KR20230140484A - Polycyclic aromatic compounds - Google Patents

Abstract

[Problem] To provide new compounds useful as materials for organic devices such as organic EL devices.
[Solution] A polycyclic aromatic compound having a structure consisting of one or two or more structural units represented by formula (1).

(A ring and B ring are an aryl ring, etc., C ring is a ring represented by formula (C), X ^c is >O or >S or >CMe ₂ etc., any two consecutive Z ^C are carbons bonded to Y ¹ and N, the other Z ^C is CR ^C , Y ¹ is B, G _A and G _B are 1 expressed by formula (G) It is a valent group, Z ^a is CR ^a , R ^C and R ^a are hydrogen or a substituent, A is >O, and the monovalent group represented by formula (G) uses any one position as the substitution position, and in the above structure, , 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 structure may be substituted with cyano, halogen, or deuterium)

Description

Polycyclic aromatic compounds {POLYCYCLIC AROMATIC COMPOUNDS}

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, organic electroluminescent devices, display devices, and lighting devices containing the polycyclic aromatic compound.

Conventionally, display devices using light-emitting elements that emit electroluminescence have been frequently studied because they allow for power savings and thinning. Moreover, 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 (possibility 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 disposed between the pair of electrodes and containing 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 Documents 1 to 4 disclose that polycyclic aromatic compounds containing boron are useful as materials for organic electroluminescent devices and the like. It has been reported that organic electroluminescent devices containing this polycyclic aromatic compound have good external quantum efficiency. Patent Document 2 and Patent Document 3 disclose structures in which heterocycles such as benzothiophene are condensed. Patent Document 4 discloses a structure in which a heterocycle such as a dibenzofuran ring is introduced into the substituent portion.

[Patent Document 1] International Publication No. 2015/102118 [Patent Document 2] International Publication No. 2020/111830 [Patent Document 3] International Publication No. 2020/251049 [Patent Document 4] International Publication No. 2019/132028

As described above, various materials have been 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 those of the past is expected.

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

As a result of intensive studies to solve the above problems, the present inventors succeeded in producing a polycyclic aromatic compound exhibiting high luminous efficiency by combining a specific condensed ring structure and a substituent in the structures of the compounds described in Patent Documents 1 to 4. did. Furthermore, it was found 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 polycyclic aromatic compounds as described below, and further materials for organic devices containing the polycyclic aromatic compounds as described below.

The present invention specifically has the following configuration.

<0> A polycyclic aromatic compound having a structure consisting of one or two or more structural units represented by formula (1);

In equation (1),

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

The C ring is a ring expressed by the formula (C),

In equation (C),

X ^c is >O, > _NR , >C(-R) ₂ , >Si(-R) ₂ , >S, or >Se, and -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, and >C(-R ) ₂ and the two R of >Si(-R) ₂ may be bonded to each other to form a ring,

Any two consecutive Z ^Cs are on one side a carbon bonded to Y ¹ and on the other side a carbon bonded to N of >NG _B ,

Other Z ^C is each independently N or CR ^C ,

R ^C is each independently hydrogen or any one substituent selected from the substituent group ZB,

However, two adjacent R ^C on the c2 ring may be bonded to each other to form an aryl ring or heteroaryl ring together with the carbons to which they are bonded, and the formed aryl ring and the formed heteroaryl ring are selected from the substituent group ZB. may be substituted with at least one substituent,

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,

G _A and G _B are each independently monovalent groups expressed by the formula (G),

In formula (G),

Z ^a is each independently N or CR ^a ,

R ^a is each independently hydrogen or any one substituent selected from the substituent group ZB, or is bonded to adjacent R ^a to form an aryl ring or heteroaryl ring with the carbons to which they are bonded, and the aryl ring formed above The ring and the formed heteroaryl ring may each be substituted with at least one substituent selected from the substituent group ZB,

A is >O, >NR ^A , >Si(-R ^A ) ₂ , >C(-R ^A ) ₂ , >S, or >Se, and R ^A 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 ^A of >Si(-R ^A ) ₂ may be bonded to each other to form a ring. , the two R ^A of >C(-R ^A ) ₂ may be bonded to each other to form a ring,

However, the monovalent group represented by formula (G) binds to N of >NG _A or >NG _B at any one position,

In the above structure, at least one aryl ring or heteroaryl ring may be condensed with at least one cycloalkane, the cycloalkane may have a substituent, and at least one -CH ₂ in the cycloalkane - may be substituted with -O-,

At least one hydrogen in the above structure may be substituted with cyano, halogen, or deuterium.

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

In equation (1),

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

The C ring is a ring expressed by the formula (C),

In equation (C),

X ^c is >O, >NR _, >C(-R) ₂ , >Si(-R) ₂ , >S, or >Se, and -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, and >C(-R ) ₂ and the two R of >Si(-R) ₂ may be bonded to each other to form a ring,

Any two consecutive Z ^Cs are on one side a carbon bonded to Y ¹ and on the other side a carbon bonded to N of >NG _B ,

Other Z ^C is each independently N or CR ^C ,

R ^C is each independently hydrogen or any one substituent selected from the substituent group ZB,

Two adjacent R ^C on the c2 ring may be bonded to each other to form an aryl ring or heteroaryl ring together with the carbons to which they are bonded, and the formed aryl ring and the formed heteroaryl ring are at least one selected from the substituent group ZB. may be substituted with a substituent of

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,

G _A and G _B are each independently monovalent groups expressed by the formula (G),

In formula (G),

Z ^a is each independently N or CR ^a ,

R ^a is each independently hydrogen or any one substituent selected from the substituent group ZB, or is bonded to adjacent R ^a to form an aryl ring or heteroaryl ring with the carbons to which they are bonded, and the aryl ring formed above The ring and the formed heteroaryl ring may each be substituted with at least one substituent selected from the substituent group ZB,

A is >O, >NR ^A , >Si(-R ^A ) ₂ , >C(-R ^A ) ₂ , >S, or >Se, and R ^A 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 ^A of >Si(-R ^A ) ₂ may be bonded to each other to form a ring. , the two R ^A of >C(-R ^A ) ₂ may be bonded to each other to form a ring,

However, the monovalent group represented by formula (G) binds to N of >NG _A or >NG _B at any one position,

In the above structure, at least one aryl ring or heteroaryl ring may be condensed with at least one cycloalkane, the cycloalkane may have a substituent, and at least one -CH ₂ in the cycloalkane - may be substituted with -O-,

However, ^when ,

^When , has at least one substituent selected from the group consisting of substituted or unsubstituted diarylamino, substituted or unsubstituted arylheteroarylamino, and substituted or unsubstituted cycloalkyl, or aryl in the above structure. At least one selected from the group consisting of a ring and a heteroaryl ring is condensed with a cycloalkane, the cycloalkane may have a substituent, and at least one -CH ₂ - in the cycloalkane is substituted with -O-. It can be done,

At least one hydrogen in the above structure may be substituted with cyano, halogen, or deuterium.

<2> A polycyclic aromatic compound according to <1>, expressed by formula (1a);

In formula (1a), Z is each independently N or CR ¹¹ ,

R ¹¹ is each independently hydrogen or any one substituent selected from the substituent group ZB, or is combined with an adjacent R ¹¹ to form an aryl ring or heteroaryl ring together with the a ring or the b ring, and the formed aryl ring and the formed heteroaryl ring may be substituted with at least one substituent selected from the substituent group ZB,

Y ¹ , G _A , and G _B have the same meaning as Y ¹ , G _A and G _B in formula (1), respectively, and X ^c and Z ^c have the same meaning as X ^c and Z ^c in formula (C), respectively. meaning,

In formula (1a), at least one of the aryl ring or heteroaryl ring may be condensed with at least one cycloalkane, the cycloalkane may have a substituent, and at least one of the aryl rings or heteroaryl rings may be condensed with at least one cycloalkane. -CH ₂ - may be substituted with -O-;

At least one hydrogen in formula (1a) may be substituted with cyano, halogen, or deuterium.

<3> G _A and G _B are each independently expressed as formula (G-1), formula (G-4), or formula (G-5), or formula (G-1), formula (G -4), or a polycyclic aromatic compound according to <1> or <2>, which is a group represented by formula (G-5), wherein one or two hydrogens in the structure are substituted with alkyl or cycloalkyl. .

<4> The polycyclic aromatic compound according to any one of <1> to <3>, wherein A is >O.

<5> The polycyclic aromatic compound according to <1>, represented by any one of formula (1a-1), formula (1a-2), or formula (1a-3);

In equation (1a-1),

Ra1, Ra2, Ra3, Rb1, Rb2, Rb3, Rb4, Rc1, Rc2, Rc3, Rc4, Rg1, Rg2, Rg3, Rg4, Rg5, Rg6, Rg7, Rg8, Rg9, Rg10, Rg11, Rg12, Rg13, and Rg14 is each independently hydrogen or any one substituent selected from the substituent group ZB,

However, two adjacent ones of Rb1, Rb2, Rb3, and Rb4 may be bonded to each other to form an aryl ring together with the carbons to which they are bonded, and the formed aryl ring may be substituted with at least one substituent selected from the substituent group ZB. You can have it,

In formula (1a-1), at least one of the aryl ring or heteroaryl ring may be condensed with at least one cycloalkane, the cycloalkane may have a substituent, and at least one of the aryl rings or heteroaryl rings may be condensed with at least one cycloalkane. One -CH ₂ - may be substituted with -O-, provided that cycloalkane does not condense in the g11 ring and the g13 ring;

In equation (1a-2),

Ra1, Ra2, Ra3, Rb1, Rb2, Rb3, Rb4, Rc1, Rc2, Rc3, Rc4, Rg1, Rg2, Rg3, Rg4, Rg5, Rg6, Rg7, Rg8, Rg9, Rg10, Rg11, Rg12, Rg13, and Rg14 is each independently hydrogen or any one substituent selected from the substituent group ZB, provided that at least one of Ra1, Ra2, Ra3, Rb1, Rb2, Rb3, Rb4, Rc1, Rc2, Rc3, and Rc4 is, It is substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino, substituted or unsubstituted arylheteroarylamino, or substituted or unsubstituted cycloalkyl, or formula (1a- In 2), at least one selected from the group consisting of an aryl ring and a heteroaryl ring is condensed with a cycloalkane, the cycloalkane may have a substituent, and at least one -CH ₂ - in the cycloalkane may be substituted with -O-,

Two adjacent ones of Rb1, Rb2, Rb3, Rb4, Rc1, Rc2, Rc3, and Rc4 may be bonded to each other to form an aryl ring or heteroaryl ring together with the carbons to which they are bonded, and the formed aryl ring may be a substituent group. may be substituted with at least one substituent selected from ZB,

In formula (1a-2), at least one of the aryl ring or heteroaryl ring may be condensed with at least one cycloalkane, the cycloalkane may have a substituent, and at least one of the aryl rings or heteroaryl rings may be condensed with at least one cycloalkane. One -CH ₂ - may be substituted with -O-;

In equation (1a-3),

Ra1, Ra2, Ra3, Rb1, Rb2, Rb3, Rb4, Rc1, Rc2, Rc3, Rc4, Rg1, Rg2, Rg3, Rg4, Rg5, Rg6, Rg7, Rg8, Rg9, Rg10, Rg11, Rg12, Rg13, and Rg14 is each independently hydrogen or any one substituent selected from the substituent group ZB,

However, two adjacent ones of Rb1, Rb2, Rb3, Rb4, Rc1, Rc2, Rc3, and Rc4 may be bonded to each other to form an aryl ring or heteroaryl ring with the carbons to which they are bonded, and the formed aryl ring may be may be substituted with at least one substituent selected from the substituent group ZB,

In formula (1a-3), at least one of the aryl ring or heteroaryl ring may be condensed with at least one cycloalkane, the cycloalkane may have a substituent, and at least one of the aryl rings or heteroaryl rings may be condensed with at least one cycloalkane. One -CH ₂ - may be substituted with -O-;

At least one hydrogen in each formula (1a-1), formula (1a-2), and formula (1a-3) may be substituted with cyano, halogen, or deuterium.

<6> A polycyclic aromatic compound according to <3>, represented by any of the following formulas;

where Me is methyl, tBu is t-butyl, and D is deuterium.

<7> A polycyclic aromatic compound according to <3>, represented by any of the following formulas;

where Me is methyl, tBu is t-butyl, tAm is t-amyl, and D is deuterium.

<8> The polycyclic aromatic compound according to <5>, represented by formula (1a-3).

<9> A polycyclic aromatic compound according to <8>, represented by any of the following formulas;

where Me is methyl and tBu is t-butyl.

<10> A material for an organic device containing the polycyclic aromatic compound according to any one of <1> to <9>.

<11> Organic, 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 <9>. Electroluminescent device.

<12> The organic electroluminescent device according to <11>, wherein the light-emitting layer includes a host and the polycyclic aromatic compound as a dopant.

<13> The organic electroluminescent device according to <12>, wherein the host is an anthracene compound, a fluorene compound, or a dibenzochrysene compound.

<14> A display device or lighting device provided with the organic electroluminescent element according to any one of <11> to <13>.

According to the present invention, a novel polyaromatic 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 aspect 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 and 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 the description of the structural formula in this specification, “hydrogen” means “hydrogen atom (H)”, and “oxygen” means “oxygen atom (O)”. Other elements may also be described similarly.

In the present specification, “Me” is methyl, “Et” is ethyl, “nBu” is n-butyl (normal butyl), “tBu” is t-butyl (tertiary butyl), “iBu” is isobutyl, and “secBu” is " is secondaryributyl, "nPr" is n-propyl (normal propyl), "iPr" is isopropyl, "tAm" is t-amyl, "2EH" is 2-ethylhexyl, "tOct" is t-octyl, " “Ph” is phenyl, “Mes” is mesityl (2,4,6-trimethylphenyl), “Ad” is 1-adamantyl, “Tf” is trifluoromethanesulfonyl, “TMS” is trimethylsilyl, “D” represents deuterium.

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 expressed in terms of carbon number, but 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 chemical 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)” replaces “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 has various forms such as enantio isomers, diastereo isomers, or rotational isomers. There are cases where isomeric structures exist. In this specification, unless otherwise specified, the described compounds may have any isomeric structure conceivable from their planar structural formula, or may be a mixture of possible isomers in any ratio. Additionally, among these isomers, isomers that do not isomerize at room temperature can be easily separated by methods such as recrystallization, sublimation purification, or distribution chromatography.

In this specification, many structural formulas of aromatic compounds are described. Aromatic compounds are described as a combination of double bonds and single bonds, but in reality, since π electrons resonate, even for single substances, there are multiple equivalent resonance structures, such as double bonds and single bonds being alternated. . In this specification, only one resonance structural formula is described for one substance, but unless otherwise specified, other organic chemically equivalent resonance structural formulas are also included. This is referred to in descriptions such as “Z=Z” described later. For example, an example of “Z=Z” in equation (1) described later is as follows. However, it is not limited to this, and naturally applies not only to the one resonance structural formula described, but also to other equivalent resonance structural formulas that can be thought of.

Meanwhile, in this specification, two expressions are used: “You may do” and “It is not possible to do, or it is possible to do,” but both expressions have the same meaning.

In this specification, “adjacent groups” means two groups each bonded to two adjacent atoms (two atoms directly bonded by a covalent bond) in the structural formula.

0. Description of rings and substituents

First, details of the rings and substituents used in this specification will be described below.

The "aryl ring" in the present specification includes, for example, an aryl ring having 6 to 30 carbon atoms, an aryl ring having 6 to 16 carbon atoms is preferable, an aryl ring having 6 to 12 carbon atoms is more preferable, and an aryl ring having 6 to 12 carbon atoms is more preferable. An aryl ring of ~10 is particularly preferred.

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 each substituted with an 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" include a heteroaryl ring having 2 to 30 carbon atoms, with a heteroaryl ring having 2 to 25 carbon atoms being preferable, a heteroaryl ring having 2 to 20 carbon atoms being more preferable, and a heteroaryl ring having 2 to 25 carbon atoms being more preferable. A heteroaryl ring with 15 carbon atoms is 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, naphthyridine ring, purine ring, pteridine ring, carbazole ring, carborine ring, acridine ring, phenoxathidine 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, dioxaboranaphthoanthracene ring (5,9-dioxa-13b-boranaphtho[3,2,1-de]anthracene ring, etc.), etc. In addition, in the dihydroacridine ring, xanthene ring, and thioxanthene ring, two of the two hydrogens of methylene are each substituted with an alkyl such as methyl as the first substituent described later, resulting in dimethyldihydroacridine ring, dimethylxanthene ring, and dimethylthioxane. It is also preferable that it is made of a ten 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 this specification, a substituent may be substituted with another substituent (a substituent may be described as “substituted or unsubstituted”). This means that at least one hydrogen of the substituent (“first substituent” or “first substituent”) is substituted with another substituent (“second substituent” or “second substituent”), or is not substituted. do. Regarding the first substituent (first substituent) and the second substituent (second substituent), the description in the specification can be referred to, respectively.

In this specification, the substituent group ZB is,

Aryl which may be substituted with at least one group selected from the group consisting of aryl, heteroaryl, diarylamino, alkyl, cycloalkyl and substituted silyl,

Heteroaryl, which may be substituted with at least one group selected from the group consisting of aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, and substituted silyl,

Diarylamino, which may be substituted with at least one group selected from the group consisting of aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, and substituted silyl (two aryls may be bonded to each other through a linking group),

Diheteroarylamino, which may be substituted with at least one group selected from the group consisting of aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, and substituted silyl (two heteroaryls may be bonded to each other through a linking group),

Arylheteroarylamino may be substituted with at least one group selected from the group consisting of aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, and substituted silyl (aryl and heteroaryl may be bonded to each other through a linking group) ,

Diarylboryl, which may be substituted with at least one group selected from the group consisting of aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, and substituted silyl (two aryls may be bonded through a single bond or linking group),

Alkyl which may be substituted with at least one group selected from the group consisting of aryl, heteroaryl, diarylamino, alkyl, cycloalkyl and substituted silyl,

Cycloalkyl, which may be substituted with at least one group selected from the group consisting of aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, and substituted silyl,

Alkoxy which may be substituted with at least one group selected from the group consisting of aryl, heteroaryl, diarylamino, alkyl, cycloalkyl and substituted silyl,

Aryloxy which may be substituted with at least one group selected from the group consisting of aryl, heteroaryl, diarylamino, alkyl, cycloalkyl and substituted silyl,

Arylthio which may be substituted with at least one group selected from the group consisting of aryl, heteroaryl, diarylamino, alkyl, cycloalkyl and substituted silyl, and

It consists of substituted silyl.

Aryl, which is the second substituent in each group of substituent group ZB, may be further substituted with aryl, heteroaryl, alkyl, or cycloalkyl. Similarly, heteroaryl, which is the second substituent, may be substituted with aryl, heteroaryl, alkyl, or cycloalkyl. It may be substituted with alkyl.

In this specification, when referring to a “substituent”, unless otherwise specified, it may be any one group selected from the substituent group ZB. For example, when a group described as “substituted or unsubstituted” is substituted, the group may be substituted with at least one group selected from the substituent group ZB.

In this specification, “aryl” includes, for example, aryl having 6 to 30 carbon atoms, with aryl having 6 to 24 carbon atoms being preferable, aryl having 6 to 20 carbon atoms being more preferable, and aryl having 6 to 16 carbon atoms. Aryl is more preferable, aryl with 6 to 12 carbon atoms is particularly preferable, and aryl with 6 to 10 carbon atoms is most preferable.

The specific “aryl” is. Monovalent groups of the above-mentioned “aryl ring” include, for example, monocyclic phenyl, bicyclic biphenylyl (2-biphenylyl, 3-biphenylyl, or 4-biphenylyl), condensation dicyclic naphthyl (1-naphthyl or 2-naphthyl), tricyclic terphenylyl (m-terphenyl-2'-yl, m-terphenyl-4'-yl, m-terphenyl-5) '-yl, o-terphenyl-3'-yl, o-terphenyl-4'-yl, p-terphenyl-2'-yl, m-terphenyl-2-yl, m-terphenyl-3- 1, m-terphenyl-4-yl, o-terphenyl-2-yl, o-terphenyl-3-yl, o-terphenyl-4-yl, p-terphenyl-2-yl, p-ter phenyl-3-yl, or p-terphenyl-4-yl), condensed tricyclic, acenaphthylene-(1-, 3-, 4-, or 5-)yl, fluorene-(1-, 2) -, 3-, 4-, or 9-) days, phenalen-(1- or 2-) days, phenanthrene-(1-, 2-, 3-, 4-, or 9-) days, or anthracene -(1-, 2-, or 9-)yl, tetracyclic tetraphenylyl (5'-phenyl-m-terphenyl-2-yl, 5'-phenyl-m-terphenyl-3-yl, 5 '-phenyl-m-terphenyl-4-yl, or m-quarterphenyl), condensed tetracyclic, triphenylen-(1- or 2-)yl, pyrene-(1-, 2-, or 4- ) yl, or naphthacene-(1-, 2-, or 5-)yl, or, which is a condensed pentacyclic system, perylene-(1-, 2-, or 3-)yl, or pentacene-(1- , 2-, 5-, or 6-) days, etc. In addition, the monovalent group of spirofluorene, etc. can be mentioned.

In addition, the aryl as the second substituent includes aryl such as phenyl (specific examples are groups described above), alkyl such as methyl (specific examples are groups described later), and cycloalkyl such as cyclohexyl or adamantyl. Structures substituted with at least one group selected from the group consisting of (groups of which specific examples will be described later) are also included.

As an example, a group in which the 9th position of fluorenyl as the second substituent is substituted with aryl such as phenyl, alkyl such as methyl, or cycloalkyl such as cyclohexyl or adamantyl.

“Arylene” is, for example, arylene with 6 to 30 carbon atoms, preferably arylene with 6 to 20 carbon atoms, arylene with 6 to 16 carbon atoms, arylene with 6 to 12 carbon atoms, or arylene with 6 to 12 carbon atoms. 10 arylene, etc.

Specific examples of “arylene” include a divalent group obtained by removing one hydrogen from the above-mentioned “aryl” (monovalent group).

Examples of “heteroaryl” include heteroaryl having 2 to 30 carbon atoms, heteroaryl having 2 to 25 carbon atoms is preferable, heteroaryl having 2 to 20 carbon atoms is more preferable, and heteroaryl having 2 to 15 carbon atoms is preferable. Aryl is more preferable, and heteroaryl having 2 to 10 carbon atoms is particularly preferable. In addition, examples of heteroaryl include heterocycles containing 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen as ring atoms in addition to carbon.

Specific examples of “heteroaryl” include the monovalent group of the “heteroaryl ring” described above, for example, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, and oxadiazolyl. , thiadiazolyl, triazolyl, tetrazolyl, pyrazolyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, indolyl, isoindolyl, 1H-indazolyl, benzoimidazolyl, benzoxa. Zolyl, benzothiazolyl, 1H-benzotriazolyl, quinolinyl, isoquinolinyl, cinnolinyl, quinazolinyl, quinoxalinyl, phenanthrolinyl, phthalazinyl, naphthyridinyl, purinyl, pteri. Dinyl, carbazolyl, acridinyl, phenoxathiinyl, phenoxazinyl, phenothiazinyl, phenazinyl, phenazoxylinyl, indolizinyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl. Nyl, naphthobenzofuranyl, thienyl, benzothienyl, isobenzothienyl, dibenzothienyl, naphthobenzothienyl, benzophosphoryl, dibenzophosphoryl, benzophosphoryl oxide ring monovalent group, di Monovalent groups of the benzophosphole oxide ring, furazanyl, thianthrenyl, indolocarbazolyl, benzoindolocarbazolyl, dibenzoindolocarbazolyl, imidazolinyl, or oxazolinyl, etc. there is. In addition, the monovalent group of spiro[fluorene-9,9'-xanthene], the monovalent group of spirobi[silafluorene], and the monovalent group of benzoselenophene can be mentioned.

In addition, heteroaryl as the second substituent includes aryl such as phenyl (specific examples are groups described above), alkyl such as methyl (specific examples are groups described later), and cyclo such as cyclohexyl or adamantyl. Structures substituted with at least one group selected from the group consisting of alkyl (a group whose specific examples will be described later) are also included.

As an example, a group in which the 9th position of carbazolyl as the second substituent is substituted with aryl such as phenyl, alkyl such as methyl, or cycloalkyl such as cyclohexyl or adamantyl. In addition, nitrogen-containing heteroaryls such as pyridyl, pyrimidinyl, triazinyl, and carbazolyl, which are further substituted with phenyl or biphenylyl, are also included in heteroaryl as the second substituent.

“Heteroarylene” is, for example, heteroarylene having 2 to 30 carbon atoms, preferably heteroarylene having 2 to 25 carbon atoms, heteroarylene having 2 to 20 carbon atoms, heteroarylene having 2 to 15 carbon atoms. , or heteroarylene having 2 to 10 carbon atoms, etc. In addition, “heteroarylene” is, for example, a divalent group such as a heterocycle containing 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen in addition to carbon as ring atoms.

Specific examples of “heteroarylene” include a divalent group obtained by removing one hydrogen from the above-mentioned “heteroaryl” (monovalent group).

“Diarylamino” is amino in which two aryls are substituted, and the description of “aryl” described above can be cited for details on this aryl.

“Diheteroarylamino” is an amino in which two heteroaryls are substituted, and the description of “heteroaryl” described above can be cited for details on this heteroaryl.

“arylheteroarylamino” is amino in which aryl and heteroaryl are substituted. For details on aryl and heteroaryl, the explanation of “aryl” and “heteroaryl” described above can be cited.

Two aryls in diarylamino as the first substituent may be bonded to each other through a linking group, and two heteroaryls in diheteroarylamino as the first substituent may be bonded to each other through a linking group, and the first substituent may be bonded to each other through a linking group. Aryl and heteroaryl of arylheteroarylamino as substituents may be bonded to each other through a linking group. Here, the description of “bonding through a linking group” indicates that, for example, two phenyls of diphenylamino form a bond through a linking group, as shown below. This description also applies to diheteroarylamino and arylheteroarylamino, formed from aryl or heteroaryl.

(* indicates binding position)

^As a _linking group _, ^specifically , ^{> O} , > ^NR >CO, >CS, >SO, >SO ₂ , and >Se. ^{R In} _addition ^{, two R} _{_} ^_ They may be combined with each other through ^Y to form a ring. X ^Y includes >O, >NR ^Y , >C(-R ^Y ) ₂ , >Si(-R ^Y ) ₂ , >S, >CO, >CS, >SO, >SO ₂ , and >Se. and R ^Y 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 2} It may be substituted. ^{Two R _} . That is ^, -C( ^-R

In addition, in this specification, when it is simply described as “diarylamino,” “diheteroarylamino,” or “arylheteroarylamino,” unless specifically limited, “two aryls of the diarylamino are adjacent to each other.” “The two heteroaryls of the diheteroarylamino are not bonded to each other or are connected to each other through a linking group” and “The aryl and heteroaryl of the arylheteroarylamino are It is assumed that the explanation “They are not connected to each other or are connected through a connector” is added.

“Alkyl” 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 6 carbon atoms (branched chain alkyl with 3 to 12 carbon atoms) is more preferable. Branched-chain alkyl with ~6 carbon atoms) is particularly preferred, and alkyl with 1-5 carbon atoms (branched-chain alkyl with 3-5 carbon atoms) is most preferred.

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-dimethyl hexyl etc. can also be mentioned.

“Alkylene” is a divalent group obtained by removing the hydrogen of any one of “alkyl”, for example, methylene, ethylene, and propylene.

“Cycloalkyl” 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, cycloalkyl with 5 to 10 carbon atoms, and cycloalkyl with 5 to 8 carbon atoms. Cycloalkyl, cycloalkyl with 5 to 6 carbon atoms, cycloalkyl with 5 carbon atoms, etc. can be mentioned. As listed below, cyclohexyl in this specification includes monocyclic cyclohexyl and the like, as well as polycyclic cyclohexyl such as adamantyl.

Specific examples of “cycloalkyl” include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, bicyclo[1.1.0]butyl, and 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(norbornyl), bicyclo[2.2.2] Octyl, adamantyl, diamantyl, decahydronaphtharenyl, decahydroazulenyl, and alkyl (especially methyl) substituents having 1 to 5 carbon atoms thereof.

Examples of “alkenyl” 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 still more preferable, and alkenyl with 2 to 4 carbon atoms is especially preferable. Regarding "alkenyl", the explanation of "alkyl" mentioned above can be referred to. It is a group in which the C-C single bond in the structure of "alkyl" is replaced with a C=C double bond, and it has not only one but two or more single bonds. Also includes groups where the bond is replaced by a double bond (also called alkadiene-yl or alkatrien-yl).

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

“Alkenylene” is a divalent group obtained by removing any hydrogen of “alkenyl”, and examples include vinylene.

Regarding "alkynyl", the explanation of "alkyl" mentioned above can be referred to. It is a group in which the C-C single bond in the structure of "alkyl" is replaced with a C≡C triple bond, and it has not only one but two or more single bonds. Also includes groups where the bond is replaced by a triple bond (also called alkadiin-yl or alkatrien-yl).

Examples of “alkoxy” 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 to 5 carbon atoms (branched chain alkoxy with 3 to 5 carbon atoms) is particularly preferable.

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

“Aryloxy” is a group in which the hydrogen of the -OH group is substituted with aryl, and the above-mentioned examples of aryl and its preferable range can be cited.

“Arylthio” is a group in which the hydrogen of the -SH group is substituted with aryl, and the above-mentioned aryl and its preferable range can be cited.

Examples of “substituted silyl” 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 each of the three hydrogens in silyl is independently substituted with alkyl, and this alkyl and its preferred range refer to the group described as “alkyl” in the first substituent described above. You can. Alkyl suitable 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.

Examples of “tricycloalkylsilyl” include groups in which three hydrogens in the silyl group are each independently substituted with cycloalkyl, and this cycloalkyl and its preferred range are as “cycloalkyl” in the first substituent described above. The explanation 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, Decahydroazrenyl, 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.

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. Silyl substituted with a group selected from: Specific examples of triarylsilyl include triphenylsilyl.

As for “aryl” in “diarylboryl” and its preferable range, the description of aryl described above can be cited. Additionally, these two aryls are single bonds or linking groups (e.g. -CH=CH-, -CR=CR-, -C≡C-, >NR, >O, >S, >C(-R) ₂ , >Si(-R) ₂ , or >Se) may be bonded. Here, R of -CR=CR-, R of >NR, R of >C(-R) ₂ , and R of >Si(-R) are aryl, heteroaryl, diarylamino, alkyl, alkenyl. , alkynyl, cycloalkyl, alkoxy, or aryloxy, and at least one hydrogen in R may be further substituted with aryl, heteroaryl, alkyl, alkenyl, alkynyl, or cycloalkyl. Additionally, two adjacent R groups may combine to form a ring, forming cycloalkylene, arylene, and heteroarylene. For details of the substituents listed here, the description of each substituent above can be cited. Additionally, in the case where "diarylboryl" is simply described in this specification, unless specifically limited, an explanation is added that "the two aryls of diarylboryl may be bonded to each other through a single bond or a linking group." Pretend it exists.

In this specification, when two groups bonded to the same atom may be bonded to each other to form a ring, they may be bonded by a single bond or a linking group (together, they are also called a linking group), and the linking group may be -CH ₂ - CH ₂ -, -CHR-CHR-, -CR ₂ -CR ₂ -, -CH=CH-, -CR=CR-, -C≡C-, -N(-R)-, -O-, -S -, -C(-R) ₂ -, -Si(-R) ₂ -, or -Se- can be mentioned, and examples include the following structures. In addition, R of -CHR-CHR-, R of -CR ₂ -CR ₂ -, R of -CR=CR-, R of -N(-R)-, R of -C(-R) ₂ -, and R of -Si(-R) ₂ - are each independently hydrogen, aryl optionally substituted with alkyl or cycloalkyl, heteroaryl optionally substituted with alkyl or cycloalkyl, or alkyl optionally substituted with cycloalkyl. , alkenyl which may be substituted with alkyl or cycloalkyl, alkynyl which may be substituted with alkyl or cycloalkyl, or cycloalkyl which may be substituted with alkyl or cycloalkyl. Additionally, two adjacent R groups may combine to form a ring to form cycloalkylene, arylene, or heteroarylene.

As a linking group, a single bond, -CR=CR-, -N(-R)-, -O-, -S-, -C(-R) ₂ -, -Si(-R) ₂ -, and - as a linking group. Se- is preferred, a single bond, -CR=CR-, -N(-R)-, -O-, -S-, and -C(-R) ₂ - as a linking group are more preferred, a single bond, -CR=CR-, -N(-R)-, -O-, and -S- as linking groups are more preferable, and a single bond is most preferable.

The position where two R are bonded by the linking group is not particularly limited as long as it is a position where bonding is possible, but it is preferable to bond at the most adjacent position. For example, when the two groups are phenyl, "C" in phenyl or It is preferable to bond at ortho (second position) positions based on the bonding position (first position) of “Si” (refer to the structural formula above).

<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), preferably one or two or more structural units represented by formula (1a). It is a polycyclic aromatic compound with a structure consisting of. The polycyclic aromatic compound of the present invention has a narrow emission half width and good color purity, and can lower the driving voltage of an organic EL device and increase the luminescence quantum yield (PLQY).

[Explanation of ring structure in compounds]

In equation (1), “A”, “B”, and “C” within the circles are symbols representing the ring structure represented by each circle. The structure represented by formula (1) is a structure in which at least four aromatic rings, which are the A ring, the B ring, and the c1 ring and c2 ring, are connected to boron and hetero elements such as oxygen, sulfur, or nitrogen to form a ring structure. has The ring structure formed is a condensed ring structure composed of at least 6 rings.

In formula (1), ring A and ring B are each independently a substituted or unsubstituted aryl ring or a substituted or unsubstituted heteroaryl ring. However, when X ^c is >S, ring B is a substituted or unsubstituted aryl ring.

Ring A forms a trivalent group having bonding hands at three consecutive atoms (preferably carbon) in the ring of the aryl ring or heteroaryl ring in the structure. In these three binding hands, the A ring bonds to ^one Y and two N's. The B ring forms a divalent group having a bond at two consecutive atoms (preferably carbon) in the ring of the aryl ring or heteroaryl ring in the structure. In these two binding hands, the B ring is bonded to Y ¹ and N.

The substituent for each of the aryl ring and heteroaryl ring may be any one selected from the substituent group ZB. For the preferable range of the substituent, refer to the preferable range of R ¹¹ described later.

The aryl ring or heteroaryl ring in the A ring is preferably bonded to Y ¹ and two Ns in a 5- or 6-membered ring. The aryl ring or heteroaryl ring in ring B is preferably bonded to Y ¹ and N in a 5- or 6-membered ring. “It is bonded to a 5-membered ring or 6-membered ring” means that a ring is formed only from this 5-membered ring or 6-membered ring, or that a ring is formed by further condensing other rings including this 5-membered ring or 6-membered ring. In other words, it means that the 5-membered ring or 6-membered ring constituting all or part of the ring is bonded to B, Y ¹ and two Ns, or Y ¹ and N. In the aryl ring or heteroaryl ring in ring A and ring B, two or three consecutive ring atoms (carbon atoms) may be directly bonded to Y ¹ and two N, or Y ¹ and N. .

Examples of 6-membered rings in ring A and ring B include benzene ring, pyridine ring, pyrazine ring, and pyrimidine ring. Examples of a 6-membered ring further condensed with another ring include a naphthalene ring, a quinoline ring, a dibenzofuran ring, a dibenzothiophene ring, and a carbazole ring. Examples of 5-membered rings include furan rings, thiophene rings, pyrrole rings, and thiazole rings. Examples of a 5-membered ring further condensed with another ring include a benzofuran ring, a benzothiophene ring, and an indole ring. The aryl ring or heteroaryl ring in ring A is preferably a benzene ring. The aryl ring or heteroaryl ring in ring B is preferably a benzene ring.

In formulas (1) and (2), ring C is a ring structure represented by formula (C). In formula (C), two consecutive Z ^C 's are a carbon bonded to Y ¹ on one side and a carbon bonded to N on the other side. That is, Y ¹ and N are adjacent to each other in the C ring. This means that, as shown below, Y ¹ and N may be bonded to two consecutive Z ^Cs of the c1 ring, and Y ¹ and N may be bonded to two consecutive Z ^Cs of the c2 ring.

In formula (C), X ^c is >O, >NR, >C(-R) ₂ , >Si(-R) ₂ , >S, or >Se, and ₂ and R of >Si(-R) ₂ are each independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, >C(-R) ₂ and the two R of >Si(-R) ₂ are bonded to each other to form a ring or are not formed. The two R's of >C(-R) ₂ and >Si(-R) ₂ may be bonded to each other to form a ring, or may not form a ring. This group is described as “substituted or unsubstituted,” and preferred substituents include aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl. Still, the aryl of the diarylamino is substituted with alkyl or cycloalkyl, or is not substituted. Regarding the first and second substituents, the phrases used herein, and their preferable ranges, the description in the specification can be referred to. X ^c is preferably >O, >C(-R) ₂ or >S, and is more preferably >S.

In formula (C), Z ^C is each independently N or CR ^C , and R ^C is each independently hydrogen or any one substituent selected from the substituent group ZB. In formula (C), the number of Z ^C for N is preferably 0 to 2, more preferably 0 to 1, and especially preferably 0. In formula (C), the number of R ^C as a substituent is preferably 0 to 1, and the other R ^C is preferably hydrogen.

Additionally, two adjacent R ^C on the c2 ring may be bonded to each other to form an aryl ring or heteroaryl ring. The formed aryl ring and heteroaryl ring may each be substituted with at least one substituent selected from substituent group ZB. At this time, the substituent selected from the substituent group ZB is preferably substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino, substituted or unsubstituted alkyl, substituted or unsubstituted Cycloalkyl, or substituted silyl. The aryl ring formed is preferably a benzene ring, a naphthalene ring, an indene ring, or a cyclopentadiene ring, and the heteroaryl ring formed is a thiophene ring, a pyrrole ring, a furan ring, a benzothiophene ring, a benzofuran ring, or an indole ring. It is preferable, and a benzene ring is most preferable.

An example of the bonding form of the ring structure represented by formula (C) with other partial structures of formula (2) is shown below. In Equation (1a), Equation (1b), Equation (1c), Equation (1d), Equation (1e), Equation (1f), Equation (1g) and Equation (1h), Z ^c is each independently CR ^C is preferred, and in formulas (1c), (1d), (1e), (1f), (1g) and (1h), Z ^c of the c2 ring is each independently CR. ^c , and as will be described later, a form in which adjacent R ^c is bonded to each other to form an aryl ring (preferably a benzene ring) is also preferable. In addition, among Equations (1a), Equations (1b), Equations (1c), Equations (1d), Equations (1e), Equations (1f), Equations (1g), and Equations (1h), Equations (1a), Equations ( 1b) is preferred, and equation (1a) is most preferred. Likewise, for explanations of each symbol and phrase, reference may be made to the description of this specification described later.

In formula (1c), formula (1d), formula (1e), formula (1f), formula (1g), and formula (1h), Z ^C of the c2 ring is each independently N or CR ^C , and Adjacent CR ^C is preferably bonded to each other to form an aryl ring or heteroaryl ring (preferably an aryl ring, more preferably a benzene ring). This preferred form is shown below. Definitions of each symbol in Equation (1c-2), Equation (1d-2), Equation (1e-2), Equation (1f-2), Equation (1g-2), and Equation (1h-2), and their preferred Regarding the range, please refer to the explanation of equation (1c), equation (1d), equation (1e), equation (1f), equation (1g) and equation (1h).

[Explanation of Y1]

In formula (1) and its preferred forms, 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, and B is most preferred. 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.

[Description of G _A and G _B ]

In formula (1) and its preferred forms, G _A and G _B are each independently monovalent groups represented by formula (G).

In formula (G), Z ^a is each independently N or CR ^a . In formula (G), Z ^a , which is N, is preferably 0 to 3, more preferably 0 to 2, further preferably 0 to 1, and especially preferably 0. Each R ^a is independently hydrogen or any one substituent selected from the substituent group ZB, or is bonded to an adjacent Ra to form an aryl ring or heteroaryl ring. The formed aryl ring and heteroaryl ring may each be substituted with at least one substituent selected from the substituent group ZB. The substituent at this time is preferably any one of the substituents selected from the substituent group ZB, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl. . It is preferable that R ^a is all hydrogen or 1 to 3 substituents are each independently selected from substituent group ZB, and R ^a is all hydrogen or 1 to 2 substituents are each independently selected from substituent group ZB. It is more preferable that it is one substituent, and it is even more preferable that all R ^a are hydrogen.

In formula (G), A is >O, >NR ^A , >Si(-R ^A ) ₂ , >C(-R ^A ) ₂ , >S, or >Se, and R ^A is each independently hydrogen, Substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, and the two R ^A of >Si(-R ^A ) ₂ , and the >C R ^A of (-R ^A ) ₂ is bonded to each other to form a ring or is not formed. As A, >O, >NR ^A , >C(-R ^A ) ₂ or >S is preferable, >O, >NR ^A or >S is more preferable, and >O is most preferable. In addition, R A of >NR ^A as ^A is preferably substituted or unsubstituted aryl or substituted or unsubstituted heteroaryl. Here, the substituent when saying “substituted or unsubstituted” is preferably aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl, and aryl of diarylamino is substituted with alkyl or cycloalkyl. You can stay.

The monovalent group represented by formula (G) combines with N of >NG _A or >NG _B at any position. The position of formula (G) that binds to N is C (carbon atom) of CH of Z ^a (corresponding to the case where R ^a of CR ^a is H), or any C (carbon atom) of R ^a of CR ^a of Z ^a ( carbon atom), any C (carbon atom) of an aryl ring or heteroaryl ring formed by two R ^a of adjacent CR a bonded to each other, an aryl ring formed by two Ra of adjacent ^{CR a bonded} to each other, or Any C (carbon atom) on R ^a which is a substituent of the heteroaryl ring, any C (carbon atom) on the substituent of the monovalent group represented by formula (G), any C on R of >NR which is A (carbon atom), any C (carbon atom) on R of >Si(-R) ₂ which is A, or any C (carbon atom) on R of >C(-R) ₂ which is A. However, C ^of CH which ^is Z ^a (corresponding to the case where R ^a of CR ^a is H), or any C (carbon atom) is preferred.

Specific examples of the monovalent group represented by formula (G) include, for example, a monovalent group represented by any of the following formulas (G-1) to (G-52). However, it is not limited to this example. Similarly, in the formula below, * represents the bonding position with N in >N-GA. In addition, regarding each symbol in the formula, the description in the specification can be referred to. In addition, the monovalent groups represented by formulas (G-1) to (G-52) may have any group selected from the substituent group ZB as a substituent. The most preferred substituent is alkyl (especially tR, which will be described later) or cycloalkyl. The monovalent groups represented by formulas (G-1) to (G-52) may be condensed with at least one cycloalkane described later.

Monovalent groups represented by formulas (G-1) to (G-52) do not have a substituent, or one or two hydrogens in the structure are substituted with alkyl (especially tR, which will be described later) or cycloalkyl. It is desirable.

Among the above, Formula (G-1), Formula (G-4), Formula (G-5), Formula (G-7), Formula (G-10), Formula (G-11), Formula (G-25) ), formula (G-34), or formula (G-39) is preferred, and formula (G-1), formula (G-4), formula (G-5), formula (G-7), formula ( Formula (G-10) or formula (G-11) is more preferable, and formula (G-1), formula (G-4) or formula (G-5) is most preferable.

G _A and G _B may be the same or different. G _A and G _B are both groups represented by the formula (G-1), or G _A is a group represented by the formula (G-5), and G _B is preferably a group represented by the formula (G-1). And, it is more preferable that they are all groups expressed by formula (G-1).

[Explanation of Z in equation (1a)]

　

In formula (1a), Z is each independently N or CR ¹¹ . In formula (1a), Z, which is N, is preferably 0 to 3, more preferably 0 to 2, further preferably 0 to 1, and especially preferably 0.

R ¹¹ of CR 11 is each independently hydrogen or any one substituent selected from the substituent group ZB, ^and two adjacent R ¹¹ are bonded to each other to form an aryl ring or heteroaryl ring together with the a ring or the b ring; You can stay. The formed aryl ring and heteroaryl ring may each be substituted with at least one substituent selected from substituent group ZB.

R ¹¹ is hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino, substituted or unsubstituted arylheteroarylamino, substituted or unsubstituted alkyl, substituted or unsubstituted. Substituted cycloalkyl, or substituted silyl is preferred.

It is preferable that each of Z is independently CR ¹¹ . At this time, it is also preferable that R ¹¹ which is the para position of Y ¹ on the benzene ring is hydrogen or a substituent other than hydrogen, and other R ¹¹ is hydrogen. In the B ring, it is more preferable that R ¹¹ at the para position of Y ¹ on the benzene ring is a substituent other than hydrogen, and other R ¹¹ is hydrogen. The substituent at this time is, for example, substituted with tertiary alkyl (t-butyl or t-amyl, etc.) represented by the formula (tR), cycloalkyl, tertiary alkyl represented by the formula (tR), or other alkyl. Optional examples include diarylamino or arylheteroarylamino. In ring A, it is more preferable that R ¹¹ which is the para position of Y ¹ on the benzene ring is hydrogen or alkyl (methyl or t-butyl, etc.), and other R ¹¹ is hydrogen.

On the ^{other hand} , when , and at least one substituent selected from the group consisting of substituted or unsubstituted cycloalkyl, or at least one selected from the group consisting of an aryl ring and a heteroaryl ring in formula (1a), as described later. It is condensed with cycloalkane.

Two adjacent R ¹¹ may be bonded to each other to form an aryl ring or heteroaryl ring together with the carbons to which they are bonded. ^{However ,} when The formed aryl ring and heteroaryl ring may be substituted with at least one substituent selected from the substituent group ZB. The substituent at this time is preferably substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, or substituted It's Silyl. The aryl of diarylamino is preferably unsubstituted or substituted with alkyl or cycloalkyl. The aryl ring formed is preferably a benzene ring, a naphthalene ring, an indene ring, or a cyclopentadiene ring, and the heteroaryl ring formed is a thiophene ring, a pyrrole ring, a furan ring, a benzothiophene ring, a benzofuran ring, or an indole ring. desirable.

[Equation (1a-1), Equation (1a-2), and Equation (1a-3)]

Additionally, as more preferable embodiments of formula (1a), the following formulas (1a-1), (1a-2), and (1a-3) can be given.

In formula (1a-1), formula (1a-2), and formula (1a-3), Ra1 to Ra3, Rb1 to Rb4, and Rc1 to Rc4 are each independently selected from hydrogen or substituent group ZB. It is one substituent, preferably hydrogen or any one substituent selected from the following substituent group ZB-2, and more preferably hydrogen or any one substituent selected from the following substituent group ZB-3. 0 to 1 of Ra1 to Ra3, 0 to 1 of Rb1 to Rb4, and 0 to 1 of Rc1 to Rc4 are any one of the substituents selected from the substituent group ZB, and the others are preferably hydrogen. Ra1, Ra3, Rb1, Rb4, and Rc1 are preferably all hydrogen.

Substituent group ZB-2 consists of:

alkyl,

Cycloalkyl (may be substituted with alkyl),

Aryl (may be substituted with alkyl or cycloalkyl which may be substituted with alkyl),

Heteroaryl (may be substituted with alkyl or cycloalkyl which may be substituted with alkyl),

Diarylamino (may be substituted with alkyl or cycloalkyl which may be substituted with alkyl), and

Arylheteroarylamino (may be substituted with alkyl or cycloalkyl which may be substituted with alkyl).

The substituent group ZB-3 consists of the following.

methyl,

t-amyl,

t-butyl,

Adamantyl (may be substituted with methyl),

Phenyl (may be substituted with methyl, t-amyl, t-butyl, or adamantyl (may be substituted with methyl)),

Biphenyl (may be substituted with methyl, t-amyl, t-butyl, or adamantyl (may be substituted with methyl)),

Dibenzofuranyl (may be substituted with methyl, t-amyl, t-butyl, or adamantyl (may be substituted with methyl)),

diarylamino (aryl of the diarylamino is selected from the group consisting of phenyl, biphenyl, and naphthyl, and may be substituted with alkyl or cycloalkyl which may be substituted with alkyl), and

Arylheteroarylamino (aryl of the arylheteroarylamino is selected from the group consisting of phenyl, biphenyl, and naphthyl, and heteroaryl is dibenzofuranyl, dibenzothienyl, or N-phenyl carbazolyl) selected from the group consisting of, and the aryl and the heteroaryl may be substituted with alkyl or cycloalkyl which may be substituted with alkyl).

In formula (1a-1), formula (1a-2), and formula (1a-3), Ra2 and Rb3 are preferably each independently diarylamino or arylheteroarylamino. Regarding possible substituents and preferred forms, reference can be made to the above description regarding diarylamino and arylheteroarylamino in substituent group ZB-3.

In formula (1a-1), formula (1a-2), and formula (1a-3), Rg1, Rg2, Rg3, Rg4, Rg5, Rg6, Rg7, Rg8, Rg9, Rg10, Rg11, Rg12, Rg13, and For Rg14, refer to the description of Ra in formula (G). Groups containing the g11 ring and g12 ring in formula (1a-1), formula (1a-2), and formula (1a-3) corresponding to the monovalent group represented by formula (G), and the g13 ring and g14 ring For the group included, reference can be made to the description of the monovalent group represented by the formula (G) above, and for example, the monovalent group represented by any of the formulas (G-1) to (G-52) A group in which A is >O can be exemplified. In addition, Rg1, Rg6, Rg8, and Rg13 are preferably all hydrogen, and 1 to 4 of them selected from the group consisting of Rg2, Rg5, Rg9, and Rg12 are each independently a group selected from the substituent group ZB-2. desirable.

In formula (1a-1), two adjacent ones of Rb1 to Rb4 may be bonded to each other to form an aryl ring together with the carbons to which they are bonded, and the formed aryl ring may have at least one substituent selected from the substituent group ZB. It may be substituted. As this substituent, it is preferable that it is any group selected from the said substituent group ZB-2.

In the structure in formula (1a-1), at least one of the aryl ring or heteroaryl ring may be condensed with at least one cycloalkane, and the cycloalkane may have a substituent, as described later, At least one -CH ₂ - in the cycloalkane may be substituted with -O-. However, cycloalkane is not condensed in the g11 ring and the g13 ring. It is preferable that none of the g11 ring, g12 ring, g13 ring, and g14 ring are condensed with cycloalkane.

In formula (1a-2), at least one of Ra1 to Ra3, Rb1 to Rb4, and Rc1 to Rc4 is substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, or substituted or unsubstituted diarylamino. , substituted or unsubstituted arylheteroarylamino, or substituted or unsubstituted cycloalkyl, or at least one selected from the group consisting of aryl rings and heteroaryl rings in formula (1a-2), as described later. Condensed with cycloalkanes.

When at least one of Ra1 to Ra3, Rb1 to Rb4, and Rc1 to Rc4 is the above substituent, preferably at least two of the group consisting of Ra1 to Ra3, the group consisting of Rb1 to Rb4, and the group consisting of Rc1 to Rc4. At least one group from each group of three groups, more preferably at least one group from each group of three groups, is substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino. , substituted or unsubstituted arylheteroarylamino, or substituted or unsubstituted cycloalkyl. For the preferred substituent and range of this substituent, reference can be made to the description regarding diarylamino and arylheteroarylamino in the above substituent group ZB-2.

In formula (1a-2), two adjacent ones of Rb1 to Rb4 and Rc1 to Rc4 may be bonded to each other to form an aryl ring or heteroaryl ring together with the carbons to which they are bonded. The formed aryl ring may be substituted with at least one substituent selected from the substituent group ZB. The substituent is preferably a group selected from ZB-2.

As described later, at least one of the aryl ring or heteroaryl ring in formula (1a-2) may be condensed with at least one cycloalkane, and the cycloalkane may have a substituent, and the cycloalkane may be At least one -CH ₂ - in may be substituted with -O-.

In formula (1a-3), Ra1 to Ra3, Rb1 to Rb4, Rc1 to Rc4, and Rg1 to Rg14 are each independently hydrogen or any one of the substituents selected from the substituent group ZB. Two adjacent ones of Rb1 to Rb4 and Rc1 to Rc4 may be bonded to each other to form an aryl ring or heteroaryl ring together with the carbons to which they are bonded. The formed aryl ring and heteroaryl ring may be substituted with at least one substituent selected from the substituent group ZB. The substituent is preferably a group selected from ZB-2.

As described later, at least one of the aryl ring or heteroaryl ring in the structure in formula (1a-3) may be condensed with at least one cycloalkane, and the cycloalkane may have a substituent. At least one -CH ₂ - in the cycloalkane may be substituted with -O-.

[Structure consisting of one or two or more structural units]

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 its preferred form. As a polycyclic aromatic compound having a structure consisting of one structural unit, a polycyclic aromatic compound represented by the formula described above as a 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 the multimer of the polycyclic aromatic compound represented by the formula described above as the structural unit represented by formula (1). I can hear it. As for a multimer, 2-6 mers are preferable, 2-3 mers are more preferable, and a dimer is especially preferable. The multimer may have a form 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) contained in the above structural unit is shared and bonded to a plurality of unit structures. Additionally, any rings (A ring, B ring, or C ring) contained in the above unit structure may be condensed and bonded to each other. Additionally, the unit structure may be a single bond or a plurality of bonds formed by linking groups such as alkylene, phenylene, or naphthylene having 1 to 3 carbon atoms. Among these, a form in which the rings are shared and bonded together is preferable.

[Cycloalkane condensation]

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

The cycloalkane may be any cycloalkane having 3 to 24 carbon atoms. At this time, 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 at least one of the cycloalkane -CH ₂ - may be substituted with -O-, but cycloalkanes containing all -CH ₂ - are preferred.

When the structure consisting of one or two or more structural units expressed in formula (1) is condensed with at least one cycloalkane, the at least one cycloalkane is a cycloalkane having 3 to 20 carbon atoms, and 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 cycloalkyl with 3 to 16 carbon atoms, which may be substituted.

As cycloalkanes, cycloalkanes with 3 to 24 carbon atoms are preferable, and more preferable examples include, in order, cycloalkanes with 3 to 20 carbon atoms, cycloalkanes with 3 to 16 carbon atoms, cycloalkanes with 3 to 14 carbon atoms, and cycloalkanes with 5 to 10 carbon atoms. Examples include alkanes, cycloalkanes with 5 to 8 carbon atoms, cycloalkanes with 5 to 6 carbon atoms, and cycloalkanes with 6 carbon atoms.

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, decahydroazurene, and alkyl (especially methyl) substituted products having 1 to 5 carbon atoms, halogen (especially fluorine) substituted products, and deuterium substituted products.

Among these, for example, the α-position carbon of a cycloalkane as represented by the structural formula below (in cycloalkanes 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. A structured structure is more desirable. This is to protect the chemically active site 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 that the aryl ring or heteroaryl ring has a structure in which partial structures represented by the following formulas (Z-11) and (Z-12) are bonded to adjacent carbon atoms, and formula (Z-11) This is more preferable.

In formulas (Z-11) and (Z-12), Me represents methyl and * represents the binding site.

The number of cycloalkanes condensed in 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 to 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. Condensed cycloalkanes may be condensed as shown in formula (Cy-1-4) and formula (Cy-2-4). This 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 substituted 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 any group selected from the substituent group ZB. Among these substituents, alkyl (for example, alkyl with 1 to 6 carbon atoms) and cycloalkyl (for example, cycloalkyl with 3 to 14 carbon atoms) are preferable. A structure in which any one hydrogen is replaced with halogen (for example, fluorine) or deuterium is also preferable. Additionally, 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, the A ring, B ring, and C ring (c1 ring or c2 ring) in a polycyclic aromatic compound having a structure consisting of one or two or more structural units represented by formula (1). A form in which any ring in is condensed with a cycloalkane can be mentioned.

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 in a preferred form thereof, either G _A or G _B A form in which the ring is ^condensed with a cycloalkane (however, when Aryl or heteroaryl in 1), that is, diarylamino condensed with a cycloalkane (condensed at its aryl portion), carbazolyl condensed with a cycloalkane (condensed at its benzene ring portion), or benzocarboxylic condensed with a cycloalkane. Bazolyl (condensed on its benzene ring portion), aryl as a substituent condensed with a cycloalkane, heteroaryl as a substituent condensed with a cycloalkane, aryl condensed with a cycloalkane as a partial structure of the substituent (e.g., the aryl portion of aryloxy). , an example having heteroaryl condensed with cycloalkane as a partial structure of the substituent (e.g., heteroaryl portion of diheteroarylamino) can be given.

In the polycyclic aromatic compound having a structure consisting of one or two or more structural units represented by formula (1), and its preferred form, the cycloalkane condensation is carried out in the A ring, B ring, or C ring. A form condensed to an aryl ring or heteroaryl ring is preferable, and a form condensed to an aryl ring or heteroaryl ring in the B ring or C ring is more preferable. Also, a form condensed on both the B ring and the C ring is also preferred.

On the other hand, 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. Additionally, 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 this principle. From this, in the polyaromatic compound having a structure consisting of one or two or more structural units represented by formula (1), and its preferred form, it is preferable that the above-described cycloalkane condensation is introduced.

[Substitution by deuterium, cyano, or halogen]

All or part of the hydrogen in the structure consisting of one or two or more structural units represented by formula (1) and its preferred form may be substituted with deuterium, cyano, or halogen.

For example, in the structural unit represented by formula (1) and a structure consisting of one or two or more preferred forms thereof, the A ring, B ring, C ring, substituents on A to C rings, Y ¹ When Si-R or Ge-R, R (=alkyl, cycloalkyl, aryl), and the hydrogen in G _A and G _B may be substituted with deuterium, cyano, or halogen, but among these, aryl or hetero Examples include an aspect in which all or part of the hydrogen in aryl is replaced with deuterium, cyano, or halogen. Halogen is fluorine, chlorine, bromine, or iodine, and is preferably fluorine, chlorine, or bromine, more preferably fluorine or chlorine, and fluorine is more preferable. In particular, a form in which hydrogen is replaced by deuterium is preferable because it improves the stability of the compound. It is preferable that one hydrogen is replaced with deuterium, it is more preferable that multiple hydrogens are replaced by deuterium, it is more preferable that all hydrogens in the aromatic part are replaced by deuterium, and it is most preferable that all hydrogens are replaced by deuterium. do.

[Preferred substituents]

In the polycyclic aromatic compound used as an emitting dopant (in other compounds used as a dopant), as a substituent containing “alkyl”, tertiary alkyl represented by the following formula (tR) is A ring, B ring, and It is one of the particularly preferable substituents for the aryl ring or heteroaryl ring in the C ring. 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 formula (tR), carbazolyl (preferably N-carbazolyl) substituted with tertiary alkyl represented by formula (tR), or formula and benzocarbazolyl (preferably N-benzocarbazolyl) substituted with tertiary alkyl represented by (tR). Examples of the substitution form of the group of the formula (tR) for diarylamino, carbazolyl and benzocarbazolyl include where some or all of the hydrogens of the aryl ring or benzene ring in these groups are substituted with the group of the formula (tR). You can.

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) uses * as the binding position.

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 the 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-methylpropyl, 1,1-diethylpropyl, 1,1-dimethylbutyl, and 1-ethyl-1. -Methylbutyl, 1,1,3,3-tetramethylbutyl, 1,1,4-trimethylpentyl, 1,1,2-trimethylpropyl, 1,1-dimethyl octyl, 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. Among these, t-butyl and t-amyl are preferred.

The emission wavelength can be adjusted by the structural steric hindrance, electron donating, and electron withdrawing properties of the substituent of the compound used as a dopant (assisting dopant or emitting dopant). Preferably, it is a group represented by the following structural formula, more preferably methyl, t-butyl, t-amyl, t-octyl, neopentyl, adamantyl, dimethyladamantyl, phenyl, o-tolyl, p -Tolyl, 2,4-xylyl, 2,5-xylyl, 2,6-xylyl, 2,4,6-methyl, 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 and tribenzoazepinyl. From the viewpoint of ease of synthesis, greater steric hindrance is preferable for selective synthesis, specifically, t-butyl, t-amyl, t-octyl, adamantyl, dimethyladamantyl, o-tolyl, p -Tolyl, 2,4-xylyl, 2,5-xylyl, 2,6-xylyl, 2,4,6-methyl, di-p-tolylamino, bis(p-(t-butyl)phenyl )Amino, 3,6-dimethylcarbazolyl and 3,6-di-t-butylcarbazolyl are preferred.

In the structural formula below, * represents the binding position.

A polycyclic aromatic compound having a structure containing one or two or more of the structural unit represented by formula (1) and its preferred form is tertiary alkyl (t-butyl or t-amyl) represented by the above-mentioned formula (tR). etc.), a structure containing at least one neopentyl or adamantyl, and preferably 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. As a substitution form of the group of formula (tR) for diarylamino (however, the two aryls of the diarylamino may not be bonded to each other or may be bonded through a linking group), carbazolyl, and benzocarbazolyl, Examples include where some or all of the hydrogens of the aryl ring or benzene ring in this group are substituted with a group of the formula (tR).

[Specific examples of polycyclic aromatic compounds]

Additional specific examples of the polycyclic aromatic compound represented by formula (1) of the present invention include the following compounds. Meanwhile, the following structure is an example.

<Method for producing polycyclic aromatic compounds>

The polycyclic aromatic compound of the present invention, which has a structure consisting of one or two or more structural units represented by formula (1), basically consists of first an A ring (a ring), a B ring (b ring), and a C ring ( An intermediate is prepared by combining ring c) with a linking group (a group containing NG _A or NG _B ) (first reaction), and then, ring A (ring a), ring B (ring b), and ring C (c ring). The final product can be prepared by combining 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 or Ullman reaction can be used, and if it is an amination reaction, general reactions such as Birchwald-Hartwig reaction, nucleophilic substitution reaction, or Goldberg amination can be used. can be used. Additionally, in the second reaction, a tandem hetero Friedel Crafts reaction (successive aromatic electron substitution reaction, hereinafter the same applies) can be used. Somewhere in the reaction process, the desired compound can be produced by using a raw material having the desired condensed ring or by adding a step to condense the 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 synthesizing the following intermediate 1 as a halogenated precursor and metalizing the halogen atom (Hal) between NG _A and NG _B in the following intermediate 1 using an organic alkali compound, and the halide of Y ¹ , Y ^{1 A} reaction step of ^{exchanging the metal with Y 1 using} a reagent selected from the group consisting of an aminated halide of The reaction including the reaction step of combining the B ring and the C ring with the above Y ¹ by a former electron substitution reaction is described below. The halogen atom (Hal) in the formula may be any of F, Cl, Br, and I, and can be appropriately selected in consideration of the reactivity of the substrate.

As metalizing reagents used in the halogen-metal exchange reaction in the scheme described so far, alkyl lithium such as methyl lithium, n-butyllithium, sec-butyllithium, and t-butyllithium, isopropyl magnesium chloride, and isopropyl bromide. Magnesium, phenyl magnesium chloride, phenyl magnesium bromide, and the lithium chloride complex of isopropyl magnesium chloride, known as a turbo Grignard reagent.

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

Furthermore, additives that promote the reaction when using alkyl lithium as a metalizing reagent include N,N,N',N'-tetramethylethylenediamine, 1,4-diazabicyclo[2.2.2]octane, N, N-dimethyl propylene urea, etc. can be mentioned.

In addition, the Lewis acids used in the schemes described so far include AlCl ₃ , AlBr ₃ , AlF ₃ , BF ₃ ·OEt ₂ , BCl ₃ , BBr ₃ , BI ₃ , GaCl ₃ , GaBr ₃ , InCl ₃ , InBr ₃ , 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, Me ₃ SiOTf, 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. You can. Additionally, this Lewis acid supported on a solid can also be used in the same way. Meanwhile, in the present specification, “OTf” means “trifluoromethylsulfonyl group” or trifluoromethylsulfonate.

In addition, the Brønsted acids used in the scheme described so far include p-toluene sulfonic acid, methanesulfonic acid, trifluoromethanesulfonic acid, fluorosulfonic acid, carboranic acid, trifluoroacetic acid, and (trifluoromethanesulfonyl). Examples include imide, tris(trifluoromethanesulfonyl)methane, hydrogen chloride, hydrogen bromide, and hydrogen fluoride. Additionally, examples of solid Bronsted acids include Amberlyst (brand name: Dow Chemical), Nafion (brand name: DuPont), Zeolite, and Teikacure (brand name: Teika Co., Ltd.).

In addition, amines that may be added in the scheme described so far include diisopropylethylamine, triethylamine, tributylamine, 1,4-diazabicyclo[2.2.2]octane, and N,N-dimethyl-p-toluidine. , N,N-dimethylaniline, pyridine, 2,6-lutidine, 2,6-di-t-butylamine, etc.

In addition, solvents used in the schemes described so far include o-dichlorobenzene, chlorobenzene, toluene, benzene, methylene chloride, chloroform, dichloroethylene, benzotrifluoride, decalin, cyclohexane, hexane, heptane, 1,2, Examples include 4-trimethyl benzene, xylene, diphenyl ether, anisole, cyclopentyl methyl ether, tetrahydrofuran, dioxane, and methyl-t-butyl ether.

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 obtained. It can be synthesized.

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 the aminated halide of Y ¹ or the alkoxylate of Y ¹ is used, amines and alcohols are produced as the aromatic electron substitution reaction progresses, so in many cases, there is no need to use a Brønsted base. However, since the removal ability of amino or alkoxy is low, the use of a Lewis acid that promotes the removal is effective.

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

<2. Organic Device>

The polycyclic aromatic compound according to 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 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 according to the present invention is preferably an organic electroluminescent device material, more preferably a material for a light-emitting layer (light-emitting material), and most preferably a dopant material for the light-emitting layer.

<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 ( 103) a hole transport layer 104 installed on the hole transport layer 104, a light emitting layer 105 installed on the hole transport layer 104, an electron transport layer 106 installed on the light emitting layer 105, and an electron injection layer 107 installed on the electron transport layer 106. 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 107 provided on the cathode 108. ), an electron transport layer 106 provided on the electron injection layer 107, a light emitting layer 105 installed on the electron transport layer 106, a hole transport layer 104 installed on the light emitting layer 105, and a hole transport layer 104 on the hole transport layer 104. It may be configured to include a hole injection layer 103 provided and an anode 102 provided on the hole injection layer 103.

All of the above layers are not necessary, 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) and the electron injection layer 107 are arbitrarily installed layers. 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 that represents 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, or may be used as a host material, but is preferably used as a material for an emitting layer and more preferably used as a dopant material.

On the other hand, as a dopant, there are examples in which 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, may be a combination of multiple types, or may be any of them. The dopant material may be contained in the entire host material, may be contained partially, or may be any one.

<Dopant material>

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. When multiple dopants are used in combination, specific examples of the dopant to be combined with the compound of the present invention are shown below.

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, 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 having 6 to 24 carbon atoms, heteroarylene having 2 to 24 carbon atoms, heteroarylarylene having 6 to 24 carbon atoms, and aryl having 6 to 24 carbon atoms. Lenheteroarylene arylene, arylene having 6 to 16 carbon atoms is preferable, arylene having 6 to 12 carbon atoms is more preferable, arylene having 6 to 10 carbon atoms is particularly preferable, and specifically, benzene ring, Bivalent groups such as biphenyl ring, terphenyl ring, and fluorene ring can be mentioned. As heteroarylene, heteroarylene having 2 to 24 carbon atoms is preferable, heteroarylene having 2 to 20 carbon atoms is more preferable, heteroarylene having 2 to 15 carbon atoms is still more preferable, and heteroarylene having 2 to 10 carbon atoms is more preferable. Ren is particularly preferred, 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, iso Quinoline ring, cinnoline ring, quinazoline ring, quinoxaline ring, phthalazine ring, naphthridine ring, purine ring, pteridine ring, carbazole ring, acridine ring, phenoxathione ring, phenoxazine ring, phenothiazine ring , phenazine ring, indolizine ring, furan ring, benzofuran ring, isobenzofuran ring, dibenzofuran ring, thiophene ring, benzothiophene ring, dibenzothiophene ring, furazane ring, oxadiazole ring and thiantrene ring. Bivalent groups such as these 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. Meanwhile, 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.

(mCP)

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 mass% of the total light emitting layer material, more preferably 80 to 99.95 mass%, and still more preferably 90 to 99.9 mass%.

<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, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino, optionally substituted diheteroarylamino, substituted or unsubstituted Arylheteroarylamino, substituted or unsubstituted alkyl, optionally substituted cycloalkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted arylthio, or It is a substituted ^silyl , and not all are not bonded to each other or are bonded to each other through a single bond or linking group, and the aryl and heteroaryl of the arylheteroarylamino are not bonded to each other or are bonded to each other through a single bond or linking group.

At least one hydrogen in the compound represented by formula (3-H) is substituted with halogen, cyano, deuterium, optionally substituted heteroaryl, or is not substituted.

Additionally, a multimer (preferably a dimer) 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 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 definition of the symbols in the following structure is the same as the above-mentioned definition.

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 dimer) 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 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 structure condensed in this way is as follows.

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

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

In addition, Ar ³ may have a substituent, and at least one hydrogen in Ar ³ is further selected from alkyl with 1 to 4 carbon atoms, cycloalkyl with 5 to 10 carbon atoms, phenyl, biphenylyl, terphenylyl, and naphthyl. , phenanthryl, fluorenyl, chrysenyl, triphenylenyl, pyrenyl, or a group represented by formula (A) (including carbazolyl groups and phenyl-substituted carbazolyl groups). 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, alkyl with 1 to 4 carbon atoms (methyl, ethyl, t-butyl, etc.), and/or cycloalkyl with 5 to 10 carbon atoms. It is a substituted silyl.

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. , it is 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(norbornyl), bicyclo[2.2.2]octyl, adamantyl, decahydronaphtharenyl, decahydro Azrenyl, etc. are mentioned, and the three hydrogens in silyl are each independently substituted with this cycloalkyl.

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

Substituted silyl includes dialkylcycloalkylsilyl in which two alkyls and one cycloalkyl are substituted, and alkyldicycloalkylsilyl in which one alkyl and two cycloalkyls are substituted, 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 *.

The group represented by formula (A) is one of the substituents that the anthracene-based compound represented by formula (3-H) and the anthracene-based compound represented by formula (3-H2) described later can 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 adjacent groups among R ²¹ to R ²⁸ may be combined 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 straight chain or branched chain, 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 preferred, and alkyl with 1 to 4 carbon atoms (branched chain alkyl with 3 to 4 carbon atoms) is particularly preferred.

Specific examples of “alkyl” include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl, n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, t-octyl, 1-methylheptyl, 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 cycloalkyl with 3 to 24 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 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( norbornyl), bicyclo[2.2.2]octyl, adamantyl, diamantyl, decahydronaphtharenyl, decahydroazrenyl, etc.

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

Specific examples of “aryl” include monocyclic phenyl, bicyclic biphenylyl, condensed bicyclic naphthyl, tricyclic terphenylyl (m-terphenylyl, o-terphenylyl, p-terphenylyl), Acenaphthylenyl, fluorenyl, phenalenyl, and phenanthryl, 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 constituent atoms.

Specific examples of “heteroaryl” include pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, pyrazolyl, and pyrazolyl. Dill, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, indolyl, isoindolyl, 1H-indazolyl, benzoimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolyl, Isoquinolyl, cinnolyl, quinazolyl, quinoxalinyl, phthalazinyl, naphthyridinyl, furinyl, pteridinyl, carbazolyl, acridinyl, phenoxathiinyl, phenoxazinyl, phenothiazinyl, Phenazinyl, indolizinyl, furyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, thienyl, benzo[b]thienyl, dibenzothienyl, furazanyl, thianthrenyl, naphthobenzofranyl. , 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 alkoxy with 3 to 18 carbon atoms) is preferable, alkoxy with 1 to 12 carbon atoms (branched alkoxy with 3 to 12 carbon atoms) is more preferable, and alkoxy with 1 to 6 carbon atoms (branched alkoxy with 3 to 12 carbon atoms) is more preferable. Branched alkoxy with 3 to 6 carbon atoms) is more preferable, and alkoxy with 1 to 4 carbon atoms (branched alkoxy with 3 to 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 preferred 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, decahydronaph. Talenyl, 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.

Examples of the “substituted amino” of “optionally substituted amino” for R ²¹ to R ²⁸ include an amino group 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 linking group) substituted amino, 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, and 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 may be cited as substituents for R ²¹ to R ²⁸ .

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). . Y and * in the formula have the same definitions as above. 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. As an aryl ring or heteroaryl ring, “aryl” or “heteroaryl” for R ²¹ to R ²⁸ described above can be used. Examples include the ring structures described above, 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 of two benzene rings in the structure of formula (A), any one ring atom formed by bonding adjacent groups among R ^{21 to} R ²⁸ in the structure of formula (A). , or directly bonded to any position of R ²⁹ in “>NR ₂₉ ” as Y in the structure of formula (A), or with N in “>NR ²⁹ ” (R ²⁹ becomes the bonding hand) It can be a time to do it. 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 formula (A-14), formulas (A-1) to formula (A-5), and A group represented by any one of formulas (A-12) to formulas (A-14) is preferred, a group represented by any of formulas (A-1) to formulas (A-4) is more preferred, and formulas (A-1) ), a group represented by any one of formulas (A-3) and formula (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 form bonded to any one of Ar3 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 ( Aryl and heteroaryl 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, alkoxy which may be substituted, It is optionally aryloxy, optionally substituted arylthio, or optionally substituted silyl, and at least one hydrogen in the compound represented by formula (3-H2) 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 (aryl and heteroaryl 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 quoted.

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). Meanwhile, 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, It is biphenylyl, terphenylyl, naphthyl, phenanthryl, fluorenyl, chrysenyl, triphenylenyl, pyrenyl, or a group represented by formula (A). In addition, 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 those represented by formula (A). and terphenylyl (particularly m-terphenyl-5'-yl), which may be substituted with one or more substituents selected from the group consisting of:

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 (3-H2) 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 the formula (3-H2) preferably has a structure in which at least three substituents selected from the group consisting of optionally substituted aryl and optionally substituted heteroaryl are bonded to the anthracene ring.

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 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 the 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, is replaced with methyl or t-butyl instead of hydrogen. These 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 -1) It may be substituted with a group represented by any one of formulas (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, a form in which all anthracene rings are deuterated, or a form in which all hydrogen atoms are deuterated is preferable.

In particular, a preferred 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 formulas (A-1) to (A-11) above, 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 of 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) ~ It may be substituted with a group represented by any one of formulas (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). Meanwhile, 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) Examples include compounds represented by the formula (3-626-Y). The hydrogen atoms in these formulas may be partially or entirely substituted with deuterium, but particularly preferred forms of deuterium substitution are listed individually. 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, the formula (3-131-Y) is called formula (3-131-O), and when Y is -S- or >NR ²⁹ , the formula is (3-131-Y). -131-S) or formula (3-131-N).

In the above formula, D is deuterium.

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)~formula (3-156-Y), formula (3-166-Y), formula (3-168-Y), formula (3-173- Y), formula (3-177-Y), formula (3-180-Y) ~ 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-. Additionally, the form of deuterium substitution is also preferable.

The anthracene compound is a compound having a reactive group at a desired position of the anthracene skeleton, and if it is an anthracene compound represented by formula (3-H), it has a reactive group in partial structures such as X, Ar ⁴ and the structure of formula (A). Using the compound as a starting material, it can be produced by applying Suzuki coupling, Negishi coupling, or 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, or 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 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 on the definition of formula (4-H), the above-mentioned description of the polycyclic aromatic compound of formula (1) can be cited.

Examples of alkenyl for R ¹ to R ¹⁰ include alkenyl having 2 to 30 carbon atoms, alkenyl having 2 to 20 carbon atoms is preferable, and alkenyl having 2 to 10 carbon atoms is 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) A monovalent group expressed by removing two hydrogen atoms can 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 the formula ( At least one hydrogen in the structures of formulas 4-Ar1) to (4-Ar5) may be substituted with phenyl, biphenylyl, naphthyl, anthracenyl, phenanthryl, methyl, ethyl, propyl, or butyl. .

These heteroaryls may be bonded to the fluorene skeleton in the above 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), Each is a compound in which R ⁹ and R ¹⁰ are bonded to form a spiro-fluorene ring in formula (4-H-1), formula (4-H-2) or formula (4-H-3).

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

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. Meanwhile, “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 may be bonded to the dibenzochrysene skeleton in formula (5-H) through a linking group), or 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 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, cycloalkyl, alkenyl, alkoxy, or aryloxy, and at least one hydrogen in these is aryl, heteroaryl, It may be substituted with alkyl or cycloalkyl,

Additionally, 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 is aryl or heteroaryl (the heteroaryl is bonded to the formed ring 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) may be substituted), arylheteroarylamino (aryl and heteroaryl may not be bonded to each other, or may be bonded through a single bond or linking group), alkyl, cycloalkylalkenyl, alkoxy, or aryloxy; At least one hydrogen may be substituted with aryl, heteroaryl, alkyl, or cycloalkyl, and at least one hydrogen in the compound represented by formula (5-H) 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 having 2 to 30 carbon atoms, preferably alkenyl having 2 to 20 carbon atoms, and alkenyl having 2 to 10 carbon atoms. This is more preferable, alkenyl having 2 to 6 carbon atoms is further 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 (5-Ar1), (5-Ar2), (5-Ar3), (5-Ar4), or (5-Ar5) A monovalent group expressed by removing two hydrogen atoms can 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 the formula ( At least one hydrogen in the structures of 5-Ar1) to (5-Ar5) may be substituted with phenyl, biphenylyl, naphthyl, anthracenyl, phenanthryl, 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, phenanthryl, a monovalent group having the structure of formula (5-Ar1), formula (5-Ar2), formula (5-Ar3), formula (5-Ar4) or formula (5-Ar5) (the structure The monovalent group having 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 the above formula (5-H)), and is preferably methyl, ethyl, propyl, or butyl.

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, Biphenylene, naphthylene, anthracenylene, methylene, ethylene, -OCH ₂ CH ₂ -, -CH ₂ CH ₂ O-, or -OCH ₂ CH ₂ O-, above formula (5-Ar1), It is a monovalent group having the structure of formula (5-Ar2), formula (5-Ar3), formula (5-Ar4), or formula (5-Ar5),

Other than at least one of the above (i.e., other than the position where the monovalent group having the above structure is substituted) is hydrogen, phenyl, biphenylyl, naphthyl, anthracenyl, methyl, ethyl, propyl, or butyl, and At least one hydrogen may be substituted with phenyl, biphenylyl, naphthyl, anthracenyl, methyl, ethyl, propyl, or butyl.

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 the above 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 dibenzochrysene compounds as hosts include compounds represented by the following structural formulas.

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 reacted with the reactive compound. The pendant-type polymer compound or its pendant-type polymer crosslinked product can also be used as a material for the light-emitting layer. As the 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 a first component, an assisting dopant (compound) as a second component, and an emitting dopant (compound) as a third component. The polycyclic aromatic compound of the present invention 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 “TAF device” (TADF Assisting Fluorescence device). The “host compound” in a TAF device 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.

“Thermal-activated delayed phosphor” is a substance that absorbs heat energy to cause reverse intersystem crossing from the lowest triplet excitation state to the lowest singlet excitation state, and is deactivated by radiation from the lowest singlet excitation state to emit delayed fluorescence. means a compound. However, “thermally activated delayed fluorescence” also includes passing through a higher-order triplet during the excitation process from the lowest triplet excited state to the lowest 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 Graduate School), 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 (manufactured by Hamamatsu Photonics, C11367-01).

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, E(1,G) is the energy level of the ground state of the host, E(1,S,Sh) is the lowest excitation singlet energy level obtained from the shoulder of the short wavelength side of the fluorescence spectrum of the host, and E(1,S,Sh) is the phosphorescence spectrum of the host. The lowest excitation triplet energy level obtained from the shoulder of the short wavelength side 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 second component, assisting dopant, is E(1,T,Sh). The lowest excitation singlet energy level obtained from the short-wavelength shoulder of the fluorescence spectrum of the sting dopant is E(2,S,Sh), and the lowest excitation triplet energy level obtained from the short-wavelength shoulder of the phosphorescence spectrum of the assisting dopant, which is the second component, is E(2,S,Sh). The term energy level is E(2,T,Sh), the energy level of the ground state of the third component, the emitting dopant, is E(3,G), and from the shoulder of the short wavelength side of the fluorescence spectrum of the third component, the emitting dopant. The lowest singlet excitation energy level obtained is E(3,S,Sh), and the lowest triplet excitation energy level obtained from the short-wavelength shoulder of the phosphorescence spectrum of the emitting dopant, which is the third component, is E(3,T,Sh). ), holes are h+, electrons are e-, and 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 singlet excitation energy level E(3,S,Sh) of the emitting dopant and emits light. do. However, some of the lowest excitation triplet energy levels E(2,T,Sh) on the assisting dopant move to the lowest excitation triplet energy level E(3,T,Sh) on the emitting dopant, or An intersystem crossing occurs from the singlet excited energy level E(3,S,Sh) to the lowest triplet excited energy level E(3,T,Sh), and continues thermally to the ground state E(3,G). become deactivated by Due to this path, some 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.

A preferable energy relationship in the organic electroluminescent device of this embodiment is shown in Figure 3. 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). For this reason, the singlet excitation energy upconverted in the assisting dopant is either upconverted on the emitting dopant, even if it intersects to the lowest triplet excitation energy level E(3,T,Sh) in the emitting dopant. , 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. Additionally, by dividing the upconversion and light emission functions into two types of molecules that can each perform well, 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 hetero arylene 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. It is preferable that the emitting dopant or assisting dopant having a high lowest triplet excitation energy level is higher than the lowest excitation triplet energy level E(2,T,Sh), E(3,T,Sh), specifically. The lowest triplet excitation energy level E(1,T,Sh) of the host compound is preferably 0.01 eV or more, compared to E(2,T,Sh) and E(3,T,Sh), and is 0.03 eV. 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 form 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 allow efficient reverse intersystem crossing. Here, in this specification, the “electron-donating substituent” (donor) refers to the substituent and partial structure where LUMO is localized in the heat-activated delayed phosphor molecule, and the “electron-accepting substituent” (acceptor) refers to the heat-activated delayed phosphor molecule. This refers to the substituent and partial structure where HOMO is localized among the activated delayed fluorescent substance molecules.

In general, thermally activated delayed phosphors using donors or acceptors have large spin orbit coupling (SOC) due to their structure, and also have small exchange interactions between HOMO and LUMO and small ΔE(ST). Therefore, a very fast inverse intersystem crossing speed is obtained. On the other hand, thermally activated delayed phosphors using donors or acceptors have large 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 for 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, dacarbazole, diphenylcarbazolylamine, tetraphenylcarbazolyldiamine, phenoxazine, dihydrophenazine, phenothiazine, dimethyldihydroacridine, diphenylamine, bis. (tert-butylphenyl)amine, N1-(4-(diphenyl amino)phenyl)-N4,N4-diphenylbenzene-1,4-diamine, dimethyltetraphenyldihydroacridinediamine, tetramethyl-dihydro Examples include indenoacridine and diphenyldihydrodibenzoazacillin. Acceptor structures include sulfonyl dibenzene, benzophenone, phenylenebis (phenylmethanone), benzonitrile, isonicotinonitrile, phthalonitrile, isophthalonitrile, paraphthalonitrile, benzene tricarbonitrile, and triazole. , oxazole, thiadiazole, benzothiazole, benzobis (thiazole), benzoxazole, benzobis (oxazole), quinoline, benzimidazole, dibenzoquinoxaline, heptaazaphenalene, thioxanthone diox Seed, dimethylanthracenone, anthracenedione, 5H-cyclopenta[1,2-b:5,4-b']dipyridine, fluorene dicarbonitrile, trisphenyltriazine, pyrazine dicarbonitrile, pyrimidine, phenyl Examples include pyrimidine, methylpyrimidine, pyridinedicarbonitrile, dibenzoquinoxaline dicarbonitrile, bis(phenylsulfonyl)benzene, dimethylthioxanthene dioxide, thianthrenetetroxide, and tris(dimethylphenyl)borane. You can. 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, It is preferable that it is a compound having at least one selected from isophthalonitrile, diphenylsulfone, triazole, oxadiazole, thiadiazole and benzophenone.

The compound used as the second component of the light-emitting layer in the TAF device is preferably a heat-activated delayed phosphor 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 heat-activated delayed phosphors in TAF devices are not limited to the following exemplary compounds. In the formula below, the wavy line indicates the binding position.

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

In the above formula (AD1), formula (AD2) and formula (AD3),

M is, each independently, a single bond, -O-, >N-Ar or >CAr ₂ , in terms of the depth of the HOMO of the partial structure it forms and the height of the lowest singlet excitation energy level and the lowest triplet excitation energy level. , preferably a single bond, -O- or >N-Ar. J is a spacer structure that divides the partial structure of the donor and the acceptor, and is each independently an arylene with 6 to 18 carbon atoms, from the perspective of the size of the conjugate estimated from the partial structure of the donor and the acceptor. , arylene with 6 to 12 carbon atoms is preferred. More specifically, examples include phenylene, methylphenylene, and dimethylphenylene. 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. is =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. From the viewpoint 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 6 to 10 carbon atoms. cycloalkyl, more preferably hydrogen, phenyl, tolyl, xylyl, mesityl, biphenyl, pyridyl, bipyridyl, triazinyl, carbazolyl, dimethylcarbazolyl, di-tert-butylcarboxyl. It is bazolyl, benzimidazole or phenylbenzimidazole, and 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. Additionally, at least one hydrogen in the compounds represented by each of the above formulas may be substituted with halogen or deuterium.

The compounds used as the second component of the light emitting layer of the present embodiment are, more specifically, 4CzBN, 4CzBN-Ph, 5CzBN, 3Cz2DPhCzBN, 4CzIPN, 2PXZ-TAZ, Cz-TRZ3, BDPCC-TPTA, MA-TA, PA- Preferred are 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 of the light-emitting layer of the present 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. It is preferable to have a structure represented by the following formula (DAD1) in which a plurality of donors D are bonded to the acceptor A 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-mentioned 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 divides 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. In the formula (DAD1), n is 2 or more and represents an integer less than or equal to the maximum number that A ¹ can be substituted for. 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 used in the present invention is not limited to these compounds.

In this aspect, the light emitting layer may be made of a single layer or multiple layers. Additionally, the host compound, the thermally activated delayed phosphor, and the compound having a boron atom may be contained in the same layer, or may be contained in at least one component each in multiple layers. The host compound, the heat-activated delayed phosphor, and the polycyclic aromatic compound of the present invention contained in the light-emitting layer may be one type or a combination of multiple types. The assisting dopant and the emitting dopant may be contained entirely or partially in the host compound as 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. The host compound, the assisting dopant, and the emitting dopant are mixed in advance and then deposited 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 (heat-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 even 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 the emitting dopant (compound having a boron atom) used varies depending on the type of the 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 be used at a low concentration to prevent concentration quenching phenomenon. It is desirable for the efficiency of the heat-activated delayed fluorescent device to use a high concentration of the assisting dopant. Additionally, in terms of efficiency of the assisting dopant thermally activated delayed fluorescence device, it is preferable that the emitting dopant is used at a low concentration compared to the assisting dopant.

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

The substrate 101 is a support for the organic electroluminescent device 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 is sufficient to maintain mechanical strength, so for example, it may 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 preferable since it is better to have fewer ions eluted from the glass. However, soda-lime glass coated with a barrier coating such as SiO ₂ is also commercially available and can be used. Additionally, in order to increase the gas barrier property, a gas barrier film such as a dense silicon oxide film may be formed on at least one side of the substrate 101. 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. Meanwhile, when at least one of the hole injection layer 103 and the hole transport layer 104 is installed between the anode 102 and the light-emitting layer 105, holes are injected into the light-emitting layer 105 through them.

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, the material can be appropriately selected and used as an anode for organic electroluminescent 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 300 Ω/□ or less functions as a device electrode, but currently, it is also possible to supply a substrate of about 10 Ω/□, so for example, 100 to 5 Ω/□, preferably 50 to 5 Ω/□. It is especially desirable to use a low resistance product of □. The thickness of ITO can be selected arbitrarily according to the resistance value, but it is often used 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, hole injection layers of organic electroluminescent devices, and Any compound can be selected and used among known compounds used in the hole 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 (polymers 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-carbazol-3-yl)-[1,1'-biphenyl]-4,4 '-diamine, N4,N4,N4',N4'-tetra[1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4,4'-diamine, 4,4 Triphenylamine derivatives such as ',4"-tris(3-methylphenyl(phenyl)amino)triphenylamine, starburst amine derivatives, etc.), stilbene derivatives, phthalocyanine derivatives (metal-free, copper phthalocyanine, etc.), pyrazoline derivatives , hydrazone compounds, benzofuran derivatives, 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 polymer systems, polycarbonate, styrene derivatives, polyvinylcarbazole, polysilanes, etc. having the above-mentioned monomer in the side chain are preferred. However, there is no particular limitation as long as it is a compound that forms a thin film necessary for manufacturing a light-emitting device, can inject holes from the anode, and can transport holes.

Additionally, it is known that the conductivity of organic semiconductors is strongly influenced by their doping. This 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. Pheiffer, T. Fritz, K. Leo, Appl. Phys. Lett., 73(6), 729-731 (1998). These generate so-called holes by 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 (in particular, zinc phthalocyanine (ZnPc), etc.) are known (Japanese Patent Laid-Open). 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. Electron 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 devices>

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 and mixing one or two or more types of electron transport/injection materials, 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 the main role is to effectively prevent holes from the anode from flowing to the cathode without recombining, the effect of improving luminous efficiency even if the electron transport ability is not very high. It has the same electron transport capacity as a material with high electron transport capacity. Therefore, the electron injection/transport layer in this embodiment may also include a layer function 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 known compounds in use.

Materials used in the electron transport layer or electron injection layer include compounds made 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, perrinone derivatives, coumarin derivatives, and naphthalimide derivatives. , quinone derivatives such as anthraquinone and diphenoquinone, phosphine oxide derivatives, carbazole derivatives, and indole derivatives. Examples of metal complexes having electron-accepting nitrogen include hydroxyazole complexes such as hydroxyphenyloxazole complex, azomethine complex, tropolone metal complex, flavonol metal complex, and benzoquinoline metal complex. These materials can be used alone, but may be mixed with other materials.

In addition, as specific examples of other electron transfer compounds, pyridine derivatives, naphthalene derivatives, fluoranthene derivatives, BO-based derivatives, phenanthroline derivatives, perrinone derivatives, coumarin derivatives, naphthalimide derivatives, anthraquinone derivatives, and diphenol derivatives. Quinone derivatives, diphenylquinone derivatives, perylene derivatives, oxadiazole derivatives (1,3-bis[(4-t-butylphenyl)1,3,4-oxadiazolyl]phenylene, etc.), thiophene 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, quinoxaline Derivative polymers, benzazole compounds, gallium complexes, pyrazole derivatives, perfluorinated phenylene derivatives, triazine derivatives, pyrazine derivatives, benzoquinoline derivatives (2,2'-bis(benzo[h]quinolin-2-yl )-9,9'-spirobifluorene, etc.), imidazopyridine derivatives, borane derivatives, benzoimidazole derivatives (tris(N-phenylbenzoimidazol-2-yl)benzene, etc.), benzoxazole derivatives, thia Sol derivatives, benzothiazole derivatives, quinoline derivatives, oligopyridine derivatives such as terpyridine, bipyridine derivatives, terpyridine derivatives (1,3-bis(2,2':6'2"-terpyridin-4'-yl )benzene, etc.), naphthyridine derivatives (bis(1-naphthyl)-4-(1,8-naphthyridin-2-yl)phenylphosphine oxide, etc.), aldazine derivatives, pyrimidine derivatives, arylnitrile derivatives, Examples include indole derivatives, phosphine oxide derivatives, bistyryl derivatives, sirole derivatives, and azoline derivatives.

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 tropolone 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, and quinolinol-based metal complexes, thiazole derivatives, benzothiazole derivatives, sirole 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 electron injection layer may further contain a substance capable of reducing the material forming the electron transport layer or electron injection layer. Various reducing substances are used as long as they have a certain reducing property, for example, alkali metals, alkaline earth metals, rare earth metals, oxides of alkali metals, halides of alkali metals, oxides of alkaline earth metals, alkaline earth metals. At least one selected from the group consisting of halides, oxides of rare earth metals, halides of rare earth metals, organic complexes of alkali metals, organic complexes of alkaline earth metals and organic complexes of rare earth metals can be preferably used.

Preferred reducing substances include alkali metals such as Na (work function 2.36 eV), K (work function 2.28 eV), Rb (work function 2.16 eV), or Cs (work function 1.95 eV), Ca (work function 2.9 eV), Examples include alkaline earth metals such as Sr (work function 2.0-2.5 eV) or Ba (work function 2.52 eV), and those 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, 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 electroluminescent 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 of these alkali metals is also preferable, and in particular, a combination containing Cs, for example, Cs and Na, Cs and K, Cs and Rb, or Cs and 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 can be improved.

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

The cathode 108 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, lithium, sodium, potassium, cesium, calcium, magnesium or alloys containing these low work function metals are effective. However, these low work function metals are generally unstable in the atmosphere. To improve this point, there is a known method of using a highly stable electrode by doping a trace 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, and vinyl chloride , hydrocarbon-based polymer compounds, etc. are laminated as a preferable 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 form each layer individually, but may be used as a polymer binder such as 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 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 to do so.

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

Each layer constituting the organic EL device is made by using a method such as vapor deposition, resistance heating deposition, electron beam deposition, sputtering, molecular stacking, printing, inkjet, spin coat or cast, coating, etc. It can be formed by forming a thin film using this method. 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~+400℃, vacuum degree 10 ^-6 ~10 ^-3 Pa, deposition speed 0.01~50㎚/sec, substrate temperature -150~+300℃, film thickness 2㎚~5㎛. 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 composed of a dopant material will be described. do. 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 deposition method or the like to serve as a cathode. By doing so, the desired organic EL device is obtained. In addition, in manufacturing the organic EL device described above, it is also possible to reverse the manufacturing order and manufacture 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 element obtained in this way, the anode should be + and the cathode should be applied with the polarity of -. When a voltage of about 2 to 40 V is applied, the transparent or translucent electrode side (anode or cathode and Light emission can be observed from both sides. 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. You can use it to run it.

Examples of the display device include panel displays such as a color flat panel display, and flexible displays such as a flexible color organic electroluminescence (EL) display (for example, Japanese Patent Application Laid-Open No. 10-335066, See Japanese Patent Laid-Open No. 2003-321546, Japanese Patent Laid-Open 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 PCs, 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 are used. do. In the case of monochrome display, pixels of the same color can be arranged, but in the case of color display, red, green, and blue pixels are displayed in a row. In this case, there are typically delta types and stripe types. The driving method for 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 operating characteristics, the active matrix is sometimes superior, so it also needs to be used differently 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 displays, etc. (e.g., 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 reduce the thickness of the backlight for liquid crystal display devices, especially for PCs, where thinning is an issue because the conventional method consists of a fluorescent lamp or a light guide plate, a backlight using an organic EL element must be 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, organic thin film solar cells, etc. 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.

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 the 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 structures.

(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 multicolor 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 device 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 is 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. Using the wavelength conversion material containing the polycyclic aromatic compound of the present invention, light from a light source or light-emitting device that generates ultraviolet light or blue light of a shorter wavelength is transmitted to a display device (a display device or a liquid crystal display device using an organic EL device). 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 substituent of the polycyclic aromatic compound 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, in addition to the polycyclic aromatic compound of the present invention, a binder resin, other additives, and a solvent. As the binder resin, for example, those described in paragraphs 0173 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 the composition for wavelength conversion. As a method of producing a wavelength conversion layer from a composition for wavelength conversion, a known film forming method may be referred to. The wavelength conversion film may consist only of a wavelength conversion layer formed from a composition containing the polycyclic aromatic compound of the present invention, or another wavelength conversion layer (for example, a wavelength conversion layer that converts blue light into green light or red light, It may also contain a wavelength conversion layer that converts to red light. Furthermore, 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.

In the examples, “APCI-MS” refers to atmospheric pressure chemical ionization mass spectrometry.

Synthesis Example (1): Synthesis of Compound (1-1)

Under nitrogen atmosphere, intermediate (X-1) (138.7g), 1-t-butyl-3,4,5-trichlorobenzene (65.6g), and dichlorobis[di-t-butyl(4-dimethyl) as palladium catalyst. Aminophenyl) phosphino] palladium (II) (Pd-132) (9.78 g), sodium-t-butoxide (NaOtBu, 39.8 g) and toluene (500 ml) were placed in a flask and heated at 120°C for 5 hours. After completion of the reaction, 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 by silica gel short pass column (eluent: heptane) to obtain 116.5 g of intermediate (X-2).

Under a nitrogen atmosphere, intermediate (X-2) (116.5g), intermediate (X-3) (70.5g), Pd-132 (5.86g) as a palladium catalyst, NaOtBu (23.86g), and toluene (500ml) were added to the flask. and heated at 120°C for 3 hours. After completion of the reaction, 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 by silica gel short pass column (eluent: toluene/heptane = 1/9 (volume ratio)) to obtain 97.7 g of intermediate (X-4).

In a flask containing intermediate (X-4) (10.3 g) and tert-butylbenzene (tBu-benzene, 100 ml), 1.60M tert-butyllithium pentane solution (tBuLi, 11.8 ml) was added at 0°C under a nitrogen atmosphere. added. After completion of the dropwise addition, 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 (4.72 g) was added, the temperature was raised to room temperature, and the mixture was stirred for 0.5 hours. After that, it was cooled to 0°C again, N,N-diisopropylethylamine (EtNiPr ₂ , 2.44 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 an aqueous solution of sodium acetate cooled in an ice bath and then ethyl acetate were 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 3.01 g of compound (1-1).

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

¹ H-NMR (500MHz, CDCl ₃ ): δ=0.38(s, 3H), 0.79(s, 9H), 0.85(s, 3H), 1.26(s, 3H), 1.30(s, 3H), 1.44- 1.62 (m, 4H), 6.08-6.15(m, 2H), 6.36-6.42(m, 2H), 6.77-6.93(m, 10H), 6.99-7.02(m, 1H), 7.18-7.25(m, 3H) ), 7.33-7.51(m, 6H), 7.58(dt, 2H), 7.62-7.71(m, 3H), 7.84(s, 1H), 7.93-7.96(m, 2H), 8.03-8.08(m, 1H) ), 8.28-8.31(m, 1H), 8.64(dd, 1H).

Synthesis Example (2): Synthesis of Compound (1-2)

Compound (1-2) was obtained in the same manner as in Synthesis Example 1 except that compound (X-4) was changed to compound (X-4-2).

m/z(M+H)=1066.46 was observed by APCI-MS, and production of the target compound (1-2) was confirmed.

Synthesis Example (3): Synthesis of Compound (1-6)

Compound (1-6) was obtained in the same manner as in Synthesis Example 1 except that compound (X-4) was changed to compound (X-4-6).

m/z(M+H)=990.43 was observed by APCI-MS, and production of the target compound (1-6) was confirmed.

Synthesis Example (4): Synthesis of Compound (1-30)

Compound (1-30) was obtained in the same manner as in Synthesis Example 1 except that compound (X-4) was changed to compound (X-4-30).

m/z(M+H)=936.38 was observed by APCI-MS, and production of the target compound (1-30) was confirmed.

Synthesis Example (5): Synthesis of Compound (1-46)

Compound (1-46) was obtained in the same manner as in Synthesis Example 1 except that compound (X-4) was changed to compound (X-4-46).

m/z(M+H)=1090.46 was observed by APCI-MS, and production of the target compound (1-46) was confirmed.

Synthesis Example (6): Synthesis of Compound (1-48)

Compound (1-48) was obtained in the same manner as in Synthesis Example 1 except that compound (X-4) was changed to compound (X-4-48).

m/z(M+H)=1118.49 was observed by APCI-MS, and production of the target compound (1-48) was confirmed.

Synthesis Example (7): Synthesis of Compound (1-49)

Compound (1-49) was obtained in the same manner as in Synthesis Example 1 except that compound (X-4) was changed to compound (X-4-49).

m/z(M+H)=1118.49 was observed by APCI-MS, and production of the target compound (1-49) was confirmed.

Synthesis Example (8): Synthesis of Compound (1-56)

Compound (1-56) was obtained in the same manner as in Synthesis Example 1 except that compound (X-4) was changed to compound (X-4-56).

m/z(M+H)=1042.46 was observed by APCI-MS, and production of the target compound (1-56) was confirmed.

Synthesis Example (9): Synthesis of Compound (1-80)

Compound (1-80) was obtained in the same manner as in Synthesis Example 1 except that compound (X-4) was changed to compound (X-4-80).

m/z(M+H)=1050.48 was observed by APCI-MS, and production of the target compound (1-80) was confirmed.

Synthesis Example (10): Synthesis of Compound (1-81)

Compound (1-81) was obtained in the same manner as in Synthesis Example 1 except that compound (X-4) was changed to compound (X-4-81).

m/z(M+H)=1050.48 was observed by APCI-MS, and production of the target compound (1-81) was confirmed.

Synthesis Example (11): Synthesis of compound (1-84)

Compound (1-84) was obtained in the same manner as in Synthesis Example 1 except that compound (X-4) was changed to compound (X-4-84).

m/z(M+H)=996.44 was observed by APCI-MS, and production of the target compound (1-84) was confirmed.

Synthesis Example (12): Synthesis of Compound (1-102)

Compound (1-102) was obtained in the same manner as in Synthesis Example 1 except that compound (X-4) was changed to compound (X-4-102).

m/z(M+H)=1106.55 was observed by APCI-MS, and production of the target compound (1-102) was confirmed.

Synthesis Example (13): Synthesis of Compound (1-113)

Compound (1-113) was obtained in the same manner as in Synthesis Example 1 except that compound (X-4) was changed to compound (X-4-113).

m/z(M+H)=1100.67 was observed by APCI-MS, and production of the target compound (1-113) was confirmed.

Synthesis Example (14): Synthesis of Compound (1-117)

Compound (1-117) was obtained in the same manner as in Synthesis Example 1 except that compound (X-4) was changed to compound (X-4-117).

m/z(M+H)=1138.74 was observed by APCI-MS, and production of the target compound (1-117) was confirmed.

Synthesis Example (15): Synthesis of compound (1-118)

Compound (1-118) was obtained in the same manner as in Synthesis Example 1 except that compound (X-4) was changed to compound (X-4-118).

m/z(M+H)=955.45 was observed by APCI-MS, and production of the target compound (1-118) was confirmed.

Synthesis Example (16): Synthesis of Compound (1-123)

Compound (1-123) was obtained in the same manner as in Synthesis Example 1 except that compound (X-4) was changed to compound (X-4-123).

m/z(M+H)=825.37 was observed by APCI-MS, and production of the target compound (1-123) was confirmed.

Synthesis Example (17): Synthesis of Compound (1-130)

Compound (1-130) was obtained in the same manner as in Synthesis Example 1 except that compound (X-4) was changed to compound (X-4-130).

m/z(M+H)=1007.48 was observed by APCI-MS, and production of the target compound (1-130) was confirmed.

Synthesis Example (18): Synthesis of Compound (1-134)

Compound (1-134) was obtained in the same manner as in Synthesis Example 1 except that compound (X-4) was changed to compound (X-4-134).

m/z(M+H)=889.40 was observed by APCI-MS, and production of the target compound (1-134) was confirmed.

Synthesis Example (19): Synthesis of Compound (1-139)

Compound (1-139) was obtained in the same manner as in Synthesis Example 1 except that compound (X-4) was changed to compound (X-4-139).

m/z(M+H)=939.47 was observed by APCI-MS, and production of the target compound (1-139) was confirmed.

Synthesis Example (20): Synthesis of compound (1-153)

Compound (1-153) was obtained in the same manner as in Synthesis Example 1 except that compound (X-4) was changed to compound (X-4-153).

m/z(M+H)=991.50 was observed by APCI-MS, and production of the target compound (1-153) was confirmed.

Synthesis Example (21): Synthesis of Compound (1-161)

Compound (1-161) was obtained in the same manner as in Synthesis Example 1 except that compound (X-4) was changed to compound (X-4-161).

m/z(M+H)=980.61 was observed by APCI-MS, and production of the target compound (1-161) was confirmed.

Synthesis Example (22): Synthesis of compound (1-164)

Compound (1-164) was obtained in the same manner as in Synthesis Example 1 except that compound (X-4) was changed to compound (X-4-164).

m/z(M+H)=1009.50 was observed by APCI-MS, and production of the target compound (1-164) was confirmed.

Synthesis Example (23): Synthesis of compound (1-173)

Compound (1-173) was obtained in the same manner as in Synthesis Example 1 except that compound (X-4) was changed to compound (X-4-173).

m/z(M+H)=1061.53 was observed by APCI-MS, and production of the target compound (1-173) was confirmed.

Synthesis Example (24): Synthesis of compound (1-174)

Compound (1-174) was obtained in the same manner as in Synthesis Example 1 except that compound (X-4) was changed to compound (X-4-174).

m/z(M+H)=985.50 was observed by APCI-MS, and production of the target compound (1-174) was confirmed.

Synthesis Example (25): Synthesis of compound (1-186)

Compound (1-186) was obtained in the same manner as in Synthesis Example 1 except that compound (X-4) was changed to compound (X-4-186).

m/z(M+H)=993.52 was observed by APCI-MS, and production of the target compound (1-186) was confirmed.

Synthesis Example (26): Synthesis of Compound (1-200)

Compound (1-200) was obtained in the same manner as in Synthesis Example 1 except that compound (X-4) was changed to compound (X-4-200).

m/z(M+H)=883.41 was observed by APCI-MS, and production of the target compound (1-200) was confirmed.

Synthesis Example (27): Synthesis of Compound (1-204)

Compound (1-204) was obtained in the same manner as in Synthesis Example 1 except that compound (X-4) was changed to compound (X-4-204).

m/z(M+H)=939.47 was observed by APCI-MS, and production of the target compound (1-204) was confirmed.

Synthesis Example (28): Synthesis of Compound (1-205)

Compound (1-205) was obtained in the same manner as in Synthesis Example 1 except that compound (X-4) was changed to compound (X-4-205).

m/z(M+H)=981.42 was observed by APCI-MS, and production of the target compound (1-205) was confirmed.

Synthesis Example (29): Synthesis of Compound (1-207)

Compound (1-207) was obtained in the same manner as in Synthesis Example 1 except that compound (X-4) was changed to compound (X-4-207).

m/z(M+H)=913.45 was observed by APCI-MS, and production of the target compound (1-207) was confirmed.

Synthesis Example (30): Synthesis of Compound (1-210)

Compound (1-210) was obtained in the same manner as in Synthesis Example 1 except that compound (X-4) was changed to compound (X-4-210).

m/z(M+H)=1240.65 was observed by APCI-MS, and production of the target compound (1-210) was confirmed.

Synthesis Example (31): Synthesis of Compound (1-211)

Compound (1-211) was obtained in the same manner as in Synthesis Example 1 except that compound (X-4) was changed to compound (X-4-211).

m/z(M+H)=1092.53 was observed by APCI-MS, and production of the target compound (1-211) was confirmed.

Synthesis Example (32): Synthesis of Compound (1-214)

Compound (1-214) was obtained in the same manner as in Synthesis Example 1 except that compound (X-4) was changed to compound (X-4-214).

m/z(M+H)=778.33 was observed by APCI-MS, and production of the target compound (1-214) was confirmed.

Synthesis Example (33): Synthesis of Compound (1-215)

Compound (1-215) was obtained in the same manner as in Synthesis Example 1 except that compound (X-4) was changed to compound (X-4-215).

m/z(M+H)=1020·51 was observed by APCI-MS, and production of the target compound (1-215) was confirmed.

Synthesis Example (34): Synthesis of Compound (1-216)

Compound (1-216) was obtained in the same manner as in Synthesis Example 1 except that compound (X-4) was changed to compound (X-4-216).

m/z(M+H)=1240.65 was observed by APCI-MS, and production of the target compound (1-216) was confirmed.

Synthesis Example (35): Synthesis of Compound (1-219)

Compound (1-219) was obtained in the same manner as in Synthesis Example 1 except that compound (X-4) was changed to compound (X-4-219).

m/z(M+H)=1168.56 was observed by APCI-MS, and production of the target compound (1-219) was confirmed.

Synthesis Example (36): Synthesis of Compound (1-220)

Compound (1-220) was obtained in the same manner as in Synthesis Example 1 except that compound (X-4) was changed to compound (X-4-220).

m/z(M+H)=874.42 was observed by APCI-MS, and production of the target compound (1-220) was confirmed.

Synthesis Example (37): Synthesis of Compound (1-225)

Compound (1-225) was obtained in the same manner as in Synthesis Example 1 except that compound (X-4) was changed to compound (X-4-225).

m/z(M+H)=940.37 was observed by APCI-MS, and production of the target compound (1-225) was confirmed.

Synthesis Example (38): Synthesis of compound (1-227)

Compound (1-227) was obtained in the same manner as in Synthesis Example 1 except that compound (X-4) was changed to compound (X-4-227).

m/z(M+H)=1276.75 was observed by APCI-MS, and production of the target compound (1-227) was confirmed.

Synthesis Example (39): Synthesis of Compound (1-228)

Compound (1-228) was obtained in the same manner as in Synthesis Example 1 except that compound (X-4) was changed to compound (X-4-228).

m/z(M+H)=1066.48 was observed by APCI-MS, and production of the target compound (1-228) was confirmed.

Synthesis Example (40): Synthesis of Compound (1-229)

Compound (1-229) was obtained in the same manner as in Synthesis Example 1 except that compound (X-4) was changed to compound (X-4-229).

m/z(M+H)=793.27 was observed by APCI-MS, and production of the target compound (1-229) was confirmed.

Synthesis Example (41): Synthesis of Compound (1-232)

Compound (1-232) was obtained in the same manner as in Synthesis Example 1 except that compound (X-4) was changed to compound (X-4-232).

m/z(M+H)=1072.46 was observed by APCI-MS, and production of the target compound (1-232) was confirmed.

Synthesis Example (42): Synthesis of Compound (1-236)

Compound (1-236) was obtained in the same manner as in Synthesis Example 1 except that compound (X-4) was changed to compound (X-4-236).

m/z(M+H)=1166.62 was observed by APCI-MS, and production of the target compound (1-236) was confirmed.

Synthesis Example (43): Synthesis of Compound (1-238)

Compound (1-238) was obtained in the same manner as in Synthesis Example 1 except that compound (X-4) was changed to compound (X-4-238).

m/z(M+H)=966.42 was observed by APCI-MS, and production of the target compound (1-238) was confirmed.

Synthesis Example (44): Synthesis of Compound (1-239)

Compound (1-239) was obtained in the same manner as in Synthesis Example 1 except that compound (X-4) was changed to compound (X-4-239).

m/z(M+H)=1154.78 was observed by APCI-MS, and production of the target compound (1-239) was confirmed.

Synthesis Example (45): Synthesis of Compound (1-241)

Compound (1-241) was obtained in the same manner as in Synthesis Example 1 except that compound (X-4) was changed to compound (X-4-241).

m/z(M+H)=1023.60 was observed by APCI-MS, and production of the target compound (1-241) was confirmed.

Synthesis Example (46): Synthesis of Compound (1-243)

Compound (1-243) was obtained in the same manner as in Synthesis Example 1 except that compound (X-4) was changed to compound (X-4-243).

m/z(M+H)=1154.58 was observed by APCI-MS, and production of the target compound (1-243) was confirmed.

Synthesis Example (47): Synthesis of Compound (1-244)

Compound (1-244) was obtained in the same manner as in Synthesis Example 1 except that compound (X-4) was changed to compound (X-4-244).

m/z(M+H)=1022.49 was observed by APCI-MS, and production of the target compound (1-244) was confirmed.

Synthesis Example (48): Synthesis of Compound (1-249)

Compound (1-249) was obtained in the same manner as in Synthesis Example 1 except that compound (X-4) was changed to compound (X-4-249).

m/z(M+H)=1042.45 was observed by APCI-MS, and production of the target compound (1-249) was confirmed.

Synthesis Example (49): Synthesis of Compound (1-250)

Compound (1-250) was obtained in the same manner as in Synthesis Example 1 except that compound (X-4) was changed to compound (X-4-250).

m/z(M+H)=1041.55 was observed by APCI-MS, and production of the target compound (1-250) was confirmed.

Synthesis Example (50): Synthesis of Compound (1-252)

Compound (1-252) was obtained in the same manner as in Synthesis Example 1 except that compound (X-4) was changed to compound (X-4-252).

m/z(M+H)=1146.52 was observed by APCI-MS, and production of the target compound (1-252) was confirmed.

Synthesis Example (51): Synthesis of Compound (1-254)

Compound (1-254) was obtained in the same manner as in Synthesis Example 1 except that compound (X-4) was changed to compound (X-4-254).

m/z(M+H)=1050.42 was observed by APCI-MS, and production of the target compound (1-254) was confirmed.

Synthesis Example (52): Synthesis of compound (1-256)

Compound (1-256) was obtained in the same manner as in Synthesis Example 1 except that compound (X-4) was changed to compound (X-4-256).

m/z(M+H)=1027.54 was observed by APCI-MS, and production of the target compound (1-256) was confirmed.

Synthesis Example (53): Synthesis of compound (1-258)

Compound (1-258) was obtained in the same manner as in Synthesis Example 1 except that compound (X-4) was changed to compound (X-4-258).

m/z(M+H)=1148.53 was observed by APCI-MS, and production of the target compound (1-258) was confirmed.

Synthesis Example (54): Synthesis of Compound (1-261)

Compound (1-261) was obtained in the same manner as in Synthesis Example 1, except that compound (X-4) was changed to compound (X-4-261).

m/z(M+H)=1006.45 was observed by APCI-MS, and production of the target compound (1-261) was confirmed.

Synthesis Example (55): Synthesis of compound (1-263)

Compound (1-263) was obtained in the same manner as in Synthesis Example 1 except that compound (X-4) was changed to compound (X-4-263).

m/z(M+H)=1128.56 was observed by APCI-MS, and production of the target compound (1-263) was confirmed.

Synthesis Example (56): Synthesis of Compound (1-265)

Compound (1-265) was obtained in the same manner as in Synthesis Example 1 except that compound (X-4) was changed to compound (X-4-265).

m/z(M+H)=1030.45 was observed by APCI-MS, and production of the target compound (1-265) was confirmed.

Synthesis Example (57): Synthesis of compound (1-268)

Compound (1-268) was obtained in the same manner as in Synthesis Example 1 except that compound (X-4) was changed to compound (X-4-268).

m/z(M+H)=1042.45 was observed by APCI-MS, and production of the target compound (1-268) was confirmed.

Synthesis Example (58): Synthesis of compound (1-269)

Compound (1-269) was obtained in the same manner as in Synthesis Example 1 except that compound (X-4) was changed to compound (X-4-269).

m/z(M+H)=1128.56 was observed by APCI-MS, and production of the target compound (1-269) was confirmed.

Synthesis Example (59): Synthesis of Compound (1-270)

Compound (1-270) was obtained in the same manner as in Synthesis Example 1 except that compound (X-4) was changed to compound (X-4-270).

m/z(M+H)=1184.63 was observed by APCI-MS, and production of the target compound (1-270) was confirmed.

Synthesis Example (60): Synthesis of Compound (1-272)

Compound (1-272) was obtained in the same manner as in Synthesis Example 1 except that compound (X-4) was changed to compound (X-4-272).

m/z(M+H)=1009.49 was observed by APCI-MS, and production of the target compound (1-272) was confirmed.

Synthesis Example (61): Synthesis of Compound (1-273)

Compound (1-273) was obtained in the same manner as in Synthesis Example 1 except that compound (X-4) was changed to compound (X-4-273).

m/z(M+H)=1147.63 was observed by APCI-MS, and production of the target compound (1-273) was confirmed.

Synthesis Example (62): Synthesis of compound (1-274)

Compound (1-274) was obtained in the same manner as in Synthesis Example 1 except that compound (X-4) was changed to compound (X-4-274).

m/z(M+H)=1037.52 was observed by APCI-MS, and production of the target compound (1-274) was confirmed.

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 in a thin film state. Furthermore, when evaluating in a thin film state, depending on the usage mode of the compound under evaluation in an organic EL device, there are cases where only the compound under evaluation is made into a thin film for evaluation, or when the compound under evaluation is dispersed in an appropriate matrix material to form a thin film for evaluation. there is. 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 first deposition boat, the pressure of the vacuum chamber is reduced to 5×10 ^-4 Pa. Next, the deposition boat containing the host compound and the deposition boat containing the dopant material are heated simultaneously, and both the host compound and dopant material are deposited 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 (Shimadzu Corporation, UV-2600). Additionally, the fluorescence spectrum or phosphorescence spectrum of the sample is measured using a spectrofluorometer (F-7000, manufactured by Hitachi Hi-Tech Co., Ltd.).

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

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

Next, the basic physical property evaluation 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, we observed luminescent components with fast and slow fluorescence lifetimes at the maximum emission wavelength, which is measured as an appropriate excitation wavelength. In measurements of the fluorescence lifetime of general organic EL materials that emit fluorescence at room temperature, the 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 luminescent component is observed in the compound being evaluated, the triplet energy with a long excitation life is transferred to the singlet energy by thermal activation, resulting in observation 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 mounting the boat, the vacuum tank is depressurized 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 Machinery Co., Ltd. PYS-201).

<Calculation of electron affinity (Ea)>

Electron affinity can be measured from the difference between the ionization potential measured by the above-described method and the energy gap calculated by the above-described 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 was observed at 77 K with excitation light at the second absorption peak from the long wavelength side of the absorption spectrum, and the lowest excitation day from the shoulder on the short wavelength side of the peak of the fluorescence spectrum. Find the doublet energy level E(S,Sh). Additionally, on a single film of the target compound formed on a glass substrate, the phosphorescence spectrum was observed at 77 K using excitation light at the second absorption peak from the long wavelength side of the absorption spectrum, and the lowest excitation was observed from the shoulder on the short wavelength side of the peak of the phosphorescence spectrum. Find the triplet energy level E(T,Sh).

<Manufacture and evaluation of organic EL devices>

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

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

<Configuration of organic EL device>

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

[Element composition A]

The material composition of each layer in the organic EL device of Example 1 is shown in Table 1 below.

In Table 1 and Table 2, “HI”, “HAT-CN”, “HT-1”, “HT-2”, “BH”, “ET-1”, “ET-2”, “Liq” , Comparative compound (1) and Comparative compound (5) described in Korean Patent Application Publication No. 2022/074408, Comparative compound (2) described in International Publication No. 2022/103018, Comparative compound (2) described in US Patent Application Publication No. 2022/02091 The chemical structures of comparative compound (3) and comparative compound (4) described in International Publication No. 2021/194216 are shown below.

(Example 1)

A 26 mm x 28 mm x 0.7 mm glass substrate (manufactured by Opto Science Co., Ltd.) made by polishing ITO 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), and ET were 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 and deposited to a film thickness of 40 nm. Next, HAT-CN was heated and deposited to a film thickness of 5 nm. Next, HT-1 was deposited to a film thickness of 5 nm. 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, forming 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, thereby obtaining an organic EL device.

(Examples 2 to 61, Comparative Examples 1 to 5)

Organic EL devices of Examples 2 to 61 and Comparative Examples 1 to 5 were obtained in the same manner as Example 1 except that each material shown in Table 2 was used instead of compound (1-1).

<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 half width (nm). For this evaluation item, for example, the value 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, causing the photons to be emitted to the outside of the light-emitting device. Since it is not emitted to the outside, 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 a voltage/current generator R6144 manufactured by Advantist, a voltage such that the luminance of the device becomes 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 in 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 is integrated in the entire observed wavelength range, 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 total 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 obtained 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 Examples 1 to 61 and Comparative Examples 1 to 5, 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.

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 (14)

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

In equation (1),
Ring A and Ring B are each independently a substituted or unsubstituted aryl ring or a substituted or unsubstituted heteroaryl ring,
The C ring is a ring expressed by the formula (C),
In equation (C),
X ^c is >O, > _NR , >C(-R) ₂ , >Si(-R) ₂ , >S, or >Se, and -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, and >C(-R ) ₂ and the two R of >Si(-R) ₂ may be bonded to each other to form a ring,
Any two consecutive Z ^Cs are on one side a carbon bonded to Y ¹ and on the other side a carbon bonded to N of >NG _B ,
Other Z ^C is each independently N or CR ^C ,
R ^C is each independently hydrogen or any one substituent selected from the substituent group ZB,
Two adjacent R ^C on the c2 ring may be bonded to each other to form an aryl ring or heteroaryl ring together with the carbons to which they are bonded, and the formed aryl ring and the formed heteroaryl ring are at least one selected from the substituent group ZB. may be substituted with a substituent of
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,
G _A and G _B are each independently monovalent groups expressed by the formula (G),
In formula (G),
Z ^a is each independently N or CR ^a ,
R ^a is each independently hydrogen or any one substituent selected from the substituent group ZB, or is bonded to adjacent R ^a to form an aryl ring or heteroaryl ring with the carbons to which they are bonded, and the aryl ring formed above The ring and the formed heteroaryl ring may each be substituted with at least one substituent selected from the substituent group ZB,
A is >O, >NR ^A , >Si(-R ^A ) ₂ , >C(-R ^A ) ₂ , >S, or >Se, and R ^A 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 ^A of >Si(-R ^A ) ₂ may be bonded to each other to form a ring. , the two R ^A of >C(-R ^A ) ₂ may be bonded to each other to form a ring,
However, the monovalent group represented by formula (G) binds to N of >NG _A or >NG _B at any one position,
In the above structure, at least one aryl ring or heteroaryl ring may be condensed with at least one cycloalkane, the cycloalkane may have a substituent, and at least one -CH ₂ in the cycloalkane - may be substituted with -O-,
However, ^when ,
^When , has at least one substituent selected from the group consisting of substituted or unsubstituted diarylamino, substituted or unsubstituted arylheteroarylamino, and substituted or unsubstituted cycloalkyl, or aryl in the above structure. At least one selected from the group consisting of a ring and a heteroaryl ring is condensed with a cycloalkane, the cycloalkane may have a substituent, and at least one -CH ₂ - in the cycloalkane is substituted with -O-. It can be done,
At least one hydrogen in the above structure may be substituted with cyano, halogen, or deuterium,
The substituent group ZB is,
Aryl which may be substituted with at least one group selected from the group consisting of aryl, heteroaryl, diarylamino, alkyl, cycloalkyl and substituted silyl,
Heteroaryl, which may be substituted with at least one group selected from the group consisting of aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, and substituted silyl,
Diarylamino, which may be substituted with at least one group selected from the group consisting of aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, and substituted silyl (two aryls may be bonded to each other through a linking group),
Diheteroarylamino, which may be substituted with at least one group selected from the group consisting of aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, and substituted silyl (two heteroaryls may be bonded to each other through a linking group),
Arylheteroarylamino, which may be substituted with at least one group selected from the group consisting of aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, and substituted silyl (aryl and heteroaryl may be bonded to each other through a linking group),
Diarylboryl, which may be substituted with at least one group selected from the group consisting of aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, and substituted silyl (two aryls may be bonded through a single bond or linking group),
Alkyl which may be substituted with at least one group selected from the group consisting of aryl, heteroaryl, diarylamino, alkyl, cycloalkyl and substituted silyl,
Cycloalkyl, which may be substituted with at least one group selected from the group consisting of aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, and substituted silyl,
Alkoxy which may be substituted with at least one group selected from the group consisting of aryl, heteroaryl, diarylamino, alkyl, cycloalkyl and substituted silyl,
Aryloxy which may be substituted with at least one group selected from the group consisting of aryl, heteroaryl, diarylamino, alkyl, cycloalkyl and substituted silyl,
Arylthio which may be substituted with at least one group selected from the group consisting of aryl, heteroaryl, diarylamino, alkyl, cycloalkyl and substituted silyl, and
It consists of substituted silyl. A polycyclic aromatic compound according to claim 1, represented by formula (1a);

In formula (1a), Z is each independently N or CR ¹¹ ,
R ¹¹ is each independently hydrogen or any one substituent selected from the substituent group ZB, or is combined with an adjacent R ¹¹ to form an aryl ring or heteroaryl ring together with the a ring or the b ring, and the formed aryl ring and the formed heteroaryl ring may be substituted with at least one substituent selected from the substituent group ZB,
Y ¹ , G _A , and G _B have the same meaning as Y ¹ , G _A and G _B in formula (1), respectively, and X ^c and Z ^c have the same meaning as X ^c and Z ^c in formula (C), respectively. meaning,
In formula (1a), at least one of the aryl ring or heteroaryl ring may be condensed with at least one cycloalkane, the cycloalkane may have a substituent, and at least one of the aryl rings or heteroaryl rings may be condensed with at least one cycloalkane. -CH ₂ - may be substituted with -O-;
At least one hydrogen in formula (1a) may be substituted with cyano, halogen, or deuterium. The method of claim 1 or 2, wherein G _A and G _B are each independently a group represented by formula (G-1), formula (G-4), or formula (G-5), or formula (G -1), a polycyclic aromatic compound in which one or two hydrogens in the structure are substituted with alkyl or cycloalkyl in the group represented by formula (G-4) or formula (G-5).
The polyaromatic compound according to any one of claims 1 to 3, wherein A is >O. The polyaromatic compound according to claim 1, which is represented by any one of formula (1a-1), formula (1a-2), or formula (1a-3);

In equation (1a-1),
Ra1, Ra2, Ra3, Rb1, Rb2, Rb3, Rb4, Rc1, Rc2, Rc3, Rc4, Rg1, Rg2, Rg3, Rg4, Rg5, Rg6, Rg7, Rg8, Rg9, Rg10, Rg11, Rg12, Rg13, and Rg14 is each independently hydrogen or any one substituent selected from the substituent group ZB,
However, two adjacent ones of Rb1, Rb2, Rb3, and Rb4 may be bonded to each other to form an aryl ring together with the carbons to which they are bonded, and the formed aryl ring may be substituted with at least one substituent selected from the substituent group ZB. You can have it,
In formula (1a-1), at least one of the aryl ring or heteroaryl ring may be condensed with at least one cycloalkane, the cycloalkane may have a substituent, and at least one of the aryl rings or heteroaryl rings may be condensed with at least one cycloalkane. One -CH ₂ - may be substituted with -O-, provided that cycloalkane does not condense in the g11 ring and the g13 ring;
In equation (1a-2),
Ra1, Ra2, Ra3, Rb1, Rb2, Rb3, Rb4, Rc1, Rc2, Rc3, Rc4, Rg1, Rg2, Rg3, Rg4, Rg5, Rg6, Rg7, Rg8, Rg9, Rg10, Rg11, Rg12, Rg13, and Rg14 is each independently hydrogen or any one substituent selected from the substituent group ZB, provided that at least one of Ra1, Ra2, Ra3, Rb1, Rb2, Rb3, Rb4, Rc1, Rc2, Rc3, and Rc4 is, It is substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino, substituted or unsubstituted arylheteroarylamino, or substituted or unsubstituted cycloalkyl, or formula (1a- In 2), at least one selected from the group consisting of an aryl ring and a heteroaryl ring is condensed with a cycloalkane, the cycloalkane may have a substituent, and at least one -CH ₂ - in the cycloalkane may be substituted with -O-,
Two adjacent ones of Rb1, Rb2, Rb3, Rb4, Rc1, Rc2, Rc3, and Rc4 may be bonded to each other to form an aryl ring or heteroaryl ring together with the carbons to which they are bonded, and the formed aryl ring may be a substituent group. may be substituted with at least one substituent selected from ZB,
In formula (1a-2), at least one of the aryl ring or heteroaryl ring may be condensed with at least one cycloalkane, the cycloalkane may have a substituent, and at least one of the aryl rings or heteroaryl rings may be condensed with at least one cycloalkane. One -CH ₂ - may be substituted with -O-;
In equation (1a-3),
Ra1, Ra2, Ra3, Rb1, Rb2, Rb3, Rb4, Rc1, Rc2, Rc3, Rc4, Rg1, Rg2, Rg3, Rg4, Rg5, Rg6, Rg7, Rg8, Rg9, Rg10, Rg11, Rg12, Rg13, and Rg14 is each independently hydrogen or any one substituent selected from the substituent group ZB,
However, two adjacent ones of Rb1, Rb2, Rb3, Rb4, Rc1, Rc2, Rc3, and Rc4 may be bonded to each other to form an aryl ring or heteroaryl ring with the carbons to which they are bonded, and the formed aryl ring may be may be substituted with at least one substituent selected from the substituent group ZB,
In formula (1a-3), at least one of the aryl ring or heteroaryl ring may be condensed with at least one cycloalkane, the cycloalkane may have a substituent, and at least one of the aryl rings or heteroaryl rings may be condensed with at least one cycloalkane. One -CH ₂ - may be substituted with -O-;
At least one hydrogen in each formula (1a-1), formula (1a-2), and formula (1a-3) may be substituted with cyano, halogen, or deuterium. The polycyclic aromatic compound according to claim 3, which is represented by any one of the following formulas;



where Me is methyl, tBu is t-butyl, and D is deuterium. The polycyclic aromatic compound according to claim 3, which is represented by any one of the following formulas;


where Me is methyl, tBu is t-butyl, tAm is t-amyl, and D is deuterium. The polycyclic aromatic compound according to claim 5, which is represented by formula (1a-3). The polycyclic aromatic compound according to claim 8, represented by any one of the following formulas;


where Me is methyl and tBu is t-butyl. A material for an organic device containing the polycyclic aromatic compound according to any one of claims 1 to 9. 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 polyaromatic compound according to any one of claims 1 to 9. device. The organic electroluminescent device according to claim 11, wherein the light-emitting layer includes a host and the polycyclic aromatic compound as a dopant. The organic electroluminescent device according to claim 12, 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 11 to 13.