JP2021111778A - 複数の有機エレクトロルミネセント材料及びこれを含む有機エレクトロルミネセントデバイス - Google Patents
複数の有機エレクトロルミネセント材料及びこれを含む有機エレクトロルミネセントデバイス Download PDFInfo
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- JP2021111778A JP2021111778A JP2020207112A JP2020207112A JP2021111778A JP 2021111778 A JP2021111778 A JP 2021111778A JP 2020207112 A JP2020207112 A JP 2020207112A JP 2020207112 A JP2020207112 A JP 2020207112A JP 2021111778 A JP2021111778 A JP 2021111778A
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- substituted
- unsubstituted
- alkyl
- organic electroluminescent
- arylamino
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- 239000000463 material Substances 0.000 title claims abstract description 106
- 150000001875 compounds Chemical class 0.000 claims abstract description 105
- -1 dehydrogen Chemical class 0.000 claims description 218
- 239000010410 layer Substances 0.000 claims description 169
- 125000003118 aryl group Chemical group 0.000 claims description 63
- 125000001072 heteroaryl group Chemical group 0.000 claims description 60
- 125000000217 alkyl group Chemical group 0.000 claims description 55
- 125000001769 aryl amino group Chemical group 0.000 claims description 55
- 230000005525 hole transport Effects 0.000 claims description 45
- 125000005104 aryl silyl group Chemical group 0.000 claims description 36
- 229910052739 hydrogen Inorganic materials 0.000 claims description 31
- 239000001257 hydrogen Substances 0.000 claims description 31
- 125000001424 substituent group Chemical group 0.000 claims description 28
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 claims description 27
- 239000002019 doping agent Substances 0.000 claims description 25
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 22
- 125000005241 heteroarylamino group Chemical group 0.000 claims description 22
- 150000002431 hydrogen Chemical class 0.000 claims description 22
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 20
- 239000012044 organic layer Substances 0.000 claims description 19
- 125000005842 heteroatom Chemical group 0.000 claims description 17
- 229910052757 nitrogen Inorganic materials 0.000 claims description 17
- 125000006323 alkenyl amino group Chemical group 0.000 claims description 16
- 229910052805 deuterium Inorganic materials 0.000 claims description 16
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 16
- 229910052760 oxygen Inorganic materials 0.000 claims description 16
- 229910052736 halogen Inorganic materials 0.000 claims description 15
- 150000002367 halogens Chemical class 0.000 claims description 15
- 125000002950 monocyclic group Chemical group 0.000 claims description 14
- 229910052717 sulfur Inorganic materials 0.000 claims description 14
- 125000003545 alkoxy group Chemical group 0.000 claims description 13
- 229910052796 boron Inorganic materials 0.000 claims description 13
- 125000003342 alkenyl group Chemical group 0.000 claims description 12
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 12
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims description 12
- 125000003367 polycyclic group Chemical group 0.000 claims description 10
- 125000000739 C2-C30 alkenyl group Chemical group 0.000 claims description 9
- 125000005103 alkyl silyl group Chemical group 0.000 claims description 9
- 125000002723 alicyclic group Chemical group 0.000 claims description 8
- 125000003282 alkyl amino group Chemical group 0.000 claims description 8
- 125000000732 arylene group Chemical group 0.000 claims description 8
- 229910052710 silicon Inorganic materials 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 229910052698 phosphorus Inorganic materials 0.000 claims description 7
- 125000005549 heteroarylene group Chemical group 0.000 claims description 6
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 125000006822 tri(C1-C30) alkylsilyl group Chemical group 0.000 claims description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000004947 alkyl aryl amino group Chemical group 0.000 claims description 2
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 2
- 125000005110 aryl thio group Chemical group 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 125000005105 dialkylarylsilyl group Chemical group 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000005415 substituted alkoxy group Chemical group 0.000 claims description 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 2
- 125000003107 substituted aryl group Chemical group 0.000 claims description 2
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 2
- 125000004665 trialkylsilyl group Chemical group 0.000 claims description 2
- 125000006193 alkinyl group Chemical group 0.000 claims 1
- 125000005106 triarylsilyl group Chemical group 0.000 claims 1
- 238000002347 injection Methods 0.000 description 27
- 239000007924 injection Substances 0.000 description 27
- 0 Cc1c(*)c2c(*)c(*)c(c(*)c(*)c3c4*3)c4c2c(*)c1* Chemical compound Cc1c(*)c2c(*)c(*)c(c(*)c(*)c3c4*3)c4c2c(*)c1* 0.000 description 24
- 230000000903 blocking effect Effects 0.000 description 24
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 23
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 19
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 12
- 125000004432 carbon atom Chemical group C* 0.000 description 11
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 11
- 238000000034 method Methods 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 9
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 9
- 150000001555 benzenes Chemical class 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 125000000304 alkynyl group Chemical group 0.000 description 6
- 235000010290 biphenyl Nutrition 0.000 description 6
- 239000004305 biphenyl Substances 0.000 description 6
- 125000001624 naphthyl group Chemical group 0.000 description 6
- 238000007740 vapor deposition Methods 0.000 description 6
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 5
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 5
- 125000000623 heterocyclic group Chemical group 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
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- 238000006243 chemical reaction Methods 0.000 description 4
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- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 3
- 235000000177 Indigofera tinctoria Nutrition 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- ABRVLXLNVJHDRQ-UHFFFAOYSA-N [2-pyridin-3-yl-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound FC(C1=CC(=CC(=N1)C=1C=NC=CC=1)CN)(F)F ABRVLXLNVJHDRQ-UHFFFAOYSA-N 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 229940097275 indigo Drugs 0.000 description 3
- COHYTHOBJLSHDF-UHFFFAOYSA-N indigo powder Natural products N1C2=CC=CC=C2C(=O)C1=C1C(=O)C2=CC=CC=C2N1 COHYTHOBJLSHDF-UHFFFAOYSA-N 0.000 description 3
- 125000005647 linker group Chemical group 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- 229910001507 metal halide Inorganic materials 0.000 description 3
- 150000005309 metal halides Chemical class 0.000 description 3
- 229910044991 metal oxide Inorganic materials 0.000 description 3
- 150000004706 metal oxides Chemical class 0.000 description 3
- 150000002790 naphthalenes Chemical group 0.000 description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 3
- 229950000688 phenothiazine Drugs 0.000 description 3
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 3
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- 238000005215 recombination Methods 0.000 description 3
- 230000006798 recombination Effects 0.000 description 3
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- 125000003003 spiro group Chemical group 0.000 description 3
- 238000006467 substitution reaction Methods 0.000 description 3
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 description 2
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical group C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 2
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical group C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
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- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 239000002841 Lewis acid Substances 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
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- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- UHOVQNZJYSORNB-MZWXYZOWSA-N benzene-d6 Chemical compound [2H]C1=C([2H])C([2H])=C([2H])C([2H])=C1[2H] UHOVQNZJYSORNB-MZWXYZOWSA-N 0.000 description 2
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- 238000000576 coating method Methods 0.000 description 2
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- 125000005299 dibenzofluorenyl group Chemical group C1(=CC=CC2=C3C(=C4C=5C=CC=CC5CC4=C21)C=CC=C3)* 0.000 description 2
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- IYYZUPMFVPLQIF-ALWQSETLSA-N dibenzothiophene Chemical group C1=CC=CC=2[34S]C3=C(C=21)C=CC=C3 IYYZUPMFVPLQIF-ALWQSETLSA-N 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
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- 239000001301 oxygen Chemical group 0.000 description 2
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- OIAQMFOKAXHPNH-UHFFFAOYSA-N 1,2-diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC=C1C1=CC=CC=C1 OIAQMFOKAXHPNH-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
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- OWPJBAYCIXEHFA-UHFFFAOYSA-N 1-phenyl-3-(3-phenylphenyl)benzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=C(C=CC=2)C=2C=CC=CC=2)=C1 OWPJBAYCIXEHFA-UHFFFAOYSA-N 0.000 description 1
- 125000006017 1-propenyl group Chemical group 0.000 description 1
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- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
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- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- UJVBZCCNLAAMOV-UHFFFAOYSA-N 2h-1,2-benzothiazine Chemical group C1=CC=C2C=CNSC2=C1 UJVBZCCNLAAMOV-UHFFFAOYSA-N 0.000 description 1
- CMLFRMDBDNHMRA-UHFFFAOYSA-N 2h-1,2-benzoxazine Chemical group C1=CC=C2C=CNOC2=C1 CMLFRMDBDNHMRA-UHFFFAOYSA-N 0.000 description 1
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
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- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- UQRONKZLYKUEMO-UHFFFAOYSA-N 4-methyl-1-(2,4,6-trimethylphenyl)pent-4-en-2-one Chemical group CC(=C)CC(=O)Cc1c(C)cc(C)cc1C UQRONKZLYKUEMO-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- 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
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- 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
-
- C—CHEMISTRY; METALLURGY
- 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
- C09K11/02—Use of particular materials as binders, particle coatings or suspension media therefor
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/54—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to two or three six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
- C07C211/61—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton with at least one of the condensed ring systems formed by three or more rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/76—Dibenzothiophenes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/027—Organoboranes and organoborohydrides
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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
- 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
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- 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
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
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Abstract
Description
R1〜R10は、それぞれ独立して、水素、重水素、ハロゲン、シアノ、置換若しくは非置換(C1〜C30)アルキル、置換若しくは非置換(C3〜C30)シクロアルキル、置換若しくは非置換(3〜7員)ヘテロシクロアルキル、置換若しくは非置換(C6〜C30)アリール、置換若しくは非置換(3〜30員)ヘテロアリール、置換若しくは非置換トリ(C1〜C30)アルキルシリル、置換若しくは非置換ジ(C1〜C30)アルキル(C6〜C30)アリールシリル、置換若しくは非置換(C1〜C30)アルキルジ(C6〜C30)アリールシリル、置換若しくは非置換トリ(C6〜C30)アリールシリル、又は
L1は、単結合、置換若しくは非置換(C6〜C30)アリーレン、又は置換若しくは非置換(3〜30員)ヘテロアリーレンを表し;
Ar1及びAr2は、それぞれ独立して、水素、重水素、置換若しくは非置換(C1〜C30)アルキル、置換若しくは非置換(C3〜C30)シクロアルキル、置換若しくは非置換(3〜7員)ヘテロシクロアルキル、置換若しくは非置換(C6〜C30)アリール、又は置換若しくは非置換(3〜30員)ヘテロアリールを表すか;或いはAr1及びAr2は、互いに結合して縮合環を形成し得;
*は、フェナントレンに結合する場所を表す。
環A、環B、及び環Cは、それぞれ独立して、B、N、O、S、Si、及びPから選択される少なくとも1つのヘテロ原子を含有し得る、置換若しくは非置換の単環式若しくは多環式(3〜50員)脂環式環若しくは芳香環、又はそれらの組合せを表し;環B及び環Cは、互いに結合して縮合環を形成し得;
Y1は、Bを表し;
X1及びX2は、それぞれ独立して、NR又はOを表し;
Rは、それぞれ独立して、水素、重水素、ハロゲン、シアノ、置換若しくは非置換(C1〜C30)アルキル、置換若しくは非置換(C6〜C30)アリール、置換若しくは非置換(3〜30員)ヘテロアリール、置換若しくは非置換(C3〜C30)シクロアルキル、置換若しくは非置換(C1〜C30)アルコキシ、置換若しくは非置換トリ(C1〜C30)アルキルシリル、置換若しくは非置換ジ(C1〜C30)アルキル(C6〜C30)アリールシリル、置換若しくは非置換(C1〜C30)アルキルジ(C6〜C30)アリールシリル、置換若しくは非置換トリ(C6〜C30)アリールシリル、置換若しくは非置換モノ−若しくはジ−(C1〜C30)アルキルアミノ、置換若しくは非置換モノ−若しくはジ−(C2〜C30)アルケニルアミノ、置換若しくは非置換モノ−若しくはジ−(C6〜C30)アリールアミノ、置換若しくは非置換モノ−若しくはジ−(3〜30員)ヘテロアリールアミノ、置換若しくは非置換(C1〜C30)アルキル(C2〜C30)アルケニルアミノ、置換若しくは非置換(C1〜C30)アルキル(C6〜C30)アリールアミノ、置換若しくは非置換(C1〜C30)アルキル(3〜30員)ヘテロアリールアミノ、置換若しくは非置換(C2〜C30)アルケニル(C6〜C30)アリールアミノ、置換若しくは非置換(C2〜C30)アルケニル(3〜30員)ヘテロアリールアミノ、又は置換若しくは非置換(3〜30員)ヘテロアリール(C6〜C30)アリールアミノを表すか;或いは環A、環B、及び環Cの少なくとも1つに結合して縮合環を形成し得る。
本開示による化合物の特定の組合せを有機層に含むことによって、従来の有機エレクトロルミネセントデバイスと比較してより長い寿命及び/又はより高い発光効率特性を有する有機エレクトロルミネセントデバイスを提供すること、並びにこれを使用して表示システム又は照明システムを製造することが可能である。加えて、この効果と共に又は或いはまた、従来の有機エレクトロルミネセントデバイスよりも藍色の光を発する有機エレクトロルミネセントデバイスを提供することができる。
但し、R1〜R10の少なくとも1つは、
*は、フェナントレンに結合する場所を表す。本開示の一実施形態によれば、R1〜R10は、それぞれ独立して、水素、重水素、置換若しくは非置換(C1〜C10)アルキル、置換若しくは非置換(C6〜C25)アリール、置換若しくは非置換(5〜25員)ヘテロアリール、又は
但し、R1〜R10の少なくとも1つは、
本開示の別の実施形態によれば、R1〜R10は、それぞれ独立して、水素、重水素、又は
但し、R1〜R10のいずれか1つは、
例えば、R1〜R10のいずれか1つは、
他は、それぞれ独立して、水素又は重水素であり得る。
L11は、単結合、置換若しくは非置換(C6〜C30)アリーレン、又は置換若しくは非置換(3〜30員)ヘテロアリーレンを表し;
Ar11及びAr12は、それぞれ独立して、置換若しくは非置換(C6〜C30)アリール、又は置換若しくは非置換(3〜30員)ヘテロアリールを表すか、或いはAr11及びAr12は、それらが結合している窒素と一緒に窒素含有(3〜30員)ヘテロアリールを形成し得;
R11〜R13は、それぞれ独立して、水素、重水素、ハロゲン、シアノ、カルボキシル、ニトロ、ヒドロキシル、置換若しくは非置換(C1〜C30)アルキル、置換若しくは非置換(C2〜C30)アルケニル、置換若しくは非置換(C2〜C30)アルキニル、置換若しくは非置換(C1〜C30)アルコキシ、置換若しくは非置換(C3〜C30)シクロアルキル、置換若しくは非置換(C3〜C30)シクロアルケニル、置換若しくは非置換(3〜7員)ヘテロシクロアルキル、置換若しくは非置換(C6〜C30)アリール、置換若しくは非置換(3〜30員)ヘテロアリール、−NR41R42、−SiR43R44R45、−SR46、−OR47、−COR48、又は−B(OR49)(OR50)を表すか、或いは隣接置換基と結合して単環式若しくは多環式(3〜30員)脂環式環若しくは芳香環、又はそれらの組合せを形成し、その炭素原子は、窒素、酸素、及び硫黄から選択される少なくとも1つのヘテロ原子と置き換えられてもよく;
R41〜R50は、それぞれ独立して、水素、重水素、ハロゲン、シアノ、カルボキシル、ニトロ、ヒドロキシル、置換若しくは非置換(C1〜C30)アルキル、置換若しくは非置換(C2〜C30)アルケニル、置換若しくは非置換(C2〜C30)アルキニル、置換若しくは非置換(C1〜C30)アルコキシ、置換若しくは非置換(C3〜C30)シクロアルキル、置換若しくは非置換(C3〜C30)シクロアルケニル、置換若しくは非置換(3〜7員)ヘテロシクロアルキル、置換若しくは非置換(C6〜C30)アリール、又は置換若しくは非置換(3〜30員)ヘテロアリールを表すか;或いは隣接置換基と結合して単環式若しくは多環式(3〜30員)脂環式環若しくは芳香環、又はそれらの組合せを形成し、その炭素原子は、窒素、酸素、及び硫黄から選択される少なくとも1つのヘテロ原子と置き換えられてもよく;
xは、1〜4の整数を表し、ここで、xが2以上の整数である場合、R11のそれぞれは、同じものであっても異なるものであってもよく;
yは、1〜3の整数を表し、ここで、yが2以上の整数である場合、R12のそれぞれは、同じものであっても異なるものであってもよく;
ヘテロアリール(エン)は、B、N、O、S、Si、及びPから選択される少なくとも1つのヘテロ原子を含有し;
ヘテロシクロアルキルは、O、S、及びNから選択される少なくとも1つのヘテロ原子を含有する。
L11及びL12は、それぞれ独立して、単結合、置換若しくは非置換(C6〜C30)アリーレン、又は置換若しくは非置換(3〜30員)ヘテロアリーレンを表し;
Ar11及びAr12は、それぞれ独立して、置換若しくは非置換(C6〜C30)アリール、又は置換若しくは非置換(3〜30員)ヘテロアリールを表し;
R21〜R28は、それぞれ独立して、水素、重水素、ハロゲン、シアノ、置換若しくは非置換(C1〜C30)アルキル、置換若しくは非置換(C6〜C30)アリール、置換若しくは非置換(3〜30員)ヘテロアリール、置換若しくは非置換(C3〜C30)シクロアルキル、置換若しくは非置換(C1〜C30)アルコキシ、置換若しくは非置換トリ(C1〜C30)アルキルシリル、置換若しくは非置換ジ(C1〜C30)アルキル(C6〜C30)アリールシリル、置換若しくは非置換(C1〜C30)アルキルジ(C6〜C30)アリールシリル、置換若しくは非置換トリ(C6〜C30)アリールシリル、置換若しくは非置換モノ−若しくはジ−(C1〜C30)アルキルアミノ、置換若しくは非置換モノ−若しくはジ−(C2〜C30)アルケニルアミノ、置換若しくは非置換モノ−若しくはジ−(C6〜C30)アリールアミノ、置換若しくは非置換モノ−若しくはジ−(3〜30員)ヘテロアリールアミノ、置換若しくは非置換(C1〜C30)アルキル(C2〜C30)アルケニルアミノ、置換若しくは非置換(C1〜C30)アルキル(C6〜C30)アリールアミノ、置換若しくは非置換(C1〜C30)アルキル(3〜30員)ヘテロアリールアミノ、置換若しくは非置換(C2〜C30)アルケニル(C6〜C30)アリールアミノ、置換若しくは非置換(C2〜C30)アルケニル(3〜30員)ヘテロアリールアミノ、又は置換若しくは非置換(3〜30員)ヘテロアリール(C6〜C30)アリールアミノを表す。
15gの9−フェナントレニル−ボロン酸(0.068mol)、28.7gの1−ブロモ−3−ヨードベンゼン(0.10mol)、3.9gのPd(PPh3)4(0.003mol)、18.7gのK2CO3(0.135mol)、510mLのトルエン、65mLのエタノール、及び65mLの蒸留水をフラスコに加え、混合物を5時間100℃で撹拌した。反応混合物を室温に冷却し、有機層を酢酸エチルで抽出した。残留水分を硫酸マグネシウムで除去し、有機層を乾燥させ、カラムクロマトグラフィーによって分離して13.9gの化合物1−1を得た(収率:61.7%)。
40.6gの化合物1−1(0.122mol)、53.3gのN−([1,1’−ビフェニル]−4−イル)−[1,1’:3’,1’’−テルフェニル]−4−アミン(0.134mol)、1.4gのPd(OAc)2(0.006mol)、5gのS−Phos(0.012mol)、23.4gのNaOt−Bu(0.244mmol)、及び610mLのトルエンをフラスコに加え、混合物を2時間150℃で還流下に撹拌した。反応混合物を室温に冷却し、有機層を酢酸エチルで抽出した。残留水分を硫酸マグネシウムで除去し、有機層を乾燥させ、カラムクロマトグラフィーによって分離して54.7gの化合物C−2を得た(収率:69.07%)。
以下の通り、本開示による有機エレクトロルミネセント化合物を使用してOLEDを製造した:OLED用のガラス基板上の透明電極酸化インジウムスズ(ITO)薄膜(10Ω/sq)(ジオマテック株式会社、日本)を、順次、アセトン、エタノール及び蒸留水での超音波洗浄にかけ、次いでイソプロパノール中に保存した。チャンバー中の真空度が10−6トールに達するまで排気した後、ITO基板を真空蒸着装置の基板ホルダーに装着した。化合物HT−1を真空蒸着装置のセルに導入し、化合物HI−1を真空蒸着装置の別のセルに導入した。2つの材料を蒸発させ、化合物HI−1を、化合物HI−1及び化合物HT−1の総量を基準として3重量%のドーピング量で蒸着させてITO基材上に10nmの厚さを有する正孔注入層を形成した。次に、化合物HT−1を正孔注入層上に蒸着させて75nmの厚さを有する第1正孔輸送層を形成した。次いで、化合物C−2を真空蒸着装置の別のセルに導入し、セルに電流を流すことによって蒸発させ、それにより第1正孔輸送層上に5nmの厚さを有する第2正孔輸送層を形成した。正孔注入層及び正孔輸送層を形成した後、以下の通り発光層をそれの上に形成した:化合物BH−1を発光層のホストとして真空蒸着装置のセルに導入し、化合物BD−2をドーパントとして別のセルに導入した。2つの材料を蒸発させ、ホスト及びドーパントの総量を基準として2重量%のドーピング量でドーパントを蒸着させて第2正孔輸送層上に20nmの厚さを有する発光層を形成した。次に、化合物ET−1を蒸着させて発光層上に5nmの厚さを有する正孔阻止層を形成した。化合物ET−2及び化合物EI−1を2つの他のセルにおいて1:1の比で蒸発させて正孔阻止層上に30nmの厚さを有する電子輸送層を形成した。2nmの厚さを有する電子注入層として化合物EI−1を蒸着させた後、80nmの厚さを有するAlカソードを別の真空蒸着装置によって蒸着させた。このようにして、OLEDを製造した。
化合物C−50を第2正孔輸送層に使用したことを除いて、デバイス実施例1と同じ方法でOLEDを製造した。
化合物BD−1を発光層のドーパントとして使用したことを除いて、デバイス実施例1と同じ方法でOLEDを製造した。
Claims (11)
- 少なくとも1つの第1化合物及び少なくとも1つの第2化合物を含む複数の有機エレクトロルミネセント材料であって、前記第1化合物が、以下の式1:
R1〜R10は、それぞれ独立して、水素、重水素、ハロゲン、シアノ、置換若しくは非置換(C1〜C30)アルキル、置換若しくは非置換(C3〜C30)シクロアルキル、置換若しくは非置換(3〜7員)ヘテロシクロアルキル、置換若しくは非置換(C6〜C30)アリール、置換若しくは非置換(3〜30員)ヘテロアリール、置換若しくは非置換トリ(C1〜C30)アルキルシリル、置換若しくは非置換ジ(C1〜C30)アルキル(C6〜C30)アリールシリル、置換若しくは非置換(C1〜C30)アルキルジ(C6〜C30)アリールシリル、置換若しくは非置換トリ(C6〜C30)アリールシリル、又は
L1は、単結合、置換若しくは非置換(C6〜C30)アリーレン、又は置換若しくは非置換(3〜30員)ヘテロアリーレンを表し;
Ar1及びAr2は、それぞれ独立して、水素、重水素、置換若しくは非置換(C1〜C30)アルキル、置換若しくは非置換(C3〜C30)シクロアルキル、置換若しくは非置換(3〜7員)ヘテロシクロアルキル、置換若しくは非置換(C6〜C30)アリール、又は置換若しくは非置換(3〜30員)ヘテロアリールを表すか、或いはAr1及びAr2は、互いに結合して縮合環を形成し得;
*は、フェナントレンに結合する場所を表す]
で表され;
前記第2化合物が、以下の式2:
環A、環B、及び環Cは、それぞれ独立して、B、N、O、S、Si、及びPから選択される少なくとも1つのヘテロ原子を含有し得る、置換若しくは非置換の単環式若しくは多環式(3〜50員)脂環式環若しくは芳香環、又はそれらの組合せを表し;環B及び環Cは、互いに結合して縮合環を形成し得;
Y1は、Bを表し;
X1及びX2は、それぞれ独立して、NR又はOを表し;
Rは、それぞれ独立して、水素、重水素、ハロゲン、シアノ、置換若しくは非置換(C1〜C30)アルキル、置換若しくは非置換(C6〜C30)アリール、置換若しくは非置換(3〜30員)ヘテロアリール、置換若しくは非置換(C3〜C30)シクロアルキル、置換若しくは非置換(C1〜C30)アルコキシ、置換若しくは非置換トリ(C1〜C30)アルキルシリル、置換若しくは非置換ジ(C1〜C30)アルキル(C6〜C30)アリールシリル、置換若しくは非置換(C1〜C30)アルキルジ(C6〜C30)アリールシリル、置換若しくは非置換トリ(C6〜C30)アリールシリル、置換若しくは非置換モノ−若しくはジ−(C1〜C30)アルキルアミノ、置換若しくは非置換モノ−若しくはジ−(C2〜C30)アルケニルアミノ、置換若しくは非置換モノ−若しくはジ−(C6〜C30)アリールアミノ、置換若しくは非置換モノ−若しくはジ−(3〜30員)ヘテロアリールアミノ、置換若しくは非置換(C1〜C30)アルキル(C2〜C30)アルケニルアミノ、置換若しくは非置換(C1〜C30)アルキル(C6〜C30)アリールアミノ、置換若しくは非置換(C1〜C30)アルキル(3〜30員)ヘテロアリールアミノ、置換若しくは非置換(C2〜C30)アルケニル(C6〜C30)アリールアミノ、置換若しくは非置換(C2〜C30)アルケニル(3〜30員)ヘテロアリールアミノ、又は置換若しくは非置換(3〜30員)ヘテロアリール(C6〜C30)アリールアミノを表すか;或いは環A、環B、及び環Cの少なくとも1つと結合して縮合環を形成し得る]
で表される、複数の有機エレクトロルミネセント材料。 - 前記置換アルキル、前記置換アリール(エン)、前記置換ヘテロアリール(エン)、前記置換シクロアルキル、前記置換ヘテロシクロアルキル、前記置換アルコキシ、前記置換トリアルキルシリル、前記置換ジアルキルアリールシリル、前記置換アルキルジアリールシリル、前記置換トリアリールシリル、前記置換モノ−若しくはジ−アルキルアミノ、前記置換モノ−若しくはジ−アルケニルアミノ、前記置換モノ−若しくはジ−アリールアミノ、前記置換モノ−若しくはジ−ヘテロアリールアミノ、前記置換アルキルアルケニルアミノ、前記置換アルキルアリールアミノ、前記置換アルキルヘテロアリールアミノ、前記置換アルケニルアリールアミノ、前記置換アルケニルヘテロアリールアミノ、前記置換ヘテロアリールアリールアミノ、及び前記置換環の置換基が、重水素;ハロゲン;シアノ;カルボキシル;ニトロ;ヒドロキシル;非置換の若しくは少なくとも1個の重水素で置換された(C1〜C30)アルキル;ハロ(C1〜C30)アルキル;(C2〜C30)アルケニル;(C2〜C30)アルキニル;(C1〜C30)アルコキシ;(C1〜C30)アルキルチオ;(C3〜C30)シクロアルキル;(C3〜C30)シクロアルケニル;(3〜7員)ヘテロシクロアルキル;(C6〜C30)アリールオキシ;(C6〜C30)アリールチオ;非置換の若しくは重水素、(C1〜C30)アルキル、(C6〜C30)アリール、及びジ(C6〜C30)アリールアミノの少なくとも1つで置換された(3〜30員)ヘテロアリール;非置換の若しくは重水素、(C1〜C30)アルキル、(3〜30員)ヘテロアリール、及びジ(C6〜C30)アリールアミノの少なくとも1つで置換された(C6〜C30)アリール;トリ(C1〜C30)アルキルシリル;トリ(C6〜C30)アリールシリル;ジ(C1〜C30)アルキル(C6〜C30)アリールシリル;(C1〜C30)アルキルジ(C6〜C30)アリールシリル;アミノ;モノ−若しくはジ−(C1〜C30)アルキルアミノ;モノ−若しくはジ−(C2〜C30)アルケニルアミノ;非置換の若しくは重水素、(C1〜C30)アルキル、(3〜30員)ヘテロアリール、及びジ(C6〜C30)アリールアミノの少なくとも1つで置換されたモノ−若しくはジ−(C6〜C30)アリールアミノ;モノ−若しくはジ−(3〜30員)ヘテロアリールアミノ;(C1〜C30)アルキル(C2〜C30)アルケニルアミノ;(C1〜C30)アルキル(C6〜C30)アリールアミノ;(C1〜C30)アルキル(3〜30員)ヘテロアリールアミノ;(C2〜C30)アルケニル(C6〜C30)アリールアミノ;(C2〜C30)アルケニル(3〜30員)ヘテロアリールアミノ;非置換の若しくは(C1〜C30)アルキル及び(C6〜C30)アリールの少なくとも1つで置換された(3〜30員)ヘテロアリール(C6〜C30)アリールアミノ;(C1〜C30)アルキルカルボニル;(C1〜C30)アルコキシカルボニル;(C6〜C30)アリールカルボニル;ジ(C6〜C30)アリールボロニル;ジ(C1〜C30)アルキルボロニル;(C1〜C30)アルキル(C6〜C30)アリールボロニル;(C6〜C30)アリール(C1〜C30)アルキル;並びに(C1〜C30)アルキル(C6〜C30)アリールからなる群から選択される少なくとも1つである、請求項1に記載の複数の有機エレクトロルミネセント材料。
- 式2が、以下の式2−1:
Y1、X1、及びX2は、それぞれ独立して、請求項1において定義される通りであり;
R21〜R31は、それぞれ独立して、水素、重水素、ハロゲン、シアノ、置換若しくは非置換(C1〜C30)アルキル、置換若しくは非置換(C6〜C30)アリール、置換若しくは非置換(3〜30員)ヘテロアリール、置換若しくは非置換(C3〜C30)シクロアルキル、置換若しくは非置換(C1〜C30)アルコキシ、置換若しくは非置換トリ(C1〜C30)アルキルシリル、置換若しくは非置換ジ(C1〜C30)アルキル(C6〜C30)アリールシリル、置換若しくは非置換(C1〜C30)アルキルジ(C6〜C30)アリールシリル、置換若しくは非置換トリ(C6〜C30)アリールシリル、置換若しくは非置換モノ−若しくはジ−(C1〜C30)アルキルアミノ、置換若しくは非置換モノ−若しくはジ−(C2〜C30)アルケニルアミノ、置換若しくは非置換モノ−若しくはジ−(C6〜C30)アリールアミノ、置換若しくは非置換モノ−若しくはジ−(3〜30員)ヘテロアリールアミノ、置換若しくは非置換(C1〜C30)アルキル(C2〜C30)アルケニルアミノ、置換若しくは非置換(C1〜C30)アルキル(C6〜C30)アリールアミノ、置換若しくは非置換(C1〜C30)アルキル(3〜30員)ヘテロアリールアミノ、置換若しくは非置換(C2〜C30)アルケニル(C6〜C30)アリールアミノ、置換若しくは非置換(C2〜C30)アルケニル(3〜30員)ヘテロアリールアミノ、又は置換若しくは非置換(3〜30員)ヘテロアリール(C6〜C30)アリールアミノを表すか;或いはR21〜R31の隣接するものは、互いに結合して環を形成し得る]
で表される請求項1に記載の複数の有機エレクトロルミネセント材料。 - 式1で表される前記化合物が正孔輸送帯材料として含まれ、式2で表される前記化合物がドーパント材料として含まれる、請求項1に記載の複数の有機エレクトロルミネセント材料。
- 第1電極と、前記第1電極に面する第2電極と、前記第1電極と前記第2電極との間の有機層とを含む有機エレクトロルミネセントデバイスであって、前記有機層が、請求項1に記載の複数の有機エレクトロルミネセント材料を含むデバイス。
- 前記有機層が、正孔輸送帯の少なくとも1つの層と発光層の少なくとも1つの層とを含み、前記正孔輸送帯の少なくとも1つの層が式1で表される前記化合物を含み、前記発光層の少なくとも1つの層が式2で表される前記化合物を含む、請求項10に記載の有機エレクトロルミネセントデバイス。
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-
2020
- 2020-01-03 KR KR1020200000822A patent/KR20210087735A/ko not_active Application Discontinuation
- 2020-12-10 CN CN202011455219.2A patent/CN113072925A/zh active Pending
- 2020-12-11 US US17/119,671 patent/US20210210684A1/en active Pending
- 2020-12-14 JP JP2020207112A patent/JP2021111778A/ja active Pending
- 2020-12-14 DE DE102020133439.7A patent/DE102020133439A1/de active Pending
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US20240237511A1 (en) | 2024-07-11 |
DE102020133439A1 (de) | 2021-07-08 |
KR20210087735A (ko) | 2021-07-13 |
CN113072925A (zh) | 2021-07-06 |
US20210210684A1 (en) | 2021-07-08 |
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