WO2023170880A1 - Dicarbazolyl benzene compound and organic electroluminescent device - Google Patents
Dicarbazolyl benzene compound and organic electroluminescent device Download PDFInfo
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- WO2023170880A1 WO2023170880A1 PCT/JP2022/010682 JP2022010682W WO2023170880A1 WO 2023170880 A1 WO2023170880 A1 WO 2023170880A1 JP 2022010682 W JP2022010682 W JP 2022010682W WO 2023170880 A1 WO2023170880 A1 WO 2023170880A1
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- dicarbazolylbenzene
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- -1 Dicarbazolyl benzene compound Chemical class 0.000 title claims abstract description 26
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 33
- 125000000524 functional group Chemical group 0.000 claims abstract description 17
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims abstract description 14
- BODVWELZYMTBLU-UHFFFAOYSA-N 1-[2-(9h-carbazol-1-yl)phenyl]-9h-carbazole Chemical compound C12=CC=CC=C2NC2=C1C=CC=C2C1=CC=CC=C1C1=CC=CC2=C1NC1=CC=CC=C12 BODVWELZYMTBLU-UHFFFAOYSA-N 0.000 claims abstract description 12
- 125000001424 substituent group Chemical group 0.000 claims abstract description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 26
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 18
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 13
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 239000000126 substance Substances 0.000 description 56
- 239000010410 layer Substances 0.000 description 44
- 150000001875 compounds Chemical class 0.000 description 30
- 239000000463 material Substances 0.000 description 17
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- 238000005481 NMR spectroscopy Methods 0.000 description 14
- 229910052799 carbon Inorganic materials 0.000 description 13
- 229910052757 nitrogen Inorganic materials 0.000 description 13
- 238000011156 evaluation Methods 0.000 description 12
- 239000007787 solid Substances 0.000 description 12
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 12
- 235000013619 trace mineral Nutrition 0.000 description 11
- 239000011573 trace mineral Substances 0.000 description 11
- 239000005416 organic matter Substances 0.000 description 10
- 239000000203 mixture Substances 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 8
- 230000005525 hole transport Effects 0.000 description 8
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 8
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- 239000012043 crude product Substances 0.000 description 6
- 235000019439 ethyl acetate Nutrition 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 150000002894 organic compounds Chemical class 0.000 description 5
- 150000001499 aryl bromides Chemical class 0.000 description 4
- 238000004770 highest occupied molecular orbital Methods 0.000 description 4
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 3
- 239000005977 Ethylene Substances 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 239000012300 argon atmosphere Substances 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 3
- 239000011259 mixed solution Substances 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- ZKGHGKNHPPZALY-UHFFFAOYSA-N 9-(3-bromophenyl)carbazole Chemical compound BrC1=CC=CC(N2C3=CC=CC=C3C3=CC=CC=C32)=C1 ZKGHGKNHPPZALY-UHFFFAOYSA-N 0.000 description 2
- NSXJEEMTGWMJPY-UHFFFAOYSA-N 9-[3-(3-carbazol-9-ylphenyl)phenyl]carbazole Chemical group C12=CC=CC=C2C2=CC=CC=C2N1C1=CC(C=2C=CC=C(C=2)N2C3=CC=CC=C3C3=CC=CC=C32)=CC=C1 NSXJEEMTGWMJPY-UHFFFAOYSA-N 0.000 description 2
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical group [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 229910052805 deuterium Inorganic materials 0.000 description 2
- 230000009477 glass transition Effects 0.000 description 2
- VBQIVFTUXFKGKW-UHFFFAOYSA-N n-[4-(4-bromophenyl)phenyl]-4-phenyl-n-(4-phenylphenyl)aniline Chemical compound C1=CC(Br)=CC=C1C1=CC=C(N(C=2C=CC(=CC=2)C=2C=CC=CC=2)C=2C=CC(=CC=2)C=2C=CC=CC=2)C=C1 VBQIVFTUXFKGKW-UHFFFAOYSA-N 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- JSRLURSZEMLAFO-UHFFFAOYSA-N 1,3-dibromobenzene Chemical compound BrC1=CC=CC(Br)=C1 JSRLURSZEMLAFO-UHFFFAOYSA-N 0.000 description 1
- LPLLWKZDMKTEMV-UHFFFAOYSA-N 1-bromo-3-(3-bromophenyl)benzene Chemical group BrC1=CC=CC(C=2C=C(Br)C=CC=2)=C1 LPLLWKZDMKTEMV-UHFFFAOYSA-N 0.000 description 1
- PKJBWOWQJHHAHG-UHFFFAOYSA-N 1-bromo-4-phenylbenzene Chemical group C1=CC(Br)=CC=C1C1=CC=CC=C1 PKJBWOWQJHHAHG-UHFFFAOYSA-N 0.000 description 1
- YXHXRBIAIVNCPG-UHFFFAOYSA-N 9-(3,5-dibromophenyl)carbazole Chemical compound BrC1=CC(Br)=CC(N2C3=CC=CC=C3C3=CC=CC=C32)=C1 YXHXRBIAIVNCPG-UHFFFAOYSA-N 0.000 description 1
- SJOKONNBSXFPSN-UHFFFAOYSA-N 9-(3-bromo-5-carbazol-9-ylphenyl)carbazole Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC(N2C3=CC=CC=C3C3=CC=CC=C32)=CC(Br)=C1 SJOKONNBSXFPSN-UHFFFAOYSA-N 0.000 description 1
- YJEUUQOJSFGEQT-UHFFFAOYSA-N 9-(3-bromophenyl)-3,6-diphenylcarbazole Chemical compound BrC1=CC=CC(N2C3=CC=C(C=C3C3=CC(=CC=C32)C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 YJEUUQOJSFGEQT-UHFFFAOYSA-N 0.000 description 1
- WOOAKXXQTAVKGL-UHFFFAOYSA-N 9-(4-bromophenyl)-3,6-diphenylcarbazole Chemical compound C1=CC(Br)=CC=C1N1C2=CC=C(C=3C=CC=CC=3)C=C2C2=CC(C=3C=CC=CC=3)=CC=C21 WOOAKXXQTAVKGL-UHFFFAOYSA-N 0.000 description 1
- CLGDYJYGBMTANB-UHFFFAOYSA-N 9-[4-(4-bromophenyl)phenyl]-3,6-diphenylcarbazole Chemical compound BrC1=CC=C(C=C1)C1=CC=C(C=C1)N1C2=CC=C(C=C2C=2C=C(C=CC12)C1=CC=CC=C1)C1=CC=CC=C1 CLGDYJYGBMTANB-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- BTFIECQCKYNJTN-UHFFFAOYSA-N n-(4-bromophenyl)-4-phenyl-n-(4-phenylphenyl)aniline Chemical compound C1=CC(Br)=CC=C1N(C=1C=CC(=CC=1)C=1C=CC=CC=1)C1=CC=C(C=2C=CC=CC=2)C=C1 BTFIECQCKYNJTN-UHFFFAOYSA-N 0.000 description 1
- VKUGPCCUCHYUFE-UHFFFAOYSA-N n-(4-bromophenyl)-n-naphthalen-2-ylnaphthalen-2-amine Chemical compound C1=CC(Br)=CC=C1N(C=1C=C2C=CC=CC2=CC=1)C1=CC=C(C=CC=C2)C2=C1 VKUGPCCUCHYUFE-UHFFFAOYSA-N 0.000 description 1
- XUTVUTNJPNJUIK-UHFFFAOYSA-N n-[4-(4-bromophenyl)phenyl]-n-naphthalen-2-ylnaphthalen-2-amine Chemical compound C1=CC(Br)=CC=C1C1=CC=C(N(C=2C=C3C=CC=CC3=CC=2)C=2C=C3C=CC=CC3=CC=2)C=C1 XUTVUTNJPNJUIK-UHFFFAOYSA-N 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 238000006862 quantum yield reaction Methods 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- FKHIFSZMMVMEQY-UHFFFAOYSA-N talc Chemical compound [Mg+2].[O-][Si]([O-])=O FKHIFSZMMVMEQY-UHFFFAOYSA-N 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/88—Carbazoles; Hydrogenated carbazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
- H10K50/15—Hole transporting layers
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
- H10K50/16—Electron transporting layers
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- H—ELECTRICITY
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
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- H—ELECTRICITY
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
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- H—ELECTRICITY
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
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- H—ELECTRICITY
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
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- H—ELECTRICITY
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
Definitions
- the present invention relates to dicarbazolylbenzene compounds and organic electroluminescent devices.
- an electron transport layer, a light emitting layer, and a hole transport layer are sandwiched between an anode and a cathode. It is desirable that the organic EL element configured in this manner has a long life. From this point of view, an organic substance suitable as a material for an electron transport layer, a light emitting layer, or a hole transport layer is required.
- JP 2021-172592A proposes a compound containing a nitrogen-containing heterocycle. In JP-A-2021-172592, the compound is used as a material for an electron transport layer, a light emitting layer, or a hole transport layer.
- the present invention aims to solve the above-mentioned problems.
- two carbazolyl groups have one or more dicarbazolyl groups bonded to each other or one or more substituted dicarbazolyl groups to which one or more functional groups are bonded
- a dicarbazolylbenzene compound having as a basic skeleton a dicarbazolylbenzene in which one or more dicarbazolyl groups or one or more substituted dicarbazolyl groups are bonded to a benzene ring, and is represented by the following structural formula (1). be done.
- R2 to R5 in Structural Formula (1) represent a substituent bonded to any position of the benzene ring constituting the carbazolyl group.
- R2 to R5 may be hydrogen.
- At least one of L1 to L3 in the above structural formula (1) is a functional group represented by the following structural formula (2), structural formula (3), or structural formula (4).
- R6 and R7 are substituted aromatic hydrocarbon groups or unsubstituted aromatic hydrocarbon groups, or substituted nitrogen-containing aromatic heterocyclic groups or unsubstituted nitrogen-containing aromatic heterocyclic groups.
- R8 in the above structural formula (3) is hydrogen, a substituted aromatic hydrocarbon group, or an unsubstituted aromatic hydrocarbon group.
- R9 and R10 in the above structural formula (4) are hydrogen.
- R9 and R10 may be substituted or unsubstituted aromatic hydrocarbon groups.
- At least one of R2 to R5 is a monovalent aromatic hydrocarbon group
- at least one of L1 to L3 is a substituted aromatic hydrocarbon or an unsubstituted aromatic hydrocarbon, or It is a substituted aromatic heterocyclic group or an unsubstituted aromatic heterocyclic group.
- an organic electroluminescent device that includes a layer containing the dicarbazolylbenzene compound described above.
- hydrogen in each compound may be replaced with deuterium.
- the deuteration rate may be high, for example, about 80%.
- the energy of the first excited triplet state (T1) is high.
- the highest occupied level (HOMO) and lowest unoccupied level (LUMO) of the above-mentioned compound are within appropriate ranges when used as a charge transport material, especially when a blue light emitting material is included in the light emitting layer.
- the charge easily moves within the molecule, so that it is difficult for the charge to become delocalized. Therefore, the molecular structure is stabilized. Furthermore, since intramolecular rotation is suppressed based on the molecular structure, thermal stability is good.
- an organic electroluminescent element including a layer containing the above compound has a longer lifespan.
- FIG. 1 is a schematic side view of an organic EL element.
- FIG. 2 is a chart showing various physical properties of dicarbazolylbenzene compounds.
- FIG. 3 is a chart showing various characteristics of an organic EL element having a light emitting layer containing an organic substance.
- FIG. 4 is a chart showing various characteristics of an organic EL element having a layer containing an organic substance.
- FIG. 1 is a schematic side view of an organic electroluminescence (EL) element 10.
- the organic EL element 10 includes a glass substrate 12, an anode 14, a hole transport layer 16, a light emitting layer 18, an electron transport layer 20, and a cathode 22.
- EL organic electroluminescence
- At least one of the hole transport layer 16, the light emitting layer 18, or the electron transport layer 20 contains a dicarbazolylbenzene compound.
- the dicarbazolylbenzene compound refers to a compound containing as a basic skeleton a benzene ring to which one or more dicarbazolyl groups are bonded, each having two carbazolyl groups bonded to each other.
- a dicarbazolylbenzene compound refers to a compound containing as a basic skeleton a benzene ring to which one or more substituted dicarbazolyl groups are bonded.
- the structural formula of the dicarbazolylbenzene compound according to this embodiment is shown in the following structural formula (1).
- R2 to R5 in the above structural formula (1) represent hydrogen or a substituent bonded to any position of the benzene ring constituting the carbazolyl group. Furthermore, at least one of L1 to L3 in the above structural formula (1) is a functional group represented by the following structural formula (2), structural formula (3), or structural formula (4).
- n in the above structural formula (2) is 0 or 1.
- structural formula (1) is transformed into the following structural formula.
- N is bonded to the benzene ring in structural formula (1).
- N is bonded to the benzene ring in structural formula (1) via a phenyl group.
- R6 and R7 in structural formula (2) represent a substituted or unsubstituted aromatic hydrocarbon group.
- R6 and R7 may be substituted or unsubstituted nitrogen-containing aromatic heterocyclic groups.
- Representative examples of the nitrogen-containing aromatic heterocyclic group include a nitrogen-containing 5-membered ring group, a nitrogen-containing 6-membered ring group, a nitrogen-containing aromatic condensed two-ring group, and a nitrogen-containing aromatic condensed three-ring group.
- Specific examples of the nitrogen-containing 5-membered cyclic group include a pyrrolyl group
- specific examples of the nitrogen-containing 6-membered cyclic group include a pyridinyl group or a pyrimidyl group.
- nitrogen-containing aromatic condensed two rings include an indolyl group and a quinolyl group
- specific examples of the nitrogen-containing aromatic condensed three rings include a carbazolyl group and a phenanthrolyl group.
- the nitrogen-containing aromatic heterocyclic group is not particularly limited to the above-mentioned substituents.
- R8 in Structural Formula (3) represents a substituted or unsubstituted aromatic hydrocarbon group.
- R8 may be a substituted or unsubstituted nitrogen-containing aromatic heterocyclic group.
- R9 and R10 in structural formula (4) are hydrogen.
- R9 and R10 may be substituted or unsubstituted aromatic hydrocarbon groups.
- All of R2 to R5 may be hydrogen. Specific examples of L1 to L3 in this case will be shown below.
- Me represents a methyl group.
- the dicarbazolylbenzene compound may be a compound in which two dicarbazolyl groups or two substituted dicarbazolyl groups are bonded to a benzene ring. Furthermore, any one of L1 to L3 bonded to the benzene ring is preferably a carbazolyl group or a substituted carbazolyl group.
- the structural formula of this compound is illustrated below. Note that this structural formula exemplifies a compound in which two dicarbazolyl groups and one carbazolyl group are bonded to a benzene ring. That is, in this compound, hydrogen contained in the dicarbazolyl group and the carbazolyl group is not substituted with a substituent.
- the dicarbazolylbenzene compound may be a compound in which two dicarbazolyl groups, two substituted dicarbazolyl groups, or one dicarbazolyl group and one substituted dicarbazolyl group are bonded to a benzene ring. .
- Two dicarbazolyl groups, two substituted dicarbazolyl groups, or one dicarbazolyl group and one substituted dicarbazolyl group are preferably at the ortho position (o-position) in the benzene ring.
- this compound is illustrated below. Note that this structural formula exemplifies a compound in which two dicarbazolyl groups are bonded to a benzene ring. That is, in this compound, hydrogen contained in the dicarbazolyl group is not substituted with a functional group. Further, the two dicarbazolyl groups are positioned at the o-position in the benzene ring.
- the dicarbazolylbenzene compound may be a compound in which two dicarbazolylbenzenes are bonded to each other.
- one dicarbazolylbenzene is a compound in which a dicarbazolyl group or a substituted dicarbazolyl group is bonded to a benzene ring. Therefore, the dicarbazolylbenzene compound in this case has a form in which a functional group containing a phenyl group is bonded to dicarbazolylbenzene.
- a functional group containing a phenyl group refers to a functional group in which a dicarbazolyl group or a substituted dicarbazolyl group is bonded to a phenyl group.
- the dicarbazolyl group or substituted dicarbazolyl group in dicarbazolylbenzene and the functional group containing a phenyl group are preferably o-positioned in the benzene ring.
- this compound is illustrated below. Note that this structural formula exemplifies a compound in which two dicarbazolylbenzenes are bonded to each other. That is, in this compound, hydrogen contained in the dicarbazolyl group is not substituted with a functional group. Furthermore, the dicarbazolyl group and the functional group containing the phenyl group are in a positional relationship such that they are at the o-position in the benzene ring.
- R2 to R5 may be monovalent aromatic hydrocarbon groups.
- at least one of L1 to L3 is a monovalent substituted aromatic hydrocarbon group or a monovalent unsubstituted aromatic hydrocarbon group.
- At least one of L1 to L3 may be a monovalent substituted aromatic heterocyclic group or a monovalent unsubstituted aromatic heterocyclic group.
- the organic EL element 10 having the layer is different from the conventional technology. It is recognized that the lifespan is longer than that of such organic EL elements.
- T1 the energy of the first excited triplet state
- HOMO highest occupied level
- LUMO lowest unoccupied level
- the molecule forms a sterically twisted structure. This limits the extent of the ⁇ conjugate. As a result, wide gaps in energy tend to occur. Such a compound is considered to be more suitable as a material for blue light emission.
- hydrogen in the organic compound described above may be replaced with deuterium.
- the deuteration rate may be high, for example, about 80%.
- dicarbazolylbenzene compounds can have various structures by bonding substituted aromatic hydrocarbon groups or substituted aromatic heterocyclic groups.
- Example 1 For 5 ml of mesitylene, 2 mmol of dicarbazole, 2 mmol of 9-(3-bromophenyl)-9H-carbazole, 0.04 mmol of Pd(OAc) 2 and 0.16 mmol of t- Bu 3 P and 3 mmol of NaO(t-Bu) were added to prepare a mixed solution. The mixture was stirred for 4 hours while being maintained at 150° C. under an argon atmosphere. The mixture was quenched by adding 3 milliliters of 1 mol/liter HCl, and the organic matter was extracted from the mixture using EtOAc. After washing the organic matter with saturated brine, the organic matter was dried with MgSO 4 . The solvent was removed under reduced pressure to obtain the crude product.
- the crude product was passed through Florisil using ethyl acetate as a developing solvent, and then the solvent was removed under reduced pressure and recrystallized using 2-propanol to obtain a whitish-brown organic substance.
- the yield was 1.13 g, and the yield was 98%.
- DCZ-1 the organic substance that is the product
- Example 2 For 2.7 ml of mesitylene, 0.33 g of dicarbazole, 0.49 g of Ar-Br (aryl bromide), 4.5 mg of Pd(OAc) 2 and 16.2 mg of t-Bu 3 P and 0.144 g of NaO(t-Bu) were added to prepare a mixed solution. The mixture was maintained at 150°C and stirred under an argon atmosphere. The aryl bromide used was 9,9'-(5-bromo-1,3-phenylene)bis(9H-carbazole), and its structural formula is as follows.
- the mixture was quenched by adding 1.5 milliliters of 1 mol/liter HCl, and the organic matter was extracted from the mixture using EtOAc. After washing the organic matter with saturated brine, the organic matter was dried with MgSO 4 . The solvent was removed under reduced pressure to obtain the crude product. Next, the crude product was purified by silica gel column using ethyl acetate as a developing solvent. The obtained purified product was reprecipitated with ethanol to obtain a white solid organic substance. The yield was 0.66 g, and the yield was 89%. After washing the organic matter with pure water and saturated brine, the organic matter was dried with MgSO 4 .
- DCZ-2 this organic substance will be referred to as DCZ-2.
- Example 3 A white color was prepared in the same manner as in Example 2 except that 0.47 g of 9-(3-bromophenyl)-3,6-diphenyl-9H-carbazole whose structural formula is shown below was used and hexane and EtOAc were used as the developing solvents. A solid organic material was obtained. The yield was 0.33 g, and the yield was 75%.
- DCZ-3 this organic substance will be referred to as DCZ-3.
- Example 4 A white solid organic substance was obtained in the same manner as in Example 3 except that 0.66 g of 1,3-dibromobenzene was used. Note that dicarbazole, Pd(OAc) 2 , t-Bu 3 P, and NaO(t-Bu) were 0.66 g, 9 mg, 32.4 mg, and 0.29 g, respectively, and mesitylene was 4 ml. In addition, chloroform was used for extraction. Chloroform was also used as the developing solvent. The yield was 0.44 g, and the yield was 59%.
- DCZ-4 this organic substance will be referred to as DCZ-4.
- Example 5 A white solid organic substance was obtained in the same manner as in Example 1, except that 1 mmol of 9-(3,5-dibromophenyl)-9H-carbazole having the structural formula shown below was used. Note that dicarbazole, Pd(OAc) 2 , t-Bu 3 P, and NaO(t-Bu) were set at 2 mmol, 0.04 mmol, 0.16 mmol, and 3 mmol, respectively, and mesitylene was set at 5 ml. . The yield was 0.81 g, and the yield was 90%.
- DCZ-6 this organic substance will be referred to as DCZ-6.
- Example 6 A white solid organic substance was obtained in the same manner as in Example 4, except that 1 mmol of N,N-bis(4-biphenylyl)-N-(4-bromophenyl)amine whose structural formula is shown below was used. . Note that dicarbazole, Pd(OAc) 2 , t-Bu 3 P, and NaO(t-Bu) are 1 mmol, 0.02 mmol, 0.08 mmol, and 1.5 mmol, respectively, and mesitylene is 4 ml. And so. The yield was 0.46 g, and the yield was 63%.
- DCZ-9 this organic substance will be referred to as DCZ-9.
- Example 7 A white solid organic substance was obtained in the same manner as in Example 5 except that 4'-bromotri(4-biphenylyl)amine having the structural formula shown below was used.
- the molar ratios of dicarbazole, 4'-bromotri(4-biphenylyl)amine, Pd(OAc) 2 , t-Bu 3 P and NaO(t-Bu) are the same as in Example 5. Note that the amount of mesitylene was 2.5 ml. The yield was 0.72 g, and the yield was 89%.
- DCZ-10 this organic substance will be referred to as DCZ-10.
- Example 8 A white solid organic substance was prepared in the same manner as in Example 2 except that 1 mmol of N-(4-bromophenyl)-N-(naphthalen-2-yl)naphthalen-2-amine whose structural formula is shown below was used. Obtained. Note that the amount of ethylene was 2.7 ml. The yield was 0.60 g, and the yield was 88%.
- DCZ-11 this organic substance will be referred to as DCZ-11.
- Example 9 Except for using 1 mmol of N-(4'-bromo-[1,1'-biphenyl]-4-yl)-N-(naphthalen-2-yl)-naphthalen-2-amine whose structural formula is shown below. A white solid organic substance was obtained in the same manner as in Example 8, including the amount of mesitylene. The yield was 0.65 g, and the yield was 87%.
- DCZ-12 this organic substance will be referred to as DCZ-12.
- Example 10 The amount of mesitylene was also included, except that 0.474 g, equivalent to 1 mmol, of 9-(4-bromophenyl)-3,6-diphenyl-9H-carbazole, whose structural formula is shown below, was used as the aryl bromide. In the same manner as in Example 9, a white solid organic substance was obtained. The yield was 0.52 g, and the yield was 71%.
- DCZ-13 this organic substance will be referred to as DCZ-13.
- Example 11 1 mmol of 9-(4'-bromo-[1,1'-biphenyl]-4-yl)-3,6-diphenyl-9H-carbazole whose structural formula is shown below was used, and ethylene was set at 5 ml. A white solid organic substance was obtained in the same manner as in Example 10 except for this. The yield was 0.70 g, and the yield was 88%.
- DCZ-14 this organic substance will be referred to as DCZ-14.
- DCZ-15 this organic substance will be referred to as DCZ-15.
- Example 13 A mixed solution was prepared in the same manner as in Example 1 except that 1 mmol of 3,3'-dibromobiphenyl was used in place of 9-(3-bromophenyl)-9H-carbazole. The mixture was stirred for 4 hours while being maintained at 150° C. under an argon atmosphere. The mixture was quenched by adding 1 mol/liter of HCl, and extracted with chloroform. After washing the organic layer with water, the organic layer was washed with saturated brine. The organics were then dried with MgSO4 . The solvent was removed under reduced pressure to obtain the crude product.
- the crude product was purified on a silica gel column using a 5:1 mixture of hexane/ethyl acetate as a developing solvent to obtain a white solid organic substance.
- the yield was 0.55 g, and the yield was 68%.
- DCZ-20 the organic substance that is the product
- the energy of the first excited triplet state (T1) of each compound is high.
- the HOMO energy (EHOMO) and lowest unoccupied level energy (ELUMO) of each compound are within appropriate ranges, especially when used as a charge transport material when a blue light emitting material is included in the light emitting layer.
- Organic EL devices each having a structure shown in FIG. 1 and having a light emitting layer containing DCZ-9 or DCZ-10 as a host material were manufactured.
- an organic EL element having the structure shown in FIG. 1 was prepared, including a light-emitting layer containing URP or 3,3'-di(9H-carbazol-9-yl)-1,1'-biphenyl as a host material.
- m-CBP 3,3'-di(9H-carbazol-9-yl)-1,1'-biphenyl
- each organic EL element was evaluated by causing it to emit fluorescence, phosphorescence, or thermally activated delayed fluorescence (TADF). Note that the lifetime is the time until the emission intensity decreases to 90% of the initial characteristic.
- TADF thermally activated delayed fluorescence
- an organic EL device using DCZ-9 or DCZ-10 as the host material of the emitting layer is different from an organic EL device using URP as the host material of the emitting layer. It showed better efficiency than EL devices.
- Element evaluation part 2 Nine types of organic EL devices having a hole injection layer (HIL), a hole transport layer (HTL), an electron block layer (EBL), and a hole block layer (HBL) were fabricated.
- HIL hole injection layer
- HTL hole transport layer
- EBL electron block layer
- HBL hole block layer
- evaluation elements 1 to 9 The substances shown in FIG. 4 were used as organic compounds contained in HIL, HTL, EBL, and HBL in Evaluation Elements 1 to 9.
- DCZ-9 or DCZ-10 is included in at least one of the HIL, HTL, EBL, and HBL layers.
- OPDA-10 contained in HTL of evaluation element 2 and HIL of evaluation element 5, respectively, is an organic compound whose chemical structural formula is shown below.
- control element 1 and control element 2 are shown in FIG. 4.
- Evaluation Elements 1 to 9 having layers containing DCZ-9 or DCZ-10 have better lifetimes than Control Elements 1 and 2 that do not have layers containing DCZ-9 or DCZ-10. It can be seen that this shows that Furthermore, the efficiency of Evaluation Elements 1 to 9 is approximately equal to or higher than that of Comparative Element 1 and Comparative Element 2. As described above, the organic EL elements (Evaluation Elements 1 to 9) having layers containing DCZ-9 or DCZ-10 are equivalent to the organic EL elements according to the prior art (Control Element 1 and Control Element 2). Demonstrates efficiency and excellent longevity.
Abstract
This dicarbazolyl benzene compound has at least one dicarbazolyl group in which two carbazolyl groups are bonded to each other or at least one substituent dicarbazolyl group to which at least one functional group is bonded. The dicarbazolyl benzene compound includes, as the basic skeleton thereof, a dicarbazolyl benzene in which at least at least one of the dicarbazolyl groups or the at least one substituent dicarbazolyl group is bonded to a benzene ring. The dicarbazolyl benzene compound has the structure represented by structural formula (1).
Description
本発明は、ジカルバゾリルベンゼン類化合物及び有機エレクトロルミネッセンス素子に関する。
The present invention relates to dicarbazolylbenzene compounds and organic electroluminescent devices.
有機エレクトロルミネッセンス（ＥＬ）素子においては、アノードとカソードとの間に、電子輸送層、発光層及び正孔輸送層が挟まれる。このように構成される有機ＥＬ素子は、長寿命化であることが望ましい。この観点から、電子輸送層、発光層又は正孔輸送層の素材として適切な有機物が求められている。この要請に対応するため、例えば、特開２０２１－１７２５９２号公報において、窒素を有する複素環を含んだ化合物が提案されている。特開２０２１－１７２５９２号公報では、前記化合物は、電子輸送層、発光層又は正孔輸送層の素材として用いられている。
In an organic electroluminescent (EL) device, an electron transport layer, a light emitting layer, and a hole transport layer are sandwiched between an anode and a cathode. It is desirable that the organic EL element configured in this manner has a long life. From this point of view, an organic substance suitable as a material for an electron transport layer, a light emitting layer, or a hole transport layer is required. In order to meet this demand, for example, JP 2021-172592A proposes a compound containing a nitrogen-containing heterocycle. In JP-A-2021-172592, the compound is used as a material for an electron transport layer, a light emitting layer, or a hole transport layer.
有機ＥＬのさらなる長寿命化が要請されている。
There is a demand for organic EL to have an even longer lifespan.
本発明は、上述した課題を解決することを目的とする。
The present invention aims to solve the above-mentioned problems.
本発明の一実施形態によれば、２個のカルバゾリル基が互いに結合した１個以上のジカルバゾリル基、又は、１個以上の官能基が結合した１個以上の置換ジカルバゾリル基を有し、前記１個以上のジカルバゾリル基又は前記１個以上の置換ジカルバゾリル基がベンゼン環に結合したジカルバゾリルベンゼンを基本骨格として含み、下記の構造式（１）で示されるジカルバゾリルベンゼン類化合物が提供される。
According to one embodiment of the present invention, two carbazolyl groups have one or more dicarbazolyl groups bonded to each other or one or more substituted dicarbazolyl groups to which one or more functional groups are bonded, Provided is a dicarbazolylbenzene compound having as a basic skeleton a dicarbazolylbenzene in which one or more dicarbazolyl groups or one or more substituted dicarbazolyl groups are bonded to a benzene ring, and is represented by the following structural formula (1). be done.
上記構造式（１）中のＬ１～Ｌ３の少なくともいずれか１個は、下記の構造式（２）、構造式（３）又は構造式（４）に示される官能基である。
At least one of L1 to L3 in the above structural formula (1) is a functional group represented by the following structural formula (2), structural formula (3), or structural formula (4).
上記構造式（２）中のｎは、０又は１である。
Ｒ６及びＲ７は、置換芳香族炭化水素基もしくは無置換芳香族炭化水素基であるか、又は、置換窒素含有芳香族複素環基もしくは無置換窒素含有芳香族複素環基である。 n in the above structural formula (2) is 0 or 1.
R6 and R7 are substituted aromatic hydrocarbon groups or unsubstituted aromatic hydrocarbon groups, or substituted nitrogen-containing aromatic heterocyclic groups or unsubstituted nitrogen-containing aromatic heterocyclic groups.
Ｒ６及びＲ７は、置換芳香族炭化水素基もしくは無置換芳香族炭化水素基であるか、又は、置換窒素含有芳香族複素環基もしくは無置換窒素含有芳香族複素環基である。 n in the above structural formula (2) is 0 or 1.
R6 and R7 are substituted aromatic hydrocarbon groups or unsubstituted aromatic hydrocarbon groups, or substituted nitrogen-containing aromatic heterocyclic groups or unsubstituted nitrogen-containing aromatic heterocyclic groups.
上記構造式（３）中のＲ８は、水素であるか、又は、置換芳香族炭化水素基もしくは無置換芳香族炭化水素基である。
R8 in the above structural formula (3) is hydrogen, a substituted aromatic hydrocarbon group, or an unsubstituted aromatic hydrocarbon group.
上記構造式（４）におけるＲ９及びＲ１０は水素である。代替的に、Ｒ９及びＲ１０は、置換もしくは無置換の芳香族炭化水素基であってもよい。
R9 and R10 in the above structural formula (4) are hydrogen. Alternatively, R9 and R10 may be substituted or unsubstituted aromatic hydrocarbon groups.
Ｒ２～Ｒ５の少なくともいずれか１つが１価の芳香族炭化水素基である場合、Ｌ１～Ｌ３の少なくともいずれか１個は、置換芳香族炭化水素もしくは無置換芳香族炭化水素であるか、又は、置換芳香族複素環基もしくは無置換芳香族複素環基である。
When at least one of R2 to R5 is a monovalent aromatic hydrocarbon group, at least one of L1 to L3 is a substituted aromatic hydrocarbon or an unsubstituted aromatic hydrocarbon, or It is a substituted aromatic heterocyclic group or an unsubstituted aromatic heterocyclic group.
本発明の別の一実施形態によれば、上記したジカルバゾリルベンゼン類化合物を含む層を備える有機エレクトロルミネッセンス素子が提供される。
According to another embodiment of the present invention, an organic electroluminescent device is provided that includes a layer containing the dicarbazolylbenzene compound described above.
なお、各化合物中の水素が重水素に置換されていてもよい。重水素化率は高くてもよく、例えば、８０％程度であってもよい。
Note that hydrogen in each compound may be replaced with deuterium. The deuteration rate may be high, for example, about 80%.
上記の化合物では、第一励起三重項状態（Ｔ１）のエネルギが高い。また、上記の化合物における最高占有準位（ＨＯＭＯ）及び最低非占有準位（ＬＵＭＯ）は、特に青色発光材料を発光層に含む場合の電荷輸送材として用いるに当たって、適切な範囲内である。また、この化合物においては、分子内で電荷が移動することが容易であるために電荷が非局在化し難い。従って、分子構造が安定する。さらに、分子の構造に基づいて分子内回転が抑制されるので、熱安定性が良好である。
In the above compounds, the energy of the first excited triplet state (T1) is high. Further, the highest occupied level (HOMO) and lowest unoccupied level (LUMO) of the above-mentioned compound are within appropriate ranges when used as a charge transport material, especially when a blue light emitting material is included in the light emitting layer. In addition, in this compound, the charge easily moves within the molecule, so that it is difficult for the charge to become delocalized. Therefore, the molecular structure is stabilized. Furthermore, since intramolecular rotation is suppressed based on the molecular structure, thermal stability is good.
以上のような理由から、上記の化合物を含む層を備える有機エレクトロルミネッセンス素子では、寿命が長期化する。
For the reasons mentioned above, an organic electroluminescent element including a layer containing the above compound has a longer lifespan.
図１は、有機エレクトロルミネッセンス（ＥＬ）素子１０の模式的側面図である。有機ＥＬ素子１０は、ガラス基板１２と、アノード１４と、正孔輸送層１６と、発光層１８と、電子輸送層２０と、カソード２２とを備える。ガラス基板１２、アノード１４及びカソード２２の素材としては、公知の素材を採用することができる。
FIG. 1 is a schematic side view of an organic electroluminescence (EL) element 10. The organic EL element 10 includes a glass substrate 12, an anode 14, a hole transport layer 16, a light emitting layer 18, an electron transport layer 20, and a cathode 22. As materials for the glass substrate 12, anode 14, and cathode 22, known materials can be used.
正孔輸送層１６、発光層１８又は電子輸送層２０の少なくとも１つは、ジカルバゾリルベンゼン類化合物を含む。本実施形態において、ジカルバゾリルベンゼン類化合物とは、２個のカルバゾリル基が互いに結合したジカルバゾリル基が１個以上結合したベンゼン環を基本骨格として含む化合物を指す。又は、ジカルバゾリルベンゼン類化合物とは、１個以上の置換ジカルバゾリル基が１個以上結合したベンゼン環を基本骨格として含む化合物を指す。本実施形態に係るジカルバゾリルベンゼン類化合物の構造式を、以下の構造式（１）に示す。
At least one of the hole transport layer 16, the light emitting layer 18, or the electron transport layer 20 contains a dicarbazolylbenzene compound. In the present embodiment, the dicarbazolylbenzene compound refers to a compound containing as a basic skeleton a benzene ring to which one or more dicarbazolyl groups are bonded, each having two carbazolyl groups bonded to each other. Alternatively, a dicarbazolylbenzene compound refers to a compound containing as a basic skeleton a benzene ring to which one or more substituted dicarbazolyl groups are bonded. The structural formula of the dicarbazolylbenzene compound according to this embodiment is shown in the following structural formula (1).
上記構造式（１）中のＲ２～Ｒ５は、水素か、又は、カルバゾリル基を構成するベンゼン環の任意の位置に結合した置換基を表す。また、上記構造式（１）中のＬ１～Ｌ３の少なくともいずれか１個は、下記の構造式（２）、構造式（３）又は構造式（４）に示される官能基である。
R2 to R5 in the above structural formula (1) represent hydrogen or a substituent bonded to any position of the benzene ring constituting the carbazolyl group. Furthermore, at least one of L1 to L3 in the above structural formula (1) is a functional group represented by the following structural formula (2), structural formula (3), or structural formula (4).
上記構造式（２）中のｎは、０又は１である。ｎ＝０であるとき、構造式（１）は以下の構造式に変形される。この場合、構造式（１）中のベンゼン環に対してＮが結合する。
n in the above structural formula (2) is 0 or 1. When n=0, structural formula (1) is transformed into the following structural formula. In this case, N is bonded to the benzene ring in structural formula (1).
これに対し、ｎ＝１であるとき、構造式（１）中のベンゼン環に対し、フェニル基を介してＮが結合する。
On the other hand, when n=1, N is bonded to the benzene ring in structural formula (1) via a phenyl group.
構造式（２）における６及びＲ７は、置換もしくは無置換の芳香族炭化水素基を表す。代替的に、Ｒ６及びＲ７は、置換もしくは無置換の窒素含有芳香族複素環基であってもよい。窒素含有芳香族複素環基の代表例としては、窒素含有５員環基、窒素含有６員環基、窒素含有芳香族縮合２環又は窒素含有芳香族縮合３環等が挙げられる。窒素含有５員環基の具体例としてはピロリル基等が挙げられ、窒素含有６員環基の具体例としてはピリジニル基又はピリミジル基等が挙げられる。窒素含有芳香族縮合２環の具体例としてはインドリル基又はキノリル基等が挙げられ、窒素含有芳香族縮合３環の具体例としては、カルバゾリル基又はフェナントロリル基等が挙げられる。窒素含有芳香族複素環基は、上記した置換基に特に限定されない。
6 and R7 in structural formula (2) represent a substituted or unsubstituted aromatic hydrocarbon group. Alternatively, R6 and R7 may be substituted or unsubstituted nitrogen-containing aromatic heterocyclic groups. Representative examples of the nitrogen-containing aromatic heterocyclic group include a nitrogen-containing 5-membered ring group, a nitrogen-containing 6-membered ring group, a nitrogen-containing aromatic condensed two-ring group, and a nitrogen-containing aromatic condensed three-ring group. Specific examples of the nitrogen-containing 5-membered cyclic group include a pyrrolyl group, and specific examples of the nitrogen-containing 6-membered cyclic group include a pyridinyl group or a pyrimidyl group. Specific examples of the nitrogen-containing aromatic condensed two rings include an indolyl group and a quinolyl group, and specific examples of the nitrogen-containing aromatic condensed three rings include a carbazolyl group and a phenanthrolyl group. The nitrogen-containing aromatic heterocyclic group is not particularly limited to the above-mentioned substituents.
構造式（３）におけるＲ８は、置換もしくは無置換の芳香族炭化水素基を表す。代替的に、Ｒ８は、置換もしくは無置換の窒素含有芳香族複素環基であってもよい。
R8 in Structural Formula (3) represents a substituted or unsubstituted aromatic hydrocarbon group. Alternatively, R8 may be a substituted or unsubstituted nitrogen-containing aromatic heterocyclic group.
構造式（４）におけるＲ９及びＲ１０は水素である。代替的に、Ｒ９及びＲ１０は、置換もしくは無置換の芳香族炭化水素基であってもよい。
R9 and R10 in structural formula (4) are hydrogen. Alternatively, R9 and R10 may be substituted or unsubstituted aromatic hydrocarbon groups.
Ｒ２～Ｒ５の全てが水素であってもよい。以下、この場合におけるＬ１～Ｌ３の具体例を示す。
All of R2 to R5 may be hydrogen. Specific examples of L1 to L3 in this case will be shown below.
［１．Ｌ２＝Ｌ３＝ＨであるときのＬ１の例］
[1. Example of L1 when L2=L3=H]
［２．Ｌ２＝ＨであるときのＬ１、Ｌ３の例］
[2. Example of L1 and L3 when L2=H]
［３．Ｌ１＝Ｌ３＝ＨであるときのＬ２の例］
[3. Example of L2 when L1=L3=H]
なお、Ｍｅはメチル基を表す。
Note that Me represents a methyl group.
ジカルバゾリルベンゼン類化合物は、２個のジカルバゾリル基又は２個の置換ジカルバゾリル基がベンゼン環に結合した化合物であってもよい。さらに、ベンゼン環に結合するＬ１～Ｌ３のいずれかが、カルバゾリル基もしくは置換カルバゾリル基であることが好ましい。この化合物の構造式を以下に例示する。なお、この構造式では、ベンゼン環に対し、２個のジカルバゾリル基と、１個のカルバゾリル基とが結合した化合物を例示している。すなわち、この化合物において、ジカルバゾリル基及びカルバゾリル基に含まれる水素は、置換基に置換されていない。
The dicarbazolylbenzene compound may be a compound in which two dicarbazolyl groups or two substituted dicarbazolyl groups are bonded to a benzene ring. Furthermore, any one of L1 to L3 bonded to the benzene ring is preferably a carbazolyl group or a substituted carbazolyl group. The structural formula of this compound is illustrated below. Note that this structural formula exemplifies a compound in which two dicarbazolyl groups and one carbazolyl group are bonded to a benzene ring. That is, in this compound, hydrogen contained in the dicarbazolyl group and the carbazolyl group is not substituted with a substituent.
ジカルバゾリルベンゼン類化合物は、ベンゼン環に対し、２個のジカルバゾリル基、２個の置換ジカルバゾリル基、又は１個のジカルバゾリル基と１個の置換ジカルバゾリル基とが結合した化合物であってもよい。２個のジカルバゾリル基、２個の置換ジカルバゾリル基、又は１個のジカルバゾリル基と１個の置換ジカルバゾリル基とは、ベンゼン環においてオルト位（ｏ－位）の位置関係であることが好ましい。
The dicarbazolylbenzene compound may be a compound in which two dicarbazolyl groups, two substituted dicarbazolyl groups, or one dicarbazolyl group and one substituted dicarbazolyl group are bonded to a benzene ring. . Two dicarbazolyl groups, two substituted dicarbazolyl groups, or one dicarbazolyl group and one substituted dicarbazolyl group are preferably at the ortho position (o-position) in the benzene ring.
この化合物の構造式を以下に例示する。なお、この構造式では、ベンゼン環に対し、２個のジカルバゾリル基が結合した化合物を例示している。すなわち、この化合物において、ジカルバゾリル基に含まれる水素は官能基に置換されていない。また、２個のジカルバゾリル基は、ベンゼン環においてｏ－位となる位置関係である。
The structural formula of this compound is illustrated below. Note that this structural formula exemplifies a compound in which two dicarbazolyl groups are bonded to a benzene ring. That is, in this compound, hydrogen contained in the dicarbazolyl group is not substituted with a functional group. Further, the two dicarbazolyl groups are positioned at the o-position in the benzene ring.
ジカルバゾリルベンゼン類化合物は、２個のジカルバゾリルベンゼンが互いに結合した化合物であってもよい。ここで、１個のジカルバゾリルベンゼンは、ジカルバゾリル基又は置換ジカルバゾリル基がベンゼン環に結合した化合物である。従って、この場合のジカルバゾリルベンゼン類化合物は、ジカルバゾリルベンゼンに対し、フェニル基を含む官能基が結合した形態となる。フェニル基を含む官能基とは、ジカルバゾリル基又は置換ジカルバゾリル基がフェニル基に結合した官能基を指す。ジカルバゾリルベンゼンにおけるジカルバゾリル基又は置換ジカルバゾリル基と、フェニル基を含む官能基とは、ベンゼン環においてｏ－位の位置関係であることが好ましい。
The dicarbazolylbenzene compound may be a compound in which two dicarbazolylbenzenes are bonded to each other. Here, one dicarbazolylbenzene is a compound in which a dicarbazolyl group or a substituted dicarbazolyl group is bonded to a benzene ring. Therefore, the dicarbazolylbenzene compound in this case has a form in which a functional group containing a phenyl group is bonded to dicarbazolylbenzene. A functional group containing a phenyl group refers to a functional group in which a dicarbazolyl group or a substituted dicarbazolyl group is bonded to a phenyl group. The dicarbazolyl group or substituted dicarbazolyl group in dicarbazolylbenzene and the functional group containing a phenyl group are preferably o-positioned in the benzene ring.
この化合物の構造式を以下に例示する。なお、この構造式では、２個のジカルバゾリルベンゼンが互いに結合した化合物を例示している。すなわち、この化合物において、ジカルバゾリル基に含まれる水素は官能基に置換されていない。また、ジカルバゾリル基と、フェニル基を含む官能基とは、ベンゼン環においてｏ－位となる位置関係である。
The structural formula of this compound is illustrated below. Note that this structural formula exemplifies a compound in which two dicarbazolylbenzenes are bonded to each other. That is, in this compound, hydrogen contained in the dicarbazolyl group is not substituted with a functional group. Furthermore, the dicarbazolyl group and the functional group containing the phenyl group are in a positional relationship such that they are at the o-position in the benzene ring.
代替的に、Ｒ２～Ｒ５は１価の芳香族炭化水素基であってもよい。この場合、Ｌ１～Ｌ３の少なくともいずれか１個は、１価の置換芳香族炭化水素基もしくは１価の無置換芳香族炭化水素基である。Ｌ１～Ｌ３の少なくともいずれか１個は、１価の置換芳香族複素環基もしくは１価の無置換芳香族複素環基であってもよい。
Alternatively, R2 to R5 may be monovalent aromatic hydrocarbon groups. In this case, at least one of L1 to L3 is a monovalent substituted aromatic hydrocarbon group or a monovalent unsubstituted aromatic hydrocarbon group. At least one of L1 to L3 may be a monovalent substituted aromatic heterocyclic group or a monovalent unsubstituted aromatic heterocyclic group.
以上のような構造を有するジカルバゾリルベンゼン類化合物を素材として含む正孔輸送層１６、発光層１８又は電子輸送層２０を形成した場合、該層を有する有機ＥＬ素子１０では、従来技術に係る有機ＥＬ素子よりも寿命が長期化することが認められる。
When the hole transport layer 16, the light emitting layer 18, or the electron transport layer 20 containing the dicarbazolylbenzene compound having the above structure as a material is formed, the organic EL element 10 having the layer is different from the conventional technology. It is recognized that the lifespan is longer than that of such organic EL elements.
このように寿命が長期化する理由は、以下のようであると考えられる。第１に、これらの化合物では、第一励起三重項状態（Ｔ１）のエネルギが高く、且つ最高占有準位（ＨＯＭＯ）及び最低非占有準位（ＬＵＭＯ）が適切である。第２に、構造式によれば、分子内で電荷が移動することが容易であり、電荷が非局在化し難いために分子構造が安定する。第３に、分子の構造に基づいて分子内回転が抑制されるので、熱安定性が良好となりホストとして適切である。
The reason why the lifespan becomes longer in this way is thought to be as follows. First, in these compounds, the energy of the first excited triplet state (T1) is high, and the highest occupied level (HOMO) and lowest unoccupied level (LUMO) are appropriate. Second, according to the structural formula, it is easy for charges to move within the molecule, and the charges are difficult to delocalize, so the molecular structure is stabilized. Thirdly, since intramolecular rotation is suppressed based on the molecular structure, it has good thermal stability and is suitable as a host.
さらに、上記した複数個の官能基がベンゼン環においてｏ－位の位置関係となるとき、分子が立体的に捻れた構造となる。このためにπ共役の延びが限定される。その結果として、エネルギにワイドギャップが生じ易くなる。このような化合物は、青色発光用の素材として一層適切であると考えられる。
Furthermore, when the plurality of functional groups described above are positioned at the o-position on the benzene ring, the molecule forms a sterically twisted structure. This limits the extent of the π conjugate. As a result, wide gaps in energy tend to occur. Such a compound is considered to be more suitable as a material for blue light emission.
なお、本発明は、上述した実施形態に限らず、本発明の要旨を逸脱することなく、種々の構成を取り得る。
Note that the present invention is not limited to the embodiments described above, and can take various configurations without departing from the gist of the present invention.
例えば、上記した有機化合物中の水素が重水素に置換されていてもよい。重水素化率は高くてもよく、例えば、８０％程度であってもよい。
For example, hydrogen in the organic compound described above may be replaced with deuterium. The deuteration rate may be high, for example, about 80%.
また、ジカルバゾリルベンゼン類化合物は、置換芳香族炭化水素基又は置換芳香族複素環基が結合することにより、様々な構造となり得る。
Further, dicarbazolylbenzene compounds can have various structures by bonding substituted aromatic hydrocarbon groups or substituted aromatic heterocyclic groups.
［化合物の合成］
以下におけるＡｃ、Ｂｕ、Ｅｔ及びＡｒは、それぞれ、アセチル基、ブチル基、エチル基及びアリール基を表す。また、ｔ－Ｂｕは三級ブチル基を意味する。さらに、Ｈ、Ｃ及びＮの「％」は質量％である。 [Synthesis of compounds]
Ac, Bu, Et and Ar in the following represent an acetyl group, a butyl group, an ethyl group and an aryl group, respectively. Further, t-Bu means a tertiary butyl group. Furthermore, "%" of H, C and N is mass %.
以下におけるＡｃ、Ｂｕ、Ｅｔ及びＡｒは、それぞれ、アセチル基、ブチル基、エチル基及びアリール基を表す。また、ｔ－Ｂｕは三級ブチル基を意味する。さらに、Ｈ、Ｃ及びＮの「％」は質量％である。 [Synthesis of compounds]
Ac, Bu, Et and Ar in the following represent an acetyl group, a butyl group, an ethyl group and an aryl group, respectively. Further, t-Bu means a tertiary butyl group. Furthermore, "%" of H, C and N is mass %.
［実施例１］
５ミリリットルのメシチレンに対し、２ミリモルのジカルバゾールと、２ミリモルの９－（３－ブロモフェニル）－９Ｈ－カルバゾールと、０．０４ミリモルのＰｄ（ＯＡｃ）2と、０．１６ミリモルのｔ－Ｂｕ3Ｐと、３ミリモルのＮａＯ（ｔ－Ｂｕ）とを添加し、混合液を調製した。該混合液を、アルゴン雰囲気下で１５０℃に保持した状態で、４時間撹拌した。混合液に１モル／リットルのＨＣｌを３ミリリットル添加してクエンチを行い、ＥｔＯＡｃを用いて混合液から有機物を抽出した。飽和食塩水で有機物を洗浄した後、該有機物をＭｇＳＯ4で乾燥した。溶媒を減圧下で除去して、粗生成物を得た。 [Example 1]
For 5 ml of mesitylene, 2 mmol of dicarbazole, 2 mmol of 9-(3-bromophenyl)-9H-carbazole, 0.04 mmol of Pd(OAc) 2 and 0.16 mmol of t- Bu 3 P and 3 mmol of NaO(t-Bu) were added to prepare a mixed solution. The mixture was stirred for 4 hours while being maintained at 150° C. under an argon atmosphere. The mixture was quenched by adding 3 milliliters of 1 mol/liter HCl, and the organic matter was extracted from the mixture using EtOAc. After washing the organic matter with saturated brine, the organic matter was dried with MgSO 4 . The solvent was removed under reduced pressure to obtain the crude product.
５ミリリットルのメシチレンに対し、２ミリモルのジカルバゾールと、２ミリモルの９－（３－ブロモフェニル）－９Ｈ－カルバゾールと、０．０４ミリモルのＰｄ（ＯＡｃ）2と、０．１６ミリモルのｔ－Ｂｕ3Ｐと、３ミリモルのＮａＯ（ｔ－Ｂｕ）とを添加し、混合液を調製した。該混合液を、アルゴン雰囲気下で１５０℃に保持した状態で、４時間撹拌した。混合液に１モル／リットルのＨＣｌを３ミリリットル添加してクエンチを行い、ＥｔＯＡｃを用いて混合液から有機物を抽出した。飽和食塩水で有機物を洗浄した後、該有機物をＭｇＳＯ4で乾燥した。溶媒を減圧下で除去して、粗生成物を得た。 [Example 1]
For 5 ml of mesitylene, 2 mmol of dicarbazole, 2 mmol of 9-(3-bromophenyl)-9H-carbazole, 0.04 mmol of Pd(OAc) 2 and 0.16 mmol of t- Bu 3 P and 3 mmol of NaO(t-Bu) were added to prepare a mixed solution. The mixture was stirred for 4 hours while being maintained at 150° C. under an argon atmosphere. The mixture was quenched by adding 3 milliliters of 1 mol/liter HCl, and the organic matter was extracted from the mixture using EtOAc. After washing the organic matter with saturated brine, the organic matter was dried with MgSO 4 . The solvent was removed under reduced pressure to obtain the crude product.
酢酸エチルを展開溶媒として粗生成物をフロリジルに通し、さらに、溶媒を減圧下で除去した２－プロパノールを用いた再結晶により、白茶色の有機物を得た。収量は１．１３ｇであり、収率は９８％であった。
The crude product was passed through Florisil using ethyl acetate as a developing solvent, and then the solvent was removed under reduced pressure and recrystallized using 2-propanol to obtain a whitish-brown organic substance. The yield was 1.13 g, and the yield was 98%.
得られた有機物につき、有機微量元素分析装置を用いて分析を行った。分子中のＣ、Ｈ及びＮは、それぞれ８７．８２％、５．０７％及び約６．９３％であった。また、核磁気共鳴（ＮＭＲ）による分析結果は、下記のとおりであった。
1ＨＮＭＲ（ＤＭＳＯ－ｄ６，３９２ＭＨｚ）；δ＝６．６４－６．７１（ｍ，３Ｈ）、６．８０－６．９２（ｍ，４Ｈ）、７．００－７．０３（ｍ，２Ｈ）、７．１３－７．２５（ｍ，５Ｈ）、７．３３－７．５２（ｍ，７Ｈ）、７．５９（ｄ，Ｊ＝７．６Ｈｚ，１Ｈ）、８．０３（ｄ，Ｊ＝７．６Ｈｚ，１Ｈ）、８．１２（ｄ，Ｊ＝７．６Ｈｚ，２Ｈ）、８．３７（ｄ，Ｊ＝７．６Ｈｚ，１Ｈ）、８．５（ｄ，Ｊ＝７．６Ｈｚ，１Ｈ）。 The obtained organic matter was analyzed using an organic trace element analyzer. C, H and N in the molecule were 87.82%, 5.07% and about 6.93%, respectively. Further, the analysis results by nuclear magnetic resonance (NMR) were as follows.
1 HNMR (DMSO-d6, 392MHz); δ = 6.64-6.71 (m, 3H), 6.80-6.92 (m, 4H), 7.00-7.03 (m, 2H) , 7.13-7.25 (m, 5H), 7.33-7.52 (m, 7H), 7.59 (d, J = 7.6Hz, 1H), 8.03 (d, J = 7.6Hz, 1H), 8.12 (d, J = 7.6Hz, 2H), 8.37 (d, J = 7.6Hz, 1H), 8.5 (d, J = 7.6Hz, 1H) ).
1ＨＮＭＲ（ＤＭＳＯ－ｄ６，３９２ＭＨｚ）；δ＝６．６４－６．７１（ｍ，３Ｈ）、６．８０－６．９２（ｍ，４Ｈ）、７．００－７．０３（ｍ，２Ｈ）、７．１３－７．２５（ｍ，５Ｈ）、７．３３－７．５２（ｍ，７Ｈ）、７．５９（ｄ，Ｊ＝７．６Ｈｚ，１Ｈ）、８．０３（ｄ，Ｊ＝７．６Ｈｚ，１Ｈ）、８．１２（ｄ，Ｊ＝７．６Ｈｚ，２Ｈ）、８．３７（ｄ，Ｊ＝７．６Ｈｚ，１Ｈ）、８．５（ｄ，Ｊ＝７．６Ｈｚ，１Ｈ）。 The obtained organic matter was analyzed using an organic trace element analyzer. C, H and N in the molecule were 87.82%, 5.07% and about 6.93%, respectively. Further, the analysis results by nuclear magnetic resonance (NMR) were as follows.
1 HNMR (DMSO-d6, 392MHz); δ = 6.64-6.71 (m, 3H), 6.80-6.92 (m, 4H), 7.00-7.03 (m, 2H) , 7.13-7.25 (m, 5H), 7.33-7.52 (m, 7H), 7.59 (d, J = 7.6Hz, 1H), 8.03 (d, J = 7.6Hz, 1H), 8.12 (d, J = 7.6Hz, 2H), 8.37 (d, J = 7.6Hz, 1H), 8.5 (d, J = 7.6Hz, 1H) ).
以上の結果から、得られた有機物の示性式はＣ42Ｈ27Ｎ3であり、分子量は５７３．７であると判断された。
From the above results, it was determined that the specific formula of the obtained organic substance was C 42 H 27 N 3 and the molecular weight was 573.7.
この場合の化学反応式を、下記に示す。
The chemical reaction formula in this case is shown below.
以下、生成物である有機物をＤＣＺ－１という。
Hereinafter, the organic substance that is the product will be referred to as DCZ-1.
［実施例２］
２．７ミリリットルのメシチレンに対し、０．３３ｇのジカルバゾールと、０．４９ｇのＡｒ－Ｂｒ（臭化アリール）と、４．５ｍｇのＰｄ（ＯＡｃ）2と、１６．２ｍｇのｔ－Ｂｕ3Ｐと、０．１４４ｇのＮａＯ（ｔ－Ｂｕ）とを添加し、混合液を調製した。該混合液を１５０℃に保持し、アルゴン雰囲気下で撹拌した。なお、用いた臭化アリールは９，９’－（５－ブロモ－１，３－フェニレン）ビス（９Ｈ－カルバゾール）であり、その構造式は以下のとおりである。 [Example 2]
For 2.7 ml of mesitylene, 0.33 g of dicarbazole, 0.49 g of Ar-Br (aryl bromide), 4.5 mg of Pd(OAc) 2 and 16.2 mg of t-Bu 3 P and 0.144 g of NaO(t-Bu) were added to prepare a mixed solution. The mixture was maintained at 150°C and stirred under an argon atmosphere. The aryl bromide used was 9,9'-(5-bromo-1,3-phenylene)bis(9H-carbazole), and its structural formula is as follows.
２．７ミリリットルのメシチレンに対し、０．３３ｇのジカルバゾールと、０．４９ｇのＡｒ－Ｂｒ（臭化アリール）と、４．５ｍｇのＰｄ（ＯＡｃ）2と、１６．２ｍｇのｔ－Ｂｕ3Ｐと、０．１４４ｇのＮａＯ（ｔ－Ｂｕ）とを添加し、混合液を調製した。該混合液を１５０℃に保持し、アルゴン雰囲気下で撹拌した。なお、用いた臭化アリールは９，９’－（５－ブロモ－１，３－フェニレン）ビス（９Ｈ－カルバゾール）であり、その構造式は以下のとおりである。 [Example 2]
For 2.7 ml of mesitylene, 0.33 g of dicarbazole, 0.49 g of Ar-Br (aryl bromide), 4.5 mg of Pd(OAc) 2 and 16.2 mg of t-Bu 3 P and 0.144 g of NaO(t-Bu) were added to prepare a mixed solution. The mixture was maintained at 150°C and stirred under an argon atmosphere. The aryl bromide used was 9,9'-(5-bromo-1,3-phenylene)bis(9H-carbazole), and its structural formula is as follows.
混合液に１モル／リットルのＨＣｌを１．５ミリリットル添加してクエンチを行い、ＥｔＯＡｃを用いて混合液から有機物を抽出した。飽和食塩水で有機物を洗浄した後、該有機物をＭｇＳＯ4で乾燥した。溶媒を減圧下で除去して、粗生成物を得た。次に、酢酸エチルを展開溶媒として粗生成物につきシリカゲルカラム精製を行った。得られた精製物をエタノールで再沈殿させ、白色固体の有機物を得た。収量は０．６６ｇであり、収率は８９％であった。純水及び飽和食塩水で有機物を洗浄した後、該有機物をＭｇＳＯ4で乾燥した。
The mixture was quenched by adding 1.5 milliliters of 1 mol/liter HCl, and the organic matter was extracted from the mixture using EtOAc. After washing the organic matter with saturated brine, the organic matter was dried with MgSO 4 . The solvent was removed under reduced pressure to obtain the crude product. Next, the crude product was purified by silica gel column using ethyl acetate as a developing solvent. The obtained purified product was reprecipitated with ethanol to obtain a white solid organic substance. The yield was 0.66 g, and the yield was 89%. After washing the organic matter with pure water and saturated brine, the organic matter was dried with MgSO 4 .
以降は実施例１と同様にして、得られた有機物につき分析を行った。分子中のＣ、Ｈ及びＮは、それぞれ、８７．６３％、４．６０％及び７．５１％であった。また、ＮＭＲによる分析結果は下記のとおりである。
1ＨＮＭＲ（ＤＭＳＯ－ｄ６，３９２ＭＨｚ）；δ＝６．６７－６．７０（ｍ，２Ｈ）、６．８３－６．８８（ｍ，４Ｈ）、７．１１－７．１３（ｍ，４Ｈ）、７．２２－７．２３（ｍ，２Ｈ）、７．２５－７．３３（ｍ，５Ｈ）、７．３９－７．６０（ｍ，１１Ｈ）、８．１７－８．１９（ｍ，４Ｈ）、８．４４－８．４６（ｍ，１Ｈ）、８．５５－８．５７（ｍ，１Ｈ）。
以上の結果から、得られた有機物の示性式はＣ54Ｈ34Ｎ4であり、分子量は７３８．８９であると判断された。この場合の有機物の構造式を、下記に示す。 Thereafter, the obtained organic substances were analyzed in the same manner as in Example 1. C, H and N in the molecule were 87.63%, 4.60% and 7.51%, respectively. Further, the results of NMR analysis are as follows.
1 HNMR (DMSO-d6, 392MHz); δ = 6.67-6.70 (m, 2H), 6.83-6.88 (m, 4H), 7.11-7.13 (m, 4H) , 7.22-7.23 (m, 2H), 7.25-7.33 (m, 5H), 7.39-7.60 (m, 11H), 8.17-8.19 (m, 4H), 8.44-8.46 (m, 1H), 8.55-8.57 (m, 1H).
From the above results, it was determined that the formula of the obtained organic substance was C 54 H 34 N 4 and the molecular weight was 738.89. The structural formula of the organic substance in this case is shown below.
1ＨＮＭＲ（ＤＭＳＯ－ｄ６，３９２ＭＨｚ）；δ＝６．６７－６．７０（ｍ，２Ｈ）、６．８３－６．８８（ｍ，４Ｈ）、７．１１－７．１３（ｍ，４Ｈ）、７．２２－７．２３（ｍ，２Ｈ）、７．２５－７．３３（ｍ，５Ｈ）、７．３９－７．６０（ｍ，１１Ｈ）、８．１７－８．１９（ｍ，４Ｈ）、８．４４－８．４６（ｍ，１Ｈ）、８．５５－８．５７（ｍ，１Ｈ）。
以上の結果から、得られた有機物の示性式はＣ54Ｈ34Ｎ4であり、分子量は７３８．８９であると判断された。この場合の有機物の構造式を、下記に示す。 Thereafter, the obtained organic substances were analyzed in the same manner as in Example 1. C, H and N in the molecule were 87.63%, 4.60% and 7.51%, respectively. Further, the results of NMR analysis are as follows.
1 HNMR (DMSO-d6, 392MHz); δ = 6.67-6.70 (m, 2H), 6.83-6.88 (m, 4H), 7.11-7.13 (m, 4H) , 7.22-7.23 (m, 2H), 7.25-7.33 (m, 5H), 7.39-7.60 (m, 11H), 8.17-8.19 (m, 4H), 8.44-8.46 (m, 1H), 8.55-8.57 (m, 1H).
From the above results, it was determined that the formula of the obtained organic substance was C 54 H 34 N 4 and the molecular weight was 738.89. The structural formula of the organic substance in this case is shown below.
以下、この有機物をＤＣＺ－２という。
Hereinafter, this organic substance will be referred to as DCZ-2.
［実施例３］
構造式が下記に示される９－（３－ブロモフェニル）－３，６－ジフェニル－９Ｈ－カルバゾールを０．４７ｇ用い、ヘキサンとＥｔＯＡｃを展開溶媒とした以外は実施例２と同様にして、白色固体の有機物を得た。収量は０．３３ｇであり、収率は７５％であった。 [Example 3]
A white color was prepared in the same manner as in Example 2 except that 0.47 g of 9-(3-bromophenyl)-3,6-diphenyl-9H-carbazole whose structural formula is shown below was used and hexane and EtOAc were used as the developing solvents. A solid organic material was obtained. The yield was 0.33 g, and the yield was 75%.
構造式が下記に示される９－（３－ブロモフェニル）－３，６－ジフェニル－９Ｈ－カルバゾールを０．４７ｇ用い、ヘキサンとＥｔＯＡｃを展開溶媒とした以外は実施例２と同様にして、白色固体の有機物を得た。収量は０．３３ｇであり、収率は７５％であった。 [Example 3]
A white color was prepared in the same manner as in Example 2 except that 0.47 g of 9-(3-bromophenyl)-3,6-diphenyl-9H-carbazole whose structural formula is shown below was used and hexane and EtOAc were used as the developing solvents. A solid organic material was obtained. The yield was 0.33 g, and the yield was 75%.
有機微量元素分析装置による分子中のＣ、Ｈ及びＮは、それぞれ、８９．２０％、４．９１％及び５．７２％であった。また、ＮＭＲによる分析結果は下記のとおりである。
1ＨＮＭＲ（ＤＭＳＯ－ｄ６，３９２ＭＨｚ）；δ＝６．７０－７．３２（ｍ，１２Ｈ）、７．３９－７．４５（ｍ，４Ｈ）、７．４９－７．５６（ｍ，７Ｈ）、７．７０－７．７３（ｍ，１Ｈ）、７．８０－７．８６（ｍ，６Ｈ）、８．１２－８．１５（ｍ，１Ｈ）、８．４２－８．４４（ｍ，１Ｈ），８．５４－８．５６（ｍ，１Ｈ）、８．６５－８．６６（ｍ，２Ｈ）。
以上の結果から、得られた有機物の示性式はＣ54Ｈ35Ｎ3であり、分子量は７２５．９であると判断された。この場合の有機物の構造式を、下記に示す。 C, H, and N in the molecule determined by an organic trace element analyzer were 89.20%, 4.91%, and 5.72%, respectively. Further, the results of NMR analysis are as follows.
1 HNMR (DMSO-d6, 392MHz); δ = 6.70-7.32 (m, 12H), 7.39-7.45 (m, 4H), 7.49-7.56 (m, 7H) , 7.70-7.73 (m, 1H), 7.80-7.86 (m, 6H), 8.12-8.15 (m, 1H), 8.42-8.44 (m, 1H), 8.54-8.56 (m, 1H), 8.65-8.66 (m, 2H).
From the above results, it was determined that the specific formula of the obtained organic substance was C 54 H 35 N 3 and the molecular weight was 725.9. The structural formula of the organic substance in this case is shown below.
1ＨＮＭＲ（ＤＭＳＯ－ｄ６，３９２ＭＨｚ）；δ＝６．７０－７．３２（ｍ，１２Ｈ）、７．３９－７．４５（ｍ，４Ｈ）、７．４９－７．５６（ｍ，７Ｈ）、７．７０－７．７３（ｍ，１Ｈ）、７．８０－７．８６（ｍ，６Ｈ）、８．１２－８．１５（ｍ，１Ｈ）、８．４２－８．４４（ｍ，１Ｈ），８．５４－８．５６（ｍ，１Ｈ）、８．６５－８．６６（ｍ，２Ｈ）。
以上の結果から、得られた有機物の示性式はＣ54Ｈ35Ｎ3であり、分子量は７２５．９であると判断された。この場合の有機物の構造式を、下記に示す。 C, H, and N in the molecule determined by an organic trace element analyzer were 89.20%, 4.91%, and 5.72%, respectively. Further, the results of NMR analysis are as follows.
1 HNMR (DMSO-d6, 392MHz); δ = 6.70-7.32 (m, 12H), 7.39-7.45 (m, 4H), 7.49-7.56 (m, 7H) , 7.70-7.73 (m, 1H), 7.80-7.86 (m, 6H), 8.12-8.15 (m, 1H), 8.42-8.44 (m, 1H), 8.54-8.56 (m, 1H), 8.65-8.66 (m, 2H).
From the above results, it was determined that the specific formula of the obtained organic substance was C 54 H 35 N 3 and the molecular weight was 725.9. The structural formula of the organic substance in this case is shown below.
以下、この有機物をＤＣＺ－３という。
Hereinafter, this organic substance will be referred to as DCZ-3.
［実施例４］
１，３－ジブロモベンゼンを０．６６ｇ用いた以外は実施例３と同様にして、白色固体の有機物を得た。なお、ジカルバゾール、Ｐｄ（ＯＡｃ）2、ｔ－Ｂｕ3Ｐ及びＮａＯ（ｔ－Ｂｕ）は、それぞれ、０．６６ｇ、９ｍｇ、３２．４ｍｇ及び０．２９ｇとし、メシチレンは４ミリリットルとした。また、抽出にはクロロホルムを用いた。展開溶媒もクロロホルムを用いた。収量は０．４４ｇであり、収率は５９％であった。 [Example 4]
A white solid organic substance was obtained in the same manner as in Example 3 except that 0.66 g of 1,3-dibromobenzene was used. Note that dicarbazole, Pd(OAc) 2 , t-Bu 3 P, and NaO(t-Bu) were 0.66 g, 9 mg, 32.4 mg, and 0.29 g, respectively, and mesitylene was 4 ml. In addition, chloroform was used for extraction. Chloroform was also used as the developing solvent. The yield was 0.44 g, and the yield was 59%.
１，３－ジブロモベンゼンを０．６６ｇ用いた以外は実施例３と同様にして、白色固体の有機物を得た。なお、ジカルバゾール、Ｐｄ（ＯＡｃ）2、ｔ－Ｂｕ3Ｐ及びＮａＯ（ｔ－Ｂｕ）は、それぞれ、０．６６ｇ、９ｍｇ、３２．４ｍｇ及び０．２９ｇとし、メシチレンは４ミリリットルとした。また、抽出にはクロロホルムを用いた。展開溶媒もクロロホルムを用いた。収量は０．４４ｇであり、収率は５９％であった。 [Example 4]
A white solid organic substance was obtained in the same manner as in Example 3 except that 0.66 g of 1,3-dibromobenzene was used. Note that dicarbazole, Pd(OAc) 2 , t-Bu 3 P, and NaO(t-Bu) were 0.66 g, 9 mg, 32.4 mg, and 0.29 g, respectively, and mesitylene was 4 ml. In addition, chloroform was used for extraction. Chloroform was also used as the developing solvent. The yield was 0.44 g, and the yield was 59%.
有機微量元素分析装置による分子中のＣ、Ｈ及びＮは、それぞれ、８７．７３％、４．７６％及び７．５８％であった。また、ＮＭＲによる分析結果は下記のとおりである。
1ＨＮＭＲ（ＣＤＣｌ3，３９２ＭＨｚ）；δ＝５．８６－５．８７（ｍ，１Ｈ）、６．３４－６．３８（ｍ，３Ｈ）、６．５０－６．６２（ｍ，６Ｈ）、６．７４－６．７８（ｍ，４Ｈ）、６．９０－７．００（ｍ，６Ｈ）、７．１９－７．３２（ｍ，４Ｈ）、７．４８－７．６０（ｍ，６Ｈ），８．１８－８．２２（ｍ，４Ｈ）。
以上の結果から、得られた有機物の示性式はＣ54Ｈ34Ｎ4であり、分子量は７３８．８９であると判断された。この場合の有機物の構造式を、下記に示す。 C, H, and N in the molecule determined by an organic trace element analyzer were 87.73%, 4.76%, and 7.58%, respectively. Further, the results of NMR analysis are as follows.
1 HNMR (CDCl 3 , 392 MHz); δ = 5.86-5.87 (m, 1H), 6.34-6.38 (m, 3H), 6.50-6.62 (m, 6H), 6.74-6.78 (m, 4H), 6.90-7.00 (m, 6H), 7.19-7.32 (m, 4H), 7.48-7.60 (m, 6H) ), 8.18-8.22 (m, 4H).
From the above results, it was determined that the formula of the obtained organic substance was C 54 H 34 N 4 and the molecular weight was 738.89. The structural formula of the organic substance in this case is shown below.
1ＨＮＭＲ（ＣＤＣｌ3，３９２ＭＨｚ）；δ＝５．８６－５．８７（ｍ，１Ｈ）、６．３４－６．３８（ｍ，３Ｈ）、６．５０－６．６２（ｍ，６Ｈ）、６．７４－６．７８（ｍ，４Ｈ）、６．９０－７．００（ｍ，６Ｈ）、７．１９－７．３２（ｍ，４Ｈ）、７．４８－７．６０（ｍ，６Ｈ），８．１８－８．２２（ｍ，４Ｈ）。
以上の結果から、得られた有機物の示性式はＣ54Ｈ34Ｎ4であり、分子量は７３８．８９であると判断された。この場合の有機物の構造式を、下記に示す。 C, H, and N in the molecule determined by an organic trace element analyzer were 87.73%, 4.76%, and 7.58%, respectively. Further, the results of NMR analysis are as follows.
1 HNMR (CDCl 3 , 392 MHz); δ = 5.86-5.87 (m, 1H), 6.34-6.38 (m, 3H), 6.50-6.62 (m, 6H), 6.74-6.78 (m, 4H), 6.90-7.00 (m, 6H), 7.19-7.32 (m, 4H), 7.48-7.60 (m, 6H) ), 8.18-8.22 (m, 4H).
From the above results, it was determined that the formula of the obtained organic substance was C 54 H 34 N 4 and the molecular weight was 738.89. The structural formula of the organic substance in this case is shown below.
以下、この有機物をＤＣＺ－４という。
Hereinafter, this organic substance will be referred to as DCZ-4.
［実施例５］
構造式が下記に示される９－（３，５－ジブロモフェニル）－９Ｈ－カルバゾールを１ミリモル用いた以外は実施例１と同様にして、白色固体の有機物を得た。なお、ジカルバゾール、Ｐｄ（ＯＡｃ）2、ｔ－Ｂｕ3Ｐ及びＮａＯ（ｔ－Ｂｕ）は、それぞれ、２ミリモル、０．０４ミリモル、０．１６ミリモル、３ミリモルとし、メシチレンは５ミリリットルとした。収量は０．８１ｇであり、収率は９０％であった。 [Example 5]
A white solid organic substance was obtained in the same manner as in Example 1, except that 1 mmol of 9-(3,5-dibromophenyl)-9H-carbazole having the structural formula shown below was used. Note that dicarbazole, Pd(OAc) 2 , t-Bu 3 P, and NaO(t-Bu) were set at 2 mmol, 0.04 mmol, 0.16 mmol, and 3 mmol, respectively, and mesitylene was set at 5 ml. . The yield was 0.81 g, and the yield was 90%.
構造式が下記に示される９－（３，５－ジブロモフェニル）－９Ｈ－カルバゾールを１ミリモル用いた以外は実施例１と同様にして、白色固体の有機物を得た。なお、ジカルバゾール、Ｐｄ（ＯＡｃ）2、ｔ－Ｂｕ3Ｐ及びＮａＯ（ｔ－Ｂｕ）は、それぞれ、２ミリモル、０．０４ミリモル、０．１６ミリモル、３ミリモルとし、メシチレンは５ミリリットルとした。収量は０．８１ｇであり、収率は９０％であった。 [Example 5]
A white solid organic substance was obtained in the same manner as in Example 1, except that 1 mmol of 9-(3,5-dibromophenyl)-9H-carbazole having the structural formula shown below was used. Note that dicarbazole, Pd(OAc) 2 , t-Bu 3 P, and NaO(t-Bu) were set at 2 mmol, 0.04 mmol, 0.16 mmol, and 3 mmol, respectively, and mesitylene was set at 5 ml. . The yield was 0.81 g, and the yield was 90%.
有機微量元素分析装置による分子中のＣ、Ｈ及びＮは、それぞれ、８７．９８％、４．６９％及び７．６５％であった。また、ＮＭＲによる分析結果は下記のとおりである。
1ＨＮＭＲ（ＣＤＣｌ3，３９２ＭＨｚ）；δ＝６．０９（ｓ，１Ｈ）、６．３５（ｄｄ，Ｊ＝７．２，７．２Ｈｚ，２Ｈ）、６．５４－６．６４（ｍ，６Ｈ）、６．７４－６．８１（ｍ，４Ｈ）、６．９（ｓ，２Ｈ）、７．００－７．０６（ｍ，６Ｈ）、７．２１－７．２９（ｍ，４Ｈ）、７．３５－７．３８（ｍ，８Ｈ）、７．５６（ｄ，Ｊ＝７．２Ｈｚ，２Ｈ）、８．０５（ｄ，Ｊ＝７．２Ｈｚ，２Ｈ）、８．２０－８．２３（ｍ，４Ｈ）。
以上の結果から、得られた有機物の示性式はＣ66Ｈ41Ｎ5であり、分子量は９０４．０９であると判断された。この場合の有機物の構造式を、下記に示す。 C, H, and N in the molecule determined by an organic trace element analyzer were 87.98%, 4.69%, and 7.65%, respectively. Further, the results of NMR analysis are as follows.
1 HNMR (CDCl 3 , 392 MHz); δ = 6.09 (s, 1H), 6.35 (dd, J = 7.2, 7.2Hz, 2H), 6.54-6.64 (m, 6H ), 6.74-6.81 (m, 4H), 6.9 (s, 2H), 7.00-7.06 (m, 6H), 7.21-7.29 (m, 4H), 7.35-7.38 (m, 8H), 7.56 (d, J=7.2Hz, 2H), 8.05 (d, J=7.2Hz, 2H), 8.20-8.23 (m, 4H).
From the above results, it was determined that the specific formula of the obtained organic substance was C 66 H 41 N 5 and the molecular weight was 904.09. The structural formula of the organic substance in this case is shown below.
1ＨＮＭＲ（ＣＤＣｌ3，３９２ＭＨｚ）；δ＝６．０９（ｓ，１Ｈ）、６．３５（ｄｄ，Ｊ＝７．２，７．２Ｈｚ，２Ｈ）、６．５４－６．６４（ｍ，６Ｈ）、６．７４－６．８１（ｍ，４Ｈ）、６．９（ｓ，２Ｈ）、７．００－７．０６（ｍ，６Ｈ）、７．２１－７．２９（ｍ，４Ｈ）、７．３５－７．３８（ｍ，８Ｈ）、７．５６（ｄ，Ｊ＝７．２Ｈｚ，２Ｈ）、８．０５（ｄ，Ｊ＝７．２Ｈｚ，２Ｈ）、８．２０－８．２３（ｍ，４Ｈ）。
以上の結果から、得られた有機物の示性式はＣ66Ｈ41Ｎ5であり、分子量は９０４．０９であると判断された。この場合の有機物の構造式を、下記に示す。 C, H, and N in the molecule determined by an organic trace element analyzer were 87.98%, 4.69%, and 7.65%, respectively. Further, the results of NMR analysis are as follows.
1 HNMR (CDCl 3 , 392 MHz); δ = 6.09 (s, 1H), 6.35 (dd, J = 7.2, 7.2Hz, 2H), 6.54-6.64 (m, 6H ), 6.74-6.81 (m, 4H), 6.9 (s, 2H), 7.00-7.06 (m, 6H), 7.21-7.29 (m, 4H), 7.35-7.38 (m, 8H), 7.56 (d, J=7.2Hz, 2H), 8.05 (d, J=7.2Hz, 2H), 8.20-8.23 (m, 4H).
From the above results, it was determined that the specific formula of the obtained organic substance was C 66 H 41 N 5 and the molecular weight was 904.09. The structural formula of the organic substance in this case is shown below.
以下、この有機物をＤＣＺ－６という。
Hereinafter, this organic substance will be referred to as DCZ-6.
［実施例６］
構造式が下記に示されるＮ，Ｎ－ビス（４－ビフェニルイル）－Ｎ－（４－ブロモフェニル）アミンを１ミリモル用いた以外は実施例４と同様にして、白色固体の有機物を得た。なお、ジカルバゾール、Ｐｄ（ＯＡｃ）2、ｔ－Ｂｕ3Ｐ及びＮａＯ（ｔ－Ｂｕ）は、それぞれ、１ミリモル、０．０２ミリモル、０．０８ミリモル、１．５ミリモルとし、メシチレンは４ミリリットルとした。収量は０．４６ｇであり、収率は６３％であった。 [Example 6]
A white solid organic substance was obtained in the same manner as in Example 4, except that 1 mmol of N,N-bis(4-biphenylyl)-N-(4-bromophenyl)amine whose structural formula is shown below was used. . Note that dicarbazole, Pd(OAc) 2 , t-Bu 3 P, and NaO(t-Bu) are 1 mmol, 0.02 mmol, 0.08 mmol, and 1.5 mmol, respectively, and mesitylene is 4 ml. And so. The yield was 0.46 g, and the yield was 63%.
構造式が下記に示されるＮ，Ｎ－ビス（４－ビフェニルイル）－Ｎ－（４－ブロモフェニル）アミンを１ミリモル用いた以外は実施例４と同様にして、白色固体の有機物を得た。なお、ジカルバゾール、Ｐｄ（ＯＡｃ）2、ｔ－Ｂｕ3Ｐ及びＮａＯ（ｔ－Ｂｕ）は、それぞれ、１ミリモル、０．０２ミリモル、０．０８ミリモル、１．５ミリモルとし、メシチレンは４ミリリットルとした。収量は０．４６ｇであり、収率は６３％であった。 [Example 6]
A white solid organic substance was obtained in the same manner as in Example 4, except that 1 mmol of N,N-bis(4-biphenylyl)-N-(4-bromophenyl)amine whose structural formula is shown below was used. . Note that dicarbazole, Pd(OAc) 2 , t-Bu 3 P, and NaO(t-Bu) are 1 mmol, 0.02 mmol, 0.08 mmol, and 1.5 mmol, respectively, and mesitylene is 4 ml. And so. The yield was 0.46 g, and the yield was 63%.
有機微量元素分析装置による分子中のＣ、Ｈ及びＮは、それぞれ、８９．１９％、５．２０％及び５．５６％であった。また、ＮＭＲによる分析結果は下記のとおりである。
1ＨＮＭＲ（ＣＤＣｌ3，３９２ＭＨｚ）；δ＝６．３０（ｄ，Ｊ＝８．５Ｈｚ，２Ｈ）、６．５８（ｄ，Ｊ＝８．５Ｈｚ，２Ｈ）、６．８４（ｄ，Ｊ＝８．５Ｈｚ，４Ｈ）、７．０４（ｄ，Ｊ＝８．５Ｈｚ，２Ｈ）、７．１１（ｄ，Ｊ＝８．５Ｈｚ，１Ｈ）、７．２０－７．２４（ｍ，２Ｈ）、７．２５－７．５０（ｍ，１６Ｈ）、７．５９（ｄ，Ｊ＝７．２Ｈｚ，４Ｈ）、８．０８（ｄ，Ｊ＝７．６Ｈｚ，２Ｈ）、８．２２（ｄ，Ｊ＝７．６Ｈｚ，１Ｈ）、８．３２（ｄ，Ｊ＝７．２Ｈｚ，１Ｈ）。
以上の結果から、得られた有機物の示性式はＣ54Ｈ37Ｎ3であり、分子量は７２７．９１であると判断された。この場合の有機物の構造式を、下記に示す。 C, H, and N in the molecule determined by an organic trace element analyzer were 89.19%, 5.20%, and 5.56%, respectively. Further, the results of NMR analysis are as follows.
1 HNMR (CDCl 3 , 392 MHz); δ = 6.30 (d, J = 8.5 Hz, 2H), 6.58 (d, J = 8.5 Hz, 2H), 6.84 (d, J = 8 .5Hz, 4H), 7.04 (d, J = 8.5Hz, 2H), 7.11 (d, J = 8.5Hz, 1H), 7.20-7.24 (m, 2H), 7 .25-7.50 (m, 16H), 7.59 (d, J = 7.2Hz, 4H), 8.08 (d, J = 7.6Hz, 2H), 8.22 (d, J = 7.6Hz, 1H), 8.32 (d, J=7.2Hz, 1H).
From the above results, it was determined that the formula of the obtained organic substance was C 54 H 37 N 3 and the molecular weight was 727.91. The structural formula of the organic substance in this case is shown below.
1ＨＮＭＲ（ＣＤＣｌ3，３９２ＭＨｚ）；δ＝６．３０（ｄ，Ｊ＝８．５Ｈｚ，２Ｈ）、６．５８（ｄ，Ｊ＝８．５Ｈｚ，２Ｈ）、６．８４（ｄ，Ｊ＝８．５Ｈｚ，４Ｈ）、７．０４（ｄ，Ｊ＝８．５Ｈｚ，２Ｈ）、７．１１（ｄ，Ｊ＝８．５Ｈｚ，１Ｈ）、７．２０－７．２４（ｍ，２Ｈ）、７．２５－７．５０（ｍ，１６Ｈ）、７．５９（ｄ，Ｊ＝７．２Ｈｚ，４Ｈ）、８．０８（ｄ，Ｊ＝７．６Ｈｚ，２Ｈ）、８．２２（ｄ，Ｊ＝７．６Ｈｚ，１Ｈ）、８．３２（ｄ，Ｊ＝７．２Ｈｚ，１Ｈ）。
以上の結果から、得られた有機物の示性式はＣ54Ｈ37Ｎ3であり、分子量は７２７．９１であると判断された。この場合の有機物の構造式を、下記に示す。 C, H, and N in the molecule determined by an organic trace element analyzer were 89.19%, 5.20%, and 5.56%, respectively. Further, the results of NMR analysis are as follows.
1 HNMR (CDCl 3 , 392 MHz); δ = 6.30 (d, J = 8.5 Hz, 2H), 6.58 (d, J = 8.5 Hz, 2H), 6.84 (d, J = 8 .5Hz, 4H), 7.04 (d, J = 8.5Hz, 2H), 7.11 (d, J = 8.5Hz, 1H), 7.20-7.24 (m, 2H), 7 .25-7.50 (m, 16H), 7.59 (d, J = 7.2Hz, 4H), 8.08 (d, J = 7.6Hz, 2H), 8.22 (d, J = 7.6Hz, 1H), 8.32 (d, J=7.2Hz, 1H).
From the above results, it was determined that the formula of the obtained organic substance was C 54 H 37 N 3 and the molecular weight was 727.91. The structural formula of the organic substance in this case is shown below.
以下、この有機物をＤＣＺ－９という。
Hereinafter, this organic substance will be referred to as DCZ-9.
［実施例７］
構造式が下記に示される４’－ブロモトリ（４－ビフェニルイル）アミンを用いた以外は実施例５と同様にして、白色固体の有機物を得た。ジカルバゾール、４’－ブロモトリ（４－ビフェニルイル）アミン、Ｐｄ（ＯＡｃ）2、ｔ－Ｂｕ3Ｐ及びＮａＯ（ｔ－Ｂｕ）のモル比は実施例５と同様である。なお、メシチレンは２．５ミリリットルとした。収量は０．７２ｇであり、収率は８９％であった。 [Example 7]
A white solid organic substance was obtained in the same manner as in Example 5 except that 4'-bromotri(4-biphenylyl)amine having the structural formula shown below was used. The molar ratios of dicarbazole, 4'-bromotri(4-biphenylyl)amine, Pd(OAc) 2 , t-Bu 3 P and NaO(t-Bu) are the same as in Example 5. Note that the amount of mesitylene was 2.5 ml. The yield was 0.72 g, and the yield was 89%.
構造式が下記に示される４’－ブロモトリ（４－ビフェニルイル）アミンを用いた以外は実施例５と同様にして、白色固体の有機物を得た。ジカルバゾール、４’－ブロモトリ（４－ビフェニルイル）アミン、Ｐｄ（ＯＡｃ）2、ｔ－Ｂｕ3Ｐ及びＮａＯ（ｔ－Ｂｕ）のモル比は実施例５と同様である。なお、メシチレンは２．５ミリリットルとした。収量は０．７２ｇであり、収率は８９％であった。 [Example 7]
A white solid organic substance was obtained in the same manner as in Example 5 except that 4'-bromotri(4-biphenylyl)amine having the structural formula shown below was used. The molar ratios of dicarbazole, 4'-bromotri(4-biphenylyl)amine, Pd(OAc) 2 , t-Bu 3 P and NaO(t-Bu) are the same as in Example 5. Note that the amount of mesitylene was 2.5 ml. The yield was 0.72 g, and the yield was 89%.
有機微量元素分析装置による分子中のＨ、Ｃ及びＮは、それぞれ、５．２７％、８９．６７％及び５．４３％であった。また、ＮＭＲによる分析結果は下記のとおりである。
1ＨＮＭＲ（ＣＤＣｌ3，３９２ＭＨｚ）；δ＝６．５１（ｓ，４Ｈ）、７．０１（ｄ，Ｊ＝８．１Ｈｚ，２Ｈ）、７．０６－７．２３（ｍ，８Ｈ）、７．２６－７．３７（ｍ，８Ｈ），７．４２－７．６３（ｍ，１５Ｈ）、７．７７（ｄ，Ｊ＝７．６Ｈｚ，２Ｈ），８．２３（ｄ，Ｊ＝７．２Ｈｚ，１Ｈ）、８．３４（ｄ，Ｊ＝８．１Ｈｚ，１Ｈ）。
以上の結果から、得られた有機物の示性式はＣ60Ｈ41Ｎ3であり、分子量は８０９．０１であると判断された。この場合の有機物の構造式を、下記に示す。 H, C, and N in the molecule determined by an organic trace element analyzer were 5.27%, 89.67%, and 5.43%, respectively. Further, the results of NMR analysis are as follows.
1 HNMR (CDCl 3 , 392 MHz); δ = 6.51 (s, 4H), 7.01 (d, J = 8.1 Hz, 2H), 7.06-7.23 (m, 8H), 7. 26-7.37 (m, 8H), 7.42-7.63 (m, 15H), 7.77 (d, J = 7.6Hz, 2H), 8.23 (d, J = 7.2Hz) , 1H), 8.34 (d, J = 8.1Hz, 1H).
From the above results, it was determined that the specific formula of the organic substance obtained was C 60 H 41 N 3 and the molecular weight was 809.01. The structural formula of the organic substance in this case is shown below.
1ＨＮＭＲ（ＣＤＣｌ3，３９２ＭＨｚ）；δ＝６．５１（ｓ，４Ｈ）、７．０１（ｄ，Ｊ＝８．１Ｈｚ，２Ｈ）、７．０６－７．２３（ｍ，８Ｈ）、７．２６－７．３７（ｍ，８Ｈ），７．４２－７．６３（ｍ，１５Ｈ）、７．７７（ｄ，Ｊ＝７．６Ｈｚ，２Ｈ），８．２３（ｄ，Ｊ＝７．２Ｈｚ，１Ｈ）、８．３４（ｄ，Ｊ＝８．１Ｈｚ，１Ｈ）。
以上の結果から、得られた有機物の示性式はＣ60Ｈ41Ｎ3であり、分子量は８０９．０１であると判断された。この場合の有機物の構造式を、下記に示す。 H, C, and N in the molecule determined by an organic trace element analyzer were 5.27%, 89.67%, and 5.43%, respectively. Further, the results of NMR analysis are as follows.
1 HNMR (CDCl 3 , 392 MHz); δ = 6.51 (s, 4H), 7.01 (d, J = 8.1 Hz, 2H), 7.06-7.23 (m, 8H), 7. 26-7.37 (m, 8H), 7.42-7.63 (m, 15H), 7.77 (d, J = 7.6Hz, 2H), 8.23 (d, J = 7.2Hz) , 1H), 8.34 (d, J = 8.1Hz, 1H).
From the above results, it was determined that the specific formula of the organic substance obtained was C 60 H 41 N 3 and the molecular weight was 809.01. The structural formula of the organic substance in this case is shown below.
以下、この有機物をＤＣＺ－１０という。
Hereinafter, this organic substance will be referred to as DCZ-10.
［実施例８］
構造式が下記に示されるＮ－（４－ブロモフェニル）－Ｎ－（ナフタレン－２－イル）ナフタレン－２－アミンを１ミリモル用いた以外は実施例２と同様にして、白色固体の有機物を得た。なお、エチレンは２．７ミリリットルとした。収量は０．６０ｇであり、収率は８８％であった。 [Example 8]
A white solid organic substance was prepared in the same manner as in Example 2 except that 1 mmol of N-(4-bromophenyl)-N-(naphthalen-2-yl)naphthalen-2-amine whose structural formula is shown below was used. Obtained. Note that the amount of ethylene was 2.7 ml. The yield was 0.60 g, and the yield was 88%.
構造式が下記に示されるＮ－（４－ブロモフェニル）－Ｎ－（ナフタレン－２－イル）ナフタレン－２－アミンを１ミリモル用いた以外は実施例２と同様にして、白色固体の有機物を得た。なお、エチレンは２．７ミリリットルとした。収量は０．６０ｇであり、収率は８８％であった。 [Example 8]
A white solid organic substance was prepared in the same manner as in Example 2 except that 1 mmol of N-(4-bromophenyl)-N-(naphthalen-2-yl)naphthalen-2-amine whose structural formula is shown below was used. Obtained. Note that the amount of ethylene was 2.7 ml. The yield was 0.60 g, and the yield was 88%.
有機微量元素分析装置による分子中のＨ、Ｃ及びＮは、それぞれ、８９．０３％、４．９６％及び６．０５％であった。また、ＮＭＲによる分析結果は下記のとおりである。
1ＨＮＭＲ（ＣＤＣｌ3，３９２ＭＨｚ）；δ＝６．２５－６．２９（ｍ，２Ｈ），６．５３－６．５７（ｍ，２Ｈ）、７．０３－７．０６（ｍ，４Ｈ）、７．１０－７．５０（ｍ，１５Ｈ）、７．６０－７．６３（ｍ，２Ｈ）、７．７６－７．８１（ｍ，４Ｈ）、８．１２－８．１４（ｍ，２Ｈ）、８．２２－８．２４（ｍ，１Ｈ）、８．３２－８．３４（ｍ，１Ｈ）。
以上の結果から、得られた有機物の示性式はＣ50Ｈ35Ｎ3であり、分子量は６７５．８４であると判断された。この場合の有機物の構造式を、下記に示す。 H, C, and N in the molecule determined by an organic trace element analyzer were 89.03%, 4.96%, and 6.05%, respectively. Further, the results of NMR analysis are as follows.
1 HNMR (CDCl 3 , 392 MHz); δ = 6.25-6.29 (m, 2H), 6.53-6.57 (m, 2H), 7.03-7.06 (m, 4H), 7.10-7.50 (m, 15H), 7.60-7.63 (m, 2H), 7.76-7.81 (m, 4H), 8.12-8.14 (m, 2H) ), 8.22-8.24 (m, 1H), 8.32-8.34 (m, 1H).
From the above results, it was determined that the formula of the obtained organic substance was C 50 H 35 N 3 and the molecular weight was 675.84. The structural formula of the organic substance in this case is shown below.
1ＨＮＭＲ（ＣＤＣｌ3，３９２ＭＨｚ）；δ＝６．２５－６．２９（ｍ，２Ｈ），６．５３－６．５７（ｍ，２Ｈ）、７．０３－７．０６（ｍ，４Ｈ）、７．１０－７．５０（ｍ，１５Ｈ）、７．６０－７．６３（ｍ，２Ｈ）、７．７６－７．８１（ｍ，４Ｈ）、８．１２－８．１４（ｍ，２Ｈ）、８．２２－８．２４（ｍ，１Ｈ）、８．３２－８．３４（ｍ，１Ｈ）。
以上の結果から、得られた有機物の示性式はＣ50Ｈ35Ｎ3であり、分子量は６７５．８４であると判断された。この場合の有機物の構造式を、下記に示す。 H, C, and N in the molecule determined by an organic trace element analyzer were 89.03%, 4.96%, and 6.05%, respectively. Further, the results of NMR analysis are as follows.
1 HNMR (CDCl 3 , 392 MHz); δ = 6.25-6.29 (m, 2H), 6.53-6.57 (m, 2H), 7.03-7.06 (m, 4H), 7.10-7.50 (m, 15H), 7.60-7.63 (m, 2H), 7.76-7.81 (m, 4H), 8.12-8.14 (m, 2H) ), 8.22-8.24 (m, 1H), 8.32-8.34 (m, 1H).
From the above results, it was determined that the formula of the obtained organic substance was C 50 H 35 N 3 and the molecular weight was 675.84. The structural formula of the organic substance in this case is shown below.
以下、この有機物をＤＣＺ－１１という。
Hereinafter, this organic substance will be referred to as DCZ-11.
［実施例９］
構造式が下記に示されるＮ－（４’－ブロモ－［１、１’－ビフェニル］－４－イル）－Ｎ－（ナフタレン－２－イル）－ナフタレン－２－アミンを１ミリモル用いた以外は、メシチレンの量も含めて実施例８と同様にして、白色固体の有機物を得た。収量は０．６５ｇであり、収率は８７％であった。 [Example 9]
Except for using 1 mmol of N-(4'-bromo-[1,1'-biphenyl]-4-yl)-N-(naphthalen-2-yl)-naphthalen-2-amine whose structural formula is shown below. A white solid organic substance was obtained in the same manner as in Example 8, including the amount of mesitylene. The yield was 0.65 g, and the yield was 87%.
構造式が下記に示されるＮ－（４’－ブロモ－［１、１’－ビフェニル］－４－イル）－Ｎ－（ナフタレン－２－イル）－ナフタレン－２－アミンを１ミリモル用いた以外は、メシチレンの量も含めて実施例８と同様にして、白色固体の有機物を得た。収量は０．６５ｇであり、収率は８７％であった。 [Example 9]
Except for using 1 mmol of N-(4'-bromo-[1,1'-biphenyl]-4-yl)-N-(naphthalen-2-yl)-naphthalen-2-amine whose structural formula is shown below. A white solid organic substance was obtained in the same manner as in Example 8, including the amount of mesitylene. The yield was 0.65 g, and the yield was 87%.
有機微量元素分析装置による分子中のＣ、Ｈ及びＮは、それぞれ、８９．５４％、５．０４％及び５．２９％であった。また、ＮＭＲによる分析結果は下記のとおりである。
1ＨＮＭＲ（ＣＤＣｌ3，３９２ＭＨｚ）；δ＝６．５２－６．５３（ｍ，４Ｈ）、６．９９－７．０２（ｍ，２Ｈ）、７．０８－７．１９（ｍ，８Ｈ）、７．２５－７．５８（ｍ，１３Ｈ）、７．６４－７．６６（ｍ，２Ｈ）、７．７７－７．８３（ｍ，６Ｈ）、８．２２－８．２４（ｍ，１Ｈ）、８．３３－８．３６（ｍ，１Ｈ）。
以上の結果から、得られた有機物の示性式はＣ56Ｈ37Ｎ3であり、分子量は７５１．９３であると判断された。この場合の有機物の構造式を、下記に示す。 C, H and N in the molecule determined by an organic trace element analyzer were 89.54%, 5.04% and 5.29%, respectively. Further, the results of NMR analysis are as follows.
1 HNMR (CDCl 3 , 392 MHz); δ = 6.52-6.53 (m, 4H), 6.99-7.02 (m, 2H), 7.08-7.19 (m, 8H), 7.25-7.58 (m, 13H), 7.64-7.66 (m, 2H), 7.77-7.83 (m, 6H), 8.22-8.24 (m, 1H) ), 8.33-8.36 (m, 1H).
From the above results, it was determined that the specific formula of the obtained organic substance was C 56 H 37 N 3 and the molecular weight was 751.93. The structural formula of the organic substance in this case is shown below.
1ＨＮＭＲ（ＣＤＣｌ3，３９２ＭＨｚ）；δ＝６．５２－６．５３（ｍ，４Ｈ）、６．９９－７．０２（ｍ，２Ｈ）、７．０８－７．１９（ｍ，８Ｈ）、７．２５－７．５８（ｍ，１３Ｈ）、７．６４－７．６６（ｍ，２Ｈ）、７．７７－７．８３（ｍ，６Ｈ）、８．２２－８．２４（ｍ，１Ｈ）、８．３３－８．３６（ｍ，１Ｈ）。
以上の結果から、得られた有機物の示性式はＣ56Ｈ37Ｎ3であり、分子量は７５１．９３であると判断された。この場合の有機物の構造式を、下記に示す。 C, H and N in the molecule determined by an organic trace element analyzer were 89.54%, 5.04% and 5.29%, respectively. Further, the results of NMR analysis are as follows.
1 HNMR (CDCl 3 , 392 MHz); δ = 6.52-6.53 (m, 4H), 6.99-7.02 (m, 2H), 7.08-7.19 (m, 8H), 7.25-7.58 (m, 13H), 7.64-7.66 (m, 2H), 7.77-7.83 (m, 6H), 8.22-8.24 (m, 1H) ), 8.33-8.36 (m, 1H).
From the above results, it was determined that the specific formula of the obtained organic substance was C 56 H 37 N 3 and the molecular weight was 751.93. The structural formula of the organic substance in this case is shown below.
以下、この有機物をＤＣＺ－１２という。
Hereinafter, this organic substance will be referred to as DCZ-12.
［実施例１０］
臭化アリールとして、構造式が下記に示される９－（４－ブロモフェニル）－３，６－ジフェニル－９Ｈ－カルバゾールを、１ミリモルに相当する０．４７４ｇ用いた以外は、メシチレンの量も含めて実施例９と同様にして、白色固体の有機物を得た。収量は０．５２ｇであり、収率は７１％であった。 [Example 10]
The amount of mesitylene was also included, except that 0.474 g, equivalent to 1 mmol, of 9-(4-bromophenyl)-3,6-diphenyl-9H-carbazole, whose structural formula is shown below, was used as the aryl bromide. In the same manner as in Example 9, a white solid organic substance was obtained. The yield was 0.52 g, and the yield was 71%.
臭化アリールとして、構造式が下記に示される９－（４－ブロモフェニル）－３，６－ジフェニル－９Ｈ－カルバゾールを、１ミリモルに相当する０．４７４ｇ用いた以外は、メシチレンの量も含めて実施例９と同様にして、白色固体の有機物を得た。収量は０．５２ｇであり、収率は７１％であった。 [Example 10]
The amount of mesitylene was also included, except that 0.474 g, equivalent to 1 mmol, of 9-(4-bromophenyl)-3,6-diphenyl-9H-carbazole, whose structural formula is shown below, was used as the aryl bromide. In the same manner as in Example 9, a white solid organic substance was obtained. The yield was 0.52 g, and the yield was 71%.
有機微量元素分析装置による分子中のＣ、Ｈ及びＮは、それぞれ、８９．４３％、４．９８％及び５．８７％であった。また、ＮＭＲによる分析結果は下記のとおりである。
1ＨＮＭＲ（ＣＤＣｌ3，３９２ＭＨｚ）；δ＝６．７８－６．８０（ｍ，２Ｈ）、６．９４－６．９６（ｍ，２Ｈ）、７．１２－７．６２（ｍ，１９Ｈ）、７．７１－７．７７（ｍ，６Ｈ）、７．９５－７．９７（ｍ，２Ｈ）、８．２８－８．３９（ｍ，４Ｈ）。
以上の結果から、得られた有機物の示性式はＣ54Ｈ35Ｎ3であり、分子量は７２５．９であると判断された。この場合の有機物の構造式を、下記に示す。 C, H and N in the molecule determined by an organic trace element analyzer were 89.43%, 4.98% and 5.87%, respectively. Further, the results of NMR analysis are as follows.
1 HNMR (CDCl 3 , 392 MHz); δ = 6.78-6.80 (m, 2H), 6.94-6.96 (m, 2H), 7.12-7.62 (m, 19H), 7.71-7.77 (m, 6H), 7.95-7.97 (m, 2H), 8.28-8.39 (m, 4H).
From the above results, it was determined that the specific formula of the obtained organic substance was C 54 H 35 N 3 and the molecular weight was 725.9. The structural formula of the organic substance in this case is shown below.
1ＨＮＭＲ（ＣＤＣｌ3，３９２ＭＨｚ）；δ＝６．７８－６．８０（ｍ，２Ｈ）、６．９４－６．９６（ｍ，２Ｈ）、７．１２－７．６２（ｍ，１９Ｈ）、７．７１－７．７７（ｍ，６Ｈ）、７．９５－７．９７（ｍ，２Ｈ）、８．２８－８．３９（ｍ，４Ｈ）。
以上の結果から、得られた有機物の示性式はＣ54Ｈ35Ｎ3であり、分子量は７２５．９であると判断された。この場合の有機物の構造式を、下記に示す。 C, H and N in the molecule determined by an organic trace element analyzer were 89.43%, 4.98% and 5.87%, respectively. Further, the results of NMR analysis are as follows.
1 HNMR (CDCl 3 , 392 MHz); δ = 6.78-6.80 (m, 2H), 6.94-6.96 (m, 2H), 7.12-7.62 (m, 19H), 7.71-7.77 (m, 6H), 7.95-7.97 (m, 2H), 8.28-8.39 (m, 4H).
From the above results, it was determined that the specific formula of the obtained organic substance was C 54 H 35 N 3 and the molecular weight was 725.9. The structural formula of the organic substance in this case is shown below.
以下、この有機物をＤＣＺ－１３という。
Hereinafter, this organic substance will be referred to as DCZ-13.
［実施例１１］
構造式が下記に示される９－（４’－ブロモ－［１，１’－ビフェニル］－４－イル）－３，６－ジフェニル－９Ｈ－カルバゾールを１ミリモル用い、且つエチレンを５ミリリットルとした以外は実施例１０と同様にして、白色固体の有機物を得た。収量は０．７０ｇであり、収率は８８％であった。 [Example 11]
1 mmol of 9-(4'-bromo-[1,1'-biphenyl]-4-yl)-3,6-diphenyl-9H-carbazole whose structural formula is shown below was used, and ethylene was set at 5 ml. A white solid organic substance was obtained in the same manner as in Example 10 except for this. The yield was 0.70 g, and the yield was 88%.
構造式が下記に示される９－（４’－ブロモ－［１，１’－ビフェニル］－４－イル）－３，６－ジフェニル－９Ｈ－カルバゾールを１ミリモル用い、且つエチレンを５ミリリットルとした以外は実施例１０と同様にして、白色固体の有機物を得た。収量は０．７０ｇであり、収率は８８％であった。 [Example 11]
1 mmol of 9-(4'-bromo-[1,1'-biphenyl]-4-yl)-3,6-diphenyl-9H-carbazole whose structural formula is shown below was used, and ethylene was set at 5 ml. A white solid organic substance was obtained in the same manner as in Example 10 except for this. The yield was 0.70 g, and the yield was 88%.
有機微量元素分析装置による分子中のＣ、Ｈ及びＮは、それぞれ、８９．９３％、４．９９％及び５．０３％であった。また、ＮＭＲによる分析結果は下記のとおりである。
1ＨＮＭＲ（ＣＤＣｌ3，３９２ＭＨｚ）；δ＝６．６１－６．６６（ｍ，４Ｈ）、７．０４－７．２１（ｍ，４Ｈ）、７．３１－７．８６（ｍ，２７Ｈ）、８．２５－８．４４（ｍ，４Ｈ）。
以上の結果から、得られた有機物の示性式はＣ60Ｈ39Ｎ3であり、分子量は８０１．９９であると判断された。この場合の有機物の構造式を、下記に示す。 C, H, and N in the molecule determined by an organic trace element analyzer were 89.93%, 4.99%, and 5.03%, respectively. Further, the results of NMR analysis are as follows.
1 HNMR (CDCl 3 , 392 MHz); δ = 6.61-6.66 (m, 4H), 7.04-7.21 (m, 4H), 7.31-7.86 (m, 27H), 8.25-8.44 (m, 4H).
From the above results, it was determined that the formula of the obtained organic substance was C 60 H 39 N 3 and the molecular weight was 801.99. The structural formula of the organic substance in this case is shown below.
1ＨＮＭＲ（ＣＤＣｌ3，３９２ＭＨｚ）；δ＝６．６１－６．６６（ｍ，４Ｈ）、７．０４－７．２１（ｍ，４Ｈ）、７．３１－７．８６（ｍ，２７Ｈ）、８．２５－８．４４（ｍ，４Ｈ）。
以上の結果から、得られた有機物の示性式はＣ60Ｈ39Ｎ3であり、分子量は８０１．９９であると判断された。この場合の有機物の構造式を、下記に示す。 C, H, and N in the molecule determined by an organic trace element analyzer were 89.93%, 4.99%, and 5.03%, respectively. Further, the results of NMR analysis are as follows.
1 HNMR (CDCl 3 , 392 MHz); δ = 6.61-6.66 (m, 4H), 7.04-7.21 (m, 4H), 7.31-7.86 (m, 27H), 8.25-8.44 (m, 4H).
From the above results, it was determined that the formula of the obtained organic substance was C 60 H 39 N 3 and the molecular weight was 801.99. The structural formula of the organic substance in this case is shown below.
以下、この有機物をＤＣＺ－１４いう。
Hereinafter, this organic substance will be referred to as DCZ-14.
［実施例１２］
ジカルバゾール化合物として、構造式が下記に示される３，３’，６，６’－テトラフェニル－９Ｈ－１，９’－ビカルバゾールを、１ミリモルに相当する０．６４ｇ用いた。 [Example 12]
As the dicarbazole compound, 0.64 g, equivalent to 1 mmol, of 3,3',6,6'-tetraphenyl-9H-1,9'-bicarbazole whose structural formula is shown below was used.
ジカルバゾール化合物として、構造式が下記に示される３，３’，６，６’－テトラフェニル－９Ｈ－１，９’－ビカルバゾールを、１ミリモルに相当する０．６４ｇ用いた。 [Example 12]
As the dicarbazole compound, 0.64 g, equivalent to 1 mmol, of 3,3',6,6'-tetraphenyl-9H-1,9'-bicarbazole whose structural formula is shown below was used.
また、臭化アリールとして、構造式が下記に示される４－ブロモビフェニルを１ミリモルに相当する０．２３３ｇ用いた。
Further, as the aryl bromide, 0.233 g of 4-bromobiphenyl whose structural formula is shown below was used, which corresponds to 1 mmol.
その後、エチレンを２．５ミリリットルとした以外は実施例１１と同様にして、白色固体の有機物を得た。収量は０．４８ｇであり、収率は６１％であった。
Thereafter, a white solid organic substance was obtained in the same manner as in Example 11, except that the amount of ethylene was changed to 2.5 ml. The yield was 0.48 g, and the yield was 61%.
有機微量元素分析装置による分子中のＣ、Ｈ及びＮは、それぞれ、９１．１９％、５．１６％及び３．４９％であった。また、ＮＭＲによる分析結果は下記のとおりである。
1ＨＮＭＲ（ＣＤＣｌ3，３９２ＭＨｚ）；δ＝６．６２－６．６７（ｍ，４Ｈ）、７．１４－７．６４（ｍ，２７Ｈ）、７．７３－７．７５（ｍ，２Ｈ）、７．８３－７．８５（ｍ，２Ｈ）、７．９２－７．９３（ｍ，１Ｈ），８．０１－８．０２（ｍ，２Ｈ）、８．５０－８．５１（ｍ，１Ｈ）、８．６５－８．６６（ｍ，１Ｈ）。
以上の結果から、得られた有機物の示性式はＣ60Ｈ39Ｎ3であり、分子量は８０１．９９であると判断された。この場合の有機物の構造式を、下記に示す。 C, H, and N in the molecule determined by an organic trace element analyzer were 91.19%, 5.16%, and 3.49%, respectively. Further, the results of NMR analysis are as follows.
1 HNMR (CDCl 3 , 392 MHz); δ = 6.62-6.67 (m, 4H), 7.14-7.64 (m, 27H), 7.73-7.75 (m, 2H), 7.83-7.85 (m, 2H), 7.92-7.93 (m, 1H), 8.01-8.02 (m, 2H), 8.50-8.51 (m, 1H) ), 8.65-8.66 (m, 1H).
From the above results, it was determined that the formula of the obtained organic substance was C 60 H 39 N 3 and the molecular weight was 801.99. The structural formula of the organic substance in this case is shown below.
1ＨＮＭＲ（ＣＤＣｌ3，３９２ＭＨｚ）；δ＝６．６２－６．６７（ｍ，４Ｈ）、７．１４－７．６４（ｍ，２７Ｈ）、７．７３－７．７５（ｍ，２Ｈ）、７．８３－７．８５（ｍ，２Ｈ）、７．９２－７．９３（ｍ，１Ｈ），８．０１－８．０２（ｍ，２Ｈ）、８．５０－８．５１（ｍ，１Ｈ）、８．６５－８．６６（ｍ，１Ｈ）。
以上の結果から、得られた有機物の示性式はＣ60Ｈ39Ｎ3であり、分子量は８０１．９９であると判断された。この場合の有機物の構造式を、下記に示す。 C, H, and N in the molecule determined by an organic trace element analyzer were 91.19%, 5.16%, and 3.49%, respectively. Further, the results of NMR analysis are as follows.
1 HNMR (CDCl 3 , 392 MHz); δ = 6.62-6.67 (m, 4H), 7.14-7.64 (m, 27H), 7.73-7.75 (m, 2H), 7.83-7.85 (m, 2H), 7.92-7.93 (m, 1H), 8.01-8.02 (m, 2H), 8.50-8.51 (m, 1H) ), 8.65-8.66 (m, 1H).
From the above results, it was determined that the formula of the obtained organic substance was C 60 H 39 N 3 and the molecular weight was 801.99. The structural formula of the organic substance in this case is shown below.
以下、この有機物をＤＣＺ－１５という。
Hereinafter, this organic substance will be referred to as DCZ-15.
［実施例１３］
９－（３－ブロモフェニル）－９Ｈ－カルバゾールに代替して１ミリモルの３、３’－ジブロモビフェニルを用いた以外は実施例１と同様にして混合液を調製した。該混合液を、アルゴン雰囲気下で１５０℃に保持した状態で、４時間撹拌した。混合液に１モル／リットルのＨＣｌを添加してクエンチを行い、クロロホルムで抽出した。有機層を水で洗浄した後、該有機層を飽和食塩水で洗浄した。その後、有機物をＭｇＳＯ4で乾燥した。溶媒を減圧下で除去して、粗生成物を得た。 [Example 13]
A mixed solution was prepared in the same manner as in Example 1 except that 1 mmol of 3,3'-dibromobiphenyl was used in place of 9-(3-bromophenyl)-9H-carbazole. The mixture was stirred for 4 hours while being maintained at 150° C. under an argon atmosphere. The mixture was quenched by adding 1 mol/liter of HCl, and extracted with chloroform. After washing the organic layer with water, the organic layer was washed with saturated brine. The organics were then dried with MgSO4 . The solvent was removed under reduced pressure to obtain the crude product.
９－（３－ブロモフェニル）－９Ｈ－カルバゾールに代替して１ミリモルの３、３’－ジブロモビフェニルを用いた以外は実施例１と同様にして混合液を調製した。該混合液を、アルゴン雰囲気下で１５０℃に保持した状態で、４時間撹拌した。混合液に１モル／リットルのＨＣｌを添加してクエンチを行い、クロロホルムで抽出した。有機層を水で洗浄した後、該有機層を飽和食塩水で洗浄した。その後、有機物をＭｇＳＯ4で乾燥した。溶媒を減圧下で除去して、粗生成物を得た。 [Example 13]
A mixed solution was prepared in the same manner as in Example 1 except that 1 mmol of 3,3'-dibromobiphenyl was used in place of 9-(3-bromophenyl)-9H-carbazole. The mixture was stirred for 4 hours while being maintained at 150° C. under an argon atmosphere. The mixture was quenched by adding 1 mol/liter of HCl, and extracted with chloroform. After washing the organic layer with water, the organic layer was washed with saturated brine. The organics were then dried with MgSO4 . The solvent was removed under reduced pressure to obtain the crude product.
ヘキサン／酢酸エチルの５：１混合液を展開溶媒として粗生成物のシリカゲルカラム精製を行い、白色固体の有機物を得た。収量は０．５５ｇであり、収率は６８％であった。
The crude product was purified on a silica gel column using a 5:1 mixture of hexane/ethyl acetate as a developing solvent to obtain a white solid organic substance. The yield was 0.55 g, and the yield was 68%.
得られた有機物についてのＮＭＲによる分析結果は、下記のとおりであった。
1ＨＮＭＲ（ＤＭＳＯ－ｄ６，３９２ＭＨｚ）；δ＝４．６７（ｓ，２Ｈ）、５．０５（ｔ，Ｊ＝７．３Ｈｚ，２Ｈ）、５．６４（ｔ，Ｊ＝７．６Ｈｚ，２Ｈ）、６．５９－６．９０（ｍ，１２Ｈ）、７．０７－７．２３（ｍ，６Ｈ）、７．４５－７．５９（ｍ，１０Ｈ）、８．５５－８．６６（ｍ，４Ｈ）。 The results of NMR analysis of the obtained organic matter were as follows.
1 HNMR (DMSO-d6, 392MHz); δ = 4.67 (s, 2H), 5.05 (t, J = 7.3Hz, 2H), 5.64 (t, J = 7.6Hz, 2H) , 6.59-6.90 (m, 12H), 7.07-7.23 (m, 6H), 7.45-7.59 (m, 10H), 8.55-8.66 (m, 4H).
1ＨＮＭＲ（ＤＭＳＯ－ｄ６，３９２ＭＨｚ）；δ＝４．６７（ｓ，２Ｈ）、５．０５（ｔ，Ｊ＝７．３Ｈｚ，２Ｈ）、５．６４（ｔ，Ｊ＝７．６Ｈｚ，２Ｈ）、６．５９－６．９０（ｍ，１２Ｈ）、７．０７－７．２３（ｍ，６Ｈ）、７．４５－７．５９（ｍ，１０Ｈ）、８．５５－８．６６（ｍ，４Ｈ）。 The results of NMR analysis of the obtained organic matter were as follows.
1 HNMR (DMSO-d6, 392MHz); δ = 4.67 (s, 2H), 5.05 (t, J = 7.3Hz, 2H), 5.64 (t, J = 7.6Hz, 2H) , 6.59-6.90 (m, 12H), 7.07-7.23 (m, 6H), 7.45-7.59 (m, 10H), 8.55-8.66 (m, 4H).
以上の結果から、得られた有機物の示性式はＣ60Ｈ38Ｎ4であり、分子量は８１４であると判断された。
From the above results, it was determined that the formula of the obtained organic substance was C 60 H 38 N 4 and the molecular weight was 814.
この場合の化学反応式を、下記に示す。
The chemical reaction formula in this case is shown below.
以下、生成物である有機物をＤＣＺ－２０という。
Hereinafter, the organic substance that is the product will be referred to as DCZ-20.
［有機物（ジカルバゾリルベンゼン類化合物）の物性評価］
ＤＣＺ－１、ＤＣＺ－２、ＤＣＺ－３、ＤＣＺ－４、ＤＣＺ－９、ＤＣＺ－１０、ＤＣＺ－１１、ＤＣＺ－１２、ＤＣＺ－１３、ＤＣＺ－１４及びＤＣＺ－１５につき、ガラス転移温度（Ｔｇ）、ＨＯＭＯ、ＬＵＭＯ、Ｓ１、Ｔ１、吸収端、蛍光極大波長、量子収率及び酸化電位を求めた。結果を、図２に一括して示す。上記の化合物のガラス転移温度は、全て１００℃以上である。従って、これらの化合物は、有機ＥＬ素子の各層の素材として好適である。 [Physical property evaluation of organic substances (dicarbazolylbenzene compounds)]
The glass transition temperature (Tg ), HOMO, LUMO, S1, T1, absorption edge, maximum fluorescence wavelength, quantum yield, and oxidation potential were determined. The results are collectively shown in FIG. 2. The glass transition temperatures of all of the above compounds are 100°C or higher. Therefore, these compounds are suitable as materials for each layer of an organic EL element.
ＤＣＺ－１、ＤＣＺ－２、ＤＣＺ－３、ＤＣＺ－４、ＤＣＺ－９、ＤＣＺ－１０、ＤＣＺ－１１、ＤＣＺ－１２、ＤＣＺ－１３、ＤＣＺ－１４及びＤＣＺ－１５につき、ガラス転移温度（Ｔｇ）、ＨＯＭＯ、ＬＵＭＯ、Ｓ１、Ｔ１、吸収端、蛍光極大波長、量子収率及び酸化電位を求めた。結果を、図２に一括して示す。上記の化合物のガラス転移温度は、全て１００℃以上である。従って、これらの化合物は、有機ＥＬ素子の各層の素材として好適である。 [Physical property evaluation of organic substances (dicarbazolylbenzene compounds)]
The glass transition temperature (Tg ), HOMO, LUMO, S1, T1, absorption edge, maximum fluorescence wavelength, quantum yield, and oxidation potential were determined. The results are collectively shown in FIG. 2. The glass transition temperatures of all of the above compounds are 100°C or higher. Therefore, these compounds are suitable as materials for each layer of an organic EL element.
図２から、各化合物の第一励起三重項状態（Ｔ１）のエネルギが高いことが分かる。また、各化合物におけるＨＯＭＯエネルギ（ＥＨＯＭＯ）及び最低非占有準位エネルギ（ＥＬＵＭＯ）は、特に青色発光材料を発光層に含む場合の電荷輸送材として用いるに当たって、適切な範囲内である。
From FIG. 2, it can be seen that the energy of the first excited triplet state (T1) of each compound is high. In addition, the HOMO energy (EHOMO) and lowest unoccupied level energy (ELUMO) of each compound are within appropriate ranges, especially when used as a charge transport material when a blue light emitting material is included in the light emitting layer.
［素子の評価その１］
ＤＣＺ－９又はＤＣＺ－１０をホスト材料として含む発光層を備え、図１に示される構造を有する有機ＥＬ素子をそれぞれ作製した。比較のため、ＵＲＰ又は３，３’－ジ（９Ｈ－カルバゾール－９－イル）－１，１’－ビフェニルをホスト材料として含む発光層を備え、図１に示される構造を有する有機ＥＬ素子をそれぞれ作製した。以下、３，３’－ジ（９Ｈ－カルバゾール－９－イル）－１，１’－ビフェニルをｍ－ＣＢＰと表記する。 [Element evaluation part 1]
Organic EL devices each having a structure shown in FIG. 1 and having a light emitting layer containing DCZ-9 or DCZ-10 as a host material were manufactured. For comparison, an organic EL element having the structure shown in FIG. 1 was prepared, including a light-emitting layer containing URP or 3,3'-di(9H-carbazol-9-yl)-1,1'-biphenyl as a host material. Each was produced. Hereinafter, 3,3'-di(9H-carbazol-9-yl)-1,1'-biphenyl will be referred to as m-CBP.
ＤＣＺ－９又はＤＣＺ－１０をホスト材料として含む発光層を備え、図１に示される構造を有する有機ＥＬ素子をそれぞれ作製した。比較のため、ＵＲＰ又は３，３’－ジ（９Ｈ－カルバゾール－９－イル）－１，１’－ビフェニルをホスト材料として含む発光層を備え、図１に示される構造を有する有機ＥＬ素子をそれぞれ作製した。以下、３，３’－ジ（９Ｈ－カルバゾール－９－イル）－１，１’－ビフェニルをｍ－ＣＢＰと表記する。 [Element evaluation part 1]
Organic EL devices each having a structure shown in FIG. 1 and having a light emitting layer containing DCZ-9 or DCZ-10 as a host material were manufactured. For comparison, an organic EL element having the structure shown in FIG. 1 was prepared, including a light-emitting layer containing URP or 3,3'-di(9H-carbazol-9-yl)-1,1'-biphenyl as a host material. Each was produced. Hereinafter, 3,3'-di(9H-carbazol-9-yl)-1,1'-biphenyl will be referred to as m-CBP.
各有機ＥＬ素子に蛍光、燐光又は熱活性化遅延蛍光（ＴＡＤＦ）を発光させて寿命を評価した。なお、寿命は、発光強度が初期特性の９０％に低下するまでの時間である。結果を、図３に併せて示す。この図３から、ＤＣＺ－９又はＤＣＺ－１０を発光層のホスト材料とする有機ＥＬ素子の寿命が、ＵＲＰ又はｍ－ＣＢＰを発光層のホスト材料とする有機ＥＬ素子の寿命に比べて優れていることが分かる。
The lifetime of each organic EL element was evaluated by causing it to emit fluorescence, phosphorescence, or thermally activated delayed fluorescence (TADF). Note that the lifetime is the time until the emission intensity decreases to 90% of the initial characteristic. The results are also shown in FIG. From FIG. 3, it can be seen that the lifetime of the organic EL device using DCZ-9 or DCZ-10 as the host material for the emissive layer is superior to that of the organic EL device using URP or m-CBP as the host material for the emissive layer. I know that there is.
また、図３には特に示していないが、蛍光を発光させた場合では、ＤＣＺ－９又はＤＣＺ－１０を発光層のホスト材料とする有機ＥＬ素子は、ＵＲＰを発光層のホスト材料とする有機ＥＬ素子よりも優れた効率を示した。
Although not particularly shown in FIG. 3, in the case of emitting fluorescence, an organic EL device using DCZ-9 or DCZ-10 as the host material of the emitting layer is different from an organic EL device using URP as the host material of the emitting layer. It showed better efficiency than EL devices.
［素子の評価その２］
正孔注入層（ＨＩＬ）、正孔輸送層（ＨＴＬ）、電子ブロック層（ＥＢＬ）及び正孔ブロック層（ＨＢＬ）を有する９種類の有機ＥＬ素子を作製した。以下、９種類の有機ＥＬ素子を、それぞれ、評価素子１～評価素子９と表記する。評価素子１～評価素子９におけるＨＩＬ、ＨＴＬ、ＥＢＬ及びＨＢＬに含まれる有機化合物として、図４に示す物質を用いた。図４に示すように、評価素子１～評価素子９においては、ＨＩＬ、ＨＴＬ、ＥＢＬ又はＨＢＬの少なくともいずれかの層にＤＣＺ－９又はＤＣＺ－１０が含まれている。 [Element evaluation part 2]
Nine types of organic EL devices having a hole injection layer (HIL), a hole transport layer (HTL), an electron block layer (EBL), and a hole block layer (HBL) were fabricated. Hereinafter, the nine types of organic EL elements will be referred to asevaluation elements 1 to 9, respectively. The substances shown in FIG. 4 were used as organic compounds contained in HIL, HTL, EBL, and HBL in Evaluation Elements 1 to 9. As shown in FIG. 4, in evaluation elements 1 to 9, DCZ-9 or DCZ-10 is included in at least one of the HIL, HTL, EBL, and HBL layers.
正孔注入層（ＨＩＬ）、正孔輸送層（ＨＴＬ）、電子ブロック層（ＥＢＬ）及び正孔ブロック層（ＨＢＬ）を有する９種類の有機ＥＬ素子を作製した。以下、９種類の有機ＥＬ素子を、それぞれ、評価素子１～評価素子９と表記する。評価素子１～評価素子９におけるＨＩＬ、ＨＴＬ、ＥＢＬ及びＨＢＬに含まれる有機化合物として、図４に示す物質を用いた。図４に示すように、評価素子１～評価素子９においては、ＨＩＬ、ＨＴＬ、ＥＢＬ又はＨＢＬの少なくともいずれかの層にＤＣＺ－９又はＤＣＺ－１０が含まれている。 [Element evaluation part 2]
Nine types of organic EL devices having a hole injection layer (HIL), a hole transport layer (HTL), an electron block layer (EBL), and a hole block layer (HBL) were fabricated. Hereinafter, the nine types of organic EL elements will be referred to as
なお、評価素子２のＨＴＬと、評価素子５のＨＩＬとにそれぞれ含まれているＯＰＤＡ－１０とは、化学構造式が以下のように示される有機化合物である。
Note that OPDA-10 contained in HTL of evaluation element 2 and HIL of evaluation element 5, respectively, is an organic compound whose chemical structural formula is shown below.
これら評価素子１～評価素子９につき、効率と、発光強度が初期特性の９０％に低下するまでの時間（寿命）と、発光強度が初期特性の９０％に低下するまでの電圧の変化（ΔＶ）とを評価した。結果を、図４に併せて示す。
For these evaluation elements 1 to 9, the efficiency, the time until the emission intensity decreases to 90% of the initial characteristics (lifetime), and the change in voltage until the emission intensity decreases to 90% of the initial characteristics (ΔV ) was evaluated. The results are also shown in FIG.
比較のため、ＤＣＺ－１等の有機化合物を含んだ層を全く有しない２種類の有機ＥＬ素子を作製した。以下、２種類の有機ＥＬ素子を、それぞれ、対照素子１及び対照素子２と表記する。なお、対照素子１及び対照素子２におけるＨＩＬ、ＨＴＬ、ＥＢＬ及びＨＢＬに含まれる有機化合物は、図４に示されている。
For comparison, two types of organic EL devices were fabricated that did not have any layer containing an organic compound such as DCZ-1. Hereinafter, the two types of organic EL elements will be referred to as control element 1 and control element 2, respectively. Note that organic compounds contained in HIL, HTL, EBL, and HBL in control element 1 and control element 2 are shown in FIG. 4.
対照素子１及び対照素子２についても、効率、寿命及びΔＶを評価した。結果を、図４に併せて示す。
Efficiency, lifetime, and ΔV were also evaluated for Control Element 1 and Control Element 2. The results are also shown in FIG.
図４から、ＤＣＺ－９又はＤＣＺ－１０を含む層を有する評価素子１～評価素子９が、ＤＣＺ－９又はＤＣＺ－１０を含む層を有しない対照素子１及び対照素子２よりも優れた寿命を示すことが分かる。また、評価素子１～評価素子９の効率は、対照素子１及び対照素子２と略同等であるか、又は上回っている。以上のように、ＤＣＺ－９又はＤＣＺ－１０を含む層を有する有機ＥＬ素子（評価素子１～評価素子９）は、従来技術に係る有機ＥＬ素子（対照素子１及び対照素子２）と同等の効率を示し、且つ優れた寿命を示す。
From FIG. 4, it can be seen that Evaluation Elements 1 to 9 having layers containing DCZ-9 or DCZ-10 have better lifetimes than Control Elements 1 and 2 that do not have layers containing DCZ-9 or DCZ-10. It can be seen that this shows that Furthermore, the efficiency of Evaluation Elements 1 to 9 is approximately equal to or higher than that of Comparative Element 1 and Comparative Element 2. As described above, the organic EL elements (Evaluation Elements 1 to 9) having layers containing DCZ-9 or DCZ-10 are equivalent to the organic EL elements according to the prior art (Control Element 1 and Control Element 2). Demonstrates efficiency and excellent longevity.
１０…有機ＥＬ素子 １２…ガラス基板
１４…アノード １６…正孔輸送層
１８…発光層 ２０…電子輸送層
２２…カソード DESCRIPTION OFSYMBOLS 10...Organic EL element 12...Glass substrate 14...Anode 16...Hole transport layer 18...Light emitting layer 20...Electron transport layer 22...Cathode
１４…アノード １６…正孔輸送層
１８…発光層 ２０…電子輸送層
２２…カソード DESCRIPTION OF
Claims (8)
- ２個のカルバゾリル基が互いに結合した１個以上のジカルバゾリル基、又は、１個以上の官能基が結合した１個以上の置換ジカルバゾリル基を有し、前記１個以上のジカルバゾリル基又は前記１個以上の置換ジカルバゾリル基がベンゼン環に結合したジカルバゾリルベンゼンを基本骨格として含み、下記の構造式（１）で示されるジカルバゾリルベンゼン類化合物。
Ｒ６及びＲ７は、置換芳香族炭化水素基もしくは無置換芳香族炭化水素基であるか、又は、置換窒素含有芳香族複素環基もしくは無置換窒素含有芳香族複素環基である。
R6 and R7 are substituted aromatic hydrocarbon groups or unsubstituted aromatic hydrocarbon groups, or substituted nitrogen-containing aromatic heterocyclic groups or unsubstituted nitrogen-containing aromatic heterocyclic groups.
- 請求項１記載のジカルバゾリルベンゼン類化合物において、前記１個以上のジカルバゾリル基として２個のジカルバゾリル基が前記ベンゼン環に結合するか、前記１個以上の置換ジカルバゾリル基として２個の置換ジカルバゾリル基が前記ベンゼン環に結合するか、又は、１個のジカルバゾリル基と１個の置換ジカルバゾリル基とが前記ベンゼン環に結合したジカルバゾリルベンゼン類化合物。 2. The dicarbazolylbenzene compound according to claim 1, wherein the one or more dicarbazolyl groups are two dicarbazolyl groups bonded to the benzene ring, or the one or more substituted dicarbazolyl groups are two substituted dicarbazolyl groups. A dicarbazolylbenzene compound in which a group is bonded to the benzene ring, or one dicarbazolyl group and one substituted dicarbazolyl group are bonded to the benzene ring.
- 請求項２記載のジカルバゾリルベンゼン類化合物において、前記ベンゼン環にカルバゾリル基又は置換カルバゾリル基がさらに結合したジカルバゾリルベンゼン類化合物。 The dicarbazolylbenzene compound according to claim 2, wherein a carbazolyl group or a substituted carbazolyl group is further bonded to the benzene ring.
- 請求項２記載のジカルバゾリルベンゼン類化合物において、前記２個のジカルバゾリル基同士、前記２個の置換ジカルバゾリル基同士、又は前記１個のジカルバゾリル基と前記１個の置換ジカルバゾリル基とがｏ－位の位置関係にあるジカルバゾリルベンゼン類化合物。 In the dicarbazolylbenzene compound according to claim 2, the two dicarbazolyl groups, the two substituted dicarbazolyl groups, or the one dicarbazolyl group and the one substituted dicarbazolyl group are o- Dicarbazolylbenzene compounds in positional relationship.
- 請求項１記載のジカルバゾリルベンゼン類化合物において、ジカルバゾリル基又は置換ジカルバゾリル基がベンゼン環に結合したジカルバゾリルベンゼンに対し、ジカルバゾリル基又は置換ジカルバゾリル基がフェニル基に結合した官能基が結合したジカルバゾリルベンゼン類化合物。 In the dicarbazolylbenzene compound according to claim 1, a functional group in which a dicarbazolyl group or a substituted dicarbazolyl group is bonded to a phenyl group is bonded to a dicarbazolylbenzene in which a dicarbazolyl group or a substituted dicarbazolyl group is bonded to a benzene ring. dicarbazolylbenzene compounds.
- 請求項５記載のジカルバゾリルベンゼン類化合物において、前記官能基が前記ジカルバゾリル基又は前記置換ジカルバゾリル基に対してｏ－位の位置関係にあるジカルバゾリルベンゼン類化合物。 The dicarbazolylbenzene compound according to claim 5, wherein the functional group is at the o-position with respect to the dicarbazolyl group or the substituted dicarbazolyl group.
- 請求項１記載のジカルバゾリルベンゼン類化合物において、Ｌ１～Ｌ３の少なくともいずれか１個がＮを含む官能基であるジカルバゾリルベンゼン類化合物。 The dicarbazolylbenzene compound according to claim 1, wherein at least one of L1 to L3 is a functional group containing N.
- 請求項１～７のいずれか１項に記載されたジカルバゾリルベンゼン類化合物を含む層を備える有機エレクトロルミネッセンス素子（１０）。 An organic electroluminescent device (10) comprising a layer containing the dicarbazolylbenzene compound according to any one of claims 1 to 7.
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| KR1020247002001A KR20240023619A (en) | 2022-03-10 | 2023-03-09 | Dicarbazolyl compounds and organic electroluminescent devices |
| PCT/JP2023/009107 WO2023171761A1 (en) | 2022-03-10 | 2023-03-09 | Dicarbazolyl compound and organic electroluminescence element |
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