Transverse current suppression material, carbazole compound, hole injection layer, and organic electroluminescent element

Abstract

To provide a transverse current suppression material, a carbazole compound, and a hole injection layer using these materials, which suppress transverse current in organic electroluminescent elements, and an organic electroluminescent element with excellent drive voltage, luminous efficiency, durability, and low transverse current.SOLUTION: A transverse current suppression material for organic electroluminescent elements is represented by Formula (1) [In Formula (1), A is represented by Formula (2) or (3) below and B is represented by Formula (4) below].SELECTED DRAWING: Figure 1

Description

[Technical Field]

[0001] This disclosure relates to transverse current suppression materials, carbazole compounds, hole injection layers, and organic electroluminescent devices for use in organic electroluminescent devices. [Background technology]

[0002] In organic electroluminescent devices, the hole injection layer is doped with an electron-donor triarylamine compound and an electron-acceptor p-dopant. Doping the triarylamine compound with a p-dopant generates holes, increasing the amount of holes injected into the organic electroluminescent device and reducing the device's driving voltage. Normally, when an electric field is applied to an organic electroluminescent device, holes move perpendicularly from the anode to the cathode along the direction of the electric field. However, in a hole injection layer doped with a p-dopant in a triarylamine compound, the generated holes can move more freely, and may move horizontally relative to the anode film. Generally, in organic electroluminescent displays, the hole injection layer and hole transport layer are used in common for multiple pixels. Therefore, if such a lateral current occurs, unintended pixels may emit light, degrading image quality. For example, Non-Patent Literature 1 discloses crosstalk as a phenomenon in which adjacent pixels emit light. [Prior art documents] [Non-patent literature]

[0003] [Non-Patent Document 1] Journal of Information Display, 2018, Vol. 19, p. 61 [Overview of the project] [Problems that the invention aims to solve]

[0004] In organic electroluminescent displays where a common hole injection layer and hole transport layer are applied to multiple pixels, conventional hole injection and hole transport layers generate transverse currents that flow horizontally with respect to the anode film, resulting in a deterioration of the image quality of the organic electroluminescent display.

[0005] Therefore, one aspect of this disclosure is aimed at providing a lateral current suppressing material, a carbazole compound, and a hole injection layer using the same, as well as an organic electroluminescent element that is excellent in driving voltage, luminescence efficiency, and durability, and has low lateral current. [Means for solving the problem]

[0006] According to one aspect of this disclosure, a transverse current suppression material for an electroluminescent device represented by formula (1) is provided:

[0007] [ka]

[0008] During the ceremony, A is represented by equation (2) or (3); B is represented by equation (4);

[0009] [ka]

[0010] During the ceremony, Ar 1 ~Ar 3 Each of them operates independently. A monocyclic, linked, or fused aromatic hydrocarbon group having 6 to 30 carbon atoms, which may be substituted, A monocyclic, linked, or fused heteroaromatic group having 3 to 30 carbon atoms, which may be substituted; Ar 1 ~Ar 3 At least one of them is a base represented by one of equations (5) to (21);

[0011] [ka]

[0012] [ka]

[0013] During the ceremony, R 1 represents a methyl group or a hydrogen atom; R 2 and R 3 Each of these independently represents a phenyl group, biphenylyl group, naphthyl group, phenanthryl group, dibenzofuranyl group, or dibenzothienyl group, which may be substituted with a methyl group.

[0014] X represents either an oxygen atom or a sulfur atom.

[0015] In other aspects of this disclosure, a carbazole compound represented by formula (22) or formula (23) is provided:

[0016] [ka]

[0017] During the ceremony, Ar 6 Each of these is an independent base selected from the following equations (24) to (45).

[0018] [ka]

[0019] [ka]

[0020] [ka]

[0021] In the formula: R 4 represents a biphenylyl group, naphthyl group, phenanthryl group, dibenzofuranyl group, or dibenzothienyl group, which may be substituted with a methyl group.

[0022] R 5 each independently represent a methyl group or a hydrogen atom.

[0023] R 6 represents a phenyl group, biphenylyl group, naphthyl group, phenanthryl group, dibenzofuranyl group, or dibenzothienyl group, which may be substituted with a methyl group.

[0024] R 7 and R 8 each independently represent a phenyl group, biphenylyl group, naphthyl group, phenanthryl group, dibenzofuranyl group, or dibenzothienyl group, which may be substituted with a methyl group, and at least one of them is a biphenylyl group, naphthyl group, phenanthryl group, dibenzofuranyl group, or dibenzothienyl group, which may be substituted with a methyl group.

[0025] In formula (22) and formula (23), Ar 6 is a group selected from formulas (24) to (31), Ar 5 is a group selected from formulas (24) to (45), and Ar 4 is an optionally substituted monocyclic, linked, or condensed aromatic hydrocarbon group having 6 to 30 carbon atoms, or an optionally substituted monocyclic, linked, or condensed heteroaromatic group having 3 to 30 carbon atoms.

[0026] In formula (22) and formula (23), Ar 6 is a group selected from formulas (32) to (44), Ar 4 and Ar 5Each of these groups is independently represented by a group selected from formulas (24) to (45), or by a monocyclic, linked, or fused aromatic hydrocarbon group having 6 to 30 carbon atoms, which may be substituted, or by a monocyclic, linked, or fused heteroaromatic group having 3 to 30 carbon atoms, which may be substituted.

[0027] According to other aspects of this disclosure, The first compound and, A hole injection layer containing a second compound, The first compound described above is The above-mentioned lateral current suppressing material, or The above-mentioned carbazole compound, A hole injection layer is provided in which the second compound is an electron-accepting p-dopant.

[0028] According to other aspects of this disclosure, An organic electroluminescent element comprising a hole injection layer, The hole injection layer, The above-mentioned lateral current suppressing material, or An organic electroluminescent element containing the above-mentioned carbazole compound is provided. [Effects of the Invention]

[0029] According to one aspect of this disclosure, an organic electroluminescent device can be provided that includes a lateral current suppressing material and a carbazole compound for suppressing lateral current flowing horizontally with respect to the anode film, a hole injection layer using these materials, and an organic electroluminescent device that is excellent in driving voltage, luminescence efficiency, and durability, and has low lateral current. [Brief explanation of the drawing]

[0030] [Figure 1] This is a schematic cross-sectional view showing an example of a stacked configuration of an organic electroluminescent element according to one aspect of the present disclosure. [Modes for carrying out the invention]

[0031] The following describes in detail a transverse current suppressing material, a carbazole compound, and a hole injection layer and an organic electroluminescent element using these materials according to one aspect of this disclosure.

[0032] Transverse current refers to an unintended current that flows perpendicular to the stacking direction of the organic layers in an organic electroluminescent element, or in other words, horizontally to the main surface of the substrate. This transverse current causes leakage current to occur between light-emitting pixels (pixels intended to emit light) and adjacent non-light-emitting pixels (pixels not intended to emit light), resulting in unintended light emission from the non-light-emitting pixels and degrading image quality. Transverse current is one of the causes of crosstalk in organic electroluminescent elements, and in recent years, there has been a growing demand to suppress the generation of this transverse current due to the increasing need for higher image quality. [Side current suppression material] A transverse current suppressing material according to one aspect of this disclosure is represented by formula (1).

[0033] [ka]

[0034] During the ceremony, A is represented by equation (2) or (3); B is represented by equation (4);

[0035] [ka]

[0036] During the ceremony, Ar 1 ~Ar 3 Each of them operates independently. A monocyclic, linked, or fused aromatic hydrocarbon group having 6 to 30 carbon atoms, which may be substituted, A monocyclic, linked, or fused heteroaromatic group having 3 to 30 carbon atoms, which may be substituted; Ar 1 ~Ar 3At least one of them is a base represented by one of equations (5) to (21);

[0037] [ka]

[0038] [ka]

[0039] [ka]

[0040] During the ceremony, R 1 represents a methyl group or a hydrogen atom; R 2 and R 3 Each of these independently represents a phenyl group, biphenylyl group, naphthyl group, phenanthryl group, dibenzofuranyl group, or dibenzothienyl group, which may be substituted with a methyl group; X represents either an oxygen atom or a sulfur atom.

[0041] Examples of the above-mentioned monocyclic, linked, or fused aromatic hydrocarbon groups having 6 to 30 carbon atoms include phenyl, biphenylyl, terphenylyl, naphthyl, fluorenyl, spirobifluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, fluoranthenyl, triphenylenyl, pyrenyl, anthryl, tetracenyl, chrysenyl, perilenyl, and pentacenyl groups, as well as those in which one or more of these groups are fused with one or more selected from the group consisting of benzene, naphthalene, and phenanthrene.

[0042] Examples of the above-mentioned monocyclic, linked, or fused heteroaromatic groups having 3 to 30 carbon atoms include pyrrolyl, thienyl, furyl, imidazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazyl, indolyl, benzothienyl, benzofuranyl, benzimidazolyl, indazolyl, benzothiazolyl, benzoisothiazolyl, 2,1,3-benzothiadiazolyl, benzoxazolyl, benzoisoxazolyl, 2,1,3-benzoxadiazolyl, quinolyl, isoquinolyl, carbazolyl, dibenzothienyl, dibenzofuranyl, phenoxazinyl, phenothiazinyl, phenazinyl, and thianthrenyl groups, as well as those in which one or more of these groups are fused with one or more selected from the group consisting of benzene, naphthalene, and phenanthrene.

[0043] As mentioned above, monocyclic, linked, or fused aromatic hydrocarbon groups having 6 to 30 carbon atoms; and monocyclic, linked, or fused heteroaromatic groups having 3 to 30 carbon atoms may have substituents. If these groups have substituents, it is preferable that each is independently substituted with one or more groups selected from the group consisting of linear, branched, or cyclic alkyl groups having 1 to 18 carbon atoms, linear, branched, or cyclic alkoxy groups having 1 to 18 carbon atoms, aromatic hydrocarbon groups having 6 to 20 carbon atoms, heteroaromatic groups having 3 to 20 carbon atoms, triphenylsilyl groups, cyano groups, fluorine atoms, and deuterium atoms. In this case, there is no particular limit to the number of substituents.

[0044] Examples of the above-mentioned linear, branched, or cyclic alkyl groups having 1 to 18 carbon atoms include methyl, propyl, isopropyl, butyl, sec-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, stearyl, cyclopropyl, cyclohexyl, and trifluoromethyl groups.

[0045] Examples of the above-mentioned linear, branched, or cyclic alkoxy groups having 1 to 18 carbon atoms include propoxy groups, isopropoxy groups, n-butoxy groups, sec-butoxy groups, tert-butoxy groups, pentyloxy groups, hexyloxy groups, stearyloxy groups, difluoromethoxy groups, and trifluoromethoxy groups.

[0046] Examples of the above-mentioned aromatic hydrocarbon groups having 6 to 20 carbon atoms include phenyl, tolyl, biphenylyl, terphenylyl, naphthyl, fluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, triphenylenyl, pyrenyl, and anthyl groups.

[0047] Examples of the above-mentioned heteroaromatic groups having 3 to 20 carbon atoms include pyrrolyl group, thienyl group, furyl group, imidazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridyl group, pyrazyl group, indolyl group, benzothienyl group, benzofuranyl group, benzimidazolyl group, indazolyl group, benzothiazolyl group, benzoisothiazolyl group, 2,1,3-benzothiadiazolyl group, benzoxazolyl group, benzoisoxazolyl group, 2,1,3-benzoxadiazolyl group, quinolyl group, isoquinolyl group, carbazolyl group, dibenzothienyl group, dibenzofuranyl group, phenoxazinyl group, phenothiazinyl group, phenazinyl group, and thianthrenyl group.

[0048] Ar 1 ~Ar 3Specific examples include phenyl group, 4-methylphenyl group, 3-methylphenyl group, 2-methylphenyl group, 2,4-dimethylphenyl group, 2,5-dimethylphenyl group, 3,4-dimethylphenyl group, 3,5-dimethylphenyl group, 2,6-dimethylphenyl group, 2,3,5-trimethylphenyl group, 2,3,6-trimethylphenyl group, 3,4,5-trimethylphenyl group, 4-biphenyl group, 3-biphenyl group, 2-biphenyl group, 2-methyl-1,1'-biphenyl-4-yl group, 3-methyl-1,1'-biphenyl Phenyl-4-yl group, 2'-methyl-1,1'-biphenyl-4-yl group, 3'-methyl-1,1'-biphenyl-4-yl group, 4'-methyl-1,1'-biphenyl-4-yl group, 2,6-dimethyl-1,1'-biphenyl-4-yl group, 2,2'-dimethyl-1,1'-biphenyl-4-yl group, 2,3'-dimethyl-1,1'-biphenyl-4-yl group, 2,4'-dimethyl-1,1'-biphenyl-4-yl group, 3,2'-dimethyl-1,1'-biphenyl-4-yl group, 2',3'-dimethyl-1,1 '-biphenyl-4-yl group, 2',4'-dimethyl-1,1'-biphenyl-4-yl group, 2',5'-dimethyl-1,1'-biphenyl-4-yl group, 2',6'-dimethyl-1,1'-biphenyl-4-yl group, 3-methyl-1,1'-biphenyl-2-yl group, 3',5'-dimethyl-1,1'-biphenyl-4-yl group, 4'-methyl-1,1'-biphenyl-2-yl group, 3'-methyl-1,1'-biphenyl-2-yl group, 2'-methyl-1,1'-biphenyl-2-yl group, 3',5'-dimethyl -1,1'-biphenyl-2-yl group, 3',4'-dimethyl-1,1'-biphenyl-2-yl group, 3,3',5'-trimethyl-1,1'-biphenyl-2-yl group, 3,3',4'-trimethyl-1,1'-biphenyl-2-yl group, 3,4'-dimethyl-1,1'-biphenyl-2-yl group, 3,3'-dimethyl-1,1'-biphenyl-2-yl group, 3,2'-dimethyl-1,1'-biphenyl-2-yl group, 3,3',4'-trimethyl-1,1'-biphenyl-2-yl group, 4,4'-dimethyl-1,1'-biphenyl-2-yl group, p-terphenyl-2-yl group, p-terphenyl-3-yl group, p-terphenyl-4-yl group, p-terphenyl-2'-yl group, m-terphenyl-2-yl group, m-terphenyl-3-yl group, m-terphenyl-4-yl group, m-terphenyl-2'-yl group, m-terphenyl-4'-yl group, m-terphenyl-5'-yl group, 3,3”-dimethyl-m-terphenyl-2'-yl group, 4,4”-dimethyl-m-terphenyl-2'-yl group, 3,5,3”,5”-tetramethyl-m-terphenyl- 2'-yl group, 3,4,3”,4”-tetramethyl-m-terphenyl-2'-yl group, o-terphenyl-2-yl group, o-terphenyl-3-yl group, o-terphenyl-4-yl group, o-terphenyl-3'-yl group, o-terphenyl-4'-yl group, 1-naphthyl group, 2-naphthyl group, 2-methylnaphthalene-1-yl group, 4-methylnaphthalene-1-yl group, 6-methylnaphthalene-2-yl group, 4-(1-naphthyl)phenyl group, 4-(2-naphthyl)phenyl group, 3-(1-naphthyl)phenyl group, 3-(2-naphthyl)phenyl group , 3-methyl-4-(1-naphthyl)phenyl group, 3-methyl-4-(2-naphthyl)phenyl group, 3-methyl-2-(4-methyl-1-naphthyl)phenyl group, 6-methyl-2-(4-methyl-1-naphthyl)phenyl group, 2-(1-naphthyl)-6-methylphenyl group, 2-(2-naphthyl)-6-methylphenyl group, 4-(1-naphthyl)biphenyl group, 4-(2-naphthyl)biphenyl group, 3-(1-naphthyl)biphenyl group, 3-(2-naphthyl)biphenyl group, 4-(2-methylnaphthalene-1-yl)phenyl group, 3-(2-methylna phthalen-1-yl)phenyl group, 4-phenylnaphthalen-1-yl group, 4-(2-methylphenyl)naphthalen-1-yl group, 4-(3-methylphenyl)naphthalen-1-yl group, 4-(4-methylphenyl)naphthalen-1-yl group, 6-phenylnaphthalen-2-yl group, 4-(2-methylphenyl)naphthalen-2-yl group, 4-(3-methylphenyl)naphthalen-2-yl group, 4-(4-methylphenyl)naphthalen-2-yl group, tetraphenylsilane-4-yl group, tetraphenylsilane-3-yl group, 2-fluorenyl group, 9,9-dimethyl-2-fluorenyl group, 9,9-diphenyl-2-fluorenyl group, 9,9-diphenyl-4-fluorenyl group, 9,9'-spirobifloren-2-yl group, 9,9'-spirobifloren-4-yl group, 4-(9,9'-spirobifloren-4-yl)phenyl group, 3-(9,9'-spirobifloren-4-yl)phenyl group, 4-(9,9'-spirobifloren-4-yl)biphenyl group, 3-(9,9'-spirobifloren-4-yl)biphenyl group, 4-(9,9'-diphenylfluorenyl- 4-yl)phenyl group, 3-(9,9'-diphenylfluoren-4-yl)phenyl group, 4-(9,9'-diphenylfluoren-4-yl)biphenyl group, 3-(9,9'-diphenylfluoren-4-yl)biphenyl group, 3-(1-triphenylenyl)biphenyl group, 9-phenanthryl group, 2-phenanthryl group, 4-(9-phenanthryl)phenyl group, 3-(9-phenanthryl)phenyl group, 4-(9-phenanthryl)biphenyl group, 3-(1-naphthyl)biphenyl group, 3-(9-phenanthryl)biphenyl group Phenyl group, 1-triphenylenyl group, 2-triphenylenyl group, 3-triphenylenyl group, 4-triphenylenyl group, 4-(1-triphenylenyl)phenyl group, 3-(1-triphenylenyl)phenyl group, 4-(1-triphenylenyl)biphenyl group, 3-(1-triphenylenyl)biphenyl group, 3-(1-triphenylenyl)biphenyl group, 11,11'-dimethylbenzo[a]fluoren-9-yl group, 11,11'-dimethylbenzo[a]fluoren-3-yl group, 11,11'-dimethylbenzo[b]fluoren -9-yl group, 11,11'-dimethylbenzo[b]fluoren-3-yl group, 11,11'-dimethylbenzo[c]fluoren-9-yl group, 11,11'-dimethylbenzo[c]fluoren-2-yl group, 3-fluoranthenyl group, 8-fluoranthenyl group, 1-imidazolyl group, 2-phenyl-1-imidazolyl group, 2-phenyl-3,4-dimethyl-1-imidazolyl group, 2,3,4-triphenyl-1-imidazolyl group, 2-(2-naphthyl)-3,4-dimethyl-1-imidazolyl group, 2-(2-naphthyl)-3,4-diphenyl-1-imidazolyl group, 1-methyl-2-imidazolyl group, 1-ethyl-2-imidazolyl group, 1-phenyl-2-imidazolyl group, 1-methyl-4-phenyl-2-imidazolyl group, 1-methyl-4,5-dimethyl-2-imidazolyl group, 1-methyl-4,5-diphenyl-2-imidazolyl group, 1-phenyl-4,5-dimethyl-2-imidazolyl group, 1-phenyl-4,5-diphenyl-2-imidazolyl group, 1-phenyl-4,5-dibiphenylyl-2-imidazolyl group, 1-methyl-3-pyrazolyl group, 1-phenyl-3-pyrazolyl group Lazolyl group, 1-methyl-4-pyrazolyl group, 1-phenyl-4-pyrazolyl group, 1-methyl-5-pyrazolyl group, 1-phenyl-5-pyrazolyl group, 2-thiazolyl group, 4-thiazolyl group, 5-thiazolyl group, 3-isothiazolyl group, 4-isothiazolyl group, 5-isothiazolyl group, 2-oxazolyl group, 4-oxazolyl group, 5-oxazolyl group, 3-isoxazolyl group, 4-isoxazolyl group, 5-isoxazolyl group, 2-pyridyl group, 3-methyl-2-pyridyl group, 4-methyl-2-pyridyl group, 5-methyl-2-pyridyl group, 6-methyl 2-pyridyl group, 3-pyridyl group, 4-methyl-3-pyridyl group, 4-pyridyl group, 2-pyrimidyl group, 2,2'-bipyridine-3-yl group, 2,2'-bipyridine-4-yl group, 2,2'-bipyridine-5-yl group, 2,3'-bipyridine-3-yl group, 2,3'-bipyridine-4-yl group, 2,3'-bipyridine-5-yl group, 5-pyrimidyl group, pyrazyl group, 1,3,5-triazyl group, 4,6-diphenyl-1,3,5-triazine-2-yl group, 1-benzoimidazolyl group, 2-methyl-1-benzoimidazolyl group, 2-phenyl-1- Benzimidazolyl group, 1-methyl-2-benzoimidazolyl group, 1-phenyl-2-benzoimidazolyl group, 1-methyl-5-benzoimidazolyl group, 1,2-dimethyl-5-benzoimidazolyl group, 1-methyl-2-phenyl-5-benzoimidazolyl group, 1-phenyl-5-benzoimidazolyl group, 1,2-diphenyl-5-benzoimidazolyl group, 1-methyl-6-benzoimidazolyl group, 1,2-dimethyl-6-benzoimidazolyl group, 1-methyl-2-phenyl-6-benzoimidazolyl group, 1-phenyl-6-benzoimidazolyl group, 1,2-diphenyl-6-benzoimidazolyl group, 1-methyl-3-indazolyl group, 1-phenyl-3-indazolyl group, 2-benzothiazolyl group, 4-benzothiazolyl group, 5-benzothiazolyl group, 6-benzothiazolyl group, 7-benzothiazolyl group, 3-benzoisothiazolyl group, 4-benzoisothiazolyl group, 5-benzoisothiazolyl group, 6-benzoisothiazolyl group, 7-benzoisothiazolyl group, 2,1,3-benzothiadiazole-4-yl group, 2,1,3-benzothiadiazole-5-yl group, 2-benzoxazolyl group, 4-benzoxazolyl group, 5-benzo Oxazolyl group, 6-benzoxazolyl group, 7-benzoxazolyl group, 3-benzoisoxazolyl group, 4-benzoisoxazolyl group, 5-benzoisoxazolyl group, 6-benzoisoxazolyl group, 7-benzoisoxazolyl group, 2,1,3-benzoxadiazolyl-4-yl group, 2,1,3-benzoxadiazolyl-5-yl group, 2-quinolyl group, 3-quinolyl group, 5-quinolyl group, 6-quinolyl group, 1-isoquinolyl group, 4-isoquinolyl group, 5-isoquinolyl group, 2-acridinyl group, 9-acridinyl group, 1,10-phenanthroline-3-yl group, 1,10-phenanthroline-5-yl group, 2-thienyl group, 3-thienyl group, 2-benzothienyl group, 3-benzothienyl group, 2-dibenzothienyl group, 4-dibenzothienyl group, 2-furanyl group, 3-furanyl group, 2-benzofuranyl group, 3-benzofuranyl group, 2-dibenzofuranyl group, 4-dibenzofuranyl group, carbazole-9-yl group, 9-methylcarbazole-2-yl group, 9-methylcarbazole 9-methylcarbazole-4-yl group, 9-phenylcarbazole-2-yl group, 9-phenylcarbazole-3-yl group, 9-phenylcarbazole-4-yl group, 9-biphenylcarbazole-2-yl group, 9-biphenylcarbazole-3-yl group, 9-biphenylcarbazole-4-yl group, 2-(9-carbazolyl)phenyl group, 3-(9-carbazolyl)phenyl group, 4- (9-carbazolyl)phenyl group, 2-(9-carbazolyl)biphenyl group, 3-(9-carbazolyl)biphenyl group, 4-(9-carbazolyl)biphenyl group, 2-(9-phenylcarbazole-3-yl)phenyl group, 3-(9-phenylcarbazole-3-yl)phenyl group, 4-(9-phenylcarbazole-3-yl)phenyl group, 2-thianthryl group, 10-phenylphenothiazine-3-yl group, 10-phenylphenothiazine-2-yl group, 10-phenylphenoxazine-3-yl group, 10-phenylphenoxazine-2-yl group, 1-methylindole-2-yl group, 1-phenylindole-2-yl group, 1-methylindole-2-yl group, 1-phenylindole-2-yl group, 4-(2-pyridyl)phenyl group, 4-(3-pyridyl)phenyl group, 4-(4-pyridyl)phenyl, group, 3-(2-pyridyl)phenyl group, 3-(3-pyridyl)phenyl group, 3-(4-pyridyl)phenyl group, 4-(2-phenylimidazole-1-yl)phenyl group, 4-(1-phenylimidazole-2-yl)phenyl group, 4-(2,3,4-triphenylimidazole-1-yl)phenyl group, 4-(1-methyl-4,5-diphenylimidazole-2-yl)phenyl group, 4-(2-methylbenzoimidazole-1-yl)phenyl group, 4-(2- Phenylbenzimidazole-1-yl)phenyl group, 4-(1-methylbenzimidazole-2-yl)phenyl group, 4-(2-phenylbenzimidazole-1-yl)phenyl group, 3-(2-methylbenzimidazole-1-yl)phenyl group, 3-(2-phenylbenzimidazole-1-yl)phenyl group, 3-(1-methylbenzimidazole-2-yl)phenyl group, 3-(2-phenylbenzimidazole-1-yl)phenyl group, 4-(3,5-diphenyltriazine-1-yl)phenyl group, 4-(2-thienyl)phenyl group, 4-(2-furanyl)phenyl group, 5-phenylthiophene-2-yl group, 5-phenylfuran-2-yl group, 4-(5-phenylthiophene-2-yl)phenyl group, 4-(5-phenylfuran-2-yl)phenyl group, 3-(5-phenylthiophene-2-yl)phenyl group, 3-(5-phenylfuran-2-yl)phenyl group, 4-(2-benzothienyl)phenyl group, 4-(3-benzothienyl)phenyl group, 3-(2-benzothienyl)phenyl group, 3-(3-benzothienyl)phenyl group, 4-(2-dibenzothienyl)phenyl group, 4-(4-dibenzothienyl)phenyl group, 3-(2-dibenzothienyl)phenyl group, 3-(4-dibenzothienyl)phenyl group, 4-(2-dibenzofuranyl)phenyl group, 4 Examples include the -(4-dibenzofuranyl)phenyl group, 3-(2-dibenzofuranyl)phenyl group, 3-(4-dibenzofuranyl)phenyl group, 4-(2-benzothienyl)phenyl group, 4-(3-benzothienyl)phenyl group, 3-(2-benzothienyl)biphenyl group, 3-(3-benzothienyl)biphenyl group, 4-(2-dibenzothienyl)biphenyl group, 3-(4-dibenzothienyl)biphenyl group, 3-(2-dibenzothienyl)biphenyl group, 3-(4-dibenzothienyl)biphenyl group, 4-(2-dibenzofuranyl)biphenyl group, 3-(2-dibenzofuranyl)biphenyl group, 3-(4-dibenzofuranyl)biphenyl group, 5-phenylpyridine-2-yl group, 4-phenylpyridine-2-yl group, 5-phenylpyridine-3-yl group, etc. ,

[0049] Ar in equation (1) 1 ~Ar 3 In this context, the substituted monocyclic, linked, or fused aromatic hydrocarbon groups having 6 to 30 carbon atoms, or the substituted monocyclic, linked, or fused heteroaromatic groups having 3 to 30 carbon atoms, exhibit excellent hole transport properties, and therefore, each is independently selected. (i) Phenyl group, biphenylyl group, terphenylyl group, naphthyl group, fluorenyl group, spirobifluorenyl group, benzofluorenyl group, phenanthryl group, fluoranthenyl group, triphenylenyl group, anthryl group, pyrenyl group, benzofuranyl group, benzothienyl group, dibenzofuranyl group, or dibenzothienyl group, (ii) The group shown in (i) above is a group substituted with one or more groups selected from the group consisting of a methyl group, an ethyl group, a methoxy group, an ethoxy group, a cyano group, a deuterium atom, a fluorine atom, a phenyl group, a biphenylyl group, a naphthyl group, a phenanthryl group, a triphenylsilyl group, a carbazolyl group, a dibenzothienyl group, and a dibenzofuranyl group, or (iii) Preferably, the group is represented by any one of the above formulas (5) to (21).

[0050] Ar 1 ~Ar 3 In this context, the substituted monocyclic, linked, or fused aromatic hydrocarbon groups having 6 to 30 carbon atoms, or the substituted monocyclic, linked, or fused heteroaromatic groups having 3 to 30 carbon atoms, exhibit excellent hole transport properties, and therefore, each is independently selected. (i') Phenyl group, biphenylyl group, terphenylyl group, naphthyl group, fluorenyl group, spirobifluorenyl group, benzofluorenyl group, phenanthryl group, fluoranthenyl group, triphenylenyl group, anthryl group, pyrenyl group, dibenzofuranyl group, or dibenzothienyl group, or (ii') It is more preferable that the group indicated in (i') above is a group substituted with one or more groups selected from the group consisting of a methyl group, a phenyl group, a biphenylyl group, a naphthyl group, a phenanthryl group, a triphenylsilyl group, a carbazolyl group, a dibenzothienyl group, and a dibenzofuranyl group.

[0051] Ar 1 ~Ar 3 Because they have excellent hole transport properties, each can be used independently. It is even more preferable that the group is a phenyl group, methylphenyl group, biphenylyl group, methylbiphenylyl group, dimethylbiphenylyl group, trimethylterphenylyl group, terphenylyl group, methylterphenylyl group, dimethylterphenylyl group, naphthyl group, 9,9-dimethylfluorenyl group, 9,9-diphenylfluorenyl group, spirobifluorenyl group, 11,11-dimethylbenzo[a]fluorene, 11,11-dimethylbenzo[b]fluorene, 7,7-dimethylbenzo[c]fluorene, phenanthryl group, fluoranthenyl group, triphenylenyl group, naphthylphenyl group, phenanthrylphenyl group, triphenylsilylphenyl group, carbazolylphenyl group, dibenzofuranyl group, dibenzothienyl group, dibenzofuranylphenyl group, or dibenzothienylphenyl group.

[0052] Ar 1 Because it is excellent at suppressing lateral current, it is preferable that the group be represented by one of the formulas (5) to (21).

[0053] Ar 1 and Ar 2 Since all of these are excellent at suppressing lateral current, it is more preferable that each of them be a group that can be independently represented by one of the equations (5) to (21).

[0054] Ar 1 and Ar 2 Since all of these are excellent at suppressing lateral current, it is even more preferable that the group be represented by one of the equations (6) to (8), (10) to (14), or (18) to (20).

[0055] In formulas (5) to (21), R 2 and R 3 Each of these groups is preferably independently a phenyl group, a methylphenyl group, a dimethylphenyl group, a trimethylphenyl group, a biphenylyl group, a methylbiphenylyl group, a dimethylbiphenylyl group, a naphthyl group, a phenanthryl group, a dibenzofuranyl group, or a dibenzothienyl group.

[0056] Since equations (5) to (21) can suppress lateral current, it is more preferable that the group be represented by one of the following equations (Y1) to (Y298).

[0057] [ka]

[0058] [ka]

[0059] [ka]

[0060] [ka]

[0061] [ka]

[0062] [ka]

[0063] [ka]

[0064] [ka]

[0065] [ka]

[0066] [ka]

[0067] [ka]

[0068] Ar 1 Because it is excellent at suppressing lateral current, it is preferable that the group be represented by one of the above formulas (Y1) to (Y298).

[0069] Ar 1 and Ar 2 Since all of these are excellent at suppressing lateral current, it is more preferable that each of them be a group that is independently represented by one of the above formulas (Y1) to (Y298).

[0070] Ar 1 and Ar 2 Since all of these are excellent at suppressing lateral current, it is even more preferable that each is independently represented by one of the above formulas (Y2)~(Y9), (Y11)~(Y18), or (Y21)~(Y298).

[0071] Ar 1 It is even more preferable that the group is represented by one of the above formulas (Y25)~(Y46), (Y58)~(Y101), (Y103)~(Y124), (Y133)~(Y200), (Y225)~(Y256), (Y263)~(Y265), or (Y281)~(Y298), as it is excellent at suppressing lateral current.

[0072] Because it excels at suppressing lateral current, Ar 1 However, the group is represented by one of the above formulas (Y25)~(Y46), (Y58)~(Y101), (Y103)~(Y124), (Y133)~(Y200), (Y225)~(Y256), (Y263)~(Y265), (Y281)~(Y298), and Ar 2 However, it is even more preferable that the group be represented by any one of the above formulas (Y1) to (Y298).

[0073] Ar1 and Ar 2 Since all of these are excellent at suppressing lateral current, it is even more preferable that each group be independently represented by one of the above formulas (Y25)~(Y46), (Y58)~(Y101), (Y103)~(Y124), (Y133)~(Y200), (Y225)~(Y256), (Y263)~(Y265), or (Y281)~(Y298).

[0074] In equation (1), Examples of A include the following equations (a1) to (a262).

[0075] Specific examples of B include equations (b1) to (b309) and equations (c1) to (c1326). However, if A is equations (a1) to (a76) or (a213) to (a216), then B is selected from equations (c1) to (c1326).

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[0152] [Carbazole compounds] A carbazole compound according to one aspect of this disclosure is represented by formula (22) or formula (23):

[0153] [ka]

[0154] During the ceremony, Ar 6 Each of these is an independent base selected from the following equations (24) to (45).

[0155] [ka]

[0156] [ka]

[0157] [ka]

[0158] During the ceremony, R 4 This represents a biphenylyl group, naphthyl group, phenanthryl group, dibenzofuranyl group, or dibenzothienyl group, which may be substituted with a methyl group.

[0159] R 5 Each of these independently represents either a methyl group or a hydrogen atom.

[0160] R 6 This represents a phenyl group, biphenylyl group, naphthyl group, phenanthryl group, dibenzofuranyl group, or dibenzothienyl group, which may be substituted with a methyl group.

[0161] R 7 and R 8 Each of these independently represents a phenyl group, biphenylyl group, naphthyl group, phenanthryl group, dibenzofuranyl group, or dibenzothienyl group, which may be substituted with a methyl group, and at least one of these is a biphenylyl group, naphthyl group, phenanthryl group, dibenzofuranyl group, or dibenzothienyl group, which may be substituted with a methyl group.

[0162] In equations (22) and (23), Ar 6 If is a base selected from equations (24) to (31), Ar 5 is a base selected from equations (24) to (45), and Ar 4 This group is represented by a monocyclic, linked, or fused aromatic hydrocarbon group having 6 to 30 carbon atoms, which may be substituted, or by a monocyclic, linked, or fused heteroaromatic group having 3 to 30 carbon atoms, which may be substituted.

[0163] In equations (22) and (23), Ar 6 If is a base selected from equations (32) to (44), Ar 4 and Ar 5 Each of these groups is independently represented by a group selected from formulas (24) to (45), or by a monocyclic, linked, or fused aromatic hydrocarbon group having 6 to 30 carbon atoms, which may be substituted, or by a monocyclic, linked, or fused heteroaromatic group having 3 to 30 carbon atoms, which may be substituted.

[0164] In formulas (22) and (23), the group represented by a monocyclic, linked, or fused aromatic hydrocarbon group having 6 to 30 carbon atoms, which may be substituted; or a monocyclic, linked, or fused heteroaromatic group having 3 to 30 carbon atoms, which may be substituted; is equivalent to the group represented by a monocyclic, linked, or fused aromatic hydrocarbon group having 6 to 30 carbon atoms, which may be substituted; or a monocyclic, linked, or fused heteroaromatic group having 3 to 30 carbon atoms, which may be substituted; as shown in formula (1) above.

[0165] Ar in equations (22) and (23) 4 In this context, the substituted monocyclic, linked, or fused aromatic hydrocarbon groups having 6 to 30 carbon atoms, or the substituted monocyclic, linked, or fused heteroaromatic groups having 3 to 30 carbon atoms, exhibit excellent hole transport properties, and therefore, each is independently selected. (i) Phenyl group, biphenylyl group, terphenylyl group, naphthyl group, fluorenyl group, spirobifluorenyl group, benzofluorenyl group, phenanthryl group, fluoranthenyl group, triphenylenyl group, anthryl group, pyrenyl group, benzofuranyl group, benzothienyl group, dibenzofuranyl group, or dibenzothienyl group, (ii) It is preferable that the group referred to in (i) above is a group substituted with one or more groups selected from the group consisting of a methyl group, an ethyl group, a methoxy group, an ethoxy group, a cyano group, a deuterium atom, a fluorine atom, a phenyl group, a biphenylyl group, a naphthyl group, a phenanthryl group, a triphenylsilyl group, a carbazolyl group, a dibenzothienyl group, and a dibenzofuranyl group.

[0166] Ar 4 In this context, the substituted monocyclic, linked, or fused aromatic hydrocarbon groups having 6 to 30 carbon atoms, or the substituted monocyclic, linked, or fused heteroaromatic groups having 3 to 30 carbon atoms, exhibit excellent hole transport properties, and therefore, each is independently selected. (i') Phenyl group, biphenylyl group, terphenylyl group, naphthyl group, fluorenyl group, spirobifluorenyl group, benzofluorenyl group, phenanthryl group, fluoranthenyl group, triphenylenyl group, anthryl group, pyrenyl group, dibenzofuranyl group, or dibenzothienyl group, or (ii') It is more preferable that the group indicated in (i') above is a group substituted with one or more groups selected from the group consisting of a methyl group, a phenyl group, a biphenylyl group, a naphthyl group, a phenanthryl group, a triphenylsilyl group, a carbazolyl group, a dibenzothienyl group, and a dibenzofuranyl group.

[0167] Ar 4 Because they have excellent hole transport properties, each can be used independently. (iv) Phenyl group, biphenylyl group, terphenylyl group, naphthyl group, fluorenyl group, spirobifluorenyl group, benzofluorenyl group, phenanthryl group, fluoranthenyl group, triphenylenyl group, anthryl group, pyrenyl group, dibenzofuranyl group, or dibenzothienyl group, or (v) The group shown in (iv) above is a group substituted with one or more groups selected from the group consisting of a methyl group, an ethyl group, a methoxy group, an ethoxy group, a cyano group, a deuterium atom, a fluorine atom, a phenyl group, a biphenylyl group, a naphthyl group, a phenanthryl group, a triphenylsilyl group, a carbazolyl group, a dibenzothienyl group, and a dibenzofuranyl group, or (vi) It is even more preferable that the group be represented by any one of the above formulas (24) to (35).

[0168] Ar 4It is particularly preferable that each of these groups independently be a phenyl group, a methylphenyl group, a dimethylphenyl group, a biphenylyl group, a methyl biphenylyl group, a dimethyl biphenylyl group, a trimethyl biphenylyl group, a terphenylyl group, a methyl terphenylyl group, a dimethyl terphenylyl group, a naphthyl group, a 9,9-dimethylfluorenyl group, a 9,9-diphenylfluorenyl group, a spirobifluorenyl group, a 11,11-dimethylbenzo[a]fluorene, a 11,11-dimethylbenzo[b]fluorene, a 7,7-dimethylbenzo[c]fluorene, a phenanthryl group, a fluoranthenyl group, a triphenylenyl group, a naphthylphenyl group, a phenanthrylphenyl group, a triphenylsilylphenyl group, a carbazolylphenyl group, a dibenzofuranyl group, a dibenzothienyl group, a dibenzofuranylphenyl group, or a dibenzothienylphenyl group.

[0169] In formulas (24) to (40), R 4 The group is preferably a biphenylyl group, a methyl biphenylyl group, a dimethyl biphenylyl group, a naphthyl group, a phenanthryl group, a dibenzofuranyl group, or a dibenzothienyl group.

[0170] In formulas (24) to (40), R 6 The group is preferably a phenyl group, methylphenyl group, dimethylphenyl group, trimethylphenyl group, biphenylyl group, methylbiphenylyl group, dimethylbiphenylyl group, naphthyl group, phenanthryl group, dibenzofuranyl group, or dibenzothienyl group.

[0171] In formulas (24) to (40), R 7 and R 8 Each of these independently represents a phenyl group, a methylphenyl group, a dimethylphenyl group, a trimethylphenyl group, a biphenylyl group, a methylbiphenylyl group, a dimethylbiphenylyl group, a naphthyl group, a phenanthryl group, a dibenzofuranyl group, or a dibenzothienyl group, and preferably at least one is a biphenylyl group, a methylbiphenylyl group, a dimethylbiphenylyl group, a naphthyl group, a phenanthryl group, a dibenzofuranyl group, or a dibenzothienyl group.

[0172] Equations (24) to (40) are excellent in suppressing lateral current, therefore, it is preferable to select one from the groups represented by the following equations (Z1) to (Z209).

[0173] [ka]

[0174] [ka]

[0175] [ka]

[0176] [ka]

[0177] [ka]

[0178] [ka]

[0179] [ka]

[0180] [ka]

[0181] [Specific examples of lateral current suppressing materials and carbazole compounds] Examples of lateral current suppressing materials and carbazole compounds according to one aspect of this disclosure are given below, including compounds of formulas (D1) to (D859), (E1) to (E772), (F1) to (F924), and (G1) to (G718), but this disclosure is not limited to these compounds.

[0182] [ka]

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[0321] [Organic electroluminescent device, hole transport layer] The following describes a lateral current suppressing material represented by formula (1) (hereinafter sometimes simply referred to as lateral current blocking material (1)), or an organic electroluminescent element containing a carbazole compound represented by formula (22) or formula (23) (hereinafter sometimes simply referred to as an organic electroluminescent element).

[0322] An organic electroluminescent element according to one aspect of the present disclosure contains a transverse current suppressing material represented by formula (1), or a carbazole compound represented by formula (22) or formula (23).

[0323] The configuration of the organic electroluminescent element is not particularly limited, but for example, the configurations shown in (i) to (v) below can be considered.

[0324] (i): Anode / Hole injection layer / Emitting layer / Cathode (ii): Anode / Hole injection layer / Hole transport layer / Emitting layer / Cathode (iii): Anode / Hole injection layer / Hole transport layer / Electron blocking layer / Emitting layer / Cathode (iv): Anode / Hole injection layer / Hole transport layer / Electron blocking layer / Emitting layer / Electron transport layer / Cathode (v): Anode / Hole injection layer / Hole transport layer / Electron blocking layer / Emitting layer / Electron transport layer / Electron injection layer / Cathode The transverse current suppressing material represented by formula (1), or the carbazole compound represented by formula (22) or formula (23), is excellent at suppressing the transverse current of organic electroluminescent elements. The hole injection layer contains the transverse current suppressing material represented by formula (1), or the carbazole compound represented by formula (22) or formula (23). In the case of an organic electroluminescent element equipped with a hole transport layer, the hole transport layer may contain the transverse current suppressing material represented by formula (1), or the carbazole compound represented by formula (22) or formula (23).

[0325] Anode and, Multiple organic layers on the anode, An organic electroluminescent element comprising a cathode on a plurality of organic layers, Preferably, one or more of the plurality of organic layers contain a carbazole compound represented by formula (22) or formula (23).

[0326] In terms of superior light emission characteristics, driving voltage, and lifespan of the organic electroluminescent element, it is preferable that at least one of the hole injection layer, hole transport layer, electron blocking layer, and light emission layer contains a carbazole compound represented by formula (22) or formula (23).

[0327] Hereinafter, an organic electroluminescent element according to one aspect of this disclosure will be described in more detail with reference to Figure 1, using the configuration described in (v) above as an example.

[0328] Although the organic electroluminescent element shown in Figure 1 has a so-called bottom-emission type element configuration, the organic electroluminescent element according to one aspect of this disclosure is not limited to a bottom-emission type element configuration. In other words, the organic electroluminescent element according to one aspect of this disclosure may have other known element configurations, such as a top-emission type.

[0329] Figure 1 is a schematic cross-sectional view showing an example of a stacked configuration of an organic electroluminescent element according to one aspect of the present disclosure.

[0330] The organic electroluminescent element 100 comprises a substrate 1, an anode 2, a hole injection layer 3, a hole transport layer 4, an electron blocking layer 5, a light-emitting layer 6, an electron transport layer 7, an electron injection layer 8, and a cathode 9 in this order. However, some of these layers may be omitted, or other layers may be added. For example, a hole blocking layer may be provided between the light-emitting layer 6 and the electron transport layer 7, or the electron blocking layer 5 may be omitted and the light-emitting layer 6 may be directly provided on the hole transport layer 4. Furthermore, a single layer that combines the functions of multiple layers, such as a hole transport / electron blocking layer that combines the functions of the hole transport layer 4 and the electron blocking layer 5, may be provided instead of the multiple layers. In addition, for example, a single-layer electron transport layer 7 may consist of multiple layers. <<Layer containing transverse current suppressing material (1)>> In the configuration example shown in Figure 1, the organic electroluminescent element 100 includes a hole injection layer 3, or the hole injection layer 3 and the hole transport layer 4, which contain the lateral current blocking material (1). In particular, it is preferable that the hole injection layer 3 and the hole transport layer 4 contain the lateral current blocking material (1). The lateral current blocking material (1) may be included in multiple layers of the organic electroluminescent element.

[0331] In the following description, we will explain an organic electroluminescent element 100 in which the hole injection layer 3 and the hole transport layer 4 include a lateral current suppressing material (1). <Circuit board 1> There are no particular limitations to the substrate 1; for example, it could be a glass plate, a quartz plate, or a plastic plate.

[0332] Examples of substrate 1 include glass plates, quartz plates, plastic plates, and plastic films. Among these, glass plates, quartz plates, and light-transmitting plastic films are preferred.

[0333] Examples of light-transmitting plastic films include films made from polyethylene terephthalate (PET), polyethylene naphthalate (PEN), polyethersulfone (PES), polyetherimide, polyetheretherketone, polyphenylene sulfide, polyarylate, polyimide, polycarbonate (PC), cellulose triacetate (TAC), cellulose acetate propionate (CAP), and the like.

[0334] In the configuration where light is extracted from the substrate 1, the substrate 1 is transparent to the wavelength of light. <Anode 2> An anode 2 is provided on substrate 1 (on the side of hole injection layer 3).

[0335] Suitable anode materials include metals, alloys, electrically conductive compounds, and mixtures thereof, all of which have a high work function (e.g., 4 eV or more). Specific examples of anode materials include metals such as Au; and conductive transparent materials such as CuI, indium tin oxide (ITO), SnO2, and ZnO.

[0336] In the case of an organic electroluminescent element in which light is extracted by passing it through an anode, the anode is formed of a conductive transparent material that allows the light to pass through or substantially allows the light to pass through. <Hole injection layer 3> A hole injection layer 3 is provided between the anode 2 and the hole transport layer 4, which will be described later.

[0337] The hole injection layer functions as a hole-injecting layer. By interposing the hole injection layer between the anode and the light-emitting layer, holes are injected into the light-emitting layer at a lower electric field. In particular, it is preferable that the hole injection layer contains a transverse current suppressing material represented by formula (1), or a carbazole compound represented by formula (22) or formula (23).

[0338] The hole injection layer may further contain an electron-accepting p-dopant.

[0339] In other words, the hole injection layer according to one aspect of this disclosure is The first compound and, A hole injection layer containing a second compound, The first compound described above is A lateral current suppressing material represented by formula (1), or A carbazole compound represented by formula (22) or formula (23), The second compound is an electron-accepting p-dopant.

[0340] Furthermore, it contains a third compound, The third compound is preferably a hole-transporting triarylamine compound.

[0341] In these cases, the content of the p-dopant is 0.5% by mass or more and 20% by mass or less. The content of the transverse current suppressing material represented by formula (1), or the carbazole compound represented by formula (22) or formula (23), is 20% by mass or more and 99.5% by mass or less.

[0342] The p-dopant only needs to have electron-accepting properties, and examples include compounds represented by the following formulas (J1) to (J51):

[0343] [ka]

[0344] [ka]

[0345] [ka]

[0346] Furthermore, the hole injection layer may further contain a hole-transporting triarylamine compound. In this case, the content of the triarylamine compound is 10% by mass or more and 79.5% by mass or less. The triarylamine compound is represented by any of formulas (36) to (38).

[0347] [ka]

[0348] During the ceremony, Ar 10 ~Ar 22 Each of them operates independently. A monocyclic, linked, or fused aromatic hydrocarbon group having 6 to 25 carbon atoms, which may be substituted, Represents a monocyclic, linked, or fused heteroaromatic group having 3 to 25 carbon atoms, which may be substituted; L 1 ~L 18 Each of them operates independently. A monocyclic, linked, or fused divalent aromatic hydrocarbon group having 6 to 25 carbon atoms, which may be substituted. A divalent heteroaromatic group having 3 to 25 carbon atoms, which may be substituted, or a monocyclic, linked, or fused ring. Represents a single bond; X is A monocyclic, linked, or fused divalent aromatic hydrocarbon group having 6 to 25 carbon atoms, which may be substituted, or Represents a divalent heteroaromatic group having 3 to 25 carbon atoms, which may be substituted, monocyclic, linked, or fused; a, b, and c each independently represent an integer between 1 and 3; d and e each independently represent the integer 1 or 2; f represents an integer, either 0 or 1. Ar 10 ~Ar 22 Each of them operates independently. (i) Phenyl group, biphenylyl group, terphenylyl group, naphthyl group, fluorenyl group, spirobifluorenyl group, benzofluorenyl group, phenanthryl group, fluoranthenyl group, triphenylenyl group, anthryl group, pyrenyl group, pyridyl group, carbazolyl group, benzofuranyl group, benzothienyl group, dibenzofuranyl group, or dibenzothienyl group, (ii) It is preferable that the group referred to in (i) above is a group substituted with one or more groups selected from the group consisting of a methyl group, an ethyl group, a methoxy group, a cyano group, a deuterium atom, a fluorine atom, a phenyl group, a biphenylyl group, a naphthyl group, a phenanthryl group, a pyridyl group, a carbazolyl group, a dibenzothienyl group, and a dibenzofuranyl group.

[0349] L 1 ~L 18 Each of them operates independently. (iii) Phenylene group, biphenylylene group, terphenylylene group, naphthylene group, pyridylene group, or fluorenylene group, (iv) The group shown in (iii) above is a group substituted with one or more groups selected from the group consisting of a methyl group, an ethyl group, a methoxy group, a cyano group, a deuterium atom, a fluorine atom, a phenyl group, a biphenylyl group, a naphthyl group, a phenanthryl group, a pyridyl group, a carbazolyl group, a dibenzothienyl group, and a dibenzofuranyl group, or (v) A single bond is preferred.

[0350] X is (vi) Phenylene group, biphenylylene group, terphenylylene group, naphthylene group, fluorenylene group, pyrenediyl group, anthracenediyl group, dibenzothiophenediyl group, dibenzofranziyl group, pyridinediyl group, carbazolediyl group, cyclohexanediyl group, adamantanediyl group, methanediyl group, or silanediyl group, or (vii) It is preferable that the group indicated in (vi) above is a group substituted with one or more groups selected from the group consisting of a methyl group, an ethyl group, a methoxy group, a cyano group, a deuterium atom, a fluorine atom, a phenyl group, a biphenylyl group, a naphthyl group, a phenanthryl group, a pyridyl group, a carbazolyl group, a dibenzothienyl group, and a dibenzofuranyl group.

[0351] Examples of hole-transporting triarylamine compounds include those represented by the following formulas (K1) to (K76):

[0352] [ka]

[0353] [ka]

[0354] [ka]

[0355] [ka]

[0356] [ka]

[0357] A hole injection layer according to one aspect of the present disclosure preferably contains two compounds, wherein the first compound is a transverse current suppressing material represented by formula (1) or a carbazole compound represented by formula (22) or formula (23), and the second compound is an electron acceptor p-dopant.

[0358] A hole injection layer according to one aspect of the present disclosure preferably contains three types of compounds, wherein the first compound is a transverse current suppressing material represented by formula (1) or a carbazole compound represented by formula (22) or formula (23), the second compound is an electron acceptor p-dopant, and the third compound is a hole transporter triarylamine compound.

[0359] Furthermore, it is preferable that the hole injection layer contains 20% or more of the transverse current suppressing material represented by formula (1) or the carbazole compound represented by formula (22) or formula (23) and 99.5% or less. <Hole transport layer 4> A hole transport layer 4 is provided between the hole injection layer 3 and the electron blocking layer 5, which will be described later.

[0360] The hole transport layer is a layer formed on top of the hole injection layer that improves hole mobility and thus improves the power efficiency of the organic light-emitting element.

[0361] The hole transport material should be a material that can smoothly inject holes from the anode and transfer them to the light-emitting layer, and should have high mobility for holes. The hole transport material is not limited as long as it is used in organic light-emitting devices, and as an example, compounds represented by formulas (K1) to (K76) exemplified in the hole injection layer can be used.

[0362] Furthermore, the hole transport layer is A lateral current suppressing material represented by the above formula (1), or The product may contain a carbazole compound represented by formula (22) or formula (23).

[0363] Both the hole transport layer and the hole injection layer are, A lateral current suppressing material represented by the above formula (1), or Preferably, the compound contains a carbazole compound represented by formula (22) or formula (23).

[0364] The hole transport layer may be a single structure made of one or more materials, or it may be a laminated structure made of multiple layers of the same or different compositions. <Electron blocking layer 5> An electron blocking layer 5 is provided between the hole transport layer 4 and the light-emitting layer 6, which will be described later.

[0365] The electron blocking layer functions as a layer that confines electrons within the light-emitting layer. That is, electrons injected from the cathode and transported to the light-emitting layer from the electron injection layer and / or electron transport layer are prevented from leaking into the hole injection layer and / or hole transport layer by the energy barrier present at the interface between the light-emitting layer and the electron blocking layer. As a result, electrons accumulate at the interface within the light-emitting layer, leading to effects such as improved luminescence efficiency, and resulting in an organic electroluminescent element with excellent light-emitting performance.

[0366] Furthermore, the electron blocking layer also has the function of transferring holes injected from the anode to the light-emitting layer. By interposing this electron blocking layer between the hole transport layer and the light-emitting layer, more holes can be injected into the light-emitting layer at a lower electric field.

[0367] The electron blocking layer material must possess at least one of the following properties: hole injection, hole transport, or electron barrier. The electron blocking layer material may be either organic or inorganic.

[0368] Specific examples of materials for the electron blocking layer include triazole derivatives, oxadiazole derivatives, imidazole derivatives, polyarylalkane derivatives, pyrazoline derivatives, pyrazolone derivatives, phenylenediamine derivatives, arylamine derivatives, aminosubstituted chalcone derivatives, oxazole derivatives, styrylanthracene derivatives, fluorenone derivatives, hydrazone derivatives, stilbene derivatives, silazane derivatives, aniline copolymers, conductive polymer oligomers (especially thiophene oligomers), porphyrin compounds, aromatic tertiary amine compounds, and styrylamine compounds. Among these, porphyrin compounds, aromatic tertiary amine compounds, and styrylamine compounds are preferred in terms of their good performance as organic electroluminescent devices, with aromatic tertiary amine compounds being particularly preferred.

[0369] Specific examples of aromatic tertiary amine compounds and styrylamine compounds include N,N,N',N'-tetraphenyl-4,4'-diaminophenyl, N,N'-diphenyl-N,N'-bis(m-tolyl)-[1,1'-biphenyl]-4,4'-diamine (TPD), 2,2-bis(4-di-p-tolylaminophenyl)propane, 1,1-bis(4-di-p-tolylaminophenyl)cyclohexane, N,N,N',N'-tetra-p-tolyl-4,4'-diaminobiphenyl, 1,1-bis(4-di-p-tolylaminophenyl)-4-phenylcyclohexane, bis(4-dimethylamino-2-methylphenyl)phenylmethane, bis(4-di-p-tolylaminophenyl)phenylmethane, N,N'-diphenyl-N,N'-di(4-methylphenyl Examples include, but are not limited to, 4,4'-diaminobiphenyl (Ciphenyl)-4,4'-diaminobiphenyl, N,N,N',N'-tetraphenyl-4,4'-diaminodiphenyl ether, 4,4'-bis(diphenylamino)quadriphenyl, N,N,N-tri(p-tolyl)amine, 4-(di-p-tolylamino)-4'-[4-(di-p-tolylamino)styryl]stilbene, 4-N,N-diphenylamino-(2-diphenylvinyl)benzene, 3-methoxy-4'-N,N-diphenylaminostilbenzene, N-phenylcarbazole, 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPD), and 4,4',4''-tris[N-(m-tolyl)-N-phenylamino]triphenylamine (MTDATA).

[0370] The electron blocking layer may be a single structure made of one or more materials, or it may be a laminated structure made of multiple layers of the same or different compositions.

[0371] The electron blocking layer may also be a transverse current suppressing material represented by formula (1) or a carbazole compound represented by formula (22) or formula (23). <Emitting layer 6> A light-emitting layer 6 is provided between the electron blocking layer 5 and the electron transport layer 7, which will be described later.

[0372] Materials for the light-emitting layer include phosphorescent materials, fluorescent materials, and thermally activated delayed fluorescence materials. In the light-emitting layer, electron-hole pairs recombine, resulting in light emission.

[0373] The luminescent layer may consist of a single low-molecular-weight material or a single polymer material, but more commonly, it consists of a host material doped with a guest compound. The luminescence primarily arises from the dopant and can have any color.

[0374] Examples of host materials include compounds having biphenylyl groups, fluorenyl groups, triphenylsilyl groups, carbazole groups, pyrenyl groups, and anthryl groups. More specifically, examples include, but are not limited to, DPVBi (4,4'-bis(2,2-diphenylvinyl)-1,1'-biphenyl), BCzVBi (4,4'-bis(9-ethyl-3-carbazovinylene)1,1'-biphenyl), TBADN (2-tert-butyl-9,10-di(2-naphthyl)anthracene), ADN (9,10-di(2-naphthyl)anthracene), CBP (4,4'-bis(carbazole-9-yl)biphenyl), CDBP (4,4'-bis(carbazole-9-yl)-2,2'-dimethylbiphenyl), 2-(9-phenylcarbazole-3-yl)-9-[4-(4-phenylphenylquinazoline-2-yl)carbazole, 9,10-bis(biphenyl)anthracene, etc.

[0375] Examples of fluorescent dopants include, but are not limited to, anthracene, pyrene, tetracene, xanthene, perylene, rubrene, coumarin, rhodamine, quinacridone, dicyanomethylenepyran compounds, thiopyran compounds, polymethine compounds, pyrylium, thiapyrillium compounds, fluorene derivatives, perifurante derivatives, indenoperylene derivatives, bis(azinyl)amine boron compounds, bis(azinyl)methane compounds, carbostyryl compounds, boron compounds, and cyclic amine compounds. Furthermore, a fluorescent dopant may be a combination of two or more types selected from these.

[0376] Examples of phosphorescent dopants include organometallic complexes of transition metals such as iridium, platinum, palladium, and osmium, but are not limited to these.

[0377] Specific examples of fluorescent dopants and phosphorescent dopants include, but are not limited to, Alq3 (tris(8-hydroxyquinoline)aluminum), DPAVBi (4,4'-bis[4-(di-p-tolylamino)styryl]biphenyl), perylene, bis[2-(4-n-hexylphenyl)quinoline](acetylacetonate)iridium(III), Ir(PPy)3 (tris(2-phenylpyridine)iridium(III)), and FirPic (bis(3,5-difluoro-2-(2-pyridyl)phenyl-(2-carboxypyridyl)iridium(III))).

[0378] Furthermore, the light-emitting material is not limited to being contained only in the light-emitting layer. For example, the light-emitting material may also be contained in a layer adjacent to the light-emitting layer (electron blocking layer 5 or electron transport layer 7). This can further increase the luminescence efficiency of the organic electroluminescent device.

[0379] The light-emitting layer may be a single-layer structure made of one or more materials, or it may be a laminated structure made of multiple layers of the same or different compositions. <Electron transport layer 7> An electron transport layer 7 is provided between the light-emitting layer 6 and the electron injection layer 8, which will be described later.

[0380] The electron transport layer has the function of transferring electrons injected from the cathode to the light-emitting layer. By interposing the electron transport layer between the cathode and the light-emitting layer, electrons are injected into the light-emitting layer at a lower electric field.

[0381] Specific examples of electron transport layer materials include tris(8-quinolinolato)aluminum derivatives, imidazole derivatives, benzimidazole derivatives, triazine derivatives, pyrimidine derivatives, pyridine derivatives, pyrazine derivatives, quinoline derivatives, quinoxaline derivatives, oxadiazole derivatives, phosphole derivatives, silole derivatives, phosphine oxide derivatives, and the like. Among these, triazine derivatives and pyrimidine derivatives are preferred because they provide good performance for organic electroluminescent devices.

[0382] Furthermore, the electron transport layer may include one or more conventionally known electron transport materials in addition to the materials described above.

[0383] Conventionally known electron transport materials include alkali metal complexes, alkaline earth metal complexes, and earth metal complexes. Examples of alkali metal complexes, alkaline earth metal complexes, and earth metal complexes include lithium 8-hydroxyquinolinate (Liq), bis(8-hydroxyquinolinate)zinc, bis(8-hydroxyquinolinate)copper, bis(8-hydroxyquinolinate)manganese, tris(8-hydroxyquinolinate)aluminum, tris(2-methyl-8-hydroxyquinolinate)aluminum, and tris(8-hydroxyquinolinate). Examples include gallium, bis(10-hydroxybenzo[h]quinolinate)beryllium, bis(10-hydroxybenzo[h]quinolinate)zinc, bis(2-methyl-8-quinolinate)chlorogallium, bis(2-methyl-8-quinolinate)(o-crezolate)gallium, bis(2-methyl-8-quinolinate)-1-naphtholatealuminum, and bis(2-methyl-8-quinolinate)-2-naphtholategallium. Inorganic compounds such as Yb, Li, and Ca may also be used.

[0384] The electron transport layer may be a single-layer structure made of one or more materials, or it may be a laminated structure made of multiple layers of the same or different compositions. <Electron injection layer 8> An electron injection layer 8 is provided between the electron transport layer 7 and the cathode 9, which will be described later.

[0385] The electron injection layer has the function of transferring electrons injected from the cathode to the light-emitting layer. By interposing the electron injection layer between the cathode and the light-emitting layer, electrons are injected into the light-emitting layer at a lower electric field.

[0386] Examples of materials for the electron injection layer include organic compounds such as fluorenone, anthraquinodimethane, diphenoquinone, thiopyrandioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, fluolenylidenemethane, anthraquinodimethane, and anthrone. In addition, inorganic compounds such as various oxides, fluorides, nitrides, and oxidized nitrides, as well as SiO2, AlO, SiN, SiON, AlON, GeO, LiO, LiON, TiO, TiON, TaO, TaON, TaN, LiF, C, and Yb, can also be used as materials for the electron injection layer. <Cathode 9> A cathode 9 is provided on the electron injection layer 8.

[0387] In the case of an organic electroluminescent element configured to extract only the light emitted after passing through the anode, the cathode can be formed from any conductive material.

[0388] Examples of cathode materials include metals with a low work function (hereinafter also referred to as electron-injection metals), alloys, electrically conductive compounds, and mixtures thereof. Here, a metal with a low work function is, for example, a metal with a work function of 4 eV or less.

[0389] Specific examples of cathode materials include sodium, sodium-potassium alloys, magnesium, lithium, magnesium / copper mixtures, magnesium / silver mixtures, magnesium / aluminum mixtures, magnesium / indium mixtures, aluminum / aluminum oxide (Al2O3) mixtures, indium, lithium / aluminum mixtures, and rare earth metals.

[0390] Among these, from the viewpoint of electron injection properties and durability against oxidation, mixtures of electron-injectable metals and metalloids, which have a higher work function and are more stable, such as magnesium / silver mixtures, magnesium / aluminum mixtures, magnesium / indium mixtures, aluminum / aluminum oxide (Al2O3) mixtures, and lithium / aluminum mixtures are preferred.

[0391] Next, we will explain how to manufacture the transverse current suppressing material (1).

[0392] The transverse current suppressing material (1) can be manufactured by the methods shown in the following synthesis pathways (p) to (s), but is not limited to these.

[0393] [ka]

[0394] [ka]

[0395] [ka]

[0396] [ka]

[0397] In formulas (39) to (45), Ar 1 Ar 2 , and Ar 3 The definitions are, respectively, Ar in equation (1). 1 Ar 2 , and Ar 3 This is the same as the definition; X 1 , X 2 and X 3 Each of these independently represents a halogen atom; X 1, X 2 and X 3 Examples of the halogen atom represented by include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom, and a chlorine atom or a bromine atom is preferable from the viewpoint of good yield of the lateral current suppressing material (1).

[0398] The reaction in the synthetic routes (p) to (s) is a method of reacting a halogen compound represented by formula (39), (42) or (44) with an amine compound represented by formula (40), (41), (43) or (45) in the presence of a palladium catalyst and a base, and the reaction conditions of a general Buchwald-Hartwig amination reaction can be applied.

[0399] The halogenated carbazole compound (39) or (44) can be produced, for example, according to Japanese Patent No. 5609256 and Japanese Patent No. 6115075, respectively. Commercially available products may also be used.

[0400] Examples of the palladium catalyst used in the aforementioned amination reaction include palladium salts such as palladium chloride, palladium acetate, palladium trifluoroacetate, and palladium nitrate. Further, complex compounds such as π-allylpalladium chloride dimer, palladium acetylacetonate, tris(dibenzylideneacetone)dipalladium, bis(dibenzylideneacetone)palladium, dichlorobis(acetonitrile)palladium, dichlorobis(benzonitrile)palladium; and palladium complexes having a tertiary phosphine as a ligand such as dichlorobis(triphenylphosphine)palladium, tetrakis(triphenylphosphine)palladium, dichloro(1,1'-bis(diphenylphosphino)ferrocene)palladium, bis(tri-tert-butylphosphine)palladium, bis(tricyclohexylphosphine)palladium, dichlorobis(tricyclohexylphosphine)palladium; and the like can be mentioned. These can also be prepared in the reaction system by adding a tertiary phosphine to a palladium salt or a complex compound.

[0401] Examples of tertiary phosphines include triphenylphosphine, trimethylphosphine, tributylphosphine, tri(tert-butyl)phosphine, tricyclohexylphosphine, tert-butyldiphenylphosphine, 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene, 2-(diphenylphosphino)-2'-(N,N-dimethylamino)biphenyl, 2-(di-tert-butylphosphino)biphenyl, 2-(dicyclohexylphosphino)biphenyl, and bis(diphenylphosphino) Examples include sphino)methane, 1,2-bis(diphenylphosphino)ethane, 1,3-bis(diphenylphosphino)propane, 1,4-bis(diphenylphosphino)butane, 1,1'-bis(diphenylphosphino)ferrocene, tri(2-furyl)phosphine, tri(o-tolyl)phosphine, tris(2,5-xylyl)phosphine, (±)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl, and 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl.

[0402] Among these, palladium complexes having a tertiary phosphine as a ligand are preferred in terms of yield, and palladium complexes having 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl, tri(o-tolyl)phosphine, tri(tert-butyl)phosphine, 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene, or tricyclohexylphosphine as ligands are even more preferred.

[0403] The molar ratio of tertiary phosphine to palladium salt or complex compound is preferably in the range of 1:10 to 10:1, and more preferably in the range of 1:2 to 3:1 for good yield. There is no limit to the amount of palladium catalyst used in the amination reaction described above, but for good yield, the molar equivalent of the palladium catalyst is preferably in the range of 0.005 to 0.5 molar equivalents relative to the amine compound.

[0404] Examples of bases used in the aforementioned amination reaction include metal hydroxide salts such as sodium hydroxide, potassium hydroxide, and calcium hydroxide; metal carbonates such as sodium carbonate, potassium carbonate, lithium carbonate, and cesium carbonate; metal acetates such as potassium acetate and sodium acetate; metal phosphates such as potassium phosphate and sodium phosphate; metal fluoride salts such as sodium fluoride, potassium fluoride, and cesium fluoride; and metal alkoxides such as sodium methoxide, potassium methoxide, sodium ethoxide, potassium isopropyl oxide, potassium tert-butoxide, and potassium tert-butoxide. Among these, potassium tert-butoxide is preferred for its good reaction yield. There are no particular restrictions on the amount of base used. For good reaction yield, the molar ratio of the base to the amine compound is preferably in the range of 1:2 to 10:1, and more preferably in the range of 1:1 to 4:1.

[0405] The aforementioned coupling and boration reactions can be carried out in a solvent.

[0406] Solvents include water, diisopropyl ether, dibutyl ether, cyclopentyl methyl ether (CPME), tetrahydrofuran (THF), 2-methyltetrahydrofuran, 1,4-dioxane, dimethoxyethane, and other ethers; aromatic hydrocarbons such as benzene, toluene, xylene, mesitylene, and tetralin; carbonate esters such as ethylene carbonate, propylene carbonate, dimethyl carbonate, diethyl carbonate, ethyl methyl carbonate, and 4-fluoroethylene carbonate; ethyl acetate, butyl acetate, methyl propionate, ethyl propionate, methyl butyrate, and γ Examples include esters such as lactones; amides such as N,N-dimethylformamide (DMF), dimethylacetamide (DMAc), and N-methylpyrrolidone (NMP); ureas such as N,N,N',N'-tetramethylurea (TMU) and N,N'-dimethylpropyleneurea (DMPU); and alcohols such as dimethyl sulfoxide (DMSO), methanol, ethanol, isopropyl alcohol, butanol, octanol, benzyl alcohol, ethylene glycol, propylene glycol, diethylene glycol, triethylene glycol, and 2,2,2-trifluoroethanol. These may be used individually or mixed in any ratio. There are no particular restrictions on the amount of solvent used. Of these, aromatic hydrocarbons are preferred in terms of good reaction yield, and toluene and xylene are even more preferred.

[0407] The aforementioned coupling and boration reactions can be carried out at temperatures appropriately selected from 0°C to 200°C, but it is preferable to carry them out at temperatures appropriately selected from 60°C to 160°C for better reaction yield.

[0408] The aforementioned amination reaction can yield the desired product by combining, as needed, common purification processes such as recrystallization, column chromatography, sublimation purification, and preparative HPLC after the reaction is complete. [Examples]

[0409] The present invention will be described in more detail below based on examples, but the present invention is not to be limited in any way by these examples. [ 1 H-NMR measurement] 1 For 1H-NMR measurements, a Bruker ASCEND HD (400MHz; manufactured by BRUKER) was used. 1 ¹H-NMR was performed using deuterated chloroform (CDCl3) as the measurement solvent and tetramethylsilane (TMS) as the internal standard. [FDMS (Field Desorption Mass Spectroscopy) Measurement] FDMS measurements were performed using a Hitachi M-80B. [Transverse current measurement] The lateral current was measured using a Keithley Instruments Source Meter 2400. [Measurement of organic electroluminescent elements] The luminescence characteristics of the organic electroluminescent elements were evaluated by applying a DC current to the fabricated elements at room temperature and using a luminance meter (product name: BM-9, manufactured by Topcon Techno House Co., Ltd.).

[0410] Synthesis Example 1 (Synthesis of 2-chloro-9-(biphenyl-4-yl)carbazole)

[0411] [ka]

[0412] In a 500 mL three-necked flask, 9.8 g (48 mmol) of 2-chloro-9H-carbazole, 10 g (58 mmol) of 4-fluorobiphenyl, 21 g (96 mmol) of tripotassium phosphate, and 230 mL of dimethyl sulfoxide were added and stirred at 180 °C for 16 hours. After cooling to room temperature, 230 mL of pure water was added and stirred, causing a solid to precipitate. The solid was then filtered and washed with water and hexane. The obtained solid was recrystallized in a mixed solvent of toluene and butanol to isolate 14 g (40 mmol) of 2-chloro-9-(biphenyl-4-yl)carbazole as a white solid (yield 80%).

[0413] The identification of the compound is 1 This was performed by 1H-NMR measurement.

[0414] 1 H-NMR(CDCl3);8.11(d,J=8.0Hz,1H),8.01(d,J=8.0Hz,1H),7.81-7.85(m,2H),7.68-7.72(m,2H),7.60-7.63(m,2H),7.51(t, J=8.0Hz,2H),7.41-7.46(m,4H),7.29-7.34(m,1H),7.24-7.28(m,1H) Synthesis Example 2 (Synthesis of 2-chloro-9-(biphenyl-2-yl)carbazole)

[0415] [ka]

[0416] Into a 500 mL three-necked flask, 9.8 g (48 mmol) of 2-chloro-9H-carbazole, 10 g (58 mmol) of 2-fluorobiphenyl, 21 g (96 mmol) of tripotassium phosphate, and 230 mL of dimethyl sulfoxide were added, and the mixture was stirred at 180°C for 16 hours. After allowing the mixture to cool to room temperature, 230 mL of pure water was added and stirred, and a solid precipitated. The solid was then collected by filtration and washed with water and hexane. The obtained solid was recrystallized from a mixed solvent of toluene and butanol to isolate 12 g (34 mmol) of 2-chloro-9-(biphenyl-2-yl)carbazole as a white solid (yield: 71%).

[0417] The compound was identified 1 by H-NMR measurement.

[0418] 1 H-NMR(CDCl3);7.98(d,J=8.0,1H),7.91(d,J=8.0,1H),7.54-7.68(m,3H),7.46-7.50(m,1H),7.24-7.30(m,1H),7.16-7.22(m,1H),7.10-7.15(m,1H),6.97-7.08(m,7H) Synthesis Example 3 (Synthesis of 2-chloro-9-(m-terphenyl-4'-yl)carbazole)

[0419]

Chemical Formula

[0420] Into a 500 mL three-necked flask, 8.2 g (40 mmol) of 2-chloro-9H-carbazole, 12 g (48 mmol) of 4'-fluoro-m-terphenyl, 17 g (80 mmol) of tripotassium phosphate, and 200 mL of dimethyl sulfoxide were added, and the mixture was stirred at 180°C for 16 hours. After allowing the mixture to cool to room temperature, 200 mL of pure water was added and stirred, and a solid precipitated. The solid was then collected by filtration and washed with water and hexane. The obtained solid was recrystallized from a mixed solvent of toluene and butanol to isolate 14 g (33 mmol) of 2-chloro-9-(m-terphenyl-4'-yl)carbazole as a white solid (yield: 79%).

[0421] The identification of the compound is 1 This was performed by 1H-NMR measurement.

[0422] 1 H-NMR(CDCl3);8.00(d,J=8.0Hz,1H),7.93(d,J=8.0Hz,1H),7.88(d,J=8.0Hz,1H),7.71-7.80(m,3H),7.49 -7.58(m,3H),7.41-7.46(m,1H),7.27-7.33(m,1H),7.17-7.23(m,1H),7.09-7.16(m,3H),6.98-7.09(m,5H) Synthesis Example 4 (Synthesis of 2-chloro-9-(p-terphenyl-2'-yl)carbazole)

[0423] [ka]

[0424] In a 500 mL three-necked flask, 8.2 g (40 mmol) of 2-chloro-9H-carbazole, 12 g (48 mmol) of 2'-fluoro-p-terphenyl, 17 g (80 mmol) of tripotassium phosphate, and 200 mL of dimethyl sulfoxide were added and the mixture was stirred at 180 °C for 16 hours. After cooling to room temperature, 200 mL of pure water was added and the mixture was stirred, causing a solid to precipitate. The solid was then filtered and washed with water and hexane. The obtained solid was recrystallized in a mixed solvent of toluene and butanol to isolate 15 g (35 mmol) of 2-chloro-9-(p-terphenyl-2'-yl)carbazole as a white solid (yield 85%).

[0425] The identification of the compound is 1 This was performed by 1H-NMR measurement.

[0426] 1H-NMR(CDCl3);8.01(d,J=8.0,1H),7.93(d,J=8.0,1H),7.84-7.88(m,1H),7.71-7.77(m,2H),7.64-7.69(m,2H),7.44-7.5 0(m,2H),7.36-7.41(m,1H),7.28-7.33(m,1H),7.18-7.23(m,1H),7.12-7.17(m,2H),7.08-7.11(m,1H),6.98-7.06(m,5H) Synthesis Example 5 (Synthesis of 2-chloro-9-(m-terphenyl-2'-yl)carbazole)

[0427] [ka]

[0428] In a 500 mL three-necked flask, 8.2 g (40 mmol) of 2-chloro-9H-carbazole, 12 g (48 mmol) of 2'-fluoro-m-terphenyl, 17 g (80 mmol) of tripotassium phosphate, and 200 mL of dimethyl sulfoxide were added and the mixture was stirred at 180 °C for 16 hours. After cooling to room temperature, 200 mL of pure water was added and the mixture was stirred, causing a solid to precipitate. The solid was then filtered and washed with water and hexane. The obtained solid was recrystallized in a mixed solvent of toluene and butanol to isolate 14 g (33 mmol) of 2-chloro-9-(m-terphenyl-2'-yl)carbazole as a white solid (yield 79%).

[0429] The identification of the compound is 1 This was performed by 1H-NMR measurement.

[0430] 1 H-NMR(CDCl3);7.83(d,J=8.0,1H),7.76(d,J=8.0,1H),7.66-7.72(m,1H), 7.59-7.64(m,2H),7.13-7.19(m,1H),7.04-7.09(m,1H),6.88-7.02(m,13H) Synthesis Example 6 (Synthesis of 2-chloro-9-(2-(2-naphthalenyl)phenyl)carbazole)

[0431] [ka]

[0432] In a 500 mL three-necked flask, 8.2 g (40 mmol) of 2-chloro-9H-carbazole, 11 g (48 mmol) of 2-(2-naphthalenyl)fluorobenzene, 17 g (80 mmol) of tripotassium phosphate, and 200 mL of dimethyl sulfoxide were added and the mixture was stirred at 180 °C for 16 hours. After cooling to room temperature, 200 mL of pure water was added and the mixture was stirred, causing a solid to precipitate. The solid was then filtered and washed with water and hexane. The obtained solid was recrystallized in a mixed solvent of toluene and butanol to isolate 14 g (34 mmol) of 2-chloro-9-(2-(2-naphthalenyl)phenyl)carbazole as a white solid (yield 86%).

[0433] The identification of the compound is 1 This was performed by 1H-NMR measurement.

[0434] 1 H-NMR(CDCl3);7.92-7.99(m,1H),7.86-7.91(m,1H),7.75-7.80(m,1H),7.47-7.70 (m,6H),7.28-7.42(m,3H),7.21-7.28(m,1H),7.07-7.17(m,4H),6.96-7.04(m,1H) Synthesis Example 7 (Synthesis of 2-chloro-9-(m-terphenyl-5'-yl)carbazole)

[0435] [ka]

[0436] In a 500 mL three-necked flask, 8.2 g (40 mmol) of 2-chloro-9H-carbazole, 12 g (48 mmol) of 5'-fluoro-m-terphenyl, 17 g (80 mmol) of tripotassium phosphate, and 200 mL of dimethyl sulfoxide were added and the mixture was stirred at 180 °C for 16 hours. After cooling to room temperature, 200 mL of pure water was added and the mixture was stirred, causing a solid to precipitate. The solid was then filtered and washed with water and hexane. The obtained solid was recrystallized in a mixed solvent of toluene and butanol to isolate 15 g (35 mmol) of 2-chloro-9-(m-terphenyl-5'-yl)carbazole as a white solid (yield 85%).

[0437] The identification of the compound is 1 This was performed by 1H-NMR measurement.

[0438] 1 H-NMR(CDCl3);8.13(d,J=8.0,1H),8.06(d,J=8.0,1H),7.91-7.96(m,1H),7.67-7.75(m,6H),7.34-7.55(m,9H),7.27-7.36(m,2H) Synthesis Example 8 (Synthesis of 2-chloro-9-(p-terphenyl-2'-yl)carbazole)

[0439] [ka]

[0440] In a 500 mL three-necked flask, 8.2 g (40 mmol) of 2-chloro-9H-carbazole, 12 g (48 mmol) of 2'-fluoro-p-terphenyl, 17 g (80 mmol) of tripotassium phosphate, and 200 mL of dimethyl sulfoxide were added and the mixture was stirred at 180 °C for 16 hours. After cooling to room temperature, 200 mL of pure water was added and the mixture was stirred, causing a solid to precipitate. The solid was then filtered and washed with water and hexane. The obtained solid was recrystallized in a mixed solvent of toluene and butanol to isolate 15 g (35 mmol) of 2-chloro-9-(p-terphenyl-2'-yl)carbazole as a white solid (yield 85%).

[0441] Compound identification was performed by FDMS measurement.

[0442] FDMS:429 Synthesis Example 9 (Synthesis of 22-chloro-9-(dibenzo[b,d]thiophene-4-yl)-9H-carbazole)

[0443] [ka]

[0444] Under a nitrogen atmosphere, 3.0 g (15 mmol) of 2-chloro-9H-carbazole, 4.7 g (18 mmol) of 4-bromodibenzo[b,d]thiophene, 2.9 g (21 mmol) of potassium carbonate, 20 mL of xylene, 33 mg (0.15 mmol) of palladium acetate, and 0.24 g (0.30 mmol) of a 25 wt% xylene solution of tri(tert-butyl)phosphine were added to a 100 mL three-necked flask and stirred at 140 °C for 22 hours. After cooling to room temperature, 200 mL of pure water was added and stirred, causing a solid to precipitate. The solid was then filtered and washed with water and hexane. The obtained solid was recrystallized in a mixed solvent of toluene and butanol to isolate 4.8 g (12 mmol) of 2-chloro-9-(dibenzo[b,d]thiophen-4-yl)-9H-carbazole, a white solid (yield 84%).

[0445] Compound identification was performed by FDMS measurement.

[0446] FDMS:383 Synthesis Example 10 (Synthesis of 9-([1,1':2',1''-terphenyl]-2-yl)-2-chloro-9H-carbazole)

[0447] [ka]

[0448] In a 300 mL three-necked flask, 7.0 g (35 mmol) of 2-chloro-9H-carbazole, 10 g (42 mmol) of 2-fluoro-1,1':2',1''-terphenyl, 15 g (69 mmol) of tripotassium phosphate, and 100 mL of dimethyl sulfoxide were added and stirred at 180 °C for 16 hours. After cooling to room temperature, 200 mL of pure water was added and stirred, causing a solid to precipitate. The solid was then filtered and washed with water and hexane. The obtained solid was recrystallized in a mixed solvent of toluene and butanol to isolate 12 g (28 mmol) of 9-([1,1':2',1''-terphenyl]-2-yl)-2-chloro-9H-carbazole, a white solid (yield 80%).

[0449] Compound identification was performed by FDMS measurement.

[0450] FDMS:423 Synthesis Example 11 (Synthesis of 2-chloro-9-(2-(dibenzo[b,d]furan-4-yl)phenyl)-9H-carbazole)

[0451] [ka]

[0452] In a 300 mL three-necked flask, 8.5 g (42 mmol) of 2-chloro-9H-carbazole, 13 g (51 mmol) of 4-(2-fluorophenyl)dibenzo[b,d]furan, 18 g (84 mmol) of tripotassium phosphate, and 100 mL of dimethyl sulfoxide were added and the mixture was stirred at 180 °C for 15 hours. After cooling to room temperature, 150 mL of pure water was added and the mixture was stirred, causing a solid to precipitate. The solid was then filtered and washed with water and hexane. The obtained solid was recrystallized in a mixed solvent of toluene and butanol to isolate 14 g (32 mmol) of 2-chloro-9-(2-(dibenzo[b,d]furan-4-yl)phenyl)-9H-carbazole, a white solid (yield 76%).

[0453] Compound identification was performed by FDMS measurement.

[0454] FDMS:423 Synthesis Example 12 (Synthesis of 2-chloro-9-(2-(phenanthrene-9-yl)phenyl)-9H-carbazole)

[0455] [ka]

[0456] In a 300 mL three-necked flask, 4.0 g (20 mmol) of 2-chloro-9H-carbazole, 6.5 g (24 mmol) of 9-(2-fluorophenyl)phenanthrene, 8.4 g (40 mmol) of tripotassium phosphate, and 120 mL of dimethyl sulfoxide were added and stirred at 180 °C for 12 hours. After cooling to room temperature, 150 mL of pure water was added and stirred, causing a solid to precipitate. The solid was then filtered and washed with water and hexane. The obtained solid was recrystallized in a mixed solvent of toluene and butanol to isolate 5.9 g (13 mmol) of 2-chloro-9-(2-(phenanthrene-9-yl)phenyl)-9H-carbazole, a white solid (yield 65%).

[0457] Compound identification was performed by FDMS measurement.

[0458] FDMS:454 Synthesis Example 13 (Synthesis of 4,4'-(2-fluoro-1,4-phenylene)didibenzo[b,d]furan)

[0459] [ka]

[0460] Under a nitrogen atmosphere, 5.0 g (30 mmol) of 1,4-dichloro-2-fluorobenzene, 15 g (70 mmol) of dibenzo[b,d]furan-4-ylboronic acid, 68 mg (0.30 mmol) of palladium acetate, 0.29 g (0.61 mmol) of XPhos, and 100 mL of THF were added to a 200 mL three-necked flask and stirred at 60°C. 15 mL (61 mmol) of 2 M tripotassium phosphate aqueous solution was added dropwise, and the mixture was stirred at 70°C for 22 hours. After cooling to room temperature, the mixture was transferred to a separatory funnel, and the organic layer was extracted with toluene. The organic layer was then washed with saturated sodium chloride aqueous solution. The organic layer was dried over anhydrous magnesium sulfate, and column chromatography was performed using a small amount of silica gel to remove highly polar components. Next, the solvent was removed under reduced pressure, and the resulting solid was recrystallized in a mixed solvent of toluene and butanol to isolate 9.9 g (23 mmol) of the white solid 4,4'-(2-fluoro-1,4-phenylene)didibenzo[b,d]furan (yield 76%).

[0461] Compound identification was performed by FDMS measurement.

[0462] FDMS:428 Synthesis Example 14 (Synthesis of 2,5-bis(dibenzo[b,d]furan-4-yl)phenyl)-2-chloro-9H-carbazole)

[0463] [ka]

[0464] In a 300 mL three-necked flask, 3.0 g (15 mmol) of 2-chloro-9H-carbazole, 7.6 g (18 mmol) of 4,4'-(2-fluoro-1,4-phenylene)didibenzo[b,d]furan obtained in Synthesis Example 14, 3.2 g (15 mmol) of tripotassium phosphate, and 60 mL of dimethyl sulfoxide were added and the mixture was stirred at 180 °C for 15 hours. After cooling to room temperature, 150 mL of pure water was added and the mixture was stirred, causing a solid to precipitate. The solid was then filtered and washed with water and hexane. The obtained solid was recrystallized in a mixed solvent of toluene and butanol to isolate 6.8 g (11 mmol) of 9-(2,5-bis(dibenzo[b,d]furan-4-yl)phenyl)-2-chloro-9H-carbazole, a white solid (yield 75%).

[0465] Compound identification was performed by FDMS measurement.

[0466] FDMS:609 Synthesis Example 15 (Synthesis of 2-(6-fluoro-[1,1'-biphenyl]-2-yl)naphthalene)

[0467] [ka]

[0468] Under a nitrogen atmosphere, 10 g (48 mmol) of 1-bromo-2-chloro-3-fluorobenzene, 8.2 g (48 mmol) of naphthalene-2-ylboronic acid, 0.11 g (0.48 mmol) of palladium acetate, 0.53 g (0.95 mmol) of 1,1'-bis(diphenylphosphino)ferrocene, and 100 mL of THF were added to a 100 mL three-necked flask and stirred at 60°C. 24 mL (95 mmol) of 4 M potassium carbonate aqueous solution was added dropwise, and the mixture was stirred at 70°C for 22 hours. After cooling to room temperature, the mixture was transferred to a separatory funnel, and the organic layer was extracted with toluene. The organic layer was then washed with saturated sodium chloride aqueous solution. The organic layer was dried over anhydrous magnesium sulfate, and column chromatography was performed using a small amount of silica gel to remove highly polar components. The solvent was then removed under reduced pressure to obtain the oil. Next, under a nitrogen stream, 5.8 g (48 mmol) of phenylboronic acid, 0.11 g (0.48 mmol) of palladium acetate, 0.46 g (0.95 mmol) of XPhos, and 100 mL of THF were added to a 100 mL three-necked flask and stirred at 60°C. 24 mL (95 mmol) of 4 M tripotassium phosphate aqueous solution was added dropwise, and the mixture was stirred at 70°C for 16 hours. After cooling to room temperature, the mixture was transferred to a separatory funnel, and the organic layer was extracted with toluene. The organic layer was then washed with saturated sodium chloride aqueous solution. The organic layer was dried with anhydrous magnesium sulfate, and column chromatography was performed using a small amount of silica gel to remove highly polar components. Next, the solvent was removed under reduced pressure, and the resulting solid was recrystallized in a mixed solvent of toluene and butanol to isolate 8.4 g (28 mmol) of the white solid 2-(6-fluoro-[1,1'-biphenyl]-2-yl)naphthalene (yield 59%).

[0469] Compound identification was performed by FDMS measurement.

[0470] FDMS:298 Synthesis Example 16 (Synthesis of 2-chloro-9-(6-(naphthalene-2-yl)-[1,1'-biphenyl]-2-yl)-9H-carbazole)

[0471] [ka]

[0472] In a 300 mL three-necked flask, 2.5 g (12 mmol) of 2-chloro-9H-carbazole, 4.4 g (15 mmol) of 2-(6-fluoro-[1,1'-biphenyl]-2-yl)naphthalene obtained in Synthesis Example 15, 2.6 g (12 mmol) of tripotassium phosphate, and 60 mL of dimethyl sulfoxide were added and the mixture was stirred at 180 °C for 30 hours. After cooling to room temperature, 100 mL of pure water was added and the mixture was stirred. Next, the aqueous layer and the organic layer were separated, and the organic layer was washed with saturated sodium chloride aqueous solution. The organic layer was dried over anhydrous magnesium sulfate, and column chromatography was performed using a small amount of silica gel to remove highly polar components. Next, the solvent was removed under reduced pressure, and the resulting solid was recrystallized in a mixed solvent of toluene and butanol to isolate 4.8 g (9.9 mmol) of 2-chloro-9-(6-(naphthalene-2-yl)-[1,1'-biphenyl]-2-yl)-9H-carbazole, a white solid (yield 80%). Compound identification was performed by FDMS measurement.

[0473] FDMS:479 Synthesis Example 17 (Synthesis of 2-chloro-9-(2-(phenanthrene-9-yl)phenyl)-9H-carbazole)

[0474] [ka]

[0475] Under a nitrogen atmosphere, 5.0 g (30 mmol) of 1,2-dichloro-4-fluorobenzene, 14 g (73 mmol) of [1,1'-biphenyl]-2-ylboronic acid, 68 mg (0.30 mmol) of palladium acetate, 0.29 g (0.61 mmol) of XPhos, and 100 mL of THF were added to a 100 mL three-necked flask and stirred at 60°C. 15 mL (61 mmol) of 4 M tripotassium phosphate aqueous solution was added dropwise, and the mixture was stirred at 70°C for 22 hours. After cooling to room temperature, 100 mL of pure water was added and stirred. The aqueous layer and organic layer were then separated, and the organic layer was washed with saturated sodium chloride aqueous solution. The organic layer was dried with anhydrous magnesium sulfate, and column chromatography was performed using a small amount of silica gel to remove highly polar components. Next, the solvent was removed under reduced pressure, and the resulting solid was recrystallized in a mixed solvent of toluene and butanol to isolate 7.8 g (19 mmol) of the white solid 4''-fluoro-1,1':2',1'':2'',1''':2''',1''''-quinkiphenyl (yield 64%).

[0476] Compound identification was performed by FDMS measurement.

[0477] FDMS:400 Synthesis Example 18 (Synthesis of 9-([1,1':2',1'':2'',1''':2''',1''''-quinkiphenyl]-4''-yl)-2-chloro-9H-carbazole)

[0478] [ka]

[0479] In a 300 mL three-necked flask, 2.0 g (9.9 mmol) of 2-chloro-9H-carbazole, 4.8 g (12 mmol) of 4''-fluoro-1,1':2',1'':2'',1''':2''',1''''-quinkiphenyl obtained in Synthesis Example 17, 2.1 g (9.9 mmol) of tripotassium phosphate, and 50 mL of dimethyl sulfoxide were added and the mixture was stirred at 180 °C for 40 hours. After cooling to room temperature, 150 mL of pure water was added and the mixture was stirred, causing a solid to precipitate. The solid was then filtered and washed with water and hexane. The obtained solid was recrystallized in a mixed solvent of toluene and butanol to isolate 4.6 g (7.9 mmol) of 9-([1,1':2',1'':2'',1''':2''',1''''-quinkiphenyl]-4''-yl)-2-chloro-9H-carbazole, a white solid (yield 80%).

[0480] Compound identification was performed by FDMS measurement.

[0481] FDMS:582 Synthesis Example 19 (Synthesis of 9-(2-bromo-6-methylphenyl)-2-chloro-9H-carbazole)

[0482] [ka]

[0483] In a 300 mL three-necked flask, 2.0 g (9.9 mmol) of 2-chloro-9H-carbazole, 2.8 g (15 mmol) of 1-bromo-2-fluoro-3-methylbenzene, 2.1 g (9.9 mmol) of tripotassium phosphate, and 45 mL of dimethyl sulfoxide were added and the mixture was stirred at 180 °C for 9 hours. After cooling to room temperature, 100 mL of pure water was added and the mixture was stirred. The aqueous layer and organic layer were then separated, and the organic layer was washed with saturated sodium chloride aqueous solution. The organic layer was dried over anhydrous magnesium sulfate, and column chromatography was performed using a small amount of silica gel to remove highly polar components. The solvent was then removed under reduced pressure, and the resulting solid was recrystallized in a mixed solvent of toluene and butanol to isolate 2.9 g (7.8 mmol) of 9-(2-bromo-6-methylphenyl)-2-chloro-9H-carbazole as a white solid (yield 79%).

[0484] Compound identification was performed by FDMS measurement.

[0485] FDMS:369 Synthesis Example 20 (Synthesis of 2-chloro-9-(2-methyl-6-(naphthalene-2-yl)phenyl)-9H-carbazole)

[0486] [ka]

[0487] Under a nitrogen atmosphere, 2.9 g (7.8 mmol) of 9-(2-bromo-6-methylphenyl)-2-chloro-9H-carbazole obtained in Synthesis Example 19, 1.5 g (8.6 mmol) of naphthalene-2-ylboronic acid, 18 mg (78 μmol) of palladium acetate, 89 mg (0.16 mmol) of 1,1'-bis(diphenylphosphino)ferrocene, and 60 mL of THF were added to a 100 mL three-necked flask and stirred at 60°C. 3.9 mL (16 mmol) of 4 M tripotassium phosphate aqueous solution was added dropwise, and the mixture was stirred at 70°C for 22 hours. After cooling to room temperature, the mixture was transferred to a separatory funnel, and the organic layer was extracted with toluene. The organic layer was then washed with saturated sodium chloride aqueous solution. The organic layer was dried over anhydrous magnesium sulfate, and column chromatography was performed using a small amount of silica gel to remove highly polar components. Next, the solvent was removed under reduced pressure, and the resulting solid was recrystallized in a mixed solvent of toluene and butanol to isolate 2.9 g (7.0 mmol) of the white solid 2-chloro-9-(2-methyl-6-(naphthalene-2-yl)phenyl)-9H-carbazole (yield 90%).

[0488] Compound identification was performed by FDMS measurement.

[0489] FDMS:417 Synthesis Example 21 (Synthesis of 2-(2-fluoro-[1,1'-biphenyl]-3-yl)naphthalene)

[0490] [ka]

[0491] Under a nitrogen atmosphere, 10 g (48 mmol) of 1-bromo-3-chloro-2-fluorobenzene, 9.0 g (53 mmol) of naphthalene-2-ylboronic acid, 0.11 g (0.48 mmol) and 0.46 g (0.95 mmol) of palladium acetate, and 100 mL of THF were added to a 100 mL three-necked flask and stirred at 60°C. 24 mL (95 mmol) of 4 M potassium carbonate aqueous solution was added dropwise, and the mixture was stirred at 70°C for 22 hours. After cooling to room temperature, the mixture was transferred to a separatory funnel, and the organic layer was extracted with toluene. The organic layer was then washed with saturated sodium chloride aqueous solution. The organic layer was dried over anhydrous magnesium sulfate, and column chromatography was performed using a small amount of silica gel to remove highly polar components. The solvent was then removed under reduced pressure to obtain the oil. Next, under a nitrogen atmosphere, 6.4 g (53 mmol) of phenylboronic acid, 0.11 g (0.48 mmol) of palladium acetate, 0.46 g (0.95 mmol) of XPhos, and 100 mL of THF were added to a 100 mL three-necked flask and stirred at 60°C. 24 mL (95 mmol) of 4 M tripotassium phosphate aqueous solution was added dropwise, and the mixture was stirred at 70°C for 16 hours. After cooling to room temperature, the mixture was transferred to a separatory funnel, and the organic layer was extracted with toluene. The organic layer was then washed with saturated sodium chloride aqueous solution. The organic layer was dried with anhydrous magnesium sulfate, and column chromatography was performed using a small amount of silica gel to remove highly polar components. Next, the solvent was removed under reduced pressure, and the resulting solid was recrystallized in a mixed solvent of toluene and butanol to isolate 10 g (34 mmol) of white solid 2-(2-fluoro-[1,1'-biphenyl]-3-yl)naphthalene (yield 71%).

[0492] Compound identification was performed by FDMS measurement.

[0493] FDMS:298 Synthesis Example 22 (Synthesis of 2-chloro-9-(3-(naphthalene-2-yl)-[1,1'-biphenyl]-2-yl)-9H-carbazole)

[0494] [ka]

[0495] In a 300 mL three-necked flask, 7.0 g (35 mmol) of 2-chloro-9H-carbazole, 12 g (42 mmol) of 2-(2-fluoro-[1,1'-biphenyl]-3-yl)naphthalene obtained in Synthesis Example 21, 7.4 g (35 mmol) of tripotassium phosphate, and 70 mL of dimethyl sulfoxide were added and the mixture was stirred at 180 °C for 12 hours. After cooling to room temperature, 150 mL of pure water was added and the mixture was stirred, causing a solid to precipitate. The solid was then filtered and washed with water and hexane. The obtained solid was recrystallized in a mixed solvent of toluene and butanol to isolate 14 g (30 mmol) of 2-chloro-9-(3-(naphthalene-2-yl)-[1,1'-biphenyl]-2-yl)-9H-carbazole, a white solid (yield 86%).

[0496] Compound identification was performed by FDMS measurement.

[0497] FDMS:479 Synthesis Example 23 (Synthesis of 1,1'-(2-fluoro-1,3-phenylene)dinaphthalene)

[0498] [ka]

[0499] Under a nitrogen atmosphere, 5.0 g (30 mmol) of 1,3-dichloro-2-fluorobenzene, 6.3 g (36 mmol) of naphthalene-1-ylboronic acid, 68 mg (0.30 mmol) of palladium acetate, 0.29 g (0.61 mmol) of XPhos, and 100 mL of THF were added to a 100 mL three-necked flask and stirred at 60°C. 15 mL (61 mmol) of 4 M tripotassium phosphate aqueous solution was added dropwise, and the mixture was stirred at 70°C for 22 hours. After cooling to room temperature, the mixture was transferred to a separatory funnel, and the organic layer was extracted with toluene. The organic layer was then washed with saturated sodium chloride aqueous solution. The organic layer was dried over anhydrous magnesium sulfate, and column chromatography was performed using a small amount of silica gel to remove highly polar components. Next, the solvent was removed under reduced pressure, and the resulting solid was recrystallized in a mixed solvent of toluene and butanol to isolate 9.5 g (27 mmol) of the white solid 1,1'-(2-fluoro-1,3-phenylene)dinaphthalene (yield 90%).

[0500] Compound identification was performed by FDMS measurement.

[0501] FDMS:348 Synthesis Example 24 (Synthesis of 2-chloro-9-(2,6-di(naphthalene-1-yl)phenyl)-9H-carbazole)

[0502] [ka]

[0503] In a 300 mL three-necked flask, 7.0 g (35 mmol) of 2-chloro-9H-carbazole, 15 g (42 mmol) of 1,1'-(2-fluoro-1,3-phenylene)dinaphthalene obtained in Synthesis Example 23, 7.4 g (35 mmol) of tripotassium phosphate, and 100 mL of dimethyl sulfoxide were added and the mixture was stirred at 180 °C for 15 hours. After cooling to room temperature, 150 mL of pure water was added and the mixture was stirred, causing a solid to precipitate. The solid was then filtered and washed with water and hexane. The obtained solid was recrystallized in a mixed solvent of toluene and butanol to isolate 15 g (29 mmol) of 2-chloro-9-(2,6-di(naphthalene-1-yl)phenyl)-9H-carbazole, a white solid (yield 83%).

[0504] Compound identification was performed by FDMS measurement.

[0505] FDMS:529 Synthesis Example 25 (Synthesis of 2'-fluoro-3,3''-dimethyl-1,1':3',1''-terphenyl)

[0506] [ka]

[0507] Under a nitrogen atmosphere, 5.0 g (30 mmol) of 1,3-dichloro-2-fluorobenzene, 4.5 g (33 mmol) of m-tol ylboronic acid, 68 mg (0.30 mmol) of palladium acetate, 0.29 g (0.61 mmol) of XPhos, and 100 mL of THF were added to a 100 mL three-necked flask and stirred at 60°C. 15 mL (61 mmol) of 4 M tripotassium phosphate aqueous solution was added dropwise, and the mixture was stirred at 70°C for 15 hours. After cooling to room temperature, the mixture was transferred to a separatory funnel, and the organic layer was extracted with toluene. The organic layer was then washed with saturated sodium chloride aqueous solution. The organic layer was dried over anhydrous magnesium sulfate, and column chromatography was performed using a small amount of silica gel to remove highly polar components. Next, the solvent was removed under reduced pressure, and the resulting solid was recrystallized in a mixed solvent of toluene and butanol to isolate 6.7 g (24 mmol) of the white solid 2'-fluoro-3,3''-dimethyl-1,1':3',1''-terphenyl (yield 80%).

[0508] Compound identification was performed by FDMS measurement.

[0509] FDMS:276 Synthesis Example 26 (Synthesis of 2-chloro-9-(3,3''-dimethyl-[1,1':3',1''-terphenyl]-2'-yl)-9H-carbazole)

[0510] [ka]

[0511] In a 300 mL three-necked flask, 3.0 g (15 mmol) of 2-chloro-9H-carbazole, 4.9 g (18 mmol) of 2'-fluoro-3,3''-dimethyl-1,1':3',1''-terphenyl obtained in Synthesis Example 25, 3.2 g (15 mmol) of tripotassium phosphate, and 30 mL of dimethyl sulfoxide were added and the mixture was stirred at 180 °C for 15 hours. After cooling to room temperature, 100 mL of pure water was added and the mixture was stirred, causing a solid to precipitate. The solid was then filtered and washed with water and hexane. The obtained solid was recrystallized in a mixed solvent of toluene and butanol to isolate 5.2 g (11 mmol) of 2-chloro-9-(3,3''-dimethyl-[1,1':3',1''-terphenyl]-2'-yl)-9H-carbazole, a white solid (yield 77%).

[0512] Compound identification was performed by FDMS measurement.

[0513] FDMS:457 Synthesis Example 27 (Synthesis of 4-(2'-fluoro-5'-methyl-[1,1'-biphenyl]-2-yl)dibenzo[b,d]furan)

[0514] [ka]

[0515] Under a nitrogen atmosphere, 5.0 g (26 mmol) of 2-bromo-1-fluoro-4-methylbenzene, 8.4 g (29 mmol) of (2-(dibenzo[b,d]furan-4-yl)phenyl)boronic acid, 59 mg (0.26 mmol) of palladium acetate, 0.25 g (0.53 mmol) of XPhos, and 100 mL of THF were added to a 100 mL three-necked flask and stirred at 60°C. 13 mL (53 mmol) of 4 M tripotassium phosphate aqueous solution was added dropwise, and the mixture was stirred at 70°C for 16 hours. After cooling to room temperature, the mixture was transferred to a separatory funnel, and the organic layer was extracted with toluene. The organic layer was then washed with saturated sodium chloride aqueous solution. The organic layer was dried over anhydrous magnesium sulfate, and column chromatography was performed using a small amount of silica gel to remove highly polar components. Next, the solvent was removed under reduced pressure, and the resulting solid was recrystallized in a mixed solvent of toluene and butanol to isolate 8.1 g (23 mmol) of the white solid 4-(2'-fluoro-5'-methyl-[1,1'-biphenyl]-2-yl)dibenzo[b,d]furan (yield 87%).

[0516] Compound identification was performed by FDMS measurement.

[0517] FDMS:382 Synthesis Example 28 (Synthesis of 9-(2'-(dibenzo[b,d]furan-4-yl)-5-methyl-[1,1'-biphenyl]-2-yl)-9H-carbazole)

[0518] [ka]

[0519] In a 300 mL three-necked flask, 2.7 g (13 mmol) of 2-chloro-9H-carbazole, 5.7 g (16 mmol) of 4-(2'-fluoro-5'-methyl-[1,1'-biphenyl]-2-yl)dibenzo[b,d]furan obtained in Synthesis Example 27, 2.8 g (13 mmol) of tripotassium phosphate, and 30 mL of dimethyl sulfoxide were added and the mixture was stirred at 180 °C for 40 hours. After cooling to room temperature, 150 mL of pure water was added and the mixture was stirred, causing a solid to precipitate. The solid was then filtered and washed with water and hexane. The obtained solid was recrystallized in a mixed solvent of toluene and butanol to isolate 5.0 g (9.9 mmol) of 9-(2'-(dibenzo[b,d]furan-4-yl)-5-methyl-[1,1'-biphenyl]-2-yl)-9H-carbazole, a white solid (yield 74%).

[0520] Compound identification was performed by FDMS measurement.

[0521] FDMS:499 Synthesis Example 29 (Synthesis of 2-chloro-9-(3',5'-dimethyl-[1,1'-biphenyl]-2-yl)-9H-carbazole)

[0522] [ka]

[0523] In a 300 mL three-necked flask, 2.7 g (13 mmol) of 2-chloro-9H-carbazole, 3.2 g (16 mmol) of 2-fluoro-3',5'-dimethyl-1,1'-biphenyl, 5.7 g (27 mmol) of tripotassium phosphate, and 30 mL of dimethyl sulfoxide were added and the mixture was stirred at 180 °C for 30 hours. After cooling to room temperature, 100 mL of pure water was added and the mixture was stirred. The aqueous layer and organic layer were then separated, and the organic layer was washed with saturated sodium chloride aqueous solution. The organic layer was dried over anhydrous magnesium sulfate, and column chromatography was performed using a small amount of silica gel to remove highly polar components. Next, the solvent was removed under reduced pressure, and the resulting solid was recrystallized in a mixed solvent of toluene and butanol to isolate 3.6 g (9.5 mmol) of 2-chloro-9-(3',5'-dimethyl-[1,1'-biphenyl]-2-yl)-9H-carbazole, a white solid (yield 71%).

[0524] Compound identification was performed by FDMS measurement.

[0525] FDMS:381 Synthesis Example 30 (Synthesis of 2-chloro-9-(2'-methyl-[1,1'-biphenyl]-2-yl)-9H-carbazole)

[0526] [ka]

[0527] In a 300 mL three-necked flask, 2.7 g (13 mmol) of 2-chloro-9H-carbazole, 3.0 g (16 mmol) of 2-fluoro-2'-methyl-1,1'-biphenyl, 5.7 g (27 mmol) of tripotassium phosphate, and 100 mL of dimethyl sulfoxide were added and stirred at 180 °C for 15 hours. After cooling to room temperature, 150 mL of pure water was added and stirred, causing a solid to precipitate. The solid was then filtered and washed with water and hexane. The obtained solid was recrystallized in a mixed solvent of toluene and butanol to isolate 3.4 g (9.4 mmol) of 2-chloro-9-(2'-methyl-[1,1'-biphenyl]-2-yl)-9H-carbazole, a white solid (yield 70%).

[0528] Compound identification was performed by FDMS measurement.

[0529] FDMS:367 Synthesis Example 31 (Synthesis of 1-(6-fluoro-2'-methyl-[1,1'-biphenyl]-3-yl)naphthalene)

[0530] [ka]

[0531] Under a nitrogen atmosphere, 5.0 g (24 mmol) of 4-bromo-2-chloro-1-fluorobenzene, 3.2 g (24 mmol) of o-trilboronic acid, 54 mg (0.24 mmol) of palladium acetate, 0.27 g (0.48 mmol) of 1,1'-bis(diphenylphosphino)ferrocene, and 75 mL of THF were added to a 100 mL three-necked flask and stirred at 60°C. 12 mL (48 mmol) of 4 M potassium carbonate aqueous solution was added dropwise, and the mixture was stirred at 70°C for 22 hours. After cooling to room temperature, the mixture was transferred to a separatory funnel, and the organic layer was extracted with toluene. The organic layer was then washed with saturated sodium chloride aqueous solution. The organic layer was dried over anhydrous magnesium sulfate, and column chromatography was performed using a small amount of silica gel to remove highly polar components. The solvent was then removed under reduced pressure to obtain the oil. Next, under a nitrogen stream, 4.1 g (24 mmol) of naphthalene-1-ylboronic acid, 54 mg (0.24 mmol) of palladium acetate, 0.23 g (0.48 mmol) of XPhos, and 80 mL of THF were added to a 100 mL three-necked flask and stirred at 60°C. 12 mL (48 mmol) of 4 M tripotassium phosphate aqueous solution was added dropwise, and the mixture was stirred at 70°C for 20 hours. After cooling to room temperature, the mixture was transferred to a separatory funnel, and the organic layer was extracted with toluene. The organic layer was then washed with saturated sodium chloride aqueous solution. The organic layer was dried with anhydrous magnesium sulfate, and column chromatography was performed using a small amount of silica gel to remove highly polar components. Next, the solvent was removed under reduced pressure, and the resulting solid was recrystallized in a mixed solvent of toluene and butanol to isolate 5.8 g (19 mmol) of the white solid 1-(6-fluoro-2'-methyl-[1,1'-biphenyl]-3-yl)naphthalene (yield 78%).

[0532] Compound identification was performed by FDMS measurement.

[0533] FDMS:312 Synthesis Example 32 (Synthesis of 2-chloro-9-methyl-9-(2'-methyl-5-(naphthalene-1-yl)-[1,1'-biphenyl]-2-yl)-9H-9l4-carbazole)

[0534] [ka]

[0535] In a 300 mL three-necked flask, 4.0 g (20 mmol) of 2-chloro-9H-carbazole, 7.4 g (24 mmol) of 1-(6-fluoro-2'-methyl-[1,1'-biphenyl]-3-yl)naphthalene obtained in Synthesis Example 31, 8.4 g (40 mmol) of tripotassium phosphate, and 40 mL of dimethyl sulfoxide were added and the mixture was stirred at 180 °C for 28 hours. After cooling to room temperature, 150 mL of pure water was added and the mixture was stirred, causing a solid to precipitate. The solid was then filtered and washed with water and hexane. The obtained solid was recrystallized in a mixed solvent of toluene and butanol to isolate 6.7 g (13 mmol) of 2-chloro-9-methyl-9-(2'-methyl-5-(naphthalene-1-yl)-[1,1'-biphenyl]-2-yl)-9H-9l4-carbazole, a white solid (yield 66%).

[0536] Compound identification was performed by FDMS measurement.

[0537] FDMS:508 Synthesis Example 33 (Synthesis of 4-chloro-9-(2'-(naphthalene-1-yl)-[1,1'-biphenyl]-4-yl)-9H-carbazole)

[0538] [ka]

[0539] In a 300 mL three-necked flask, 4.1 g (20 mmol) of 2-chloro-9H-carbazole, 7.3 g (24 mmol) of 1-(4'-fluoro-[1,1'-biphenyl]-2-yl)naphthalene, 8.6 g (41 mmol) of tripotassium phosphate, and 50 mL of dimethyl sulfoxide were added and the mixture was stirred at 180 °C for 35 hours. After cooling to room temperature, 150 mL of pure water was added and the mixture was stirred, causing a solid to precipitate. The solid was then filtered and washed with water and hexane. The obtained solid was recrystallized in a mixed solvent of toluene and butanol to isolate 8.3 g (17 mmol) of 4-chloro-9-(2'-(naphthalene-1-yl)-[1,1'-biphenyl]-4-yl)-9H-carbazole, a white solid (yield 85%).

[0540] Compound identification was performed by FDMS measurement.

[0541] FDMS:479 Synthesis Example 34 (Synthesis of 4-chloro-9-(2-(dibenzo[b,d]thiophen-4-yl)phenyl)-9H-carbazole)

[0542] [ka]

[0543] In a 300 mL three-necked flask, 4.5 g (22 mmol) of 2-chloro-9H-carbazole, 7.5 g (27 mmol) of 4-(2-fluorophenyl)dibenzo[b,d]thiophene, 9.5 g (45 mmol) of tripotassium phosphate, and 50 mL of dimethyl sulfoxide were added and the mixture was stirred at 180 °C for 15 hours. After cooling to room temperature, 150 mL of pure water was added and the mixture was stirred, causing a solid to precipitate. The solid was then filtered and washed with water and hexane. The obtained solid was recrystallized in a mixed solvent of toluene and butanol to isolate 7.5 g (16 mmol) of 4-chloro-9-(2-(dibenzo[b,d]thiophen-4-yl)phenyl)-9H-carbazole, a white solid (yield 73%).

[0544] Compound identification was performed by FDMS measurement.

[0545] FDMS:459 Synthesis Example 35 (Synthesis of 4-chloro-9-(2'-(naphthalene-2-yl)-[1,1'-biphenyl]-3-yl)-9H-carbazole)

[0546] [ka]

[0547] In a 300 mL three-necked flask, 3.0 g (15 mmol) of 4-chloro-9H-carbazole, 5.3 g (18 mmol) of 2-(3'-fluoro-[1,1'-biphenyl]-2-yl)naphthalene, 6.3 g (30 mmol) of tripotassium phosphate, and 30 mL of dimethyl sulfoxide were added and the mixture was stirred at 180 °C for 35 hours. After cooling to room temperature, 150 mL of pure water was added and the mixture was stirred, causing a solid to precipitate. The solid was then filtered and washed with water and hexane. The obtained solid was recrystallized in a mixed solvent of toluene and butanol to isolate 5.7 g (12 mmol) of 4-chloro-9-(2'-(naphthalene-2-yl)-[1,1'-biphenyl]-3-yl)-9H-carbazole, a white solid (yield 80%).

[0548] Compound identification was performed by FDMS measurement.

[0549] FDMS: 479 Synthesis Example 36 (Synthesis of 4-chloro-9-(4-phenylnaphthalene-1-yl)-9H-carbazole)

[0550] [ka]

[0551] In a 300 mL three-necked flask, 6.0 g (30 mmol) of 2-chloro-9H-carbazole, 7.9 g (36 mmol) of 1-fluoro-4-phenylnaphthalene, 13 g (60 mmol) of tripotassium phosphate, and 70 mL of dimethyl sulfoxide were added and the mixture was stirred at 180 °C for 15 hours. After cooling to room temperature, 150 mL of pure water was added and the mixture was stirred, causing a solid to precipitate. The solid was then filtered and washed with water and hexane. The obtained solid was recrystallized in a mixed solvent of toluene and butanol to isolate 10 g (25 mmol) of 4-chloro-9-(4-phenylnaphthalene-1-yl)-9H-carbazole, a white solid (yield 83%).

[0552] Compound identification was performed by FDMS measurement.

[0553] FDMS:403 Synthesis Example 37 (Synthesis of 9-(4-([1,1'-biphenyl]-4-yl)naphthalene-1-yl)-4-chloro-9H-carbazole)

[0554] [ka]

[0555] In a 300 mL three-necked flask, 6.0 g (30 mmol) of 2-chloro-9H-carbazole, 11 g (36 mmol) of 1-([1,1'-biphenyl]-4-yl)-4-fluoronaphthalene, 13 g (60 mmol) of tripotassium phosphate, and 100 mL of dimethyl sulfoxide were added and the mixture was stirred at 180 °C for 15 hours. After cooling to room temperature, 150 mL of pure water was added and the mixture was stirred, causing a solid to precipitate. The solid was then filtered and washed with water and hexane. The obtained solid was recrystallized in a mixed solvent of toluene and butanol to isolate 12 g (26 mmol) of 9-(4-([1,1'-biphenyl]-4-yl)naphthalene-1-yl)-4-chloro-9H-carbazole, a white solid (yield 87%).

[0556] Compound identification was performed by FDMS measurement.

[0557] FDMS:479 Synthesis Example 38 (Synthesis of 4-chloro-9-(2-phenylnaphthalene-1-yl)-9H-carbazole)

[0558] [ka]

[0559] In a 300 mL three-necked flask, 5.5 g (27 mmol) of 2-chloro-9H-carbazole, 7.3 g (33 mmol) of 1-fluoro-2-phenylnaphthalene, 12 g (55 mmol) of tripotassium phosphate, and 60 mL of dimethyl sulfoxide were added and the mixture was stirred at 180 °C for 15 hours. After cooling to room temperature, 150 mL of pure water was added and the mixture was stirred, causing a solid to precipitate. The solid was then filtered and washed with water and hexane. The obtained solid was recrystallized in a mixed solvent of toluene and butanol to isolate 8.5 g (21 mmol) of 4-chloro-9-(2-phenylnaphthalene-1-yl)-9H-carbazole, a white solid (yield 77%).

[0560] Compound identification was performed by FDMS measurement.

[0561] FDMS:403 Synthesis Example 39 (Synthesis of 2-chloro-9-(4,4''-dimethyl-[1,1':3',1''-terphenyl]-4'-yl)-9H-carbazole)

[0562] [ka]

[0563] In a 300 mL three-necked flask, 5.0 g (25 mmol) of 2-chloro-9H-carbazole, 8.2 g (30 mmol) of 4'-fluoro-4,4''-dimethyl-1,1':3',1''-terphenyl, 11 g (50 mmol) of tripotassium phosphate, and 100 mL of dimethyl sulfoxide were added and the mixture was stirred at 180 °C for 15 hours. After cooling to room temperature, 50 mL of pure water was added and the mixture was stirred, causing a solid to precipitate. The solid was then filtered and washed with water and hexane. The obtained solid was recrystallized in a mixed solvent of toluene and butanol to isolate 7.9 g (17 mmol) of 2-chloro-9-(4,4''-dimethyl-[1,1':3',1''-terphenyl]-4'-yl)-9H-carbazole, a white solid (yield 70%).

[0564] Compound identification was performed by FDMS measurement.

[0565] FDMS:423 Synthesis Example 40 (Synthesis of 4-chloro-9-(1-phenylnaphthalene-2-yl)-9H-carbazole)

[0566] [ka]

[0567] In a 300 mL three-necked flask, 5.0 g (25 mmol) of 2-chloro-9H-carbazole, 6.6 g (30 mmol) of 2-fluoro-1-phenylnaphthalene, 11 g (50 mmol) of tripotassium phosphate, and 50 mL of dimethyl sulfoxide were added and the mixture was stirred at 180 °C for 15 hours. After cooling to room temperature, 150 mL of pure water was added and the mixture was stirred, causing a solid to precipitate. The solid was then filtered and washed with water and hexane. The obtained solid was recrystallized in a mixed solvent of toluene and butanol to isolate 8.1 g (20 mmol) of 4-chloro-9-(1-phenylnaphthalene-2-yl)-9H-carbazole, a white solid (yield 81%).

[0568] Compound identification was performed by FDMS measurement.

[0569] FDMS:403 Synthesis Example 41 (Synthesis of 9-([1,1':3',1''-terphenyl]-2-yl)-4-chloro-9H-carbazole)

[0570] [ka]

[0571] In a 300 mL three-necked flask, 7.5 g (37 mmol) of 2-chloro-9H-carbazole, 11 g (45 mmol) of 2-fluoro-1,1':3',1''-terphenyl, 16 g (74 mmol) of tripotassium phosphate, and 80 mL of dimethyl sulfoxide were added and the mixture was stirred at 180 °C for 15 hours. After cooling to room temperature, 150 mL of pure water was added and the mixture was stirred, causing a solid to precipitate. The solid was then filtered and washed with water and hexane. The obtained solid was recrystallized in a mixed solvent of toluene and butanol to isolate 12 g (28 mmol) of 9-([1,1':3',1''-terphenyl]-2-yl)-4-chloro-9H-carbazole, a white solid (yield 76%).

[0572] Compound identification was performed by FDMS measurement.

[0573] FDMS:429 Synthesis Example 42 (Synthesis of 4-chloro-9-(2-(dibenzo[b,d]thiophen-2-yl)-5-methylphenyl)-9H-carbazole)

[0574] [ka]

[0575] In a 300 mL three-necked flask, 3.0 g (15 mmol) of 2-chloro-9H-carbazole, 5.2 g (18 mmol) of 2-(2-fluoro-4-methylphenyl)dibenzo[b,d]thiophene, 6.3 g (30 mmol) of tripotassium phosphate, and 100 mL of dimethyl sulfoxide were added and the mixture was stirred at 180 °C for 15 hours. After cooling to room temperature, 150 mL of pure water was added and the mixture was stirred, causing a solid to precipitate. The solid was then filtered and washed with water and hexane. The obtained solid was recrystallized in a mixed solvent of toluene and butanol to isolate 4.4 g (9.4 mmol) of 4-chloro-9-(2-(dibenzo[b,d]thiophen-2-yl)-5-methylphenyl)-9H-carbazole, a white solid (yield 63%).

[0576] Compound identification was performed by FDMS measurement.

[0577] FDMS:473 Example 1 (Synthesis of compound (D68))

[0578] [ka]

[0579] Under a nitrogen atmosphere, 3.1 g (8.7 mmol) of 9-([1,1'-biphenyl]-4-yl)-2-chloro-9H-carbazole obtained in Synthesis Example 1, 2.8 g (8.7 mmol) of N-([1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-2-amine, 1.0 g (10 mmol) of sodium-tert-butoxide, 20 mL of xylene, 20 mg (87 μmol) of palladium acetate, and 0.21 g (0.26 mmol) of a 25 wt% xylene solution of tri(tert-butyl)phosphine were added to a 100 mL three-neck flask and stirred at 140 °C for 22 hours. After cooling to room temperature, 22 mL of pure water was added and stirred. The aqueous layer and organic layer were then separated, and the organic layer was further washed with saturated sodium chloride aqueous solution. The organic layer was dried with anhydrous magnesium sulfate, and then column chromatography was performed using a small amount of silica gel to remove highly polar components. Next, the solvent was removed under reduced pressure, and the resulting solid was recrystallized in a mixed solvent of toluene and butanol to isolate 4.0 g (6.3 mmol) of compound (D68) as a white solid (72% yield). The sublimation temperature of D68 was confirmed to be 300°C, and the sublimated D68 was confirmed to be glassy.

[0580] Compound identification was performed by FDMS measurement.

[0581] FDMS:638 Example 2 (Synthesis of D116)

[0582] [ka]

[0583] Under a nitrogen atmosphere, 3.8 g (9.9 mmol) of 2-chloro-9-(dibenzo[b,d]thiophene-4-yl)-9H-carbazole obtained in Synthesis Example 9, 3.0 g (9.0 mmol) of 4-(9H-carbazol-9-yl)-N-phenylaniline, 1.0 g (11 mmol) of sodium-tert-butoxide, 30 mL of xylene, 20 mg (90 μmol) of palladium acetate, and 0.22 g (0.27 mmol) of a 25 wt% xylene solution of tri(tert-butyl)phosphine were added to a 100 mL three-neck flask and stirred at 140 °C for 16 hours. After cooling to room temperature, 22 mL of pure water was added and stirred. Next, the aqueous layer and organic layer were separated, and the organic layer was further washed with saturated sodium chloride aqueous solution. The organic layer was dried with anhydrous magnesium sulfate, and column chromatography was performed using a small amount of silica gel to remove highly polar components. Next, the solvent was removed under reduced pressure, and the resulting solid was recrystallized in a mixed solvent of toluene and butanol to isolate 4.2 g (6.2 mmol) of the compound (D116) as a white solid (yield 69%). The sublimation temperature of D116 was 310°C, and it was confirmed that the sublimated D116 was glassy.

[0584] Compound identification was performed by FDMS measurement.

[0585] FDMS:681 Example 3 (Synthesis of compound (D166))

[0586] [ka]

[0587] Under a nitrogen atmosphere, 2.5 g (7.8 mmol) of 9-phenyl-2-bromocarbazole, 2.6 g (6.5 mmol) of N-(p-biphenyl-4-yl)-N-(o-terphenyl-4-yl)amine obtained in Synthesis Example 20, 1.3 g (0.82 mmol) of sodium-tert-butoxide, 22 mL of o-xylene, 4.4 mg (20 μmol) of palladium acetate, and 48 mg (59 μmol) of a 25 wt% toluene solution of tri(tert-butyl)phosphine were added to a 100 mL three-neck flask and stirred at 140 °C for 20 hours. After cooling to room temperature, 22 mL of pure water was added and stirred. The aqueous layer and organic layer were then separated, and the organic layer was washed with saturated sodium chloride aqueous solution. The organic layer was dried over anhydrous magnesium sulfate, and column chromatography was performed using a small amount of silica gel to remove highly polar components. Next, the solvent was removed under reduced pressure, and the resulting solid was recrystallized in a mixed solvent of toluene and butanol to isolate 2.5 g (4.4 mmol) of compound (D165) as a white solid (yield 68%). The sublimation temperature of D166 was 310°C, and it was confirmed that the sublimated product of D166 was glassy.

[0588] Compound identification was performed by FDMS measurement.

[0589] FDMS:612 Example 4 (Synthesis of compound (D169))

[0590] [ka]

[0591] Under a nitrogen atmosphere, 1.8 g (6.3 mmol) of 2-chloro-9-phenyl-9H-carbazole, 2.7 g (6.0 mmol) of N-([1,1':2',1''-terphenyl]-3'-yl)-6-phenylnaphthalene-2-amine, 0.75 g (7.8 mmol) of sodium tert-butoxide, 20 mL of xylene, 14 mg (60 μmol) of palladium acetate, and 0.15 g (0.18 mmol) of a 25 wt% xylene solution of tri(tert-butyl)phosphine were added to a 100 mL three-neck flask and stirred at 140 °C for 22 hours. After cooling to room temperature, 22 mL of pure water was added and stirred. The aqueous layer and organic layer were then separated, and the organic layer was washed with saturated sodium chloride aqueous solution. The organic layer was dried over anhydrous magnesium sulfate, and column chromatography was performed using a small amount of silica gel to remove highly polar components. Next, the solvent was removed under reduced pressure, and the resulting solid was recrystallized in a mixed solvent of toluene and butanol to isolate 3.1 g (4.5 mmol) of the white solid N-([1,1':2',1''-terphenyl]-3'-yl)-9-phenyl-N-(6-phenylnaphthalen-2-yl)-9H-carbazole-2-amine (74% yield). The sublimation temperature of D169 was 315°C, and it was confirmed that the sublimated product of D169 was glassy.

[0592] Compound identification was performed by FDMS measurement.

[0593] FDMS:688 Example 5 (Synthesis of compound (D180))

[0594] [ka]

[0595] Under a nitrogen atmosphere, 2.1 g (7.7 mmol) of 2-chloro-9-phenyl-9H-carbazole, 3.0 g (7.3 mmol) of N-(2-(dibenzo[b,d]furan-4-yl)phenyl)-[1,1'-biphenyl]-4-amine, 0.91 g (9.5 mmol) of sodium-tert-butoxide, 20 mL of xylene, 16 mg (73 μmol) of palladium acetate, and 0.18 g (0.22 mmol) of a 25 wt% xylene solution of tri(tert-butyl)phosphine were added to a 100 mL three-neck flask and stirred at 140 °C for 22 hours. After cooling to room temperature, 22 mL of pure water was added and stirred. The aqueous layer and organic layer were then separated, and the organic layer was washed with saturated sodium chloride aqueous solution. The organic layer was dried over anhydrous magnesium sulfate, and column chromatography was performed using a small amount of silica gel to remove highly polar components. Next, the solvent was removed under reduced pressure, and the resulting solid was recrystallized in a mixed solvent of toluene and butanol to isolate 3.6 g (5.5 mmol) of the compound (D180) as a white solid (76% yield). The sublimation temperature of D180 was confirmed to be 270°C, and the sublimated product of D180 was confirmed to be glassy.

[0596] Compound identification was performed by FDMS measurement.

[0597] FDMS:652 Example 6 (Synthesis of compound (D184))

[0598] [ka]

[0599] Under a nitrogen atmosphere, 2.7 g (6.2 mmol) of 9-([1,1':3',1''-terphenyl]-5'-yl)-2-chloro-9H-carbazole, 2.5 g (5.9 mmol) of N-([1,1':4',1''-terphenyl]-4-yl)phenanthrene-9-amine, 0.74 g (7.7 mmol) of sodium-tert-butoxide, 20 mL of xylene, 13 mg (59 μmol) of palladium acetate, and 0.14 g (0.18 mmol) of a 25 wt% xylene solution of tri(tert-butyl)phosphine were added to a 100 mL three-neck flask and stirred at 140 °C for 22 hours. After cooling to room temperature, 22 mL of pure water was added and stirred. The aqueous layer and organic layer were then separated, and the organic layer was washed with saturated sodium chloride aqueous solution. The organic layer was dried with anhydrous magnesium sulfate, and highly polar components were removed by column chromatography using a small amount of silica gel. The solvent was then removed under reduced pressure, and the resulting solid was recrystallized in a mixed solvent of toluene and butanol to isolate 3.5 g (4.3 mmol) of compound (D184) as a white solid (73% yield). The sublimation temperature of D184 was confirmed to be 285°C, and the sublimated product was found to be glassy.

[0600] Compound identification was performed by FDMS measurement.

[0601] FDMS:423 Example 7 (Synthesis of compound (D188))

[0602] [ka]

[0603] Under a nitrogen atmosphere, 2.4 g (7.4 mmol) of N-(9,9-dimethylfluoren-2-yl)-N-(9-phenylcarbazole-2-yl)amine, 2.3 g (6.1 mmol) of 4-bromodibenzofuran, 0.77 g (8.0 mmol) of sodium-tert-butoxide, 20 mL of o-xylene, 4.1 mg (18 μmol) of palladium acetate, and 45 mg (55 μmol) of a 25 wt% toluene solution of tri(tert-butyl)phosphine were added to a 100 mL three-neck flask and stirred at 140 °C for 20 hours. After cooling to room temperature, 20 mL of pure water was added and stirred. The aqueous layer and organic layer were then separated, and the organic layer was washed with saturated sodium chloride aqueous solution. The organic layer was dried over anhydrous magnesium sulfate, and column chromatography was performed using a small amount of silica gel to remove highly polar components. Next, the solvent was removed under reduced pressure, and the resulting solid was recrystallized in a mixed solvent of toluene and butanol to isolate 3.0 g (4.0 mmol) of the yellow solid compound (D188) (yield 80%). The sublimation temperature of D188 was confirmed to be 325°C, and the sublimated product of D188 was confirmed to be glassy.

[0604] Compound identification was performed by FDMS measurement.

[0605] FDMS:616 Example 8 (Synthesis of compound (D194))

[0606] [ka]

[0607] Under a nitrogen atmosphere, 3.4 g (11 mmol) of 9-phenyl-2-bromocarbazole, 3.3 g (8.9 mmol) of N-(biphenyl-4-yl)-N-(4-phenylnaphthalen-1-yl)amine, 1.1 g (12 mmol) of sodium-tert-butoxide, 30 mL of o-xylene, 6.0 mg (27 μmol) of palladium acetate, and 65 mg (80 μmol) of a 25 wt% toluene solution of tri(tert-butyl)phosphine were added to a 100 mL three-neck flask and stirred at 140 °C for 22 hours. After cooling to room temperature, 37 mL of pure water was added and stirred. The aqueous layer and organic layer were then separated, and the organic layer was washed with saturated sodium chloride aqueous solution. The organic layer was dried over anhydrous magnesium sulfate, and column chromatography was performed using a small amount of silica gel to remove highly polar components. Next, the solvent was removed under reduced pressure, and the resulting solid was recrystallized in a mixed solvent of toluene and butanol to isolate 4.8 g (7.9 mmol) of the compound (D194) as a white solid (yield 89%). The sublimation temperature of D194 was confirmed to be 300°C, and the sublimated product of D194 was confirmed to be glassy.

[0608] Compound identification was performed by FDMS measurement.

[0609] FDMS:612 Example 9 (Synthesis of compound (D273))

[0610] [ka]

[0611] Under a nitrogen atmosphere, 2.2 g (6.2 mmol) of 9-([1,1'-biphenyl]-2-yl)-2-chloro-9H-carbazole obtained in Synthesis Example 2, 1.9 g (5.9 mmol) of N-([1,1':4',1''-terphenyl]-4-yl)phenanthrene-9-amine, 0.74 g (7.7 mmol) of sodium-tert-butoxide, 20 mL of xylene, 13 mg (59 μmol) of palladium acetate, and 0.14 g (0.18 mmol) of a 25 wt% xylene solution of tri(tert-butyl)phosphine were added to a 100 mL three-neck flask and stirred at 140 °C for 8 hours. After cooling to room temperature, 40 mL of pure water was added and stirred. The aqueous layer and organic layer were then separated, and the organic layer was further washed with saturated sodium chloride aqueous solution. The organic layer was dried with anhydrous magnesium sulfate, and then column chromatography was performed using a small amount of silica gel to remove highly polar components. Next, the solvent was removed under reduced pressure, and the resulting solid was recrystallized in a mixed solvent of toluene and butanol to isolate 3.2 g (5.0 mmol) of compound (D273) as a white solid (yield 84%). The sublimation temperature of D273 was 270°C, and it was confirmed that the sublimated product of D273 was glassy.

[0612] Compound identification was performed by FDMS measurement.

[0613] FDMS:638 Example 10 (Synthesis of compound (D278))

[0614] [ka]

[0615] Under a nitrogen stream, 2.7 g (6.2 mmol) of 9-([1,1':3',1''-terphenyl]-5'-yl)-2-chloro-9H-carbazole obtained in Synthesis Example 7, 2.5 g (5.9 mmol) of N-([1,1':4',1''-terphenyl]-4-yl)phenanthrene-9-amine, 0.74 g (7.7 mmol) of sodium-tert-butoxide, 20 mL of xylene, 13 mg (59 μmol) of palladium acetate, and 0.14 g (0.18 mmol) of a 25 wt% xylene solution of tri(tert-butyl)phosphine were added to a 100 mL three-neck flask and stirred at 140 °C for 22 hours. After cooling to room temperature, 22 mL of pure water was added and stirred. The aqueous layer and organic layer were then separated, and the organic layer was washed with saturated sodium chloride aqueous solution. The organic layer was dried with anhydrous magnesium sulfate, and then column chromatography was performed using a small amount of silica gel to remove highly polar components. Next, the solvent was removed under reduced pressure, and the resulting solid was recrystallized in a mixed solvent of toluene and butanol to isolate 3.5 g (4.3 mmol) of compound (D278) as a white solid (yield 73%). The sublimation temperature of D278 was 330°C, and it was confirmed that the sublimated product of D278 was glassy.

[0616] Compound identification was performed by FDMS measurement.

[0617] FDMS:814 Example 11 (Synthesis of compound (D285))

[0618] [ka]

[0619] Under a nitrogen atmosphere, 2.5 g (5.8 mmol) of 9-([1,1':2',1''-terphenyl]-2-yl)-2-chloro-9H-carbazole obtained in Synthesis Example 10, 2.4 g (5.5 mmol) of N-(4-(9,9-dimethyl-9H-fluoren-2-yl)phenyl)-[1,1'-biphenyl]-4-amine, 0.69 g (7.1 mmol) of sodium-tert-butoxide, 20 mL of xylene, 12 mg (55 μmol) of palladium acetate, and 0.13 g (0.16 mmol) of a 25 wt% xylene solution of tri(tert-butyl)phosphine were added to a 100 mL three-neck flask and stirred at 140 °C for 22 hours. After cooling to room temperature, 22 mL of pure water was added and stirred. The aqueous layer and organic layer were then separated, and the organic layer was washed with saturated sodium chloride aqueous solution. The organic layer was dried with anhydrous magnesium sulfate, and then column chromatography was performed using a small amount of silica gel to remove highly polar components. Next, the solvent was removed under reduced pressure, and the resulting solid was recrystallized in a mixed solvent of toluene and butanol to isolate 3.2 g (3.8 mmol) of compound (D285) as a white solid (70% yield). The sublimation temperature of D285 was confirmed to be 300°C, and the sublimated product of D285 was confirmed to be glassy.

[0620] Compound identification was performed by FDMS measurement.

[0621] FDMS:423 Example 12 (Synthesis of compound (D288))

[0622] [ka]

[0623] Under a nitrogen atmosphere, 2.9 g (7.1 mmol) of 9-(2-(naphthalene-2-yl)phenyl)-2-chlorocarbazole obtained in Synthesis Example 6, 1.9 g (5.9 mmol) of N,N-bis(biphenyl-4-yl)amine, 0.74 g (7.7 mmol) of sodium-tert-butoxide, 20 mL of o-xylene, 4.0 mg (18 μmol) of palladium acetate, and 43 mg (53 μmol) of a 25 wt% toluene solution of tri(tert-butyl)phosphine were added to a 100 mL three-neck flask and stirred at 140 °C for 22 hours. After cooling to room temperature, 20 mL of pure water was added and stirred. The aqueous layer and organic layer were then separated, and the organic layer was washed with saturated sodium chloride aqueous solution. The organic layer was dried over anhydrous magnesium sulfate, and column chromatography was performed using a small amount of silica gel to remove highly polar components. Next, the solvent was removed under reduced pressure, and the resulting solid was recrystallized in a mixed solvent of toluene and butanol to isolate 2.8 g (4.0 mol) of the compound (D288) as a white solid (yield 68%). The sublimation temperature of D288 was confirmed to be 340°C, and the sublimated product of D288 was confirmed to be glassy.

[0624] Compound identification was performed by FDMS measurement.

[0625] FDMS:688 Example 13 (Synthesis of compound (D289))

[0626] [ka]

[0627] Under a nitrogen atmosphere, 3.8 g (8.5 mmol) of 2-chloro-9-(2-(dibenzo[b,d]furan-4-yl)phenyl)-9H-carbazole obtained in Synthesis Example 11, 2.6 g (8.1 mmol) of di([1,1'-biphenyl]-4-yl)amine, 1.0 g (11 mmol) of sodium-tert-butoxide, 20 mL of xylene, 18 mg (81 μmol) of palladium acetate, and 0.20 g (0.24 mmol) of a 25 wt% xylene solution of tri(tert-butyl)phosphine were added to a 100 mL three-neck flask and stirred at 140 °C for 22 hours. After cooling to room temperature, 22 mL of pure water was added and stirred. The aqueous layer and organic layer were then separated, and the organic layer was further washed with saturated sodium chloride aqueous solution. The organic layer was dried over anhydrous magnesium sulfate, and column chromatography was performed using a small amount of silica gel to remove highly polar components. Next, the solvent was removed under reduced pressure, and the resulting solid was recrystallized in a mixed solvent of toluene and butanol to isolate 4.4 g (6.1 mmol) of the compound (D289) as a white solid (75% yield). The sublimation temperature of D289 was confirmed to be 280°C, and the sublimated product of D289 was confirmed to be glassy.

[0628] Compound identification was performed by FDMS measurement.

[0629] FDMS:728 Example 14 (Synthesis of compound (D291))

[0630] [ka]

[0631] Under a nitrogen atmosphere, 3.9 g (8.5 mmol) of 2-chloro-9-(2-(phenanthren-9-yl)phenyl)-9H-carbazole obtained in Synthesis Example 12, 2.6 g (8.1 mmol) of N-phenyltriphenylen-1-amine, 1.0 g (11 mmol) of sodium-tert-butoxide, 20 mL of xylene, 18 mg (81 μmol) of palladium acetate, and 0.20 g (0.24 mmol) of a 25 wt% xylene solution of tri(tert-butyl)phosphine were added to a 100 mL three-neck flask and stirred at 140 °C for 22 hours. After cooling to room temperature, 22 mL of pure water was added and stirred. The aqueous layer and organic layer were then separated, and the organic layer was washed with saturated sodium chloride aqueous solution. The organic layer was dried over anhydrous magnesium sulfate, and column chromatography was performed using a small amount of silica gel to remove highly polar components. Next, the solvent was removed under reduced pressure, and the resulting solid was recrystallized in a mixed solvent of toluene and butanol to isolate 4.6 g (6.2 mmol) of the compound (D291) as a white solid (76% yield). The sublimation temperature of D291 was confirmed to be 300°C, and the sublimated product of D291 was confirmed to be glassy.

[0632] Compound identification was performed by FDMS measurement.

[0633] FDMS:736 Example 15 (Synthesis of compound (D312))

[0634] [ka]

[0635] Under a nitrogen atmosphere, 9-(2,5-bis(dibenzo[b,d]furan-4-yl)phenyl)-2-chloro-9H-carbazole (1.05 Eq), N-([1,1'-biphenyl]-4-yl)-7,7-dimethyl-7H-benzo[c]fluoren-5-amine (1 Eq), sodium-tert-butoxide (1.3 Eq), 20 mL of xylene, palladium acetate (0.01 Eq), and a 25 wt% xylene solution of tri(tert-butyl)phosphine (0.03 Eq) were added to a 100 mL three-neck flask and stirred at 140 °C for 22 hours. After cooling to room temperature, 22 mL of pure water was added and stirred. The aqueous layer and organic layer were then separated, and the organic layer was washed with saturated sodium chloride aqueous solution. The organic layer was dried over anhydrous magnesium sulfate, and column chromatography was performed using a small amount of silica gel to remove highly polar components. Next, the solvent was removed under reduced pressure, and the resulting solid was recrystallized in a mixed solvent of toluene and butanol to obtain a white solid (80%) of compound (D312). The sublimation temperature of D312 was 340°C, and it was confirmed that the sublimated D312 was glassy.

[0636] Compound identification was performed by FDMS measurement.

[0637] FDMS:984 Example 16 (Synthesis of compound (D336))

[0638] [ka]

[0639] Under a nitrogen stream, 3.1 g (6.4 mmol) of 2-chloro-9-(6-(naphthalene-2-yl)-[1,1'-biphenyl]-2-yl)-9H-carbazole obtained in Synthesis Example 16, 2.5 g (6.1 mmol) of N-phenyl-9,9'-spirobi[fluorene]-2-amine, 0.77 g (8.0 mmol) of sodium-tert-butoxide, 20 mL of xylene, 14 mg (61 μmol) of palladium acetate, and 0.15 g (0.18 mmol) of a 25 wt% xylene solution of tri(tert-butyl)phosphine were added to a 100 mL three-neck flask and stirred at 140 °C for 22 hours. After cooling to room temperature, 22 mL of pure water was added and stirred. The aqueous layer and organic layer were then separated, and the organic layer was further washed with saturated sodium chloride aqueous solution. The organic layer was dried with anhydrous magnesium sulfate, and then column chromatography was performed using a small amount of silica gel to remove highly polar components. Next, the solvent was removed under reduced pressure, and the resulting solid was recrystallized in a mixed solvent of toluene and butanol to isolate 3.1 g (3.6 mmol) of compound (D336) as a white solid (yield 59%). The sublimation temperature of D336 was 310°C, and it was confirmed that the sublimated D336 was glassy.

[0640] Compound identification was performed by FDMS measurement.

[0641] FDMS:850 Example 17 (Synthesis of compound (D350))

[0642] [ka]

[0643] Under a nitrogen atmosphere, 3.0 g (5.2 mmol) of 9-([1,1':2',1'':2'',1''':2''',1''''-quinkiphenyl]-4''-yl)-2-chloro-9H-carbazole obtained in Synthesis Example 18, 2.2 g (5.0 mmol) of N-(4-(dibenzo[b,d]thiophen-4-yl)phenyl)-4'-methyl-[1,1'-biphenyl]-4-amine, 0.62 g (6.5 mmol) of sodium-tert-butoxide, 20 mL of xylene, 11 mg (50 μmol) of palladium acetate, and 0.12 g (0.15 mmol) of a 25 wt% xylene solution of tri(tert-butyl)phosphine were added to a 100 mL three-neck flask and stirred at 140 °C for 22 hours. After cooling to room temperature, 22 mL of pure water was added and stirred. Next, the aqueous layer and the organic layer were separated, and the organic layer was washed with saturated sodium chloride aqueous solution. The organic layer was dried with anhydrous magnesium sulfate, and column chromatography was performed using a small amount of silica gel to remove highly polar components. Then, the solvent was removed under reduced pressure, and the resulting solid was recrystallized in a mixed solvent of toluene and butanol to isolate 3.0 g (3.0 mmol) of the compound (D350) as a white solid (yield 60%). The sublimation temperature of D350 was confirmed to be 350°C, and the sublimated D350 was confirmed to be glassy.

[0644] Compound identification was performed by FDMS measurement.

[0645] FDMS:986 Example 18 (Synthesis of compound (D352))

[0646] [ka]

[0647] Under a nitrogen atmosphere, 4.9 g (12 mmol) of 2-chloro-9-(2-methyl-6-(naphthalene-2-yl)phenyl)-9H-carbazole obtained in Synthesis Example 20, 3.6 g (11 mmol) of di([1,1'-biphenyl]-4-yl)amine, 1.4 g (15 mmol) of sodium-tert-butoxide, 20 mL of xylene, 25 mg (0.11 mmol) of palladium acetate, and 0.27 g (0.34 mmol) of a 25 wt% xylene solution of tri(tert-butyl)phosphine were added to a 100 mL three-neck flask and stirred at 140 °C for 22 hours. After cooling to room temperature, 22 mL of pure water was added and stirred. The aqueous layer and organic layer were then separated, and the organic layer was washed with saturated sodium chloride aqueous solution. The organic layer was dried over anhydrous magnesium sulfate, and column chromatography was performed using a small amount of silica gel to remove highly polar components. Next, the solvent was removed under reduced pressure, and the resulting solid was recrystallized in a mixed solvent of toluene and butanol to isolate 5.8 g (8.3 mmol) of the compound (D352) as a white solid (yield 74%). The sublimation temperature of D352 was 290°C, and it was confirmed that the sublimated product of D352 was glassy.

[0648] Compound identification was performed by FDMS measurement.

[0649] FDMS:702 Example 19 (Synthesis of Compound D357)

[0650] [ka]

[0651] Under a nitrogen atmosphere, 5.5 g (10 mmol) of 2-chloro-9-(2,6-di(naphthalene-1-yl)phenyl)-9H-carbazole obtained in Synthesis Example 24, 3.3 g (9.9 mmol) of 4-(9H-carbazole-9-yl)-N-phenylaniline, 1.2 g (13 mmol) of sodium-tert-butoxide, 20 mL of xylene, 22 mg (99 μmol) of palladium acetate, and 0.16 g (0.20 mmol) of a 25 wt% xylene solution of tri(tert-butyl)phosphine were added to a 100 mL three-neck flask and stirred at 140 °C for 22 hours. After cooling to room temperature, 22 mL of pure water was added and stirred. Next, the aqueous layer and organic layer were separated, and the organic layer was further washed with saturated sodium chloride aqueous solution. The organic layer was dried over anhydrous magnesium sulfate, and column chromatography was performed using a small amount of silica gel to remove highly polar components. Next, the solvent was removed under reduced pressure, and the resulting solid was recrystallized in a mixed solvent of toluene and butanol to isolate 6.9 g (8.4 mmol) of the compound (D357) as a white solid (yield 85%). The sublimation temperature of D357 was confirmed to be 330°C, and the sublimated product of D357 was confirmed to be glassy.

[0652] Compound identification was performed by FDMS measurement.

[0653] FDMS:827 Example 20 (Synthesis of compound (D360))

[0654] [ka]

[0655] Under a nitrogen stream, 4.6 g (9.6 mmol) of 2-chloro-9-(3-(naphthalene-2-yl)-[1,1'-biphenyl]-2-yl)-9H-carbazole obtained in Synthesis Example 22, 2.5 g (9.1 mmol) of N-(3,4-dimethylphenyl)-[1,1'-biphenyl]-4-amine, 1.1 g (12 mmol) of sodium-tert-butoxide, 20 mL of xylene, 21 mg (91 μmol) of palladium acetate, and 0.15 g (0.18 mmol) of a 25 wt% xylene solution of tri(tert-butyl)phosphine were added to a 100 mL three-neck flask and stirred at 140 °C for 22 hours. After cooling to room temperature, 22 mL of pure water was added and stirred. The aqueous layer and organic layer were then separated, and the organic layer was further washed with saturated sodium chloride aqueous solution. The organic layer was dried with anhydrous magnesium sulfate, and highly polar components were removed by column chromatography using a small amount of silica gel. The solvent was then removed under reduced pressure, and the resulting solid was recrystallized in a mixed solvent of toluene and butanol to isolate 5.0 g (7.0 mmol) of compound (D360) as a white solid (77% yield). The sublimation temperature of D360 was confirmed to be 280°C, and the sublimated D360 was found to be glassy.

[0656] Compound identification was performed by FDMS measurement.

[0657] FDMS:716 Example 21 (Synthesis of D429)

[0658] [ka]

[0659] Under a nitrogen atmosphere, 1.4 g (5.1 mmol) of 2-chloro-9-phenyl-9H-carbazole, 2.0 g (4.9 mmol) of 5'-phenyl-N-(p-tolyl)-[1,1':3',1''-terphenyl]-4-amine, 0.61 g (6.3 mmol) of sodium-tert-butoxide, 20 mL of xylene, 11 mg (49 μmol) of palladium acetate, and 79 mg (97 μmol) of a 25 wt% xylene solution of tri(tert-butyl)phosphine were added to a 100 mL three-neck flask and stirred at 140 °C for 22 hours. After cooling to room temperature, 22 mL of pure water was added and stirred. The aqueous layer and organic layer were then separated, and the organic layer was washed with saturated sodium chloride aqueous solution. The organic layer was dried over anhydrous magnesium sulfate, and column chromatography was performed using a small amount of silica gel to remove highly polar components. Next, the solvent was removed under reduced pressure, and the resulting solid was recrystallized in a mixed solvent of toluene and butanol to isolate 2.5 g (3.9 mmol) of the compound (D429) as a white solid (80% yield). The sublimation temperature of D429 was confirmed to be 330°C, and the sublimated product of D429 was confirmed to be glassy.

[0660] Compound identification was performed by FDMS measurement.

[0661] FDMS:652 Example 22 (Synthesis of compound (D657))

[0662] [ka]

[0663] Under a nitrogen atmosphere, 2.0 g (6.2 mmol) of 2-chloro-9-(naphthalene-1-yl)-9H-carbazole, 2.6 g (5.9 mmol) of N-([1,1':3',1''-terphenyl]-4'-yl)-9,9-dimethyl-9H-fluoren-2-amine, 0.74 g (7.7 mmol) of sodium-tert-butoxide, 20 mL of xylene, 13 mg (59 μmol) of palladium acetate, and 96 mg (0.12 mmol) of a 25 wt% xylene solution of tri(tert-butyl)phosphine were added to a 100 mL three-neck flask and stirred at 140 °C for 22 hours. After cooling to room temperature, 22 mL of pure water was added and stirred. The aqueous layer and organic layer were then separated, and the organic layer was washed with saturated sodium chloride aqueous solution. The organic layer was dried with anhydrous magnesium sulfate, and highly polar components were removed by column chromatography using a small amount of silica gel. The solvent was then removed under reduced pressure, and the resulting solid was recrystallized in a mixed solvent of toluene and butanol to isolate 3.2 g (4.3 mmol) of compound (D657) as a white solid (73% yield). The sublimation temperature of D657 was confirmed to be 270°C, and the sublimated product was found to be glassy.

[0664] Compound identification was performed by FDMS measurement.

[0665] FDMS:728 Example 23 (Synthesis of compound (D757))

[0666] [ka]

[0667] Under a nitrogen atmosphere, 2.1 g (5.7 mmol) of 2-chloro-9-(4'-methyl-[1,1'-biphenyl]-4-yl)-9H-carbazole, 2.4 g (5.4 mmol) of N-([1,1':2',1''-terphenyl]-3-yl)fluorante-3-amine, 0.67 g (7.0 mmol) of sodium-tert-butoxide, 20 mL of xylene, 12 mg (54 μmol) of palladium acetate, and 87 mg (0.11 mmol) of a 25 wt% xylene solution of tri(tert-butyl)phosphine were added to a 100 mL three-neck flask and stirred at 140 °C for 22 hours. After cooling to room temperature, 22 mL of pure water was added and stirred. The aqueous layer and organic layer were then separated, and the organic layer was washed with saturated sodium chloride aqueous solution. The organic layer was dried with anhydrous magnesium sulfate, and then column chromatography was performed using a small amount of silica gel to remove highly polar components. Next, the solvent was removed under reduced pressure, and the resulting solid was recrystallized in a mixed solvent of toluene and butanol to isolate 3.1 g (4.0 mmol) of compound (D757) as a white solid (yield 74%). The sublimation temperature of D757 was 330°C, and it was confirmed that the sublimated product of D757 was glassy.

[0668] Compound identification was performed by FDMS measurement.

[0669] FDMS:776 Example 24 (Synthesis of compound (D805))

[0670] [ka]

[0671] Under a nitrogen atmosphere, 5.0 g (11 mmol) of 2-chloro-9-(3,3''-dimethyl-[1,1':3',1''-terphenyl]-2'-yl)-9H-carbazole obtained in Synthesis Example 26, 4.0 g (10 mmol) of 11,11-dimethyl-N-(naphthalene-1-yl)-11H-benzo[a]fluoren-9-amine, 1.3 g (13 mmol) of sodium-tert-butoxide, 20 mL of xylene, 23 mg (0.10 mmol) of palladium acetate, and 0.17 g (0.21 mmol) of a 25 wt% xylene solution of tri(tert-butyl)phosphine were added to a 100 mL three-neck flask and stirred at 140 °C for 22 hours. After cooling to room temperature, 22 mL of pure water was added and stirred. The aqueous layer and organic layer were then separated, and the organic layer was further washed with saturated sodium chloride aqueous solution. The organic layer was dried with anhydrous magnesium sulfate, and then column chromatography was performed using a small amount of silica gel to remove highly polar components. Next, the solvent was removed under reduced pressure, and the resulting solid was recrystallized in a mixed solvent of toluene and butanol to isolate 6.7 g (8.3 mmol) of compound (D805) as a white solid (80% yield). The sublimation temperature of D805 was 280°C, and it was confirmed that the sublimated product of D805 was glassy.

[0672] Compound identification was performed by FDMS measurement.

[0673] FDMS:805 Example 25 (Synthesis of compound (D818))

[0674] [ka]

[0675] Under a nitrogen atmosphere, 4.0 g (7.4 mmol) of 2-chloro-9-(2'-(dibenzo[b,d]furan-4-yl)-5-methyl-[1,1'-biphenyl]-2-yl)-9H-carbazole obtained in Synthesis Example 27, 3.2 g (7.1 mmol) of N-(4-(phenanthren-9-yl)phenyl)dibenzo[b,d]thiophene-4-amine, 0.89 g (9.2 mmol) of sodium-tert-butoxide, 20 mL of xylene, 16 mg (71 μmol) of palladium acetate, and 0.11 g (0.14 mmol) of a 25 wt% xylene solution of tri(tert-butyl)phosphine were added to a 100 mL three-neck flask and stirred at 140 °C for 22 hours. After cooling to room temperature, 22 mL of pure water was added and stirred. Next, the aqueous layer and the organic layer were separated, and the organic layer was washed with saturated sodium chloride aqueous solution. The organic layer was dried with anhydrous magnesium sulfate, and column chromatography was performed using a small amount of silica gel to remove highly polar components. Then, the solvent was removed under reduced pressure, and the resulting solid was recrystallized in a mixed solvent of toluene and butanol to isolate 4.8 g (5.0 mmol) of compound (D818) as a white solid (yield 71%). The sublimation temperature of D818 was confirmed to be 350°C, and the sublimated D818 was confirmed to be glassy.

[0676] Compound identification was performed by FDMS measurement.

[0677] FDMS:948 Example 26 (Synthesis of compound (D844))

[0678] [ka]

[0679] Under a nitrogen atmosphere, 3.3 g (7.7 mmol) of 9-([1,1':3',1''-terphenyl]-2'-yl)-2-chloro-9H-carbazole obtained in Synthesis Example 5, 2.0 g (7.3 mmol) of N-(3,4-dimethylphenyl)-[1,1'-biphenyl]-4-amine, 0.91 g (9.5 mmol) of sodium-tert-butoxide, 20 mL of xylene, 16 mg (73 μmol) of palladium acetate, and 0.12 g (0.15 mmol) of a 25 wt% xylene solution of tri(tert-butyl)phosphine were added to a 100 mL three-neck flask and stirred at 140 °C for 22 hours. After cooling to room temperature, 22 mL of pure water was added and stirred. The aqueous layer and organic layer were then separated, and the organic layer was further washed with saturated sodium chloride aqueous solution. The organic layer was dried with anhydrous magnesium sulfate, and then column chromatography was performed using a small amount of silica gel to remove highly polar components. Next, the solvent was removed under reduced pressure, and the resulting solid was recrystallized in a mixed solvent of toluene and butanol to isolate 3.9 g (5.9 mmol) of compound (D844) as a white solid (80% yield). The sublimation temperature of D844 was 270°C, and it was confirmed that the sublimated product of D844 was glassy.

[0680] Compound identification was performed by FDMS measurement.

[0681] FDMS:666 Example 27 (Synthesis of compound (D850))

[0682] [ka]

[0683] Under a nitrogen atmosphere, 3.8 g (9.8 mmol) of 2-chloro-9-(3',5'-dimethyl-[1,1'-biphenyl]-2-yl)-9H-carbazole obtained in Synthesis Example 29, 4.0 g (9.4 mmol) of N-phenyl-4-(triphenylsilyl)aniline, 1.2 g (12 mmol) of sodium-tert-butoxide, 20 mL of xylene, 21 mg (94 μmol) of palladium acetate, and 0.15 g (0.19 mmol) of a 25 wt% xylene solution of tri(tert-butyl)phosphine were added to a 100 mL three-neck flask and stirred at 140 °C for 22 hours. After cooling to room temperature, 22 mL of pure water was added and stirred. Next, the aqueous layer and organic layer were separated, and the organic layer was further washed with saturated sodium chloride aqueous solution. The organic layer was dried over anhydrous magnesium sulfate, and column chromatography was performed using a small amount of silica gel to remove highly polar components. Next, the solvent was removed under reduced pressure, and the resulting solid was recrystallized in a mixed solvent of toluene and butanol to isolate 4.4 g (5.7 mmol) of the compound (D850) as a white solid (yield 61%). The sublimation temperature of D850 was confirmed to be 310°C, and the sublimated product of D850 was confirmed to be glassy.

[0684] Compound identification was performed by FDMS measurement.

[0685] FDMS:772 Example 28 (Synthesis of compound (D853))

[0686] [ka]

[0687] Under a nitrogen atmosphere, 2.6 g (7.1 mmol) of 2-chloro-9-(2'-methyl-[1,1'-biphenyl]-2-yl)-9H-carbazole obtained in Synthesis Example 30, 3.3 g (6.8 mmol) of N-([1,1'-biphenyl]-4-yl)-4'-(9H-carbazole-9-yl)-[1,1'-biphenyl]-4-amine, 0.85 g (8.8 mmol) of sodium-tert-butoxide, 20 mL of xylene, 15 mg (68 μmol) of palladium acetate, and 0.11 g (0.14 mmol) of a 25 wt% xylene solution of tri(tert-butyl)phosphine were added to a 100 mL three-neck flask and stirred at 140 °C for 22 hours. After cooling to room temperature, 22 mL of pure water was added and stirred. Next, the aqueous layer and the organic layer were separated, and the organic layer was washed with saturated sodium chloride aqueous solution. The organic layer was dried with anhydrous magnesium sulfate, and column chromatography was performed using a small amount of silica gel to remove highly polar components. Then, the solvent was removed under reduced pressure, and the resulting solid was recrystallized in a mixed solvent of toluene and butanol to isolate 4.2 g (5.2 mmol) of compound (D853) as a white solid (yield 76%). The sublimation temperature of D853 was confirmed to be 330°C, and the sublimated product of D853 was confirmed to be glassy.

[0688] Compound identification was performed by FDMS measurement.

[0689] FDMS:817 Example 29 (Synthesis of compound (D859))

[0690] [ka]

[0691] Under a nitrogen atmosphere, 3.6 g (7.6 mmol) of 2-chloro-9-(2'-methyl-5-(naphthalene-1-yl)-[1,1'-biphenyl]-2-yl)-9H-carbazole obtained in Synthesis Example 32, 2.6 g (7.2 mmol) of N-(2-methyl-[1,1'-biphenyl]-4-yl)phenanthrene-9-amine, 0.90 g (9.4 mmol) of sodium-tert-butoxide, 20 mL of xylene, 16 mg (72 μmol) of palladium acetate, and 0.12 g (0.14 mmol) of a 25 wt% xylene solution of tri(tert-butyl)phosphine were added to a 100 mL three-neck flask and stirred at 140 °C for 22 hours. After cooling to room temperature, 22 mL of pure water was added and stirred. The aqueous layer and organic layer were then separated, and the organic layer was washed with saturated sodium chloride aqueous solution. The organic layer was dried with anhydrous magnesium sulfate, and then column chromatography was performed using a small amount of silica gel to remove highly polar components. Next, the solvent was removed under reduced pressure, and the resulting solid was recrystallized in a mixed solvent of toluene and butanol to isolate 3.8 g (4.6 mmol) of compound (D859) as a white solid (yield 64%). The sublimation temperature of D859 was 335°C, and it was confirmed that the sublimated product of D859 was glassy.

[0692] Compound identification was performed by FDMS measurement.

[0693] FDMS:816 Example 30 (Synthesis of compound (E103))

[0694] [ka]

[0695] Under a nitrogen atmosphere, 2.0 g (7.2 mmol) of 4-chloro-9-phenyl-9H-carbazole, 3.0 g (6.9 mmol) of N-([1,1':4',1''-terphenyl]-2-yl)-9,9-dimethyl-9H-fluoren-2-amine, 0.86 g (8.9 mmol) of sodium-tert-butoxide, 20 mL of xylene, 15 mg (69 μmol) of palladium acetate, and 0.11 g (0.14 mmol) of a 25 wt% xylene solution of tri(tert-butyl)phosphine were added to a 100 mL three-neck flask and stirred at 140 °C for 22 hours. After cooling to room temperature, 22 mL of pure water was added and stirred. The aqueous layer and organic layer were then separated, and the organic layer was washed with saturated sodium chloride aqueous solution. The organic layer was dried over anhydrous magnesium sulfate, and column chromatography was performed using a small amount of silica gel to remove highly polar components. Next, the solvent was removed under reduced pressure, and the resulting solid was recrystallized in a mixed solvent of toluene and butanol to isolate 3.8 g (5.6 mmol) of the compound (E103) as a white solid (yield 81%). The sublimation temperature of E103 was confirmed to be 300°C, and the sublimated product of E103 was confirmed to be glassy.

[0696] Compound identification was performed by FDMS measurement.

[0697] FDMS:678 Example 31 (Synthesis of compound (E107))

[0698] [ka]

[0699] Under a nitrogen atmosphere, 1.8 g (6.5 mmol) of 4-chloro-9-phenyl-9H-carbazole, 3.0 g (6.2 mmol) of N-([1,1':2',1''-terphenyl]-4'-yl)-7,7-dimethyl-7H-benzo[c]fluoren-5-amine, 0.77 g (8.0 mmol) of sodium-tert-butoxide, 20 mL of xylene, 14 mg (62 μmol) of palladium acetate, and 0.10 g (0.12 mmol) of a 25 wt% xylene solution of tri(tert-butyl)phosphine were added to a 100 mL three-neck flask and stirred at 140 °C for 22 hours. After cooling to room temperature, 22 mL of pure water was added and stirred. The aqueous layer and organic layer were then separated, and the organic layer was washed with saturated sodium chloride aqueous solution. The organic layer was dried with anhydrous magnesium sulfate, and then column chromatography was performed using a small amount of silica gel to remove highly polar components. Next, the solvent was removed under reduced pressure, and the resulting solid was recrystallized in a mixed solvent of toluene and butanol to isolate 2.8 g (3.9 mmol) of compound (E107) as a white solid (yield 63%). The sublimation temperature of E107 was 310°C, and it was confirmed that the sublimated product of E107 was glassy.

[0700] Compound identification was performed by FDMS measurement.

[0701] FDMS:728 Example 32 (Synthesis of compound (E111))

[0702] [ka]

[0703] Under a nitrogen atmosphere, 2.8 g (6.5 mmol) of 9-([1,1':3',1''-terphenyl]-2'-yl)-4-chloro-9H-carbazole, 2.5 g (6.2 mmol) of bis(9,9-dimethyl-9H-fluoren-2-yl)amine, 0.78 g (8.1 mmol) of sodium-tert-butoxide, 20 mL of xylene, 14 mg (62 μmol) of palladium acetate, and 0.10 g (0.12 mmol) of a 25 wt% xylene solution of tri(tert-butyl)phosphine were added to a 100 mL three-neck flask and stirred at 140 °C for 22 hours. After cooling to room temperature, 22 mL of pure water was added and stirred. The aqueous layer and organic layer were then separated, and the organic layer was washed with saturated sodium chloride aqueous solution. The organic layer was dried over anhydrous magnesium sulfate, and column chromatography was performed using a small amount of silica gel to remove highly polar components. Next, the solvent was removed under reduced pressure, and the resulting solid was recrystallized in a mixed solvent of toluene and butanol to isolate 4.0 g (5.0 mmol) of the compound (E111) as a white solid (80% yield). The sublimation temperature of E111 was confirmed to be 315°C, and the sublimated product of E111 was confirmed to be glassy.

[0704] Compound identification was performed by FDMS measurement.

[0705] FDMS:794 Example 33 (Compound (E161))

[0706] [ka]

[0707] Under a nitrogen atmosphere, 1.8 g (6.5 mmol) of 4-chloro-9-phenyl-9H-carbazole, 2.6 g (6.2 mmol) of N-([1,1':4',1''-terphenyl]-2'-yl)anthracen-9-amine, 0.77 g (8.0 mmol) of sodium-tert-butoxide, 20 mL of xylene, 14 mg (62 μmol) of palladium acetate, and 0.10 g (0.12 mmol) of a 25 wt% xylene solution of tri(tert-butyl)phosphine were added to a 100 mL three-neck flask and stirred at 140 °C for 22 hours. After cooling to room temperature, 22 mL of pure water was added and stirred. The aqueous layer and organic layer were then separated, and the organic layer was washed with saturated sodium chloride aqueous solution. The organic layer was dried over anhydrous magnesium sulfate, and column chromatography was performed using a small amount of silica gel to remove highly polar components. Next, the solvent was removed under reduced pressure, and the resulting solid was recrystallized in a mixed solvent of toluene and butanol to isolate 2.7 g (4.1 mmol) of the compound (E161) as a white solid (yield 66%). The sublimation temperature of E161 was confirmed to be 285°C, and the sublimated product of E161 was confirmed to be glassy.

[0708] Compound identification was performed by FDMS measurement.

[0709] FDMS:662 Example 34 (Synthesis of Compound (E169))

[0710] [ka]

[0711] Under a nitrogen atmosphere, 2.2 g (7.9 mmol) of 4-chloro-9-phenyl-9H-carbazole, 3.0 g (7.5 mmol) of N-([1,1'-biphenyl]-4-yl)-[1,1':3',1''-terphenyl]-2-amine, 0.94 g (9.8 mmol) of sodium-tert-butoxide, 20 mL of xylene, 17 mg (75 μmol) of palladium acetate, and 0.12 g (0.15 mmol) of a 25 wt% xylene solution of tri(tert-butyl)phosphine were added to a 100 mL three-neck flask and stirred at 140 °C for 22 hours. After cooling to room temperature, 22 mL of pure water was added and stirred. The aqueous layer and organic layer were then separated, and the organic layer was washed with saturated sodium chloride aqueous solution. The organic layer was dried over anhydrous magnesium sulfate, and column chromatography was performed using a small amount of silica gel to remove highly polar components. Next, the solvent was removed under reduced pressure, and the resulting solid was recrystallized in a mixed solvent of toluene and butanol to isolate 3.4 g (5.4 mmol) of the compound (E169) as a white solid (71% yield). The sublimation temperature of E169 was confirmed to be 300°C, and the sublimated product of E169 was confirmed to be glassy.

[0712] Compound identification was performed by FDMS measurement.

[0713] FDMS:638 Example 35 (Synthesis of Compound (E179))

[0714] [ka]

[0715] Under a nitrogen atmosphere, 2.3 g (8.2 mmol) of 4-chloro-9-phenyl-9H-carbazole, 3.5 g (7.9 mmol) of N-(2-(dibenzo[b,d]thiophen-2-yl)phenyl)-4'-fluoro-[1,1'-biphenyl]-4-amine, 0.98 g (10 mmol) of sodium-tert-butoxide, 20 mL of xylene, 18 mg (79 μmol) of palladium acetate, and 0.13 g (0.16 mmol) of a 25 wt% xylene solution of tri(tert-butyl)phosphine were added to a 100 mL three-neck flask and stirred at 140 °C for 22 hours. After cooling to room temperature, 22 mL of pure water was added and stirred. The aqueous layer and organic layer were then separated, and the organic layer was washed with saturated sodium chloride aqueous solution. The organic layer was dried over anhydrous magnesium sulfate, and column chromatography was performed using a small amount of silica gel to remove highly polar components. Next, the solvent was removed under reduced pressure, and the resulting solid was recrystallized in a mixed solvent of toluene and butanol to isolate 2.9 g (4.2 mmol) of the compound (E179) as a white solid (yield 54%). The sublimation temperature of E179 was confirmed to be 305°C, and the sublimated product of E179 was confirmed to be glassy.

[0716] Compound identification was performed by FDMS measurement.

[0717] FDMS:686 Example 36 (Synthesis of compound (E228))

[0718] [ka]

[0719] Under a nitrogen atmosphere, 2.6 g (9.3 mmol) of 4-chloro-9-phenyl-9H-carbazole, 3.4 g (8.8 mmol) of N-(2-(naphthalene-2-yl)phenyl)dibenzo[b,d]furan-3-amine, 1.1 g (11 mmol) of sodium-tert-butoxide, 20 mL of xylene, 20 mg (88 μmol) of palladium acetate, and 0.14 g (0.18 mmol) of a 25 wt% xylene solution of tri(tert-butyl)phosphine were added to a 100 mL three-neck flask and stirred at 140 °C for 22 hours. After cooling to room temperature, 22 mL of pure water was added and stirred. The aqueous layer and organic layer were then separated, and the organic layer was washed with saturated sodium chloride aqueous solution. The organic layer was dried over anhydrous magnesium sulfate, and column chromatography was performed using a small amount of silica gel to remove highly polar components. Next, the solvent was removed under reduced pressure, and the resulting solid was recrystallized in a mixed solvent of toluene and butanol to isolate 4.3 g (6.8 mmol) of the compound (E228) as a white solid (77% yield). The sublimation temperature of E228 was confirmed to be 300°C, and the sublimated product of E228 was confirmed to be glassy.

[0720] Compound identification was performed by FDMS measurement.

[0721] FDMS:626 Example 37 (Synthesis of compound (E264))

[0722] [ka]

[0723] Under a nitrogen atmosphere, 2.4 g (4.9 mmol) of 4-chloro-9-(2'-(naphthalene-1-yl)-[1,1'-biphenyl]-4-yl)-9H-carbazole, 2.0 g (4.7 mmol) of 7,7-dimethyl-N-(3'-methyl-[1,1'-biphenyl]-4-yl)-7H-benzo[c]fluoren-9-amine, 0.59 g (6.1 mmol) of sodium-tert-butoxide, 20 mL of xylene, 11 mg (47 μmol) of palladium acetate, and 76 mg (94 μmol) of a 25 wt% xylene solution of tri(tert-butyl)phosphine were added to a 100 mL three-neck flask obtained in Synthesis Example 33, and the mixture was stirred at 140 °C for 22 hours. After cooling to room temperature, 22 mL of pure water was added and the mixture was stirred. Next, the aqueous layer and the organic layer were separated, and the organic layer was washed with saturated sodium chloride aqueous solution. The organic layer was dried with anhydrous magnesium sulfate, and column chromatography was performed using a small amount of silica gel to remove highly polar components. Then, the solvent was removed under reduced pressure, and the resulting solid was recrystallized in a mixed solvent of toluene and butanol to isolate 3.0 g (3.4 mmol) of the compound (E264) as a white solid (yield 73%). The sublimation temperature of E264 was confirmed to be 340°C, and the sublimated E264 was confirmed to be glassy.

[0724] Compound identification was performed by FDMS measurement.

[0725] FDMS:868 Example 38 (Synthesis of compound (E268))

[0726] [ka]

[0727] Under a nitrogen atmosphere, 3.7 g (8.0 mmol) of 4-chloro-9-(2-(dibenzo[b,d]thiophen-4-yl)phenyl)-9H-carbazole obtained in Synthesis Example 34, 2.3 g (7.6 mmol) of N-(4-ethylphenyl)dibenzo[b,d]thiophen-2-amine, 0.95 g (9.9 mmol) of sodium-tert-butoxide, 20 mL of xylene, 17 mg (76 μmol) of palladium acetate, and 0.12 g (0.15 mmol) of a 25 wt% xylene solution of tri(tert-butyl)phosphine were added to a 100 mL three-neck flask and stirred at 140 °C for 22 hours. After cooling to room temperature, 22 mL of pure water was added and stirred. The aqueous layer and organic layer were then separated, and the organic layer was further washed with saturated sodium chloride aqueous solution. The organic layer was dried with anhydrous magnesium sulfate, and then column chromatography was performed using a small amount of silica gel to remove highly polar components. Next, the solvent was removed under reduced pressure, and the resulting solid was recrystallized in a mixed solvent of toluene and butanol to isolate 4.8 g (6.6 mmol) of the compound (E268) as a white solid (yield 87%). The sublimation temperature of E268 was confirmed to be 300°C, and the sublimated product of E268 was confirmed to be glassy.

[0728] Compound identification was performed by FDMS measurement.

[0729] FDMS:726 Example 39 (Synthesis of compound (E303))

[0730] [ka]

[0731] Under a nitrogen atmosphere, 4.7 g (9.7 mmol) of 4-chloro-9-(2'-(naphthalene-2-yl)-[1,1'-biphenyl]-3-yl)-9H-carbazole, 3.1 g (9.2 mmol) of 11,11-dimethyl-N-phenyl-11H-benzo[a]fluoren-9-amine, 1.2 g (12 mmol) of sodium-tert-butoxide, 20 mL of xylene, 21 mg (92 μmol) of palladium acetate, and 0.15 g (0.18 mmol) of a 25 wt% xylene solution of tri(tert-butyl)phosphine were added to a 100 mL three-neck flask and stirred at 140 °C for 22 hours. After cooling to room temperature, 22 mL of pure water was added and stirred. The aqueous layer and organic layer were then separated, and the organic layer was washed with saturated sodium chloride aqueous solution. The organic layer was dried with anhydrous magnesium sulfate, and then column chromatography was performed using a small amount of silica gel to remove highly polar components. Next, the solvent was removed under reduced pressure, and the resulting solid was recrystallized in a mixed solvent of toluene and butanol to isolate 5.0 g (6.5 mmol) of compound (E303) as a white solid (70% yield). The sublimation temperature of E303 was 320°C, and it was confirmed that the sublimated E303 was glassy.

[0732] Compound identification was performed by FDMS measurement.

[0733] FDMS:778 Example 40 (Synthesis of compound (E329))

[0734] [ka]

[0735] Under a nitrogen stream, 2.5 g (6.2 mmol) of 4-chloro-9-(4-phenylnaphthalen-1-yl)-9H-carbazole obtained in Synthesis Example 36, 2.5 g (5.9 mmol) of N-(4-(dibenzo[b,d]furan-4-yl)phenyl)-3'-methyl-[1,1'-biphenyl]-4-amine, 0.73 g (7.6 mmol) of sodium-tert-butoxide, 20 mL of xylene, 13 mg (59 μmol) of palladium acetate, and 95 mg (0.12 mmol) of a 25 wt% xylene solution of tri(tert-butyl)phosphine were added to a 100 mL three-neck flask and stirred at 140 °C for 22 hours. After cooling to room temperature, 22 mL of pure water was added and stirred. The aqueous layer and organic layer were then separated, and the organic layer was further washed with saturated sodium chloride aqueous solution. The organic layer was dried with anhydrous magnesium sulfate, and highly polar components were removed by column chromatography using a small amount of silica gel. The solvent was then removed under reduced pressure, and the resulting solid was recrystallized in a mixed solvent of toluene and butanol to isolate 3.7 g (4.7 mmol) of the compound (E329) as a white solid (80% yield). The sublimation temperature of E329 was confirmed to be 335°C, and the sublimated product of E329 was confirmed to be glassy.

[0736] Compound identification was performed by FDMS measurement.

[0737] FDMS:792 Example 41 (Synthesis of compound (E330))

[0738] [ka]

[0739] Under a nitrogen atmosphere, 4.5 g (9.3 mmol) of 9-(4-([1,1'-biphenyl]-4-yl)naphthalen-1-yl)-4-chloro-9H-carbazole obtained in Synthesis Example 37, 2.0 g (8.9 mmol) of 4-(tert-butyl)-N-phenylaniline, 1.1 g (12 mmol) of sodium-tert-butoxide, 20 mL of xylene, 20 mg (89 μmol) of palladium acetate, and 0.14 g (0.18 mmol) of a 25 wt% xylene solution of tri(tert-butyl)phosphine were added to a 100 mL three-neck flask and stirred at 140 °C for 22 hours. After cooling to room temperature, 22 mL of pure water was added and stirred. The aqueous layer and organic layer were then separated, and the organic layer was further washed with saturated sodium chloride aqueous solution. The organic layer was dried with anhydrous magnesium sulfate, and then column chromatography was performed using a small amount of silica gel to remove highly polar components. Next, the solvent was removed under reduced pressure, and the resulting solid was recrystallized in a mixed solvent of toluene and butanol to isolate 5.2 g (7.8 mmol) of compound (E330) as a white solid (yield 88%). The sublimation temperature of E330 was 295°C, and it was confirmed that the sublimated E330 was glassy.

[0740] Compound identification was performed by FDMS measurement.

[0741] FDMS:423 Example 42 (Synthesis of compound (E341))

[0742] [ka]

[0743] Under a nitrogen atmosphere, 1.3 g (3.2 mmol) of 4-chloro-9-(2-phenylnaphthalen-1-yl)-9H-carbazole obtained in Synthesis Example 38, 1.6 g (3.1 mmol) of N-(4-(triphenylsilyl)phenyl)dibenzo[b,d]furan-2-amine, 0.39 g (4.0 mmol) of sodium-tert-butoxide, 20 mL of xylene, 6.9 mg (31 μmol) of palladium acetate, and 50 mg (62 μmol) of a 25 wt% xylene solution of tri(tert-butyl)phosphine were added to a 100 mL three-neck flask and stirred at 140 °C for 22 hours. After cooling to room temperature, 22 mL of pure water was added and stirred. The aqueous layer and organic layer were then separated, and the organic layer was washed with saturated sodium chloride aqueous solution. The organic layer was dried over anhydrous magnesium sulfate, and column chromatography was performed using a small amount of silica gel to remove highly polar components. Next, the solvent was removed under reduced pressure, and the resulting solid was recrystallized in a mixed solvent of toluene and butanol to isolate 1.8 g (2.0 mmol) of the compound (E341) as a white solid (yield 65%). The sublimation temperature of E341 was confirmed to be 345°C, and the sublimated product of E341 was confirmed to be glassy.

[0744] Compound identification was performed by FDMS measurement.

[0745] FDMS:884 Example 43 (Synthesis of compound (E674))

[0746] [ka]

[0747] Under a nitrogen atmosphere, 3.6 g (9.0 mmol) of 4-chloro-9-(3-phenylnaphthalen-2-yl)-9H-carbazole obtained in Synthesis Example 40, 3.3 g (8.6 mmol) of N-(4-(naphthalen-2-yl)phenyl)dibenzo[b,d]furan-4-amine, 1.1 g (11 mmol) of sodium-tert-butoxide, 20 mL of xylene, 19 mg (86 μmol) of palladium acetate, and 0.14 g (0.17 mmol) of a 25 wt% xylene solution of tri(tert-butyl)phosphine were added to a 100 mL three-neck flask and stirred at 140 °C for 22 hours. After cooling to room temperature, 22 mL of pure water was added and stirred. The aqueous layer and organic layer were then separated, and the organic layer was further washed with saturated sodium chloride aqueous solution. The organic layer was dried with anhydrous magnesium sulfate, and then column chromatography was performed using a small amount of silica gel to remove highly polar components. Next, the solvent was removed under reduced pressure, and the resulting solid was recrystallized in a mixed solvent of toluene and butanol to isolate 4.9 g (6.5 mmol) of compound (E674) as a white solid (yield 76%). The sublimation temperature of E674 was 320°C, and it was confirmed that the sublimated product of E674 was glassy.

[0748] Compound identification was performed by FDMS measurement.

[0749] FDMS:752 Example 44 (Synthesis of compound (E770))

[0750] [ka]

[0751] Under a nitrogen atmosphere, 1.6 g (5.7 mmol) of 4-chloro-9-phenyl-9H-carbazole, 1.9 g (5.4 mmol) of 4,4''-dimethyl-N-phenyl-[1,1':4',1''-terphenyl]-2'-amine, 0.68 g (7.1 mmol) of sodium-tert-butoxide, 20 mL of xylene, 12 mg (54 μmol) of palladium acetate, and 88 mg (0.11 mmol) of a 25 wt% xylene solution of tri(tert-butyl)phosphine were added to a 100 mL three-neck flask and stirred at 140 °C for 22 hours. After cooling to room temperature, 22 mL of pure water was added and stirred. The aqueous layer and organic layer were then separated, and the organic layer was washed with saturated sodium chloride aqueous solution. The organic layer was dried over anhydrous magnesium sulfate, and column chromatography was performed using a small amount of silica gel to remove highly polar components. Next, the solvent was removed under reduced pressure, and the resulting solid was recrystallized in a mixed solvent of toluene and butanol to isolate 2.5 g (4.2 mmol) of the compound (E770) as a white solid (yield 77%). The sublimation temperature of E770 was confirmed to be 260°C, and the sublimated product of E770 was confirmed to be glassy.

[0752] Compound identification was performed by FDMS measurement.

[0753] FDMS:590 Example 45 (Synthesis of compound (F166))

[0754] [ka]

[0755] Under a nitrogen atmosphere, 4.2 g (9.8 mmol) of 9-([1,1':4',1''-terphenyl]-2-yl)-2-chloro-9H-carbazole obtained in Synthesis Example 8, 3.0 g (9.3 mmol) of N-([1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-2-amine, 1.2 g (12 mmol) of sodium-tert-butoxide, 20 mL of xylene, 21 mg (93 μmol) of palladium acetate, and 0.15 g (0.19 mmol) of a 25 wt% xylene solution of tri(tert-butyl)phosphine were added to a 100 mL three-neck flask and stirred at 140 °C for 22 hours. After cooling to room temperature, 22 mL of pure water was added and stirred. The aqueous layer and organic layer were then separated, and the organic layer was further washed with saturated sodium chloride aqueous solution. The organic layer was dried with anhydrous magnesium sulfate, and then column chromatography was performed using a small amount of silica gel to remove highly polar components. Next, the solvent was removed under reduced pressure, and the resulting solid was recrystallized in a mixed solvent of toluene and butanol to isolate 5.3 g (7.5 mmol) of compound (F166) as a white solid (80% yield). The sublimation temperature of F166 was 285°C, and it was confirmed that the sublimated product of F166 was glassy.

[0756] Compound identification was performed by FDMS measurement.

[0757] FDMS:714 Example 46 (Synthesis of compound (F228))

[0758] [ka]

[0759] Under a nitrogen atmosphere, 1.8 g (4.2 mmol) of 9-([1,1':4',1''-terphenyl]-2'-yl)-2-chloro-9H-carbazole obtained in Synthesis Example 4, 1.9 g (4.0 mmol) of N-([1,1':4',1''-terphenyl]-4-yl)-[1,1':2',1''-terphenyl]-4'-amine, 0.50 g (5.2 mmol) of sodium-tert-butoxide, 20 mL of xylene, 9.0 mg (40 μmol) of palladium acetate, and 65 mg (80 μmol) of a 25 wt% xylene solution of tri(tert-butyl)phosphine were added to a 100 mL three-neck flask and stirred at 140 °C for 22 hours. After cooling to room temperature, 22 mL of pure water was added and stirred. The aqueous layer and organic layer were then separated, and the organic layer was further washed with saturated sodium chloride aqueous solution. The organic layer was dried with anhydrous magnesium sulfate, and highly polar components were removed by column chromatography using a small amount of silica gel. The solvent was then removed under reduced pressure, and the resulting solid was recrystallized in a mixed solvent of toluene and butanol to isolate 2.9 g (3.3 mmol) of the compound (F228) as a white solid (83% yield). The sublimation temperature of F228 was confirmed to be 330°C, and the sublimated product was found to be glassy.

[0760] Compound identification was performed by FDMS measurement.

[0761] FDMS:866 Example 47 (Synthesis of compound (F320))

[0762] [ka]

[0763] Under a nitrogen atmosphere, 3.4 g (7.9 mmol) of 9-([1,1':2',1''-terphenyl]-4-yl)-2-chloro-9H-carbazole, 2.6 g (7.5 mmol) of N-(2-(naphthalen-2-yl)phenyl)naphthalen-2-amine, 0.94 g (9.8 mmol) of sodium tert-butoxide, 20 mL of xylene, 17 mg (75 μmol) of palladium acetate, and 0.12 g (0.15 mmol) of a 25 wt% xylene solution of tri(tert-butyl)phosphine were added to a 100 mL three-neck flask and stirred at 140 °C for 22 hours. After cooling to room temperature, 22 mL of pure water was added and stirred. The aqueous layer and organic layer were then separated, and the organic layer was washed with saturated sodium chloride aqueous solution. The organic layer was dried with anhydrous magnesium sulfate, and then column chromatography was performed using a small amount of silica gel to remove highly polar components. Next, the solvent was removed under reduced pressure, and the resulting solid was recrystallized in a mixed solvent of toluene and butanol to isolate 3.8 g (5.2 mmol) of the compound (F320) as a white solid (yield 69%). The sublimation temperature of F320 was confirmed to be 300°C, and the sublimated product of F320 was confirmed to be glassy.

[0764] Compound identification was performed by FDMS measurement.

[0765] FDMS:738 Example 48 (Synthesis of compound (F424))

[0766] [ka]

[0767] Under a nitrogen atmosphere, 3.0 g (7.0 mmol) of 9-([1,1':2',1''-terphenyl]-2-yl)-2-chloro-9H-carbazole, 3.0 g (6.6 mmol) of N-(2-(dibenzo[b,d]furan-4-yl)phenyl)-9,9-dimethyl-9H-fluoren-2-amine, 0.83 g (8.6 mmol) of sodium-tert-butoxide, 20 mL of xylene, 15 mg (66 μmol) of palladium acetate, and 0.11 g (0.13 mmol) of a 25 wt% xylene solution of tri(tert-butyl)phosphine were added to a 100 mL three-neck flask and stirred at 140 °C for 22 hours. After cooling to room temperature, 22 mL of pure water was added and stirred. The aqueous layer and organic layer were then separated, and the organic layer was washed with saturated sodium chloride aqueous solution. The organic layer was dried with anhydrous magnesium sulfate, and highly polar components were removed by column chromatography using a small amount of silica gel. The solvent was then removed under reduced pressure, and the resulting solid was recrystallized in a mixed solvent of toluene and butanol to isolate 4.5 g (5.3 mmol) of the compound (F424) as a white solid (80% yield). The sublimation temperature of F424 was confirmed to be 325°C, and the sublimated product was found to be glassy.

[0768] Compound identification was performed by FDMS measurement.

[0769] FDMS:844 Example 49 (Synthesis of compound (F839))

[0770] [ka]

[0771] Under a nitrogen stream, 2.4 g (5.5 mmol) of 9-([1,1':3',1''-terphenyl]-2'-yl)-2-chloro-9H-carbazole obtained in Synthesis Example 5, 2.5 g (5.3 mmol) of N-(2-(dibenzo[b,d]thiophen-4-yl)phenyl)fluoranthene-3-amine, 0.66 g (6.8 mmol) of sodium-tert-butoxide, 20 mL of xylene, 12 mg (53 μmol) of palladium acetate, and 85 mg (0.11 mmol) of a 25 wt% xylene solution of tri(tert-butyl)phosphine were added to a 100 mL three-neck flask and stirred at 140 °C for 22 hours. After cooling to room temperature, 22 mL of pure water was added and stirred. The aqueous layer and organic layer were then separated, and the organic layer was further washed with saturated sodium chloride aqueous solution. The organic layer was dried with anhydrous magnesium sulfate, and then column chromatography was performed using a small amount of silica gel to remove highly polar components. Next, the solvent was removed under reduced pressure, and the resulting solid was recrystallized in a mixed solvent of toluene and butanol to isolate 2.3 g (2.7 mmol) of compound (F839) as a white solid (yield 51%). The sublimation temperature of F839 was 315°C, and it was confirmed that the sublimated product of F839 was glassy.

[0772] Compound identification was performed by FDMS measurement.

[0773] FDMS:868 Example 50 (Synthesis of compound (F901))

[0774] [ka]

[0775] Under a nitrogen atmosphere, 3.6 g (7.9 mmol) of 2-chloro-9-(4,4''-dimethyl-[1,1':3',1''-terphenyl]-4'-yl)-9H-carbazole obtained in Synthesis Example 39, 2.6 g (7.5 mmol) of N-(2-(naphthalen-1-yl)phenyl)naphthalen-1-amine, 0.94 g (9.8 mmol) of sodium-tert-butoxide, 20 mL of xylene, 17 mg (75 μmol) of palladium acetate, and 0.12 g (0.15 mmol) of a 25 wt% xylene solution of tri(tert-butyl)phosphine were added to a 100 mL three-neck flask and stirred at 140 °C for 22 hours. After cooling to room temperature, 22 mL of pure water was added and stirred. The aqueous layer and organic layer were then separated, and the organic layer was further washed with saturated sodium chloride aqueous solution. The organic layer was dried with anhydrous magnesium sulfate, and then column chromatography was performed using a small amount of silica gel to remove highly polar components. Next, the solvent was removed under reduced pressure, and the resulting solid was recrystallized in a mixed solvent of toluene and butanol to isolate 4.6 g (5.9 mmol) of compound (F901) as a white solid (yield 79%). The sublimation temperature of F901 was 290°C, and it was confirmed that the sublimated product of F901 was glassy.

[0776] Compound identification was performed by FDMS measurement.

[0777] FDMS:766 Example 51 (Synthesis of compound (G360))

[0778] [ka]

[0779] Under a nitrogen stream, 2.0 g (4.6 mmol) of 9-([1,1':3',1''-terphenyl]-2-yl)-4-chloro-9H-carbazole obtained in Synthesis Example 41, 2.2 g (4.2 mmol) of N-(2-(dibenzo[b,d]thiophen-2-yl)phenyl)-10-phenylanthracene-9-amine, 0.52 g (5.4 mmol) of sodium-tert-butoxide, 20 mL of xylene, 9.4 mg (42 μmol) of palladium acetate, and 67 mg (83 μmol) of a 25 wt% xylene solution of tri(tert-butyl)phosphine were added to a 100 mL three-neck flask and stirred at 140 °C for 22 hours. After cooling to room temperature, 22 mL of pure water was added and stirred. The aqueous layer and organic layer were then separated, and the organic layer was further washed with saturated sodium chloride aqueous solution. The organic layer was dried with anhydrous magnesium sulfate, and then column chromatography was performed using a small amount of silica gel to remove highly polar components. Next, the solvent was removed under reduced pressure, and the resulting solid was recrystallized in a mixed solvent of toluene and butanol to isolate 2.6 g (2.8 mmol) of the compound (G360) as a white solid (yield 68%). The sublimation temperature of G360 was confirmed to be 350°C, and the sublimated product of G360 was confirmed to be glassy.

[0780] Compound identification was performed by FDMS measurement.

[0781] FDMS:920 Example 52 (Synthesis of compound (G702))

[0782] [ka]

[0783] Under a nitrogen stream, 1.9 g (4.0 mmol) of 4-chloro-9-(2-(dibenzo[b,d]thiophen-2-yl)-5-methylphenyl)-9H-carbazole obtained in Synthesis Example 42, 1.8 g (3.8 mmol) of N-(2-(phenanthren-9-yl)phenyl)pyrene-2-amine, 0.48 g (5.0 mmol) of sodium-tert-butoxide, 20 mL of xylene, 8.6 mg (38 μmol) of palladium acetate, and 62 mg (77 μmol) of a 25 wt% xylene solution of tri(tert-butyl)phosphine were added to a 100 mL three-neck flask and stirred at 140 °C for 22 hours. After cooling to room temperature, 22 mL of pure water was added and stirred. The aqueous layer and organic layer were then separated, and the organic layer was further washed with saturated sodium chloride aqueous solution. The organic layer was dried with anhydrous magnesium sulfate, and then column chromatography was performed using a small amount of silica gel to remove highly polar components. Next, the solvent was removed under reduced pressure, and the resulting solid was recrystallized in a mixed solvent of toluene and butanol to isolate 1.6 g (1.7 mmol) of the compound (G702) as a white solid (yield 45%). The sublimation temperature of G702 was confirmed to be 350°C, and the sublimated product of G702 was confirmed to be glassy.

[0784] Compound identification was performed by FDMS measurement.

[0785] FDMS:906 [Example of a transverse current measuring element] Example 53 (Evaluation of transverse current of compound D68) A glass substrate with 160 nm thick comb-shaped ITO electrodes is used to measure the lateral current. Two comb-shaped ITO electrodes are formed on this glass substrate, with an electrode width of 20 μm and a length of 2 mm. The gap between the two comb-shaped electrodes is 80 μm.

[0786] The above glass substrate was ultrasonically cleaned with ultrapure water. Surface treatment was performed by ozone ultraviolet cleaning. The glass substrate was introduced into a vacuum deposition chamber and 1.0 × 10 -4The pressure was reduced using a vacuum pump until it reached Pa. Then, each layer was fabricated according to the deposition conditions for each layer in the following order. Each organic material was deposited using the resistance heating method. (Preparation of hole injection layer) A 10 nm hole injection layer was fabricated by depositing a 10 nm film of the lateral current-suppressing compound (D68), which was purified by sublimation in Example 1, and 1,2,3-tris[(4-cyano-2,3,5,6-tetrafluorophenyl)methylene]cyclopropane in a ratio of 99:1 (mass ratio). (Preparation of hole transport layer) In Example 1, the compound (D68), which is a transverse current suppressing material purified by sublimation, was deposited as a 100 nm film at a rate of 0.2 nm / second to create a hole transport layer.

[0787] Under a nitrogen atmosphere, a glass plate for sealing was bonded with UV-curing resin to create a transverse current evaluation element. A voltage of 20V was applied between the comb-shaped electrodes of the element fabricated in this way, and the current flowing through it was measured as the transverse current. The results are shown in Table 1.

[0788] Example 54-104 (Transverse current evaluation of compound (D116)-(G702)) A transverse current evaluation element was fabricated in the same manner as in Example 53, except that compound (D116)-(G702), which was sublimated and purified in Example 2-52, was used instead of compound (D68). The transverse current measured for the transverse current evaluation element in the same manner as in Example 53 is shown in Table 1.

[0789] Comparative Example 1-4 (Synthesis of compounds (a)-(d), evaluation of transverse current) The known compounds (a)-(d) were synthesized and purified by sublimation.

[0790] A lateral current evaluation element was fabricated in the same manner as in Example 53, except that compounds (a)-(d) were used instead of compound (D4). The lateral current measured for the lateral current evaluation element in the same manner as in Example 53 is shown in Table 1.

[0791] [ka]

[0792] Reference Example 1-2 (Synthesis of compound (e)-(f), evaluation of transverse current) The known compounds (e)-(f) were synthesized and purified by sublimation.

[0793] A transverse current evaluation element was fabricated in the same manner as in Example 53, except that compounds (e)-(f) were used instead of compound (D4). The transverse current measured for the transverse current evaluation element in the same manner as in Example 53 is shown in Table 1.

[0794] [ka]

[0795] [Table 1]

[0796] Example 105 (Evaluation of transverse current of a mixed film of compound (D180) and compound (d)) A lateral current evaluation element was fabricated in the same manner as in Example 53, except that a mixed film of compound (D180) and compound (d) (weight ratio 50:50) was used instead of compound (D4). The lateral currents measured in the same manner as in Example 53 are shown in Table 2.

[0797] Example 106 (Evaluation of transverse current of a mixed film of compound (D853) and compound (d)) A lateral current evaluation element was fabricated in the same manner as in Example 53, except that a mixed film of compound (D853) and compound (d) (weight ratio 50:50) was used instead of compound (D4). The lateral currents measured in the same manner as in Example 53 are shown in Table 2.

[0798] Example 107 (Evaluation of transverse current of a mixed film of compound (E111) and compound (c)) A lateral current evaluation element was fabricated in the same manner as in Example 53, except that a mixed film of compound (E111) and compound (c) (weight ratio 50:50) was used instead of compound (D4). The lateral currents measured in the same manner as in Example 53 are shown in Table 2.

[0799] Example 108 (Evaluation of transverse current of a mixed film of compound (E228) and compound (c)) A lateral current evaluation element was fabricated in the same manner as in Example 53, except that a mixed film of compound (E111) and compound (c) (weight ratio 50:50) was used instead of compound (D4). The lateral currents measured in the same manner as in Example 53 are shown in Table 2.

[0800] Example 109 (Evaluation of transverse current of a mixed film of compound (F320) and compound (e)) A lateral current evaluation element was fabricated in the same manner as in Example 53, except that a mixed film of compound (F320) and compound (e) (weight ratio 30:70) was used instead of compound (D4). The lateral currents measured in the same manner as in Example 53 are shown in Table 2.

[0801] [Table 2]

[0802] [Examples of Organic Electroluminescent Elements] The fabrication of the organic electroluminescent element and the structural formulas and abbreviations of the compounds used are shown below.

[0803] [ka]

[0804] Example 110 (Evaluation of the device for compound (D273)) A glass substrate with transparent ITO electrodes was prepared, on which a 2 mm wide indium-tin (ITO) film (thickness 110 nm) was patterned in stripes. Next, this substrate was cleaned with isopropyl alcohol and then surface-treated with ozone ultraviolet cleaning. The glass substrate was introduced into a vacuum deposition chamber, and a 1.0 × 10⁻⁶ -4 The pressure was reduced to Pa. Then, each layer was fabricated according to the deposition conditions for each layer, in the following order.

[0805] (Preparation of hole injection layer) A hole injection layer was fabricated by depositing a 10 nm film of compound (D273) and 1,2,3-tris[(4-cyano-2,3,5,6-tetrafluorophenyl)methylene]cyclopropane in a 99:1 (mass ratio).

[0806] (Preparation of hole transport layer) A hole transport layer was fabricated by depositing compound (D273) at a rate of 0.2 nm / second to a thickness of 100 nm.

[0807] (Fabrication of electron-blocking layers) An electron blocking layer was fabricated by depositing an EBL film at a speed of 0.15 nm / second to a thickness of 5 nm.

[0808] (Fabrication of the light-emitting layer) A luminescent layer was fabricated by depositing HOST and DOPANT in a 95:5 (mass ratio) ratio at a thickness of 20 nm. The deposition rate was 0.18 nm / second.

[0809] (Fabrication of electron transport layer) The first electron transport layer was fabricated by depositing a 6nm HBL film at a speed of 0.05nm / second.

[0810] (Fabrication of electron injection layer) A second electron transport layer was fabricated by depositing ETL and Liq in a 50:50 (mass ratio) layer at a 25 nm thickness. The deposition rate was 0.15 nm / second.

[0811] (Cathode fabrication) Finally, a metal mask was positioned perpendicular to the ITO stripes on the substrate, and the cathode was deposited. The cathode consisted of three layers: ytterbium, silver / magnesium (mass ratio 9 / 1), and silver, deposited in that order at 2 nm, 12 nm, and 90 nm, respectively. The deposition rate for ytterbium was 0.02 nm / second, for silver / magnesium it was 0.5 nm / second, and for silver it was 0.2 nm / second.

[0812] Therefore, the light-emitting area is 4mm 2 We fabricated an organic electroluminescent device.

[0813] Furthermore, this element was sealed in a nitrogen atmosphere glove box with oxygen and moisture concentrations of 1 ppm or less. The sealing was performed using UV-curing epoxy resin (manufactured by Moresco) to seal the glass sealing cap and the film-deposited substrate (element).

[0814] The element fabricated in this way draws 10 mA / cm². 2 The current was applied, and the voltage and luminous efficiency were measured. The results are shown in Table 3.

[0815] Examples 111-116 (Evaluation of devices using compounds (D336), (D350), (E103), (E264), (F228), and (F901)) Organic electroluminescent elements were fabricated in the same manner as in Example 110, except that compounds (D336), (D350), (E103), (E264), (F228), and (F901) were used instead of compound (D273). The results are shown in Table 3.

[0816] Comparative Examples 5-7 (Evaluation of devices for compound (g), compound (h), and compound (i)) Organic electroluminescent elements were fabricated in the same manner as in Example 110, except that compounds (g), (h), and (i) were used instead of compound (D273). The results are shown in Table 3.

[0817] [ka]

[0818] [Table 3] [Explanation of Symbols]

[0819] 1 circuit board 2 Anode 3. Hole injection layer 4. Hole transport layer 5 Electron blocking layer 6. Emitting layer 7. Electron transport layer 8 Electron Injection Layer 9 Cathode

Claims

1. Carbazole compounds represented by formula (22) or formula (23): 【Chemistry 1】 During the ceremony, Ar ６ These are groups selected from the following formulas (24) to (44), and represented by (Z1) to (Z209). 【Chemistry 2】 【Transformation 3】 【Chemistry 4】 During the ceremony, R ４ This represents a biphenylyl group, naphthyl group, phenanthryl group, dibenzofuranyl group, or dibenzothienyl group, which may be substituted with a methyl group. R ５ Each of these independently represents either a methyl group or a hydrogen atom. R ６ This represents a phenyl group, biphenylyl group, naphthyl group, phenanthryl group, dibenzofuranyl group, or dibenzothienyl group, which may be substituted with a methyl group. R ７ and R ８ Each of these independently represents a phenyl group, biphenylyl group, naphthyl group, phenanthryl group, dibenzofuranyl group, or dibenzothienyl group, which may be substituted with a methyl group, and at least one of these is a biphenylyl group, naphthyl group, phenanthryl group, dibenzofuranyl group, or dibenzothienyl group, which may be substituted with a methyl group. In equations (22) and (23), Ar ６ If is a base selected from equations (24) to (31), Ar ５ is a group selected from groups represented by formulae (24) to (45), and Ar ４ is a group represented by an optionally substituted monocyclic, linked or condensed ring aromatic hydrocarbon group having 6 to 30 carbon atoms, or an optionally substituted monocyclic, linked or condensed ring heteroaromatic group having 3 to 30 carbon atoms. In equations (22) and (23), Ar ６ If is a base selected from equations (32) to (44), Ar ４ and Ar ５ Each of these groups is independently represented by a group selected from formulas (24) to (45), or by a monocyclic, linked, or fused aromatic hydrocarbon group having 6 to 30 carbon atoms, which may be substituted, or by a monocyclic, linked, or fused heteroaromatic group having 3 to 30 carbon atoms, which may be substituted. 【Transformation 5】 【Transformation 6】 【Transformation 7】 【Transformation 8】 【Chemistry 9】 【Chemistry 10】 【Chemistry 11】

2. The first compound and A hole injection layer containing a second compound, The first compound is the carbazole compound described in claim 1, A hole injection layer in which the second compound is an electron-accepting p-dopant.

3. It further contains a third compound, The hole implantation layer according to claim 2, wherein the third compound is a hole-transporting triarylamine compound.

4. The hole injection layer according to claim 2 or 3, wherein the content of the carbazole compound according to claim 1 is 20% by mass or more and 99.5% by mass or less.

5. An organic electroluminescent element comprising a hole injection layer, The hole injection layer, An organic electroluminescent element containing the carbazole compound described in claim 1.

6. The organic electroluminescent element according to claim 5, wherein the hole injection layer is the hole injection layer according to any one of claims 2 to 4.

7. Further equipped with a hole transport layer, The hole transport layer is An organic electroluminescent element according to claim 5, comprising the carbazole compound according to claim 1.

8. Anode and, Multiple organic layers on the anode, An organic electroluminescent element comprising a cathode on a plurality of organic layers, An organic electroluminescent element in which one or more of the plurality of organic layers contain the carbazole compound described in claim 1.

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