Polycyclic aromatic compound

Abstract

This polycyclic aromatic compound represented by formula (1) is useful as a material for an organic device such as an organic electroluminescent element. (In the formula, L indicates the presence of at least one crosslinking by a linking group represented by formula (1-a) or formula (1-b); Cy represents a structure that is composed of one or more structural units represented by formula (Cy); LAa represents a trivalent group; LAb represents a divalent group; LB represents a single bond or a divalent group; * indicates the bonding position to a nitrogen atom that is represented by X; ring A and ring B each represent a substituted or unsubstituted aryl ring or a substituted or unsubstituted heteroaryl ring: two rings B may be bonded to each other by the intermediary of Lcy; and Y is >B-. At least one selected from the group consisting of the aryl ring and the heteroaryl ring in formula (1) may be condensed with at least one cycloalkane, and at least one hydrogen in formula (1) may be replaced with deuterium.)

Description

Polycyclic aromatic compounds

[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 also relates to a material for an organic device, an organic electroluminescent element, a display device, and a lighting device, each containing the polycyclic aromatic compound.

[0002] Conventionally, display devices using electroluminescent light-emitting elements have been extensively studied because of their potential for power saving and thinning, and organic electroluminescent devices made from organic materials have been actively investigated because they can be easily made lighter and larger. In particular, the development of organic materials that have the luminescence properties of blue, one of the three primary colors of light, and organic materials that have the ability to transport charges such as holes and electrons (potentially becoming semiconductors or superconductors), regardless of whether they are polymer compounds or low-molecular compounds, has been actively studied.

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

[0004] Among these, Patent Document 1 discloses that a polycyclic aromatic compound containing boron is useful as a material for organic electroluminescent devices and the like.

[0005] International Publication No. 2015 / 102118

[0006] As described above, various materials have been developed for use in organic EL elements, but in order to increase the options for materials for organic EL elements, it is desirable to develop materials made of novel compounds. An object of the present invention is to provide novel compounds useful as materials for organic devices such as organic EL elements.

[0007] The present inventors conducted extensive research to solve the above problems and succeeded in producing a novel polycyclic aromatic compound having a structure similar to that of the compound described in Patent Document 1. They also discovered that an excellent organic EL device can be obtained by constructing an organic EL device by disposing a layer containing this polycyclic aromatic compound between a pair of electrodes, and thus completed the present invention. Specifically, the present invention provides the following polycyclic aromatic compounds, as well as materials for organic devices containing the following polycyclic aromatic compounds. Specifically, the present invention has the following configurations.

[0008] <1> A polycyclic aromatic compound represented by formula (1); In formula (1), Cy represents a structure consisting of one or more structural units represented by formula (Cy), L represents the presence of at least one crosslink formed by a linking group represented by formula (1-a) or formula (1-b),

[0009]

[0010] In each of formulas (1-a) and (1-b), L Aａ are each independently a trivalent group, and L Aｂ are each independently a divalent group, B are each independently a single bond or a divalent group, * indicates the bonding position to X, in formula (Cy), ring A and two rings B are each independently a substituted or unsubstituted aryl ring or a substituted or unsubstituted heteroaryl ring, and the two rings B are each independently a substituted or unsubstituted heteroaryl ring, ｃｙ and L ｃｙ is a single bond or a linking group, and Y is >B-, >P-, >P(=O)-, >P(=S)-, >Al-, >Ga-, >As-, >Si(-R Ｙ ) - or >Ge(-R Ｙ )- and R Ｙare each independently a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted alkyl, or a substituted or unsubstituted cycloalkyl, two of X in the structure are nitrogen atoms bonded to * in the linking group represented by formula (1-a) or formula (1-b), and when there are four or more Xs in the structure that are not Xs shared by two structural units, there may be one or more pairs of two Xs that are nitrogen atoms bonded to * in the linking group represented by formula (1-a) or formula (1-b), and when there are three or more Xs in the structure, the other Xs are each independently a nitrogen atom shared by two structural units, or >N-R ＮＸ , >O, >S, >C(-R ＣＸ ) ２ , >Ge(-R ＧＸ ) ２ , >Si(-R ＩＸ ) ２ , or >Se, and R ＮＸ , R ＣＸ , R ＧＸ , and R ＩＸ are each independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, and >C(-R ＣＸ ) ２ The two R's ＣＸ may be bonded to each other to form a ring, and >Si(-R ＩＸ ) ２ The two R's ＩＸ may be bonded to each other to form a ring, R ＮＸ , at least one R ＣＸ and at least one R ＩＸ may be bonded to at least one of ring A and ring B via a linking group or a single bond, and at least one selected from the group consisting of an aryl ring and a heteroaryl ring in formula (1) may be condensed with at least one cycloalkane, and when the cycloalkane has a bridged structure, at least one —CH ２ -CH ２- may be -CH=CH-, and when the cycloalkane has a bridged structure, the cycloalkane ring may be condensed with an aryl ring or a heteroaryl ring, the cycloalkane may be substituted with at least one substituent, and at least one -CH ２ - may be replaced by -O-, and in formula (1), at least one hydrogen may be replaced by deuterium, and at least one nitrogen may be replaced by nitrogen-15 ( １５ N), and at least one sulfur may be replaced by sulfur-33 ( ３３ S), sulfur-34 ( ３４ S) or sulfur-36 ( ３６ S), and at least one oxygen may be replaced by oxygen-17 ( １７ O) or oxygen-18 ( １８ O), and at least one carbon may be replaced by carbon-13 ( １３ C), and at least one boron may be replaced by boron-11 ( １１ B) may be substituted.

[0011] <2> L Ａａ are each independently represented by the formula (L Ａａ－１ ) is a group represented by L Ａｂ are each independently represented by the formula (L Ａｂ－１ The polycyclic aromatic compound according to <1>, wherein the group is a group represented by Formula (L Ａａ－１ ) and formula (L Ａｂ－１ In the formula (I), ring Aa and ring Ab each independently represent a substituted or unsubstituted aryl ring, a substituted or unsubstituted heteroaryl ring, or a substituted or unsubstituted cycloalkane ring, * represents the bonding position to the nitrogen atom represented by X, and # represents L Ｂ This is the bonding position with

[0012] <3> L Ａａ are each independently represented by the formula (L Ａａ－２ ) is a group represented by L Ａｂ are each independently represented by the formula (L Ａｂ－２ The polycyclic aromatic compound according to <1>, wherein the group is a group represented by

[0013] Formula (L Ａａ－２ ) and formula (L Ａｂ－２ In the formula, each Z is independently N or C-R Ｚ or Z = Z are each independently >O, >N-R ＮＺ , >C(-R ＣＺ ) ２ , >Si(-R ＩＺ ) ２ , >S, or >Se, and R ＮＺ , R ＣＺ , and R ＩＺ are each independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, and >C(-R ＣＺ ) ２ The two R's ＣＺ may be bonded to each other to form a ring, and >Si(-R ＩＺ ) ２ The two R's ＩＺ may be bonded to each other to form a ring, R Ｚ are each independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino (two aryls may be bonded to each other via a linking group), substituted or unsubstituted diheteroarylamino (two heteroaryls may be bonded to each other via a linking group), substituted or unsubstituted arylheteroarylamino (an aryl and a heteroaryl may be bonded to each other via a linking group), substituted or unsubstituted diarylboryl (two aryls may be bonded to each other via a single bond or a linking group), substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted arylthio, or substituted silyl, Ｚmay be bonded to each other to form an aryl ring or a heteroaryl ring together with a ring having the carbon atoms to which they are bonded as constituent atoms, and the formed aryl ring and heteroaryl ring may have a substituent, * is the bonding position to the nitrogen atom which is X, and # is L Ｂ This is the bonding position with

[0014] <4> L Ａａ are each independently represented by the formula (L Ａａ－２ -1) ~Formula (L Ａａ－２ -4), and L Ａｂ are each independently represented by the formula (L Ａｂ－２ -1) ~Formula (L Ａｂ－２ The polycyclic aromatic compound according to <1>, wherein the compound is a group represented by any one of the following:

[0015] Formula (L Ａａ－２ -1) ~Formula (L Ａａ－２ -4), formula (L Ａｂ－２ -1) ~Formula (L Ａｂ－２ -9) In the formula, each A is independently >O, >N-R ＮＡ , >C(-R ＣＡ ) ２ , >Si(-R ＩＡ ) ２ , >S, >Se, or >Te, and R ＮＡ , R ＣＡ , and R ＩＡ are each independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, and >C(-R ＣＡ ) ２ The two R's ＣＡ may be bonded to each other to form a ring, and >Si(-R ＩＡ ) ２ The two R's ＩＡ may be bonded to each other to form a ring, at least one hydrogen atom of the group represented by each of the above formulae may be replaced by alkyl, * is the bonding position to the nitrogen atom represented by X, and # is L Ｂ This is the bonding position with

[0016] <5> LＢ are each independently represented by the formula (L ｂ ), formula (L ｂ２ ), or formula (L ｂ３ <4> The polycyclic aromatic compound according to any one of <1> to <4>, wherein the group is a group represented by Formula (L ｂ ) inside, X Ｌ are each independently a single bond, —O—, —S—, —Se—, —Te—, or —(N—R Ｌ ) -, -(P-R Ｌ )-,-(O=P-R Ｌ ) -, -(C(-R Ｌ ) ２ )-,-(C=O)-,-(Ge(-R Ｌ ) ２ )-,-(Sn(-R Ｌ ) ２ )-, -SO-, -SO ２ -, -(Si(-R Ｌ ) ２ )-,-(S=P-R Ｌ ) -, -(B-R Ｌ ) - or -(Bi-R Ｌ )- and R Ｌ are each independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, and —(C(—R Ｌ ) ２ )-,-(Ge(-R Ｌ ) ２ )-,-(Sn(-R Ｌ ) ２ )-, and -(Si(-R Ｌ ) ２ )- each of the two R Ｌ may be bonded to each other to form a ring, each Ar is independently a substituted or unsubstituted alkylene having 2 to 12 carbon atoms, a substituted or unsubstituted arylene, or a substituted or unsubstituted heteroarylene, and at least one —CH ２ -CH ２ - may be replaced by cycloalkylene or vinylene, j is an integer of 1 to 10, and # is L Ａａ or LＡｂ is the bonding position with Formula (L ｂ２ ) inside, X Ｌ , Ar, and # are represented by the formula (L ｂ ) in Ｌ , Ar, and #, respectively; X Ｌ１ is -O-, -S-, -Se-, -Te-, -(N-R Ｌ ) -, -(P-R Ｌ )-,-(O=P-R Ｌ ) -, -(C(-R Ｌ ) ２ )-,-(C=O)-,-(Ge(-R Ｌ ) ２ )-,-(Sn(-R Ｌ ) ２ )-, -SO-, -SO ２ -, -(Si(-R Ｌ ) ２ )-,-(S=P-R Ｌ ) -, -(B-R Ｌ ) - or -(Bi-R Ｌ )- and R Ｌ is the formula (L ｂ ) in R Ｌ each j2 is independently an integer of 0 to 5, and j3 is an integer of 2 to 5, provided that when each j2 is 0, j3 may be 1; Formula (L ｂ３ ) inside, X Ｌ , Ar, and # each independently represent a group represented by the formula (L ｂ ) in Ｌ , Ar, and #, each j2 independently represents an integer of 0 to 5, M ｃｏｍｐ Is > (M Ｔ ) n-(L ＭＴ ) m, and M Ｔ are each independently a transition metal atom, and L ＭＴ are each independently M Ｔ where n is an integer of 1 to 3, and m is an integer of 0 to 5. Ｂ are each independently represented by the formula (L ｂ<7> The polycyclic aromatic compound according to <5>, wherein L is a group represented by B are each independently represented by any one of the following formulas: In the above formula, Ar is a group represented by the formula (L ｂ has the same meaning as Ar in Ｌ１ are each independently —O—, —S—, —Se—, —Te—, —(N—R Ｌ ) -, -(P-R Ｌ )-,-(O=P-R Ｌ ) -, -(C(-R Ｌ ) ２ )-,-(C=O)-,-(Ge(-R Ｌ ) ２ )-,-(Sn(-R Ｌ ) ２ )-, -SO-, -SO ２ -, -(Si(-R Ｌ ) ２ )-,-(S=P-R Ｌ ) -, -(B-R Ｌ ) - or -(Bi-R Ｌ )- and R Ｌ are each independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, and —C(—R Ｌ ) ２ -, -(Ge(-R Ｌ ) ２ )-,-(Sn(-R Ｌ ) ２ ), and -(Si(-R Ｌ ) ２ )- each of the two R ＩＬ may be bonded to each other to form a ring, and # is L Ａａ or L Ａｂ This is the bonding position with

[0017] <8> The polycyclic aromatic compound according to <1>, in which the linking groups represented by formula (1-a) or formula (1-b) are each independently represented by any one of the following formulas:

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

[0019] <9> The polycyclic aromatic compound according to <1>, represented by any one of the following formulas:

[0020]

[0021]

[0022]

[0023]

[0024]

[0025]

[0026]

[0027]

[0028]

[0029]

[0030]

[0031]

[0032]

[0033]

[0034]

[0035]

[0036]

[0037]

[0038] In the formula, Me is methyl, tBu is t-butyl, tAm is t-amyl, and D is deuterium.

[0039] <10> An organic electroluminescent device having a pair of electrodes consisting of an anode and a cathode and an organic layer disposed between the pair of electrodes, the organic layer containing the polycyclic aromatic compound according to any one of <1> to <9>. <11> The organic electroluminescent device according to <10>, wherein the organic layer is an emitting layer. <12> The organic electroluminescent device according to <11>, wherein the emitting layer contains a host material, a thermally activated delayed fluorescent material or a phosphorescent material as an assisting dopant, and the polycyclic aromatic compound as an emitting dopant. <13> A display device or lighting device comprising the organic electroluminescent device according to any one of <10> to <12>.

[0040] The present invention provides a novel polycyclic aromatic compound useful as a material for organic devices such as organic electroluminescent elements. The polycyclic aromatic compound of the present invention can be used in the production of organic devices such as organic electroluminescent elements.

[0041] 1 is a schematic cross-sectional view showing an example of an organic electroluminescent device.

[0042] The present invention will be described in detail below. The following description of the constituent elements may be based on representative embodiments or specific examples, but the present invention is not limited to such embodiments. In this specification, a numerical range expressed using "to" means a range that includes the numerical values ​​before and after "to" as the lower and upper limits. In this specification, "hydrogen" in the description of a structural formula means "hydrogen atom (H)." Similarly, "carbon atom (C)" may be referred to as "carbon." In this specification, the term "adjacent groups" refers to two groups bonded to two adjacent atoms (two atoms directly bonded by a covalent bond) in a structural formula.

[0043] In this specification, "Me" represents methyl, "Et" represents ethyl, "nBu" represents n-butyl (normal butyl), "tBu" represents t-butyl (tertiary butyl), "iBu" represents isobutyl, "secBu" represents secondary butyl, "nPr" represents n-propyl (normal propyl), "iPr" represents isopropyl, "tAm" represents t-amyl, "2EH" represents 2-ethylhexyl, "tOct" represents t-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. In this specification, an organic electroluminescent element may be referred to as an "organic EL element."

[0044] In this specification, chemical structures and substituents are sometimes represented by the number of carbon atoms. However, when a chemical structure is substituted with a substituent or when a substituent is further substituted with a substituent, the number of carbon atoms refers to the number of carbon atoms in each of the chemical structure and the substituent, and does not refer to the total number of carbon atoms in the chemical structure and the substituent, or the total number of carbon atoms in the substituent and the substituent. For example, "substituent B of Y carbon atoms substituted with substituent A of X carbon atoms" means that "substituent B of Y carbon atoms" is substituted with "substituent A of X carbon atoms," and the number of carbon atoms Y is not the total number of carbon atoms in substituents A and B. Furthermore, for example, "substituent B of Y carbon atoms substituted with substituent A" means that "substituent B of Y carbon atoms" is substituted with "substituent A (with no carbon number limitation)," and the number of carbon atoms Y is not the total number of carbon atoms in substituents A and B.

[0045] This specification describes many structural formulas of aromatic compounds. Aromatic compounds are described by combining double bonds and single bonds, but in reality, because π electrons resonate, a single substance can have multiple equivalent resonance structures, in which double bonds and single bonds alternate. Although this specification describes only one resonance structure per substance, other organically equivalent resonance structures are also included unless otherwise specified.

[0046] In this specification, the expression "may be" is sometimes used, but this has the same meaning as "not being, or being."

[0047] <Explanation of Rings and Substituents> First, the details of rings and substituents used in this specification are explained below. As used herein, the "aryl ring" includes, for example, an aryl ring having 6 to 30 carbon atoms, preferably an aryl ring having 6 to 16 carbon atoms, more preferably an aryl ring having 6 to 12 carbon atoms, and particularly preferably an aryl ring having 6 to 10 carbon atoms.

[0048] Specific examples of the "aryl ring" include a monocyclic benzene ring, a bicyclic bicyclic bicyclic naphthalene ring and an indene ring, tricyclic terphenyl rings (m-terphenyl, o-terphenyl, p-terphenyl), fused tricyclic acenaphthylene ring, fluorene ring, phenalene ring, phenanthrene ring, anthracene ring, and 9,10-dihydroanthracene ring, fused tetracyclic triphenylene ring, pyrene ring, naphthacene ring, and chrysene ring, and fused pentacyclic perylene ring and pentacene ring. The fluorene ring, benzofluorene ring, and indene ring also include structures in which a fluorene ring, benzofluorene ring, cyclopentane ring, etc. are spiro-bonded, respectively. The fluorene ring, benzofluorene ring, 9,10-dihydroanthracene ring, and indene ring also include rings in which two of the two hydrogen atoms of the methylene in the ring structure are replaced by alkyl such as methyl as the first substituent described below, thereby forming a dimethylfluorene ring, dimethylbenzofluorene ring, dimethylindene ring, etc. Rings in which two methylene atoms of a 9,10-dihydroanthracene ring are bridged (such as a 9,10-dihydro-9,10-methanoanthracene ring and a 9,10-dihydro-9,10-o-benzonoanthracene ring) are also considered to be included in the aryl ring.

[0049] As used herein, examples of the "heteroaryl ring" include heteroaryl rings having 2 to 30 carbon atoms, 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. Furthermore, examples of the "heteroaryl ring" include heterocycles containing, as ring-constituting atoms other than carbon, 1 to 5 heteroatoms selected from oxygen, sulfur, nitrogen, boron, selenium, phosphorus, and tellurium.

[0050] Specific examples of the "heteroaryl ring" include a pyrrole ring, an oxazole ring, an isoxazole ring, a thiazole ring, an isothiazole ring, an imidazole ring, an oxadiazole ring (such as a furazan ring), a thiadiazole ring, a triazole ring, a tetrazole ring, a pyrazole ring, a pyridine ring, a pyrimidine ring, a pyridazine ring, a pyrazine ring, a triazine ring, an indole ring, an isoindole ring, a 1H-indazole ring, a benzimidazole ring, a benzoxazole ring, a benzothiazole ring, a 1H-benzotriazole ring, a quinoline ring, an isoquinoline ring, a cinnoline ring, a quinazoline ring, a quinoxaline ring, a phthalazine ring, a naphthyridine ring, a purine ring, a pteridine ring, a carbazole ring, an acridine ring, a phenoxathiin ring, a phenoxazine ring, a phenothiazine ring, and a phenazine ring. , a phenazasiline ring, an indolizine ring, a furan ring, a benzofuran ring, an isobenzofuran ring, a dibenzofuran ring, a thiophene ring, a benzothiophene ring, a dibenzothiophene ring, a thianthrene ring, an indolocarbazole ring (such as an indolo[3,2,1-jk]carbazole ring), a benzoindolocarbazole ring, a dibenzoindolocarbazole ring, a naphthobenzofuran ring, a dioxin ring, a dihydroacridine ring, a xanthene ring, a thioxanthene ring, a dibenzodioxin ring, a benzoxazinophenoxazine ring (such as a [1,4]benzoxazino[2,3,4-kl]phenoxazine ring), at least one of the two —O— in the benzoxazinophenoxazine ring is —NH—, —O—, —S—, —C(═O)—, —C(═S)—, —S(═O)—, or —S(═O) ２ -, -Se(=O)-, -Se(=O) ２-, -P(=O)-, -BH-, -SnH ２ a ring substituted with -, -Se-, or -Te- (either of the two -O- may be replaced with a single bond), a dioxaboranaphthoanthracene ring (e.g., a 5,9-dioxa-13b-bora-13bH-naphtho[3,2,1-de]anthracene ring), or a ring in which at least one of the two -O- in the dioxaboranaphthoanthracene ring is replaced with -NH-, -O-, -S-, -C(=O)-, -C(=S)-, -S(=O)-, or -S(=O) ２ -, -Se(=O)-, -Se(=O) ２ -, -P(=O)-, -SnH ２ a ring substituted with -, -Se-, or -Te- (either of the two -O- groups may be replaced with a single bond), a 4,8,12-trioxa-12c-bora-4H,8H-dibenzo[cd,mn]pyrene ring, or a ring in which at least one of the three -O- groups in the 4,8,12-trioxa-12c-bora-4H,8H-dibenzo[cd,mn]pyrene ring is replaced with -, -Se-, or -Te-; ２ -, -Se(=O)-, -Se(=O) ２ -, -P(=O)-, -BH-, -SnH ２Examples include a ring substituted with -, -Se-, or -Te- (any one of the above three -O- may be replaced with a single bond), a benzoselenophene ring, a dibenzoselenophene ring, an azacarbazole ring, an azadibenzothiophene ring, an azadibenzofuran ring, an azadibenzoselenophene ring, an azatriphenylene ring, an imidazoimidazole ring, an indoloindole ring, a benzofurocarbazole ring, a benzothienocarbazole ring, an indenocarbazole ring, a selenophenocarbazole ring, a spiro[fluorene-9,9'-xanthene] ring, a spirobi[silafluorene] ring, and a tribenzazepine ring. In addition, dihydroacridine rings, xanthene rings, and thioxanthene rings are also preferably those in which two of the two hydrogen atoms of the methylene in the structure are replaced by alkyl such as methyl as the first substituent described below, thereby forming a dimethyldihydroacridine ring, dimethylxanthene ring, dimethylthioxanthene ring, etc. In addition, bicyclic rings such as bipyridine rings, phenylpyridine rings, and pyridylphenyl rings, and tricyclic rings such as terpyridyl rings, bispyridylphenyl rings, and pyridylbiphenyl rings are also exemplified as "heteroaryl rings." In addition, "heteroaryl rings" also include pyran rings.

[0051] In this specification, a substituent may be substituted with a further substituent. For example, a specific substituent may be described as "substituted or unsubstituted." This means that the specific substituent is substituted with at least one further substituent, or is not substituted. In the same sense, the term "optionally substituted" may also be used. In this specification, the specific substituent may be referred to as a "first substituent," and the further substituent may be referred to as a "second substituent."

[0052] In this specification, the substituent group Zα consists of the substituents of the substituent group Z and a substituent represented by the formula (A30) described below.

[0053] In this specification, the substituent group Z includes: aryl optionally substituted with at least one group selected from the group consisting of aryl, heteroaryl, alkyl, cycloalkyl, cyano, substituted silyl, substituted germyl, and halogen; heteroaryl optionally substituted with at least one group selected from the group consisting of aryl, heteroaryl, alkyl, cycloalkyl, cyano, substituted silyl, substituted germyl, and halogen; diarylamino optionally substituted with at least one group selected from the group consisting of aryl, heteroaryl, alkyl, cycloalkyl, cyano, substituted silyl, substituted germyl, and halogen (two aryls may be bonded to each other via a linking group); diheteroarylamino optionally substituted with at least one group selected from the group consisting of aryl, heteroaryl, alkyl, cycloalkyl, cyano, substituted silyl, substituted germyl, and halogen (two heteroaryls may be bonded to each other via a linking group); arylheteroarylamino optionally substituted with at least one group selected from the group consisting of aryl, heteroaryl, alkyl, cycloalkyl, cyano, substituted silyl, substituted germyl, and halogen (two heteroaryls may be bonded to each other via a linking group); diarylboryl optionally substituted with at least one group selected from the group consisting of aryl, heteroaryl, alkyl, cycloalkyl, cyano, substituted silyl, substituted germyl, and halogen (two aryls may be bonded via a single bond or a linking group); alkyl optionally substituted with at least one group selected from the group consisting of aryl, heteroaryl, cycloalkyl, cyano, substituted silyl, substituted germyl, and halogen; cycloalkyl optionally substituted with at least one group selected from the group consisting of aryl, heteroaryl, alkyl, cycloalkyl, cyano, substituted silyl, substituted germyl, and halogen; alkoxy optionally substituted with at least one group selected from the group consisting of aryl, heteroaryl, cycloalkyl, cyano, substituted silyl, substituted germyl, and halogen;Aryloxy optionally substituted with at least one group selected from the group consisting of aryl, heteroaryl, alkyl, cycloalkyl, cyano, substituted silyl, substituted germyl, and halogen; arylthio optionally substituted with at least one group selected from the group consisting of aryl, heteroaryl, alkyl, cycloalkyl, cyano, substituted silyl, substituted germyl, and halogen; alkenyl optionally substituted with at least one group selected from the group consisting of aryl, heteroaryl, alkyl, cycloalkyl, cyano, substituted silyl, substituted germyl, and halogen; substituted silyl, substituted germyl, cyano, and halogen. The aryl, which is the second substituent in each group of substituent group Z, may be further substituted with an aryl, heteroaryl, alkyl, cycloalkyl, cyano, or halogen. Similarly, the heteroaryl, which is the second substituent, may be substituted with an aryl, heteroaryl, alkyl, cycloalkyl, cyano, or halogen.

[0054] In this specification, when referring to a "substituent," the type of the substituent is not particularly limited, but unless otherwise specified, it may be any group selected from substituent group Z. For example, when a "substituted or unsubstituted" group is substituted, it may be substituted with at least one group selected from substituent group Z.

[0055] In this specification, preferred examples of the substituent when a group described as "substituted or unsubstituted" is substituted include alkyl, cycloalkyl, substituted silyl, substituted germyl, cyano, halogen, aryl, and heteroaryl, wherein at least one hydrogen atom of the aryl and the heteroaryl may each independently be substituted with alkyl, cycloalkyl, substituted silyl, substituted germyl, cyano, or halogen. More preferred examples include alkyl, cycloalkyl, substituted silyl, substituted germyl, cyano, halogen, aryl, and heteroaryl, wherein at least one hydrogen atom of the aryl and the heteroaryl may each independently be substituted with alkyl or cycloalkyl.

[0056] In this specification, "aryl" refers to, for example, an aryl having 6 to 30 carbon atoms, and preferably an aryl having 6 to 20 carbon atoms, an aryl having 6 to 16 carbon atoms, an aryl having 6 to 12 carbon atoms, or an aryl having 6 to 10 carbon atoms.

[0057] Specific examples of "aryl" include monovalent groups obtained by removing one hydrogen atom from the above-mentioned "aryl ring." For example, phenyl is a monocyclic ring system, biphenylyl (2-biphenylyl, 3-biphenylyl, or 4-biphenylyl) is a bicyclic ring system, naphthyl (1-naphthyl or 2-naphthyl) is a fused bicyclic ring system, terphenylyl (m-terphenyl-2'-yl, m-terphenyl-4'-yl, m-terphenyl-5'-yl, o-terphenyl-3'-yl, o-terphenyl-4'-yl, p-terphenyl-2'-yl, m-terphenyl-2-yl, m-terphenyl-3-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) is a tricyclic ring system, acenaphthylene-(1-, 3-, 4-, or 5-) is a fused tricyclic ring system, -)yl, fluoren-(1-, 2-, 3-, 4-, or 9-)yl, phenalen-(1- or 2-)yl, phenanthrene-(1-, 2-, 3-, 4-, or 9-)yl, or anthracene-(1-, 2-, or 9-)yl, the tetracyclic ring systems quaterphenylyl (5'-phenyl-m-terphenyl-2-yl, 5'-phenyl-m-terphenyl-3-yl, 5'-phenyl and m-quaterphenyl-4-yl, or m-quaterphenyl), fused tetracyclic ring systems such as triphenylene-(1- or 2-)yl, pyrene-(1-, 2-, or 4-)yl, or naphthacene-(1-, 2-, or 5-)yl, or fused pentacyclic ring systems such as perylene-(1-, 2-, or 3-)yl, or pentacene-(1-, 2-, 5-, or 6-)yl. Other examples include monovalent groups of spirofluorene.

[0058] The aryl as the second substituent also includes a structure in which the aryl is substituted with at least one group selected from the group consisting of aryl such as phenyl (specific examples are the groups described above), alkyl such as methyl (specific examples are the groups described below), and cycloalkyl such as cyclohexyl or adamantyl (specific examples are the groups described below). One example of this is a group in which the 9-position of fluorenyl as the second substituent is substituted with aryl such as phenyl, alkyl such as methyl, or cycloalkyl such as cyclohexyl or adamantyl.

[0059] The "arylene" is, for example, an arylene having 6 to 30 carbon atoms, and 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. Specific examples of the "arylene" include a divalent group obtained by removing one hydrogen atom from the above-mentioned "aryl" (monovalent group).

[0060] The "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. The "heteroaryl" contains, in addition to carbon, one or more, preferably 1 to 5, heteroatoms selected from oxygen, sulfur, nitrogen, and the like as ring-constituting atoms.

[0061] Specific examples of the "heteroaryl" include monovalent groups obtained by removing one hydrogen atom from the above-mentioned "heteroaryl ring". 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, Examples include acridinyl, phenoxathiinyl, phenoxazinyl, phenothiazinyl, phenazinyl, phenazasilinyl, indolizinyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, naphthobenzofuranyl, thienyl, benzothienyl, isobenzothienyl, dibenzothienyl, naphthobenzothienyl, a monovalent group of a benzophospholeoxide ring, a monovalent group of a dibenzophospholeoxide ring, furazanyl, thianthrenyl, indolocarbazolyl, benzoindolocarbazolyl, dibenzoindolocarbazolyl, imidazolinyl, and oxazolinyl. Other examples include a monovalent group of spiro[fluorene-9,9'-xanthene], a monovalent group of spirobi[silafluorene], and a monovalent group of benzoselenophene.

[0062] 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 such as phenyl (specific examples are listed above), alkyl such as methyl (specific examples are listed below), and cycloalkyl such as cyclohexyl or adamantyl (specific examples are listed below). One example is a group in which the 9-position of the carbazolyl as the second substituent is substituted with aryl such as phenyl, alkyl such as methyl, or cycloalkyl such as cyclohexyl or adamantyl. Furthermore, the heteroaryl as the second substituent also includes groups in which a nitrogen-containing heteroaryl such as pyridyl, pyrimidinyl, triazinyl, or carbazolyl is further substituted with phenyl, biphenylyl, or the like.

[0063] The "heteroarylene" is, for example, a heteroarylene having 2 to 30 carbon atoms, and 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. The "heteroarylene" is, for example, a divalent group such as a heterocycle containing, in addition to carbon, 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen as ring-constituting atoms. Specific examples of the "heteroarylene" include divalent groups obtained by removing one hydrogen atom from the above-mentioned "heteroaryl" (monovalent group).

[0064] "Diarylamino" is an amino group substituted with two aryl groups, and the details of the aryl group can be found in the explanation of "aryl" above. "Diheteroarylamino" is an amino group substituted with two heteroaryl groups, and the details of the heteroaryl group can be found in the explanation of "heteroaryl" above. "Arylheteroarylamino" is an amino group substituted with an aryl and a heteroaryl, and the details of the aryl and heteroaryl group can be found in the explanation of "aryl" and "heteroaryl" above.

[0065] The two aryls in the diarylamino as the first substituent may be bonded to each other via a linking group, the two heteroaryls in the diheteroarylamino as the first substituent may be bonded to each other via a linking group, and the aryl and heteroaryl in the arylheteroarylamino as the first substituent may be bonded to each other via a linking group. Here, the expression "bonded via a linking group" means that, for example, the two phenyls in diphenylamino form a bond via a linking group, as shown below. This explanation also applies to diheteroarylamino and arylheteroarylamino formed by aryls or heteroaryls.

[0066]

[0067] Specific examples of the linking group include >O and >N—R Ｘ , >C(-R Ｘ ) ２ , -C(-R Ｘ ) = C(-R Ｘ ) -, >Si(-R Ｘ ) ２ , >S, >CO, >CS, >SO, >SO ２ , >SeO, >SeO ２ , >PO, >B(-R Ｘ ), and >Se. Ｘ are each independently an alkyl, a cycloalkyl, an aryl, or a heteroaryl, which may be substituted with an alkyl, a cycloalkyl, an aryl, or a heteroaryl. Ｘ ) ２ , -C(-R Ｘ ) = C(-R Ｘ ) -, >Si(-R Ｘ ) ２ The two R's in each Ｘ represents a single bond or a linking group X Ｙ They may be bonded to each other via X to form a ring. Ｙ As for >O, >N-R Ｙ , >C(-R Ｙ ) ２ , >Si(-R Ｙ ) ２, >S, >CO, >CS, >SO, >SO ２ , and >Se, and R Ｙ are each independently alkyl, cycloalkyl, aryl, or heteroaryl, which may be substituted with alkyl, cycloalkyl, aryl, or heteroaryl. Ｙ >C(-R Ｙ ) ２ and >Si(-R Ｙ ) ２ In the case of Ｙ do not bond to form a ring. Further examples of the linking group include alkenylene. Any hydrogen atom in the alkenylene can be independently selected from R ２Ｘ and R ２Ｘ are each independently alkyl, cycloalkyl, substituted silyl, aryl, or heteroaryl, which may be substituted with alkyl, cycloalkyl, substituted silyl, or aryl. Ｘ ) = C(-R Ｘ )- Two R in Ｘ may be bonded to each other to form an aryl ring (such as a benzene ring) or a heteroaryl ring together with the C═C to which they are attached. That is, —C(—R Ｘ ) = C(-R Ｘ )- may be arylene (such as 1,2-phenylene) or heteroarylene.

[0068] In this specification, unless otherwise specified, when "diarylamino," "diheteroarylamino," or "arylheteroarylamino" is simply described, it is assumed that the following explanation is added: "two aryls of the diarylamino may be bonded to each other via a linking group," "two heteroaryls of the diheteroarylamino may be bonded to each other via a linking group," and "aryl and heteroaryls of the arylheteroarylamino may be bonded to each other via a linking group," respectively.

[0069] "Diarylboryl" is a boryl substituted with two aryls, and the details of the aryls can be found in the above description of "aryl". The two aryls can be joined by a single bond or a linking group (e.g., -CH=CH-, -CR=CR-, -C≡C-, >N-R, >O, >S, >C(-R)). ２ , >Si(-R) ２ , -C(=O)-, >C=S, >S=O, >S(=O) ２ ,>Se(=O),>Se(=O) ２ , >P(=O), >B(-R), or >Se). Here, the R of -CR=CR-, the R of >N-R, and the >C(-R) ２ R in >Si(-R), R in >B(-R), and R in >B(-R) are aryl, heteroaryl, diarylamino, alkyl, alkenyl, alkynyl, cycloalkyl, alkoxy, or aryloxy, and at least one hydrogen atom in the R may be further substituted with an aryl, heteroaryl, alkyl, alkenyl, alkynyl, or cycloalkyl. Two adjacent Rs may be bonded to each other to form a ring, forming a cycloalkylene, arylene, or heteroarylene. For details of the substituents listed here, the above-mentioned descriptions of "aryl," "arylene," "heteroaryl," "heteroarylene," and "diarylamino," as well as the below-mentioned descriptions of "alkyl," "alkenyl," "alkynyl," "cycloalkyl," "cycloalkylene," "alkoxy," and "aryloxy" may be cited. Furthermore, in this specification, when simply referring to "diarylboryl," unless otherwise specified, the following explanation is added: "The two aryls in the diarylboryl may be bonded to each other via a single bond or a linking group."

[0070] The "alkyl" may be either straight-chain or branched-chain, for example, a straight-chain alkyl having 1 to 24 carbon atoms or a branched-chain alkyl having 3 to 24 carbon atoms, and preferably an alkyl having 1 to 18 carbon atoms (branched-chain alkyl having 3 to 18 carbon atoms), an alkyl having 1 to 12 carbon atoms (branched-chain alkyl having 3 to 12 carbon atoms), an alkyl having 1 to 6 carbon atoms (branched-chain alkyl having 3 to 6 carbon atoms), an alkyl having 1 to 5 carbon atoms (branched-chain alkyl having 3 to 5 carbon atoms), an alkyl having 1 to 4 carbon atoms (branched-chain alkyl having 3 to 4 carbon atoms), etc.

[0071] Specific examples of "alkyl" include 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, s-butyl, t-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, t-pentyl (t-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-dimethylhexyl Examples of the alkyl group include methylheptyl, 2,6-dimethyl-4-heptyl, n-octyl, t-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, and n-eicosyl.

[0072] An "alkylene" is a divalent group obtained by removing any hydrogen from an "alkyl", such as methylene, ethylene, or propylene.

[0073] For "alkenyl," the above explanation of "alkyl" can be referred to, and it is a group in which a C-C single bond in the structure of "alkyl" is replaced with a C=C double bond, and also includes groups in which not only one but two or more single bonds are replaced with double bonds (also called alkadiene-yl or alkatriene-yl).

[0074] Specific examples of "alkenyl" include alkenyl having 2 to 30 carbon atoms, 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, and 5-hexenyl.

[0075] "Alkenylene" is a divalent group obtained by removing any hydrogen from "alkenyl", and examples include vinylene.

[0076] For "alkynyl", the above explanation of "alkyl" can be referred to, and it is a group in which a C-C single bond in the "alkyl" structure is replaced with a C≡C triple bond, and also includes groups in which not only one but two or more single bonds are replaced with triple bonds (also called alkadiyn-yl or alkatriyn-yl).

[0077] The "cycloalkyl" is, for example, a cycloalkyl having 3 to 24 carbon atoms, and 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.

[0078] Specific examples of "cycloalkyl" include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, or alkyl (particularly methyl) substituted derivatives thereof having 1 to 5 carbon atoms or 1 to 4 carbon atoms, bicyclo[1.1.0]butyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.0]pentyl, bicyclo[2.1.1]hexyl, bicyclo[3.1.0]hexyl, bicyclo[2.2.1]heptyl (norbornyl), bicyclo[2.2.2]octyl, adamantyl, diamantyl, decahydronaphthalenyl, and decahydroazulenyl.

[0079] "Cycloalkylene" is, for example, cycloalkylene having 3 to 24 carbon atoms, preferably cycloalkylene having 3 to 20 carbon atoms, cycloalkylene having 3 to 16 carbon atoms, cycloalkylene having 3 to 14 carbon atoms, cycloalkylene having 3 to 12 carbon atoms, cycloalkylene having 5 to 10 carbon atoms, cycloalkylene having 5 to 8 carbon atoms, cycloalkylene having 5 to 6 carbon atoms, or cycloalkylene having 5 carbon atoms. Specific examples of "cycloalkylene" include a structure obtained by removing one hydrogen atom from the above-mentioned "cycloalkyl" (monovalent group) to form a divalent group.

[0080] "Cycloalkenyl" refers to a group having a structure in which at least one pair of single bonds between two carbon atoms in the above-mentioned "cycloalkyl" is replaced with a double bond (for example, -CH ２ -CH ２ Examples of the aryl group include 1-cyclohexenyl, 1-cyclopentenyl, and the like, which are groups in which - is replaced by -CH=CH- and do not fall under the category of aryl.

[0081] "Alkoxy" is a group represented by "Alk-O- (Alk is alkyl)", and the above explanation of "alkyl" can be cited for details of the alkyl.

[0082] "Aryloxy" is a group represented by "Ar-O- (Ar is aryl)", and the above explanation of "aryl" can be cited for details of the aryl. "Arylthio" is a group represented by "Ar-S- (Ar is aryl)", and the above explanation of "aryl" can be cited for details of the aryl.

[0083] The "substituted silyl" is, for example, a silyl substituted with at least one of aryl, alkyl, and cycloalkyl, and is preferably triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, or alkyldicycloalkylsilyl.

[0084] "Triarylsilyl" is a silyl group substituted with three aryl groups, and the above description of "aryl" can be cited for details of this aryl. Specific examples of "triarylsilyl" include triphenylsilyl, diphenylmononaphthylsilyl, monophenyldinaphthylsilyl, and trinaphthylsilyl.

[0085] "Trialkylsilyl" is a silyl group substituted with three alkyl groups, and the details of this alkyl can be found in the above description of "alkyl". Specific examples of the "trialkylsilyl" include trimethylsilyl, triethylsilyl, tri-n-propylsilyl, triisopropylsilyl, tri-n-butylsilyl, triisobutylsilyl, tri-s-butylsilyl, tri-t-butylsilyl, ethyldimethylsilyl, n-propyldimethylsilyl, isopropyldimethylsilyl, n-butyldimethylsilyl, isobutyldimethylsilyl, s-butyldimethylsilyl, t-butyldimethylsilyl, methyldiethylsilyl, n-propyldiethylsilyl, isopropyldiethylsilyl, n-butyldiethylsilyl, s-butyldiethylsilyl, t-butyldiethylsilyl, methyldi-n-propylsilyl, ethyldi-n-propylsilyl, n-butyldi-n-propylsilyl, s-butyldi-n-propylsilyl, t-butyldi-n-propylsilyl, methyldiisopropylsilyl, ethyldiisopropylsilyl, n-butyldiisopropylsilyl, s-butyldiisopropylsilyl, and t-butyldiisopropylsilyl.

[0086] "Tricycloalkylsilyl" is a silyl group substituted with three cycloalkyl groups. For details of this cycloalkyl, refer to the explanation of "cycloalkyl" above. Specific examples of "tricycloalkylsilyl" include tricyclopentylsilyl and tricyclohexylsilyl.

[0087] "Dialkylcycloalkylsilyl" is a silyl group substituted with two alkyls and one cycloalkyl, and the details of the alkyl and cycloalkyl can be found in the explanations of "alkyl" and "cycloalkyl" above.

[0088] "Alkyldicycloalkylsilyl" is a silyl group substituted with one alkyl and two cycloalkyl, and the details of the alkyl and cycloalkyl can be found in the explanations of "alkyl" and "cycloalkyl" above.

[0089] The "substituted germyl" is, for example, a germyl substituted with at least one of aryl, alkyl, and cycloalkyl, and is preferably triarylgermyl, trialkylgermyl, tricycloalkylgermyl, dialkylcycloalkylgermyl, or alkyldicycloalkylgermyl.

[0090] "Triarylgermyl" is a germyl group substituted with three aryl groups, and the above description of "aryl" can be cited for details of this aryl. Specific examples of "triarylgermyl" include triphenylgermyl, diphenylmononaphthylgermyl, monophenyldinaphthylgermyl, and trinaphthylgermyl.

[0091] "Trialkylgermyl" is a germyl group substituted with three alkyl groups, and the details of this alkyl group can be found in the above description of "alkyl." Specific examples of the "trialkylgermyl" include trimethylgermyl, triethylgermyl, tri-n-propylgermyl, triisopropylgermyl, tri-n-butylgermyl, triisobutylgermyl, tri-s-butylgermyl, tri-t-butylgermyl, ethyldimethylgermyl, n-propyldimethylgermyl, isopropyldimethylgermyl, n-butyldimethylgermyl, isobutyldimethylgermyl, s-butyldimethylgermyl, t-butyldimethylgermyl, methyldiethylgermyl, n-propyldiethylgermyl, isopropyldiethylgermyl, n-butyldiethylgermyl, s-butyldiethylgermyl, t-butyldiethylgermyl, methyldi-n-propylgermyl, ethyldi-n-propylgermyl, n-butyldi-n-propylgermyl, s-butyldi-n-propylgermyl, t-butyldi-n-propylgermyl, methyldiisopropylgermyl, ethyldiisopropylgermyl, n-butyldiisopropylgermyl, s-butyldiisopropylgermyl, and t-butyldiisopropylgermyl.

[0092] "Tricycloalkylgermyl" is a germyl group substituted with three cycloalkyl groups, and the above description of "cycloalkyl" can be cited for details of this cycloalkyl. Specific examples of "tricycloalkylgermyl" include tricyclopentylgermyl and tricyclohexylgermyl.

[0093] "Dialkylcycloalkylgermyl" is a germyl group substituted with two alkyls and one cycloalkyl, and the details of the alkyl and cycloalkyl can be found in the explanations of "alkyl" and "cycloalkyl" above.

[0094] "Alkyldicycloalkylgermyl" is a germyl group substituted with one alkyl and two cycloalkyl, and the details of the alkyl and cycloalkyl can be found in the explanations of "alkyl" and "cycloalkyl" above.

[0095] "Substituted stannyl" is, for example, stannyl substituted with at least one of aryl, alkyl, and cycloalkyl, and is preferably triarylstannyl, trialkylstannyl, tricycloalkylstannyl, dialkylcycloalkylstannyl, or alkyldicycloalkylstannyl.

[0096] "Triarylstannyl" is a stannyl group substituted with three aryls, and the above description of "aryl" can be cited for details of this aryl. Specific examples of "triarylstannyl" include triphenylstannyl, diphenylmononaphthylstannyl, monophenyldinaphthylstannyl, and trinaphthylstannyl.

[0097] "Trialkylstannyl" is a stannyl group substituted with three alkyl groups, and the details of this alkyl can be found in the above description of "alkyl." Specific examples of "trialkylstannyl" include trimethylstannyl, triethylstannyl, tri-n-propylstannyl, triisopropylstannyl, tri-n-butylstannyl, triisobutylstannyl, tri-s-butylstannyl, tri-t-butylstannyl, ethyldimethylstannyl, n-propyldimethylstannyl, isopropyldimethylstannyl, n-butyldimethylstannyl, isobutyldimethylstannyl, s-butyldimethylstannyl, t-butyldimethylstannyl, methyldiethylstannyl, n-propyldiethylstannyl, isopropyldiethylstannyl, n-butyldiethylstannyl, s-butyldiethylstannyl, t-butyldiethylstannyl, methyldi-n-propylstannyl, ethyldi-n-propylstannyl, n-butyldi-n-propylstannyl, s-butyldi-n-propylstannyl, t-butyldi-n-propylstannyl, methyldiisopropylstannyl, ethyldiisopropylstannyl, n-butyldiisopropylstannyl, s-butyldiisopropylstannyl, and t-butyldiisopropylstannyl.

[0098] "Tricycloalkylstannyl" is a stannyl group substituted with three cycloalkyl groups, and the details of this cycloalkyl can be found in the above description of "cycloalkyl." Specific examples of "tricycloalkylstannyl" include tricyclopentylstannyl and tricyclohexylstannyl.

[0099] "Dialkylcycloalkylstannyl" is a stannyl group substituted with two alkyls and one cycloalkyl, and the details of the alkyl and cycloalkyl can be found in the explanations of "alkyl" and "cycloalkyl" above.

[0100] "Alkyldicycloalkylstannyl" is a stannyl group substituted with one alkyl and two cycloalkyl groups, and the details of the alkyl and cycloalkyl groups can be found in the explanations of "alkyl" and "cycloalkyl" above.

[0101] "Halogen" is fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, more preferably fluorine or chlorine, and even more preferably fluorine.

[0102] When cyano or halogen is substituted, it is also preferable that all or part of the hydrogen atoms in the aryl or heteroaryl in the structure are replaced with cyano or halogen.

[0103] The substituent represented by formula (A30) has the following structure.

[0104] In formula (A30), Ak represents hydrogen, a substituted or unsubstituted alkyl, a substituted or unsubstituted alkenyl, a substituted or unsubstituted cycloalkyl, or a substituted or unsubstituted cycloalkenyl, and at least one —CH ２ - may be replaced by -O- or -S-, R Ａｋ is a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted alkyl, or a substituted or unsubstituted cycloalkyl; R Ａｋ may be bonded to Ak via a linking group or a single bond, and * indicates the bonding position.

[0105] In formula (A30), since Ak is the above-mentioned substituent, it does not conjugate with the unshared electron pair on N, so that the unshared electron pair can be conjugated with the π electron to which it is bonded, and a larger wavelength change is possible compared to when an aryl or the like is present at the same position. The same applies to the influence on the multiple resonance effect, and a larger improvement in thermally activated delayed fluorescence (TADF) properties is possible.

[0106] R Ａｋis preferably aryl which may be substituted with alkyl or cycloalkyl, heteroaryl which may be substituted with alkyl or cycloalkyl, alkyl or cycloalkyl, more preferably aryl which may be substituted with alkyl, heteroaryl which may be substituted with alkyl, alkyl or cycloalkyl, still more preferably aryl which may be substituted with alkyl, and particularly preferably phenyl which may be substituted with methyl.

[0107] In formula (A30), Ak is preferably alkyl having 1 to 6 carbon atoms or cycloalkyl having 3 to 14 carbon atoms, more preferably alkyl having 1 to 4 carbon atoms or cycloalkyl having 3 to 8 carbon atoms, still more preferably alkyl having 1 to 4 carbon atoms, and particularly preferably methyl.

[0108] R Ａｋ and Ak may be the same or different, and are preferably different.

[0109] R Ａｋ may be bonded to Ak via a linking group or a single bond. In this case, the linking group may be >O, >S, or >Si(—R) ２ Examples include: Si(-R) ２ R is hydrogen, aryl having 6 to 12 carbon atoms, alkyl having 1 to 6 carbon atoms, or cycloalkyl having 3 to 14 carbon atoms. Ａｋ Examples of the structure in which is bonded to Ak via a linking group or a single bond include the following.

[0110] In the above formulas, * indicates a bonding position.

[0111] [When two groups bonded to the same atom are bonded to each other] In the present specification, when it is said that two groups bonded to the same atom may be bonded to each other to form a ring, they may be bonded to each other by a single bond or a linking group (collectively also referred to as a linking group), and examples of the linking group include -CH ２ -CH ２ -, -CHR-CHR-, -CR ２ -CR ２-, -CH=CH-, -CR=CR-, -C≡C-, -N(-R)-, -O-, -S-, -C(-R) ２ -, -Si(-R) ２ -, -C(=O)-, -C(=S)-, -S(=O)-, -S(=O) ２ -, -Se(=O)-, -Se(=O) ２ -, -P(=O)-, -B(-R)-, or -Se-, and examples thereof include the following structures: ２ -CR ２ -R, -CR=CR-R, -N(-R)-R, -C(-R) ２ -R, -B(-R)-R, and -Si(-R) ２ Each R in - is independently hydrogen, aryl which may be substituted with alkyl or cycloalkyl, heteroaryl which may be substituted with alkyl or cycloalkyl, alkyl which may be substituted with cycloalkyl, alkenyl which may be substituted with alkyl or cycloalkyl, alkynyl which may be substituted with alkyl or cycloalkyl, or cycloalkyl which may be substituted with alkyl or cycloalkyl. Two adjacent Rs may be bonded to form a ring, thereby forming a cycloalkylene, arylene, or heteroarylene.

[0112]

[0113] The bonding group includes a single bond, and a linking group such as -CR=CR-, -N(-R)-, -O-, -S-, and -C(-R) ２ -, -Si(-R) ２ -, -C(=O)-, and -Se- are preferred, and a single bond, -CR=CR-, -N(-R)-, -O-, -S-, -C(=O)-, and -C(-R)- as a linking group are preferred. ２ - is more preferred, a single bond, and -CR=CR-, -N(-R)-, -O-, and -S- as linking groups are even more preferred, and a single bond is most preferred.

[0114] The position at which two Rs are bonded by the bonding group is not particularly limited as long as it is a position at which bonding is possible, but it is preferable that they be bonded at the most adjacent positions. For example, when the two groups are phenyl, it is preferable that they be bonded at positions ortho (2-position) relative to the bonding position (1-position) of "C" or "Si" in the phenyl (see the structural formula above).

[0115] <Stereoisomers, etc.> The polycyclic aromatic compound of the present invention may exist as an enantiomer or diastereomer depending on the type of substituent, etc., and regardless of the structural formula described, any pure stereoisomer, any mixture of stereoisomers, racemate, etc. are all intended to be encompassed within the scope of the present invention.

[0116] <1. Polycyclic Aromatic Compounds> <Overall Structure> Polycyclic aromatic compounds in which aromatic rings are linked by heteroatoms such as boron, nitrogen, oxygen, and sulfur have already been found to have large HOMO-LUMO gaps (band gaps Eg in thin films). This is because six-membered rings containing heteroatoms have low aromaticity, suppressing the decrease in the HOMO-LUMO gap that accompanies the expansion of the conjugated system. It has also been found that the HOMO-LUMO gap can be arbitrarily changed depending on the type and linking method of the heteroatom. This is thought to be due to the fact that the HOMO and LUMO energies can be arbitrarily changed depending on the spatial extent and energy of the unoccupied orbitals or lone pairs of the heteroatoms.

[0117] These polycyclic aromatic compounds have narrow half-widths of their fluorescence emission peaks because SOMO1 and SOMO2 in the excited state are localized on each atom due to electronic perturbation of the heteroatoms, and when used as dopants in organic EL devices, they can produce light emission with high color purity. Ｓ１Ｔ１ The HOMO and LUMO energies can be adjusted by introducing substituents, which allows the ionization potential and electron affinity to be optimized depending on the surrounding materials.

[0118] In the present invention, we have succeeded in producing a polycyclic aromatic compound represented by formula (1), which has two or more nitrogen atoms connecting aromatic rings, and in which these two nitrogen atoms are further linked to form a hoop on the plane formed by the polycyclic aromatic structure. We have found that this compound makes it possible to produce organic electroluminescent devices that emit light with long life and high efficiency. We have also found that this compound enables emission of light with higher color purity and a narrow emission full width at half maximum (FWHM). This is thought to be due to the formation of a hoop, which creates a fixed molecular structure.

[0119]

[0120] In formula (1), Cy represents a structure consisting of one or more structural units represented by formula (Cy), L represents the presence of at least one crosslink formed by a linking group represented by formula (1-a) or formula (1-b), and at least two of X in the above structure are nitrogen atoms bonded to * in the linking group represented by formula (1-a) or formula (1-b), respectively.

[0121] The symbols in each formula will be described in detail later.

[0122] <Structure Composed of One or Two or More Structural Units Represented by Formula (Cy)> In the polycyclic aromatic compound of the present invention, Cy represents a structure composed of one or two or more structural units represented by formula (Cy). A polycyclic aromatic compound having a structure composed of one structural unit represented by formula (Cy) is a structure represented by formula (Cy). An example of a structure composed of two or more structural units represented by formula (Cy) is a polymer of the structure represented by formula (Cy). The polymer is preferably a dimer to a hexamer, more preferably a dimer to a trimer, and particularly preferably a dimer. The polymer may be in a form having a plurality of the structural units, and may be in a form in which any ring contained in the structural unit is bonded to multiple structural units so as to be shared by the multiple structural units, or in which any ring contained in the structural unit is bonded to multiple structural units so as to be fused together. Furthermore, the structural units may be bonded to multiple structural units via a linking group such as a single bond, an alkylene having 1 to 3 carbon atoms, phenylene, or naphthylene. Among these, a form in which the structural units are bonded to each other so as to be shared by the ring is preferred. In the polycyclic aromatic compound having a structure consisting of two or more structural units represented by formula (Cy), the two or more structural units may be the same or different from each other.

[0123] Examples of structures consisting of two or more structural units represented by formula (Cy) include the structures shown below. In the following formula, when ring B is a 5- or 6-membered monocyclic ring, the two rings B may be connected to each other by steric hindrance. ｃｙ For sites where it is thought that a bond cannot be formed via L ｃｙ The description is omitted.

[0124]

[0125]

[0126]

[0127]

[0128] In the above formula, a ring that is the A ring of at least one structural unit and the B ring of at least one structural unit as a result of sharing a ring with multiple structural units is represented by "A'". Furthermore, the A ring that is a benzene ring is represented by "a". LL is a single bond or a linking group, and the linking group is preferably a substituted or unsubstituted arylene or a substituted or unsubstituted heteroarylene.

[0129] In each of the above formulae, a structure in which ring A, ring B, and ring A' are all benzene rings and all Y's are B (boron) is an example of a preferred structure.

[0130] <Explanation of Ring Structure in Structural Unit Represented by Formula (Cy)> In formula (Cy), "A" and "B" in the circles are symbols indicating the ring structure represented by each circle. The structure represented by formula (Cy) has a structure in which at least three aromatic rings in ring A and ring B are connected by boron and nitrogen to form a further ring structure. The formed ring structure is a fused ring structure composed of at least five rings.

[0131] Ring A and the two rings B are each independently a substituted or unsubstituted aryl ring or a substituted or unsubstituted heteroaryl ring.

[0132] Ring A forms a trivalent group having bonds to three consecutive elements (preferably carbon) on the aryl ring or heteroaryl ring in the structure. These three bonds are respectively bonded to Y and two Xs. In a structure consisting of two or more structural units represented by formula (Cy) as described above, ring A may form a tetravalent, pentavalent, or hexavalent group. In ring A, the ring having the above-mentioned elements having three bonds as ring constituent elements is preferably a 5-membered ring or a 6-membered ring. This ring may further be condensed with another ring. An example of a 6-membered ring is a benzene ring. Examples of 6-membered rings further condensed with other rings include a naphthalene ring, an anthracene ring, a benzanthracene ring, a fluoranthene ring, a perylene ring, a pentacene ring, a benzofluoranthene ring, a xanthene ring, a quinoline ring, an isoquinoline ring, a quinazoline ring, a dibenzofuran ring, a dibenzothiophene ring, a carbazole ring, a dibenzoselenophene ring, a pyrene ring, a triphenylene ring, a spirobifluorene ring, an indolo[3,2,1-jk]carbazole ring, a 9,10-dihydro-9,10-o-benzonoanthracene ring, or a ring represented by any of the following: Examples of five-membered rings include a furan ring, a thiophene ring, a pyrrole ring, and a thiazole ring. Examples of five-membered rings fused with other rings include a benzofuran ring, a benzothiophene ring, and an indole ring. An example of a fused ring is an indene ring. A benzene ring is preferred as the aryl or heteroaryl ring in ring A.

[0133] Each B ring forms a divalent group having bonds to two adjacent elements (preferably carbon) on the aryl ring or heteroaryl ring in the structure. These two bonds are respectively bonded to Y and one of the X. In a structure consisting of two or more structural units represented by formula (Cy) as described above, B ring may sometimes form a trivalent, tetravalent, or pentavalent group. In each B ring, the ring having the above-mentioned two bonded elements as ring constituent elements is preferably a 5- or 6-membered ring. This ring may further be condensed with another ring. Examples of 6-membered rings include a benzene ring and a pyridine ring. Examples of 6-membered rings further condensed with other rings include a naphthalene ring, an anthracene ring, a benzanthracene ring, a fluoranthene ring, a perylene ring, a pentacene ring, a benzofluoranthene ring, a xanthene ring, a quinoline ring, a benzofuran ring, a benzothiophene ring, an indole ring, a benzoselenophene ring, a dibenzofuran ring, a dibenzothiophene ring, a carbazole ring, a dibenzoselenophene ring, a pyrene ring, a triphenylene ring, a spirobifluorene ring, an indolo[3,2,1-jk]carbazole ring, a 9,10-dihydro-9,10-o-benzonoanthracene ring, or a ring represented by any of the following: Examples of five-membered rings include a furan ring, a thiophene ring, a pyrrole ring, a thiazole ring, and a selenophene ring. Examples of five-membered rings fused with other rings include a benzofuran ring, a benzothiophene ring, an indole ring, and a benzoselenophene ring. An example of a fused ring is an indene ring.

[0134] The aryl or heteroaryl ring in Ring B is preferably, independently of one another, a benzene ring, a furan ring, a thiophene ring, a pyrrole ring, a thiazole ring, an indene ring, a benzofuran ring, a benzothiophene ring, a benzoselenophene ring, or an indole ring, more preferably a benzene ring, an indene ring, a benzofuran ring, or a benzothiophene ring. It is more preferably that one Ring B is a benzene ring and the other Ring B is a benzene ring, an indene ring, a benzofuran ring, or a benzothiophene ring, and particularly preferably that one Ring B is a benzene ring and the other Ring B is a benzene ring, an indene ring, a benzofuran ring, or a benzothiophene ring.

[0135] In formula (Cy), the two B rings are L ｃｙ may be bonded via L ｃｙ The dashed lines between the B rings indicate that the two B rings may be unbonded or bonded.

[0136] That is, the structure (structural unit) represented by formula (Cy) is a structure (structural unit) represented by formula (Cy-1) or formula (Cy-2) below.

[0137] L ｃｙ is a single bond or a linking group. When two B rings are not bonded, L ｃｙ When two B rings are bonded together, each of the two B rings has L at a ring-constituting atom (preferably carbon) of the aryl ring or heteroaryl ring in the B ring. Ｃｙ It is preferably directly bonded to

[0138] L ｃｙ Examples of the linking group include —CH ２ -CH ２ -, -CHR-CHR-, -CR ２ -CR ２ -, -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 -, -Ge(-R) ２ -, -Sn(-R) ２ -, -Se-, or -Te-. ２ -CR ２ -" R, "-CR=CR-" R, "-N(-R)-" R, "-C(-R) ２ -" R, "-B(-R)-" R, "-Ge(-R) ２ -"R, "-Sn(-R) ２ -"R, and "-Si(-R) ２ Each R in "-" is independently hydrogen or a substituent, and is preferably hydrogen, aryl which may be substituted with alkyl or cycloalkyl, heteroaryl which may be substituted with alkyl or cycloalkyl, alkyl which may be substituted with alkyl or cycloalkyl, alkenyl which may be substituted with alkyl or cycloalkyl, alkynyl which may be substituted with alkyl or cycloalkyl, or cycloalkyl which may be substituted with alkyl or cycloalkyl. Two Rs bonded to the same atom may be bonded to each other to form a ring. Furthermore, two adjacent Rs may be bonded to each other to form an epoxy ring, an aziridine ring, a cycloalkylene ring, an arylene ring, or a heteroarylene ring. These rings may have a substituent, and the substituent is preferably alkyl or cycloalkyl.

[0139] In the substituted or unsubstituted aryl ring or substituted or unsubstituted heteroaryl ring in ring A and ring B, the substituent when referred to as "substituted or unsubstituted (substituted or unsubstituted)" includes at least one substituent selected from the substituent group Zα. Furthermore, the substituent may be a substituted or unsubstituted diarylphosphino such as diphenylphosphino, or a substituted or unsubstituted diarylphosphinyl such as diphenylphosphinyl. When multiple substituents are present, the multiple substituents may be the same or different. Preferred substituents include substituted or unsubstituted alkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino, substituted or unsubstituted arylheteroarylamino, substituted silyl, substituted germyl, or halogen, with t-butyl, t-amyl, or phenyl optionally substituted with halogen, t-butyl, diphenylamino, substituted or unsubstituted carbazolyl, or halogen being more preferred. For other preferred substituents, the description in <Preferred Substituents> below can be referred to.

[0140] <Y> In a structure consisting of one or more structural units represented by formula (Cy), Y each independently represents >B-, >P-, >P(=O)-, >P(=S)-, >Al-, >Ga-, >As-, >Si(-R Ｙ ) - or >Ge(-R Ｙ )-, and R in Y Ｙ are each independently substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl. Y is >B-, >P-, >P(=O)-, >P(=S)-, or >Si(-R Ｙ )- is preferred, and >B- is particularly preferred.

[0141] <X> Two of X in a structure consisting of one or two or more structural units represented by formula (Cy) are nitrogen atoms bonded to either * of the linking group represented by formula (1-a) or formula (1-b). Furthermore, when a structure consisting of two or more structural units represented by formula (Cy) contains four or more Xs that are not shared by two structural units, there may be one or more pairs of two Xs that are nitrogen atoms bonded to * of another linking group represented by formula (1-a) or formula (1-b).

[0142] The two Xs (nitrogen atoms) bonded to the two *s in a linking group represented by formula (1-a) or formula (1-b) are two Xs in one structural unit when Cy is composed of one structural unit represented by formula (Cy); when Cy is composed of two or more structural units represented by formula (Cy) and three or more Xs are present, they may be two Xs in one structural unit or Xs in two different structural units.

[0143] When three or more Xs are present, the other Xs are each independently a nitrogen atom shared by two structural units, or >O, >N—R ＮＸ , >C(-R ＣＸ ) ２ , >Si(-R ＩＸ ) ２ , >S, >Se, or >Ge (-R ＧＸ ) ２ , and R ＮＸ , R ＣＸ , R ＩＸ , and R ＧＸ are each independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, and >C(-R ＣＸ ) ２ The two R's ＣＸ may be bonded to each other to form a ring, and >Si(-R ＩＸ ) ２ The two R's ＩＸ may be bonded to each other to form a ring, and >Ge(-R ＧＸ ) ２ The two R's ＧＸmay be bonded to each other to form a ring, R ＮＸ , at least one R ＣＸ and at least one R ＩＸ are each connected to the R ＮＸ , R ＣＸ , or R ＩＸ may be bonded to one or two of the rings to which X containing the following is bonded (the aryl or heteroaryl rings in ring A and ring B).

[0144] R ＮＸ is preferably a substituted or unsubstituted aryl or a substituted or unsubstituted heteroaryl, more preferably a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted terphenyl, a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted dibenzothienyl, or a substituted or unsubstituted N-arylcarbazolyl, and even more preferably a phenyl which may be substituted with at least one t-butyl, a biphenyl which may be substituted with at least one t-butyl, a terphenyl which may be substituted with at least one t-butyl, or a dibenzofuranyl which may be substituted with at least one t-butyl. ＮＸ The aryl ring or heteroaryl ring in R is preferably condensed with a cycloalkane. ＣＸ is preferably a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, or a substituted or unsubstituted alkyl, and more preferably a substituted or unsubstituted phenyl or methyl. ＩＸ is preferably a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, or a substituted or unsubstituted alkyl, and more preferably a substituted or unsubstituted phenyl or methyl.

[0145] In the polycyclic aromatic compound containing the structural unit represented by formula (1) used as an emitting dopant in the light-emitting layer of an organic EL device, each X independently represents >N-R ＮＸ , >S, >O, or >Se, and >N—R ＮＸ , >O, or >S, and more preferably >N-R ＮＸOr more preferably >S, and >N-R ＮＸ It is particularly preferred that:

[0146] <Explanation of change in ring structure due to bonding between X and ring> R in X ＮＸ , R ＣＸ and R ＩＸ may be bonded to one or two rings, including itself, to which X is bonded, via a single bond or a linking group. ＮＸ , R ＣＸ and R ＩＸ may be bonded to at least one of ring A and ring B via a single bond or a linking group.

[0147] R ＮＸ , R ＣＸ and R ＩＸ When each of these is bonded to a ring, the linking group is —CH ２ -CH ２ -, -CHR-CHR-, -CR ２ -CR ２ -, -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 -, -Ge(-R) ２ -, -Sn(-R) ２ -, -Te-, or -Se-. ２ -CR ２ -" R, "-CR=CR-" R, "-N(-R)-" R, "-C(-R) ２ -" R, "-B(-R)-" R, and "-Si(-R) ２Each R in "-" is independently hydrogen or a substituent, and the substituent is preferably aryl which may be substituted with alkyl or cycloalkyl, heteroaryl which may be substituted with alkyl or cycloalkyl, alkyl which may be substituted with alkyl or cycloalkyl, alkenyl which may be substituted with alkyl or cycloalkyl, alkynyl which may be substituted with alkyl or cycloalkyl, or cycloalkyl which may be substituted with alkyl or cycloalkyl. Two Rs bonded to the same atom may be bonded to each other to form a ring. Furthermore, two adjacent Rs may be bonded to each other to form a cyclopropane ring, an aziridine ring, a cycloalkylene ring, an arylene ring, or a heteroarylene ring. These rings may also be substituted with alkyl or cycloalkyl.

[0148] >N-R ＮＸ R in ＮＸ Examples of the fused ring formed by bonding with a benzene ring as an aryl ring in ring A, ring B, or ring C (ring c) include a carbazole ring (where R is phenyl). ＮＸ is bonded by a single bond), a phenoxazine ring (R is phenyl ＮＸ is bonded by —O—), a phenothiazine ring (R is phenyl ＮＸ is bonded by -S-), or an acridone ring (R is phenyl ＮＸ From the viewpoint of obtaining a highly efficient element, >N-R ＮＸ R in ＮＸ is preferably bonded to the ring in ring A via a single bond.

[0149] Furthermore, the following partial structure (A10) may be formed by the above-mentioned linkage.

[0150] In formula (A10), R Ａ１ ~R Ａ４ are each independently hydrogen, optionally substituted alkyl, or optionally substituted cycloalkyl; R Ａ１ ~R Ａ４Any two to four of these may be bonded to each other by a linking group or a single bond, and one of the two rings to which X is bonded is bonded at the two * positions, and the other ring is bonded at the ** position. That is, N in formula (A10) is X １ or X ２ But > N-R ＮＸ When it is said that ＮＸ where N is N. The atoms on the ring bonded at the two * positions may be adjacent atoms (preferably carbon atoms). The partial structure represented by formula (A10) contains an N-C bond with a weak bond dissociation energy (BDE), but the presence of another bond forming a ring promotes a reverse reaction (recombination reaction) even when the N-C bond is broken, resulting in a more stable structure. Therefore, organic EL devices manufactured using polycyclic aromatic compounds having such structures are expected to have a longer device life. When a polycyclic aromatic compound contains a structure represented by formula (A10), the number of such structures may be one or two (preferably one).

[0151] In formula (A10), R Ａ１ ~R Ａ４ Any two to four of R may be linked to each other via a linking group or a single bond. Ａ１ ~R Ａ４ is any two (R Ａ１ and R Ａ４ , R Ａ１ and R Ａ４ and R Ａ２ and R Ａ３ , R Ａ１ and R Ａ２ , R Ａ３ and R Ａ４ , R Ａ１ and R Ａ２ and R Ａ３ and R Ａ４ ) are preferably bonded to each other via a linking group or a single bond, and R Ａ１ and R Ａ４are more preferably bonded to each other via a linking group or a single bond. An example of a divalent group formed by bonding to each other is alkylene. At least one hydrogen atom in the alkylene may be substituted with an alkyl or cycloalkyl, and at least one (preferably one) —CH ２ The - may be substituted with -O- and -S-. The divalent group formed by bonding together is preferably a linear alkylene group having 2 to 5 carbon atoms, more preferably a linear alkylene group having 3 or 4 carbon atoms, and more preferably a linear alkylene group having 4 carbon atoms (-(CH ２ ) ４ -) is more preferred. ２ ) ４ It is particularly preferred that the -) is unsubstituted.

[0152] The remaining R that is not involved in the linkage by the linking group or single bond Ａ１ ~R Ａ４ are each independently preferably hydrogen or an alkyl which may be substituted, more preferably an alkyl having 1 to 6 carbon atoms which may be substituted, further preferably an unsubstituted alkyl having 1 to 6 carbon atoms, and most preferably methyl. That is, the partial structure represented by formula (A10) is preferably a structure represented by formula (A11) below.

[0153] In formula (A11), Me is methyl, and is bonded to one of the two rings to which X is bonded at the two * positions, and to the other ring at the ** position.

[0154] <Examples of Structures Composed of One or Two or More Structural Units Represented by Formula (Cy)> Preferred examples of Cy (structures composed of one or two or more structural units represented by formula (Cy)) include groups represented by any of the following formulas:

[0155]

[0156]

[0157]

[0158] In formulas (Cy-1-1) to (Cy-1-51) and (Cy-2-1) to (Cy-2-6), A ＣＹ >O, >S, >Se, >Te, >SO, >SO ２ , >C(-R ＣＹ ) ２ , >C=O, >Si(-R ＣＹ ) ２ , >Ge(-R ＣＹ ) ２ , or >Sn(-R ＣＹ ) ２ and R ＣＹ are each independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, and >C(-R ＣＹ ) ２ , >Si(-R ＣＹ ) ２ , >Ge(-R ＣＹ ) ２ , and >Sn(-R ＣＹ ) ２ The two R's ＣＹ may be bonded to each other to form a ring, X ＸＣＹ are each independently or >N-R ＸＣＹ , >O, >S, >Se, >Te, >SO, >SO ２ , >C(-R ＸＣＹ ) ２ , >C=O, >Si(-R ＸＣＹ ) ２ , >Ge(-R ＸＣＹ ) ２ , >Sn(-R ＸＣＹ ) ２ , or a single bond, R ＸＣＹ are each independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, and >C(-R ＸＣＹ ) ２ , >Si(-R ＸＣＹ ) ２ , >Ge(-R ＸＣＹ ) ２ , and >Sn(-R ＸＣＹ ) ２The two R's ＸＣＹ may be bonded to each other to form a ring.

[0159] In formulas (Cy-1-1) to (Cy-1-45) and formulas (Cy-2-1) to (Cy-2-6), * represents L (L in formula (1-a) Ａａ Or L in formula (1-b) Ａｂ ) indicates the bonding position. In addition, in the case of a structure consisting of two or more structural units represented by formula (Cy), there may be four or more *'s in the formula. In such a case, it is preferable that one L is bonded to two *'s in each structural unit represented by formula (Cy). This is because it is thought that hoops formed by L's are more likely to be formed above and below the plane formed by the polycyclic aromatic structure, improving the chemical stability of the ring structure (see the structural example below).

[0160]

[0161] <L and Linking Group Represented by Formula (1-a) or Formula (1-b)> L indicates that at least one bridge formed by a linking group represented by Formula (1-a) or Formula (1-b) is present in Formula (1). In the linking group represented by Formula (1-a) or Formula (1-b), two *'s are bonded to two X's (nitrogen atoms), respectively. Therefore, when Cy is a structure consisting of one structural unit represented by Formula (Cy), the polycyclic aromatic compound represented by Formula (1) can be represented by the following Formula (1-1-a). When Cy is a structure consisting of two or more structural units represented by Formula (Cy) and there are four or more X's that are not shared by the two structural units, two or more of the above linking groups can be present in the polycyclic aromatic compound represented by Formula (1). For example, among the examples of structures consisting of two or more structural units represented by Formula (Cy), there are four X's that are not shared by the two structural units in Formula (P1-R2-1). In this case, one linking group may be present as shown in the following formula (P1-R2-1-1-a), or two may be present as shown in the following formula (P1-R2-1-2-a). L means L1 in formula (1-1-a) and formula (P1-R2-1-1-a), etc., and L1 and L2 in formula (P1-R2-1-2-a), etc.

[0162]

[0163] In the above formula, L1 and L2 each independently represent a linking group represented by formula (1-a) or formula (1-b), and X' has the same meaning as X, except that the nitrogen atom bonded to * in the linking group represented by formula (1-a) or formula (1-b) or the nitrogen atom shared by two structural units is excluded.

[0164]

[0165] In each of the formulas (1-a) and (1-b), L Aａ are each independently a trivalent group, and L Aｂ are each independently a divalent group, and L B are each independently a single bond or a divalent group, and * indicates the bonding position with the nitrogen atom represented by X. Ｂ may be the same or different, but are preferably the same, particularly from the viewpoint of production.

[0166] L Ａａ and L Ａｂ Preferably, the ring structure includes at least one ring structure, such as an aryl ring, a heteroaryl ring, a cycloalkane ring, a cycloalkene ring, and at least one CH or CH in the cycloalkane ring or the cycloalkene ring. ２ Examples include rings in which a heteroatom is replaced by a heteroatom.

[0167] L Ａａ Preferred examples of the formula (L Ａａ－１ ) and L Ａｂ Preferred examples of the formula (L Ａｂ－１ ) groups represented by the formula (I) are exemplified.

[0168] Formula (L Ａａ－１ ) and formula (L Ａｂ－１ In the above, ring Aa and ring Ab are each independently a substituted or unsubstituted aryl ring, a substituted or unsubstituted heteroaryl ring, or a substituted or unsubstituted cycloalkane ring.

[0169] The Aa ring forms a trivalent group having bonds to three elements (for example, three consecutive elements (preferably carbon) on the ring) of the aryl ring, heteroaryl ring, or cycloalkane ring in the structure. These three bonds are respectively connected to a nitrogen atom and two L Ｂ is bonded to. In the Aa ring, the ring having the element having three bonds as a ring constituent element is preferably a five-membered ring or a six-membered ring. This ring may be further fused with another ring. Examples of six-membered rings include a benzene ring and a cyclohexane ring. Examples of six-membered rings further fused with another ring include a naphthalene ring, a tetrahydronaphthalene ring, an anthracene ring, a xanthene ring, a quinoline ring, an isoquinoline ring, a quinazoline ring, a dibenzofuran ring, a dibenzothiophene ring, a carbazole ring, a pyrene ring, a triphenylene ring, a spirobifluorene ring, an indolo[3,2,1-jk]carbazole ring, and a ring represented by any of the following:

[0170] Examples of five-membered rings include a cyclopentane ring, a furan ring, a thiophene ring, a pyrrole ring, and a thiazole ring. Examples of five-membered rings fused with other rings include a benzofuran ring, a benzothiophene ring, and an indole ring. An example of a fused ring is an indene ring. As the aryl ring, heteroaryl ring, or cycloalkane ring in ring Aa, a benzene ring, a xanthene ring (particularly a 9,9-dimethylxanthene ring), or a dibenzofuran ring is preferred.

[0171] Each Ab ring forms a divalent group having bonds to two elements (for example, two elements (preferably carbon) adjacent to each other on the ring) on ​​the aryl ring, heteroaryl ring, or cycloalkane ring in its structure. These two bonds are respectively connected to a nitrogen atom and L. Ｂis bonded to. In the ring Ab, the ring having the element having the two bonds as a ring constituent element is preferably a five-membered ring or a six-membered ring. This ring may be further fused with another ring. Examples of six-membered rings include a benzene ring and a cyclohexane ring. Examples of six-membered rings further fused with another ring include a naphthalene ring, a tetrahydronaphthalene ring, an anthracene ring, a xanthene ring, a quinoline ring, an isoquinoline ring, a quinazoline ring, a dibenzofuran ring, a dibenzothiophene ring, a carbazole ring, a pyrene ring, a triphenylene ring, a spirobifluorene ring, an indolo[3,2,1-jk]carbazole ring, and a ring represented by any of the following:

[0172] Examples of five-membered rings include a cyclopentane ring, a furan ring, a thiophene ring, a pyrrole ring, and a thiazole ring. Examples of five-membered rings fused with other rings include a benzofuran ring, a benzothiophene ring, and an indole ring. An example of a fused ring is an indene ring. As the aryl ring, heteroaryl ring, or cycloalkane ring in ring Ab, a benzene ring, a xanthene ring (particularly a 9,9-dimethylxanthene ring), or a dibenzofuran ring is preferred.

[0173] In the substituted or unsubstituted aryl ring, substituted or unsubstituted heteroaryl ring, or substituted or unsubstituted cycloalkane ring in the Aa and Ab rings, the substituent when referred to as "substituted or unsubstituted (substituted or unsubstituted)" includes at least one substituent selected from the substituent group Zα. Furthermore, the substituent may be a substituted or unsubstituted diarylphosphino such as diphenylphosphino, or a substituted or unsubstituted diarylphosphinyl such as diphenylphosphinyl. When multiple substituents are present, the multiple substituents may be the same or different. Preferred substituents include substituted or unsubstituted alkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino, substituted or unsubstituted arylheteroarylamino, substituted silyl, substituted germyl, or halogen, with t-butyl or phenyl optionally substituted with halogen, t-butyl, diphenylamino, substituted or unsubstituted carbazolyl, or halogen being more preferred. For other preferred substituents, the description in <Preferred Substituents> below can be referenced.

[0174] Formula (L Ａａ－１ ) and formula (L Ａｂ－１ In the formula, * indicates the bonding position to the nitrogen atom of X, and # indicates the bonding position to the nitrogen atom of L. Ｂ This is the bonding position with

[0175] L Ａａ More specific examples of the formula (L Ａａ－２ ) and L Ａｂ A more specific example of the formula (L Ａｂ－２ ) groups represented by the formula (I) are exemplified.

[0176] Formula (L Ａａ－２ ) and formula (L Ａｂ－２ In the formula, each Z is independently N or C-R Ｚ or Z = Z are each independently >O, >N-R ＮＺ , >C(-R ＣＺ ) ２ , >Si(-R ＩＺ ) ２, >S, or >Se. ＮＺ , R ＣＺ , and R ＩＺ are each independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, and >C(-R ＣＺ ) ２ The two R's ＣＺ may be bonded to each other to form a ring, and >Si(-R ＩＺ ) ２ The two R's ＩＺ may be bonded to each other to form a ring. Each Z independently represents N or C—R Ｚ It is preferable that C-R Ｚ It is more preferable that:

[0177] R Ｚ are each independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino, substituted or unsubstituted diheteroarylamino, substituted or unsubstituted arylheteroarylamino, substituted or unsubstituted diarylboryl, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted arylthio, substituted germyl, substituted stannyl, or substituted silyl, preferably hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino, substituted or unsubstituted alkyl, substituted silyl, or substituted or unsubstituted cycloalkyl, more preferably hydrogen or substituted or unsubstituted alkyl, and even more preferably hydrogen, methyl, or t-butyl.

[0178] Two adjacent C-R Ｚmay be bonded to each other to form an aryl ring or a heteroaryl ring (together with the ring having the carbon atoms to which they are bonded as constituent atoms). Examples of the aryl ring or heteroaryl ring formed include a xanthene ring and a dibenzofuran ring. The aryl ring and heteroaryl ring formed may have a substituent, and examples of the substituent include the above-mentioned R Ｚ is a substituent. Ａａ－２ ) and formula (L Ａｂ－２ In the formula, * indicates the bonding position to the nitrogen atom of X, and # indicates the bonding position to the nitrogen atom of L. Ｂ This is the bonding position with

[0179] L Ａａ Further specific examples of the formula (L Ａａ－２ -1) ~Formula (L Ａａ－２ -6), and L Ａｂ Further specific examples of the formula (L Ａｂ－２ -1) ~Formula (L Ａｂ－２ -22).

[0180]

[0181] Formula (L Ａａ－２ -1) ~Formula (L Ａａ－２ -6), formula (L Ａｂ－２ -1) ~Formula (L Ａｂ－２ -22) In the formula, each A is independently >O, >N-R ＮＡ , >C(-R ＣＡ ) ２ , >Si(-R ＩＡ ) ２ , >S, >Se, or >Te. Ｌ２ are each independently N or C-R ＡＬ２ It is. ＮＡ , R ＡＬ２ , R ＣＡ , and R ＩＡare each independently hydrogen, a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted silyl, a substituted germyl, a substituted or unsubstituted alkyl, or a substituted or unsubstituted cycloalkyl, and the substituents of the aryl and the heteroaryl are preferably alkyl, cycloalkyl, substituted silyl, or substituted germyl. ＣＡ ) ２ The two R's ＣＡ may be bonded to each other to form a ring, and >Si(-R ＩＡ ) ２ The two R's ＩＡ may be bonded to each other to form a ring. At least one hydrogen atom in the group represented by each of the above formulas may be substituted with an alkyl, cycloalkyl, substituted silyl, substituted germyl, aryl, or heteroaryl, and at least one hydrogen atom in the aryl and heteroaryl may be substituted with an alkyl, cycloalkyl, substituted silyl, or substituted germyl. In each of the above formulas, * represents the bonding position to the nitrogen atom represented by X, and # represents the bonding position to the nitrogen atom represented by L Ｂ This is the bonding position with

[0182] L Ａａ From the viewpoint of ease of production, the compound of the formula (L Ａａ－２ A group represented by L-1) is preferred. Ａｂ From the viewpoint of ease of production, the compound of the formula (L Ａｂ－２ -1), formula (L Ａｂ－２ -4), formula (L Ａｂ－２ -5), and formula (L Ａｂ－２ A group represented by any one of formulas (L-6) is preferred. Ａｂ－２ -4), formula (L Ａｂ－２ In formula (L-5), A is preferably >O. Ａｂ－２ -6), one A is >O and the other A is >C(-CH ３ ) ２ It is preferable that:

[0183] In each of the formulas (1-a) and (1-b), L Ｂ Preferred examples of the formula (L ｂ ) groups represented by the formula (I) are exemplified.

[0184] Formula (L ｂ ) Medium, X Ｌ are each independently a single bond, —O—, —S—, —Se—, —Te—, or —(N—R Ｌ ) -, -(P-R Ｌ )-,-(O=P-R Ｌ ) -, -(C(-R Ｌ ) ２ )-,-(C=O)-,-(Ge(-R Ｌ ) ２ )-,-(Sn(-R Ｌ ) ２ )-, -SO-, -SO ２ -, -(Si(-R Ｌ ) ２ )-,-(S=P-R Ｌ ) -, -(B-R Ｌ ) - or -(Bi-R Ｌ )-. Each R is independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted silyl, substituted germyl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, and the substituent of the aryl and heteroaryl is preferably alkyl, cycloalkyl, substituted silyl, or substituted germyl. -(C(-R Ｌ ) ２ )-,-(Ge(-R Ｌ ) ２ )-,-(Sn(-R Ｌ ) ２ ), and -(Si(-R Ｌ ) ２ )- each of the two R ＩＬ may be bonded to each other to form a ring.

[0185] Formula (L ｂ In the formula (I), each Ar is independently a substituted or unsubstituted alkylene having 2 to 12 carbon atoms, a substituted or unsubstituted arylene, or a substituted or unsubstituted heteroarylene, and at least one —CH ２ -CH ２- may be replaced by cycloalkylene or vinylene, and at least one hydrogen in the alkylene is independently replaced by R ＣＬ Examples of the substituent on each of the alkylene, arylene, and heteroarylene in Ar include a substituent selected from the substituent group Zα, as well as a substituted or unsubstituted alkynyl and azide, and a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted alkyl, a substituted or unsubstituted cycloalkyl, a halogen atom, a cyano atom, an acetylenyl atom, or an azide atom is preferred.

[0186] Formula (L ｂ ) More specific examples of Ar include the following formula (Ar Ｌｂ -1) to (Ar Ｌｂ -254).

[0187]

[0188]

[0189]

[0190]

[0191]

[0192] Formula (Ar Ｌｂ -1) to Formula (Ar Ｌｂ -254) Medium, A Ｌｂ are each independently >O, >S, >Se, >Te, >SO, >SO ２ , >C(-R ＣＹ ) ２ , >C=O, >Si(-R ＣＹ ) ２ , >Ge(-R ＣＹ ) ２ , or >Sn(-R ＣＹ ) ２ and R ＣＹare each independently hydrogen, a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted silyl, a substituted germyl, a substituted or unsubstituted alkyl, or a substituted or unsubstituted cycloalkyl, and the substituents of the aryl and the heteroaryl are preferably alkyl, cycloalkyl, substituted silyl, or substituted germyl. ＣY ) ２ , the above >Si(-R ＣＹ ) ２ , the above >Ge(-R ＣＹ ) ２ , and the above >Sn(-R ＣＹ ) ２ The two R's ＣY may be bonded to each other to form a ring, and two R CY may be bonded to each other to form a ring.

[0193] Formula (Ar Ｌｂ -1) to Formula (Ar Ｌｂ -254) # is X Ｌ１ Or the bonding position with other Ar or L in formula (1) (L in formula (1-a) Ａａ Or L in formula (1-b) Ａｂ ) is the bonding position with the formula (Ar Ｌｂ -1) to Formula (Ar Ｌｂ -254), at least one hydrogen atom may be substituted, and the preferred forms of substitution can be found in the description herein.

[0194] Formula (L ｂ ) In the #, L Ａａ or L Ａｂ This is the bonding position with

[0195] X Ｌ are each independently a single bond, —O—, —S—, or —(N—R Ｌ ) - or -(C(-R Ｌ ) ２ )-(R Ｌ Preferably, Ar is independently a substituted or unsubstituted alkylene having 2 to 10 carbon atoms, a substituted or unsubstituted phenylene, or a substituted or unsubstituted dibenzofuranylene.

[0196] Formula (L ｂ In the formula (I), j is an integer of 1 to 10, preferably 1 to 5.

[0197] Formula (L ｂ Preferred examples of the group represented by the formula include groups represented by any of the following formulae:

[0198]

[0199] In the above formula, Ar １ is the formula (L ｂ The meaning and preferred range of X are the same as those of Ar in X. Ｌ１ are each independently —O—, —S—, —Se—, —Te—, —(N—R Ｌ ) -, -(P-R Ｌ )-,-(O=P-R Ｌ ) -, -(C(-R Ｌ ) ２ )-,-(C=O)-,-(Ge(-R Ｌ ) ２ )-,-(Sn(-R Ｌ ) ２ )-, -SO-, -SO ２ -, -(Si(-R Ｌ ) ２ )-,-(S=P-R Ｌ ) -, -(B-R Ｌ ) - or -(Bi-R Ｌ )- and R Ｌ is the formula (L ｂ ) in R Ｌ The definition and preferred range are also the same. Ａａ or L Ａｂ This is the bonding position with

[0200] L Ｂ Another preferred example of the formula (L ｂ２ ) groups represented by the formula (I) are exemplified.

[0201] Formula (L ｂ２ ) Medium, X Ｌ and Ar each independently represent a group represented by the formula (L ｂ ) in Ｌ and Ar have the same meanings and preferred ranges as L. Ａａ or LＡｂ This is the bonding position with X Ｌ１ are each independently represented by the formula (L ｂ -1) in X Ｌ１ The formula (L ｂ２ ) in Ｌ１ are -O-, -S-, -(Si(-R Ｌ ) ２ ) -, -(N-R Ｌ ) -, -(C(-R Ｌ ) ２ ), or -(C=O)- is preferred. Each j2 is independently an integer of 0 to 5, preferably 1 or 2. j3 is an integer of 2 to 5, preferably 2 or 3. However, when all j2 are 0, j3 may be 1.

[0202] Formula (L ｂ２ ) is a more specific example of the following formula (L ｂ２ -1) ~Formula (L ｂ２ -4) is an example of the structure.

[0203] L Ｂ Yet another preferred example of the formula (L ｂ３ ) groups represented by the formula (I) are exemplified.

[0204] Formula (L ｂ３ ) Medium, X Ｌ and Ar each independently represent a group represented by the formula (L ｂ ) in Ｌ and Ar have the same meanings and preferred ranges as L. Ａａ or L Ａｂ Each j2 is independently an integer of 0 to 5, preferably 1 or 2. M ｃｏｍｐ Is > (M Ｔ ) n-(L ＭＴ ) m. Ｔ ) n-(L ＭＴ ) in m, M Ｔ are each independently a transition metal atom, and L ＭＴ are each independently M Ｔn is an integer of 1 to 3, more preferably 1 or 2, and still more preferably 1. m is an integer of 0 to 5, more preferably 0 to 2, more preferably 0 or 1, and most preferably 0.

[0205] >(M Ｔ ) n-(L ＭＴ ) M in m Ｔ may be in any oxidation state. Ｔ Examples of the metal include Co, Rh, Ir, Nb, Pd, Pt, Fe, Ru, Rh, Os, Cr, Mo, W, Mn, Tc, Re, Cu, Ag, and Au, preferably Ir, Pd, Pt, Ru, Os, Re, Cu, Ag, or Au, more preferably Ir, Pt, Cu, or Au, and even more preferably Ir, Pt, or Au. In terms of oxidation number, Ir(III), Pt(II), or Au(I) is preferred.

[0206] >(M Ｔ ) n-(L ＭＴ ) L in m ＭＴ is a ligand. The ligand is preferably a neutral ligand, a monoanionic ligand, or a dianionic ligand, and the ligand is preferably a monodentate ligand or a bidentate ligand.

[0207] Suitable monoanionic monodentate ligands include hydrides, deuterides, alkyl acetylides (e.g., methyl-C≡C-, tert-butyl-C≡C-), aryl acetylides (e.g., phenyl-C≡C-), cyanides, cyanates, isocyanates, thiocyanates, isothiocyanates, aliphatic or is selected from aromatic alkoxides (e.g., methoxide, ethoxide, propoxide, iso-propoxide, tert-butoxide, phenoxide), aliphatic or aromatic thioalkoxides (e.g., methanethiolate, ethanethiolate, propanethiolate, iso-propanethiolate, tert-thiobutoxide, thiophenoxide), amides (e.g., dimethylamide, diethylamide, di-iso-propylamide, morpholide), carboxylic acid esters (e.g., acetate, trifluoroacetate, propionate, benzoate), aryls (e.g., phenyl, naphthyl), and anionic heteroaryls (e.g., nitrogen-containing heterocycles such as pyrrolide, imidazolide, pyrazolide, etc.). Also, cyclopentadienyl (Cp-), transition metal M Ｔ and alkyl, e.g., methyl, a transition metal M Ｔ and alkylaryl, such as benzyl, bonded by a sigma bond.

[0208] Suitable neutral, monoanionic, or dianionic bidentate ligands include diamines (e.g., ethylenediamine, N,N,N',N'-tetramethylethylenediamine, propylenediamine, N,N,N',N'-tetramethylpropylenediamine, cis- or trans-diaminocyclohexane, cis- or trans-N,N,N',N'-tetramethyldiaminocyclohexane), imines (e.g., 2-[1-(furan-2-yl)-2-methyl-1,3-diamino-2,4-diamine, 2-[1-(furan-2-yl) ... 2-[1-(2-methylphenylimino)ethyl]pyridine, 2-[1-(2,6-di-iso-propylphenylimino)ethyl]pyridine, 2-[1-(methylimino)ethyl]pyridine, 2-[1-(ethylimino)ethyl]pyridine, 2-[1-(iso-propylimino)ethyl]pyridine, 2-[1-(tert-butylimino)ethyl]pyridine), diimines (e.g., 1,2-bis(methyl 1,2-bis(isopropylimino)ethane, 1,2-bis(tert-butylimino)ethane, 2,3-bis(methylimino)butane, 2,3-bis(ethylimino)butane, 2,3-bis(isopropylimino)butane, 2,3-bis(tert-butylimino)butane, 1,2-bis(phenylimino)ethane, 1,2-bis(2-methylphenylimino)ethane 1,2-bis(2,6-di-iso-propylphenylimino)ethane, 1,2-bis(2,6-di-tert-butylphenylimino)ethane, 2,3-bis(phenylimino)butane, 2,3-bis(2-methylphenylimino)butane, 2,3-bis(2,6-di-iso-propylphenylimino)butane, 2,3-bis(2,6-di-tert-butylphenylimino)butane), heterocycles containing two nitrogen atoms (e.g., 2,2-bipyridine, o-phenanthroline), diphosphines (e.g., bis(diphenylphosphino)methane, bis(diphenylphosphino)ethane, bis(diphenylphosphino)propane, bis(diphenylphosphino)butane, bis(dimethylphosphino)methane, bis(dimethylphosphino)ethane, bis(dimethylphosphino)propane, bis(diethylphosphino)methane, bis(diethylphosphino)ethane, bis(diethylphosphino)propane, bis(di-tert-butylphosphino)methane, bis(di-tert-butylphosphino)ethane, bis(tert-butylphosphino)propane), 1,3-diketonates derived from 1,3-diketones (e.g., acetylacetone, benzoylacetone, 1,5-diphenylacetylacetone, dibenzoylmethane, biphenylsulfonyl ethers, bis(1,1,1-trifluoroacetyl)methane, 2,2,6,6-tetramethyl-3,5-heptanedione), 3-ketonates derived from 3-ketoesters (e.g., ethyl acetoacetate), carboxylic acid esters derived from aminocarboxylic acids (e.g., pyridine-2-carboxylic acid, quinoline-2-carboxylic acid), glycine, N,N-dimethylglycine, alanine, N,N-dimethylaminoalanine, salicyliminates derived from salicylimines (e.g., methyl salicylimine, ethyl salicylimine, phenyl salicylimine), dialkoxides derived from dialcohols (e.g., ethylene glycol, 1,3-propylene glycol), and dithiolates derived from dithiols (e.g., 1,2-ethylenedithiol-1,3-propylenedithiol).

[0209] Preferred neutral monodentate ligands are in particular carbon monoxide, nitric oxide, alkyl cyanides (e.g., acetonitrile), aryl cyanides (e.g., benzonitrile), alkyl isocyanides (e.g., methyl isonitrile), aryl isocyanides (e.g., benzoisonitrile), amines (e.g., trimethylamine, triethylamine, morpholine), phosphines, in particular halophosphines, trialkylphosphines, triarylphosphines or alkylarylphosphines (e.g., trifluorophosphine, trimethylphosphine, tricyclohexylphosphine, tri-tert-butylphosphine, triphenylphosphine, tris(pentafluorophenyl)phosphine, sphines), phosphites (e.g., trimethyl phosphite, triethyl phosphite), arsines (e.g., trifluoroarsine, trimethylarsine, tricyclohexylarsine, tri-tert-butylarsine, triphenylarsine, tris(pentafluorophenyl)arsine), stibines (e.g., trifluorostibine, trimethylstibine, tricyclohexylstibine, tri-tert-butylstibine, triphenylstibine, tris(pentafluorophenyl)stibine), nitrogen-containing heterocycles (e.g., pyridine, pyridazine, pyrazine, pyrimidine, triazine), and carbenes, particularly Arduengo carbene.

[0210] Neutral monodentate or bidentate ligands that may also be mentioned are ligands based on dienes, preferably 1,4-diphenyl-1,3-butadiene, 1-phenyl-1,3-pentadiene, 2,4-hexadiene, η4-cyclooctadiene and η2-cyclooctadiene (1,3 and 1,5 respectively).

[0211] Also L ＭＴ The ligand may be an orthometalated ligand which coordinates one carbon atom and one nitrogen or oxygen atom, and preferred examples include the following:

[0212] In the above formula, M Ｔ and each Y is independently BR ｅ , N.R. ｅ , P.R.ｅ , O, S, Se, C=O, S=O, SO ２ , C.R. ｅ R ｆ , SiR ｅ R ｆ , or GeR ｅ R ｆ and each aromatic carbon C—H in the ring may be independently substituted with N; R ｅ and R ｆ may be optionally fused or linked to form a ring, R ａ , R ｂ , R ｃ , and R ｄ R may be independently unsubstituted or substituted with 1 to the maximum number of possible substitutions. ａ , R ｂ , R ｃ , R ｄ , R ｅ , and R ｆ are each independently hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, or a combination thereof, with the proviso that R ａ , R ｂ , R ｃ , and R ｄ Any two adjacent substituents in may be fused or linked to form a ring or to form a multidentate ligand.

[0213] Also, structures corresponding to ligands, particularly orthometalated ligands as described above, are represented by the formula M ｃｏｍｐ It may be incorporated as

[0214] Preferred examples of the linking group represented by formula (1-a) or formula (1-b) include the following.

[0215]

[0216] <Preferred structural examples> Preferred structural examples of the polycyclic aromatic compound represented by formula (1) include structures represented by any of the following formulas. In each of the following formulas, XＬ is the formula (L ｂ ) in X Ｌ A has the same meaning as the formula (L Ａａ－２ -1) ~Formula (L Ａａ－２ -4), formula (L Ａｂ－２ -1) ~Formula (L Ａｂ－２ -9) has the same meaning as A, and the preferred range is also the same. n is an integer of 0 to 10. In addition, at least one hydrogen atom of the group represented by each of the following formulas may be replaced by a substituent.

[0217]

[0218] <Preferred Substituents> In polycyclic aromatic compounds represented by formula (1) used as emitting dopants (and in other compounds used as dopants), a tertiary alkyl represented by formula (tR) (a monovalent group represented by formula (tR)) is particularly preferred as an "alkyl"-containing substituent. This is because such a bulky substituent increases the intermolecular distance, thereby improving the luminescence quantum yield (PLQY). Also preferred are substituents in which the tertiary alkyl represented by formula (tR) is substituted with another substituent as a second substituent. Specific examples include diarylamino substituted with a tertiary alkyl represented by formula (tR), carbazolyl (preferably N-carbazolyl) substituted with a tertiary alkyl represented by formula (tR), or benzocarbazolyl (preferably N-benzocarbazolyl) substituted with a tertiary alkyl represented by formula (tR). Substitution of the group of formula (tR) on diarylamino, carbazolyl and benzocarbazolyl includes examples in which some or all of the hydrogen atoms on the aryl ring or benzene ring in these groups are replaced with the group of formula (tR).

[0219]

[0220] In the formula (tR), R ａ , R ｂ , and R ｃ are each independently alkyl having 1 to 24 carbon atoms. ａ , R ｂ , and R ｃIn each of the alkyl groups having 1 to 24 carbon atoms, one or two or more non-adjacent —CH ２ - and terminal CH ３ Not inside - CH ２ It may be a group in which - is replaced by -O-. In the group represented by formula (tR), * is the bonding position.

[0221] R ａ , R ｂ and R ｃ The "alkyl having 1 to 24 carbon atoms" may be either a straight chain or a branched chain, and examples thereof include a straight chain alkyl having 1 to 24 carbon atoms or a branched chain alkyl having 3 to 24 carbon atoms, an alkyl having 1 to 18 carbon atoms (branched chain alkyl having 3 to 18 carbon atoms), an alkyl having 1 to 12 carbon atoms (branched chain alkyl having 3 to 12 carbon atoms), an alkyl having 1 to 6 carbon atoms (branched chain alkyl having 3 to 6 carbon atoms), and an alkyl having 1 to 4 carbon atoms (branched chain alkyl having 3 to 4 carbon atoms).

[0222] R in formula (tR) ａ , R ｂ , and R ｃ The total number of carbon atoms in the group is preferably 3 to 20, and particularly preferably 3 to 10.

[0223] R ａ , R ｂ , and R ｃ Specific examples of alkyl include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl, n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, t-octyl, 1-methylheptyl, 2 1-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 2,6-dimethyl-4-heptyl, 3,5,5-trimethylhexyl, n-decyl, n-undecyl, 1-methyldecyl, n-dodecyl, n-tridecyl, 1-hexylheptyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, and n-eicosyl.

[0224] Examples of the group represented by formula (tR) include t-butyl, t-amyl, 1-ethyl-1-methylpropyl, 1,1-diethylpropyl, 1,1-dimethylbutyl, 1-ethyl-1-methylbutyl, 1,1,3,3-tetramethylbutyl, 1,1,4-trimethylpentyl, 1,1,2-trimethylpropyl, 1,1-dimethyloctyl, 1,1-dimethylpentyl, 1,1-dimethylheptyl, 1,1,5-trimethylhexyl, 1-ethyl- Examples include 1-methylhexyl, 1-ethyl-1,3-dimethylbutyl, 1,1,2,2-tetramethylpropyl, 1-butyl-1-methylpentyl, 1,1-diethylbutyl, 1-ethyl-1-methylpentyl, 1,1,3-trimethylbutyl, 1-propyl-1-methylpentyl, 1,1,2-trimethylpropyl, 1-ethyl-1,2,2-trimethylpropyl, 1-propyl-1-methylbutyl, 1,1-dimethylhexyl, etc. Of these, t-butyl and t-amyl are preferred.

[0225] The substituent is also preferably a substituent represented by formula (A30).

[0226] The emission wavelength can be adjusted by the steric hindrance, electron donating property, and electron withdrawing property of the structure of the substituent possessed by the compound used as a dopant (assisting dopant or emitting dopant). Preferred are groups represented by the following structural formulas, and more preferred are methyl, t-butyl, t-amyl, t-octyl, neopentyl, adamantyl, phenyl, o-tolyl, p-tolyl, 2,4-xylyl, 2,5-xylyl, 2,6-xylyl, 2,4,6-mesityl, diphenylamino, di-p-tolylamino, bis(p-(t-butyl)phenyl)amino, carbazolyl, 3,6-dimethylcarbazolyl, and 3,6-di-t-butyl. Preferred are methyl, t-butyl, t-amyl, t-octyl, neopentyl, adamantyl, phenyl, o-tolyl, 2,6-xylyl, 2,4,6-mesityl, diphenylamino, di-p-tolylamino, bis(p-(t-butyl)phenyl)amino, carbazolyl, 3,6-dimethylcarbazolyl, 3,6-di-t-butylcarbazolyl, and tribenzazepinyl. From the viewpoint of ease of synthesis, larger steric hindrance is preferred for selective synthesis, and specifically, t-butyl, t-amyl, t-octyl, adamantyl, o-tolyl, p-tolyl, 2,4-xylyl, 2,5-xylyl, 2,6-xylyl, 2,4,6-mesityl, di-p-tolylamino, bis(p-(t-butyl)phenyl)amino, 3,6-dimethylcarbazolyl, and 3,6-di-t-butylcarbazolyl are preferred.

[0227] In the following structural formula, * represents a bond position.

[0228]

[0229]

[0230]

[0231]

[0232]

[0233]

[0234]

[0235]

[0236]

[0237]

[0238]

[0239]

[0240]

[0241] The polycyclic aromatic compound represented by formula (1) preferably has a structure containing at least one tertiary alkyl (such as t-butyl or t-amyl), neopentyl, or adamantyl group represented by the above-mentioned formula (tR), and preferably contains a tertiary alkyl (such as t-butyl or t-amyl) represented by formula (tR). This is because such bulky substituents increase the intermolecular distance, thereby improving the luminescence quantum yield (PLQY). Diarylamino is also preferred as the substituent. Furthermore, diarylamino substituted with a group represented by formula (tR), carbazolyl (preferably N-carbazolyl) substituted with a group represented by formula (tR), or benzocarbazolyl (preferably N-benzocarbazolyl) substituted with a group represented by formula (tR) are also preferred. Examples of the substitution of a group represented by formula (tR) on diarylamino, carbazolyl, and benzocarbazolyl include those in which some or all of the hydrogen atoms on the aryl ring or benzene ring in these groups are substituted with a group represented by formula (tR).

[0242] In the structure consisting of one or more structural units represented by formula (1), the substituent on the aryl ring or heteroaryl ring may be a substituent represented by the following formula (A20).

[0243] The substituent represented by formula (A20) is bonded to two adjacent atoms on the aryl or heteroaryl ring at two *'s. In formula (A20), L represents >N-R, >O, >Si(-R) ２or >S, wherein R of the >N-R is a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted alkyl, or a substituted or unsubstituted cycloalkyl, and the >Si(-R) ２ R is hydrogen, an optionally substituted aryl, an optionally substituted alkyl, or an optionally substituted cycloalkyl, and may be bonded to each other by a linking group, and the >N-R and >Si(-R) ２ At least one of R may be bonded to the aryl ring or heteroaryl ring via a linking group or a single bond, r is an integer of 1 to 4, and R Ａ are each independently hydrogen, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, and any R Ａ is any other R Ａ and may be bonded to each other via a linking group or a single bond.

[0244] Examples of the above substituent include any of the following substituents.

[0245] In each formula, * may be bonded to two or three consecutive (adjacent) atoms on any aryl or heteroaryl ring.

[0246] <Cycloalkane Condensation> At least one selected from the group consisting of aryl rings and heteroaryl rings in the polycyclic aromatic compound represented by formula (1) may be condensed with at least one cycloalkane.

[0247] The cycloalkane may be a cycloalkane having 3 to 24 carbon atoms. In this case, at least one hydrogen atom in the cycloalkane may be substituted with an aryl having 6 to 30 carbon atoms, a heteroaryl having 2 to 30 carbon atoms, an alkyl having 1 to 24 carbon atoms, or a cycloalkyl having 3 to 24 carbon atoms, and at least one —CH ２ - may be replaced by -O-.

[0248] The cycloalkane is preferably a cycloalkane having 3 to 20 carbon atoms, in which at least one hydrogen atom may be substituted with an aryl having 6 to 16 carbon atoms, a heteroaryl having 2 to 22 carbon atoms, an alkyl having 1 to 12 carbon atoms, or a cycloalkyl having 3 to 16 carbon atoms.

[0249] 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, and cycloalkanes having 5 carbon atoms.

[0250] 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, and decahydroazulene, as well as alkyl (particularly methyl)-substituted, halogen (particularly fluorine)-substituted, and deuterium-substituted derivatives of these compounds having 1 to 5 carbon atoms.

[0251] Among the above examples, for example, as shown in the structural formula below, a structure having at least one substituent on the α-carbon of the cycloalkane (in a cycloalkane fused to an aryl ring or heteroaryl ring, the carbon adjacent to the carbon at the condensation site) is preferred, a structure having two substituents on the α-carbon is more preferred, and a structure having two substituents on each of the two α-carbons (four substituents in total) is even more preferred. Examples of such substituents include alkyl (particularly methyl) having 1 to 5 carbon atoms, halogen (particularly fluorine), and deuterium. In particular, a structure in which a partial structure represented by formula (B11) or (B12) below is bonded to adjacent carbon atoms in an aryl ring or heteroaryl ring is preferred, and a structure in which a partial structure represented by formula (B11) below is bonded is more preferred. For the same reason, a structure in which a partial structure represented by formula (B13) below is bonded, in which adjacent carbon atoms in an aryl ring or heteroaryl ring are substituted with oxygen atoms, is also preferred.

[0252] In each of formulas (B11), (B12) and (B13), * indicates a bonding position.

[0253] The number of cycloalkanes fused to one aryl ring or heteroaryl ring is preferably 1 to 3, more preferably 1 or 2, and even more preferably 1. For example, an example in which one or more cycloalkanes are fused to one benzene ring (phenyl) is shown below. * indicates the bonding position, and the position may be any carbon that constitutes the benzene ring but not the cycloalkane. Cycloalkanes fused as in formula (Cy-1-4) and formula (Cy-2-4) may also be fused together. The same applies when the fused ring (group) is an aryl ring or heteroaryl ring other than a benzene ring (phenyl), or when the fused cycloalkane is a cycloalkane other than cyclopentane or cyclohexane.

[0254]

[0255] At least one —CH in the cycloalkane ２- may be substituted with -O-. For example, one or more -CH in a cycloalkane fused to one benzene ring (phenyl) ２ Examples in which - is replaced by -O- are shown below. The same applies even when the fused ring (group) is an aryl ring or heteroaryl ring other than a benzene ring (phenyl), or when the fused cycloalkane is a cycloalkane other than cyclopentane or cyclohexane.

[0256]

[0257] The cycloalkane may be substituted with at least one substituent, and this substituent may be any substituent selected from the substituent group Z. Among these substituents, alkyl (e.g., alkyl having 1 to 6 carbon atoms) and cycloalkyl (e.g., cycloalkyl having 3 to 14 carbon atoms) are preferred. It is also preferred that any hydrogen atom is replaced with a halogen (e.g., fluorine) or deuterium. When substituted with cycloalkyl, the substitution may be in a form that forms a spiro structure. For example, an example in which a spiro structure is formed in a cycloalkane fused to one benzene ring (phenyl) is shown below. In each structural formula, * means a benzene ring included in the skeletal structure of the compound when it is a benzene ring, and means a bond substituting the skeletal structure of the compound when it is a phenyl.

[0258]

[0259] The cycloalkane may have a bridged structure. When the cycloalkane has a bridged structure, at least one ethylene structure (—CH ２ -CH ２ -) may be an ethene structure (-CH=CH-). In addition, when the cycloalkane has a bridged structure, it may be further condensed with an aryl ring or a heteroaryl ring. Specific examples are shown below.

[0260] In each of formulae (C11) to (C21), * indicates the bonding position to the adjacent carbon atom in the aryl ring or heteroaryl ring.

[0261] Examples of the cycloalkane condensation include a form in which an aryl ring or a heteroaryl ring in either the A ring or the B ring in the polycyclic aromatic compound represented by formula (1) is condensed with a cycloalkane, a form in which an aryl ring or a heteroaryl ring in the linking group represented by formula (1-a) or formula (1-b) is condensed with a cycloalkane, and a form in which X is >N-R ＮＸ R ＮＸ and a form in which an aryl ring or heteroaryl ring in the above-mentioned group is fused with a cycloalkane when any of the other substituents is a group containing an aryl ring or heteroaryl ring, and a form in which an aryl ring or heteroaryl ring in the above-mentioned group is fused with a cycloalkane.

[0262] Furthermore, by introducing a cycloalkane structure into the polycyclic aromatic compound represented by formula (1), further reductions in melting point and sublimation temperature can be expected. This means that sublimation purification, which is almost essential as a method for purifying materials for organic devices such as organic EL elements that require high purity, can be performed at relatively low temperatures, thereby avoiding thermal decomposition of the materials. This also applies to the vacuum deposition process, which is an effective means for producing organic devices such as organic EL elements. Since the process can be performed at relatively low temperatures, thermal decomposition of the materials can be avoided, resulting in high-performance organic devices. Furthermore, the introduction of a cycloalkane structure improves solubility in organic solvents, making it possible to apply this to element production using a coating process. However, the present invention is not particularly limited to these principles.

[0263] <Replacement with heavy stable isotopes> Unless otherwise specified, each element in the polycyclic aromatic compound represented by formula (1) contains multiple naturally occurring isotopes in their natural abundance ratios. However, all or some of the elements in each structural formula may be present in amounts exceeding their natural abundance ratios (for example, boron-11 ( １１ B) may contain a heavy stable isotope (at 90 atom % or more). In this specification, this is simply referred to as "substituting" a "heavy stable isotope". More specifically, at least one hydrogen can be substituted with deuterium, and at least one nitrogen can be substituted with nitrogen-15 (１５ N), and at least one sulfur can be replaced by sulfur-33 ( ３３ S), sulfur-34 ( ３４ S) or sulfur-36 ( ３６ S), and at least one oxygen can be replaced by oxygen-17 ( １７ O) or oxygen-18 ( １８ O), and at least one carbon can be replaced by carbon-13 ( １３ C), and at least one boron can be replaced by boron-11 ( １１ B). By replacing at least some elements with heavy stable isotopes, in particular at least one boron can be replaced with boron-11 ( １１ By replacing the polycyclic aromatic compound represented by formula (1) with B), the life of the organic electroluminescent device using the polycyclic aromatic compound represented by formula (1) can be extended.

[0264] <Replacement with Deuterium> All or a part of the hydrogen in the polycyclic aromatic compound represented by formula (1) may be deuterium. From the viewpoint of the life and high efficiency of the device, particularly the life of the device, it is more preferable that the hydrogen in the polycyclic aromatic compound is replaced with deuterium.

[0265] For example, any hydrogen atom in the ring A or ring B of the polycyclic aromatic compound represented by formula (1), any hydrogen atom in the linking group represented by formula (1-a) or formula (1-b), or X is >N-R ＮＸ R ＮＸ In the polycyclic aromatic compound represented by formula (1), hydrogen atoms can be replaced with deuterium atoms, and among these, hydrogen atoms in the aryl and heteroaryl groups can be replaced with deuterium atoms. From the viewpoint of durability, it is also preferable that all or some of the hydrogen atoms in the polycyclic aromatic compound represented by formula (1) are deuterated. In particular, it is also preferable that all or some of the hydrogen atoms at the benzyl positions in the polycyclic aromatic compound represented by formula (1) are deuterated.

[0266] <Specific Examples of Polycyclic Aromatic Compounds> Specific examples of the polycyclic aromatic compounds represented by formula (1) include any of the following compounds: However, the polycyclic aromatic compounds represented by formula (1) are not limited to the following specific examples.

[0267]

[0268]

[0269]

[0270]

[0271]

[0272]

[0273]

[0274]

[0275]

[0276]

[0277]

[0278]

[0279]

[0280]

[0281]

[0282]

[0283]

[0284]

[0285]

[0286]

[0287] <Method for producing polycyclic aromatic compound> [Production method via intermediate 1 or intermediate 2] The polycyclic aromatic compound represented by formula (1) is basically produced by forming a precursor structure for introducing a hoop structure, such as intermediate 1 or intermediate 2 shown below, using a method described in a known document such as WO 2015 / 102118, and then introducing the hoop structure.

[0288]

[0289] In Intermediate 1 and Intermediate 2, P Ｘ are each independently a reactive group. The reactive group may be a halogen, a pseudohalogen, or -SiX ３ , -Si(OR) ３ or a reactive group capable of electrophilic substitution, such as boronic acid, boronic acid ester, -ZnX, -Sn(R) ３ , -MgX, or -SH, -OH, -NH ２ A nucleophilic reactive group such as —NRH can be used, where X is a halogen and R is an alkyl.

[0290] Intermediate 1 and Intermediate 2 are each provided with L Ｂ By reacting the bifunctional intermediate 3, which is a precursor of the structure, a polycyclic aromatic compound having a hoop structure represented by formula (1) can be synthesized. Ｙ are each independently a reactive group, and the reactive group P Ｘ The bond between the intermediate 1 or intermediate 2 and the intermediate 3 can be formed by a reaction group (P Ｘ and P Ｙ The reaction can be carried out by appropriately setting the reaction conditions etc. depending on the properties of the intermediate 1. Basically, when intermediate 1 is used, 1 equivalent of intermediate 3 is used, and when intermediate 2 is used, 2 equivalents of intermediate 3 are used. ＢWhen synthesizing compounds in which the P of the intermediate 2 is different from the P of the intermediate 2, the compounds can be synthesized by introducing two kinds of the intermediate 3 stepwise. Ｘ By making each of the reactants different, the reactivity of the reaction in the two steps can be appropriately adjusted to improve the selectivity of the reaction.

[0291]

[0292] [Production method via intermediate 3 or intermediate 4] Ａａ , and L Ｂ The reactive group P Ｘ can be reacted by a commonly known homocoupling reaction to synthesize the polycyclic aromatic compound represented by formula (1). The homocoupling reaction may be an oxidation reaction, a reduction reaction, or a radical reaction.

[0293] [Production Method via Intermediate 5 or Intermediate 6] Furthermore, by carrying out a ring-closing metathesis (RCM) reaction using Intermediate 5 or Intermediate 6, polycyclic aromatic compounds containing an alkenylene structure and represented by the following formula (1'-1) and formula (1'-2) can be synthesized. In Intermediate 5, Intermediate 6, Formula (1'-1), and Formula (1'-2), L Ｂｘ A specific example of the form is L Ｂ Reference can be made to the description herein regarding R Ｘ is hydrogen or a substituent.

[0294]

[0295] The ring-closing metathesis reaction can be carried out by appropriately using a commonly known catalyst (such as a Schrock catalyst, a Grubbs catalyst, or a Hoveyda-Grubbs catalyst).

[0296] The polycyclic aromatic compound represented by formula (1) can be synthesized by further reacting the alkenylene structure moiety using the following formulas (1'-1) and (1'-2). In this case, a commonly known reaction capable of returning the alkenylene (double bond), such as a hydrogenation reaction, a cyclization reaction (epoxidation reaction, aziridination reaction, cyclopropanation reaction, cyclobutanation reaction, Diels-Alder reaction, etc.), or an addition reaction (radical reaction, addition reaction of an organometallic compound), can be appropriately used.

[0297] Examples of metalation reagents used in the halogen-metal exchange reaction in the schemes explained so far include alkyllithiums such as methyllithium, n-butyllithium, sec-butyllithium, and t-butyllithium; isopropylmagnesium chloride, isopropylmagnesium bromide, phenylmagnesium chloride, phenylmagnesium bromide; and lithium chloride complexes of isopropylmagnesium chloride, known as turboGrignard reagents.

[0298] Furthermore, examples of the metalation reagent used in the ortho-metal exchange reaction in the schemes described so far include, in addition to the above-mentioned reagents, organic alkali compounds such as lithium diisopropylamide, lithium tetramethylpiperidide, lithium hexamethyldisilazide, potassium hexamethyldisilazide, lithium chloride tetramethylpiperidinylmagnesium-lithium chloride complex, and lithium tri-n-butylmagnesium oxide.

[0299] Furthermore, when alkyllithium is used as the metallation reagent, examples of additives that promote the reaction include N,N,N',N'-tetramethylethylenediamine, 1,4-diazabicyclo[2.2.2]octane, and N,N-dimethylpropyleneurea.

[0300] The Lewis acid used in the schemes described above is AlCl ３ , AlBr ３ , AlF ３ , B.F. ３ ・OEt ２ , BCl ３ , BBr３ , B.I. ３ , GaCl ３ , GaBr ３ , InCl ３ , InBr ３ , In(OTf) ３ , SnCl ４ , SnBr ４ , AgOTf, ScCl ３ , Sc(OTf) ３ , ZnCl ２ , ZnBr ２ , Zn(OTf) ２ , MgCl ２ , MgBr ２ , Mg(OTf) ２ , LiOTf, NaOTf, KOTf, Me ３ SiOTf, Cu(OTf) ２ , CuCl ２ , YCl ３ , Y(OTf) ３ , TiCl ４ , TiBr ４ , ZrCl ４ , ZrBr ４ , FeCl ３ , FeBr ３ , CoCl ３ , CoBr ３ In addition, these Lewis acids supported on a solid can also be used.

[0301] Examples of Bronsted acids that can be used in the schemes described above include p-toluenesulfonic acid, methanesulfonic acid, trifluoromethanesulfonic acid, fluorosulfonic acid, carborane acid, trifluoroacetic acid, (trifluoromethanesulfonyl)imide, tris(trifluoromethanesulfonyl)methane, hydrogen chloride, hydrogen bromide, and hydrogen fluoride. Examples of solid Bronsted acids include Amberlyst (trade name: Dow Chemical), Nafion (trade name: DuPont), zeolite, and Teikacure (trade name: Teika Corporation).

[0302] Furthermore, examples of amines that may be added in the schemes described above include diisopropylethylamine, triethylamine, tributylamine, 1,4-diazabicyclo[2.2.2]octane, N,N-dimethyl-p-toluidine, N,N-dimethylaniline, pyridine, 2,6-lutidine, and 2,6-di-t-butylamine.

[0303] In addition, examples of solvents used in the schemes described so far include o-dichlorobenzene, chlorobenzene, toluene, benzene, methylene chloride, chloroform, dichloroethylene, benzotrifluoride, decalin, cyclohexane, hexane, heptane, 1,2,4-trimethylbenzene, xylene, diphenyl ether, anisole, cyclopentyl methyl ether, tetrahydrofuran, dioxane, and methyl t-butyl ether.

[0304] In the above scheme, a Brønsted base or Lewis acid may be used to promote the tandem hetero-Friedel-Crafts reaction. However, when using boron halides such as boron trifluoride, boron trichloride, boron tribromide, or boron triiodide, acids such as hydrogen fluoride, hydrogen chloride, hydrogen bromide, and hydrogen iodide are generated as the aromatic electrophilic substitution reaction proceeds, so the use of a Brønsted base to capture the acid is effective. On the other hand, when using boron aminated halides or boron alkoxides, amines and alcohols are generated as the aromatic electrophilic substitution reaction proceeds, so the use of a Brønsted base is often unnecessary, but because the amino and alkoxy groups have low elimination ability, the use of a Lewis acid to promote their elimination is effective.

[0305] The polycyclic aromatic compounds of the present invention also include compounds in which at least some of the hydrogen atoms have been replaced with deuterium atoms or compounds in which the hydrogen atoms have been replaced with various substituents. Such compounds can be synthesized in the same manner as described above by using raw materials in which the desired positions have been deuterated or derivatized.

[0306] 2. Organic Devices The polycyclic aromatic compound of the present invention can be used as a material for organic devices, such as organic electroluminescent devices, organic field-effect transistors, and organic thin-film solar cells.

[0307] The polycyclic aromatic compound according to the present invention can be used as a material for an organic device. Examples of the organic device include an organic electroluminescent element, an organic field-effect transistor, and an organic thin-film solar cell, and the like, but the organic electroluminescent element is preferred. The polycyclic aromatic compound according to the present invention is preferably a material for an organic electroluminescent element, more preferably a material for an emitting layer (light-emitting material), and most preferably a dopant material for the emitting layer.

[0308] <2-1. Organic Electroluminescent Device> <2-1-1. Structure of Organic Electroluminescent Device> Fig. 1 is a schematic cross-sectional view showing an example of an organic EL device. The organic EL device 100 shown in Fig. 1 has 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.

[0309] The organic EL element 100 may be fabricated in the reverse order, for example, to have a substrate 101, a cathode 108 provided on the substrate 101, an electron injection layer 107 provided on the cathode 108, an electron transport layer 106 provided on the electron injection layer 107, an emitting layer 105 provided on the electron transport layer 106, a hole transport layer 104 provided on the 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.

[0310] Not all of the above layers are essential, and the minimum structural unit is 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 may be optionally provided. Each of the above layers may consist of a single layer or multiple layers.

[0311] The layers constituting the organic EL element may be configured as follows: "substrate / anode / hole injection layer / hole transport layer / light-emitting layer / electron transport layer / electron injection layer / cathode" as described above, or "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 injection layer / cathode", or "substrate / anode / hole injection layer / hole transport layer / light-emitting layer / electron injection layer / cathode". The configuration may be any of the following: "substrate / anode / light-emitting layer / electron transport layer / electron injection layer / cathode", "substrate / anode / hole transport layer / light-emitting ... 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 transport layer / cathode", or "substrate / anode / light-emitting layer / electron injection layer / cathode".

[0312] <2-1-2. Light-Emitting Layer in Organic Electroluminescent Device> The polycyclic aromatic compound of the present invention is preferably used as a material for forming one or more organic layers in an organic electroluminescent device, and more preferably as a material for forming a light-emitting layer. The light-emitting layer 105 is a layer that emits light by recombining holes injected from the anode 102 and electrons injected from the cathode 108 between electrodes to which an electric field is applied. The material for the light-emitting layer 105 may be any compound that is excited and emits light by the recombination of holes and electrons (light-emitting compound), and is preferably a compound that can be formed into a stable thin film and exhibits strong luminescence (fluorescence) efficiency in a solid state.

[0313] The light-emitting layer may be a single layer or multiple layers, each formed from materials for the light-emitting layer (host material, dopant material). The host material and the dopant material may each be one type or a combination of multiple types. The dopant material may be contained entirely or partially in the host material. As a doping method, the dopant material can be formed by co-evaporation with the host material, or it may be mixed with the host material in advance and then vapor-deposited simultaneously.

[0314] The amount of the host material used varies depending on the type of host material and may be determined according to the properties of the host material. The amount of the host material used is preferably 50 to 99.999% by mass, more preferably 80 to 99.95% by mass, and even more preferably 90 to 99.9% by mass, of the total mass of the materials for the light-emitting layer. When the host material is a combination of a hole-transporting host material and an electron-transporting host material, the amount of the host material used is the combined mass of the hole-transporting host material and the electron-transporting host material. The ratio of the amount of the hole-transporting host material to the amount of the electron-transporting host material used may be 1:9 to 9:1 by mass, preferably 4:6 to 6:4, and more preferably approximately 1:1.

[0315] The amount of dopant material used varies depending on the type of dopant material and may be determined according to the properties of the dopant material. The amount of dopant material used is preferably 0.001 to 50% by mass, more preferably 0.05 to 20% by mass, and even more preferably 0.1 to 10% by mass, of the total mass of the materials for the light-emitting layer. The above range is preferable in that, for example, concentration quenching can be prevented.

[0316] The dopant material may be a combination of an emitting dopant and an assisting dopant material. As the assisting dopant material, either a thermally activated delayed fluorescent material or a phosphorescent material can be preferably used.

[0317] When an assisting dopant material is used, the amounts of the host material, the assisting dopant material, and the emitting dopant material to be used are approximately 40 to 99% by mass, 59 to 1% by mass, and 20 to 0.001% by mass, respectively, based on the total mass of the materials for the light-emitting layer.

[0318] The polycyclic aromatic compound of the present invention is more preferably used as a material for forming an emitting layer, and more preferably used as a dopant. The polycyclic aromatic compound containing the structural unit represented by formula (1) can be used as an emitting dopant in a TTF device that utilizes the phenomenon of generation of a singlet exciton from multiple triplet excitons (triplet-triplet fusion (TTF)).

[0319] Furthermore, the polycyclic aromatic compound of the present invention may be used as an emitting dopant in an organic EL device (hereinafter, sometimes referred to as a "TADF device") that exhibits thermally activated delayed fluorescence (TADF) as a "thermally activated delayed fluorescent material." In a "thermally activated delayed fluorescent material," by reducing the energy difference between the lowest excited singlet state and the lowest excited triplet state, reverse intersystem crossing transfer from the lowest excited triplet state, which usually has a low transition probability, to the lowest excited singlet state occurs with high efficiency, resulting in emission from the singlet state (thermally activated delayed fluorescence, TADF). In normal fluorescent emission, 75% of triplet excitons generated by current excitation pass through a thermal deactivation pathway and cannot be extracted as fluorescence. On the other hand, in TADF, all excitons can be used for fluorescent emission, thereby realizing a highly efficient organic EL device.

[0320] The polycyclic aromatic compound of the present invention can be used as an emitting dopant for a "TADF element", an emitting dopant for an organic electroluminescent element (TAF element) using another thermally activated delayed fluorescent substance as an assisting dopant, or an emitting dopant for an organic electroluminescent element (PSF element) using a phosphorescent material as an assisting dopant. From the viewpoint that the fewer materials used in the element, the easier it is to manufacture, it is preferable to use it as an emitting dopant for a TADF element, and the former is more preferable. From the viewpoint of efficiency, it is preferable to use it as an emitting dopant for a TAF element and an emitting dopant for a PSF element, and it is more preferable to use it as an emitting dopant for a TAF element.

[0321] In general, a material with a faster delayed fluorescence lifetime is considered to have better TADF properties. Specifically, when a light-emitting material with a delayed fluorescence lifetime of 20 μsec or less is used as an emitting dopant in a light-emitting device, it can provide high device efficiency and a long device lifetime.

[0322] Generally, ΔE Ｓ１Ｔ１ The smaller the value of ΔE, the better the TADF property. Ｓ１Ｔ１ is the lowest excited singlet energy level (E Ｓ１ ) and the lowest excited triplet energy level (E Ｔ１ ) is the energy difference between

[0323] <Host Material> Examples of host materials include fused ring derivatives of anthracene, pyrene, and the like, which have long been known as light emitters; bisstyryl derivatives such as bisstyrylanthracene derivatives and distyrylbenzene derivatives; tetraphenylbutadiene derivatives; cyclopentadiene derivatives; fluorene derivatives; benzofluorene derivatives; N-phenylcarbazole derivatives; carbazonitrile derivatives; and dibenzochrysene derivatives. Other examples include compounds represented by formulas (H1), (H2), and (H3), hole-transporting host materials (HH), and electron-transporting host materials (EH). From the viewpoint of durability, it is also preferable that some or all of the hydrogen atoms in the host material are deuterated. Furthermore, it is also preferable to form an emitting layer by combining a host compound in which some or all of the hydrogen atoms are deuterated with a dopant compound in which some or all of the hydrogen atoms are deuterated.

[0324] The lowest excited triplet energy level (E Ｔ１ ) is the highest E in the light-emitting layer from the viewpoint of promoting the generation of TADF without inhibiting it in the light-emitting layer. Ｔ１ E of a dopant or assisting dopant having Ｔ１ It is preferable that the TADF activity is higher than the host material.

[0325] The host material may be one kind or a combination of two or more kinds. In the case of a combination of two or more kinds, a combination of a hole-transporting host material and an electron-transporting host material is preferred.

[0326] [Compound Represented by Any of Formulas (H1), (H2), and (H3)] As the host material, for example, a compound represented by any of the following formulas (H1), (H2), and (H3) can be used.

[0327] In formulas (H1), (H2) and (H3), L １ is a single bond or a divalent group containing at least an arylene or heteroarylene. １is a single bond, or an arylene having 6 to 24 carbon atoms, a heteroarylene having 2 to 24 carbon atoms, a heteroarylenearylene having 6 to 24 carbon atoms, or an aryleneheteroarylenearylene having 6 to 24 carbon atoms, or any two of these are joined by —O—, —S—, —CH ２ -, -Si(-Arx) ２ - (Arx is aryl), or a divalent group formed by linking with cycloalkylene. １ The arylene in L is preferably an arylene having 6 to 16 carbon atoms, more preferably an arylene having 6 to 12 carbon atoms, and particularly preferably an arylene having 6 to 10 carbon atoms, and specific examples thereof include divalent groups such as a benzene ring, a biphenyl ring, a terphenyl ring, and a fluorene ring. １ The heteroarylene in the formula (I) is preferably a heteroarylene having 2 to 24 carbon atoms. At least one hydrogen atom in the compounds represented by the formula (I) may be substituted with at least one group selected from the substituent group Z or deuterium, for example, alkyl having 1 to 6 carbon atoms, cyano, halogen, or deuterium.

[0328] Preferred specific examples include compounds represented by any of the structural formulas listed below, in which at least one hydrogen may be substituted with halogen, cyano, alkyl having 1 to 4 carbon atoms (e.g., methyl or t-butyl), phenyl, naphthyl, or the like.

[0329] (mCP)

[0330]

[0331]

[0332]

[0333] [Anthracene Compound] Examples of the anthracene compound as a host include a compound represented by formula (3-H) and a compound represented by formula (3-H2).

[0334] In formula (3-H), X and Ar ４are each independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino, optionally substituted diheteroarylamino, substituted or unsubstituted arylheteroarylamino, substituted or unsubstituted alkyl, optionally substituted cycloalkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted arylthio, or substituted silyl; and all of X and Ar ４ and cannot be hydrogen at the same time. At least one hydrogen in the compound represented by formula (3-H) may be substituted with halogen, cyano, deuterium or an optionally substituted heteroaryl.

[0335] Furthermore, a multimer (preferably a dimer) may be formed using the structure represented by formula (3-H) as a unit structure. In this case, for example, unit structures represented by formula (3-H) may be bonded to each other via X, and examples of X include a single bond, an arylene (such as phenylene, biphenylene, and naphthylene), and a heteroarylene (a divalent group such as a pyridine ring, a dibenzofuran ring, a dibenzothiophene ring, a carbazole ring, a benzocarbazole ring, and a phenyl-substituted carbazole ring).

[0336] Preferred embodiments of the above anthracene compounds are described below: The symbols in the following structures are defined as above.

[0337] In formula (3-H), X's are each independently a group represented by formula (3-X1), formula (3-X2), or formula (3-X3), and the group represented by formula (3-X1), formula (3-X2), or formula (3-X3) is bonded to the anthracene ring of formula (3-H) at *. Preferably, two X's are not simultaneously groups represented by formula (3-X3). More preferably, two X's are not simultaneously groups represented by formula (3-X2).

[0338] Furthermore, a multimer (preferably a dimer) may be formed using the structure represented by formula (3-H) as a unit structure. In this case, for example, unit structures represented by formula (3-H) may be bonded to each other via X, and examples of X include a single bond, an arylene (such as phenylene, biphenylene, and naphthylene), and a heteroarylene (a divalent group such as a pyridine ring, a dibenzofuran ring, a dibenzothiophene ring, a carbazole ring, a benzocarbazole ring, and a phenyl-substituted carbazole ring).

[0339] The naphthylene moieties in formula (3-X1) and formula (3-X2) may be fused with one benzene ring, resulting in the following fused structure:

[0340] Ar １ and Ar ２ are each independently hydrogen, phenyl, biphenylyl, terphenylyl, quaterphenylyl, naphthyl, phenanthryl, fluorenyl, benzofluorenyl, chrysenyl, triphenylenyl, pyrenyl, or a group represented by formula (A) (including carbazolyl, benzocarbazolyl, and phenyl-substituted carbazolyl). １ or Ar ２ 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 *.

[0341] Ar ３ is phenyl, biphenylyl, terphenylyl, quaterphenylyl, naphthyl, phenanthryl, fluorenyl, benzofluorenyl, chrysenyl, triphenylenyl, pyrenyl, or a group represented by formula (A) (including carbazolyl, benzocarbazolyl, and phenyl-substituted carbazolyl). ３ is a group represented by formula (A), the group represented by formula (A) is bonded to the single bond represented by a straight line in formula (3-X3) at the *. That is, the anthracene ring of formula (3-H) and the group represented by formula (A) are directly bonded.

[0342] Also, Ar ３may have a substituent, and Ar ３ At least one hydrogen atom in Ar may be further substituted with an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, phenyl, biphenylyl, terphenylyl, naphthyl, phenanthryl, fluorenyl, chrysenyl, triphenylenyl, pyrenyl, or a group represented by formula (A) (including carbazolyl and phenyl-substituted carbazolyl). ３ In the case where the substituent of is a group represented by formula (A), the group represented by formula (A) is Ar ３ and combine.

[0343] Ar ４ are each independently hydrogen, phenyl, biphenylyl, terphenylyl, naphthyl, or silyl substituted with alkyl having 1 to 4 carbon atoms (such as methyl, ethyl, t-butyl, etc.) and / or cycloalkyl having 5 to 10 carbon atoms.

[0344] Furthermore, hydrogen atoms in the chemical structure of the anthracene compound represented by formula (3-H) may be substituted with a group represented by formula (A). When substituted with a group represented by formula (A), the group represented by formula (A) substitutes at least one hydrogen atom in the compound represented by formula (3-H) at the *.

[0345] The group represented by formula (A) is one of the substituents that the anthracene compound represented by formula (3-H) may have.

[0346] In formula (A), Y is —O—, —S— or >N—R ２９ and R ２１ ~R ２８ are each independently 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 Adjacent groups among R may be bonded to each other to form a hydrocarbon ring, an aryl ring, or a heteroaryl ring; ２９ is hydrogen or optionally substituted aryl. Y in formula (A) is preferably —O—.

[0347] R ２１ ~R ２８ The "substituted amino" in the "optionally substituted amino" includes diarylamino, diheteroarylamino, arylheteroarylamino, and the like.

[0348] Y as ">N-R ２９ " R in ２９ is hydrogen or optionally substituted aryl.

[0349] R ２１ ~R ２８ Among these, adjacent groups may be bonded to each other to form a hydrocarbon ring, an aryl ring, or a heteroaryl ring. The group represented by formula (A-1) below does not form a ring, and examples of the group represented by formulas (A-2) to (A-14) below include groups represented by formulas (A-1) to (A-14). At least one hydrogen atom in the group represented by any of formulas (A-1) to (A-14) may be substituted with alkyl, cycloalkyl, aryl, heteroaryl, alkoxy, aryloxy, arylthio, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, alkyldicycloalkylsilyl, diaryl (the two aryls may be bonded to each other via a linking group), substituted amino, diheteroaryl-substituted amino, arylheteroaryl-substituted amino, halogen, hydroxy, or cyano.

[0350]

[0351] Examples of rings formed by bonding adjacent groups to each other include hydrocarbon rings such as cyclohexane rings, and examples of aryl and heteroaryl rings include the above-mentioned R ２１ ~R ２８These rings are formed so as to be fused with one or two benzene rings in formula (A-1).

[0352] The group represented by formula (A) is a group obtained by removing one hydrogen atom from any position of formula (A), and * indicates the position. That is, the group represented by formula (A) may have any position as a bonding position. For example, any carbon atom on the two benzene rings in the structure of formula (A), R ２１ ~R ２８ an atom on any ring formed by bonding adjacent groups to each other, or ">N-R" as Y in the structure of formula (A) ２９ " R in ２９ Any position in the ２９ " in N (R ２９ The same applies to the groups represented by any of formulae (A-1) to (A-14).

[0353] Examples of the group represented by formula (A) include groups represented by any of formulas (A-1) to (A-14), preferably groups represented by any of formulas (A-1) to (A-5) and (A-12) to (A-14), more preferably groups represented by any of formulas (A-1) to (A-4), still more preferably groups represented by any of formulas (A-1), (A-3) and (A-4), and particularly preferably groups represented by formula (A-1).

[0354] Examples of the group represented by formula (A) include the following groups: wherein Y and * are defined as above.

[0355]

[0356] In the compound represented by formula (3-H), the group represented by formula (A) is a naphthalene ring in formula (3-X1) or formula (3-X2), a single bond in formula (3-X3), and Ar in formula (3-X3). ３ The preferred form is a combination of any one of the following:

[0357] All or part of the hydrogen atoms in the chemical structure of the anthracene compound represented by formula (3-H) may be deuterium atoms.

[0358] The anthracene compound as the host may be, for example, a compound represented by the following formula (3-H2).

[0359] In formula (3-H2), Ar ｃ is an optionally substituted aryl or an optionally substituted heteroaryl, and R ｃ is hydrogen, alkyl, or cycloalkyl; Ar １１ , Ar １２ , Ar １３ , Ar １４ , Ar １５ , Ar １６ , Ar １７ , and Ar １８ are each independently hydrogen, an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted diarylamino (two aryls may be bonded to each other via a linking group), an optionally substituted diheteroarylamino (two heteroaryls may be bonded to each other via a linking group), an optionally substituted arylheteroarylamino (an aryl and a heteroaryl may be bonded to each other via a linking group), an optionally substituted alkyl, an optionally substituted cycloalkyl, an optionally substituted alkenyl, an optionally substituted alkoxy, an optionally substituted aryloxy, an optionally substituted arylthio, or an optionally substituted silyl, and at least one hydrogen in the compound represented by formula (3-H2) is optionally substituted with halogen, cyano, or deuterium.

[0360] The "optionally substituted aryl" is also preferably a group represented by any one of the following formulae (3-H2-X1) to (3-H2-X8).

[0361]

[0362] In formulas (3-H2-X1) to (3-H2-X8), * indicates a bonding position. ２１ , Ar ２２ , and Ar ２３ are each independently hydrogen, phenyl, biphenylyl, terphenylyl, quaterphenylyl, naphthyl, phenanthryl, fluorenyl, benzofluorenyl, chrysenyl, triphenylenyl, pyrenyl, anthracenyl, or a group represented by formula (A). In the description of formula (3-H2), the group represented by formula (A) is the same as that described in the anthracene compound represented by formula (3-H).

[0363] In formulas (3-H2-X4) to (3-H2-X8), Ar ２４ , Ar ２５ , Ar ２６ , Ar ２７ , Ar ２８ , Ar ２９ , and Ar ３０ are each independently hydrogen, phenyl, biphenylyl, terphenylyl, naphthyl, phenanthryl, fluorenyl, chrysenyl, triphenylenyl, pyrenyl, or a group represented by formula (A). In addition, any one or more hydrogen atoms in each of the groups represented by formulas (3-H2-X1) to (3-H2-X8) may be substituted with alkyl having 1 to 6 carbon atoms (preferably methyl or t-butyl).

[0364] Furthermore, preferred examples of the "optionally substituted aryl" include terphenylyl (particularly m-terphenyl-5'-yl) which may be substituted with one or more substituents selected from the group consisting of phenyl, biphenylyl, terphenylyl, naphthyl, phenanthryl, fluorenyl, chrysenyl, triphenylenyl, pyrenyl, and groups represented by formula (A).

[0365] The "optionally substituted heteroaryl" also includes a group represented by formula (A). In addition, specific examples of the "optionally substituted aryl" and the "optionally substituted heteroaryl" include dibenzofuryl, naphthobenzofuryl, phenyl-substituted dibenzofuryl, etc.

[0366] At least one hydrogen atom in the compound represented by formula (3-H2) may be substituted with a halogen atom, cyano atom, or deuterium atom. In this case, "halogen" includes fluorine, chlorine, bromine, and iodine. In particular, a compound represented by formula (3-H2) in which all hydrogen atoms are substituted with deuterium atoms is preferred.

[0367] In formula (3-H2), R ｃ is hydrogen, alkyl, or cycloalkyl, preferably hydrogen, methyl, or t-butyl, and more preferably hydrogen. １１ ~Ar １８ It is preferable that at least two of the substituents be an optionally substituted aryl or an optionally substituted heteroaryl. That is, the anthracene compound represented by formula (3-H2) preferably has a structure in which at least three substituents selected from the group consisting of an optionally substituted aryl and an optionally substituted heteroaryl are bonded to an anthracene ring.

[0368] The anthracene compound represented by formula (3-H2) is Ar １１ ~Ar １８ It is more preferable that two of the groups are optionally substituted aryl or optionally substituted heteroaryl, and the other six are hydrogen, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted alkenyl, or optionally substituted alkoxy. That is, it is more preferable that the anthracene compound represented by formula (3-H2) has a structure in which three substituents selected from the group consisting of optionally substituted aryl and optionally substituted heteroaryl are bonded to the anthracene ring.

[0369] The anthracene compound represented by formula (3-H2) is Ar１１ ~Ar １８ It is more preferred that any two of are optionally substituted aryl or optionally substituted heteroaryl, and the other six are hydrogen, methyl, or t-butyl.

[0370] Furthermore, in formula (3-H2), R ｃ is hydrogen, and Ar １１ ~Ar １８ It is preferred that any six of these are hydrogen.

[0371] The anthracene compound represented by formula (3-H2) is preferably an anthracene compound represented by the following formula (3-H2-A), (3-H2-B), (3-H2-C), (3-H2-D), or (3-H2-E).

[0372] In formula (3-H2-A), (3-H2-B), (3-H2-C), (3-H2-D) or (3-H2-E), Ar ｃ ', Ar １１ ', Ar １２ ', Ar １３ ', Ar １４ ', Ar １５ ', Ar １７ ', and Ar １８ Ar' are each independently phenyl, biphenylyl, terphenylyl, quaterphenylyl, naphthyl, phenanthryl, fluorenyl, benzofluorenyl, chrysenyl, triphenylenyl, pyrenyl, or a group represented by formula (A), and at least one hydrogen atom in these groups may be substituted with phenyl, biphenylyl, terphenylyl, quaterphenylyl, naphthyl, phenanthryl, fluorenyl, benzofluorenyl, chrysenyl, triphenylenyl, pyrenyl, or a group represented by formula (A). When both hydrogen atoms of the methylenes in the fluorenyl and benzofluorenyl are substituted with phenyl, these phenyls may be bonded to each other via a single bond. ｃ ', Ar １１ ', Ar １２ ', Ar １３ ', Ar １４ ', Ar １５ ', Ar１７ ', and Ar １８ A carbon atom of the anthracene ring to which no ' is bonded may have a methyl or t-butyl bonded in place of a hydrogen atom.

[0373] Ar ｃ ', Ar １１ ', Ar １２ ', Ar １３ ', Ar １４ ', Ar １５ ', Ar １７ ', and Ar １８ When each of "3-H2-X1" and "3-H2-X2" is a substituted or unsubstituted phenyl or a substituted or unsubstituted naphthyl, it is preferably a group represented by any one of the above formulae (3-H2-X1) to (3-H2-X8).

[0374] Ar ｃ ', Ar １１ ', Ar １２ ', Ar １３ ', Ar １４ ', Ar １５ ', Ar １７ ', and Ar １８ It is more preferable that each of the ' is independently phenyl, biphenylyl (particularly biphenyl-2-yl or biphenyl-4-yl), terphenylyl (particularly m-terphenyl-5'-yl), naphthyl, phenanthryl, fluorenyl, or a group represented by any one of the above formulas (A-1) to (A-4), and in this case, at least one hydrogen atom in these groups may be substituted by phenyl, biphenylyl, naphthyl, phenanthryl, fluorenyl, or a group represented by any one of the above formulas (A-1) to (A-4).

[0375] In addition, at least one hydrogen atom in the compound represented by formula (3-H2-A), (3-H2-B), (3-H2-C), (3-H2-D), or (3-H2-E) may be substituted with a halogen atom, a cyano atom, or a deuterium atom. A deuterated form is preferred, and a form in which all anthracene rings are deuterated or a form in which all hydrogen atoms are deuterated is preferred.

[0376] Particularly preferred anthracene compounds represented by formula (3-H2) include anthracene compounds represented by the following formula (3-H2-Aa).

[0377] In formula (3-H2-Aa), Ar ｃ ', Ar １４ ', and Ar １５ Each of Ar' independently represents phenyl, biphenylyl, terphenylyl, naphthyl, phenanthryl, fluorenyl, benzofluorenyl, chrysenyl, triphenylenyl, pyrenyl, or a group represented by any one of the above formulas (A-1) to (A-11), and at least one hydrogen atom in these groups may be substituted with phenyl, biphenylyl, terphenylyl, naphthyl, phenanthryl, fluorenyl, benzofluorenyl, chrysenyl, triphenylenyl, pyrenyl, or a group represented by any one of formulas (A-1) to (A-11). Here, when both hydrogen atoms of methylene groups in fluorenyl and benzofluorenyl are substituted with phenyl, these phenyls may be bonded to each other via a single bond. In addition, Ar ｃ ', Ar １４ ', and Ar １５ A carbon atom on the anthracene ring to which "'" is not bonded may be substituted with methyl or t-butyl in place of hydrogen. At least one hydrogen in the compound represented by formula (3-H2-Aa) may be substituted with halogen or cyano, and at least one hydrogen in the compound represented by formula (3-H2-Aa) may be substituted with deuterium.

[0378] In formula (3-H2-Aa), Ar ｃ ', Ar １４ ', and Ar １５ are each preferably independently phenyl, biphenylyl, terphenylyl, naphthyl, phenanthryl, fluorenyl, or a group represented by any one of the above formulae (A-1) to (A-4), and at least one hydrogen atom in these groups may be substituted by phenyl, naphthyl, phenanthryl, fluorenyl, or a group represented by any one of the formulae (A-1) to (A-4).

[0379] In the compound represented by formula (3-H2-Aa), at least the carbon atom at the 10-position of the anthracene ring (Ar ｃ It is preferable that the hydrogen bonded to the carbon atom to which Ar is bonded (the carbon atom to which Ar is bonded is the 9th position) is replaced 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 formula (3-H2-Ab), D is deuterium, and Ar ｃ ', Ar １４ ', and Ar １５ The definition of D in formula (3-H2-Ab) is the same as that in formula (3-H2-Aa). D in formula (3-H2-Ab) indicates that at least this position is deuterium, and any one or more other hydrogen atoms in formula (3-H2-Ab) may also be deuterium, and it is also preferred that all hydrogen atoms in formula (3-H2-Ab) are deuterium.

[0380]

[0381] Specific examples of anthracene compounds include compounds represented by formulae (3-131-Y) to (3-182-Y), (3-183-N), (3-184-Y) to (3-284-Y), (3-500) to (3-557), (3-600) to (3-605), and (3-606-Y) to (3-626-Y). The hydrogen atoms in these formulae may be partially or completely substituted with deuterium, and particularly preferred forms of deuterium substitution are listed individually. Y in the formulae is -O-, -S-, >N-R ２９ (R ２９ is the same as above) or >C(-R ３０ ) ２ (R ３０ may be either an optionally linked aryl or alkyl, and R ２９ is, for example, phenyl, R ３０ For example, when Y is O, the formula (3-131-Y) becomes the formula (3-131-O), and when Y is -S- or >N-R, ２９ In the case of (3-131-S) or (3-131-N), respectively.

[0382]

[0383]

[0384]

[0385]

[0386]

[0387]

[0388]

[0389]

[0390]

[0391]

[0392]

[0393]

[0394]

[0395]

[0396]

[0397]

[0398]

[0399]

[0400]

[0401] In the above formula, D is deuterium.

[0402] Among these compounds, the compounds of 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 -O- or >N-R ２９ is preferred, and —O— is more preferred. Deuterium-substituted forms are also preferred.

[0403] The above anthracene compound is a compound having a reactive group at a desired position of the anthracene skeleton, and an anthracene compound represented by formula (3-H) in which X, Ar ４ The compound can be produced by applying Suzuki coupling, Negishi coupling, or other known coupling reactions using a compound having a reactive group in a partial structure such as the structure of formula (A) as a starting material. Examples of reactive groups in these reactive compounds include halogens and boronic acids. Specific production methods can be found in, for example, the synthesis methods described in paragraphs

[0089] to

[0175] of WO 2014 / 141725.

[0404] [Fluorene Compound] The compound represented by formula (4-H) basically functions as a host.

[0405] In formula (4-H), R １ From R １０are each independently hydrogen, aryl, heteroaryl (the heteroaryl may be bonded to the fluorene skeleton in formula (4-H) via a single bond or a linking group), diarylamino (two aryls may be bonded to each other via a linking group), diheteroarylamino (two heteroaryls may be bonded to each other via a linking group), arylheteroarylamino (aryl and heteroaryl may be bonded to each other via a linking group), alkyl, cycloalkyl, alkenyl, alkoxy, or aryloxy, in which at least one hydrogen may be substituted with an aryl, heteroaryl, alkyl, or cycloalkyl; 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 each independently bond to form a fused ring or a spiro ring, and at least one hydrogen atom in the formed ring may be substituted with an aryl, a heteroaryl (the heteroaryl may be bonded to the formed ring via a single bond or a linking group), a diarylamino (two aryls may be bonded to each other via a linking group), a diheteroarylamino (two heteroaryls may be bonded to each other via a linking group), an arylheteroarylamino (an aryl and a heteroaryl may be bonded to each other via a linking group), an alkyl, a cycloalkyl, an alkenyl, an alkoxy, or an aryloxy, and at least one hydrogen atom in these may be substituted with an aryl, a heteroaryl, an alkyl, or a cycloalkyl; and at least one hydrogen atom in a compound represented by formula (4-H) may be substituted with a halogen atom, a cyano, or a deuterium atom.

[0406] Specific examples of heteroaryl include monovalent groups 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).

[0407]

[0408] In formula (4-Ar1) to formula (4-Ar5), Y １ are each independently O, S, or N—R, and R is phenyl, biphenylyl, naphthyl, anthracenyl, or hydrogen, and at least one hydrogen in the structures of formulae (4-Ar1) to (4-Ar5) may be substituted with phenyl, biphenylyl, naphthyl, anthracenyl, phenanthryl, methyl, ethyl, propyl, or butyl.

[0409] These heteroaryls may be bonded to the fluorene skeleton in formula (4-H) via a single bond or a linking group. That is, the fluorene skeleton and the heteroaryl in formula (4-H) may be bonded not only directly but also via a linking group. Examples of such linking groups include phenylene, biphenylene, naphthylene, anthracenylene, methylene, ethylene, -OCH ２ CH ２ -, -CH ２ CH ２ O- or -OCH ２ CH ２ Examples include O-.

[0410] Furthermore, 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 are each independently bonded to form a fused ring, R ９ and R １０ may be bonded to form a spiro ring. １ From R ８The fused ring formed by is a ring fused to the benzene ring in formula (4-H), and is an aliphatic ring or an aromatic ring. An aromatic ring is preferable, and examples of the structure including the benzene ring in formula (4-H) include a naphthalene ring and a phenanthrene ring. R ９ and R １０ The spiro ring formed by the formula (4-H) is a ring spiro-bonded to the five-membered ring in formula (4-H), and is an aliphatic ring or an aromatic ring. An aromatic ring, such as a fluorene ring, is preferred.

[0411] 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 in formula (4-H), R １ and R ２ a compound having a condensed benzene ring formed by bonding of R ３ and R ４ a compound having a condensed benzene ring formed by bonding of R １ From R ８ is a compound in which none of the above is bound.

[0412]

[0413] R in formula (4-H-1), formula (4-H-2) and formula (4-H-3) １ From R １０ The definition of R in formula (4-H) corresponds to １ From R １０ and R in formula (4-H-1) and formula (4-H-2) １１ From R １４ The definition of R in formula (4-H) １ From R １０ is the same as

[0414] The compound represented by formula (4-H) is more preferably a compound represented by the following formula (4-H-1A), formula (4-H-2A), or formula (4-H-3A), wherein R ９ and R １０ are bonded to form a spiro-fluorene ring.

[0415]

[0416] R in formula (4-H-1A), formula (4-H-2A) and formula (4-H-3A) ２ From R ７ The definition of is the corresponding R in formula (4-H-1), formula (4-H-2) and formula (4-H-3). ２ From R ７ and R in formula (4-H-1A) and formula (4-H-2A) is the same as １１ From R １４ The definition of R in formula (4-H-1) and formula (4-H-2) is also １１ From R １４ is the same as

[0417] In addition, all or part of the hydrogen atoms in the compound represented by formula (4-H) may be substituted with halogen, cyano or deuterium.

[0418] More specific examples of the fluorene compound as the host of the present invention include compounds represented by the following structural formulas.

[0419] [Dibenzochrysene Compound] The dibenzochrysene compound as a host is, for example, a compound represented by the following formula (5-H).

[0420] In formula (5-H), R １ From R １６ are each independently hydrogen, aryl, heteroaryl (the heteroaryl may be bonded to the dibenzochrysene skeleton in formula (5-H) via a single bond or a linking group), diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkenyl, alkoxy, or aryloxy, in which at least one hydrogen may be substituted with an aryl, heteroaryl, alkyl, or cycloalkyl; and R １ From R １６Adjacent groups among these may be bonded to each other to form a fused ring, and at least one hydrogen atom in the formed ring may be substituted with an aryl, heteroaryl (the heteroaryl may be bonded to the formed ring via a single bond or a linking group), diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkenyl, alkoxy, or aryloxy, and at least one hydrogen atom in these may be substituted with an aryl, heteroaryl, alkyl, or cycloalkyl; and at least one hydrogen atom in the compound represented by formula (5-H) may be substituted with a halogen atom, cyano, or deuterium.

[0421] Examples of the alkenyl in the definition of formula (5-H) include alkenyl having 2 to 30 carbon atoms, 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 include 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, and 5-hexenyl.

[0422] Specific examples of heteroaryl include monovalent groups represented by removing any one hydrogen atom from a compound of the following formula (5-Ar1), formula (5-Ar2), formula (5-Ar3), formula (5-Ar4), or formula (5-Ar5).

[0423]

[0424] In formula (5-Ar1) to formula (5-Ar5), Y １ are each independently O, S, or N—R, where R is phenyl, biphenylyl, naphthyl, anthracenyl, or hydrogen, and at least one hydrogen in the structures of formulae (5-Ar1) to (5-Ar5) may be substituted with phenyl, biphenylyl, naphthyl, anthracenyl, phenanthryl, methyl, ethyl, propyl, or butyl.

[0425] These heteroaryls may be bonded to the dibenzochrysene skeleton in formula (5-H) via a single bond or a linking group. That is, the dibenzochrysene skeleton and the heteroaryl in formula (5-H) may be bonded not only directly but also via a linking group. Examples of such linking groups include phenylene, biphenylene, naphthylene, anthracenylene, methylene, ethylene, -OCH ２ CH ２ -, -CH ２ CH ２ O- or -OCH ２ CH ２ Examples include O-.

[0426] 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 and R １５ are each independently hydrogen, phenyl, biphenylyl, naphthyl, anthracenyl, phenanthryl, a monovalent group having a structure of formula (5-Ar1), formula (5-Ar2), formula (5-Ar3), formula (5-Ar4) or formula (5-Ar5) (the monovalent group having such a structure is phenylene, biphenylene, naphthylene, anthracenylene, methylene, ethylene, —OCH ２ CH ２ -, -CH ２ CH ２ O- or -OCH ２ CH ２ (which may be bonded to the dibenzochrysene skeleton in formula (5-H) via O—), is preferably methyl, ethyl, propyl, or butyl.

[0427] 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 and R １４ At least one (preferably one or two, more preferably one) of the groups is a single bond, phenylene, biphenylene, naphthylene, anthracenylene, methylene, ethylene, or —OCH ２ CH ２ -, -CH ２ CH ２ O- or -OCH ２ CH ２ A monovalent group having a structure of formula (5-Ar1), (5-Ar2), (5-Ar3), (5-Ar4), or (5-Ar5) via O-, and other than the at least one (i.e., other than the position substituted by the monovalent group having the structure) is hydrogen, phenyl, biphenylyl, naphthyl, anthracenyl, methyl, ethyl, propyl, or butyl, and at least one hydrogen in these may be substituted with phenyl, biphenylyl, naphthyl, anthracenyl, methyl, ethyl, propyl, or butyl.

[0428] Furthermore, R in formula (5-H) ２ , R ３ , R ６ , R ７ , R １０ , R １１ , R １４ and R １５ When a monovalent group having a structure represented by formula (5-Ar1) to formula (5-Ar5) is selected as the group, at least one hydrogen atom in the structure is selected from the group represented by formula (5-Ar1) to formula (5-Ar5). １ From R １６ may be bonded to any one of the following to form a single bond.

[0429] More specific examples of the dibenzochrysene compound as the host of the present invention include compounds represented by the following structural formulas.

[0430]

[0431] [Hole-transporting host material (HH) and electron-transporting host material (EH)] The host material may be one type or a combination of two or more types. In the case of a combination of two or more types, a combination of a hole-transporting host material and an electron-transporting host material is preferred. The hole-transporting host material (HH) and the electron-transporting host material (EH) satisfy the following relationship with respect to their HOMO (highest occupied molecular orbital) and LUMO (lowest unoccupied molecular orbital): the HOMO of the hole-transporting host material (HH) is shallower than the HOMO of the electron-transporting host material (EH), and the LUMO of the electron-transporting host material (EH) is deeper than the LUMO of the hole-transporting host material (HH). It is also preferable that the HOMO of the emitting dopant is shallower than the HOMO of the hole-transporting host material (HH), or that the LUMO of the emitting dopant is deeper than the LUMO of the electron-transporting host material (EH).

[0432] In addition, the lowest excited triplet energy level (E Ｔ１ ) is the highest E in the light-emitting layer from the viewpoint of promoting the generation of TADF without inhibiting it in the light-emitting layer. Ｔ１ E of an emitting dopant or an assisting dopant having Ｔ１ It is preferable that it is higher than

[0433] It is also preferable to use a hole-transporting host material in the hole-transporting layer adjacent to the light-emitting layer and an electron-transporting host material in the electron-transporting layer adjacent to this light-emitting layer. This is because carrier leakage and energy leakage from the light-emitting layer to the adjacent layer are less likely to occur, resulting in a highly efficient organic EL device. The host material (hole-transporting host material) in the light-emitting layer and the material of the hole-transporting layer may be the same or different. Furthermore, the host material (electron-transporting host material) in the light-emitting layer and the material of the electron-transporting layer may be the same or different.

[0434] [Hole-Transporting Host Material (HH)] A preferred example of the hole-transporting host material (HH) is a compound represented by formula (HH-1) or having a partial structure represented by formula (HH-1) and a structure containing at least three rings selected from the group consisting of aryl rings and heteroaryl rings. This compound preferably does not contain any of an imine structure (—N═C—; including a partial structure of a heteroaryl ring), boron (>B—), and cyano (CN).

[0435]

[0436] In formula (HH-1), Q is >O, >S, or >N-A. Ｈ In formula (HH-1), one carbon atom adjacent to the carbon atom to which Q is bonded in each of the two phenyls may be bonded to each other via L, and L is a single bond, >O, >S, or >C(-A Ｈ ) ２ and A Ｈ is hydrogen, aryl, or heteroaryl, and >C(-A Ｈ ) ２ The two A's in Ｈ may be bonded to each other.

[0437] When the hole-transporting host material contains a structure represented by formula (HH-1) as a partial structure, it may contain one such partial structure, but it is also preferable to contain two or more such partial structures. When two or more such partial structures are contained, the two or more partial structures may be the same or different. The two or more partial structures may be bonded to each other via a single bond, may be bonded so that any rings contained in the partial structures are shared, or may be bonded so that any rings contained in the partial structures are fused to each other. The partial structure may further have a substituent selected from aryl, heteroaryl, diarylamino, or aryloxy.

[0438] The compound represented by the above formula (HH-1) or having a partial structure represented by formula (HH-1) has a structure containing at least three rings selected from the group consisting of aryl rings and heteroaryl rings. The number of rings contained is preferably 6 or more, more preferably 8 or more. The number is preferably 20 or less, more preferably 15 or less, and even more preferably 10 or less. The number of rings refers to the number of single rings, and for fused rings, the number is the number of single rings constituting the fused rings.

[0439] The hole-transporting host material is preferably a compound containing one or more partial structures selected from the group consisting of a triarylamine structure, a carbazole ring, a dibenzofuran ring, a dibenzothiophene ring, and a fused polycyclic ring containing phenoxazine or phenothiazine. The hole-transporting host material may contain one such partial structure, but preferably contains two or more. When containing two or more partial structures, the two or more partial structures may be the same or different from each other.

[0440] Specific examples of the hole-transporting host material include the following compounds.

[0441]

[0442]

[0443]

[0444]

[0445]

[0446]

[0447]

[0448]

[0449]

[0450]

[0451]

[0452]

[0453] [Electron-Transporting Host Material (EH)] Examples of the electron-transporting host material (EH) include compounds represented by formulae (EH-1A) to (EH-1D) or compounds having a partial structure represented by formulae (EH-1A) to (EH-1D) and a structure including at least three rings selected from the group consisting of aryl rings and heteroaryl rings.

[0454]

[0455] In formulae (EH-1A) to (EH-1D), Ar is a heteroaryl ring containing N═C as a partial structure constituting the ring, Z is a single bond, —O—, —S—, or —N(-A Ｅ )-, and the carbon atom adjacent to the carbon atom to which Z is bonded and the A to which Z is bonded are Ｅ and may be bonded to each other via L, and L is a single bond, >O, >S or >C(-A Ｅ ) ２ and A Ｅ is aryl, heteroaryl, or triarylsilyl, and in formula (EH-1C), any one of A Ｅ may be diarylamino, and two A's bonded to the same atom Ｅ may be bonded to each other via L, X is C, P or S, when X is C, n=2 and m=1, when X is P, n=3 and m=1, when X is S, n=2 and m=1 to 2.

[0456] Compounds represented by the above formulae (EH-1A) to (EH-1D) or having a partial structure represented by formulae (EH-1A) to (EH-1D) have a structure containing at least three rings selected from the group consisting of aryl rings and heteroaryl rings. The number of rings contained is preferably 4 or more, more preferably 6 or more, and even more preferably 8 or more. The number is preferably 20 or less, more preferably 15 or less, and even more preferably 10 or less. The number of rings refers to the number of monocyclic rings, and for fused rings, the number is the number counting the monocyclic rings that constitute the fused rings.

[0457] When the electron-transporting host material contains a structure represented by formula (EH-1A) to (EH-1D) as a partial structure, it may contain one of these partial structures, but it is also preferable to contain two or more of these partial structures. When two or more partial structures are contained, the two or more partial structures may be the same or different. The two or more partial structures may be bonded to each other by a single bond, may be bonded so that any rings contained in the partial structures are shared, or may be bonded so that any rings contained in the partial structures are fused to each other. The partial structure may further have a substituent selected from aryl, heteroaryl, diarylamino, or aryloxy.

[0458] Specific examples of the electron transporting host material include the following compounds.

[0459]

[0460]

[0461]

[0462]

[0463]

[0464]

[0465]

[0466]

[0467] Other preferred examples of the electron-transporting host material (a compound having a partial structure represented by formula (EH-1)) include a polycyclic aromatic compound represented by formula (EH-1b) below, or a multimer of a polycyclic aromatic compound having a plurality of structures represented by formula (EH-1b) below.

[0468] In formula (EH-1b), R １ , R ２ , R ３ , R ４ and R ５ (Hereinafter, “R １ Each of the groups (also referred to as "groups") independently represents hydrogen or a substituent. The substituent may be a substituent selected from the group Z of substituents. In formula (EH-1b), X １ and X ２ are each independently >N—R (amine nitrogen), >O, >C(—R) ２ , >S or >Se, and X １ and X ２ Both are > C(-R) ２ The above-mentioned >N-R and >C(-R) ２ In the formula, R is independently hydrogen or a substituent selected from the substituent group Z, and may be further substituted with an aryl, heteroaryl, alkyl, or cycloalkyl (these are referred to as second substituents), and the above >N-R and >C(-R) ２ Each R may be independently bonded to at least one of the rings a, b, and c via a linking group or a single bond. １ , Y ２ , Y ３ , Y ４ , Y ５ and Y ６ (hereinafter referred to as "Y １ Each of the groups (also referred to as "=C(-R)-" or "=N-" (pyridinic nitrogen) independently represents ═C(-R)- or ═N- (pyridinic nitrogen), and at least one of the groups is ═N- (pyridinic nitrogen), and each of the R in the ═C(-R)- is independently hydrogen or a substituent selected from the substituent group Z. １ , R ２ , R３ , R ４ and R ５ , and the Y １ ~Y ６ Adjacent groups among the Rs in =C(-R)- as represented by the formula (EH-1b) may bond to each other to form an aryl ring or a heteroaryl ring together with at least one of the rings a, b, and c, and at least one hydrogen atom in the formed ring may be substituted with an aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (the two aryls may be bonded via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, or aryloxy (all of these, first substituents), and at least one hydrogen atom in these may be further substituted with an aryl, heteroaryl, alkyl, or cycloalkyl (all of these, second substituents). At least one hydrogen atom in the compound and structure represented by formula (EH-1b) may be substituted with a cyano, halogen, or deuterium.

[0469] In formula (EH-1b), R １ , R ２ , R ３ , R ４ and R ５ are all hydrogen, or R ３ and R ４ are both hydrogen, and R １ , R ２ and R ５Preferably, one or more selected from the group consisting of are substituents other than hydrogen, and the rest are hydrogen. Preferred substituents are alkyl, aryl which may be substituted with alkyl or heteroaryl, heteroaryl which may be substituted with alkyl or aryl, or diarylamino which may be substituted with alkyl or aryl. In this case, the alkyl is preferably an alkyl having 1 to 6 carbon atoms (e.g., methyl, t-butyl), the aryl is preferably phenyl or biphenyl, and the heteroaryl is preferably triazinyl, carbazolyl (e.g., 2-carbazolyl, 3-carbazolyl, 9-carbazolyl), pyrimidinyl, pyridinyl, dibenzofuranyl, or dibenzothienyl. Specific examples include phenyl, biphenyl, diphenyltriazinyl, carbazolyltriazinyl, monophenylpyrimidinyl, diphenylpyrimidinyl, carbazolyltriazinyl, pyridinyl, dibenzofuranyl, and dibenzothienyl.

[0470] Y １ etc. are each independently ═C(—R)— or ═N—, and at least one is ═N—. １ ~Y ６ Any of the groups may be =N-. １ and Y ６ is ═N- (the a ring is a pyrimidine ring), Y １ or Y ６ is =N− (a ring is a pyridine ring), Y ２ and Y ５ is ═N—(ring b and ring c are pyridine rings), Y ３ and Y ４ is ═N—(ring b and ring c are pyridine rings), Y ２ ~Y ５ is ═N—(ring b and ring c are pyrimidine rings), Y １ , Y ３ , Y ４ and Y ６ is ═N—(ring a is a pyrimidine ring, rings b and c are pyridine rings), Y １ , Y ２ , Y ５ and Y ６is ═N—(ring a is a pyrimidine ring, rings b and c are pyridine rings), Y １ ~Y ６ is ═N—(ring a, ring b and ring c are pyrimidine rings), Y ２ or Y ５ is ═N— (ring b or ring c is a pyridine ring).

[0471] In addition to the above =N- configuration, X １ and X ２ is preferably >O, and a polycyclic aromatic compound containing a partial structure represented by any of the following formulas is preferred.

[0472] In particular, polycyclic aromatic compounds containing a partial structure represented by formula (EH-1b-N1) have a high E Ｓ１ , high E Ｔ１ , small ΔE Ｓ１Ｔ１ Specific examples of the polycyclic aromatic compound represented by formula (EH-1b) are shown below.

[0473]

[0474]

[0475] [Combination of Hole-Transporting Host Material and Electron-Transporting Host Material] The combination of the hole-transporting host material and the electron-transporting host material is such that the HOMO, LUMO, and lowest excited triplet energy level (E Ｔ１ Regarding the HOMO and LUMO, a combination is selected in which the HOMO (HH) of the hole-transporting host material is shallower than the HOMO (EH) of the electron-transporting host material, and the LUMO (EH) of the electron-transporting host material is deeper than the LUMO (HH) of the hole-transporting host material.

[0476] The hole-transporting host material and the electron-transporting host material may be combined to form an association called an exciplex. It is generally known that exciplexes are easily formed between a material with a relatively deep LUMO level and a material with a shallow HOMO level. The interaction between the hole-transporting host material and the electron-transporting host material, specifically, whether an exciplex is formed, can be determined by forming a single-layer film consisting of only the hole-transporting host material and the electron-transporting host material under the same conditions as those for forming the light-emitting layer, measuring the emission spectrum (fluorescence spectrum, phosphorescence spectrum), and comparing the obtained emission spectrum with the emission spectrum exhibited by each of the hole-transporting host material and the electron-transporting host material alone. This can be determined by the spectrum of a mixed film containing the hole-transporting host material and the electron-transporting host material exhibiting an emission wavelength different from both the spectrum of the film of the hole-transporting host material and the spectrum of the film of the electron-transporting host material. Specifically, a difference of 10 nm or more in the peak wavelength of the spectrum can be used as an indicator.

[0477] Specific examples of the combination of a hole-transporting host material and an electron-transporting host material that do not form an exciplex include the following combinations: Ｔ１ In order to satisfy the physical property values ​​of (1), the hole-transporting host material is preferably a compound having carbazole, dibenzofuran, dibenzothiophene, triarylamine, indolocarbazole, or benzoxazinophenoxazine as a partial structure, more preferably a compound having carbazole, dibenzofuran, or dibenzothiophene as a partial structure, and even more preferably a compound having carbazole as a partial structure. Similarly, the electron-transporting host material is preferably a compound having pyridine, triazine, phosphine oxide, benzofuropyridine, or dibenzoxasiline as a partial structure, more preferably a compound having triazine, phosphine oxide, benzofuropyridine, or dibenzoxasiline as a partial structure, and even more preferably a compound having triazine.

[0478] Specific examples of the combination of a hole-transporting host material and an electron-transporting host material that form an exciplex include the following combinations: Ｔ１ In order to satisfy the physical property values ​​of (1), the hole-transporting host material is preferably a compound having carbazole, triarylamine, indolocarbazole, or benzoxazinophenoxazine as a partial structure, more preferably a compound having triarylamine, indolocarbazole, or benzoxazinophenoxazine as a partial structure, and even more preferably a compound having triarylamine as a partial structure. Similarly, the electron-transporting host material is preferably a compound having pyridine, triazine, phosphine oxide, or benzofuropyridine as a partial structure, more preferably a compound having triazine, phosphine oxide, benzofuropyridine, or dibenzoxasiline as a partial structure, and even more preferably a compound having phosphine oxide or triazine.

[0479] <Dopant Material> As a dopant material that can be used other than the polycyclic aromatic compound of the present invention, known compounds can be used, and can be selected from a variety of materials depending on the desired emission color.Specific examples include fused ring derivatives of phenanthrene, anthracene, pyrene, tetracene, pentacene, perylene, naphthopyrene, dibenzopyrene, rubrene, and chrysene, benzoxazole derivatives, benzothiazole derivatives, benzimidazole derivatives, benzotriazole derivatives, oxazole derivatives, oxadiazole derivatives, thiazole derivatives, imidazole derivatives, thiadiazole derivatives, triazole derivatives, pyrazoline derivatives, stilbene derivatives, thiophene derivatives, and tetraphenylbutadiene. derivatives, cyclopentadiene derivatives, bisstyryl derivatives such as bisstyryl anthracene derivatives and distyrylbenzene derivatives (JP-A-1-245087), bisstyrylarylene derivatives (JP-A-2-247278), diazaindacene derivatives, furan derivatives, benzofuran derivatives, isobenzofuran derivatives such as phenylisobenzofuran, dimesitylisobenzofuran, di(2-methylphenyl)isobenzofuran, di(2-trifluoromethylphenyl)isobenzofuran, and phenylisobenzofuran coumarin derivatives such as dibenzofuran derivatives, 7-dialkylaminocoumarin derivatives, 7-piperidinocoumarin derivatives, 7-hydroxycoumarin derivatives, 7-methoxycoumarin derivatives, 7-acetoxycoumarin derivatives, 3-benzothiazolylcoumarin derivatives, 3-benzimidazolylcoumarin derivatives, and 3-benzoxazolylcoumarin derivatives, dicyanomethylenepyran derivatives, dicyanomethylenethiopyran derivatives, polymethine derivatives, cyanine derivatives, oxobenzanthracene derivatives, xanthene derivatives, rhodamine derivatives, conductors, fluorescein derivatives, pyrylium derivatives, carbostyril derivatives, acridine derivatives, oxazine derivatives, phenylene oxide derivatives, quinacridone derivatives, quinazoline derivatives, pyrrolopyridine derivatives, furopyridine derivatives, 1,2,5-thiadiazolopyrene derivatives, pyrromethene derivatives, perinone derivatives, pyrrolopyrrole derivatives, squarylium derivatives, violanthrone derivatives, phenazine derivatives, acridone derivatives, deazaflavin derivatives, fluorene derivatives, and benzofluorene derivatives.

[0480] As the dopant material, it is also preferable to use the boron-containing polycyclic aromatic compounds described in WO 2015 / 102118, WO 2020 / 162600, paragraphs 0097 to 0269 of JP 2021-077890, etc. The above-mentioned dopant materials can also be used as light-emitting layer materials in the form of polymer compounds obtained by polymerizing a reactive compound substituted with a reactive substituent as a monomer, or a crosslinked polymer thereof, or a pendant polymer compound obtained by reacting a main-chain polymer with the reactive compound, or a crosslinked pendant polymer thereof. In this case, the reactive substituent can be as described for the polycyclic aromatic compound represented by formula (1).

[0481] <Assisting dopant (thermally activated delayed fluorescent material or phosphorescent material)> The light-emitting layer preferably contains an assisting dopant together with the emitting dopant and the host material. The assisting dopant is preferably a thermally activated delayed fluorescent material or a phosphorescent material. The polycyclic aromatic compound of the present invention can be preferably used as an emitting dopant in a TAF element or a PSF element.

[0482] In this embodiment, known host compounds can be used, such as compounds having at least one of a carbazole ring and a furan ring. Among these, it is preferable to use a compound in which at least one of furanyl and carbazolyl is bonded to at least one of arylene and heteroarylene. Specific examples include mCP (1,3-bis(N-carbazol-9-yl)benzene) and mCBP (3,3'-di(9H-carbazol-9-yl)-1,1'-biphenyl). A TADF-active compound may also be used as the host compound. In this embodiment, it is also preferable to use a combination of a hole-transporting host material and an electron-transporting host material (e.g., compounds HH-1-115 and EH-1-99) as the host.

[0483] The lowest excited triplet energy level E(1,T,Sh), determined from the shoulder on the short-wavelength side of the peak of the phosphorescence spectrum of the host compound, is preferably higher than the lowest excited triplet energy levels E(2,T,Sh) or E(3,T,Sh) of the emitting dopant or assisting dopant having the highest lowest excited triplet energy level in the emitting layer, from the viewpoint of promoting without inhibiting the generation of TADF in the emitting layer. Specifically, the lowest excited triplet energy level E(1,T,Sh) of the host compound is preferably higher than E(2,T,Sh) or E(3,T,Sh) by 0.01 eV or more, more preferably by 0.03 eV or more, and even more preferably by 0.1 eV or more. Furthermore, the lowest excited triplet energy level E of the host material is preferably 2.70 eV or more, more preferably 2.73 eV or more, and even more preferably 2.80 eV or more.

[0484] [Thermally activated delayed fluorescent substance] "Thermally activated delayed fluorescent substance" refers to a compound that absorbs thermal energy to undergo reverse intersystem crossing from the lowest excited triplet state to the lowest excited singlet state, and then radiatively deactivates from the lowest excited singlet state to emit delayed fluorescence. However, "thermally activated delayed fluorescent substance" also includes compounds that undergo a higher triplet state during the excitation process from the lowest excited triplet state to the lowest excited singlet state. In the present invention, when a sample containing the target compound is measured for its fluorescence lifetime at 300 K, if a slow fluorescent component is observed, the target compound is determined to be a "thermally activated delayed fluorescent substance." Here, the slow fluorescent component refers to a compound with a fluorescence lifetime of 0.1 μsec or more.

[0485] In an emitting layer further comprising a "thermally activated delayed phosphor" as an assisting dopant, the polycyclic aromatic compound of the present invention can function as an emitting dopant. That is, the "thermally activated delayed phosphor" can function as an assisting dopant that assists the emission of the polycyclic aromatic compound of the present invention. In this specification, an organic electroluminescent device using a thermally activated delayed phosphor as an assisting dopant may be referred to as a "TAF element" (TADF Assisting Fluorescence element). The "host compound" in the TAF element refers to a compound whose lowest excited singlet energy level, determined from the shoulder on the short-wavelength side of the peak of the fluorescence spectrum, is higher than that of the thermally activated delayed phosphor as an assisting dopant and the emitting dopant.

[0486] The thermally activated delayed fluorescent substance (TADF compound) used in the TAF element is preferably a donor-acceptor type thermally activated delayed fluorescent substance (DA type TADF compound) designed to localize the HOMO (highest occupied molecular orbital) and LUMO (lowest unoccupied molecular orbital) in the molecule using an electron-donating substituent called a donor and an electron-accepting substituent called an acceptor, thereby causing efficient reverse intersystem crossing.

[0487] In this specification, the term "electron-donating substituent" (donor) refers to a substituent or partial structure in which HOMO is localized in a thermally activated delayed fluorescent substance molecule, and the term "electron-accepting substituent" (acceptor) refers to a substituent or partial structure in which LUMO is localized in a thermally activated delayed fluorescent substance molecule.

[0488] In general, thermally activated delayed fluorescent materials using donors or acceptors have large spin-orbit coupling (SOC) due to their structure, and small exchange interaction between HOMO and LUMO, resulting in a low ΔE Ｓ１Ｔ１Since the value is small, a very fast reverse intersystem crossing rate can be obtained.By using the polycyclic aromatic compound of the present invention as an emitting dopant and a thermally activated delayed phosphor (TADF material) as an assisting dopant, it is possible to obtain a device that satisfies any one or all of high efficiency, high color purity, and long life.The thermally activated delayed phosphor may be a compound whose emission spectrum at least partially overlaps with the absorption spectrum of the polycyclic aromatic compound of the present invention.The polycyclic aromatic compound of the present invention and the TADF compound may both be contained in the same layer, or in adjacent layers or other adjacent layers.

[0489] The thermally activated delayed phosphor in the TAF element can be, for example, a compound in which a donor and an acceptor are bonded directly or via a spacer.The electron-donating group (donor structure) and the electron-accepting group (acceptor structure) used in the thermally activated delayed phosphor of the present invention can be, for example, the structure described in Chemistry of Materials, 2017, 29, 1946-1963. Examples of donor structures include carbazole, dimethylcarbazole, di-tert-butylcarbazole, dimethoxycarbazole, tetramethylcarbazole, benzofluorocarbazole, benzothienocarbazole, phenyldihydroindolocarbazole, phenylbicarbazole, bicarbazole, tercarbazole, diphenylcarbazolylamine, tetraphenylcarbazolyldiamine, phenoxazine, dihydrophenazine, phenothiazine, dimethyldihydroacridine, diphenylamine, bis(tert-butylphenyl)amine, N1-(4-(diphenylamino)phenyl)-N4,N4-diphenylbenzene-1,4-diamine, dimethyltetraphenyldihydroacridinediamine, tetramethyl-dihydro-indenoacridine, and diphenyl-dihydrodibenzazasiline.Examples of acceptor structures include sulfonyldibenzene, benzophenone, phenylenebis(phenylmethanone), benzonitrile, isonicotinonitrile, phthalonitrile, isophthalonitrile, paraphthalonitrile, benzenetricarbonitrile, triazole, oxazole, thiadiazole, benzothiazole, benzobis(thiazole), benzoxazole, benzobis(oxazole), quinoline, benzimidazole, dibenzoquinoxaline, heptaazaphenalene, thioxanthone dioxide, dimethylanthracenone, anthracenedione, 5H-cyclopenta[1,2-b:5,4-b']dipyridine, fluorene dicarbonitrile, triphenyltriazine, pyrazine dicarbonitrile, pyrimidine, phenylpyrimidine, methylpyrimidine, pyridine dicarbonitrile, dibenzoquinoxaline dicarbonitrile, bis(phenylsulfonyl)benzene, dimethylthioxanthene dioxide, thianthrene tetraoxide, 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 partial structure selected from carbazole, phenoxazine, acridine, triazine, pyrimidine, pyrazine, thioxanthene, benzonitrile, phthalonitrile, isophthalonitrile, diphenyl sulfone, triazole, oxadiazole, thiadiazole, and benzophenone.

[0490] The compound used as the assisting dopant of the luminescent layer in the TAF element is preferably a thermally activated delayed phosphor, and its emission spectrum is at least partially overlapped with the absorption peak of the emitting dopant.The following will be exemplified compounds that can be used as the thermally activated delayed phosphor of the luminescent layer in the TAF element.However, the compounds that can be used as the thermally activated delayed phosphor in the TAF element are not limited to the following exemplified compounds.

[0491]

[0492]

[0493]

[0494]

[0495]

[0496] Furthermore, as the thermally activated delayed phosphor, a compound represented by any one of the following formulae (AD1), (AD2) and (AD3) can also be used.

[0497] In the above formulae (AD1), (AD2) and (AD3), M each independently represents a single bond, —O—, >N—Ar or >CAR ２ and is preferably a single bond, -O-, or >N-Ar from the viewpoint of the depth of the HOMO and the height of the lowest excited singlet energy level and the lowest excited triplet energy level of the partial structure to be formed. J is a spacer structure separating the donor partial structure and the acceptor partial structure, and each J is independently an arylene having 6 to 18 carbon atoms. From the viewpoint of the magnitude of conjugation exuding from the donor partial structure and the acceptor partial structure, an arylene having 6 to 12 carbon atoms is preferred. More specific examples include phenylene, methylphenylene, and dimethylphenylene. Q is each independently ═C(—H)— or ═N—, and is preferably ═N— from the viewpoint of the shallowness of the LUMO and the height of the lowest excited singlet energy level and the lowest excited triplet energy level of the partial structure to be formed. Each Ar is independently hydrogen, aryl having 6 to 24 carbon atoms, heteroaryl having 2 to 24 carbon atoms, alkyl having 1 to 12 carbon atoms, or cycloalkyl having 3 to 18 carbon atoms. Furthermore, at least one hydrogen atom in the compounds represented by each of the above formulas may be substituted with halogen or deuterium.

[0498] More specifically, the compound used as the second component of the light-emitting layer in the TAF element 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, or DCzmCzTrz.

[0499] The compound used as the second component of the light-emitting layer in the TAF element may be a donor-acceptor type TADF compound represented by D-A, in which one donor D and one acceptor A are bonded directly or via a linking group, but a compound having a structure represented by the following formula (DAD1), in which multiple donors D are bonded to one acceptor A via a direct bond or a linking group, is preferred because it will result in better properties for the organic electroluminescent element. (D １ -L １ ) n-A １ (DAD1) Formula (DAD1) includes compounds represented by the following formula (DAD2): ２ -L ２ -A ２ -L ３ -D ３ (DAD2) In the formula (DAD1) and the formula (DAD2), D １ , D ２ and D ３ Each independently represents a donor group. As the donor group, the above-described donor structure can be used. １ and A ２ Each of L independently represents an acceptor group. As the acceptor group, the above-described acceptor structure can be used. １ , L ２ and L ３each independently represents 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 having 6 to 18 carbon atoms, more preferably an arylene having 6 to 12 carbon atoms. １ , L ２ and L ３ It is more preferable that each of A is independently phenylene, methylphenylene or dimethylphenylene. １ represents an integer equal to or less than the maximum number of substitutions that can be made. For example, n may be selected within the range of 2 to 10, or within the range of 2 to 6. When n is 2, the compound is represented by formula (DAD2). １ may be the same or different, and n L １ and may be the same or different. Preferred specific examples of the compounds represented by formula (DAD1) and formula (DAD2) include 2PXZ-TAZ and the following compounds, but the second component that can be used in the present invention is not limited to these compounds.

[0500]

[0501] [Phosphorescent Material] In the light-emitting layer, a phosphorescent material may be used as an assisting dopant. In this specification, an organic electroluminescent device using a phosphorescent material as an assisting dopant is sometimes referred to as a phosphorescence-assisted element, a phosphor-sensitized fluorescent element, or a PSF element. Phosphorescent materials utilize the intramolecular spin-orbit interaction (heavy atom effect) of metal atoms to obtain light emission from an excited triplet state. As such phosphorescent materials, for example, luminescent metal complexes can be used. Examples of luminescent metal complexes include compounds represented by the following formulas (B-1) and (B-2):

[0502]

[0503] In formula (B-1), M is at least one selected from the group consisting of Ir, Pt, Au, Eu, Ru, Re, Ag, and Cu, n is an integer of 1 to 3, and each "X-Y" is independently a bidentate ligand. In formula (B-2), M is at least one selected from the group consisting of Pt, Re, and Cu, and "W-X-Y-Z" is a tetradentate ligand. In formula (B-1), from the viewpoints of efficiency and life, M is preferably Ir, and n is preferably 3. In formula (B-2), M is preferably Pt from the viewpoints of efficiency and life. The ligand (X-Y) in formula (B-1) has at least one ligand selected from the group consisting of the following. The ligand (W-X-Y-Z) in formula (B-2) has at least one ligand selected from the group consisting of the following as a part.

[0504]

[0505] In the formula, Y is bonded to the central metal M at ---, and each Y is independently BR ｅ , N.R. ｅ , P.R. ｅ , O, S, Se, C=O, S=O, SO ２ , C.R. ｅ R ｆ , SiR ｅ R ｆ , or GeR ｅ R ｆ each aromatic carbon C—H in the ring may be independently substituted with N; R ｅ and R ｆ may be optionally fused or linked to form a ring, R ａ , R ｂ , R ｃ , and R ｄ may each independently be unsubstituted or substituted with from 1 to the maximum number of possible substitutions; ａ , R ｂ , R ｃ , R ｄ , R ｅ , and R ｆare each independently hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, or a combination thereof, with the proviso that R ａ , R ｂ , R ｃ , and R ｄ Any two adjacent substituents in may be fused or linked to form a ring or to form a multidentate ligand.

[0506] Examples of the compound represented by formula (B-1) include Ir(ppy) ３ , Ir(ppy) ２ (acac), Ir(mppy) ３ , Ir(PPy) ２ (m-bppy), BtpIr(acac), Ir(btp) ２ (acac), Ir(2-phq) ３ , Hex-Ir(phq) ３ , Ir(fbi) ２ (acac), fac-Tris(2-(3-p-xylyl)phenyl)pyridine iridium(III), Eu(dbm) ３ (Phen), Ir (piq) ３ , Ir(piq) ２ (acac), Ir(Fliq) ２ (acac), Ir(Flq) ２ (acac), Ru (dtb-bpy) ３ ・2 (PF ６ ), Ir(2-phq) ３ , Ir(BT) ２ (acac), Ir(DMP) ３ , Ir(Mphq) ３ IR (phq) ２ tpy, fac-Ir(ppy) ２ Pc, Ir(dp)PQ ２ , Ir(Dpm)(Piq) ２ , Hex-Ir(piq) ２ (acac), Hex-Ir (piq) ３, Ir(dmpq) ３ , Ir(dmpq) ２ (acac), FPQIrpic, etc.

[0507] Other examples of the compound represented by formula (B-1) include the following compounds:

[0508]

[0509]

[0510] <2-1-3. Anode in Organic Electroluminescent Device> The anode 102 serves to inject holes into the light-emitting layer 105. When either the hole injection layer 103 or the 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 via the hole injection layer 103 or the hole transport layer 104.

[0511] The resistance of the transparent electrode is not limited as long as it can supply a current sufficient for the light emitting element to emit light, but a low resistance is desirable from the viewpoint of the power consumption of the light emitting element.

[0512] <2-1-4. Hole Injection Layer and Hole Transport Layer in Organic Electroluminescent Device> The hole injection layer 103 serves to efficiently inject holes migrating from the anode 102 into the light-emitting layer 105 or the hole transport layer 104. The hole transport layer 104 serves to efficiently transport holes injected from the anode 102 or holes injected from the anode 102 via the hole injection layer 103 to the light-emitting layer 105. The hole injection layer 103 and the hole transport layer 104 are each formed by laminating or mixing one or more hole injection / transport materials, or by a mixture of a hole injection / transport material and a polymer binder. Alternatively, a layer may be formed by adding a p-type dopant such as iron(III) chloride to the hole injection / transport material.

[0513] As materials for forming the hole injection layer 103 and the hole transport layer 104, any compound can be selected from compounds conventionally used as charge transport materials for holes in photoconductive materials, p-type semiconductors, and known compounds used in hole injection layers and hole transport layers of organic EL elements.

[0514] It is also known that the conductivity of organic semiconductors is strongly affected by their doping. Such organic semiconductor matrix materials are composed of compounds with good electron-donating or electron-accepting properties. Strong electron acceptors such as tetracyanoquinone dimethane (TCNQ) or 2,3,5,6-tetrafluorotetracyano-1,4-benzoquinone dimethane (F4TCNQ) are known for doping with electron-donating substances.

[0515] <2-1-5. Electron Blocking Layer in Organic Electroluminescent Device> An electron blocking layer that prevents diffusion of electrons from the light-emitting layer may be provided between the hole injection / transport layer and the light-emitting layer. The electron blocking layer may be formed using a compound represented by any one of the above formulas (H1), (H2), and (H3). The polycyclic aromatic compound of the present invention may be used as a material for forming the electron blocking layer.

[0516] <2-1-6. Electron Injection Layer and Electron Transport Layer in Organic Electroluminescent Device> The electron injection layer 107 plays a role of efficiently injecting electrons moving from the cathode 108 into the light-emitting layer 105 or the electron transport layer 106. The electron transport layer 106 plays a role of efficiently transporting electrons injected from the cathode 108 or electrons injected from the cathode 108 via the electron injection layer 107 to the light-emitting layer 105. The electron transport layer 106 and the electron injection layer 107 are each formed by laminating or mixing one or more electron transport / injection materials, or by a mixture of an electron transport / injection material and a polymer binder.

[0517] The material (electron transport material) forming the electron transport layer 106 or the electron injection layer 107 can be arbitrarily selected from compounds conventionally used as electron transport compounds in photoconductive materials and known compounds used in the electron injection layer and electron transport layer of organic EL devices. In this specification, materials used for the electron injection layer and electron transport layer are collectively referred to as "electron transport compounds." The materials used for the electron injection layer and the electron transport layer may be the same or different.

[0518] The material used in the electron transport layer or the electron injection layer preferably contains at least one selected from the group consisting of a compound having an aromatic ring or a heteroaromatic ring constituted by one or more atoms selected from carbon, hydrogen, oxygen, sulfur, silicon, and phosphorus, a pyrrole derivative and a fused ring derivative thereof, and a metal complex having an electron-accepting nitrogen.

[0519] Specific examples of other electron transport compounds include pyridine derivatives, naphthalene derivatives, fluoranthene derivatives, BO derivatives, anthracene derivatives, phenanthroline derivatives, perinone derivatives, coumarin derivatives, naphthalimide derivatives, anthraquinone derivatives, diphenoquinone derivatives, diphenylquinone derivatives, perylene derivatives, oxadiazole derivatives (e.g., 1,3-bis[(4-t-butylphenyl)1,3,4-oxadiazolyl]phenylene), thiophene derivatives, triazole derivatives (e.g., N-naphthyl-2,5-diphenyl-1,3,4-triazole), thiadiazole derivatives, metal complexes of oxine derivatives, quinolinol metal complexes, quinoxaline derivatives, polymers of quinoxaline derivatives, benzazole compounds, gallium complexes, pyrazole derivatives, perfluorinated phenylene derivatives, triazine derivatives, pyrazine derivatives, benzoquinone Examples of the derivatives include phosphorus 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), aldazine derivatives, pyrimidine derivatives, arylnitrile derivatives, indole derivatives, phosphine oxide derivatives, bisstyryl derivatives, silole derivatives, and azoline derivatives.

[0520] Metal complexes having an electron-accepting nitrogen atom can also be used, and examples thereof include hydroxyazole complexes such as quinolinol metal complexes and hydroxyphenyloxazole complexes, azomethine complexes, tropolone metal complexes, flavonol metal complexes, and benzoquinoline metal complexes.

[0521] The above-mentioned materials may be used alone or in combination with other materials.

[0522] Among the above-mentioned materials, borane derivatives, pyridine derivatives, fluoranthene derivatives, BO-based derivatives, anthracene derivatives, benzofluorene derivatives, phosphine oxide derivatives, pyrimidine derivatives, arylnitrile derivatives, triazine derivatives, benzimidazole derivatives, phenanthroline derivatives, quinolinol-based metal complexes, thiazole derivatives, benzothiazole derivatives, silole derivatives, and azoline derivatives are preferred.

[0523] The polycyclic aromatic compound of the present invention may be used as a material for forming an electron injection layer or an electron transport layer.

[0524] The electron transport layer or the electron injection layer may further contain a substance capable of reducing the material forming the electron transport layer or the electron injection layer. Various substances can be used as this reducing substance as long as they have a certain level of reducing ability. For example, at least one selected from the group consisting of alkali metals, alkaline earth metals, rare earth metals, alkali metal oxides, alkali metal halides, alkaline earth metal oxides, alkaline earth metal halides, rare earth metal oxides, rare earth metal halides, alkali metal organic complexes, alkaline earth metal organic complexes, and rare earth metal organic complexes can be suitably used.

[0525] Preferred reducing substances include alkali metals such as Na (work function 2.36 eV), K (2.28 eV), Rb (2.16 eV), and Cs (1.95 eV), and alkaline earth metals such as Ca (2.9 eV), Sr (2.0 to 2.5 eV), and Ba (2.52 eV), with substances having a work function of 2.9 eV or less being particularly preferred.

[0526] <2-1-7. Cathode in Organic Electroluminescent Device> The cathode 108 plays a role in injecting electrons into the light-emitting layer 105 via the electron injection layer 107 and the electron transport layer 106 .

[0527] The material for forming the cathode 108 is not particularly limited as long as it is a substance that can efficiently inject electrons into the organic layer, and the same materials as those for forming the anode 102 can be used. Among these, metals such as tin, indium, calcium, aluminum, silver, copper, nickel, chromium, gold, platinum, iron, zinc, lithium, sodium, potassium, cesium, and magnesium, or alloys thereof (such as magnesium-silver alloys, magnesium-indium alloys, and aluminum-lithium alloys such as lithium fluoride / aluminum), are preferred.

[0528] <2-1-8. Method for producing organic electroluminescence device> Each layer constituting an organic EL device can be formed by forming the material to be constituting each layer into a thin film by a method such as vapor deposition, resistance heating vapor deposition, electron beam vapor deposition, sputtering, molecular lamination, printing, inkjet printing, spin coating or casting, coating, etc. The film thickness of each layer thus formed is not particularly limited and can be set appropriately depending on the properties of the material.

[0529] Next, as an example of a method for fabricating an organic EL device, we will explain a method for fabricating an organic EL device consisting of an anode, a hole injection layer, a hole transport layer, an emitting layer composed of a host material and a dopant material, an electron transport layer, an electron injection layer, and a cathode. A thin film of an anode material is formed on a suitable substrate by vapor deposition or other methods to form an anode, and then a thin film of a hole injection layer and a hole transport layer is formed on the anode. A thin film of a host material and a dopant material is co-deposited on the anode to form an emitting layer. An electron transport layer and an electron injection layer are then formed on the emitting layer, and a thin film of a cathode material is further formed by vapor deposition or other methods to form a cathode, thereby obtaining the desired organic EL device. It should be noted that the above-described organic EL device can also be fabricated in the reverse order, i.e., cathode, electron injection layer, electron transport layer, emitting layer, hole transport layer, hole injection layer, and anode.

[0530] <2-1-9. Application Examples of Organic Electroluminescent Devices> Organic EL elements can also be applied to display devices, lighting devices, etc. Display devices or lighting devices including organic EL elements can be manufactured by a known method, such as by connecting the organic EL elements to a known driving device, and can be driven appropriately using a known driving method, such as DC driving, pulse driving, or AC driving.

[0531] <2-2. Other Organic Devices> The polycyclic aromatic compound according to the present invention can be used to produce organic field effect transistors, organic thin-film solar cells, and the like, in addition to the organic electroluminescent devices described above.

[0532] <3. Wavelength Conversion Material> The polycyclic aromatic compound of the present invention can be used as a wavelength conversion material. Currently, the application of multicolor technology using color conversion methods to liquid crystal displays, organic electroluminescence (EL) displays, lighting, and the like is being actively investigated. Color conversion refers to the wavelength conversion of light emitted from an illuminant to light of a longer wavelength, for example, converting ultraviolet or blue light to green or red light. By forming this wavelength conversion material with color conversion function into a film and combining it with, for example, a blue light source, it becomes possible to extract the three primary colors of blue, green, and red from the blue light source, i.e., to extract white light. By combining such a blue light source with a wavelength conversion film with color conversion function as a light source unit, and combining it with a liquid crystal drive unit and a color filter, it becomes possible to fabricate a full-color display. Furthermore, if there is no liquid crystal drive unit, it can be used as a white light source as is, and can be applied as a white light source for, for example, LED lighting. Furthermore, by using a blue organic EL element as a light source in combination with a wavelength conversion film that converts blue light to green and red light, it becomes possible to fabricate a full-color organic EL display without using a metal mask. Furthermore, by using blue micro-LEDs as a light source in combination with wavelength conversion films that convert blue light into green and red light, it becomes possible to create low-cost full-color micro-LED displays.

[0533] The present invention will be described in more detail below with reference to examples, but is not limited thereto. In the examples, "APCI-MS" means atmospheric pressure chemical ionization mass spectrometry, "MALDI-TOF-MS" means matrix-assisted laser desorption / ionization mass spectrometry, and "FT-ICR MALDI-TOF-MS" means Fourier transform ion cyclotron resonance mass spectrometry.

[0534] <<Synthesis Examples>> Synthesis Example (1): Synthesis of Compound (1-1)

[0535] Under a nitrogen atmosphere, a flask containing 2-bromo-4-(t-butyl)aniline (35.0 g), m-chlorophenylboronic acid (26.4 g), palladium acetate (1.0 g), potassium carbonate (25.4 g), SPhos (dicyclohexyl(2',6'-dimethoxy-[1,1'-biphenyl]-2-yl)phosphine, 3.8 g), TBAB (tetrabutylammonium bromide, 4.9 g), CPME (cyclopentyl methyl ether, 400 ml), and water (40 ml) was stirred at reflux temperature for 6 hours. The reaction solution was cooled to room temperature, and water was added thereto to separate the organic layer, which was then washed with water. The organic layer was concentrated under reduced pressure and purified on silica gel using toluene and heptane, yielding 29.1 g of intermediate (Int-1-1).

[0536]

[0537] Under a nitrogen atmosphere, intermediate (Int-1-1-1) (25.0 g), 4-(t-butyl)iodobenzene (30.0 g), Pd-132 (dichlorobis[di-t-butyl(4-dimethylaminophenyl)phosphino]palladium(II), 2.0 g), NaOtBu (13.9 g), and toluene (300 mL) were stirred at 90°C for 1 hour. After the reaction, water and toluene were added and the mixture was stirred, and then the organic layer was washed twice with water and concentrated to obtain a crude product, which was purified using a silica gel column (eluent: toluene / heptane) to obtain 31.2 g of intermediate (Int-1-1-2).

[0538]

[0539] Under a nitrogen atmosphere, intermediate (Int-1-1-2) (33.4 g), 1-(t-butyl)-3,5-diiodobenzene (15.0 g), Pd-132 (0.8 g), NaOtBu (9.3 g), and toluene (400 mL) were stirred at 70° C. for 2 hours. After the reaction, water and toluene were added and the mixture was stirred. The organic layer was washed twice with water and concentrated to obtain a crude product, which was purified using a silica gel column (eluent: toluene / heptane) to obtain 22.2 g of intermediate (Int-1-1-3).

[0540]

[0541] Under a nitrogen atmosphere, boron tribromide (32.9 g) was added to a flask containing intermediate (Int-1-1-3) (15.0 g) and ortho-dichlorobenzene (150 ml) at room temperature. After the dropwise addition was completed, the temperature was raised to 180°C and the mixture was stirred for 24 hours. Thereafter, the mixture was cooled again to room temperature, and N,N-diisopropylethylamine (10.6 g) was added and stirred until the heat generation subsided. Thereafter, the reaction solvent was distilled off under reduced pressure at 60°C. Next, the mixture was filtered using silica gel (eluent: toluene), and the solvent was distilled off under reduced pressure to obtain a crude product. The obtained crude product was purified using silica gel column chromatography (eluent: toluene / hexane) to obtain 1.3 g of intermediate (Int-1-1).

[0542]

[0543] Under a nitrogen atmosphere, a flask containing intermediate (Int-1-1) (1.0 g), 1,3-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene (0.54 g), palladium acetate (24 mg), potassium carbonate (0.30 g), SPhos (89 mg), TBAB (70 mg), CPME (30 ml), and water (3 ml) was stirred at reflux temperature for 18 hours. The reaction solution was cooled to room temperature, and water was added to separate the organic layer, which was then washed with water. The organic layer was concentrated under reduced pressure, and the resulting solid was purified on silica gel using toluene and heptane to obtain 0.017 g of compound (1-1).

[0544]

[0545] APCI-MS revealed m / z (M+H)=927.58, confirming the production of the target product.

[0546] Alternatively, compound (1-1) can also be synthesized by the following method. Under a nitrogen atmosphere, toluene (2.0 ml) and N,N-dimethylacetamide (2.0 ml) were added to a Schlenk tube containing intermediate (Int-1-1) (98 mg, 0.11 mmol), 4,4,5,5-tetramethyl-2-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]1,3,2-dioxaborolane (37 mg, 0.11 mmol), tripotassium phosphate (142 mg, 0.67 mmol), and dichlorobis[di-tert-butyl(p-dimethylaminophenyl)phosphino]palladium(II) (17 mg, 0.024 mmol) at room temperature. The mixture was stirred at room temperature for 15 minutes and then at 90°C for 20 hours. The mixture was then filtered under reduced pressure using silica gel as a filter aid and toluene as an eluent to obtain a crude product. The obtained crude product was subjected to reverse-phase silica gel column chromatography (developing solvent: acetonitrile / dichloromethane=9 / 1) to obtain compound (1-1), 3,21,27,31,39-penta-tert-butyl-24,29,34-[1,2,3]benzeno-5,9:10,14:15,19-tri(metheno)tetrabenzo[b,e,h,y][1,7]diaza[4]boracyclohexacosine (7 mg, yield 7%), as a yellow solid.

[0547] The structure of compound (1-1), 3,21,27,31,39-penta-tert-butyl-24,29,34-[1,2,3]benzeno-5,9:10,14:15,19-tri(metheno)tetrabenzo[b,e,h,y][1,7]diaza[4]boracyclohexacosine, was confirmed by NMR measurement and mass spectrometry. １ H-NMR (495MHz, CD ３CN): δ = 0.95 (s, 9H), 1.34 (s, 18H), 1.49 (s, 18H), 6.09 (s, 1H), 6.48 (s, 2H), 6.64 (d, J = 9.1 HRMS (MALDI-TOF / MS) m / z [M] ＋　 C ６８ H ７１ BN ２ Calculated value 926.5705, measured value 926.5746.

[0548] Synthesis Example (2): Synthesis of Compound (1-10)

[0549] Under a nitrogen atmosphere, 3-chloro-4-(t-butyl)aniline (25.0 g), 4-(t-butyl)iodobenzene (42.5 g), Pd-132 (2.9 g), NaOtBu (19.6 g), and toluene (500 mL) were stirred for 1 hour at 70° C. After the reaction, water and toluene were added and stirred, and then the organic layer was concentrated. The resulting crude product was purified using a silica gel column (eluent: toluene / heptane) to obtain 31.2 g of intermediate (Int-1-10-1).

[0550]

[0551] Under a nitrogen atmosphere, intermediate (Int-1-10-1) (27.3 g), 1-(t-butyl)-3,5-diiodobenzene (15.0 g), Pd-132 (0.8 g), NaOtBu (9.4 g), and toluene (500 mL) were stirred at 70° C. for 2 hours under a nitrogen atmosphere. After the reaction, water and toluene were added and the mixture was stirred, and then the organic layer was washed twice with water and concentrated to obtain a crude product. The crude product was purified using a silica gel short column (eluent: toluene / heptane) to obtain 26.9 g of intermediate (Int-1-10-2).

[0552]

[0553] Under a nitrogen atmosphere, boron tribromide (39.5 g) was added to a flask containing intermediate (Int-1-10-2) (15.0 g) and ortho-dichlorobenzene (200 ml) at room temperature. After the dropwise addition was completed, the temperature was raised to 180°C and the mixture was stirred for 24 hours. The mixture was then cooled to room temperature again, and N,N-diisopropylethylamine (13.0 g) was added, followed by stirring until the heat generation subsided. The reaction solvent was then distilled off. The mixture was then filtered using silica gel (eluent: toluene), and the solvent was distilled off under reduced pressure to obtain a crude product. The obtained crude product was purified by silica gel column chromatography (eluent: toluene / hexane) to obtain intermediate (Int-1-10-3) (3.9 g).

[0554]

[0555] Under a nitrogen atmosphere, intermediate (Int-1-10-3) (3.0 g), intermediate (Int-1-10-3-2) (2.0 g), Pd-132 (0.17 g), NaOtBu (0.56 g), and toluene (500 mL) were stirred at reflux temperature for 42 hours. After the reaction, water and toluene were added and the mixture was stirred. The organic layer was concentrated, and the resulting crude product was purified using a silica gel column (eluent: toluene / heptane) to obtain 0.069 g of compound (1-10).

[0556]

[0557] By APCI-MS, m / z (M+H)=1124.67 was observed, confirming the production of the target product.

[0558] Synthesis Example (3): Synthesis of Compound (1-12)

[0559] Under a nitrogen atmosphere, 2-chloro-4-(t-butyl)aniline (30.0 g), 4-(t-butyl)iodobenzene (51.0 g), Pd-132 (3.5 g), NaOtBu (23.5 g), and toluene (500 mL) were stirred for 5 hours at 70° C. After the reaction, water and toluene were added and stirred, and then the organic layer was concentrated. The resulting crude product was purified using a silica gel column (eluent: toluene / heptane) to obtain 46.9 g of intermediate (Int-1-12-1).

[0560]

[0561] Under a nitrogen atmosphere, intermediate (Int-1-12-1) (45.0 g), 1-(t-butyl)-3,5-diiodobenzene (25.0 g), Pd-132 (1.38 g), NaOtBu (15.6 g), and toluene (400 mL) were stirred for 2 hours at 70° C. After the reaction, water and toluene were added and the mixture was stirred, and then the organic layer was concentrated. The resulting crude product was purified using a silica gel column (eluent: toluene / heptane) to obtain 44.2 g of intermediate (Int-1-12-2).

[0562]

[0563] Under a nitrogen atmosphere, boron tribromide (105.2 g) was added to a flask containing intermediate (Int-1-12-2) (40.0 g) and ortho-dichlorobenzene (500 ml) at room temperature. After the dropwise addition was completed, the temperature was raised to 180°C and the mixture was stirred for 24 hours. The mixture was then cooled to room temperature again, and N,N-diisopropylethylamine (34.0 g) was added, followed by stirring until the heat generation subsided. The reaction solvent was then distilled off under reduced pressure. The resulting crude product was purified by silica gel column chromatography (eluent: toluene / hexane) to obtain intermediate (Int-12-3) (16.9 g).

[0564]

[0565] Under a nitrogen atmosphere, a flask containing intermediate (Int-1-12-3) (16.0 g), (3-(4-penten-1-yloxy)phenyl)boronic acid (12.9 g), palladium acetate (0.47 g), SPhos (1.71 g), potassium carbonate (14.4 g), TBAB (1.34 g), CPME (300 ml), and water (30 ml) was stirred at reflux temperature for 19 hours. The reaction solution was cooled to room temperature, and water was added thereto to separate the organic layer, which was then washed with water. The organic layer was concentrated under reduced pressure, and the resulting solid was purified on silica gel using toluene and heptane to obtain 19.3 g of intermediate (Int-1-12).

[0566]

[0567] 500 mL of dichloromethane was heated to reflux in a flask under a nitrogen atmosphere. Second-generation Grubbs catalyst (Grubbs 2nd, dichloro[1,3-bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene](benzylidene)(tricyclohexylphosphine)ruthenium(II), 0.12 g) was added to the flask, and a solution of intermediate (Int-1-12) (3.0 g) in 200 mL of dichloromethane was slowly added dropwise over 8 hours. After the dropwise addition was completed, the mixture was heated to reflux for an additional 15 hours. The reaction solution was allowed to cool to room temperature, and the solvent was distilled off under reduced pressure. The crude product was roughly purified using a silica gel short column (eluent: toluene) and then purified using a silica gel column (eluent: toluene / heptane) to obtain 0.012 g of compound (1-12).

[0568] APCI-MS showed m / z (M+H)=993.65, confirming the production of the target product.

[0569] Synthesis Example (4): Synthesis of Compound (1-13)

[0570] Compound (1-12) (1.0 g), Pd / C (N.E. ChemCat, Type STD, 0.05 g), 20 mL of toluene, and 10 mL of THF were placed in a 50 mL stainless steel autoclave, and hydrogen gas was then introduced until the pressure gauge indicated 3 atm. The reaction was allowed to proceed in the autoclave at 60°C for 24 hours. After the reaction, the autoclave was cooled to room temperature, the internal pressure was released, and the reaction mixture was filtered. The crude product was roughly purified using a silica gel short column (eluent: toluene) and then purified using a silica gel column (eluent: toluene / heptane), yielding 0.75 g of compound (1-13).

[0571] APCI-MS showed m / z (M+H)=995.66, confirming the production of the target product.

[0572] Synthesis Example (5): Synthesis of Compound (1-14)

[0573] Under a nitrogen atmosphere, intermediate (Int-1-14) (1.50 g) synthesized by the method described in Journal of the American Chemical Society, 2023, 145, 1505-1511, intermediate (Int-1-14-3-2) (1.77 g), Pd-132 (88 mg), NaOtBu (0.30 g), and toluene (500 mL) were stirred at 70° C. for 30 hours under a nitrogen atmosphere. After the reaction, water and toluene were added and stirred, and the organic layer was concentrated. The resulting crude product was purified using a silica gel column (eluent: toluene / heptane) to obtain 0.011 g of compound (1-14).

[0574]

[0575] APCI-MS revealed m / z (M+H)=1379.67, confirming the production of the target product.

[0576] Synthesis Example (6): Synthesis of Compound (1-15)

[0577] Under a nitrogen atmosphere, NMP (N-methylpyrrolidone, 5.6 mL), bis(tri-t-butylphosphine)palladium(0) (49 mg), and intermediate (Int-1-15) (3.0 g) were added to μ-1,4-butanediyldiiodide dizinc (0.5 M, THF solution, 9.8 mL) prepared by the method described in Chinese Patent Publication No. 101029052, and the mixture was stirred at 100° C. for 20 hours. After cooling to room temperature, 1 M aqueous hydrochloric acid was added to terminate the reaction, and water and toluene were added and stirred. The organic layer was then washed twice with water and concentrated. The resulting crude product was purified using a silica gel short column (eluent: toluene / heptane) to obtain 0.077 g of compound (1-15).

[0578]

[0579] APCI-MS revealed m / z (M+H)=907.61, confirming the production of the target product.

[0580] Synthesis Example (7): Synthesis of Compound (1-16) Compound (1-16) was obtained from intermediate (Int-1-16) in the same manner as in Synthesis Example (1).

[0581] APCI-MS showed m / z (M+H)=989.40, confirming the production of the target product.

[0582] Synthesis Example (8): Synthesis of Compound (1-17) Compound (1-17) was obtained from intermediate (Int-1-17) in the same manner as in Synthesis Example (1).

[0583] By APCI-MS, m / z (M+H)=1164.46 was observed, confirming the production of the target product.

[0584] Synthesis Example (9): Synthesis of Compound (1-18) Compound (1-18) was obtained from intermediate (Int-1-18) in the same manner as in Synthesis Example (1).

[0585] APCI-MS showed m / z (M+H)=960.54, confirming the production of the target product.

[0586] Synthesis Example (10): Synthesis of Compound (1-19) Compound (1-19) was obtained from intermediate (Int-1-19) in the same manner as in Synthesis Example (1).

[0587] APCI-MS showed m / z (M+H) = 829.43, confirming the production of the target product.

[0588] Synthesis Example (11): Synthesis of Compound (1-20) Compound (1-20) was obtained from intermediate (Int-1-20) in the same manner as in Synthesis Example (1).

[0589] APCI-MS showed m / z (M+H) = 889.47, confirming the production of the target product.

[0590] Synthesis Example (12): Synthesis of Compound (1-21) Compound (1-21) was obtained from intermediate (Int-1-21) in the same manner as in Synthesis Example (4).

[0591] By APCI-MS, m / z (M+H)=1021.58 was observed, confirming the production of the target product.

[0592] Synthesis Example (13): Synthesis of Compound (1-22) Compound (1-22) was obtained from intermediate (Int-1-22) in the same manner as in Synthesis Example (6).

[0593] By APCI-MS, m / z (M+H) = 1345.67 was observed, confirming the production of the target product.

[0594] Synthesis Example (14): Synthesis of Compound (1-23) Compound (1-23) was obtained from intermediate (Int-1-23) in the same manner as in Synthesis Example (6).

[0595] APCI-MS revealed m / z (M+H)=874.35, confirming the production of the target product.

[0596] Synthesis Example (15): Synthesis of Compound (1-24) Compound (1-24) was obtained from intermediate (Int-1-24) in the same manner as in Synthesis Example (1).

[0597] By APCI-MS, m / z (M+H)=1086.50 was observed, confirming the production of the target product.

[0598] Synthesis Example (16): Synthesis of Compound (1-25) Compound (1-25) was obtained from intermediate (Int-1-25) in the same manner as in Synthesis Example (1).

[0599] APCI-MS revealed m / z (M+H)=1083.67, confirming the production of the target product.

[0600] Synthesis Example (17): Synthesis of Compound (1-26) Compound (1-26) was obtained from intermediate (Int-1-26) in the same manner as in Synthesis Example (1).

[0601] APCI-MS revealed m / z (M+H)=957.62, confirming the production of the target product.

[0602] Synthesis Example (18): Synthesis of Compound (1-27) Compound (1-27) was obtained from intermediate (Int-1-27) in the same manner as in Synthesis Example (1).

[0603] APCI-MS revealed m / z (M+H)=939.50, confirming the production of the target product.

[0604] Synthesis Example (19): Synthesis of Compound (1-28) Compound (1-28) was obtained from intermediate (Int-1-28) in the same manner as in Synthesis Example (1).

[0605] APCI-MS revealed m / z (M+H)=1070.64, confirming the production of the target product.

[0606] Synthesis Example (20): Synthesis of Compound (1-61)

[0607] A flask was charged with intermediate (Int-1-61) (1.1 g, 1.00 equiv.) and THF (300 mL). The resulting solution was stirred until all solids dissolved, and bis(triphenylphosphine)palladium(II) dichloride (0.07 g, 0.100 equiv.) was added, followed by H ２ O (60 mL) was added, and potassium fluoride (0.06 g, 1 equivalent) was further added. This solution was stirred at room temperature for 30 hours in the air. After the reaction, the reaction mixture was filtered through Celite, and dichloromethane was further poured through the Celite. The resulting solution was washed successively with water and brine, dried over sodium sulfate, and the solvent was removed under reduced pressure to obtain a crude product. This crude product was purified by silica gel column chromatography (eluent: toluene / heptane) to obtain 0.03 g of compound (1-61).

[0608] APCI-MS revealed m / z (M+H)=851.55, confirming the production of the target product.

[0609] Synthesis Example (21): Synthesis of Compound (1-62) Compound (1-62) was obtained from intermediate (Int-1-62) in the same manner as in Synthesis Example (1).

[0610] By APCI-MS, m / z (M+H)=1091.49 was observed, confirming the production of the target product.

[0611] Synthesis Example (22): Synthesis of Compound (1-65) Compound (1-65) was obtained from intermediate (Int-1-65) in the same manner as in Synthesis Example (1).

[0612] APCI-MS showed m / z (M+H)=962.54, confirming the production of the target product.

[0613] Synthesis Example (23): Synthesis of Compound (1-66) Compound (1-66) was obtained from intermediate (Int-1-66) in the same manner as in Synthesis Example (1).

[0614] By APCI-MS, m / z (M+H)=1078.62 was observed, confirming the production of the target product.

[0615] Synthesis Example (24): Synthesis of Compound (1-67) Compound (1-67) was obtained from intermediate (Int-1-67) in the same manner as in Synthesis Example (1).

[0616] By APCI-MS, m / z (M+H)=1231.67 was observed, confirming the production of the target product.

[0617] Synthesis Example (25): Synthesis of Compound (1-68) Compound (1-68) was obtained from intermediate (Int-1-68) in the same manner as in Synthesis Example (1).

[0618] APCI-MS revealed m / z (M+H)=1203.63, confirming the production of the target product.

[0619] Synthesis Example (26): Synthesis of Compound (1-69) Compound (1-69) was obtained from intermediate (Int-1-69) in the same manner as in Synthesis Example (1).

[0620] By APCI-MS, m / z (M+H)=1332.61 was observed, confirming the production of the target product.

[0621] Synthesis Example (27): Synthesis of Compound (1-70) Compound (1-70) was obtained from intermediate (Int-1-70) in the same manner as in Synthesis Example (1).

[0622] APCI-MS revealed m / z (M+H)=1475.67, confirming the production of the target product.

[0623] Synthesis Example (28): Synthesis of Compound (1-71) Compound (1-71) was obtained from intermediate (Int-1-71) in the same manner as in Synthesis Example (1).

[0624] By APCI-MS, m / z (M+H)=1397.74 was observed, confirming the production of the target product.

[0625] Synthesis Example (29): Synthesis of Compound (1-72) Compound (1-72) was obtained from intermediate (Int-1-72) in the same manner as in Synthesis Example (1).

[0626] APCI-MS revealed m / z (M+H) = 1263.72, confirming the production of the target product.

[0627] Synthesis Example (30): Synthesis of Compound (1-73) Compound (1-73) was obtained from intermediate (Int-1-73) in the same manner as in Synthesis Example (1).

[0628] By APCI-MS, m / z (M+H)=1034.56 was observed, confirming the production of the target product.

[0629] Synthesis Example (31): Synthesis of Compound (1-75) Compound (1-75) was obtained from intermediate (Int-1-75) in the same manner as in Synthesis Example (1).

[0630] APCI-MS showed m / z (M+H)=979.43, confirming the production of the target product.

[0631] Synthesis Example (32): Synthesis of Compound (1-76) Compound (1-76) was obtained from intermediate (Int-1-76) in the same manner as in Synthesis Example (1).

[0632] APCI-MS revealed m / z (M+H)=790.35, confirming the production of the target product.

[0633] Synthesis Example (33): Synthesis of Compound (1-77) Compound (1-77) was obtained from intermediate (Int-1-77) in the same manner as in Synthesis Example (1).

[0634] APCI-MS revealed m / z (M+H)=1086.37, confirming the production of the target product.

[0635] Synthesis Example (34): Synthesis of Compound (1-80) Compound (1-80) was obtained from intermediate (Int-1-80) in the same manner as in Synthesis Example (1).

[0636] By APCI-MS, m / z (M+H)=1206.66 was observed, confirming the production of the target product.

[0637] Synthesis Example (35): Synthesis of Compound (1-83) Compound (1-83) was obtained from intermediate (Int-1-83) in the same manner as in Synthesis Example (1).

[0638] APCI-MS revealed m / z (M+H)=992.61, confirming the production of the target product.

[0639] Synthesis Example (36): Synthesis of Compound (1-87) Compound (1-87) was obtained from intermediate (Int-1-87) in the same manner as in Synthesis Example (1).

[0640] APCI-MS revealed m / z (M+H)=947.52, confirming the production of the target product.

[0641] Synthesis Example (37): Synthesis of Compound (1-89) Compound (1-89) was obtained from intermediate (Int-1-89) in the same manner as in Synthesis Example (1).

[0642] By APCI-MS, m / z (M+H)=1183.61 was observed, confirming the production of the target product.

[0643] Synthesis Example (38): Synthesis of Compound (1-90) Compound (1-90) was obtained from intermediate (Int-1-90) in the same manner as in Synthesis Example (1).

[0644] By APCI-MS, m / z (M+H)=1086.59 was observed, confirming the production of the target product.

[0645] Synthesis Example (39): Synthesis of Compound (1-91) Compound (1-91) was obtained from intermediate (Int-1-91) in the same manner as in Synthesis Example (1).

[0646] APCI-MS revealed m / z (M+H)=977.59, confirming the production of the target product.

[0647] Synthesis Example (40): Synthesis of Compound (1-92) Compound (1-92) was obtained from intermediate (Int-1-92) in the same manner as in Synthesis Example (1).

[0648] By APCI-MS, m / z (M+H)=1027.61 was observed, confirming the production of the target product.

[0649] Synthesis Example (41): Synthesis of Compound (1-93) Compound (1-93) was obtained from intermediate (Int-1-93) in the same manner as in Synthesis Example (1).

[0650] By APCI-MS, m / z (M+H)=1110.63 was observed, confirming the production of the target product.

[0651] Synthesis Example (42): Synthesis of Compound (1-94) Compound (1-94) was obtained from intermediate (Int-1-94) in the same manner as in Synthesis Example (1).

[0652] APCI-MS showed m / z (M+H)=929.57, confirming the production of the target product.

[0653] Synthesis Example (43): Synthesis of Compound (1-98) Compound (1-98) was obtained from intermediate (Int-1-98) in the same manner as in Synthesis Example (1).

[0654] By APCI-MS, m / z (M+H)=1043.59 was observed, confirming the production of the target product.

[0655] Synthesis Example (44): Synthesis of Compound (1-99) Compound (1-99) was obtained from intermediate (Int-1-99) in the same manner as in Synthesis Example (1).

[0656] By APCI-MS, m / z (M+H)=1003.57 was observed, confirming the production of the target product.

[0657] Synthesis Example (45): Synthesis of Compound (1-104) Compound (1-104) was obtained from intermediate (Int-1-104) in the same manner as in Synthesis Example (1).

[0658] APCI-MS showed m / z (M+H)=928.57, confirming the production of the target product.

[0659] Synthesis Example (46): Synthesis of Compound (1-107)

[0660] <Synthesis of Intermediate (Int-1-107)> Under a nitrogen atmosphere, intermediate (Int-1-1) (2.8 g), bis(pinacolato)diboron (2.0 g), [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride dichloromethane adduct (0.25 g), potassium acetate (2.9 g), and dimethyl sulfoxide (30 mL) were placed in a flask and stirred at 80°C for 20 hours. After the reaction, water and then toluene were added and the mixture was stirred, followed by separation of the organic layer. The separated organic layer was further washed with water and brine, and the organic layer was dried over magnesium sulfate. This organic layer was filtered through Celite and then concentrated under reduced pressure. Heptane was poured into the resulting crude product, and the precipitated solid was filtered, yielding 0.69 g of crude intermediate (Int-1-107).

[0661] <Synthesis of Compound (1-107)> Under a nitrogen atmosphere, a flask containing intermediate (Int-1-107) (1.1 g), 3,5-dichloro-2-phenylpyrimidine (0.22 g), palladium acetate (24 mg), potassium carbonate (0.30 g), SPhos (89 mg), TBAB (70 mg), CPME (30 ml), and water (3 ml) was stirred at reflux temperature for 18 hours. The reaction solution was cooled to room temperature, and water was added thereto to separate the organic layer, which was then washed with water. The organic layer was concentrated under reduced pressure, and the resulting solid was purified on silica gel using toluene and heptane to obtain 0.022 g of compound (1-107).

[0662] By APCI-MS, m / z (M+H)=1005.60 was observed, confirming the production of the target product.

[0663] Synthesis Example (47): Synthesis of Compound (1-111) Compound (1-111) was obtained from intermediate (Int-1-1) in the same manner as in Synthesis Example (1).

[0664] By APCI-MS, m / z (M+H)=1006.60 was observed, confirming the production of the target product.

[0665] Synthesis Example (48): Synthesis of Compound (1-112) Compound (1-112) was obtained from Intermediate (Int-1-1) in the same manner as in Synthesis Example (1).

[0666] By APCI-MS, m / z (M+H)=1004.61 was observed, confirming the production of the target product.

[0667] Synthesis Example (49): Synthesis of Compound (1-116) Compound (1-116) was obtained from intermediate (Int-1-116) in the same manner as in Synthesis Example (1).

[0668] By APCI-MS, m / z (M+H)=1029.60 was observed, confirming the production of the target product.

[0669] Synthesis Example (50): Synthesis of Compound (1-119) Compound (1-119) was obtained from intermediate (Int-1-119) in the same manner as in Synthesis Example (46).

[0670] APCI-MS showed m / z (M+H)=945.59, confirming the production of the target product.

[0671] Synthesis Example (51): Synthesis of Compound (1-120) Compound (1-120) was obtained from intermediate (Int-1-120) in the same manner as in Synthesis Example (46).

[0672] By APCI-MS, m / z (M+H)=1055.74 was observed, confirming the production of the target product.

[0673] Synthesis Example (52): Synthesis of Compound (1-121) Compound (1-121) was obtained from intermediate (Int-1-121) in the same manner as in Synthesis Example (46).

[0674] APCI-MS revealed m / z (M+H)=992.61, confirming the production of the target product.

[0675] Synthesis Example (53): Synthesis of Compound (1-123) Compound (1-123) was obtained from intermediate (Int-1-123) in the same manner as in Synthesis Example (46).

[0676] APCI-MS showed m / z (M+H)=991.54, confirming the production of the target product.

[0677] Synthesis Example (54): Synthesis of Compound (1-126) Compound (1-126) was obtained from intermediate (Int-1-126) in the same manner as in Synthesis Example (1).

[0678] APCI-MS revealed m / z (M+H)=1163.74, confirming the production of the target product.

[0679] Synthesis Example (55): Synthesis of Compound (1-127) Compound (1-127) was obtained from intermediate (Int-1-127) in the same manner as in Synthesis Example (46).

[0680] APCI-MS revealed m / z (M+H)=1119.62, confirming the production of the target product.

[0681] Synthesis Example (56): Synthesis of Compound (1-130) Compound (1-130) was obtained from intermediate (Int-1-130) in the same manner as in Synthesis Example (6).

[0682] By APCI-MS, m / z (M+H)=1445.68 was observed, confirming the production of the target product.

[0683] Synthesis Example (57): Synthesis of Compound (1-133) Compound (1-133) was obtained from Intermediate (Int-1-1) in the same manner as in Synthesis Example (1).

[0684] By APCI-MS, m / z (M+H)=1004.61 was observed, confirming the production of the target product.

[0685] Synthesis Example (58): Synthesis of Compound (1-135) Compound (1-135) was obtained from intermediate (Int-1-135) in the same manner as in Synthesis Example (1).

[0686] By APCI-MS, m / z (M+H)=1304.60 was observed, confirming the production of the target product.

[0687] Synthesis Example (59): Synthesis of Compound (1-137) Compound (1-137) was obtained from intermediate (Int-1-137) in the same manner as in Synthesis Example (1).

[0688] By APCI-MS, m / z (M+H)=1118.56 was observed, confirming the production of the target product.

[0689] Synthesis Example (60): Synthesis of Compound (1-138) Compound (1-138) was obtained from intermediate (Int-1-138) in the same manner as in Synthesis Example (1).

[0690] By APCI-MS, m / z (M+H)=1046.56 was observed, confirming the production of the target product.

[0691] Synthesis Example (61): Synthesis of Compound (1-139) Compound (1-139) was obtained from intermediate (Int-1-139) in the same manner as in Synthesis Example (1).

[0692] APCI-MS revealed m / z (M+H)=1056.47, confirming the production of the target product.

[0693] Synthesis Example (62): Synthesis of Compound (1-141) Compound (1-141) was obtained from intermediate (Int-1-141) in the same manner as in Synthesis Example (1).

[0694] APCI-MS revealed m / z (M+H)=1078.48, confirming the production of the target product.

[0695] Synthesis Example (63): Synthesis of Compound (1-143) Compound (1-143) was obtained from intermediate (Int-1-143) in the same manner as in Synthesis Example (1).

[0696] By APCI-MS, m / z (M+H)=1204.57 was observed, confirming the production of the target product.

[0697] Synthesis Example (64): Synthesis of Compound (1-144) Compound (1-144) was obtained from intermediate (Int-1-144) in the same manner as in Synthesis Example (1).

[0698] APCI-MS revealed m / z (M+H)=1454.72, confirming the production of the target product.

[0699] Synthesis Example (65): Synthesis of Compound (1-145) Compound (1-145) was obtained from intermediate (Int-1-145) in the same manner as in Synthesis Example (1).

[0700] By APCI-MS, m / z (M+H)=1008.49 was observed, confirming the production of the target product.

[0701] Synthesis Example (66): Synthesis of Compound (1-146) Compound (1-146) was obtained from intermediate (Int-1-146) in the same manner as in Synthesis Example (1).

[0702] APCI-MS revealed m / z (M+H)=921.53, confirming the production of the target product.

[0703] Synthesis Example (67): Synthesis of Compound (1-148) Compound (1-148) was obtained from intermediate (Int-1-148) in the same manner as in Synthesis Example (1).

[0704] APCI-MS showed m / z (M+H)=915.49, confirming the production of the target product.

[0705] Synthesis Example (68): Synthesis of Compound (1-150) Compound (1-150) was obtained from intermediate (Int-1-150) in the same manner as in Synthesis Example (1).

[0706] APCI-MS revealed m / z (M+H)=1063.52, confirming the production of the target product.

[0707] Synthesis Example (69): Synthesis of Compound (1-151) Compound (1-151) was obtained from intermediate (Int-1-151) in the same manner as in Synthesis Example (1).

[0708] By APCI-MS, m / z (M+H)=1021.56 was observed, confirming the production of the target product.

[0709] Synthesis Example (70): Synthesis of Compound (1-152) Compound (1-152) was obtained from intermediate (Int-1-152) in the same manner as in Synthesis Example (1).

[0710] APCI-MS revealed m / z (M+H)=1047.58, confirming the production of the target product.

[0711] Synthesis Example (71): Synthesis of Compound (1-153) Compound (1-153) was obtained from intermediate (Int-1-1) in the same manner as in Synthesis Example (1).

[0712] APCI-MS revealed m / z (M+H)=1358.72, confirming the production of the target product.

[0713] Synthesis Example (72): Synthesis of Compound (1-155) Compound (1-155) was obtained from intermediate (Int-1-155) in the same manner as in Synthesis Example (46).

[0714] By APCI-MS, m / z (M+H)=1129.60 was observed, confirming the production of the target product.

[0715] Synthesis Example (73): Synthesis of Compound (1-157) Compound (1-157) was obtained from intermediate (Int-1-157) in the same manner as in Synthesis Example (46).

[0716] By APCI-MS, m / z (M+H)=1437.90 was observed, confirming the production of the target product.

[0717] Synthesis Example (74): Synthesis of Compound (1-159) Compound (1-1599) was obtained from intermediate (Int-1-159) in the same manner as in Synthesis Example (1).

[0718] APCI-MS revealed m / z (M+H)=977.50, confirming the production of the target product.

[0719] Synthesis Example (75): Synthesis of Compound (1-162) Compound (1-162) was obtained from intermediate (Int-1-162) in the same manner as in Synthesis Example (1).

[0720] APCI-MS showed m / z (M+H)=911.35, confirming the production of the target product.

[0721] Synthesis Example (76): Synthesis of Compound (1-164) Compound (1-164) was obtained from intermediate (Int-1-164) in the same manner as in Synthesis Example (1).

[0722] APCI-MS revealed m / z (M+H)=1513.93, confirming the production of the target product.

[0723] Synthesis Example (77): Synthesis of Compound (1-167) Compound (1-167) was obtained from intermediate (Int-1-167) in the same manner as in Synthesis Example (1).

[0724] By APCI-MS, m / z (M+H) = 1367.41 was observed, confirming the production of the target product.

[0725] Synthesis Example (78): Synthesis of Compound (1-170) Compound (1-170) was obtained from intermediate (Int-1-170) in the same manner as in Synthesis Example (1).

[0726] By APCI-MS, m / z (M+H)=1016.62 was observed, confirming the production of the target product.

[0727] Synthesis Example (79): Synthesis of Compound (1-171) Compound (1-171) was obtained from intermediate (Int-1-171) in the same manner as in Synthesis Example (1).

[0728] APCI-MS revealed m / z (M+H)=1129.69, confirming the production of the target product.

[0729] Synthesis Example (80): Synthesis of Compound (1-172) Compound (1-172) was obtained from intermediate (Int-1-172) in the same manner as in Synthesis Example (1).

[0730] By APCI-MS, m / z (M+H)=1029.63 was observed, confirming the production of the target product.

[0731] Synthesis Example (81): Synthesis of Compound (1-173) Compound (1-173) was obtained from intermediate (Int-1-173) in the same manner as in Synthesis Example (1).

[0732] APCI-MS showed m / z (M+H)=977.52, confirming the production of the target product.

[0733] Synthesis Example (82): Synthesis of Compound (1-176) Compound (1-1766) was obtained from intermediate (Int-1-176) in the same manner as in Synthesis Example (1).

[0734] APCI-MS showed m / z (M+H) = 865.44, confirming the production of the target product.

[0735] Synthesis Example (83): Synthesis of Compound (1-181) Compound (1-181) was obtained from intermediate (Int-1-181) in the same manner as in Synthesis Example (1).

[0736] By APCI-MS, m / z (M+H)=1015.53 was observed, confirming the production of the target product.

[0737] Synthesis Example (84): Synthesis of Compound (1-183) Compound (1-183) was obtained from intermediate (Int-1-183) in the same manner as in Synthesis Example (1).

[0738] APCI-MS showed m / z (M+H)=983.53, confirming the production of the target product.

[0739] Synthesis Example (85): Synthesis of Compound (1-188) Compound (1-188) was obtained from intermediate (Int-1-188) in the same manner as in Synthesis Example (1).

[0740] By APCI-MS, m / z (M+H)=1086.56 was observed, confirming the production of the target product.

[0741] Synthesis Example (86): Synthesis of Compound (1-189) Compound (1-189) was obtained from intermediate (Int-1-189) in the same manner as in Synthesis Example (1).

[0742] By APCI-MS, m / z (M+H) = 1199.53 was observed, confirming the production of the target product.

[0743] Synthesis Example (87): Synthesis of Compound (1-190) Compound (1-190) was obtained from intermediate (Int-1-190) in the same manner as in Synthesis Example (1).

[0744] APCI-MS showed m / z (M+H)=1499.72, confirming the production of the target product.

[0745] Synthesis Example (88): Synthesis of Compound (1-192) Compound (1-192) was obtained from intermediate (Int-1-192) in the same manner as in Synthesis Example (1).

[0746] APCI-MS revealed m / z (M+H) = 1328.54, confirming the production of the target product.

[0747] Synthesis Example (89): Synthesis of Compound (1-193) Compound (1-193) was obtained from intermediate (Int-1-193) in the same manner as in Synthesis Example (1).

[0748] By APCI-MS, m / z (M+H)=1376.48 was observed, confirming the production of the target product.

[0749] Synthesis Example (90): Synthesis of Compound (1-200) Compound (1-200) was obtained from intermediate (Int-1-200) in the same manner as in Synthesis Example (1).

[0750] APCI-MS revealed m / z (M+H)=1653.75, confirming the production of the target product.

[0751] Synthesis Example (91): Synthesis of Compound (1-201) Compound (1-201) was obtained from intermediate (Int-1-201) in the same manner as in Synthesis Example (1).

[0752] APCI-MS revealed m / z (M+H)=975.54, confirming the production of the target product.

[0753] Synthesis Example (92): Synthesis of Compound (1-203) Compound (1-203) was obtained from intermediate (Int-1-203) in the same manner as in Synthesis Example (1).

[0754] By APCI-MS, m / z (M+H)=1011.51 was observed, confirming the production of the target product.

[0755] Synthesis Example (93): Synthesis of Compound (1-205) Compound (1-205) was obtained from intermediate (Int-1-205) in the same manner as in Synthesis Example (46).

[0756] APCI-MS revealed m / z (M+H)=969.48, confirming the production of the target product.

[0757] Synthesis Example (94): Synthesis of Compound (1-207) Compound (1-207) was obtained from intermediate (Int-1-207) in the same manner as in Synthesis Example (46), except that potassium carbonate was changed to cesium fluoride.

[0758] APCI-MS revealed m / z (M+H)=891.47, confirming the production of the target product.

[0759] Synthesis Example (95): Synthesis of Compound (1-211) Compound (1-211) was obtained from Intermediate (Int-1-1) in the same manner as in Synthesis Example (1).

[0760] By APCI-MS, m / z (M+H)=1060.58 was observed, confirming the production of the target product.

[0761] Synthesis Example (96): Synthesis of Compound (1-214-2) Compound (1-214-2) was obtained from Intermediate (Int-1-1) in the same manner as in Synthesis Example (1).

[0762] By APCI-MS, m / z (M+H) = 1257.69 was observed, confirming the production of the target product.

[0763] Synthesis Example (97): Synthesis of Compound (1-216) Compound (1-216) was obtained from intermediate (Int-1-216) in the same manner as in Synthesis Example (6).

[0764] APCI-MS revealed m / z (M+H)=1090.68, confirming the production of the target product.

[0765] Synthesis Example (98): Synthesis of Compound (1-219) Compound (1-219) was obtained from intermediate (Int-1-219) in the same manner as in Synthesis Example (46).

[0766] APCI-MS revealed m / z (M+H)=1082.63, confirming the production of the target product.

[0767] Synthesis Example (99): Synthesis of Compound (1-221) Compound (1-221) was obtained from intermediate (Int-1-221) in the same manner as in Synthesis Example (1).

[0768] APCI-MS revealed m / z (M+H)=1113.63, confirming the production of the target product.

[0769] Synthesis Example (100): Synthesis of Compound (1-222) Compound (1-222) was obtained from intermediate (Int-1-222) in the same manner as in Synthesis Example (1).

[0770] By APCI-MS, m / z (M+H)=1175.55 was observed, confirming the production of the target product.

[0771] Synthesis Example (101): Synthesis of Compound (1-223) Compound (1-223) was obtained from intermediate (Int-1-223) in the same manner as in Synthesis Example (1).

[0772] By APCI-MS, m / z (M+H)=1221.53 was observed, confirming the production of the target product.

[0773] Synthesis Example (102): Synthesis of Compound (1-225) Compound (1-225) was obtained from intermediate (Int-1-225) in the same manner as in Synthesis Example (1).

[0774] APCI-MS revealed m / z (M+H) = 1147.54, confirming the production of the target product.

[0775] Synthesis Example (103): Synthesis of Compound (1-231) Compound (1-231) was obtained from intermediate (Int-1-231) in the same manner as in Synthesis Example (1).

[0776] By APCI-MS, m / z (M+H) = 1147.51 was observed, confirming the production of the target product.

[0777] Synthesis Example (104): Synthesis of Compound (1-233) Compound (1-233) was obtained from intermediate (Int-1-233) in the same manner as in Synthesis Example (1).

[0778] APCI-MS revealed m / z (M+H)=1061.40, confirming the production of the target product.

[0779] Synthesis Example (105): Synthesis of compound (1-234) Compound (1-234) was obtained as an isomer mixture from intermediate (Int-1-234) in the same manner as in Synthesis example (1), except that 1,3-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene was used in an amount three times the equivalent.

[0780] APCI-MS revealed m / z (M+H)=1783.69, confirming the production of the target product.

[0781] Synthesis Example (106): Synthesis of Compound (1-237) Compound (1-237) was obtained from intermediate (Int-1-237) in the same manner as in Synthesis Example (1).

[0782] By APCI-MS, m / z (M+H)=1253.47 was observed, confirming the production of the target product.

[0783] Synthesis Example (107): Synthesis of Compound (1-239) Compound (1-239) was obtained from intermediate (Int-1-239) in the same manner as in Synthesis Example (1).

[0784] By APCI-MS, m / z (M+H)=1214.57 was observed, confirming the production of the target product.

[0785] Synthesis Example (108): Synthesis of Compound (1-260) Compound (1-260) was obtained as an isomer mixture from intermediate (Int-1-1) in the same manner as in Synthesis Example (6).

[0786] APCI-MS showed m / z (M+H)=933.63, confirming the production of the target product.

[0787] Synthesis Example (109): Synthesis of Compound (1-262) This was performed with reference to the description in Chemical Science, 2015, 6, 6102-6105. Intermediate (Int-1-262) (0.11 g), Pt(cod)Cl ２ (37.4 g) and CsF (182 mg) were dissolved in 1,4-dioxane (20 mL) and stirred at reflux under an inert atmosphere for 24 hours. After that, the mixture was cooled to room temperature and the 1,4-dioxane was removed under vacuum. The residue was washed with a small amount of CH ２ Cl ２ and filtered. ２ Cl ２ The crude product was removed by CH ２ Cl ２ The product was purified by recrystallization from methanol to obtain compound (1-262).

[0788]

[0789] MALDI-TOF-MS revealed m / z (M) = 1153.60, confirming the production of the target product.

[0790] Synthesis Example (110): Synthesis of Compound (1-263) This was performed with reference to the description in Journal of the American Chemical Society Au, 2022, 2, 1857-1868. ２ CO ２ (205 mg, 0.63 mmol) and Au ２ Cl ２ A mixture of (dcpm) (88.5 mg, 0.10 mmol) was dissolved in degassed toluene / H ２ The mixture was stirred in a 2 mL / EtOH (10 mL / 2 mL / 2 mL) mixture at 50° C. for 7 days. The reaction mixture was allowed to cool to room temperature, and the precipitate was collected by suction filtration, washed with EtOH (10 mL), and dried in vacuo to obtain compound (1-263).

[0791]

[0792] By FT-ICR MALDI-TOF, m / z (M+H) = 1653.79 was observed, confirming the production of the target product.

[0793] <<Preparation and Evaluation of Vapor Deposition-Type Organic EL Devices>> Next, the preparation and evaluation of organic EL devices using the polycyclic aromatic compounds of the present invention will be described. <Configuration of Organic EL Devices> Organic EL devices were produced using the polycyclic aromatic compounds of the present invention. The material configurations of each layer in the organic EL devices (fluorescence-emitting devices) of Examples B1 to B6 and Comparative Example B1 are shown in Table 1 below.

[0794]

[0795] The chemical structural formulas of "HAT-CN," "HT-1," "HT-2," "ET-1," "ET-2," "BH," "HT-1-C," "SiCzCz," "SiTrzCz2," "PtON-TBBI," and "Comparative Compound (1)" in Tables 1 to 4 are shown below. "ITO" is indium-tin oxide.

[0796]

[0797]

[0798] <Element of Example B1> A 26 mm × 28 mm × 0.7 mm glass substrate (manufactured by Optoscience Co., Ltd.) on which an ITO film having a thickness of 180 nm was formed by sputtering and polished to 120 nm was used as a transparent support substrate. This transparent support substrate was fixed to a substrate holder of a commercially available vapor deposition apparatus (manufactured by Showa Vacuum Co., Ltd.), and molybdenum vapor deposition boats containing HAT-CN, HT-1, HT-2, BH, compound (1-1), ET-1, and ET-2, and aluminum nitride vapor deposition boats containing LiF and aluminum were attached.

[0799] The following layers were formed in order on the ITO film of the transparent support substrate. －４ The pressure was reduced to 10 Pa, and first, HAT-CN was heated and vapor-deposited to a thickness of 5 nm, then HT-1 was heated and vapor-deposited to a thickness of 90 nm, and then HT-2 was heated and vapor-deposited to a thickness of 10 nm to form a hole layer. Next, BH and compound (1-1) were simultaneously heated and vapor-deposited to a thickness of 20 nm to form an emitting layer. The vapor deposition rate was adjusted so that the mass ratio of BH to compound (1-1) was approximately 97:3. Furthermore, ET-1 was heated and vapor-deposited to a thickness of 20 nm, and then ET-2 was heated and vapor-deposited to a thickness of 10 nm to form an electron transport layer. The vapor deposition rate for each layer was 0.01 to 1 nm / sec. Thereafter, LiF was heated and vapor-deposited at a vapor deposition rate of 0.01 to 0.1 nm / sec to a thickness of 1 nm, and then aluminum was heated and vapor-deposited to a thickness of 100 nm to form a cathode, thereby obtaining an organic EL device.

[0800] When a DC voltage was applied to both electrodes of the obtained organic EL device (the dopant material of the emitting layer was compound (1-1)), blue light was emitted having a peak top at about 457 nm. The full width at half maximum (FWHM) of the emission spectrum was about 21.6 nm.

[0801] <Elements of Examples B2 to B36 and Comparative Examples B1 to B3> Organic EL elements of Examples B2 to B36 and Comparative Examples B1 to B3 were obtained in the same manner as in Example B1, except that each of the compounds shown in Tables 2 and 3 was used as a dopant material instead of compound (1-1).

[0802] When a DC voltage was applied to both electrodes of the obtained organic EL device of Comparative Example B1 (the dopant material of the emitting layer was Comparative Compound (1)), blue light emission having a peak top at about 462 nm was obtained. The full width at half maximum (FWHM) of the emission spectrum was about 24.2 nm.

[0803] <Evaluation of Organic EL Characteristics> For the organic EL elements of Examples B1 to B36 and Comparative Example B1, a DC voltage of 1000 cd / m was applied between the ITO electrode as the anode and the LiF / aluminum electrode as the cathode. ２ The external quantum efficiency during light emission and the device life were measured. ２ The time during which the device is continuously driven at the voltage required for light emission and maintains 90% or more of the initial luminance is shown in Table 2.

[0804] The quantum efficiency of a light-emitting element can be classified into internal quantum efficiency and external quantum efficiency, and the internal quantum efficiency indicates the rate at which external energy injected as electrons (or holes) into the light-emitting layer of the light-emitting element is converted purely into photons. On the other hand, the external quantum efficiency is calculated based on the amount of these photons emitted to the outside of the light-emitting element, and since some of the photons generated in the light-emitting layer are absorbed or continuously reflected inside the light-emitting element and are not emitted to the outside of the light-emitting element, the external quantum efficiency is lower than the internal quantum efficiency.

[0805] The external quantum efficiency was measured as follows: Using a voltage / current generator R6144 manufactured by Advantest Corporation, the luminance of the element was measured at 1000 cd / m ２The element emits light by applying a voltage such that the voltage is equal to or greater than 100 V. The spectral radiance in the visible light region was measured perpendicular to the light-emitting surface using a TOPCON SR-3AR spectroradiometer. Assuming that the light-emitting surface is a perfectly diffusing surface, the measured spectral radiance value of each wavelength component was divided by the wavelength energy and multiplied by π to obtain the number of photons at each wavelength. Next, the number of photons was integrated over the entire observed wavelength region to obtain the total number of photons emitted from the element. The applied current value divided by the elementary charge was used to obtain the number of carriers injected into the element, and the total number of photons emitted from the element divided by the number of carriers injected into the element was used to obtain the external quantum efficiency. The full width at half maximum (FWHM) of the above-mentioned emission spectrum was determined as the width between the wavelengths above and below which the intensity was 50%, centered on the maximum emission wavelength.

[0806]

[0807] The material configuration of each layer in the organic EL element (PSF type element) of Example C1 is shown in Table 3 below.

[0808] The following layers were formed in order on the ITO film of the transparent support substrate. －４The pressure was reduced to 10 Pa, and first, HAT-CN was heated and evaporated to a thickness of 10 nm to form a hole injection layer. Next, HT-1-C was heated and evaporated to a thickness of 60 nm to form hole transport layer 1, and SiCzCz was further heated and evaporated to a thickness of 5 nm to form hole transport layer 2. Next, SiCzCz, SiTrzCz2, PtON-TBBI, and compound (1-14) were simultaneously heated and evaporated to a thickness of 35 nm. The evaporation rate was adjusted so that the mass ratio of SiCzCz, SiTrzCz2, PtON-TBBI, and compound (1-14) was approximately 60:26:13:1. Next, mSiTrz was heated and evaporated to a thickness of 5 nm to form electron transport layer 1, and further mSiTrz and Liq were heated and evaporated to a thickness of 30 nm to form electron transport layer 2. The deposition rate was adjusted so that the mass ratio of SiTrz to Liq was approximately 1:1. The deposition rate for each layer was 0.01 to 1 nm / sec. Thereafter, LiF was heated and deposited at a deposition rate of 0.01 to 0.1 nm / sec to a thickness of 1 nm, and then aluminum was heated and deposited to a thickness of 100 nm to form a cathode, thereby obtaining an organic EL device. At this time, the deposition rate of aluminum was adjusted to 1 to 10 nm / sec.

[0809] For the organic EL element of Example C1, a DC voltage was applied between the ITO electrode as the anode and the LiF / aluminum electrode as the cathode, and a brightness of 1000 cd / m ２ The external quantum efficiency during light emission and the device life were measured. ２ The time during which the device is continuously driven at the voltage required for light emission and maintains 90% or more of the initial luminance is shown in Table 4.

[0810] REFERENCE SIGNS LIST 100 Organic electroluminescent element 101 Substrate 102 Anode 103 Hole injection layer 104 Hole transport layer 105 Light-emitting layer 106 Electron transport layer 107 Electron injection layer 108 Cathode

Claims

A polycyclic aromatic compound represented by formula (1); In formula (1), Cy represents a structure consisting of one or more structural units represented by formula (Cy), L represents the presence of at least one bridge formed by a linking group represented by formula (1-a) or formula (1-b), In each of formulas (1-a) and (1-b), L Aａ are each independently a trivalent group, and L Aｂ are each independently a divalent group, L B are each independently a single bond or a divalent group, * indicates the bonding position with X, In the formula (Cy), ring A and two rings B are each independently a substituted or unsubstituted aryl ring or a substituted or unsubstituted heteroaryl ring; The two B rings are L ｃｙ and L ｃｙ is a single bond or a linking group, Y is >B-, >P-, >P(=O)-, >P(=S)-, >Al-, >Ga-, >As-, >Si(-R Ｙ ) - or >Ge(-R Ｙ )- and R Ｙ are each independently substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl; Two of X in the structure are nitrogen atoms bonded to * in the linking group represented by formula (1-a) or formula (1-b), and when there are four or more Xs in the structure that are not Xs shared by two structural units, there may be one or more pairs of two Xs that are nitrogen atoms bonded to * in the linking group represented by formula (1-a) or formula (1-b), When three or more Xs are present in the structure, the other Xs are each independently a nitrogen atom shared by two structural units, or >N-R ＮＸ , >O, >S, >C(-R ＣＸ ) ２ , >Ge(-R ＧＸ ) ２ , >Si(-R ＩＸ ) ２ , or >Se, and R ＮＸ , R ＣＸ , R ＧＸ , and R ＩＸ are each independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl; >C(-R ＣＸ ) ２ The two R's ＣＸ may be bonded to each other to form a ring, and >Si(-R ＩＸ ) ２ The two R's ＩＸ may be bonded to each other to form a ring, R ＮＸ , at least one R ＣＸ and at least one R ＩＸ may be bonded to at least one of ring A and ring B via a linking group or a single bond, In formula (1), at least one selected from the group consisting of an aryl ring and a heteroaryl ring may be condensed with at least one cycloalkane, and when the cycloalkane has a bridged structure, at least one —CH ２ -CH ２ - may be -CH=CH-, and when the cycloalkane has a bridged structure, the cycloalkane ring may be condensed with an aryl ring or a heteroaryl ring, the cycloalkane may be substituted with at least one substituent, and at least one -CH ２ - may be replaced by -O-, In formula (1), at least one hydrogen may be replaced with deuterium, and at least one nitrogen may be replaced with nitrogen-15 ( １５ N), and at least one sulfur may be replaced by sulfur-33 ( ３３ S), sulfur-34 ( ３４ S) or sulfur-36 ( ３６ S), and at least one oxygen may be replaced by oxygen-17 ( １７ O) or oxygen-18 ( １８ O), and at least one carbon may be replaced by carbon-13 ( １３ C), and at least one boron may be replaced by boron-11 ( １１ B) may be substituted. L Ａａ are each independently represented by the formula (L Ａａ－１ ) is a group represented by L Ａｂ are each independently represented by the formula (L Ａｂ－１ 2. The polycyclic aromatic compound according to claim 1, wherein the group is a group represented by Formula (L Ａａ－１ ) and formula (L Ａｂ－１ ) inside, ring Aa and ring Ab each independently represent a substituted or unsubstituted aryl ring, a substituted or unsubstituted heteroaryl ring, or a substituted or unsubstituted cycloalkane ring; * is the bonding position to the nitrogen atom which is X, # is L Ｂ This is the bonding position with L Ａａ are each independently represented by the formula (L Ａａ－２ ) is a group represented by L Ａｂ are each independently represented by the formula (L Ａｂ－２ 2. The polycyclic aromatic compound according to claim 1, wherein the group is a group represented by Formula (L Ａａ－２ ) and formula (L Ａｂ－２ ) inside, Each Z is independently N or C-R Ｚ or Z = Z are each independently >O, >N-R ＮＺ , >C(-R ＣＺ ) ２ , >Si(-R ＩＺ ) ２ , >S, or >Se, and R ＮＺ , R ＣＺ , and R ＩＺ are each independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, and >C(-R ＣＺ ) ２ The two R's ＣＺ may be bonded to each other to form a ring, and >Si(-R ＩＺ ) ２ The two R's ＩＺ may be bonded to each other to form a ring, R Ｚ are each independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino (two aryls may be bonded to each other via a linking group), substituted or unsubstituted diheteroarylamino (two heteroaryls may be bonded to each other via a linking group), substituted or unsubstituted arylheteroarylamino (an aryl and a heteroaryl may be bonded to each other via a linking group), substituted or unsubstituted diarylboryl (two aryls may be bonded to each other via a single bond or a linking group), substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted arylthio, or substituted silyl; Two adjacent C-R Ｚ may be bonded to each other to form an aryl ring or a heteroaryl ring together with a ring having the carbon atoms to which they are bonded as constituent atoms, and the formed aryl ring and heteroaryl ring may have a substituent, * is the bonding position to the nitrogen atom which is X, # is L Ｂ This is the bonding position with L Ａａ are each independently represented by the formula (L Ａａ－２ -1) ~Formula (L Ａａ－２ -4), and L Ａｂ are each independently represented by the formula (L Ａｂ－２ -1) ~Formula (L Ａｂ－２ 2. The polycyclic aromatic compound according to claim 1, wherein the group is a group represented by any one of the following: Formula (L) Ａａ－２ -1) ~ Formula (L) Ａａ－２ -4), Formula (L) Ａｂ－２ -1) ~ Formula (L) Ａｂ－２ -9) Middle Each A is independently >O, >N-R ＮＡ , >C(-R ＣＡ ) ２ , >Si(-R ＩＡ ) ２ , >S, >Se, or >Te, and R ＮＡ , R ＣＡ , and R ＩＡ are each independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, and >C(-R ＣＡ ) ２ The two R's ＣＡ may be bonded to each other to form a ring, and >Si(-R ＩＡ ) ２ The two R's ＩＡ may be bonded to each other to form a ring, At least one hydrogen atom in the group represented by each of the above formulas may be replaced by alkyl. * is the bonding position to the nitrogen atom which is X, # is L Ｂ This is the bonding position with L Ｂ are each independently represented by the formula (L ｂ ), formula (L ｂ２ ), or formula (L ｂ３ 2. The polycyclic aromatic compound according to claim 1, wherein the group is a group represented by Formula (L) ｂ )middle, X Ｌ are each independently a single bond, —O—, —S—, —Se—, —Te—, or —(N—R Ｌ ) -, -(P-R Ｌ )-,-(O=P-R Ｌ ) -, -(C(-R Ｌ ) ２ )-,-(C=O)-,-(Ge(-R Ｌ ) ２ )-,-(Sn(-R Ｌ ) ２ )-, -SO-, -SO ２ -, -(Si(-R Ｌ ) ２ )-,-(S=P-R Ｌ ) -, -(B-R Ｌ ) - or -(Bi-R Ｌ )- and R Ｌ are each independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, and —(C(—R Ｌ ) ２ )-,-(Ge(-R Ｌ ) ２ )-,-(Sn(-R Ｌ ) ２ )-, and -(Si(-R Ｌ ) ２ )- each of the two R Ｌ may be bonded to each other to form a ring, Ar's each independently represent a substituted or unsubstituted alkylene having 2 to 12 carbon atoms, a substituted or unsubstituted arylene, or a substituted or unsubstituted heteroarylene, and at least one —CH ２ -CH ２ - may be replaced by cycloalkylene or vinylene, j is an integer of 1 to 10, # is L Ａａ or L Ａｂ is the bonding position with Formula (L) ｂ２ )middle, X Ｌ , Ar, and # are represented by the formula (L ｂ ) in Ｌ , Ar, and #, respectively; X Ｌ１ is -O-, -S-, -Se-, -Te-, -(N-R Ｌ ) -, -(P-R Ｌ )-,-(O=P-R Ｌ ) -, -(C(-R Ｌ ) ２ )-,-(C=O)-,-(Ge(-R Ｌ ) ２ )-,-(Sn(-R Ｌ ) ２ )-, -SO-, -SO ２ -, -(Si(-R Ｌ ) ２ )-,-(S=P-R Ｌ ) -, -(B-R Ｌ ) - or -(Bi-R Ｌ )- and R Ｌ is the formula (L ｂ ) in R Ｌ is synonymous with Each j2 is independently an integer of 0 to 5, and j3 is an integer of 2 to 5, provided that when each j2 is 0, j3 may be 1; Formula (L) ｂ３ )middle, X Ｌ , Ar, and # each independently represent a group represented by the formula (L ｂ ) in Ｌ , Ar, and #, respectively; j2 each independently represents an integer from 0 to 5; M ｃｏｍｐ Is > (M Ｔ ) n-(L ＭＴ ) m, and M Ｔ are each independently a transition metal atom, and L ＭＴ are each independently M Ｔ where n is an integer of 1 to 3 and m is an integer of 0 to 5. L Ｂ are each independently represented by the formula (L ｂ 6. The polycyclic aromatic compound according to claim 5, wherein the group is a group represented by the formula: L B are each independently represented by any one of the following formulas: In the above formula, Ar is a group represented by the formula (L ｂ ) has the same meaning as Ar in X Ｌ１ are each independently —O—, —S—, —Se—, —Te—, —(N—R Ｌ ) -, -(P-R Ｌ )-,-(O=P-R Ｌ ) -, -(C(-R Ｌ ) ２ )-,-(C=O)-,-(Ge(-R Ｌ ) ２ )-,-(Sn(-R Ｌ ) ２ )-, -SO-, -SO ２ -, -(Si(-R Ｌ ) ２ )-,-(S=P-R Ｌ ) -, -(B-R Ｌ ) - or -(Bi-R Ｌ )- and R Ｌ are each independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, and —C(—R Ｌ ) ２ -, -(Ge(-R Ｌ ) ２ )-,-(Sn(-R Ｌ ) ２ ), and -(Si(-R Ｌ ) ２ )- each of the two R ＩＬ may be bonded to each other to form a ring, # is L Ａａ or L Ａｂ This is the bonding position with The polycyclic aromatic compound according to claim 1, wherein the linking groups represented by formula (1-a) or formula (1-b) are each independently represented by any one of the following formulas: In the formula, Me is methyl, tBu is t-butyl, tAm is t-amyl, and D is deuterium. 　 The polycyclic aromatic compound according to claim 1, which is represented by any one of the following formulas: In the formula, Me is methyl, tBu is t-butyl, tAm is t-amyl, and D is deuterium. 　 An organic electroluminescent device comprising a pair of electrodes consisting of an anode and a cathode and an organic layer disposed between the pair of electrodes, wherein the organic layer contains the polycyclic aromatic compound according to any one of claims 1 to 9. 　 The organic electroluminescent device according to claim 10 , wherein the organic layer is a light-emitting layer.

12. The organic electroluminescent device according to claim 11, wherein the light-emitting layer comprises a host material, a thermally activated delayed fluorescent material or a phosphorescent material as an assisting dopant, and the polycyclic aromatic compound as an emitting dopant. 　 A display device or a lighting device comprising the organic electroluminescent device according to claim 10.

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