Polycyclic aromatic compound

Abstract

The polycyclic aromatic compound represented by formula (1) can be effectively used as a material for an organic device such as an organic electroluminescent element. In the formula, Ra1-Ra3, Rb1-Rb4, and Rc1-Rc4 are hydrogen or substituents, at least one of Rc1-Rc4 is a substituted or unsubstituted aryl group, Y1 is B, at least one of X1 and X2 is > N-RNX in which RNX is a group represented by formula (G-1) or formula (G-2), the other X1 and X2 are > N-Ar (Ar is an aryl group or the like) or the like, Rd2-Rd8 and Re2-Re10 are hydrogen or substituents, at least one selected from the group consisting of Re5-Re10 is an alkyl group, a cycloalkyl group, or an aryl group, and Rb1-Rb4 and Rc1-Rc4 are hydrogen or substituents. Or the aryl ring in formula (G-2) is condensed by at least one cycloalkane. # imgabs0 #

Description

Technical Field

[0001] The present invention relates to a polycyclic aromatic compound. In particular, the present invention relates to a polycyclic aromatic compound containing nitrogen and boron. The present invention further relates to a material for an organic device, an organic electroluminescent element, and a display device and a lighting device, each containing the polycyclic aromatic compound. Background Art

[0002] Previously, display devices using light-emitting elements that perform electroluminescence have been studied in various ways because they can achieve power saving or thinning. Furthermore, organic electroluminescent elements containing organic materials have been actively studied because they can easily be made lightweight or large-sized. In particular, regarding the development of organic materials having light-emitting characteristics such as blue, which is one of the primary colors of light, and regarding the development of organic materials having charge transport capabilities (with the possibility of becoming semiconductors or superconductors) including holes, electrons, etc., both high-molecular compounds and low-molecular compounds have been actively studied to date.

[0003] An organic electroluminescent element has a structure including: a pair of electrodes including an anode and a cathode, and one or more layers disposed between the pair of electrodes and containing an organic compound. Among the layers containing an organic compound, there are a light-emitting layer, or a charge transport / injection layer that transports or injects charges such as holes and electrons, etc., and various organic materials suitable for these layers have been developed.

[0004] Among them, Patent Document 1 discloses that a polycyclic aromatic compound containing boron is effectively used as a material for an organic electroluminescent element, etc. It has been reported that an organic electroluminescent element containing the polycyclic aromatic compound has good external quantum efficiency. Patent Documents 2 to 4 disclose a polycyclic aromatic compound containing boron condensed with a heterocycle such as benzofuran.

[0005] Prior Art Documents

[0006] Patent Documents

[0007] Patent Document 1: International Publication No. 2015 / 102118

[0008] Patent Document 2: Specification of U.S. Patent Application Publication No. 2022 / 0310924

[0009] Patent Document 3: International Publication No. 2021 / 107743

[0010] Patent Document 4: International Publication No. 2022 / 191570 Summary of the Invention

[0011] Problems to be Solved by the Invention

[0012] As described above, various materials have been developed as materials used in organic electroluminescence (EL) elements. However, in order to increase the selection of materials for organic EL elements, it is desired to develop a material including a novel compound.

[0013] An object of the present invention is to provide a novel compound which can be effectively used as a material for an organic device such as an organic EL element.

[0014] Technical means of solving problems

[0015] The present inventors have made intensive research to solve the above-mentioned problems, and have successfully produced novel polycyclic aromatic compounds with better luminescent properties among polycyclic aromatic compounds having structures similar to the compounds described in Patent Documents 1 to 4. In addition, it has been found that an excellent organic EL element can be obtained by configuring a layer containing the polycyclic aromatic compound between a pair of electrodes to form an organic EL element, thereby completing the present invention. That is, the present invention provides the following polycyclic aromatic compounds, and further provides materials for organic devices containing the following polycyclic aromatic compounds, etc.

[0016] Specifically, the present invention has the following structures.

[0017] <1> A polycyclic aromatic compound having a structure consisting of one or two or more structural units represented by formula (1);

[0018] [Chemistry 1]

[0019]

[0020] In formula (1),

[0021] R a1 ~R a3 , R b1 ~R b4 and R c1 ~R c4 are each independently hydrogen or a substituent,

[0022] R a1 ~R a3 , R b1 ~R b4 and R c1 ~R c4 The two adjacent groups in the group may be bonded to each other and, together with the two carbon atoms to which they are bonded, form a substituted or unsubstituted aryl ring or a substituted or unsubstituted heteroaryl ring,

[0023] Among them, R c1 ~R c4At least one of them is a substituted or unsubstituted aryl or a substituted or unsubstituted heteroaryl.

[0024] Y 1 is B, P, P═O, P═S, Al, Ga, As, Si-R or Ge-R, where R of the Si-R and the Ge-R is a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted alkyl, or a substituted or unsubstituted cycloalkyl.

[0025] X 1 and X 2 are each independently >O, >N-R NX , >C(-R CX )2, >Si(-R IX )2, >S, or >Se, and R NX is hydrogen, a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted alkyl, or a substituted or unsubstituted cycloalkyl, and R CX are each independently hydrogen, a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted alkyl, or a substituted or unsubstituted cycloalkyl, and two Rs CX can be bonded to each other to form a ring, and R IX are each independently hydrogen, a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted alkyl, or a substituted or unsubstituted cycloalkyl, and two Rs IX can be bonded to each other to form a ring. Additionally, R NX and / or R CX can be bonded to R a3 and / or R b1 , or R a1 and / or R c4 through a linking group or a single bond.

[0026] Among them, at least one selected from the group consisting of X 1 and X 2 is >N-R NX represented by the formula (G-1) or the formula (G-2). NX .

[0027] [Chemical formula 2]

[0028]

[0029] In the formula (G-1),

[0030] R d2 to R d8 are each independently hydrogen or a substituent.

[0031] R d2 ~R d8 Two adjacent groups in can be bonded to each other and, together with the two carbon atoms to which they are bonded, form a substituted or unsubstituted aryl ring or a substituted or unsubstituted heteroaryl ring.

[0032] * indicates the bonding position to the nitrogen atom.

[0033] In formula (G-2),

[0034] R e2 ~R e10 are each independently hydrogen or a substituent.

[0035] Wherein, at least one selected from the group consisting of R e6 ~R e10 is a substituent selected from the group consisting of an alkyl group, a cycloalkyl group which may be substituted by at least one alkyl group, and an aryl group which may be substituted by at least one alkyl group or a cycloalkyl group which may be substituted by an alkyl group, or at least one of the aryl ring or heteroaryl ring in formula (G-2) is condensed with at least one cycloalkane, at least one hydrogen in the cycloalkane may be substituted, and at least one -CH2- in the cycloalkane may be substituted by -O-.

[0036] * indicates the bonding position to the nitrogen atom.

[0037] At least one of the aryl ring or heteroaryl ring in the structure may be condensed with at least one cycloalkane, at least one hydrogen in the cycloalkane may be substituted, and at least one -CH2- in the cycloalkane may be substituted by -O-.

[0038] In the structure, at least one hydrogen may be substituted by deuterium, at least one nitrogen may be substituted by nitrogen-15 ( 15 N), at least one sulfur may be substituted by sulfur-33 ( 33 S), sulfur-34 ( 34 S) or sulfur-36 ( 36 S), at least one oxygen may be substituted by oxygen-17 ( 17 O) or oxygen-18 ( 18 O), at least one carbon may be substituted by carbon-13 ( 13 C), and at least one boron may be substituted by boron-11 ( 11 B).

[0039] <2> The polycyclic aromatic compound according to <1>, wherein the aryl rings and heteroaryl rings located at R c1 ~R c4 are not condensed with cycloalkanes.

[0040] <3> The polycyclic aromatic compound according to <1> or <2>, wherein Rc3 is an aryl group that can be alkyl-substituted, R c1 , R c2 and R c4 are all hydrogen.

[0041] <4>The polycyclic aromatic compound according to <3>, wherein R c3 is a phenyl group that can be tert-butyl-substituted.

[0042] <5>The polycyclic aromatic compound according to <4>,

[0043] which has a structure composed of one of the structural units represented by formula (1),

[0044] Y 1 is B,

[0045] R a1 , R a3 , R b1 , R b4 , R c1 and R c4 are each hydrogen,

[0046] R a2 is hydrogen, an unsubstituted alkyl group, a cycloalkyl group that can be methyl-substituted, an aryl group that can be alkyl- or cycloalkyl-(which can be methyl-substituted)-substituted, a heteroaryl group that can be alkyl- or cycloalkyl-(which can be methyl-substituted)-substituted, a diarylamino group that can be alkyl- or cycloalkyl-(which can be methyl-substituted)-substituted, an arylheteroarylamino group that can be alkyl- or cycloalkyl-(which can be methyl-substituted)-substituted, or a carbazolyl group that can be alkyl- or cycloalkyl-(which can be methyl-substituted)-substituted,

[0047] R b2 and R b3 are each independently hydrogen, an unsubstituted alkyl group, a cycloalkyl group that can be methyl-substituted, an aryl group that can be alkyl- or cycloalkyl-(which can be methyl-substituted)-substituted, a heteroaryl group that can be alkyl- or cycloalkyl-(which can be methyl-substituted)-substituted, a diarylamino group that can be alkyl- or cycloalkyl-(which can be methyl-substituted)-substituted, an arylheteroarylamino group that can be alkyl- or cycloalkyl-(which can be methyl-substituted)-substituted, or a carbazolyl group that can be alkyl- or cycloalkyl-(which can be methyl-substituted)-substituted,

[0048] R c2 and R c3 any one of them is an aryl group that can be alkyl-substituted, and the other is hydrogen or an aryl group that can be alkyl-substituted,

[0049] X 1 and X 2 are each independently >N-R NX ,

[0050] When R is other than the group represented by formula (G-1) or the group represented by formula (G-2), NX said R NX is an aryl group which may be substituted by an alkyl group or a cycloalkyl group which may be substituted by an alkyl group (excluding the group represented by formula (G-2)) or a heteroaryl group which may be substituted by an alkyl group or a cycloalkyl group (which may be substituted by an alkyl group) (excluding the group represented by formula (G-1)),

[0051] In formula (G-1),

[0052] R d2 to R d8 are each independently hydrogen, an unsubstituted alkyl group, a cycloalkyl group which may be substituted by a methyl group, an aryl group which may be substituted by an alkyl group or a cycloalkyl group (which may be substituted by a methyl group), or a heteroaryl group which may be substituted by an alkyl group or a cycloalkyl group (which may be substituted by a methyl group),

[0053] R d2 to R d8 Two adjacent groups among them may be bonded to each other and together with the two carbon atoms to which they are bonded form a benzene ring, and the benzene ring may be substituted by an unsubstituted alkyl group, a cycloalkyl group which may be substituted by a methyl group, an aryl group which may be substituted by an alkyl group or a cycloalkyl group (which may be substituted by a methyl group), or a heteroaryl group which may be substituted by an alkyl group or a cycloalkyl group (which may be substituted by a methyl group),

[0054] In formula (G-2),

[0055] At least one selected from the group consisting of R e6 to R e10 is an unsubstituted alkyl group, a cycloalkyl group which may be substituted by a methyl group, or an aryl group which may be substituted by an alkyl group or a cycloalkyl group (which may be substituted by a methyl group), or two adjacent groups among R e2 to R e10 are bonded to each other to form a partial structure represented by formula (B-1) or formula (B-2),

[0056] At least one of the aryl ring or heteroaryl ring other than the c-ring in formula (1) may have formula (B-1) or formula (B-2) as a substituent,

[0057] [Chemical formula 3]

[0058]

[0059] In formula (B-1) or formula (B-2), * represents the position bonded to the adjacent ring-constituting atoms respectively,

[0060] At least one hydrogen in the structure may be substituted by deuterium.

[0061] <6> The polycyclic aromatic compound according to any one of <1> to <5>, wherein at least one selected from the group consisting of X 1 and X2 At least one of the groups consisting of is R NX >N-R which is a group represented by formula (G-1) NX and does not contain R NX >N-R which is a group represented by formula (G-2) NX as X 1 or X 2 .

[0062] <7> The polycyclic aromatic compound according to <6> is represented by any one of the following formulas;

[0063] [Chemical formula 4]

[0064]

[0065] [Chemical formula 5]

[0066]

[0067] [Chemical formula 6]

[0068]

[0069] [Chemical formula 7]

[0070]

[0071] [Chemical formula 8]

[0072]

[0073] [Chemical formula 9]

[0074]

[0075] [Chemical formula 10]

[0076]

[0077] [Chemical formula 11]

[0078]

[0079] In the formula, Me is methyl, tBu is tert-butyl, and D is deuterium.

[0080] <8> The polycyclic aromatic compound according to <7> is represented by formula (1-9-2), formula (1-9-5), formula (1-9-9), formula (1-11-8), formula (1-17-10), formula (1-19-1), formula (1-19-3), formula (1-21-1) or formula (1-21-4).

[0081] <9>The polycyclic aromatic compound according to any one of <1> to <5>, wherein at least one selected from the group consisting of X 1 and X 2 is R NX is >N-R of the group represented by formula (G-2) NX , and does not include R NX is >N-R of the group represented by formula (G-1) NX as X 1 or X 2 .

[0082] <10>The polycyclic aromatic compound according to <9> is represented by any one of the following formulas;

[0083] [Chemical formula 12]

[0084]

[0085] [Chemical formula 13]

[0086]

[0087] [Chemical formula 14]

[0088]

[0089] [Chemical formula 15]

[0090]

[0091] [Chemical formula 16]

[0092]

[0093] [Chemical formula 17]

[0094]

[0095] [Chemical formula 18]

[0096]

[0097] [Chemical formula 19]

[0098]

[0099] [Chemical formula 20]

[0100]

[0101] [Chemical formula 21]

[0102]

[0103] In the formula, Me represents methyl, tBu represents tert-butyl, tAm represents tert-amyl, and D represents deuterium.

[0104] <11> The polycyclic aromatic compound according to <10> is represented by formula (1-1-1), formula (1-1-3), formula (1-1-5), formula (1-1-10), formula (1-2-7), formula (1-3-4), formula (1-3-6), formula (1-3-9), formula (1-3-10), formula (1-4-2), formula (1-5-8), formula (1-6-2), formula (1-6-6), formula (1-6-10), formula (1-8-2), formula (1-16-6), formula (1-20-1), formula (1-20-3), formula (1-20-4), formula (1-20-7), formula (1-20-10), formula (1-21-12), or formula (1-21-15).

[0105] <12> The polycyclic aromatic compound according to <10> is represented by formula (1-1-1) or formula (1-20-10).

[0106] <13> The polycyclic aromatic compound according to any one of <1> to <5>, wherein any one of X 1 or X 2 is >N-R where R NX is a group represented by formula (G-1), and the other is >N-R where R NX is a group represented by formula (G-2). NX is a group represented by formula (G-2). NX .

[0107] <14> The polycyclic aromatic compound according to <13> is represented by any one of the following formulas;

[0108] [Chemical formula 22]

[0109]

[0110] [Chemical formula 23]

[0111]

[0112] In the formula, Me represents methyl, tBu represents tert-butyl, tAm represents tert-amyl, and D represents deuterium.

[0113] <15> The polycyclic aromatic compound according to <14> is represented by formula (1-17-1), formula (1-17-3), formula (1-17-5), or formula (1-21-23).

[0114] <16> The polycyclic aromatic compound according to <6> is represented by any one of the following formulas;

[0115] [Chemical formula 24]

[0116]

[0117] In the formula, Me is methyl and tBu is tert-butyl.

[0118] <17> The polycyclic aromatic compound according to <1> is represented by any one of the following formulas;

[0119] [Chemical formula 25]

[0120]

[0121] [Chemical formula 26]

[0122]

[0123] In the formula, Me is methyl, tBu is tert-butyl, and D is deuterium.

[0124] <18> A material for an organic device contains the polycyclic aromatic compound according to any one of <1> to <17>.

[0125] <19> An organic electroluminescent element includes: a pair of electrodes including an anode and a cathode; and a light-emitting layer disposed between the pair of electrodes, and the light-emitting layer contains the polycyclic aromatic compound according to any one of <1> to <17>.

[0126] <20> The organic electroluminescent element according to <19>, wherein the light-emitting layer includes a host and the polycyclic aromatic compound as a dopant.

[0127] <21> The organic electroluminescent element according to <20>, wherein the host is an anthracene compound, a fluorene compound, or a dibenzo compound.

[0128] <22> A display device or a lighting device includes the organic electroluminescent element according to any one of <19> to <21>.

[0129] Effects of the Invention

[0130] According to the present invention, there is provided a novel polycyclic aromatic compound that can be effectively used as a material for organic devices such as organic electroluminescent elements. The polycyclic aromatic compound of the present invention can be used to manufacture organic devices such as organic electroluminescent elements. Description of the Drawings

[0131] Figure 1 is a schematic cross-sectional view showing an example of an organic electroluminescent element. Detailed Description

[0132] ​Hereinafter, the present invention will be described in detail. The description of the constituent elements described below is sometimes based on representative embodiments or specific examples, but the present invention is not limited to such embodiments. In addition, in this specification, the numerical range represented by "~" means a range including the numerical values described before and after "~" as the lower limit value and the upper limit value. Further, in this specification, "hydrogen" in the description of the structural formula means "hydrogen atom (H)". Similarly, "carbon atom (C)" is sometimes referred to as "carbon".

[0133] In this specification, when referring to "adjacent groups", it means two groups that are bonded to two adjacent atoms (two atoms directly bonded by a covalent bond) in the structural formula, respectively.

[0134] In this specification, "Me" represents methyl, "Et" represents ethyl, "nBu" represents normal butyl, "tBu" represents tertiary butyl, "iBu" represents isobutyl, "secBu" represents secondary butyl, "nPr" represents normal propyl, "iPr" represents isopropyl, "tAm" represents tertiary amyl, "2EH" represents 2-ethylhexyl, "tOct" represents tertiary octyl, "Ph" represents phenyl, "Mes" represents mesityl (2,4,6-trimethylphenyl), "Ad" represents 1-adamantyl, "Tf" represents trifluoromethanesulfonyl, "TMS" represents trimethylsilyl, and "D" represents deuterium.

[0135] In this specification, the organic electroluminescent element is sometimes referred to as "organic EL element".

[0136] In this specification, the chemical structure or substituent is sometimes represented by the number of carbon atoms. However, when a substituent is substituted in the chemical structure, or when a substituent is further substituted on the substituent, etc., the number of carbon atoms refers to the number of carbon atoms of the chemical structure or substituent respectively, and does not refer to the total number of carbon atoms of the chemical structure and the substituent, or the total number of carbon atoms of the substituent and the substituent. For example, the so-called "substituent B having a carbon number of Y substituted with a substituent A having a carbon number of X" means that the "substituent A having a carbon number of X" is substituted on the "substituent B having a carbon number of Y", and the carbon number Y is not the total number of carbon atoms of substituent A and substituent B. Further, for example, the so-called "substituent B having a carbon number of Y substituted with a substituent A" means that the "(substituent A having an unspecified carbon number)" is substituted on the "substituent B having a carbon number of Y", and the carbon number Y is not the total number of carbon atoms of substituent A and substituent B.

[0137] The chemical structural formulas described in this specification (including general formulas depicted by Markush structural formulas such as formula (1) described later) are planar structural formulas. Therefore, in reality, there may sometimes be various isomeric structures such as enantiomers, diastereomers, and rotational isomers. In this specification, unless otherwise specified, the compounds described may be any isomeric structure that can be conceived based on their planar structural formulas. Additionally, they may also be mixtures of any ratio composed of possible isomers.

[0138] In this specification, the structural formulas of many aromatic compounds are described by combining double bonds and single bonds. However, in reality, due to the resonance of π electrons, for a single substance, there are also multiple equivalent resonance structures such as the alternating replacement of double bonds and single bonds. In this specification, only one resonance structural formula is described for one substance, but unless otherwise specified, it also includes other resonance structural formulas that are equivalent in organic chemistry.

[0139] In addition, in this specification, it is sometimes expressed as "can ~", but it has the same meaning as "not ~, or through ~".

[0140] <Explanation of Rings and Substituents>

[0141] First, the details of the rings and substituents used in this specification are described below.

[0142] As the "aryl ring" in this specification, for example, aryl rings having 6 to 30 carbon atoms can be cited, preferably aryl rings having 6 to 16 carbon atoms, more preferably aryl rings having 6 to 12 carbon atoms, and particularly preferably aryl rings having 6 to 10 carbon atoms.

[0143] As specific "aryl rings", the following can be cited: a benzene ring which is a monocyclic system, a biphenyl ring which is a bicyclic system, a naphthalene ring and an indene ring which are condensed bicyclic systems, a terphenyl ring (meta - terphenyl, ortho - terphenyl, para - terphenyl) which is a tricyclic system, an acenaphthene ring, a fluorene ring, a phenalene ring, a phenanthrene ring, an anthracene ring which are condensed tricyclic systems, a triphenylene ring, a pyrene ring, a tetracene ring which are condensed tetracyclic systems, rings, a perylene ring, a pentacene ring which are condensed pentacyclic systems, etc. In addition, the fluorene ring, benzo[a]fluorene ring, and indene ring also respectively include structures in which a fluorene ring, benzo[a]fluorene ring, cyclopentane ring, etc. are spiro - bonded. Furthermore, the fluorene ring, benzo[a]fluorene ring, and indene ring also include rings in which two of the two hydrogens of the methylene group in their structures are respectively substituted with an alkyl group such as a methyl group which is a first substituent described later to form a dimethylfluorene ring, a dimethylbenzo[a]fluorene ring, a dimethylindene ring, etc.

[0144] As the "heteroaryl ring" in this specification, for example, heteroaryl rings having 2 to 30 carbon atoms can be cited, preferably heteroaryl rings having 2 to 25 carbon atoms, more preferably heteroaryl rings having 2 to 20 carbon atoms, still more preferably heteroaryl rings having 2 to 15 carbon atoms, and particularly preferably heteroaryl rings having 2 to 10 carbon atoms. In addition, as the "heteroaryl ring", for example, heterocycles containing 1 to 5 heteroatoms selected from oxygen, sulfur, nitrogen, boron, selenium, phosphorus, and tellurium as ring-constituting atoms in addition to carbon can be cited.

[0145] As specific "heteroaryl rings", for example, the following can be cited: pyrrole ring, oxazole ring, isoxazole ring, thiazole ring, isothiazole ring, imidazole ring, oxadiazole ring (furazan ring, etc.), thiadiazole ring, triazole ring, tetrazole ring, pyrazole ring, pyridine ring, pyrimidine ring, pyridazine ring, pyrazine ring, triazine ring, indole ring, isoindole ring, 1H-indazole ring, benzimidazole ring, benzoxazole ring, benzothiazole ring, 1H-benzotriazole ring, quinoline ring, isoquinoline ring, cinnoline ring, quinazoline ring, quinoxaline ring, phthalazine ring, naphthyridine ring, purine ring, pteridine ring, carbazole ring, acridine ring, phenoxathiin ring, phenoxazine ring, phenothiazine ring, phenazine ring, phenazasiline ring, indolizine ring, furan ring, benzofuran ring, isobenzofuran ring, dibenzofuran ring, thiophene ring, benzothiophene ring, dibenzothiophene ring, thianthrene ring, indolocarbazole ring, benzindolocarbazole ring, dibenzindolocarbazole ring, naphthobenzofuran ring, dioxin ring, dihydroacridine ring, xanthene ring, thioxanthene ring, dibenzodioxin ring, dioxaboronaphthacene ring (5,9-dioxa-13b-bora-13bH-naphtho[3,2,1-de]anthracene ring, etc.), benzoselenophene ring, dibenzoselenophene ring, azacarbazole ring, azadibenzothiophene ring, azadibenzofuran ring, azadibenzoselenophene ring, azatriphenylene ring, imidazoimidazole ring, indoloindole ring, benzofurancarbazole ring, benzothiophenocarbazole ring, indencarbazole ring, and selenophenocarbazole ring, spiro[fluorene-9,9'-xanthene] ring, spirobis[silicon fluorene] ring, etc. In addition, in the dihydroacridine ring, xanthene ring, and thioxanthene ring, it is also preferable that two of the two hydrogens of the methylene group in their structures are respectively substituted with alkyl groups such as methyl which is described later as the first substituent to form rings such as dimethyldihydroacridine ring, dimethylxanthene ring, and dimethylthioxanthene ring. In addition, as the bicyclic bipyridine ring, phenylpyridine ring, pyridylphenyl ring, and as the tricyclic terpyridine ring, bipyridylphenyl ring, pyridylbiphenyl ring can also be cited as "heteroaryl rings". In addition, the pyran ring is also included in the "heteroaryl ring".

[0146] In this specification, substituents are sometimes further substituted with additional substituents. For example, with respect to a specific substituent, it is sometimes described as "substituted or unsubstituted". This means that the specific substituent is substituted with at least one additional substituent or is unsubstituted. In the same sense, it is sometimes also referred to as "substitutable". In this specification, the specific substituent at this time is sometimes referred to as the "first substituent", and the additional substituent is referred to as the "second substituent".

[0147] In this specification, the substituent group Zα includes the substituents of the substituent group Z and the substituents represented by the following formula (A30).

[0148] In this specification, the substituent group Z includes:

[0149] aryl, which may be substituted with at least one group selected from the group consisting of aryl, heteroaryl, alkyl, cycloalkyl, cyano, and halogen,

[0150] heteroaryl, which may be substituted with at least one group selected from the group consisting of aryl, heteroaryl, alkyl, cycloalkyl, cyano, and halogen,

[0151] diaryl amino, which may be substituted with at least one group selected from the group consisting of aryl, heteroaryl, alkyl, cycloalkyl, cyano, and halogen, and the two aryl groups in the diaryl amino may be bonded to each other via a linking group,

[0152] diheteroaryl amino, which may be substituted with at least one group selected from the group consisting of aryl, heteroaryl, alkyl, cycloalkyl, cyano, and halogen, and the two heteroaryl groups in the diheteroaryl amino may be bonded to each other via a linking group,

[0153] aryl heteroaryl amino, which may be substituted with at least one group selected from the group consisting of aryl, heteroaryl, alkyl, cycloalkyl, cyano, and halogen, and the aryl group and the heteroaryl group in the aryl heteroaryl amino may be bonded to each other via a linking group,

[0154] diaryl boron group, which may be substituted with at least one group selected from the group consisting of aryl, heteroaryl, alkyl, cycloalkyl, cyano, and halogen, and the two aryl groups in the diaryl boron group may be bonded via a single bond or a linking group,

[0155] alkyl, which may be substituted with at least one group selected from the group consisting of aryl, heteroaryl, cycloalkyl, cyano, and halogen,

[0156] cycloalkyl, which may be substituted with at least one group selected from the group consisting of aryl, heteroaryl, alkyl, cycloalkyl, cyano, and halogen,

[0157] An alkoxy group, which may be substituted by at least one group selected from the group consisting of an aryl group, a heteroaryl group, a cycloalkyl group, a cyano group, and a halogen.

[0158] An aryloxy group, which may be substituted by at least one group selected from the group consisting of an aryl group, a heteroaryl group, an alkyl group, a cycloalkyl group, a cyano group, and a halogen.

[0159] An arylthio group, which may be substituted by at least one group selected from the group consisting of an aryl group, a heteroaryl group, an alkyl group, a cycloalkyl group, a cyano group, and a halogen.

[0160] An alkenyl group, which may be substituted by at least one group selected from the group consisting of an aryl group, a heteroaryl group, an alkyl group, a cycloalkyl group, a cyano group, and a halogen.

[0161] A substituted silyl group, a cyano group, and a halogen.

[0162] The aryl group as the second substituent in each group of the substituent group Z may be further substituted by an aryl group, a heteroaryl group, an alkyl group, a cycloalkyl group, a cyano group, or a halogen. Similarly, the heteroaryl group as the second substituent may be substituted by an aryl group, a heteroaryl group, an alkyl group, a cycloalkyl group, a cyano group, or a halogen.

[0163] In the present specification, in the case of being referred to as a "substituent", the type of the substituent is not particularly limited, and when there is no other special description, any group selected from the substituent group Z may be used. For example, when a "substituted or unsubstituted" group is substituted, the group only needs to be substituted by at least one group selected from the substituent group Z.

[0164] In the present specification, an "aryl group" is, for example, an aryl group having 6 to 30 carbon atoms, preferably an aryl group having 6 to 20 carbon atoms, an aryl group having 6 to 16 carbon atoms, an aryl group having 6 to 12 carbon atoms, or an aryl group having 6 to 10 carbon atoms, etc.

[0165] A specific "aryl" can be exemplified by a monovalent group formed by removing one hydrogen from the "aryl ring". For example: phenyl which is a monocyclic system, biphenyl (2-biphenyl, 3-biphenyl, or 4-biphenyl) which is a bicyclic system, naphthyl (1-naphthyl or 2-naphthyl) which is a condensed bicyclic system, terphenyl (m-terphenyl-2'-yl, m-terphenyl-4'-yl, m-terphenyl-5'-yl, o-terphenyl-3'-yl, o-terphenyl-4'-yl, p-terphenyl-2'-yl, m-terphenyl-2-yl, m-terphenyl-3-yl, m-terphenyl-4-yl, o-terphenyl-2-yl, o-terphenyl-3-yl, o-terphenyl-4-yl, p-terphenyl-2-yl, p-terphenyl-3-yl, or p-terphenyl-4-yl) which is a tricyclic system, acenaphthylen-(1-, 3-, 4-, or 5-)yl, fluoren-(1-, 2-, 3-, 4-, or 9-)yl, phenalen-(1- or 2-)yl, phenanthren-(1-, 2-, 3-, 4-, or 9-)yl, or anthracen-(1-, 2-, or 9-)yl which are condensed tricyclic systems, tetraphenyl (5'-phenyl-m-terphenyl-2-yl, 5'-phenyl-m-terphenyl-3-yl, 5'-phenyl-m-terphenyl-4-yl, or m-tetraphenyl) which is a tetracyclic system, triphenylene-(1- or 2-)yl, pyren-(1-, 2-, or 4-)yl, or tetracen-(1-, 2-, or 5-)yl which are condensed tetracyclic systems, or perylen-(1-, 2-, or 3-)yl, or pentacen-(1-, 2-, 5-, or 6-)yl which are condensed pentacyclic systems, etc. In addition, a monovalent group of spirofluorene, etc. can be exemplified.

[0166] In addition, in the aryl as the second substituent, a structure in which the aryl is substituted with at least one group selected from the group consisting of aryls such as phenyl (specific examples are the groups described above), alkyls such as methyl (specific examples are the groups described later), and cycloalkyls such as cyclohexyl or adamantyl (specific examples are the groups described later) is also included.

[0167] As an example thereof, a group in which the 9-position of a fluorenyl group as the second substituent is substituted with an aryl such as phenyl, an alkyl such as methyl, or a cycloalkyl such as cyclohexyl or adamantyl can be exemplified.

[0168] "Arylene" is, for example, an arylene having 6 to 30 carbon atoms, preferably an arylene having 6 to 20 carbon atoms, an arylene having 6 to 16 carbon atoms, an arylene having 6 to 12 carbon atoms, or an arylene having 6 to 10 carbon atoms, etc.

[0169] A specific "arylene" can be exemplified by a divalent group formed by removing one hydrogen from the "aryl" (monovalent group).

[0170] "Heteroaryl" is, for example, a heteroaryl having 2 to 30 carbon atoms, preferably a heteroaryl having 2 to 25 carbon atoms, a heteroaryl having 2 to 20 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, or a heteroaryl having 2 to 10 carbon atoms. In the "heteroaryl", in addition to carbon, there are one or more, preferably 1 to 5 heteroatoms selected from oxygen, sulfur, nitrogen, etc. as ring-constituting atoms.

[0171] As a specific "heteroaryl", a monovalent group formed by removing one hydrogen from the "heteroaryl ring" can be cited. For example: pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, pyrazolyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, indolyl, isoindolyl, 1H-indazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolinyl, isoquinolinyl, cinnolinyl, quinazolinyl, quinoxalinyl, phenanthrolinyl, phthalazinyl, naphthyridinyl, purinyl, pteridinyl, carbazolyl, acridinyl, phenoxathiinyl, phenoxazinyl, phenothiazinyl, phenazinyl, phenazasilinyl, indolizinyl, furyl, benzofuryl, isobenzofuryl, dibenzofuryl, naphthobenzofuryl, thienyl, benzothienyl, isobenzothienyl, dibenzothienyl, naphthobenzothienyl, a monovalent group of a benzophosphole oxide ring, a monovalent group of a dibenzophosphole oxide ring, furazanyl, thianthrenyl, indolocarbazolyl, benzindolocarbazolyl, dibenzindolocarbazolyl, imidazolinyl, or oxazolinyl, etc. In addition, a monovalent group of spiro[fluorene-9,9'-xanthene], a monovalent group of spirobis[silafluorene], and a monovalent group of benzoselenophene can be cited.

[0172] In addition, the heteroaryl as the second substituent also includes a structure in which the heteroaryl is substituted with at least one group selected from the group consisting of aryl groups such as phenyl (specific examples are the groups described above), alkyl groups such as methyl (specific examples are the groups described later), and cycloalkyl groups such as cyclohexyl or adamantyl (specific examples are the groups described later).

[0173] As an example, a group in which the 9-position of the carbazolyl as the second substituent is substituted with an aryl group such as phenyl, an alkyl group such as methyl, or a cycloalkyl group such as cyclohexyl or adamantyl can be cited. In addition, groups in which nitrogen-containing heteroaryls such as pyridyl, pyrimidinyl, triazinyl, and carbazolyl are further substituted with phenyl or biphenyl are also included in the heteroaryl as the second substituent.

[0174] "Heteroarylene" is, for example, a heteroarylene having 2 to 30 carbon atoms, preferably a heteroarylene having 2 to 25 carbon atoms, a heteroarylene having 2 to 20 carbon atoms, a heteroarylene having 2 to 15 carbon atoms, or a heteroarylene having 2 to 10 carbon atoms. In addition, "heteroarylene" is, for example, a divalent group such as a heterocycle containing 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen as ring-constituting atoms in addition to carbon.

[0175] Specific "heteroarylene" may be, for example, a divalent group formed by removing one hydrogen atom from the above-mentioned "heteroaryl" (monovalent group).

[0176] "Diaryl amino" is an amino group substituted by two aryl groups. For details of the aryl groups, reference may be made to the description of the above-mentioned "aryl".

[0177] "Diheteroaryl amino" is an amino group substituted by two heteroaryl groups. For details of the heteroaryl groups, reference may be made to the description of the above-mentioned "heteroaryl".

[0178] "Aryl heteroaryl amino" is an amino group substituted by an aryl group and a heteroaryl group. For details of the aryl group and the heteroaryl group, reference may be made to the descriptions of the above-mentioned "aryl" and "heteroaryl".

[0179] As the aryl group in "diaryl amino", "diheteroaryl amino" and "aryl heteroaryl amino", phenyl, biphenyl (preferably o-biphenyl), naphthyl, phenanthryl, fluorenyl or terphenyl is preferred. As the heteroaryl group in "diaryl amino", "diheteroaryl amino" and "aryl heteroaryl amino", carbazolyl, dibenzofuranyl, dibenzothiophenyl is preferred. The two aryl groups of diaryl amino may be the same or different.

[0180] The two aryl groups in the diaryl amino as the first substituent may be bonded to each other via a linking group. The two heteroaryl groups in the diheteroaryl amino as the first substituent may be bonded to each other via a linking group. The aryl group and the heteroaryl group in the aryl heteroaryl amino as the first substituent may be bonded to each other via a linking group. Here, the description "bonded via a linking group" means, for example, that the two phenyl groups of diphenyl amino form a bond through a linking group as shown below. In addition, the above description also applies to diheteroaryl amino and aryl heteroaryl amino formed by an aryl group or a heteroaryl group.

[0181] [Chemical formula 27]

[0182]

[0183] Specific examples of the linking group include: >O, >N-R X , >C(-R X )2, -C(-R X )=C(-R X )-, >Si(-R X )2, >S, >CO, >CS, >SO, >SO2, >SeO, >SeO2, >PO, >B(-R X ) and >Se. R XEach independently is an alkyl group, a cycloalkyl group, an aryl group, or a heteroaryl group, which may be substituted with an alkyl group, a cycloalkyl group, an aryl group, or a heteroaryl group. Additionally, >C(-R X )2, -C(-R X )=C(-R X )-, >Si(-R X )2, for each of the two Rs X may be bonded to each other via a single bond or a linking group X Y to form a ring. As X Y , examples include >O, >N-R Y , >C(-R Y )2, >Si(-R Y )2, >S, >CO, >CS, >SO, >SO2, and >Se, and Rs Y each independently is an alkyl group, a cycloalkyl group, an aryl group, or a heteroaryl group, which may be substituted with an alkyl group, a cycloalkyl group, an aryl group, or a heteroaryl group. Among them, when X Y is >C(-R Y )2 and >Si(-R Y )2, the two Rs Y do not bond to further form a ring. Furthermore, as a linking group, an alkenylene group may also be mentioned. Any hydrogen of the alkenylene group may be independently substituted with R 2X , and Rs 2X each independently is an alkyl group, a cycloalkyl group, a substituted silyl group, an aryl group, and a heteroaryl group, which may be substituted with an alkyl group, a cycloalkyl group, a substituted silyl group, and an aryl group. The two Rs X in -C(-R X )=C(-R X )- may bond to each other and together with the C=C to which they are bonded form an aryl ring (such as a benzene ring) or a heteroaryl ring. That is, -C(-R X )=C(-R X )- may become an arylene group (such as 1,2-phenylene) or a heteroarylene group.

[0184] In addition, in the present specification, when only "diaryl amino", "diheteroaryl amino", or "aryl heteroaryl amino" is described, unless otherwise specified, it is assumed that the explanations "the two aryl groups of the diaryl amino may be bonded to each other via a linking group", "the two heteroaryl groups of the diheteroaryl amino may be bonded to each other via a linking group", and "the aryl group and the heteroaryl group of the aryl heteroaryl amino may be bonded to each other via a linking group" are respectively added.

[0185] "Diarylboranyl" is a boranyl group in which two aryl groups are substituted. For details of the aryl groups, reference may be made to the description of "aryl". In addition, the two aryl groups may be bonded via a single bond or a linking group (e.g., -CH=CH-, -CR=CR-, -C≡C-, >N-R, >O, >S, >CO, >C=S, >S=O, >S(=O)2, >Se(=O), >Se(=O)2, >P(=O), >B(-R), >C(-R)2, >Si(-R)2, or >Se). Here, R in -CR=CR-, R in >N-R, R in >B(-R), R in >C(-R)2, and R in >Si(-R)2 is an aryl group, a heteroaryl group, a diarylamino group, an alkyl group, an alkenyl group, an alkynyl group, a cycloalkyl group, an alkoxy group, or an aryloxy group, and at least one hydrogen in the R may be further substituted with an aryl group, a heteroaryl group, an alkyl group, an alkenyl group, an alkynyl group, or a cycloalkyl group. In addition, two adjacent Rs may be bonded to each other to form a ring, forming a cycloalkylidene group, an arylene group, and a heteroarylene group. For details of the substituents listed here, reference may be made to the descriptions of "aryl", "arylene", "heteroaryl", "heteroarylene", and "diarylamino", as well as the descriptions of "alkyl", "alkenyl", "alkynyl", "cycloalkyl", "cycloalkylidene", "alkoxy", and "aryloxy" described below. In addition, in this specification, when only "diarylboranyl" is described, unless otherwise specified, it is assumed that the description "the two aryl groups of the diarylboranyl group may be bonded to each other via a single bond or a linking group" is added.

[0186] "Alkyl" may be either straight-chain or branched-chain, for example, a straight-chain alkyl group having 1 to 24 carbon atoms or a branched-chain alkyl group having 3 to 24 carbon atoms, preferably an alkyl group having 1 to 18 carbon atoms (a branched-chain alkyl group having 3 to 18 carbon atoms), an alkyl group having 1 to 12 carbon atoms (a branched-chain alkyl group having 3 to 12 carbon atoms), an alkyl group having 1 to 6 carbon atoms (a branched-chain alkyl group having 3 to 6 carbon atoms), an alkyl group having 1 to 5 carbon atoms (a branched-chain alkyl group having 3 to 5 carbon atoms), an alkyl group having 1 to 4 carbon atoms (a branched-chain alkyl group having 3 to 4 carbon atoms), etc.

[0187] Specific "alkyl groups" are, for example: methyl, ethyl, n-propyl, isopropyl, 1-ethyl-1-methylpropyl, 1,1-diethylpropyl, 1,1,2-trimethylpropyl, 1,1,2,2-tetramethylpropyl, 1-ethyl-1,2,2-trimethylpropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-ethylbutyl, 1,1-dimethylbutyl, 3,3-dimethylbutyl, 1,1-diethylbutyl, 1-ethyl-1-methylbutyl, 1-propyl-1-methylbutyl, 1,1,3-trimethylbutyl, 1-ethyl-1,3-dimethylbutyl, n-pentyl, isopentyl, neopentyl, tert-pentyl (t-pentyl) (tert-amyl), 1-methylpentyl, 2-propylpentyl, 1,1-dimethylpentyl, 1-ethyl-1-methylpentyl, 1-propyl-1-methylpentyl, 1-butyl-1-methylpentyl, 1,1,4-trimethylpentyl, n-hexyl, 1-methylhexyl, 2-ethylhexyl, 1,1-dimethylhexyl, 1-ethyl-1-methylhexyl, 1,1,5-trimethylhexyl, 3,5,5-trimethylhexyl, n-heptyl, 1-methylheptyl, 1-hexylheptyl, 1,1-dimethylheptyl, 2,2-dimethylheptyl, 2,6-dimethyl-4-heptyl, n-octyl, tert-octyl (1,1,3,3-tetramethylbutyl), 1,1-dimethyloctyl, n-nonyl, n-decyl, 1-methyldecyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, or n-icosyl, etc.

[0188] "Alkylene" is a divalent group obtained by removing any one hydrogen of "alkyl", for example: methylene, ethylene, propylene.

[0189] Regarding "alkenyl", reference may be made to the description of "alkyl" above. It is a group in which the C-C single bond in the structure of "alkyl" is replaced by a C=C double bond, and also includes a group in which not only one but two or more single bonds are replaced by double bonds (also called diene-group or triene-group).

[0190] Specifically, examples of "alkenyl" include alkenyl groups having 2 to 30 carbon atoms, preferably alkenyl groups having 2 to 20 carbon atoms, more preferably alkenyl groups having 2 to 10 carbon atoms, still more preferably alkenyl groups having 2 to 6 carbon atoms, and particularly preferably alkenyl groups having 2 to 4 carbon atoms. Preferred alkenyl groups are vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, or 5-hexenyl.

[0191] "Alkenylene" is a divalent group obtained by removing any one hydrogen of "alkenyl", and examples thereof include vinylidene.

[0192] Regarding "alkynyl", reference may be made to the description of "alkyl", which is a group in which the C-C single bond in the structure of "alkyl" is replaced by a C≡C triple bond, and also includes a group in which not only one but two or more single bonds are replaced by triple bonds (also referred to as diynyl or triynyl).

[0193] "Cycloalkyl" is, for example, a cycloalkyl having 3 to 24 carbon atoms, preferably a cycloalkyl having 3 to 20 carbon atoms, a cycloalkyl having 3 to 16 carbon atoms, a cycloalkyl having 3 to 14 carbon atoms, a cycloalkyl having 3 to 12 carbon atoms, a cycloalkyl having 5 to 10 carbon atoms, a cycloalkyl having 5 to 8 carbon atoms, a cycloalkyl having 5 to 6 carbon atoms, or a cycloalkyl having 5 carbon atoms, etc.

[0194] Specific examples of "cycloalkyl" include: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, or alkyl (especially methyl) substituents having 1 to 5 or 1 to 4 carbon atoms of these, 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 (norbornanyl), bicyclo[2.2.2]octyl, adamantyl, diadamantyl, decahydronaphthyl, or decahydroazulenyl, etc.

[0195] "Cycloalkylene" is, for example, a cycloalkylene having 3 to 24 carbon atoms, preferably a cycloalkylene having 3 to 20 carbon atoms, a cycloalkylene having 3 to 16 carbon atoms, a cycloalkylene having 3 to 14 carbon atoms, a cycloalkylene having 3 to 12 carbon atoms, a cycloalkylene having 5 to 10 carbon atoms, a cycloalkylene having 5 to 8 carbon atoms, a cycloalkylene having 5 to 6 carbon atoms, or a cycloalkylene having 5 carbon atoms, etc.

[0196] Specific examples of "cycloalkylene" can be exemplified by the structure obtained by removing one hydrogen from the above-mentioned "cycloalkyl" (monovalent group) to form a divalent group.

[0197] "Cycloalkenyl" can be exemplified by a group having a structure in which at least one of the single bonds between two carbons in the above-mentioned "cycloalkyl" becomes a double bond (for example, a group in which -CH2-CH2- is replaced by -CH=CH-), and a group not equivalent to an aryl group. Specifically, 1-cyclohexenyl, 1-cyclopentenyl, etc. can be exemplified.

[0198] "Alkoxy" is a group represented by "Alk-O- (Alk is alkyl)", and for the details of the above-mentioned alkyl, reference may be made to the description of "alkyl".

[0199] "Aryloxy" is a group represented by "Ar-O- (Ar is aryl)", and for the details of the above-mentioned aryl, reference may be made to the description of "aryl".

[0200] "Arylthio group" refers to a group represented by "Ar-S- (where Ar is an aryl group). For details of the aryl group, reference may be made to the description of the "aryl group".

[0201] "Substituted silyl group" is, for example, a silyl group substituted with at least one of an aryl group, an alkyl group, and a cycloalkyl group, preferably a triaryl silyl group, a trialkyl silyl group, a tricycloalkyl silyl group, a dialkylcycloalkyl silyl group, or an alkyl dicycloalkyl silyl group.

[0202] "Triaryl silyl group" is a silyl group substituted with three aryl groups. For details of the aryl group, reference may be made to the description of the "aryl group".

[0203] Specific examples of the "triaryl silyl group" include triphenyl silyl group, diphenylmononaphthyl silyl group, monophenyldinaphthyl silyl group, or trinaphthyl silyl group, etc.

[0204] "Trialkyl silyl group" is a silyl group substituted with three alkyl groups. For details of the alkyl group, reference may be made to the description of the "alkyl group".

[0205] Specific examples of the "trialkyl silyl group" include: trimethyl silyl group, triethyl silyl group, tri-n-propyl silyl group, triisopropyl silyl group, tri-n-butyl silyl group, triisobutyl silyl group, tri-sec-butyl silyl group, tri-tert-butyl silyl group, ethyldimethyl silyl group, n-propyldimethyl silyl group, isopropyldimethyl silyl group, n-butyldimethyl silyl group, isobutyldimethyl silyl group, sec-butyldimethyl silyl group, tert-butyldimethyl silyl group, methyldiethyl silyl group, n-propyldiethyl silyl group, isopropyldiethyl silyl group, n-butyldiethyl silyl group, sec-butyldiethyl silyl group, tert-butyldiethyl silyl group, methyldi-n-propyl silyl group, ethyldi-n-propyl silyl group, n-butyldi-n-propyl silyl group, sec-butyldi-n-propyl silyl group, tert-butyldi-n-propyl silyl group, methyldiisopropyl silyl group, ethyldiisopropyl silyl group, n-butyldiisopropyl silyl group, sec-butyldiisopropyl silyl group, or tert-butyldiisopropyl silyl group, etc.

[0206] "Tricycloalkyl silyl group" is a silyl group substituted with three cycloalkyl groups. For details of the cycloalkyl group, reference may be made to the description of the "cycloalkyl group".

[0207] Specific examples of the "tricycloalkyl silyl group" include tricyclopentyl silyl group or tricyclohexyl silyl group, etc.

[0208] "Dialkylcycloalkyl silyl group" is a silyl group substituted with two alkyl groups and one cycloalkyl group. For details of the alkyl group and the cycloalkyl group, reference may be made to the descriptions of the "alkyl group" and the "cycloalkyl group".

[0209] "Alkyl bicycloalkylsilyl" is a silyl group substituted by one alkyl group and two cycloalkyl groups. For the details of the alkyl group and cycloalkyl group, the descriptions of the "alkyl group" and "cycloalkyl group" can be cited.

[0210] "Halogen" is fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, more preferably fluorine or chlorine, and still more preferably fluorine.

[0211] In addition, when cyanide or halogen is substituted, it is also preferably in a form in which all or part of the hydrogen in the aryl group or heteroaryl group in the structure is substituted by cyanide or halogen.

[0212] The substituent represented by formula (A30) has the following structure.

[0213] [Chemical formula 28]

[0214]

[0215] In formula (A30),

[0216] Ak is hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted cycloalkyl group or a substituted or unsubstituted cycloalkenyl group, and at least one -CH2- in the alkyl group, cycloalkyl group and cycloalkenyl group can be substituted by -O- or -S-.

[0217] R Ak is a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted alkyl group or a substituted or unsubstituted cycloalkyl group. R Ak can be bonded to Ak through a linking group or a single bond, and * is the bonding position.

[0218] In formula (A30), since Ak is the substituent and is not conjugated with the non-bonding electron pair on N, the non-bonding electron pair can be conjugated with the π electrons of the bonding target. Compared with the case where an aryl group or the like is present at the same position, a greater wavelength change can be achieved. In addition, the same is true for the influence on the multiple resonance effect, and a greater improvement in thermally activated delayed fluorescence (TADF) properties can be achieved.

[0219] R Ak is preferably an aryl group that can be substituted by an alkyl group or a cycloalkyl group, a heteroaryl group that can be substituted by an alkyl group or a cycloalkyl group, an alkyl group or a cycloalkyl group, more preferably an aryl group that can be substituted by an alkyl group, a heteroaryl group that can be substituted by an alkyl group, an alkyl group or a cycloalkyl group, still more preferably an aryl group that can be substituted by an alkyl group, and particularly preferably a phenyl group that can be substituted by a methyl group.

[0220] In formula (A30), Ak is preferably an alkyl group having 1 to 6 carbon atoms or a cycloalkyl group having 3 to 14 carbon atoms, more preferably an alkyl group having 1 to 4 carbon atoms or a cycloalkyl group having 3 to 8 carbon atoms, still more preferably an alkyl group having 1 to 4 carbon atoms, and still more preferably a methyl group.

[0221] R Ak may be the same as or different from Ak, and is preferably different.

[0222] R Ak may be bonded to Ak through a linking group or a single bond. Examples of the linking group at this time include >O, >S, or >Si(-R)2, etc. R in >Si(-R)2 is hydrogen, an aryl group having 6 to 12 carbon atoms, an alkyl group having 1 to 6 carbon atoms, or a cycloalkyl group having 3 to 14 carbon atoms. As an example of the structure in which R Ak is bonded to Ak through a linking group or a single bond, the following structures can be cited.

[0223] [Chemical formula 29]

[0224]

[0225] In each of the above formulas, * is the bonding position.

[0226] [Case where two groups bonded to the same atom are bonded to each other]

[0227] In this specification, regarding two groups bonded to the same atom, when it is mentioned that they can be bonded to each other to form a ring, it is sufficient that they are bonded through a single bond or a linking group (these are also collectively referred to as bonding groups). Examples of the linking group include -CH2-CH2-, -CHR-CHR-, -CR2-CR2-, -CH=CH-, -CR=CR-, -C≡C-, -N(-R)-, -O-, -S-, -C(-R)2-, -C(=O)-, -C(=S)-, -S(=O)-, -S(=O)2-, -Se(=O)-, -Se(=O)2-, -P(=O)-, -B(-R)-, -Si(-R)2-, or -Se-. For example, the following structures can be cited. In addition, R in -CHR-CHR-, R in -CR2-CR2-, R in -CR=CR-, R in -N(-R)-, R in -C(-R)2-, R in -B(-R)-, and R in -Si(-R)2- are each independently hydrogen, an aryl group optionally substituted with an alkyl or cycloalkyl group, a heteroaryl group optionally substituted with an alkyl or cycloalkyl group, an alkyl group optionally substituted with a cycloalkyl group, an alkenyl group optionally substituted with an alkyl or cycloalkyl group, an alkynyl group optionally substituted with an alkyl or cycloalkyl group, or a cycloalkyl group optionally substituted with an alkyl or cycloalkyl group. In addition, two adjacent Rs may be bonded to each other to form a ring, and may form a sub-cycloalkyl group, a sub-aryl group, or a sub-heteroaryl group.

[0228] [Chemical formula 30]

[0229]

[0230] As the bonding group, a single bond, -CR=CR- as the linking group, -N(-R)-, -O-, -S-, -C(-R)2-, -Si(-R)2-, and -Se- are preferred, and a single bond, -CR=CR- as the linking group, -N(-R)-, -O-, -S-, and -C(-R)2- are more preferred, and further a single bond, -CR=CR- as the linking group, -N(-R)-, -O-, and -S- are even more preferred, and a single bond is most preferred.

[0231] Regarding the positions where two Rs are bonded through the bonding group, if they are positions where bonding is possible, there is no particular limitation, and bonding is preferably carried out at the closest adjacent positions. For example, when the two groups are phenyl groups, bonding is preferably carried out between the positions at the ortho position (2-position) with reference to the bonding position (1-position) of "C" or "Si" in the phenyl group (refer to the said structural formula).

[0232] <Stereoisomers, etc.>

[0233] The polycyclic aromatic compound of the present invention may have enantiomers or diastereomers depending on the type of substituents, etc. However, regardless of the structural formula described, any pure form of any stereoisomer, any mixture of stereoisomers, racemates, etc. are all included within the scope of the present invention.

[0234] <Explanation of substitution with isotopes>

[0235] In the polycyclic aromatic compound containing a structure composed of one or more of the structural units represented by formula (1), each element is an element containing multiple naturally occurring isotopes in the natural abundance ratio in the absence of special description. Among them, at least one atom of the element in each structural formula may also contain a heavy stable isotope exceeding the natural abundance ratio (for example, 90 atom% or more). In this specification, it is simply referred to as "substituted with" "heavy stable isotope". More specifically, at least one hydrogen can be substituted with deuterium, at least one nitrogen can be substituted with nitrogen-15 ( 15 N), at least one sulfur can be substituted with sulfur-33 ( 33 S), sulfur-34 ( 34 S) or sulfur-36 ( 36 S), at least one oxygen can be substituted with oxygen-17 ( 17 O) or oxygen-18 ( 18 O), at least one carbon can be substituted with carbon-13 ( 13 C), at least one boron can be substituted with boron-11 ( 11 B). By substituting at least a part of the elements with heavy stable isotopes, especially by using boron-11 (11 B) Substituting at least one boron can achieve high performance of an organic electroluminescent element using a polycyclic aromatic compound having a structure composed of one or more of the structural units represented by formula (1) as a dopant.

[0236] The polycyclic aromatic compound having a structure composed of one or more of the structural units represented by formula (1) is preferably selected from the group consisting of deuterium, nitrogen-15 ( 15 N), sulfur-33 ( 33 S), sulfur-34 ( 34 S), sulfur-36 ( 36 S), oxygen-17 ( 17 O), oxygen-18 ( 18 O), carbon-13 ( 13 C), and boron-11 ( 11 B), and is more preferably substituted with at least one selected from the group consisting of deuterium, nitrogen-15 ( 15 N), and boron-11 ( 11 B), and still more preferably substituted with deuterium. In addition, in this specification, the case of substituting hydrogen with deuterium is sometimes referred to as "substituting hydrogen with deuterium" or "deuteration", etc. That is, in one embodiment, at least one hydrogen in the polycyclic aromatic compound having a structure composed of one or more of the structural units represented by formula (1) can be substituted with deuterium.

[0237] In the description of the polycyclic aromatic compound having a structure composed of one or more of the structural units represented by formula (1), when boron is only expressed as "B" or "boron", as long as there is no special description, it means that the raw material with the natural abundance ratio of the isotope of the element is used for synthesis. In contrast, in the case of indicating the mass number of the element such as " 11 B", it means a compound obtained by synthesis using a raw material in which the abundance ratio of the target element is artificially increased as the raw material related to the element. The same applies to other elements such as hydrogen, nitrogen, sulfur, oxygen, or carbon. In addition, in the polycyclic aromatic compound of the present invention, even if the isotope ratio of at least one atom is an arbitrary ratio different from the natural ratio, it is included in the present invention.

[0238] Moreover, in the polycyclic aromatic compound of the present invention, when the specific mass number of the element is not indicated, even if the isotope ratio of at least one atom in the polycyclic aromatic compound molecule is an arbitrary ratio different from the natural ratio, it is included in the present invention.

[0239] <1. Polycyclic Aromatic Compound>

[0240] <Overall Structure>

[0241] Regarding polycyclic aromatic compounds formed by linking aromatic rings with heteroelements such as boron, nitrogen, oxygen, and sulfur, it has been found that they have a large gap between the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO) (band gap Eg in the thin film). The reason is that the aromaticity of the 6-membered ring containing heteroelements is low, and the reduction of the HOMO-LUMO gap accompanying the expansion of the conjugated system is suppressed. In addition, it has been found that the HOMO-LUMO gap can be arbitrarily changed according to the type and linking method of the heteroelements. It is considered that the reason is that the energies of the HOMO and LUMO are arbitrarily changed according to the spatial expansion and energy of the empty orbitals or lone pairs of the heteroelements.

[0242] Due to the electronic perturbation of the heteroelements in these polycyclic aromatic compounds, the singly occupied molecular orbitals (SOMO) 1 and SOMO 2 in the excited state are locally present on each atom, resulting in a narrow half-value width of the fluorescence emission peak. Therefore, when used as a dopant in an organic EL element, high-color-purity light emission can be obtained. For the same reason, ΔE S1T1 becomes smaller, showing thermally activated delayed fluorescence, and high efficiency can be obtained when used as an emission dopant in an organic EL element.

[0243] Furthermore, by introducing substituents, the energies of the HOMO and LUMO can be arbitrarily changed, so the ionization potential or electron affinity can be optimized according to the surrounding materials.

[0244] In the present invention, it has been found that, in particular, a polycyclic aromatic compound formed by linking aromatic rings such as benzene rings and benzofuran rings with heteroelements such as boron and nitrogen and having a structure composed of one or more of the structural units represented by the formula (1) containing a specific group can produce an organic electroluminescent element with a longer lifespan and higher luminous efficiency compared to polycyclic aromatic compounds with similar structures.

[0245] The polycyclic aromatic compound of the present invention is a polycyclic aromatic compound having a structure composed of one or more of the structural units represented by the formula (1).

[0246] [Chemical Formula 31]

[0247]

[0248] In formula (1), selected from X 1 and X 2At least one in the group composed of is R NX is a base represented by formula (G-1) or a base represented by formula (G-2) >N-R NX , R c1 ~R c4 At least one of is a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

[0249] [Chemical formula 32]

[0250]

[0251] The following explains each symbol in formula (1).

[0252] <Regarding Y 1 >

[0253] In formula (1), Y 1 is B, P, P=O, P=S, Al, Ga, As, Si-R or Ge-R, and R of the Si-R and the Ge-R is a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted cycloalkyl group. As R, an aryl group having 6 to 10 carbon atoms (such as phenyl, naphthyl, etc.), an alkyl group having 1 to 5 carbon atoms (such as methyl, ethyl, etc.) or a cycloalkyl group having 5 to 10 carbon atoms (preferably cyclohexyl or adamantyl) is particularly preferred.

[0254] Y 1 is preferably B, P=O or P=S, and more preferably B.

[0255] <Regarding X 1 and X 2 >

[0256] X in formula (1) 1 and X 2 are each independently >O, >N-R NX , >C(-R CX )2, >Si(-R IX )2, >S, or >Se. X 1 and X 2 are each independently preferably >N-R NX .

[0257] R NX is hydrogen, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted cycloalkyl group. As described later, formula (1) contains at least one R NX is a base represented by formula (G-1) or a base represented by formula (G-2) >N-R NX As X 1or X 2 .

[0258] R other than the group represented by formula (G-1) or the group represented by formula (G-2) NX is preferably another substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group

[0259] more preferably a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted fluorenyl group, or a substituted or unsubstituted carbazolyl group, and more preferably a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted carbazolyl group

[0260] even more preferably a phenyl group which may be substituted by an alkyl group or a cycloalkyl group (which may be substituted by an alkyl group), a fluorenyl group which may be substituted by an alkyl group or a cycloalkyl group (which may be substituted by an alkyl group), a dibenzothienyl group which may be substituted by an alkyl group or a cycloalkyl group (which may be substituted by an alkyl group), or a carbazolyl group which may be substituted by an alkyl group or a cycloalkyl group (which may be substituted by an alkyl group).

[0261] R other than the group represented by formula (G-1) or the group represented by formula (G-2) NX specifically, preferred examples include groups which may be substituted by methyl, tert-butyl, tert-pentyl or adamantyl (which may be substituted by methyl) as a phenyl group, a fluorenyl group, a carbazolyl group or a dibenzothienyl group, and most preferably a phenyl group which may be substituted by an alkyl group or a cycloalkyl group (which may be substituted by methyl).

[0262] R CX are each independently hydrogen, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted cycloalkyl group, and two Rs CX may be bonded to each other to form a ring. R CX is preferably methyl or phenyl. R IX are each independently hydrogen, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted cycloalkyl group, and two Rs IX may be bonded to each other to form a ring. R IX is preferably methyl or phenyl. In addition, as described later, R NX and / or R CX may be bonded to R a3 and / or R b1 , or R a1 and / or R c4 through a linking group or a single bond.

[0263] is selected from X 1 and X 2At least one in the group formed is R NX >N-R which is a group represented by formula (G-1) or a group represented by formula (G-2) NX . Hereinafter, R NX >N-R which is a group represented by formula (G-1) NX is sometimes referred to as ">N-(G-1)", and R NX >N-R which is a group represented by formula (G-2) NX is sometimes referred to as ">N-(G-2)". That is, either X 1 or X 2 can be >N-(G-1) or >N-(G-2), or both can be >N-(G-1) or >N-(G-2). X 1 and X 2 can each be >N-(G-1). In this case, the two >N-(G-1) can be the same or different. X 1 and X 2 can also each be >N-(G-2). In this case, the two >N-(G-2) can be the same or different. It can also be that one of X 1 and X 2 is >N-(G-1) and the other is >N-(G-2).

[0264] X 1 and X 2 are preferably such that either one is >N-(G-1) or >N-(G-2), and the other is >N-R NX (R NX can be a group represented by formula (G-1), can be a group represented by formula (G-2), or can be other groups), >C(-R CX )2, or >O, and more preferably either one is >N-(G-1) or >N-(G-2), and the other is >N-R NX (R NX can be a group represented by formula (G-1), can be a group represented by formula (G-2), or can be other groups).

[0265] The group represented by formula (G-1)

[0266] [Chemical formula 33]

[0267]

[0268] In formula (G-1), R d2 ~R d8 are each independently hydrogen or a substituent, and R d2 ~R d8Two adjacent groups among them can be bonded to each other and together with the two carbon atoms to which they are bonded, form a substituted or unsubstituted aryl ring or a substituted or unsubstituted heteroaryl ring.

[0269] As R d2 ~R d8 When it is a substituent and the substituents for the above-formed rings, at least one substituent selected from the substituent group Zα can be mentioned. Preferably, it is at least one substituent selected from the substituent group Z. More preferably, it is a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted diarylamino group.

[0270] More preferably, it is an unsubstituted alkyl group, a cycloalkyl group which may be substituted with a methyl group, an aryl group which may be substituted with an alkyl group or a cycloalkyl group (which may be substituted with a methyl group), or a heteroaryl group which may be substituted with an alkyl group or a cycloalkyl group (which may be substituted with a methyl group).

[0271] Further preferably, it is an adamantyl group (which may be substituted with a methyl group, a tert-butyl group, or a tert-pentyl group), or a phenyl group (which may be substituted with a methyl group, a tert-butyl group, a tert-pentyl group, or an adamantyl group (which may be substituted with a methyl group)). Examples of preferred substituents described later can also be referred to. When multiple of R d2 ~R d8 are substituents, the multiple substituents may be the same or different.

[0272] Preferably, R d2 ~R d8 are all hydrogen, or at least one selected from the group consisting of R d3 , R d6 and R d8 is an aryl group which may be substituted with an alkyl group (preferably a tert-butyl group), or an alkyl group (preferably a tert-butyl group), and the others are hydrogen.

[0273] As the ring formed by two adjacent groups among R d2 ~R d8 bonded to each other and together with the two carbon atoms to which they are bonded, there is no particular limitation, and examples include: benzene ring, naphthalene ring, indene ring, fluorene ring, pyridine ring, furan ring, thiophene ring, pyrrole ring, benzofuran ring, benzothiophene ring, indole ring, selenophene ring, benzoselenophene ring, etc. More preferably, it is a benzene ring. The above-formed rings may each independently have substituents. As the substituents, at least one substituent selected from the substituent group Zα can be mentioned. Preferably, it is at least one substituent selected from the substituent group Z. More preferably, it is a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted diarylamino group.

[0274] Furthermore, it is preferably an unsubstituted alkyl group, a cycloalkyl group which may be substituted by a methyl group, an aryl group which may be substituted by an alkyl group or a cycloalkyl group (which may be substituted by a methyl group), or a heteroaryl group which may be substituted by an alkyl group or a cycloalkyl group (which may be substituted by a methyl group).

[0275] Particularly preferably, it is an adamantyl group (which may be substituted by a methyl group, a tert-butyl group, or a tert-pentyl group), or a phenyl group (which may be substituted by a methyl group, a tert-butyl group, a tert-pentyl group, or an adamantyl group (which may be substituted by a methyl group)).

[0276] It is also preferably a structure in which at least one of the aryl ring or heteroaryl ring in formula (G-1) is condensed with a cycloalkane as described later. Particularly preferably, it is a structure in which a partial structure represented by formula (B-1) or formula (B-2) described later is bonded.

[0277] In formula (G-1), * represents the bonding position to the nitrogen atom (>N-R NX of N).

[0278] Examples of the group represented by formula (G-1) are as follows. In the following formulas, * represents the bonding position to the nitrogen atom.

[0279] [Chemical formula 34]

[0280]

[0281] Among formulas (G-1-1) to (G-1-34), the group represented by formula (G-1-1), formula (G-1-2), formula (G-1-3), formula (G-1-4), formula (G-1-7), formula (G-1-8), formula (G-1-9), formula (G-1-10), formula (G-1-11), formula (G-1-12), formula (G-1-13), formula (G-1-14), formula (G-1-15), formula (G-1-16), formula (G-1-17), formula (G-1-18), formula (G-1-19), formula (G-1-20), formula (G-1-21), formula (G-1-25), formula (G-1-26), formula (G-1-27), formula (G-1-28), formula (G-1-33), or formula (G-1-34) is preferred; the group represented by formula (G-1-1), formula (G-1-2), formula (G-1-3), formula (G-1-4), formula (G-1-5), formula (G-1-7), formula (G-1-8), formula (G-1-11), formula (G-1-12), formula (G-1-13), formula (G-1-14), formula (G-1-15), formula (G-1-16), formula (G-1-17), formula (G-1-18), formula (G-1-19), formula (G-1-20), formula (G-1-21), formula (G-1-33), or formula (G-1-34) is more preferred; the group represented by formula (G-1-1), formula (G-1-2), formula (G-1-3), formula (G-1-4), formula (G-1-7), or formula (G-1-8) is still more preferred; and the group represented by formula (G-1-1), formula (G-1-2), formula (G-1-3), formula (G-1-4), or formula (G-1-8) is most preferred.

[0282] The group represented by formula (G-2)

[0283] [Chemical formula 35]

[0284]

[0285] In formula (G-2), * represents the bonding position to the nitrogen atom (>N-R NX of N), and R e2 to R e10 are each independently hydrogen or a substituent. Among them, at least one selected from the group consisting of R e6 to R e10 is a substituent e, or at least one of the aryl ring or heteroaryl ring in formula (G-2) is condensed with at least one cycloalkane, at least one hydrogen in the cycloalkane may be substituted, and at least one -CH2- in the cycloalkane may be substituted with -O-. In addition, when the benzene ring to which R e2 to R e5 is bonded is condensed with a cycloalkane as described above, and Re6 ~R e10 When the benzene ring to which it is bonded is not condensed with a cycloalkane as described above, it is preferable that at least one selected from the group consisting of R e6 ~R e10 is a substituent e. The substituent e is a substituent selected from the group consisting of an alkyl group, a cycloalkyl group which may be substituted with at least one alkyl group, and an aryl group which may be substituted with at least one alkyl group or a cycloalkyl group which may be substituted with an alkyl group.

[0286] As the substituent e, an unsubstituted alkyl group, a cycloalkyl group which may be substituted with a methyl group, or an aryl group which may be substituted with an alkyl group or a cycloalkyl group (which may be substituted with a methyl group) is more preferable, and further preferably a methyl group, a tert-butyl group, a tert-pentyl group, a adamantyl group which may be substituted with a methyl group, or a phenyl group (which may be substituted with a methyl group, a tert-butyl group, a tert-pentyl group or an adamantyl group which may be substituted with a methyl group).

[0287] In addition, as described above, when the formula (G-2) has a structure condensed with a cycloalkane, it also corresponds to a structure in which two adjacent groups in R e2 ~R e5 are bonded to each other, it is preferable that at least one selected from the group consisting of R e6 ~R e10 is a substituent e.

[0288] As the substituent when R e2 ~R e10 is a substituent, at least one substituent selected from the substituent group Zα can be mentioned, preferably at least one substituent selected from the substituent group Z, more preferably a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted diarylamino group,

[0289] more preferably an unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, or an aryl group which may be substituted with an alkyl group, and further preferably a methyl group, a tert-butyl group, a tert-pentyl group, a adamantyl group which may be substituted with a methyl group, or a phenyl group (which may be substituted with a methyl group, a tert-butyl group, a tert-pentyl group or an adamantyl group which may be substituted with a methyl group), particularly preferably a methyl group, a tert-butyl group, or a phenyl group which may be substituted with a tert-butyl group. Examples of preferred substituents described later can also be referred to. When a plurality of R e2 ~R e10 are substituents, the plurality of substituents may be the same or different.

[0290] R e2 ~R e10 preferably has 1 to 4 substituents and the others are hydrogen, and more preferably has 1 to 3 substituents and the others are hydrogen. For example, a structure in which R e9 is a substituent, Re8 is the structure of the substituent, or R e7 and R e9 is the structure of the substituent, etc. Particularly preferably, R e8 is a substituent.

[0291] It is also preferred that the aryl ring or heteroaryl ring in formula (G-2) has a structure condensed with a cycloalkane as described later. At least one hydrogen in the cycloalkane may be substituted, and at least one -CH2- in the cycloalkane may be substituted by -O-. The structure condensed with the cycloalkane corresponds to R e2 ~R e10 Two adjacent groups in are bonded to each other and together with the two carbon atoms to which they are bonded form a cycloolefin (such as cyclohexene, cyclopentene, etc.) structure. This structure is preferably the partial structure represented by formula (B-1) or formula (B-2) described later.

[0292] As an example of the group represented by formula (G-2), more specifically, a group represented by any of the following formulas can be cited. In the following formulas, * represents the bonding position to the nitrogen atom. In addition, at least one hydrogen of the benzene ring of the group represented by each of the following formulas may be substituted by a methyl group.

[0293] [Chemical formula 36]

[0294]

[0295] [Chemical formula 37]

[0296]

[0297] Among the above, the group represented by formula (G-2-1), formula (G-2-2), formula (G-2-3), formula (G-2-4), formula (G-2-5), formula (G-2-8), formula (G-2-9), formula (G-2-10), formula (G-2-12), formula (G-2-13), formula (G-2-14), formula (G-2-15), formula (G-2-16), or formula (G-2-17) is preferred, and the group represented by formula (G-2-1), formula (G-2-2), formula (G-2-8), formula (G-2-9) or formula (G-2-10), formula (G-2-12) is more preferred.

[0298] R NX is bonded to R via a linking group or a single bond a3 and / or R b1 or R a1 and / or R c4 in a bonded situation

[0299] In formula (1), as X 1 or X 2 in >N-R NX and >C(-R CX )2, R NX and R CX can be respectively bonded to R a3 and / or Rb1 , or R a1 and / or R c4 bond. That is, X 1 R NX and R CX can be connected to R by a linking group or a single bond a3 and / or R b1 Bond, X 2 R NX and R CX can be connected to R a1 and / or R c4 As the linking group, it is preferred that -O-, -S-, -C(=O)- or -C(-R 13 )2-. For example, to introduce X relative to the a ring which is a benzene ring 1 and X 2 It can be formed in any one of the following ways, so that, for example, a carbazole ring, a phenoxazine ring, a phenothiazine ring or an acridone ring can be formed.

[0300] In addition, it is also preferred that >NR NX R NX is a substituted or unsubstituted cycloalkyl group, and R a3 , R a1 , R b1 or R c4 The cycloalkyl group is preferably a substituted or unsubstituted cyclopentyl group or a substituted or unsubstituted cyclohexyl group.

[0301] As a particularly preferred example of the fused ring formed as described above, there can be mentioned a structure represented by formula (A11). In formula (A11), * in "as X" 1 or X 2 NR NX and>C(-R CX )2 in R NX and R CX can be connected to R by a linking group or a single bond a3 and / or R b1 , or R a1 and / or R c4 The definition of "bonded" corresponds to a form of bonding via a single bond. As described above, in this case, the two carbon atoms substituted by the methyl group are asymmetric carbon atoms, and the compound represented by formula (1) may exist in diastereomers and enantiomers. The compound represented by formula (1) may be any of these isomers, and may also be a form in which possible isomers are mixed in any ratio.

[0302] [Chemistry 38]

[0303]

[0304] In formula (A11), at the position of * and **, 1 or X 2 One of the two rings to be bonded is bonded to the other ring at the best position.

[0305] Similarly, examples include >NR NX R NX The following examples are examples of a form in which the phenyl group is bonded to the a ring, b ring or c ring via a single bond.

[0306] [Chemistry 39]

[0307]

[0308] In formula (A12), at the position of * and **, 1 or X 2 One of the two rings to be bonded is bonded to the other ring at the best position.

[0309] <R a1 ~R a3 , R b1 ~R b4 and R c1 ~R c4 >

[0310] In formula (1), R a1 ~R a3 , R b1 ~R b4 and R c1 ~R c4 are independently hydrogen or a substituent, R a1 ~R a3 , R b1 ~R b4 and R c1 ~R c4 The two adjacent groups in the formula (R) may be bonded to each other and, together with the two carbon atoms to which they are bonded, form a substituted or unsubstituted aryl ring or a substituted or unsubstituted heteroaryl ring, wherein R c1 ~R c4 At least one of is a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group.

[0311] As R a1 ~R a3 , R b1 ~R b4 and R c1 ~R c4When it is a substituent, as the substituent for the formed ring above, at least one substituent selected from the substituent group Zα can be cited, preferably at least one substituent selected from the substituent group Z.

[0312] More preferably, it is a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted aryl heteroaryl amino group, or a substituted or unsubstituted diarylamino group.

[0313] Furthermore preferably, it is an unsubstituted alkyl group, a cycloalkyl group which may be substituted with a methyl group, an aryl group which may be substituted with an alkyl group or a cycloalkyl group (which may be substituted with a methyl group), a heteroaryl group which may be substituted with an alkyl group or a cycloalkyl group (which may be substituted with a methyl group), a diarylamino group which may be substituted with an alkyl group or a cycloalkyl group (which may be substituted with a methyl group), an aryl heteroaryl amino group which may be substituted with an alkyl group or a cycloalkyl group (which may be substituted with a methyl group), or a carbazolyl group which may be substituted with an alkyl group or a cycloalkyl group (which may be substituted with a methyl group).

[0314] Particularly preferably, it is a methyl group, a tert-butyl group, a tert-pentyl group, an adamantyl group which may be substituted with a methyl group, or any of the following groups which may be substituted with a methyl group, a tert-butyl group, a tert-pentyl group or an adamantyl group (which may be substituted with a methyl group):

[0315] A phenyl group, a phenyl dibenzofuranyl amino group, a biphenyl dibenzofuranyl amino group, or a naphthyl dibenzofuranyl amino group, a diphenylamino group, a phenyl naphthyl amino group, or a phenyl biphenyl amino group, a carbazolyl group.

[0316] It may also have the following structure: In the aryl ring or heteroaryl ring of the aryl group, the heteroaryl group, the diarylamino group, the aryl heteroaryl amino group, the phenyl group, the carbazolyl group, the phenyl dibenzofuranyl amino group, the biphenyl dibenzofuranyl amino group, the naphthyl dibenzofuranyl amino group, the diphenylamino group, the phenyl naphthyl amino group, the phenyl biphenyl amino group, the carbazolyl group, any two adjacent carbon atoms are bonded with a partial structure represented by the following formula (B-1) or formula (B-2). As the substituent, examples of the preferred substituents described later can also be referred to. In addition, particularly preferably, it is a tert-butyl group.

[0317] R c1 ~R c4 At least one of them is a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group. Here, the substituent for the aryl group or the heteroaryl group is preferably selected from the group consisting of an alkyl group and a substituted or unsubstituted cycloalkyl group (preferably a cycloalkyl group which may be substituted with a methyl group, and more preferably an adamantyl group which may be substituted with a methyl group).

[0318] R c1 ~R c4At least one of them is preferably an aryl group that can be alkyl-substituted, more preferably a phenyl group that can be alkyl-substituted, and still more preferably an unsubstituted phenyl group.

[0319] R c1 ~R c4 Among them, one or two are preferred, and still more preferably one is a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group. The group that is a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group is preferably one or two of R c2 and R c3 Among them, more preferably one of R c2 and R c3 Among them, still more preferably any one of R c3 . Particularly preferably, R c3 is a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group (preferably a phenyl group that can be tert-butyl-substituted), and R c1 , R c2 and R c4 are all hydrogen.

[0320] In R a1 ~R a3 Among them, preferably R a2 is hydrogen or a substituent, and R a1 and R a3 are each hydrogen. As the substituent when R a2 is a substituent, preferably a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted aryl heteroaryl amino group, or a substituted or unsubstituted diarylamino group,

[0321] More preferably, an unsubstituted alkyl group, a cycloalkyl group that can be methyl-substituted, an aryl group that can be substituted by an alkyl group or a cycloalkyl group (which can be methyl-substituted), a heteroaryl group that can be substituted by an alkyl group or a cycloalkyl group (which can be methyl-substituted), a diarylamino group that can be substituted by an alkyl group or a cycloalkyl group (which can be methyl-substituted), an aryl heteroaryl amino group that can be substituted by an alkyl group or a cycloalkyl group (which can be methyl-substituted), a carbazolyl group that can be substituted by an alkyl group or a cycloalkyl group (which can be methyl-substituted),

[0322] Still more preferably, methyl, tert-butyl, tert-pentyl, an adamantyl group that can be methyl-substituted, or any of the following groups that can be substituted by methyl, tert-butyl, tert-pentyl or an adamantyl group (which can be methyl-substituted): phenyl, phenyl dibenzofuranyl amino group, biphenyl dibenzofuranyl amino group, or naphthyl dibenzofuranyl amino group, diphenylamino group, phenyl naphthyl amino group, or phenyl biphenyl amino group, carbazolyl group.

[0323] It is also preferably in the following structure: in the aryl ring or heteroaryl ring of the aryl, heteroaryl, diarylamino, arylheteroarylamino, phenyl, phenyldibenzofuranylamino, biphenyldibenzofuranylamino, naphthyldibenzofuranylamino, diphenylamino, phenylnaphthylamino, phenylbiphenylamino, carbazolyl, any two adjacent carbon atoms are bonded with the partial structure represented by the following formula (B-1) or formula (B-2).

[0324] As R a2 , it is more preferably tert-butyl, diphenylamino or carbazolyl, and further preferably tert-butyl.

[0325] In R b1 ~R b4 , it is preferred that R b2 or R b3 is hydrogen or a substituent, and the others are hydrogen respectively. More preferably, R b2 or R b3 is a substituent, and the others are hydrogen respectively. Further preferably, R b2 is a substituent, and the others are hydrogen respectively.

[0326] As R b1 ~R b4 (especially R b2 or R b3 ) is a substituent, the substituent is preferably a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted diarylamino group, a substituted or unsubstituted arylheteroarylamino group, or a substituted or unsubstituted carbazolyl group,

[0327] More preferably, it is an unsubstituted alkyl group, a cycloalkyl group that can be substituted by methyl, an aryl group that can be substituted by an alkyl group or a cycloalkyl group (which can be substituted by methyl), a heteroaryl group that can be substituted by an alkyl group or a cycloalkyl group (which can be substituted by methyl), a diarylamino group that can be substituted by an alkyl group or a cycloalkyl group (which can be substituted by methyl), an arylheteroarylamino group that can be substituted by an alkyl group or a cycloalkyl group (which can be substituted by methyl), or a carbazolyl group that can be substituted by an alkyl group or a cycloalkyl group (which can be substituted by methyl),

[0328] Further preferably, it is methyl, tert-butyl, tert-pentyl, adamantyl that can be substituted by methyl, or any of the following groups that can be substituted by methyl, tert-butyl, tert-pentyl or adamantyl (which can be substituted by methyl): phenyl, phenyldibenzofuranylamino, biphenyldibenzofuranylamino, naphthyldibenzofuranylamino, diphenylamino, phenylnaphthylamino, phenylbiphenylamino, carbazolyl.

[0329] It is also preferably a structure in which any two adjacent carbon atoms in the aryl group, the heteroaryl group, the diarylamino group, the arylheteroarylamino group, the phenyl group, the carbazolyl group, the phenyldibenzofuranylamino group, the biphenyldibenzofuranylamino group, the naphthyldibenzofuranylamino group, the diphenylamino group, the phenylnaphthylamino group, the phenylbiphenylamino group, the aryl ring or the heteroaryl ring are bonded to a partial structure represented by the formula (B-1) or the formula (B-2) described later.

[0330] As R b1 ~R b4 The substituent is preferably a substituted or unsubstituted diarylamino group, a substituted or unsubstituted arylheteroarylamino group, or a substituted or unsubstituted carbazolyl group, more preferably a tert-butyl group, a diphenylamino group which may be substituted by a tert-butyl group or a phenyl group, or a carbazolyl group which may be substituted by a tert-butyl group or a phenyl group, and further preferably a tert-butyl group or a diphenylamino group which may be substituted by a tert-butyl group or a phenyl group.

[0331] As R a1 ~R a3 , R b1 ~R b4 and R c1 ~R c4 The ring formed by two adjacent groups bonded to each other and the two carbon atoms bonded to them is not particularly limited, and examples thereof include: a benzene ring, a naphthalene ring, an indene ring, a fluorene ring, a pyridine ring, a furan ring, a thiophene ring, a pyrrole ring, a benzofuran ring, a benzothiophene ring, an indole ring, a selenophene ring, a benzoselenophene ring, or a carbazole ring, and is preferably a benzene ring, a naphthalene ring, an indene ring, a benzofuran ring, a benzothiophene ring, an indole ring, or a carbazole ring. In addition, R is also preferably c1 ~R c4 The situation where two adjacent groups are bonded to each other without forming a ring.

[0332] As a more preferable embodiment of the polycyclic aromatic compound represented by the formula (1), a polycyclic aromatic compound represented by the following formula (1-A) can be mentioned.

[0333] [Chemistry 40]

[0334]

[0335] In formula (1-A), the definitions of symbols and the like in the formula and their preferred ranges can be referred to the description in the present specification.

[0336] <Structure composed of one or two or more structural units>

[0337] The polycyclic aromatic compound of the present invention is a polycyclic aromatic compound having a structure composed of one or more of the structural units represented by formula (1). As the polycyclic aromatic compound having a structure composed of one of the structural units, the polycyclic aromatic compound represented by formula (1) can be cited. As the polycyclic aromatic compound having a structure composed of two or more of the structural units represented by formula (1), a compound corresponding to a polymer of the polycyclic aromatic compound represented by the formula described above as the structural unit represented by formula (1) can be cited. The polymer is preferably a dimer to hexamer, more preferably a dimer to trimer, and particularly preferably a dimer. The polymer only needs to be in a form having a plurality of the structural units in one compound, and may be in a form bonded in such a way that any ring (a ring, b ring or c ring) contained in the structural unit is shared among the plurality of structural units, or may be in a form bonded in such a way that any rings (a ring, b ring or c ring) contained in the structural unit are condensed with each other. In addition, it may also be in a form in which a plurality of the structural units are bonded by a linking group such as a single bond, an alkylene group having 1 to 3 carbon atoms, a phenylene group, or a naphthylene group. Among these, a form bonded by sharing a ring is preferred.

[0338] <Preferred substituents>

[0339] Among polycyclic aromatic compounds used as emission dopants (and also among compounds used as dopants), as a substituent containing "alkyl", the tertiary alkyl group represented by the following formula (tR) is one of the particularly preferred groups. The reason is that due to such a bulky substituent, the intermolecular distance increases, and thus the luminescence quantum yield (photoluminescence quantum yield, PLQY) is improved. In addition, a substituent in which the tertiary alkyl group represented by formula (tR) is substituted on another substituent is also preferred. Specifically, a diarylamino group substituted with the tertiary alkyl group represented by formula (tR), a carbazolyl group (preferably an N-carbazolyl group) substituted with the tertiary alkyl group represented by formula (tR), or a benzocarbazolyl group (preferably an N-benzocarbazolyl group) substituted with the tertiary alkyl group represented by formula (tR) can be cited. As the substitution form of the group of formula (tR) for the diarylamino group, carbazolyl group, and benzocarbazolyl group, examples in which part or all of the hydrogen of the aryl ring or benzene ring in these groups is substituted with the group of formula (tR) can be cited.

[0340] [Chemical formula 41]

[0341]

[0342] In formula (tR), R a 、R b and R cEach is independently an alkyl group having 1 to 24 carbon atoms, any -CH2- in the alkyl group may be replaced by -O-, and the group represented by formula (tR) has * as the bonding position.

[0343] As R a 、R b and R c The "alkyl group having 1 to 24 carbon atoms" for R, R, and R can be either a straight-chain or a branched-chain, and examples include: a straight-chain alkyl group having 1 to 24 carbon atoms or a branched-chain alkyl group having 3 to 24 carbon atoms, an alkyl group having 1 to 18 carbon atoms (a branched-chain alkyl group having 3 to 18 carbon atoms), an alkyl group having 1 to 12 carbon atoms (a branched-chain alkyl group having 3 to 12 carbon atoms), an alkyl group having 1 to 6 carbon atoms (a branched-chain alkyl group having 3 to 6 carbon atoms), an alkyl group having 1 to 4 carbon atoms (a branched-chain alkyl group having 3 to 4 carbon atoms).

[0344] R in formula (tR) a 、R b and R c The total number of carbon atoms of R, R, and R is preferably 3 to 20 carbon atoms, and particularly preferably 3 to 10 carbon atoms.

[0345] As R a 、R b and R c Specific examples of the alkyl group for R, R, and R include: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 2,6-dimethyl-4-heptyl, 3,5,5-trimethylhexyl, n-decyl, n-undecyl, 1-methyldecyl, n-dodecyl, n-tridecyl, 1-hexylheptyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, n-eicosyl, etc.

[0346] Examples of the group represented by the formula (tR) include a tert-butyl group, a tert-pentyl group, a 1-ethyl-1-methylpropyl group, a 1,1-diethylpropyl group, a 1,1-dimethylbutyl group, a 1-ethyl-1-methylbutyl group, a 1,1,3,3-tetramethylbutyl group, a 1,1,4-trimethylpentyl group, a 1,1,2-trimethylpropyl group, a 1,1-dimethyloctyl group, a 1,1-dimethylpentyl group, a 1,1-dimethylheptyl group, a 1,1,5-trimethylhexyl group, a 1-ethyl-1-methylhexyl group, a 1-ethyl-1,3-dimethylbutyl group, a 1,1,2,2-tetramethylpropyl group, a 1-butyl-1-methylpentyl group, a 1,1-diethylbutyl group, a 1-ethyl-1-methylpentyl group, a 1,1,3-trimethylbutyl group, a 1-propyl-1-methylpentyl group, a 1,1,2-trimethylpropyl group, a 1-ethyl-1,2,2-trimethylpropyl group, a 1-propyl-1-methylbutyl group, a 1,1-dimethylhexyl group, etc. Among these, a tert-butyl group and a tert-pentyl group are preferred.

[0347] As the substituent, a substituent represented by the formula (A30) is also preferred.

[0348] The emission wavelength can be adjusted by the steric hindrance, electron-donating property, and electron-withdrawing property of the structure of the substituent of the compound used as a dopant (co-dopant or emission dopant). Preferred are groups represented by the following structural formulas, more preferably a methyl group, a tert-butyl group, a tert-pentyl group, a tert-octyl group, a neopentyl group, an adamantyl group, a phenyl group, an o-tolyl group, a p-tolyl group, a 2,4-xylyl group, a 2,5-xylyl group, a 2,6-xylyl group, a 2,4,6-mesityl group, a diphenylamino group, a di-p-tolylamino group, a bis(p-(tert-butyl)phenyl)amino group, a carbazolyl group, a 3,6-dimethylcarbazolyl group, a 3,6-di-tert-butylcarbazolyl group, and a phenoxy group, and still more preferably a methyl group, a tert-butyl group, a tert-pentyl group, a tert-octyl group, a neopentyl group, an adamantyl group, a phenyl group, an o-tolyl group, a 2,6-xylyl group, a 2,4,6-mesityl group, a diphenylamino group, a di-p-tolylamino group, a bis(p-(tert-butyl)phenyl)amino group, a carbazolyl group, a 3,6-dimethylcarbazolyl group, a 3,6-di-tert-butylcarbazolyl group, and a tribenzoazepinyl group. From the viewpoint of ease of synthesis, groups with large steric hindrance are preferred because of selective synthesis. Specifically, preferred are a tert-butyl group, a tert-pentyl group, a tert-octyl group, an adamantyl group, an o-tolyl group, a p-tolyl group, a 2,4-xylyl group, a 2,5-xylyl group, a 2,6-xylyl group, a 2,4,6-mesityl group, a di-p-tolylamino group, a bis(p-(tert-butyl)phenyl)amino group, a 3,6-dimethylcarbazolyl group, and a 3,6-di-tert-butylcarbazolyl group.

[0349] In the following structural formula, * indicates the bonding position.

[0350] [Chemical formula 42]

[0351]

[0352] [Chemical formula 43]

[0353]

[0354] [Chemical formula 44]

[0355]

[0356] [Chemical formula 45]

[0357]

[0358] [Chemical formula 46]

[0359]

[0360] [Chemical formula 47]

[0361]

[0362] [Chemical formula 48]

[0363]

[0364] [Chemical formula 49]

[0365]

[0366] [Chemical formula 50]

[0367]

[0368] [Chemical formula 51]

[0369]

[0370] [Chemical formula 52]

[0371]

[0372] [Chemical formula 53]

[0373]

[0374] [Chemical formula 54]

[0375]

[0376] [Chemical formula 55]

[0377]

[0378] A polycyclic aromatic compound having a structure composed of one or more of the structural units represented by the formula (1) preferably has a structure containing at least one tertiary alkyl group (such as tert-butyl or tert-amyl), neopentyl group, or adamantyl group represented by the formula (tR), more preferably contains a tertiary alkyl group (such as tert-butyl or tert-amyl) represented by the formula (tR). The reason is that through such a bulky substituent, the intermolecular distance increases, and thus the luminescence quantum yield (PLQY) is improved. In addition, as the substituent, a diarylamino group is also preferred. Further, a diarylamino group substituted with a group of the formula (tR), a carbazolyl group substituted with a group of the formula (tR) (preferably an N-carbazolyl group), or a benzocarbazolyl group substituted with a group of the formula (tR) (preferably an N-benzocarbazolyl group) is also preferred. As the substitution form of the group of the formula (tR) for the diarylamino group, carbazolyl group, and benzocarbazolyl group, examples include those in which hydrogen of a part or all of the aryl ring or benzene ring in these groups is substituted with a group of the formula (tR).

[0379] In a structure composed of one or more of the structural units represented by the formula (1), the substituent of the aryl ring or heteroaryl ring may be a substituent represented by the following formula (A20).

[0380] [Chemical formula 56]

[0381]

[0382] The substituent represented by the formula (A20) is bonded to two atoms adjacent to each other on the ring of the aryl ring or heteroaryl ring at the two * positions respectively. In the formula (A20), L is >N-R, >O, >Si(-R)2, or >S, the R of >N-R is a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted cycloalkyl group, the R of >Si(-R)2 is hydrogen, a substitutable aryl group, a substitutable alkyl group, or a substitutable cycloalkyl group, and they may be bonded to each other through a linking group. In addition, at least one of the R of >N-R and >Si(-R)2 may be bonded to the aryl ring or heteroaryl ring through a linking group or a single bond.

[0383] r is an integer from 1 to 4.

[0384] R A are each independently hydrogen, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted cycloalkyl group, and any R A may be bonded to any other R A through a linking group or a single bond.

[0385] Examples of the substituent include substituents represented by any of the following.

[0386] [Chemical formula 57]

[0387]

[0388] In each formula, it is only necessary to bond to two or three atoms that are consecutive (adjacent) on the ring of any aryl ring or heteroaryl ring at the * position, respectively.

[0389] <Cycloalkane condensation>

[0390] At least one selected from the group consisting of aryl rings and heteroaryl rings in a polycyclic aromatic compound having a structure composed of one or more structural units represented by formula (1) may be condensed with at least one cycloalkane. Among them, the case where the aryl ring and heteroaryl ring at the position of R c1 ~R c4 are not condensed with cycloalkanes is one of the preferred forms.

[0391] As the cycloalkane, a cycloalkane having 3 to 24 carbon atoms is sufficient. At least one hydrogen in the cycloalkane at this time may be substituted with an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, an alkyl group having 1 to 24 carbon atoms, or a cycloalkyl group having 3 to 24 carbon atoms, and at least one -CH2- in the cycloalkane may be substituted with -O-.

[0392] The cycloalkane is preferably a cycloalkane having 3 to 20 carbon atoms, and at least one hydrogen in the cycloalkane may be substituted with an aryl group having 6 to 16 carbon atoms, a heteroaryl group having 2 to 22 carbon atoms, an alkyl group having 1 to 12 carbon atoms, or a cycloalkyl group having 3 to 16 carbon atoms.

[0393] Examples of the "cycloalkane" include cycloalkanes having 3 to 24 carbon atoms, cycloalkanes having 3 to 20 carbon atoms, cycloalkanes having 3 to 16 carbon atoms, cycloalkanes having 3 to 14 carbon atoms, cycloalkanes having 5 to 10 carbon atoms, cycloalkanes having 5 to 8 carbon atoms, cycloalkanes having 5 to 6 carbon atoms, cycloalkanes having 5 carbon atoms, and the like.

[0394] Specific examples of the cycloalkane include cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctane, cyclononane, cyclodecane, norbornane (bicyclo[2.2.1]heptane), bicyclo[1.1.0]butane, bicyclo[1.1.1]pentane, bicyclo[2.1.0]pentane, bicyclo[2.1.1]hexane, bicyclo[3.1.0]hexane, bicyclo[2.2.2]octane, adamantane, diamantane, decahydronaphthalene, decahydroazulene, and C1-C5 alkyl (especially methyl) substituents, halogen (especially fluorine) substituents, deuterium substituents, etc. of these.

[0395] In the above example, a structure having at least one substituent on the carbon at the α-position of the cycloalkane (in the cycloalkane condensed to an aryl ring or a heteroaryl ring, the carbon at the position adjacent to the carbon at the condensation site) is preferably as shown in the following structural formula, more preferably a structure having two substituents on the carbon at the α-position, and still more preferably a structure in which both α-position carbons have two substituents (a structure having a total of four substituents). Examples of the substituent include an alkyl group having 1 to 5 carbon atoms (especially a methyl group), a halogen (especially fluorine), and deuterium. Particularly preferred is a structure in which a partial structure represented by the following formula (B-1) or formula (B-2) is bonded to adjacent carbon atoms in an aryl ring or a heteroaryl ring.

[0396] [Chemical formula 58]

[0397]

[0398] In formula (B-1) and formula (B-2), * represents the bonding position (the position bonded to adjacent ring-constituting atoms respectively).

[0399] The number of cycloalkanes condensed to one aryl ring or heteroaryl ring is preferably 1 to 3, more preferably 1 or 2, and still more preferably 1. For example, examples of one or more cycloalkanes condensed to one benzene ring (phenyl) are shown below. * represents the bonding position, and the position can be any carbon atom constituting the benzene ring and not constituting the cycloalkane. The cycloalkanes condensed as in formula (Cy-1-4) and formula (Cy-2-4) can also be condensed with each other. This is the same whether the condensed ring (group) is an aryl ring or a heteroaryl ring other than the benzene ring (phenyl), or the condensed cycloalkane is a cycloalkane other than cyclopentane or cyclohexane.

[0400] [Chemical formula 59]

[0401]

[0402] At least one -CH2- in the cycloalkane can be replaced by -O-. For example, examples of one or more -CH2- in the cycloalkane condensed to one benzene ring (phenyl) being replaced by -O- are shown below. This is the same whether the condensed ring (group) is an aryl ring or a heteroaryl ring other than the benzene ring (phenyl), or the condensed cycloalkane is a cycloalkane other than cyclopentane or cyclohexane.

[0403] [Chemical formula 60]

[0404]

[0405] The cycloalkane may be substituted with at least one substituent, and as the substituent, any substituent selected from the substituent group Z can be cited. Among these substituents, an alkyl group (for example, an alkyl group having 1 to 6 carbon atoms) and a cycloalkyl group (for example, a cycloalkyl group having 3 to 14 carbon atoms) are preferable. In addition, it is also preferable that any hydrogen is substituted with a halogen (for example, fluorine) or deuterium. In addition, when the cycloalkyl group is substituted, it may be a substitution form that forms a spiro ring structure. For example, the following shows an example in which a spiro ring structure is formed in a cycloalkane condensed to one benzene ring (phenyl group). Regarding *, in the case of a benzene ring, it refers to the benzene ring contained in the skeleton structure of the compound, and in the case of a phenyl group, it refers to the bonding bond substituted in the skeleton structure of the compound.

[0406] [Chemical formula 61]

[0407]

[0408] As the form of condensation of the cycloalkane, first, there can be cited the form in which the a-ring, b-ring, and c-ring in a polycyclic aromatic compound having a structure composed of one or more of the structural units represented by the formula (1) are condensed with the cycloalkane, and the form in which the aryl ring or heteroaryl ring in R a1 ~R a3 , and R b1 ~R b4 is condensed with the cycloalkane. In addition, in the polycyclic aromatic compound of the present invention, the case where the aryl ring or heteroaryl ring in R c1 ~R c4 is not condensed with the cycloalkane becomes one of the preferred forms.

[0409] As other forms of condensation of the cycloalkane, there can be cited a polycyclic aromatic compound having a structure composed of one or more of the structural units represented by the formula (1) and having, for example, >N-R NX in which R NX is an aryl group condensed with the cycloalkane, a diarylamino group condensed with the cycloalkane (condensed to its aryl part), a carbazolyl group condensed with the cycloalkane (condensed to its benzene ring part), or a benzocarbazolyl group condensed with the cycloalkane (condensed to its benzene ring part).

[0410] In addition, by introducing a cycloalkane structure into a polycyclic aromatic compound having a structure composed of one or more of the structural units represented by the formula (1), a further decrease in the melting point or sublimation temperature can be expected. This means that in sublimation purification, which is almost indispensable as a purification method for materials for organic devices such as organic EL elements that require high purity, purification can be carried out at a lower temperature, so thermal decomposition of the material can be avoided. In addition, the same applies to the vacuum evaporation process, which is a powerful means for fabricating organic devices such as organic EL elements. The process can be carried out at a lower temperature, so thermal decomposition of the material can be avoided, and as a result, high-performance organic devices can be obtained. In addition, since the solubility in an organic solvent is increased by introducing a cycloalkane structure, it can also be applied to the fabrication of elements using a coating process. However, the present invention is not particularly limited to these principles.

[0411] <Substitution using deuterium>

[0412] All or part of the hydrogen in the polycyclic aromatic compound having a structure composed of one or more of the structural units represented by the formula (1) may be deuterium.

[0413] For example, in a polycyclic aromatic compound having a structure composed of one or more of the structural units represented by the formula (1), the hydrogen in the aryl ring or heteroaryl ring in the a-ring, b-ring, c-ring, and their substituents may be substituted with deuterium. Among these, a form in which all or part of the hydrogen in the aryl or heteroaryl is substituted with deuterium can be cited. In addition, from the viewpoint of durability, it is also preferable that all or part of the hydrogen in the polycyclic aromatic compound having a structure composed of one or more of the structural units represented by the formula (1) is deuterated.

[0414] <Specific examples of polycyclic aromatic compounds>

[0415] As further specific examples of the polycyclic aromatic compound having a structure composed of one or more of the structural units represented by the formula (1), the following compounds can be cited.

[0416] [Chemical formula 62]

[0417]

[0418] [Chemical formula 63]

[0419]

[0420] [Chemical formula 64]

[0421]

[0422] [Chemical formula 65]

[0423]

[0424] [Chemical Formula 66]

[0425]

[0426] [Chemical Formula 67]

[0427]

[0428] [Chemical Formula 68]

[0429]

[0430] [Chemical Formula 69]

[0431]

[0432] [Chemical Formula 70]

[0433]

[0434] [Chemical Formula 71]

[0435]

[0436] [Chemical Formula 72]

[0437]

[0438] [Chemical Formula 73]

[0439]

[0440] [Chemical Formula 74]

[0441]

[0442] [Chemical Formula 75]

[0443]

[0444] [Chemical Formula 76]

[0445]

[0446] [Chemical Formula 77]

[0447]

[0448] [Chemical Formula 78]

[0449]

[0450] [Chemical Formula 79]

[0451]

[0452] [Chemical formula 80]

[0453]

[0454] [Chemical formula 81]

[0455]

[0456] [Chemical formula 82]

[0457]

[0458] [Chemical formula 83]

[0459]

[0460] [Chemical formula 84]

[0461]

[0462] [Chemical formula 85]

[0463]

[0464] In addition, the compound represented by formula (1-2-1) and the compound represented by formula (1-5-9) are X 1 and X 2 mutually opposite structural isomers, but the compound represented by formula (1-5-9) is preferred.

[0465] <Method for producing polycyclic aromatic compound>

[0466] For a polycyclic aromatic compound having a structure composed of one or more of the structural units represented by formula (1), basically, first, a condensed ring containing an a-ring, a b-ring, and a c-ring is bonded using a bonding group (including a group containing X 1 or X 2 ), thereby producing an intermediate (first reaction). Thereafter, a bonding group (including Y 1The condensation ring containing ring a, ring b, and ring c is bonded by the base), and the final product can be produced therefrom (second reaction). In the first reaction, for example, in the case of an etherification reaction, general reactions such as nucleophilic substitution reaction and Ullmann Reaction can be used. In the case of an amination reaction, general reactions such as Buchwald-Hartwig Reaction, nucleophilic substitution reaction, and Goldberg Amination can be used. In addition, in the second reaction, a tandem hetero-Friedel-Crafts reaction (successive aromatic electrophilic substitution reaction, the same applies hereinafter) can be used. The target compound can be produced by using a raw material having a desired condensation ring at some point in the reaction process or by adding a process for condensing the rings.

[0467] [Method for producing intermediate 1]

[0468] The polycyclic aromatic compound of the present invention can be produced by a production method including the following steps. For each of the following steps, reference can be made to the description in International Publication No. 2015 / 102118.

[0469] Hereinafter, a reaction including the following reaction steps is described: synthesizing the following intermediate 1 from a halogenated precursor, using an organic base compound to metalize the halogen atom (Hal) between X 1 and X 2 ; using a reagent selected from the group consisting of a halide of Y 1 , an aminated halide of Y 1 , an alkoxylate of Y 1 , and an aryloxylate of Y 1 to exchange the metal with Y 1 ; and using a Brønsted base to bond ring b and ring c by successive aromatic electrophilic substitution reaction using the Y 1 . The halogen atom (Hal) in the formula can be any one of F, Cl, Br, and I, and can be appropriately selected in consideration of the reactivity of the substrate.

[0470] [Chemical formula 86]

[0471]

[0472] As the metallating agent used in the halogen-metal exchange reaction in the process described so far, examples include: alkyllithiums such as methyllithium, n-butyllithium, sec-butyllithium, tert-butyllithium, isopropylmagnesium chloride, isopropylmagnesium bromide, phenylmagnesium chloride, phenylmagnesium bromide, and the lithium chloride complex of isopropylmagnesium chloride known as Turbo Grignard Reagent, etc.

[0473] In addition, as the metallating agent used in the ortho-metal exchange reaction in the process described so far, in addition to the above-mentioned reagents, examples also include: organic base compounds such as lithium diisopropylamide, lithium tetramethylpiperidide, lithium hexamethyldisilazide, potassium hexamethyldisilazide, lithium tetramethylpiperidylmagnesium chloride-lithium chloride complex, lithium tri-n-butylmagnate, etc.

[0474] Furthermore, as the additive that promotes the reaction when using alkyllithium as the metallating agent, examples include: N,N,N',N'-tetramethylethylenediamine, 1,4-diazabicyclo[2.2.2]octane, N,N-dimethylpropyleneurea, etc.

[0475] In addition, as the Lewis acids used in the process described so far, examples include: AlCl3, AlBr3, AlF3, BF3·OEt2, BCl3, BBr3, BI3, GaCl3, GaBr3, InCl3, InBr3, In(OTf)3, SnCl4, SnBr4, AgOTf, ScCl3, Sc(OTf)3, ZnCl2, ZnBr2, Zn(OTf)2, MgCl2, MgBr2, Mg(OTf)2, LiOTf, NaOTf, KOTf, Me3SiOTf, Cu(OTf)2, CuCl2, YCl3, Y(OTf)3, TiCl4, TiBr4, ZrCl4, ZrBr4, FeCl3, FeBr3, CoCl3, CoBr3, etc. In addition, substances obtained by supporting these Lewis acids on a solid can also be used in the same way.

[0476] In addition, as the Brønsted acids used in the process described so far, examples include: p-toluenesulfonic acid, methanesulfonic acid, trifluoromethanesulfonic acid, fluorosulfonic acid, carboxylic acid, trifluoroacetic acid, (trifluoromethanesulfonyl)imide, tris(trifluoromethanesulfonyl)methane, hydrogen chloride, hydrogen bromide, hydrogen fluoride, etc. In addition, as the solid Brønsted acids, examples include: Amberlist (trade name: Dow Chemical), Nafion (trade name: DuPont), zeolite, Taycacure (trade name: Tayca Corporation), etc.

[0477] In addition, as amines that can be added in the process described so far, examples include: diisopropylethylamine, triethylamine, tributylamine, 1,4-diazabicyclo[2.2.2]octane, N,N-dimethyl-p-toluidine, N,N-dimethylaniline, pyridine, 2,6-lutidine, 2,6-di-tert-butylamine, and the like.

[0478] In addition, as solvents used in the process described so far, examples include: o-dichlorobenzene, chlorobenzene, toluene, benzene, dichloromethane, chloroform, dichloroethylene, benzotrifluoride, decalin, cyclohexane, hexane, heptane, 1,2,4-trimethylbenzene, xylene, diphenyl ether, anisole, cyclopentyl methyl ether, tetrahydrofuran, dioxane, methyl tert-butyl ether, and the like.

[0479] Here, an example of Y is described. 1 As an example of B, but by appropriately changing the raw materials, Y can also be synthesized. 1 Compounds of P, P=O, P=S, Al, Ga, As, Si-R, or Ge-R.

[0480] In the said process, to promote the tandem Friedel-Crafts reaction, Bronsted bases or Lewis acids can also be used. Among them, when using the trifluoride of Y, 1 the trichloride of Y, 1 the tribromide of Y, 1 the triiodide of Y, 1 etc., halides of Y, 1 acids such as hydrogen fluoride, hydrogen chloride, hydrogen bromide, and hydrogen iodide are generated as the aromatic electrophilic substitution reaction proceeds. Therefore, it is effective to use a Bronsted base that captures the acid. On the other hand, when using the amino halide of Y, 1 the alkoxide of Y, 1 amines and alcohols are generated as the aromatic electrophilic substitution reaction proceeds. Therefore, in most cases, a Bronsted base does not need to be used. However, since the leaving ability of the amino group or alkoxy group is low, it is effective to use a Lewis acid that promotes its leaving.

[0481] In addition, the polycyclic aromatic compounds of the present invention also include compounds in which at least a part of the hydrogen is substituted with deuterium or compounds substituted with various substituents. Such compounds can be synthesized in the same manner as above by using deuterated and derivatized raw materials at the desired positions.

[0482] <2. Organic devices>

[0483] The polycyclic aromatic compounds of the present invention can be used as materials for organic devices. As organic devices, for example, organic electroluminescent elements, organic field effect transistors, or organic thin film solar cells, etc. can be cited.

[0484] The polycyclic aromatic compounds and their polymers of the present invention can be used as materials for organic devices. Examples of the organic devices include organic electroluminescent elements, organic field effect transistors, or organic thin film solar cells, etc., and an organic electroluminescent element is preferred. The polycyclic aromatic compounds and their polymers of the present invention are preferably materials for organic electroluminescent elements, more preferably materials for the light emitting layer (luminescent materials), and most preferably dopant materials for the light emitting layer.

[0485] <2-1. Organic electroluminescent element>

[0486] <2-1-1. Structure of organic electroluminescent element>

[0487] Figure 1 It is a schematic cross-sectional view showing an example of an organic EL element.

[0488] Figure 1 The organic EL element 100 shown includes: a substrate 101, an anode 102 provided on the substrate 101, a hole injection layer 103 provided on the anode 102, a hole transport layer 104 provided on the hole injection layer 103, a light emitting layer 105 provided on the hole transport layer 104, an electron transport layer 106 provided on the light emitting layer 105, an electron injection layer 107 provided on the electron transport layer 106, and a cathode 108 provided on the electron injection layer 107.

[0489] In addition, the organic EL element 100 can also be formed with the manufacturing order reversed to form, for example, the following structure, which includes: a substrate 101, a cathode 108 provided on the substrate 101, an electron injection layer 107 provided on the cathode 108, an electron transport layer 106 provided on the electron injection layer 107, a light emitting layer 105 provided on the electron transport layer 106, a hole transport layer 104 provided on the light emitting layer 105, a hole injection layer 103 provided on the hole transport layer 104, and an anode 102 provided on the hole injection layer 103.

[0490] Not all of the above layers are indispensable layers. Taking the minimum structural unit as the structure including the anode 102, the light emitting layer 105, and the cathode 108, the hole injection layer 103, the hole transport layer 104, the electron transport layer 106, and the electron injection layer 107 are layers that can be optionally provided. In addition, each of the above layers can include a single layer or multiple layers.

[0491] As the form of the layer constituting the organic EL element, in addition to the structural form of "substrate / anode / hole injection layer / hole transport layer / light-emitting layer / electron transport layer / electron injection layer / cathode", it may also be "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 / light-emitting layer / electron transport layer / cathode", "substrate / anode / light-emitting layer / electron transport layer / cathode", "substrate / anode / light-emitting layer / electron injection layer / cathode".

[0492] <2-1-2. Light-emitting layer in organic electroluminescent element>

[0493] The polycyclic aromatic compound of the present invention is preferably used as a material for forming any one or more organic layers in the organic electroluminescent element, and more preferably used as a material for forming the 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. As the material for forming the light-emitting layer 105, any compound (luminescent compound) that is excited by the recombination of holes and electrons to emit light may be used, and a compound that can form a stable thin film shape and exhibits strong luminescence (fluorescence) efficiency in the solid state is preferred. The polycyclic aromatic compound of the present invention can be used as a material for the light-emitting layer, and can be used as a dopant material or a host material, but is preferably used as a material for the light-emitting layer, and more preferably used as a dopant material.

[0494] In addition, as a dopant, there is an example of using an auxiliary dopant and an emitting dopant in combination, but in this specification, when only "dopant" is described, it refers to a luminescent dopant used alone.

[0495] The light-emitting layer can be a single layer or can include multiple layers, either is acceptable, and each is formed by materials for the light-emitting layer (host material, dopant material). The host material and the dopant material can each be one type or a combination of multiple types, either is acceptable. The dopant material can be included in the entire host material or in a part of the host material, either is acceptable. As a doping method, it can be formed by co-evaporation with the host material, or can be co-evaporated after being premixed with the host material. The following shows specific examples of dopants combined with the compound of the present invention in the case of setting multiple dopants.

[0496] [Chemical formula 87]

[0497]

[0498] [Chemical formula 88]

[0499]

[0500] [Chemical formula 89]

[0501]

[0502] [Chemical formula 90]

[0503]

[0504] [Chemical formula 91]

[0505]

[0506] The usage amount of the host material varies depending on the type of the host material, and it can be determined as long as it is coordinated with the characteristics of the host material. The benchmark of the usage amount of the host material is preferably 50% by mass to 99.999% by mass of the total mass of the materials for the light-emitting layer, more preferably 80% by mass to 99.95% by mass, and still more preferably 90% by mass to 99.9% by mass.

[0507] The usage amount of the dopant material varies depending on the type of the dopant material, and it can be determined as long as it is coordinated with the characteristics of the dopant material. The benchmark of the usage amount of the dopant material is preferably 0.001% by mass to 50% by mass of the total mass of the materials for the light-emitting layer, more preferably 0.05% by mass to 20% by mass, and still more preferably 0.1% by mass to 10% by mass. If it is within the above range, it is preferable in terms of preventing, for example, the concentration quenching phenomenon.

[0508] <Host material>

[0509] As the host material, examples include anthracene, pyrene, dibenzo which have been known as light emitters since before Condensed ring derivatives such as fluorene, distyryl anthracene derivatives or distyryl benzene derivatives such as distyryl derivatives, tetraphenyl butadiene derivatives, cyclopentadiene derivatives, fluorene derivatives, benzo fluorene derivatives, etc.

[0510] In addition, as the host material, for example, a compound represented by any one of the following formulas (H1), (H2) and (H3) can be used.

[0511] [Chemical formula 92]

[0512]

[0513] In formulas (H1), (H2) and (H3), L 1 is a single bond or a divalent group containing at least an arylene or heteroarylene. Specifically, L 1 is a single bond, or as long as it is an arylene having 6 to 24 carbon atoms, a heteroarylene having 2 to 24 carbon atoms, a heteroarylene arylene having 6 to 24 carbon atoms or an arylene heteroarylene arylene having 6 to 24 carbon atoms, or any two of these are linked by -O-, -S-, -CH2-, -Si(-Arx)2- (Arx is an aryl group) or a cycloalkylene group to form a divalent group. As the arylene in L 1 , an arylene having 6 to 16 carbon atoms is preferred, an arylene having 6 to 12 carbon atoms is more preferred, an arylene having 6 to 10 carbon atoms is particularly preferred. Specifically, divalent groups such as a benzene ring, a biphenyl ring, a terphenyl ring and a fluorene ring can be listed. As the heteroarylene in L 1 , a heteroarylene having 2 to 24 carbon atoms is preferred, a heteroarylene having 2 to 20 carbon atoms is more preferred, a heteroarylene having 2 to 15 carbon atoms is further preferred, a heteroarylene having 2 to 10 carbon atoms is particularly preferred. Specifically, it can be listed: pyrrole ring, oxazole ring, isoxazole ring, thiazole ring, isothiazole ring, imidazole ring, oxadiazole ring (furazan ring, etc.), thiadiazole ring, triazole ring, tetrazole ring, pyrazole ring, pyridine ring, pyrimidine ring, pyridazine ring, pyrazine ring, triazine ring, indole ring, isoindole ring, 1H-indazole ring, benzimidazole ring, benzoxazole ring, benzothiazole ring, 1H-benzotriazole ring, quinoline ring, isoquinoline ring, cinnoline ring, quinazoline ring, quinoxaline ring, phthalazine ring, naphthyridine ring, purine ring, pteridine ring, carbazole ring, acridine ring, phenoxathiin ring, phenoxazine ring, phenothiazine ring, phenazine ring, indolizine ring, furan ring, benzofuran ring, isobenzofuran ring, dibenzofuran ring, thiophene ring, benzothiophene ring, dibenzothiophene ring, and thianthrene ring, etc. divalent groups. At least one hydrogen in the compound represented by each formula can be substituted by at least one group selected from the substituent group Z or deuterium. For example, it can be substituted by an alkyl group having 1 to 6 carbon atoms, a cyano group, a halogen or deuterium.

[0514] As a preferred specific example, compounds represented by any of the following listed structural formulas can be cited. Further, in the following listed structural formulas, at least one hydrogen may be substituted with a halogen, a cyano group, an alkyl group having 1 to 4 carbon atoms (e.g., a methyl group or a tert-butyl group), a phenyl group, a naphthyl group, or the like.

[0515] [Chemical formula 93]

[0516]

[0517] [Chemical formula 94]

[0518]

[0519] [Chemical formula 95]

[0520]

[0521] [Chemical formula 96]

[0522]

[0523] <Anthracene compound>

[0524] As the main anthracene compounds, for example, compounds represented by formula (3-H) and compounds represented by formula (3-H2) can be cited.

[0525] [Chemical formula 97]

[0526]

[0527] In formula (3-H),

[0528] X and Ar 4 are each independently hydrogen or selected from a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted diarylamino group, an optionally substituted diheteroarylamino group, a substituted or unsubstituted arylheteroarylamino group, a substituted or unsubstituted alkyl group, an optionally substituted cycloalkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted arylthio group, or a substituted silyl group, and all of X and Ar 4 do not simultaneously become hydrogen.

[0529] At least one hydrogen in the compound represented by formula (3-H) may be substituted with a halogen, a cyano group, deuterium, or an optionally substituted heteroaryl group.

[0530] Alternatively, the structure represented by formula (3-H) can also be used as a unit structure to form a polymer (preferably a dimer). In such a case, for example, a form in which the unit structures represented by formula (3-H) are bonded to each other via X can be cited. As the X, a single bond, an arylene group (such as a phenylene group, a biphenylene group, and a naphthylene group), a heteroarylene group (a group having a divalent bonding valence such as a pyridine ring, a dibenzofuran ring, a dibenzothiophene ring, a carbazole ring, a benzocarbazole ring, and a phenyl-substituted carbazole ring), etc. can be cited.

[0531] The preferred forms of the anthracene compound will be described below. The definitions of the symbols in the following structures are the same as those described above.

[0532] [Chemical formula 98]

[0533]

[0534] In formula (3-H), X is independently a group represented by formula (3-X1), formula (3-X2), or formula (3-X3). The groups represented by formula (3-X1), formula (3-X2), or formula (3-X3) are bonded to the anthracene ring of formula (3-H) at the *. Preferably, two Xs do not simultaneously become the group represented by formula (3-X3). More preferably, two Xs do not simultaneously become the group represented by formula (3-X2) either.

[0535] Alternatively, the structure represented by formula (3-H) can also be used as a unit structure to form a polymer (preferably a dimer). In such a case, for example, a form in which the unit structures represented by formula (3-H) are bonded to each other via X can be cited. As the X, a single bond, an arylene group (such as a phenylene group, a biphenylene group, and a naphthylene group), a heteroarylene group (a group having a divalent bonding valence such as a pyridine ring, a dibenzofuran ring, a dibenzothiophene ring, a carbazole ring, a benzocarbazole ring, and a phenyl-substituted carbazole ring), etc. can be cited.

[0536] The naphthylene moiety in formula (3-X1) and formula (3-X2) can be condensed with one benzene ring. The structure condensed in such a manner is as follows.

[0537] [Chemical formula 99]

[0538]

[0539] Ar 1 and Ar 2 are each independently hydrogen, phenyl, biphenyl, terphenyl, quaterphenyl, naphthyl, phenanthryl, fluorenyl, benzofluorenyl, group, triphenylene, pyrenyl, or a group represented by formula (A) (also including carbazolyl, benzocarbazolyl, and phenyl-substituted carbazolyl). In addition, in Ar 1 or Ar 2When it is a group represented by formula (A), the group represented by formula (A) is bonded to the naphthalene ring in formula (3-X1) or formula (3-X2) at the *.

[0540] Ar 3 is phenyl, biphenyl, terphenyl, quaterphenyl, naphthyl, phenanthryl, fluorenyl, benzofluorenyl, group, triphenylene, pyrenyl, or a group represented by formula (A) (also including carbazolyl, benzocarbazolyl, and phenyl-substituted carbazolyl). In addition, when Ar 3 is a group represented by formula (A), the group represented by formula (A) is bonded to the single bond represented by the straight line in formula (3-X3) at the *. That is, the anthracene ring of formula (3-H) is directly bonded to the group represented by formula (A).

[0541] In addition, Ar 3 may have a substituent, and at least one hydrogen in Ar 3 may further be substituted by an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, fluorenyl, group, triphenylene, pyrenyl, or a group represented by formula (A) (also including carbazolyl and phenyl-substituted carbazolyl). In addition, when the substituent that Ar 3 has is a group represented by formula (A), the group represented by formula (A) is bonded to Ar in formula (3-X3) at the *. 3

[0542] Ar 4 are each independently hydrogen, phenyl, biphenyl, terphenyl, naphthyl, or a silyl group substituted by an alkyl group having 1 to 4 carbon atoms (such as methyl, ethyl, tert-butyl, etc.) and / or a cycloalkyl group having 5 to 10 carbon atoms.

[0543] In addition, the hydrogen in the chemical structure of the anthracene compound represented by formula (3-H) may also be substituted by a group represented by formula (A). When substituted by a group represented by formula (A), the group represented by formula (A) substitutes at least one hydrogen in the compound represented by formula (3-H) at the *.

[0544] The group represented by formula (A) is one of the substituents that the anthracene compound represented by formula (3-H) may have.

[0545] [Chemical 100]

[0546]

[0547] In formula (A), Y is -O-, -S-, or >N-R 29 , R 21 ~R 28 ​Each independently is hydrogen, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted arylthio, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, alkyldicycloalkylsilyl, optionally substituted amino, halogen, hydroxy or cyano, R 21 ~R 28 The adjacent groups in may be bonded to each other to form a hydrocarbon ring, an aryl ring or a heteroaryl ring, R 29 is hydrogen or optionally substituted aryl.

[0548] Y in formula (A) is preferably -O-.

[0549] As the "substituted amino" in R 21 ~R 28 Examples of the "substituted amino" in the "optionally substituted amino" include diarylamino, diheteroarylamino, arylheteroarylamino, etc.

[0550] As ">N-R 29 " in Y, R 29 is hydrogen or optionally substituted aryl.

[0551] R 21 ~R 28 The adjacent groups in may be bonded to each other to form a hydrocarbon ring, an aryl ring or a heteroaryl ring. In the case where no ring is formed, it is a group represented by the following formula (A-1). As the case where a ring is formed, for example, groups represented by the following formula (A-2) to formula (A-14) can be cited. In addition, at least one hydrogen in the group represented by any one of formula (A-1) to formula (A-14) can be substituted by alkyl, cycloalkyl, aryl, heteroaryl, alkoxy, aryloxy, arylthio, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, alkyldicycloalkylsilyl, diaryl (two aryls can be bonded to each other via a linking group) substituted amino, diheteroaryl substituted amino, arylheteroaryl substituted amino, halogen, hydroxy or cyano.

[0552] [Chemical formula 101]

[0553]

[0554] As the ring formed by the adjacent groups bonding to each other, if it is a hydrocarbon ring, for example, a cyclohexane ring can be cited. As the aryl ring or heteroaryl ring, the ring structures described in the "aryl" or "heteroaryl" in R 21 ~R 28 can be cited, and the ring is formed by condensing with one or two benzene rings in formula (A-1).

[0555] The group represented by formula (A) is a group obtained by removing one hydrogen from any position of formula (A), and * represents said position. That is, the group represented by formula (A) can have any position as the bonding position. For example, it can be any carbon atom on the two benzene rings in the structure of formula (A), an atom on any ring formed by bonding adjacent groups among R 21 ~R 28 in the formula, or an R in “>N-R 29 ” which is Y in the structure of formula (A), or any position in R 29 in “>N-R 29 ” or an N (R 29 is the bonding bond) directly bonded group. The same applies to the groups represented by any one of formulas (A-1) to (A-14).

[0556] As the group represented by formula (A), for example, the groups represented by any one of formulas (A-1) to (A-14) can be cited. Preferably, it is the group represented by any one of formulas (A-1) to (A-5) and formulas (A-12) to (A-14). More preferably, it is the group represented by any one of formulas (A-1) to (A-4). Further preferably, it is the group represented by any one of formulas (A-1), (A-3), and (A-4). Particularly preferably, it is the group represented by formula (A-1).

[0557] As the group represented by formula (A), for example, the following groups can be cited. The definitions of Y and * in the formula are the same as above.

[0558] [Chemical formula 102]

[0559]

[0560] [Chemical formula 103]

[0561]

[0562] In the compound represented by formula (3-H), the group represented by formula (A) is preferably in a form bonded to any one of the naphthalene ring in formula (3-X1) or formula (3-X2), the single bond in formula (3-X3), and Ar 3 in formula (3-X3).

[0563] In addition, all or part of the hydrogens in the chemical structure of the anthracene compound represented by formula (3-H) can be deuterium.

[0564] The anthracene compound as the main body can be, for example, the compound represented by the following formula (3-H2).

[0565] [Chemical formula 104]

[0566]

[0567] In formula (3-H2), Ar c is a substituted aryl or a substituted heteroaryl, R c is hydrogen, an alkyl group, or a cycloalkyl group, Ar 11 , Ar 12 , Ar 13 , Ar 14 , Ar 15 , Ar 16 , Ar 17 , and Ar 18 are each independently hydrogen, a substituted aryl, a substituted heteroaryl, a substituted diarylamino (the two aryl groups may be bonded to each other via a linking group), a substituted diheteroarylamino (the two heteroaryl groups may be bonded to each other via a linking group), a substituted arylheteroarylamino (the aryl group and the heteroaryl group may be bonded to each other via a linking group), a substituted alkyl, a substituted cycloalkyl, a substituted alkenyl, a substituted alkoxy, a substituted aryloxy, a substituted arylthio, or a substituted silyl group. At least one hydrogen in the compound represented by formula (3-H2) may be substituted with a halogen, a cyano group, or deuterium.

[0568] As the "substituted aryl", a group represented by any one of the following formulae (3-H2-X1) to (3-H2-X8) is also preferred.

[0569] [Chemical formula 105]

[0570]

[0571] In formulae (3-H2-X1) to (3-H2-X8), * represents the bonding position. In formulae (3-H2-X1) to (3-H2-X3), Ar 21 , Ar 22 , and Ar 23 are each independently hydrogen, phenyl, biphenyl, terphenyl, quaterphenyl, naphthyl, phenanthryl, fluorenyl, benzo[fluorene]yl, a [group name], triphenylene, pyrenyl, anthryl, or a group represented by formula (A). In addition, in the description of formula (3-H2), the group represented by formula (A) is the same as the group described in the anthracene compound represented by formula (3-H).

[0572] In formulae (3-H2-X4) to (3-H2-X8), Ar 24 , Ar 25 , Ar 26 , Ar 27 , Ar 28 , Ar 29 , and Ar 30Each independently is hydrogen, phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, fluorenyl, anthryl, triphenylene, pyrenyl, or a group represented by formula (A). Further, any one or more hydrogens in each of the groups represented by formula (3-H2-X1) to formula (3-H2-X8) may be substituted with an alkyl group having 1 to 6 carbon atoms (preferably methyl or tert-butyl).

[0573] Furthermore, as a preferred example of the "aryl group which may be substituted", a terphenyl (especially meta-terphenyl-5'-yl) which may be substituted with one or more substituents selected from the group consisting of phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, fluorenyl, anthryl, triphenylene, pyrenyl, and the group represented by formula (A) can be mentioned.

[0574] As the "heteroaryl group which may be substituted", the group represented by formula (A) can also be mentioned. In addition, as specific examples of the "aryl group which may be substituted" and the "heteroaryl group which may be substituted", dibenzofuranyl, naphthobenzofuranyl, phenyl-substituted dibenzofuranyl, etc. can be mentioned.

[0575] At least one hydrogen in the compound represented by formula (3-H2) may be substituted with a halogen, a cyano group, or deuterium. As the "halogen" in this case, fluorine, chlorine, bromine, and iodine can be mentioned. Particularly preferred is a compound in which all hydrogens in the compound represented by formula (3-H2) are substituted with deuterium.

[0576] In formula (3-H2), R c is hydrogen, an alkyl group, or a cycloalkyl group, preferably hydrogen, methyl, or tert-butyl, and more preferably hydrogen.

[0577] In formula (3-H2), preferably at least two of Ar 11 to Ar 18 are an aryl group which may be substituted or a heteroaryl group which may be substituted. That is, the anthracene compound represented by formula (3-H2) preferably has a structure in which at least three substituents selected from the group consisting of an aryl group which may be substituted and a heteroaryl group which may be substituted are bonded to the anthracene ring.

[0578] In the anthracene compound represented by formula (3-H2), more preferably two of Ar 11 to Ar 18 are an aryl group which may be substituted or a heteroaryl group which may be substituted, and the other six are hydrogen, an alkyl group which may be substituted, a cycloalkyl group which may be substituted, an alkenyl group which may be substituted, or an alkoxy group which may be substituted. That is, the anthracene compound represented by formula (3-H2) more preferably has a structure in which three substituents selected from the group consisting of an aryl group which may be substituted and a heteroaryl group which may be substituted are bonded to the anthracene ring.

[0579] Among the anthracene compounds represented by formula (3-H2), Ar is more preferably 11 ~Ar 18 Any two of them are optionally substituted aryl or optionally substituted heteroaryl, and the other six are hydrogen, methyl, or tert-butyl.

[0580] Furthermore, in formula (3-H2), it is preferable that R c is hydrogen, and Ar 11 ~Ar 18 Six of them are hydrogen.

[0581] The anthracene compound represented by formula (3-H2) is preferably an anthracene compound represented by the following formula (3-H2-A), formula (3-H2-B), formula (3-H2-C), formula (3-H2-D), or formula (3-H2-E).

[0582] [Chemical 106]

[0583]

[0584] In formula (3-H2-A), formula (3-H2-B), formula (3-H2-C), formula (3-H2-D), or formula (3-H2-E), Ar c' , Ar 11' , Ar 12' , Ar 13' , Ar 14' , Ar 15' , Ar 17' , and Ar 18' are each independently phenyl, biphenyl, terphenyl, quaterphenyl, naphthyl, phenanthryl, fluorenyl, benzo[a]fluorenyl, -yl, triphenylene, pyrenyl, or a group represented by formula (A), and at least one hydrogen in these groups may be substituted by phenyl, biphenyl, terphenyl, quaterphenyl, naphthyl, phenanthryl, fluorenyl, benzo[a]fluorenyl, -yl, triphenylene, pyrenyl, or a group represented by formula (A). Here, when the hydrogens of the methylene groups in fluorenyl and benzo[a]fluorenyl are both substituted by phenyl, these phenyls may be bonded to each other by a single bond. The carbon atoms 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 may be bonded with methyl or tert-butyl in place of hydrogen.

[0585] When Ar c' , Ar 11' , Ar 12' , Ar 13', Ar 14' , Ar 15' , Ar 17' and Ar 18' When Ar is a substituted or unsubstituted phenyl group or a substituted or unsubstituted naphthyl group respectively, it is preferably a group represented by any one of the formulas (3-H2-X1) to (3-H2-X8).

[0586] Ar c' , Ar 11' , Ar 12' , Ar 13' , Ar 14' , Ar 15' , Ar 17' and Ar 18' More preferably, they are each independently a phenyl group, a biphenyl group (especially biphenyl-2-yl or biphenyl-4-yl), a terphenyl group (especially m-terphenyl-5'-yl), a naphthyl group, a phenanthryl group, a fluorenyl group, or a group represented by any one of the formulas (A-1) to (A-4). At this time, at least one hydrogen in these groups may be substituted by a phenyl group, a biphenyl group, a naphthyl group, a phenanthryl group, a fluorenyl group, or a group represented by any one of the formulas (A-1) to (A-4).

[0587] In addition, at least one hydrogen in the compound represented by the formula (3-H2-A), formula (3-H2-B), formula (3-H2-C), formula (3-H2-D), or formula (3-H2-E) may be substituted by a halogen, a cyano group, or deuterium. In addition, a deuterated form is preferred, and a form in which the anthracene ring is completely deuterated or a form in which all hydrogen atoms are deuterated is preferred.

[0588] As a particularly preferred anthracene compound represented by the formula (3-H2), an anthracene compound represented by the following formula (3-H2-Aa) can be cited.

[0589] [Chemical formula 107]

[0590]

[0591] In the formula (3-H2-Aa), Ar c' , Ar 14' and Ar 15' are each independently a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a phenanthryl group, a fluorenyl group, a benzo[9,10]fluorenyl group, a group, a triphenylene group, a pyrenyl group, or a group represented by any one of the formulas (A-1) to (A-11). At least one hydrogen in these groups may be substituted by a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a phenanthryl group, a fluorenyl group, a benzo[9,10]fluorenyl group, substituted by a group selected from a group consisting of a fluorene group, a triphenylene group, a pyrene group, or any one of the groups represented by Formula (A-1) to Formula (A-11). Here, when the hydrogens of the methylene groups in the fluorene group and the benzofluorene group are each substituted by a phenyl group, these phenyl groups may be bonded to each other by a single bond. In addition, the carbon atoms of the anthracene ring of Ar c' 、Ar 14' and Ar 15' may be substituted with a methyl group or a tert-butyl group in place of a hydrogen atom. At least one hydrogen atom in the compound represented by Formula (3-H2-Aa) may be substituted with a halogen or a cyano group, and at least one hydrogen atom in the compound represented by Formula (3-H2-Aa) is substituted with deuterium.

[0592] In Formula (3-H2-Aa), Ar c' 、Ar 14' and Ar 15' are each preferably independently a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a phenanthryl group, a fluorene group, or any one of the groups represented by Formula (A-1) to Formula (A-4), and at least one hydrogen atom in these groups may be substituted with a phenyl group, a naphthyl group, a phenanthryl group, a fluorene group, or any one of the groups represented by Formula (A-1) to Formula (A-4).

[0593] In the compound represented by Formula (3-H2-Aa), preferably, the hydrogen atom bonded to at least the carbon atom at the 10-position of the anthracene ring (the carbon atom to which Ar c' is bonded is defined as the 9-position) is substituted with deuterium. That is, the compound represented by Formula (3-H2-Aa) is preferably a compound represented by the following Formula (3-H2-Ab). In addition, in Formula (3-H2-Ab), D is deuterium, and Ar c' 、Ar 14' and Ar 15' have the same definitions as in Formula (3-H2-Aa). D in Formula (3-H2-Ab) means that at least the said position is deuterium, and any one or more other hydrogen atoms in Formula (3-H2-Ab) may be deuterium at the same time, and preferably all the hydrogen atoms in Formula (3-H2-Ab) are deuterium.

[0594] [Chemical Formula 108]

[0595]

[0596] As specific examples of the anthracene compound, for example, compounds represented by formula (3-131-Y) to formula (3-182-Y), formula (3-183-N), formula (3-184-Y) to formula (3-284-Y), and formula (3-500) to formula (3-557), and formula (3-600) to formula (3-605), and formula (3-606-Y) to formula (3-626-Y) can be cited. The hydrogen atoms in these formulas may be partially or entirely replaced by deuterium, but for particularly preferred forms of deuterium substitution, they are listed individually. Y in the formula may be -O-, -S-, >N-R 29 (R 29 has the same definition as above) or >C(-R 30 )2 (R 30 is a connectable aryl group or alkyl group), and R 29 is, for example, a phenyl group, and R 30 is, for example, a methyl group. Regarding the formula numbers, for example, when Y is O, formula (3-131-Y) is set as formula (3-131-O), and when Y is -S- or >N-R 29 , they are set as formula (3-131-S) and formula (3-131-N), respectively.

[0597] [Chemical formula 109]

[0598]

[0599] [Chemical formula 110]

[0600]

[0601] [Chemical formula 111]

[0602]

[0603] [Chemical formula 112]

[0604]

[0605] [Chemical formula 113]

[0606]

[0607] [Chemical formula 114]

[0608]

[0609] [Chemical formula 115]

[0610]

[0611] [Chemical formula 116]

[0612]

[0613] [Chemical Formula 117]

[0614]

[0615] [Chemical Formula 118]

[0616]

[0617] [Chemical Formula 119]

[0618]

[0619] [Chemical Formula 120]

[0620]

[0621] [Chemical Formula 121]

[0622]

[0623] [Chemical Formula 122]

[0624]

[0625] [Chemical Formula 123]

[0626]

[0627] [Chemical Formula 124]

[0628]

[0629] [Chemical Formula 125]

[0630]

[0631] [Chemical Formula 126]

[0632]

[0633] [Chemical Formula 127]

[0634]

[0635] [Chemical Formula 128]

[0636]

[0637] In the above formula, D is deuterium.

[0638] Among these compounds, those represented by Formula (3-131-Y) to Formula (3-134-Y), Formula (3-138-Y), Formula (3-140-Y) to Formula (3-143-Y), Formula (3-150-Y), Formula (3-153-Y) to Formula (3-156-Y), Formula (3-166-Y), Formula (3-168-Y), Formula (3-173-Y), Formula (3-177-Y), Formula (3-180-Y) to Formula (3-183-N), Formula (3-185-Y), Formula (3-190-Y), Formula (3-223-Y), Formula (3-241-Y), Formula (3-250-Y), Formula (3-252-Y) to Formula (3-254-Y), Formula (3-270-Y) to Formula (3-284-Y), Formula (3-501), Formula (3-507), Formula (3-508), Formula (3-509), Formula (3-513), Formula (3-514), Formula (3-519), Formula (3-521), Formula (3-538) to Formula (3-547), or Formula (3-600) to Formula (3-605), and Formula (3-606-Y) to Formula (3-626-Y) are preferred. In addition, Y is preferably -O- or >N-R 29 , more preferably -O-. In addition, the deuterium-substituted form is also preferred.

[0639] The anthracene compound can use a compound having a reactive group at a desired position on the anthracene skeleton, and a compound having a reactive group on partial structures such as X, Ar 4 and the structural part of Formula (A) as starting materials, and apply Suzuki coupling, Negishi coupling, or other known coupling reactions for production. Examples of the reactive group of the reactive compound include halogen or boric acid. As a specific production method, for example, reference can be made to the synthesis methods in paragraphs

[0089] to

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

[0640] <Fluorene compound>

[0641] The compound represented by Formula (4-H) basically functions as a host.

[0642] [Chemical Formula 129]

[0643]

[0644] In Formula (4-H),

[0645] R 1 to R 10Each independently is hydrogen, aryl, heteroaryl (the heteroaryl may be bonded to the fluorene skeleton in formula (4-H) via a linking group), diarylamino (the two aryl groups may be bonded to each other via a linking group), diheteroarylamino (the two heteroaryl groups may be bonded to each other via a linking group), arylheteroarylamino (the aryl group and the heteroaryl group may be bonded to each other via a linking group), alkyl, cycloalkyl, alkenyl, alkoxy or aryloxy, and at least one hydrogen among these may be substituted with aryl, heteroaryl, alkyl or cycloalkyl. Additionally, 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 each other to form a condensed ring or a spiro ring, and at least one hydrogen in the formed ring may be substituted with aryl, heteroaryl (the heteroaryl may be bonded to the formed ring via a linking group), diarylamino (the two aryl groups may be bonded to each other via a linking group), diheteroarylamino (the two heteroaryl groups may be bonded to each other via a linking group), arylheteroarylamino (the aryl group and the heteroaryl group may be bonded to each other via a linking group), alkyl, cycloalkyl, alkenyl, alkoxy or aryloxy, and at least one hydrogen among these may be substituted with aryl, heteroaryl, alkyl or cycloalkyl. At least one hydrogen in the compound represented by formula (4-H) may be substituted with halogen, cyano or deuterium.

[0646] In addition, as specific examples of the heteroaryl, a monovalent group represented by removing any one hydrogen atom from a compound of the following formula (4-Ar1), formula (4-Ar2), formula (4-Ar3), formula (4-Ar4) or formula (4-Ar5) may also be mentioned.

[0647] [Chemical 130]

[0648]

[0649] In formula (4-Ar1) to formula (4-Ar5), Y 1 each independently is O, S or N-R, R is phenyl, biphenyl, naphthyl, anthracenyl or hydrogen, and at least one hydrogen in the structure of formula (4-Ar1) to formula (4-Ar5) may be substituted with phenyl, biphenyl, naphthyl, anthracenyl, phenanthryl, methyl, ethyl, propyl or butyl.

[0650] These heteroaryls may be bonded to the fluorene skeleton in formula (4-H) via a linking group. That is, the fluorene skeleton in formula (4-H) and the heteroaryl may be directly bonded, and may also be bonded via a linking group therebetween. Examples of the linking group include: phenylene, biphenylene, naphthylene, anthrylene, methylene, ethylene, -OCH2CH2-, -CH2CH2O-, or -OCH2CH2O-, etc.

[0651] In addition, R in formula (4-H) 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 5 and R 6 , R 6 and R 7 or R 7 and R 8 may be independently bonded respectively to form a condensed ring, and 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 on the benzene ring in formula (4-H), and is an aliphatic ring or an aromatic ring. Preferably it is an aromatic ring, and examples of the structure including the benzene ring in formula (4-H) include a naphthalene ring or a phenanthrene ring, etc. The spiro ring formed by R 9 and R 10 is a ring formed by spiro-bonding on the 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, etc.

[0652] 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), and is respectively a compound formed by condensation of the benzene ring formed by bonding of R 1 and R 2 in formula (4-H), a compound formed by condensation of the benzene ring formed by bonding of R 3 and R 4 in formula (4-H), or a compound in which none of R 1 to R 8 in formula (4-H) is bonded.

[0653] [Chemical 131]

[0654]

[0655] R 1 to R 10The definition of is the same as the corresponding R in formula (4-H). 1 to R 10 The R in formula (4-H-1) and formula (4-H-2) is the same as that in formula (4-H). 11 to R 14 The definition of is also the same as the R in formula (4). 1 to R 10 The same.

[0656] The compound represented by formula (4-H) is further preferably a compound represented by the following formula (4-H-1A), formula (4-H-2A) or formula (4-H-3A), and is a compound in which R 9 and R 10 are bonded to form a spiro-fluorene ring.

[0657] [Chemical formula 132]

[0658]

[0659] The definition of R in formula (4-H-1A), formula (4-H-2A) and formula (4-H-3A) is the same as the corresponding R in formula (4-H-1), formula (4-H-2) and formula (4-H-3), and the definition of R 2 to R 7 in formula (4-H-1A) and formula (4-H-2A) is also the same as the R in formula (4-H-1) and formula (4-H-2). 2 to R 7 The same. 11 to R 14 The definition of is also the same as the R in formula (4-H-1) and formula (4-H-2). 11 to R 14 The same.

[0660] In addition, all or part of the hydrogen in the compound represented by formula (4-H) can be substituted by halogen, cyano or deuterium.

[0661] More specific examples of the fluorene compound as the main body of the present invention include compounds represented by the following structural formulas.

[0662] [Chemical formula 133]

[0663]

[0664] <Dibenzo Compound>

[0665] The main dibenzo Compound is, for example, a compound represented by the following formula (5-H).

[0666] [Chemical formula 134]

[0667]

[0668] In formula (5-H), R 1 to R 16 are each independently hydrogen, aryl, heteroaryl (the heteroaryl may be bonded to the dibenzo in formula (5-H) via a linking group) skeleton), diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkenyl, alkoxy or aryloxy, and at least one hydrogen in these may be substituted with aryl, heteroaryl, alkyl or cycloalkyl. Further, adjacent groups among R 1 to R 16 may be bonded to each other to form a condensed ring, and at least one hydrogen in the formed ring may be substituted with aryl, heteroaryl (the heteroaryl may be bonded to the formed ring via a linking group), diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkenyl, alkoxy or aryloxy, and at least one hydrogen in these may be substituted with aryl, heteroaryl, alkyl or cycloalkyl. At least one hydrogen in the compound represented by formula (5-H) may be substituted with halogen, cyano or deuterium.

[0669] As the alkenyl in the definition of formula (5-H), for example, alkenyl having 2 to 30 carbon atoms can be mentioned, preferably alkenyl having 2 to 20 carbon atoms, more preferably alkenyl having 2 to 10 carbon atoms, still more preferably alkenyl having 2 to 6 carbon atoms, and particularly preferably alkenyl having 2 to 4 carbon atoms. Preferred alkenyls are vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, or 5-hexenyl.

[0670] In addition, as specific examples of the heteroaryl, monovalent groups represented by removing any one hydrogen atom from the compounds of the following formula (5-Ar1), formula (5-Ar2), formula (5-Ar3), formula (5-Ar4) or formula (5-Ar5) can also be mentioned.

[0671] [Chemical formula 135]

[0672]

[0673] In formula (5-Ar1) to formula (5-Ar5), Y 1 are each independently O, S or N-R, R is phenyl, biphenyl, naphthyl, anthracenyl or hydrogen, and at least one hydrogen in the structures of formula (5-Ar1) to formula (5-Ar5) may be substituted with phenyl, biphenyl, naphthyl, anthracenyl, phenanthryl, methyl, ethyl, propyl, or butyl.

[0674] These heteroaryls may be bonded to the dibenzo in formula (5-H) via a linking group Skeletal bond. That is, the dibenzo in formula (5-H) The skeleton and the heteroaryl can be bonded not only directly but also via a linking group therebetween. Examples of the linking group include: phenylene, biphenylene, naphthylene, anthrylene, methylene, ethylene, -OCH2CH2-, -CH2CH2O-, or -OCH2CH2O-, etc.

[0675] The compound represented by formula (5-H) is preferably R 1 、R 4 、R 5 、R 8 、R 9 、R 12 、R 13 and R 16 is hydrogen. In this case, R in formula (5-H) 2 、R 3 、R 6 、R 7 、R 10 、R 11 、R 14 、R 15 is preferably independently of each other hydrogen, phenyl, biphenyl, naphthyl, anthryl, 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 monovalent group having the structure can be bonded to the dibenzo in formula (5-H) via phenylene, biphenylene, naphthylene, anthrylene, methylene, ethylene, -OCH2CH2-, -CH2CH2O-, or -OCH2CH2O-), methyl, ethyl, propyl, or butyl. skeleton bond).

[0676] The compound represented by formula (5-H) is more preferably R 1 、R 2 、R 4 、R 5 、R 7 、R 8 、R 9 、R 10 、R 12 、R 13 、R 15 and R 16 is hydrogen. In this case, R in formula (5-H) 3 、R 6 、R 11 、R 14At least one (preferably one or two, more preferably one) of them is a monovalent group having a structure of formula (5-Ar1), formula (5-Ar2), formula (5-Ar3), formula (5-Ar4) or formula (5-Ar5) with an intervening single bond, phenylene, biphenylene, naphthylene, anthrylene, methylene, ethylene, -OCH2CH2-, -CH2CH2O- or -OCH2CH2O-. Other than the at least one (i.e., other than the position substituted by the monovalent group having the structure), it is hydrogen, phenyl, biphenyl, naphthyl, anthryl, methyl, ethyl, propyl or butyl, and at least one hydrogen among these may be substituted by phenyl, biphenyl, naphthyl, anthryl, methyl, ethyl, propyl or butyl.

[0677] In addition, as R in formula (5-H) 2 , R 3 , R 6 , R 7 , R 10 , R 11 , R 14 and R 15 , in the case of selecting a monovalent group having a structure represented by formula (5-Ar1) to formula (5-Ar5), 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.

[0678] More specific examples of the dibenzo compound which is the main body of the present invention include compounds represented by the following structural formulas.

[0679] [Chemical formula 136]

[0680]

[0681] [Chemical formula 137]

[0682]

[0683] The material for the light-emitting layer (host material and dopant material) can also be used as the following polymer compound or its polymer crosslinked body, or the following pendant polymer compound or its pendant polymer crosslinked body: The polymer compound is obtained by polymerizing a reactive compound in which a reactive substituent is substituted in the material for the light-emitting layer (host material and dopant material) as a monomer, and the pendant polymer compound is obtained by reacting a main-chain polymer with the reactive compound. As the reactive substituent in this case, the description in the polycyclic aromatic compound represented by formula (1) can be cited.

[0684] <Light-emitting layer containing auxiliary dopant and emission dopant>

[0685] The light-emitting layer in an organic electroluminescent element may contain a host compound as a first component, a co-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 the emitting dopant. As the co-dopant (compound), a thermally activated delayed phosphor can be used.

[0686] In the following description, an organic electroluminescent element using a thermally activated delayed phosphor as a co-dopant is sometimes referred to as a "TAF element" (TADF Assisting Fluorescence element). The "host compound" in a TAF element means a compound in which the lowest excited singlet state energy level obtained from the shoulder peak 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.

[0687] The so-called "thermally activated delayed phosphor" refers to a compound that absorbs thermal energy and undergoes reverse intersystem crossing from the lowest excited triplet state to the lowest excited singlet state, and emits and deactivates from the lowest excited singlet state, thereby being able to emit delayed fluorescence. Among them, the so-called "thermally activated delayed fluorescence" also includes the case of passing through a higher-order triplet state during the excitation process from the lowest excited triplet state to the lowest excited singlet state. For example, there can be cited papers published by Monkman et al. of Durham University (《NATURE COMMUNICATIONS》(7: 13680, Digital Object Identifier (DOI): 10.1038 / ncomms13680)), papers published by Hosokai et al. of the National Institute of Advanced Industrial Science and Technology (Hosokai et al., 《Science Advances (Sci. Adv.)》(2017; 3: e1603282)), papers published by Sato et al. of Kyoto University (《Scientific Reports》(7: 4820, DOI: 10.1038 / s41598-017-05007-7)), and a society presentation made by Sato et al. of Kyoto University (the 98th Spring Annual Meeting of the Chemical Society of Japan, presentation number: 2I4-15, 《Mechanism of High-Efficiency Luminescence in Organic Electroluminescence Using Diazaboranaphthoanthracene (DABNA) as a Luminescent Molecule》, Graduate School of Engineering, Kyoto University), etc. In the present invention, regarding a sample containing the target compound, it is determined that the target compound is a "thermally activated delayed phosphor" based on the observation of a slow fluorescence component when measuring the fluorescence lifetime at 300K. Here, the so-called slow fluorescence component refers to a component with a fluorescence lifetime of 0.1 μsec or more. The measurement of the fluorescence lifetime can be carried out, for example, using a fluorescence lifetime measurement device (manufactured by Hamamatsu Photonics, C11367-01).

[0688] The polycyclic aromatic compound of the present invention can function as an emission dopant, and the "thermally activated delayed phosphor" can function as an auxiliary dopant for assisting the luminescence of the polycyclic aromatic compound of the present invention.

[0689] In this embodiment, as the host compound, known compounds can be used. For example, compounds having at least one of a carbazole ring and a furan ring can be cited. Among them, compounds formed by bonding at least one of a furyl group and a carbazolyl group to at least one of an arylene group and a heteroarylene group are preferably used. As specific examples, mCP or mCBP, etc. can be cited.

[0690] In terms of the view of promoting rather than hindering the generation of TADF in the light-emitting layer, the lowest excited triplet state energy level E(1,T,Sh) of the host compound obtained from the shoulder peak on the short wavelength side of the peak of the phosphorescence spectrum is preferably higher than the lowest excited triplet state energy levels E(2,T,Sh) and E(3,T,Sh) of the emission dopant or co-dopant having the highest lowest excited triplet state energy level in the light-emitting layer. Specifically, compared with E(2,T,Sh) and E(3,T,Sh), the lowest excited triplet state energy level E(1,T,Sh) of the host compound is preferably 0.01 eV or more, more preferably 0.03 eV or more, and still more preferably 0.1 eV or more. In addition, a TADF-active compound may also be used as the host compound.

[0691] In the host compound, for example, a compound represented by any one of the formulas (H1), (H2), and (H3) can be used.

[0692] <Thermally Activated Delayed Fluorophore (Co-dopant)>

[0693] The thermally activated delayed fluorophore (TADF compound) used in the TAF element is preferably the following donor-acceptor type thermally activated delayed fluorophore (D-A type TADF compound): It is designed to localize the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO) in the molecule by using an electron-donating substituent called a donor and an electron-accepting substituent called an acceptor to generate efficient reverse intersystem crossing. Here, in this specification, the so-called "electron-donating substituent" (donor) refers to the substituent and partial structure where HOMO is locally present in the thermally activated delayed fluorophore molecule, and the so-called "electron-accepting substituent" (acceptor) refers to the substituent and partial structure where LUMO is locally present in the thermally activated delayed fluorophore molecule.

[0694] Generally, due to structural reasons, the thermally activated delayed fluorophore using a donor or an acceptor has a large spin-orbit coupling (SOC), a small exchange interaction between HOMO and LUMO, and a small ΔE(ST), so a very fast reverse intersystem crossing speed can be obtained.

[0695] However, by using a suitable emission dopant such as the polycyclic aromatic compound of the present invention and using a thermally activated delayed phosphor using a donor or an acceptor as an auxiliary dopant, an element satisfying any one or all of high efficiency, high color purity, and long life can be provided. The thermally activated delayed phosphor may be any compound as long as its emission spectrum overlaps at least a part of the absorption spectrum of the polycyclic aromatic compound of the present invention. The polycyclic aromatic compound of the present invention and the thermally activated delayed phosphor may be both contained in the same layer or may be contained in adjacent layers.

[0696] As the thermally activated delayed phosphor in the TAF element, for example, a compound in which a donor and an acceptor are directly bonded or bonded via a spacer can be used. As the electron-donating group (donor structure) and the electron-accepting group (acceptor structure) used in the thermally activated delayed phosphor of the present invention, for example, the structures described in "Chemistry of Materials" (2017, 29, 1946-1963) can be used. As the donor structure, examples include: carbazole, dimethylcarbazole, di-tert-butylcarbazole, dimethoxycarbazole, tetramethylcarbazole, benzofluorocarbazole, benzothienocarbazole, phenyldihydroindolocarbazole, phenylbiscarbazole, biscarbazole, tercarbazole, diphenylcarbazolylamine, tetraphenylcarbazolyl diamine, phenoxazine, dihydrophenoxazine, phenothiazine, dimethyldihydroacridine, diphenylamine, bis(tert-butylphenyl)amine, N1-(4-(diphenylamino)phenyl)-N4,N4-diphenylbenzene-1,4-diamine, dimethyltetraphenyldihydroacridine diamine, tetramethyl-dihydro-indenoacridine, and diphenyl-dihydrodibenzazasiline. As the acceptor structure, examples include: sulfonyldiphenyl, benzophenone, phenylenebis(phenyl ketone), benzonitrile, isonicitrile, phthalonitrile, isophthalonitrile, terephthalonitrile, benzenetricarbonitrile, triazole, oxazole, thiadiazole, benzothiazole, benzobis(thiazole), benzoxazole, benzobis(oxazole), quinoline, benzimidazole, dibenzoquinoxaline, heptazaphenalene, thioxanthene dioxide, dimethylanthrone, anthraquinone, 5H-cyclohepta[1,2-b:5,4-b']bipyridine, fluorenedicarbonitrile, triphenyltriazine, pyrazinedicarbonitrile, pyrimidine, phenylpyrimidine, methylpyrimidine, pyridinedicarbonitrile, dibenzoquinoxalinedicarbonitrile, bis(phenylsulfonyl)benzene, dimethylthioxanthene dioxide, thianthrene tetroxide, and tris(dimethylphenyl)borane. In particular, the compound having thermally activated delayed fluorescence in the TAF element is preferably a compound having at least one selected from carbazole, phenoxazine, acridine, triazine, pyrimidine, pyrazine, thioxanthene, benzonitrile, phthalonitrile, isophthalonitrile, diphenylsulfone, triazole, oxadiazole, thiadiazole, and benzophenone as a partial structure.

[0697] The compound used as the second component of the light-emitting layer in the TAF element is a thermally activated delayed phosphor, and preferably a compound whose emission spectrum overlaps at least partially with the absorption peak of the emission dopant. Hereinafter, compounds that can be used as the second component (thermally activated delayed phosphor) of the light-emitting layer in the TAF element are exemplified. Among them, the compounds that can be used as thermally activated delayed phosphors in the TAF element are not construed as being limited to the following exemplified compounds.

[0698] [Chemical formula 138]

[0699]

[0700] [Chemical formula 139]

[0701]

[0702] [Chemical formula 140]

[0703]

[0704] [Chemical formula 141]

[0705]

[0706] [Chemical formula 142]

[0707]

[0708] Furthermore, as the thermally activated delayed phosphor, a compound represented by any one of the following formulas (AD1), (AD2), and (AD3) can also be used.

[0709] [Chemical formula 143]

[0710]

[0711] In the formulas (AD1), (AD2) and (AD3), M is independently a single bond, -O-, >N-Ar or >CAr2, and is preferably a single bond, -O- or >N-Ar in terms of the depth of the HOMO of the formed partial structure and the heights of the lowest excited singlet state energy level and the lowest excited triplet state energy level. J is a spacer structure that separates the donor partial structure and the acceptor partial structure, and is independently an arylene group having 6 to 18 carbon atoms, and is preferably an arylene group having 6 to 12 carbon atoms in terms of the size of the conjugation exuded from the donor partial structure and the acceptor partial structure. More specifically, examples include: phenylene, methylphenylene and dimethylphenylene. Q is independently =C(-H)- or =N-, and is preferably =N- in terms of the shallowness of the LUMO of the formed partial structure and the heights of the lowest excited singlet state energy level and the lowest excited triplet state energy level. Ar is independently hydrogen, an aryl group having 6 to 24 carbon atoms, a heteroaryl group having 2 to 24 carbon atoms, an alkyl group having 1 to 12 carbon atoms or a cycloalkyl group having 3 to 18 carbon atoms, and is preferably hydrogen, an aryl group having 6 to 12 carbon atoms, a heteroaryl group having 2 to 14 carbon atoms, an alkyl group having 1 to 4 carbon atoms or a cycloalkyl group having 6 to 10 carbon atoms in terms of the depth of the HOMO of the formed partial structure and the heights of the lowest excited singlet state energy level and the lowest excited triplet state energy level. More preferably, it is hydrogen, phenyl, tolyl, xylyl, mesityl, biphenyl, pyridyl, bipyridyl, triazinyl, carbazolyl, dimethylcarbazolyl, di-tert-butylcarbazolyl, benzimidazolyl or phenylbenzimidazolyl, and even more preferably hydrogen, phenyl or carbazolyl. m is 1 or 2. n is an integer of (6 - m) or less, and is preferably an integer of 4 to (6 - m) in terms of steric hindrance. Further, at least one hydrogen in the compound represented by each of the above formulas may be substituted with a halogen or deuterium.

[0712] More specifically, the compound used as the second component in the present embodiment is preferably 4CzBN, 4CzBN-Ph, 5CzBN, 3Cz2DPhCzBN, 4CzIPN, 2PXZ-TAZ, Cz-TRZ3, BDPCC-TPTA, MA-TA, PA-TA, FA-TA, PXZ-TRZ, DMAC-TRZ, BCzT, DCzTrz, DDCzTRz, spiroAC-TRZ, Ac-HPM, Ac-PPM, Ac-MPM, TCzTrz, TmCzTrz and DCzmCzTrz.

[0713] The compound used as the second component in this embodiment may be a donor-acceptor type TADF compound represented by D-A in which a donor D and an acceptor A are directly bonded or bonded via a linking group. However, a compound having a structure represented by the following formula (DAD1) in which a plurality of donors D are directly bonded or bonded via a linking group to one acceptor A is a compound that makes the characteristics of the organic electroluminescent element more excellent, and thus is preferred.

[0714] (D 1 -L 1 )n-A 1 (DAD1)

[0715] The compound represented by the following formula (DAD2) is included in the formula (DAD1).

[0716] D 2 -L 2 -A 2 -L 3 -D 3 (DAD2)

[0717] In the formula (DAD1) and the formula (DAD2), D 1 , D 2 and D 3 each independently represent a donor group. As the donor group, the above-described donor structure can be used. A 1 and A 2 each independently represent an acceptor group. As the acceptor group, the above-described acceptor structure can be used. L 1 , L 2 and L 3 each independently represent a single bond or a conjugated linking group. The conjugated linking group is a spacer structure that separates the donor group and the acceptor group, and is preferably an arylene group having 6 to 18 carbon atoms, more preferably an arylene group having 6 to 12 carbon atoms. L 1 , L 2 and L 3 More preferably, they are each independently a phenylene group, a methylphenylene group, or a dimethylphenylene group. In the formula (DAD1), n is 2 or more and is an integer equal to or less than the maximum number of substitutions that A 1 can undergo. For example, n can be selected in the range of 2 to 10, or in the range of 2 to 6. When n is 2, it is the compound represented by the formula (DAD2). The n D 1 can be the same or different, and the n L 1 can be the same or different. As preferred specific examples of the compounds represented by the formula (DAD1) and the formula (DAD2), 2PXZ-TAZ or the following compounds can be cited, but the second component that can be used in the present invention is not limited to these compounds.

[0718] [Chemical formula 144]

[0719]

[0720] In this embodiment, the light-emitting layer may be a single layer or may include multiple layers, either of which is acceptable. Additionally, the host compound, the thermally activated delayed phosphor, and the polycyclic aromatic compound of the present invention may be included in the same layer or at least one component of each may be included in multiple layers. The host compound, the thermally activated delayed phosphor, and the polycyclic aromatic compound of the present invention included in the light-emitting layer may each be one type or a combination of multiple types, either of which is acceptable. The auxiliary dopant and the emission dopant may be included in the entirety of the host compound serving as the matrix or may be included in a part of the host compound serving as the matrix. The light-emitting layer doped with the auxiliary dopant and the emission dopant can be formed by the following methods: a method of forming a film of the host compound, the auxiliary dopant, and the emission dopant by ternary co-evaporation; a method of simultaneously evaporating the host compound, the auxiliary dopant, and the emission dopant after pre-mixing them; a wet film-forming method of coating a light-emitting layer-forming composition (coating) prepared by dissolving the host compound, the auxiliary dopant, and the emission dopant in an organic solvent, etc.

[0721] The usage amount of the host compound varies depending on the type of the host compound and can be determined as long as it is coordinated with the characteristics of the host compound. The benchmark of the usage amount of the host compound is preferably 40% by mass to 99% by mass, more preferably 50% by mass to 98% by mass, and still more preferably 60% by mass to 95% by mass of the total mass of the materials for the light-emitting layer. If it is within the above range, it is preferable, for example, in terms of efficient charge transport and efficient energy transfer to the dopant.

[0722] The usage amount of the auxiliary dopant (thermally activated delayed phosphor) varies depending on the type of the auxiliary dopant and can be determined as long as it is coordinated with the characteristics of the auxiliary dopant. The benchmark of the usage amount of the auxiliary dopant is preferably 1% by mass to 60% by mass, more preferably 2% by mass to 50% by mass, and still more preferably 5% by mass to 30% by mass of the total mass of the materials for the light-emitting layer. If it is within the above range, it is preferable, for example, in terms of efficiently transferring energy to the emission dopant.

[0723] The usage amount of the emission dopant (compound having a boron atom) varies depending on the type of the emission dopant and can be determined as long as it is coordinated with the characteristics of the emission dopant. The benchmark of the usage amount of the emission dopant is preferably 0.001% by mass to 30% by mass, more preferably 0.01% by mass to 20% by mass, and still more preferably 0.1% by mass to 10% by mass of the total mass of the materials for the light-emitting layer. If it is within the above range, it is preferable, for example, in terms of preventing the concentration quenching phenomenon.

[0724] In terms of preventing concentration quenching, it is preferable that the amount of the emission dopant used is at a low concentration. In terms of the efficiency of the thermally activated delayed fluorescence mechanism, it is preferable that the amount of the auxiliary dopant material used is at a high concentration. Further, in terms of the efficiency of the thermally activated delayed fluorescence mechanism of the auxiliary dopant, it is preferable that the amount of the emission dopant used is at a low concentration compared to the amount of the auxiliary dopant used.

[0725] <2-1-3. Substrate in the organic electroluminescent element>

[0726] The substrate 101 is a support for the organic EL element 100, and quartz, glass, metal, plastic, etc. can generally be used. The substrate 101 is formed into a plate shape, a film shape, or a sheet shape according to the purpose, and for example, a glass plate, a metal plate, a metal foil, a plastic film, a plastic sheet, etc. can be used. Among them, a glass plate and a plate made of a transparent synthetic resin such as polyester, polymethacrylate, polycarbonate, and polysulfone are preferable. In the case of a glass substrate, soda-lime glass or non-alkali glass can be used. In addition, the thickness is only required to be a thickness sufficient to maintain mechanical strength, so for example, it is sufficient to be 0.2 mm or more. As the upper limit value of the thickness, for example, it is 2 mm or less, and preferably 1 mm or less. Regarding the material of the glass, since the fewer eluted ions from the glass, the better, non-alkali glass is preferable. Since soda-lime glass with an isolation coating such as SiO2 is also commercially available, the soda-lime glass can be used. In addition, in order to improve the gas barrier property, a gas barrier film such as a fine silicon oxide film can be provided on at least one surface of the substrate 101. In the case where a plate, a film, or a sheet made of a synthetic resin with a low gas barrier property is used as the substrate 101, it is particularly preferable to provide a gas barrier film.

[0727] <2-1-4. Anode in the organic electroluminescent element>

[0728] The anode 102 functions to inject holes into the light-emitting layer 105. In addition, when either a hole injection layer 103 or a hole transport layer 104 is provided between the anode 102 and the light-emitting layer 105, holes are injected into the light-emitting layer 105 through these layers.

[0729] Examples of materials for forming the anode 102 include inorganic compounds and organic compounds. Examples of inorganic compounds include metals (such as aluminum, gold, silver, nickel, palladium, chromium, etc.), metal oxides (such as indium oxide, tin oxide, indium tin oxide (ITO), indium zinc oxide (IZO), etc.), metal halides (such as copper iodide, etc.), copper sulfide, carbon black, ITO glass, Nesa glass, etc. Examples of organic compounds include polythiophenes such as poly(3-methylthiophene), polypyrrole, conductive polymers such as polyaniline, etc. In addition, it can be appropriately selected and used from substances used as anodes of organic EL elements.

[0730] The resistance of the transparent electrode only needs to be able to supply sufficient current for the light emission of the light-emitting element, so there is no limitation. From the perspective of the power consumption of the light-emitting element, a low resistance is ideal. For example, an ITO substrate with a resistance of 300 Ω / square or less functions as an element electrode, but currently, substrates with a resistance of about 10 Ω / square can also be supplied. Therefore, it is particularly ideal to use a low-resistance product such as 100 Ω / square to 5 Ω / square, preferably 50 Ω / square to 5 Ω / square. The thickness of ITO can be arbitrarily selected according to the resistance value, and it is usually used between 50 nm and 300 nm in most cases.

[0731] <2-1-5. Hole injection layer and hole transport layer in organic electroluminescent element>

[0732] The hole injection layer 103 functions to efficiently inject the holes migrated from the anode 102 into the light-emitting layer 105 or the hole transport layer 104. The hole transport layer 104 functions to efficiently transport the holes injected from the anode 102 or the holes injected from the anode 102 via the hole injection layer 103 to the light-emitting layer 105. The hole injection layer 103 and the hole transport layer 104 are respectively formed by laminating and mixing one or more hole injection / transport materials, or formed by a mixture of a hole injection / transport material and a polymer binder. In addition, an inorganic salt such as iron(III) chloride can be added to the hole injection / transport material to form a layer.

[0733] As a hole injection / transport material, it is necessary to efficiently inject / transport holes from the positive electrode between the electrodes to which an electric field is applied. It is ideal to have a high hole injection efficiency and efficiently transport the injected holes. Therefore, a material with a small ionization potential, a large hole mobility, excellent stability, and less likely to generate trap impurities during manufacturing and use is preferred.

[0734] As materials for forming the hole injection layer 103 and the hole transport layer 104, any compound can be selected from compounds that have been conventionally used as charge transport materials for holes in photoconductive materials, p-type semiconductors, and known compounds used in the hole injection layer and the hole transport layer of organic EL elements since before. Specific examples of these are carbazole derivatives (N-phenylcarbazole, polyvinylcarbazole, etc.), biscarbazole derivatives such as bis(N-arylcarbazole) or bis(N-alkylcarbazole), triarylamine derivatives (4,4',4”-tris(N-carbazolyl)triphenylamine, polymers having an aromatic tertiary amino group in the main chain or side chain, 1,1-bis(4-di-p-tolylaminophenyl)cyclohexane, N,N'-diphenyl-N,N'-bis(3-methylphenyl)-4,4'-diaminobiphenyl, N,N'-diphenyl-N,N'-dinaphthyl-4,4'-diaminobiphenyl, N,N'-diphenyl-N,N'-bis(3-methylphenyl)-4,4'-diphenyl-1,1'-diamine, N,N'-dinaphthyl-N,N'-diphenyl-4,4'-diphenyl-1,1'-diamine, N 4 ,N 4 '-diphenyl-N 4 ,N 4 '-bis(9-phenyl-9H-carbazol-3-yl)-[1,1'-biphenyl]-4,4'-diamine, N 4 ,N 4 ,N 4 ',N 4 ',N

[0735] '-tetrakis[1,1'-biphenyl]-4-yl-[1,1'-biphenyl]-4,4'-diamine, triphenylamine derivatives such as 4,4',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 or thiophene derivatives, oxadiazole derivatives, quinoxaline derivatives (for example, 1,4,5,8,9,12-hexaazatriphenylene-2,3,6,7,10,11-hexacarbonitrile, etc.), heterocyclic compounds such as porphyrin derivatives, polysilanes, etc. In the polymer system, polycarbonates or styrene derivatives having the monomer in the side chain, polyvinylcarbazole, and polysilanes are preferred, but as long as it is a compound that can inject holes from the anode and further transport holes to form a thin film required for the production of a light-emitting element, there is no particular limitation.In addition, it is also known that the conductivity of an organic semiconductor is strongly affected by doping. Such an organic semiconductor matrix material contains a compound with good electron-donating properties or a compound with good electron-accepting properties. For doping an electron-donating substance, strong electron acceptors such as tetracyanoquinonedimethane (TCNQ) or 2,3,5,6-tetrafluorotetracyano-1,4-benzoquinonedimethane (F4TCNQ) are known (for example, refer to the literature "M. Pfeiffer, A. Beyer, T. Fritz, K. Leo, Appl. Phys. Lett., 73(22), 3202 - 3204 (1998)" and the literature "J. Blochwitz, M. Pfeiffer, T. Fritz, K. Leo, Appl. Phys. Lett., 73(6), 729 - 731 (1998)"). These generate so-called holes through the electron transfer process of an electron-donating base material (hole transport material). The conductivity of the base material changes considerably according to the number and mobility of the holes. As matrix materials having hole transport properties, for example, benzidine derivatives (such as N,N'-bis(3-methylphenyl)-N,N'-bis(phenyl)benzidine (TPD)) or starburst amine derivatives (such as 4,4',4”-tris(N,N-diphenylamino)triphenylamine (TDATA)), or specific metal phthalocyanines (especially zinc phthalocyanine (ZnPc), etc.) (Japanese Patent Laid-Open No. 2005-167175) are known. The polycyclic aromatic compound of the present invention can be used as a material for forming a hole injection layer or a material for forming a hole transport layer.

[0736] <2-1-6. Electron blocking layer in organic electroluminescent element>

[0737] An electron blocking layer for preventing the diffusion of electrons from the light-emitting layer can also be provided between the hole injection / transport layer and the light-emitting layer. For forming the electron blocking layer, any of the compounds represented by the above formula (H1), formula (H2), and formula (H3) can be used. The polycyclic aromatic compound of the present invention can be used as a material for forming an electron blocking layer.

[0738] <2-1-7. Electron injection layer and electron transport layer in organic electroluminescent element>

[0739] The electron injection layer 107 functions to efficiently inject the electrons migrated from the cathode 108 into the light-emitting layer 105 or the electron transport layer 106. The electron transport layer 106 functions to efficiently transport the electrons injected from the cathode 108 or the electrons injected from the cathode 108 via the electron injection layer 107 to the light-emitting layer 105. The electron transport layer 106 and the electron injection layer 107 are each formed by laminating and mixing one or more than two kinds of electron transport / injection materials, or formed by a mixture of an electron transport / injection material and a polymer binder.

[0740] The so-called electron injection / transport layer is a layer that is responsible for injecting electrons from the cathode and then transporting the electrons. Ideally, it has a high electron injection efficiency and can efficiently transport the injected electrons. Therefore, a material with a large electron affinity, a large electron mobility, excellent stability, and that is not likely to generate trap impurities during manufacturing and use is preferred. However, when considering the transport balance between holes and electrons, in the case of mainly functioning to efficiently prevent the holes from the anode from recombining and flowing to the cathode side, even if the electron transport ability is not so high, it has the effect of improving the light emission efficiency equally to a material with a high electron transport ability. Therefore, the electron injection / transport layer in the present embodiment may also include the function of a layer that can efficiently prevent hole migration.

[0741] As the material (electron transport material) for forming the electron transport layer 106 or the electron injection layer 107, it can be arbitrarily selected from the compounds that have been conventionally used as electron transfer compounds in photoconductive materials and the known compounds used in the electron injection layer and electron transport layer of organic EL elements.

[0742] As a material used in an electron transport layer or an electron injection layer, it is preferably at least one selected from the following compounds: a compound containing an aromatic ring or a heteroaromatic ring containing one or more atoms selected from carbon, hydrogen, oxygen, sulfur, silicon, and phosphorus; a pyrrole derivative and its condensed ring derivative; and a metal complex having an electron-accepting nitrogen. Specifically, examples include condensed ring aromatic ring derivatives such as naphthalene and anthracene, styryl aromatic ring derivatives represented by 4,4'-bis(diphenylvinyl)biphenyl, perylenequinone derivatives, coumarin derivatives, naphthalenedicarboximide derivatives, quinone derivatives such as anthraquinone or biphenylquinone, phosphine oxide derivatives, aryl nitrile derivatives, and indole derivatives. As a metal complex having an electron-accepting nitrogen, for example, hydroxyazole complexes such as hydroxyphenyl oxazole complexes, azomethine complexes, tropolone metal complexes, flavonol metal complexes, and benzoquinoline metal complexes can be cited. These materials can be used alone or in combination with different materials.

[0743] In addition, specific examples of other electron transfer compounds include: pyridine derivatives, naphthalene derivatives, fluoranthene derivatives, BO series derivatives, anthracene derivatives, phenanthroline derivatives, perylenequinone derivatives, coumarin derivatives, naphthalenedicarboximide derivatives, anthraquinone derivatives, biphenylquinone derivatives, diphenylquinone derivatives, perylene derivatives, oxadiazole derivatives (such as 1,3-bis[(4-tert-butylphenyl)-1,3,4-oxadiazolyl]phenylene), thiophene derivatives, triazole derivatives (such as N-naphthyl-2,5-diphenyl-1,3,4-triazole), thiadiazole derivatives, metal complexes of 8-hydroxyquinoline derivatives, hydroxyquinoline-based metal complexes, quinoxaline derivatives, polymers of quinoxaline derivatives, benzoxazole compounds, gallium complexes, pyrazole derivatives, perfluorinated phenylene derivatives, triazine derivatives, pyrazine derivatives, benzoquinoline derivatives (such as 2,2'-bis(benzo[h]quinolin-2-yl)-9,9'-spirobifluorene), imidazopyridine derivatives, borane derivatives, benzimidazole derivatives (such as tris(N-phenylbenzimidazol-2-yl)benzene), benzoxazole derivatives, thiazole derivatives, benzothiazole derivatives, quinoline derivatives, oligopyridine derivatives such as terpyridine, bipyridine derivatives, terpyridine derivatives (such as 1,3-bis(2,2':6',2”-terpyridin-4'-yl)benzene), naphthyridine derivatives (such as bis(1-naphthyl)-4-(1,8-naphthyridin-2-yl)phenylphosphine oxide), azine derivatives, pyrimidine derivatives, aryl nitrile derivatives, indole derivatives, phosphine oxide derivatives, distyryl derivatives, silole derivatives, and oxazoline derivatives.

[0744] In addition, metal complexes having an electron-accepting nitrogen can also be used, and examples thereof include: hydroxyazole complexes such as hydroxyquinoline-based metal complexes or hydroxyphenyl oxazole complexes, azomethine complexes, tropolone metal complexes, flavonol metal complexes, and benzoquinoline metal complexes.

[0745] The above materials can be used alone or in combination with different materials.

[0746] Among the above materials, borane derivatives, pyridine derivatives, fluoranthene derivatives, BO-based derivatives, anthracene derivatives, benzofluorene derivatives, phosphine oxide derivatives, pyrimidine derivatives, aryl nitrile derivatives, triazine derivatives, benzimidazole derivatives, phenanthroline derivatives, hydroxyquinoline-based metal complexes, thiazole derivatives, benzothiazole derivatives, silafluorene derivatives, and oxazoline derivatives are preferred.

[0747] The polycyclic aromatic compound of the present invention can also be used as a material for forming an electron injection layer or an electron transport layer.

[0748] A substance capable of reducing the material for forming the electron transport layer or the electron injection layer may also be included in the electron transport layer or the electron injection layer. As long as the reducing substance has a certain reducing property, various substances can be used. For example, at least one selected from the group consisting of alkali metals, alkaline earth metals, rare earth metals, oxides of alkali metals, halides of alkali metals, oxides of alkaline earth metals, halides of alkaline earth metals, oxides of rare earth metals, halides of rare earth metals, organic complexes of alkali metals, organic complexes of alkaline earth metals, and organic complexes of rare earth metals can be preferably used.

[0749] As preferred reducing substances, 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), or alkaline earth metals such as Ca (work function 2.9 eV), Sr (work function 2.0 eV to 2.5 eV), or Ba (work function 2.52 eV) can be cited. Substances with a work function of 2.9 eV or less are particularly preferred. Among these, more preferred reducing substances are alkali metals such as K, Rb, or Cs, and further preferably Rb or Cs, and most preferably Cs. These alkali metals have particularly high reducing ability. By adding a relatively small amount of the alkali metal to the material forming the electron transport layer or electron injection layer, an increase in the emission luminance or an extension of the lifetime in the organic EL element can be achieved. In addition, as reducing substances with a work function of 2.9 eV or less, combinations of two or more of these alkali metals are also preferred, and combinations containing Cs are particularly preferred, such as combinations of Cs and Na, Cs and K, Cs and Rb, or Cs and Na and K. By including Cs, the reducing ability can be effectively exerted, and by adding it to the material forming the electron transport layer or electron injection layer, an increase in the emission luminance or an extension of the lifetime in the organic EL element can be achieved.

[0750] <2-1-8. Cathode in Organic Electroluminescent Element>

[0751] The cathode 108 functions to inject electrons into the light-emitting layer 105 via the electron injection layer 107 and the electron transport layer 106.

[0752] As the material for forming the cathode 108, there is no particular limitation as long as it is a substance that can inject electrons into the organic layer well, and the same materials as those for 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 (such as magnesium-silver alloy, magnesium-indium alloy, aluminum-lithium alloys such as lithium fluoride / aluminum, etc.) are preferred. In order to improve the element characteristics by increasing the electron injection efficiency, lithium, sodium, potassium, cesium, calcium, magnesium, or alloys containing these low work function metals are effective. However, generally, most of these low work function metals are unstable in the atmosphere. To improve this point, for example, a method of doping a trace amount of lithium, cesium, or magnesium into the organic layer and using an electrode with high stability is known. 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.

[0753] Furthermore, the following can be cited as preferred examples: Metals such as platinum, gold, silver, copper, iron, tin, aluminum, and indium, or alloys using these metals, as well as inorganic substances such as silicon dioxide, titanium dioxide, and silicon nitride, polyvinyl alcohol, vinyl chloride, hydrocarbon-based polymer compounds, etc. are laminated to protect the electrodes. The manufacturing method of these electrodes is not particularly limited as long as it is a method capable of achieving conduction such as resistance heating, electron beam evaporation, sputtering, ion plating, and coating.

[0754] <2-1-9. Binders that can be used in each layer>

[0755] The materials used in the above hole injection layer, hole transport layer, light-emitting layer, electron transport layer, and electron injection layer can form each layer independently, or can be dispersed in solvent-soluble resins such as polyvinyl chloride, polycarbonate, polystyrene, poly(N-vinylcarbazole), polymethyl methacrylate, polybutyl methacrylate, polyester, polysulfone, polyphenylene ether, polybutadiene, hydrocarbon resin, ketone resin, phenoxy resin, polyamide, ethyl cellulose, vinyl acetate resin, acrylonitrile-butadiene-styrene (ABS) resin, polyurethane resin, etc., or hardenable resins such as phenolic resin, xylene resin, petroleum resin, urea resin, melamine resin, unsaturated polyester resin, alkyd resin, epoxy resin, silicone resin, etc. for use.

[0756] <2-1-10. Manufacturing method of organic electroluminescent element>

[0757] Each layer constituting the organic EL element can be formed by forming a film of the material that should constitute each layer using methods such as evaporation method, resistance heating evaporation, electron beam evaporation, sputtering, molecular lamination method, printing method, inkjet method, spin coating method, or casting method, coating method, etc. The film thickness of each layer formed in the above manner is not particularly limited and can be appropriately set according to the properties of the material, but is usually in the range of 2 nm to 5000 nm. The film thickness can generally be measured using a quartz oscillator type film thickness measuring device, etc. In the case of thinning by the evaporation method, the evaporation conditions vary depending on the type of material, the target crystal structure and association structure of the formed film, etc. Generally, the evaporation conditions are preferably appropriately set within the range of boat heating temperature of +50°C to +400°C, vacuum degree of 10 -6 Pa to 10 -3 Pa, evaporation rate of 0.01 nm / sec to 50 nm / sec, substrate temperature of -150°C to +300°C, and film thickness of 2 nm to 5 μm.

[0758] Next, as an example of a method for manufacturing an organic EL element, a method for manufacturing an organic EL element including an anode / hole injection layer / hole transport layer / light-emitting layer containing a host material and a dopant material / electron transport layer / electron injection layer / cathode will be described. After forming an anode by forming a thin film of an anode material on an appropriate substrate using a vapor deposition method or the like, thin films of a hole injection layer and a hole transport layer are formed on the anode. The host material and the dopant material are co-evaporated on the thin film to form a thin film as the light-emitting layer, an electron transport layer and an electron injection layer are formed on the light-emitting layer, and then a thin film containing a cathode material is formed as the cathode using a vapor deposition method or the like, thereby obtaining the target organic EL element. In addition, in the manufacture of the organic EL element, the manufacturing order can be reversed, and it can be manufactured in the order of cathode, electron injection layer, electron transport layer, light-emitting layer, hole transport layer, hole injection layer, and anode.

[0759] When a DC voltage is applied to the organic EL element obtained in the above manner, it is only necessary to apply the anode as the + polarity and the cathode as the - polarity. If a voltage of about 2V to 40V is applied, light emission can be observed from the transparent or semi-transparent electrode side (anode or cathode, and both). In addition, the organic EL element also emits light when a pulsed current or an alternating current is applied. In addition, the waveform of the applied alternating current can be arbitrary.

[0760] <2-1-11. Application examples of organic electroluminescent elements>

[0761] The organic EL element can also be applied to a display device or a lighting device.

[0762] A display device or a lighting device including an organic EL element can be manufactured by a known method such as connecting the organic EL element to a known driving device, and known driving methods such as DC driving, pulsed driving, and AC driving can be appropriately used for driving.

[0763] Examples of the display device include panel displays such as color flat panel displays, and flexible displays such as flexible color organic electroluminescent (EL) displays (for example, refer to Japanese Patent Laid-Open No. 10-335066, Japanese Patent Laid-Open No. 2003-321546, Japanese Patent Laid-Open No. 2004-281086, etc.). In addition, as the display mode of the display, for example, any one of a matrix mode and a segment mode can be cited. In addition, matrix display and segment display can coexist on the same panel.

[0764] In a matrix, pixels for display are two-dimensionally arranged in a lattice pattern or a mosaic pattern, etc., so that characters or images are displayed by a collection of pixels. The shape or size of the pixels is determined according to the use. For example, in the display of images and characters on a personal computer, a monitor, or a television, quadrangular pixels with a side length of 300 μm or less are usually used. In addition, in the case of a large display such as a display panel, pixels with a side length in the millimeter range are used. In the case of monochromatic display, pixels of the same color are simply arranged. In the case of color display, red, green, and blue pixels are arranged side by side for display. In the above cases, typical ones are the triangular type and the stripe type. Moreover, as a driving method of the matrix, either a line-sequential driving method or an active matrix can be used. The line-sequential driving has the advantage of simple structure, but in consideration of the operating characteristics, sometimes the active matrix is more excellent. Therefore, the driving method also needs to be distinguished according to the use.

[0765] In the segment type, a pattern is formed in such a way as to display predetermined information, and a determined area is made to emit light. For example, the display of time or temperature in a digital clock or a thermometer, the display of the operating state of an audio device or an induction cooker, and the display on a car panel, etc. can be cited.

[0766] As a lighting device, for example, lighting devices such as indoor lighting, backlights of liquid crystal display devices, etc. (for example, refer to Japanese Patent Laid-Open No. 2003-257621, Japanese Patent Laid-Open No. 2003-277741, Japanese Patent Laid-Open No. 2004-119211, etc.) can be cited. The backlight is mainly used to improve the visibility of a display device that does not emit light by itself, and is used for liquid crystal display devices, clocks, audio devices, car panels, display boards, signs, etc. In particular, as a backlight for personal computer applications where thinning is a problem in liquid crystal display devices, considering that the existing methods are difficult to thin due to the inclusion of fluorescent lamps or light guide plates, the backlight using an organic EL element has the characteristics of being thin and lightweight.

[0767] <2-2. Other organic devices>

[0768] The polycyclic aromatic compound of the present invention can be used not only for the above-mentioned organic electroluminescent element, but also for the production of organic field effect transistors, organic thin film solar cells, etc.

[0769] An organic field effect transistor is a transistor that uses an electric field generated by voltage input to control current. In addition to a source electrode and a drain electrode, a gate electrode is also provided. An organic field effect transistor is a transistor in which an electric field is generated when a voltage is applied to the gate electrode, and the flow of electrons (or holes) flowing between the source electrode and the drain electrode can be arbitrarily blocked to control the current. Compared with a single transistor (bipolar transistor), a field effect transistor is easy to miniaturize and is often used as a component constituting an integrated circuit, etc.

[0770] Regarding the structure of an organic field effect transistor, generally, a source electrode and a drain electrode are provided in contact with an organic semiconductor active layer formed using the polycyclic aromatic compound of the present invention, and a gate electrode is provided via an insulating layer (dielectric layer) in contact with the organic semiconductor active layer. As an example of its element structure, the following structure can be cited.

[0771] (1) Substrate / gate electrode / insulator layer / source electrode, drain electrode / organic semiconductor active layer

[0772] (2) Substrate / gate electrode / insulator layer / organic semiconductor active layer / source electrode, drain electrode

[0773] (3) Substrate / organic semiconductor active layer / source electrode, drain electrode / insulator layer / gate electrode

[0774] (4) Substrate / source electrode, drain electrode / organic semiconductor active layer / insulator layer / gate electrode

[0775] The organic field effect transistor configured in this way can be used as a pixel driving switch element of an active matrix driving liquid crystal display or an organic electroluminescent display, etc.

[0776] Organic thin film solar cells have a structure in which an anode, a hole transport layer, a photoelectric conversion layer, an electron transport layer, and a cathode of ITO or the like are stacked on a transparent substrate such as glass. The photoelectric conversion layer has a p-type semiconductor layer on the anode side and an n-type semiconductor layer on the cathode side. The polycyclic aromatic compounds of the present invention can be used as materials for hole transport layers, p-type semiconductor layers, n-type semiconductor layers, and electron transport layers according to their physical properties. In organic thin film solar cells, the polycyclic aromatic compounds of the present invention can function as hole transport materials or electron transport materials. In addition to the above layers, organic thin film solar cells may also appropriately include a hole blocking layer, an electron blocking layer, an electron injection layer, a hole injection layer, a smoothing layer, and the like. In organic thin film solar cells, known materials used for organic thin film solar cells can be appropriately selected for use in combination.

[0777] <3. Wavelength conversion materials>

[0778] The polycyclic aromatic compound of the present invention can be used as a wavelength conversion material.

[0779] At present, active research is being conducted on applying color conversion-based multicolorization technologies to liquid crystal displays, organic EL displays, lighting, etc. Color conversion refers to converting the light emitted from a light-emitting body into light with a longer wavelength. For example, it means converting ultraviolet light or blue light into green light or red light emission. By forming a wavelength conversion material having the color conversion function into a film and combining it with a blue light source, for example, it is possible to extract the three primary colors of blue, green, and red, that is, white light, from the blue light source. By using such a white light source formed by combining a blue light source and a wavelength conversion film having 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 fabricate a full-color display. In addition, without a liquid crystal driving part, it can be directly used as a white light source. For example, it can be applied as a white light source for light-emitting diode (LED) lighting, etc. Further, by using a blue organic EL element as a light source and combining it with a wavelength conversion film that converts blue light into green light and red light, it is possible to fabricate a full-color organic EL display without using a metal mask. Furthermore, by using a blue micro LED as a light source and combining it with a wavelength conversion film that converts blue light into green light and red light, it is possible to fabricate a low-cost full-color micro LED display.

[0780] The polycyclic aromatic compound of the present invention can be used as the wavelength conversion material. A wavelength conversion material containing the polycyclic aromatic compound of the present invention can be used to convert ultraviolet light or light from a light source or light-emitting element that generates blue light with a shorter wavelength into highly color-pure blue light or green light suitable for use in a display device (a display device using an organic EL element or a liquid crystal display device). The adjustment of the converted color can be carried out by appropriately selecting substituents of the polycyclic aromatic compound of the present invention, a binder resin used in the wavelength conversion composition described later, and the like. The wavelength conversion material is prepared as a wavelength conversion composition containing the polycyclic aromatic compound of the present invention. In addition, the wavelength conversion film can also be formed using the wavelength conversion composition.

[0781] In addition to the polycyclic aromatic compound of the present invention, the wavelength conversion composition may further contain a binder resin, other additives, and a solvent. As the binder resin, for example, the resins 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 can be made to the description of the solvent contained in the composition for forming a light-emitting layer.

[0782] The wavelength conversion film includes a wavelength conversion layer formed by curing a wavelength conversion composition. As a method for producing a wavelength conversion layer from a wavelength conversion composition, known film formation methods can be referred to. The wavelength conversion film may include only a wavelength conversion layer formed from a composition containing the polycyclic aromatic compound of the present invention, or may include other wavelength conversion layers (for example, a wavelength conversion layer that converts blue light into green light or red light, a wavelength conversion layer that converts blue light or green light into red light). Further, the wavelength conversion film may also include a substrate layer or a barrier layer for preventing the color conversion layer from deteriorating due to oxygen, moisture, or heat.

[0783] Examples

[0784] Hereinafter, the present invention will be described in more detail by way of examples, but the present invention is not limited to these examples.

[0785] In the examples, APCI-MS (atmospheric pressure chemical ionization - mass spectrometry) refers to atmospheric pressure chemical ionization mass spectrometry.

[0786] <<Synthesis Example>>

[0787] <<Synthesis Example (1): Synthesis of Compound (1 - 1 - 1)>>

[0788] [Chemical Formula 145]

[0789]

[0790] Under a nitrogen atmosphere, 41.4 g of intermediate (Int - 1 - 1 - 1 - 1), 23.8 g of 5 - tert - butyl - 1,2,3 - trichlorobenzene, 2.1 g of dichloro bis[di - tert - butyl(4 - dimethylaminophenyl)phosphino]palladium(II) (Pd - 132) as a palladium catalyst, 14.4 g of tBuONa, and toluene (ml) were placed in a flask and heated at the reflux temperature for 8 hours. After the reaction was completed, water and ethyl acetate were added to the reaction solution and stirred, and then the organic layer was separated and washed with water. Thereafter, the crude product obtained by concentrating the organic layer was purified using a silica gel short - path column (eluent: toluene / heptane = 1 / 4 (volume ratio)) to obtain intermediate (Int - 1 - 1 - 1 - 2) (55.5 g).

[0791] [Chemical Formula 146]

[0792]

[0793] Under a nitrogen atmosphere, the intermediate (Int-1-1-1-2) (30.7 g), the intermediate (Int-1-1-3) (17.1 g), Pd-132 (1.1 g) as a palladium catalyst, tBuONa (7.2 g), and toluene (300 ml) were placed in a flask and heated at the reflux temperature for 6 hours. After completion of the reaction, water and ethyl acetate were added to the reaction solution and stirred, and then the organic layer was separated and washed with water. Thereafter, the crude product obtained by concentrating the organic layer was purified using a silica gel short column (eluent: toluene / heptane = 1 / 5 (volume ratio)) to obtain the intermediate (Int-1-1-1) (22.2 g).

[0794] [Chemical formula 147]

[0795]

[0796] Under a nitrogen atmosphere and at 0 °C, 1.60 M tert-butyllithium pentane solution (13.8 ml) was added to a flask containing the intermediate (Int-1-1-1) (9.2 g) and tert-butylbenzene (100 ml). After completion of the dropwise addition, the temperature was raised to 70 °C and stirred for 0.5 hour, and then the components with a boiling point lower than that of tert-butylbenzene were distilled off under reduced pressure. The mixture was cooled to -50 °C and boron tribromide (3.8 g) was added, and then the temperature was raised to room temperature and stirred for 0.5 hour. Thereafter, it was cooled again to 0 °C and N,N-diisopropylethylamine (3.9 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, an aqueous sodium acetate solution cooled by an ice bath was added, and then ethyl acetate was added for liquid separation. The organic layer was concentrated and purified using a silica gel short column (eluent: toluene / heptane = 1 / 5 (volume ratio)). The obtained crude product was recrystallized from toluene to obtain the compound (1-1-1) (2.0 g).

[0797] [Chemical formula 148]

[0798]

[0799] The target product with m / z (M+H) = 893.56 was confirmed by APCI-MS.

[0800] Synthesis Example (2): Synthesis of Compound (1-1-3)

[0801] In the same manner as in Synthesis Example (1), the compound (1-1-3) was obtained from the intermediate (Int-1-1-3).

[0802] [Chemical formula 149]

[0803]

[0804] The target substance with m / z(M+H)=949.62 was confirmed by APCI-MS.

[0805] Synthesis Example (3): Synthesis of Compound (1-1-5)

[0806] In the same manner as in Synthesis Example (1), Compound (1-1-5) was obtained from Intermediate (Int-1-1-5).

[0807] [Chemical Formula 150]

[0808]

[0809] The target substance with m / z(M+H)=851.51 was confirmed by APCI-MS.

[0810] Synthesis Example (4): Synthesis of Compound (1-1-10)

[0811] In the same manner as in Synthesis Example (1), Compound (1-1-10) was obtained from Intermediate (Int-1-1-10).

[0812] [Chemical Formula 151]

[0813]

[0814] The target substance with m / z(M+H)=1057.71 was confirmed by APCI-MS.

[0815] Synthesis Example (5): Synthesis of Compound (1-2-7)

[0816] In the same manner as in Synthesis Example (1), Compound (1-2-7) was obtained from Intermediate (Int-1-2-7).

[0817] [Chemical Formula 152]

[0818]

[0819] The target substance with m / z(M+H)=1015.67 was confirmed by APCI-MS.

[0820] Synthesis Example (6): Synthesis of Compound (1-3-4)

[0821] In the same manner as in Synthesis Example (1), Compound (1-3-4) was obtained from Intermediate (Int-1-3-4).

[0822] [Chemical Formula 153]

[0823]

[0824] The target substance with m / z(M+H)=1023.64 was confirmed by APCI-MS.

[0825] Synthesis Example (7): Synthesis of Compound (1-3-6)

[0826] In the same manner as in Synthesis Example (1), Compound (1-3-6) was obtained from Intermediate (Int-1-3-6).

[0827] [Chemical Formula 154]

[0828]

[0829] The target substance with m / z(M+H)=1055.70 was confirmed by APCI-MS.

[0830] Synthesis Example (8): Synthesis of Compound (1-3-9)

[0831] In the same manner as in Synthesis Example (1), Compound (1-3-9) was obtained from Intermediate (Int-1-3-9).

[0832] [Chemical Formula 155]

[0833]

[0834] The target substance with m / z(M+H)=1091.70 was confirmed by APCI-MS.

[0835] Synthesis Example (9): Synthesis of Compound (1-3-10)

[0836] In the same manner as in Synthesis Example (1), Compound (1-3-10) was obtained from Intermediate (Int-1-3-10).

[0837] [Chemical Formula 156]

[0838]

[0839] The target substance with m / z(M+H)=1375.95 was confirmed by APCI-MS.

[0840] Synthesis Example (10): Synthesis of Compound (1-4-2)

[0841] In the same manner as in Synthesis Example (1), Compound (1-4-2) was obtained from Intermediate (Int-1-4-2).

[0842] [Chemical Formula 157]

[0843]

[0844] The target substance with m / z(M+H)=1169.75 was confirmed by APCI-MS.

[0845] Synthesis Example (11): Synthesis of Compound (1-4-5)

[0846] In the same manner as in Synthesis Example (1), Compound (1-4-5) was obtained from Intermediate (Int-1-4-5).

[0847] [Chemical Formula 158]

[0848]

[0849] The target substance with m / z(M+H)=1267.86 was confirmed by APCI-MS.

[0850] Synthesis Example (12): Synthesis of Compound (1-5-8)

[0851] In the same manner as in Synthesis Example (1), Compound (1-5-8) was obtained from Intermediate (Int-1-5-8).

[0852] [Chemical Formula 159]

[0853]

[0854] The target substance with m / z(M+H)=1057.71 was confirmed by APCI-MS.

[0855] Synthesis Example (13): Synthesis of Compound (1-6-2)

[0856] In the same manner as in Synthesis Example (1), Compound (1-6-2) was obtained from Intermediate (Int-1-6-2).

[0857] [Chemical Formula 160]

[0858]

[0859] The target substance with m / z(M+H)=1133.75 was confirmed by APCI-MS.

[0860] Synthesis Example (14): Synthesis of Compound (1-6-6)

[0861] In the same manner as in Synthesis Example (1), Compound (1-6-6) was obtained from Intermediate (Int-1-6-6).

[0862] [Chemical Formula 161]

[0863]

[0864] The target compound with m / z(M+H)=1209.78 was confirmed by APCI-MS.

[0865] Synthesis Example (15): Synthesis of Compound (1-6-10)

[0866] In the same manner as in Synthesis Example (1), Compound (1-6-10) was obtained from Intermediate (Int-1-6-10).

[0867] [Chemical Formula 162]

[0868]

[0869] The target compound with m / z(M+H)=1209.78 was confirmed by APCI-MS.

[0870] Synthesis Example (16): Synthesis of Compound (1-7-3)

[0871] In the same manner as in Synthesis Example (1), Compound (1-7-3) was obtained from Intermediate (Int-1-7-3).

[0872] [Chemical Formula 163]

[0873]

[0874] The target compound with m / z(M+H)=1059.73 was confirmed by APCI-MS.

[0875] Synthesis Example (17): Synthesis of Compound (1-8-2)

[0876] In the same manner as in Synthesis Example (1), Compound (1-8-2) was obtained from Intermediate (Int-1-8-2).

[0877] [Chemical Formula 164]

[0878]

[0879] The target compound with m / z(M+H)=1136.66 was confirmed by APCI-MS.

[0880] Synthesis Example (18): Synthesis of Compound (1-8-6)

[0881] In the same manner as in Synthesis Example (1), Compound (1-8-6) was obtained from Intermediate (Int-1-8-6).

[0882] [Chemical Formula 165]

[0883]

[0884] The target substance with m / z(M+H)=1282.87 was confirmed by APCI-MS.

[0885] Synthesis Example (19): Synthesis of Compound (1-9-2)

[0886] In the same manner as in Synthesis Example (1), Compound (1-9-2) was obtained from Intermediate (Int-1-9-2).

[0887] [Chemical Formula 166]

[0888]

[0889] The target substance with m / z(M+H)=1072.60 was confirmed by APCI-MS.

[0890] Synthesis Example (20): Synthesis of Compound (1-9-5)

[0891] In the same manner as in Synthesis Example (1), Compound (1-9-5) was obtained from Intermediate (Int-1-9-5).

[0892] [Chemical Formula 167]

[0893]

[0894] The target substance with m / z(M+H)=906.42 was confirmed by APCI-MS.

[0895] Synthesis Example (21): Synthesis of Compound (1-9-9)

[0896] In the same manner as in Synthesis Example (1), Compound (1-9-9) was obtained from Intermediate (Int-1-9-9).

[0897] [Chemical Formula 168]

[0898]

[0899] The target substance with m / z(M+H)=982.45 was confirmed by APCI-MS.

[0900] Synthesis Example (22): Synthesis of Compound (1-11-8)

[0901] In the same manner as in Synthesis Example (1), Compound (1-11-8) was obtained from Intermediate (Int-1-11-8).

[0902] [Chemical Formula 169]

[0903]

[0904] The target substance with m / z(M+H)=849.46 was confirmed by APCI-MS.

[0905] Synthesis Example (23): Synthesis of Compound (1-15-2)

[0906] In the same manner as in Synthesis Example (1), Compound (1-15-2) was obtained from Intermediate (Int-1-15-2).

[0907] [Chemical Formula 170]

[0908]

[0909] The target substance with m / z(M+H)=1015.63 was confirmed by APCI-MS.

[0910] Synthesis Example (24): Synthesis of Compound (1-15-9)

[0911] In the same manner as in Synthesis Example (1), Compound (1-15-9) was obtained from Intermediate (Int-1-15-9).

[0912] [Chemical Formula 171]

[0913]

[0914] The target substance with m / z(M+H)=1149.47 was confirmed by APCI-MS.

[0915] Synthesis Example (25): Synthesis of Compound (1-16-6)

[0916] In the same manner as in Synthesis Example (1), Compound (1-16-6) was obtained from Intermediate (Int-1-16-6).

[0917] [Chemical Formula 172]

[0918]

[0919] The target substance with m / z(M+H)=1071.60 was confirmed by APCI-MS.

[0920] Synthesis Example (26): Synthesis of Compound (1-16-8)

[0921] In the same manner as in Synthesis Example (1), Compound (1-16-8) was obtained from Intermediate (Int-1-16-8).

[0922] [Chemical Formula 173]

[0923]

[0924] The target substance with m / z(M+H)=1197.74 was confirmed by APCI-MS.

[0925] Synthesis Example (27): Synthesis of Compound (1-17-1)

[0926] In the same manner as in Synthesis Example (1), Compound (1-17-1) was obtained from Intermediate (Int-1-17-1).

[0927] [Chemical Formula 174]

[0928]

[0929] The target substance with m / z(M+H)=1206.70 was confirmed by APCI-MS.

[0930] Synthesis Example (28): Synthesis of Compound (1-17-3)

[0931] In the same manner as in Synthesis Example (1), Compound (1-17-3) was obtained from Intermediate (Int-1-17-3).

[0932] [Chemical Formula 175]

[0933]

[0934] The target substance with m / z(M+H)=1093.68 was confirmed by APCI-MS.

[0935] Synthesis Example (29): Synthesis of Compound (1-17-5)

[0936] In the same manner as in Synthesis Example (1), Compound (1-17-5) was obtained from Intermediate (Int-1-17-5).

[0937] [Chemical Formula 176]

[0938]

[0939] The target substance with m / z(M+H)=1169.71 was confirmed by APCI-MS.

[0940] Synthesis Example (30): Synthesis of Compound (1-17-10)

[0941] In the same manner as in Synthesis Example (1), Compound (1-17-10) was obtained from Intermediate (Int-1-17-10).

[0942] [Chemical Formula 177]

[0943]

[0944] The target substance with m / z(M+H)=1016.53 was confirmed by APCI-MS.

[0945] Synthesis Example (31): Synthesis of Compound (1-19-1)

[0946] In the same manner as in Synthesis Example (1), Compound (1-19-1) was obtained from Intermediate (Int-1-19-1).

[0947] [Chemical Formula 178]

[0948]

[0949] The target substance with m / z(M+H)=940.64 was confirmed by APCI-MS.

[0950] Synthesis Example (32): Synthesis of Compound (1-19-3)

[0951] In the same manner as in Synthesis Example (1), Compound (1-19-3) was obtained from Intermediate (Int-1-19-3).

[0952] [Chemical Formula 179]

[0953]

[0954] The target substance with m / z(M+H)=1017.52 was confirmed by APCI-MS.

[0955] Synthesis Example (33): Synthesis of Compound (1-19-8)

[0956] In the same manner as in Synthesis Example (1), Compound (1-19-8) was obtained from Intermediate (Int-1-19-8).

[0957] [Chemical Formula 180]

[0958]

[0959] The target substance with m / z(M+H)=1145.70 was confirmed by APCI-MS.

[0960] Synthesis Example (34): Synthesis of Compound (1-20-1)

[0961] In the same manner as in Synthesis Example (1), Compound (1-20-1) was obtained from Intermediate (Int-1-20-1).

[0962] [Chemical Formula 181]

[0963]

[0964] The target substance with m / z (M+H) = 845.46 was confirmed by APCI-MS.

[0965] Synthesis Example (35): Synthesis of Compound (1-20-2)

[0966] In the same manner as in Synthesis Example (1), Compound (1-20-2) was obtained from Intermediate (Int-1-20-2).

[0967] [Chemical Formula 182]

[0968]

[0969] The target substance with m / z (M+H) = 989.65 was confirmed by APCI-MS.

[0970] Synthesis Example (36): Synthesis of Compound (1-20-3)

[0971] In the same manner as in Synthesis Example (1), Compound (1-20-3) was obtained from Intermediate (Int-1-20-3).

[0972] [Chemical Formula 183]

[0973]

[0974] The target substance with m / z (M+H) = 901.44 was confirmed by APCI-MS.

[0975] Synthesis Example (37): Synthesis of Compound (1-20-4)

[0976] In the same manner as in Synthesis Example (1), Compound (1-20-4) was obtained from Intermediate (Int-1-20-4).

[0977] [Chemical Formula 184]

[0978]

[0979] The target substance with m / z (M+H) = 953.56 was confirmed by APCI-MS.

[0980] Synthesis Example (38): Synthesis of Compound (1-20-7)

[0981] In the same manner as in Synthesis Example (1), Compound (1-20-7) was obtained from Intermediate (Int-1-20-7).

[0982] [Chemical Formula 185]

[0983]

[0984] The target substance with m / z(M+H)=893.56 was confirmed by APCI-MS.

[0985] Synthesis Example (39): Synthesis of Compound (1-20-10)

[0986] In the same manner as in Synthesis Example (1), Compound (1-20-10) was obtained from Intermediate (Int-1-20-10).

[0987] [Chemical Formula 186]

[0988]

[0989] The target substance with m / z(M+H)=969.59 was confirmed by APCI-MS.

[0990] Synthesis Example (40): Synthesis of Compound (1-21-1)

[0991] In the same manner as in Synthesis Example (1), Compound (1-21-1) was obtained from Intermediate (Int-1-21-1).

[0992] [Chemical Formula 187]

[0993]

[0994] The target substance with m / z(M+H)=1123.73 was confirmed by APCI-MS.

[0995] Synthesis Example (41): Synthesis of Compound (1-21-4)

[0996] In the same manner as in Synthesis Example (1), Compound (1-21-4) was obtained from Intermediate (Int-1-21-4).

[0997] [Chemical Formula 188]

[0998]

[0999] The target substance with m / z(M+H)=1046.58 was confirmed by APCI-MS.

[1000] Synthesis Example (42): Synthesis of Compound (1-21-12)

[1001] In the same manner as in Synthesis Example (1), Compound (1-21-12) was obtained from Intermediate (Int-1-21-12).

[1002] [Chemical Formula 189]

[1003]

[1004] The target substance with m / z (M+H) = 1135.76 was confirmed by APCI-MS.

[1005] Synthesis Example (43): Synthesis of Compound (1-21-15)

[1006] In the same manner as in Synthesis Example (1), Compound (1-21-15) was obtained from Intermediate (Int-1-21-15).

[1007] [Chemical Formula 190]

[1008]

[1009] The target substance with m / z (M+H) = 1130.71 was confirmed by APCI-MS.

[1010] Synthesis Example (44): Synthesis of Compound (1-21-23)

[1011] In the same manner as in Synthesis Example (1), Compound (1-21-23) was obtained from Intermediate (Int-1-21-23).

[1012] [Chemical Formula 191]

[1013]

[1014] The target substance with m / z (M+H) = 997.58 was confirmed by APCI-MS.

[1015] Synthesis Example (45): Synthesis of Compound (1-22-1)

[1016] In the same manner as in Synthesis Example (1), Compound (1-22-1) was obtained from Intermediate (Int-1-22-1).

[1017] [Chemical Formula 192]

[1018]

[1019] The target substance with m / z (M+H) = 1038.51 was confirmed by APCI-MS.

[1020] Synthesis Example (46): Synthesis of Compound (1-22-4)

[1021] In the same manner as in Synthesis Example (1), Compound (1-22-4) was obtained from Intermediate (Int-1-22-4).

[1022] [Chemical Formula 193]

[1023]

[1024] The target product was confirmed by APCI-MS with m / z (M+H) = 905.52.

[1025] Synthesis Example (47): Synthesis of Compound (1-22-5)

[1026] In addition to changing boron tribromide (BBr3) to boron atoms, which have been replaced as isotopes 11 B atoms of matter ( 11 The same procedure as in Synthesis Example (1) was followed except for the addition of BBr3) to obtain compound (1-22-5) from intermediate (Int-1-22-5).

[1027] [Chemistry 194]

[1028]

[1029] The target product was confirmed by APCI-MS with m / z (M+H) = 795.41.

[1030] <Possibility of application to organic EL devices>

[1031] The compounds of the present invention are expected to have an appropriate energy gap (Eg), a high lowest triplet excited energy level (E T ) and a small ΔEST, and therefore, for example, can be expected to be applied to a light-emitting layer and a charge transport layer, and in particular, can be expected to be applied to a light-emitting layer.

[1032] <<Fabrication and evaluation of vapor deposition type organic EL elements>>

[1033] Next, the preparation and evaluation of an organic EL device using the polycyclic aromatic compound of the present invention will be described.

[1034] <Structure of organic EL element>

[1035] An organic EL device is produced using the polycyclic aromatic compound of the present invention.

[1036] The material structures of the respective layers in the organic EL devices of Examples B1 to B47 and Comparative Examples B1 to B6 are shown in Table 1 below.

[1037] [Table 1]

[1038]

[1039] The chemical structures of "HI", "HAT-CN", "HT-1", "HT-2", "BH", "ET-1", "ET-2", "Liq", "Comparative Compound (1)" described in International Publication No. 2022 / 050710, "Comparative Compound (2)" and "Comparative Compound (4)" described in the specification of U.S. Patent Application Publication No. 2022 / 0310924, "Comparative Compound (3)" and "Comparative Compound (5)" described in International Publication No. 2021 / 107743, and "Comparative Compound (6)" described in International Publication No. 2022 / 191570 are shown below in Table 1 and Table 3.

[1040] [Chemical Formula 195]

[1041]

[1042] [Chemical Formula 196]

[1043]

[1044] <Components of Comparative Example B1>

[1045] A 26 mm × 28 mm × 0.7 mm glass substrate (manufactured by Opto Science Co., Ltd.) with the ITO film formed by sputtering ground to a thickness of 150 nm is used as the transparent support substrate. The transparent support substrate is fixed to the substrate holder of a commercially available evaporation device (manufactured by Showa Vacuum Co., Ltd.), and molybdenum evaporation boats containing HI, HAT-CN, HT-1, HT-2, BH, Comparative Compound (1), ET-1, and ET-2 respectively, and aluminum nitride evaporation boats containing Liq, LiF, and aluminum respectively are installed.

[1046] The following layers are sequentially formed on the ITO film of the transparent support substrate. The vacuum chamber is evacuated to 5×10 -4Pa, first, heat HI and perform evaporation deposition in such a way that the film thickness becomes 40 nm. Then, heat HAT-CN and perform evaporation deposition in such a way that the film thickness becomes 5 nm. Then, heat HT-1 and perform evaporation deposition in such a way that the film thickness becomes 45 nm. Then, heat HT-2 and perform evaporation deposition in such a way that the film thickness becomes 10 nm to form a hole layer containing four layers. Then, heat BH and Comparative Compound (1) simultaneously and perform evaporation deposition in such a way that the film thickness becomes 25 nm to form a light-emitting layer. Adjust the evaporation rate so that the mass ratio of BH to Comparative Compound (1) becomes approximately 97 to 3. Further, heat ET-1 and perform evaporation deposition in such a way that the film thickness becomes 5 nm. Then, heat ET-2 and Liq simultaneously and perform evaporation deposition in such a way that the film thickness becomes 25 nm to form an electron layer containing two layers. Adjust the evaporation rate so that the mass ratio of ET-2 to Liq becomes approximately 50 to 50. The evaporation rate of each layer is 0.01 nm / second to 1 nm / second. Thereafter, heat LiF and perform evaporation deposition at an evaporation rate of 0.01 nm / second to 0.1 nm / second in such a way that the film thickness becomes 1 nm. Then, heat aluminum and perform evaporation deposition in such a way that the film thickness becomes 100 nm to form a cathode, thereby obtaining an organic EL element.

[1047] <Elements of Example B1 to B47 and Comparative Example B2 to B6>

[1048] Except for using each compound described in Tables 2 to 3 instead of Comparative Compound (1) as the dopant material, perform in the same manner as Comparative Example B1 to obtain the organic EL elements of Example B1 to B47 and Comparative Example B2 to B6.

[1049] <Evaluation of Organic EL Characteristics>

[1050] For the organic EL elements of Example B1 to B47 and Comparative Example B2 to B6, set the ITO electrode as the anode and the LiF / aluminum electrode as the cathode, apply a DC voltage, and measure the driving voltage, external quantum efficiency, and element lifetime during light emission at 1000 cd / m 2 In addition, the element lifetime is the time to continuously drive at the voltage during light emission at 1000 cd / m 2 to maintain a brightness of 95% or more of the initial brightness. The results are shown in Tables 2 and 3.

[1051] The quantum efficiency of a light-emitting element has an internal quantum efficiency and an external quantum efficiency. The internal quantum efficiency represents the ratio of the external energy injected into the light-emitting layer of the light-emitting element as an electron (or hole) that is purely converted into photons. On the other hand, the external quantum efficiency is calculated based on the amount of photons released to the outside of the light-emitting element. A part of the photons generated in the light-emitting layer is internally absorbed by the light-emitting element or continuously reflected without being released to the outside of the light-emitting element. Therefore, the external quantum efficiency is lower than the internal quantum efficiency.

[1052] The method for measuring the spectral radiance (emission spectrum) and the external quantum efficiency is as described below. Using a voltage / current generator R6144 manufactured by Advantest Corporation, a voltage is applied to make the element emit light such that the brightness of the element reaches 1000 cd / m 2 . Using a spectral radiance meter SR-3AR manufactured by TOPCON Corporation, the spectral radiance in the visible light region was measured from a direction perpendicular to the light-emitting surface. Assuming that the light-emitting surface is a perfectly diffusing surface, the value of the spectral radiance of each wavelength component measured is divided by the wavelength energy and multiplied by π to obtain the number of photons at each wavelength. Subsequently, the number of photons is accumulated in the entire observed wavelength region and set as the total number of photons released from the element. The value obtained by dividing the applied current value by the elementary charge is set as the number of carriers injected into the element, and the value obtained by dividing the total number of photons released from the element by the number of carriers injected into the element is the external quantum efficiency.

[1053] [Table 2-1]

[1054]

[1055] [Table 2-2]

[1056] Example B44 Compound (1-21-23) 8.5 305 Example B45 Compound (1-22-1) 8.6 315 Example B46 Compound (1-22-4) 8.2 300 Example B47 Compound (1-22-5) 8.5 369

[1057] [Table 3]

[1058]

[1059] Industrial availability

[1060] The polycyclic aromatic compound of the present invention can be effectively used 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 element. By using the polycyclic aromatic compound of the present invention as a dopant for the light-emitting layer, an organic electroluminescent element with a long lifespan, a low driving voltage, and a high luminous efficiency, particularly a long lifespan and a high luminous efficiency, can be obtained.

[1061] Explanation of reference numerals

[1062] 100: Organic electroluminescent element

[1063] 101: Substrate

[1064] 102: Anode

[1065] 103: Hole injection layer

[1066] 104: Hole transport layer

[1067] 105: Light emitting layer

[1068] 106: Electron transport layer

[1069] 107: Electron injection layer

[1070] 108: Cathode

Claims

1. A polycyclic aromatic compound having a structure composed of one or more of the structural units represented by formula (1); [Chemical formula 1] In formula (1), R a1 ~R a3 , R b1 ~R b4 and R c1 ~R c4 are independently hydrogen or a substituent, R a1 to R a3 , R b1 to R b4 and R c1 to R c4 adjacent two groups among them can be bonded to each other and together with the two carbon atoms to which they are bonded form a substituted or unsubstituted aryl ring or a substituted or unsubstituted heteroaryl ring Among them, R c1 ~R c4 at least one of which is a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group Y 1 is B, P, P=O, P=S, Al, Ga, As, Si-R or Ge-R, where R of the Si-R and the Ge-R is a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted cycloalkyl group; X 1 and X 2 are each independently >O, >N-R NX , >C(-R CX )2, >Si(-R IX )2, >S, or >Se, where R NX is hydrogen, a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted alkyl, or a substituted or unsubstituted cycloalkyl, and R CX are each independently hydrogen, a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted alkyl, or a substituted or unsubstituted cycloalkyl, and two Rs CX may be bonded to each other to form a ring, and R IX are each independently hydrogen, a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted alkyl, or a substituted or unsubstituted cycloalkyl, and two Rs IX may be bonded to each other to form a ring. Additionally, R NX and / or R CX may be bonded to R a3 and / or R b1 , or R a1 and / or R c4 via a linking group or a single bond Wherein, at least one selected from the group consisting of X 1 and X 2 is R NX >N-R which is a group represented by formula (G-1) or formula (G-2) NX , [Chemical formula 2] In formula (G-1), R d2 ~R d8 are each independently hydrogen or a substituent, R d2 ~R d8 Two adjacent groups in can be bonded to each other and together with the two carbon atoms to which they are bonded form a substituted or unsubstituted aryl ring or a substituted or unsubstituted heteroaryl ring. * represents the bonding position to the nitrogen atom, In formula (G-2), R e2 ~R e10 are each independently hydrogen or a substituent, Wherein, at least one selected from the group consisting of R e6 ~R e10 is a substituent selected from the group consisting of an alkyl group, a cycloalkyl group which may be substituted by at least one alkyl group, and an aryl group which may be substituted by at least one alkyl group or a cycloalkyl group which may be substituted by an alkyl group, or at least one of the aryl ring or heteroaryl ring in formula (G-2) is condensed with at least one cycloalkane, at least one hydrogen in the cycloalkane may be substituted, and at least one -CH2- in the cycloalkane may be substituted by -O- * represents the bonding position to the nitrogen atom, At least one of the aryl rings or heteroaryl rings in the structure may be condensed with at least one cycloalkane, at least one hydrogen in the cycloalkane may be substituted, and at least one -CH2- in the cycloalkane may be substituted with -O-; In the structure, at least one hydrogen may be replaced by deuterium, at least one nitrogen may be replaced by nitrogen-15 ( 15 N), at least one sulfur may be replaced by sulfur-33 ( 33 S), sulfur-34 ( 34 S), or sulfur-36 ( 36 S), at least one oxygen may be replaced by oxygen-17 ( 17 O) or oxygen-18 ( 18 O), at least one carbon may be replaced by carbon-13 ( 13 C), at least one boron may be replaced by boron-11 ( 11 B).

2. The polycyclic aromatic compound according to claim 1, wherein, Located at R c1 ~R c4 The aryl ring and heteroaryl ring are not condensed with the cycloalkane.

3. The polycyclic aromatic compound according to claim 1, wherein, R c3 is an aryl group that can be alkyl-substituted, R c1 , R c2 and R c4 are all hydrogen.

4. The polycyclic aromatic compound according to claim 3, wherein, R c3 is a phenyl group which may be substituted by a tert-butyl group.

5. The polycyclic aromatic compound according to claim 1, which has a structure composed of one of the structural units represented by formula (1), Y 1 is B R a1 、R a3 、R b1 、R b4 、R c1 and R c4 are hydrogen, R a2 is hydrogen, unsubstituted alkyl, cycloalkyl optionally substituted by methyl, aryl optionally substituted by alkyl or cycloalkyl (optionally substituted by methyl), heteroaryl optionally substituted by alkyl or cycloalkyl (optionally substituted by methyl), diarylamino optionally substituted by alkyl or cycloalkyl (optionally substituted by methyl), arylheteroarylamino optionally substituted by alkyl or cycloalkyl (optionally substituted by methyl), or carbazolyl optionally substituted by alkyl or cycloalkyl (optionally substituted by methyl). R b2 and R b3 each independently is hydrogen, unsubstituted alkyl, cycloalkyl optionally substituted by methyl, aryl optionally substituted by alkyl or cycloalkyl (optionally substituted by methyl), heteroaryl optionally substituted by alkyl or cycloalkyl (optionally substituted by methyl), diarylamino optionally substituted by alkyl or cycloalkyl (optionally substituted by methyl), arylheteroarylamino optionally substituted by alkyl or cycloalkyl (optionally substituted by methyl), or carbazolyl optionally substituted by alkyl or cycloalkyl (optionally substituted by methyl). R c2 and R c3 any one of which is an aryl group which may be alkyl-substituted, and the other is hydrogen or an aryl group which may be alkyl-substituted, X 1 and X 2 are each independently > N-R NX , When R is other than the group represented by formula (G-1) or the group represented by formula (G-2), NX said R NX is an aryl group which may be substituted by an alkyl group or a cycloalkyl group which may be substituted by an alkyl group (excluding the group represented by formula (G-2)), or a heteroaryl group which may be substituted by an alkyl group or a cycloalkyl group (which may be substituted by an alkyl group) (excluding the group represented by formula (G-1)). In formula (G-1), R d2 ~R d8 are each independently hydrogen, unsubstituted alkyl, cycloalkyl which may be substituted by methyl, aryl which may be substituted by alkyl or cycloalkyl (which may be substituted by methyl), or heteroaryl which may be substituted by alkyl or cycloalkyl (which may be substituted by methyl). R d2 ~R d8 Two adjacent groups among them can be bonded to each other and together with the two carbon atoms to which they are bonded form a benzene ring, and the benzene ring can be substituted by an unsubstituted alkyl group, a cycloalkyl group which may be substituted by a methyl group, an aryl group which may be substituted by an alkyl group or a cycloalkyl group (which may be substituted by a methyl group), or a heteroaryl group which may be substituted by an alkyl group or a cycloalkyl group (which may be substituted by a methyl group). In formula (G-2), At least one selected from the group consisting of R e6 ~R e10 is an unsubstituted alkyl group, a cycloalkyl group which may be substituted with a methyl group, or an aryl group which may be substituted with an alkyl group or a cycloalkyl group (which may be substituted with a methyl group), or R e2 ~R e10 Two adjacent groups in are bonded to each other to form a partial structure represented by formula (B-1) or formula (B-2). At least one of the aryl rings or heteroaryl rings other than the c ring in formula (1) may have formula (B-1) or formula (B-2) as a substituent, [Chemical formula 3] In formula (B-1) or formula (B-2), * represents the positions bonding to the adjacent ring-constituting atoms respectively, At least one hydrogen in the structure may be substituted with deuterium.

6. The polycyclic aromatic compound according to claim 1, wherein, At least one selected from the group consisting of X 1 and X 2 is R NX >N-R which is a group represented by formula (G-1) NX and does not contain R NX >N-R which is a group represented by formula (G-2) NX As X 1 or X 2 .

7. The polycyclic aromatic compound according to claim 6, which is represented by any one of the following formulas; [Chemical formula 4] [Chemical formula 5] [Chemical formula 6] [Chemical formula 7] [Chemical formula 8] [Chemical formula 9] [Chemical formula 10] [Chemical formula 11] In the formula, Me is methyl, tBu is tert-butyl, and D is deuterium.

8. The polycyclic aromatic compound according to claim 7, which is represented by formula (1-9-2), formula (1-9-5), formula (1-9-9), formula (1-11-8), formula (1-17-10), formula (1-19-1), formula (1-19-3), formula (1-21-1) or formula (1-21-4).

9. The polycyclic aromatic compound according to claim 1, wherein, At least one selected from the group consisting of X 1 and X 2 is R NX >N-R which is a group represented by formula (G-2) NX , and does not contain R NX >N-R which is a group represented by formula (G-1) NX As X 1 or X 2 .

10. The polycyclic aromatic compound according to claim 9, which is represented by any one of the following formulas; [Chemical formula 12] [Chemical formula 13] [Chemical formula 14] [Chemical formula 15] [Chemical formula 16] [Chemical formula 17] [Chemical formula 18] [Chemical formula 19] [Chemical formula 20] [Chemical formula 21] In the formula, Me is methyl, tBu is tert-butyl, tAm is tert-amyl, and D is deuterium.

11. The polycyclic aromatic compound according to claim 10, which is represented by formula (1-1-1), formula (1-1-3), formula (1-1-5), formula (1-1-10), formula (1-2-7), formula (1-3-4), formula (1-3-6), formula (1-3-9), formula (1-3-10), formula (1-4-2), formula (1-5-8), formula (1-6-2), formula (1-6-6), formula (1-6-10), formula (1-8-2), formula (1-16-6), formula (1-20-1), formula (1-20-3), formula (1-20-4), formula (1-20-7), formula (1-20-10), formula (1-21-12) or formula (1-21-15).

12. The polycyclic aromatic compound according to claim 10, which is represented by formula (1-1-1) or formula (1-20-10).

13. The polycyclic aromatic compound according to claim 1, wherein, X 1 or X 2 any one of which is R NX >N-R which is a group represented by formula (G-1) NX and the other is R NX >N-R which is a group represented by formula (G-2) NX .

14. The polycyclic aromatic compound according to claim 12, which is represented by any one of the following formulas; [Chemical formula 22] [Chemical formula 23] In the formula, Me is methyl, tBu is tert-butyl, tAm is tert-amyl, and D is deuterium.

15. The polycyclic aromatic compound according to claim 14, which is represented by formula (1-17-1), formula (1-17-3), formula (1-17-5), or formula (1-21-23).

16. The polycyclic aromatic compound according to claim 6, which is represented by any one of the following formulas; [Chemical formula 24] In the formula, Me is methyl, and tBu is tert-butyl.

17. The polycyclic aromatic compound according to claim 1, which is represented by any one of the following formulas; [Chemical formula 25] [Chemical formula 26] In the formula, Me is methyl, tBu is tert-butyl, and D is deuterium.

18. A material for an organic device, containing the polycyclic aromatic compound according to any one of claims 1 to 17.

19. An organic electroluminescent element, comprising: A pair of electrodes, including an anode and a cathode; And a light-emitting layer disposed between the pair of electrodes, the light-emitting layer containing the polycyclic aromatic compound according to any one of claims 1 to 17.

20. The organic electroluminescent element according to claim 19, wherein, The light-emitting layer includes a host and the polycyclic aromatic compound as a dopant.

21. The organic electroluminescent element according to claim 20, wherein, The main body is an anthracene compound, a fluorene compound, or a dibenzo compound.

22. A display device or a lighting device, including the organic electroluminescent element according to claim 19.

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