Polycyclic aromatic compounds

Abstract

This invention provides novel compounds useful as materials for organic devices such as organic light-emitting diodes (OLEDs). [Solution] A polycyclic aromatic compound having a structure consisting of one or more structural units represented by the following formula (1); In formula (1) of TIFF2026143515000162.tif37170, rings A, B, and C are optionally substituted aryl rings or optionally substituted heteroaryl rings; Y 1 is B, P, P=O, P=S, Al, Ga, As, Si-R, or Ge-R; X 1 and X 2 is >O, >NR, >C(-R)2, >Si(-R)2, >S, or >Se; at least one hydrogen in the structure may be substituted with cyano, halogen, or deuterium; provided that at least one hydrogen in the structure is substituted with a cycloalkyl, and at least one of the aryl or heteroaryl rings is condensed with a cycloalkane.

Description

[Technical Field]

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

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

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

[0004] In this context, Patent Document 1 discloses that a boron-containing polycyclic aromatic compound is useful as a material for organic electroluminescent devices. It has been reported that organic electroluminescent devices containing this polycyclic aromatic compound have good external quantum efficiency. Patent Document 2 discloses a compound in which a cycloalkyl group such as adamantyl is introduced as a bulky substituent to suppress concentration quenching in a boron-containing polycyclic aromatic compound, thereby enabling increased efficiency and lifespan of organic electroluminescent devices using this compound. Patent Document 3 discloses a polycyclic aromatic compound containing a condensed cycloalkane structure. This structure has a low sublimation temperature due to its condensed cycloalkane structure, has high stability, and is effective in obtaining organic electroluminescent devices with excellent efficiency and long lifespan characteristics, while the condensed cycloalkyl structure is also expected to suppress concentration quenching. [Prior art documents] [Patent Documents]

[0005] [Patent Document 1] International Publication No. 2015 / 102118 [Patent Document 2] Japanese Patent Publication No. 2020-520976 [Patent Document 3] International Publication No. 2020 / 017931 [Overview of the project] [Problems that the invention aims to solve]

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

[0007] The present inventors have diligently studied to solve the above problems and have succeeded in producing a novel polycyclic aromatic compound having a structure similar to the compound described in Patent Document 1, but with superior luminescence properties. Specifically, by combining a condensed cycloalkyl structure, which has the effect of suppressing concentration quenching, with a cycloalkyl substitution structure, they have succeeded in producing a polycyclic aromatic compound that provides high luminescence efficiency. Furthermore, they have found that an excellent organic EL element can be obtained by arranging a layer containing this polycyclic aromatic compound between a pair of electrodes to construct an organic EL element, thus completing the present invention. In other words, the present invention provides the following polycyclic aromatic compounds, and further, materials for organic devices containing the following polycyclic aromatic compounds.

[0008] Specifically, the present invention has the following configuration.

[0009] [1] Polycyclic aromatic compounds having a structure consisting of one or more structural units represented by the following formula (1); [ka] In formula (1), Rings A, B, and C are each independently a substituted or substituted aryl ring or a substituted heteroaryl ring; Y 1 is B, P, P=O, P=S, Al, Ga, As, Si-R, or Ge-R, where R in Si-R and Ge-R is a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted alkyl, or a substituted or unsubstituted cycloalkyl; X 1 and X 2Each of these is independently >O, >NR, >C(-R)2, >Si(-R)2, >S, or >Se, where R in >NR is hydrogen, a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted alkyl, or a substituted or unsubstituted cycloalkyl; each of the >C(-R)2 and >Si(-R)2 is independently hydrogen, a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted alkyl, or a substituted or unsubstituted cycloalkyl; the two Rs in >C(-R)2 and >Si(-R)2 may be bonded to each other to form a ring; and at least one R in >NR, >C(-R)2, and >Si(-R)2 may be bonded to at least one of the A ring and the B ring, or to at least one of the A ring and the C ring, by a linking group or single bond; At least one hydrogen atom in the above structure may be substituted with cyano, halogen, or deuterium; However, at least one hydrogen atom in the above structure is substituted with a substituted or unsubstituted cycloalkyl group, In the above structure, at least one of the aryl ring or heteroaryl ring is condensed with at least one cycloalkane, at least one hydrogen in the cycloalkane may be substituted, and at least one -CH2- in the cycloalkane may be substituted with -O-.

[0010] [2] The polycyclic aromatic compounds described in [1], wherein the structural unit represented by formula (1) is the structural unit represented by formula (2) below; [ka]

[0011] In formula (2), Each Z is independent of N or CR. Z The CR Z R ZEach of these is independently a hydrogen, aryl, heteroaryl, diarylamino (where the two aryls are not bonded to each other, or are bonded via a single bond or a linking group), diheteroarylamino (where the two heteroaryls are not bonded to each other, or are bonded via a single bond or a linking group), arylheteroarylamino (where the aryl and heteroaryl are not bonded to each other, or are bonded via a single bond or a linking group), diarylboryl (where the two aryls are not bonded to each other, or are bonded via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, or substituted silyl, wherein at least one hydrogen in these may be substituted with an aryl, heteroaryl, alkyl, or cycloalkyl; Two adjacent R Z These may bond to each other to form an aryl ring or a heteroaryl ring, and the formed aryl ring and heteroaryl ring may each be substituted with aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (the two aryls may be bonded via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, or substituted silyl, and at least one hydrogen in these may be substituted with aryl, heteroaryl, alkyl, or cycloalkyl; Each of Z=Z may independently be >O, >NR, >C(-R)2, >Si(-R)2, >S, or >Se, and each of the R in >NR, >C(-R)2, and >Si(-R)2 may independently be hydrogen, a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted alkyl, or a substituted or unsubstituted cycloalkyl, and the two Rs in >C(-R)2 and >Si(-R)2 may be bonded to each other to form a ring; Y 1is B, P, P=O, P=S, Al, Ga, As, Si-R or Ge-R, wherein R in said Si-R and Ge-R is substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl; X 1 is >O, >N-R, >C(-R)2, >Si(-R)2, >S or >Se, wherein R in said >N-R is hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl; R in said >C(-R)2 and R in said >Si(-R)2 are each independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl; the two R groups in said >C(-R)2 and said >Si(-R)2 may be bonded to each other to form a ring; R in said >N-R, R in said >C(-R)2 and R in said >Si(-R)2 may be bonded to one or two R groups in said Z which is the aforementioned C-R Z via a linking group or a single bond; Z ; G is aryl substituted with cycloalkyl or heteroaryl substituted with cycloalkyl; at least one hydrogen in the structure may be substituted with cyano, halogen or deuterium; provided that in said structure, at least one of the aryl ring, the heteroaryl ring, or the ring formed by R in said C-R Z Z is fused with at least one cycloalkane, at least one hydrogen in said cycloalkane may be substituted, and at least one -CH2- in said cycloalkane may be substituted with -O-. [3] The polycyclic aromatic compound according to [1] or [2], which has at least one adamantyl group.

[0012] [4] The polycyclic aromatic compound according to any one of [1] to [3], which has a structure represented by formula (1i);​ [ka]

[0013] During the ceremony, Z a Each is independently N or CR Za And Z b Each is independently N or CR Zb And Z c Each is independently N or CR Zc And R Za , R Zb and R Zc Each of these is independently a hydrogen, aryl, heteroaryl, diarylamino (where the two aryls are not bonded to each other or are bonded via a single bond or a linking group), diheteroarylamino (where the two heteroaryls are not bonded to each other or are bonded via a single bond or a linking group), arylheteroarylamino (where the aryl and heteroaryl are not bonded to each other or are bonded via a single bond or a linking group), diarylboryl (where the two aryls are not bonded to each other or are bonded via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, or substituted silyl, wherein at least one hydrogen in these may be substituted with an aryl, heteroaryl, alkyl, or cycloalkyl. Two adjacent R Za , two adjacent R Zb and two adjacent R ZcThese may bond to each other to form an aryl ring or a heteroaryl ring, and the formed aryl ring and heteroaryl ring may be substituted with aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (the two aryls may be bonded via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, or substituted silyl, and at least one hydrogen in these may be substituted with aryl, heteroaryl, alkyl, or cycloalkyl; Y 1 is B, P, P=O, P=S, Al, Ga, As, Si-R, or Ge-R, where R in Si-R and Ge-R is a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted alkyl, or a substituted or unsubstituted cycloalkyl; X 1 and X 2 These are independently >O, >NR, >C(-R)2, >Si(-R)2, >S, or >Se, where X 1 and X 2 Either one of them is >NG, and the R in >NR is hydrogen, a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted alkyl, or a substituted or unsubstituted cycloalkyl, and the R in >C(-R)2 and the R in >Si(-R)2 are independently hydrogen, a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted alkyl, or a substituted or unsubstituted cycloalkyl, and the two Rs in >C(-R)2 and the R in >Si(-R)2 may be bonded to each other to form a ring, and the R in >NR, the R in >C(-R)2 and the R in >Si(-R)2 are linked by a linking group or single bond to the CR Z The R in Z is Z It may be combined with one or two of the following: G is a cycloalkyl-substituted aryl or cycloalkyl-substituted heteroaryl; In the above structure, at least one selected from the group consisting of aryl rings and heteroaryl rings is condensed with at least one cycloalkane, wherein at least one hydrogen in the cycloalkane may be substituted, and at least one -CH2- in the cycloalkane may be substituted with -O-; At least one hydrogen atom in the above structure may be substituted with cyano, halogen, or deuterium.

[0014] [5] The polycyclic aromatic compound according to [4], wherein the b ring and c1 ring in formula (1i) are each condensed with at least one cycloalkane, at least one hydrogen in the cycloalkane may be substituted, and at least one -CH2- in the cycloalkane may be substituted with -O-.

[0015] [6] A polycyclic aromatic compound as described in [4], represented by any one of the following formulas; [ka] [ka] [ka] In the above formula, Me is methyl, tBu is t-butyl, and D is deuterium.

[0016] [7] A polycyclic aromatic compound according to any of [1] to [3] having the structure represented by formula (1a); [ka]

[0017] During the ceremony, Z a Each is independently N or CR Za And Z b Each is independently N or CR Zb And Z cEach is independently N or CR Zc And R Za , R Zb and R Zc Each of these is independently a hydrogen, aryl, heteroaryl, diarylamino (where the two aryls are not bonded to each other or are bonded via a single bond or a linking group), diheteroarylamino (where the two heteroaryls are not bonded to each other or are bonded via a single bond or a linking group), arylheteroarylamino (where the aryl and heteroaryl are not bonded to each other or are bonded via a single bond or a linking group), diarylboryl (where the two aryls are not bonded to each other or are bonded via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, or substituted silyl, wherein at least one hydrogen in these may be substituted with an aryl, heteroaryl, alkyl, or cycloalkyl. Two adjacent R Za , two adjacent R Zb and two adjacent R Zc These may bond to each other to form an aryl ring or a heteroaryl ring, and the formed aryl ring and heteroaryl ring may be substituted with aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (the two aryls may be bonded via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, or substituted silyl, and at least one hydrogen in these may be substituted with aryl, heteroaryl, alkyl, or cycloalkyl; X c>O, >NR, >C(-R)2, >Si(-R)2, >S, or >Se, where R in >NR, >C(-R)2, and >Si(-R)2 is independently hydrogen, a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted alkyl, or a substituted or unsubstituted cycloalkyl, and the two Rs in >C(-R)2 and >Si(-R)2 are bonded to each other to form a ring, or are not bonded to each other; Y 1 is B, P, P=O, P=S, Al, Ga, As, Si-R, or Ge-R, where R in Si-R and Ge-R is a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted alkyl, or a substituted or unsubstituted cycloalkyl; X 1 and X 2 These are independently >O, >NR, >C(-R)2, >Si(-R)2, >S, or >Se, where X 1 and X 2 Either one of them is >NG, and the R in >NR is hydrogen, a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted alkyl, or a substituted or unsubstituted cycloalkyl, and the R in >C(-R)2 and the R in >Si(-R)2 are independently hydrogen, a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted alkyl, or a substituted or unsubstituted cycloalkyl, and the two Rs in >C(-R)2 and the R in >Si(-R)2 may be bonded to each other to form a ring, and the R in >NR, the R in >C(-R)2 and the R in >Si(-R)2 are linked by a linking group or single bond to the CR Z The R in Z is Z It may be combined with one or two of the following: G is a cycloalkyl-substituted aryl or cycloalkyl-substituted heteroaryl; In the above structure, at least one selected from the group consisting of aryl rings and heteroaryl rings is condensed with at least one cycloalkane, wherein at least one hydrogen in the cycloalkane may be substituted, and at least one -CH2- in the cycloalkane may be substituted with -O-; At least one hydrogen atom in the above structure may be substituted with cyano, halogen, or deuterium.

[0018] [8] A polycyclic aromatic compound as described in [7], represented by any one of the following formulas; [ka] In the above formula, Me is methyl and tBu is t-butyl.

[0019] A material for organic devices containing a polycyclic aromatic compound as described in any of [9] [1] to [8].

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

[11] The organic electroluminescent element according to

[10] , wherein the light-emitting layer comprises a host and the polycyclic aromatic compound as a dopant.

[12] The organic electroluminescent device according to

[11] , wherein the host is an anthracene compound, a fluorene compound, or a dibenzochrysene compound.

[13] A display device or lighting device equipped with an organic electroluminescent element as described in any of

[10] to

[12] . [Effects of the Invention]

[0020] The present invention provides novel polycyclic aromatic compounds useful as materials for organic devices such as organic electroluminescent devices. The polycyclic aromatic compounds of the present invention can be used in the manufacture of organic devices such as organic electroluminescent devices. [Brief explanation of the drawing]

[0021] [Figure 1] This is a schematic cross-sectional view showing an example of an organic field light-emitting device. [Figure 2] This is an energy level diagram showing the energy relationships between the host, assisting dopant, and emitting dopant of a TAF device using a common fluorescent dopant. [Figure 3] This is an energy level diagram showing an example of the energy relationship between the host, assisting dopant, and emitting dopant in an organic electroluminescent device according to one aspect of the present invention. [Modes for carrying out the invention]

[0022] The present invention will be described in detail below. The following descriptions of constituent elements may be based on representative embodiments or specific examples, but the present invention is not limited to such embodiments. In this specification, numerical ranges represented by "~" mean a range that includes the numbers written before and after "~" as the lower and upper limits. Also, in this specification, "hydrogen" in the description of structural formulas means "hydrogen atom (H)". In this specification, an organic electroluminescent element may be referred to as an organic EL element.

[0023] In this specification, chemical structures and substituents are sometimes expressed in terms of carbon number. However, when a substituent is substituted into a chemical structure, or when a substituent is further substituted into another substituent, the carbon number refers to the carbon number of the chemical structure and the substituent itself, and does not refer to the total carbon number of the chemical structure and substituent, or the total carbon number of the substituents. For example, "substituent B with carbon number Y substituted by substituent A with carbon number X" means that "substituent A with carbon number X" is substituted into "substituent B with carbon number Y," and carbon number Y is not the total carbon number of substituent A and substituent B. Also, for example, "substituent B with carbon number Y substituted by substituent A" means that "substituent A (without carbon number limitation)" is substituted into "substituent B with carbon number Y," and carbon number Y is not the total carbon number of substituent A and substituent B.

[0024] 1. Polycyclic aromatic compounds The polycyclic aromatic compounds of the present invention are polycyclic aromatic compounds having a structure consisting of one or more structural units represented by formula (1). The polycyclic aromatic compounds of the present invention have high luminescence quantum yield (PLQY), a narrow emission half-width, and excellent color purity.

[0025] [ka]

[0026] In formula (1), ring A, ring B, and ring C are each independently an optionally substituted aryl ring or an optionally substituted heteroaryl ring.

[0027] The aryl ring or heteroaryl ring in rings A, B, and C is Y 1 and X 1 and / or X 2 It is preferable that it is bonded by a 5-membered ring or a 6-membered ring. 1 and X 1 and / or X 2 "Bonded by a 5-membered or 6-membered ring" means that the ring is formed by this 5-membered or 6-membered ring alone, or that other rings are fused to include this 5-membered or 6-membered ring to form a ring. In other words, all or part of the 5-membered or 6-membered rings make up Y 1 and X 1 and / or X 2 This means that it is bonded to Y. In aryl or heteroaryl rings in rings A, B, and C, two or three consecutive ring constituent atoms (carbon atoms) are Y 1 and X 1 and / or X 2 It is sufficient if they are directly bonded to Y. That is, in the aryl ring or heteroaryl ring of the B ring, any pair of consecutive ring constituent atoms (carbon atoms) is Y 1 and X 1It is directly bonded to, and in the aryl ring or heteroaryl ring of the C ring, any pair of consecutive ring constituent atoms (carbon atoms) is Y 1 and X 2 It is directly bonded to and in the aryl ring or heteroaryl ring of ring A, any set of three consecutive ring constituent atoms (carbon atoms) is Y 1 , X 1 and X 2 It is directly linked to it.

[0028] Examples of the "aryl ring" in ring A, ring B, or ring C of formula (1) include aryl rings having 6 to 30 carbon atoms, preferably aryl rings having 6 to 16 carbon atoms, more preferably aryl rings having 6 to 12 carbon atoms, and particularly preferably aryl rings having 6 to 10 carbon atoms.

[0029] Specific examples of "aryl rings" include the monocyclic benzene ring, the bicyclic biphenyl ring, the condensed bicyclic naphthalene ring and indene ring, the tricyclic terphenyl ring (m-terphenyl, o-terphenyl, p-terphenyl), the condensed tricyclic acenaphthylene ring, fluorene ring, phenalene ring, phenanthrene ring, and anthracene ring, the condensed tetracyclic triphenylene ring, pyrene ring, naphthalene ring, and chrysene ring, and the condensed pentacyclic perylene ring and pentacene ring. Furthermore, the fluorene ring, benzofluorene ring, and indene ring also include structures in which a fluorene ring, benzofluorene ring, and cyclopentane ring are spiro-linked, respectively. Furthermore, the fluorene ring, benzofluorene ring, and indene ring also include those in which two of the two hydrogen atoms of the methylene group are replaced by alkyl groups such as methyl as the first substituent described later, resulting in the dimethylfluorene ring, dimethylbenzofluorene ring, and dimethylindene ring, respectively.

[0030] Examples of the "heteroaryl ring" in ring A, ring B, or ring C of formula (1) include heteroaryl rings having 2 to 30 carbon atoms, with heteroaryl rings having 2 to 25 carbon atoms being preferred, heteroaryl rings having 2 to 20 carbon atoms being more preferred, heteroaryl rings having 2 to 15 carbon atoms being even more preferred, and heteroaryl rings having 2 to 10 carbon atoms being particularly preferred. Examples of the "heteroaryl ring" include heterocycles containing 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen in addition to carbon as ring constituent atoms.

[0031] Specific examples of "heteroaryl rings" include, for example, pyrrole rings, oxazole rings, isoxazole rings, thiazole rings, isothiazole rings, imidazole rings, oxadiazole rings, thiadiazole rings, triazole rings, tetrazole rings, pyrazole rings, pyridine rings, pyrimidine rings, pyridazine rings, pyrazine rings, triazine rings, indole rings, isoindole rings, 1H-indazole rings, benzimidazole rings, benzoxazole rings, benzothiazole rings, 1H-benzotriazole rings, quinoline rings, isoquinoline rings, sinnoline rings, quinazoline rings, quinoxaline rings, phthalazine rings, naphth Examples include lysine rings, purine rings, pteridine rings, carbazole rings, acridine rings, phenoxatiin rings, phenoxazine rings, phenothiazine rings, phenazine rings, phenazacillin rings, indoridine rings, furan rings, benzofuran rings, isobenzofuran rings, dibenzofuran rings, thiophene rings, benzothiophene rings, dibenzothiophene rings, furazan rings, thianthlene rings, indolocarbazole rings, benzoindocarbazole rings, dibenzoindocarbazole rings, naphthobenzofuran rings, dioxin rings, dihydroacridine rings, xanthene rings, thioxanthene rings, and dibenzodioxin rings. Furthermore, for dihydroacridine rings, xanthene rings, and thioxanthene rings, it is also preferable that two of the two hydrogen atoms of the methylene ring are substituted with alkyl groups such as methyl as the first substituent described later, resulting in dimethyldihydroacridine rings, dimethylxanthene rings, and dimethylthioxanthene rings. Furthermore, bicyclic rings such as bipyridine rings, phenylpyridine rings, and pyridylphenyl rings, and tricyclic rings such as terpyridyl rings, bispyridylphenyl rings, and pyridylbiphenyl rings can also be listed as "heteroaryl rings." In addition, pyran rings are also included in the definition of "heteroaryl rings."

[0032] At least one hydrogen in the above-mentioned "aryl ring" or "heteroaryl ring" may be substituted with a first substituent, which is a substituted or unsubstituted "aryl", a substituted or unsubstituted "heteroaryl", a substituted or unsubstituted "diarylamino", a substituted or unsubstituted "diheteroarylamino", a substituted or unsubstituted "arylheteroarylamino", a substituted or unsubstituted "diarylboryl", a substituted or unsubstituted "alkyl", a substituted or unsubstituted "cycloalkyl", a substituted or unsubstituted "alkoxy", a substituted or unsubstituted "aryloxy", or a substituted "silyl". Examples of this first substituent include the monovalent group of the above-mentioned "aryl ring" or "heteroaryl", the aryl in "diarylamino", the heteroaryl in "diheteroarylamino", the aryl and heteroaryl in "arylheteroarylamino", the aryl in "diarylboryl", and the aryl in "aryloxy".

[0033] Specifically, examples of "aryls" include aryls having 6 to 30 carbon atoms, with aryls having 6 to 24 carbon atoms being preferred, aryls having 6 to 20 carbon atoms being more preferred, aryls having 6 to 16 carbon atoms being even more preferred, aryls having 6 to 12 carbon atoms being particularly preferred, and aryls having 6 to 10 carbon atoms being most preferred.

[0034] Specific examples of aryls include, for instance, the monocyclic aryl phenyl, the bicyclic aryl (2-,3-,4-)biphenylyl, the condensed bicyclic aryls (1-,2-)naphthyl, (2-,3-,4-,5-,6-,7-)indenyl, and the tricyclic aryl terpheniryl (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, p-terphenyl (Lu-4-yl), the condensed tricyclic aryls are acenaphthylene-(1-,3-,4-,5-)yl, fluoren-(1-,2-,3-,4-,9-)yl, phenalen-(1-,2-)yl, (1-,2-,3-,4-,9-)phenanthryl, and the tetracyclic aryl is quaterpheniryl (5'-phenyl-m-terphenyl-2-yl, 5'-phenyl-m-terphenyl Examples include ru-3-yl, 5'-phenyl-m-terphenyl-4-yl, m-quaterphenylyl), the condensed tetracyclic aryls triphenylene-(1-,2-)yl, pyren-(1-,2-,4-)yl, naphthasen-(1-,2-,5-)yl, and the condensed pentacyclic aryls perylene-(1-,2-,3-)yl, pentasene-(1-,2-,5-,6-)yl.

[0035] Furthermore, examples of "heteroaryls" include heteroaryls having 2 to 30 carbon atoms, with heteroaryls having 2 to 25 carbon atoms being preferred, heteroaryls having 2 to 20 carbon atoms being more preferred, heteroaryls having 2 to 15 carbon atoms being even more preferred, and heteroaryls having 2 to 10 carbon atoms being particularly preferred. Examples of heteroaryls include heterocycles containing 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen in addition to carbon as ring constituent atoms.

[0036] Specific heteroaryls include, for example, furyl, thienyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, pyrazolyl, oxadiazolyl, flazanil, thiadiazolyl, triazolyl, tetrazolyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, benzofuranil, isobenzofuranil, dibenzofuranil, benzo[b]thienyl, dibenzothienyl, and yin. Examples include drill, isoindolyl, 1H-indazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolyl, isoquinolyl, cinnolyl, quinazolyl, quinoxalinyl, phthalazinyl, naphthilidinyl, prinyl, pteridinyl, carbazolyl, acridinyl, phenoxazinyl, phenothiazinyl, phenazinyl, phenoxathiinyl, thianthrenyl, and indolidinyl.

[0037] As the first substituents, "diarylamino," "diheteroarylamino," and "arylheteroarylamino" can be referenced from the "aryl" and "heteroaryl" described above, along with their preferred ranges.

[0038] Furthermore, in diarylamino as the first substituent, the two aryls are either not bonded to each other or are bonded to each other via a linking group. In diheteroarylamino as the first substituent, the two heteroaryls are either not bonded to each other or are bonded to each other via a linking group. In arylheteroarylamino as the first substituent, the aryl and heteroaryl are either not bonded to each other or are bonded to each other via a linking group. Here, the phrase "bonded via a linking group" means, for example, that the two phenyls in diphenylamino form a bond via a linking group, as shown below. This explanation also applies to diheteroarylaminos and arylheteroarylaminos formed with aryls and heteroaryls.

[0039] [ka]

[0040] Specific examples of the linking group include >O, >N-R X , >C(-R X )2, >Si(-R X )2, >S, >CO, >CS, >SO, >SO2, and >Se. Each R X is independently alkyl, cycloalkyl, aryl or heteroaryl, and these may be substituted with alkyl, cycloalkyl, aryl or heteroaryl. Further, in >C(-R X )2 and >Si(-R X )2, R X may be bonded via a single bond or a linking group X Y to form a ring. Examples of X Y include >O, >N-R Y , >C(-R Y )2, >Si(-R Y )2, >S, >CO, >CS, >SO, >SO2, and >Se. Each R Y is independently alkyl, cycloalkyl, aryl or heteroaryl, and these may be substituted with alkyl, cycloalkyl, aryl or heteroaryl, provided that when X Y is >C(-R Y )2 or >Si(-R Y )2, the two R Y groups do not bond to each other to form an additional ring. Alkenylene is also mentioned as an example of the linking group. Any hydrogen of the alkenylene may be independently substituted with R X , and each R X is independently alkyl, cycloalkyl, substituted silyl, aryl or heteroaryl, and these may be substituted with alkyl, cycloalkyl, substituted silyl or aryl.

[0041] In this specification, when "diarylamino," "diheteroarylamino," or "arylheteroarylamino" is simply referred to, unless otherwise specified, it is assumed that the following explanations are included: "The two aryls in diarylamino are either not bonded to each other or are bonded to each other via a linking group," "The two heteroaryls in the diheteroarylamino are either not bonded to each other or are bonded to each other via a linking group," and "The aryl and heteroaryls in the arylheteroarylamino are either not bonded to each other or are bonded to each other via a linking group."

[0042] Furthermore, the "alkyl" as the first substituent may be either linear or branched, for example, a linear alkyl having 1 to 24 carbon atoms or a branched alkyl having 3 to 24 carbon atoms. A C1 to 18 alkyl (a branched alkyl having 3 to 18 carbon atoms) is preferred, a C1 to 12 alkyl (a branched alkyl having 3 to 12 carbon atoms) is more preferred, a C1 to 8 alkyl (a branched alkyl having 3 to 8 carbon atoms) is even more preferred, a C1 to 6 alkyl (a branched alkyl having 3 to 6 carbon atoms) is particularly preferred, and a C1 to 5 alkyl (a branched alkyl having 3 to 5 carbon atoms) is most preferred.

[0043] Specific alkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl(t-amyl), n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, and t-octyl(1,1,3,3-tetramethylbutyl) Examples include 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 2,6-dimethyl-4-heptyl, 3,5,5-trimethylhexyl, n-decyl, n-undecyl, 1-methyldecyl, n-dodecyl, n-tridecyl, 1-hexylheptyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, and n-eicosyl. Other examples include 1-ethyl-1-methylpropyl, 1,1-diethylpropyl, 1,1-dimethylbutyl, 1-ethyl-1-methylbutyl, 1,1,4-trimethylpentyl, 1,1,2-trimethylpropyl, 1,1-dimethyloctyl, 1,1-dimethylpentyl, 1,1-dimethylheptyl, 1,1,5-trimethylhexyl, 1-ethyl-1-methylhexyl, 1-ethyl-1,3-dimethylbutyl, 1,1,2,2-tetramethylpropyl, 1-butyl-1-methylpentyl, 1,1-diethylbutyl, 1-ethyl-1-methylpentyl, 1,1,3-trimethylbutyl, 1-propyl-1-methylpentyl, 1,1,2-trimethylpropyl, 1-ethyl-1,2,2-trimethylpropyl, 1-propyl-1-methylbutyl, and 1,1-dimethylhexyl.

[0044] As substituents containing the above-mentioned "alkyl," the tertiary-alkyl represented by the following formula (tR) is one of the particularly preferred substituents to the aryl or heteroaryl rings in the A, B, and C rings. This is because such bulky substituents increase the intermolecular distance, thereby improving the quantum emission yield (PLQY). Furthermore, substituents in which the tertiary-alkyl represented by formula (tR) is substituted as a second substituent are also preferred. Specifically, examples include diarylamino substituted with the tertiary-alkyl represented by (tR), carbazolyl (preferably N-carbazol) substituted with the tertiary-alkyl represented by (tR), or benzocarbazol (preferably N-benzocarbazol) substituted with the tertiary-alkyl represented by (tR). For "diarylamino," the group described as the "first substituent" is mentioned. Examples of substitutions of the (tR) group on diarylamino, carbazolyl, and benzocarbazolyl groups include cases where some or all of the hydrogen atoms in the aryl or benzene ring of these groups are substituted with the (tR) group.

[0045] [ka]

[0046] In the formula (tR), R a , R b , and R c Each of these is an alkyl group having 1 to 24 carbon atoms, and any -CH2- in the alkyl group may be substituted with -O-, and the group represented by formula (tR) is substituted with at least one hydrogen in the structure containing the structural unit represented by formula (1) in *.

[0047] R a , R b and R cThe "alkyl group having 1 to 24 carbon atoms" may be either linear or branched, and examples thereof include linear alkyl groups having 1 to 24 carbon atoms, branched alkyl groups having 3 to 24 carbon atoms, alkyl groups having 1 to 18 carbon atoms (branched alkyl groups having 3 to 18 carbon atoms), alkyl groups having 1 to 12 carbon atoms (branched alkyl groups having 3 to 12 carbon atoms), alkyl groups having 1 to 6 carbon atoms (branched alkyl groups having 3 to 6 carbon atoms), and alkyl groups having 1 to 4 carbon atoms (branched alkyl groups having 3 to 4 carbon atoms).

[0048] R in formula (tR) of formula (1) a , R b , and R c preferably has a total number of carbon atoms of 3 to 20, and 3 to 10 is particularly preferred.

[0049] R a , R b , and R c Specific examples of the alkyl group include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl, n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, t-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 2,6-dimethyl-4-heptyl, 3,5,5-trimethylhexyl, n-decyl, n-undecyl, 1-methyldecyl, n-dodecyl, n-tridecyl, 1-hexylheptyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, n-eicosyl and the like.

[0050] Examples of groups represented by formula (tR) include t-butyl, t-amyl, 1-ethyl-1-methylpropyl, 1,1-diethylpropyl, 1,1-dimethylbutyl, 1-ethyl-1-methylbutyl, 1,1,3,3-tetramethylbutyl, 1,1,4-trimethylpentyl, 1,1,2-trimethylpropyl, 1,1-dimethyloctyl, 1,1-dimethylpentyl, 1,1-dimethylheptyl, 1,1,5-trimethylhexyl, 1-ethyl- Examples include 1-methylhexyl, 1-ethyl-1,3-dimethylbutyl, 1,1,2,2-tetramethylpropyl, 1-butyl-1-methylpentyl, 1,1-diethylbutyl, 1-ethyl-1-methylpentyl, 1,1,3-trimethylbutyl, 1-propyl-1-methylpentyl, 1,1,2-trimethylpropyl, 1-ethyl-1,2,2-trimethylpropyl, 1-propyl-1-methylbutyl, and 1,1-dimethylhexyl. Of these, t-butyl and t-amyl are preferred.

[0051] Examples of "cycloalkyl" as the first substituent include cycloalkyls with 3 to 24 carbon atoms, cycloalkyls with 3 to 20 carbon atoms, cycloalkyls with 3 to 16 carbon atoms, cycloalkyls with 3 to 14 carbon atoms, cycloalkyls with 5 to 10 carbon atoms, cycloalkyls with 5 to 8 carbon atoms, cycloalkyls with 5 to 6 carbon atoms, and cycloalkyls with 5 carbon atoms. As will be listed later, cycloalkyls in this specification include not only monocyclic cyclohexyls but also polycyclic ones such as adamantyls.

[0052] Specific examples of cycloalkyls include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, 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, decahydroazlenyl, and alkyl (especially methyl) substituted derivatives of these with 1 to 5 carbon atoms.

[0053] As the first substituent, "alkoxy" can be, for example, a linear alkoxy having 1 to 24 carbon atoms or a branched alkoxy having 3 to 24 carbon atoms. An alkoxy having 1 to 18 carbon atoms (a branched alkoxy having 3 to 18 carbon atoms) is preferred, an alkoxy having 1 to 12 carbon atoms (a branched alkoxy having 3 to 12 carbon atoms) is more preferred, an alkoxy having 1 to 6 carbon atoms (a branched alkoxy having 3 to 6 carbon atoms) is even more preferred, and an alkoxy having 1 to 5 carbon atoms (a branched alkoxy having 3 to 5 carbon atoms) is particularly preferred.

[0054] Specific examples of alkoxys include methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, s-butoxy, t-butoxy, t-amyloxy, pentyloxy, hexyloxy, heptyloxy, and octyloxy.

[0055] Furthermore, as the first substituent, a "substituted silyl" can be a silyl substituted with three substituents selected from the group consisting of alkyl, cycloalkyl, and aryl. Examples include trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, alkyldicycloalkylsilyl, triarylsilyl, dialkylarylsilyl, and alkyldiarylsilyl.

[0056] A "trialkylsilyl" is a group in which each of the three hydrogen atoms in the silyl group is independently substituted with an alkyl group. This alkyl group can be the same group described as "alkyl" in the first substituent mentioned above. Preferred alkyl groups for substitution are those having 1 to 5 carbon atoms, specifically including methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, t-butyl, and t-amyl.

[0057] Specific examples of trialkylsilyls include trimethylsilyl, triethylsilyl, tripropylsilyl, triisopropylsilyl, tributylsilyl, trisec-butylsilyl, trit-butylsilyl, trit-amylsilyl, ethyldimethylsilyl, propyldimethylsilyl, isopropyldimethylsilyl, butyldimethylsilyl, sec-butyldimethylsilyl, t-butyldimethylsilyl, t-amyldimethylsilyl, methyldiethylsilyl, propyldiethylsilyl, isopropyldiethylsilyl, butyldiethylsilyl, sec-butyldiethylsilyl, t-butyldiethylsilyl, t-amyldiethylsilyl, methyldipropylsilyl, ethyldipropylsilyl, t-amyldipropylsilyl, methyldiisopropylsilyl, ethyldiisopropylsilyl, butyldiisopropylsilyl, sec-butyldiisopropylsilyl, t-butyldiisopropylsilyl, t-amyldiisopropylsilyl, and t-amyldiisopropylsilyl.

[0058] "Tricycloalkylsilyl" refers to a group in which each of the three hydrogen atoms in the silyl group is independently substituted with a cycloalkyl group. This cycloalkyl group can be the same as the "cycloalkyl" group described above in the first substituent. Preferred cycloalkyl groups for substitution are those having 5 to 10 carbon atoms, specifically cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.0]pentyl, bicyclo[2.1.1]hexyl, bicyclo[3.1.0]hexyl, bicyclo[2.2.1]heptyl, bicyclo[2.2.2]octyl, adamantyl, decahydronaphthalenyl, decahydroazlenyl, and the like.

[0059] Specific examples of tricycloalkylsilyls include tricyclopentylsilyl and tricyclohexylsilyl.

[0060] Specific examples of dialkylcycloalkylsilyls substituted with two alkyl groups and one cycloalkyl group, and alkyldicycloalkylsilyls substituted with one alkyl group and two cycloalkyl groups, include silyls substituted with groups selected from the specific alkyl and cycloalkyl groups mentioned above.

[0061] Specific examples of dialkylarylsilyls, alkyldiarylsilyls, and triarylsilyls, which are substituted with two alkyl groups and one aryl group, respectively, include silyls substituted with groups selected from the specific alkyl and aryl groups mentioned above. A particularly specific example of a triarylsilyl is triphenylsilyl.

[0062] Furthermore, the explanation of aryl in the first substituent "diarylboryl" can be referenced from the explanation of aryl described above. In addition, these two aryls may be linked by a single bond or by a linking group (e.g., >C(-R)2, >O, >S, or >NR). Here, R in >C(-R)2 and >NR is aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, alkoxy, or aryloxy (the above are the first substituents), and the first substituent may be further substituted with aryl, heteroaryl, alkyl, or cycloalkyl (the above are the second substituents). Specific examples of these groups can be referenced from the explanation of aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, alkoxy, or aryloxy as the first substituent described above. Also, when "diarylboryl" is simply described in this specification, unless otherwise specified, it is assumed that the explanation that "the two aryls of diarylboryl may be linked by a single bond or by a linking group" is included.

[0063] The first substituent, which is a substituted or unsubstituted "aryl", substituted or unsubstituted "heteroaryl", substituted or unsubstituted "diarylamino", substituted or unsubstituted "diheteroarylamino", substituted or unsubstituted "arylheteroarylamino", substituted or unsubstituted "diarylboryl", substituted or unsubstituted "alkyl", substituted or unsubstituted "cycloalkyl", substituted or unsubstituted "alkoxy", substituted or unsubstituted "aryloxy", or substituted "silyl", may have at least one hydrogen substituted with the second substituent, as described as substituted or unsubstituted. Examples of this second substituent include aryl, heteroaryl, alkyl, or cycloalkyl, and specific examples can be found in the descriptions of the monovalent group of the "aryl ring" or "heteroaryl ring" and the "alkyl" or "cycloalkyl" as the first substituent described above. Furthermore, the aryl and heteroaryl groups as the second substituent also include structures in which the aryl or heteroaryl is substituted with an aryl group such as phenyl (specific examples are the groups mentioned above), an alkyl group such as methyl or t-butyl (specific examples are the groups mentioned above), or a cycloalkyl group such as cyclohexyl (specific examples are the groups mentioned above). One example of this is a group in which the 9th position of the second substituent, carbazolyl, is substituted with an aryl group such as phenyl, an alkyl group such as methyl, or a cycloalkyl group such as cyclohexyl.

[0064] The emission wavelength can be adjusted by the steric hindrance, electron-donating, and electron-withdrawing properties of the structure of the first substituent. Preferably, the group is represented by the following structural formula, and more preferably, methyl, t-butyl, t-amyl, t-octyl, neopentyl, adamantyl, phenyl, o-tolyl, p-tolyl, 2,4-xylyl, 2,5-xylyl, 2,6-xylyl, 2,4,6-mesityl, diphenylamino, di-p-tolylamino, bis(p-(t-butyl)phenyl)amino, carbazolyl, 3,6-dimethylcarbazolyl, 3,6- The compounds are di-t-butylcarbazol and phenoxy, and more preferably methyl, t-butyl, t-amyl, t-octyl, neopentyl, adamantyl, phenyl, o-tolyl, 2,6-xylyl, 2,4,6-mesityl, diphenylamino, di-p-tolylamino, bis(p-(t-butyl)phenyl)amino, carbazolyl, 3,6-dimethylcarbazolyl, and 3,6-di-t-butylcarbazolyl. From the viewpoint of ease of synthesis, greater steric hindrance is preferable for selective synthesis, and specifically, t-butyl, t-amyl, t-octyl, adamantyl, o-tolyl, p-tolyl, 2,4-xylyl, 2,5-xylyl, 2,6-xylyl, 2,4,6-mesityl, di-p-tolylamino, bis(p-(t-butyl)phenyl)amino, 3,6-dimethylcarbazolyl, and 3,6-di-t-butylcarbazolyl are preferred.

[0065] In the structural formula below, "Me" represents methyl, "tBu" represents t-butyl, "tAm" represents t-amyl, "tOct" represents t-octyl, and * indicates a bond position. [ka]

[0066] [ka]

[0067] [ka]

[0068]

change

[0069]

change

[0070]

change

[0071]

change

[0072]

change

[0073]

change

[0074]

change

[0075]

change

[0076]

change

[0077]

change

[0078] Polycyclic aromatic compounds having a structure consisting of one or more structural units represented by formula (1) are preferably structures containing at least one tert-alkyl (such as t-butyl or t-amyl), neopentyl, or adamantyl represented by formula (tR) above, and are preferably those containing a tert-alkyl (such as t-butyl or t-amyl) represented by formula (tR). This is because such bulky substituents increase the intermolecular distance, thereby improving the luminescence quantum yield (PLQY). Diarylaminos are also preferred as substituents. Furthermore, diarylaminos substituted with the group of formula (tR), carbazolyls (preferably N-carbazol) substituted with the group of formula (tR), or benzocarbazols (preferably N-benzocarbazol) substituted with the group of formula (tR) are also preferred. Examples of substitutions of the (tR) group on diarylamino, carbazolyl, and benzocarbazolyl groups include cases where some or all of the hydrogen atoms in the aryl or benzene ring of these groups are substituted with the (tR) group.

[0079] In formula (1), Y 1 Each of these is independently B, P, P=O, P=S, Al, Ga, As, Si-R, or Ge-R, where R in Si-R and Ge-R is an aryl group having 6 to 12 carbon atoms, an alkyl group having 1 to 6 carbon atoms, or a cycloalkyl group having 3 to 14 carbon atoms. Y in formula (1) 1 In Si-R and Ge-R, R is an aryl, alkyl, or cycloalkyl group, and the above-mentioned groups are examples of such aryl, alkyl, or cycloalkyl groups. Particularly preferred are aryl groups with 6 to 10 carbon atoms (e.g., phenyl, naphthyl), alkyl groups with 1 to 5 carbon atoms (e.g., methyl, ethyl), or cycloalkyl groups with 5 to 10 carbon atoms (preferably cyclohexyl or adamantyl). 1 The preferred elements are B, P, P=O, or P=S, with B being more preferred.

[0080] X in equation (1) 1 and X 2are each independently >O, >N-R, >Si(-R)2, >C(-R)2, >S, or >Se. X in formula (1) 1 and X 2 preferably has at least one of them being >N-R; it is more preferred that both are >N-R, or one of X 1 and X 2 is >N-R and the other is >C(-R)2, or one of X 1 and X 2 is >N-R and the other is >O, and it is further preferred that both are independently >N-R.

[0081] X in formula (1) 1 and X 2 preferably has at least one >N-R wherein R is aryl substituted with cycloalkyl or heteroaryl substituted with cycloalkyl. As the cycloalkyl in this case, cyclohexyl, adamantyl, or a substituted cycloalkyl represented by any of formula (c11), formula (c12) or formula (c11) described later is preferred.

[0082] X 1 or X 2 R in >N-R which is X116 or X117 is hydrogen, optionally substituted aryl (provided that amino is excluded as a substituent), optionally substituted heteroaryl, optionally substituted alkyl or optionally substituted cycloalkyl. X 1 and X 2 Each R in >Si(-R)2 which is X118 and X119 is independently hydrogen, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkyl or optionally substituted cycloalkyl.

[0083] X 1 or X 2The R in >Si(-R)2 and >C(-R)2 are independently hydrogen, an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted alkyl, or an optionally substituted cycloalkyl, and it is preferable that the two Rs are the same, and the two Rs may be bonded together to form a ring.

[0084] X 1 or X 2 For aryl, heteroaryl, alkyl, and cycloalkyl elements in R of >NR, >Si(-R)2, or >C(-R)2, refer to their descriptions as first substituents above.

[0085] X 1 or X 2 The R in >NR is preferably an optionally substituted aryl, optionally substituted heteroaryl, or optionally substituted cycloalkyl, and more preferably an optionally substituted aryl or optionally substituted heteroaryl. Examples of cycloalkyls are given below. Here, preferred aryls are phenyl, biphenylyl (especially 2-biphenylyl), and terphenylyl (especially terphenyl-2'-yl), and preferred heteroaryls are benzothienyl (2-benzothienyl, 6-benzothienyl, etc.), benzofuranyl (2-benzofuranyl, 3-benzofuranyl, 5-benzofuranyl, etc.), dibenzofuranyl (4-dibenzofuranyl, etc.), dimethylxanthenyl (2-dimethylxanthenyl, etc.), dibenzodioxynyl, etc. Preferred substituents are tert-alkyl (especially t-butyl) or cycloalkyl (especially adamantyl) represented by the above formula (tR). The number of substituents in aryls and heteroaryls is preferably 0 to 2, more preferably 1 or 2, and even more preferably 1. It is also preferable that the aryl ring in the above aryl is condensed with a cycloalkane which may be substituted as described later. Specific examples of cycloalkanes can be found in the following sections.

[0086] X 1 or X 2 As R in >NR, preferred examples other than cycloalkyl-substituted aryls or cycloalkyl-substituted heteroaryls include optionally substituted 2-biphenylyls, optionally substituted terphenyl-2'-yls, and cycloalkane-condensed aryls (which may be substituted). Among optionally substituted 2-biphenylyls, 2-biphenylyls substituted with 1 to 3 t-butyls are particularly preferred. Among optionally substituted terphenyl-2'-yls, unsubstituted [1,1':3',1''-terphenyl]-2'-yl is particularly preferred. Among cycloalkane-condensed aryls, the following are particularly preferred.

[0087] [ka] (Me represents methyl, tBu represents t-butyl, and * indicates the bond position.)

[0088] X 1 and X 2 When both of them are >NR, X 1 and X 2 It is also preferable that one of the R in >NR is an aryl (which may be substituted) condensed with a cycloalkane.

[0089] X 1 or X 2 In >NR, >Si(-R)2, and >C(-R)2, R may be linked to the A ring and / or the B ring, or the A ring and / or the C ring, by a linking group or a single bond. That is, X 1 In >NR, >Si(-R)2 and >C(-R)2, R may be linked to the A ring and / or B ring by a linking group or a single bond, X 2In >NR, >Si(-R)2, and >C(-R)2, R may be linked to the A ring and / or C ring by a linking group or a single bond. Preferred linking groups are -O-, -S-, or -C(-R)2-. The R in "-C(-R)2-" is hydrogen, alkyl, or cycloalkyl. This specification is represented by the following formula (1-3-1), X 1 Ya X 2 This can be represented by compounds having a ring structure in which X is incorporated into fused rings B' and C'. That is, for example, with respect to the benzene ring B (or C), X 1 (or X 2 These compounds have a B' ring (or C' ring) formed by the condensation of another ring, incorporating the B' ring. The resulting condensed ring B' (or C') is, for example, a carbazole ring, a phenoxazine ring, a phenothiazine ring, or an acridine ring.

[0090] Furthermore, the above regulations are expressed by the following formulas (1-3-2) and (1-3-3), X 1 and / or X 2 It can also be represented by compounds having a ring structure in which X is incorporated into the fused ring A'. That is, for example, with respect to ring A which is a benzene ring, X 1 (and / or X 2 These compounds have an A' ring formed by the condensation of another ring, incorporating the A' ring. The resulting condensed ring A' is, for example, a carbazole ring, a phenoxazine ring, a phenothiazine ring, or an acridine ring.

[0091] [ka]

[0092] As an example, it is also preferable that the R in >NR is a cycloalkyl group which may be substituted and is bonded to the A, B, or C ring by a single bond. As the cycloalkyl group, a substituted cyclopentyl or a substituted cyclohexyl is preferred.

[0093] As a particularly preferred example of the fused ring formed as described above, the structure represented by formula (A11) can be cited. In this case, the two carbon atoms substituted with methyl are chiral carbons, and the compound represented by formula (1) may exist as a diastereomer or an enantiomer. However, the compound represented by formula (1) may be any of these isomers, or it may be in the form of a mixture of possible isomers in any ratio.

[0094] [ka]

[0095] In formula (A11), Me is methyl, and X is present at the two * positions. 1 or X 2 The compound is bonded to one of the two rings at the position of **. Examples of such structures include the compounds represented by formulas (1-17), (1-32), (1-56), and (1-72), which will be discussed later.

[0096] The above preferred range of R is >NR to X 1 or X 2 By using the compound of the present invention, which has the properties of the present invention, as a light-emitting material in the manufacture of the device, the light-emitting efficiency and device lifespan can be further improved.

[0097] X in equation (1) 1 or X 2In >Si(-R)2, R is hydrogen, an optionally substituted aryl group, an optionally substituted heteroaryl group, an optionally substituted alkyl group, or an optionally substituted cycloalkyl group. Here, the substitution when substituted can be the second substituent mentioned above. The aryl, heteroaryl, alkyl, or cycloalkyl groups can be the groups mentioned above as the first substituent, respectively. Particularly preferred are aryl groups having 6 to 10 carbon atoms (e.g., phenyl, naphthyl), heteroaryl groups having 2 to 15 carbon atoms (e.g., carbazolyl), alkyl groups having 1 to 5 carbon atoms (e.g., methyl, ethyl), or cycloalkyl groups having 5 to 10 carbon atoms (preferably cyclohexyl or adamantyl).

[0098] X in equation (1) 1 or X 2 In >C(-R)2, R is hydrogen, an optionally substituted aryl group, an optionally substituted heteroaryl group, an optionally substituted alkyl group, or an optionally substituted cycloalkyl group. When substituted, the substituents include the second substituents mentioned above. The groups listed above as the first substituents are examples of the aryl, heteroaryl, alkyl, or cycloalkyl groups. Particularly preferred are aryl groups with 6 to 10 carbon atoms (e.g., phenyl, naphthyl), heteroaryl groups with 2 to 15 carbon atoms (e.g., carbazolyl), alkyl groups with 1 to 5 carbon atoms (e.g., methyl, ethyl), or cycloalkyl groups with 5 to 10 carbon atoms (preferably cyclohexyl or adamantyl).

[0099] In equation (1), X 1 , X 2Examples of linking groups when bonded to the A ring and / or B ring include -O-, -S-, or -C(-R)2-, where R in "-C(-R)2-" is hydrogen, alkyl, or cycloalkyl, and the alkyl or cycloalkyl groups described above are examples of the first substituents. Particularly preferred are alkyl groups with 1 to 5 carbon atoms (e.g., methyl, ethyl, etc.) or cycloalkyl groups with 5 to 10 carbon atoms (preferably cyclohexyl or adamantyl).

[0100] At least one hydrogen in formula (1) is substituted with a substituted or unsubstituted cycloalkyl group. A cycloalkyl group having 5 to 10 carbon atoms is preferred, and cyclohexyl or adamantyl is preferred. Furthermore, substituted cycloalkyl groups of formulas (c11), (c12), or (c13) below are also preferred, in which the hydrogen of the tertiary carbon of cyclohexyl or adamantyl is substituted with methyl. This description also applies to cycloalkyl groups substituted with aryl or heteroaryl groups in G of formula (2), which will be described later. In formulas (c11), (c12), and (c13), * represents the bond position. Note that the groups represented by formulas (c11) and (c12) below are methyl-substituted adamantyl groups, and therefore both are cycloalkyl groups having 10 carbon atoms.

[0101] [ka]

[0102] The polycyclic aromatic compounds according to the present invention can be used as materials for organic devices. Examples of organic devices include organic field-light-emitting devices, organic field-effect transistors, and organic thin-film solar cells. In particular, in organic field-light-emitting devices, the polycyclic aromatic compound having a structure consisting of one or more structural units represented by formula (1) of the present invention or formula (2) described later is used as the dopant material for the light-emitting layer, Y 1 B, X 1 and X 2Compounds in which each is independently >NR or >O are preferred, Y 1 B, X 1 and X 2 A compound in which one of the elements is >NR and the other is >NR or >O is more preferable, Y 1 B, X 1 and X 2 Compounds in which each of the following is independently >NR are most preferred, and as the host material for the light-emitting layer, Y 1 B, X 1 and X 2 A compound in which one of the atoms is >O and the other is >NR or >O is preferred, Y 1 B, X 1 and X 2 Compounds in which both > O are more preferred, and as electron transport material, Y 1 B, X 1 and X 2 Compounds in which all of the following are >O, or Y 1 P=O, X 1 and X 2 Compounds in which all of the following are >O are preferably used.

[0103] The polycyclic aromatic compound of the present invention is a polycyclic aromatic compound having a structure consisting of one or more structural units represented by formula (1). Examples of polycyclic aromatic compounds having a structure consisting of one of the above structural units include the polycyclic aromatic compound represented by the formula described above as the structural unit represented by formula (1). Examples of polycyclic aromatic compounds having a structure consisting of two or more structural units represented by formula (1) include compounds corresponding to the polymer of the polycyclic aromatic compound represented by the formula described above as the structural unit represented by formula (1). The polymer is preferably a 2-6 hexamer, more preferably a 2-3 metricer, and particularly preferably a dimer. The polymer may be in a form in which a single compound has multiple of the above unit structures, and may be in a form in which any ring (A ring, B ring, or C ring) included in the above structural unit is shared among multiple unit structures, or may be in a form in which any rings (A ring, B ring, or C ring) included in the above unit structures are condensed together. Furthermore, the above unit structure may also be in a form in which multiple linking groups such as single bonds and alkylenes, phenylenes, and naphthylenes having 1 to 3 carbon atoms are bonded together. Of these, a form in which the rings are shared is preferred.

[0104] In polycyclic aromatic compounds having a structure consisting of one or more structural units represented by formula (1), at least one selected from the group consisting of aryl rings and heteroaryl rings is condensed with at least one cycloalkane. The same applies to polycyclic aromatic compounds represented by formula (2), which will be described later, and the following explanation also applies to polycyclic aromatic compounds represented by formula (2). In polycyclic aromatic compounds having a structure consisting of one or more structural units represented by formula (1), the number of structures in which an aryl ring or heteroaryl ring is condensed with a cycloalkane may be one or more, preferably 1 to 4, and more preferably 2 or 3.

[0105] The cycloalkane can be any cycloalkane having 3 to 24 carbon atoms. In this case, at least one hydrogen atom in the cycloalkane may be substituted with an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, an alkyl group having 1 to 24 carbon atoms, or a cycloalkyl group having 3 to 24 carbon atoms, and at least one -CH2- in the cycloalkane may be substituted with an -O- group.

[0106] In a structure consisting of one or more structural units represented by formula (1), if at least one selected from the group consisting of aryl rings and heteroaryl rings is condensed with at least one cycloalkane, it is preferable that the at least one cycloalkane is a cycloalkane having 3 to 20 carbon atoms, wherein at least one hydrogen atom in the cycloalkane may be substituted with an aryl ring having 6 to 16 carbon atoms, a heteroaryl ring having 2 to 22 carbon atoms, an alkyl ring having 1 to 12 carbon atoms, or a cycloalkyl ring having 3 to 16 carbon atoms.

[0107] Examples of "cycloalkanes" include cycloalkanes with 3 to 24 carbon atoms, cycloalkanes with 3 to 20 carbon atoms, cycloalkanes with 3 to 16 carbon atoms, cycloalkanes with 3 to 14 carbon atoms, cycloalkanes with 5 to 10 carbon atoms, cycloalkanes with 5 to 8 carbon atoms, cycloalkanes with 5 to 6 carbon atoms, and cycloalkanes with 5 carbon atoms.

[0108] Specific examples of cycloalkanes include cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctane, cyclononane, cyclodecane, bicyclo[1.1.0]butane, bicyclo[1.1.1]pentane, bicyclo[2.1.0]pentane, bicyclo[2.1.1]hexane, bicyclo[3.1.0]hexane, bicyclo[2.2.1]heptane (norbornane), bicyclo[2.2.2]octane, adamantane, diamantane, decahydronaphthalene, and decahydroazulene, as well as alkyl (especially methyl), halogen (especially fluorine), and deuterium-substituted compounds of these compounds having 1 to 5 carbon atoms.

[0109] Among these, a structure in which the α-carbon of the cycloalkane (the carbon adjacent to the carbon at the condensation site in a cycloalkyl condensed to an aryl or heteroaryl ring) is substituted is preferred, as shown in the structural formula below; a structure in which the α-carbon is substituted with two or more substituents is more preferred; and a structure in which two α-carbons are substituted with a total of four substituents is even more preferred. Examples of such substituents include alkyl (especially methyl) substituted compounds having 1 to 5 carbon atoms, halogen (especially fluorine) substituted compounds, and deuterium substituted compounds. In particular, a structure in which a substructure represented by the following formula (Z) is bonded to an adjacent carbon atom in an aryl or heteroaryl ring is preferred.

[0110] [ka] In formula (Z), Me represents a methyl group, and * indicates the bond position.

[0111] The number of cycloalkanes condensed to a single aryl or heteroaryl ring is preferably 1 to 3, more preferably 1 or 2, and even more preferably 1. For example, the following shows an example in which one or more cycloalkanes are condensed to a single benzene ring (phenyl). * indicates the bonding position, and this position may be any carbon that constitutes the benzene ring but not the cycloalkane. Condensed cycloalkanes may also be condensed together, as in formulas (Cy-1-4) and (Cy-2-4). The same applies when the ring (group) to be condensed is an aryl or heteroaryl ring other than a benzene ring (phenyl), and when the cycloalkane to be condensed is a cycloalkane other than cyclopentane or cyclohexane.

[0112] [ka]

[0113] At least one -CH2- in a cycloalkane may be substituted with -O-. For example, the following shows a cycloalkane condensed to a single benzene ring (phenyl) in which one or more -CH2- groups are substituted with -O-. The same applies when the condensed ring (group) is an aromatic ring or heteroaromatic ring other than a benzene ring (phenyl), or when the condensed cycloalkane is a cycloalkane other than cyclopentane or cyclohexane.

[0114] [ka]

[0115] At least one hydrogen atom in the cycloalkane may be substituted. Examples of such substituents include aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl, alkyl, cycloalkyl, alkoxy, aryloxy, substituted silyl, deuterium, cyano, or halogen. Details of these substituents can be found in the description of the first substituent above. Among these substituents, alkyl (e.g., alkyls with 1 to 6 carbon atoms), cycloalkyl (e.g., cycloalkyls with 3 to 14 carbon atoms), halogen (e.g., fluorine), and deuterium are preferred. Furthermore, when a cycloalkyl molecule is substituted, it may be in a form that forms a spiro structure, an example of which is shown below.

[0116] [ka]

[0117] Examples of cycloalkane condensation include, firstly, the aryl and heteroaryl rings in the A, B, and C rings of polycyclic aromatic compounds having a structure consisting of one or more structural units represented by formula (1), the aryl and heteroaryl rings that are the a, b, and c rings in formula (2) described later, and the aryl and heteroaryl rings in a fused ring that are condensed with a cycloalkane.

[0118] Other forms of cycloalkane condensation include polycyclic aromatic compounds having a structure consisting of one or more structural units represented by formula (1), or polycyclic aromatic compounds represented by formula (2) described later, such as those where R is an aryl condensed with a cycloalkane (>NR), a diarylamino condensed with a cycloalkane (condensation to this aryl moiety), a carbazolyl condensed with a cycloalkane (condensation to this benzene ring moiety), or a benzocarbazolyl condensed with a cycloalkane (condensation to this benzene ring moiety). For "diarylamino," the group described above as the "first substituent" is an example.

[0119] Furthermore, as a more specific example, in the polycyclic aromatic compound represented by formula (2) described later, Y in ring a. 1 R at the para position Z Examples include diarylamino compounds condensed with a cycloalkane (the cycloalkane condenses on the aryl portion) or carbazolyl compounds condensed with a cycloalkane (the cycloalkane condenses on the benzene ring portion).

[0120] In polycyclic aromatic compounds having a structure consisting of one or more structural units represented by formula (1), and in polycyclic aromatic compounds represented by formula (2) described later, the cycloalkane condensation is preferably in the form of condensation on the A(a) ring, the B(b) ring, or the C(c) ring, and more preferably in the form of condensation on the A(a) ring and the B(b) ring. A form in which both the A(a) ring and the B(b) ring are condensed is also preferred.

[0121] Furthermore, by introducing a cycloalkane structure to the polycyclic aromatic compound of the present invention, a decrease in melting point and sublimation temperature can be expected. This means that in sublimation purification, which is almost indispensable as a purification method for organic devices such as organic EL elements that require high purity, purification can be performed at a relatively low temperature, thus avoiding thermal decomposition of the material. The same applies to the vacuum deposition process, which is a powerful means of fabricating organic devices such as organic EL elements, as the process can be carried out at a relatively low temperature, thus avoiding thermal decomposition of the material and resulting in the acquisition of high-performance organic devices. In addition, since the solubility in organic solvents is improved by introducing a cycloalkane structure, it can also be applied to the fabrication of elements using coating processes. However, the present invention is not particularly limited to these principles.

[0122] In a structure consisting of one or more structural units represented by formula (1), all or part of the hydrogen atoms may be deuterium, cyano, or halogen. The same applies to the polycyclic aromatic compounds represented by formula (2), which will be described later, and the following explanation also applies to the polycyclic aromatic compounds represented by formula (2).

[0123] For example, in a structure consisting of one or more structural units represented by formula (1), the A ring, B ring, C ring (A to C rings are aryl rings or heteroaryl rings), substituents on the A to C rings, Y 1 When R is Si-R or Ge-R, R (=alkyl, cycloalkyl, aryl, or heteroaryl), and X 1 and X 2When R is >NR, >C(-R)2, or >Si(-R)2, the hydrogen in R (=alkyl, cycloalkyl, aryl, or heteroaryl) may be substituted with deuterium, cyano, or halogen, among which embodiments include those in which all or some of the hydrogen in the aryl or heteroaryl is substituted with deuterium, cyano, or halogen. The halogen is fluorine, chlorine, bromine, or iodine, preferably fluorine, chlorine, or bromine, more preferably fluorine or chlorine, and even more preferably fluorine. Furthermore, from the viewpoint of durability, it is also preferable that all or some of the hydrogen in the structure consisting of one or more structural units represented by formula (1) is deuterated, and more preferably all of it is deuterated.

[0124] A preferred example of a polycyclic aromatic compound having a structure consisting of one or more structural units represented by formula (1) is the polycyclic aromatic compound represented by formula (2) below. For details on the substituents, ring structures, and preferred ranges in formula (2), please refer to the corresponding descriptions of formula (1).

[0125] [ka]

[0126] In equation (2), Y 1 and X 1 Y in equation (1) 1 and X 1 These are synonymous with each other.

[0127] In equation (2), Z is independently either N or CR. Z The CR Z R ZEach of these is independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl, alkyl, cycloalkyl, alkoxy, aryloxy, or substituted silyl, where at least one hydrogen is substituted with aryl, heteroaryl, alkyl, or cycloalkyl. For details of the substituents listed herein, refer to the descriptions of the first and second substituents above.

[0128] Two adjacent R Z These atoms may bond to each other to form an aryl ring or a heteroaryl ring, and the formed aryl ring and heteroaryl ring may each be substituted with aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl, alkyl, cycloalkyl, alkoxy, aryloxy, or substituted silyl, and at least one hydrogen atom in these may be substituted with aryl, heteroaryl, alkyl, or cycloalkyl, and for details of the substituents listed herein, refer to the descriptions of the first substituent and the second substituent above.

[0129] In formula (2), Z=Z may independently be >O, >NR, >C(-R)2, >Si(-R)2, >S, or >Se, and more preferably >O, >NR, >C(-R)2, or >S. The R in >NR, >C(-R)2, and >Si(-R)2 may independently be hydrogen, a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted alkyl, or a substituted or unsubstituted cycloalkyl, and the two Rs in >C(-R)2 and >Si(-R)2 may be bonded to each other to form a ring. For details of the substituents listed here, please refer to the description of the first substituent above.

[0130] In rings such as b-rings and c-rings, when the "Z=Z" part is replaced with >O, ​​>NR, >C(-R)2, >Si(-R)2, >S, or >Se, the resulting rings include cyclopentadiene rings, pyrrole rings, furan rings, and thiophene rings. Furthermore, if the remaining Z is adjacent to them, they form a CR ring. Z And that R Z When bonded to form a benzene ring, it may form an indene ring, an indole ring, a benzofuran ring, or a benzothiophene ring. The formed ring may have substituents. Examples include, in ring b, one Z=Z is >NR, >O, >S, >C(-R)2 and the remaining Z is CH, and one Z=Z is >NR, >O, >S, >C(-R)2 and the remaining Z are adjacent and both are CR Z And these R Z Examples of how these elements bond to each other to form a benzene ring are shown below. However, the forms that the b-ring, c-ring, etc., can take are not limited to the examples below.

[0131] [ka]

[0132] Also, CR Z R Z Examples of how these compounds combine to form aryl rings such as cyclopentadiene rings, pyrrole rings, furan rings, thiophene rings, indene rings, indole rings, benzofuran rings, or benzothiophene rings, as well as heteroaryl rings, are shown below. [ka]

[0133] In the example above, in equation (2), Y 1 and X 1 Although an example was given regarding the b-ring that is bonded, this explanation can be similarly applied to the a-ring or c-ring in equation (2).

[0134] X in equation (1) 1 and X 2The above statement that in formula (2), R in at least one of >NR, >Si(-R)2 and >C(-R)2 may be bonded to the A ring and / or B ring by a linking group or a single bond, is incorrect. Z R in Z is Z This corresponds to the provision that "is bonded to one or two of the following." Specifically, the above R is the spatially closest CR in each of the following rings. Z It may also be bonded to Z, and in equation (2), X 1 The R inside condenses into the a-ring and / or b-ring.

[0135] In equation (2), there are 0 to 4 rings (monorings) containing Z, which is N, preferably 0 to 3, more preferably 0 to 2, and particularly preferably 0 to 1. In each of the above equations, Z is always CR. Z It is also preferable that it be so.

[0136] In formula (2), in a ring (monocyclic) containing Z which is N, it is preferable that one or two of the multiple Zs are N, and when two are N, it is preferable that the two Ns are not adjacent to each other. When the 6-membered ring is a ring containing Z which is N, it is preferably a pyridine ring, pyrimidine ring, pyridazine ring, or 1,2,3-triazine ring, and more preferably a pyridine ring or pyrimidine ring. When the 5-membered ring is a ring containing Z which is N, it is preferably a thiazole ring or an oxazole ring.

[0137] Preferred examples of polycyclic aromatic compounds having a structure consisting of one or more structural units represented by formula (1) include compounds represented by formulas (1a), (1b), (1c), (1d), (1e), (1f), (1g), (1h), or (1i). [ka]

[0138] [ka]

[0139] In equations (1a), (1b), (1c), (1d), (1e), (1f), (1g), (1h), and (1i), Z a Each is independently N or CR Za And Z b Each is independently N or CR Zb And Z c Each is independently N or CR Zc And R Za , R Zb and R Zc Each of these is independently a hydrogen, aryl, heteroaryl, diarylamino (where the two aryls are not bonded to each other or are bonded via a single bond or a linking group), diheteroarylamino (where the two heteroaryls are not bonded to each other or are bonded via a single bond or a linking group), arylheteroarylamino (where the aryl and heteroaryl are not bonded to each other or are bonded via a single bond or a linking group), diarylboryl (where the two aryls are not bonded to each other or are bonded via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, or substituted silyl, wherein at least one hydrogen in these may be substituted with an aryl, heteroaryl, alkyl, or cycloalkyl. Two adjacent R Za , two adjacent R Zb and two adjacent R ZcThese may bond to each other to form an aryl ring or a heteroaryl ring, and the formed aryl ring and heteroaryl ring may be substituted with aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (the two aryls may be bonded via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, or substituted silyl, and at least one hydrogen in these may be substituted with aryl, heteroaryl, alkyl, or cycloalkyl; X c >O, >NR, >C(-R)2, >Si(-R)2, >S, or >Se, where R in >NR, >C(-R)2, and >Si(-R)2 is independently hydrogen, a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted alkyl, or a substituted or unsubstituted cycloalkyl, and the two Rs in >C(-R)2 and >Si(-R)2 are bonded to each other to form a ring, or are not bonded to each other; Y 1 is B, P, P=O, P=S, Al, Ga, As, Si-R, or Ge-R, where R in Si-R and Ge-R is a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted alkyl, or a substituted or unsubstituted cycloalkyl; X 1 and X 2 These are independently >O, >NR, >C(-R)2, >Si(-R)2, >S, or >Se, where X 1 and X 2Either one of them is >NG, and the R in >NR is hydrogen, a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted alkyl, or a substituted or unsubstituted cycloalkyl, and the R in >C(-R)2 and the R in >Si(-R)2 are independently hydrogen, a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted alkyl, or a substituted or unsubstituted cycloalkyl, and the two Rs in >C(-R)2 and the R in >Si(-R)2 may be bonded to each other to form a ring, and the R in >NR, the R in >C(-R)2 and the R in >Si(-R)2 are linked by a linking group or single bond to the CR Z The R in Z is Z It may be combined with one or two of the following: G is a cycloalkyl-substituted aryl or cycloalkyl-substituted heteroaryl; In each of the structures represented by formulas (1a), (1b), (1c), (1d), (1e), (1f), (1g), (1h), and (1i), at least one selected from the group consisting of aryl rings and heteroaryl rings is condensed with at least one cycloalkane, wherein at least one hydrogen in the cycloalkane may be substituted, and at least one -CH2- in the cycloalkane may be substituted with -O-; At least one hydrogen atom in the above structure may be substituted with cyano, halogen, or deuterium.

[0140] In the structures represented by formulas (1a) and (1b), it is preferable that at least one of the b-ring or c1-ring is condensed with a cycloalkane, and more preferably that both are condensed with a cycloalkane. In formulas (1c), (1d), (1e), (1f), (1g), and (1h), it is preferable that at least one of the b-ring or c2-ring is condensed with a cycloalkane, and more preferably that both are condensed with a cycloalkane. In formula (1i), it is preferable that both the b-ring and c1-ring are condensed with a cycloalkane. Furthermore, in formula (1i), it is also preferable that one of the b-ring and c1-ring is condensed with a cycloalkane, the other is not condensed with a cycloalkane, and the ring has at least one substituent selected from the group consisting of substituted or unsubstituted diarylamino, substituted or unsubstituted arylheteroarylamino, and substituted or unsubstituted diheteroarylamino as a substituent (substituted or unsubstituted diarylamino is more preferred).

[0141] In formulas (2), (1a), (1b), (1c), (1d), (1e), (1f), (1g), (1h), and (1i), G is a cycloalkyl-substituted aryl or cycloalkyl-substituted heteroaryl, preferably a cycloalkyl-substituted aryl, more preferably a cycloalkyl-substituted phenyl or cycloalkyl-substituted biphenyl, and even more preferably a cycloalkyl-substituted phenyl. The aryl, heteroaryl and phenyl may be further substituted. For "cycloalkyl," "aryl," and "heteroaryl" as used here, refer to the above description. For "may be substituted," refer to the above description regarding the first and second substituents, but the substituent is preferably an alkyl or an alkyl-substituted aryl, more preferably an alkyl, even more preferably t-butyl or methyl, and most preferably methyl. As the cycloalkyl, a cycloalkyl having 5 to 10 carbon atoms (preferably cyclohexyl or adamantyl) is preferred, and adamantyl is most preferred. Furthermore, methyl-substituted adamantyl, in which a methyl group is further substituted onto adamantyl, is also preferred.

[0142] For G, substituents represented by formula (G01) or formula (G02) are preferred, and substituents represented by formula (G11) or formula (G12) are more preferred. In formulas (G01), (G02), (G11), and (G12), * represents the bond position with the nitrogen atom, and Cy represents cycloalkyl. In formulas (G01) and (G02), Rg is independently a substituted or unsubstituted alkyl, a substituted or unsubstituted aryl, or a substituted or unsubstituted heteroaryl, but alkyl is preferred. Also, k and l are integers from 1 to 4.

[0143] [ka]

[0144] Further specific examples of the polycyclic aromatic compound represented by formula (1) of the present invention include the following compounds. In the following structural formulas, "Me" represents methyl, "tBu" represents t-butyl, and "D" represents deuterium. Note that the following structure is just one example.

[0145] [ka]

[0146] [ka]

[0147] [ka]

[0148] [ka]

[0149] [ka]

[0150] [ka]

[0151] [ka]

[0152] [ka]

[0153] [ka]

[0154]

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[0155]

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[0156]

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[0157]

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[0158]

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[0159]

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[0160]

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[0161]

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[0162]

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[0163]

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[0164]

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[0165] [ka]

[0166] [ka]

[0167] [ka]

[0168] The polycyclic aromatic compounds of the present invention can be produced by the following procedure.

[0169] Method for producing polycyclic aromatic compounds Polycyclic aromatic compounds having a structure consisting of one or more structural units represented by formula (1) or formula (2) are basically formed by first bonding the A ring (a ring), B ring (b ring), and C ring (c ring) with a bonding group (X 1 Ya X 2 An intermediate is produced by bonding the rings with a group containing (Y) (first reaction), and then the A ring (a ring), B ring (b ring), and C ring (c ring) are bonded with a group containing (Y) 1 The final product can be produced by bonding with a group containing (second reaction). In the first reaction, for example, if it is an etherification reaction, general reactions such as nucleophilic substitution reactions and Ullmann reactions can be used, and if it is an amination reaction, general reactions such as the Buchwald-Hartwig reaction can be used. In the second reaction, a tandem hetero-Friedel-Crafts reaction (sequential aromatic electrophilic substitution reaction, the same applies below) can be used. By using a starting material having the desired fused ring at some point in the reaction process, or by adding a ring condensation step, the compound can be produced as a fused ring in which at least one ring selected from the group consisting of rings A, B, and C is composed of two or more rings selected from the group consisting of a monocyclic aryl ring, a monocyclic heteroaryl ring, and a cyclopentadiene ring.

[0170] Manufacturing method via intermediate-1 The polycyclic aromatic compounds of the present invention can be produced by a manufacturing method comprising the following steps. For details of each step, please refer to International Publication No. 2015 / 102118.

[0171] Using an organic alkali compound, X in the following intermediate-1 1 and X 2 The reaction step involves metallizing the halogen atoms (Hal) between them, and Y 1 Halides of Y 1 Amination halogens, Y 1 Alkoxy compounds and Y 1 Using a reagent selected from the group consisting of aryl oxyides, the metal and Y 1 A reaction step to exchange and, using a Brønsted base, a continuous aromatic electrophilic substitution reaction is carried out, resulting in the Y 1 The reaction, which includes a reaction step to bond the B ring and the C ring, is described below.

[0172] [ka]

[0173] Examples of metallating reagents used in the halogen-metal exchange reaction in the scheme described above include alkyllithium compounds such as methyllithium, n-butyllithium, sec-butyllithium, and t-butyllithium; isopropylmagnesium chloride; isopropylmagnesium bromide; phenylmagnesium chloride; phenylmagnesium bromide; and lithium chloride complexes of isopropylmagnesium chloride, known as turbogrignard reagents.

[0174] In addition to the reagents mentioned above, other organic alkali compounds used as metalling reagents in the orthometal exchange reaction in the scheme described above include lithium diisopropylamide, lithium tetramethylpiperidide, lithium hexamethyldisilazide, potassium hexamethyldisilazide, lithium tetramethylpiperidinylmagnesium chloride-lithium chloride complex, and lithium tri-n-butylmagnesate.

[0175] Furthermore, when alkyllithium is used as a metalling reagent, additives that can accelerate the reaction include N,N,N',N'-tetramethylethylenediamine, 1,4-diazabicyclo[2.2.2]octane, and N,N-dimethylpropylene urea.

[0176] Furthermore, Lewis acids used in the schemes described above include AlCl3, AlBr3, AlF3, BF3·OEt2, BCl3, BBr3, GaCl3, GaBr3, InCl3, InBr3, In(OTf)3, SnCl4, SnBr4, AgOTf, ScCl3, Sc(OTf)3, ZnCl2, ZnBr2, Zn(OTf)2, MgCl2, MgBr2, Mg(OTf)2, LiOTf, NaOTf, KOTf, Me3SiOTf, Cu(OTf)2, CuCl2, YCl3, Y(OTf)3, TiCl4, TiBr4, ZrCl4, ZrBr4, FeCl3, FeBr3, CoCl3, and CoBr3. These Lewis acids can also be used in a similar manner when supported on a solid.

[0177] Furthermore, examples of Brønsted acids used in the schemes described above include p-toluenesulfonic acid, methanesulfonic acid, trifluoromethanesulfonic acid, fluorosulfonic acid, carborane acid, trifluoroacetic acid, (trifluoromethanesulfonyl)imide, tris(trifluoromethanesulfonyl)methane, hydrogen chloride, hydrogen bromide, and hydrogen fluoride. Examples of solid Brønsted acids include Amberlist (trade name: Dow Chemical), Nafion (trade name: DuPont), zeolite, and TeikaCure (trade name: Teika Corporation).

[0178] Furthermore, amines that may be added to the schemes described above include diisopropylethylamine, triethylamine, tributylamine, 1,4-diazabicyclo[2.2.2]octane, N,N-dimethyl-p-toluidine, N,N-dimethylaniline, pyridine, 2,6-lutidine, and 2,6-di-t-butylamine.

[0179] Furthermore, solvents used in the schemes described above include o-dichlorobenzene, chlorobenzene, toluene, benzene, methylene chloride, chloroform, dichloroethylene, benzotrifluoride, decalin, cyclohexane, hexane, heptane, 1,2,4-trimethylbenzene, xylene, diphenyl ether, anisole, cyclopentyl methyl ether, tetrahydrofuran, dioxane, and methyl-t-butyl ether.

[0180] Here, Y 1 However, although an example of B was described, by appropriately changing the raw materials, Y can be produced. 1 However, compounds with P, P=O, P=S, Al, Ga, As, Si-R, or Ge-R can also be synthesized.

[0181] In the above scheme, a Brønsted base or Lewis acid may be used to accelerate the tandem hetero-Friedel-Crafts reaction. However, Y 1 trifluoride, Y 1 trichloride, Y 1 Tribromide of Y 1 Y such as triiodide 1 When using halides, as the aromatic electrophilic substitution reaction progresses, acids such as hydrogen fluoride, hydrogen chloride, hydrogen bromide, and hydrogen iodide are produced, so the use of a Brønsted base to capture the acids is effective. On the other hand, Y 1 Amination halogens, Y 1 When using alkoxy compounds, amines and alcohols are produced as the aromatic electrophilic substitution reaction progresses, so in many cases, it is not necessary to use a Brønsted base. However, because the leaving ability of aminos and alkoxys is low, the use of a Lewis acid to promote their elimination is effective.

[0182] Furthermore, the polycyclic aromatic compounds of the present invention also include compounds in which at least some hydrogen atoms are substituted with deuterium or cyano compounds, and compounds in which they are substituted with halogens such as fluorine or chlorine. Such compounds can be synthesized in the same manner as described above by using raw materials in which the desired positions have been deuterated, cyanated, fluorinated, or chlorinated.

[0183] 2. Organic devices The polycyclic aromatic compounds of the present invention can be used as materials for organic devices. Examples of organic devices include organic field-light-emitting devices, organic field-effect transistors, and organic thin-film solar cells.

[0184] 2-1. Organic electroluminescent devices 2-1-1. Structure of an organic electroluminescent device Figure 1 is a schematic cross-sectional view showing an example of an organic EL element. The organic EL element 100 shown in Figure 1 comprises a substrate 101, an anode 102 provided on the substrate 101, a hole injection layer 103 provided on the anode 102, a hole transport layer 104 provided on the hole injection layer 103, a light-emitting layer 105 provided on the hole transport layer 104, an electron transport layer 106 provided on the light-emitting layer 105, an electron injection layer 107 provided on the electron transport layer 106, and a cathode 108 provided on the electron injection layer 107.

[0185] The organic EL element 100 may also be configured by reversing the manufacturing order, for example, by having a substrate 101, a cathode 108 provided on the substrate 101, an electron injection layer 107 provided on the cathode 108, an electron transport layer 106 provided on the electron injection layer 107, an emissive layer 105 provided on the electron transport layer 106, a hole transport layer 104 provided on the emissive layer 105, a hole injection layer 103 provided on the hole transport layer 104, and an anode 102 provided on the hole injection layer 103.

[0186] Not all of the above layers are necessarily required; the minimum configuration unit consists of an anode 102, a light-emitting layer 105, and a cathode 108, and the hole injection layer 103, hole transport layer 104, electron transport layer 106, and electron injection layer 107 are optional layers. Furthermore, each of the above layers may consist of a single layer or multiple layers.

[0187] In addition to the above-mentioned "substrate / anode / hole injection layer / hole transport layer / emissive layer / electron transport layer / electron injection layer / cathode" configurations, other configurations of layers constituting an organic EL element include "substrate / anode / hole transport layer / emissive layer / electron transport layer / electron injection layer / cathode", "substrate / anode / hole injection layer / emissive layer / electron transport layer / electron injection layer / cathode", "substrate / anode / hole injection layer / hole transport layer / emissive layer / electron injection layer / cathode", and "substrate / anode / hole injection layer / hole transport layer / emissive layer / electron transport The configuration may also be "transport layer / cathode", "substrate / anodode / emissive layer / electron transport layer / electron injection layer / cathode", "substrate / anodode / hole transport layer / emissive layer / electron injection layer / cathode", "substrate / anodode / hole transport layer / emissive layer / electron transport layer / cathode", "substrate / anodode / hole injection layer / emissive layer / electron injection layer / cathode", "substrate / anodode / hole injection layer / emissive layer / electron transport layer / cathode", "substrate / anodode / emissive layer / electron transport layer / cathode", or "substrate / anodode / emissive layer / electron injection layer / cathode".

[0188] 2-1-2. Light-emitting layer in organic electroluminescent device The polycyclic aromatic compounds of the present invention are preferably used as materials for forming one or more organic layers in an organic electroluminescent device, and more preferably as materials for forming a light-emitting layer. The light-emitting layer 105 is a layer that emits light by recombining holes injected from the anode 102 and electrons injected from the cathode 108 between electrodes to which an electric field is applied. The material for forming the light-emitting layer 105 can be any compound that emits light when excited by the recombination of holes and electrons (luminescent compound), and it is preferable that it can form a stable thin film shape and exhibits strong luminescence (fluorescence) efficiency in the solid state. The polycyclic aromatic compounds of the present invention can be used as materials for the light-emitting layer, may be used as dopant materials, or may be used as host materials, but it is preferable to use them as materials for the light-emitting layer, and more preferably as dopant materials.

[0189] In addition, there are examples where assisting dopants and emitting dopants are used in combination as dopants, and these examples will be discussed later. In this specification, when the term "dopant" is used alone, it refers to a luminescent dopant.

[0190] The light-emitting layer may consist of a single layer or multiple layers, each formed from a light-emitting layer material (host material, dopant material). The host material and dopant material may each be of one type or a combination of multiple types. The dopant material may be contained throughout the host material or partially contained within it. As for the doping method, it can be formed by co-deposition with the host material, but it may also be mixed with the host material beforehand and then deposited simultaneously.

[0191] The amount of host material used varies depending on the type of host material and should be determined according to the characteristics of that host material. The guideline for the amount of host material used is preferably 50 to 99.999% by mass of the total mass of the light-emitting layer material, more preferably 80 to 99.95% by mass, and even more preferably 90 to 99.9% by mass.

[0192] The amount of dopant material used varies depending on the type of dopant material and should be determined according to the characteristics of that dopant material. A guideline for the amount of dopant used is preferably 0.001 to 50% by mass of the total mass of the light-emitting layer material, more preferably 0.05 to 20% by mass, and even more preferably 0.1 to 10% by mass. Within this range, for example, it is preferable in that it can prevent density quenching.

[0193] Host materials Examples of host materials include condensed ring derivatives such as anthracene, pyrene, dibenzochrycene, or fluorene, which have been known as luminescent materials for some time; bisstyryl derivatives such as bisstyrylanthracene derivatives and distyrylbenzene derivatives; tetraphenylbutadiene derivatives; cyclopentadiene derivatives; fluorene derivatives; benzofluorene derivatives; and dibenzochrycene compounds. When the polycyclic aromatic compound of the present invention is the dopant material, anthracene compounds, fluorene compounds, or dibenzochrycene compounds are preferred as the host material.

[0194] Furthermore, as the host material, for example, a compound represented by any of the following formulas (H1), (H2), and (H3) can be used. [ka]

[0195] In formulas (H1), (H2), and (H3), L 1The compounds are arylenes having 6 to 24 carbon atoms, heteroarylenes having 2 to 24 carbon atoms, heteroarylene-arylenes having 6 to 24 carbon atoms, and arylene-heteroarylene-arylenes having 6 to 24 carbon atoms, with arylenes having 6 to 16 carbon atoms being preferred, arylenes having 6 to 12 carbon atoms being more preferred, and arylenes having 6 to 10 carbon atoms being particularly preferred. Specifically, examples include divalent groups such as benzene rings, biphenyl rings, terphenyl rings, and fluorene rings. As for heteroarylenes, heteroarylenes having 2 to 24 carbon atoms are preferred, heteroarylenes having 2 to 20 carbon atoms are more preferred, heteroarylenes having 2 to 15 carbon atoms are even more preferred, and heteroarylenes having 2 to 10 carbon atoms are particularly preferred. Specifically, pyrrole ring, oxazole ring, isoxazole ring, thiazole ring, isothiazole ring, imidazole ring, oxadiazole ring, thiadiazole ring, triazole ring, tetrazole ring, pyrazole ring, pyridine ring, pyrimidine ring, pyridazine ring, pyrazine ring, triazine ring, indole ring, isoindole ring, 1H-indazole ring, and Examples of divalent groups include the nzoimidazole ring, benzoxazole ring, benzothiazole ring, 1H-benzotriazole ring, quinoline ring, isoquinoline ring, sinnoline ring, quinazoline ring, quinoxaline ring, phthalazine ring, naphthyridine ring, purine ring, pteridine ring, carbazole ring, acridine ring, phenoxatiin ring, phenoxazine ring, phenothiazine ring, phenazine ring, indoridine ring, furan ring, benzofuran ring, isobenzofuran ring, dibenzofuran ring, thiophene ring, benzothiophene ring, dibenzothiophene ring, furazan ring, oxadiazole ring, and thiantrene ring. In each of the compounds represented by the above formulas, at least one hydrogen atom may be substituted with an alkyl, cyano, halogen, or deuterium atom having 1 to 6 carbon atoms.

[0196] Preferred specific examples include compounds represented by any of the structural formulas listed below. In the structural formulas listed below, at least one hydrogen atom may be substituted with a halogen, cyano, a C1-C4 alkyl group (e.g., methyl or t-butyl), phenyl, or naphthyl.

[0197] [ka]

[0198] [ka]

[0199] [ka]

[0200] [ka]

[0201] <Anthracene compounds> Examples of anthracene compounds that can be used as hosts include the compounds represented by formula (3-H) and the compounds represented by formula (3-H2). [ka]

[0202] In formula (3-H), X and Ar 4 Each is independently hydrogen, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted diarylamino, optionally substituted diheteroarylamino, optionally substituted arylheteroarylamino, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted alkenyl, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted arylthio or optionally substituted silyl, and all X and Ar 4 They do not become hydrogen at the same time. At least one hydrogen atom in the compound represented by formula (3-H) may be substituted with a halogen, cyano, deuterium, or an optionally substituted heteroaryl.

[0203] Furthermore, a polymer (preferably a dimer) may be formed using the structure represented by formula (3-H) as the unit structure. In this case, for example, the unit structures represented by formula (3-H) may be bonded together via X, and X may be a single bond, arylene (phenylene, biphenylene, naphthylene, etc.), and heteroarylene (pyridine ring, dibenzofuran ring, dibenzothiophene ring, carbazole ring, benzocarbazole ring, and phenyl-substituted carbazole ring, etc., which are groups having a divalent bond value).

[0204] Details of each group in the compound represented by formula (3-H) can be found by referring to the explanation in formula (1) above, and will be further explained in the section on preferred embodiments below.

[0205] Preferred embodiments of the above anthracene compounds are described below. The definition of the symbols in the following structures is the same as the definition described above. [ka]

[0206] In formula (3-H), each X is independently a group represented by formula (3-X1), formula (3-X2), or formula (3-X3), and the groups represented by formula (3-X1), formula (3-X2), or formula (3-X3) bond to the anthracene ring of formula (3-H) at *. Preferably, two Xs do not simultaneously become the group represented by formula (3-X3). More preferably, two Xs do not simultaneously become the group represented by formula (3-X2).

[0207] Furthermore, a polymer (preferably a dimer) may be formed using the structure represented by formula (3-H) as the unit structure. In this case, for example, the unit structures represented by formula (3-H) may be bonded together via X, and X may be a single bond, arylene (phenylene, biphenylene, naphthylene, etc.), and heteroarylene (pyridine ring, dibenzofuran ring, dibenzothiophene ring, carbazole ring, benzocarbazole ring, and phenyl-substituted carbazole ring, etc., which are groups having a divalent bond value).

[0208] The naphthylene moieties in formulas (3-X1) and (3-X2) may be condensed with a single benzene ring. The resulting structure is as follows: [ka]

[0209] Ar 1 and Ar 2 Each of these is independently hydrogen, phenyl, biphenylyl, terphenylyl, quaterphenylyl, naphthyl, phenanthryl, fluorenyl, benzofluorenyl, crisenyl, triphenylenyl, pyrenyl, or a group represented by formula (A) (including carbazolyl, benzocarbazolyl, and phenyl-substituted carbazolyl). 1 or Ar 2 If the group is represented by formula (A), then the group represented by formula (A) is bonded to the naphthalene ring in formula (3-X1) or formula (3-X2) at its *.

[0210] Ar 3 This refers to phenyl, biphenylyl, terphenylyl, quaterphenylyl, naphthyl, phenanthryl, fluorenyl, benzofluorenyl, crisenyl, triphenylenyl, pyrenyl, or a group represented by formula (A) (including carbazolyl, benzocarbazolyl, and phenyl-substituted carbazolyl). Note that Ar 3If the group is represented by formula (A), then the group represented by formula (A) bonds with the single bond represented by the line in formula (3-X3) at its *. That is, the anthracene ring of formula (3-H) and the group represented by formula (A) bond directly.

[0211] Also, Ar 3 It may have substituents, Ar 3 At least one hydrogen in may be further substituted with an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, a phenyl group, a biphenylyl group, a terphenylyl group, a naphthyl group, a phenanthryl group, a fluorenyl group, a crisenyl group, a triphenylenyl group, a pyrenyl group, or a group represented by formula (A) (including carbazolyl and phenyl-substituted carbazolyl groups). Note that Ar 3 If the substituent on is the group represented by formula (A), then the group represented by formula (A) is the Ar in formula (3-X3) in its * 3 It combines with it.

[0212] Ar 4 These are silyls that are independently substituted with hydrogen, phenyl, biphenylyl, terphenylyl, naphthyl, or C1-C4 alkyl (methyl, ethyl, t-butyl, etc.) and / or C5-C10 cycloalkyl.

[0213] Examples of alkyl groups with 1 to 4 carbon atoms that can substitute for silyls include methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, t-butyl, and cyclobutyl, with each of the three hydrogen atoms in the silyl molecule being independently substituted by one of these alkyl groups.

[0214] Specific examples of "silyls substituted with alkyl groups having 1 to 4 carbon atoms" include trimethylsilyl, triethylsilyl, tripropylsilyl, triisopropylsilyl, tributylsilyl, trisec-butylsilyl, trit-butylsilyl, ethyldimethylsilyl, propyldimethylsilyl, isopropyldimethylsilyl, butyldimethylsilyl, sec-butyldimethylsilyl, t-butyldimethylsilyl, methyldiethylsilyl, propyldiethylsilyl, isopropyldiethylsilyl, butyldiethylsilyl, sec-butyldiethylsilyl, t-butyldiethylsilyl, methyldipropylsilyl, ethyldipropylsilyl, butyldipropylsilyl, sec-butyldipropylsilyl, t-butyldipropylsilyl, methyldiisopropylsilyl, ethyldiisopropylsilyl, butyldiisopropylsilyl, sec-butyldiisopropylsilyl, and t-butyldiisopropylsilyl.

[0215] Examples of cycloalkyl groups with 5 to 10 carbon atoms that can substitute for silyl include cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.0]pentyl, bicyclo[2.1.1]hexyl, bicyclo[3.1.0]hexyl, bicyclo[2.2.1]heptyl (norbornyl), bicyclo[2.2.2]octyl, adamantyl, decahydronaphthalenyl, and decahydroazlenyl, where the three hydrogen atoms in the silyl are each independently substituted by one of these cycloalkyl groups.

[0216] Specific examples of "silyls substituted with cycloalkyl groups having 5 to 10 carbon atoms" include tricyclopentylsilyl and tricyclohexylsilyl.

[0217] Substituted silyls include dialkylcycloalkylsilyls, which are substituted with two alkyl groups and one cycloalkyl group, and alkyldicycloalkylsilyls, which are substituted with one alkyl group and two cycloalkyl groups. The groups mentioned above are specific examples of the alkyl and cycloalkyl groups to be substituted.

[0218] Furthermore, the hydrogen atoms in the chemical structure of the anthracene compound represented by formula (3-H) may be substituted with the group represented by formula (A). When substituted with the group represented by formula (A), the group represented by formula (A) substitutes for at least one hydrogen atom in the compound represented by formula (3-H) at that *.

[0219] The group represented by formula (A) is one of the substituents that an anthracene compound represented by formula (3-H) may have. [ka]

[0220] In equation (A), Y is -O-, -S-, or >NR 29 And R 21 ~R 28 Each is independently hydrogen, an optionally substituted alkyl, an optionally substituted cycloalkyl, an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted alkoxy, an optionally substituted aryloxy, an optionally substituted arylthio, a trialkylsilyl, a tricycloalkylsilyl, a dialkylcycloalkylsilyl, an alkyldicycloalkylsilyl, an optionally substituted amino, a halogen, a hydroxyl, or a cyano, and R 21 ~R 28 Among these, adjacent groups may be bonded to each other to form a hydrocarbon ring, an aryl ring, or a heteroaryl ring, R 29 is hydrogen or an aryl that may be substituted. In equation (A), Y is preferably -O-.

[0221] R 21 ~R 28In the "alkyl which may be substituted" part, the "alkyl" can be either linear or branched, for example, a linear alkyl having 1 to 24 carbon atoms or a branched alkyl having 3 to 24 carbon atoms. A alkyl having 1 to 18 carbon atoms (a branched alkyl having 3 to 18 carbon atoms) is preferred, a alkyl having 1 to 12 carbon atoms (a branched alkyl having 3 to 12 carbon atoms) is more preferred, a alkyl having 1 to 6 carbon atoms (a branched alkyl having 3 to 6 carbon atoms) is even more preferred, and a alkyl having 1 to 4 carbon atoms (a branched alkyl having 3 to 4 carbon atoms) is particularly preferred.

[0222] Specific examples of "alkyl" include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl, n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, t-octyl, 1-methylheptyl, Examples include 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 2,6-dimethyl-4-heptyl, 3,5,5-trimethylhexyl, n-decyl, n-undecyl, 1-methyldecyl, n-dodecyl, n-tridecyl, 1-hexylheptyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, and n-eicosyl.

[0223] R 21 ~R 28 Examples of "cycloalkyl" in "may be substituted" include cycloalkyls with 3 to 24 carbon atoms, cycloalkyls with 3 to 20 carbon atoms, cycloalkyls with 3 to 16 carbon atoms, cycloalkyls with 3 to 14 carbon atoms, cycloalkyls with 5 to 10 carbon atoms, cycloalkyls with 5 to 8 carbon atoms, cycloalkyls with 5 to 6 carbon atoms, and cycloalkyls with 5 carbon atoms.

[0224] Specific examples of "cycloalkyl" include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, and their alkyl (especially methyl) substituted derivatives having 1 to 4 carbon atoms, as well as 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 decahydroazlenyl.

[0225] R 21 ~R 28 In the "aryl that may be substituted" in this expression, examples of "aryl" include aryls having 6 to 30 carbon atoms, preferably aryls having 6 to 16 carbon atoms, more preferably aryls having 6 to 12 carbon atoms, and particularly preferably aryls having 6 to 10 carbon atoms.

[0226] Specific examples of "aryl" include monocyclic phenyl, bicyclic biphenylyl, condensed bicyclic naphthyl, tricyclic terpheniryl (m-terpheniryl, o-terpheniryl, p-terpheniryl), condensed tricyclic acenaphthirenyl, fluorenyl, phenalenyl, phenantrenyl, tetracyclic triphenylenyl, pyrenyl, naphthacenyl, and condensed pentacyclic perilenyl, pentacenyl, etc.

[0227] R 21 ~R 28 In the "heteroaryl that may be substituted" in this context, examples of "heteroaryl" include heteroaryls having 2 to 30 carbon atoms, with heteroaryls having 2 to 25 carbon atoms being preferred, heteroaryls having 2 to 20 carbon atoms being more preferred, heteroaryls having 2 to 15 carbon atoms being even more preferred, and heteroaryls having 2 to 10 carbon atoms being particularly preferred. Examples of heteroaryls include heterocycles containing 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen in addition to carbon as ring constituent atoms.

[0228] Specific examples of "heteroaryls" include pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, pyrazolyl, pyridyl, pyrimidinyl, pyridadinyl, pyrazinyl, triazinyl, indolyl, isoindolyl, 1H-indazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolyl, isoxyl Examples include noryl, cinnoryl, quinazolyl, quinoxalinyl, phthalazinyl, naphthilidinyl, prinyl, pteridinyl, carbazolyl, acridinyl, phenoxathiinyl, phenoxadinyl, phenothiazinyl, phenadinyl, indolidinyl, furyl, benzofuranil, isobenzofuranil, dibenzofuranil, thienyl, benzo[b]thienyl, dibenzothienyl, flazanil, thiantrenil, naphtobenzofuranil, and naphtobenzothienyl.

[0229] R 21 ~R 28 In the "alkoxy that may be substituted" in the formula, examples of "alkoxy" include linear alkoxys with 1 to 24 carbon atoms or branched alkoxys with 3 to 24 carbon atoms. Alkoxys with 1 to 18 carbon atoms (branched alkoxys with 3 to 18 carbon atoms) are preferred, alkoxys with 1 to 12 carbon atoms (branched alkoxys with 3 to 12 carbon atoms) are more preferred, alkoxys with 1 to 6 carbon atoms (branched alkoxys with 3 to 6 carbon atoms) are even more preferred, and alkoxys with 1 to 4 carbon atoms (branched alkoxys with 3 to 4 carbon atoms) are particularly preferred.

[0230] Specific examples of "alkoxys" include methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, s-butoxy, t-butoxy, pentyloxy, hexyloxy, heptyloxy, and octyloxy.

[0231] R 21 ~R 28In the phrase "aryloxy which may be substituted," the "aryloxy" refers to a group in which the hydrogen of the -OH group is substituted with an aryl group, and this aryl is the R mentioned above. 21 ~R 28 We can cite the base described as "aryl" in this context.

[0232] R 21 ~R 28 In the context of "arylthio which may be substituted", the "arylthio" refers to a group in which the hydrogen of the -SH group is substituted with an aryl group, and this aryl is the same as the R mentioned above. 21 ~R 28 We can cite the base described as "aryl" in this context.

[0233] R 21 ~R 28 In this context, "trialkylsilyl" refers to a group in which the three hydrogen atoms of the silyl group are each independently substituted with alkyl groups, and this alkyl group is the R mentioned above. 21 ~R 28 The group described as "alkyl" in the above can be referenced. Preferred alkyl groups for substitution are alkyl groups having 1 to 4 carbon atoms, specifically including methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, t-butyl, and cyclobutyl.

[0234] Specific examples of "trialkylsilyls" include trimethylsilyl, triethylsilyl, tripropylsilyl, triisopropylsilyl, tributylsilyl, trisec-butylsilyl, trit-butylsilyl, ethyldimethylsilyl, propyldimethylsilyl, isopropyldimethylsilyl, butyldimethylsilyl, sec-butyldimethylsilyl, t-butyldimethylsilyl, methyldiethylsilyl, propyldiethylsilyl, isopropyldiethylsilyl, butyldiethylsilyl, sec-butyldiethylsilyl, t-butyldiethylsilyl, methyldipropylsilyl, ethyldipropylsilyl, butyldipropylsilyl, sec-butyldipropylsilyl, t-butyldipropylsilyl, methyldiisopropylsilyl, ethyldiisopropylsilyl, butyldiisopropylsilyl, sec-butyldiisopropylsilyl, and t-butyldiisopropylsilyl.

[0235] R 21 ~R 28 In this context, "tricycloalkylsilyl" refers to a group in which the three hydrogen atoms of the silyl group are each independently substituted with a cycloalkyl group, and this cycloalkyl group is the R mentioned above. 21 ~R 28 The group described as "cycloalkyl" in the above can be cited. Preferred cycloalkyls for substitution are cycloalkyls having 5 to 10 carbon atoms, specifically including cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.0]pentyl, bicyclo[2.1.1]hexyl, bicyclo[3.1.0]hexyl, bicyclo[2.2.1]heptyl, bicyclo[2.2.2]octyl, adamantyl, decahydronaphthalenyl, decahydroazlenyl, and the like.

[0236] Specific examples of "tricycloalkylsilyls" include tricyclopentylsilyl and tricyclohexylsilyl.

[0237] Specific examples of dialkylcycloalkylsilyls substituted with two alkyl groups and one cycloalkyl group, and alkyldicycloalkylsilyls substituted with one alkyl group and two cycloalkyl groups, include silyls substituted with groups selected from the specific alkyl and cycloalkyl groups mentioned above.

[0238] R 21 ~R 28 In the context of "aminos that may be substituted," examples of "substituted aminos" include aminos in which two hydrogens are substituted with aryl or heteroaryl groups. Aminos in which two hydrogens are substituted with aryl groups are diaryl-substituted aminos (the two aryls are either not bonded to each other or are bonded via a linking group), aminos in which two hydrogens are substituted with heteroaryl groups are diheteroaryl-substituted aminos, and aminos in which two hydrogens are substituted with aryl and heteroaryl groups are arylheteroaryl-substituted aminos. These aryl and heteroaryl groups are the same as those mentioned above in R 21 ~R 28 The bases described as "aryl" and "heteroaryl" in the above can be cited.

[0239] Specific examples of "substituted amino acids" include diphenylamino, dinaphthylamino, phenylnaphthylamino, dipyridylamino, phenylpyridylamino, and naphthylpyridylamino.

[0240] R 21 ~R 28 Examples of "halogens" in this context include fluorine, chlorine, bromine, and iodine.

[0241] R 21 ~R 28 Some of the groups described above may be substituted as described above, and examples of substituents in this case include alkyl, cycloalkyl, aryl, or heteroaryl groups. These alkyl, cycloalkyl, aryl, or heteroaryl groups are the R groups described above. 21 ~R 28The groups described as "alkyl," "cycloalkyl," "aryl," or "heteroaryl" in the above context can be referenced.

[0242] Y as ">NR" 29 R in " 29 is hydrogen or an aryl that may be substituted, and this aryl is as described above R 21 ~R 28 The group described as "aryl" in the above can be cited, and its substituent is R 21 ~R 28 The groups described as substituents on can be cited.

[0243] R 21 ~R 28 Adjacent groups may bond to each other to form a hydrocarbon ring, an aryl ring, or a heteroaryl ring. The group that does not form a ring is represented by formula (A-1) below, while the group that does form a ring is represented by formulas (A-2) to (A-14) below, for example. At least one hydrogen in any of the groups represented by formulas (A-1) to (A-14) may be substituted with alkyl, cycloalkyl, aryl, heteroaryl, alkoxy, aryloxy, arylthio, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, alkyldicycloalkylsilyl, diaryl (the two aryls are either not bonded to each other or are bonded via a linking group)-substituted amino, diheteroaryl-substituted amino, arylheteroaryl-substituted amino, halogen, hydroxyl, or cyano.

[0244] [ka]

[0245] Examples of rings formed by the bonding of adjacent groups include the cyclohexane ring in the case of hydrocarbon rings, and the aforementioned R in the case of aryl rings and heteroaryl rings. 21 ~R 28Examples include the ring structures described as "aryl" and "heteroaryl" in formula (A-1), where these rings are formed to condense with one or two benzene rings.

[0246] The group represented by formula (A) is a group obtained by removing one hydrogen atom from any position in formula (A), where * indicates the position. In other words, the group represented by formula (A) may have any position as its bonded position. For example, either carbon atom on the two benzene rings in the structure of formula (A), or R in the structure of formula (A). 21 ~R 28 Among them, any atom on a ring formed by the bonding of adjacent groups to each other, or as Y in the structure of formula (A), ">NR 29 R in " 29 Any position in the middle, or ">NR 29 N(R) in " 29 It can be a group that directly bonds with (which forms a bonding site). The same applies to the group represented by any of formulas (A-1) to (A-14).

[0247] Examples of the group represented by formula (A) include any of the groups represented by formulas (A-1) to (A-14), with groups represented by any of formulas (A-1) to (A-5) and formulas (A-12) to (A-14) being preferred, groups represented by any of formulas (A-1) to (A-4) being more preferred, groups represented by any of formulas (A-1), (A-3), and (A-4) being even more preferred, and the group represented by formula (A-1) being particularly preferred.

[0248] Examples of groups represented by formula (A) include the following. The definitions of Y and * in the formula are the same as above. [ka]

[0249] [ka]

[0250] In the compound represented by formula (3-H), the group represented by formula (A) is the naphthalene ring in formula (3-X1) or formula (3-X2), the single bond in formula (3-X3) and / or the Ar in formula (3-X3). 3 A form in which it is combined with is preferred.

[0251] Furthermore, all or part of the hydrogen atoms in the chemical structure of the anthracene compound represented by formula (3-H) may be deuterium.

[0252] The anthracene compound used as a host may be, for example, a compound represented by the following formula (3-H2). [ka]

[0253] In formula (3-H2), Ar c R is an optionally substituted aryl or optionally substituted heteroaryl, c is hydrogen, alkyl, or cycloalkyl, and Ar 11 Ar 12 Ar 13 Ar 14 Ar 15 Ar 16 Ar 17 , and Ar 18 Each of these is independently a hydrogen, an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted diarylamino, an optionally substituted diheteroarylamino, an optionally substituted arylheteroarylamino, an optionally substituted alkyl, an optionally substituted cycloalkyl, an optionally substituted alkenyl, an optionally substituted alkoxy, an optionally substituted aryloxy, an optionally substituted arylthio, or an optionally substituted silyl, wherein at least one hydrogen in the compound represented by formula (3-H2) may be substituted with a halogen, cyano, or deuterium.

[0254] The definitions of "optionally substituted aryl," "optionally substituted heteroaryl," "optionally substituted diarylamino," "optionally substituted diheteroarylamino," "optionally substituted arylheteroarylamino," "optionally substituted alkyl," "optionally substituted cycloalkyl," "optionally substituted alkenyl," "optionally substituted alkoxy," "optionally substituted aryloxy," "optionally substituted arylthio," or "optionally substituted silyl" in formula (3-H) are the same as those in formula (3-H) above, and the explanations in formula (3-H) can be referenced.

[0255] The "aryl group that may be substituted" is preferably a group represented by any of the following formulas (3-H2-X1) to (3-H2-X7).

[0256] [ka]

[0257] In equations (3-H2-X1) to (3-H2-X7), * indicates the bond position. In equations (3-H2-X1) to (3-H2-X3), Ar 21 Ar 22 , and Ar 23 Each of these is independently hydrogen, phenyl, biphenylyl, terphenylyl, quaterphenylyl, naphthyl, phenanthryl, fluorenyl, benzofluorenyl, crisenyl, triphenylenyl, pyrenyl, anthracenyl, or a group represented by formula (A). In the explanation of formula (3-H2), the group represented by formula (A) is the same as that explained for the anthracene compounds represented by formula (3-H).

[0258] In equations (3-H2-X4) to (3-H2-X7), Ar 24 Ar 25 Ar 26 Ar 27 and Ar 28Each of these is independently hydrogen, phenyl, biphenylyl, terphenylyl, naphthyl, phenanthryl, fluorenyl, crisenyl, triphenylenyl, pyrenyl, or a group represented by formula (A). In addition, one or more hydrogens in each of the groups represented by formulas (3-H2-X1) to (3-H2-X7) may be substituted with an alkyl group having 1 to 6 carbon atoms (preferably methyl or t-butyl).

[0259] Furthermore, preferred examples of "optionally substituted aryls" include terpheniryl (in particular m-terphenyl-5'-yl), which may be substituted with one or more substituents selected from the group consisting of phenyl, biphenylyl, terphenylyl, naphthyl, phenanthryl, fluorenyl, crisenyl, triphenylenyl, pyrenyl, and the group represented by formula (A).

[0260] Examples of "optionally substituted heteroaryls" include the group represented by formula (A). Other specific examples of "optionally substituted aryls" and "optionally substituted heteroaryls" include dibenzofuryl, naphthobenzofuryl, and phenyl-substituted dibenzofuryl.

[0261] At least one hydrogen atom in the compound represented by formula (3-H2) may be substituted with a halogen, cyanopropyl alcohol, or deuterium. Examples of halogens in this case include fluorine, chlorine, bromine, and iodine. Compounds in which all hydrogen atoms in the compound represented by formula (3-H2) are substituted with deuterium are particularly preferred.

[0262] In formula (3-H2), R c The element is hydrogen, alkyl, or cycloalkyl, preferably hydrogen, methyl, or t-butyl, and more preferably hydrogen. In formula (3-H2), Ar 11 ~Ar 18Preferably, at least two of the substituents are optionally substituted aryl or optionally substituted heteroaryl. That is, the anthracene compound represented by formula (3-H2) preferably has a structure in which at least three substituents selected from the group consisting of optionally substituted aryl and optionally substituted heteroaryl are bonded to the anthracene ring.

[0263] Anthracene compounds represented by formula (3-H2) are Ar 11 ~Ar 18 It is more preferable that two of the substituents are optionally substituted aryl or optionally substituted heteroaryl, and the other six substituents are hydrogen, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted alkenyl, or optionally substituted alkoxy. In other words, it is more preferable that the anthracene compound represented by formula (3-H2) has a structure in which three substituents selected from the group consisting of optionally substituted aryl and optionally substituted heteroaryl are bonded to the anthracene ring.

[0264] Anthracene compounds represented by formula (3-H2) are Ar 11 ~Ar 18 It is more preferable that any two of the elements are optionally substituted aryl or optionally substituted heteroaryl, and the other six are hydrogen, methyl, or t-butyl.

[0265] Furthermore, in equation (3-H2), R c is hydrogen and Ar 11 ~Ar 18 It is preferable that any six of them are hydrogen.

[0266] The anthracene compound represented by formula (3-H2) is preferably an anthracene compound represented by the following formulas: (3-H2-A), (3-H2-B), (3-H2-C), (3-H2-D), or (3-H2-E). [ka]

[0267] In formulas (3-H2-A), (3-H2-B), (3-H2-C), (3-H2-D), or (3-H2-E), Ar c ', Ar 11 ', Ar 12 ', Ar 13 ', Ar 14 ', Ar 15 ', Ar 17 ', and Ar 18 Each of the following groups is independently phenyl, biphenylyl, terphenylyl, quaterphenylyl, naphthyl, phenanthryl, fluorenyl, benzofluorenyl, crisenyl, triphenylenyl, pyrenyl, or a group represented by formula (A), and at least one hydrogen in these groups may be substituted with phenyl, biphenylyl, terphenylyl, quaterphenylyl, naphthyl, phenanthryl, fluorenyl, benzofluorenyl, crisenyl, triphenylenyl, pyrenyl, or a group represented by formula (A). Here, when both the hydrogen of the methylene group in fluorenyl and benzofluorenyl are substituted with phenyl, these phenyl groups may be bonded to each other by single bonds. c ', Ar 11 ', Ar 12 ', Ar 13 ', Ar 14 ', Ar 15 ', Ar 17 ', and Ar 18 The carbon atoms of the anthracene ring that are not bonded may have methyl or t-butyl atoms bonded to them instead of hydrogen atoms.

[0268] Ar c ', Ar 11 ', Ar 12 ', Ar 13 ', Ar 14 ', Ar 15 ', Ar 17 ', and Ar 18When each of these is a substituted or unsubstituted phenyl or a substituted or unsubstituted naphthyl, it is preferable that the group is represented by any of the above formulas (3-H2-X1) to (3-H2-X7).

[0269] Ar c ', Ar 11 ', Ar 12 ', Ar 13 ', Ar 14 ', Ar 15 ', Ar 17 ', and Ar 18 Each of the groups is more preferably independently phenyl, biphenylyl (especially biphenyl-2-yl or biphenyl-4-yl), terphenylyl (especially m-terphenyl-5'-yl), naphthyl, phenanthryl, fluorenyl, or any of the above formulas (A-1) to (A-4), in which case at least one hydrogen in these groups may be substituted with phenyl, biphenylyl, naphthyl, phenanthryl, fluorenyl, or any of the above formulas (A-1) to (A-4).

[0270] Furthermore, at least one hydrogen atom in the compounds represented by formulas (3-H2-A), (3-H2-B), (3-H2-C), (3-H2-D), or (3-H2-E) may be substituted with a halogen, cyano, or deuterium. The deuterated form is preferred, and a form in which the entire anthracene ring is deuterated, or a form in which all hydrogen atoms are deuterated, is preferred.

[0271] Particularly preferred anthracene compounds represented by the formula (3-H2) include the anthracene compounds represented by the following formula (3-H2-Aa). [ka]

[0272] In formula (3-H2-Aa), Ar c ', Ar 14 ', and Ar 15Each of the following groups is independently phenyl, biphenylyl, terphenylyl, naphthyl, phenanthryl, fluorenyl, benzofluorenyl, crisenyl, triphenylenyl, pyrenyl, or any of the above formulas (A-1) to (A-11), and at least one hydrogen in these groups may be substituted with phenyl, biphenylyl, terphenylyl, naphthyl, phenanthryl, fluorenyl, benzofluorenyl, crisenyl, triphenylenyl, pyrenyl, or any of the above formulas (A-1) to (A-11). Here, when both the hydrogen of the methylene group in fluorenyl and benzofluorenyl are substituted with phenyl, these phenyl groups may be bonded to each other by single bonds. Also, Ar c ', Ar 14 ', and Ar 15 Carbon atoms on an anthracene ring that are not bonded to a ' group may be substituted with methyl or t-butyl instead of hydrogen. At least one hydrogen in the compound represented by formula (3-H2-Aa) may be substituted with a halogen or cyano, and at least one hydrogen in the compound represented by formula (3-H2-Aa) may be substituted with deuterium.

[0273] In formula (3-H2-Aa), Ar c ', Ar 14 ', and Ar 15 Each of the groups is preferably independently phenyl, biphenylyl, terphenylyl, naphthyl, phenanthryl, fluorenyl, or any of the groups represented by formulas (A-1) to (A-4) above, and at least one hydrogen in these groups may be substituted with phenyl, naphthyl, phenanthryl, fluorenyl, or any of the groups represented by formulas (A-1) to (A-4).

[0274] In the compound represented by formula (3-H2-Aa), at least the carbon at position 10 of the anthracene ring (Ar cIt is preferable that the hydrogen bonded to the carbon atom to which the ' is attached (with the carbon atom at position 9) is substituted with deuterium. That is, the compound represented by formula (3-H2-Aa) is preferably the compound represented by the following formula (3-H2-Ab). In formula (3-H2-Ab), D is deuterium, and Ar c ', Ar 14 ', and Ar 15 ' is the same as the definition in formula (3-H2-Aa). In formula (3-H2-Ab), D indicates that at least this position is deuterium, and one or more of the other hydrogens in formula (3-H2-Aa) may also be deuterium, and it is also preferable that all of the hydrogens in formula (3-H2-Aa) are deuterium.

[0275] [ka]

[0276] Specific examples of anthracene compounds include the compounds represented by the following formulas. In the following structural formulas, "Me" represents methyl, "D" represents deuterium, and "tBu" represents t-butyl.

[0277] [ka]

[0278] [ka]

[0279] [ka]

[0280] [ka]

[0281] [ka]

[0282] [ka]

[0283] [ka]

[0284] [ka]

[0285] Other specific examples of anthracene compounds include compounds represented by any of the following formulas selected from the group consisting of formulas (3-131-Y) to (3-182-Y), formula (3-183-N), formula (3-184-Y) to (3-269-Y), formula (3-500) to (3-557), and formula (3-600) to (3-620). In formulas (3-131-Y) to (3-182-Y), formula (3-183-N), formula (3-184-Y) to (3-269-Y), formula (3-500) to (3-557), and formula (3-600) to (3-620), hydrogen atoms may be partially or completely substituted with deuterium. In the formulas, Y is -O-, -S-, >NR 29 (R 29 (This is the same definition as above) or >C(-R 30 )2(R 30 R may be either a linked aryl or alkyl group, 29 For example, phenyl, R 30 For example, methyl. The formula numbering is as follows: for example, if Y is O, formula (3-131-Y) becomes formula (3-131-O), and Y is -S- or >NR. 29 In these cases, the equations are (3-131-S) or (3-131-N), respectively.

[0286] [ka]

[0287]

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[0288]

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[0289]

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[0290]

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[0291]

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[0292]

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[0293]

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[0294]

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[0295]

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[0296]

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[0297]

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[0298]

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[0299]

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[0300]

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[0301]

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[0302]

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[0303]

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[0304]

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[0305] Among these compounds, formulas (3-131-Y)~(3-134-Y), (3-138-Y), (3-140-Y)~(3-143-Y), (3-150-Y), (3-153-Y)~(3-156-Y), (3-166-Y), (3-168-Y), (3-173-Y), (3-177-Y), (3-180-Y)~(3-183-N), (3-185-Y), and (3-19 Compounds represented by formulas (0-Y), (3-223-Y), (3-241-Y), (3-250-Y), (3-252-Y) to (3-254-Y), (3-501), (3-507), (3-508), (3-509), (3-513), (3-514), (3-519), (3-521), (3-538) to (3-547), or (3-600) to (3-620) are preferred. Furthermore, Y is preferably -O-.

[0306] The above anthracene compounds include compounds having a reactive group at a desired position on the anthracene skeleton, and anthracene compounds represented by formula (3-H), where X and Ar 4 The compounds can be produced by applying Suzuki coupling, Negishi coupling, or other known coupling reactions, using compounds having reactive groups in substructures such as the structure of formula (A) as starting materials. Examples of reactive groups in these reactive compounds include halogens and boronic acids. For specific production methods, refer to the synthesis methods in paragraphs

[0089] to

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

[0307] <Fluorene compounds> The compound represented by formula (4-H) basically functions as a host. [ka]

[0308] In formula (4-H), R 1 From R 10Each of these is independently a hydrogen, aryl, heteroaryl (the heteroaryl may be bonded to the fluorene skeleton in formula (4-H) via a linking group), diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkenyl, alkoxy, or aryloxy, and at least one hydrogen in these may be substituted with an aryl, heteroaryl, alkyl, or cycloalkyl, and R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 5 and R 6 , R 6 and R 7 , R 7 and R 8 or R 9 and R 10 Each of these may be independently bonded to form a fused ring or spiro ring, and at least one hydrogen in the formed ring may be substituted with an aryl, heteroaryl (the heteroaryl may be bonded to the formed ring via a linking group), diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkenyl, alkoxy, or aryloxy, and at least one hydrogen in these may be substituted with an aryl, heteroaryl, alkyl, or cycloalkyl, and at least one hydrogen in the compound represented by formula (4-H) may be substituted with a halogen, cyano, or deuterium.

[0309] For details of each group in the definition of formula (4-H), refer to the explanation for the polycyclic aromatic compound of formula (1) described above.

[0310] R 1 From R 10Examples of alkenyls include alkenyls having 2 to 30 carbon atoms, with alkenyls having 2 to 20 carbon atoms being preferred, alkenyls having 2 to 10 carbon atoms being more preferred, alkenyls having 2 to 6 carbon atoms being even more preferred, and alkenyls having 2 to 4 carbon atoms being particularly preferred. Preferred alkenyls are vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, or 5-hexenyl.

[0311] Furthermore, as specific examples of heteroaryls, monovalent groups can also be given, which are represented by removing any one hydrogen atom from the compounds of the following formulas: (4-Ar1), (4-Ar2), (4-Ar3), (4-Ar4), or (4-Ar5).

[0312] [ka]

[0313] In equations (4-Ar1) to (4-Ar5), Y 1 Each of these is independently O, S, or NR, where R is phenyl, biphenylyl, naphthyl, anthracenyl, or hydrogen, and at least one hydrogen in the structures of formulas (4-Ar1) to (4-Ar5) may be substituted with phenyl, biphenylyl, naphthyl, anthracenyl, phenantrenyl, methyl, ethyl, propyl, or butyl.

[0314] These heteroaryls may be bonded to the fluorene skeleton in formula (4-H) via linking groups. That is, the fluorene skeleton in formula (4-H) and the heteroaryls may not only be directly bonded, but may also be bonded to each other via linking groups. Examples of such linking groups include phenylene, biphenylene, naphthylene, anthracenylene, methylene, ethylene, -OCH2CH2-, -CH2CH2O-, or -OCH2CH2O-.

[0315] Also, R in equation (4-H) 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 5 and R 6 , R 6 and R 7 or R 7 and R 8 Each of them independently bonds to form a fused ring, R 9 and R 10 They may be bonded together to form a spiro ring. 1 From R 8 The condensed ring formed by this process is a ring that condenses with the benzene ring in formula (4-H), and is either an aliphatic or aromatic ring. Preferably, it is an aromatic ring, and examples of structures including the benzene ring in formula (4-H) include naphthalene rings and phenanthrene rings. 9 and R 10 The spiro ring formed by this process is a ring that spirobonds to the 5-membered ring in formula (4-H), and is either an aliphatic or aromatic ring. Preferably, it is an aromatic ring, such as a fluorene ring.

[0316] The compound represented by formula (4-H) is preferably a compound represented by the following formulas (4-H-1), (4-H-2), or (4-H-3), where in each case R in formula (4-H) 1 and R 2 A compound in which a benzene ring formed by the bonding of R is condensed, in formula (4-H). 3 and R 4 A compound in which a benzene ring formed by the bonding of R is condensed, in formula (4-H). 1 From R 8 It is a compound in which none of the following are bonded.

[0317] [ka]

[0318] R in equations (4-H-1), (4-H-2), and (4-H-3) 1 From R10 The definition of is the corresponding R in equation (4-H). 1 From R 10 This is the same as R in equations (4-H-1) and (4-H-2). 11 From R 14 The definition of R in equation (4-H) is also 1 From R 10 It is the same as this.

[0319] The compound represented by formula (4-H) is more preferably the compound represented by the following formulas (4-H-1A), (4-H-2A), or (4-H-3A), where R is present in formulas (4-H-1), (4-H-1), or (4-H-3), respectively. 9 and R 10 This is a compound in which a spirofluorene ring is formed by the bonding of two molecules.

[0320] [ka]

[0321] R in equations (4-H-1A), (4-H-2A), and (4-H-3A) 2 From R 7 The definition of is the corresponding R in equations (4-H-1), (4-H-2), and (4-H-3). 2 From R 7 This is the same as R in equations (4-H-1A) and (4-H-2A). 11 From R 14 The definition of R in equations (4-H-1) and (4-H-2) is also 11 From R 14 It is the same as this.

[0322] Furthermore, in the compound represented by formula (4-H), all or part of the hydrogen atoms may be substituted with halogens, cyanosides, or deuterium.

[0323] A more specific example of a fluorene compound used as a host in the present invention is the compound represented by the following structural formula. Note that "Me" indicates methyl. [ka]

[0324] <Dibenzocricene compounds> Dibenzocricene compounds used as hosts are, for example, compounds represented by the following formula (5-H). [ka]

[0325] In formula (5-H), R 1 From R 16 Each of these is independently a hydrogen, aryl, heteroaryl (the heteroaryl may be bonded to the dibenzochrysene skeleton in formula (5-H) via a linking group), diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkenyl, alkoxy, or aryloxy, wherein at least one hydrogen in these may be substituted with an aryl, heteroaryl, alkyl, or cycloalkyl, and R 1 From R 16 Adjacent groups may bond to each other to form a fused ring, and at least one hydrogen in the formed ring may be substituted with an aryl, heteroaryl (the heteroaryl may be bonded to the formed ring via a linking group), diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkenyl, alkoxy, or aryloxy, and at least one hydrogen in these may be substituted with an aryl, heteroaryl, alkyl, or cycloalkyl, and at least one hydrogen in the compound represented by formula (5-H) may be substituted with a halogen, cyano, or deuterium.

[0326] For details of each group in the definition of formula (5-H), refer to the explanation for the polycyclic aromatic compound of formula (1) described above.

[0327] Examples of alkenyls in the definition of formula (5-H) include alkenyls having 2 to 30 carbon atoms, with alkenyls having 2 to 20 carbon atoms being preferred, alkenyls having 2 to 10 carbon atoms being more preferred, alkenyls having 2 to 6 carbon atoms being even more preferred, and alkenyls having 2 to 4 carbon atoms being particularly preferred. Preferred alkenyls are vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, or 5-hexenyl.

[0328] Furthermore, as specific examples of heteroaryls, monovalent groups can also be represented by removing any one hydrogen atom from the compounds of the following formulas: (5-Ar1), (5-Ar2), (5-Ar3), (5-Ar4), or (5-Ar5).

[0329] [ka]

[0330] In equations (5-Ar1) to (5-Ar5), Y 1 Each of these is independently O, S, or NR, where R is phenyl, biphenylyl, naphthyl, anthracenyl, or hydrogen, and at least one hydrogen in the structures of formulas (5-Ar1) to (5-Ar5) may be substituted with phenyl, biphenylyl, naphthyl, anthracenyl, phenantrenyl, methyl, ethyl, propyl, or butyl.

[0331] These heteroaryls may be bonded to the dibenzochrysene skeleton in formula (5-H) via a linking group. That is, the dibenzochrysene skeleton in formula (5-H) and the heteroaryls may not only be directly bonded, but may also be bonded to each other via a linking group. Examples of such linking groups include phenylene, biphenylene, naphthylene, anthracenylene, methylene, ethylene, -OCH2CH2-, -CH2CH2O-, or -OCH2CH2O-.

[0332] The compound represented by formula (5-H) is preferably R 1 , R 4 , R 5 , R 8 , R 9 , R 12 , R 13 and R 16 is hydrogen. In this case, R in equation (5-H) 2 , R 3 , R 6 , R 7 , R 10 , R 11 , R 14 and R 15 Preferably, each of these is independently hydrogen, phenyl, biphenylyl, naphthyl, anthracenyl, phenantrenyl, a monovalent group having the structure of formula (5-Ar1), formula (5-Ar2), formula (5-Ar3), formula (5-Ar4), or formula (5-Ar5) (the monovalent group having this structure may be bonded to the dibenzochrysene skeleton in formula (5-H) via phenylene, biphenylene, naphthylene, anthracenylene, methylene, ethylene, -OCH2CH2-, -CH2CH2O-, or -OCH2CH2O-), methyl, ethyl, propyl, or butyl.

[0333] The compound represented by formula (5-H) is more preferably R 1 , R 2 , R 4 , R 5 , R 7 , R 8 , R 9 , R 10 , R 12 , R 13 , R 15 and R 16 is hydrogen. In this case, R in equation (5-H) 3 , R 6 , R 11 and R 14At least one (preferably one or two, more preferably one) of the groups is a monovalent group having the structure of formula (5-Ar1), formula (5-Ar2), formula (5-Ar3), formula (5-Ar4), or formula (5-Ar5) via a single bond, phenylene, biphenylene, naphthylene, anthracenylene, methylene, ethylene, -OCH2CH2-, -CH2CH2O-, or -OCH2CH2O-, and the other groups (i.e., the positions other than those substituted by the monovalent group having the aforementioned structure) are hydrogen, phenyl, biphenylyl, naphthyl, anthracenyl, methyl, ethyl, propyl, or butyl, wherein at least one hydrogen in these groups may be substituted with phenyl, biphenylyl, naphthyl, anthracenyl, methyl, ethyl, propyl, or butyl.

[0334] Also, R in equation (5-H) 2 , R 3 , R 6 , R 7 , R 10 , R 11 , R 14 and R 15 If a monovalent group having a structure represented by formulas (5-Ar1) to (5-Ar5) is selected, then at least one hydrogen in that structure is R in formula (5-H). 1 From R 16 It may also bond with either of them to form a single bond.

[0335] A more specific example of a dibenzochrysene compound used as a host in the present invention is the compound represented by the following structural formula. Note that "tBu" indicates t-butyl. [ka]

[0336] [ka]

[0337] The above-mentioned materials for the light-emitting layer (host material and dopant material) can also be used as materials for the light-emitting layer as polymer compounds obtained by polymerizing reactive compounds in which reactive substituents are substituted as monomers, or as polymer crosslinks thereof, or as pendant-type polymer compounds obtained by reacting a main-chain polymer with the reactive compound, or as pendant-type polymer crosslinks thereof. In this case, the explanation for the polycyclic aromatic compound represented by formula (1) can be referred to for the reactive substituent.

[0338] Emitting layer containing assisting dopant and emitting dopant The light-emitting layer in an organic electroluminescent device may include a host compound as a first component, an assisting dopant (compound) as a second component, and an emitting dopant (compound) as a third component. The polycyclic aromatic compound of the present invention may also be used as the emitting dopant. A thermally activated delayed phosphor can be used as the assisting dopant (compound).

[0339] In the following explanation, an organic electroluminescent device that uses a thermally activated delayed phosphor as an assisting dopant may be referred to as a "TAF device" (TADF Assisting Fluorescence device). In a TAF device, the "host compound" refers to a compound whose excitation singlet energy level, determined from the short-wavelength shoulder of the fluorescence spectrum peak, is higher than that of the thermally activated delayed phosphor as the second component and the emitting dopant as the third component.

[0340] A "thermally activated delayed phosphor" refers to a compound that absorbs thermal energy, undergoes a reverse intersystem crossing from an excited triplet state to an excited singlet state, and then radiates deactivation from that excited singlet state to emit delayed fluorescence. However, "thermally activated delayed fluorescence" also includes compounds that undergo a higher-order triplet state during the excitation process from the excited triplet state to the excited singlet state. For example, there is a paper by Monkman et al. from the University of Durham (NATURE COMMUNICATIONS, 7:13680, DOI: 10.1038 / ncomms13680), a paper by Hosokai et al. from the National Institute of Advanced Industrial Science and Technology (Hosokai et al., Sci. Adv. 2017;3: e1603282), a paper by Sato et al. from Kyoto University (Scientific Reports, 7:4820, DOI:10.1038 / s41598-017-05007-7), and a conference presentation by Sato et al. from Kyoto University (The 98th Annual Meeting of the Chemical Society of Japan, Presentation No.: 2I4-15, Mechanism of High-Efficiency Luminescence in Organic Electroluminescence Using DABNA as a Luminescent Molecule, Graduate School of Engineering, Kyoto University). In this invention, a target compound is determined to be a "thermally activated delayed phosphor" if a slow fluorescence component is observed when the fluorescence lifetime of a sample containing the target compound is measured at 300 K. Here, a slow fluorescence component refers to one with a fluorescence lifetime of 0.1 μsec or more. Fluorescence lifetime can be measured, for example, using a fluorescence lifetime analyzer (Hamamatsu Photonics, C11367-01).

[0341] The polycyclic aromatic compounds of the present invention can function as emitting dopants, and the "thermally activated delayed phosphor" can function as an assisting dopant that assists the luminescence of the polycyclic aromatic compounds of the present invention.

[0342] Figure 2 shows the energy level diagram of the light-emitting layer of a TAF device using a common fluorescent dopant as the emitting dopant (ED). In the figure, the energy level of the host ground state is E(1,G), the excited singlet energy level obtained from the short-wavelength shoulder of the host fluorescence spectrum is E(1,S,Sh), the excited triplet energy level obtained from the short-wavelength shoulder of the host phosphorescence spectrum is E(1,T,Sh), the energy level of the second component, the assisting dopant, ground state is E(2,G), the excited singlet energy level obtained from the short-wavelength shoulder of the second component, the assisting dopant, is E(2,S,Sh), and the phosphorescence of the second component, the assisting dopant... Let E(2,T,Sh) be the excited triplet energy level determined from the short-wavelength shoulder of the spectrum, E(3,G) be the ground state energy level of the third component, the emitting dopant, E(3,S,Sh) be the excited singlet energy level determined from the short-wavelength shoulder of the fluorescence spectrum of the third component, the emitting dopant, E(3,S,Sh) be the excited triplet energy level determined from the short-wavelength shoulder of the phosphorescence spectrum of the third component, the emitting dopant, E(3,T,Sh) be the excited triplet energy level determined from the short-wavelength shoulder of the phosphorescence spectrum of the third component, the emitting dopant, h+ represent holes, e- represent electrons, and FRET (Fluorescence Resonance Energy Transfer) be the fluorescence resonance energy transfer. In a TAF device, when a general fluorescent dopant is used as the emitting dopant (ED), the energy upconverted by the assisting dopant is transferred to the excited singlet energy level E(3,S,Sh) of the emitting dopant and emits light. However, some of the excited triplet energy E(2,T,Sh) on the assisting dopant moves to the excited triplet energy level E(3,T,Sh) of the emitting dopant, or intersystem crossing occurs on the emitting dopant from the excited singlet energy level E(3,S,Sh) to the excited triplet energy level E(3,T,Sh), followed by thermal deactivation to the ground state E(3,G). Through this pathway, some of the energy is not used for emission, resulting in wasted energy.

[0343] In contrast, the organic electroluminescent device of this embodiment can efficiently utilize the energy transferred from the assisting dopant to the emitting dopant for light emission, thereby achieving high luminescence efficiency. This is presumed to be due to the following light emission mechanism.

[0344] Figure 3 shows the preferred energy relationships in the organic electroluminescent device of this embodiment. In the organic electroluminescent device of this embodiment, the compound having a boron atom as the emitting dopant has a high excited triplet energy level E(3,T,Sh). Therefore, even if the excited singlet energy upconverted by the assisting dopant undergoes intersystem crossing to the excited triplet energy level E(3,T,Sh) by the emitting dopant, it is either upconverted on the emitting dopant or recovered to the excited triplet energy level E(2,T,Sh) on the assisting dopant (thermally activated delayed phosphor). Thus, the generated excitation energy can be used for luminescence without waste. Furthermore, by separating the upconversion and luminescence functions into two types of molecules, each suited to its respective role, the residence time of high energy is reduced, and the burden on the compound is expected to decrease.

[0345] In this embodiment, known host compounds can be used, for example, compounds having at least one of a carbazole ring and a furan ring, and among these, it is preferable to use a compound in which at least one of furanil and carbazolyl is bonded to at least one of arylene and heteroarylene. Specific examples include mCP and mCBP.

[0346] The excited triplet energy level E(1,T,Sh), determined from the short-wavelength shoulder of the phosphorescence spectrum of the host compound, is preferably higher than the excited triplet energy levels E(2,T,Sh) and E(3,T,Sh) of the emitter or assisting dopant having the highest excited triplet energy level in the light-emitting layer, from the viewpoint of promoting TADF generation in the light-emitting layer without inhibiting it. Specifically, the excited triplet energy level E(1,T,Sh) of the host compound is preferably 0.01 eV or higher, more preferably 0.03 eV or higher, and even more preferably 0.1 eV or higher, compared to E(2,T,Sh) and E(3,T,Sh). Furthermore, a TADF-active compound may be used as the host compound.

[0347] For example, the host compound can be a compound represented by any of the above formulas (H1), (H2), and (H3).

[0348] <Thermally activated delayed phosphors (assisting dopants)> The thermally activated delay phosphor (TADF compound) used in TAF elements is preferably a donor-acceptor type thermally activated delay phosphor (DA-type TADF compound) designed to enable efficient reverse intersystem crossing by localizing the HOMO (Highest Occupied Molecular Orbital) and LUMO (Lowest Unoccupied Molecular Orbital) within the molecule using an electron-donating substituent called a donor and an electron-accepting substituent called an acceptor. Hereinafter, "electron-donating substituent" (donor) refers to substituents and substructures in which the HOMO orbital is localized within the thermally activated delay phosphor molecule, and "electron-accepting substituent" (acceptor) refers to substituents and substructures in which the LUMO orbital is localized within the thermally activated delay phosphor molecule.

[0349] Generally, thermally activated delayed phosphors using donors and acceptors exhibit large spin-orbit coupling (SOC) due to their structure, and small exchange interaction between the HOMO and LUMO, resulting in a small ΔE(ST) and thus very fast reverse intersystem crossing velocities. On the other hand, thermally activated delayed phosphors using donors and acceptors exhibit large structural relaxation in the excited state (in some molecules, the stable structure differs between the ground state and the excited state; therefore, when a conversion from the ground state to the excited state occurs due to an external stimulus, the structure subsequently changes to the stable structure in the excited state), resulting in a broad emission spectrum. Therefore, using them as luminescent materials may reduce color purity.

[0350] As a thermally activated delayed phosphor in a TAF element, for example, a compound in which the donor and acceptor are directly or via a spacer can be used. As the electron-donating group (donor structure) and electron-accepting group (acceptor structure) used in the thermally activated delayed phosphor of the present invention, for example, the structures described in Chemistry of Materials, 2017, 29, 1946-1963 can be used. Examples of donor structures include carbazole, dimethylcarbazole, di-tert-butylcarbazole, dimethoxycarbazole, tetramethylcarbazole, benzofluorocarbazole, benzothienocarbazole, phenyldihydroindocarbazole, phenylbicarbazole, bicarbazole, tercarbazole, diphenylcarbazolylamine, tetraphenylcarbazolyldiamine, phenoxazine, dihydrophenazine, phenothiazine, dimethyldihydroacridine, diphenylamine, bis(tert-butylphenyl)amine, N1-(4-(diphenylamino)phenyl)-N4,N4-diphenylbenzene-1,4-diamine, dimethyltetraphenyldihydroacridinediamine, tetramethyl-dihydroindenoacridine, and diphenyl-dihydrodibenzoazacillin.Acceptor structures include sulfonyl dibenzene, benzophenone, phenylenebis(phenylmethanone), benzonitrile, isonicotinonitrile, phthalonitrile, isophthalonitrile, paraphthalonitrile, benzenetricarbonite, triazole, oxazole, thiadiazole, benzothiazole, benzobis(thiazole), benzoxazole, benzobis(oxazole), quinoline, benzimidazole, dibenzoquinoxaline, heptazaphenalene, thioxanthone dioxide, dimethylanthracenone, anthracendione, 5H-cyclopenta[1,2-b:5,4-b']dipyridine, fluorange carbonite, triphenyltriazine, pyrazinedicarbonite, pyrimidine, phenylpyrimidine, methylpyrimidine, pyridinedicarbonite, dibenzoquinoxalinedicarbonite, bis(phenylsulfonyl)benzene, dimethylthioxanthone dioxide, thianthrene tetraoxide, and tris(dimethylphenyl)borane. In particular, the compounds having thermally activated delayed fluorescence in the TAF element are preferably compounds having at least one selected from carbazole, phenoxazine, acridine, triazine, pyrimidine, pyrazine, thioxanthene, benzonitrile, phthalonitrile, isophthalonitrile, diphenylsulfone, triazole, oxadiazole, thiadiazole, and benzophenone as a substructure.

[0351] The compound used as the second component of the light-emitting layer in a TAF element is preferably a thermally activated delayed phosphor whose emission spectrum overlaps at least partially with the absorption peak of the emitting dopant. Below, examples of compounds that can be used as the second component (thermally activated delayed phosphor) of the light-emitting layer in a TAF element are given. However, the compounds that can be used as thermally activated delayed phosphors in a TAF element are not limited to the following example compounds. In the following formula, Me represents methyl, t-Bu represents t-butyl, and the dashed line represents the bond position.

[0352] [ka]

[0353] [ka]

[0354] [ka]

[0355] [ka]

[0356] [ka]

[0357] Furthermore, as a thermally activated delayed phosphor, a compound represented by any of the following formulas (AD1), (AD2), and (AD3) can also be used. [ka]

[0358] In the above formulas (AD1), (AD2), and (AD3), M is independently a single bond, -O-, >N-Ar, or >CAr2, and is preferably a single bond, -O-, or >N-Ar from the viewpoint of the depth of the HOMO of the formed substructure and the height of the excited singlet energy level and excited triplet energy level. J is a spacer structure that separates the donor substructure and the acceptor substructure, and is independently an arylene having 6 to 18 carbon atoms, and is preferably an arylene having 6 to 12 carbon atoms from the viewpoint of the magnitude of conjugation that leaches from the donor substructure and the acceptor substructure. More specifically, phenylene, methylphenylene, and dimethylphenylene are examples. Q is independently =C(-H)- or =N-, and is preferably =N- from the viewpoint of the shallowness of the LUMO of the formed substructure and the height of the excited singlet energy level and excited triplet energy level. Ar is independently hydrogen, a C6-C24 aryl, a C2-C24 heteroaryl, a C1-C12 alkyl, or a C3-C18 cycloalkyl, preferably hydrogen, a C6-C12 aryl, a C2-C14 heteroaryl, a C1-C4 alkyl, or a C6-C10 cycloalkyl, more preferably hydrogen, phenyl, tolyl, xylyl, mesityl, biphenyl, pyridyl, bipyridyl, triazyl, carbazolyl, dimethylcarbazolyl, ditert-butylcarbazolyl, benzimidazolyl, or phenylbenzimidazolyl, and even more preferably hydrogen, phenyl, or carbazolyl. m is 1 or 2. n is an integer from 1 to (6-m), preferably an integer from 4 to (6-m) from the viewpoint of steric hindrance. Furthermore, at least one hydrogen atom in each of the above formulas may be substituted with a halogen or deuterium.

[0359] More specifically, the compounds used as the second component in this embodiment are preferably 4CzBN, 4CzBN-Ph, 5CzBN, 3Cz2DPhCzBN, 4CzIPN, 2PXZ-TAZ, Cz-TRZ3, BDPCC-TPTA, MA-TA, PA-TA, FA-TA, PXZ-TRZ, DMAC-TRZ, BCzT, DCzTrz, DDCzTRz, spiroAC-TRZ, Ac-HPM, Ac-PPM, Ac-MPM, TCzTrz, TmCzTrz, and DCzmCzTrz.

[0360] The compound used as the second component in this embodiment may be a donor-acceptor type TADF compound represented by DA, in which one donor D and one acceptor A are directly bonded or bonded via a linking group. However, it is preferable that the compound has a structure represented by the following formula (DAD1), in which multiple donor Ds are directly bonded or bonded via linking groups to one acceptor A, as this results in better characteristics of the organic electroluminescent element. (D 1 -L 1 )nA 1 (DAD1) Formula (DAD1) includes compounds represented by the following formula (DAD2). D 2 -L 2 -A 2 -L 3 -D 3 (DAD2) In equations (DAD1) and (DAD2), D 1 , D 2 and D 3 Each of these independently represents a donor group. The donor structure described above can be used as the donor group. A 1 and A 2 Each of these independently represents an acceptor group. The above acceptor structure can be used as the acceptor group. 1 , L 2 and L 3Each of these independently represents a single bond or a conjugated linkage group. The conjugated linkage group is a spacer structure that separates the donor group and the acceptor group, and is preferably an arylene having 6 to 18 carbon atoms, and more preferably an arylene having 6 to 12 carbon atoms. 1 , L 2 and L 3 It is even more preferable that each of them is independently phenylene, methylphenylene, or dimethylphenylene. In formula (DAD1), n ​​is 2 or more, and A 1 n represents an integer less than or equal to the maximum number of substitutions possible. n can be selected, for example, from 2 to 10 or from 2 to 6. When n is 2, the compound is represented by formula (DAD2). n D 1 They may be the same or different, and n L 1 These may be the same or different. Preferred specific examples of the compounds represented by formulas (DAD1) and (DAD2) include 2PXZ-TAZ and the following compounds, but the second component that can be used in the present invention is not limited to these compounds.

[0361] [ka]

[0362] In this embodiment, the light-emitting layer may consist of a single layer or multiple layers. Furthermore, the host compound, the thermally activated delayed phosphor, and the polycyclic aromatic compound of the present invention may be contained in the same layer, or at least one component may be contained in multiple layers. The host compound, thermally activated delayed phosphor, and polycyclic aromatic compound of the present invention contained in the light-emitting layer may each be one type or a combination of multiple types. The assisting dopant and the emitting dopant may be contained entirely or partially in the host compound as a matrix. The light-emitting layer doped with the assisting dopant and the emitting dopant can be formed by a ternary co-evaporation method of depositing the host compound, assisting dopant and emitting dopant, a method of pre-mixing the host compound, assisting dopant and emitting dopant and then simultaneously depositing them, or a wet deposition method in which a light-emitting layer forming composition (paint) prepared by dissolving the host compound, assisting dopant and emitting dopant in an organic solvent is applied.

[0363] The amount of host compound used varies depending on the type of host compound and should be determined according to the characteristics of that host compound. A guideline for the amount of host compound used is preferably 40-99% by mass of the total mass of the light-emitting layer material, more preferably 50-98% by mass, and even more preferably 70-95% by mass. Within this range, for example, efficient charge transport and efficient energy transfer to the dopant are preferable.

[0364] The amount of assisting dopant (thermally activated delayed phosphor) used varies depending on the type of assisting dopant and should be determined according to the characteristics of that assisting dopant. A guideline for the amount of assisting dopant used is preferably 1 to 60% by mass of the total mass of the light-emitting layer material, more preferably 2 to 50% by mass, and even more preferably 5 to 30% by mass. Within this range, for example, it is preferable in that energy can be efficiently transferred to the emitting dopant.

[0365] The amount of emitting dopant (a compound containing boron atoms) used varies depending on the type of emitting dopant and should be determined according to the characteristics of that emitting dopant. A guideline for the amount of emitting dopant used is preferably 0.001 to 30% by mass of the total mass of the luminescent layer material, more preferably 0.01 to 20% by mass, and even more preferably 0.1 to 10% by mass. Within this range, for example, it is preferable in that it can prevent density quenching.

[0366] A lower concentration of the emitting dopant is preferable in that it can prevent concentration quenching. A higher concentration of the assisting dopant is preferable in terms of the efficiency of the thermally activated delayed fluorescence mechanism. Furthermore, in terms of the efficiency of the thermally activated delayed fluorescence mechanism of the assisting dopant, a lower concentration of the emitting dopant compared to the assisting dopant is preferable.

[0367] 2-1-3. Substrates in Organic Electroluminescent Devices The substrate 101 is a support for the organic EL element 100, and is typically made of quartz, glass, metal, or plastic. The substrate 101 is formed in the form of a plate, film, or sheet depending on the purpose, and can be made of glass, metal, metal foil, plastic film, or plastic sheet, for example. Among these, glass plates and transparent synthetic resin plates such as polyester, polymethacrylate, polycarbonate, or polysulfone are preferred. If a glass substrate is used, soda-lime glass or alkali-free glass can be used, and the thickness only needs to be sufficient to maintain mechanical strength, for example, 0.2 mm or more is sufficient. The upper limit of the thickness is, for example, 2 mm or less, preferably 1 mm or less. Regarding the glass material, alkali-free glass is preferred because it is better to have fewer ions eluted from the glass, but soda-lime glass with a barrier coating such as SiO2 is also commercially available and can be used. Furthermore, to enhance the gas barrier properties, the substrate 101 may be provided with a gas barrier film, such as a dense silicon oxide film, on at least one side. It is particularly preferable to provide a gas barrier film when using a synthetic resin plate, film, or sheet with low gas barrier properties as the substrate 101.

[0368] 2-1-4. Anode in an Organic Electroluminescent Device The anode 102 plays the role of injecting holes into the light-emitting layer 105. If a hole injection layer 103 and / or a hole transport layer 104 are provided between the anode 102 and the light-emitting layer 105, holes will be injected into the light-emitting layer 105 via these layers.

[0369] Materials for forming the anode 102 include inorganic compounds and organic compounds. Examples of inorganic compounds include metals (aluminum, gold, silver, nickel, palladium, chromium, etc.), metal oxides (indium oxide, tin oxide, indium-tin oxide (ITO), indium-zinc oxide (IZO), etc.), metal halides (copper iodide, etc.), copper sulfide, carbon black, ITO glass, and NESA glass. Examples of organic compounds include polythiophenes such as poly(3-methylthiophene), conductive polymers such as polypyrrole and polyaniline. In addition, other materials used as anodes in organic EL elements can be appropriately selected and used.

[0370] The resistance of the transparent electrode is not limited as long as it can supply sufficient current for the light-emitting element to emit light, but from the viewpoint of the power consumption of the light-emitting element, low resistance is desirable. For example, an ITO substrate with a resistance of 300 Ω / □ or less will function as an element electrode, but since substrates of about 10 Ω / □ are now available, it is particularly desirable to use a low-resistance product of, for example, 100 to 5 Ω / □, preferably 50 to 5 Ω / □. The thickness of the ITO can be arbitrarily selected according to the resistance value, but it is usually used between 50 and 300 nm.

[0371] 2-1-5. Hole injection layer and hole transport layer in organic electroluminescent element The hole injection layer 103 plays the role of efficiently injecting holes moving from the anode 102 into the light-emitting layer 105 or the hole transport layer 104. The hole transport layer 104 plays the role of efficiently transporting holes injected from the anode 102 or holes injected from the anode 102 via the hole injection layer 103 to the light-emitting layer 105. The hole injection layer 103 and the hole transport layer 104 are each formed by laminating and mixing one or more types of hole injection / transport materials, or by a mixture of hole injection / transport materials and a polymer binder. Alternatively, an inorganic salt such as iron(III) chloride may be added to the hole injection / transport material to form a layer.

[0372] For hole-injecting and transporting materials, it is necessary to efficiently inject and transport holes from the positive electrode between electrodes under an applied electric field. Therefore, it is desirable to have high hole injection efficiency and efficient transport of the injected holes. To achieve this, it is preferable to have a low ionization potential, high hole mobility, excellent stability, and a material that does not easily generate trapping impurities during manufacturing and use.

[0373] As the material for forming the hole injection layer 103 and the hole transport layer 104, any compound can be selected from among compounds conventionally used as charge transport materials for holes in photoconductive materials, p-type semiconductors, and known compounds used in hole injection layers and hole transport layers of organic EL devices. Specific examples include carbazole derivatives (N-phenylcarbazole, polyvinylcarbazole, etc.), biscarbazole derivatives such as bis(N-arylcarbazole) or bis(N-alkylcarbazole), triarylamine derivatives (4,4',4”-tris(N-carbazol)triphenylamine, polymers having aromatic tertiary amino acids in the main chain or side chain, 1,1-bis(4-di-p-tolylaminophenyl)cyclohexane, N,N'-diphenyl-N,N'-di(3-methylphenyl)-4,4'-diaminobiphenyl, N,N'-diphenyl-N,N'-dinaphthyl-4,4'-diaminobiphenyl, N,N'-diphenyl-N,N'-di(3-methylphenyl)-4,4'-diphenyl-1,1'-diamine, N,N'-dinaphthyl-N,N'-diphenyl-4,4'-diphenyl-1,1'-diamine, N 4 ,N 4’ -diphenyl-N 4 ,N 4’ -Bis(9-phenyl-9H-carbazole-3-yl)-[1,1'-biphenyl]-4,4'-diamine, N 4 ,N 4 ,N 4’ ,N 4’Triphenylamine derivatives such as -tetra[1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4,4'-diamine, 4,4',4”-tris(3-methylphenyl(phenyl)amino)triphenylamine, starburstamine derivatives, etc., stilbene derivatives, phthalocyanine derivatives (metal-free, copper phthalocyanine, etc.), pyrazoline derivatives, hydrazone compounds, benzofuran derivatives and thiophene derivatives, oxadiazole derivatives, quinoxaline derivatives Examples include conductors (e.g., 1,4,5,8,9,12-hexaazatriphenylene-2,3,6,7,10,11-hexacarbonitrine), heterocyclic compounds such as porphyrin derivatives, and polysilanes. Among polymer systems, polycarbonates, styrene derivatives, polyvinylcarbazoles, and polysilanes having the monomers in their side chains are preferred, but the compound is not particularly limited as long as it can form a thin film necessary for fabricating a light-emitting device, allow holes to be injected from the anode, and transport holes.

[0374] Furthermore, the conductivity of organic semiconductors is known to be strongly influenced by doping. Such organic semiconductor matrix materials are composed of compounds with good electron-donating properties or compounds with good electron-accepting properties. Strong electron acceptors such as tetracyanoquinone dimethane (TCNQ) or 2,3,5,6-tetrafluorotetracyano-1,4-benzoquinone dimethane (F4TCNQ) are known for doping with electron-donating substances (see, for example, "M. Pfeiffer, A. Beyer, T. Fritz, K. Leo, Appl. Phys. Lett., 73(22), 3202-3204 (1998)" and "J. Blochwitz, M. Pfeiffer, T. Fritz, K. Leo, Appl. Phys. Lett., 73(6), 729-731 (1998)"). These generate so-called holes through an electron transfer process in the electron-donating base material (hole transporter). The conductivity of the base material changes considerably depending on the number and mobility of holes. Examples of matrix materials having hole transport properties include benzidine derivatives (such as TPD) or starburst amine derivatives (such as TDATA), or certain metal phthalocyanines (especially zinc phthalocyanine (ZnPc)) (Japanese Patent Publication No. 2005-167175). The polycyclic aromatic compounds of the present invention may be used as materials for forming hole injection layers or hole transport layers.

[0375] 2-1-6. Electron-stopping layer in organic electroluminescent devices An electron blocking layer may be provided between the hole injection / transport layer and the light-emitting layer to prevent the diffusion of electrons from the light-emitting layer. For forming the electron blocking layer, any compound represented by one of the above formulas (H1), (H2), and (H3) can be used. The polycyclic aromatic compounds of the present invention may also be used as materials for forming electron blocking layers.

[0376] 2-1-7. Electron injection layer and electron transport layer in organic electroluminescent devices The electron injection layer 107 plays the role of efficiently injecting electrons moving from the cathode 108 into the light-emitting layer 105 or the electron transport layer 106. The electron transport layer 106 plays the role of efficiently transporting electrons injected from the cathode 108 or electrons injected from the cathode 108 via the electron injection layer 107 to the light-emitting layer 105. The electron transport layer 106 and the electron injection layer 107 are each formed by laminating and mixing one or more types of electron transport / injection materials, or by a mixture of electron transport / injection materials and a polymer binder.

[0377] The electron injection and transport layer is responsible for injecting electrons from the cathode and transporting them. It is desirable for this layer to have high electron injection efficiency and to efficiently transport the injected electrons. To achieve this, it is preferable for the material to have high electron affinity, high electron mobility, excellent stability, and to be a material that does not easily generate trapping impurities during manufacturing and use. However, when considering the balance between hole and electron transport, if the main role is to efficiently prevent holes from the anode from flowing to the cathode side without recombining, then even if the electron transport capacity is not very high, the effect of improving luminescence efficiency will be equivalent to that of a material with high electron transport capacity. Therefore, the electron injection and transport layer in this embodiment may also include the function of a layer that can efficiently prevent the movement of holes.

[0378] The material used to form the electron transport layer 106 or electron injection layer 107 (electron transport material) can be arbitrarily selected from compounds conventionally used as electron transfer compounds in photoconductive materials, and known compounds used in the electron injection layer and electron transport layer of organic EL elements.

[0379] The materials used in the electron transport layer or electron injection layer preferably contain at least one selected from compounds consisting of aromatic rings or heteroaromatic rings composed of one or more atoms selected from carbon, hydrogen, oxygen, sulfur, silicon, and phosphorus, pyrrole derivatives and their fused ring derivatives, and metal complexes having electron-accepting nitrogen. Specifically, examples include fused ring aromatic ring derivatives such as naphthalene and anthracene, styryl aromatic ring derivatives represented by 4,4'-bis(diphenylethenyl)biphenyl, perinone derivatives, coumarin derivatives, naphthalimide derivatives, quinone derivatives such as anthraquinone and diphenoquinone, phosphorus oxide derivatives, arylnitrile derivatives, and indole derivatives. Examples of metal complexes having electron-accepting nitrogen include hydroxyazole complexes such as hydroxyphenyloxazole complexes, azomethine complexes, tropolone metal complexes, flavonol metal complexes, and benzoquinoline metal complexes. These materials can be used individually or in combination with different materials.

[0380] Furthermore, specific examples of other electron transfer compounds include pyridine derivatives, naphthalene derivatives, fluorantene derivatives, BO derivatives, anthracene derivatives, phenanthroline derivatives, perinone derivatives, coumarin derivatives, naphthalimide derivatives, anthraquinone derivatives, diphenoquinone derivatives, diphenylquinone derivatives, perylene derivatives, oxadiazole derivatives (such as 1,3-bis[(4-t-butylphenyl)1,3,4-oxadiazolyl]phenylene), thiophene derivatives, triazole derivatives (such as N-naphthyl-2,5-diphenyl-1,3,4-triazole), thiadiazole derivatives, metal complexes of oxine derivatives, quinolinol-based metal complexes, quinoxaline derivatives, polymers of quinoxaline derivatives, benzazole compounds, gallium complexes, pyrazole derivatives, perfluorinated phenylene derivatives, triazine derivatives, pyrazine derivatives, and benzox Examples include noline derivatives (such as 2,2'-bis(benzo[h]quinoline-2-yl)-9,9'-spirobifluorene), imidazopyridine derivatives, borane derivatives, benzimidazole derivatives (such as tris(N-phenylbenzimidazole-2-yl)benzene), benzoxazole derivatives, thiazole derivatives, benzothiazole derivatives, quinoline derivatives, oligopyridine derivatives such as terpyridine, bipyridine derivatives, terpyridine derivatives (such as 1,3-bis(4'-(2,2':6',2”-terpyridinyl))benzene), naphthyridine derivatives (such as bis(1-naphthyl)-4-(1,8-naphthyridine-2-yl)phenylphosphine oxide), aldazine derivatives, pyrimidine derivatives, arylnitrile derivatives, indole derivatives, phosphorus oxide derivatives, bisstyryl derivatives, silole derivatives, and azoline derivatives.

[0381] Furthermore, metal complexes containing electron-accepting nitrogen can also be used, such as quinolinol-based metal complexes, hydroxyazole complexes such as hydroxyphenyl oxazole complexes, azomethine complexes, tropolone metal complexes, flavonol metal complexes, and benzoquinoline metal complexes.

[0382] The materials mentioned above can be used individually, but they can also be used in combination with other materials.

[0383] Among the materials mentioned above, borane derivatives, pyridine derivatives, fluorantene derivatives, BO derivatives, anthracene derivatives, benzofluorene derivatives, phosphine oxide derivatives, pyrimidine derivatives, arylnitrile derivatives, triazine derivatives, benzimidazole derivatives, phenanthroline derivatives, quinolinol-based metal complexes, thiazole derivatives, benzothiazole derivatives, silole derivatives, and azoline derivatives are preferred.

[0384] The polycyclic aromatic compounds of the present invention may be used as materials for forming electron injection layers or electron transport layers.

[0385] The electron transport layer or electron injection layer may further contain a substance capable of reducing the material forming the electron transport layer or electron injection layer. This reducing substance can be any substance having a certain reducing property; for example, at least one selected from the group consisting of alkali metals, alkaline earth metals, rare earth metals, alkali metal oxides, alkali metal halides, alkaline earth metal oxides, alkaline earth metal halides, rare earth metal oxides, rare earth metal halides, alkali metal organic complexes, alkaline earth metal organic complexes, and rare earth metal organic complexes can be suitably used.

[0386] Preferred reducing substances include alkali metals such as Na (work function 2.36 eV), K (2.28 eV), Rb (2.16 eV), or Cs (1.95 eV), and alkaline earth metals such as Ca (2.9 eV), Sr (2.0-2.5 eV), or Ba (2.52 eV), with substances having a work function of 2.9 eV or less being particularly preferred. Of these, alkali metals K, Rb, or Cs are more preferred reducing substances, Rb or Cs are even more preferred, and Cs is the most preferred. These alkali metals have particularly high reducing ability, and their addition in relatively small amounts to materials forming electron transport layers or electron injection layers can improve the luminescence brightness and extend the lifespan of organic EL devices. Furthermore, combinations of two or more alkali metals are also preferred as reducing substances with a work function of 2.9 eV or less, and combinations including Cs, such as Cs and Na, Cs and K, Cs and Rb, or Cs, Na, and K, are particularly preferred. By including Cs, the reducing ability can be efficiently exhibited, and by adding it to the material forming the electron transport layer or electron injection layer, improvements in luminescence brightness and extended lifespan can be achieved in organic EL devices.

[0387] 2-1-8. Cathode in Organic Electroluminescent Devices The cathode 108 plays the role of injecting electrons into the light-emitting layer 105 via the electron injection layer 107 and the electron transport layer 106.

[0388] The material forming the cathode 108 is not particularly limited as long as it can efficiently inject electrons into the organic layer, but the same material as the material forming the anode 102 can be used. Among these, metals such as tin, indium, calcium, aluminum, silver, copper, nickel, chromium, gold, platinum, iron, zinc, lithium, sodium, potassium, cesium, and magnesium, or their alloys (such as magnesium-silver alloys, magnesium-indium alloys, and aluminum-lithium alloys such as lithium fluoride / aluminum), are preferred. To increase electron injection efficiency and improve device characteristics, alloys containing lithium, sodium, potassium, cesium, calcium, magnesium, or these low work function metals are effective. However, these low work function metals are generally unstable in the atmosphere. To improve this, for example, a method is known in which the organic layer is doped with trace amounts of lithium, cesium, or magnesium to use electrodes with high stability. Other dopants that can be used include inorganic salts such as lithium fluoride, cesium fluoride, lithium oxide, and cesium oxide. However, they are not limited to these.

[0389] Furthermore, for electrode protection, it is preferable to laminate metals such as platinum, gold, silver, copper, iron, tin, aluminum, and indium, or alloys using these metals, as well as inorganic materials such as silica, titania, and silicon nitride, polyvinyl alcohol, vinyl chloride, and hydrocarbon polymer compounds. The method for fabricating these electrodes is not particularly limited as long as conductivity can be achieved, such as resistance heating, electron beam deposition, sputtering, ion plating, and coating.

[0390] 2-1-9. Binding agents that may be used in each layer The materials used in the hole injection layer, hole transport layer, light emission layer, electron transport layer, and electron injection layer described above can form each layer individually, but they can also be dispersed in solvent-soluble resins such as polyvinyl chloride, polycarbonate, polystyrene, poly(N-vinylcarbazole), polymethyl methacrylate, polybutyl methacrylate, polyester, polysulfone, polyphenylene oxide, polybutadiene, hydrocarbon resins, ketone resins, phenoxy resins, polyamides, ethylcellulose, vinyl acetate resins, ABS resins, and polyurethane resins, or in curable resins such as phenolic resins, xylene resins, petroleum resins, urea resins, melamine resins, unsaturated polyester resins, alkyd resins, epoxy resins, and silicone resins as polymer binders.

[0391] 2-1-10. Method for fabricating organic electroluminescent devices Each layer constituting an organic EL element can be formed by thinning the material to be composed of each layer using methods such as vapor deposition, resistance heating deposition, electron beam deposition, sputtering, molecular stacking, printing, inkjet, spin coating or casting, or coating. There are no particular limitations on the thickness of each layer formed in this way, and it can be set appropriately according to the properties of the material, but it is usually in the range of 2 nm to 5000 nm. The thickness can usually be measured with a quartz crystal oscillating film thickness analyzer. When thinning using vapor deposition, the deposition conditions vary depending on the type of material, the desired crystal structure and association structure of the film, etc. Generally, the deposition conditions are a boat heating temperature of +50 to +400°C and a vacuum of 10°C. -6 ~10 -3 It is preferable to appropriately set the Pa, deposition rate to 0.01 to 50 nm / second, substrate temperature to -150 to +300°C, and film thickness to 2 nm to 5 μm.

[0392] Next, as an example of a method for fabricating an organic EL element, we will describe a method for fabricating an organic EL element consisting of an anode, a hole injection layer, a hole transport layer, an emissive layer made of host material and dopant material, an electron transport layer, an electron injection layer, and a cathode. An anode is fabricated by forming a thin film of anode material on a suitable substrate by vapor deposition or the like, and then thin films of a hole injection layer and a hole transport layer are formed on this anode. A thin film of host material and dopant material is co-deposited on this to form an emissive layer, and then an electron transport layer and an electron injection layer are formed on this emissive layer. Furthermore, a thin film made of cathode material is formed by vapor deposition or the like to form the cathode, thereby obtaining the desired organic EL element. In addition, in the fabrication of the organic EL element described above, it is also possible to reverse the fabrication order and fabricate the cathode, electron injection layer, electron transport layer, emissive layer, hole transport layer, hole injection layer, and anode in that order.

[0393] When applying a DC voltage to the organic EL element obtained in this way, the voltage should be applied with the anode as + and the cathode as -. When a voltage of approximately 2 to 40V is applied, light emission can be observed from the transparent or semi-transparent electrode side (anode or cathode, or both). Furthermore, this organic EL element will also emit light when a pulsed current or alternating current is applied. The waveform of the applied AC current can be arbitrary.

[0394] 2-1-11. Application Examples of Organic Electroluminescent Devices Organic EL elements can also be applied to display devices or lighting equipment. A display device or lighting device equipped with an organic EL element can be manufactured by known methods, such as connecting the organic EL element to a known driving device, and can be driven using known driving methods such as DC driving, pulse driving, or AC driving as appropriate.

[0395] Examples of display devices include panel displays such as color flat panel displays, and flexible displays such as flexible color organic electroluminescent (EL) displays (see, for example, Japanese Patent Publication No. 10-335066, Japanese Patent Publication No. 2003-321546, and Japanese Patent Publication No. 2004-281086). Examples of display methods include matrix and / or segment displays. Matrix and segment displays may coexist on the same panel.

[0396] In a matrix display, pixels for display are arranged two-dimensionally, such as in a grid or mosaic pattern, and characters or images are displayed using a collection of pixels. The shape and size of the pixels are determined by the application. For example, for displaying images and characters on personal computers, monitors, and televisions, square pixels with sides of 300 μm or less are usually used, while for large displays such as display panels, pixels with sides on the order of millimeters are used. For monochrome displays, pixels of the same color can be arranged, but for color displays, red, green, and blue pixels are arranged side by side. In this case, there are typically delta type and stripe type displays. The matrix can be driven by either a line-sequential drive method or an active matrix. Line-sequential drive has the advantage of a simpler structure, but considering the operating characteristics, the active matrix may be superior in some cases, so it is necessary to choose the appropriate method depending on the application.

[0397] In segment-based displays, a pattern is formed to display predetermined information, and a designated area is illuminated. Examples include time and temperature displays in digital clocks and thermometers, operating status displays in audio equipment and induction cooktops, and panel displays in automobiles.

[0398] Examples of lighting devices include lighting devices such as indoor lighting and backlights for liquid crystal displays (see, for example, Japanese Patent Publication No. 2003-257621, Japanese Patent Publication No. 2003-277741, and Japanese Patent Publication No. 2004-119211). Backlights are mainly used to improve the visibility of non-self-illuminating display devices and are used in liquid crystal displays, clocks, audio equipment, automobile panels, display boards, and signs. In particular, for liquid crystal displays, especially backlights for personal computers where miniaturization is a challenge, conventional methods using fluorescent lamps or light guide plates make miniaturization difficult. Therefore, backlights using organic EL elements are characterized by their thinness and light weight.

[0399] 2-2. Other Organic Devices The polycyclic aromatic compounds according to the present invention can be used not only in the organic field-light-emitting device described above, but also in the fabrication of organic field-effect transistors or organic thin-film solar cells.

[0400] An organic field-effect transistor (OCT) is a type of transistor that controls current using an electric field generated by a voltage input. In addition to source and drain electrodes, it has a gate electrode. When a voltage is applied to the gate electrode, an electric field is generated, allowing the current to be controlled by arbitrarily blocking the flow of electrons (or holes) between the source and drain electrodes. Compared to simple transistors (bipolar transistors), OTCs are easier to miniaturize and are frequently used as components in integrated circuits.

[0401] The structure of an organic field-effect transistor typically includes a source electrode and a drain electrode in contact with an organic semiconductor active layer formed using the polycyclic aromatic compound according to the present invention, and a gate electrode further separated by an insulating layer (dielectric layer) in contact with the organic semiconductor active layer. Examples of such device structures include the following: (1) Substrate / Gate electrode / Insulator layer / Source electrode / Drain electrode / Organic semiconductor active layer (2) Substrate / Gate electrode / Insulator layer / Organic semiconductor active layer / Source electrode / Drain electrode (3) Substrate / Organic semiconductor active layer / Source electrode and drain electrode / Insulator layer / Gate electrode (4) Substrate / Source electrode / Drain electrode / Organic semiconductor active layer / Insulator layer / Gate electrode Organic field-effect transistors configured in this way can be applied as pixel driving switching elements in active-matrix driven liquid crystal displays and organic electroluminescent displays.

[0402] Organic thin-film solar cells have a structure in which an anode such as ITO, a hole transport layer, a photoelectric conversion layer, an electron transport layer, and a cathode are stacked on a transparent substrate such as glass. The photoelectric conversion layer has a p-type semiconductor layer on the anode side and an n-type semiconductor layer on the cathode side. The polycyclic aromatic compound according to the present invention can be used as a material for the hole transport layer, p-type semiconductor layer, n-type semiconductor layer, and electron transport layer, depending on its physical properties. The polycyclic aromatic compound according to the present invention can function as a hole transport material or an electron transport material in organic thin-film solar cells. In addition to the above, organic thin-film solar cells may appropriately include a hole blocking layer, an electron blocking layer, an electron injection layer, a hole injection layer, a smoothing layer, etc. Organic thin-film solar cells can be appropriately selected and combined with known materials used in organic thin-film solar cells.

[0403] 3. Wavelength conversion materials The polycyclic aromatic compounds of the present invention can be used as wavelength conversion materials. Currently, there is much research into applying multi-color technology using color conversion methods to liquid crystal displays, organic EL displays, and lighting. Color conversion refers to the conversion of light emitted from a light source to longer wavelength light, for example, converting ultraviolet light or blue light into green light or red light. By creating a film of a wavelength conversion material with this color conversion function and combining it with, for example, a blue light source, it becomes possible to extract the three primary colors of blue, green, and red from the blue light source, i.e., to extract white light. By using such a white light source, which combines a blue light source with a wavelength conversion film with color conversion function, as a light source unit and combining it with a liquid crystal drive unit and a color filter, it becomes possible to manufacture a full-color display. Furthermore, if the liquid crystal drive unit is not required, it can be used as a white light source as is, and can be applied as a white light source for LED lighting, for example. In addition, by using a blue organic EL element as a light source and combining it with a wavelength conversion film that converts blue light into green and red light, it becomes possible to manufacture a full-color organic EL display without using a metal mask. Furthermore, by using a blue microLED as a light source in combination with a wavelength conversion film that converts blue light into green and red light, it becomes possible to create low-cost full-color microLED displays.

[0404] The polycyclic aromatic compounds of the present invention can be used as wavelength conversion materials. Using a wavelength conversion material containing the polycyclic aromatic compounds of the present invention, light from light sources and light-emitting elements that generate ultraviolet light or shorter wavelength blue light can be converted into blue or green light with high color purity suitable for use in display devices (display devices using organic EL elements or liquid crystal displays). The color to be converted can be adjusted by appropriately selecting substituents on the polycyclic aromatic compounds of the present invention, binder resins used in the wavelength conversion composition described later, etc. The wavelength conversion material can be prepared as a wavelength conversion composition containing the polycyclic aromatic compounds of the present invention. Alternatively, a wavelength conversion film may be formed using this wavelength conversion composition.

[0405] The wavelength conversion composition may contain, in addition to the polycyclic aromatic compound of the present invention, a binder resin, other additives, and a solvent. As the binder resin, for example, those described in paragraphs 0173 to 0176 of International Publication No. 2016 / 190283 can be used. As the other additive, compounds described in paragraphs 0177 to 0181 of International Publication No. 2016 / 190283 can be used. As the solvent, refer to the description of solvents included in the above-mentioned light-emitting layer forming composition.

[0406] The wavelength conversion film includes a wavelength conversion layer formed by curing a wavelength conversion composition. Known film formation methods can be used as a method for producing the wavelength conversion layer from the wavelength conversion composition. The wavelength conversion film may consist solely of a wavelength conversion layer formed from a composition containing the polycyclic aromatic compound of the present invention, or it may include other wavelength conversion layers (for example, a wavelength conversion layer that converts blue light to green or red light, or a wavelength conversion layer that converts blue or green light to red light). Furthermore, the wavelength conversion film may include a substrate layer and a barrier layer to prevent degradation of the color conversion layer due to oxygen, moisture, or heat. [Examples]

[0407] The present invention will be described in more detail below with reference to examples, but the present invention is not limited to these examples.

[0408] Synthesis example (1): Synthesis of compound (1-1)

[0409] Under a nitrogen atmosphere, intermediate (X-1) (50.0 g), 3,4,5-trichlorotoluene (26.3 g), dichlorobis[di-t-butyl(4-dimethylaminophenyl)phosphino]palladium (Pd-132) (0.910 g) as a palladium catalyst, tBuONa (18.5 g), and toluene (500 ml) were placed in a flask and heated at 120°C for 5 hours. After the reaction was complete, water and ethyl acetate were added to the reaction mixture and stirred, and the organic layer was separated and washed with water. Subsequently, the organic layer was concentrated and the resulting crude product was purified using a silica gel short column (eluent: toluene / heptane = 1 / 4 (volume ratio)) to obtain 54.2 g of intermediate (X-2). [ka]

[0410] Under a nitrogen atmosphere, intermediate (X-2) (30.0 g), intermediate (X-3) (24.2 g), palladium catalysts Pd-132 (0.774 g), tBuONa (7.88 g), and toluene (300 ml) were placed in a flask and heated at 120°C for 3 hours. After the reaction was complete, water and ethyl acetate were added to the reaction mixture and stirred, and the organic layer was separated and washed with water. The organic layer was then concentrated, and the resulting crude product was purified using a silica gel short column (eluent: toluene / heptane = 1 / 4 (volume ratio)) to obtain 46.3 g of intermediate (X-4). [ka]

[0411] To a flask containing intermediate (X-4) (19.0 g) and tert-butylbenzene (190 ml), 25.0 ml of 1.60 M tert-butyllithium pentane solution was added at 0°C under a nitrogen atmosphere. After the addition was complete, the temperature was raised to 70°C and stirred for 0.5 hours, then components with a lower boiling point than tert-butylbenzene were removed by distillation under reduced pressure. The mixture was cooled to -50°C, boron tribromide (10.0 g) was added, and the temperature was raised to room temperature and stirred for 0.5 hours. Then, it was cooled again to 0°C, N,N-diisopropylethylamine (5.15 g) was added, and the mixture was stirred at room temperature until the exothermic reaction subsided, then the temperature was raised to 100°C and heated and stirred for 1 hour. The reaction mixture was cooled to room temperature, and liquid-liquid separation was performed by adding aqueous sodium acetate, which had been cooled in an ice bath, followed by ethyl acetate. The organic layer was concentrated and purified by silica gel short column (eluent: chlorobenzene). The crude product obtained was recrystallized with toluene to yield 3.12 g of compound (1-1). [ka]

[0412] The structure of the compound obtained by NMR measurement was confirmed. 1 H-NMR (CDCl3): δ=8.89(d,2H), 7.58(d,1H), 7.31-7.27(m,3H), 7.09(dd,1H), 6.48(s,1H), 6.44(s,1H), 6.04(s,1H), 5 .89(s,1H), 2.22-2.14(m,6H), 2.09-2.03(m,6H), 1.91-1.66(m,24H), 1.53-1.39(m,18H), 1.28(s,6H), 1.07(s,12H).

[0413] Synthesis example (2): Synthesis of compounds (1-42) Compound (1-42) was obtained from intermediate (X-5) in the same manner as in synthesis example (1). [ka]

[0414] The structure of the compound obtained by NMR measurement was confirmed. 1 H-NMR (CDCl3): δ=8.98(d,2H), 7.88(d,2H), 7.66(s,1H), 7.53-7.47(m,1H), 7.28-7.27(m,2H), 7.18(s,1H), 6.57(s,1H), 6.56(d,1H), 6.01(dd,1H), 5.96(dd,1H), 2.16(d,4H), 2.05-2.01(m,6 H), 1.90-1.81(m,12H), 1.78-1.76(m,2H), 1.73-1.71(m,3H), 1.69-1.55(m,2H), 1.56-1.47(m,1 2H), 1.43(s,9H), 1.12(s,3H), 1.09(s,3H), 1.01(s,9H), 0.99(s,3H), 0.80(s,9H), 0.76(s,3H).

[0415] Synthesis example (3): Synthesis of compound (1-106) Compound (1-106) was obtained from intermediate (X-6) in the same manner as in synthesis example (1). [ka]

[0416] The structure of the compound obtained by NMR measurement was confirmed. 1 H-NMR (CDCl3): δ=8.95(s,2H), 8.06(d,1H), 8.00(d,1H), 7.70(t,1H), 7.55(d,1H), 7 .49(t,2H), 7.27(dd,3H), 6.49(d,2H), 5.99(d,2H), 2.16(s,3H), 2.04(d,6H), 1.89( s,3H), 1.86(s,3H), 1.83(s,6H), 1.77-1.75(m,2H), 1.73-1.69(m,4H), 1.64-1.59(m ,2H), 1.51(s,6H), 1.49(d,6H), 1.11(d,6H), 0.97(s,3H), 0.84(s,9H), 0.73(s,3H).

[0417] Synthesis example (4): Synthesis of compound (1-107) Compound (1-107) was obtained from intermediate (X-7) in the same manner as in synthesis example (1). [ka]

[0418] The structure of the compound obtained by NMR measurement was confirmed. 1 H-NMR(CDCl3): δ=8.98-8.92(m,2H), 8.01(s,1H), 7.96(d,1H), 7.85-7.78(m,2 H), 7.57(t,1H), 7.48(t,1H), 7.28(s,2H), 6.58-6.52(m,2H), 6.10-5.95(m,2H ), 2.19-2.12(m,6H), 2.07-2.03(m,6H), 1.90-1.81(m,12H), 1.79-1.64(m,8H) , 1.53-1.47(m,12H), 1.12-1.08(m,6H), 1.03(s,3H), 0.98(s,3H), 0.92(s,9H).

[0419] Synthesis example (5): Synthesis of compounds (1-92) Compound (1-92) was obtained from intermediate (X-8) in the same manner as in synthesis example (1). EI-MS: m / z = 1020. [ka]

[0420] Synthesis example (6): Synthesis of compounds (1-130)

[0421] Under a nitrogen atmosphere, intermediate (X-2) (20.0 g), intermediate (X-9) (18.1 g), palladium catalysts Pd-132 (1.29 g), tBuONa (7.56 g), and toluene (300 ml) were placed in a flask and heated at 120°C for 3 hours. After the reaction was complete, water and ethyl acetate were added to the reaction mixture and stirred, and the organic layer was separated and washed with water. The organic layer was then concentrated, and the resulting crude product was purified using a silica gel short column (eluent: toluene / heptane = 1 / 4 (volume ratio)) to obtain 25.0 g of intermediate (X-10). [ka]

[0422] Compound (1-130) was obtained from intermediate (X-10) in the same manner as in synthesis example (1). EI-MS: m / z = 900. [ka]

[0423] Synthesis example (7): Synthesis of compounds (1-132) Compound (1-132) was obtained from intermediate (X-11) in the same manner as in synthesis example (1). EI-MS: m / z = 970. [ka]

[0424] Synthesis example (8): Synthesis of compounds (1-139) Compound (1-139) was obtained from intermediate (X-13) in the same manner as in synthesis example (1). EI-MS: m / z = 1024. [ka]

[0425] Synthesis example (9): Synthesis of compound (1-151) Compound (1-151) was obtained from intermediate (X-14) in the same manner as in synthesis example (1). EI-MS: m / z = 914. [ka]

[0426] Synthesis example (10): Synthesis of compounds (1-152) Compound (1-152) was obtained from intermediate (X-15) in the same manner as in synthesis example (1). EI-MS: m / z = 860. [ka]

[0427] Synthesis example (11): Synthesis of compounds (1-23) Compound (1-23) was obtained from intermediate (X-16) in the same manner as in synthesis example (1). EI-MS: m / z = 937. [ka]

[0428] Synthesis example (12): Synthesis of compounds (1-153) Compound (1-153) was obtained from intermediate (X-17) in the same manner as in synthesis example (1). EI-MS: m / z = 1079. [ka]

[0429] Synthesis example (13): Synthesis of compounds (1-154) Compound (1-154) was obtained from intermediate (X-18) in the same manner as in synthesis example (1). EI-MS: m / z = 1100. [ka]

[0430] Synthesis example (14): Synthesis of compounds (1-155) Compound (1-155) was obtained from intermediate (X-19) in the same manner as in synthesis example (1). EI-MS: m / z = 1004. [ka]

[0431] Synthesis example (15): Synthesis of compounds (1-156) Compound (1-156) was obtained from intermediate (X-20) in the same manner as in synthesis example (1). EI-MS: m / z = 1046. [ka]

[0432] Synthesis example (16): Synthesis of compounds (1-157) Compound (1-157) was obtained from intermediate (X-21) in the same manner as in synthesis example (1). [ka]

[0433] The structure of the compound obtained by NMR measurement was confirmed. 1H-NMR (CDCl3): δ=8.77(br,1H), 8.70(br,1H), 7.70(d,2H), 7.60(d,1H), 7.42-7.38(m,2H), 7 .31-7.27(m,4H), 7.17(d,4H), 7.01(d,4H), 6.92(br,1H), 6.51(br,1H), 6.32(s,1H), 6.17(br ,1H), 6.07(br,1H), 2.16(br,3H), 2.05(s,3H), 2.04(s,3H), 1.87(s,6H), 1.84(br,6H), 1.75 -1.67(m,8H), 1.44(s,6H), 1.38(s,6H), 1.34(s,6H), 1.17(s,18H), 1.08(s,6H), 0.97(s,9H).

[0434] Synthesis example (17): Synthesis of compounds (1-158) Compound (1-158) was obtained from intermediate (X-22) in the same manner as in synthesis example (1). EI-MS: m / z = 1109. [ka]

[0435] Synthesis example (18): Synthesis of compounds (1-159) Compound (1-159) was obtained from intermediate (X-23) in the same manner as in synthesis example (1). EI-MS: m / z = 1242. [ka]

[0436] Synthesis example (19): Synthesis of compounds (1-162) Compound (1-162) was obtained from intermediate (X-24) in the same manner as in synthesis example (1). EI-MS: m / z = 1332. [ka]

[0437] Synthesis example (20): Synthesis of compounds (1-165) Compound (1-165) was obtained from intermediate (X-25) in the same manner as in synthesis example (1). EI-MS: m / z = 1194. [ka]

[0438] Synthesis example (21): Synthesis of compounds (1-169) Compound (1-169) was obtained from intermediate (X-26) in the same manner as in synthesis example (1). EI-MS: m / z = 1318. [ka]

[0439] Synthesis example (22): Synthesis of compounds (1-170) Compound (1-170) was obtained from intermediate (X-27) in the same manner as in synthesis example (1). EI-MS: m / z = 1318. [ka]

[0440] Synthesis example (23): Synthesis of compound (1-171) Compound (1-171) was obtained from intermediate (X-28) in the same manner as in synthesis example (1). EI-MS: m / z = 1235. [ka]

[0441] By appropriately changing the raw material compounds, other compounds of the present invention can be synthesized by a method similar to the synthesis example described above.

[0442] <Methods for evaluating basic physical properties> Sample preparation When evaluating the absorption and luminescence properties (fluorescence and phosphorescence) of a compound under evaluation, the compound may be evaluated in a solvent after dissolving it, or in a thin film state. Furthermore, when evaluating in a thin film state, depending on how the compound is used in an organic EL device, the compound may be evaluated as a thin film, or the compound may be dispersed in an appropriate matrix material and then evaluated as a thin film. Here, a thin film obtained by vapor-depositing only the compound under evaluation is called a "single film," and a thin film obtained by applying and drying a coating solution containing the compound under evaluation and a matrix material is called a "coated film."

[0443] Commercially available materials such as PMMA (polymethyl methacrylate) can be used as the matrix material. In this example, PMMA and the compound to be evaluated are dissolved in toluene, and then a thin film is formed on a transparent quartz support substrate (10 mm × 10 mm) by spin coating to prepare the sample.

[0444] Furthermore, thin film samples where the matrix material is a host compound are prepared as follows: A transparent quartz support substrate (10 mm × 10 mm × 1.0 mm) is fixed to the substrate holder of a commercially available deposition apparatus (manufactured by Choshu Sangyo Co., Ltd.), a molybdenum deposition boat containing the host compound and a molybdenum deposition boat containing the dopant material are attached, and then the vacuum chamber is set to 5 × 10 -4 The pressure was reduced to Pa. Next, the deposition boat containing the host compound and the deposition boat containing the dopant material were heated simultaneously, and the host compound and dopant material were co-deposited to an appropriate film thickness to form a mixed thin film (sample) of the host compound and dopant material. Here, the deposition rate was controlled according to the set mass ratio of the host compound and dopant material.

[0445] Evaluation of absorption and emission properties The absorption spectrum of the sample will be measured using a UV-Vis-Near-Infrared spectrophotometer (Shimadzu Corporation, UV-2600). The fluorescence spectrum or phosphorescence spectrum of the sample will be measured using a spectrofluorometer (Hitachi High-Tech Corporation, F-7000).

[0446] For fluorescence spectrum measurement, the sample is excited at an appropriate excitation wavelength at room temperature and photoluminescence is measured. For phosphorescence spectrum measurement, the sample is immersed in liquid nitrogen (temperature 77K) using the attached cooling unit and measured. To observe the phosphorescence spectrum, an optical chopper was used to adjust the delay time from excitation light irradiation to the start of measurement. The sample is excited at an appropriate excitation wavelength and photoluminescence is measured.

[0447] Furthermore, the fluorescence quantum yield (PLQY) is measured using an absolute PL quantum yield analyzer (Hamamatsu Photonics K.K., C9920-02G).

[0448] Next, we will describe the evaluation of the basic physical properties of the polycyclic aromatic compound of the present invention.

[0449] Evaluation of fluorescence lifetime (delayed fluorescence) The fluorescence lifetime was measured at 300K using a fluorescence lifetime analyzer (Hamamatsu Photonics K.K., C11367-01). Specifically, both the fast- and slow-emission components of the fluorescence lifetime were observed at the maximum emission wavelength measured with an appropriate excitation wavelength. In typical room-temperature fluorescence lifetime measurements of organic EL materials that emit fluorescence, the slow-emission component involving the phosphorescent triplet component is rarely observed due to thermal deactivation of the triplet component. If a slow-emission component is observed in the compound under evaluation, it indicates that the triplet energy with a long excitation lifetime was shifted to the singlet energy due to thermal activation and observed as delayed fluorescence.

[0450] Calculation of the energy gap (Eg) The long-wavelength end A (nm) of the absorption spectrum obtained by the method described above is used to calculate Eg = 1240 / A.

[0451] Measurement of ionization potential (Ip) A transparent support substrate (28mm x 26mm x 0.7mm) coated with ITO (indium tin oxide) is fixed to the substrate holder of a commercially available deposition apparatus (manufactured by Choshu Sangyo Co., Ltd.), and a molybdenum deposition boat containing the target compound is attached. Then, the vacuum chamber is set to 5 x 10 -4 The pressure is reduced to Pa. Next, the deposition boat is heated to evaporate the target compound, forming a single film (Neat film) of the target compound.

[0452] The obtained individual films are used as samples, and the ionization potential of the target compound is measured using a photoelectron spectrometer (Sumitomo Heavy Industries, Ltd. PYS-201).

[0453] Calculation of electron affinity (Ea) The electron affinity can be estimated from the difference between the ionization potential measured by the method described above and the energy gap calculated by the method described above.

[0454] Measurement of excited singlet energy level E(S,Sh) and excited triplet energy level E(T,Sh) For a single film of the target compound formed on a glass substrate, the fluorescence spectrum is observed at 77K using the second absorption peak from the long wavelength side of the absorption spectrum as the excitation light, and the excited singlet energy level E(S,Sh) is determined from the short-wavelength shoulder of the peak of the fluorescence spectrum. Also, for a single film of the target compound formed on a glass substrate, the phosphorescence spectrum is observed at 77K using the second absorption peak from the long wavelength side of the absorption spectrum as the excitation light, and the excited triplet energy level E(T,Sh) is determined from the short-wavelength shoulder of the peak of the phosphorescence spectrum.

[0455] <Evaluation of Organic EL Devices> As described above, the compounds of the present invention have an appropriate energy gap (Eg) and a high triplet excitation energy (E T Because it is characterized by a small ΔEST, it is expected to be applied to light-emitting layers and charge transport layers, and is particularly expected to be applied to light-emitting layers.

[0456] Evaluation items and evaluation methods The evaluation items include driving voltage (V), emission wavelength (nm), CIE chromaticity (x,y), external quantum efficiency (%), maximum wavelength (nm) and full width at half maximum (nm) of the emission spectrum. These evaluation items can be measured using values ​​at appropriate emission brightness.

[0457] The quantum efficiency of a light-emitting device has two components: internal quantum efficiency and external quantum efficiency. Internal quantum efficiency indicates the proportion of external energy injected into the light-emitting layer of the device as electrons (or holes) that is purely converted into photons. External quantum efficiency, on the other hand, is calculated based on the amount of these photons emitted to the outside of the device. Since some of the photons generated in the light-emitting layer are absorbed or reflected within the device and not emitted to the outside, the external quantum efficiency is lower than the internal quantum efficiency.

[0458] The measurement methods for spectral radiance (emission spectrum) and external quantum efficiency are as follows: An Advantest R6144 voltage / current generator was used to apply voltage, causing the device to emit light. A TOPCON SR-3AR spectroradiometer was used to measure the spectral radiance in the visible light region from a direction perpendicular to the emission surface. Assuming the emission surface is a perfectly diffusive surface, the number of photons at each wavelength is obtained by dividing the measured spectral radiance value by the wavelength energy and multiplying by π. Next, the number of photons across the entire observed wavelength range was integrated to obtain the total number of photons emitted from the device. The applied current value divided by the elementary charge is used as the number of carriers injected into the device, and the external quantum efficiency is obtained by dividing the total number of photons emitted from the device by the number of carriers injected into the device. Furthermore, the full width at half maximum of the emission spectrum is determined as the width between the wavelengths above and below the maximum emission wavelength where the intensity is 50%.

[0459] Next, we will describe the fabrication and evaluation of organic EL elements using the polycyclic aromatic compounds of the present invention.

[0460] Organic EL element configuration Organic EL elements were manufactured using the polycyclic aromatic compound of the present invention.

[0461] [Component Configuration A] Table 1 below shows the material composition of each layer in the organic EL elements of Examples 1 to 23 and Comparative Examples 1 to 5. [Table 1-1] [Table 1-2]

[0462] In Table 1, "HI" is N 4 ,N 4’ -diphenyl-N 4 ,N 4’ -Bis(9-phenyl-9H-carbazole-3-yl)-[1,1'-biphenyl]-4,4'-diamine, "HAT-CN" is 1,4,5,8,9,12-hexaazatriphenylenehexacarbonnitrile, "HT-1" is N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-N-[4-(9-phenyl-9H-carbazole-3-yl)phenyl]-9H-fluoren-2-amine, and "HT-2" is N,N-bis(4-(dibenzo[b,d]furan) The compound is -4-yl)phenyl)-[1,1':4',1”-terphenyl]-4-amine, where "BH" is 2-(10-phenylanthracene-9-yl)dibenzo[b,d]furan, "ET-1" is 9,9'-[(5-(6-(1,1'-biphenyl)-4-yl)-2-phenylpyrimidine-4-yl)-1,3-phenylene]bis(9H-carbazole), and "ET-2" is 3-(6-(10-phenylanthracene-9-yl)naphthalene-2-yl)pyridine. The chemical structures of "Liq" and comparative compound 1 (compound described in International Publication No. 2020 / 017931), comparative compound 2 (compound described in Japanese Patent Publication No. 2020-520976), comparative compound 3 (compound described in International Publication No. 2017 / 138526), ​​comparative compound 4 (compound described in International Publication No. 2020 / 218079), and comparative compound 5 (compound described in International Publication No. 2020 / 080872) are shown below.

[0463] [ka]

[0464] [ka]

[0465] (Example 1) A 26mm x 28mm x 0.7mm glass substrate (manufactured by OptoScience Co., Ltd.), which had been polished to 150nm by sputtering an ITO film to a thickness of 180nm, was used as the transparent support substrate. This transparent support substrate was fixed to the substrate holder of a commercially available deposition apparatus (manufactured by Showa Vacuum Co., Ltd.), and molybdenum deposition boats containing HI, HAT-CN, HT-1, HT-2, BH, compound (1-1), ET-1, and ET-2, respectively, and aluminum nitride deposition boats containing Liq, LiF, and aluminum, respectively, were attached.

[0466] The following layers are sequentially formed on the ITO film of the transparent support substrate. The vacuum chamber is 5 × 10 -4 The pressure was reduced to Pa. First, HI was heated and deposited to a thickness of 40 nm. Next, HAT-CN was heated and deposited to a thickness of 5 nm. Then, HT-1 was heated and deposited to a thickness of 45 nm. Next, HT-2 was heated and deposited to a thickness of 10 nm to form a hole layer consisting of four layers. Next, BH and compound (1-1) were heated simultaneously and deposited to a thickness of 25 nm to form an emissive layer. The deposition rate was adjusted so that the mass ratio of BH to compound (1-1) was approximately 97:3. Furthermore, ET-1 was heated and deposited to a thickness of 5 nm. Next, ET-2 and Liq were heated simultaneously and deposited to a thickness of 25 nm to form a two-layer electron layer. The deposition rate was adjusted so that the mass ratio of ET-2 to Liq was approximately 50:50. The deposition rate for each layer was 0.01 to 1 nm / second. Subsequently, LiF was heated and deposited at a deposition rate of 0.01 to 0.1 nm / second to achieve a film thickness of 1 nm. Then, aluminum was heated and deposited to a film thickness of 100 nm to form a cathode, thereby obtaining an organic EL device.

[0467] (Examples 2-23 and Comparative Examples 1-5) Instead of compound (1-1), use compound (1-42), compound (1-106), compound (1-107), compound (1-92), compound (1-130), compound (1-132), compound (1-139), compound (1-151), compound (1-152), compound (1-23), compound (1-153), compound (1-154), compound (1-155), compound (1-156), compound ( Organic EL elements for Examples 2-23 and Comparative Examples 1-5 were obtained in the same manner as in Example 1, except that compounds (1-157), (1-158), (1-159), (1-162), (1-165), (1-169), (1-170), (1-171), comparative compound 1, comparative compound 2, comparative compound 3, comparative compound 4, and comparative compound 5 were used, respectively.

[0468] Evaluation items and evaluation methods The evaluation items include driving voltage (V), emission wavelength (nm), CIE chromaticity (x,y), external quantum efficiency (%), maximum wavelength (nm) and full width at half maximum (nm) of the emission spectrum. These evaluation items are, for example, 1000 cd / m². 2 The value at the time of emission can be used.

[0469] The quantum efficiency of a light-emitting device has two components: internal quantum efficiency and external quantum efficiency. Internal quantum efficiency indicates the proportion of external energy injected into the light-emitting layer of the device as electrons (or holes) that is purely converted into photons. External quantum efficiency, on the other hand, is calculated based on the amount of these photons emitted to the outside of the device. Since some of the photons generated in the light-emitting layer are absorbed or reflected within the device and not emitted to the outside, the external quantum efficiency is lower than the internal quantum efficiency.

[0470] The measurement method for spectral radiance (emission spectrum) and external quantum efficiency is as follows: Using an Advantest R6144 voltage / current generator, the device's radiance was 1000 cd / m². 2A voltage is applied to cause the element to emit light. A TOPCON SR-3AR spectroradiometer is used to measure the spectral radiance in the visible light region from a direction perpendicular to the light-emitting surface. Assuming the light-emitting surface is a perfectly diffusive surface, the number of photons at each wavelength is obtained by dividing the measured spectral radiance value of each wavelength component by the wavelength energy and multiplying by π. Next, the number of photons is integrated across the entire observed wavelength range to obtain the total number of photons emitted from the element. The number of carriers injected into the element is obtained by dividing the applied current value by the elementary charge, and the external quantum efficiency is obtained by dividing the total number of photons emitted from the element by the number of carriers injected into the element. The full width at half maximum of the emission spectrum is determined as the width between the wavelengths above and below the maximum emission wavelength where the intensity is 50%.

[0471] For the organic EL elements of Examples 1-23 and Comparative Examples 1-5, a DC voltage was applied with the ITO electrode as the anode and the LiF / aluminum electrode as the cathode, resulting in a reading of 1000 cd / m². 2 We measured the characteristics of the light emission and also measured the time it took to maintain a brightness of 90% or more of the initial brightness. The results are shown in Table 2.

[0472] [Table 2] [Explanation of Symbols]

[0473] 100 Organic Electroluminescent Devices 101 circuit board 102 Anode 103 Hole injection layer 104 Hole transport layer 105 Light-emitting layer 106 Electron transport layer 107 Electron injection layer 108 Cathode

Claims

1. Polycyclic aromatic compounds having a structure consisting of one or more structural units represented by the following formula (1); 【Chemistry 1】 In formula (1), Rings A, B, and C are each independently a substituted or substituted aryl ring or a substituted heteroaryl ring; Y １ is B, P, P=O, P=S, Al, Ga, As, Si-R, or Ge-R, where R in Si-R and Ge-R is a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted alkyl, or a substituted or unsubstituted cycloalkyl; X １ and X ２ are each independently >O, >N-R, >C(-R) ２ , >Si(-R) ２ , >S, or >Se, wherein R in said >N-R is hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, and said >C(-R) ２ and >Si(-R) ２ each R is independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, said >C(-R) ２ and said two R groups of >Si(-R) ２ may be bonded to each other to form a ring, R in said >N-R, said >C(-R) ２ and said >Si(-R) ２ at least one R may be bonded to at least one of said ring A and said ring B, or at least one of said ring A and said ring C via a linking group or a single bond; At least one hydrogen atom in the above structure may be substituted with cyano, halogen, or deuterium; However, at least one hydrogen atom in the above structure is substituted with a substituted or unsubstituted cycloalkyl group, In the above structure, at least one of the aryl ring or heteroaryl ring is condensed with at least one cycloalkane, and at least one hydrogen in the cycloalkane may be substituted, and at least one -CH in the cycloalkane ２ The dash may be replaced by -O-.

2. The polycyclic aromatic compound according to claim 1, wherein the structural unit represented by formula (1) is the structural unit represented by the following formula (2); 【Chemistry 2】 In formula (2), Each Z is independent of N or C-R Ｚ The C-R Ｚ R Ｚ Each of these is independently a hydrogen, aryl, heteroaryl, diarylamino (where the two aryls are not bonded to each other, or are bonded via a single bond or a linking group), diheteroarylamino (where the two heteroaryls are not bonded to each other, or are bonded via a single bond or a linking group), arylheteroarylamino (where the aryl and heteroaryl are not bonded to each other, or are bonded via a single bond or a linking group), diarylboryl (where the two aryls are not bonded to each other, or are bonded via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, or substituted silyl, wherein at least one hydrogen in these may be substituted with an aryl, heteroaryl, alkyl, or cycloalkyl; Two adjacent R Ｚ These may bond to each other to form an aryl ring or a heteroaryl ring, and the formed aryl ring and heteroaryl ring may each be substituted with aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (the two aryls may be bonded via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, or substituted silyl, and at least one hydrogen in these may be substituted with aryl, heteroaryl, alkyl, or cycloalkyl; Z = Z are independently >O, >N-R, and >C(-R). ２ , >Si(-R) ２ , >S, or >Se may also be the same as >N-R, the >C(-R) ２ and the above >Si(-R) ２ Each R is independently hydrogen, a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted alkyl, or a substituted or unsubstituted cycloalkyl, and the above >C(-R) ２ and the above >Si(-R) ２ The two Rs may be bonded to each other to form a ring; Y １ is B, P, P=O, P=S, Al, Ga, As, Si-R, or Ge-R, where R in Si-R and Ge-R is a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted alkyl, or a substituted or unsubstituted cycloalkyl; X １ is >O, >N-R, >C(-R) ２ , >Si(-R) ２ , >S, or >Se, where R in >N-R is hydrogen, a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted alkyl, or a substituted or unsubstituted cycloalkyl, and the >C(-R) ２ , and the above >Si(-R) ２ Each R is independently hydrogen, a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted alkyl, or a substituted or unsubstituted cycloalkyl, and the above >C(-R) ２ and the above >Si(-R) ２ The two Rs may be bonded to each other to form a ring, and the R in >N-R and the R in >C(-R) ２ and the above >Si(-R) ２ The R is a linking group or a single bond, and the C-R Ｚ The R in Z is such that Ｚ It may be combined with one or two of the following: G is a cycloalkyl-substituted aryl or cycloalkyl-substituted heteroaryl; At least one hydrogen atom in the above structure may be substituted with cyano, halogen, or deuterium; However, in the above structure, the aryl ring, heteroaryl ring, or the C-R Ｚ R Ｚ At least one of the rings formed by is condensed with at least one cycloalkane, and at least one hydrogen in the cycloalkane may be substituted, and at least one -CH in the cycloalkane ２ The dash may be replaced by -O-.

3. The polycyclic aromatic compound according to claim 1 or 2, having at least one adamantyl.

4. A polycyclic aromatic compound according to any one of claims 1 to 3, having a structure represented by formula (1i); 【Transformation 3】 During the ceremony, Z ａ Each is independently N or CR Ｚａ Z ｂ Each is independently N or CR Ｚｂ Z ｃ Each is independently N or CR Ｚｃ And R Ｚａ , R Ｚｂ and R Ｚｃ Each of these is independently a hydrogen, aryl, heteroaryl, diarylamino (where the two aryls are not bonded to each other or are bonded via a single bond or a linking group), diheteroarylamino (where the two heteroaryls are not bonded to each other or are bonded via a single bond or a linking group), arylheteroarylamino (where the aryl and heteroaryl are not bonded to each other or are bonded via a single bond or a linking group), diarylboryl (where the two aryls are not bonded to each other or are bonded via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, or substituted silyl, wherein at least one hydrogen in these may be substituted with an aryl, heteroaryl, alkyl, or cycloalkyl. Two adjacent R Ｚａ , two adjacent R Ｚｂ and two adjacent R Ｚｃ These may bond to each other to form an aryl ring or a heteroaryl ring, and the formed aryl ring and heteroaryl ring may be substituted with aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (the two aryls may be bonded via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, or substituted silyl, and at least one hydrogen in these may be substituted with aryl, heteroaryl, alkyl, or cycloalkyl; Y １ is B, P, P=O, P=S, Al, Ga, As, Si-R, or Ge-R, where R in Si-R and Ge-R is a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted alkyl, or a substituted or unsubstituted cycloalkyl; X １ and X ２ These are, independently, >O, >N-R, and >C(-R). ２ , >Si(-R) ２ , >S, or >Se, however X １ and X ２ Either one of them is >N-G, and R in >N-R is hydrogen, a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted alkyl, or a substituted or unsubstituted cycloalkyl, and >C(-R) ２ , and the above >Si(-R) ２ Each R is independently hydrogen, a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted alkyl, or a substituted or unsubstituted cycloalkyl, and the above >C(-R) ２ and the above >Si(-R) ２ The two Rs may be bonded to each other to form a ring, and the R in >N-R and the R in >C(-R) ２ and the above >Si(-R) ２ The R is a linking group or a single bond, and the C-R Ｚ The R in Z is such that Ｚ It may be combined with one or two of the following: G is a cycloalkyl-substituted aryl or cycloalkyl-substituted heteroaryl; In the above structure, at least one selected from the group consisting of aryl rings and heteroaryl rings is condensed with at least one cycloalkane, and at least one hydrogen in the cycloalkane may be substituted, and at least one -CH in the cycloalkane ２ The hyphen may be replaced by -O-; At least one hydrogen atom in the above structure may be substituted with cyano, halogen, or deuterium.

5. In formula (1i), the b ring and the c1 ring are each condensed with at least one cycloalkane, and at least one hydrogen in the cycloalkane may be substituted, and at least one -CH in the cycloalkane ２ The polycyclic aromatic compound according to claim 4, wherein the - may be substituted with -O-.

6. A polycyclic aromatic compound according to claim 4, represented by any one of the following formulas; 【Chemistry 4】 【Transformation 5】 【Transformation 6】 In the above formula, Me is methyl, tBu is t-butyl, and D is deuterium.

7. A polycyclic aromatic compound according to any one of claims 1 to 3, having a structure represented by formula (1a); 【Transformation 7】 During the ceremony, Z ａ Each is independently N or CR Ｚａ Z ｂ Each is independently N or CR Ｚｂ Z ｃ Each is independently N or CR Ｚｃ And R Ｚａ , R Ｚｂ and R Ｚｃ Each of these is independently a hydrogen, aryl, heteroaryl, diarylamino (where the two aryls are not bonded to each other or are bonded via a single bond or a linking group), diheteroarylamino (where the two heteroaryls are not bonded to each other or are bonded via a single bond or a linking group), arylheteroarylamino (where the aryl and heteroaryl are not bonded to each other or are bonded via a single bond or a linking group), diarylboryl (where the two aryls are not bonded to each other or are bonded via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, or substituted silyl, wherein at least one hydrogen in these may be substituted with an aryl, heteroaryl, alkyl, or cycloalkyl. Two adjacent R Ｚａ , two adjacent R Ｚｂ and two adjacent R Ｚｃ These may bond to each other to form an aryl ring or a heteroaryl ring, and the formed aryl ring and heteroaryl ring may be substituted with aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (the two aryls may be bonded via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, or substituted silyl, and at least one hydrogen in these may be substituted with aryl, heteroaryl, alkyl, or cycloalkyl; X ｃ >O, >N-R, >C(-R) ２ , >Si(-R) ２ , >S, or >Se, and the above >N-R, the above >C(-R) ２ and the above >Si(-R) ２ Each R is independently hydrogen, a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted alkyl, or a substituted or unsubstituted cycloalkyl, and the above >C(-R) ２ and the above >Si(-R) ２ The two Rs are either bonded to each other to form a ring, or they are not; Y １ is B, P, P=O, P=S, Al, Ga, As, Si-R, or Ge-R, where R in Si-R and Ge-R is a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted alkyl, or a substituted or unsubstituted cycloalkyl; X １ and X ２ are each independently >O, >N-R, >C(-R) ２ or >Si(-R) ２ , >S, or >Se, provided that one of X １ and X ２ is >N-G, R in said >N-R is hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, and R in said >C(-R) ２ and said >Si(-R) ２ is each independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, two R groups in said >C(-R) ２ and said >Si(-R) ２ may be bonded to each other to form a ring, R in said >N-R, R in said >C(-R) ２ and R in said >Si(-R) ２ may be bonded to one or two of said R in said Z which is C-R Ｚ via a linking group or a single bond, Ｚ ​ G is a cycloalkyl-substituted aryl or cycloalkyl-substituted heteroaryl; In the above structure, at least one selected from the group consisting of aryl rings and heteroaryl rings is condensed with at least one cycloalkane, and at least one hydrogen in the cycloalkane may be substituted, and at least one -CH in the cycloalkane ２ The hyphen may be replaced by -O-; At least one hydrogen atom in the above structure may be substituted with cyano, halogen, or deuterium.

8. A polycyclic aromatic compound according to claim 7, represented by any one of the following formulas; 【Transformation 8】 In the above formula, Me is methyl and tBu is t-butyl.

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

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

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

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

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

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