Organic electroluminescent devices and anthracene compounds

Abstract

The present invention relates to an organic electroluminescent device with improved energy efficiency having a light-emitting layer comprising an anthracene compound represented by the following formula (H) and a polycyclic aromatic compound which is a monomer represented by the following formula (D) or a polymer having a plurality of partial structures represented by the formula (D). In the above formula (H), R1 to R10 are hydrogen or aryl, etc., R21 to R30 are hydrogen, etc., X is >O, >NR (R is aryl, etc.), or >C(-R)2 (R is methyl, etc.), L is a single bond or arylene, etc., and n is an integer from 1 to 3, and at least one hydrogen in the formula (H) may be substituted with deuterium, etc., and in the above formula (D), ring A, ring B, and ring C are aryl rings or heteroaryl rings, and at least one hydrogen in these rings may be substituted, X1 and X2 are >O, >C(-R)2 (R is methyl, etc.), or >NR (R is aryl, etc.), and at least one hydrogen in the formula (D) may be substituted with deuterium, etc.

Description

Technology Field

[0001] The present invention relates to an organic electroluminescent device, and a display device and a lighting device using the same.

[0002] The present invention also relates to an anthracene compound that can be used for manufacturing the organic electroluminescent device. Background Technology

[0003] Conventionally, display devices using electroluminescent light-emitting elements have been extensively studied because they enable power saving and thinning. Additionally, organic electroluminescent elements made of organic materials (hereinafter referred to as organic EL elements) have been actively explored because they facilitate lightweighting and large-scale expansion. In particular, the development of organic materials with light-emitting characteristics such as blue, one of the three primary colors of light, and the combination of multiple materials that provide optimal light-emitting characteristics have been actively studied so far, regardless of whether they are polymer compounds or low-molecular-weight compounds.

[0004] An organic EL device has a structure comprising a pair of electrodes consisting of a positive electrode and a negative electrode, and one or more layers containing an organic compound disposed between the pair of electrodes. The layers containing the organic compound include a light-emitting layer or a charge transport / injection layer that transports or injects charges such as holes and electrons, but various organic materials suitable for these layers are being developed.

[0005] Recently, polycyclic aromatic compounds formed by condensing multiple aromatic rings with boron as a central atom have been reported as materials for light-emitting layers (Patent Document 1). In addition, Patent Document 2 reports that an excellent organic EL device can be obtained by configuring an organic EL device by placing a light-emitting layer containing this polycyclic aromatic compound as a dopant material and a specific anthracene-based compound as a host material between a pair of electrodes.

[0006] Patent document 3 describes the use of a compound having a structure with an anthracene backbone and a benzoxanthene backbone in the light-emitting layer or electron transport layer of an organic EL device. Prior art literature

[0007] International Publication No. 2015 / 102118, International Publication No. 2016 / 152544, U.S. Patent Publication No. 2015-001479 Specification The problem to be solved

[0008] As disclosed in the aforementioned patent documents, various materials and combinations are being developed as materials used in organic EL devices. By examining more specific combinations or additive materials, it is expected that an organic EL device will be provided that not only possesses desired luminescence characteristics but also has more practical and desirable characteristics. The present invention aims to provide an organic EL device with improved energy efficiency. means of solving the problem

[0009] The inventors, after carefully examining the above-mentioned problem, discovered that energy efficiency is improved by using a light-emitting layer comprising a compound having a structure having an anthracene skeleton and a benzoxanthene skeleton, and a polycyclic aromatic compound formed by condensing a plurality of aromatic rings with boron as the central atom, and based on this finding, completed the present invention.

[0010] Specifically, the present invention has the following configuration.

[0011] [1] An organic electroluminescent device having a pair of electrodes consisting of an anode and a cathode and a light-emitting layer disposed between the pair of electrodes,

[0012] The above-mentioned light-emitting layer comprises an anthracene compound represented by the following formula (H) and a polycyclic aromatic compound which is a monomer represented by the following formula (D) or a polymer having a plurality of partial structures represented by the following formula (D), forming an organic electroluminescent device.

[0013]

[0014] (among Equation (H),

[0015] R 1 ~R 10 Each is independently an aryl, alkyl, or heteroaryl, alkyl, or cycloalkyl that may be substituted with hydrogen, alkyl, or cycloalkyl, and may be substituted with cycloalkyl.

[0016] However, R 1 ~R 10 Any n of them constitute L, and

[0017] R 21 ~R 30 Each is independently an aryl, alkyl, or heteroaryl, alkyl, or cycloalkyl that may be substituted with hydrogen, alkyl, or cycloalkyl, and may be substituted with cycloalkyl.

[0018] R 21 ~R 30 Adjacent groups may be bonded to form an aryl ring or a heteroaryl ring, and at least one hydrogen in the formed ring may be substituted with an aryl, alkyl, or cycloalkyl group, which may be substituted with an alkyl or cycloalkyl group, a heteroaryl, alkyl, or cycloalkyl group, which may be substituted with an alkyl or cycloalkyl group.

[0019] However, R 21 ~R 30 One of them makes up L,

[0020] X is each independently >O, >S, >NR, >C(-R)2, >Si(-R)2, or >Se, and R of >NR, >C(-R)2, and >Si(-R)2 is each independently an aryl that may be substituted with an alkyl or cycloalkyl, a heteroaryl that may be substituted with an alkyl or cycloalkyl, an alkyl, or a cycloalkyl.

[0021] As X, the two Rs in the above >C(-R)2 or >Si(-R)2 may be bonded to each other to form a ring, and

[0022] As X, R of the above >NR is R by means of a connector or single coupling 21 or R 30 It may be combined with,

[0023] L is, R 1 ~R 10 The carbon atom and R to which either of them bonds 21 ~R 30 One of them bonds to the carbon atom, and

[0024] L is a single bond, an alkylene, an arylene that may be substituted with an alkyl or cycloalkyl group, or a heteroarylene that may be substituted with an alkyl or cycloalkyl group, and

[0025] n is an integer from 1 to 3, and

[0026] When n is 2 or 3, plural L, plural X, plural R 21 , multiple R 22 , multiple R 23 , multiple R 24 , multiple R 25 , multiple R 26 , multiple R 27 , multiple R 28 , multiple R 29 , multiple R 30 Each may be identical or different from one another,

[0027] At least one hydrogen in the compound represented by formula (H) may be substituted with a substituted silyl, cyano, halogen, or deuterium.

[0028]

[0029] (among Equation (D),

[0030] Rings A, B, and C are each independently aryl rings or heteroaryl rings, and at least one hydrogen in these rings may be substituted, and

[0031] X 1 and X 2Each is independently >O, >C(-R)2, or >NR, wherein R of >NR may be substituted an aryl, a heteroaryl, an alkyl, or a cycloalkyl, and furthermore, R of >NR may be bonded to at least one ring among the A ring, B ring, and C ring by means of a linker or a single bond, and R of >C(-R)2 may be independently an aryl that may be substituted with an alkyl or cycloalkyl, a heteroaryl, an alkyl, or a cycloalkyl that may be substituted with an alkyl or cycloalkyl, and two Rs in >C(-R)2 may be bonded to each other to form a ring.

[0032] In the above monomer or the above polymer, at least one selected from the group consisting of an aryl ring and a heteroaryl ring may be condensed into 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-.

[0033] The B ring and the C ring in the above monomer or the above polymer may be connected via a single bond or through -O-, -S-, or -C(-R)2-, and the R of the -C(-R)2- is hydrogen, alkyl, or cycloalkyl, and two Rs may be bonded to each other to form a ring.

[0034] At least one hydrogen in the monomer or the polymer may be substituted with cyano, halogen, or deuterium.

[0035] [2] An organic electroluminescent device described in [1], wherein the above anthracene compound is represented by the following formula (HA), the following formula (HB), the following formula (HC), the following formula (HD), or the following formula (HE).

[0036]

[0037]

[0038] Among the above equations (HA), (HB), (HC), (HD), and (HE),

[0039] R 1 , R 2 , R 3 , R 6 , R 7 , R 8 , R 9 , and R 10 Silver, each independently, hydrogen, an aryl having 6 to 30 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, an alkyl having 1 to 12 carbon atoms, a cycloalkyl having 3 to 16 carbon atoms, or the following formula (BO):

[0040]

[0041] It is a monovalent group obtained by removing one hydrogen from a compound represented by, and

[0042] R 21 ~R 30 Each is independently hydrogen, an aryl having 6 to 16 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, an alkyl having 1 to 12 carbon atoms, or a cycloalkyl having 3 to 16 carbon atoms, and R 21 ~R 30 Adjacent groups may be bonded to form an aryl ring having 6 to 10 carbon atoms or a heteroaryl ring having 2 to 10 carbon atoms, and at least one hydrogen in the formed ring may be substituted with an aryl having 6 to 16 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, an alkyl having 1 to 12 carbon atoms, or a cycloalkyl having 3 to 16 carbon atoms.

[0043] However, R 21 ~R 30 One of them makes up L,

[0044] X is, each independently, >O, >S, >NR, >C(-R)2, or >Si(-R)2, and R of >NR, >C(-R)2, and >Si(-R)2 is, each independently, an aryl having 6 to 16 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, an alkyl having 1 to 12 carbon atoms, or a cycloalkyl having 3 to 16 carbon atoms.

[0045] R of the above >NR as X is -O-, -S-, -C(-R)2-, or R by single bonding 21 or R 30 It may be bonded to, and R of the above -C(-R)2- is an alkyl having 1 to 12 carbon atoms or a cycloalkyl having 3 to 16 carbon atoms, and

[0046] L is, respectively, a single bond, an alkylene having 1 to 6 carbon atoms, an arylene having 6 to 16 carbon atoms that may be substituted with an alkyl having 1 to 5 carbon atoms or a cycloalkyl having 5 to 10 carbon atoms, or a heteroarylene having 2 to 15 carbon atoms that may be substituted with an alkyl having 1 to 5 carbon atoms or a cycloalkyl having 5 to 10 carbon atoms.

[0047] At least one hydrogen in each of the compounds represented by formula (HA), formula (HB), formula (HC), formula (HD), and formula (HE) may be substituted with a substituted silyl, cyano, halogen, or deuterium.

[0048] [3] An organic electroluminescent device described in [2], wherein the above anthracene compound is represented by the formula (HA) or the formula (HB).

[0049] [4] R 2 , R 3 , R 6 , and R 7 Silver is all hydrogen, and

[0050] R 9 It is a monovalent group obtained by removing one hydrogen from an aryl group having 6 to 18 carbon atoms, or a compound represented by the formula (BO), and

[0051] R 21 ~R 30Of these, all are hydrogen except for one constituting L,

[0052] X is, each independently, >O, >S, >NR, or >C(-R)2, wherein R of >NR is an aryl having 6 to 16 carbon atoms, and R of >C(-R)2 is all methyl.

[0053] L is a single bond or an arylene having 6 to 10 carbon atoms, and

[0054] At least one hydrogen in the compound represented by each of formulas (HA) and (HB) may be substituted with a substituted silyl, cyano, halogen, or deuterium.

[0055] [3] Organic field light-emitting diode described in [3].

[0056] [5] An organic light-emitting diode described in [4], wherein the above anthracene compound is represented by any one of the following structural formulas.

[0057]

[0058]

[0059] (In the formula, D represents deuterium and Me represents methyl.)

[0060] [6] An organic electroluminescent device described in [2], wherein the above anthracene compound is represented by formula (HC), formula (HD) or formula (HE).

[0061] [7] R 1 , R 8 , and R 10 All of them are aryls with 6 to 18 carbon atoms, and

[0062] R 21 ~R 30 Of these, all are hydrogen except for one constituting L,

[0063] X is, each independently, >O, >S, >NR, or >C(-R)2, wherein R of >NR is an aryl having 6 to 16 carbon atoms, and R of >C(-R)2 is all methyl.

[0064] L is a single bond or an arylene having 6 to 10 carbon atoms, and

[0065] At least one hydrogen in the compound represented by each of formulas (HC), (HD), and (HE) may be substituted with a substituted silyl, cyano, halogen, or deuterium.

[0066] [6] Organic field light-emitting diode described in [6].

[0067] [8] An organic light-emitting diode described in [7], wherein the above anthracene compound is represented by any one of the following structural formulas.

[0068]

[0069] (In the formula, D represents deuterium.)

[0070] [9] An organic electroluminescent device described in [2] in which all hydrogens in a compound represented by formula (HA), formula (HB), formula (HC), formula (HD) or formula (HE) are substituted with deuterium.

[0071]

[10] An organic light-emitting diode described in any one of [1] to [9], wherein the above polycyclic aromatic compound is a monomer represented by the following formula (Da), (Db), (Dc), (Dd), (De), or (Df), or a polycyclic aromatic compound having multiple partial structures represented by the formula (Da), (Db), (Dc), (Dd), (De), or (Df).

[0072]

[0073] (among Equation (Da), Equation (Db), Equation (Dc), Equation (Dd), Equation (De), and Equation (Df),

[0074] R 1 ~R 11Each is independently a hydrogen, aryl, heteroaryl, diarylamino, diheteroylamino, arylheteroylamino, diarylboryl (the two aryls may be connected via a single bond or a linker), alkyl, cycloalkyl, alkoxy, aryloxy, or substituted silyl, wherein at least one hydrogen in these may be substituted with an aryl, heteroaryl, alkyl, cycloalkyl, or substituted silyl, and furthermore, R 1 ~R 11 Adjacent groups may be bonded to form an aryl ring or a heteroaryl ring together with an a-ring, a b-ring, or a c-ring, and at least one hydrogen in the formed ring may be substituted with an aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryls may be bonded via a single bond or a linker), alkyl, cycloalkyl, alkoxy, aryloxy, or substituted silyl, and at least one hydrogen therein may be substituted with an aryl, heteroaryl, alkyl, cycloalkyl, or substituted silyl.

[0075] X X Each is independently >O, >S, >NR, or >C(-R)2, wherein R of >NR is an aryl that may be substituted, a heteroaryl that may be substituted, an alkyl that may be substituted, or a cycloalkyl that may be substituted, and furthermore, R of >C(-R)2 is each independently an aryl that may be substituted with hydrogen, an alkyl or cycloalkyl, a heteroaryl that may be substituted with an alkyl or cycloalkyl, an alkyl, or a cycloalkyl.

[0076] X 1 and X 2Each is independently >O, >C(-R)2, or >NR, wherein R of >NR is an aryl having 6 to 12 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, an alkyl having 1 to 6 carbon atoms, or a cycloalkyl having 3 to 14 carbon atoms, wherein the aryl having 6 to 12 carbon atoms and the heteroaryl having 2 to 15 carbon atoms in R of >NR may all be substituted with an alkyl having 1 to 6 carbon atoms, a cycloalkyl having 3 to 14 carbon atoms, or a substituted silyl, and R of >NR may be bonded to at least one of an a-ring, a b-ring, and a c-ring by means of -O-, -S-, -C(-R)2-, or a single bond.

[0077] The R of the above >C(-R)2 is each independently an aryl having 6 to 12 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, an alkyl having 1 to 6 carbon atoms, or a cycloalkyl having 3 to 14 carbon atoms, and the aryl having 6 to 12 carbon atoms and the heteroaryl having 2 to 15 carbon atoms in the R of the above >C(-R)2 may all be substituted with an alkyl having 1 to 6 carbon atoms, a cycloalkyl having 3 to 14 carbon atoms, or a substituted silyl, and the two Rs in the above >C(-R)2 may be bonded to each other to form a ring.

[0078] In the monomer or the polymer, at least one of the a-ring, b-ring, c-ring, the formed ring, the aryl, and the heteroaryl may be condensed into at least one cycloalkane having 3 to 24 carbon atoms, and at least one hydrogen in the cycloalkane may be substituted with an aryl having 6 to 30 carbon atoms, a heteroaryl having 2 to 30 carbon atoms, an alkyl having 1 to 24 carbon atoms, or a cycloalkyl having 3 to 24 carbon atoms, and at least one -CH2- in the cycloalkane may be substituted with -O-.

[0079] At least one hydrogen in the monomer or the polymer may be substituted with cyano, halogen, or deuterium, and

[0080] In the case of a multimer, it is a dimer or trimer having two or three substructures represented by formulas (Da), (Db), (Dc), (Dd), (De), or (Df).

[0081]

[11] The above polycyclic aromatic compound is a polycyclic aromatic compound having a plurality of monomers represented by formula (Da) or a polycyclic aromatic compound having a portion structure represented by formula (Da), as described in

[10] , an organic electroluminescent device.

[0082]

[12] An organic light-emitting diode described in

[11] , wherein the above polycyclic aromatic compound is represented by any one of the following structural formulas.

[0083]

[0084]

[0085] (In the formula, D represents deuterium, Me represents methyl, and tBu represents tert-butyl.)

[0086]

[13] The above polycyclic aromatic compound is a polycyclic aromatic compound having a plurality of monomers represented by formula (Db) or a polycyclic aromatic compound having a portion structure represented by formula (Db), as described in

[10] , an organic electroluminescent device.

[0087]

[14] An organic light-emitting diode described in

[13] , wherein the above polycyclic aromatic compound is represented by any one of the following structural formulas.

[0088]

[0089] (In the formula, Me represents methyl and tBu represents tert-butyl.)

[0090]

[15] An organic electroluminescent device described in any one of [1] to

[14] , having at least one of an electron transport layer and an electron injection layer disposed between the cathode and the light-emitting layer, wherein at least one of the electron transport layer and the electron injection layer contains at least one selected from the group consisting of a boran derivative, a pyridine derivative, a fluoranthene derivative, a BO-based derivative, anthracene derivative, a benzofluorene derivative, a phosphine oxide derivative, a pyrimidine derivative, an arylnitrile derivative, a triazine derivative, a benzimidazole derivative, a phenanthroline derivative, a quinolinol-based metal complex, a thiazole derivative, a benzothiazole derivative, a silol derivative, and an azoline derivative.

[0091]

[16] An organic electroluminescent device described in

[15] , wherein at least one of the electron transport layer and electron injection layer further comprises at least one selected from the group consisting of alkali metal, alkaline earth metal, rare earth metal, oxide of alkali metal, halide of alkali metal, oxide of alkaline earth metal, halide of alkaline earth metal, oxide of rare earth metal, halide of rare earth metal, organic complex of alkali metal, organic complex of alkaline earth metal and organic complex of rare earth metal.

[0092]

[17] A display device equipped with an organic light-emitting element as described in any one of [1] to

[16] .

[0093]

[18] A lighting device equipped with an organic light-emitting element as described in any one of [1] to

[16] .

[0094]

[19] A compound represented by the following formula (HA') or the following formula (HB').

[0095]

[0096] Among formulas (HA') and (HB'),

[0097] R 2 , R 3 , R 6 , R 7 , and R 9Silver, each independently, hydrogen, an aryl having 6 to 30 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, an alkyl having 1 to 12 carbon atoms, a cycloalkyl having 3 to 16 carbon atoms, or the following formula (BO):

[0098]

[0099] It is a monovalent group obtained by removing one hydrogen from a compound represented by, and

[0100] R 21 ~R 30 Each is independently hydrogen, an aryl having 6 to 16 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, an alkyl having 1 to 12 carbon atoms, or a cycloalkyl having 3 to 16 carbon atoms, and R 21 ~R 30 Adjacent groups may be bonded to form an aryl ring having 6 to 10 carbon atoms or a heteroaryl ring having 2 to 10 carbon atoms, and at least one hydrogen in the formed ring may be substituted with an aryl having 6 to 16 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, an alkyl having 1 to 12 carbon atoms, or a cycloalkyl having 3 to 16 carbon atoms.

[0101] However, R 21 ~R 30 One of them makes up L,

[0102] R is, respectively, an aryl having 6 to 16 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, an alkyl having 1 to 12 carbon atoms, or a cycloalkyl having 3 to 16 carbon atoms, and

[0103] R is -O-, -S-, -C(-R)2-, or R by a single bond. 21 or R 30 It may be bonded to, and R of the above -C(-R)2- is an alkyl having 1 to 12 carbon atoms or a cycloalkyl having 3 to 16 carbon atoms, and

[0104] L is, respectively, a single bond, an alkylene having 1 to 6 carbon atoms, an arylene having 6 to 16 carbon atoms that may be substituted with an alkyl having 1 to 5 carbon atoms or a cycloalkyl having 5 to 10 carbon atoms, or a heteroarylene having 2 to 15 carbon atoms that may be substituted with an alkyl having 1 to 5 carbon atoms or a cycloalkyl having 5 to 10 carbon atoms.

[0105] At least one hydrogen in each of the compounds represented by formula (HA') and formula (HB') may be substituted with a substituted silyl, cyano, halogen, or deuterium.

[0106]

[20] R 2 , R 3 , R 6 , R 7 All of it is hydrogen, and R 9 is a monovalent group obtained by removing one hydrogen from an unsubstituted aryl having 6 to 30 carbon atoms or a compound represented by the formula (BO), and is a monovalent group obtained by removing one hydrogen from an unsubstituted aryl having 6 to 12 carbon atoms or a compound represented by the formula (BO), R is an unsubstituted aryl having 6 to 16 carbon atoms, and L is a compound described in

[19] in which all are single bonds.

[0107]

[21] A compound represented by the following formula (HC') or the following formula (HE').

[0108]

[0109] Among equations (HC') and (HE'),

[0110] R 1 , R 2 , R 3 , R 6 , R 7 , and R 8 Silver, each independently, hydrogen, an aryl having 6 to 30 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, an alkyl having 1 to 12 carbon atoms, a cycloalkyl having 3 to 16 carbon atoms, or the following formula (BO):

[0111]

[0112] It is a monovalent group obtained by removing one hydrogen from a compound represented by, and

[0113] R 21 ~R 30 Each is independently hydrogen, an aryl having 6 to 16 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, an alkyl having 1 to 12 carbon atoms, or a cycloalkyl having 3 to 16 carbon atoms, and R 21 ~R 30 Adjacent groups may be bonded to form an aryl ring having 6 to 10 carbon atoms or a heteroaryl ring having 2 to 10 carbon atoms, and at least one hydrogen in the formed ring may be substituted with an aryl having 6 to 16 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, an alkyl having 1 to 12 carbon atoms, or a cycloalkyl having 3 to 16 carbon atoms.

[0114] However, R 21 ~R 30 One of them makes up L,

[0115] X is, each independently, >O, >S, >NR, >C(-R)2, or >Si(-R)2, and R of >NR, >C(-R)2, and >Si(-R)2 is, each independently, an aryl having 6 to 16 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, an alkyl having 1 to 12 carbon atoms, or a cycloalkyl having 3 to 16 carbon atoms.

[0116] R of the above >NR as X is -O-, -S-, -C(-R)2-, or R by single bonding 21 or R 30 It may be bonded to, and R of the above -C(-R)2- is an alkyl having 1 to 12 carbon atoms or a cycloalkyl having 3 to 16 carbon atoms, and

[0117] L is, respectively, a single bond, an alkylene having 1 to 6 carbon atoms, an arylene having 6 to 16 carbon atoms that may be substituted with an alkyl having 1 to 5 carbon atoms or a cycloalkyl having 5 to 10 carbon atoms, or a heteroarylene having 2 to 15 carbon atoms that may be substituted with an alkyl having 1 to 5 carbon atoms or a cycloalkyl having 5 to 10 carbon atoms.

[0118] At least one hydrogen in each of the compounds represented by formula (HC') and formula (HE') may be substituted with a substituted silyl, cyano, halogen, or deuterium.

[0119]

[22] R 2 , R 3 , R 6 , R 7 All of it is hydrogen, and R 1 and R 8 Compounds described in

[21] , each independently unsubstituted aryls with 6 to 30 carbon atoms, where L is a single bond.

[0120]

[23] A compound represented by the following formula (HD').

[0121]

[0122] Among the (HD') formulas,

[0123] R 2 , R 3 , R 6 , R 7 , and R 10 Silver, each independently, hydrogen, an aryl having 6 to 30 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, an alkyl having 1 to 12 carbon atoms, a cycloalkyl having 3 to 16 carbon atoms, or the following formula (BO):

[0124]

[0125] It is a monovalent group obtained by removing one hydrogen from a compound represented by, and

[0126] R 21 ~R 30 R, an aryl having 6 to 16 carbon atoms where any one of them is unsubstituted. 21 ~R 30 One of them constitutes L, R 21 ~R 30 Of the others, any one is an unsubstituted aryl having 6 to 16 carbon atoms, and the others are hydrogens,

[0127] X is, each independently, >O, >S, >NR, >C(-R)2, or >Si(-R)2, and R of >NR, >C(-R)2, and >Si(-R)2 is, each independently, an aryl having 6 to 16 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, an alkyl having 1 to 12 carbon atoms, or a cycloalkyl having 3 to 16 carbon atoms.

[0128] R of the above >NR as X is -O-, -S-, -C(-R)2-, or R by single bonding 21 or R 30 It may be bonded to, and R of the above -C(-R)2- is an alkyl having 1 to 12 carbon atoms or a cycloalkyl having 3 to 16 carbon atoms, and

[0129] L is, respectively, a single bond, an alkylene having 1 to 6 carbon atoms, an arylene having 6 to 16 carbon atoms that may be substituted with an alkyl having 1 to 5 carbon atoms or a cycloalkyl having 5 to 10 carbon atoms, or a heteroarylene having 2 to 15 carbon atoms that may be substituted with an alkyl having 1 to 5 carbon atoms or a cycloalkyl having 5 to 10 carbon atoms.

[0130] At least one hydrogen in the compound represented by formula (HD') may be substituted with a substituted silyl, cyano, halogen, or deuterium.

[0131]

[24] R 2 , R 3 , R 6 , R 7 All of it is hydrogen, and R 10 The compound described in

[23] is an unsubstituted aryl with 6 to 30 carbon atoms. Effects of the invention

[0132] The present invention can provide an organic EL device with high efficiency and a long lifespan. In a preferred embodiment of the present invention, an organic EL device with a narrower half-width of the emission spectrum and improved color purity can also be provided. Brief explanation of the drawing

[0133] Figure 1 is a schematic cross-sectional view showing an example of an organic EL device. Specific details for implementing the invention

[0134] The present invention will be described in detail below. The description of the constituent elements described below may be based on representative embodiments or specific examples, but the present invention is not limited to such embodiments. Furthermore, in this specification, a numerical range indicated by "~" refers to a range that includes the values ​​described before and after "~" as lower and upper limits. Additionally, in the description of structural formulas in this specification, "hydrogen" refers to a "hydrogen atom (H)."

[0135] In this specification, chemical structures or substituents may be represented by the number of carbon atoms; however, the number of carbon atoms in cases where a substituent is substituted into a chemical structure or where a substituent is also substituted into a substituent refers to the number of carbon atoms of each chemical structure or substituent, and does not refer to the total number of carbon atoms of the chemical structure and the substituents, or the total number of carbon atoms of the substituents. For example, "substituent B of carbon number Y substituted by substituent A of carbon number X" means that "substituent A of carbon number X" substitutes "substituent B of carbon number Y," and carbon number Y is not the total number of carbon atoms of substituent A and substituent B. Furthermore, for example, "substituent B of carbon number Y substituted by substituent A" means that "substituent A (without limiting the number of carbon atoms)" substitutes "substituent B of carbon number Y," and carbon number Y is not the total number of carbon atoms of substituent A and substituent B.

[0136] Organic field light-emitting diodes

[0137] The organic electroluminescent device of the present invention comprises a pair of electrodes consisting of an anode and a cathode, and a light-emitting layer disposed between the pair of electrodes. The light-emitting layer comprises at least one of an anthracene compound represented by formula (H), a polycyclic aromatic compound represented by formula (D), and a polymer of a polycyclic aromatic compound having a plurality of partial structures represented by formula (D).

[0138] 1. Anthracene compounds represented by formula (H)

[0139] The organic EL device of the present invention comprises an anthracene-based compound represented by the following formula (H) in the light-emitting layer. It is preferable that the anthracene-based compound represented by the following formula (H) be included in the light-emitting layer as a host material.

[0140]

[0141] In equation (H), R 1 ~R 10 ...is, respectively, an aryl, alkyl, or heteroaryl, alkyl, or cycloalkyl that may be substituted with hydrogen, alkyl, or cycloalkyl, provided that R 1 ~R 10 Any n of them constitute L.

[0142] Anthracene compounds represented by formula (H) have a structure in which n groups represented by the following formula (H-sub) are bonded to the anthracene skeleton. That is, R other than the n groups represented by formula (H-sub) in formula (H) 1 ~R 10 All of them are not represented by the expression (H-sub). This is also true for the expressions (HA), (HB), (HC), (HD) and the following expression (HE) described later.

[0143]

[0144] In the equation (H-sub), L, X, R 21 ~R 30is L, X, R in equation (H) 21 ~R 30 Each has the same meaning, and * indicates the combination position.

[0145] In the group represented by the equation (H-sub), R 21 ~R 30 Any one of them may constitute L, but R 21 , R 22 , R 23 , R 24 , R 25 , R 28 or R 29 It is desirable that, R 23 , R 28 or R 29 It is more preferable that, in an anthracene compound represented by formula (H), when there are two or three groups represented by formula (H-sub), the position of the ring constituent atom to which L is bonded (R 21 ~R 30 Any one of them may be identical or different, but it is preferable that they be identical.

[0146] In equation (H), R other than the n constituting L 1 ~R 10 It is preferable that each of the following be independently hydrogen, an aryl having 6 to 30 carbon atoms that may be substituted with an alkyl having 1 to 24 carbon atoms or a cycloalkyl having 3 to 24 carbon atoms, a heteroaryl having 2 to 30 carbon atoms that may be substituted with an alkyl having 1 to 24 carbon atoms or a cycloalkyl having 3 to 24 carbon atoms, an alkyl having 1 to 24 carbon atoms, or a cycloalkyl having 3 to 24 carbon atoms; it is more preferable that each of the following be independently hydrogen, an unsubstituted aryl having 6 to 30 carbon atoms, or an unsubstituted heteroaryl having 2 to 30 carbon atoms; and it is even more preferable that each of the following be hydrogen, an unsubstituted aryl having 6 to 12 carbon atoms, a heteroaryl having 2 to 12 carbon atoms, or a monovalent group obtained by removing hydrogen from any one of the compounds represented by the following formula (BO).

[0147]

[0148] In equation (H), R other than the n constituting L 1 ~R 10 It is preferable that all of them be hydrogen, or that one or two are non-hydrogen and the rest are hydrogen.

[0149] In equation (H), R 21 ~R 30 is, respectively, an aryl, alkyl, or heteroaryl, alkyl, or cycloalkyl that may be substituted with hydrogen, alkyl, or cycloalkyl. Also, R 21 ~R 30 Adjacent groups may be bonded to form an aryl ring or a heteroaryl ring, and at least one hydrogen in the formed ring may be substituted with an aryl that may be substituted with an alkyl or cycloalkyl, a heteroaryl that may be substituted with an alkyl or cycloalkyl, an alkyl, or a cycloalkyl. However, R 21 ~R 30 One of them constitutes L.

[0150] R 21 ~R 30 When adjacent groups are bonded to form an aryl ring or a heteroaryl ring, the aryl ring or heteroaryl ring is preferably an aryl ring having 6 to 10 carbon atoms or a heteroaryl ring having 2 to 10 carbon atoms, and at least one hydrogen in the formed ring may be substituted with an aryl having 6 to 30 carbon atoms that may be substituted with an alkyl having 1 to 24 carbon atoms or a cycloalkyl having 3 to 24 carbon atoms, a heteroaryl having 2 to 30 carbon atoms that may be substituted with an alkyl having 1 to 24 carbon atoms or a cycloalkyl having 3 to 24 carbon atoms, an alkyl having 1 to 24 carbon atoms, or a cycloalkyl having 3 to 24 carbon atoms.

[0151] R 21 ~R 30Examples of "aryl rings" formed when adjacent groups combine to form an aryl ring include, specifically, the monocyclic benzene ring, the dicyclic biphenyl ring, the condensed dicyclic naphthalene ring, the indene ring, the tricyclic terphenyl ring (m-terphenyl, o-terphenyl, p-terphenyl), the condensed tricyclic acenaphtylene ring, fluorene ring, phenalene ring, phenanthrene ring, the condensed tetracyclic triphenylene ring, pyrene ring, naphthacene ring, and the condensed pentacyclic perylene ring, pentacene ring.

[0152] R 21 ~R 30 As for the "heteroaryl ring" when adjacent groups combine to form a heteroaryl ring, for example, the pyrrole ring, oxazole ring, isooxazole ring, thiazole ring, isothiaazole ring, imidazole ring, oxadiazole ring, thiadiazole ring, triazole ring, tetrazole ring, pyrazol ring, pyridine ring, pyrimidine ring, pyridazine ring, pyrazine ring, triazine ring, indole ring, isoindole ring, 1H-indazole ring, benzimidazole ring, benzoxazole ring, benzothiaazole ring, 1H-benzotriazole ring, quinoline ring, isoquinoline ring, cinnoline ring, quinazolin ring, quinoxaline ring, phthalazine ring, naphthiridine ring, purine ring, pteridine ring, carbazole ring, acridine ring, phenoxatin ring, phenoxazine ring, There are phenothiazine rings, phenazine rings, phenazasirin rings, indolezine rings, furan rings, benzofuran rings, isobenzofuran rings, dibenzofuran rings, thiophene rings, benzothiophene rings, dibenzothiophene rings, furazane rings, thianthren rings, indolocarbazole rings, benzindolocarbazole rings, benzobenzindolocarbazole rings, naphthobenzofuran rings, etc.

[0153] In Equation (H), R other than the one constituting L 21 ~R 30It is preferable that each of the following be hydrogen, an aryl having 6 to 30 carbon atoms that may be substituted with an alkyl having 1 to 24 carbon atoms or a cycloalkyl having 3 to 24 carbon atoms, a heteroaryl having 2 to 30 carbon atoms that may be substituted with an alkyl having 1 to 24 carbon atoms or a cycloalkyl having 3 to 24 carbon atoms, an alkyl having 1 to 24 carbon atoms, or a cycloalkyl having 3 to 24 carbon atoms, and it is even more preferable that all of them be hydrogen.

[0154] In formula (H), X is each independently >O, >S, >NR, >C(-R)2, >Si(-R)2, or >Se, and is preferably >O, >S, >NR, >C(-R)2, or >Si(-R)2, more preferably O, >S, >NR, or >C(-R)2, and even more preferably O or >NR.

[0155] R of >NR, >C(-R)2, and >Si(-R)2 as X in formula (H) is, respectively, an aryl that may be substituted with an alkyl or cycloalkyl, a heteroaryl that may be substituted with an alkyl or cycloalkyl, an alkyl, or a cycloalkyl; preferably, an aryl that may be substituted with an alkyl having 1 to 24 carbons or a cycloalkyl having 3 to 24 carbons, an aryl having 6 to 30 carbons that may be substituted with an alkyl having 1 to 24 carbons or a cycloalkyl having 3 to 24 carbons, a heteroaryl having 2 to 30 carbons that may be substituted with an alkyl having 1 to 24 carbons or a cycloalkyl having 3 to 24 carbons, an alkyl having 1 to 24 carbons, or a cycloalkyl having 3 to 24 carbons.

[0156] As X in formula (H), the two Rs of >C(-R)2 or >Si(-R)2 may be bonded to each other to form a ring. The formed ring is preferably a cycloalkane ring having 3 to 12 carbon atoms. In addition, as X in formula (H), the R of >NR is formed by a linker or a single bond, R 21 or R 30 It may be bonded to. For example, hydrogen R 21 or R 30This, bonded to R to substitute with hydrogen (R is R in equation (H) 21 The carbon atom or R at this bonded position 30 It may be bonded to the carbon atom at the bonded position. Examples of linkers in this case include -O-, -S-, or -C(-R)2-, and R of -C(-R)2- is an alkyl group having 1 to 24 carbon atoms or a cycloalkyl group having 3 to 24 carbon atoms.

[0157] R of >NR as X in formula (H) is preferably an aryl having 6 to 30 carbon atoms that may be substituted with an alkyl having 1 to 24 carbon atoms or a cycloalkyl having 3 to 24 carbon atoms, a heteroaryl having 2 to 30 carbon atoms that may be substituted with an alkyl having 1 to 24 carbon atoms or a cycloalkyl having 3 to 24 carbon atoms, an alkyl having 1 to 24 carbon atoms, or a cycloalkyl having 3 to 24 carbon atoms; more preferably an aryl having 6 to 30 carbon atoms that may be substituted with an alkyl having 1 to 24 carbon atoms or a cycloalkyl having 3 to 24 carbon atoms, even more preferably an unsubstituted aryl having 6 to 10 carbon atoms, and particularly preferably an unsubstituted phenyl.

[0158] R in >C(-R)2 and >Si(-R)2 as X in formula (H) is preferably, respectively, an aryl having 6 to 30 carbon atoms that may be substituted with an alkyl having 1 to 24 carbon atoms or a cycloalkyl having 3 to 24 carbon atoms, a heteroaryl having 2 to 30 carbon atoms that may be substituted with an alkyl having 1 to 24 carbon atoms or a cycloalkyl having 3 to 24 carbon atoms, an alkyl having 1 to 24 carbon atoms, or a cycloalkyl having 3 to 24 carbon atoms; it is more preferably an alkyl having 1 to 24 carbon atoms, and even more preferably an alkyl having 1 to 6 carbon atoms. It is particularly preferable that R in >C(-R)2 as X in formula (H) is methyl in all cases.

[0159] L is, R 1 ~R 10 The carbon atom that bonds to any one of them and R 21 ~R30 L is a single bond or a divalent linker that bonds a carbon atom to which any one of them is bonded. L is a single bond, an alkylene, an arylene that may be substituted with an alkyl or cycloalkyl, or a heteroarylene that may be substituted with an alkyl or cycloalkyl; it is preferably a single bond, an alkylene having 1 to 6 carbon atoms, an arylene having 6 to 30 carbon atoms that may be substituted with an alkyl having 1 to 24 carbon atoms or a cycloalkyl having 3 to 24 carbon atoms, or a heteroarylene having 2 to 30 carbon atoms that may be substituted with an alkyl having 1 to 24 carbon atoms or a cycloalkyl having 3 to 24 carbon atoms, more preferably an arylene having 6 to 30 carbon atoms or a heteroarylene having 2 to 30 carbon atoms, and even more preferably a single bond or an arylene having 6 to 30 carbon atoms. Specifically, L can be a single bond, 1,4-phenylene, 1,3-phenylene, 1,2-phenylene, 2,7-naphthylene, 2,6-naphthylene, 1,4-naphthylene, 2,8-dibenzofuranilene, 2,8-dibenzothiophenylene, 4,6-dibenzofuranilene, 4,6-dibenzothiophenylene, 2,7-N-phenylcarbazolilene, 3,6-N-phenylcarbazolilene, 1,8-N-phenylcarbazolilene, etc., and a single bond, 1,4-phenylene, 1,3-phenylene, 1,2-phenylene, 2,7-naphthylene, 2,6-naphthylene, or 1,4-naphthylene is preferred, and a single bond is more preferred.

[0160] n is an integer from 1 to 3.

[0161] When n is 2, 2 L, 2 X, 2 R 21 , 2 R 22 , 2 R 23 , 2 R 24 , 2 R 25 , 2 R 26 , 2 R 27 , 2 R 28 , 2 R 29 , 2 R 30 Each may be identical or different from one another, but it is desirable for them to all be identical.

[0162] When n is 3, 3 L, 3 X, 3 R 21 , 3 R 22 , 3 R 23 , 3 R 24 , 3 R 25 , 3 R 26 , 3 R 27 , 3 R 28 , 3 R 29 , 3 R 30 Each of them may be identical, any two may be identical, or all three may be different, but it is preferable that they are all identical.

[0163] R in equation (H) 1 ~R 10 Among them, it is preferable that the n locations constituting L are not adjacent to each other, and specifically, the locations represented by Equation (HA), Equation (HB), Equation (HC), Equation (HD), or Equation (HE), which will be described later, are preferable.

[0164] At least one hydrogen in the compound represented by formula (H) may be substituted with a substituted silyl, cyano, halogen, or deuterium. For example, at least one group represented by formula (H-sub) or R in formula (H) 1 ~R 10A compound in which one or more hydrogens in an aryl or heteroaryl are substituted with substituted silyl, cyano, or halogen, particularly a compound in which one hydrogen in the group represented by formula (H-sub) is substituted with trimethylsilyl or cyano, can be cited as a preferred example. Furthermore, a compound in which at least one hydrogen in the compound represented by formula (H) is substituted with deuterium is preferred from the perspective of the durability of the compound, and it is more preferable that all hydrogens of the anthracene ring (hydrogens bonded to the anthracene ring and hydrogens in the substituents bonded to the anthracene ring) are substituted with deuterium, or that all hydrogens are substituted with deuterium, and even more preferable that all hydrogens are substituted with deuterium.

[0165] In the description of the compound represented by formula (H), "aryl" is a monovalent group formed by an aryl ring. As for the "aryl ring," R 21 ~R 30 Examples of the "aryl ring" when adjacent groups combine to form an aryl ring include those mentioned above. Specifically, examples of aryls in compounds represented by formula (H) include phenyl, 1-naphthyl, 2-naphthyl, 2-biphenylyl, 3-biphenylyl, 4-biphenylyl, 5'-m-terphenylyl, etc.

[0166] In the description of the compound represented by formula (H), “heteroaryl” is a monovalent group formed by a heteroaryl ring.

[0167] As a "heteroaryl ring," R 21 ~R 30 The aforementioned can be cited as an example of a "heteroaryl ring" when adjacent groups combine to form a heteroaryl ring.

[0168] As a “heteroaryl,” a monovalent group obtained by removing one hydrogen from a compound represented by the following formula (BO) can also be cited as a preferred example.

[0169]

[0170] As a monovalent group obtained by removing any one hydrogen from a compound represented by the formula (BO), there are, for example, the following groups. In the formula, * indicates a bonding position.

[0171]

[0172] In describing the compound represented by formula (H), the "alkyl" referred to as "alkyl" may be either a straight chain or a branched chain.

[0173] Specific alkyls include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, tert-pentyl (tert-amyl), n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, tert-octyl (1,1,3,3-tetramethylbutyl), 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 2,6-dimethyl-4-heptyl, 3,5,5-trimethylhexyl, n-decyl, n-undecyl, 1-methyldecyl, n-dodecyl, n-tridecyl, 1-hexylheptyl, Examples include n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, and n-eicosyl.

[0174] In addition, for example, 1-ethyl-1-methylpropyl, 1,1-diethylpropyl, 1,1-dimethylbutyl, 1-ethyl-1-methylbutyl, 1,1,4-trimethylpentyl, 1,1,2-trimethylpropyl, 1,1-dimethyloctyl, 1,1-dimethylpentyl, 1,1-dimethylheptyl, 1,1,5-trimethylhexyl, 1-ethyl-1-methylhexyl, 1-ethyl-1,3-dimethylbutyl, 1,1,2,2-tetramethylpropyl, 1-butyl-1-methylpentyl, 1,1-diethylbutyl, 1-ethyl-1-methylpentyl, 1,1,3-trimethylbutyl, 1-propyl-1-methylpentyl, 1,1,2-trimethylpropyl, 1-ethyl-1,2,2-trimethylpropyl, 1-propyl-1-methylbutyl, There are also 1,1-dimethylhexyl, etc.

[0175] Examples of specific “cycloalkyl” when referring to “cycloalkyl” in the description of the compound represented by formula (H) include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, norbornenyl, bicyclo[1.0.1]butyl, bicyclo[1.1.1]pentyl, bicyclo[2.0.1]pentyl, bicyclo[1.2.1]hexyl, bicyclo[3.0.1]hexyl, bicyclo[2.1.2]heptyl, bicyclo[2.2.2]octyl, adamantyl, diamantyl, decahydronaphthalenyl, decahydroazulenyl, and their carbon alkyl (especially methyl) substituents having 1 to 5 carbon atoms. In addition, in this specification, "cycloalkyl" includes not only monocyclic types such as cyclohexyl, but also polycyclic types such as adamantyl.

[0176] As for the “substituted silyl” in the compound represented by formula (H), for example, there is 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. Preferred examples of the “substituted silyl” in the compound represented by formula (H) include trimethylsilyl and triphenylsilyl.

[0177] The anthracene compound represented by formula (H) is preferably an anthracene compound represented by formula (HA), formula (HB), formula (HC), formula (HD), or formula (HE).

[0178]

[0179]

[0180] Among equations (HA), (HB), (HC), (HD), and (HE), R 1 , R 2 , R 3 , R 6 , R 7 , R 8 , R9 and R 10 Each is independently a monovalent group obtained by removing hydrogen from any one of hydrogen, an aryl having 6 to 30 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, an alkyl having 1 to 12 carbon atoms, a cycloalkyl having 3 to 16 carbon atoms, or a compound represented by the formula (BO), and R 21 ~R 30 R is, each independently, hydrogen, an aryl having 6 to 16 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, an alkyl having 1 to 12 carbon atoms, or a cycloalkyl having 3 to 16 carbon atoms. 21 ~R 30 Adjacent groups may be bonded to form an aryl ring having 6 to 10 carbon atoms or a heteroaryl ring having 2 to 10 carbon atoms, and at least one hydrogen in the formed ring may be substituted with an aryl having 6 to 16 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, an alkyl having 1 to 12 carbon atoms, or a cycloalkyl having 3 to 16 carbon atoms, provided that R 21 ~R 30 One of them constitutes L.

[0181] Among formulas (HA), (HB), (HC), (HD), and (HE), X is each independently >O, >S, >NR, >C(-R)2, or >Si(-R)2. R of >NR, >C(-R)2, and >Si(-R)2 is each independently an aryl having 6 to 16 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, an alkyl having 1 to 12 carbon atoms, or a cycloalkyl having 3 to 16 carbon atoms. R of >NR as X is -O-, -S-, -C(-R)2-, or R by means of a single bond 21 or R 30 It may be combined with. R of the above -C(-R)2- is an alkyl having 1 to 12 carbon atoms or a cycloalkyl having 3 to 16 carbon atoms. X is preferably independently O, >S, >NR, or >C(-R)2, and more preferably O or >NR.

[0182] Among formulas (HA), (HB), (HC), (HD) and (HE), L is, respectively, a single bond, an alkylene having 1 to 6 carbon atoms, an arylene having 6 to 16 carbon atoms that may be substituted with an alkyl having 1 to 5 carbon atoms or a cycloalkyl having 5 to 10 carbon atoms, or a heteroarylene having 2 to 15 carbon atoms that may be substituted with an alkyl having 1 to 5 carbon atoms or a cycloalkyl having 5 to 10 carbon atoms. It is preferable that L is a single bond.

[0183] In equation (HA), R 2 , R 3 , R 6 , R 7 Preferably, each is independently hydrogen or an unsubstituted aryl having 6 to 30 carbon atoms, and more preferably hydrogen. R 9 It is preferable that the group be a monovalent group obtained by removing one hydrogen from an unsubstituted aryl having 6 to 30 carbon atoms or a compound represented by the formula (BO), and it is more preferable that the group be a monovalent group obtained by removing one hydrogen from an unsubstituted aryl having 6 to 12 carbon atoms or a compound represented by the formula (BO). The same applies to the formula (HA') described below.

[0184] In equation (HB), R 2 , R 3 , R 6 , R 7 It is preferable that each be independently hydrogen or an unsubstituted aryl having 6 to 30 carbon atoms, and more preferable that it be hydrogen. The same applies to the formula (HB') described below.

[0185] In equation (HC), R 2 , R 3 , R 6 , R 7 Preferably, each is independently hydrogen or an unsubstituted aryl having 6 to 30 carbon atoms, and more preferably hydrogen. R 1 and R 8It is preferable that each be an independent unsubstituted aryl having 6 to 30 carbon atoms, and more preferable that they be unsubstituted aryls having 6 to 12 carbon atoms. The same applies to the formula (HC') described below.

[0186] In equation (HD), R 2 , R 3 , R 6 , R 7 Preferably, each is independently hydrogen or an unsubstituted aryl having 6 to 30 carbon atoms, and more preferably hydrogen. R 10 It is preferable that it be an unsubstituted aryl having 6 to 30 carbon atoms, and more preferable that it be an unsubstituted aryl having 6 to 12 carbon atoms. The same applies to the formula (HD') described below.

[0187] In equation (HE), R 2 , R 3 , R 6 , R 7 It is preferable that each be independently hydrogen or an unsubstituted aryl having 6 to 30 carbon atoms, and more preferable that it be hydrogen. The same applies to the formula (HE') described below.

[0188] In equations (HA), (HB), (HC), (HD), and (HE), R other than the one constituting L 21 ~R 30 It is more desirable that all of it be hydrogen.

[0189] At least one hydrogen in each of the compounds represented by formulas (HA), (HB), (HC), (HD), and (HE) may be substituted with a substituted silyl, cyano, halogen, or deuterium. A compound in which at least one hydrogen is substituted with deuterium is preferred from the standpoint of durability of the compound, and it is more preferable that all hydrogens of the anthracene ring are substituted with deuterium, or that all hydrogens are substituted with deuterium, and even more preferable that all hydrogens are substituted with deuterium.

[0190] Regarding the preferred ranges of each substituent, etc. in Formula (HA), Formula (HB), Formula (HC), Formula (HD), and Formula (HE), for those not specifically described, the description of the preferred range of the corresponding substituent, etc. in Formula (H) may be referenced.

[0191] Examples of particularly desirable anthracene compounds represented by formula (H) include anthracene compounds represented by formulas (HA'), (HB'), (HC'), (HD'), or (HE').

[0192]

[0193]

[0194] In equations (HA'), (HB'), (HC'), (HD'), and (HE'), R 1 , R 2 , R 3 , R 6 , R 7 , R 8 , R 9 and R 10 Each is a monovalent group obtained by removing hydrogen from any one of hydrogen, an aryl having 6 to 30 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, an alkyl having 1 to 12 carbon atoms, a cycloalkyl having 3 to 16 carbon atoms, or a compound represented by the formula (BO).

[0195] In equations (HA'), (HB'), (HC'), (HD'), and (HE'), R 21 ~R 30 Each is independently hydrogen, an aryl having 6 to 16 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, an alkyl having 1 to 12 carbon atoms, or a cycloalkyl having 3 to 16 carbon atoms, and R 21 ~R 30Adjacent groups may be bonded to form an aryl ring having 6 to 10 carbon atoms or a heteroaryl ring having 2 to 10 carbon atoms, and at least one hydrogen in the formed ring may be substituted with an aryl having 6 to 16 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, an alkyl having 1 to 12 carbon atoms, or a cycloalkyl having 3 to 16 carbon atoms. However, R 21 ~R 30 One of them constitutes L.

[0196] In formulas (HB'), (HC'), (HD'), and (HE'), X is each independently >O, >S, >NR, >C(-R)2, or >Si(-R)2; R of >NR, >C(-R)2, and >Si(-R)2 and R' of formula (HA') are each independently an aryl having 6 to 16 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, an alkyl having 1 to 12 carbon atoms, or a cycloalkyl having 3 to 16 carbon atoms; and R' of formula (HA') and R of >NR as X is -O-, -S-, -C(-R)2-, or R by means of a single bond 21 or R 30 It may be combined with. R of the above -C(-R)2- is an alkyl having 1 to 12 carbon atoms or a cycloalkyl having 3 to 16 carbon atoms.

[0197] In formulas (HA'), (HB'), (HC'), (HD') and (HE'), L is, respectively, a single bond, an alkylene having 1 to 6 carbon atoms, an arylene having 6 to 16 carbon atoms that may be substituted with an alkyl having 1 to 5 carbon atoms or a cycloalkyl having 5 to 10 carbon atoms, or a heteroarylene having 2 to 15 carbon atoms that may be substituted with an alkyl having 1 to 5 carbon atoms or a cycloalkyl having 5 to 10 carbon atoms.

[0198] At least one hydrogen in each of the compounds represented by formula (HA'), formula (HB'), formula (HC'), formula (HD') and formula (HE') may be substituted with a substituted silyl, cyano, halogen, or deuterium.

[0199] Regarding the preferred ranges of each substituent, etc. in Formula (HA'), Formula (HB'), Formula (HC'), Formula (HD'), and Formula (HE'), reference may be made to the descriptions of the preferred ranges of the corresponding substituents, etc. in Formula (HA), Formula (HB), Formula (HC), Formula (HD), and Formula (HE), respectively. In particular, in Formula (HA'), Formula (HB'), Formula (HC'), and Formula (HE'), R 21 ~R 30 It is preferable that all elements except for one constituting L are hydrogen. However, in formula (HD'), R 21 ~R 30 It is preferable that, except for one of the groups constituting L, one is an unsubstituted aryl having 6 to 16 carbon atoms, and the others are hydrogen.

[0200] In addition, in formulas (HB'), (HC'), (HD'), and (HE'), X is preferably independently >O, >NR, or >C(-R)2, and R of >NR is preferably an aryl having 6 to 16 carbon atoms, and R of >C(-R)2 is preferably methyl. In formula (HA'), R' is preferably an aryl having 6 to 16 carbon atoms, and more preferably phenyl. In addition, in formulas (HA'), (HB'), (HC'), (HD'), and (HE'), L is preferably a single bond or an arylene having 6 to 10 carbon atoms, and more preferably a single bond.

[0201] At least one hydrogen in each of the compounds represented by formulas (HA'), (HB'), (HC'), (HD'), and (HE') may be substituted with a substituted silyl, cyano, halogen, or deuterium. For each of the compounds represented by formulas (HA'), (HB'), (HC'), (HD'), and (HE'), a compound in which at least one hydrogen is substituted with deuterium is preferred from the perspective of the durability of the compound, and it is more preferable that all hydrogens of the anthracene ring are substituted with deuterium, or that all hydrogens are substituted with deuterium, and it is even more preferable that all hydrogens are substituted with deuterium.

[0202] And in the anthracene compound represented by formula (H) (preferably formula (HA), formula (HB), formula (HC), formula (HD), or formula (HE), more preferably formula (HA'), formula (HB'), formula (HC'), formula (HD'), or formula (HE')), atrope isomers, etc. may be present, but the anthracene compound represented by formula (H) may be any isomer that may exist, and may also be a mixture of these isomers in any mixing ratio.

[0203] More specific examples of anthracene compounds represented by formula (H) include compounds represented by the following structural formula. In the following structural formula, “D” represents deuterium and “Me” represents methyl.

[0204]

[0205]

[0206]

[0207]

[0208]

[0209]

[0210]

[0211]

[0212]

[0213]

[0214]

[0215]

[0216]

[0217]

[0218]

[0219]

[0220]

[0221]

[0222]

[0223]

[0224]

[0225]

[0226]

[0227]

[0228]

[0229]

[0230]

[0231]

[0232]

[0233]

[0234]

[0235]

[0236]

[0237]

[0238]

[0239]

[0240]

[0241]

[0242]

[0243]

[0244]

[0245]

[0246]

[0247]

[0248]

[0249]

[0250]

[0251]

[0252]

[0253]

[0254] Anthracene compounds represented by formula (H) can be prepared by applying Suzuki coupling, Negishi coupling, or other known coupling reactions, using as starting materials a compound having a reactive group at a desired position on the anthracene site and a compound having a reactive group at a polycyclic structure site containing X. Examples of reactive groups for these reactive compounds include halogens and boric acids. As for specific manufacturing methods, reference can be made to the synthesis methods described in paragraphs

[0089] to

[0175] of International Publication No. 2014 / 141725. Additionally, they can be prepared by referring to the method described in U.S. Patent Publication No. 2015-001479.

[0255] 2. A polycyclic aromatic compound that is a monomer represented by formula (D) or a polymer having multiple substructures represented by formula (D).

[0256] The organic EL device of the present invention comprises a polycyclic aromatic compound having a plurality of monomers represented by the following formula (D) or a plurality of partial structures represented by the following formula (D) in the light-emitting layer. It is preferable that the polycyclic aromatic compound be included in the light-emitting layer as a dopant material. The polycyclic aromatic compound is preferably a monomer represented by the formula (Da), formula (Db), formula (Dc), formula (Dd), formula (De), or formula (Df), or a polycyclic aromatic compound having a plurality of partial structures represented by the formulas (Da), formula (Db), formula (Dc), formula (Dd), formula (De), or formula (Df).

[0257]

[0258] In addition, in each structural formula, “A” to “C” and “a” to “c” are symbols representing ring structures represented as rings, benzene rings, or five-membered rings, respectively, and other symbols are the same as the definitions described above.

[0259] In formula (D), the A ring, the B ring, and the C ring are each independently an aryl ring or a heteroaryl ring. At least one hydrogen in these rings may be substituted with a substituent.

[0260] It is preferable that at least one of the A ring, B ring, and C ring is an aryl ring having at least one substituent or a heteroaryl ring having at least one substituent, it is more preferable that the A ring, B ring, and C ring are all aryl rings having at least one substituent or heteroaryl rings having at least one substituent, and it is even more preferable that each of the A ring, B ring, and C ring is an aryl ring having one substituent or a heteroaryl ring having one substituent.

[0261] In this case, the substituents preferred are a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted diarylamino, a substituted or unsubstituted diheterolamino, a substituted or unsubstituted arylheteroarylamino (an amino having an aryl and a heteroaryl), a substituted or unsubstituted diarylboryl (the two aryls may be connected via a single bond or a linker), 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 substituents when these groups have a substituent include aryl, heteroaryl, alkyl, cycloalkyl, diarylamino, and a substituted silyl.

[0262] In particular, as substituents, cycloalkyls such as substituted or unsubstituted alkyls (particularly neopentyl) and adamantyl are preferred. Additionally, tertiary alkyls (tR) are preferred. This is because the intermolecular distance increases due to such bulky substituents, thereby improving the luminescence quantum yield (PLQY). Additionally, substituted or unsubstituted diarylaminos are also preferred as substituents.

[0263] The above tertiary alkyl is represented by the following formula (tR).

[0264]

[0265] In equation (tR), R a , R b , and R c Each is independently an alkyl having 1 to 24 carbon atoms, and any -CH2- in the alkyl may be substituted with -O-, and the group represented by formula (tR) is substituted with at least one hydrogen in the compound or structure represented by formula (D) in *.

[0266] R a , R b , and R c As for the “alkyl having 1 to 24 carbon atoms,” it may be either a straight chain or a branched chain, for example, a straight chain alkyl having 1 to 24 carbon atoms or a branched chain alkyl having 3 to 24 carbon atoms, an alkyl having 1 to 18 carbon atoms (a branched chain alkyl having 3 to 18 carbon atoms), an alkyl having 1 to 12 carbon atoms (a branched chain alkyl having 3 to 12 carbon atoms), an alkyl having 1 to 6 carbon atoms (a branched chain alkyl having 3 to 6 carbon atoms), or an alkyl having 1 to 4 carbon atoms (a branched chain alkyl having 3 to 4 carbon atoms).

[0267] R in equation (tR) of equation (D) a , R b , and R c The total number of carbon atoms is preferably 3 to 20, and particularly preferably 3 to 10.

[0268] R a , R b , and R cSpecific alkyls include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 2,6-dimethyl-4-heptyl, 3,5,5-trimethylhexyl, n-decyl, n-undecyl, 1-methyldecyl, n-dodecyl, n-tridecyl, 1-hexylheptyl, n-tetradecyl, n-pentadecyl, Examples include n-hexadecyl, n-heptadecyl, n-octadecyl, and n-eicosyl.

[0269] The group represented by formula (tR) is, for example, tert-butyl, tert-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-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, Examples include 1,1,2-trimethylpropyl, 1-ethyl-1,2,2-trimethylpropyl, 1-propyl-1-methylbutyl, 1,1-dimethylhexyl groups, etc. Among these, tert-butyl and tert-amyl are preferred.

[0270] Other preferred examples of substituents in the A, B, and C rings include, for example, diarylamino substituted with a group of formula (tR), carbazolyl substituted with a group of formula (tR), or benzocarbazolyl substituted with a group of formula (tR). For “diarylamino,” the group described below as the “first substituent” may be given as an example. As for the substitution of the group of formula (tR) into diarylamino, carbazolyl, and benzocarbazolyl, examples may be given in which some or all hydrogens of the aryl ring or benzene ring in these groups are substituted with a group of formula (tR).

[0271] The aryl or heteroaryl rings in the A, B, and C rings are B (boron), X 1 and X 2 It is desirable to have a 5-membered or 6-membered ring that shares a bond with the central condensation 2-ring structure of the formula (D).

[0272] Here, "condensed two-ring structure" refers to B (boron), X shown in the center of formula (D). 1 and X 2 It refers to a structure formed by the condensation of two saturated hydrocarbon rings, including [the ring]. Furthermore, "a six-membered ring sharing a bond with a condensed two-ring structure" refers to a six-membered ring (e.g., a benzene ring) condensed into the above-mentioned condensed two-ring structure. Additionally, "an aryl ring (which is an A ring) or a heteroaryl ring having this six-membered ring" means that an A ring is formed solely by this six-membered ring, or that an A ring is formed by the condensation of another ring, etc., into this six-membered ring, including this six-membered ring. In other words, the "aryl ring (which is an A ring) having a six-membered ring" referred to here means that a six-membered ring constituting all or part of an A ring is condensed into the above-mentioned condensed two-ring structure. The same explanation applies to "B rings," "C rings," and "five-membered rings."

[0273] The A ring in formula (D) is the a ring in formulas (Da), (Db), (Dc), (Dd), (De), and (Df) and its substituent R1 ~R 3 It corresponds to. The B ring in formula (D) corresponds to the b ring in formulas (Da), (Db), and (Dc) and its substituent R 8 ~R 11 , the b-ring and its substituent R in formula (Dd). 10 and R 11 , and the b-ring and its substituent R in formulas (De), and (Df). 8 and R 9 It corresponds to. The C ring in formula (D) corresponds to the c ring in formula (Da) and its substituent R 4 ~R 7 , the c-ring and its substituent R in formulas (Db), (Dd), and (Df). 4 and R 5 , and the c-ring and its substituent R in formulas (Dc) and (De). 6 and R 7 It corresponds to. That is, Equation (Da) corresponds to a selected structure in which a ring having at least a 6-membered ring structure is selected as an A-C ring of Equation (D), and Equations (Db), (Dc), (Dd), (De), and (Df) correspond to selected structures in which a ring having at least a 6-membered ring structure and a ring having at least a 5-membered ring structure are selected as A-C rings of Equation (D), respectively. In this sense, each ring of Equation (Da) is represented by lowercase a-c.

[0274] X in equations (Db), (Dc), (Dd), (De), and (Df) XEach is independently >O, >S, >NR, or >C(-R)2. Here, R of >NR is an aryl that may be substituted, a heteroaryl that may be substituted, an alkyl that may be substituted, or a cycloalkyl that may be substituted; it is preferably an aryl that may be substituted, and more preferably an unsubstituted aryl. Additionally, R of >C(-R)2 is each independently an aryl that may be substituted with hydrogen, an alkyl or cycloalkyl, a heteroaryl that may be substituted with an alkyl or cycloalkyl, an alkyl, or a cycloalkyl; it is preferably an alkyl, and more preferably a methyl. It is preferable that the two Rs in >C(-R)2 are identical. It is also preferable that the two Rs in >C(-R)2 are bonded to each other to form a ring.

[0275] X X It is preferable that each independently >O, >S, or >NR, more preferable that >O or >S, and even more preferable that >S.

[0276] In equations (Da), (Db), (Dc), (Dd), (De), and (Df), R 1 ~R 11 Each is independently hydrogen, aryl, heteroaryl, diarylamino, diheteroylamino, arylheteroylamino, diarylboryl (two aryls may be connected via a single bond or a linker), alkyl, cycloalkyl, alkoxy, aryloxy, or substituted silyl, wherein at least one hydrogen in these may be substituted with an aryl, heteroaryl, alkyl, cycloalkyl, or substituted silyl.

[0277] R 1 ~R 11It is preferable that each be independently hydrogen, alkyl (particularly, the above tertiary alkyl (tR), neopentyl, etc.), cycloalkyl (e.g., adamantyl, etc.), substituted or unsubstituted diarylamino, or substituted silyl (triphenylsilyl, trimethylsilyl, etc.).

[0278] R in equations (Da), (Db), (Dc), (Dd), (De), and (Df) 1 ~R 3 Of these, 0 to 1 are non-hydrogen (especially the preferred substituents mentioned above), and the rest are hydrogen, and R 4 ~R 7 Of these, 0 to 1 are non-hydrogen (especially the preferred substituents mentioned above), and the rest are hydrogen, and R 8 ~R 11 Of these, 0 to 1 are non-hydrogen (especially the preferred substituents mentioned above), and it is preferable that the others are hydrogen.

[0279] R 1 ~R 3 Among them, one is a non-hydrogen (especially the preferred substituent mentioned above), and the others are hydrogen, and R 4 ~R 7 Among them, one is a non-hydrogen (especially the preferred substituent mentioned above), and the others are hydrogen, and R 8 ~R 11 Of these, one is a non-hydrogen (especially the preferred substituent mentioned above), and it is more preferable that the other is hydrogen.

[0280] In equations (Da), (Db), (Dc), (Dd), (De), and (Df), the substituent R of the a, b, and c rings 1 ~R 11Adjacent groups may be bonded to form an aryl ring or a heteroaryl ring together with an a-ring, a b-ring, or a c-ring, and at least one hydrogen in the formed ring may be substituted with aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryls may be bonded via a single bond or a linker), alkyl, cycloalkyl, alkoxy, aryloxy, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, or alkyldicycloalkylsilyl, and at least one hydrogen in these may be substituted with aryl, heteroaryl, alkyl, or cycloalkyl. Accordingly, the polycyclic aromatic compounds represented by formulas (Da), (Db), (Dc), (Dd), (De), and (Df) have their ring structures changed by the mutual bonding of substituents in the a-ring, b-ring, and c-ring. For example, for a polycyclic aromatic compound represented by formula (Da), the ring structure constituting the compound is changed as shown in, for example, formulas (Da-1) and (Da-2) below. The A' ring, B' ring, and C' ring in each formula correspond to the A ring, B ring, and C ring, respectively, in formula (D).

[0281]

[0282] The A' ring, B' ring, and C' ring in the above formulas (Da-1) and (Da-2) are, as explained in formula (Da), substituent R 1 ~R 11 It represents an aryl ring or heteroaryl ring formed by bonding adjacent groups together with the a-ring, b-ring, and c-ring, respectively (it can also be called a condensed ring formed by the condensation of another ring structure with the a-ring, b-ring, or c-ring). Additionally, although not shown in the formula, there are compounds in which the a-ring, b-ring, and c-ring are all transformed into the A'-ring, B'-ring, and C'-ring. Furthermore, as can be seen from the above formulas (Da-1) and (Da-2), for example, R of the b-ring in formula (Da).8 and R of the c ring 7 , b ring's R 11 and R of the α-ring 1 , R of the c ring 4 and R of the α-ring 3 The back does not fall under "adjacent spheres," and unless specifically mentioned otherwise, they do not combine. That is, "adjacent spheres" refers to spheres adjacent on the same ring.

[0283] The compound represented by the above formula (Da-1) or formula (Da-2) is, for example, a compound having an A' ring (or B' ring or C' ring) formed by the condensation of a benzene ring, an indole ring, a pyrrole ring, a furan ring, a thiophene ring, a benzofuran ring, a benzothiophene ring, a cyclopentadiene ring, or an indene ring with respect to a benzene ring, which is an a ring (or a b ring or a c ring), and the formed condensed ring A' (or condensed ring B' or condensed ring C') is each a naphthalene ring, a carbazole ring, an indole ring, a benzofuran ring, a benzothiophene ring, a dibenzofuran ring, a dibenzothiophene ring, an indene ring, or a fluorene ring.

[0284] In addition, in formulas (Db), (Dc), (Dd), (De), and (Df), a condensed ring formed by the condensation of another ring structure may be formed in each of the same way as in the a-ring, b-ring, or c-ring. For example, a benzene ring that is an a-ring or a b-ring may form a condensed ring by the condensation of another ring structure, just like the benzene ring in formula (Da).

[0285] In equations (Db), (Dc), (Dd), (De), and (Df), for a five-membered ring that is a b-ring or a c-ring, R 4 ~R 11 It is particularly desirable that adjacent groups combine to form a ring, thereby forming a condensed ring. For example, in the c-ring of formulas (Db) and (Dc), and the b-ring and c-ring of formulas (Dd), (De), and (Df), R 3 ~R 11By combining adjacent groups to form a ring, a condensation ring, such as a B' ring or a C' ring, can be formed. Examples of condensation rings where the formed ring is a benzene ring include the indole ring, benzofuran ring, and benzothiophene ring.

[0286] As an example, in the 5-membered ring c of formula (Db), R 4 and R 5 Examples of condensed rings formed by combining to form benzene rings are shown below.

[0287]

[0288] In equation (Db-1), R 1 , R 2 , R 3 , R 8 , R 9 , R 10 , R 11 , X X , X 1 and X 2 is identical in meaning to each of in Equation (Db), and the preferred range is also the same. R 4b , R 5b , R 6b , R 7b is a hydrogen, or a substituent selected from the group consisting of aryl, heteroaryl, diarylamino, diheterorylamino, arylheterorylamino, diarylboryl (the two aryls may be connected via a single bond or a linker), alkyl, cycloalkyl, alkoxy, aryloxy, and substituted silyl, wherein at least one hydrogen in these substituents may be substituted with an aryl, heteroaryl, alkyl, cycloalkyl, or substituted silyl. 4b , R 5b , R 6b , R 7bOf these, 0 to 2 are substituents other than hydrogen, and the rest are hydrogen, which is preferable, and 1 is a substituent other than hydrogen, and the rest are hydrogen, which is even more preferable. For the preferred range of substituents other than hydrogen, refer to the description of the substituents described below as the first substituent (which may also have a second substituent). As for the substituents other than hydrogen, it is particularly preferable to be alkyl (particularly, the above tertiary alkyl (tR), neopentyl, etc.), cycloalkyl (e.g., adamantyl, etc.), or substituted or unsubstituted diarylamino.

[0289] For example, in equations (Db), (Dc), (Dd), (De), and (Df), for example, X X When α > 0, the b-ring or c-ring becomes a furan ring, but the ring corresponding to the B'-ring or C'-ring of formula (Da-1) formed by the condensation of a benzene ring with respect to this furan ring is a benzofuran ring.

[0290] Also, for example, in equations (Db), (Dc), (Dd), (De), and (Df), for example, X X When α > S, the b-ring or c-ring becomes a thiophene ring, but the ring corresponding to the B'-ring or C'-ring of formula (Da-1) formed by the condensation of a benzene ring with respect to a thiophene ring is a benzothiophene ring.

[0291] X in Equation (D) 1 and X 2 is independently >O, >C(-R)2, or >NR. X in Equation (D) 1 and X 2 It is preferable that at least one is >NR, and that all are >NR or X 1 and X 2 It is more desirable for one of them to be >NR and the other to be >C(-R)2, and it is most desirable for both to be >NR. X 1 and X 2In >C(-R)2, R is each independently an aryl that may be substituted with an alkyl or cycloalkyl, a heteroaryl that may be substituted with an alkyl or cycloalkyl, or a cycloalkyl. In >C(-R)2, it is preferable that the two Rs are identical, and the two Rs may be combined to form a ring. Examples of such compounds include the following compound (D-303).

[0292]

[0293] X 1 and X 2 R of >NR in is an aryl that may be substituted (preferably excluding amino as a substituent), a heteroaryl that may be substituted, an alkyl that may be substituted, or a cycloalkyl that may be substituted.

[0294] X 1 and X 2 In the context, R of >NR is preferably an aryl having 6 to 12 carbon atoms or an alkyl having 1 to 6 carbon atoms that may be substituted with an alkyl having 1 to 5 carbon atoms or a cycloalkyl having 5 to 10 carbon atoms; it is more preferably an aryl having 6 to 12 carbon atoms that may be substituted with an alkyl having 1 to 5 carbon atoms; it is more preferably a phenyl that may be substituted; and even more preferably an orthobiphenyl (a phenyl having a phenyl group at the ortho position relative to N) that may be substituted. X 1 and X 2 It is particularly desirable that only one of the >NRs is orthobiphenyl. An example of such a compound is the following compound (D-202).

[0295]

[0296] X 1 and X 2In >NR, R may be bonded to at least one of the A, B, and C rings by a linker or a single bond. As a linker, -O-, -S-, or -C(-R)2- is preferred. Furthermore, R of "-C(-R)2-" is hydrogen, alkyl, or cycloalkyl. This rule applies, for example, to X represented by the following formula (Da-3-1). 1 Ina X 2 It can be expressed as a compound having a ring structure accepted into the condensation ring B' and the condensation ring C'. That is, for example, for the benzene ring which is the b-ring (or c-ring) in formula (Da), X 1 (or X 2 It is a compound having a B' ring (or C' ring) formed by the condensation of another ring by accepting ). The condensed ring B' (or condensed ring C') formed is, for example, a carbazole ring, a phenoxin ring, a phenothiazine ring, or an acridine ring.

[0297] In addition, the above regulation is X, represented by the following formula (Da-3-2) or formula (Da-3-3). 1 and / or X 2 It can also be expressed as a compound having a ring structure accepted into the condensation ring A'. That is, for example, with respect to the benzene ring, which is the a-ring in formula (Da), X 1 (and / or X 2 It is a compound having an A' ring formed by accepting another ring and condensing it. The condensed ring A' formed is, for example, a carbazole ring, a phenoxin ring, a phenothiazine ring, or an acridine ring.

[0298]

[0299] The B ring and the C ring of formula (D), or the b ring and the c ring of formula (Da), may be joined by a linker or a single bond represented by Xz. Examples of such forms include the forms of formula (Da-7-1) or formula (Da-7-2). As linkers, -O-, -S-, or -C(-R)2- are preferred. Furthermore, R in the above "-C(-R)2-" may be hydrogen, alkyl, or cycloalkyl, and two Rs may form a ring.

[0300]

[0301] As for the “aryl ring” which is the A ring, B ring, and C ring of formula (D), for example, there is an aryl ring having 6 to 30 carbon atoms, an aryl ring having 6 to 16 carbon atoms is preferred, an aryl ring having 6 to 12 carbon atoms is more preferred, and an aryl ring having 6 to 10 carbon atoms is particularly preferred.

[0302] Specific examples of “aryl rings” include the monocyclic benzene ring, the dicyclic biphenyl ring, the condensed dicyclic naphthalene ring and indene ring, the tricyclic terphenyl ring (m-terphenyl, o-terphenyl, p-terphenyl), the condensed tricyclic acenaphtylene ring, fluorene ring, phenalene ring, and phenanthrene ring, the condensed tetracyclic triphenylene ring, pyrene ring, and naphthacene ring, and the condensed pentacyclic perylene ring and pentacene ring.

[0303] As for the “heteroaryl ring” of the A, B, and C rings of formula (D), for example, there is a heteroaryl ring having 2 to 30 carbon atoms, a heteroaryl ring having 2 to 25 carbon atoms is preferred, a heteroaryl ring having 2 to 20 carbon atoms is more preferred, a heteroaryl ring having 2 to 15 carbon atoms is even more preferred, and a heteroaryl ring having 2 to 10 carbon atoms is particularly preferred. In addition, as for the “heteroaryl ring,” for example, there is a complex ring containing 1 to 5 hetero atoms selected from oxygen, sulfur, and nitrogen in addition to carbon as ring constituent atoms. And, this “heteroaryl ring” is a five-membered ring including Xx in formulas (Db), (Dc), (Dd), (De), and (Df), or “R” defined in formulas (Da), (Db), (Dc), (Dd), (De), and (Df). 1 ~R 11 It corresponds to a "heteroaryl ring formed by the combination of adjacent groups with an a-ring, a b-ring, or a c-ring."

[0304] Specific "heteroaryl rings" include, for example, the pyrrole ring, oxazole ring, isooxazole ring, thiazole ring, isothiaazole ring, imidazole ring, oxadiazole ring, thiadiazole ring, triazole ring, tetrazole ring, pyrazol ring, pyridine ring, pyrimidine ring, pyridazine ring, pyrazine ring, triazine ring, indole ring, isoindole ring, 1H-indazole ring, benzimidazole ring, benzoxazole ring, benzothiaazole ring, 1H-benzotriazole ring, quinoline ring, isoquinoline ring, cinnoline ring, quinazolin ring, quinoxaline ring, phthalazine ring, naphthiridine ring, purine ring, pteridine ring, carbazole ring, acridine ring, phenoxathine ring, phenoxazine ring, phenothiazine ring, phenazine ring, There are phenazacyrin, indolezyne, furan, benzofuran, isobenzofuran, dibenzofuran, thiophene, benzothiophen, dibenzothiophen, furazane, thianthren, indolocarbazole, benzindolocarbazole, benzobenzindolocarbazole, naphthobenzofuran, etc.

[0305] Preferably, at least one hydrogen in the above "aryl ring" or "heteroaryl ring" is 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 "diarylboryl" (the two aryls may be connected via a single bond or a linker), a substituted or unsubstituted "alkyl," a substituted or unsubstituted "cycloalkyl," a substituted or unsubstituted "alkoxy," a substituted or unsubstituted "aryloxy," or a substituted "silyl." However, the "aryl" or "heteroaryl" as the first substituent, the aryl of "diarylamino," the heteroaryl of "diheteroarylamino," and the hydrogen of "arylheteroarylamino" Examples of aryls and heteroaryls, the aryls of "diarylboryl," and the aryls of "aryloxy" include the monovalent groups of the aforementioned "aryl ring" or "heteroaryl ring."

[0306] In addition, as the "alkyl" as the first substituent, it may be either a straight chain or a branched chain, and for example, a straight-chain alkyl having 1 to 24 carbon atoms or a branched-chain alkyl having 3 to 24 carbon atoms may be applied. An alkyl having 1 to 18 carbon atoms (a branched-chain alkyl having 3 to 18 carbon atoms) is preferred, an alkyl having 1 to 12 carbon atoms (a branched-chain alkyl having 3 to 12 carbon atoms) is more preferred, an alkyl having 1 to 8 carbon atoms (a branched-chain alkyl having 3 to 8 carbon atoms) is even more preferred, an alkyl having 1 to 6 carbon atoms (a branched-chain alkyl having 3 to 6 carbon atoms) is particularly preferred, and an alkyl having 1 to 5 carbon atoms (a branched-chain alkyl having 3 to 5 carbon atoms) is most preferred.

[0307] Specific alkyls include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, tert-pentyl (tert-amyl), n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, tert-octyl (1,1,3,3-tetramethylbutyl), 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 2,6-dimethyl-4-heptyl, 3,5,5-trimethylhexyl, n-decyl, n-undecyl, 1-methyldecyl, n-dodecyl, n-tridecyl, 1-hexylheptyl, Examples include n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, and n-eicosyl.

[0308] In addition, for example, 1-ethyl-1-methylpropyl, 1,1-diethylpropyl, 1,1-dimethylbutyl, 1-ethyl-1-methylbutyl, 1,1,4-trimethylpentyl, 1,1,2-trimethylpropyl, 1,1-dimethyloctyl, 1,1-dimethylpentyl, 1,1-dimethylheptyl, 1,1,5-trimethylhexyl, 1-ethyl-1-methylhexyl, 1-ethyl-1,3-dimethylbutyl, 1,1,2,2-tetramethylpropyl, 1-butyl-1-methylpentyl, 1,1-diethylbutyl, 1-ethyl-1-methylpentyl, 1,1,3-trimethylbutyl, 1-propyl-1-methylpentyl, 1,1,2-trimethylpropyl, 1-ethyl-1,2,2-trimethylpropyl, 1-propyl-1-methylbutyl, There are also 1,1-dimethylhexyl, etc.

[0309] In addition, examples of “cycloalkyl” as the first substituent include cycloalkyl having 3 to 24 carbon atoms, cycloalkyl having 3 to 20 carbon atoms, cycloalkyl having 3 to 16 carbon atoms, cycloalkyl having 3 to 14 carbon atoms, cycloalkyl having 5 to 10 carbon atoms, cycloalkyl having 5 to 8 carbon atoms, cycloalkyl having 5 to 6 carbon atoms, cycloalkyl having 5 carbon atoms, etc.

[0310] Specific examples of cycloalkyls include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, and their C1- to C5 alkyl (especially methyl) substituents, norbornenyl, bicyclo[1.0.1]butyl, bicyclo[1.1.1]pentyl, bicyclo[2.0.1]pentyl, bicyclo[1.2.1]hexyl, bicyclo[3.0.1]hexyl, bicyclo[2.1.2]heptyl, bicyclo[2.2.2]octyl, adamantyl, diamantyl, decahydronaphthalenyl, decahydroazulenyl, etc.

[0311] In addition, as the "alkoxy" as the first substituent, for example, there is a straight-chain alkoxy having 1 to 24 carbon atoms or a branched-chain alkoxy having 3 to 24 carbon atoms. An alkoxy having 1 to 18 carbon atoms (a branched-chain alkoxy having 3 to 18 carbon atoms) is preferred, an alkoxy having 1 to 12 carbon atoms (a branched-chain alkoxy having 3 to 12 carbon atoms) is more preferred, an alkoxy having 1 to 6 carbon atoms (a branched-chain alkoxy having 3 to 6 carbon atoms) is even more preferred, and an alkoxy having 1 to 5 carbon atoms (a branched-chain alkoxy having 3 to 5 carbon atoms) is particularly preferred.

[0312] Specific alkoxys include methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, sec-butoxy, tert-butoxy, tert-amyloxy, pentyloxy, hexyloxy, heptyloxy, octyloxy, etc.

[0313] In addition, as the "substituted silyl" as the first substituent, there are, for example, silyls substituted with three substituents selected from the group consisting of alkyl, cycloalkyl, and aryl. Examples include trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, alkyldicycloalkylsilyl, triarylsilyl, dialkylarylsilyl, and alkyldiarylsilyl.

[0314] As for "trialkylsilyl," an example may be a group in which three hydrogens in the silyl are each independently substituted with an alkyl group, and this alkyl group may be the group described as the "alkyl" in the first substituent mentioned above. The alkyl preferred for substitution is an alkyl having 1 to 5 carbon atoms, and specifically, examples may include methyl, ethyl, propyl, i-propyl, butyl, sec-butyl, tert-butyl, tert-amyl, etc.

[0315] Specific trialkylsilyls include trimethylsilyl, triethylsilyl, tripropylsilyl, trii-propylsilyl, tributylsilyl, trisec-butylsilyl, tritert-butylsilyl, sat-amylsilyl, ethyldimethylsilyl, propyldimethylsilyl, i-propyldimethylsilyl, butyldimethylsilyl, sec-butyldimethylsilyl, tert-butyldimethylsilyl, tert-amyldimethylsilyl, methyldiethylsilyl, propyldiethylsilyl, i-propyldiethylsilyl, butyldiethylsilyl, sec-butyldiethylsilyl, tert-butyldiethylsilyl, tert-amyldiethylsilyl, methyldipropylsilyl, ethyldipropylsilyl, butyldipropylsilyl, sec-butyldipropylsilyl, tert-butyldipropylsilyl, tert-amyldipropylsilyl, methyldii-propylsilyl, Examples include ethyldi-propylsilyl, butyldi-propylsilyl, sec-butyldi-propylsilyl, tert-butyldi-propylsilyl, tert-amyldi-propylsilyl, etc.

[0316] As for "tricycloalkylsilyl," examples include groups in which three hydrogens in the silyl are each independently substituted with cycloalkyl, and these cycloalkyls may be the groups described as "cycloalkyl" in the first substituent mentioned above. The preferred cycloalkyl for substitution is a cycloalkyl having 5 to 10 carbon atoms, and specifically, examples include cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, bicyclo[1.1.1]pentyl, bicyclo[2.0.1]pentyl, bicyclo[1.2.1]hexyl, bicyclo[3.0.1]hexyl, bicyclo[2.1.2]heptyl, bicyclo[2.2.2]octyl, adamantyl, decahydronaphthalenyl, decahydroazulenyl, etc.

[0317] Specific examples of tricycloalkylsilyls include tricyclopentylsilyl and tricyclohexylsilyl.

[0318] Specific examples of dialkylcycloalkylsilyls substituted with two alkyl and one cycloalkyl groups, and alkyldicycloalkylsilyls substituted with one alkyl and two cycloalkyl groups, include silyls substituted with groups selected from the specific alkyl and cycloalkyl groups mentioned above.

[0319] Specific examples of dialkylarylsilyls substituted with two alkyl and one aryl group, alkyldiarylsilyls substituted with one alkyl and two aryl groups, and triarylsilyls substituted with three aryl groups may include silyls substituted with groups selected from the specific alkyl and aryl groups mentioned above. Specific examples of triarylsilyls include triphenylsilyl.

[0320] In addition, regarding the "aryl" in the "dialylboryl" of the first substituent, the description of the aryl described above may be cited. Furthermore, these two aryls may be connected through a single bond or a linker (e.g., >C(-R)2, >O, >S, or >NR). Here, R of >C(-R)2 and >NR is an aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, alkoxy, or aryloxy (the first substituent), and the first substituent may also be substituted with an aryl, heteroaryl, alkyl, or cycloalkyl (the second substituent), and as specific examples of these groups, the description of the aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, alkoxy, or aryloxy described above as the first substituent may be cited.

[0321] The first substituent, a substituted or unsubstituted "aryl," a substituted or unsubstituted "heteroaryl," a substituted or unsubstituted "diarylamino," a substituted or unsubstituted "diheteroarylamino," a substituted or unsubstituted "diarylboryl" (the two aryls may be connected via a single bond or a linker), a substituted or unsubstituted "alkyl," a substituted or unsubstituted "cycloalkyl," a substituted or unsubstituted "alkoxy," a substituted or unsubstituted "aryloxy," or a substituted "silyl," may have at least one hydrogen in them substituted with a second substituent, as described as substituted or unsubstituted. As the second substituent, for example, aryl, heteroaryl, alkyl, cycloalkyl, or substituted silyl may be used, and specific examples thereof may be described by referring to the description of the monovalent group of the aforementioned "aryl ring" or "heteroaryl ring" and the description of the "alkyl" or "cycloalkyl" as the first substituent. In addition, among the aryl or heteroaryl as the second substituent, a structure in which at least one hydrogen therein is substituted with an aryl such as phenyl (the group described in the specific example), an alkyl such as methyl or tert-butyl (the group described in the specific example), or a cycloalkyl such as cyclohexyl (the group described in the specific example) is also included in the aryl or heteroaryl as the second substituent. As an example, when the second substituent is a carbazolyl, the carbazolyl in which at least one hydrogen at the 9th position is substituted with an aryl such as phenyl, an alkyl such as methyl, or a cycloalkyl such as cyclohexyl is also included as the heteroaryl as the second substituent.

[0322] The emission wavelength can be adjusted by the steric hindrance, electron-donating, and electron-absorbing properties of the structure of the first substituent. Preferably, it is a group represented by the following structural formula, more preferably methyl, tert-butyl, tert-amyl, tert-octyl, neopentyl, cyclohexyl, adamanthyl, phenyl, o-tolyl, p-tolyl, 2,4-xylyl, 2,5-xylyl, 2,6-xylyl, 2,4,6-methityl, diphenylamino, di-p-tolylamino, bis(p-(tert-butyl)phenyl)amino, carbazolyl, 3,6-dimethylcarbazolyl, 3,6-di-tert-butylcarbazolyl, and phenoxy, and even more preferably methyl, tert-butyl, tert-amyl, tert-octyl, neopentyl, adamanthyl, phenyl, o-tolyl, 2,6-xylyl, 2,4,6-methityl, diphenylamino, di-p-tolylamino, These are bis(p-(tert-butyl)phenyl)amino, carbazolyl, 3,6-dimethylcarbazolyl, and 3,6-di-tert-butylcarbazolyl. From the perspective of ease of synthesis, those with large steric hindrance are preferred for selective synthesis, and specifically, tert-butyl, tert-amyl, tert-octyl, adamantyl, o-tolyl, p-tolyl, 2,4-xylyl, 2,5-xylyl, 2,6-xylyl, 2,4,6-methyl, di-p-tolylamino, bis(p-(tert-butyl)phenyl)amino, 3,6-dimethylcarbazolyl, and 3,6-di-tert-butylcarbazolyl are preferred.

[0323] In the following structural formula, “Me” is methyl, “tBu” is tert-butyl, “tAm” is tert-amyl, “tOct” is tert-octyl, and * indicates the bonding position.

[0324]

[0325]

[0326]

[0327]

[0328]

[0329]

[0330]

[0331]

[0332]

[0333]

[0334]

[0335]

[0336]

[0337]

[0338] X of Equation (D) 1 and X 2 R of >NR in is an aryl, heteroaryl, alkyl, or cycloalkyl that may be substituted with the second substituent described above (however, X 1 and X 2 It is preferable not to substitute an amino group for the aryl as R of >NR in >NR). Examples of this aryl, heteroaryl, alkyl, or cycloalkyl group include the aforementioned groups. Furthermore, as the second substituent therein, for example, alkyls such as methyl, tertiary-butyl, and amyl, or substituted silyls such as p-tertiary-butylphenyl and trimethylsilyl are preferred. The substitution position of the alkyl group is preferably the para position relative to the substitution position of the above N. X 1 and X 2 As R of >NR in, particularly, an aryl having 6 to 10 carbon atoms (e.g., phenyl, naphthyl, etc.), a heteroaryl having 2 to 15 carbon atoms (e.g., carbazolyl, etc.), an alkyl having 1 to 5 carbon atoms (e.g., methyl, ethyl, etc.), or a cycloalkyl having 5 to 10 carbon atoms (preferably cyclohexyl or adamantyl) that may be substituted with a second substituent is preferred. This description is for X in formulas (Da), (Db), (Dc), (Dd), (De), and (Df). 1 and X2 The same applies.

[0339] X of Equation (D) 1 and X 2 The R in >C(-R)2 is an aryl, heteroaryl, alkyl, or cycloalkyl that may each be independently substituted with hydrogen or the aforementioned second substituent. Examples of this aryl, heteroaryl, alkyl, or cycloalkyl group include the aforementioned groups. In particular, an aryl having 6 to 10 carbon atoms (e.g., phenyl, naphthyl, etc.), a heteroaryl having 2 to 15 carbon atoms (e.g., carbazolyl, etc.), an alkyl having 1 to 5 carbon atoms (e.g., methyl, ethyl, etc.), or a cycloalkyl having 5 to 10 carbon atoms (preferably cyclohexyl or adamantyl) is preferred. It is preferable that the two Rs in >C(-R)2 are identical, and the two Rs may also be bonded to form a ring. In particular, it is preferable that both Rs in >C(-R)2 are methyl.

[0340] This explanation is for X in equations (Da), (Db), (Dc), (Dd), (De), and (Df). 1 and X 2 The same applies.

[0341] X in Equation (D) 1 and X 2 As a linker when R of >NR is bonded to at least one of the A ring, B ring, and C ring, examples include -O-, -S-, -C(-R)2-, or a single bond, and among these, R of "-C(-R)2-" is hydrogen, alkyl, or cycloalkyl, and examples of such alkyl or cycloalkyl include the aforementioned groups. In particular, alkyl having 1 to 5 carbon atoms (e.g., methyl, ethyl, etc.) or cycloalkyl having 5 to 10 carbon atoms (preferably cyclohexyl or adamantyl) is preferred.

[0342] This explanation is for X in equations (Da), (Db), (Dc), (Dd), (De), and (Df). 1 and X2 The same applies.

[0343] The polycyclic aromatic compound included in the light-emitting layer is, in the present invention, a monomer represented by formula (D) or a polymer having multiple partial structures represented by formula (D). The monomer represented by formula (D) is, that is, a compound represented by formula (D). The polymer is preferably a dimer to a hexamer, more preferably a dimer to a trimer, and particularly preferably a dimer. The polymer may be a form having multiple substructures represented by formula (D) within a single compound, for example, a form in which multiple substructures are bonded by a single bond, a linker having 1 to 3 carbon atoms, an alkylene, a phenylene, a naphthylene, etc. (linked polymer), or a form in which any ring (A ring, B ring, or C ring, or a ring, b ring, or c ring, etc.) included in the substructures is shared among multiple substructures (ring-covalent polymer), and also a form in which any ring (A ring, B ring, or C ring, or a ring, b ring, or c ring) included in the substructures is bonded by condensing with each other (ring-condensed polymer). However, ring-covalent polymers and ring-condensed polymers are preferred, and ring-covalent polymers are more preferred.

[0344] As such a polymer, for example, a polymer having multiple partial structures represented by formula (Da) can be exemplified by polycyclic aromatic compounds represented by the following formulas (Da-4), (Da-4-1), (Da-4-2), (Da-5-1) to (Da-5-4), or (Da-6). The polycyclic aromatic compound represented by the following formula (Da-4) is a polycyclic aromatic compound having multiple partial structures represented by formula (Da) in one compound by sharing the benzene ring, which is the a-ring in formula (Da). Additionally, the polycyclic aromatic compound represented by the following formula (Da-4-1) is a polycyclic aromatic compound having two partial structures represented by formula (Da) in one compound by sharing the benzene ring, which is the a-ring in formula (Da). In addition, the polycyclic aromatic compound represented by the following formula (Da-4-2) is a polycyclic aromatic compound having three partial structures represented by the formula (Da) in one compound by sharing the benzene ring which is the a-ring in the formula (Da). In addition, the polycyclic aromatic compounds represented by the following formulas (Da-5-1) to (Da-5-4) are polycyclic aromatic compounds having multiple partial structures represented by the formula (Da) in one compound by sharing the benzene ring which is the b-ring (or c-ring) in the formula (Da). In addition, the polycyclic aromatic compound represented by the following formula (Da-6) is a polycyclic aromatic compound having multiple partial structures represented by the formula (Da) in one compound by condensing a benzene ring which is the b-ring (or a-ring, c-ring) of a certain partial structure and a benzene ring which is the b-ring (or a-ring, c-ring) of a certain partial structure, as explained in the formula (Da).

[0345]

[0346]

[0347] The polycyclic aromatic compound may be a multimer comprising a multimerized form represented by formula (Da-4), formula (Da-4-1), or formula (Da-4-2) and a multimerized form represented by any one of formulas (Da-5-1) to (Da-5-4) or formula (Da-6), a multimer comprising a multimerized form represented by any one of formulas (Da-5-1) to (Da-5-4) and a multimerized form represented by formula (Da-6), or a multimer comprising a multimerized form represented by formula (Da-4), formula (Da-4-1), or formula (Da-4-2) and a multimerized form represented by any one of formulas (Da-5-1) to (Da-5-4) and a multimerized form represented by formula (Da-6).

[0348] In addition, hydrogen in the chemical structure of a polycyclic aromatic compound that is a monomer represented by formula (D) or a polymer having multiple partial structures represented by formula (D) may be all or partly deuterium, cyano, or halogen. For example, in formula (D), the A ring, B ring, C ring (the A-C rings are aryl or heteroaryl rings), a substituent to the A-C rings, and X 1 and X 2 When α >NR or >C(-R)2, the hydrogen in R (=alkyl, cycloalkyl, aryl) may be substituted with deuterium, cyano, or halogen, but examples may be given in which all or part 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.

[0349] In addition, at least one selected from the group consisting of aryl rings and heteroaryl rings in the chemical structure of a polycyclic aromatic compound that is a monomer represented by formula (D) or a polymer having multiple partial structures represented by formula (D), may be condensed into at least one cycloalkane. The same applies to a monomer represented by formula (Da), formula (Db), formula (Dc), formula (Dd), formula (De), or formula (Df), or a polycyclic aromatic compound that is a polymer having multiple partial structures represented by formula (Da), formula (Db), formula (Dc), formula (Dd), formula (De), or formula (Df).

[0350] For example, an aryl ring and a heteroaryl ring among the aryl ring and heteroaryl ring which are the A ring, B ring, C ring, a ring, b ring, and c ring; an aryl (aryl portion in aryl, diarylamino, arylheteroarylamino, diarylboryl or aryloxy) and a heteroaryl (a heteroaryl portion in heteroaryl, diheteroarylamino or arylheteroarylamino) as first and second substituents in the A- to C rings; an aryl (same as above) and a heteroaryl (same as above) as first and second substituents for the a ring, b ring, and c ring; and X 1 , X 2 At least one of the aryl (same as above) and heteroaryl (same as above) as R of >NR, and >C(-R)2 may be condensed into at least one cycloalkane.

[0351] Preferably, an aryl ring and a heteroaryl ring which are A, B, C, a, b, and c rings; an aryl (an aryl portion in aryl, diarylamino, diarylboryl, or aryloxy) and a heteroaryl (a heteroaryl portion in heteroaryl or diheteroarylamino) as first substituents among the A to C rings; an aryl (same as above) and a heteroaryl (same as above) as first substituents for the a to c rings; and X 1 , X 2At least one of the aryl (same as above) and heteroaryl (same as above) as R of >NR and >C(-R)2 may be condensed into at least one cycloalkane.

[0352] More preferably, an aryl ring which is an A ring, a B ring, a C ring, an a ring, a b ring, a c ring; an aryl (aryl portion in aryl or diarylamino) and a heteroaryl (a heteroaryl portion in heteroaryl) as a first substituent among the A to C rings; an aryl (same as above) and a heteroaryl (same as above) as a first substituent to the a ring, b ring, and c ring; and X 1 , X 2 At least one of the aryl (same as above) as R of phosphorus >NR and >C(-R)2 may be condensed into at least one cycloalkane.

[0353] More preferably, an aryl ring which is an A ring, a B ring, a C ring, an a ring, a b ring, or a c ring; an aryl as a first substituent among the A to C rings (an aryl portion of an aryl or diarylamino); an aryl as a first substituent for the a ring, a b ring, or a c ring (identical to the above); and X 1 , X 2 At least one of the aryl (same as above) as R of phosphorus >NR and >C(-R)2 may be condensed into at least one cycloalkane.

[0354] Examples of “cycloalkanes” include cycloalkanes having 3 to 24 carbon atoms, cycloalkanes having 3 to 20 carbon atoms, cycloalkanes having 3 to 16 carbon atoms, cycloalkanes having 3 to 14 carbon atoms, cycloalkanes having 5 to 10 carbon atoms, cycloalkanes having 5 to 8 carbon atoms, cycloalkanes having 5 to 6 carbon atoms, and cycloalkanes having 5 carbon atoms.

[0355] Specific examples of cycloalkanes include cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctane, cyclononane, cyclodecane, norbornene, bicyclo[1.0.1]butane, bicyclo[1.1.1]pentane, bicyclo[2.0.1]pentane, bicyclo[1.2.1]hexane, bicyclo[3.0.1]hexane, bicyclo[2.1.2]heptane, bicyclo[2.2.2]octane, adamantane, diamantane, decahydronaphthalene and decahydroazulene, and their carbon-1 to 5 alkyl (especially methyl) substituents, halogen (especially fluorine) substituents and deuterium substituents.

[0356] Among these, a structure in which at least one hydrogen is substituted at the carbon at the α position of a cycloalkane (in a cycloalkyl that condenses into an aromatic ring or a heteroaromatic ring, a carbon at a position adjacent to the carbon at the condensation site) is preferred, a structure in which two hydrogens are substituted at the carbon at the α position is more preferred, and a structure in which a total of four hydrogens are substituted at two carbons at the α positions is even more preferred. Examples of these substituents include alkyl (particularly methyl) substituents having 1 to 5 carbon atoms, halogen (particularly fluorine) substituents, and deuterium substituents.

[0357] In particular, it is preferable that the structure be such that a partial structure represented by the following formula (B10) or formula (B11) is bonded to an adjacent carbon atom in an aryl ring or a heteroaryl ring.

[0358]

[0359] In the formula, Me represents methyl, and * represents the bonding position.

[0360] In formulas (B10) and (B11), Me represents methyl. * indicates a bonding position, and the group represented by formula (B10) or formula (B11) is bonded to two adjacent elements in the ring of an aryl ring or heteroaryl ring.

[0361] Examples of compounds having such a structure include the following compounds.

[0362]

[0363] The number of cycloalkanes condensed to one aryl ring or heteroaryl ring is preferably 1 to 3, more preferably 1 or 2, and even more preferably 1. For example, an example in which one or more cycloalkanes are condensed to one benzene ring (phenyl) is shown below. Cycloalkanes condensed as in formulas (Cy-1-4) and (Cy-2-4) may be condensed together. The same applies when the ring (group) being condensed is an aromatic ring or a complex aromatic ring other than the benzene ring (phenyl), and when the cycloalkane being condensed is a cycloalkane other than cyclopentane or cyclohexane.

[0364]

[0365] At least one -CH2- in the cycloalkane may be substituted with -O-. For example, an example in which one or more -CH2- in a cycloalkane condensed to one benzene ring (phenyl) are substituted with -O- is shown below. The same applies even if the ring (group) being condensed is an aromatic ring or a complex aromatic ring other than the benzene ring (phenyl), or if the cycloalkane being condensed is a cycloalkane other than cyclopentane or cyclohexane.

[0366]

[0367] At least one hydrogen in the cycloalkane may be substituted, and as such a substituent, examples include aryl, heteroaryl, diarylamino, diheterorylamino, arylheterorylamino, diarylboryl (two aryls may be connected via a single bond or a linker), alkyl, cycloalkyl, alkoxy, aryloxy, substituted silyl, deuterium, cyano, or halogen, and details thereof may be referenced from the description of the first substituent above. Among these substituents, alkyl (e.g., alkyl having 1 to 6 carbon atoms), cycloalkyl (e.g., cycloalkyl having 3 to 14 carbon atoms), halogen (e.g., fluorine), and deuterium are preferred. Furthermore, when a cycloalkyl is substituted, it may be a substituent form that forms a spiro structure. Examples thereof are shown below.

[0368]

[0369] As another form of cycloalkane condensation, there are examples of polycyclic aromatic compounds having, for instance, >NR where R is an aryl condensed with a cycloalkane, a diarylamino condensed with a cycloalkane (condensed in this aryl portion), a carbazolyl condensed with a cycloalkane (condensed in this benzene ring portion), or a benzocarbazolyl condensed with a cycloalkane (condensed in this benzene ring portion). Regarding "diarylamino," the group described as the "first substituent" above can be cited as an example.

[0370] Furthermore, as a more specific example, R in equation (Da), equation (Db), equation (Dc), equation (Dd), equation (De), or equation (Df). 2 Examples include a diarylamino condensed with a cycloalkane (condensed in the aryl portion) or a carbazolyl condensed with a cycloalkane (condensed in the benzene ring portion).

[0371] More specific examples of the polycyclic aromatic compounds of the present invention include compounds represented by the following structural formulas. In the following structural formulas, “D” represents deuterium, “Me” represents methyl, “Et” represents ethyl, “tBu” represents tert-butyl, “tAm” represents tert-amyl, and “TMS” represents trimethylsilyl.

[0372]

[0373]

[0374]

[0375]

[0376]

[0377]

[0378]

[0379]

[0380]

[0381]

[0382]

[0383]

[0384]

[0385]

[0386]

[0387]

[0388]

[0389]

[0390]

[0391]

[0392]

[0393]

[0394]

[0395]

[0396] A polycyclic aromatic compound having a monomer represented by formula (D) or a multimer having a substructure represented by formula (D) can be prepared by referring to the method described in Japanese Patent Publication No. 2018-043984.

[0397] 3. Structure of Organic Light Emitting Diodes

[0398] FIG. 1 shows a schematic cross-sectional view of an example of an organic EL light-emitting device. The organic EL device (100) shown in FIG. 1 has a substrate (101), an anode (102) installed on the substrate (101), a hole injection layer (103) installed on the anode (102), a hole transport layer (104) installed on the hole injection layer (103), a light-emitting layer (105) installed on the hole transport layer (104), an electron transport layer (106) installed on the light-emitting layer (105), an electron injection layer (107) installed on the electron transport layer (106), and a cathode (108) installed on the electron injection layer (107).

[0399] And, the organic EL element (100) may be configured such that, for example, the manufacturing order is reversed, it has a substrate (101), a cathode (108) installed on the substrate (101), an electron injection layer (107) installed on the cathode (108), an electron transport layer (106) installed on the electron injection layer (107), a light-emitting layer (105) installed on the electron transport layer (106), a hole transport layer (104) installed on the light-emitting layer (105), a hole injection layer (103) installed on the hole transport layer (104), and an anode (102) installed on the hole injection layer (103).

[0400] The above layers are not necessarily omitted, and the minimum constituent unit is configured to consist of an anode (102), a light-emitting layer (105), and a cathode (108), while the hole injection layer (103), hole transport layer (104), electron transport layer (106), and electron injection layer (107) are layers that are installed arbitrarily. In addition, each of the above layers may consist of a single layer or multiple layers.

[0401] As for the types of layers constituting an organic EL device, in addition to the above-described configuration of “substrate / anode / hole injection layer / hole transport layer / emissive layer / electron transport layer / electron injection layer / cathode”, “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”, “substrate / anode / hole injection layer / hole transport layer / emissive layer / electron transport layer / cathode”, “substrate / anode / emissive layer / electron transport layer / electron injection layer / cathode”, “substrate / anode / emissive layer / electron transport layer / electron injection layer / cathode”, It is also a configuration of “substrate / anode / hole transport layer / emissive layer / electron transport layer / cathode”, “substrate / anode / hole injection layer / emissive layer / electron injection layer / cathode”, “substrate / anode / hole injection layer / emissive layer / electron transport layer / cathode”, “substrate / anode / emissive layer / electron transport layer / cathode”, and “substrate / anode / emissive layer / electron injection layer / cathode”.

[0402] 4. Substrates in Organic Light Emitting Devices

[0403] The substrate (101) is a support for the organic EL element (100), and typically, quartz, glass, metal, plastic, etc. are used. Depending on the purpose, the substrate (101) is formed into a plate, film, or sheet type, and for example, a glass plate, a metal plate, a metal foil, a plastic film, a plastic sheet, etc. are used. Among these, a glass plate and a plate made of a transparent synthetic resin such as polyester, polymethacrylate, polycarbonate, or polysulfone are preferred. If it is a glass substrate, soda-lime glass or alkali-free glass, etc. are used, and the thickness should be sufficient to maintain mechanical strength, so for example, 0.2 mm or more. As for the upper limit of the thickness, for example, 2 mm or less, preferably 1 mm or less. Regarding the material of the glass, it is desirable to have few ions leached from the glass, so alkali-free glass is preferred, but since soda-lime glass with a barrier coating such as SiO2 is commercially available, this can be used. In addition, a gas barrier film, such as a dense silicon oxide film, may be formed on at least one side of the substrate (101) to increase gas barrier properties, and in particular, when a plate, film, or sheet made of a synthetic resin with low gas barrier properties is used as the substrate (101), it is preferable to form a gas barrier film.

[0404] 5. Anode in Organic Light Emitting Diodes

[0405] The anode (102) serves to inject holes into the light-emitting layer (105). In addition, if a hole injection layer (103) and / or a hole transport layer (104) are installed between the anode (102) and the light-emitting layer (105), holes are injected into the light-emitting layer (105) through them.

[0406] Examples of materials 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, or NESA glass. Examples of organic compounds include polythiophenes such as poly(3-methylthiophene), conductive polymers such as polypyrrole and polyaniline. In addition, materials used as anodes for organic EL devices can be appropriately selected and used.

[0407] The resistance of the transparent electrode is not limited as long as it can supply a sufficient current for the light emission of the light-emitting device, but from the perspective of the power consumption of the light-emitting device, it is desirable to have low resistance. For example, an ITO substrate with a resistance of 300 Ω / □ or less functions as a device electrode, but since it is currently possible to supply substrates of about 10 Ω / □, it is particularly desirable to use a low-resistance product with a resistance of, for example, 100 to 5 Ω / □, preferably 50 to 5 Ω / □. The thickness of the ITO can be arbitrarily selected to match the resistance value, but it is typically used between 50 and 300 nm.

[0408] 6. Hole injection layer and hole transport layer in organic light-emitting diodes

[0409] The hole injection layer (103) serves to efficiently inject holes moving from the anode (102) into the light-emitting layer (105) or into the hole transport layer (104). The hole transport layer (104) serves to efficiently transport holes injected from the anode (102) or holes injected from the anode (102) through the hole injection layer (103) to the light-emitting layer (105). The hole injection layer (103) and the hole transport layer (104) are each formed by stacking and mixing one or more types of hole injection / transport materials, or by a mixture of a hole injection / transport material and a polymer binder. Additionally, the layer may be formed by adding an inorganic salt, such as iron(III) chloride, to the hole injection / transport material.

[0410] As a hole injection and transport material, it is necessary to efficiently inject and transport holes from the anode between electrodes to which an electric field is applied, and it is desirable to have high hole injection efficiency and to efficiently transport the injected holes. To achieve this, it is desirable to use a material that has a low ionization potential, high hole mobility, excellent stability, and does not easily form trapping impurities during manufacturing and use.

[0411] As a material for forming the hole injection layer (103) and the hole transport layer (104), any compound can be selected and used from among compounds that have been conventionally used as charge transport materials for holes in optical conductive materials, p-type semiconductors, and known compounds used in the hole injection layer and hole transport layer of organic EL devices. Specific examples of these include carbazole derivatives (N-phenylcarbazole, polyvinylcarbazole, etc.), biscarbazole derivatives such as bis(N-arylcarbazole) or bis(N-alkylcarbazole), triarylamine derivatives (polymers having aromatic tertiary aminos 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 4Triphenylamine derivatives such as '-tetra[1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4,4'-diamine, 4,4',4"-tris(3-methylphenyl(phenyl)amino)triphenylamine, N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazole-3-yl)phenyl)-9H-fluorene-2-amine, N,N-bis(4-(dibenzo[b,d]furan-4-yl)phenyl)-[1,1':4',1"-terphenyl]-4-amine, stavastamine derivatives, etc.), stilbene derivatives, phthalocyanine derivatives (metal-free, copper phthalocyanine, etc.), pyrazolin derivatives, hydrazone compounds, benzofuran derivatives or thiophene derivatives, oxadiazole derivatives, quinoxaline derivatives (e.g., These include heterocyclic compounds such as 1,4,5,8,9,12-hexa-azatriphenylene-2,3,6,7,10,11-hexacarbonitrile, etc.), porphyrin derivatives, and polysilanes. In the polymer system, polycarbonates or styrene derivatives having the above monomer in a side chain, polyvinylcarbazole, and polysilanes are preferred, but they are not particularly limited as long as they are compounds that can form a thin film necessary for fabricating a light-emitting device, inject holes from the anode, and transport holes.

[0412] In addition, it is known that the conductivity of organic semiconductors is strongly influenced by their doping. Such organic semiconductor matrix materials are composed of compounds with good electron-donating properties or compounds with good electron-accepting properties. Strong electron-accepting agents such as tetracyanoquinone dimethane (TCNQ) or 2,3,5,6-tetrafluorotetracyano-1,4-benzoquinone dimethane (F4TCNQ) are known for doping electron-donating materials (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 an electron-donating base material (hole transport material). The conductivity of the base material changes significantly depending on the number and mobility of the holes. As matrix materials having hole transport characteristics, examples include benzidine derivatives (TPD, etc.) or stavastamine derivatives (TDATA, etc.), or specific metal phthalocyanines (particularly zinc phthalocyanine (ZnPc), etc.) are known (Japanese Patent Publication No. 2005-167175).

[0413] 7. Emissive layer in organic light-emitting diodes

[0414] The light-emitting layer (105) is a layer that emits light by recombining holes injected from the anode (102) and electrons injected from the cathode (108) between electrodes to which an electric field is applied. As a material for forming the light-emitting layer (105), it is preferable to use a compound (luminescent compound) that is excited and emits light by the recombination of holes and electrons, can form a stable thin film shape, and at the same time exhibits strong luminescence (fluorescence) efficiency in a solid state. In the present invention, as a material for the light-emitting layer, at least one of an anthracene-based compound represented by formula (H) and a polycyclic aromatic compound that is a monomer represented by formula (D) or a polymer having multiple partial structures represented by formula (D) is used. The anthracene-based compound represented by formula (H) may be used as a host material, and the polycyclic aromatic compound represented by formula (D) or a polymer having multiple partial structures represented by formula (D) may be used as a dopant material.

[0415] The light-emitting layer may be a single layer or composed of multiple layers, and is formed by a material for the light-emitting layer (host material, dopant material). The host material and the dopant material may each be of a single type or a combination of multiple types. The dopant material may be included in the entire host material or partially included. As for the doping method, it can be formed by a co-deposition method with the host material, but it may also be mixed with the host material in advance and then deposited simultaneously.

[0416] The amount of host material used varies depending on the type of host material and can be determined according to the characteristics of the host material. The standard amount of host material used is preferably 50 to 99.999 mass% of the total material for the light-emitting layer, more preferably 80 to 99.95 mass%, and even more preferably 90 to 99.9 mass%.

[0417] The amount of dopant material used varies depending on the type of dopant material and should be determined in accordance with the characteristics of the dopant material. The standard amount of dopant used is preferably 0.001 to 50 mass% of the total material for the light-emitting layer, more preferably 0.05 to 20 mass%, and even more preferably 0.1 to 10 mass%. The above range is desirable, for example, in that it can prevent the concentration quenching phenomenon.

[0418] As a host material, an anthracene-based compound represented by formula (H) may be used. In addition, other condensed ring derivatives such as anthracene, pyrene, dibenzocrisene, or fluorene, which are conventionally known as luminescent materials, bisstyryl derivatives such as bisstyrylanthracene derivatives or distyrylbenzene derivatives, tetraphenylbutadiene derivatives, cyclopentadiene derivatives, and carbazole derivatives may be used in combination.

[0419] 8. Electron injection layer and electron transport layer in organic light-emitting diodes

[0420] The electron injection layer (107) serves to efficiently inject electrons moving from the cathode (108) into the light-emitting layer (105) or the electron transport layer (106). The electron transport layer (106) serves to efficiently transport electrons injected from the cathode (108) or electrons injected from the cathode (108) through the electron injection layer (107) to the light-emitting layer (105). The electron transport layer (106) and the electron injection layer (107) are each formed by stacking and mixing one or more types of electron transport / injection materials, or by a mixture of electron transport / injection materials and a polymer binder.

[0421] The electron injection and transport layer is a layer responsible for injecting electrons from the cathode and transporting electrons, and it is desirable to have high electron injection efficiency and efficiently transport the injected electrons. To this end, it is desirable to use a material that has high electron affinity, high electron mobility, excellent stability, and does not easily generate trapped impurities during manufacturing and use. However, when considering the balance of hole and electron transport, if the layer primarily performs the role of efficiently preventing holes from the anode from flowing toward the cathode without recombination, it does not need to have such high electron transport capability to have an effect equivalent to that of a material with high electron transport capability in improving luminous efficiency. Therefore, the electron injection and transport layer in this embodiment may also include the function of a layer capable of efficiently preventing the movement of holes.

[0422] As a material (electron transport material) forming the electron transport layer (106) or electron injection layer (107), any of the compounds conventionally used as electron transfer compounds in photoconductive materials, and known compounds used in the electron injection layer and electron transport layer of an organic EL device may be selected and used.

[0423] As a material used in an electron transport layer or an electron injection layer, it is preferable to contain at least one selected from compounds consisting of aromatic rings or complex aromatic rings composed of one or more atoms selected from carbon, hydrogen, oxygen, sulfur, silicon, and phosphorus, pyrrole derivatives and their condensed ring derivatives, and metal complexes having electron-accepting nitrogen. Specifically, examples include condensed ring aromatic derivatives such as naphthalene and anthracene, styryl aromatic derivatives represented by 4,4'-bis(diphenylethenyl)biphenyl, perinone derivatives, coumarin derivatives, naphthalimide derivatives, quinone derivatives such as anthraquinone or diphenoquinone, phosphoroxide 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 may be used alone, but they may also be used in combination with other materials.

[0424] In addition, as specific examples of other electron transfer compounds, pyridine derivatives, naphthalene derivatives, anthracene derivatives, benzofluorene derivatives, phenanthroline derivatives, perinone derivatives, coumarin derivatives, naphthalimide derivatives, anthraquinone derivatives, diphenoquinone derivatives, diphenylquinone derivatives, perylene derivatives, oxadiazole derivatives (1,3-bis[(4-tert-butylphenyl)1,3,4-oxadiazolyl]phenylene, etc.), thiophene derivatives, triazole derivatives (N-naphthyl-2,5-diphenyl-1,3,4-triazole, etc.), thiadiazole derivatives, metal complexes of auxin derivatives, quinolinol metal complexes, quinoxaline derivatives, polymers of quinoxaline derivatives, benzazole compounds, gallium complexes, pyrazol derivatives, perfluorophenylene derivatives, triazine derivatives, pyrazine derivatives, and benzoquinoline Examples include derivatives (2,2'-bis(benzo[h]quinoline-2-yl)-9,9'-spirobifluorene, etc.), imidazopyridine derivatives, borane derivatives, benzimidazole derivatives (tris(N-phenylbenzimidazole-2-yl)benzene, etc.), benzoxazole derivatives, benzothiazole derivatives, quinoline derivatives, oligopyridine derivatives such as terpyridine, bipyridine derivatives, terpyridine derivatives (1,3-bis(4'-(2,2':6',2"-terpyridinyl))benzene, etc.), naphthiridine derivatives (bis(1-naphthyl)-4-(1,8-naphthiridine-2-yl)phenylphosphine oxide, etc.), aldazine derivatives, arylnitrile derivatives, indole derivatives, phosphine oxide derivatives, bisstyryl derivatives, etc.

[0425] In addition, metal complexes having electron-accepting nitrogen may be used, for example, quinolinol-based metal complexes, hydroxyazole complexes such as hydroxyphenyloxazole complexes, azomethine complexes, tropolone metal complexes, flavonol metal complexes, and benzoquinoline metal complexes.

[0426] The aforementioned materials may be used alone, but may also be used in combination with other materials.

[0427] Among the aforementioned materials, boran derivatives, pyridine derivatives, fluoranthene derivatives, BO-based derivatives, anthracene derivatives, benzofluorene derivatives, phosphine oxide derivatives, pyrimidine derivatives, arylnitrile derivatives, triazine derivatives, benzimidazole derivatives, phenanthroline derivatives, and quinoline metal complexes are preferred.

[0428] Boran derivatives

[0429] Boran derivatives are compounds represented by, for example, the following formula (ETM-1), and are disclosed in detail in Japanese Patent Publication No. 2007-27587.

[0430]

[0431] In Equation (ETM-1), R 11 and R 12 Each is independently at least one of hydrogen, alkyl, cycloalkyl, a substituted aryl, a substituted silyl, a substituted nitrogen-containing heterocyclic ring, or a cyano, and R 13 ~R 16 Each is independently an alkyl that may be substituted, a cycloalkyl that may be substituted, or an aryl that may be substituted; X is an arylene that may be substituted; Y is an aryl having 16 or fewer carbon atoms that may be substituted, a boryl that may be substituted, or a carbazolyl that may be substituted; and n is independently an integer from 0 to 3. In addition, examples of substituents in the case of "may be substituted" or "substituted" include aryl, heteroaryl, alkyl, or cycloalkyl.

[0432] Among the compounds represented by formula (ETM-1), compounds represented by the following formula (ETM-1-1) or compounds represented by the following formula (ETM-1-2) are preferred.

[0433]

[0434] In Equation (ETM-1-1), R 11and R 12 Each is independently at least one of hydrogen, alkyl, cycloalkyl, a substituted aryl, a substituted silyl, a substituted nitrogen-containing heterocyclic ring, or a cyano, and R 13 ~R 16 Each is independently an alkyl that may be substituted, a cycloalkyl that may be substituted, or an aryl that may be substituted, and R 21 and R 22 Each is independently at least one of hydrogen, alkyl, cycloalkyl, a substituted aryl, a substituted silyl, a substituted nitrogen-containing heterocyclic ring, or a cyano, and X 1 ...is an arylene having 20 or fewer carbon atoms that may be substituted, where n is independently an integer from 0 to 3, and m is independently an integer from 0 to 4. In addition, examples of substituents that may be "substituted" or "substituted" include aryl, heteroaryl, alkyl, or cycloalkyl.

[0435]

[0436] In Equation (ETM-1-2), R 11 and R 12 Each is independently at least one of hydrogen, alkyl, cycloalkyl, a substituted aryl, a substituted silyl, a substituted nitrogen-containing heterocyclic ring, or a cyano, and R 13 ~R 16 Each is independently an alkyl that may be substituted, a cycloalkyl that may be substituted, or an aryl that may be substituted, and X 1 ...is an arylene having 20 or fewer carbon atoms that may be substituted, and n is independently an integer from 0 to 3. In addition, examples of substituents that may be "substituted" or "substituted" include aryl, heteroaryl, alkyl, or cycloalkyl.

[0437] X1 As a specific example, a divalent group represented by any one of the following equations (X-1) to (X-9) can be cited.

[0438]

[0439] (among each formula, R a Each is independently an alkyl, cycloalkyl, or substituted phenyl group, and * indicates the bonding position.)

[0440] Specific examples of this boran derivative include, for instance, the following compounds.

[0441]

[0442] This borane derivative can be manufactured using known raw materials and known synthesis methods.

[0443] Pyridine derivatives

[0444] The pyridine derivative is, for example, a compound represented by the following formula (ETM-2), and preferably a compound represented by formula (ETM-2-1) or formula (ETM-2-2).

[0445]

[0446] f is an n-valent aryl ring (preferably an n-valent benzene ring, naphthalene ring, anthracene ring, fluorene ring, benzofluorene ring, phenalene ring, phenanthrene ring, or triphenylene ring), where n is an integer from 1 to 4.

[0447] In Equation (ETM-2-1), R 11 ~R 18 Each is independently hydrogen, alkyl (preferably an alkyl having 1 to 24 carbon atoms), cycloalkyl (preferably a cycloalkyl having 3 to 12 carbon atoms), or aryl (preferably an aryl having 6 to 30 carbon atoms).

[0448] In Equation (ETM-2-2), R 11 and R 12is, each independently, hydrogen, alkyl (preferably an alkyl having 1 to 24 carbon atoms), cycloalkyl (preferably a cycloalkyl having 3 to 12 carbon atoms), or aryl (preferably an aryl having 6 to 30 carbon atoms), and R 11 and R 12 It may combine to form a ring.

[0449] In each formula, the “pyridine substituent” is any one of the following formulas (Py-1) to (Py-15) (* in the formula indicates the bonding position), and each pyridine substituent may be independently substituted with an alkyl group having 1 to 4 carbon atoms or a cycloalkyl group having 5 to 10 carbon atoms. Specific examples include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, or tert-butyl, and methyl is preferred. Additionally, the pyridine substituent may be bonded to the φ, anthracene ring, or fluorene ring in each formula through phenylene or naphthylene.

[0450]

[0451] The pyridine substituent is any one of formulas (Py-1) to (Py-15) (* in the formulas indicates the bonding position), but among these, it is preferably any one of the following formulas (Py-21) to (Py-44).

[0452]

[0453] At least one hydrogen in each pyridine derivative may be substituted with deuterium, and one of the two “pyridine substituents” in formula (ETM-2-1) and formula (ETM-2-2) may be substituted with an aryl group.

[0454] R 11 ~R 18As for the “alkyl” in the formula, it may be either a straight chain or a branched chain, for example, a straight-chain alkyl having 1 to 24 carbon atoms or a branched-chain alkyl having 3 to 24 carbon atoms. A preferred “alkyl” is an alkyl having 1 to 18 carbon atoms (a branched-chain alkyl having 3 to 18 carbon atoms). A more preferred “alkyl” is an alkyl having 1 to 12 carbon atoms (a branched-chain alkyl having 3 to 12 carbon atoms). An even more preferred “alkyl” is an alkyl having 1 to 6 carbon atoms (a branched-chain alkyl having 3 to 6 carbon atoms). A particularly preferred “alkyl” is an alkyl having 1 to 4 carbon atoms (a branched-chain alkyl having 3 to 4 carbon atoms).

[0455] Specific "alkyl" groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 2,6-dimethyl-4-heptyl, 3,5,5-trimethylhexyl, n-decyl, n-undecyl, 1-methyldecyl, n-dodecyl, n-tridecyl, 1-hexylheptyl, n-tetradecyl, n-pentadecyl, Examples include n-hexadecyl, n-heptadecyl, n-octadecyl, and n-eicosyl.

[0456] As for the alkyl having 1 to 4 carbon atoms substituted on the pyridine-based substituent, the description of the above alkyl may be cited.

[0457] R 11 ~R 18Examples of "cycloalkyl" include cycloalkyls having 3 to 12 carbon atoms. A preferred "cycloalkyl" is a cycloalkyl having 3 to 10 carbon atoms. A more preferred "cycloalkyl" is a cycloalkyl having 3 to 8 carbon atoms. An even more preferred "cycloalkyl" is a cycloalkyl having 3 to 6 carbon atoms. Specific examples of "cycloalkyl" include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclopentyl, cycloheptyl, methylcyclohexyl, cyclooctyl, or dimethylcyclohexyl.

[0458] R 11 ~R 18 As for the “aryl” in the example, the preferred aryl is an aryl having 6 to 30 carbon atoms, the more preferred aryl having 6 to 18 carbon atoms, even more preferably an aryl having 6 to 14 carbon atoms, and particularly preferably an aryl having 6 to 12 carbon atoms.

[0459] Specific "aryls having 6 to 30 carbon atoms" include the monocyclic aryl phenyl, the condensed dicyclic aryl (1-, 2-)naphthyl, the condensed tricyclic aryl acenaphthylene-(1-, 3-, 4-, 5-)yl, fluorene-(1-, 2-, 3-, 4-, 9-)yl, phenalene-(1-, 2-)yl, (1-, 2-, 3-, 4-, 9-)phenanthrile, the condensed tetracyclic aryls triphenylene-(1-, 2-)yl, pyrene-(1-, 2-, 4-)yl, naphthacene-(1-, 2-, 5-)yl, and the condensed pentacyclic aryls perylene-(1-, 2-, 3-)yl, pentacene-(1-, 2-, Examples include 5-, 6-), etc.

[0460] Preferred “aryl having 6 to 30 carbon atoms” may be phenyl, naphthyl, phenanthyl, crisenyl, or triphenylenyl, more preferably phenyl, 1-naphthyl, 2-naphthyl, or phenanthyl, and particularly preferably phenyl, 1-naphthyl, or 2-naphthyl.

[0461] R in Equation (ETM-2-2) 11 and R 12They may be combined to form a ring, and as a result, cyclobutane, cyclopentane, cyclopentene, cyclopentadiene, cyclohexane, fluorene, or indene, etc. may be spiro-bonded to the 5-membered ring of the fluorene skeleton.

[0462] Specific examples of this pyridine derivative include, for instance, the following compounds.

[0463]

[0464] This pyridine derivative can be manufactured using known raw materials and known synthesis methods.

[0465] Fluoranthene derivatives

[0466] Fluoranthene derivatives are compounds represented by, for example, formula (ETM-3), and are disclosed in detail in International Publication No. 2010 / 134352.

[0467]

[0468] In Equation (ETM-3), X 12 ~X 21 ... represents hydrogen, halogen, straight-chain, branched-chain, or cyclic alkyl, straight-chain, branched-chain, or cyclic alkoxy, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl. Here, examples of substituents in the case of substitution include aryl, heteroaryl, alkyl, or cycloalkyl.

[0469] Specific examples of this fluoranthene derivative include, for instance, the following compounds.

[0470]

[0471] <BO계 유도체>

[0472] BO derivatives are, for example, polycyclic aromatic compounds represented by the following formula (ETM-4), or polymers of polycyclic aromatic compounds having multiple structures represented by the following formula (ETM-4).

[0473]

[0474] R 1 ~R 11 Each is independently hydrogen, aryl, heteroaryl, diarylamino, diheteroylamino, arylheteroylamino, alkyl, cycloalkyl, alkoxy, or aryloxy, and at least one hydrogen therein may be substituted with an aryl, heteroaryl, alkyl, or cycloalkyl.

[0475] Also, R 1 ~R 11 Adjacent groups may be bonded to form an aryl ring or a heteroaryl ring together with an a-ring, a b-ring, or a c-ring, and at least one hydrogen in the formed ring may be substituted with an aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkoxy, or aryloxy, and at least one hydrogen in these may be substituted with an aryl, heteroaryl, alkyl, or cycloalkyl.

[0476] In addition, at least one hydrogen in the compound or structure represented by formula (ETM-4) may be substituted with a halogen or deuterium.

[0477] For the description of the substituents or the cyclic form in Formula (ETM-4), the description of the polycyclic aromatic compound represented by Formula (D) or Formula (Da) may be cited.

[0478] Specific examples of this BO derivative include, for instance, the following compounds.

[0479]

[0480] This BO derivative can be manufactured using known raw materials and known synthesis methods.

[0481] Anthracene derivatives

[0482] Anthracene derivatives are compounds represented by, for example, the following formula (ETM-5).

[0483]

[0484] Ar1 Each is independently a single bond, divalent benzene, naphthalene, anthracene, fluorene, or phenylene.

[0485] Ar 2 Each is independently an aryl having 6 to 20 carbon atoms, preferably an aryl having 6 to 16 carbon atoms, more preferably an aryl having 6 to 12 carbon atoms, and particularly preferably an aryl having 6 to 10 carbon atoms. Specific examples of "aryls having 6 to 20 carbon atoms" include monocyclic aryls such as phenyl, (o-, m-, p-)tolyl, (2,3-, 2,4-, 2,5-, 2,6-, 3,4-, 3,5-)xylyl, mesithyl(2,4,6-trimethylphenyl), (o-, m-, p-)cumenyl, dicyclic aryls such as (2-, 3-, 4-)biphenylyl, condensed dicyclic aryls such as (1-, 2-)naphthyl, and tricyclic aryls such as terphenylyl(m-terphenyl-2'-yl, m-terphenyl-4'-yl, m-terphenyl-5'-yl, o-terphenyl-3'-yl, o-terphenyl-4'-yl, p-terphenyl-2'-yl, m-terphenyl-2-yl, m-terphenyl-3-yl, m-terphenyl-4-yl, o-terphenyl-2-yl, o-terphenyl-3-yl, o-terphenyl-4-yl, p-terphenyl-2-yl, p-terphenyl-3-yl, p-terphenyl-4-yl), condensed tricyclic aryls, anthracene-(1-, 2-, 9-)yl, acenaphthylene-(1-, 3-, 4-, 5-)yl, fluorene-(1-, 2-, 3-, 4-, 9-)yl, phenalene-(1-, 2-)yl, (1-, 2-, 3-, 4-, 9-)phenanthrile, condensed tetracyclic aryls triphenylene-(1-, 2-)yl, pyrene-(1-, 2-, 4-)yl, tetracene-(1-, 2-, 5-)yl, condensed pentacyclic Examples of aryls include perylene-(1-, 2-, 3-). Specific examples of "aryls having 6 to 10 carbon atoms" include phenyl, biphenylyl, naphthyl, terphenylyl, anthracenyl, acenaphthylenyl, fluorenyl, phenalenyl, phenanthryl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, etc.

[0486] R 1 ~R 4Each is independently hydrogen, a carbon-1 to carbon-6 alkyl, a carbon-3 to carbon-6 cycloalkyl, or a carbon-6 to carbon-20 aryl.

[0487] R 1 ~R 4 For the alkyl group having 1 to 6 carbon atoms, it may be either a straight chain or a branched chain. That is, it is a straight-chain alkyl having 1 to 6 carbon atoms or a branched-chain alkyl having 3 to 6 carbon atoms. More preferably, it is an alkyl having 1 to 4 carbon atoms (a branched-chain alkyl having 3 to 4 carbon atoms). Specific examples include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, or 2-ethylbutyl, and methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, or tert-butyl are preferred, and methyl, ethyl, or tert-butyl are more preferred.

[0488] R 1 ~R 4 Specific examples of cycloalkyls having 3 to 6 carbon atoms include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclopentyl, cycloheptyl, methylcyclohexyl, cyclooctyl, or dimethylcyclohexyl.

[0489] R 1 ~R 4 Regarding the aryl having 6 to 20 carbon atoms, an aryl having 6 to 16 carbon atoms is preferred, an aryl having 6 to 12 carbon atoms is more preferred, and an aryl having 6 to 10 carbon atoms is particularly preferred. As a specific example of the "aryl having 6 to 20 carbon atoms," Ar 2Specific examples of “aryl having 6 to 20 carbon atoms” may be cited. A preferred “aryl having 6 to 20 carbon atoms” is phenyl, biphenyllyl, terphenyllyl, or naphthyl, more preferably phenyl, biphenyllyl, 1-naphthyl, 2-naphthyl, or m-terphenyl-5'-yl, even more preferably phenyl, biphenyllyl, 1-naphthyl, or 2-naphthyl, and most preferably phenyl.

[0490] Specific examples of these anthracene derivatives include, for instance, the following compounds.

[0491]

[0492] These anthracene derivatives can be manufactured using known raw materials and known synthesis methods.

[0493] Benzofluorene derivatives

[0494] Benzofluorene derivatives are compounds represented by, for example, the following formula (ETM-6).

[0495]

[0496] Ar 1 Each is independently an aryl having 6 to 20 carbon atoms, and Ar of formula (ETM-5). 2 The same description as "aryl having 6 to 20 carbon atoms" in [the text] may be cited. An aryl having 6 to 16 carbon atoms is preferred, an aryl having 6 to 12 carbon atoms is more preferred, and an aryl having 6 to 10 carbon atoms is particularly preferred. Specific examples include phenyl, biphenylyl, naphthyl, terphenylyl, anthracenyl, acenaphthylenyl, fluorenyl, phenalenyl, phenanthryl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, etc.

[0497] Ar 2 Each is independently hydrogen, alkyl (preferably an alkyl having 1 to 24 carbon atoms), cycloalkyl (preferably a cycloalkyl having 3 to 12 carbon atoms), or aryl (preferably an aryl having 6 to 30 carbon atoms), and two Ar 2 It may combine to form a ring.

[0498] Ar 2 As for the “alkyl” in the formula, it may be either a straight chain or a branched chain, for example, a straight-chain alkyl having 1 to 24 carbon atoms or a branched-chain alkyl having 3 to 24 carbon atoms. A preferred “alkyl” is an alkyl having 1 to 18 carbon atoms (a branched-chain alkyl having 3 to 18 carbon atoms). A more preferred “alkyl” is an alkyl having 1 to 12 carbon atoms (a branched-chain alkyl having 3 to 12 carbon atoms). An even more preferred “alkyl” is an alkyl having 1 to 6 carbon atoms (a branched-chain alkyl having 3 to 6 carbon atoms). A particularly preferred “alkyl” is an alkyl having 1 to 4 carbon atoms (a branched-chain alkyl having 3 to 4 carbon atoms). Specific examples of “alkyl” include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, etc.

[0499] Ar 2 Examples of "cycloalkyl" include cycloalkyls having 3 to 12 carbon atoms. A preferred "cycloalkyl" is a cycloalkyl having 3 to 10 carbon atoms. A more preferred "cycloalkyl" is a cycloalkyl having 3 to 8 carbon atoms. An even more preferred "cycloalkyl" is a cycloalkyl having 3 to 6 carbon atoms. Specific examples of "cycloalkyl" include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclopentyl, cycloheptyl, methylcyclohexyl, cyclooctyl, or dimethylcyclohexyl.

[0500] Ar 2 As for the “aryl” in the example, the preferred aryl is an aryl having 6 to 30 carbon atoms, the more preferred aryl having 6 to 18 carbon atoms, even more preferably an aryl having 6 to 14 carbon atoms, and particularly preferably an aryl having 6 to 12 carbon atoms.

[0501] Specific examples of “aryls having 6 to 30 carbon atoms” include phenyl, naphthyl, acenaphthyrenyl, fluorenyl, phenalenyl, phenanthryl, triphenylenyl, pyrenyl, naphthacenyl, perylenyl, pentacenyl, etc.

[0502] 2 Ar 2 They may be combined to form a ring, and as a result, cyclobutane, cyclopentane, cyclopentene, cyclopentadiene, cyclohexane, fluorene, or indene, etc. may be spiro-bonded to the 5-membered ring of the fluorene skeleton.

[0503] Specific examples of this benzofluorene derivative include, for instance, the following compounds.

[0504]

[0505] This benzofluorene derivative can be manufactured using known raw materials and known synthesis methods.

[0506] Phosphine oxide derivatives

[0507] Phosphine oxide derivatives are compounds represented by, for example, the following formula (ETM-7-1). Details are also described in International Publication No. 2013 / 079217 and International Publication No. 2013 / 079678.

[0508]

[0509] R 5 is a substituted or unsubstituted alkyl having 1 to 20 carbon atoms, a cycloalkyl having 3 to 16 carbon atoms, an aryl having 6 to 20 carbon atoms, or a heteroaryl having 5 to 20 carbon atoms, and

[0510] R 6 is CN, substituted or unsubstituted, an alkyl having 1 to 20 carbon atoms, a cycloalkyl having 3 to 16 carbon atoms, a heteroalkyl having 1 to 20 carbon atoms, an aryl having 6 to 20 carbon atoms, a heteroaryl having 5 to 20 carbon atoms, an alkoxy having 1 to 20 carbon atoms, or an aryloxy having 6 to 20 carbon atoms, and

[0511] R 7 and R 8Each is independently a substituted or unsubstituted aryl having 6 to 20 carbon atoms or a heteroaryl having 5 to 20 carbon atoms, and

[0512] R 9 It is oxygen or sulfur, and

[0513] j is 0 or 1, k is 0 or 1, r is an integer from 0 to 4, and q is an integer from 1 to 3.

[0514] Here, examples of substituents that are substituted include aryl, heteroaryl, alkyl, or cycloalkyl.

[0515] Phosphine oxide derivatives may be, for example, compounds represented by the following formula (ETM-7-2).

[0516]

[0517] R 1 ~R 3 The group may be the same or different and is selected from hydrogen, alkyl, cycloalkyl, aralkyl, alkenyl, cycloalkenyl, alkynyl, alkoxy, alkylthio, cycloalkylthio, aryl ether (aryl ether group), arylthioether (arylthioether group), aryl, heterocyclic group, halogen, cyano, formyl, carbonyl, carboxyl, amino, nitro, silyl, and condensation rings formed between adjacent substituents.

[0518] Ar 1 It may be the same or different, and is arylene or heteroarylene. Ar 2 is, may be identical or different, and is an aryl or heteroaryl. However, Ar 1 and Ar 2 At least one of them has a substituent or forms a condensation ring with an adjacent substituent. n is an integer from 0 to 3, where when n is 0, the unsaturated structural part does not exist, and when n is 3, R 1 It does not exist.

[0519] Among these substituents, the alkyl group represents a saturated aliphatic hydrocarbon group such as, for example, methyl, ethyl, propyl, or butyl, and it may be unsubstituted or substituted. There are no particular restrictions on the substituents when substituted, such as alkyl, aryl, or heterocyclic groups, and this applies to the description below as well. In addition, the number of carbon atoms of the alkyl group is not particularly limited, but is typically in the range of 1 to 20 for ease of availability and cost.

[0520] In addition, the cycloalkyl group represents a saturated alicyclic hydrocarbon group such as, for example, cyclopropyl, cyclohexyl, norbornyl, and adamantyl, and it may be unsubstituted or substituted. The number of carbon atoms in the alkyl portion is not particularly limited, but is typically in the range of 3 to 20.

[0521] In addition, the aryl group represents an aromatic hydrocarbon group formed from an aliphatic hydrocarbon, such as benzyl or phenylethyl, for example, and both the aliphatic hydrocarbon and the aromatic hydrocarbon may be unsubstituted or substituted. The number of carbon atoms in the aliphatic portion is not particularly limited, but is typically in the range of 1 to 20.

[0522] In addition, the alkenyl represents an unsaturated aliphatic hydrocarbon group containing a double bond, such as vinyl, allyl, or butadienyl, and it may be unsubstituted or substituted. The number of carbon atoms in the alkenyl is not particularly limited, but is typically in the range of 2 to 20.

[0523] In addition, the cycloalkenyl represents an unsaturated alicyclic hydrocarbon group containing a double bond, such as cyclopentenyl, cyclopentadienyl, and cyclohexenyl, and it may be unsubstituted or substituted.

[0524] In addition, the alkynyl represents an unsaturated aliphatic hydrocarbon group containing a triple bond, such as acetylenyl, for example, and it may be unsubstituted or substituted. The number of carbon atoms in the alkynyl is not particularly limited, but is typically in the range of 2 to 20.

[0525] In addition, the alkoxy represents an aliphatic hydrocarbon group formed by an ether bond, such as a methoxy, for example, and the aliphatic hydrocarbon group may be unsubstituted or substituted. The number of carbon atoms in the alkoxy is not particularly limited, but is typically in the range of 1 to 20.

[0526] In addition, alkylthio is a group in which the oxygen atom of the ether bond of the alkoxy is substituted with a sulfur atom.

[0527] In addition, cycloalkylthio is a group in which the oxygen atom of the ether bond of the cycloalkoxy is substituted with a sulfur atom.

[0528] In addition, the aryl ether represents an aromatic hydrocarbon group through an ether bond, such as phenoxy, for example, and the aromatic hydrocarbon group may be unsubstituted or substituted. The number of carbon atoms in the aryl ether is not particularly limited, but is typically in the range of 6 to 40.

[0529] In addition, arylthioether is a group in which the oxygen atom of the ether bond of an aryl ether is replaced by a sulfur atom.

[0530] In addition, the aryl represents an aromatic hydrocarbon group, such as, for example, phenyl, naphthyl, biphenylyl, phenanthyl, terphenyl, and pyrenyl. The aryl may be unsubstituted or substituted. The number of carbon atoms in the aryl is not particularly limited, but is typically in the range of 6 to 40.

[0531] In addition, the complex cyclic group represents a cyclic structural group having atoms other than carbon, such as furanyl, thienyl, oxazolyl, pyridyl, quinolinyl, and carbazolyl, and it may be unsubstituted or substituted. The number of carbon atoms in the complex cyclic group is not particularly limited, but is typically in the range of 2 to 30.

[0532] Halogens represent fluorine, chlorine, bromine, and iodine.

[0533] Formyl, carbonyl, and amino may include groups substituted with aliphatic hydrocarbons, alicyclic hydrocarbons, aromatic hydrocarbons, heterocyclic hydrocarbons, etc.

[0534] In addition, aliphatic hydrocarbons, alicyclic hydrocarbons, aromatic hydrocarbons, and heterocyclic hydrocarbons may be unsubstituted or substituted.

[0535] The silyl represents a silicon compound group, such as trimethylsilyl, for example, and may be unsubstituted or substituted. The number of carbon atoms in the silyl is not particularly limited, but is typically in the range of 3 to 20. Also, the number of silicon atoms is typically 1 to 6.

[0536] The condensation ring formed between adjacent substituents is, for example, Ar 1 and R 2 , Ar 1 and R 3 , Ar 2 and R 2 , Ar 2 and R 3 , R 2 and R 3 , Ar 1 and Ar 2 It is a condensation ring of the codomain or non-codomain formed between etc. Here, when n is 1, 2 R 1 They may form conjugated or non-conjugated condensed rings. These condensed rings may include nitrogen, oxygen, and sulfur atoms in their internal structure and may further condense with other rings.

[0537] Specific examples of this phosphine oxide derivative include, for instance, the following compounds.

[0538]

[0539] This phosphine oxide derivative can be manufactured using known raw materials and known synthesis methods.

[0540] Pyrimidine derivatives

[0541] The pyrimidine derivative is, for example, a compound represented by the following formula (ETM-8), and preferably a compound represented by the following formula (ETM-8-1). Details are also provided in International Publication No. 2011 / 021689.

[0542]

[0543] Ar is, each independently, an aryl that may be substituted or a heteroaryl that may be substituted. n is an integer from 1 to 4, preferably an integer from 1 to 3, and more preferably 2 or 3.

[0544] As for the “aryl” of the “aryl that may be substituted,” for example, there is an aryl having 6 to 30 carbon atoms, preferably an aryl having 6 to 24 carbon atoms, more preferably an aryl having 6 to 20 carbon atoms, and even more preferably an aryl having 6 to 12 carbon atoms.

[0545] Specific "aryls" include the monocyclic aryl phenyl, the dicyclic aryl (2-, 3-, 4-)biphenylyl, the condensed dicyclic aryl (1-, 2-)naphthyl, the tricyclic aryl terphenylyl (m-terphenyl-2'-yl, m-terphenyl-4'-yl, m-terphenyl-5'-yl, o-terphenyl-3'-yl, o-terphenyl-4'-yl, p-terphenyl-2'-yl, m-terphenyl-2-yl, m-terphenyl-3-yl, m-terphenyl-4-yl, o-terphenyl-2-yl, o-terphenyl-3-yl, o-terphenyl-4-yl, p-terphenyl-2-yl, p-terphenyl-3-yl, p-terphenyl-4-yl), the condensed tricyclic aryl, acenaphthylene-(1-, 3-, 4-, Examples include 5-), fluorene-(1-, 2-, 3-, 4-, 9-)yl, phenalene-(1-, 2-)yl, (1-, 2-, 3-, 4-, 9-)phenanthrile, tetracyclic aryls such as quadrphenylyl (5'-phenyl-m-terphenyl-2-yl, 5'-phenyl-m-terphenyl-3-yl, 5'-phenyl-m-terphenyl-4-yl, m-quaternphenylyl), condensed tetracyclic aryls such as triphenylene-(1-, 2-)yl, pyrene-(1-, 2-, 4-)yl, naphthacene-(1-, 2-, 5-)yl, and condensed pentacyclic aryls such as perylene-(1-, 2-, 3-)yl, pentacene-(1-, 2-, 5-)yl. there is.

[0546] As for the “heteroaryl” of the “heteroaryl that may be substituted,” for example, there are heteroaryls having 2 to 30 carbon atoms, heteroaryls having 2 to 25 carbon atoms are preferred, heteroaryls having 2 to 20 carbon atoms are more preferred, heteroaryls having 2 to 15 carbon atoms are even more preferred, and heteroaryls having 2 to 10 carbon atoms are particularly preferred. In addition, as for the heteroaryl, for example, there are heterocyclic rings containing 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen in addition to carbon as ring constituent atoms.

[0547] Specific heteroaryls include, for example, furyl, thienyl, pyrrolyl, oxazolyl, isooxazolyl, thiazolyl, isothiazolyl, imidazolyl, pyrazolyl, oxathiazolyl, furazanyl, thiadiazolyl, triazolyl, tetrazolyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, benzofuranyl, isobenzofuranyl, benzo[b]thienyl, indolyl, isoindolyl, 1H-indazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolyl, isoquinolyl, cinnolyl, quinazolyl, quinoxalinyl, phthalazinyl, naftiridinyl, furinyl, pteridinyl, carbazolyl, There are acridinyl, phenoxazinil, phenothiazinil, phenazinil, phenoxatiinil, thiantrenil, indolidinil, etc.

[0548] In addition, the above aryl and heteroaryl may be substituted, and each may be substituted with, for example, the above aryl or heteroaryl.

[0549] Specific examples of this pyrimidine derivative include, for instance, the following compounds.

[0550]

[0551] This pyrimidine derivative can be manufactured using known raw materials and known synthesis methods.

[0552] Arylnitrile derivatives

[0553] Arylnitrile derivatives are, for example, compounds represented by the following formula (ETM-9), or polymers in which they are linked by multiple bonds, such as single bonds. Details are provided in the specification of U.S. Application Publication No. 2014 / 0197386.

[0554]

[0555] Ar ni From the perspective of fast electron transport, a large number of carbon atoms is desirable, while from the perspective of high T1, a small number of carbon atoms is desirable. Ar niSpecifically, for use in a layer adjacent to a light-emitting layer, it is desirable that the T1 be high, and the aryl has 6 to 20 carbon atoms, preferably 6 to 14 carbon atoms, and more preferably 6 to 10 carbon atoms. In addition, the number of substitutions n of the nitrile group is desirable to be large from the perspective of high T1 and low from the perspective of high S1. Specifically, the number of substitutions n of the nitrile group is an integer from 1 to 4, preferably an integer from 1 to 3, more preferably an integer from 1 to 2, and even more preferably 1.

[0556] Ar is, independently, an aryl or a heteroaryl that may be substituted. It is preferable that it be a donor heteroaryl in terms of high S1 and high T1, and it is preferable that the donor heteroaryl be small in terms of use as an electron transport layer. In terms of charge transport properties, it is preferable that it be an aryl or heteroaryl with a large number of carbon atoms and has many substituents. Specifically, the number of substituents m of Ar is an integer from 1 to 4, preferably an integer from 1 to 3, and more preferably 1 to 2.

[0557] As for the “aryl” of the “aryl that may be substituted,” for example, there is an aryl having 6 to 30 carbon atoms, preferably an aryl having 6 to 24 carbon atoms, more preferably an aryl having 6 to 20 carbon atoms, and even more preferably an aryl having 6 to 12 carbon atoms.

[0558] Specific "aryls" include the monocyclic aryl phenyl, the dicyclic aryl (2-, 3-, 4-)biphenylyl, the condensed dicyclic aryl (1-, 2-)naphthyl, the tricyclic aryl terphenylyl (m-terphenyl-2'-yl, m-terphenyl-4'-yl, m-terphenyl-5'-yl, o-terphenyl-3'-yl, o-terphenyl-4'-yl, p-terphenyl-2'-yl, m-terphenyl-2-yl, m-terphenyl-3-yl, m-terphenyl-4-yl, o-terphenyl-2-yl, o-terphenyl-3-yl, o-terphenyl-4-yl, p-terphenyl-2-yl, p-terphenyl-3-yl, p-terphenyl-4-yl), the condensed tricyclic aryl, acenaphthylene-(1-, 3-, 4-, Examples include 5-), fluorene-(1-, 2-, 3-, 4-, 9-)yl, phenalene-(1-, 2-)yl, (1-, 2-, 3-, 4-, 9-)phenanthrile, tetracyclic aryls such as quadrphenylyl (5'-phenyl-m-terphenyl-2-yl, 5'-phenyl-m-terphenyl-3-yl, 5'-phenyl-m-terphenyl-4-yl, m-quaternphenylyl), condensed tetracyclic aryls such as triphenylene-(1-, 2-)yl, pyrene-(1-, 2-, 4-)yl, naphthacene-(1-, 2-, 5-)yl, and condensed pentacyclic aryls such as perylene-(1-, 2-, 3-)yl, pentacene-(1-, 2-, 5-)yl. there is.

[0559] As for the “heteroaryl” of the “heteroaryl that may be substituted,” for example, there are heteroaryls having 2 to 30 carbon atoms, heteroaryls having 2 to 25 carbon atoms are preferred, heteroaryls having 2 to 20 carbon atoms are more preferred, heteroaryls having 2 to 15 carbon atoms are even more preferred, and heteroaryls having 2 to 10 carbon atoms are particularly preferred. In addition, as for the heteroaryl, for example, there are heterocyclic rings containing 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen in addition to carbon as ring constituent atoms.

[0560] Specific heteroaryls include, for example, furyl, thienyl, pyrrolyl, oxazolyl, isooxazolyl, thiazolyl, isothiazolyl, imidazolyl, pyrazolyl, oxadiazolyl, furazanyl, thiadiazolyl, triazolyl, tetrazolyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, benzofuranyl, isobenzofuranyl, benzo[b]thienyl, indolyl, isoindolyl, 1H-indazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolyl, isoquinolyl, cinnolyl, quinazolyl, quinoxalinyl, phthalazinyl, naftiridinyl, furinyl, pteridinyl, carbazolyl, There are acridinyl, phenoxazinil, phenothiazinil, phenazinil, phenoxatiinil, thiantrenil, indolidinil, etc.

[0561] In addition, the above aryl and heteroaryl may be substituted, and each may be substituted with, for example, the above aryl or heteroaryl.

[0562] The arylnitrile derivative may be a polymer in which the compound represented by formula (ETM-9) is bonded multiple times, such as by a single bond. In this case, in addition to the single bond, it may be bonded by an aryl ring (preferably a polyvalent benzene ring, naphthalene ring, anthracene ring, fluorene ring, benzofluorene ring, phenalene ring, phenanthrene ring, or triphenylene ring).

[0563] Specific examples of this arylnitrile derivative include, for example, the following compounds.

[0564]

[0565] This arylnitrile derivative can be manufactured using known raw materials and known synthesis methods.

[0566] Triazine derivatives

[0567] Triazine derivatives are, for example, compounds represented by the following formula (ETM-10), and preferably compounds represented by the following formula (ETM-10-1). Details are provided in the specification of U.S. Application Publication No. 2011 / 0156013.

[0568]

[0569] Ar is, each independently, an aryl that may be substituted or a heteroaryl that may be substituted. n is an integer from 1 to 3, preferably 2 or 3.

[0570] As for the “aryl” of the “aryl that may be substituted,” for example, there is an aryl having 6 to 30 carbon atoms, preferably an aryl having 6 to 24 carbon atoms, more preferably an aryl having 6 to 20 carbon atoms, and even more preferably an aryl having 6 to 12 carbon atoms.

[0571] Specific "aryls" include the monocyclic aryl phenyl, the dicyclic aryl (2-, 3-, 4-)biphenylyl, the condensed dicyclic aryl (1-, 2-)naphthyl, the tricyclic aryl terphenylyl (m-terphenyl-2'-yl, m-terphenyl-4'-yl, m-terphenyl-5'-yl, o-terphenyl-3'-yl, o-terphenyl-4'-yl, p-terphenyl-2'-yl, m-terphenyl-2-yl, m-terphenyl-3-yl, m-terphenyl-4-yl, o-terphenyl-2-yl, o-terphenyl-3-yl, o-terphenyl-4-yl, p-terphenyl-2-yl, p-terphenyl-3-yl, p-terphenyl-4-yl), the condensed tricyclic aryl, acenaphthylene-(1-, 3-, 4-, Examples include 5-), fluorene-(1-, 2-, 3-, 4-, 9-)yl, phenalene-(1-, 2-)yl, (1-, 2-, 3-, 4-, 9-)phenanthrile, tetracyclic aryls such as quadrphenylyl (5'-phenyl-m-terphenyl-2-yl, 5'-phenyl-m-terphenyl-3-yl, 5'-phenyl-m-terphenyl-4-yl, m-quaternphenylyl), condensed tetracyclic aryls such as triphenylene-(1-, 2-)yl, pyrene-(1-, 2-, 4-)yl, naphthacene-(1-, 2-, 5-)yl, and condensed pentacyclic aryls such as perylene-(1-, 2-, 3-)yl, pentacene-(1-, 2-, 5-)yl. there is.

[0572] As for the “heteroaryl” of the “heteroaryl that may be substituted,” for example, there are heteroaryls having 2 to 30 carbon atoms, heteroaryls having 2 to 25 carbon atoms are preferred, heteroaryls having 2 to 20 carbon atoms are more preferred, heteroaryls having 2 to 15 carbon atoms are even more preferred, and heteroaryls having 2 to 10 carbon atoms are particularly preferred. In addition, as for the heteroaryl, for example, there are heterocyclic rings containing 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen in addition to carbon as ring constituent atoms.

[0573] Specific heteroaryls include, for example, furyl, thienyl, pyrrolyl, oxazolyl, isooxazolyl, thiazolyl, isothiazolyl, imidazolyl, pyrazolyl, oxathiazolyl, furazanyl, thiadiazolyl, triazolyl, tetrazolyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, benzofuranyl, isobenzofuranyl, benzo[b]thienyl, indolyl, isoindolyl, 1H-indazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolyl, isoquinolyl, cinnolyl, quinazolyl, quinoxalinyl, phthalazinyl, naftiridinyl, furinyl, pteridinyl, carbazolyl, There are acridinyl, phenoxazinil, phenothiazinil, phenazinil, phenoxatiinil, thiantrenil, indolidinil, etc.

[0574] In addition, the above aryl and heteroaryl may be substituted, and each may be substituted with, for example, the above aryl or heteroaryl.

[0575] Specific examples of this triazine derivative include, for instance, the following compounds.

[0576]

[0577] This triazine derivative can be manufactured using known raw materials and known synthesis methods.

[0578] Benzimidazole derivatives

[0579] Benzimidazole derivatives are compounds represented by, for example, the following formula (ETM-11).

[0580]

[0581] f is an n-valent aryl ring (preferably an n-valent benzene ring, naphthalene ring, anthracene ring, fluorene ring, benzofluorene ring, phenalene ring, phenanthrene ring, or triphenylene ring), where n is an integer from 1 to 4, and the “benzimidazole-based substituent” is a substituent in which pyridyl in the “pyridine-based substituent” of formula (ETM-2), formula (ETM-2-1), and formula (ETM-2-2) is substituted with benzimidazolyl, and one or more hydrogens in the benzimidazole derivative may be substituted with deuterium.

[0582] * indicates the connection position.

[0583] R in the above benzimidazolyl 11 Silver, hydrogen, an alkyl having 1 to 24 carbon atoms, a cycloalkyl having 3 to 12 carbon atoms, or an aryl having 6 to 30 carbon atoms, and R in formulas (ETM-2-1) and (ETM-2-2). 11 You can quote the explanation of.

[0584] f It is also preferable that it be an anthracene ring or a fluorene ring, and in this case, the structure may be described in Formula (ETM-2-1) or Formula (ETM-2-2), and R in each formula 11 ~R 18 The explanation in Formula (ETM-2-1) or Formula (ETM-2-2) may be cited. Additionally, although Formula (ETM-2-1) or Formula (ETM-2-2) describes a form in which two pyridine substituents are combined, when substituting them with benzimidazole substituents, both pyridine substituents may be substituted with benzimidazole substituents (i.e., n=2), or one pyridine substituent may be substituted with a benzimidazole substituent and the other pyridine substituent R 11 ~R18 It may be substituted with (i.e., n=1). Also, for example, R in Equation (ETM-2-1) 11 ~R 18 Substitute one or more of them with benzimidazole-based substituents and the “pyridine-based substituent” R 11 ~R 18 It can be replaced with .

[0585] Specific examples of this benzimidazole derivative include, for example, 1-phenyl-2-(4-(10-phenylanthracen-9-yl)phenyl)-1H-benzo[d]imidazole, 2-(4-(10-(naphthalene-2-yl)anthracen-9-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole, 2-(3-(10-(naphthalene-2-yl)anthracen-9-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole, 5-(10-(naphthalene-2-yl)anthracen-9-yl)-1,2-diphenyl-1H-benzo[d]imidazole, 1-(4-(10-(naphthalene-2-yl)anthracen-9-yl)phenyl)-2-phenyl-1H-benzo[d]imidazole, Examples include 2-(4-(9,10-di(naphthalene-2-yl)anthracene-2-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole, 1-(4-(9,10-di(naphthalene-2-yl)anthracene-2-yl)phenyl)-2-phenyl-1H-benzo[d]imidazole, 5-(9,10-di(naphthalene-2-yl)anthracene-2-yl)-1,2-diphenyl-1H-benzo[d]imidazole, etc.

[0586]

[0587] This benzimidazole derivative can be manufactured using known raw materials and known synthesis methods.

[0588] <Phenanthroline derivatives>

[0589] Phenanthroline derivatives are compounds represented by, for example, the following formula (ETM-12) or formula (ETM-12-1). Details are provided in International Publication No. 2006 / 021982.

[0590]

[0591] fis an n-valent aryl ring (preferably an n-valent benzene ring, naphthalene ring, anthracene ring, fluorene ring, benzofluorene ring, phenalene ring, phenanthrene ring, or triphenylene ring), where n is an integer from 1 to 4.

[0592] R of each equation 11 ~R 18 Each is independently hydrogen, alkyl (preferably an alkyl having 1 to 24 carbon atoms), cycloalkyl (preferably a cycloalkyl having 3 to 12 carbon atoms), or aryl (preferably an aryl having 6 to 30 carbon atoms). In addition, in formula (ETM-12-1), R 11 ~R 18 One of them is Arilhwanin f It is a combined hand with.

[0593] In each phenanthroline derivative, one or more hydrogens may be substituted with deuterium.

[0594] R 11 ~R 18 As for the alkyl, cycloalkyl, and aryl in , R in formula (ETM-2) 11 ~R 18 You can quote the explanation of. Also, f In addition to the examples above, there are, for instance, the following structural formulas. In the following structural formulas, R is independently hydrogen, methyl, ethyl, isopropyl, cyclohexyl, phenyl, 1-naphthyl, 2-naphthyl, biphenyllyl, or terphenyllyl, and * indicates a bonding position.

[0595]

[0596] Specific examples of this phenanthroline derivative include, for example, 4,7-diphenyl-1,10-phenanthroline, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline, 9,10-di(1,10-phenanthroline-2-yl)anthracene, 2,6-di(1,10-phenanthroline-5-yl)pyridine, 1,3,5-tri(1,10-phenanthroline-5-yl)benzene, 9,9'-difluoro-bis(1,10-phenanthroline-5-yl), vasocuproin, 1,3-bis(2-phenyl-1,10-phenanthroline-9-yl)benzene, or compounds represented by the following structural formulas.

[0597]

[0598] This phenanthroline derivative can be manufactured using known raw materials and known synthesis methods.

[0599] Quinolinol metal complexes

[0600] Quinolinol metal complexes include, for example, compounds represented by the following formula (ETM-13).

[0601]

[0602] During the meal, R 1 ~R 6 Each is independently hydrogen, fluorine, alkyl, cycloalkyl, aralkyl, alkenyl, cyano, alkoxy, or aryl, M is Li, Al, Ga, Be, or Zn, and n is an integer from 1 to 3.

[0603] Specific examples of quinolinol-based metal complexes include 8-quinolinol lithium, tris(8-quinolinoleate)aluminum, tris(4-methyl-8-quinolinoleate)aluminum, tris(5-methyl-8-quinolinoleate)aluminum, tris(3,4-dimethyl-8-quinolinoleate)aluminum, tris(4,5-dimethyl-8-quinolinoleate)aluminum, tris(4,6-dimethyl-8-quinolinoleate)aluminum, bis(2-methyl-8-quinolinoleate)(phenolate)aluminum, bis(2-methyl-8-quinolinoleate)(2-methylphenolate)aluminum, and bis(2-methyl-8-quinolinoleate)(3-methylphenolate)aluminum. Bis(2-methyl-8-quinolinoleate)(4-methylphenolate)aluminum, Bis(2-methyl-8-quinolinoleate)(2-phenylphenolate)aluminum, Bis(2-methyl-8-quinolinoleate)(3-phenylphenolate)aluminum, Bis(2-methyl-8-quinolinoleate)(4-phenylphenolate)aluminum, Bis(2-methyl-8-quinolinoleate)(2,3-dimethylphenolate)aluminum, Bis(2-methyl-8-quinolinoleate)(2,6-dimethylphenolate)aluminum, Bis(2-methyl-8-quinolinoleate)(3,4-dimethylphenolate)aluminum, Bis(2-methyl-8-quinolinoleate)(3,5-dimethylphenolate)aluminum, Bis(2-methyl-8-quinolinoleate)(3,5-di-tert-butylphenolate)aluminum, Bis(2-methyl-8-quinolinoleate)(2,6-diphenylphenolate)aluminum, Bis(2-methyl-8-quinolinoleate)(2,4,6-triphenylphenolate)aluminum, Bis(2-methyl-8-quinolinoleate)(2,4,6-trimethylphenolate)aluminum, Bis(2-methyl-8-quinolinoleate)(2,4,5,6-tetramethylphenolate)aluminum, Bis(2-methyl-8-quinolinoleate)(1-naphtholate)aluminum, Bis(2-methyl-8-quinolinoleate)(2-naphtholate)aluminum, Bis(2,4-dimethyl-8-quinolinoleate)(2-phenylphenolate)aluminum, bis(2,4-dimethyl-8-quinolinoleate)(3-phenylphenolate)aluminum, bis(2,4-dimethyl-8-quinolinoleate)(4-phenylphenolate)aluminum, bis(2,4-dimethyl-8-quinolinoleate)(3,5-Dimethylphenolate)aluminum, bis(2,4-dimethyl-8-quinolinoleate)(3,5-di-tert-butylphenolate)aluminum, bis(2-methyl-8-quinolinoleate)aluminum-μ-oxo-bis(2-methyl-8-quinolinoleate)aluminum, bis(2,4-dimethyl-8-quinolinoleate)aluminum-μ-oxo-bis(2,4-dimethyl-8-quinolinoleate)aluminum, bis(2-methyl-4-ethyl-8-quinolinoleate)aluminum-μ-oxo-bis(2-methyl-4-ethyl-8-quinolinoleate)aluminum, Examples include bis(2-methyl-4-methoxy-8-quinolinoleate)aluminum-μ-oxo-bis(2-methyl-4-methoxy-8-quinolinoleate)aluminum, bis(2-methyl-5-cyano-8-quinolinoleate)aluminum-μ-oxo-bis(2-methyl-5-cyano-8-quinolinoleate)aluminum, bis(2-methyl-5-trifluoromethyl-8-quinolinoleate)aluminum-μ-oxo-bis(2-methyl-5-trifluoromethyl-8-quinolinoleate)aluminum, bis(10-hydroxybenzo[h]quinoline)beryllium, etc.

[0604] This quinolinol-based metal complex can be manufactured using known raw materials and known synthesis methods.

[0605] <Thiazol Derivatives and Benzothiazole Derivatives>

[0606] Thiazole derivatives are compounds represented by, for example, the following formula (ETM-14-1).

[0607]

[0608] Benzothiazole derivatives are compounds represented by, for example, the following formula (ETM-14-2).

[0609]

[0610] of each formula fis an n-valent aryl ring (preferably an n-valent benzene ring, naphthalene ring, anthracene ring, fluorene ring, benzofluorene ring, phenalene ring, phenanthrene ring, or triphenylene ring), where n is an integer from 1 to 4, and the “thiazole-based substituent” or “benzothiazole-based substituent” is a substituent in which the pyridyl in the “pyridine-based substituent” of Formula (ETM-2), Formula (ETM-2-1), and Formula (ETM-2-2) is substituted with the following thiazolyl or benzothiolyl, and at least one hydrogen in the thiazole derivative and the benzothiazole derivative may be substituted with a deuterium.

[0611] * indicates the connection position.

[0612] f It is also preferable that it be an anthracene ring or a fluorene ring, and in this case, the structure may be described in Formula (ETM-2-1) or Formula (ETM-2-2), and R in each formula 11 ~R 18 The explanation in Equation (ETM-2-1) or Equation (ETM-2-2) may be cited. Additionally, although Equation (ETM-2-1) or Equation (ETM-2-2) describes a form in which two pyridine substituents are combined, when substituting them with thiazole substituents (or benzothiazole substituents), both pyridine substituents may be substituted with thiazole substituents (or benzothiazole substituents) (i.e., n=2), or one pyridine substituent may be substituted with a thiazole substituent (or benzothiazole substituent) and the other pyridine substituent R 11 ~R 18 It may be substituted with (i.e., n=1). Also, for example, R in Equation (ETM-2-1). 11 ~R 18 At least one of them is substituted with a thiazole substituent (or benzothiazole substituent), and the “pyridine substituent” is R 11 ~R 18 It can be replaced with .

[0613] These thiazole derivatives or benzothiazole derivatives can be manufactured using known raw materials and known synthesis methods.

[0614] Silol derivatives

[0615] Silol derivatives are compounds represented by, for example, the following formula (ETM-15). Details are provided in Japanese Patent Publication No. Hei 9-194487.

[0616]

[0617] X and Y are each independently alkyl, cycloalkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy, aryl, heteroaryl, and may be substituted. For details regarding these groups, the descriptions in Formula (D) and Formula (Da), etc., and the description in Formula (ETM-7-2) may be cited. Additionally, alkenyloxy and alkynyloxy are groups in which the alkyl portion of the alkoxy is substituted with alkenyl or alkynyl, respectively, and for details regarding these alkenyl and alkynyl groups, the description in Formula (ETM-7-2) may be cited.

[0618] In addition, X and Y may combine to form a cycloalkyl ring (and a ring in which a portion thereof is unsaturated), and details of this cycloalkyl ring may be referred to in the description of the cycloalkyl in formulas (D) and (Da), etc.

[0619] R 1 ~R 4Each is independently hydrogen, halogen, alkyl, cycloalkyl, alkoxy, aryloxy, amino, alkyl carbonyl, aryl carbonyl, alkoxycarbonyl, aryloxycarbonyl, azo group, alkyl carbonyloxy, aryl carbonyloxy, alkoxycarbonyloxy, aryloxycarbonyloxy, sulfinyl, sulfonyl, sulfanyl, silyl, carbamoyl, aryl, heteroaryl, alkenyl, alkynyl, nitro, formyl, nitroso, formyloxy, isocyano, cyanate group, isocyanate group, thiocyanate group, isothiocyanate group, or cyano, and these may be substituted with alkyl, cycloalkyl, aryl, or halogen, and may form a condensation ring with an adjacent substituent.

[0620] R 1 ~R 4 For details regarding the halogen, alkyl, cycloalkyl, alkoxy, aryloxy, amino, aryl, heteroaryl, alkenyl, and alkynyl, the descriptions in formulas (D) and (Da), etc. may be cited.

[0621] R 1 ~R 4 For details regarding the alkyl, aryl, and alkoxy groups among the alkyl carbonyl, aryl carbonyl, alkoxycarbonyl, aryloxycarbonyl, alkylcarbonyloxy, arylcarbonyloxy, alkoxycarbonyloxy, and aryloxycarbonyloxy, the explanation in formula (D) and formula (Da), etc., may be cited.

[0622] Examples of silyls include a silyl group in which at least one of the three hydrogens of the silyl is independently substituted with an aryl, alkyl, or cycloalkyl group, and trisubstituted silyls are preferred, such as triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, and alkyldicycloalkylsilyl. For details regarding the aryl, alkyl, and cycloalkyl groups in these examples, the descriptions in formulas (D) and (Da), etc., may be referenced.

[0623] The condensation ring formed between adjacent substituents is, for example, R 1 and R 2 , R 2 and R 3 , R 3 and R 4 It is a conjugated or non-conjugated condensation ring formed between the rings. These condensation rings may include nitrogen, oxygen, or sulfur atoms in their internal structure, and may also condense with other rings.

[0624] However, preferably, R 1 and R 4 If α is phenyl, X and Y are not alkyl or phenyl. Additionally, preferably, R 1 and R 4 If ga is a thienyl, X and Y are alkyl, R 2 and R 3 is, alkyl, aryl, alkenyl, or R 2 and R 3 It is a structure that does not simultaneously satisfy the cycloalkyl group that forms a ring by bonding. Additionally, preferably, R 1 and R 4 If is silyl, R 2 , R 3 , X and Y are each independently not hydrogen or an alkyl group having 1 to 6 carbon atoms. Additionally, preferably, R 1 and R 2 In the case of a structure in which a benzene ring is condensed, X and Y are not alkyl and phenyl.

[0625] These silol derivatives can be manufactured using known raw materials and known synthesis methods.

[0626] Azoline derivatives

[0627] Azoline derivatives are compounds represented, for example, by the following formula (ETM-16). Details are provided in International Publication No. 2017 / 014226.

[0628]

[0629] Among the formula (ETM-16),

[0630] φ is a m-valent group derived from an aromatic hydrocarbon having 6 to 40 carbon atoms or a m-valent group derived from an aromatic heterocyclic ring having 2 to 40 carbon atoms, and at least one hydrogen in φ may be substituted with an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 14 carbon atoms, an aryl group having 6 to 18 carbon atoms, or a heteroaryl group having 2 to 18 carbon atoms.

[0631] Y is independently -O-, -S-, or >N-Ar, Ar is an aryl having 6 to 12 carbon atoms or a heteroaryl having 2 to 12 carbon atoms, and at least one hydrogen in Ar may be substituted with an alkyl having 1 to 4 carbon atoms, a cycloalkyl having 5 to 10 carbon atoms, an aryl having 6 to 12 carbon atoms, or a heteroaryl having 2 to 12 carbon atoms, and R 1 ~R 5 Each is independently hydrogen, an alkyl having 1 to 4 carbon atoms, or a cycloalkyl having 5 to 10 carbon atoms, provided that Ar in >N-Ar and R 1 ~R 5 One of them is a site that combines with L, and

[0632] L is selected from a group consisting of a divalent group represented by the following formula (L-1) and a divalent group represented by the following formula (L-2), each independently.

[0633]

[0634] Among equation (L-1), X 1 ~X 6 are each independently =CR 6 - or =N- and X 1 ~X 6 At least 2 of them are =CR 6 -is, X 1 ~X 6 2 of =CR 6 R in - 6 is the site that binds to φ or the azoline ring, and the other =CR 6 R in - 6 is hydrogen, and

[0635] In Equation (L-2), X 7 ~X 14 are each independently =CR 6 - or =N- and X 7 ~X 14 At least 2 of the middle ones are = CR 6 -is, X 7 ~X 14 2 of them = CR 6 R in - 6 is the site that binds to φ or the azoline ring, and the other =CR 6 R in - 6 is hydrogen, and

[0636] At least one hydrogen in L may be substituted with a C1-4 alkyl, a C5-10 cycloalkyl, a C6-10 aryl, or a C2-10 heteroaryl, and

[0637] m is an integer from 1 to 4, and when m is 2 to 4, the group formed by the azoline ring and L may be the same or different, and,

[0638] At least one hydrogen in the compound represented by formula (ETM-16) may be substituted with deuterium.

[0639] Specific azoline derivatives are compounds represented by the following formula (ETM-16-1) or formula (ETM-16-2).

[0640]

[0641] Among Equations (ETM-16-1) and (ETM-16-2),

[0642] φ is a m-valent group derived from an aromatic hydrocarbon having 6 to 40 carbon atoms or a m-valent group derived from an aromatic heterocyclic ring having 2 to 40 carbon atoms, and at least one hydrogen in φ may be substituted with an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 14 carbon atoms, an aryl group having 6 to 18 carbon atoms, or a heteroaryl group having 2 to 18 carbon atoms.

[0643] In formula (ETM-16-1), Y is independently -O-, -S-, or >N-Ar, Ar is an aryl having 6 to 12 carbon atoms or a heteroaryl having 2 to 12 carbon atoms, and at least one hydrogen in Ar may be substituted with an alkyl having 1 to 4 carbon atoms, a cycloalkyl having 5 to 10 carbon atoms, an aryl having 6 to 12 carbon atoms, or a heteroaryl having 2 to 12 carbon atoms.

[0644] In Equation (ETM-16-1), R 1 ~R 4 Each is independently hydrogen, an alkyl having 1 to 4 carbon atoms, or a cycloalkyl having 5 to 10 carbon atoms, provided that R 1 and R 2 is the same, and also R 3 and R 4 is identical,

[0645] In Equation (ETM-16-2), R 1 ~R 5 Each is independently hydrogen, an alkyl having 1 to 4 carbon atoms, or a cycloalkyl having 5 to 10 carbon atoms, provided that R 1 and R 2 is the same, and also R 3 and R 4 is identical,

[0646] Among Equations (ETM-16-1) and (ETM-16-2),

[0647] L is selected from a group consisting of a divalent group represented by the following formula (L-1) and a divalent group represented by the following formula (L-2), each independently.

[0648]

[0649] Among equation (L-1), X 1 ~X 6 are each independently =CR 6 - or =N- and X 1 ~X 6 At least 2 of them are =CR 6 -is, X 1 ~X 6 2 of =CR 6R in - 6 is the site that binds to φ or the azoline ring, and the other =CR 6 R in - 6 is hydrogen, and

[0650] In Equation (L-2), X 7 ~X 14 are each independently =CR 6 - or =N- and X 7 ~X 14 At least 2 of them are =CR 6 -is, X 7 ~X 14 2 of =CR 6 R in - 6 is the site that binds to φ or the azoline ring, and the other =CR 6 R in - 6 is hydrogen, and

[0651] At least one hydrogen in L may be substituted with a C1-4 alkyl, a C5-10 cycloalkyl, a C6-10 aryl, or a C2-10 heteroaryl, and

[0652] m is an integer from 1 to 4, and when m is 2 to 4, the group formed by the azoline ring and L may be the same or different, and,

[0653] At least one hydrogen in the compound represented by formula (ETM-16-1) or formula (ETM-16-2) may be substituted with deuterium.

[0654] Preferably, φ is selected from the group consisting of a monovalent group represented by the following formulas (φ1-1) to (φ1-18), a divalent group represented by the following formulas (φ2-1) to (φ2-34), a trivalent group represented by the following formulas (φ3-1) to (φ3-3), and a tetravalent group represented by the following formulas (φ4-1) to (φ4-2), and at least one hydrogen in φ may be substituted with an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 14 carbon atoms, an aryl group having 6 to 18 carbon atoms, or a heteroaryl group having 2 to 18 carbon atoms.

[0655]

[0656]

[0657]

[0658] Z in the formula is >CR2, >N-Ar, >NL, -O-, or -S-; R in >CR2 is each independently an alkyl having 1 to 4 carbon atoms, a cycloalkyl having 5 to 10 carbon atoms, an aryl having 6 to 12 carbon atoms, or a heteroaryl having 2 to 12 carbon atoms, and R may be bonded to form a ring; Ar in >N-Ar is an aryl having 6 to 12 carbon atoms or a heteroaryl having 2 to 12 carbon atoms; and L in >NL is L from formula (ETM-16), formula (ETM-16-1), or formula (ETM-16-2). * in the formula indicates a bonding position.

[0659] Preferably, L is a divalent group of a ring selected from the group consisting of benzene, naphthalene, pyridine, pyrazine, pyrimidine, pyridazine, triazine, quinoline, isoquinoline, naphthiridine, phthalazine, quinoxaline, quinazolin, cinnoline, and pteridine, and at least one hydrogen in L may be substituted with an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, or a heteroaryl group having 2 to 10 carbon atoms.

[0660] Preferably, the Ar in >N-Ar as Y or Z is selected from the group consisting of phenyl, naphthyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, naphthiridinyl, phthalazinyl, quinoxalinyl, quinazolinyl, cinnolyl, and pteridinyl, and at least one hydrogen in the Ar in >N-Ar as Y may be substituted with an alkyl having 1 to 4 carbon atoms, a cycloalkyl having 5 to 10 carbon atoms, or an aryl having 6 to 10 carbon atoms.

[0661] Preferably, R 1 ~R 4Each is independently hydrogen, an alkyl having 1 to 4 carbon atoms, or a cycloalkyl having 5 to 10 carbon atoms, provided that R 1 and R 2 is identical, and R 3 and R 4 is identical, and also R 1 ~R 4 Not all of them become hydrogen at the same time, and, m is 1 or 2, and when m is 2, the group formed by the azoline ring and L is the same.

[0662] Specific examples of azoline derivatives include the following compounds. In addition, "Me" in the structural formula represents methyl.

[0663]

[0664] More preferably, φ is selected from the group consisting of divalent groups represented by the following formulas (φ2-1), (φ2-31), (φ2-32), (φ2-33) and (φ2-34), and at least one hydrogen of φ may be substituted with an aryl group having 6 to 18 carbon atoms.

[0665]

[0666] (* indicates the connection position.)

[0667] L is a divalent group in a ring selected from the group consisting of benzene, pyridine, pyrazine, pyrimidine, pyridazine, and triazine, and at least one hydrogen in L may be substituted with a C1-4 alkyl, a C5-10 cycloalkyl, a C6-10 aryl, or a C2-14 heteroaryl.

[0668] The Ar in >N-Ar as Y is selected from the group consisting of phenyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, and triazinyl, and at least one hydrogen in the Ar may be substituted with an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, or an aryl group having 6 to 10 carbon atoms.

[0669] R1 ~R 4 Each is independently hydrogen, an alkyl having 1 to 4 carbon atoms, or a cycloalkyl having 5 to 10 carbon atoms, provided that R 1 and R 2 is identical, and R 3 and R 4 is identical, and also R 1 ~R 4 Not all of them become hydrogen at the same time, and,

[0670] m is 2, and the group formed by the azoline ring and L is the same.

[0671] Other specific examples of azoline derivatives include, for instance, the following compounds. In addition, "Me" in the structural formula represents methyl.

[0672]

[0673] For details regarding the alkyl, cycloalkyl, aryl, or heteroaryl in each of the above formulas defining this azoline derivative, the descriptions in formulas (D) and (Da), etc. may be cited.

[0674] This azoline derivative can be manufactured using known raw materials and known synthesis methods.

[0675] Reducing substances

[0676] The electron transport layer or electron injection layer may further include a material capable of reducing the material forming the electron transport layer or electron injection layer. Various materials may be used as this reducing material as long as they have a certain reducing property, and 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 may be preferably used.

[0677] Examples of desirable reducing materials include alkali metals such as Na (work function 2.36 eV), K (work function 2.28 eV), Rb (work function 2.16 eV), or Cs (work function 1.95 eV), or alkaline earth metals such as Ca (work function 2.9 eV), Sr (work function 2.0 to 2.5 eV), or Ba (work function 2.52 eV), and materials with a work function of 2.9 eV or less are particularly preferred. Among these, more desirable reducing materials are alkali metals such as K, Rb, or Cs, more preferably Rb or Cs, and most preferred is Cs. These alkali metals have particularly high reducing ability, and by adding a relatively small amount to a material forming an electron transport layer or an electron injection layer, improvements in luminous brightness or a long lifespan in organic EL devices are achieved. In addition, as a reducing material having a work function of 2.9 eV or less, a combination of two or more of these alkali metals is also preferred, and in particular, a combination including Cs is preferred, for example, a combination of Cs and Na, Cs and K, Cs and Rb, or Cs and Na and K. By including Cs, the reducing ability can be efficiently exerted, and by adding it to a material forming an electron transport layer or an electron injection layer, the luminous brightness of the organic EL device or the lifespan can be improved.

[0678] 9. Cathode in Organic Light Emitting Diodes

[0679] The cathode (108) serves to inject electrons into the light-emitting layer (105) through the electron injection layer (107) and the electron transport layer (106).

[0680] The material forming the negative electrode (108) is not particularly limited as long as it is a material capable of efficiently injecting electrons into the organic layer, but the same material as the material forming the positive electrode (102) can be used. Among these, metals such as tin, indium, calcium, aluminum, silver, copper, nickel, chromium, gold, platinum, iron, zinc, lithium, sodium, potassium, cesium, and magnesium, or alloys thereof (magnesium-silver alloy, magnesium-indium alloy, aluminum-lithium alloy such as lithium fluoride / aluminum, etc.) are preferred. In order to increase the 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 to use a highly stable electrode by doping a small amount of lithium, cesium, or magnesium into the organic layer. Other dopants may include inorganic salts such as lithium fluoride, cesium fluoride, lithium oxide, and cesium oxide. However, they are not limited to these.

[0681] In addition, 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, hydrocarbon-based polymer compounds, etc. The method of fabricating this electrode is also not particularly limited as long as it is conductive, such as resistance heating, electron beam deposition, sputtering, ion plating, and coating.

[0682] 10. Binding agents that may be used on each layer

[0683] The materials used for the hole injection layer, hole transport layer, light-emitting layer, electron transport layer, and electron injection layer above can form each layer individually, but they can also be used by dispersing them in solvent-soluble resins such as polyvinyl chloride, polycarbonate, polystyrene, poly(N-vinylcarbazole), polymethyl methacrylate, polybutyl methacrylate, polyester, polysulfone, polyphenylene oxide, polybutadiene, hydrocarbon resin, ketone resin, phenoxy resin, polyamide, ethylcellulose, vinyl acetate resin, ABS resin, and polyurethane resin, or in curable resins such as phenol resin, xylene resin, petroleum resin, urea resin, melamine resin, unsaturated polyester resin, alkyd resin, epoxy resin, and silicone resin, as polymer binders.

[0684] <<Method for Fabricating Organic Field-Emitting Light Emitting Devices>>

[0685] Each layer constituting an organic EL device can be formed by making the materials constituting each layer into thin films using methods such as deposition, resistance heating deposition, electron beam deposition, sputtering, molecular stacking, printing, inkjet printing, spin coating, casting, or coating. The film thickness of each layer formed in this way is not particularly limited and can be appropriately set according to the properties of the material, but is typically in the range of 2 nm to 5000 nm. Film thickness can usually be measured using a crystal oscillator-type film thickness measuring device. When forming thin films using deposition, the deposition conditions vary depending on the type of material, the crystal structure and assembly structure intended for the film, etc. Generally, the deposition conditions are a boat heating temperature of +50 to +400 ℃ and a vacuum level of 10 -6 ~10 -3 It is desirable to appropriately set the Pa, deposition rate to 0.01 to 50 nm / sec, substrate temperature to -150 to +300 ℃, and film thickness to 2 nm to 5 µm.

[0686] Next, as an example of a method for fabricating an organic EL device, a method for fabricating an organic EL device comprising an anode, a hole injection layer, a hole transport layer, an emitting layer composed of a host material and a dopant material, an electron transport layer, an electron injection layer, and a cathode will be described. After fabricating an anode by forming a thin film of an anode material on a suitable substrate using a deposition method or the like, thin films of a hole injection layer and a hole transport layer are formed on this anode. On this, a host material and a dopant material are co-deposited to form a thin film to form an emitting layer, and an electron transport layer and an electron injection layer are formed on this emitting layer. Additionally, a thin film composed of a cathode material is formed using a deposition method or the like to form a cathode, thereby obtaining the desired organic EL device. Furthermore, in the fabrication of the aforementioned organic EL device, the fabrication order may be reversed, and fabrication can be performed in the order of cathode, electron injection layer, electron transport layer, emitting layer, hole transport layer, hole injection layer, and anode.

[0687] When a DC voltage is applied to the organic EL device obtained in this way, the positive electrode is applied with + polarity and the negative electrode with - polarity, and when a voltage of about 2 to 40 V is applied, light emission can be observed from the transparent or translucent electrode side (positive or negative electrode, and both). In addition, this organic EL device emits light when a pulsed current or an alternating current is applied. Also, the waveform of the applied alternating current can be arbitrarily chosen.

[0688] <<Applications of Organic Field-Emitting Light Emitting Devices>>

[0689] In addition, the present invention can be applied to a display device equipped with an organic EL element or a lighting device equipped with an organic EL element. A display device or lighting device equipped with an organic EL element can be manufactured by a known method, such as connecting an organic EL element according to the present embodiment with a known driving device, and can be driven by appropriately using a known driving method, such as direct current driving, pulse driving, or alternating current driving.

[0690] As display devices, examples include panel displays such as color flat panel displays, flexible displays such as flexible color organic electroluminescent (EL) displays (see, for example, Japanese Patent Publication No. Hei 10-335066, Japanese Patent Publication No. 2003-321546, Japanese Patent Publication No. 2004-281086, etc.). Furthermore, as display methods, examples include matrix and / or segment methods. Also, matrix displays and segment displays may coexist within the same panel.

[0691] In a matrix, pixels for display are arranged two-dimensionally, such as in a grid or mosaic pattern, and characters or images are displayed as a collection of pixels. The shape and size of the pixels are determined according to the application. For example, for image and character display in computers, monitors, and televisions, square pixels with sides of typically 300 μm or less are 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 are arranged, but for color displays, red, green, and blue pixels are arranged to display. In this case, there are typically delta and stripe types. Furthermore, either a linear sequential driving method or an active matrix method can be used as the driving method for this matrix. Although linear sequential driving has the advantage of a simpler structure, the active matrix method may be superior when considering operational characteristics, so it is necessary to distinguish and use them according to the application.

[0692] In the segment method (type), a pattern is formed to display predetermined information, and a determined area is illuminated. Examples include the display of time or temperature on digital clocks or thermometers, the display of operating status on audio devices or electronic cookers, and panel displays in automobiles.

[0693] 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, Japanese Patent Publication No. 2004-119211, etc.). Backlights are primarily used to improve the visibility of non-self-emissive display devices and are used in liquid crystal displays, clocks, audio devices, automotive panels, display boards, and signs. In particular, regarding backlights for liquid crystal displays, especially for computers where thinning is a challenge, considering that conventional methods consist of fluorescent lamps or light guide plates, making thinning difficult, the backlight using the light-emitting element according to the present embodiment is characterized by being thin and lightweight.

[0694] [Example]

[0695] The present invention will be explained more specifically below by way of examples, but the present invention is not limited thereto. First, examples of the synthesis of polycyclic aromatic compounds will be described below.

[0696] Synthesis Example (A0): Synthesis of an Intermediate (IC)

[0697]

[0698] Under a nitrogen atmosphere, 1,2-dibromobenzene (10.0 g) and 4-methoxy-1-naphthol (6.2 g) were dissolved in dimethylformamide (200 ml), cesium carbonate (46.3 g) and tetrakis(triphenylphosphine)palladium (0) (2.3 g) were added, and the mixture was stirred at 150°C for 15 hours. After the reaction, water and ethyl acetate were added to the reaction solution to separate the organic layer, and the mixture was washed with water. Subsequently, the organic layer was concentrated to obtain a crude product. The crude product was purified using a silica gel column (eluent: toluene) to obtain an intermediate (IA) (2.9 g).

[0699]

[0700] Under a nitrogen atmosphere, an intermediate (IA) (2.9g) was dissolved in dichloromethane (100ml) and cooled to -70℃. Thereby, a dichloromethane solution of boron tribromide (1M, 15.6ml) was added dropwise. After raising the temperature to room temperature and stirring for 2 hours, the reaction solution was ice-cooled and water (80ml) was added dropwise. The aqueous layer was extracted with dichloromethane, and the organic layer was combined and concentrated to obtain a crude product. By washing the obtained crude product with dichloromethane, an intermediate (IB) was obtained (2.3g).

[0701]

[0702] Under a nitrogen atmosphere, pyridine (60 ml) was added to intermediate (1-B) (2.3 g) and cooled to 0°C, and trifluoromethanesulfonic acid anhydride (Tf2O, 3.6 g) was added dropwise. After raising the temperature to room temperature and stirring for 2 hours, a sol mix was added to the reaction solution to obtain crystals. By washing the obtained crystals with a sol mix, an intermediate (IC) was obtained (1.8 g).

[0703]

[0704] Synthesis Example (A1): Synthesis of Compound (H-1)

[0705] Under a nitrogen atmosphere, an intermediate (IC) (1.8 g) was dissolved in toluene (100 ml), 4,4,5,5-tetramethyl-2-(10-phenylanthracene-9-yl)-1,3,2-dioxaborane (2.2 g), potassium carbonate (1.4 g), tetrabutylammonium bromide (TBAB, 0.4 g), and bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium (Pd-132, 0.35 g) were added, and the mixture was heated under reflux and stirred for 5 hours. After the reaction, water and ethyl acetate were added to the reaction mixture to obtain a crude product. The obtained crude product was purified using a silica gel shot column (eluent: chlorobenzene) to obtain compound (H-1) (0.5 g).

[0706] EI-MS: m / z=470.

[0707] 1H-NMR (CDCl3): δ=7.89(d, 2H), 7.73(d, 2H), 7.63(m, 3H), 7.57(m, 3H), 7.51(m, 1H), 7.45(d, 1H), 7.33(m, 3H), 7.25(m, 2H), 7.18(m, 4H), 6.85(d, 1H).

[0708]

[0709] Synthesis Example (A2): Synthesis of Compound (H-3)

[0710]

[0711] Compound (H-3) was synthesized using the same method as synthesis example (A1).

[0712] EI-MS: m / z=520.

[0713] Synthesis Example (A3): Synthesis of Compound (H-6)

[0714]

[0715] Compound (H-6) was synthesized using the same method as in synthesis example (A1).

[0716] EI-MS: m / z=546.

[0717] Synthesis Example (A4): Synthesis of Compound (H-26)

[0718]

[0719] Compound (H-26) was synthesized using the same method as in synthesis example (A1).

[0720] EI-MS: m / z=596.

[0721] 1 H-NMR (CDCl3): δ=8.53(d, 1H), 8.12(d, 1H), 8.02(d, 1H), 7.95(m, 2H), 7.75(m, 6H), 7.60(m, 5H), 7.52(m, 2H), 7.33(m, 4H).

[0722] Synthesis Example (A5): Synthesis of Compound (H-35)

[0723]

[0724] Compound (H-35) was synthesized using the same method as synthesis example (A1).

[0725] EI-MS: m / z=470.

[0726] Synthesis Example (A6): Synthesis of Compound (H-280)

[0727]

[0728] Compound (H-280) was synthesized using the same method as in synthesis example (A1).

[0729] EI-MS: m / z=545.

[0730] Synthesis Example (A7): Synthesis of Compound (H-420)

[0731]

[0732] Compound (H-420) was synthesized using the same method as in synthesis example (A1).

[0733] EI-MS: m / z=496.

[0734] Synthesis Example (A8): Synthesis of Compound (H-565)

[0735]

[0736] Compound (H-565) was synthesized using the same method as in synthesis example (A1).

[0737] EI-MS: m / z=662.

[0738] Synthesis Example (A9): Synthesis of Compound (H-640)

[0739]

[0740] Compound (H-640) was synthesized using the same method as in synthesis example (A1).

[0741] EI-MS: m / z=737.

[0742] Synthesis Example (A10): Synthesis of Compound (H-655)

[0743]

[0744] Compound (H-655) was synthesized using the same method as in synthesis example (A1).

[0745] EI-MS: m / z=610.

[0746] Synthesis Example (A11): Synthesis of Compound (H-688)

[0747]

[0748] Compound (H-688) was synthesized using the same method as in synthesis example (A1).

[0749] EI-MS: m / z=760.

[0750] Synthesis Example (A12): Synthesis of Compound (H-725)

[0751]

[0752] Compound (H-1) (1g), 5% platinum-carbon (5% Pt / C, 300mg), heavy water (D2O, 40ml), cyclohexane (cHex, 20ml) and isopropyl alcohol (IPA, 5ml) were placed in a flask under an argon atmosphere and heated to 100°C. After the reaction, water and chloroform were added for fractional extraction, the organic layer was dried with magnesium sulfate and filtered, and the crude obtained by concentrating the organic layer was recrystallized to obtain compound (H-725).

[0753] EI-MS: m / z=492.

[0754] Synthesis Example (A13): Synthesis of Compound (H-771)

[0755]

[0756] Compound (H-771) was synthesized using the same method as in synthesis example (A1).

[0757] EI-MS: m / z=546.

[0758] Synthesis Example (A14): Synthesis of Compound (H-780)

[0759]

[0760] Compound (H-780) was synthesized using the same method as in synthesis example (A12).

[0761] EI-MS: m / z=572.

[0762] Synthesis Example (A15): Synthesis of Compound (H-785)

[0763]

[0764] Compound (H-785) was synthesized using the same method as in synthesis example (A1).

[0765] EI-MS: m / z=838.

[0766] Synthesis Example (A16): Synthesis of Compound (H-798)

[0767]

[0768] Compound (H-798) was synthesized using the same method as in synthesis example (A1).

[0769] EI-MS: m / z=826.

[0770] Synthesis Example (A17): Synthesis of Compound (H-70)

[0771]

[0772] Compound (H-70) was synthesized using the same method as in synthesis example (A1).

[0773] 1 H-NMR (CDCl3): δ=8.49(d, 1H), 8.23(d, 1H), 8.13(d, 1H), 8.05(d, 1H), 7.87(d, 2H), 7.75(m, 4H), 7.62(m, 4H), 7.52(m, 4H), 7.33(m, 4H).

[0774] By appropriately modifying the compounds of the raw materials, other anthracene compounds of the present invention can be synthesized by a method based on the aforementioned synthesis examples.

[0775] Synthesis Example (B1): Synthesis of Compound (D-114)

[0776]

[0777] Under a nitrogen atmosphere, a flask containing methyl 4-methoxysalicylate (50.0 g) and pyridine (dehydrated, 350 ml) was cooled in an ice bath. Next, trifluoromethanesulfonic acid anhydride (154.9 g) was added dropwise to this solution. After the dropwise addition was finished, the ice bath was removed, the mixture was stirred at room temperature for 2 hours, and water was added to stop the reaction. After separating the solution with toluene, methyl 4-methoxy-2-(((trifluoromethyl)sulfonyl)oxy)benzoate (86.0 g) was obtained by purifying with a silica gel short-pass column (eluent: toluene).

[0778]

[0779] Under a nitrogen atmosphere, tetrakis(triphenylphosphine)palladium (0) (Pd(PPh3)4, 2.5 g) was added to a suspension of methyl 4-methoxy-2-(((trifluoromethyl)sulfonyl)oxy)benzoate (23.0 g), (4-(diphenylamino)phenyl)boronic acid (25.4 g), tripotassium phosphate (31.1 g), toluene (184 ml), ethanol (27.6 ml), and water (27.6 ml), and stirred at reflux temperature for 3 hours. The reaction mixture was cooled to room temperature, water and toluene were added to separate the liquids, and the solvent of the organic layer was removed by distillation under reduced pressure. The obtained solid was purified using a silica gel column (eluent: heptane / toluene mixed solvent) to obtain methyl 4'-(diphenylamino)-5-methoxy-[1,1'-biphenyl]-2-carboxylate (29.7g). At this time, referring to the method described on page 94 of “Guide to Organic Chemistry Experiments (1) - Methods for Handling and Separating / Purifying Substances -” published by Kagaku Dojin Co., Ltd., the target product was eluted by gradually increasing the proportion of toluene in the eluent.

[0780]

[0781] Under a nitrogen atmosphere, a tetrahydrofuran (THF, 111.4 ml) solution containing methyl 4'-(diphenylamino)-5-methoxy-[1,1'-biphenyl]-2-carboxylate (11.4 g) was cooled in a water bath, and a THF solution of methyl magnesium bromide (1.0 M, 295 ml) was added dropwise to the solution. After the dropwise addition was finished, the water bath was removed, the temperature was raised to the reflux temperature, and the mixture was stirred for 4 hours. Afterward, the mixture was cooled in an ice bath, an aqueous ammonia chloride solution was added to stop the reaction, ethyl acetate was added to separate the liquids, and the solvent was removed by distillation under reduced pressure. The obtained solid was purified with a silica gel column (eluent: toluene) to obtain 2-(5'-(diphenylamino)-5-methoxy-[1,1'-biphenyl]-2-yl)propan-2-ol (8.3g).

[0782]

[0783] Under a nitrogen atmosphere, a flask containing 2-(5'-(diphenylamino)-5-methoxy-[1,1'-biphenyl]-2-yl)propan-2-ol (27.0 g), the catalyst TAYCACURE-15 (Teika Co., Ltd., 13.5 g), and toluene (162 ml) was stirred at reflux temperature for 2 hours. The reaction mixture was cooled to room temperature, and TAYCACURE-15 was removed by passing it through a silica gel short-pass column (eluent: toluene). Then, the solvent was removed by distillation under reduced pressure to obtain 6-methoxy-9,9'-dimethyl-N,N-diphenyl-9H-fluorene-2-amine (25.8 g).

[0784]

[0785] Under a nitrogen atmosphere, a flask containing 6-methoxy-9,9'-dimethyl-N,N-diphenyl-9H-fluorene-2-amine (25.0 g), pyridine hydrochloride (36.9 g), and N-methyl-2-pyrrolidone (NMP, 22.5 ml) was stirred at reflux temperature for 6 hours. The reaction mixture was cooled to room temperature, and water and ethyl acetate were added to separate the liquids. After removing the solvent by distillation under reduced pressure, 7-(diphenylamino)-9,9'-dimethyl-9H-fluorene-3-ol (22.0 g) was obtained by purification using a silica gel column (eluent: toluene).

[0786]

[0787] Under a nitrogen atmosphere, a flask containing 7-(diphenylamino)-9,9'-dimethyl-9H-fluorene-3-ol (14.1 g), 2-bromo-1,3-difluorobenzene (3.6 g), potassium carbonate (12.9 g), and NMP (30 ml) was heated and stirred at reflux temperature for 5 hours. After the reaction stopped, the reaction mixture was cooled to room temperature, and water was added to collect the precipitate by suction filtration. The obtained precipitate was washed with water, then with methanol, and purified using a silica gel column (eluent: heptane / toluene mixed solvent) to obtain 6,6'-((2-bromo-1,3-phenylene)bis(oxy))bis(9,9-dimethyl-N,N-diphenyl-9H-fluorene-2-amine) (12.6 g). At this time, the proportion of toluene in the eluent was gradually increased to elute the target product.

[0788]

[0789] Under a nitrogen atmosphere, a flask containing 6,6'-((2-bromo-1,3-phenylene)bis(oxy))bis(9,9-dimethyl-N,N-diphenyl-9H-fluorene-2-amine) (11.0 g) and xylene (60.5 ml) was cooled to -40°C, and 2.6 M n-butyllithium hexane solution (5.1 ml) was added dropwise. After the addition was finished, the mixture was stirred at -40°C for 0.5 hours, then heated to 60°C and stirred for 3 hours. Afterward, the reaction mixture was depressurized to remove low-boiling point components by distillation, then cooled to -40°C, and triboron bromide (4.3 g) was added. After raising the temperature to room temperature and stirring for 0.5 hours, the mixture was cooled to 0°C, N-ethyl-N-isopropylpropane-2-amine (3.8 g) was added, and the mixture was heated and stirred at 125°C for 8 hours. The reaction mixture was cooled to room temperature, sodium acetate aqueous solution was added to stop the reaction, and then toluene was added to separate the liquids. The organic layer was purified by a silica gel short-pass column, then by a silica gel column (eluent: a mixed solution of heptane / toluene = 4 / 1 (volume ratio)), and further by an activated carbon column (eluent: toluene) to obtain compound (D-114) (1.2 g).

[0790]

[0791] The structure of the compound (D-114) obtained by NMR measurement was confirmed.

[0792] 1 H-NMR (400MHz, CDCl3): δ=8.64(s, 2H), 7.75(m, 3H), 7.69(d, 2H), 7.30(t, 8H), 7.25(s, 2H), 7.20(m, 10H), 7.08(m, 6H), 1.58(s, 12H).

[0793] Synthesis Example (B2): Synthesis of Compound (D-52)

[0794]

[0795] Under a nitrogen atmosphere, 3-bromo-N,N-diphenylaniline (35g), 4-tert-butylaniline (19.3g), dichlorobis(di-tert-butyl(4-dimethylaminophenyl)phosphino)palladium (Pd-132, 76mg) as a palladium catalyst, sodium-tert-butoxide (NaOtBu, 15.6g), and xylene (200ml) were placed in a flask and heated at 120°C for 2 hours. After the reaction was finished, water and ethyl acetate were added to the reaction mixture and stirred, after which the organic layer was separated and washed with water. Subsequently, the crude product obtained by concentrating the organic layer was purified using a silica gel shot column (eluent: toluene / heptane = 1 / 1 (volume ratio)) to obtain an intermediate (I-1) (40g).

[0796]

[0797] Under a nitrogen atmosphere, intermediate (I-1) (10.0 g), intermediate (I-2) (12.3 g), Pd-132 (0.2 g) as a palladium catalyst, NaOtBu (3.7 g), and xylene (60 ml) were placed in a flask and heated at 120°C for 1 hour. After the reaction was finished, water and ethyl acetate were added to the reaction mixture and stirred, after which the organic layer was separated and washed with water. Subsequently, the crude product obtained by concentrating the organic layer was purified using a silica gel shot column (eluent: toluene / heptane = 1 / 4 (volume ratio)) to obtain intermediate (I-3) (18.5 g).

[0798]

[0799] To a flask containing intermediate (I-3) (15.0 g) and tert-butylbenzene (100 ml), 1.56 M tert-butyllithium pentane solution (50.1 ml) was added at 0°C under a nitrogen atmosphere. After the dropwise addition was finished, the temperature was raised to 70°C and stirred for 0.5 hours, after which the component with a lower boiling point than tert-butylbenzene was removed by distillation under reduced pressure. The mixture was cooled to -50°C and boron tribromide (19.1 g) was added, the temperature was raised to room temperature and stirred for 0.5 hours. Afterward, the mixture was cooled again to 0°C and N,N-diisopropylethylamine (9.9 g) was added. 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 solution was cooled to room temperature, followed by the addition of an aqueous sodium acetate solution cooled in an ice bath, and then ethyl acetate to separate the liquids. After concentrating the organic layer, it was purified using a silica gel shot column (eluent: chlorobenzene). The obtained crude product was recrystallized with toluene to obtain compound (D-52) (9.6 g).

[0800] EI-MS: m / z=812.

[0801]

[0802] Synthesis Example (B3): Synthesis of Compound (D-7)

[0803]

[0804] Compound (D-7) was synthesized using the same method as synthesis example (B2).

[0805] The structure of the compound obtained by NMR measurement was confirmed.

[0806] 1 H-NMR (500MHz, CDCl3): δ=1.47(s, 36H), 2.17(s, 3H), 5.97(s, 2H), 6.68(d, 2H), 7.28(d, 4H), 7.49(dd, 2H), 7.67(d, 4H), 8.97(d, 2H).

[0807] Synthesis Example (B4): Synthesis of Compound (D-69)

[0808]

[0809] Compound (D-69) was synthesized using the same method as synthesis example (B2).

[0810] The structure of the compound obtained by NMR measurement was confirmed.

[0811] 1 H-NMR (CDCl3): δ=1.20(s, 9H), 1.37(s, 18H), 1.46(s, 9H), 1.47(s, 9H), 2.18(s, 3H), 5.97(s, 1H), 6.08(d, 1H), 6.63(d, 1H), 6.66(d, 1H), 7.20(d, 2H), 7.27(d, 2H), 7.32(dd, 1H), 7.48(dd, 1H), 7.61(t, 1H), 7.67(d, 2H), 8.84(d, 1H), 8.94(d, 1H).

[0812] Synthesis Example (B5): Synthesis of Compound (D-202)

[0813]

[0814] Compound (D-202) was synthesized using the same method as in Synthesis Example (B2). The structure of the obtained compound was confirmed by NMR measurement.

[0815] 1 H-NMR: δ=1.1(s, 9H), 1.4(s, 9H), 1.5(s, 9H), 1.5(s, 9H), 1.5(s, 9H), 2.2(s, 3H), 5.9(s, 1H), 6.1(s, 1H), 6.7(m, 2H), 7.0(d, 2H), 7.1(d, 2H), 7.2(d, 1H), 7.3(m, 2H), 7.4(m, 1H), 7.5(m, 1H), 7.6(dd, 1H), 7.7(m, 3H), 8.9(d, 1H), 8.9(d, 1H).

[0816] Synthesis Example (B6): Synthesis of Compound (D-215)

[0817]

[0818] Compound (D-215) was synthesized using the same method as synthesis example (B2).

[0819] The structure of the compound obtained by NMR measurement was confirmed.

[0820] 1 H-NMR (CDCl3): δ=1.21(s, 18H), 1.36(s, 36H), 1.48-1.66(m, 12H), 1.89(s, 3H), 6.18(s, 2H), 6.78(s, 2H), 7.22(d, 4H), 7.25-7.28(m, 2H), 7.59(t, 2H), 8.86(d, 2H).

[0821] Synthesis Example (B7): Synthesis of Compound (D-201)

[0822]

[0823] Compound (D-201) was synthesized using the same method as synthesis example (B2).

[0824] The structure of the compound obtained by NMR measurement was confirmed.

[0825] 1 H-NMR (CDCl3): δ=0.62(t, 6H), 0.75(t, 6H), 1.29(s, 12H), 1.43(s, 12H), 1.62(q, 4H), 1.75(q, 4H), 5.63(s, 2H), 6.70(d, 2H), 6.86(m, 2H), 6.92(d, 4H), 7.05(m, 4H), 7.14(d, 4H), 7.38(m, 6H), 8.85(d, 2H).

[0826] Synthesis Example (B8): Synthesis of Compound (D-270)

[0827]

[0828] Compound (D-270) was synthesized using the same method as synthesis example (B2).

[0829] The structure of the compound obtained by NMR measurement was confirmed.

[0830] 1H-NMR (CDCl3): δ=1.32(s, 18H), 1.46(s, 18H), 5.55(s, 2H).

[0831] Synthesis Example (B9): Synthesis of Compound (D-206)

[0832]

[0833] Compound (D-206) was synthesized using the same method as synthesis example (B2).

[0834] The structure of the compound obtained by NMR measurement was confirmed.

[0835] 1 H-NMR (CDCl3): δ=1.08(s, 6H), 1.27(s, 6H), 1.42(s, 6H), 1.46(s, 9H), 1.47(s, 9H), 1.48(s, 6H), 1.69-1.81(m, 8H), 2.18(s, 3H), 5.97(s, 1H), 6.06(s, 1H), 6.52(s, 1H), 6.67(d, 1H), 7.08(dd, 1H), 7.25-7.29(m, 3H), 7.48(dd, 1H), 7.59(d, 1H), 7.67(d, 2H), 8.89(s, 1H), 8.97(d, 1H).

[0836] Synthesis Example (B10): Synthesis of Compound (D-18)

[0837]

[0838] A flask containing intermediate (I-4) (15 g) and toluene (300 ml) was heated to 70°C under a nitrogen atmosphere to completely dissolve the intermediate (I-4). After cooling the flask to -20°C, tetramethylethylenediamine (TMEDA, 20.8 g) and a 1.00 M mixed solution of sec-butyllithium cyclohexane and n-hexane (89 ml) were added. The temperature was raised to 0°C and stirred for 3 hours, then 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (33.3 g) was added and refluxed for 1 hour. Water and toluene were added to separate the liquids, and the solvent of the organic layer was removed by distillation under reduced pressure. The obtained solid was washed using Sol Mix A-11 (product name: Japan Alcohol Sales Co., Ltd.), dissolved in toluene, and left at 0°C for 1 hour. The precipitated precipitate was filtered, and the filtrate was passed through a silica gel column (eluent: toluene / heptane = 1 / 5 mixed solvent (volume ratio)). After removing the solvent by distillation, the intermediate (I-5) (9.5g) was obtained as a white solid by redepositing with a mixed solvent of ethyl acetate and Sol Mix A-11.

[0839]

[0840] A flask containing intermediate (I-5) (8.7g), aluminum chloride (12.5g), N,N-diisopropylethylamine (DIPEA, 6.0g), and chlorobenzene (44ml) was stirred at 120°C for 1 hour under a nitrogen atmosphere. The reaction mixture, cooled to room temperature, was poured into ice water (200ml), and toluene was added to extract the organic layer. The solvent of the organic layer was removed by distillation under reduced pressure, and the resulting solid was dissolved in chloroform and passed through a silica gel short-pass column (eluent: toluene). The crude product obtained by distillation under reduced pressure was reprecipitated using cyclopentylmethyl ether and sol mix A-11 to obtain compound (D-18) (6.2g, yield 70%) as a yellow solid.

[0841]

[0842] The structure of the compound obtained by NMR measurement was confirmed.

[0843] 1 H-NMR (400MHz, CDCl3): δ=8.95(d, 2H), 7.45(dd, 6H), 7.13(d, 4H), 7.08-7.04(m, 4H), 6.95-6.88(m, 6H), 6.75(d, 2H), 5.56(s, 2H), 1.46(s, 18H), 1.33(s, 18H).

[0844] Synthesis Example (B11): Synthesis of Compound (D-155)

[0845]

[0846] Under a nitrogen atmosphere, a flask containing 7-(diphenylamino)-9,9'-dimethyl-9H-fluorene-3-ol (9.0 g), 1,2-dibromo-3-fluorobenzene (7.9 g), potassium carbonate (8.2 g), and NMP (45 ml) was heated and stirred at reflux temperature for 2 hours. After the reaction stopped, the reaction mixture was cooled to room temperature, and water was added to collect the precipitate by suction filtration. The obtained precipitate was washed with water and then with a sol mixer, and then purified using a silica gel column (eluent: heptane / toluene = 3 / 1 (volume ratio)) to obtain 6-(2,3-dibromophenoxy)-9,9-dimethyl-N,N-diphenyl-9H-fluorene-2-amine (12.4 g, yield: 84.8%).

[0847]

[0848] Under a nitrogen atmosphere, a flask containing 6-(2,3-dibromophenoxy)-9,9-dimethyl-N,N-diphenyl-9H-fluorene-2-amine (10.0 g), di([1,1'-biphenyl]-4-yl)amine (5.3 g), palladium acetate (0.15 g), dicyclohexyl(2',6'-diisopropoxy-[1,1'-biphenyl]-2-yl)phosphane (0.61 g), NaOtBu (2.4 g), and toluene (35 ml) was heated at 80°C for 6 hours. After cooling the reaction mixture to room temperature, water and toluene were added to separate the liquids. Furthermore, by purifying with a silica gel column (eluent: heptane / toluene = 2 / 1 (volume ratio)), 6-(2-bromo-3-(di([1,1'-biphenyl]-4-yl)amino)phenoxy)-9,9-dimethyl-N,N-diphenyl-9H-fluorene-2-amine (7.4g, yield: 53.1%) was obtained.

[0849]

[0850] Under a nitrogen atmosphere, 6-(2-bromo-3-(di([1,1'-biphenyl]-4-yl)amino)phenoxy)-9,9-dimethyl-N,N-diphenyl-9H-fluorene-2-amine) (7.9 g) and THF (42 ml) were placed in a flask, cooled to -40°C, and 1.6 M n-butyllithium hexane solution (6 ml) was added dropwise. After the addition was finished, the mixture was stirred at this temperature for 1 hour, and then trimethylborate (1.7 g) was added. The mixture was heated to room temperature and stirred for 2 hours. Afterward, water (100 ml) was slowly added dropwise. Next, the reaction mixture was extracted with ethyl acetate, dried with anhydrous sodium sulfate, and then the drying agent was removed to obtain dimethyl(2-(di([1,1'-biphenyl]-4-yl)amino)-6-((7-(diphenylamino)-9,9-dimethyl-9H-fluorene-3-yl)oxy)phenyl)boronate (7.0 g, yield: 100%).

[0851]

[0852] Under a nitrogen atmosphere, dimethyl(2-(di([1,1'-biphenyl]-4-yl)amino)-6-((7-(diphenylamino)-9,9-dimethyl-9H-fluorene-3-yl)oxy)phenyl)boronate (6.5g), aluminum chloride (10.3g), and toluene (39ml) were placed in a flask and stirred for 3 minutes. Then, N-ethyl-N-isopropylpropane-2-amine (2.5g) was added, and the mixture was heated and stirred at 105°C for 1 hour. After heating was finished, the reaction mixture was cooled, and ice water (20ml) was added. Afterwards, the reaction mixture was extracted with toluene, and the organic layer was purified using a silica gel short-pass column (eluent: toluene), followed by a silica gel column (eluent: heptane / toluene = 3 / 1 (volume ratio)), then reprecipitated with heptane, and further purified using an NH2 silica gel column (eluent: heptane / toluene = 1 / 1 (volume ratio)). Finally, by sublimation purification, compound (D-155) (0.74 g, yield: 12.3%) was obtained.

[0853]

[0854] The structure of the compound obtained by NMR measurement was confirmed.

[0855] 1 H-NMR (CDCl3): δ=9.22(s, 1H), 8.78(s, 1H), 7.96(d, 2H), 7.80∼7.77(m, 6H), 7.71(d, 1H), 7.59∼7.44(m, 8H), 7.39(t, 1H), 7.32∼7.29(m, 4H), 7.71(d, 1H), 7.19(dd, 4H), 7.12∼7.06(m, 4H), 7.00(d, 1H), 6.45(d, 1H), 1.57(s, 6H).

[0856] Synthesis Example (B12): Synthesis of Compound (D-249)

[0857]

[0858] Compound (D-249) was synthesized using the same method as synthesis example (B2).

[0859] EI-MS: m / z=756.

[0860] Synthesis Example (B13): Synthesis of Compound (D-255)

[0861]

[0862] Compound (D-255) was synthesized using the same method as synthesis example (B2).

[0863] EI-MS: m / z=811.

[0864] Synthesis Example (B14): Synthesis of Compound (D-253)

[0865]

[0866] Compound (D-253) was synthesized using the same method as synthesis example (B2).

[0867] EI-MS: m / z=889.

[0868] Synthesis Example (B15): Synthesis of Compound (D-254)

[0869]

[0870] Compound (D-254) was synthesized using the same method as synthesis example (B2).

[0871] EI-MS: m / z=867.

[0872] Synthesis Example (B16): Synthesis of Compound (D-264)

[0873]

[0874] Compound (D-264) was synthesized using the same method as synthesis example (B2).

[0875] EI-MS: m / z=944.

[0876] Synthesis Example (B17): Synthesis of Compound (D-300)

[0877]

[0878] Tri-p-tolylamine (0.287 g, 1.00 mmol), tri-boron iodide (0.783 g, 2.00 mmol), and o-dichlorobenzene (10.0 mL) were heated and stirred at 150°C for 2 hours under a nitrogen atmosphere. The reaction mixture was cooled to room temperature, and 2-isopropenphenylmagnesium bromide (5.25 mL, 1.2 M, 6.30 mmol) was added. Afterward, the mixture was filtered using a Florisil shortpass column (eluent: toluene), and the solvent was removed by distillation under reduced pressure. The obtained crude product was isolated and purified by washing with hexane, and 2,8-dimethyl-10-(2-(pro-1-phen-2-yl)phenyl)-5-(p-tolyl)-5,10-dihydrodibenzo[b,e][1,4]azabolin was obtained in a yield of 0.309 g, with a yield of 75%.

[0879]

[0880] The structure of the compound obtained by NMR measurement was confirmed.

[0881] 1 H-NMR (CDCl3): δ=2.05(s, 3H), 2.31(s, 6H), 2.54(s, 3H), 4.78(s, 2H), 6.74(d, 2H) 7.20-7.28(m, 4H), 7.37-7.48(m, 5H), 7.56(d, 1H), 7.68(s, 2H).

[0882] 13 C-NMR (CDCl3): δ=20.6(s, 2C), 21.3(s, 1C), 23.8(s, 1C), 116.7(s, 2C), 116.9(s, 1C), 126.0(d, 2C), 126.8(s, 1C), 128.2(s, 2C), 130.0(d, 4C), 131.4(d, 4C), 133.0(s, 1C), 133.7(s, 2C), 136.4(s, 2C), 138.6(s, 1C), 139.3(s, 1C), 145.1(s, 1C), 147.0(d, 2C).

[0883] 2,8-dimethyl-10-(2-(pro-1-phen-2-yl)phenyl)-5-(p-tolyl)-5,10-dihydrodibenzo[b,e][1,4]azabolin (82.2 mg, 0.20 mmol), scandium trifluoromethanesulfonic acid (0.100 g, 0.20 mmol), and 1,2-dichloroethane (55.0 mL) were heated and stirred at 95°C for 24 hours under a nitrogen atmosphere. After cooling the reaction mixture to room temperature, it was filtered using a Florisil shortpass column (eluent: toluene), and the solvent was removed by distillation under reduced pressure. The obtained crude product was isolated and purified using a silica gel column (eluent: hexane / toluene = 6 / 1 (volume ratio)) to obtain compound (D-300) at a yield of 32.0 mg, with a yield of 39%.

[0884]

[0885] The structure of the compound obtained by NMR measurement was confirmed.

[0886] 1 H-NMR (CDCl3): δ=1.98(s, 6H), 2.48(s, 3H), 2.53(s, 3H), 2.76(s, 3H), 6.61(d, 1H), 6.75(d, 1H), 7.14-7.31(m, 4H), 7.40-7.47(m, 3H), 7.57(dt, 1H), 7.81(d, 1H), 8.44(d, 1H), 8.50(s, 1H).

[0887] 13C-NMR (CDCl3): δ=20.9(s, 1C), 21.4(s, 1C), 24.3(s, 1C), 32.6(s, 2C), 43.5(s, 1C), 114.0(s, 1C), 116.6(s, 1C), 124.7(s, 1C), 125.8(s, 1C), 127.0(s, 1C), 128.4(s, 2C), 130.1(s, 2C), 130.5(s, 1C), 131.4(s, 2C), 133.0(s, 1C), 135.2(s, 1C), 135.5(s, 1C), 137.7(s, 1C), 138.4(s, 1C), 139.5(s, 1C), 144.3(s, 1C), 145.4(s, 1C), 151.4(s, 1C), 159.5(s, 1C).

[0888] By appropriately modifying the compounds of the raw materials, other polycyclic aromatic compounds of the present invention can be synthesized by a method based on the synthesis example described above.

[0889] Next, to explain the present invention in more detail, examples of organic EL devices using compounds of the present invention are shown, but the present invention is not limited to these.

[0890] Evaluation of Deposition-Type Organic EL Devices

[0891] Organic EL devices of Examples 1 to 42 and Comparative Examples 1 to 4 were fabricated, and each had 1000 cd / m² 2 The driving voltage (V), external quantum efficiency (%), and the time maintained at 90% or more of the initial brightness (device lifespan), which are characteristics during light emission, were measured.

[0892] The quantum efficiency of a light-emitting device consists of internal quantum efficiency and external quantum efficiency. Internal quantum efficiency represents the ratio at which external energy injected as electrons (or holes) into the light-emitting layer of the light-emitting device is purely converted into photons. On the other hand, external quantum efficiency is calculated based on the amount of photons emitted to the outside of the light-emitting device. Since some of the photons generated in the light-emitting layer are absorbed within the device or continuously reflected and are not emitted to the outside, the external quantum efficiency is lower than the internal quantum efficiency.

[0893] The method for measuring external quantum efficiency is as follows. Using the R6144 voltage / current generator manufactured by Advantist, the device brightness is 1000 cd / m² 2 The device was induced to emit light by applying a voltage that becomes [this]. Using the SR-3AR spectroradiometer manufactured by TOPCON, the spectral radiance in the visible light region was measured from a direction perpendicular to the emission surface. Assuming the emission surface is a perfectly diffuse surface, the value obtained by dividing the measured spectral radiance value of each wavelength component by the wavelength energy and multiplying by π is the number of photons at each wavelength. Next, the number of photons over the entire observed wavelength range was integrated to obtain the total number of photons emitted from the device. The value obtained by dividing the applied current value by the small charge is the number of carriers injected into the device, and the value obtained by dividing the total number of photons emitted from the device by the number of carriers injected into the device is the external quantum efficiency.

[0894] <Example 1>

[0895] The layer configuration of the organic EL device prepared in Example 1 is shown in Table 1.

[0896] [Table 1]

[0897]

[0898] A glass substrate of 26 mm × 28 mm × 0.7 mm (manufactured by Offtoscience Co., Ltd.), in which an ITO film of 180 nm thickness was prepared by sputtering and polished to 150 nm, was used as a transparent support substrate. This transparent support substrate was fixed to a substrate holder of a commercially available deposition apparatus (manufactured by Joshu Industry Co., Ltd.), and a tantalum deposition boat containing HI, HAT-CN, HT-1, HT-2, compound (H-1), compound (D-114), ET-1, and ET-2, respectively, and an aluminum nitride deposition boat containing Liq, magnesium, and silver, respectively, were mounted.

[0899] Each of the following layers was formed sequentially on the ITO film of the transparent support substrate. The vacuum chamber was 5×10 -4The pressure was reduced to Pa, and first, HI was heated and deposited to a film thickness of 40 nm to form a hole injection layer 1. Next, HAT-CN was heated and deposited to a film thickness of 5 nm to form a hole injection layer 2. Next, HT-1 was heated and deposited to a film thickness of 45 nm to form a hole transport layer 1. Next, HT-2 was heated and deposited to a film thickness of 10 nm to form a hole transport layer 2. Next, compound (H-1) and compound (D-114) were heated simultaneously and deposited to a film thickness of 25 nm to form an emissive layer. The deposition rate was adjusted so that the mass ratio of compound (H-1) and compound (D-114) was approximately 98:2. Next, ET-1 was heated and deposited to a film thickness of 5 nm to form an electron transport layer 1. Next, ET-2 and Liq were heated simultaneously and deposited to a film thickness of 25 nm to form electron transport layer 2. The deposition rate was controlled so that the mass ratio of ET-2 to Liq was approximately 50:50. The deposition rate of each layer was 0.01 to 1 nm / sec. Subsequently, Liq was heated and deposited at a deposition rate of 0.01 to 0.1 nm / sec to a film thickness of 1 nm, and then magnesium and silver were heated simultaneously and deposited to a film thickness of 100 nm to form a cathode, thereby obtaining an organic EL device. At this time, the deposition rate was controlled between 0.1 and 10 nm / sec so that the atomic ratio of magnesium to silver was 10:1.

[0900] A DC voltage is applied using the ITO electrode as the anode and the magnesium / silver electrode as the cathode, and 1000 cd / m² 2 When measuring the characteristics during light emission, blue light emission was obtained. The driving voltage was 4.21 V, the external quantum efficiency was 6.78%, and the device lifetime was 263 hours.

[0901] This indicates the material of each layer in the organic EL device fabricated in Example 1. "HI" is N 4 ,N 4 '-diphenyl-N 4 ,N4 '-bis(9-phenyl-9H-carbazole-3-yl)-[1,1'-biphenyl]-4,4'-diamine, "HAT-CN" is 1,4,5,8,9,12-hexaazatriphenylenehexacarbonitrile, "HT-1" is N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazole-3-yl)phenyl)-9H-fluorene-2-amine, and "HT-2" is N,N-bis(4-(dibenzo[b,d]furan-4-yl)phenyl)-[1,1':4',1"-terphenyl]-4-amine. Also, "ET-1" is, 1-(4-(10-([1,1'-biphenyl]-4-yl)anthracene-9-yl)phenyl)-2-ethyl-1H-benzo[d]imidazole, and “ET-2” is 9,9'-[(5-(6-(1,1'-biphenyl)-4-yl)-2-phenylpyrimidine-4-yl)-1,3-phenylene]bis(9H-carbazole). “Liq”, and, together with the comparative compounds (1) to (4) used in the comparative examples described below, the chemical structures are shown below.

[0902]

[0903] <Examples 2–49 and Comparative Examples 1–4>

[0904] An organic EL device was fabricated in the same procedure as in Example 1 (except that the combination of host and dopant in the light-emitting layer was changed according to Tables 2A to 2D below), and EL characteristics were measured.

[0905] [Table 2A]

[0906]

[0907] [Table 2B]

[0908]

[0909] [Table 2C]

[0910]

[0911] [Table 2D]

[0912]

[0913] For the above, some of the compounds according to the present invention have been evaluated as materials for organic EL devices and shown to be excellent materials, but other compounds that have not been evaluated also have the same basic framework and have a similar overall structure, and it can be understood by those skilled in the art that they are equally excellent materials for organic EL devices. Industrial applicability

[0914] According to a preferred embodiment of the present invention, by fabricating an organic EL device having a light-emitting layer comprising an anthracene compound of a specific structure and a polycyclic aromatic compound, an organic EL device with excellent driving voltage, quantum efficiency, and device lifespan can be provided. Explanation of the symbols

[0915] 100: Organic field light-emitting diode 101: Board 102: Anode 103: Hole injection layer 104: Precision Transport Layer 105: Emissive layer 106: Electron transport layer 107: Electron injection layer 108: Cathode

Claims

Claim 1 delete Claim 2 delete Claim 3 delete Claim 4 delete Claim 5 delete Claim 6 delete Claim 7 delete Claim 8 delete Claim 9 delete Claim 10 delete Claim 11 delete Claim 12 delete Claim 13 delete Claim 14 delete Claim 15 delete Claim 16 delete Claim 17 delete Claim 18 delete Claim 19 Compounds represented by the following formula (HA): Among the above formula (HA"), R 2 , R 3 , R 6 , R 7 and R 9 Each is independently hydrogen, an aryl having 6 to 30 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, an alkyl having 1 to 12 carbon atoms, a cycloalkyl having 3 to 16 carbon atoms, or the following formula (BO) It is a monovalent group obtained by removing one hydrogen from a compound represented by, and R 21 ~R 30 Each is independently hydrogen, an aryl having 6 to 16 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, an alkyl having 1 to 12 carbon atoms, or a cycloalkyl having 3 to 16 carbon atoms, provided that R 21 ~R 30 Any one of them constitutes L, and X is each independently >O, >NR, or >C(-R)2, and R of the >NR and >C(-R)2 is each independently an aryl having 6 to 16 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, an alkyl having 1 to 12 carbon atoms, or a cycloalkyl having 3 to 16 carbon atoms, and as X, the two Rs of the >C(-R)2 may be bonded to each other to form a ring, and R is -O-, -S-, -C(-R)2-, or R by means of a single bond 21 or R 30 It may be bonded to, and R of the -C(-R)2- is an alkyl having 1 to 12 carbon atoms or a cycloalkyl having 3 to 16 carbon atoms, L is a single bond, and at least one hydrogen in each of the compounds represented by the formula (HA") may be substituted with a substituted silyl, cyano, halogen, or deuterium. Claim 20 In Paragraph 19, R 2 , R 3 , R 6 , R 7 All of it is hydrogen, and R 9 A compound in which is a monovalent group obtained by removing one hydrogen from an unsubstituted aryl having 6 to 30 carbon atoms or a compound represented by the formula (BO), and is a monovalent group obtained by removing one hydrogen from an unsubstituted aryl having 6 to 12 carbon atoms or a compound represented by the formula (BO), wherein R is an unsubstituted aryl having 6 to 16 carbon atoms, and L is a compound in which all are single bonds. Claim 21 Compounds represented by the following formula (HC') or the following formula (HE'): Among the above equations (HC') and (HE'), R 1 , R 2 , R 3 , R 6 , R 7 and R 8 Each is independently hydrogen, an aryl having 6 to 30 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, an alkyl having 1 to 12 carbon atoms, a cycloalkyl having 3 to 16 carbon atoms, or the following formula (BO) It is a monovalent group obtained by removing one hydrogen from a compound represented by, and R 21 ~R 30 Each is independently hydrogen, an aryl having 6 to 16 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, an alkyl having 1 to 12 carbon atoms, or a cycloalkyl having 3 to 16 carbon atoms, and R 21 ~R 30 Adjacent groups may be bonded to form an aryl ring having 6 to 10 carbon atoms or a heteroaryl ring having 2 to 10 carbon atoms, and at least one hydrogen in the formed ring may be substituted with an aryl having 6 to 16 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, an alkyl having 1 to 12 carbon atoms, or a cycloalkyl having 3 to 16 carbon atoms, provided, however, R 21 ~R 30 One of them constitutes L, and X is each independently >O, >S, >NR, >C(-R)2, or >Si(-R)2, and R of >NR, >C(-R)2 and >Si(-R)2 is each independently an aryl having 6 to 16 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, an alkyl having 1 to 12 carbon atoms, or a cycloalkyl having 3 to 16 carbon atoms, and R of >NR as X is -O-, -S-, -C(-R)2-, or R by means of a single bond 21 or R 30 It may be bonded to, and R of the above -C(-R)2- is an alkyl having 1 to 12 carbon atoms or a cycloalkyl having 3 to 16 carbon atoms, and L is each independently a single bond, an alkylene having 1 to 6 carbon atoms, an arylene having 6 to 16 carbon atoms that may be substituted with an alkyl having 1 to 5 carbon atoms or a cycloalkyl having 5 to 10 carbon atoms, or a heteroarylene having 2 to 15 carbon atoms that may be substituted with an alkyl having 1 to 5 carbon atoms or a cycloalkyl having 5 to 10 carbon atoms, and at least one hydrogen in each of the compounds represented by the above formulas (HC') and (HE') may be substituted with a substituted silyl, cyano, halogen, or deuterium. Claim 22 In Paragraph 21, R 2 , R 3 , R 6 , R 7 All of it is hydrogen, and R 1 and R 8 A compound in which each is an independent, unsubstituted aryl having 6 to 30 carbon atoms, and L is a single bond. Claim 23 delete Claim 24 delete

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