonded to each other to form a hydrocarbon ring, aryl ring or heteroaryl ring, and R ²⁹ may be hydrogen or substituted. It's Aril.

Y in formula (A) is preferably -O-.

The “alkyl” of “optionally substituted alkyl” for R ²¹ to ^{R 28} may be either linear or branched, for example, straight chain alkyl with 1 to 24 carbon atoms or branched chain with 3 to 24 carbon atoms. Alkyl may be mentioned. Alkyl with 1 to 18 carbon atoms (branched chain alkyl with 3 to 18 carbon atoms) is preferable, alkyl with 1 to 12 carbon atoms (branched chain alkyl with 3 to 12 carbon atoms) is more preferable, and alkyl with 1 to 6 carbon atoms (branched chain alkyl with 3 to 12 carbon atoms) is more preferable. Branched-chain alkyl with ~6 carbon atoms) is more preferable, and alkyl with 1-4 carbon atoms (branched-chain alkyl with 3-4 carbon atoms) is particularly preferable.

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-methyl heptyl, 2-ethyl Hexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 2,6-dimethyl-4-heptyl, 3,5,5-trimethylhexyl, n-decyl, n-undecyl, 1-methyldecyl , n-dodecyl, n-tridecyl, 1-hexylheptyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, n-eicosyl, etc. .

Examples of “cycloalkyl” of “optionally substituted cycloalkyl” for R ²¹ to ^{R 28} include cycloalkyl with 3 to 24 carbon atoms, cycloalkyl with 3 to 20 carbon atoms, cycloalkyl with 3 to 16 carbon atoms, and 3 to 3 carbon atoms. Cycloalkyl with 14 carbon atoms, cycloalkyl with 5 to 10 carbon atoms, cycloalkyl with 5 to 8 carbon atoms, cycloalkyl with 5 to 6 carbon atoms, cycloalkyl with 5 carbon atoms, etc.

Specific examples of “cycloalkyl” include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, and alkyl (especially methyl) substituents of these having 1 to 4 carbon atoms, and 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( norbornenyl), bicyclo[2.2.2]octyl, adamantyl, diamantyl, decahydronaphtharenyl, decahydroazulenyl, etc.

Examples of “aryl” in “optionally substituted aryl” for R ²¹ to ^{R 28} include aryl having 6 to 30 carbon atoms, with aryl having 6 to 16 carbon atoms being preferable, and aryl having 6 to 12 carbon atoms. Aryl is more preferred, and aryl having 6 to 10 carbon atoms is particularly preferred.

Specific examples of “aryl” include monocyclic phenyl, bicyclic biphenylyl, condensed bicyclic naphthyl, tricyclic terphenylyl (m-terphenylyl, o-terphenylyl, p-terphenylyl), Examples include acenaphthyrenyl, fluorenyl, phenalenyl, and phenanthrenyl, which are condensed tricyclic systems; triphenylenyl, pyrenyl, and naphthacenyl, which are condensed tetracyclic systems; and perylenyl and pentacenyl, which are condensed pentacyclic systems. .

Examples of “heteroaryl” of “optionally substituted heteroaryl” for R ²¹ to ^{R 28} include heteroaryl having 2 to 30 carbon atoms, with heteroaryl having 2 to 25 carbon atoms being preferable, Heteroaryl with 2 to 20 carbon atoms is more preferable, heteroaryl with 2 to 15 carbon atoms is still more preferable, and heteroaryl with 2 to 10 carbon atoms is especially preferable. Examples of heteroaryl include heterocycles containing 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen in addition to carbon as ring atoms.

Specific examples of “heteroaryl” include pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, pyrazolyl, and pyrazolyl. diyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, indolyl, isoindolyl, 1H-indazolyl, benzoimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolyl, Isoquinolyl, cinnolyl, quinazolyl, quinoxalinyl, phthalazinyl, naphthyridinyl, purinyl, pteridinyl, carbazolyl, acridinyl, phenoxathiinyl, phenoxazinyl, phenothiazinyl, Phenazinyl, indolizinyl, furyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, thienyl, benzo[b]thienyl, dibenzothienyl, furazanyl, thianthrenyl, naphthobenzofuranyl. , naphthobenzothienyl, etc.

Examples of the “alkoxy” of “optionally substituted alkoxy” for R ²¹ to ^{R 28} include straight-chain alkoxy with 1 to 24 carbon atoms or branched chain alkoxy with 3 to 24 carbon atoms. Alkoxy with 1 to 18 carbon atoms (branched chain alkoxy with 3 to 18 carbon atoms) is preferable, alkoxy with 1 to 12 carbon atoms (branched chain alkoxy with 3 to 12 carbon atoms) is more preferable, and alkoxy with 1 to 6 carbon atoms (branched chain alkoxy with 3 to 12 carbon atoms) is more preferable. Branched-chain alkoxy with ~6 carbon atoms) is more preferable, and alkoxy with 1-4 carbon atoms (branched-chain alkoxy with 3-4 carbon atoms) is particularly preferable.

Specific examples of “alkoxy” include methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, s-butoxy, t-butoxy, pentyloxy, hexyloxy, heptyloxy, octyloxy, etc. You can.

The “aryloxy” of “optionally substituted aryloxy” for R ²¹ to ^{R 28} is a group in which the hydrogen of the -OH group is substituted with aryl, and this aryl is the “aryloxy” for R ²¹ to R ²⁸ described above. The group described as “aryl” can be cited.

The “arylthio” of “optionally substituted arylthio” in R ²¹ to ^{R 28} is a group in which the hydrogen of the -SH group is substituted with aryl, and this aryl is the “arylthio” in R ²¹ to R ²⁸ described above. The group described as “aryl” can be cited.

Examples of “trialkylsilyl” for R ²¹ to ^{R 28} include groups in which three hydrogens in the silyl group are each independently substituted with alkyl, and this alkyl is the “alkyl” for R ²¹ to R ²⁸ described above. 」 can be cited. Alkyl suitable for substitution is alkyl having 1 to 4 carbon atoms, and specific examples include methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, t-butyl, and cyclobutyl.

Specific examples of “trialkylsilyl” include trimethylsilyl, triethylsilyl, tripropylsilyl, triisopropylsilyl, tributylsilyl, trisec-butylsilyl, trit-butylsilyl, ethyldimethylsilyl, propyldimethylsilyl, and isopropyl. Dimethylsilyl, butyldimethylsilyl, sec-butyldimethylsilyl, t-butyldimethylsilyl, methyldiethylsilyl, propyldiethylsilyl, isopropyldiethylsilyl, butyldiethylsilyl, sec-butyldiethylsilyl, t-butyl Diethylsilyl, methyldipropylsilyl, ethyldipropylsilyl, butyldipropylsilyl, sec-butyldipropylsilyl, t-butyldipropylsilyl, methylisopropylsilyl, ethyldiisopropylsilyl, butyldiisopropylsilyl, sec-butyldiisopropylsilyl, t-butyldiisopropylsilyl, etc. can be mentioned.

Examples of “tricycloalkylsilyl” for R ²¹ to ^{R 28} include groups in which three hydrogens in the silyl group are each independently substituted with cycloalkyl, and this cycloalkyl is substituted for R ²¹ to R ²⁸ above. The group described as “cycloalkyl” may be cited. Cycloalkyl preferred for substitution is cycloalkyl having 5 to 10 carbon atoms, specifically cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, bicyclo[1.1.1]pentyl, and 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, decahydronaphtharenyl, Decahydroazulenyl, etc. can be mentioned.

Specific examples of “tricycloalkylsilyl” include tricyclopentylsilyl, tricyclohexylsilyl, and the like.

Specific examples of dialkylcycloalkylsilyl substituted with two alkyls and one cycloalkyl and alkyldicycloalkylsilyl substituted with one alkyl and two cycloalkyls are substituted with a group selected from the above-mentioned specific alkyl and cycloalkyl. You can pick up one silyl.

Examples of the “substituted amino” of the “optionally substituted amino” for R ²¹ to ^{R 28} include amino in which two hydrogens are substituted with aryl or heteroaryl. Amino in which two hydrogens are substituted with aryl is diaryl (the two aryls may not be bonded to each other or may be bonded through a linker), and amino in which two hydrogens are substituted with heteroaryl is diheteroaryl-substituted amino. , and an amino in which two hydrogens are substituted with aryl and heteroaryl is an arylheteroaryl-substituted amino. This aryl or heteroaryl can refer to the groups described as “aryl” or “heteroaryl” for R ²¹ to ^{R 28} described above.

Specific examples of “substituted amino” include diphenylamino, dinaphthylamino, phenylnaphthylamino, dipyridylamino, phenylpyridylamino, naphthylpyridylamino, etc.

Examples of “halogen” in R ²¹ to ^{R 28} include fluorine, chlorine, bromine, and iodine.

Among the groups described as R ²¹ to ^{R 28} , some may be substituted as described above, and examples of the substituent in this case include alkyl, cycloalkyl, aryl, or heteroaryl. This alkyl, cycloalkyl, aryl or heteroaryl can refer to the groups described as “alkyl”, “cycloalkyl”, “aryl” or “heteroaryl” for R ²¹ to R ²⁸ described above.

R ²⁹ in “>NR ²⁹ ” as Y is hydrogen or optionally substituted aryl. As this aryl, the group described as “aryl” in R ²¹ to ^{R 28} described above can be cited, and as the substituent, The groups described as substituents for R ²¹ to ^{R 28} may be cited.

Adjacent groups among R ²¹ to R ²⁸ may be bonded to each other to form a hydrocarbon ring, an aryl ring, or a heteroaryl ring. When a ring is not formed, it is a group represented by the following formula (A-1), and when a ring is formed, for example, a group is represented by the following formulas (A-2) to (A-14). . In addition, at least one hydrogen in the group represented by any one of formulas (A-1) to (A-14) is alkyl, cycloalkyl, aryl, heteroaryl, alkoxy, aryloxy, arylthio, trialkylsilyl, Tricycloalkylsilyl, dialkylcycloalkylsilyl, alkyldicycloalkylsilyl, diaryl (two aryls may not be bonded to each other or may be bonded through a linking group) Substituted amino, diheteroaryl Substituted amino, arylheteroaryl substituted It may be substituted with amino, halogen, hydroxy or cyano.

As a ring formed by bonding adjacent groups to each other, if it is a hydrocarbon ring, for example, a cyclohexane ring can be given, and as an aryl ring or heteroaryl ring, "aryl" or "heteroaryl" in R ²¹ to R ²⁸ mentioned above can be used. The ring structures described can be mentioned, and these rings are formed by condensation with one or two benzene rings in formula (A-1).

The group represented by formula (A) is a group obtained by removing one hydrogen from any position in formula (A), and * indicates the position. That is, the group represented by formula (A) may have any one position as the bonding position. For example, any one carbon atom on two benzene rings in the structure of formula (A), any one cyclic atom formed by bonding adjacent groups among R ²¹ to R ²⁸ in the structure of formula (A), or Directly at any position of R ²⁹ in “>NR ²⁹ ” as Y in the structure of formula (A), or with N (R ²⁹ becomes the bonding hand) in “>NR ²⁹ ” It can be a binding group. The same applies to groups represented by any of formulas (A-1) to (A-14).

Examples of the group represented by formula (A) include groups represented by any one of formulas (A-1) to (A-14), formulas (A-1) to formula (A-5), and A group represented by any one of formulas (A-12) to (A-14) is preferable, a group represented by any of formulas (A-1) to formula (A-4) is more preferable, and the group represented by formula (A-1) is more preferable. ), a group represented by any one of formulas (A-3) and (A-4) is more preferable, and a group represented by formula (A-1) is particularly preferable.

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

In the compound represented by formula (3-H), the group represented by formula (A) is a naphthalene ring in formula (3-X1) or formula (3-X2), a single bond in formula (3-X3), and a group represented by formula (A). A form bonded to any one of Ar ³ in (3-X3) is preferable.

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

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

In formula (3-H2), Ar ^c is optionally substituted aryl or optionally substituted heteroaryl, R ^c is hydrogen, alkyl, or cycloalkyl, and Ar ¹¹ , Ar ¹² , Ar ¹³ , Ar ¹⁴ , Ar ¹⁵ , Ar ¹⁶ , Ar ¹⁷ , and Ar ¹⁸ are each independently hydrogen, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted diarylamino (two aryls are not bonded to each other or , may be bonded through a linking group), diheteroarylamino which may be substituted (two heteroaryls may not be bonded to each other or may be bonded through a single bond or a linking group), arylheteroarylamino which may be substituted ( Two heteroaryls may not be bonded to each other or may be bonded through a single bond or linking group), optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted alkenyl, optionally substituted alkoxy, optionally substituted It is optionally aryloxy, optionally substituted arylthio, or optionally substituted silyl, and at least one hydrogen in the compound represented by formula (1) may be substituted with halogen, cyano, or deuterium.

In formula (3-H2), “aryl which may be substituted,” “heteroaryl which may be substituted,” and “diarylamino which may be substituted (two aryls may not be bonded to each other or may be bonded through a linking group. )”, “Diheteroarylamino which may be substituted (two heteroaryls may not be bonded to each other or may be bonded through a single bond or linking group)”, “arylheteroarylamino which may be substituted (two heteroaryls may not be bonded to each other or may be bonded through a single bond or linking group)”, “Alkyl which may be substituted”, “Cycloalkyl which may be substituted”, “Alkenyl which may be substituted”, “Alkenyl which may be substituted” The definitions of “alkoxy”, “optionally substituted aryloxy”, “optionally substituted arylthio”, or “optionally substituted silyl” are the same as those in formula (3-H) above, and in formula (1) The explanation may be cited.

As “optionally substituted aryl”, a group represented by any of the following formulas (3-H2-X1) to (3-H2-X8) is also preferable.

In formulas (3-H2-X1) to (3-H2-X8), * represents the binding position. In formulas (3-H2-X1) to (3-H2-X3), Ar ²¹ , Ar ²² , and Ar ²³ are each independently hydrogen, phenyl, biphenylyl, terphenylyl, or quarterphenylyl. , naphthyl, phenanthryl, fluorenyl, benzofluorenyl, chrysenyl, triphenylenyl, pyrenyl, anthracenyl, or a group represented by formula (A). In addition, in the description of formula (3-H2), the group represented by formula (A) is the same as that described for the anthracene compound represented by formula (3-H).

In formulas (3-H2-X4) to (3-H2-X8), Ar ²⁴ , Ar ²⁵ , Ar ²⁶ , Ar ²⁷ , Ar ²⁸ , Ar ²⁹ , and Ar ³⁰ are each independently hydrogen, phenyl, , biphenylyl, terphenylyl, naphthyl, phenanthryl, fluorenyl, chrysenyl, triphenylenyl, pyrenyl, or a group represented by formula (A). Additionally, any one or two or more hydrogens in each of the groups represented by formulas (3-H2-X1) to (3-H2-X8) are alkyl (preferably methyl or It may be substituted with t-butyl).

Furthermore, preferred examples of “optionally substituted aryl” include phenyl, biphenylyl, terphenylyl, naphthyl, phenanthryl, fluorenyl, chrysenyl, triphenylenyl, pyrenyl, and and terphenylyl (particularly m-terphenyl-5'-yl), which may be substituted with one or more substituents selected from the group consisting of groups.

Examples of “optionally substituted heteroaryl” include groups represented by formula (A). In addition, specific examples of “optionally substituted aryl” and “optionally substituted heteroaryl” include dibenzofuryl, naphthobenzofuryl, and phenyl-substituted dibenzofuryl.

At least one hydrogen in the compound represented by formula (1) may be substituted with halogen, cyano, or deuterium. Examples of “halogen” in this case include fluorine, chlorine, bromine, and iodine. In particular, a compound in which all hydrogens in the compound represented by the formula (3-H2) are replaced with deuterium is preferable.

In formula (3-H2), R ^c is hydrogen, alkyl, or cycloalkyl, preferably hydrogen, methyl, or t-butyl, and more preferably hydrogen.

In formula (3-H2), at least two of Ar ¹¹ to Ar ¹⁸ are preferably 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 an anthracene ring.

The anthracene compound represented by the formula (3-H2) is an aryl that may be substituted or heteroaryl that may be substituted, where two of Ar ¹¹ to ^{Ar 18} are hydrogen, alkyl which may be substituted, and heteroaryl which may be substituted. More preferably, it is cycloalkyl, optionally substituted alkenyl, or optionally substituted alkoxy. That is, the anthracene compound represented by the formula (3-H2) more preferably 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.

The anthracene compound represented by the formula (3-H2) is aryl where any two of Ar ¹¹ to ^{Ar 18} may be substituted or heteroaryl which may be substituted, and the other six are hydrogen, methyl, or t-butyl. desirable.

Furthermore, in the formula (3-H2), it is preferable that R ^c is hydrogen and any six of Ar ¹¹ to Ar ¹⁸ are hydrogen.

Anthracene compounds represented by formula (3-H2) have the following formula (3-H2-A), (3-H2-B), (3-H2-C), (3-H2-D), or (3- It is preferable that it is an anthracene compound represented by H2-E).

In formula (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 ' are each independently phenyl, biphenylyl, terphenylyl, quarterphenylyl, naphthyl, phenanthryl, fluorescein Nyl, benzofluorenyl, chrysenyl, triphenylenyl, pyrenyl, or a group represented by formula (A), and at least one hydrogen in this group is phenyl, biphenylyl, terphenylyl, or quarter. It may be substituted with phenylyl, naphthyl, phenanthryl, fluorenyl, benzofluorenyl, chrysenyl, triphenylenyl, pyrenyl, or a group represented by formula (A). Here, when all of the hydrogens of methylene in fluorenyl and benzofluorenyl are substituted with phenyl, the phenyl may be bonded to each other by a single bond. The carbon atom of the anthracene ring to which Ar ^c ', Ar ¹¹ ', Ar ¹² ', Ar ¹³ ', Ar ¹⁴ ', Ar ¹⁵ ', Ar ¹⁷ ', and Ar ¹⁸ ' are not bonded has methyl or t-butyl instead of hydrogen. It may be combined.

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

Ar ^c ', Ar ¹¹ ', Ar ¹² ', Ar ¹³ ', Ar ¹⁴ ', Ar ¹⁵ ', Ar ¹⁷ ', and Ar ¹⁸ ' are each independently phenyl, biphenylyl (particularly, biphenyl-2-yl or biphenyl-4-yl), terphenylyl (especially m-terphenyl-5'-yl), naphthyl, phenanthryl, fluorenyl, or formula (A-1) to formula (A) It is more preferable that it is a group represented by any one of -4), and at this time, at least one hydrogen in this group is phenyl, biphenylyl, naphthyl, phenanthryl, fluorenyl, or the formula (A It may be substituted with a group represented by any one of -1) to formula (A-4).

In addition, in compounds represented by the formula (3-H2-A), (3-H2-B), (3-H2-C), (3-H2-D), or (3-H2-E) At least one hydrogen may be substituted with halogen, cyano, or deuterium. Also, a deuterated form is preferable, and a form in which all anthracene rings are deuterated, or a form in which all hydrogen atoms are deuterated, is preferable.

A particularly preferable anthracene compound represented by the formula (3-H2) includes an anthracene compound represented by the following formula (3-H2-Aa).

In formula (3-H2-Aa), Ar ^c ', Ar ¹⁴ ', and Ar ¹⁵ ' are each independently selected from phenyl, biphenylyl, terphenylyl, naphthyl, phenanthryl, fluorenyl, and benzofluore. Nyl, chrysenyl, triphenylenyl, pyrenyl, or a group represented by any of the above formulas (A-1) to (A-11), and at least one hydrogen in this group is phenyl, biphenylyl, , terphenylyl, naphthyl, phenanthryl, fluorenyl, benzofluorenyl, chrysenyl, triphenylenyl, pyrenyl, or a group represented by any one of formulas (A-1) to (A-11). It may be substituted. Here, when all of the hydrogens of methylene in fluorenyl and benzofluorenyl are substituted with phenyl, the phenyl may be bonded to each other by a single bond. Additionally, the carbon atom on the anthracene ring to which Ar ^c ', Ar ¹⁴ ', and Ar ¹⁵ ' are not bonded may be substituted with methyl or t-butyl instead of hydrogen. At least one hydrogen in the compound represented by the formula (3-H2-Aa) may be substituted with halogen or cyano, and at least one hydrogen in the compound represented by the formula (3-H2-Aa) may be substituted with halogen or cyano. It is replaced with deuterium.

In formula (3-H2-Aa), Ar ^c ', Ar ¹⁴ ', and Ar ¹⁵ ' are each independently phenyl, biphenylyl, terphenylyl, naphthyl, phenanthryl, fluorenyl, or the formula ( It is preferable that it is a group represented by any one of formulas A-1) to (A-4), and at least one hydrogen in this group is phenyl, naphthyl, phenanthryl, fluorenyl, or formula (A-1) ~ may be substituted with a group represented by any one of formula (A-4).

In the compound represented by the formula (3-H2-Aa), it is preferable that at least the hydrogen bonded to the carbon at the 10th position of the anthracene ring (the carbon to which Ar ^c ' is bonded is taken at the 9th position) is substituted with deuterium. . That is, the compound represented by the formula (3-H2-Aa) is preferably a compound represented by the following formula (3-H2-Ab). Additionally, in formula (3-H2-Ab), D is deuterium, and Ar ^c ', Ar ¹⁴ ', and Ar ¹⁵ ' are the same as the definitions in formula (3-H2-Aa). D in the formula (3-H2-Ab) indicates that at least this position is deuterium, any one or more of the other hydrogens in the formula (3-H2-Ab) may be deuterium at the same time, and formula (3-H2 It is also preferable that all hydrogens in -Ab) are deuterium.

　

In addition, specific examples of anthracene compounds include, for example, compounds represented by formulas (3-131-Y) to (3-182-Y), formulas (3-183-N), and formulas (3-184-Y). ) to Equation (3-284-Y), and Equation (3-500) to Equation (3-557), and Equation (3-600) to Equation (3-605), and Equation (3-606-Y) to A compound represented by the formula (3-626-Y) can be mentioned. The hydrogen atoms in these formulas may be partially or completely substituted with deuterium, but particularly preferred forms of deuterium substitution are listed individually. Y in the formula is -O-, -S-, >NR ²⁹ (R ²⁹ is defined as above) or >C(-R ³⁰ ) ₂ (R ³⁰ is aryl or alkyl that may be connected). R ²⁹ is, for example, phenyl, and R ³⁰ is, for example, methyl. The formula number is, for example, when Y is O, formula (3-131-Y) is formula (3-131-O), and when Y is -S- or >NR ²⁹ , formula (3- 131-S) or formula (3-131-N).

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

The anthracene compound includes a compound having a reactive group at a desired position of the anthracene skeleton, and, in the case of an anthracene compound represented by formula (3-H), a compound having a reactive group in partial structures such as X, Ar ⁴ and the structure of formula (A). It can be manufactured by using as a starting material, Suzuki coupling, Negishi coupling, and other known coupling reactions. Reactive groups of these reactive compounds include halogen and boronic acid. As a specific manufacturing method, for example, the synthesis method in paragraphs [0089] to [0175] of International Publication No. 2014/141725 can be referred to.

<Fluorene compound>

The compound represented by formula (4-H) basically functions as a host.

In formula (4-H),

R ¹ to R ¹⁰ are each independently hydrogen, aryl, heteroaryl (the heteroaryl may be bonded to the fluorene skeleton in the formula (4-H) through a linking group), or diarylamino (two Aryl may not be bonded to each other or may be bonded through a linking group), diheteroarylamino (two heteroaryls may not be bonded to each other or may be bonded through a single bond or linking group), arylheteroarylamino (aryl and Heteroaryl may not be bonded to each other, or may be bonded through a single bond or linking group), alkyl, cycloalkyl, alkenyl, alkoxy, or aryloxy, and at least one hydrogen in these is aryl, heteroaryl, alkyl, or It may be substituted with cycloalkyl, and may also be 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 may be independently bonded to form a condensed ring or spiro ring, and at least one hydrogen in the formed ring may be aryl, heteroaryl (the heteroaryl may be bonded to the formed ring through a linking group), or dia Rylamino (two aryls may not be bonded to each other or may be bonded through a linking group), diheteroarylamino (two heteroaryls may not be bonded to each other or may be bonded through a single bond or a linking group), arylhetero Arylamino (aryl and heteroaryl may not be bonded to each other or may be bonded through a single bond or linking group), alkyl, cycloalkyl, alkenyl, alkoxy, or aryloxy, and at least one of these may be substituted. Hydrogen may be substituted with aryl, heteroaryl, alkyl, or cycloalkyl, and at least one hydrogen in the compound represented by formula (4-H) may be substituted with halogen, cyano, or deuterium.

For details of each group in the definition of formula (4-H), the description of the polycyclic aromatic compound of formula (1) described above can be cited.

Examples of alkenyl for R ¹ to R ¹⁰ include alkenyl having 2 to 30 carbon atoms, with alkenyl having 2 to 20 carbon atoms being preferable, and alkenyl having 2 to 10 carbon atoms being more preferable. , alkenyl having 2 to 6 carbon atoms is more preferable, and alkenyl having 2 to 4 carbon atoms is particularly preferable. Preferred alkenyls include vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-phenyl tenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, or 5-hexenyl.

In addition, as a specific example of heteroaryl, any one of the compounds of the following formula (4-Ar1), (4-Ar2), (4-Ar3), (4-Ar4), or (4-Ar5) Monovalent groups expressed by excluding the hydrogen atom may also be mentioned.

In formulas (4-Ar1) to (4-Ar5), Y ¹ is each independently O, S or NR, R is phenyl, biphenylyl, naphthyl, anthracenyl or hydrogen, and formula (4 At least one hydrogen in the structures of -Ar1) to (4-Ar5) may be substituted with phenyl, biphenylyl, naphthyl, anthracenyl, phenanthrenyl, methyl, ethyl, propyl, or butyl. .

These heteroaryls may be bonded to the fluorene skeleton in formula (4-H) through a linking group. That is, the fluorene skeleton in formula (4-H) and the heteroaryl may not only be bonded directly, but may also be bonded through a linking group between them. Examples of this linking group include phenylene, biphenylene, naphthylene, anthracenylene, methylene, ethylene, -OCH ₂ CH ₂ -, -CH ₂ CH ₂ O-, or -OCH ₂ CH ₂ O-. there is.

In addition, 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 or R ⁷ and R ⁸ in formula (4-H) are each independently combined In the condensed ring, R ⁹ and R ¹⁰ may be bonded to form a spiro ring. The condensed ring formed by R ¹ to R ⁸ is a ring condensed to a benzene ring in the formula (4-H) and is an aliphatic ring or an aromatic ring. It is preferably an aromatic ring, and examples of structures including a benzene ring in formula (4-H) include a naphthalene ring and a phenanthrene ring. The spiro ring formed by R ⁹ and R ¹⁰ is a ring that is spiro-bonded to a 5-membered ring in formula (4-H) and is an aliphatic ring or an aromatic ring. Preferably it is an aromatic ring, and examples include a fluorene ring.

The compound represented by formula (4-H) is preferably a compound represented by the following formula (4-H-1), formula (4-H-2), or formula (4-H-3), respectively. , a compound obtained by condensation of the benzene ring formed by combining R ¹ and R ² in formula (4-H), a compound obtained by condensation of the benzene ring formed by combining R ³ and R ⁴ in formula (4-H), formula (4 In -H), it is a compound in which all of R ¹ to R ⁸ are not bonded.

The definitions of R 1 to R 10 in formula (4-H-1), formula (4-H-2) and formula (4-H-3) are the corresponding ^{R 1 to} R ¹⁰ in formula (4-H). It is the same as R ¹⁰ , and the definitions of R ¹¹ to R ¹⁴ in formulas (4-H-1) and (4-H-2) are also the same as for R ¹ to R ¹⁰ in formula (4-H). do.

The compound represented by the formula (4-H) is more preferably a compound represented by the following formula (4-H-1A), formula (4-H-2A), or formula (4-H-3A). , are compounds in which R ⁹ and R ¹⁰ are bonded to form a spiro-fluorene ring in formula (4-H-1), formula (4-H-1) or formula (4-H-3), respectively.

　

The definitions of R ² to R ⁷ in Formulas (4-1A), (4-2A) and (4-3A) are Formulas (4-1), (4-2) and (4-3) ) are the same as the corresponding R ² to R ⁷ , and the definitions of R ¹¹ to R ¹⁴ in Formulas (4-1A) and (4-2A) are also defined in Formulas (4-1) and (4-2) ) are the same as R ¹¹ to R ¹⁴ in .

Additionally, all or part of the hydrogen in the compound represented by formula (4-H) may be substituted with halogen, cyano, or deuterium.

More specific examples of the fluorene compound as the host of the present invention include compounds represented by the following structural formula. Additionally, “Me” represents methyl.

<Dibenzochrysene compound>

The dibenzochrysene compound as the host is, for example, a compound represented by the following formula (5-H).

In formula (5-H), R ¹ to R ¹⁶ are each independently hydrogen, aryl, heteroaryl (the heteroaryl is bonded to the dibenzochrysene skeleton in formula (5-H) through a linking group, may be present), diarylamino (two aryls may not be bonded to each other or may be bonded through a linking group), diheteroarylamino (two heteroaryls may not be bonded to each other or may be bonded through a single bond or linking group) ), arylheteroarylamino (aryl and heteroaryl may not be bonded to each other or may be bonded through a single bond or linking group), alkyl, cycloalkyl, alkenyl, alkoxy, or aryloxy, and at least one of these The hydrogen may be substituted with aryl, heteroaryl, alkyl, or cycloalkyl, and adjacent groups among R ¹ to R ¹⁶ may be bonded to form a condensed ring, and at least one hydrogen in the formed ring may be Aryl, heteroaryl (the heteroaryl may be bonded to the formed ring through a linking group), diarylamino (two aryls may not be bonded to each other or may be bonded through a linking group), diheteroarylamino (2 Heteroaryl may not be bonded to each other or may be bonded through a single bond or a linking group), arylheteroarylamino (aryl and heteroaryl may not be bonded to each other or may be bonded through a single bond or linking group), alkyl, Compounds that may be substituted with cycloalkyl, alkenyl, alkoxy, or aryloxy, and at least one hydrogen thereof may be substituted with aryl, heteroaryl, alkyl, or cycloalkyl, and are represented by the formula (5-H) At least one hydrogen may be substituted with halogen, cyano, or deuterium.

For details of each group in the definition of formula (5-H), the description of the polycyclic aromatic compound of formula (1) described above can be cited.

Examples of alkenyl in the definition of formula (5-H) include alkenyl with 2 to 30 carbon atoms, preferably alkenyl with 2 to 20 carbon atoms, and alkenyl with 2 to 10 carbon atoms. More preferable is alkenyl having 2 to 6 carbon atoms, and alkenyl having 2 to 4 carbon atoms is particularly preferable. Preferred alkenyls include vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-phenyl tenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, or 5-hexenyl.

In addition, as a specific example of heteroaryl, any one of the compounds of the following formula (5-Ar1), (5-Ar2), (5-Ar3), (5-Ar4), or (5-Ar5) Monovalent groups expressed by excluding the hydrogen atom may also be mentioned.

In formulas (5-Ar1) to (5-Ar5), Y ¹ is each independently O, S or NR, R is phenyl, biphenylyl, naphthyl, anthracenyl or hydrogen, and At least one hydrogen in the structures of -Ar1) to (5-Ar5) may be substituted with phenyl, biphenylyl, naphthyl, anthracenyl, phenanthrenyl, methyl, ethyl, propyl, or butyl. .

These heteroaryls may be bonded to the dibenzochrysene skeleton in formula (5-H) through a linking group. That is, the dibenzochrysene skeleton in formula (5-H) and the heteroaryl may not only be bonded directly, but may also be bonded through a linking group between them. Examples of this linking group include phenylene, biphenylene, naphthylene, anthracenylene, methylene, ethylene, -OCH ₂ CH ₂ -, -CH ₂ CH ₂ O-, or -OCH ₂ CH ₂ O-. there is.

In the compound represented by formula (5-H), preferably, R ¹ , R ⁴ , R ⁵ , R ⁸ , R ⁹ , R ¹² , R ¹³ and R ¹⁶ are hydrogen. In this case, R ² , R ³ , R ⁶ , R ⁷ , R ¹⁰ , R ¹¹ , R ¹⁴ and R ¹⁵ in formula (5-H) are each independently hydrogen, phenyl, biphenylyl, naphthyl, Anthracenyl, phenanthrenyl, 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 the structure is phenylene, biphenylene, naphthylene, anthracenylene, methylene, ethylene, -OCH ₂ CH ₂ -, -CH ₂ CH ₂ O-, or -OCH ₂ CH ₂ O-. (may be bonded to the dibenzochrysene skeleton in formula (5-H)), methyl, ethyl, propyl, or butyl is preferable.

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, at least one (preferably one or two, more preferably one) of R ³ , R ⁶ , R ¹¹ and R ¹⁴ in formula (5-H) is a single bond, phenylene, or Through phenylene, naphthylene, anthracenylene, methylene, ethylene, -OCH ₂ CH ₂ -, -CH ₂ CH ₂ O-, or -OCH ₂ CH ₂ O-, formula (5-Ar1), formula ( 5-Ar2), (5-Ar3), formula (5-Ar4), or formula (5-Ar5), and is a monovalent group other than at least one of the above (i.e., substituted by a monovalent group having the above structure) (other than the position) is hydrogen, phenyl, biphenylyl, naphthyl, anthracenyl, methyl, ethyl, propyl, or butyl, and at least one hydrogen in these is phenyl, biphenylyl, naphthyl, or anthracenyl. , methyl, ethyl, propyl, or butyl may be substituted.

In addition, R ² , R ³ , R ⁶ , R ⁷ , R ¹⁰ , R ¹¹ , R ¹⁴ and R ¹⁵ in formula (5-H) are represented by formulas (5-Ar1) to (5-Ar5). When a monovalent group having a structure is selected, at least one hydrogen in the structure may be bonded to any one of R ¹ to R ¹⁶ in formula (5-H) to form a single bond.

More specific examples of the dibenzochrysene compound as the host of the present invention include compounds represented by the following structural formula. Additionally, “tBu” represents t-butyl.

The above-mentioned materials for the emitting layer (host material and dopant material) are polymer compounds obtained by polymerizing a reactive compound substituted with a reactive substituent as a monomer, or a polymer crosslinked product thereof, or a main chain polymer and the reactive compound. The reacted pendant polymer compound or its pendant polymer crosslinked product can also be used as a material for the light-emitting layer. As a reactive substituent in this case, the description for the polycyclic aromatic compound represented by formula (1) can be cited.

<Emitting layer containing assisting dopant and emitting dopant>

The light-emitting layer in the organic electroluminescent element may contain a host compound as the first component, an assisting dopant (compound) as the second component, and an emitting dopant (compound) as the third component. The polycyclic aromatic compound of the present invention is also preferably used as an emitting dopant. A thermally activated delayed phosphor can be used as the assisting dopant (compound).

In the following description, an organic electroluminescent device using a thermally activated delayed phosphor as an assisting dopant may be referred to as a “TADF device” (TADF Assisting Fluorescence device). The “host compound” in a TAF element means that the lowest singlet excitation energy level obtained from the shoulder on the short wavelength side of the peak of the fluorescence spectrum is higher than that of the thermally activated delayed phosphor as the second component and the emitting dopant as the third component. It means high compound.

“Thermally activated delayed phosphor” refers to a compound that absorbs heat energy, causes reverse intersystem crossing from the triplet excited state to the singlet excited state, and emits delayed fluorescence by radiation deactivation from the singlet excited state. do. However, “thermally activated delayed fluorescence” also includes passing through a higher-order triplet during the excitation process from the triplet excited state to the singlet excited state. For example, a paper by Monkman of Durham University (NATURE COMMUNICATIONS, 7:13680, DOI:10.1038/ncomms13680), a paper by Hosokai of the Institute of Industrial Technology (Hosokai et al., Sci.Adv.2017;3: e1603282), a paper by Sato and others at Kyoto University (Scientific Reports, 7:4820, DOI:10.1038/s41598-017-05007-7), and also a conference presentation by Sato and others at Kyoto University (98th Spring Annual Meeting of the Chemical Society of Japan, Publication number: 2I4-15, Mechanism of high-efficiency light emission in organic electroluminescence using DABNA as a light-emitting molecule, Kyoto University Graduate School of Engineering, etc. In the present invention, when the fluorescence lifetime of a sample containing the target compound is measured at 300K, the target compound is determined to be a “heat-activated delayed phosphor” based on the observation of a slow fluorescence component. Here, the slow fluorescence component refers to a fluorescence lifetime of 0.1 μsec or more. Measurement of fluorescence lifetime can be performed, for example, using a fluorescence lifetime measuring device (C11367-01, manufactured by Hamamatsu Photonics Co., Ltd.).

The polycyclic aromatic compound of the present invention can function as an emitting dopant, and the “heat-activated delayed phosphor” can function as an assisting dopant that assists the light emission of the polycyclic aromatic compound of the present invention.

Figure 2 shows the energy level diagram of the light emitting layer of a TAF device using a general fluorescent dopant as an emitting dopant (ED). In the figure, the ground state energy level of the host is E(1, G), the lowest excitation singlet energy level obtained from the shoulder of the short-wavelength side of the host's fluorescence spectrum is E(1, S, Sh), and the short-wavelength side of the host's phosphorescence spectrum is E(1, S, Sh). The lowest triplet excitation energy level obtained from the shoulder is E(1, T, Sh), the ground state energy level of the assisting dopant, which is the second component, is E(2, G), and the fluorescence of the assisting dopant, which is the second component. The lowest excitation singlet energy level obtained from the shoulder on the short-wavelength side of the spectrum is E(2, S, Sh), and the lowest excitation triplet energy level obtained from the shoulder on the short-wavelength side of the phosphorescence spectrum of the assisting dopant, which is the second component, is E(2, S, Sh). 2, T, Sh), the ground state energy level of the third component, the emitting dopant, E(3, G), the lowest excited singlet energy level obtained from the shoulder of the short wavelength side of the fluorescence spectrum of the third component, the emitting dopant. is E(3, S, Sh), the lowest excitation triplet energy level obtained from the shoulder of the short wavelength side of the phosphorescence spectrum of the emitting dopant, which is the third component, is E(3, T, Sh), holes are h+, and electrons are e. -, Fluorescence resonance energy transfer is called FRET (Fluorescence Resonance Energy Transfer). In a TAF device, when a general fluorescent dopant is used as an emitting dopant (ED), the energy upconverted from the assisting dopant moves to the lowest excited singlet energy level E(3, S, Sh) of the emitting dopant and emits light. do. However, some of the lowest excitation triplet energy E(2, T, Sh) on the assisting dopant moves to the lowest excitation triplet energy level E(3, T, Sh) of the emitting dopant, or moves to the lowest excitation triplet energy level E(3, T, Sh) on the emitting dopant. An intersystem crossing occurs from the singlet energy level E(3, S, Sh) to the lowest excited triplet energy level E(3, T, Sh) and continues thermally to the ground state E(3, G). lose your life Due to this path, some of the energy is not used for light emission, resulting in energy waste.

In contrast, in the organic electroluminescent device of this embodiment, the energy transferred from the assisting dopant to the emitting dopant can be efficiently used for light emission, and thus high light emission efficiency can be realized. This is presumed to be due to the following light emission mechanism.

FIG. 3 shows a preferable energy relationship in the organic electroluminescent device of this embodiment. In the organic electroluminescent device of this embodiment, a compound having a boron atom as an emitting dopant has a high lowest triplet excitation energy level E(3, T, Sh). Because of this, the lowest excitation singlet energy upconverted in the assisting dopant is upconverted on the emitting dopant, even if it intersects to the lowest excitation triplet energy level E(3, T, Sh) in the emitting dopant. Alternatively, it is recovered to the lowest excitation triplet energy level E(2, T, Sh) on the assisting dopant (thermally activated delayed phosphor). Therefore, the generated excitation energy can be used for light emission without waste. In addition, by dividing the molecule into two types that can improve the functions of upconversion and light emission, it is expected that the residence time of high energy will be reduced and the burden on the compound will be reduced.

In this embodiment, known host compounds can be used, and examples include compounds having at least one of a carbazole ring and a furan ring, and among them, at least one of furanyl and carbazolyl, and an aryl ring. It is preferable to use a compound in which at least one of lene and heteroarylene is bonded. Specific examples include mCP and mCBP.

The lowest excitation triplet energy level E(1, T, Sh), obtained from the shoulder on the short wavelength side of the peak of the phosphorescence spectrum of the host compound, is the lowest in the light-emitting layer from the viewpoint of promoting rather than inhibiting the generation of TADF in the light-emitting layer. Compared to the lowest triplet excitation energy level E(2, T, Sh), E(3, T, Sh) of the emitting dopant or assisting dopant having a high lowest triplet excitation energy level, it is preferable that it is higher, and the specific In other words, the lowest triplet excitation energy level E(1, T, Sh) of the host compound is preferably 0.01 eV or more, and 0.03 eV compared to E(2, T, Sh) and E(3, T, Sh). More than this is more preferable, and 0.1 eV or more is even more preferable. Additionally, a compound with TADF activity may be used as the host compound.

As the host compound, for example, a compound represented by any of the above formulas (H1), (H2), and (H3) can be used.

<Thermally activated delayed phosphor (assisting dopant)>

The thermally activated delayed phosphor (TADF compound) used in TAF devices uses an electron-donating substituent called a donor and an electron-accepting substituent called an acceptor to create HOMO (Highest Occupied Molecular Orbital) and LUMO (Lowest Unoccupied) within the molecule. It is preferable that it is a donor-acceptor type thermally activated delayed phosphor (D-A type TADF compound) designed to localize the molecular orbital and cause efficient reverse intersystem crossing. Here, in this specification, the “electron-donating substituent” (donor) refers to the substituent and partial structure where the HOMO orbital is localized in the thermally activated delayed phosphor molecule, and the “electron-accepting substituent” (acceptor) refers to, This refers to the substituent and partial structure in which the LUMO orbital is localized among the thermally activated delayed phosphor molecules.

In general, thermally activated delayed phosphors using donors or acceptors have large spin orbit coupling (SOC) due to their structure, and at the same time, the exchange interaction between HOMO and LUMO is small and ΔE(ST) is small. Therefore, a very fast inverse intersystem crossing speed is obtained. On the other hand, thermally activated delayed phosphors using donors or acceptors have greater structural relaxation in the excited state (for some molecules, the stable structures are different in the ground state and excited state, so external stimulation causes the structural relaxation to change from the ground state to the excited state). When the conversion occurs, the structure changes to a stable structure in the excited state) and provides a wide luminescence spectrum, so there is a possibility that color purity may be reduced when used as a luminescent material.

As a thermally activated delayed phosphor in a TAF device, for example, a compound in which a donor and an acceptor are bonded directly or through 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 structure described in Chemistry of Materials, 2017, 29, 1946-1963 You can use it. Donor structures include carbazole, dimethylcarbazole, di-tert-butylcarbazole, dimethoxycarbazole, tetramethylcarbazole, benzofluorocarbazole, benzothienocarbazole, phenyldihydroindolocarbazole, Phenylbicarbazole, bicarbazole, tercarbazole, diphenylcarbazolylamine, tetraphenylcarbazolyldiamine, phenoxazine, dihydrophenazine, phenothiazine, dimethyldihydroacridine, diphenylamine, bis. (tert-butyl phenyl)amine, N1-(4-(diphenylamino)phenyl)-N4,N4-diphenylbenzene-1,4-diamine, dimethyltetraphenyldihydroacridinediamine, tetramethyl-dihydroinde Noacridine, diphenyldihydrodibenzoazacillin, etc. are mentioned. Acceptor structures include sulfonyl dibenzene, benzophenone, phenylenebis (phenylmethanone), benzonitrile, isonicotinonitrile, phthalonitrile, isophthalonitrile, paraphthalonitrile, benzene tricarbonitrile, and triazole. , oxazole, thiadiazole, benzothiazole, benzobis (thiazole), benzooxazole, benzobis (oxazole), quinoline, benzoimidazole, dibenzoquinoxaline, heptaazaphenalene, thioxanthone dioxide , dimethylanthracenone, anthracenedione, 5H-cyclopenta[1,2-b:5,4-b']dipyridine, fluorene dicarbonitrile, triephenyltriazine, pyrazine dicarbonitrile, pyrimidine, phenyl Examples include pyrimidine, methylpyrimidine, pyridine dicarbonitrile, dibenzoquinoxaline dicarbonitrile, bis(phenylsulfonyl)benzene, dimethylthioxanethene dioxide, thiantrenetetroxide, and tris(dimethylphenyl)borane. In particular, compounds having heat-activated delayed fluorescence in the TAF device include, as partial structures, carbazole, phenoxazine, acridine, triazine, pyrimidine, pyrazine, thioxanthene, benzonitrile, phthalonitrile, and isophene. It is preferable that it is a compound containing at least one selected from talonitrile, diphenylsulfone, triazole, oxadiazole, thiadiazole and benzophenone.

The compound used as the second component of the light-emitting layer in the TAF element is a thermally activated delayed phosphor, and is preferably a compound whose luminescence spectrum overlaps at least partially with the absorption peak of the emitting dopant. Below, compounds that can be used as the second component (heat-activated delayed phosphor) of the light-emitting layer in the TAF element are exemplified. However, compounds that can be used as thermally activated delayed phosphors in TAF devices are not limited to the following exemplary compounds. In the formula below, Me represents methyl, tBu represents t-butyl, and the broken line represents the bonding position.

Additionally, as a heat-activated delayed phosphor, a compound represented by any of the following formulas (AD1), (AD2), and (AD3) can also be used.

In the above formulas (AD1), (AD2), and (AD3), M is each independently a single bond, -O-, >N-Ar, or >CAr ₂ , and is the depth and lowest excitation of the HOMO of the partial structure formed. In terms of the height of the singlet energy level and the lowest excited triplet energy level, it is preferably a single bond, -O- or >N-Ar. J is a spacer structure that divides the partial structure of the donor and the partial structure of the acceptor, and is each independently an arylene with 6 to 18 carbon atoms. In terms of the size of the conjugate oozing from the partial structure of the donor and the partial structure of the acceptor, Arylene with 6 to 12 carbon atoms is preferred. More specifically, phenylene, methylphenylene, and dimethylphenylene can be mentioned. Q is, each independently, =C(-H)- or =N-, preferably in terms of the shallowness of the LUMO of the forming partial structure and the height of the lowest singlet excitation energy level and the lowest triplet excitation energy level. , =N-. Ar is each independently hydrogen, aryl with 6 to 24 carbon atoms, heteroaryl with 2 to 24 carbon atoms, alkyl with 1 to 12 carbon atoms, or cycloalkyl with 3 to 18 carbon atoms, and has the depth and minimum of the HOMO of the partial structure to be formed. In terms of the height of the singlet excitation energy level and the lowest triplet excitation energy level, preferably hydrogen, aryl with 6 to 12 carbon atoms, heteroaryl with 2 to 14 carbon atoms, alkyl with 1 to 4 carbon atoms, or alkyl with 6 to 10 carbon atoms Cycloalkyl, more preferably hydrogen, phenyl, tolyl, xylyl, mesityl, biphenyl, pyridyl, bipyridyl, triazyl, carbazolyl, dimethylcarbazolyl, di-tert-butylcarba. Zolyl, benzoimidazole or phenyl benzoimidazole, and even more preferably hydrogen, phenyl or carbazolyl. m is 1 or 2. n is an integer of (6-m) or less, and is preferably an integer of 4 to (6-m) from the viewpoint of steric hindrance. In addition, at least one hydrogen in the compound represented by each of the above formulas may be substituted with halogen or deuterium.

More specifically, the compounds used as the second component in this embodiment include 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.

The compound used as the second component in this embodiment may be a donor-acceptor type TADF compound represented by D-A in which one donor D and one acceptor A are bonded directly or through a linking group, but one acceptor A It is preferable to have a structure represented by the following formula (DAD1) in which a plurality of donors D are bonded directly or through a linking group because the characteristics of the organic electroluminescent device are improved.

(D ¹ -L ¹ )nA ¹ (DAD1)

Formula (DAD1) includes a compound represented by the following formula (DAD2).

D ² -L ² -A ² -L ³ -D ³ (DAD2)

In formulas (DAD1) and (DAD2), D ¹ , D ² and D ³ each independently represent a donor group. As the donor group, the structure of the donor group described above can be adopted. A ¹ and A ² each independently represent an acceptor group. As the acceptor group, the above acceptor structure can be adopted. L ¹ , L ² and L ³ each independently represent a single bond or a conjugate linking group. The conjugate linking group is a spacer structure that separates the donor group and the acceptor group, and is preferably an arylene with 6 to 18 carbon atoms, and more preferably an arylene with 6 to 12 carbon atoms. It is more preferable that L ¹ , L ² and L ³ are each independently phenylene, methylphenylene or dimethylphenylene. n in the formula (DAD1) is 2 or more and represents an integer less than or equal to the maximum number that A ¹ can be replaced. For example, n may be selected from the range of 2 to 10, or may be selected from the range of 2 to 6. When n is 2, it becomes a compound represented by the formula (DAD2). n pieces of D ¹ may be the same or different, and n pieces of L ¹ 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 employed in the present invention is not limited to these compounds.

In this embodiment, the light emitting layer may be a single layer or may be composed of multiple layers. In addition, 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 may be contained as at least one component in multiple layers. The host compound, the thermally activated delayed phosphor, and the polycyclic aromatic compound of the present invention contained in the light-emitting layer may be one type, a combination of multiple types, or any of them. The assisting dopant and the emitting dopant may be contained entirely or partially in the host compound as the matrix. The light-emitting layer doped with an assisting dopant and an emitting dopant is formed by forming a host compound, an assisting dopant, and an emitting dopant into a film by a three-way co-deposition method, by mixing the host compound, the assisting dopant, and the emitting dopant in advance and then depositing them simultaneously. It can be formed by a wet film forming method, etc., in which a composition (paint) for forming an emitting layer prepared by dissolving a host compound, an assisting dopant, and an emitting dopant in an organic solvent is applied.

The amount of host compound used varies depending on the type of host compound, and can be determined according to the characteristics of the host compound. The standard for the usage amount of the host compound is preferably 40 to 99.999% by mass, more preferably 50 to 99.99% by mass, and even more preferably 60 to 99.9% by mass of the total light emitting layer material. The above range is preferable, for example, in terms of efficient charge transport and efficient energy transfer to the dopant.

The amount of assisting dopant (thermally activated delayed phosphor) used varies depending on the type of assisting dopant, and can be determined according to the characteristics of the assisting dopant. The standard for the usage amount of the assisting dopant is preferably 1 to 60% by mass, more preferably 2 to 50% by mass, and still more preferably 5 to 30% by mass of the total light emitting layer material. The above range is preferable, for example, in terms of efficiently transferring energy to the emitting dopant.

The amount of emitting dopant (compound having a boron atom) used varies depending on the type of emitting dopant, and can be determined according to the characteristics of the emitting dopant. The standard for the usage amount of the emitting dopant is preferably 0.001 to 30% by mass, more preferably 0.01 to 20% by mass, and even more preferably 0.1 to 10% by mass of the total light emitting layer material. The above range is preferable because, for example, concentration quenching phenomenon can be prevented.

It is preferable that the emitting dopant is used at a low concentration in order to prevent concentration quenching phenomenon. It is desirable for the efficiency of the thermally activated delayed fluorescence device to use a high concentration of the assisting dopant. Additionally, from the viewpoint of efficiency of the thermally activated delayed fluorescence mechanism of the assisting dopant, it is preferable that the amount of the emitting dopant used is low in concentration compared to the amount of the assisting dopant used.

<2-1-3. Substrate in organic electroluminescent device>

The substrate 101 is a support for the organic EL element 100, and usually quartz, glass, metal, plastic, etc. are used. The substrate 101 is formed in a plate shape, a film shape, or a sheet shape depending on the purpose, and for example, a glass plate, a metal plate, a metal foil, a plastic film, a plastic sheet, etc. are used. Among them, glass plates and plates made of transparent synthetic resins such as polyester, polymethacrylate, polycarbonate, and polysulfone are preferable. In the case of a glass substrate, soda-lime glass, alkali-free glass, etc. are used, and the thickness just needs to be sufficient to maintain mechanical strength, so for example, it can be 0.2 mm or more. The upper limit of the thickness is, for example, 2 mm or less, and preferably 1 mm or less. Regarding the material of the glass, alkali-free glass is preferred because it is better to have fewer ions eluted from the glass. However, soda-lime glass coated with a barrier coat such as SiO ₂ is also commercially available and can be used. In addition, in order to increase the gas barrier property, the substrate 101 may be formed with a gas barrier film such as a dense silicon oxide film on at least one side. In particular, a plate, film or sheet made of synthetic resin with low gas barrier property may be used as the substrate. When used as (101), it is desirable to form a gas barrier film.

<2-1-4. Anode in organic electroluminescent device>

The anode 102 serves to inject holes into the light emitting layer 105. Additionally, when either the hole injection layer 103 or the transport layer 104 is provided between the anode 102 and the light-emitting layer 105, holes are injected into the light-emitting layer 105 through these.

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

The resistance of the transparent electrode is not limited as long as it can supply sufficient current for light emission of the light-emitting element, but it is preferable to have low resistance from the viewpoint of power consumption of the light-emitting element. For example, an ITO substrate of 300Ω/□ or less will function as a device electrode, but currently, it is also possible to supply substrates of about 10Ω/□, so for example, 100 to 5Ω/□, preferably 50 to 5Ω/□. It is particularly desirable to use a low-resistance product. The thickness of ITO can be arbitrarily selected according to the resistance value, but is usually between 50 and 300 nm.

<2-1-5. Hole injection layer and hole transport layer in organic electroluminescent device>

The hole injection layer 103 serves to efficiently inject holes moving from the anode 102 into the light emitting layer 105 or the hole transport layer 104. The hole transport layer 104 serves to efficiently transport holes injected from the anode 102 or holes injected from the anode 102 through the hole injection layer 103 to the light emitting layer 105. The hole injection layer 103 and the hole transport layer 104 are formed by laminating or mixing one or two or more types of hole injection/transport materials, or a mixture of a hole injection/transport material and a polymer binder, respectively. Additionally, an inorganic salt such as iron (III) chloride may be added to the hole injection/transport material to form a layer.

As a hole injection/transport material, it is necessary to efficiently inject and transport holes from the positive electrode between electrodes to which an electric field is applied, so it is desirable to have high hole injection efficiency and efficiently transport the injected holes. For this purpose, it is desirable to use a material that has a small ionization potential, a high hole mobility, and excellent stability, and in which impurities that become traps are unlikely to be generated during manufacture and use.

Materials forming the hole injection layer 103 and the hole transport layer 104 include compounds conventionally used as hole charge transport materials in photoconductive materials, p-type semiconductors, and hole injection layers and holes in organic EL devices. Any compound can be selected and used among known compounds used in the transport layer. Specific examples of these include carbazole derivatives (N-phenylcarbazole, polyvinylcarbazole, etc.), biscarbazole derivatives such as bis(N-arylcarbazole) or bis(N-alkylcarbazole), and triarylamine. Derivatives (4,4',4"-tris(N-carbazolyl)triphenylamine, polymer having aromatic tertiary amino in the main 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, N4,N4'-diphenyl-N4,N4'-bis(9-phenyl-9H-car basol-3-yl)-[1,1'-biphenyl]-4,4'-diamine, N4,N4,N4',N4'-tetra[1,1'-biphenyl]-4-yl)- Triphenylamine derivatives such as [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-based compounds, benzofuran derivatives or thiophene derivatives, oxadiazole derivatives, quinoxaline derivatives (e.g., 1,4, 5,8,9,12-hexaazatriphenylene-2,3,6,7,10,11-hexacarbonitrile, etc.), heterocyclic compounds such as porphyrin derivatives, polysilanes, etc. In the polymer system, polycarbonate, styrene derivatives, polyvinylcarbazole, and polysilane having the above-mentioned monomer in the side chain are preferable, but they form a thin film necessary for manufacturing a light-emitting device, can inject holes from the anode, and also create holes. There is no particular limitation as long as it is a compound that can be transported.

Additionally, it is known that the conductivity of organic semiconductors is strongly influenced by their doping. Such an organic semiconductor matrix material is composed of a compound with good electron donating properties or a compound with good electron accepting properties. For doping of electron-donating materials, strong electron acceptors such as tetracyanoquinonedimethane (TCNQ) or 2,3,5,6-tetrafluorotetracyano-1,4-benzoquinonedimethane (F4TCNQ) are used. It is known (e.g., “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 an electron-donating base material (hole transport material). Depending on the number and mobility of holes, the conductivity of the base material changes significantly. As matrix materials with hole transport properties, for example, benzidine derivatives (TPD, etc.) or starburst amine derivatives (TDATA, etc.), or specific metal phthalocyanines (especially zinc phthalocyanine (ZnPc), etc.) are known (Japanese Patent Publication). Publication No. 2005-167175). The polycyclic aromatic compound of the present invention may be used as a material for forming a hole injection layer or a material for forming a hole transport layer.

<2-1-6. Electronic blocking layer in organic electroluminescent device>

An electron blocking layer may be formed between the hole injection/transport layer and the light-emitting layer to prevent diffusion of electrons from the light-emitting layer. To form the electron blocking layer, a compound represented by any of the above-mentioned formulas (H1), (H2), and (H3) can be used. The polycyclic aromatic compound of the present invention may be used as a material for forming an electron blocking layer.

<2-1-7. Electron injection layer and electron transport layer in organic electroluminescent device>

The electron injection layer 107 serves to efficiently inject electrons moving from the cathode 108 into the light emitting layer 105 or the electron transport layer 106. The electron transport layer 106 serves to efficiently transport electrons injected from the cathode 108 or electrons injected from the cathode 108 through the electron injection layer 107 to the light emitting layer 105. The electron transport layer 106 and the electron injection layer 107 are formed by laminating or mixing one or two or more types of electron transport/injection material, or a mixture of an electron transport/injection material and a polymer binder, respectively.

The electron injection/transport layer is a layer that injects electrons from the cathode and is responsible for transporting the electrons. It is desirable that the electron injection efficiency is high and the injected electrons are transported efficiently. For this purpose, it is desirable to use a material that has high electron affinity, high electron mobility, and excellent stability, and that impurities that become traps are unlikely to be generated during production and use. However, when considering the transport balance between holes and electrons, if it mainly plays a role in efficiently preventing holes from the anode from flowing to the cathode without recombining, even if the electron transport ability is not very high, it improves luminous efficiency. The effect is equivalent to that of materials with high electron transport capacity. Therefore, the electron injection/transport layer in the present embodiment may also include a function of a layer that can efficiently prevent the movement of holes.

The material (electron transport material) forming the electron transport layer 106 or the electron injection layer 107 includes compounds conventionally used as electron transport compounds in photoconductive materials, and compounds used in the electron injection layer and electron transport layer of organic EL elements. It can be used by arbitrarily selecting from among the known compounds in use.

Materials used in the electron transport layer or electron injection layer include compounds consisting of an aromatic ring or heteroaromatic ring composed of one or more atoms selected from carbon, hydrogen, oxygen, sulfur, silicon, and phosphorus, pyrrole derivatives and condensed ring derivatives thereof, and It is preferable to contain at least one type selected from metal complexes having electron-accepting nitrogen. Specifically, condensed ring aromatic ring derivatives such as naphthalene and anthracene, styryl aromatic ring derivatives such as 4,4'-bis(diphenylethenyl)biphenyl, perinone derivatives, coumarin derivatives, and naphthalimide derivatives. , quinone derivatives such as anthraquinone and diphenoquinone, phosphine oxide derivatives, aryl nitrile derivatives, and indole derivatives. Examples of metal complexes having electron-accepting nitrogen include hydroxyazole complexes such as hydroxyphenyloxazole complex, azomethine complex, troporone metal complex, flavonol metal complex, and benzoquinoline metal complex. These materials can be used alone, but may also be mixed with other materials.

Additionally, as specific examples of other electron transfer compounds, pyridine derivatives, naphthalene derivatives, fluoranthene derivatives, BO-based derivatives, anthracene derivatives, phenanthroline derivatives, perrinone derivatives, coumarin derivatives, naphthalimide derivatives, and anthraquinone derivatives. , Diphenoquinone derivatives, diphenyl quinone derivatives, perylene derivatives, oxadiazole derivatives (1,3-bis[(4-t-butylphenyl)1,3,4-oxadiazolyl]phenylene, etc.), Ti Ophene derivatives, triazole derivatives (N-naphthyl-2,5-diphenyl-1,3,4-triazole, etc.), thiadiazole derivatives, metal complexes of auxin derivatives, quinolinol-based metal complexes, quinoxaline derivatives , polymers of quinoxaline derivatives, benzazole compounds, gallium complexes, pyrazole derivatives, perfluorinated phenylene derivatives, triazine derivatives, pyrazine derivatives, benzoquinoline derivatives (2,2'-bis(benzo[h]quinoline- 2-yl)-9,9'-spirofluorene, etc.), imidazopyridine derivatives, borane derivatives, benzoimidazole derivatives (tris(N-phenylbenzimidazol-2-yl)benzene, etc.), benzoxazole derivatives , thiazole derivatives, benzothiazole derivatives, quinoline derivatives, oligopyridine derivatives such as terpyridine, bipyridine derivatives, terpyridine derivatives (1,3-bis(2,2':6',2"-terpyridine-4 '-yl)benzene, etc.), naphthyridine derivatives (bis(1-naphthyl)-4-(1,8-naphthyridin-2-yl)phenyl phosphine oxide, etc.), aldazine derivatives, pyrimidine derivatives, aryl Nitrile derivatives, indole derivatives, phosphine oxide derivatives, bistyryl derivatives, silol derivatives, and azoline derivatives can be mentioned.

Additionally, a metal complex having an electron-accepting nitrogen can also be used, for example, a quinolinol-based metal complex, a hydroxyazole complex such as a hydroxyphenyloxazole complex, an azomethine complex, a troporone metal complex, or a flavonol metal complex. and benzoquinoline metal complexes.

The above-mentioned materials can be used alone, but may also be used in combination with other materials.

Among the above-mentioned materials, borane derivatives, pyridine derivatives, fluoranthene derivatives, BO-based 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, silol derivatives and azoline derivatives are preferred.

The polycyclic aromatic compound of the present invention may be used as a material for forming an electron injection layer or a material for forming an electron transport layer.

The electron transport layer or the electron injection layer may further contain a substance capable of reducing the material forming the electron transport layer or the electron injection layer. As for this reducing substance, as long as it has a certain reducing property, various substances are used, for example, alkali metal, alkaline earth metal, rare earth metal, oxide of alkali metal, halide of alkali metal, oxide of alkaline earth metal, alkaline earth. At least one selected from the group consisting of 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 preferably used.

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), Ca (2.9 eV), and Sr (2.0 eV). alkaline earth metals such as (~2.5 eV) or Ba (copper, 2.52 eV), and materials with a work function of 2.9 eV or less are particularly preferable. Among these, more preferable reducing substances are alkali metals of K, Rb or Cs, even more preferably Rb or Cs, and most preferable is Cs. These alkali metals have a particularly high reducing ability, and by adding a relatively small amount to the material forming the electron transport layer or electron injection layer, the luminance of the organic EL device can be improved and its lifespan can be improved. In addition, as a reducing material with a work function of 2.9 eV or less, a combination of two or more alkali metals is also preferable, especially a combination containing Cs, for example, Cs and Na, Cs and K, Cs and Rb, or Cs. A combination of Na and K is preferred. By including Cs, the reducing ability can be efficiently exerted, and by adding it to the material forming the electron transport layer or electron injection layer, the luminance of the organic EL device can be improved and its lifespan increased.

<2-1-8. Cathode in organic electroluminescent device>

It serves to inject electrons into the light emitting layer 105 through the electron injection layer 107 and the electron transport layer 106.

The material forming the cathode 108 is not particularly limited as long as it is a material that can efficiently inject electrons into the organic layer, but the same material as the material forming the anode 102 can be used. Among them, metals such as tin, indium, calcium, aluminum, silver, copper, nickel, chromium, gold, platinum, iron, zinc, lithium, sodium, potassium, cesium and magnesium, or alloys thereof (magnesium-silver alloy, magnesium -Indium alloy, aluminum-lithium alloy such as lithium fluoride/aluminum, etc.) are preferable. In order to improve device characteristics by increasing electron injection efficiency, 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 problem, there is a known method of using a highly stable electrode by doping a small amount of lithium, cesium or magnesium into the organic layer, for example. As other dopants, inorganic salts such as lithium fluoride, cesium fluoride, lithium oxide, and cesium oxide can also be used. However, it is not limited to these.

In addition, to protect the electrode, metals such as platinum, gold, silver, copper, iron, tin, aluminum and indium, or alloys using these metals, inorganic substances such as silica, titania and silicon nitride, polyvinyl alcohol, vinyl chloride, and hydrocarbons. Laminating a polymer compound or the like is a preferred example. The manufacturing method of these electrodes is not particularly limited as long as conduction can be achieved, such as resistance heating, electron beam evaporation, sputtering, ion plating, and coating.

<2-1-9. Binders that can be used in each layer>

The materials used for the above hole injection layer, hole transport layer, light-emitting layer, electron transport layer, and electron injection layer can be used alone to form each layer, but the polymer binder may be polyvinyl chloride, polycarbonate, polystyrene, or poly(N-vinylcarboxylic acid). Bazole), polymethyl methacrylate, polybutyl methacrylate, polyester, polysulfone, polyphenylene oxide, polybutadiene, hydrocarbon resin, ketone resin, phenoxy resin, polyamide, ethyl cellulose, vinyl acetate resin, ABS It is used by dispersing with solvent-soluble resins such as resins and polyurethane resins, and curable resins such as phenol resins, xylene resins, petroleum resins, urea resins, melamine resins, unsaturated polyester resins, alkyd resins, epoxy resins, and silicone resins. It is also possible.

<2-1-10. Manufacturing method of organic electroluminescent device>

Each layer constituting the organic EL device is formed by using a method such as vapor deposition, resistance heating evaporation, electron beam evaporation, sputtering, molecular stacking, printing, inkjet, spin coat or cast, or coating method. It can be formed by making it into a thin film. There is no particular limitation on the film thickness of each layer formed in this way, and it can be set appropriately depending on the properties of the material, but is usually in the range of 2 nm to 5000 nm. The film thickness can usually be measured with a crystal oscillation type film thickness measuring device or the like. When thinning a film using a vapor deposition method, the deposition conditions vary depending on the type of material, the target crystal structure and association structure of the film, etc. Deposition conditions are generally boat heating temperature +50 to +400°C, vacuum degree of 10 ^-6 to ^{10 -3} Pa, deposition rate of 0.01 to 50 nm/sec, substrate temperature of -150 to +300°C, and film thickness of 2 nm to 5 μm. It is desirable to set it appropriately within the range.

Next, as an example of a method of manufacturing an organic EL device, a method of manufacturing an organic EL device composed of an anode/hole injection layer/hole transport layer/host material and a light emitting layer/electron transport layer/electron injection layer/cathode made of a dopant material is described. Explain. After producing an anode by forming a thin film of an anode material by a vapor deposition method or the like on a suitable substrate, thin films of a hole injection layer and a hole transport layer are formed on this anode. A host material and a dopant material are co-deposited on this to form a thin film to form a light-emitting layer. An electron transport layer and an electron injection layer are formed on this light-emitting layer, and a thin film made of a cathode material is formed by a vapor deposition method to form a cathode, thereby forming the desired organic material. An EL device is obtained. In addition, when manufacturing the organic EL device described above, it is also possible to reverse the manufacturing order and fabricate the cathode, electron injection layer, electron transport layer, light emitting layer, hole transport layer, hole injection layer, and anode in that order.

When applying a direct current voltage to the organic EL device obtained in this way, it can be applied with the anode as + and the cathode as -, and when a voltage of about 2 to 40 V is applied, the transparent or translucent electrode side (anode or cathode) , and both sides) can be observed. Additionally, this organic EL element emits light even when pulse current or alternating current is applied. Additionally, the waveform of the applied alternating current may be arbitrary.

<2-1-11. Application examples of organic electroluminescent devices>

Organic EL elements can also be applied to display devices or lighting devices.

A display device or lighting device equipped with an organic EL element can be manufactured by known methods, such as connecting an organic EL element and a known driving device, and known driving methods such as direct current driving, pulse driving, and alternating current driving can be used as appropriate. It can be driven using .

Examples of display devices include panel displays such as color flat panel displays, and flexible displays such as flexible color organic electroluminescence (EL) displays (for example, Japanese Patent Application Laid-Open No. 10-335066, See Japanese Patent Publication No. 2003-321546, Japanese Patent Publication No. 2004-281086, etc.). Additionally, examples of the display method include either a matrix method or a segment method. Additionally, the matrix display and segment display may coexist in the same panel.

In a matrix, pixels for display are arranged two-dimensionally, such as in a grid or mosaic, and characters or images are displayed as a set of pixels. The shape and size of the pixel are determined depending on the purpose. For example, for image and text display on computers, monitors, and televisions, square pixels with a side of 300 ㎛ or less are usually used, and in the case of large displays such as display panels, pixels on the order of mm per side are used. I do it. In the case of black-and-white display, pixels of the same color can be arranged, but in the case of color display, pixels of red, green, and blue are arranged and displayed. In this case, there are typically delta types and stripe types. The driving method of this matrix may be either a line-sequential driving method or an active matrix driving method. Line-sequential driving has the advantage of having a simple structure, but when considering operation characteristics, the active matrix method is sometimes superior, so it is necessary to use it separately depending on the application.

In the segment method (type), a pattern is formed to display predetermined information, and a defined area is emitted. Examples include time and temperature displays in digital clocks and thermometers, operating status displays in audio devices and electronic cookers, and panel displays in automobiles.

Examples of lighting devices include lighting devices such as indoor lighting, backlights of liquid crystal display devices, etc. (for example, Japanese Patent Application Laid-Open No. 2003-257621, Japanese Patent Application Laid-Open No. 2003-277741, Japanese Patents (See Public Notice No. 2004-119211, etc.). Backlights are mainly used to improve the visibility of display devices that do not emit light themselves, and are used in liquid crystal displays, clocks, audio devices, automobile panels, display boards, and signs. In particular, considering that it is difficult to make thinner backlights for liquid crystal display devices, especially for computers, where thinning is an issue, because the conventional method consists of fluorescent lamps or light guide plates, backlights using organic EL elements are thin and lightweight. It becomes a characteristic.

<2-2. Other organic devices>

The polycyclic aromatic compound according to the present invention can be used in the production of organic field-effect transistors or organic thin-film solar cells in addition to the organic electroluminescent devices described above.

An organic field effect transistor is a transistor that controls current by an electric field generated by voltage input, and has a gate electrode in addition to the source electrode and drain electrode. It is a transistor that generates an electric field when a voltage is applied to the gate electrode and can control the current by arbitrarily blocking the flow of electrons (or holes) flowing between the source and drain electrodes. Field effect transistors are easier to miniaturize than simple transistors (bipolar transistors), and are often used as elements constituting integrated circuits and the like.

The structure of an organic field effect transistor is usually such that a source electrode and a drain electrode are provided in contact with an organic semiconductor active layer formed using a polycyclic aromatic compound according to the present invention, and an insulating layer (dielectric layer) in contact with the organic semiconductor active layer is provided in between. Then, the gate electrode can be installed. Examples of the device structure include the following structure.

(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

The organic field effect transistor constructed in this way can be applied as a pixel driving switching element of an active matrix driving type liquid crystal monitor or organic light emitting device display.

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 a hole transport layer, a p-type semiconductor layer, an n-type semiconductor layer, and an 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 electron transport material in an organic thin film solar cell. The organic thin film solar cell may be appropriately provided with a hole blocking layer, an electron blocking layer, an electron injection layer, a hole injection layer, a smoothing layer, etc. in addition to the above. For an organic thin film solar cell, known materials used in organic thin film solar cells can be appropriately selected and used in combination.

<3. Wavelength Conversion Materials>

The polycyclic aromatic compound of the present invention can be used as a wavelength conversion material.

Currently, the application of multi-color technology using color conversion methods to liquid crystal monitors, organic EL displays, lighting, etc. is being actively studied. Color conversion refers to converting light emission from a light emitting body into light of a longer wavelength, for example, converting ultraviolet light or blue light into green light or red light emission. By forming a wavelength conversion material with this color conversion function into a film and combining it with a blue light source, for example, it becomes possible to extract the three primary colors of blue, green, and red from the blue light source, that is, to extract white light. By using a white light source that combines such a blue light source and a wavelength conversion film with a color conversion function as a light source unit and combining it with a liquid crystal driving part and a color filter, it is possible to produce a full color display. In addition, if there is no liquid crystal driving part, it can be used as a white light source, for example, it can be applied as a white light source such as LED lighting. Additionally, by using a blue organic EL element as a light source in combination with a wavelength conversion film that converts blue light into green light and red light, it becomes possible to produce a full-color organic EL display without using a metal mask. Furthermore, by using blue micro LED as a light source and using it in combination with a wavelength conversion film that converts blue light into green light and red light, it becomes possible to produce a low-cost, full-color micro LED display.

The polycyclic aromatic compound of the present invention can be used as this wavelength conversion material. A display device (a display device or a liquid crystal display device using an organic EL element) uses a wavelength conversion material containing the polycyclic aromatic compound of the present invention to emit light from a light source or light-emitting element that generates ultraviolet light or blue light of a shorter wavelength. It can be converted into blue or green light with high color purity suitable for use in. The color to be converted can be adjusted by appropriately selecting the polycyclic aromatic compound substituent of the present invention, the binder resin used in the composition for wavelength conversion described later, etc. The wavelength conversion material can be prepared as a composition for wavelength conversion containing the polycyclic aromatic compound of the present invention. Additionally, a wavelength conversion film may be formed using this composition for wavelength conversion.

The composition for wavelength conversion may contain a binder resin, other additives, and a solvent in addition to the polycyclic aromatic compound of the present invention. As the binder resin, for example, those described in paragraphs 0173 to 0176 of International Publication No. 2016/190283 can be used. As other additives, the compounds described in paragraphs 0177 to 0181 of International Publication No. 2016/190283 can be used. As the solvent, reference may be made to the description of the solvent contained in the composition for forming the emitting layer.

The wavelength conversion film includes a wavelength conversion layer formed by curing a wavelength conversion composition. As a method of producing a wavelength conversion layer from a composition for wavelength conversion, a known film forming method can be referred to. The wavelength conversion film may be composed only of a wavelength conversion layer formed from a composition containing the polycyclic aromatic compound of the present invention, or may be composed of another wavelength conversion layer (for example, a wavelength conversion layer that converts blue light into green light or red light, or a wavelength conversion layer that converts blue light or green light. It may also contain a wavelength conversion layer that converts to red light. Additionally, the wavelength conversion film may include a base layer or a barrier layer to prevent the color conversion layer from being deteriorated by oxygen, moisture, or heat.

[Example]

Hereinafter, the present invention will be described in more detail through examples, but the present invention is not limited to these.

Synthesis example (1):

Synthesis of compound (1-1)

Under nitrogen atmosphere, intermediate (X-1) (50.0 g), 1-t-butyl-3,4,5-trichlorobenzene (32.0 g), and dichlorobis [di-t-butyl (4-dimethyl) as palladium catalyst. Aminophenyl) phosphino] palladium (II) (Pd-132) (0.909 g), sodium-t-butoxide (NaOtBu, 18.5 g) and toluene (500 ml) were placed in a flask and heated at 120°C for 5 hours. After the reaction was completed, water and ethyl acetate were added to the reaction solution and stirred, and the organic layer was separated and washed with water. Thereafter, the crude product obtained by concentrating the organic layer was purified using a silica gel short-pass column (eluent: heptane) to obtain 49.3 g of intermediate (X-2).

Under a nitrogen atmosphere, intermediate (X-2) (30.0 g), intermediate (X-3) (26.6 g), Pd-132 (0.719 g) as a palladium catalyst, NaOtBu (7.32 g), and toluene (300 ml) were added to the flask. and heated at 120°C for 3 hours. After the reaction was completed, water and ethyl acetate were added to the reaction solution and stirred, and the organic layer was separated and washed with water. Thereafter, the crude product obtained by concentrating the organic layer was purified using a silica gel short pass column (eluent: toluene/heptane = 1/9 (volume ratio)) to obtain 43.8 g of intermediate (X-4).

In a flask containing intermediate (X-4) (21.5 g) and tert-butylbenzene (tBu-benzene, 215 ml), 1.60 M tert-butyllithium pentane solution (tBuLi, 25.0 ml) was added at 0°C under a nitrogen atmosphere. was added. After the dropwise addition was completed, the temperature was raised to 70°C and stirred for 0.5 hours, and components with a lower boiling point than tert-butylbenzene were removed by distillation under reduced pressure. It was cooled to -50°C, boron tribromide (10.0 g) was added, the temperature was raised to room temperature, and the mixture was stirred for 0.5 hours. Afterwards, it was cooled again to 0°C, N,N-diisopropylethylamine (EtNiPr ₂ , 5.15 g) was added, and the mixture was stirred at room temperature until the heat generation subsided, then the temperature was raised to 100°C and heated and stirred for 1 hour. . The reaction solution was cooled to room temperature, and aqueous sodium acetate solution cooled in an ice bath, followed by ethyl acetate, was added to separate the layers. The organic layer was concentrated and purified using a silica gel short pass column (eluent: chlorobenzene). The obtained crude product was recrystallized from toluene to obtain 2.05 g of compound (1-1).

The structure of the obtained compound was confirmed by NMR measurement.

¹ H-NMR(CDCl ₃ ):δ=8.96-8.86(m, 2H), 7.66-7.55(m, 2H), 7.40-7.24(m, 3H), 7.16-7.06(m, 1H), 6.95(d) , 1H), 6.72-6.64(m, 2H), 6.42(d, 1H), 6.20-6.12(m, 2H), 1.82-1.61(m, 18H), 1.56-1.38(m, 18H), 1.34(s) , 9H), 1.29-1.22(m, 15H), 1.14-1.04(m, 9H), 0.93-0.87(m, 12H).

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

<Evaluation method for basic properties>

<Preparation of samples>

When evaluating the absorption characteristics and luminescence properties (fluorescence and phosphorescence) of a compound to be evaluated, the compound to be evaluated may be dissolved in a solvent and evaluated in the solvent, or evaluated in a thin film state. Furthermore, in the case of evaluation in a thin film state, depending on the mode of use of the compound to be evaluated in an organic EL device, there is a case where only the compound to be evaluated is thinned and evaluated, or the compound to be evaluated is dispersed in an appropriate matrix material to be thinned. There are cases where it is evaluated. Here, a thin film obtained by depositing only the compound to be evaluated is referred to as a “single film,” and a thin film obtained by applying and drying a coating solution containing the compound to be evaluated and a matrix material is referred to as a “coated film.”

As a matrix material, commercially available PMMA (polymethyl methacrylate) or the like can be used. In this example, PMMA and the compound to be evaluated were dissolved in toluene, and then a thin film was formed on a quartz transparent support substrate (10 mm x 10 mm) by spin coating to prepare a sample.

Additionally, a thin film sample when the matrix material is a host compound is produced as follows. A transparent support substrate made of quartz (10 mm After mounting the deposition boat, the vacuum tank is depressurized to 5×10 ^-4 Pa. Next, the deposition boat containing the host compound and the deposition boat containing the dopant material are simultaneously heated to deposit both the host compound and dopant material to an appropriate film thickness to form a mixed thin film (sample) of the host compound and dopant material. did. Here, the deposition rate is controlled according to the set mass ratio of the host compound and the dopant material.

<Evaluation of absorption characteristics and luminescence characteristics>

The absorption spectrum of the sample is measured using an ultraviolet-visible-near-infrared spectrophotometer (UV-2600, Shimadzu Corporation). In addition, the fluorescence spectrum or phosphorescence spectrum of the sample is measured using a spectrofluorescence photometer (Hitachi Hi-Tech Co., Ltd., F-7000).

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

Additionally, the fluorescence quantum yield (PLQY) is measured using an absolute PL quantum yield measuring device (C9920-02G, manufactured by Hamamatsu Photonics Co., Ltd.).

Next, the evaluation of basic physical properties of the polycyclic aromatic compound of the present invention is described.

<Evaluation of fluorescence lifetime (delayed fluorescence)>

The fluorescence lifetime was measured at 300K using a fluorescence lifetime measuring device (C11367-01, manufactured by Hamamatsu Photonics Co., Ltd.). Specifically, the fast and slow emission components of the fluorescence lifetime were observed at the maximum emission wavelength measured as the appropriate excitation wavelength. In measurements of the fluorescence lifetime of general organic EL materials that emit fluorescence at room temperature, a slow emission component involving the triplet component derived from phosphorescence is rarely observed due to deactivation of the triplet component by heat. When a slow luminescence component is observed in the compound under evaluation, it indicates that triplet energy with a long excitation life is transferred to singlet energy by thermal activation and observed as delayed fluorescence.

<Calculation of energy gap (Eg)>

Eg = 1240/A is calculated from A (nm) at the long-wavelength end of the absorption spectrum obtained by the above-described method.

<Measurement of ionization potential (Ip)>

A transparent support substrate (28 mm After installing, reduce the pressure of the vacuum tank to 5×10 ^-4 Pa. Next, the deposition boat is heated to evaporate the target compound to form a single film (neat film) of the target compound.

Using the obtained single film as a sample, the ionization potential of the target compound is measured using a photoelectron spectrometer (Sumitomo Heavy Industries Co., Ltd. PYS-201).

<Calculation of electron affinity (Ea)>

The electron affinity can be estimated from the difference between the ionization potential measured by the above-mentioned method and the energy gap calculated by the above-mentioned method.

<Measurement of the lowest singlet excited energy level E(S, Sh) and lowest triplet excited energy level E(T, Sh)>

For a single film of the target compound formed on a glass substrate, the fluorescence spectrum is observed at 77 K with excitation light for the second absorption peak on the long-wavelength side of the absorption spectrum, and the lowest excitation is from the shoulder on the short-wavelength side of the peak of the fluorescence spectrum. Find the singlet energy level E(S, Sh).

Additionally, on a single film of the target compound formed on a glass substrate, a phosphorescence spectrum was observed at 77 K with excitation light showing the second absorption peak on the long-wavelength side of the absorption spectrum, and the peak of the phosphorescence spectrum was measured from the shoulder on the short-wavelength side to the lowest. Here, the triplet energy level E(T, Sh) is obtained.

<Evaluation of organic EL devices>

As described above, the compound of the present invention has the characteristics of an appropriate energy gap (Eg), high triplet excitation energy (E _T ), and small ΔEST, so it can be expected to be applied to, for example, a light-emitting layer and a charge transport layer. , In particular, application to the light emitting layer can be expected.

<Evaluation items and evaluation methods>

Evaluation items include driving voltage (V), emission wavelength (nm), CIE chromaticity (x, y), external quantum efficiency (%), maximum wavelength of emission spectrum (nm), and full width at half maximum (nm). For these evaluation items, values at appropriate emission luminance can be used.

The quantum efficiency of a light-emitting device includes internal quantum efficiency and external quantum efficiency. Internal quantum efficiency represents the rate at which external energy injected as electrons (or holes) into the light-emitting layer of the light-emitting device is converted purely into photons. On the other hand, the external quantum efficiency is calculated based on the amount of photons emitted to the outside of the light-emitting device, and a portion of the photons generated in the light-emitting layer is absorbed or continuously reflected inside the light-emitting device, thereby causing the photons to be emitted to the outside of the light-emitting device. Because it is not emitted, the external quantum efficiency is lower than the internal quantum efficiency.

The method of measuring spectral radiance (emission spectrum) and external quantum efficiency is as follows. The device was made to emit light by applying voltage using a voltage/current generator R6144 manufactured by Advantist. Using a spectral radiance meter SR-3AR manufactured by TOPCON, the spectral radiance in the visible region was measured from the direction perpendicular to the light emitting surface. Assuming that the light-emitting surface is a completely diffusing surface, the value of the measured spectral radiance of each wavelength component divided by the wavelength energy and multiplied by π is the number of photons at each wavelength. Next, the number of photons was integrated in the entire observed wavelength range, which was taken as the total number of photons emitted from the device. The value obtained by dividing the applied current value by the small charge is the number of carriers injected into the device, and the number divided by the number of total photons emitted from the device by the number of carriers injected into the device is the external quantum efficiency. Additionally, the half width of the emission spectrum can be obtained as the width between the upper and lower wavelengths at which the intensity is 50%, with the maximum emission wavelength as the center.

Next, the fabrication and evaluation of an organic EL device using the polycyclic aromatic compound of the present invention will be described.

<Configuration of organic EL device>

An organic EL device was manufactured using the polycyclic aromatic compound of the present invention.

[Device composition A]

The material composition of each layer in the organic EL device of Example 1 and Comparative Examples 1 to 4 is shown in Table 1 below.

[Table 1]

In Table 1, "HI" is N ⁴ ,N ^4' -diphenyl-N ⁴ ,N ^4' -bis(9-phenyl-9H-carbazol-3-yl)-[1,1'-biphenyl ]-4,4'-diamine, “HAT-CN” is 1,4,5,8,9,12-hexaazatriphenylene hexacarbonitrile, and “HT-1” is N-([1, 1'-biphenyl]-4-yl-9,9-dimethyl-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-9H-fluoren-2-amine, HT-2" is N,N-bis(4-(dibenzo[b,d]furan-4-yl)phenyl)-[1,1':4',1"-terphenyl]-4-amine. , "BH" is 2-(10-phenylanthracen-9-yl)dibenzo[b,d]furan, and "ET-1" is 9,9'-[(5-(6-(1, 1'-biphenyl)-4-yl)-2-phenylpyrimidin-4-yl)-1,3-phenylene]bis(9H-carbazole), and “ET-2” is 4-(6- (10-phenylanthracen-9-yl)naphthalen-2-yl)pyridine. “Liq”, comparative compound (1) (compound described in International Publication No. 2015/102118), comparative compound (2) (International Publication No. The chemical structures are shown below along with the compound described in 2019/132028), comparative compound (3) (compound described in International Publication No. 2020/017931), and comparative compound (4) (compound described in International Publication No. 2020/218079). represents.

(Example 1)

A 26 mm x 28 mm x 0.7 mm glass substrate (manufactured by Opto Science Co., Ltd.) made by polishing ITO formed to a thickness of 180 nm by sputtering to 150 nm was used as a transparent support substrate. This transparent support substrate was fixed to the substrate holder of a commercially available vapor deposition device (manufactured by Showa Vacuum Co., Ltd.), and HI, HAT-CN, HT-1, HT-2, BH, compound (1-1), ET- A molybdenum deposition boat containing 1 and ET-2, respectively, and an aluminum nitride deposition boat containing Liq, LiF, and aluminum, respectively, were installed.

The following layers are sequentially formed on the ITO film of the transparent support substrate. The vacuum chamber was depressurized to 5×10 ^-4 Pa, and first, HI was heated to deposit a film thickness of 40 nm, then HAT-CN was heated to deposit a film thickness of 5 nm, and then HT-1. was heated and deposited to a film thickness of 45 nm, and then HT-2 was heated and deposited to a film thickness of 10 nm to form a four-layer hole layer. Next, BH and compound (1-1) were heated simultaneously and deposited to a film thickness of 25 nm to form a light-emitting layer. The deposition rate was adjusted so that the mass ratio of BH and compound (1-1) was about 97:3. Furthermore, ET-1 was heated and deposited to a film thickness of 5 nm, and then ET-2 and Liq were simultaneously heated and deposited to a film thickness of 25 nm to form a two-layer electronic layer. The deposition rate was adjusted so that the mass ratio of ET-2 and Liq was approximately 50:50. The deposition rate of each layer was 0.01 to 1 nm/sec. After that, LiF was heated and deposited at a deposition rate of 0.01 to 0.1 nm/sec to a film thickness of 1 nm, and then aluminum was heated and deposited to a film thickness of 100 nm to form a cathode, and an organic EL device was obtained.

(Comparative Examples 1 to 4)

In the same manner as Example 1 except that Comparative Compound (1), Comparative Compound (2), Comparative Compound (3), and Comparative Compound (4) were used instead of Compound (1-1), the organic compounds of Comparative Examples 1 to 4 were An EL device was obtained.

<Evaluation items and evaluation methods>

Evaluation items include driving voltage (V), emission wavelength (nm), CIE chromaticity (x, y), external quantum efficiency (%), maximum wavelength of emission spectrum (nm), and full width at half maximum (nm). For these evaluation items, for example, values at the time of light emission of 1000 cd/m ² can be used.

The quantum efficiency of a light-emitting device includes internal quantum efficiency and external quantum efficiency. The internal quantum efficiency represents the rate at which external energy injected as electrons (or holes) into the light-emitting layer of the light-emitting device is converted purely into photons. On the other hand, the external quantum efficiency is calculated based on the amount of photons emitted to the outside of the light-emitting device, and the photons generated in the light-emitting layer are partially absorbed or continuously reflected inside the light-emitting device, thereby reaching the outside of the light-emitting device. Because it is not emitted, the external quantum efficiency is lower than the internal quantum efficiency.

The method of measuring spectral radiance (emission spectrum) and external quantum efficiency is as follows. Using the voltage/current generator R6144 manufactured by Advantist, a voltage that causes the luminance of the device to be 1000 cd/m ² is applied to cause the device to emit light. Using a spectral radiance meter SR-3AR manufactured by TOPCON, the spectral radiance in the visible light region is measured from a direction perpendicular to the light emitting surface. Assuming that the light-emitting surface is a completely diffusing surface, the value of the measured spectral radiance of each wavelength component divided by the wavelength energy and multiplied by π is the number of photons at each wavelength. Next, the number of photons is integrated in the observed radio field region and is taken as the total number of photons emitted from the device. The value of the applied current divided by the basic charge is the number of carriers injected into the device, and the number of photons emitted from the device divided by the number of carriers injected into the device is the external quantum efficiency. Additionally, the half width of the emission spectrum is calculated as the width between the upper and lower wavelengths at which the intensity is 50%, with the maximum emission wavelength as the center.

For the organic EL devices of Example 1 and Comparative Examples 1 to 4, a direct current voltage was applied using the ITO electrode as the anode and the LiF/aluminum electrode as the cathode, and the characteristics at 1000 cd/m ² light emission were measured.

The results are shown in Table 2.

[Table 2]

The polycyclic aromatic compound of the present invention is useful as a material for organic devices, particularly as a material for a light-emitting layer for forming a light-emitting layer of an organic electroluminescent device. By using the polycyclic aromatic compound of the present invention as a dopant for the light-emitting layer, a low-voltage, high-efficiency light-emitting organic electroluminescent device can be obtained.

100 Organic electroluminescent device
101 substrate
102 anode
103 hole injection layer
104 hole transport layer
105 emitting layer
106 electron transport layer
107 electron injection layer
108 cathode

Claims (9)

A polycyclic aromatic compound having a structure consisting of one or two or more structural units represented by the following formula (1);

In equation (1),
Ring A, ring B, and ring C are each independently a substituted or unsubstituted aryl ring, or a substituted or unsubstituted heteroaryl ring;
Y ¹ is B, P, P=O, P=S, Al, Ga, As, Si-R, or Ge-R, and R of 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} _{_} Aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, or a monovalent group represented by the formula (G), wherein >C(-R) ₂ , and >Si (-R) ₂ R is each independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, and >C (- R) ₂ and the two R of the >Si(-R) ₂ may be combined with each other to form a ring, and among the R of the >NR, the >C(-R) ₂ and the >Si(-R) ₂ At least one R may be bonded to at least one of the A ring and the B ring, or to at least one of the A ring and the C ring through a single bond or a linking group,
However, at least one of X ¹ and X ² is >NR where R is a monovalent group represented by formula (G),
In equation (G),
L is a single bond, alkylene, cycloalkylene, arylene or heteroarylene, of which at least one hydrogen may be substituted, and the (GA) ring and (GB) ring are each independently substituted or unsubstituted. It is an aryl ring, or a substituted or unsubstituted heteroaryl ring;
X ³ and X ⁴ are each independently >O, >NR, >C(-R) ₂ , >Si(-R) ₂ , >S, or >Se, and ) ₂ , and the R of >Si(-R) ₂ is each independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl and the two R of the >C(-R) ₂ and the >Si(-R) ₂ may be combined with each other to form a ring, and the R of the >NR, the >C(-R) ₂ and the > At least one R of Si(-R) ₂ is a single bond with at least one of the (GA) ring and the (GB) ring, or a single bond with at least one of the (GA) ring and the (GB) ring, or through a linking group. It can be combined,
In the structure represented by formula (1), at least one of the aryl ring or heteroaryl ring may be condensed with at least one cycloalkane, and at least one hydrogen in the cycloalkane may be substituted, At least one -CH ₂ - in the cycloalkane may be substituted with -O-, and;
At least one hydrogen in the structure represented by formula (1) may be substituted with cyano, halogen, or deuterium. According to paragraph 1,
A polycyclic aromatic compound in which the structural unit represented by formula (1) is a structural unit represented by the following formula (2);

In equation (2),
Z in ring a, b, and c is each independently N or CR ¹¹ , and R ¹¹ of CR ¹¹ is each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, Arylheteroarylamino, diarylboryl, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio, or substituted silyl, where at least one hydrogen is aryl, heteroaryl, diarylamino, alkyl. , cycloalkyl, or substituted silyl;
The two aryls of the diarylamino are not bonded to each other or are bonded through a linking group, and the two heteroaryls of the diheteroarylamino are not bonded to each other or are bonded through a linking group, and the two heteroaryls of the arylheteroarylamino are not bonded to each other or are bonded through a linking group. Aryl and heteroaryl are not bonded to each other or are bonded to each other through a linking group, and the two aryls of the diarylboryl are not bonded to each other or are bonded to each other through a single bond or linking group;
Two adjacent R ¹¹ may be bonded to each other to form an aryl ring or heteroaryl ring, and the formed aryl ring and heteroaryl ring are respectively aryl, heteroaryl, diarylamino, diheteroarylamino, and arylheteroarylamino. , diarylboryl, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio, or substituted silyl, and at least one hydrogen in these is aryl, heteroaryl, diarylamino, alkyl. , cycloalkyl, or substituted silyl;
The two aryls of the diarylamino are not bonded to each other or are bonded through a linking group, and the two heteroaryls of the diheteroarylamino are not bonded to each other or are bonded through a linking group, and the two heteroaryls of the arylheteroarylamino are not bonded to each other or are bonded through a linking group. Aryl and heteroaryl are not bonded to each other or are bonded to each other through a linking group, and the two aryls of the diarylboryl are not bonded to each other or are bonded to each other through a single bond or linking group;
Z=Z may each independently be >O, >NR, >C(-R) ₂ , >Si(-R) ₂ , >S, or >Se, wherein the >NR and the >C(-R) ₂ and R of >Si(-R) ₂ is each independently hydrogen, aryl, heteroaryl, alkyl, or cycloalkyl, and at least one hydrogen therein is aryl, heteroaryl, diarylamino, alkyl, or cycloalkyl. may be further substituted with alkyl or substituted silyl, and the two R of >C(-R) ₂ and >Si(-R) ₂ may be bonded to each other to form a ring;
Y ¹ is B, or P=O,
_X ^{1 and} _{_} Alkyl, cycloalkyl, or a monovalent group represented by the formula (G-2), wherein at least one hydrogen is further substituted with aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl. R of >C(-R) ₂ and >Si(-R) ₂ may be hydrogen, aryl, heteroaryl, alkyl, or cycloalkyl, and at least one hydrogen thereof may be aryl, heteroaryl, or cycloalkyl. It may be further substituted with aryl, diarylamino, alkyl, cycloalkyl, or substituted silyl, and the two R of >C(-R) ₂ and >Si(-R) ₂ may be bonded to each other to form a ring. And at least one R among R of >NR, >C(-R) ₂ and R of >Si(-R) ₂ is -O-, -S-, -C(-R) ₂ - Alternatively, it may be bonded to one or two C of Z which is CR ¹¹ by a single bond, provided that at least one of X ¹ and X ² is a monovalent group where R is represented by the formula (G-2) > NR,
In equation (G-2),
Z ^G in the Ga ring and Gb ring is each independently N or CR ¹² , and R ¹² of CR ¹² is each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, or arylhetero. Arylamino, diarylboryl, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio, or substituted silyl, where at least one hydrogen is aryl, heteroaryl, diarylamino, alkyl, or cyclo. It may be substituted with alkyl or substituted silyl;
The two aryls of the diarylamino are not bonded to each other or are bonded through a linking group, and the two heteroaryls of the diheteroarylamino are not bonded to each other or are bonded through a linking group, and the two heteroaryls of the arylheteroarylamino are not bonded to each other or are bonded through a linking group. Aryl and heteroaryl are not bonded to each other or are bonded to each other through a linking group, and the two aryls of the diarylboryl are not bonded to each other or are bonded to each other through a single bond or linking group;
Two adjacent R ¹² may be bonded to each other to form an aryl ring or heteroaryl ring, and the formed aryl ring and heteroaryl ring are respectively aryl, heteroaryl, diarylamino, diheteroarylamino, and arylheteroaryl. It may be substituted with amino, diarylboryl, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio, or substituted silyl, and at least one hydrogen in these is aryl, heteroaryl, diarylamino, It may be substituted with alkyl, cycloalkyl, or substituted silyl;
The two aryls of the diarylamino are not bonded to each other or are bonded through a linking group, and the two heteroaryls of the diheteroarylamino are not bonded to each other or are bonded through a linking group, and the two heteroaryls of the arylheteroarylamino are not bonded to each other or are bonded through a linking group. Aryl and heteroaryl are not bonded to each other or are bonded to each other through a linking group, and the two aryls of the diarylboryl are not bonded to each other or are bonded to each other through a single bond or linking group;
Z ^G =Z ^G may each independently be >O, >NR, >C(-R) ₂ , >Si(-R) ₂ , >S, or >Se, and the >NR, the >C(-R ) ₂ and the R of >Si(-R) ₂ are each independently hydrogen, aryl, heteroaryl, substituted alkyl, or cycloalkyl, and at least one hydrogen in these is aryl, heteroaryl, diarylamino , may be substituted with alkyl, cycloalkyl, or substituted silyl, and the two R of >C(-R) ₂ and >Si(-R) ₂ may be bonded to each other to form a ring;
X ³ and X ⁴ are each independently >O, >NR, >C(-R) ₂ , >Si(-R) ₂ , >S, or >Se, and ) ₂ , and the >Si(-R) ₂ , R is each independently hydrogen, aryl, heteroaryl, alkyl, or cycloalkyl, and at least one hydrogen in these is aryl, heteroaryl, It may be substituted with diarylamino, alkyl, cycloalkyl, or substituted silyl, and the two R of >C(-R) ₂ and >Si(-R) ₂ may be bonded to each other to form a ring, and At least one R of the >NR, the >C(-R) ₂ and the >Si(-R) ₂ is -O-, -S-, -C(-R ¹⁴ ) ₂ - or a single bond may be bonded to one or two Cs in Z ^G which is CR ¹² , and R ¹⁴ of -C(-R ¹⁴ ) ₂ - is hydrogen, alkyl, or cycloalkyl,
L is a single bond, arylene or heteroarylene, and at least one hydrogen of the arylene and the heteroarylene may be substituted with aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl. ,
In the structure represented by formula (2), at least one of the aryl ring or heteroaryl ring may be condensed with at least one cycloalkane, and at least one hydrogen in the cycloalkane may be substituted, At least one -CH ₂ - in the cycloalkane may be substituted with -O-, and;
At least one hydrogen in the structure represented by formula (2) may be substituted with cyano, halogen, or deuterium. According to paragraph 2,
In formula (2), Y ¹ is B, and in the above structure, at least one of the aryl ring or heteroaryl ring is condensed with at least one cycloalkane, and at least one hydrogen in the cycloalkane is may be substituted, and at least one -CH ₂ - in the cycloalkane may be substituted with -O-. According to claims 1 to 3,
A polycyclic aromatic compound represented by the following formula.
A material for an organic device containing the polycyclic aromatic compound according to any one of claims 1 to 4. An organic electric field 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 the polycyclic aromatic compound according to any one of claims 1 to 4. Light-emitting device. According to clause 6,
An organic electroluminescent device in which the light-emitting layer includes a host and the polycyclic aromatic compound as a dopant. In clause 7,
An organic electroluminescent device wherein the host is an anthracene compound, a fluorene compound, or a dibenzochrysene compound. A display or lighting device comprising the organic electroluminescent element according to any one of claims 6 to 8.