CN106749412A - The carbazole analog derivative and the organic luminescent device using the derivative of a kind of meta phosphine oxygen groups substitution - Google Patents
The carbazole analog derivative and the organic luminescent device using the derivative of a kind of meta phosphine oxygen groups substitution Download PDFInfo
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- CN106749412A CN106749412A CN201611175687.8A CN201611175687A CN106749412A CN 106749412 A CN106749412 A CN 106749412A CN 201611175687 A CN201611175687 A CN 201611175687A CN 106749412 A CN106749412 A CN 106749412A
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- derivative
- oxygen groups
- analog derivative
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- SCHRRICRQNJJKN-UHFFFAOYSA-N P.[O] Chemical group P.[O] SCHRRICRQNJJKN-UHFFFAOYSA-N 0.000 title claims abstract description 26
- 238000006467 substitution reaction Methods 0.000 title claims abstract description 18
- 125000000609 carbazolyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 title claims 6
- 150000004982 aromatic amines Chemical class 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 9
- 125000001072 heteroaryl group Chemical group 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- 239000012044 organic layer Substances 0.000 claims description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- 239000005864 Sulphur Substances 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical group [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- 150000008378 aryl ethers Chemical class 0.000 claims description 3
- 150000004832 aryl thioethers Chemical class 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 229910052805 deuterium Inorganic materials 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 239000011737 fluorine Chemical group 0.000 claims description 3
- 229910052757 nitrogen Chemical group 0.000 claims description 3
- 150000002431 hydrogen Chemical group 0.000 claims 3
- 150000001716 carbazoles Chemical class 0.000 abstract description 20
- 239000000463 material Substances 0.000 abstract description 16
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 abstract description 6
- HQALDKFFRYFTKP-UHFFFAOYSA-N 2-[4-[4-(2-benzyl-1-benzothiophen-3-yl)phenyl]-2-bromo-6-(3-methoxyphenyl)phenoxy]acetic acid Chemical compound COC1=CC=CC(C=2C(=C(Br)C=C(C=2)C=2C=CC(=CC=2)C=2C3=CC=CC=C3SC=2CC=2C=CC=CC=2)OCC(O)=O)=C1 HQALDKFFRYFTKP-UHFFFAOYSA-N 0.000 abstract description 3
- ASUOLLHGALPRFK-UHFFFAOYSA-N phenylphosphonoylbenzene Chemical group C=1C=CC=CC=1P(=O)C1=CC=CC=C1 ASUOLLHGALPRFK-UHFFFAOYSA-N 0.000 abstract description 3
- 229940125904 compound 1 Drugs 0.000 description 52
- 230000008859 change Effects 0.000 description 27
- 150000001875 compounds Chemical class 0.000 description 27
- 238000001819 mass spectrum Methods 0.000 description 26
- 239000010410 layer Substances 0.000 description 24
- 230000015572 biosynthetic process Effects 0.000 description 20
- 238000003786 synthesis reaction Methods 0.000 description 20
- 238000006243 chemical reaction Methods 0.000 description 12
- 238000001704 evaporation Methods 0.000 description 11
- 230000008020 evaporation Effects 0.000 description 11
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 238000007738 vacuum evaporation Methods 0.000 description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 229910002027 silica gel Inorganic materials 0.000 description 6
- 239000000741 silica gel Substances 0.000 description 6
- 229960001866 silicon dioxide Drugs 0.000 description 6
- 230000005540 biological transmission Effects 0.000 description 5
- 239000012043 crude product Substances 0.000 description 5
- AOSZTAHDEDLTLQ-AZKQZHLXSA-N (1S,2S,4R,8S,9S,11S,12R,13S,19S)-6-[(3-chlorophenyl)methyl]-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-azapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one Chemical compound C([C@@H]1C[C@H]2[C@H]3[C@]([C@]4(C=CC(=O)C=C4[C@@H](F)C3)C)(F)[C@@H](O)C[C@@]2([C@@]1(C1)C(=O)CO)C)N1CC1=CC=CC(Cl)=C1 AOSZTAHDEDLTLQ-AZKQZHLXSA-N 0.000 description 4
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- IWZSHWBGHQBIML-ZGGLMWTQSA-N (3S,8S,10R,13S,14S,17S)-17-isoquinolin-7-yl-N,N,10,13-tetramethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-amine Chemical compound CN(C)[C@H]1CC[C@]2(C)C3CC[C@@]4(C)[C@@H](CC[C@@H]4c4ccc5ccncc5c4)[C@@H]3CC=C2C1 IWZSHWBGHQBIML-ZGGLMWTQSA-N 0.000 description 4
- ONBQEOIKXPHGMB-VBSBHUPXSA-N 1-[2-[(2s,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-4,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)propan-1-one Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1OC1=CC(O)=CC(O)=C1C(=O)CCC1=CC=C(O)C=C1 ONBQEOIKXPHGMB-VBSBHUPXSA-N 0.000 description 4
- UNILWMWFPHPYOR-KXEYIPSPSA-M 1-[6-[2-[3-[3-[3-[2-[2-[3-[[2-[2-[[(2r)-1-[[2-[[(2r)-1-[3-[2-[2-[3-[[2-(2-amino-2-oxoethoxy)acetyl]amino]propoxy]ethoxy]ethoxy]propylamino]-3-hydroxy-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-[(2r)-2,3-di(hexadecanoyloxy)propyl]sulfanyl-1-oxopropan-2-yl Chemical compound O=C1C(SCCC(=O)NCCCOCCOCCOCCCNC(=O)COCC(=O)N[C@@H](CSC[C@@H](COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)C(=O)NCC(=O)N[C@H](CO)C(=O)NCCCOCCOCCOCCCNC(=O)COCC(N)=O)CC(=O)N1CCNC(=O)CCCCCN\1C2=CC=C(S([O-])(=O)=O)C=C2CC/1=C/C=C/C=C/C1=[N+](CC)C2=CC=C(S([O-])(=O)=O)C=C2C1 UNILWMWFPHPYOR-KXEYIPSPSA-M 0.000 description 4
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- DVKJDTZKQLNZFD-UHFFFAOYSA-N CC(C)(c1ccccc1-c1ccc2)c1c2-[n]1c(cc(cc2)P(c3ccccc3)(c3cccc(C)c3)=O)c2c(cc2)c1cc2-c(cc1)cc2c1c([s]c1c3cccc1)c3[s]2 Chemical compound CC(C)(c1ccccc1-c1ccc2)c1c2-[n]1c(cc(cc2)P(c3ccccc3)(c3cccc(C)c3)=O)c2c(cc2)c1cc2-c(cc1)cc2c1c([s]c1c3cccc1)c3[s]2 DVKJDTZKQLNZFD-UHFFFAOYSA-N 0.000 description 1
- CUIAEZAJOFYNSY-UHFFFAOYSA-N CC1C(c2ccccn2)=CC=CC1[n]1c(cc(cc2)P(c3ccccc3)(c3ccccc3)=O)c2c(cc2)c1cc2-c(cc1)cc2c1c([s]c1c3cccc1)c3[s]2 Chemical compound CC1C(c2ccccn2)=CC=CC1[n]1c(cc(cc2)P(c3ccccc3)(c3ccccc3)=O)c2c(cc2)c1cc2-c(cc1)cc2c1c([s]c1c3cccc1)c3[s]2 CUIAEZAJOFYNSY-UHFFFAOYSA-N 0.000 description 1
- DRSHXJFUUPIBHX-UHFFFAOYSA-N COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 Chemical compound COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 DRSHXJFUUPIBHX-UHFFFAOYSA-N 0.000 description 1
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 description 1
- YFPJFKYCVYXDJK-UHFFFAOYSA-N Diphenylphosphine oxide Chemical compound C=1C=CC=CC=1[P+](=O)C1=CC=CC=C1 YFPJFKYCVYXDJK-UHFFFAOYSA-N 0.000 description 1
- NUGPIZCTELGDOS-QHCPKHFHSA-N N-[(1S)-3-[4-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)piperidin-1-yl]-1-pyridin-3-ylpropyl]cyclopentanecarboxamide Chemical compound C(C)(C)C1=NN=C(N1C1CCN(CC1)CC[C@@H](C=1C=NC=CC=1)NC(=O)C1CCCC1)C NUGPIZCTELGDOS-QHCPKHFHSA-N 0.000 description 1
- LFZAGIJXANFPFN-UHFFFAOYSA-N N-[3-[4-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)piperidin-1-yl]-1-thiophen-2-ylpropyl]acetamide Chemical compound C(C)(C)C1=NN=C(N1C1CCN(CC1)CCC(C=1SC=CC=1)NC(C)=O)C LFZAGIJXANFPFN-UHFFFAOYSA-N 0.000 description 1
- FIWILGQIZHDAQG-UHFFFAOYSA-N NC1=C(C(=O)NCC2=CC=C(C=C2)OCC(F)(F)F)C=C(C(=N1)N)N1N=C(N=C1)C1(CC1)C(F)(F)F Chemical compound NC1=C(C(=O)NCC2=CC=C(C=C2)OCC(F)(F)F)C=C(C(=N1)N)N1N=C(N=C1)C1(CC1)C(F)(F)F FIWILGQIZHDAQG-UHFFFAOYSA-N 0.000 description 1
- WDWGXXCEUNEXMB-UHFFFAOYSA-N O=P(C1C=CC=CC1)(c1ccccc1)c(cc1)cc2c1c(ccc(-c(cc1)cc3c1c([s]c1c4cccc1)c4[s]3)c1)c1[n]2-c1cccc(Sc2ccccc2)c1 Chemical compound O=P(C1C=CC=CC1)(c1ccccc1)c(cc1)cc2c1c(ccc(-c(cc1)cc3c1c([s]c1c4cccc1)c4[s]3)c1)c1[n]2-c1cccc(Sc2ccccc2)c1 WDWGXXCEUNEXMB-UHFFFAOYSA-N 0.000 description 1
- VGHZEXBNZSODKS-UHFFFAOYSA-N O=P(C1C=CC=CC1)(c1ccccc1)c1ccc(c(ccc(-c(cc2)cc3c2c([s]c2c4cccc2)c4[s]3)c2)c2[n]2-c(cc3)ccc3-c3ccccn3)c2c1 Chemical compound O=P(C1C=CC=CC1)(c1ccccc1)c1ccc(c(ccc(-c(cc2)cc3c2c([s]c2c4cccc2)c4[s]3)c2)c2[n]2-c(cc3)ccc3-c3ccccn3)c2c1 VGHZEXBNZSODKS-UHFFFAOYSA-N 0.000 description 1
- DSFRFYHDVUBZIO-UHFFFAOYSA-N O=P(c1ccccc1)(c1ccccc1)c(cc1)cc2c1c(ccc(-c(cc1)cc3c1c([s]c1c4cccc1)c4[s]3)c1)c1[n]2-c1cccc(Oc2cccc3c2cccc3)c1 Chemical compound O=P(c1ccccc1)(c1ccccc1)c(cc1)cc2c1c(ccc(-c(cc1)cc3c1c([s]c1c4cccc1)c4[s]3)c1)c1[n]2-c1cccc(Oc2cccc3c2cccc3)c1 DSFRFYHDVUBZIO-UHFFFAOYSA-N 0.000 description 1
- NLJBEBZGTDDJLY-UHFFFAOYSA-N O=P(c1ccccc1)(c1ccccc1)c1ccc(Cc(ccc(-c(cc2)cc3c2c([s]c2c4cccc2)c4[s]3)c2)c2N2C3C=CC(c4ccccc4)=CC3)c2c1 Chemical compound O=P(c1ccccc1)(c1ccccc1)c1ccc(Cc(ccc(-c(cc2)cc3c2c([s]c2c4cccc2)c4[s]3)c2)c2N2C3C=CC(c4ccccc4)=CC3)c2c1 NLJBEBZGTDDJLY-UHFFFAOYSA-N 0.000 description 1
- ARAVQKGHVJRQKZ-UHFFFAOYSA-N O=P(c1ccccc1)(c1ccccc1)c1ccc(c(ccc(-c(cc2)cc3c2c([s]c2c4cccc2)c4[s]3)c2)c2[n]2-c3c(ccc4cccc(cc5)c44)c4c5cc3)c2c1 Chemical compound O=P(c1ccccc1)(c1ccccc1)c1ccc(c(ccc(-c(cc2)cc3c2c([s]c2c4cccc2)c4[s]3)c2)c2[n]2-c3c(ccc4cccc(cc5)c44)c4c5cc3)c2c1 ARAVQKGHVJRQKZ-UHFFFAOYSA-N 0.000 description 1
- CBJLYVUYBXYHJS-UHFFFAOYSA-N O=P(c1ccccc1)(c1ccccc1)c1ccc(c(ccc(-c(cc2)cc3c2c([s]c2c4cccc2)c4[s]3)c2)c2[n]2-c3cccc4c3cccc4)c2c1 Chemical compound O=P(c1ccccc1)(c1ccccc1)c1ccc(c(ccc(-c(cc2)cc3c2c([s]c2c4cccc2)c4[s]3)c2)c2[n]2-c3cccc4c3cccc4)c2c1 CBJLYVUYBXYHJS-UHFFFAOYSA-N 0.000 description 1
- 238000006069 Suzuki reaction reaction Methods 0.000 description 1
- 238000006887 Ullmann reaction Methods 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 238000005885 boration reaction Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 230000017858 demethylation Effects 0.000 description 1
- 238000010520 demethylation reaction Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical class [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical class CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical class COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 1
Classifications
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- 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
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6561—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
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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
- 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
- H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
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- H—ELECTRICITY
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- H10K85/624—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing six or more rings
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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
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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
- 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
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- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
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- 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
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- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
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Abstract
The present invention provides the carbazole analog derivative and the organic luminescent device using the derivative of a kind of meta phosphine oxygen groups substitution, belongs to organic photoelectrical material technical field.The carbazole analog derivative that the carbazole analog derivative of meta phosphine oxygen groups substitution has structure shown in formula (I), meta phosphine oxygen groups substitution of the present invention connects benzothiophene derivative as core with carbazole meta, while meta connection diphenyl phosphine oxide group.Organic luminescent device prepared by the carbazole analog derivative that a kind of meta phosphine oxygen groups provided using the present invention are replaced, substantially reduces with luminous efficiency and external quantum efficiency higher, and driving voltage.
Description
Technical field
The present invention relates to organic photoelectrical material technical field, and in particular to a kind of carbazoles of meta phosphine oxygen groups substitution spreads out
Organic luminescent device biological and using the derivative.
Background technology
Organic electroluminescent refer to organic material under electric field action, excited by electric current and electric field and luminous showed
As.Organic electroluminescent LED (OLED) is the Display Technique of new generation that display is realized using this phenomenon.From U.S. in 1987
State Kodak Company Tang C.W. and Vanslyke S.A. made first organic electroluminescence device of function admirable with
Come, ORGANIC ELECTROLUMINESCENCE DISPLAYS has the advantage that the great interest for causing people due to it.
In the research of OLED, the selection of organic material plays conclusive effect.The organic material master used in OLED
There are hole-injecting material, hole mobile material, luminescent material, electron transport material and electron injection material etc., and main body material
Material is the main material of luminescent layer.In general, all of hole or electron-transporting type material of main part doping guest emitter are formed
Luminescent layer, exciton recombination region can optionally it is on the upper side certain on one side, so as to cause device efficiency and photochromic change, very seriously
The energy between triplet that may cause be quenched, efficiency roll-off is serious under causing high brightness.
The content of the invention
In view of this, it is an object of the invention to provide a kind of meta phosphine oxygen groups substitution carbazole analog derivative and use
The organic luminescent device of the derivative, derivative of the present invention connects benzothiophene derivative as core with carbazole meta, while meta
Connection diphenyl phosphine oxide group obtains the electronics and hole bipolar transmission section bar material of a kind of novelty, can be applied to as material of main part
Organic luminescent device.Organic luminescent device prepared by the carbazole analog derivative replaced using meta phosphine oxygen groups of the present invention, has
Luminous efficiency higher, lower driving voltage, and external quantum efficiency higher.
Present invention firstly provides a kind of carbazole analog derivative of meta phosphine oxygen groups substitution, with as described in formula (I)
Structural formula：
Wherein, R is selected from hydrogen, deuterium, fluorine, cyano group, substituted or unsubstituted C6-C50 aryl, substituted or unsubstituted C7-C50
It is any one in aralkyl, the arylamine of substituted or unsubstituted C6-C50, the heteroaromatic of substituted or unsubstituted C4-C40
Kind.
Preferably, R is selected from hydrogen, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C7-C30 aralkyl, takes
Generation or unsubstituted C6-C30 arylamine, the heteroaromatic of substituted or unsubstituted C4-C30 in any one.
Further preferably, R group is selected from any one in following structure：
X is selected from hydrogen, C6-C24 aryl, the aralkyl of C7-C30, the arylamine of C6-C16, the aryl ether of C6-C16, C6-C16
Aryl thioethers, the heteroaromatic of C4-C30 in any one；
Y is selected from carbon or nitrogen；
Z is selected from oxygen or sulphur.
According to the present invention, the carbazole analog derivative of the meta phosphine oxygen groups substitution is not particularly limited, and is preferably as follows institute
Show：
The present invention also provides a kind of organic luminescent device, including first electrode, second electrode and is placed between two electrodes
One or more organic layers, it is characterised in that the carbazole analog derivative of at least one organic layer parlor position phosphine oxygen groups substitution.
Beneficial effects of the present invention：
Compared with prior art, the present invention is provided a kind of carbazole analog derivative of meta phosphine oxygen groups substitution and is spread out using this
Biological organic luminescent device, the carbazole analog derivative of meta phosphine oxygen groups substitution has structure shown in formula (I).Institute of the present invention
State the carbazole analog derivative containing phosphine oxygen groups and benzothiophene derivative is connected as core with carbazole meta, while meta connection diphenyl
Phosphine oxide group obtains the electronics and hole bipolar transmission section bar material of a kind of novelty, can be applied to organic illuminator as material of main part
Part.
Test result indicate that, prepared by the carbazole analog derivative that the meta phosphine oxygen groups provided using the present invention are replaced organic
Luminescent device, luminous efficiency reaches as high as 8.9cd/A, and driving voltage is minimum can reach 6.9V, and maximum external quantum efficiency is
17.6%, it is a kind of excellent OLED material.
Specific embodiment
Technical scheme below in conjunction with the embodiment of the present invention is clearly and completely described, it is clear that described implementation
Example is only a part of embodiment of the invention, rather than whole embodiments.Based on the embodiment in the present invention, this area is common
The every other embodiment that technical staff is obtained under the premise of creative work is not made, belongs to the model of present invention protection
Enclose.
It should be noted that unless otherwise prescribed, the implication of scientific and technical terminology used in the present invention and people in the art
The implication that member is generally understood is identical.
Aryl of the present invention refers to after removing a hydrogen atom on the aromatic core carbon of aromatic hydrocarbon molecule, to be left the total of univalent perssad
Claim.
Arylamine of the present invention refers to the amine for replacing base with an armaticity, i.e.-NH2,-NH- or nitrogen-containing group connection
Onto an aromatic hydrocarbon, one or more phenyl ring are usually contained in the structure of aromatic hydrocarbon.
Aromatic heterocycle of the present invention refers to that one or more the aromatic core carbon in aryl are obtained by hetero atom replacement
The general name of group, the hetero atom includes but is not limited to oxygen, sulphur and nitrogen-atoms, and the aromatic heterocycle can be mono-cyclic aromatic
Race's heterocyclic radical or condensed nucleus aromatic heterocyclic radical.
Present invention firstly provides the carbazole analog derivative of meta phosphine oxygen groups substitution, shown in its general structure such as formula (I)：
Wherein, R is selected from hydrogen, deuterium, fluorine, cyano group, substituted or unsubstituted C6-C50 aryl, substituted or unsubstituted C7-C50
It is any one in aralkyl, the arylamine of substituted or unsubstituted C6-C50, the heteroaromatic of substituted or unsubstituted C4-C40
Kind.
Preferably, R is selected from hydrogen, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C7-C30 aralkyl, takes
Generation or unsubstituted C6-C30 arylamine, the heteroaromatic of substituted or unsubstituted C4-C30 in any one.
Further preferably, R group is selected from any one in following structure：
X is selected from hydrogen, C6-C24 aryl, the aralkyl of C7-C30, the arylamine of C6-C16, the aryl ether of C6-C16, C6-C16
Aryl thioethers, the heteroaromatic of C4-C30 any one；
Y is selected from carbon or nitrogen；
Z is selected from oxygen or sulphur.
According to the present invention, the carbazole analog derivative of the meta phosphine oxygen groups substitution is not particularly limited, and is preferably as follows institute
Show：
It is enumerated above some specific structure shapes of the carbazole analog derivative of meta phosphine oxygen groups substitution of the present invention
Formula, but the carbazole analog derivative of meta phosphine oxygen groups of the present invention substitution is not limited to these listed chemical constitutions, it is all
Be based on structure shown in formula (I), R be for group as defined above should all be included.
A kind of carbazoles derivative preparation method of the substitution of meta phosphine oxygen groups shown in formula (I) of the present invention, including by Formula II
Shown compound by Suzuki, cyclization, boration, Suzuki coupling prepare VII, VII again with chloro diphenyl phosphine oxide alkane
Parent nucleus IX is obtained by n-BuLi coupling.Compound shown in Formula IX and the derivative containing R substituent are carried out into ullmann
Coupling or buchward coupling reactions obtain the compound shown in formula (I).
The present invention does not have particular/special requirement to the reaction condition of above-mentioned all kinds of reactions, with well known to those skilled in the art such
The normal condition of reaction.The present invention has no particular limits to the source of the raw material employed in above-mentioned all kinds of reactions, can
Think commercially available prod or prepared using preparation method well-known to those skilled in the art.Wherein, the selection of the R is ibid
It is described, will not be repeated here.
The present invention also provides a kind of organic luminescent device.What the organic luminescent device was well known to those skilled in the art
Organic luminescent device, organic luminescent device of the present invention preferably includes first electrode, second electrode, positioned at described first
One or more organic layers between electrode and second electrode.The organic layer preferably include hole injection layer, hole transmission layer,
At least one of which in electronic barrier layer, luminescent layer, hole blocking layer, electron transfer layer and electron injecting layer.Described luminescent layer
In containing derivative of the present invention preparation luminous organic material.
Embodiment 1：The preparation of compound 1
Step1, takes the compound III of 100mmol, adds compound II, the 300mmol potassium carbonate of 105mmol, 1mmol
Four triphenyl phosphorus palladiums, toluene 300ml, ethanol 60ml, water 60ml.Argon gas is replaced three times, and 5h, crude product mistake are reacted under reflux temperature
Silicagel column, obtains product 81mmol IV.
Step2, takes 81mmol compound IV, adds TFMS 300ml, room temperature reaction 24h.It is slow after the completion of reaction
Pour into water/pyridine=8:In 1 mixed liquor 6L.Heated solution reacts 30min to flowing back, and makes demethylation process reaction complete.It is cold
But after, crude product crosses silicagel column, obtains product 40mmol V.
Step3,40mmol compounds V is dissolved in anhydrous THF 200ml, cools to -78 degrees Celsius, is slowly added dropwise
80mmol n-BuLis, are warmed up to room temperature naturally, and reaction overnight, next day, adds 80mmol trimethylborates, stirs 2h.Add
Excessive watery hydrochloric acid is quenched reaction, and EA extractions, dry, concentration, crude product cross silicagel column and obtains 32mmol products VI.
Step4, takes the compound VI of 30mmol, adds the compound bromo carbazole of 15mmol, 45mmol potassium carbonate,
The triphenyl phosphorus palladiums of 0.15mmol tetra-, toluene 100ml, ethanol 10ml, water 10ml.Argon gas is replaced three times, and 5h is reacted under reflux temperature,
Crude product crosses silicagel column, obtains product 24mmol VII.
Step5, compound VII 24mmol are dissolved in anhydrous THF 100ml, cool to -78 degrees Celsius, slow drop
Plus 50mmol n-BuLis, room temperature is warmed up to naturally, react overnight, next day, plus diphenyl phosphine oxide 50mmol, 3h is stirred at room temperature.
It is being to slowly warm up to back flow reaction 3h.Silicagel column is crossed after the completion of reaction and obtains product 12mmol IX.
Step6, takes the compound IX of 12mmol, adds the bromobenzene of 12mmol, 36mmo potassium tert-butoxides, 0.5mmol Pd2
(dba)3, toluene 100ml, argon gas displacement three times, addition 0.5mmol tri-butyl phosphines, again argon gas displacement three times, reflux temperature
Lower reaction 10h, crude product crosses silicagel column, obtains product 7mmol compounds 1.
Mass spectrum m/z：681.98 (calculated value 681.13) the above results confirm that it is target product to obtain product.
Embodiment 2：The synthesis of compound 2
Compound 1 in embodiment 1 is replaced with into compound 2, other steps are same as Example 1, obtain compound
2.Mass spectrum m/z：756.98 (calculated values：757.17).
Embodiment 3：The synthesis of compound 3
Compound 1 in embodiment 1 is replaced with into compound 3, other steps are same as Example 1, obtain compound
3.Mass spectrum m/z：731.88 (calculated values：731.15).
Embodiment 4：The synthesis of compound 4
Compound 1 in embodiment 1 is replaced with into compound 4, other steps are same as Example 1, obtain compound
4.Mass spectrum m/z：745.00 (calculated values：745.17).
Embodiment 5：The synthesis of compound 5
Compound 1 in embodiment 1 is replaced with into compound 5, other steps are same as Example 1, obtain compound
5.Mass spectrum m/z：805.51 (calculated values：805.15).
Embodiment 6：The synthesis of compound 6
Compound 1 in embodiment 1 is replaced with into compound 6, other steps are same as Example 1, obtain compound
6.Mass spectrum m/z：823.88 (calculated values：823.18).
Embodiment 7：The synthesis of compound 7
Compound 1 in embodiment 1 is replaced with into compound 7, other steps are same as Example 1, obtain compound
7.Mass spectrum m/z：789.53 (calculated values：789.14).
Embodiment 8：The synthesis of compound 8
Compound 1 in embodiment 1 is replaced with into compound 8, other steps are same as Example 1, obtain compound
8.Mass spectrum m/z：797.60 (calculated values：797.20).
Embodiment 9：The synthesis of compound 9
Compound 1 in embodiment 1 is replaced with into compound 9, other steps are same as Example 1, obtain compound
9.Mass spectrum m/z：758.53 (calculated values：758.16).
Embodiment 10：The synthesis of compound 10
Compound 1 in embodiment 1 is replaced with into compound 10, other steps are same as Example 1, obtain compound
10.Mass spectrum m/z：758.96 (calculated values：758.16).
Embodiment 11：The synthesis of compound 11
Compound 1 in embodiment 1 is replaced with into compound 11, other steps are same as Example 1, obtain compound
11.Mass spectrum m/z：835.96 (calculated values：835.19).
Embodiment 12：The synthesis of compound 12
Compound 1 in embodiment 1 is replaced with into compound 12, other steps are same as Example 1, obtain compound
12.Mass spectrum m/z：848.96 (calculated values：848.21).
Embodiment 13：The synthesis of compound 13
Compound 1 in embodiment 1 is replaced with into compound 13, other steps are same as Example 1, obtain compound
13.Mass spectrum m/z：845.96 (calculated values：846.19).
Embodiment 14：The synthesis of compound 14
Compound 1 in embodiment 1 is replaced with into compound 14, other steps are same as Example 1, obtain compound
14.Mass spectrum m/z：846.20 (calculated values：846.19).
Embodiment 15：The synthesis of compound 15
Compound 1 in embodiment 1 is replaced with into compound 15, other steps are same as Example 1, obtain compound
15.Mass spectrum m/z：913.65 (calculated values：913.22).
Embodiment 16：The synthesis of compound 16
Compound 1 in embodiment 1 is replaced with into compound 16, other steps are same as Example 1, obtain compound
16.Mass spectrum m/z：898.36 (calculated values：898.22).
Embodiment 17：The synthesis of compound 17
Compound 1 in embodiment 1 is replaced with into compound 17, other steps are same as Example 1, obtain compound
17.Mass spectrum m/z：1101.25 (calculated values：1101.25).
Embodiment 18：The synthesis of compound 18
Compound 1 in embodiment 1 is replaced with into compound 18, other steps are same as Example 1, obtain compound
18.Mass spectrum m/z：781.56 (calculated values：781.17).
Embodiment 19：The synthesis of compound 19
Compound 1 in embodiment 1 is replaced with into compound 19, other steps are same as Example 1, obtain compound
19.Mass spectrum m/z：919.30 (calculated values：919.21).
Embodiment 20：The synthesis of compound 20
Compound 1 in embodiment 1 is replaced with into compound 20, other steps are same as Example 1, obtain compound
20.Mass spectrum m/z：919.63 (meters 919.21).
Embodiment 21：The synthesis of compound 21
Compound 1 in embodiment 1 is replaced with into compound 21, other steps are same as Example 1, obtain compound
21.Mass spectrum m/z：879.77 (calculated values：879.15).
Embodiment 22：The synthesis of compound 22
Compound 1 in embodiment 1 is replaced with into compound 22, other steps are same as Example 1, obtain compound
22.Mass spectrum m/z：923.63 (calculated values：923.24).
Embodiment 23：The synthesis of compound 23
Compound 1 in embodiment 1 is replaced with into compound 23, other steps are same as Example 1, obtain compound
23.Mass spectrum m/z：805.43 (calculated values：805.13).
Embodiment 24：The synthesis of compound 24
Compound 1 in embodiment 1 is replaced with into compound 24, other steps are same as Example 1, obtain compound
24.Mass spectrum m/z：820.02 (calculated values：820.13).
Embodiment 25：The synthesis of compound 25
Compound 1 in embodiment 1 is replaced with into compound 25, other steps are same as Example 1, obtain compound
25.Mass spectrum m/z：784.88 (calculated values：784.18).
Embodiment 26：The synthesis of compound 26
Compound 1 in embodiment 1 is replaced with into compound 26, other steps are same as Example 1, obtain compound
26.Mass spectrum m/z：953.77 (calculated values：953.27).
Contrast Application Example 1：
Transparent glass is taken for anode, in being dried as vacuum chamber after ultrasonic cleaning, 5 × 10 is evacuated to-5Pa, upper
, used as hole transmission layer, evaporation rate is 0.1nm/s to state vacuum evaporation NPB in anode grid substrate, and evaporation thickness is 70nm.In hole
Used as luminescent layer, doping concentration is 15wt% to vacuum evaporation mCP/FIrpic in transport layer, and evaporation rate is 0.005nm/s, is steamed
Plating thickness is 30nm.The vacuum evaporation Alq on luminescent layer3Used as electron transfer layer, evaporation rate is 0.01nm/s, evaporation thickness
It is 50nm.Vacuum evaporation Al layers used as negative electrode on the electron transport layer, and thickness is 200nm.
Application example 1：
Transparent glass is taken for anode, in being dried as vacuum chamber after ultrasonic cleaning, 5 × 10 is evacuated to-5Pa, upper
, used as hole transmission layer, evaporation rate is 0.1nm/s to state vacuum evaporation NPB in anode grid substrate, and evaporation thickness is 70nm.In hole
Used as luminescent layer, doping concentration is 15wt% to vacuum evaporation compound 1/FIrpic in transport layer, and evaporation rate is 0.005nm/
S, evaporation thickness is 30nm.The vacuum evaporation Alq on luminescent layer3Used as electron transfer layer, evaporation rate is 0.01nm/s, evaporation
Thickness is 50nm.Vacuum evaporation Al layers used as negative electrode on the electron transport layer, and thickness is 200nm.
Application example 2：
Change the compound 1 in Application Example 1 into compound 2.The luminescent properties of the device are measured, 1 is the results are shown in Table.
Application example 3：
Change the compound 1 in Application Example 1 into compound 3.The luminescent properties of the device are measured, 1 is the results are shown in Table.
Application example 4：
Change the compound 1 in Application Example 1 into compound 4.The luminescent properties of the device are measured, 1 is the results are shown in Table.
Application example 5：
Change the compound 1 in Application Example 1 into compound 5.The luminescent properties of the device are measured, 1 is the results are shown in Table.
Application example 6：
Change the compound 1 in Application Example 1 into compound 6.The luminescent properties of the device are measured, 1 is the results are shown in Table.
Application example 7：
Change the compound 1 in Application Example 1 into compound 7.The luminescent properties of the device are measured, 1 is the results are shown in Table.
Application example 8：
Change the compound 1 in Application Example 1 into compound 8.The luminescent properties of the device are measured, 1 is the results are shown in Table.
Application example 9：
Change the compound 1 in Application Example 1 into compound 9.The luminescent properties of the device are measured, 1 is the results are shown in Table.
Application example 10：
Change the compound 1 in Application Example 1 into compound 10.The luminescent properties of the device are measured, 1 is the results are shown in Table.
Application example 11：
Change the compound 1 in Application Example 1 into compound 11.The luminescent properties of the device are measured, 1 is the results are shown in Table.
Application example 12：
Change the compound 1 in Application Example 1 into compound 12.The luminescent properties of the device are measured, 1 is the results are shown in Table.
Application example 13：
Change the compound 1 in Application Example 1 into compound 13.The luminescent properties of the device are measured, 1 is the results are shown in Table.
Application example 14：
Change the compound 1 in Application Example 1 into compound 14.The luminescent properties of the device are measured, 1 is the results are shown in Table.
Application example 15：
Change the compound 1 in Application Example 1 into compound 15.The luminescent properties of the device are measured, 1 is the results are shown in Table.
Application example 16：
Change the compound 1 in Application Example 1 into compound 16.The luminescent properties of the device are measured, 1 is the results are shown in Table.
Application example 17：
Change the compound 1 in Application Example 1 into compound 17.The luminescent properties of the device are measured, 1 is the results are shown in Table.
Application example 18：
Change the compound 1 in Application Example 1 into compound 18.The luminescent properties of the device are measured, 1 is the results are shown in Table.
Application example 19：
Change the compound 1 in Application Example 1 into compound 19.The luminescent properties of the device are measured, 1 is the results are shown in Table.
Application example 20：
Change the compound 1 in Application Example 1 into compound 20.The luminescent properties of the device are measured, 1 is the results are shown in Table.
Application example 21：
Change the compound 1 in Application Example 1 into compound 21.The luminescent properties of the device are measured, 1 is the results are shown in Table.
Application example 22：
Change the compound 1 in Application Example 1 into compound 22.The luminescent properties of the device are measured, 1 is the results are shown in Table.
Application example 23：
Change the compound 1 in Application Example 1 into compound 23.The luminescent properties of the device are measured, 1 is the results are shown in Table.
Application example 24：
Change the compound 1 in Application Example 1 into compound 24.The luminescent properties of the device are measured, 1 is the results are shown in Table.
Application example 25：
Change the compound 1 in Application Example 1 into compound 25.The luminescent properties of the device are measured, 1 is the results are shown in Table.
Application example 26：
Change the compound 1 in Application Example 1 into compound 26.The luminescent properties of the device are measured, 1 is the results are shown in Table.
Measurement embodiment 1：The luminescent properties of comparative sample and sample 1-26, measurement comparative sample and sample 1-26 are
Using Keithley SMU235, PR650 evaluates driving voltage, luminous efficiency, external quantum efficiency.Comparative sample and sample 1-
26 are equally tested.The results are shown in Table 1：
The characteristics of luminescence of luminescent device prepared by the embodiment of the present invention of table 1
Although the present invention has carried out special description with exemplary embodiment, but it is understood that without departing from following patent
It is required that in the case of the spirit and scope of the invention for being limited, those of ordinary skill in the art it can be carried out various forms and
Change in details.
Claims (5)
1. the carbazole analog derivative that a kind of meta phosphine oxygen groups replace, shown in its general structure such as formula (I)：
Wherein, R is selected from hydrogen, deuterium, fluorine, cyano group, substituted or unsubstituted C6-C50 aryl, substituted or unsubstituted C7-C50 aralkyls
Any one in base, the arylamine of substituted or unsubstituted C6-C50, the heteroaromatic of substituted or unsubstituted C4-C40.
2. the carbazole analog derivative that a kind of meta phosphine oxygen groups according to claim 1 replace, it is characterised in that described
R is selected from hydrogen, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C7-C30 aralkyl, substituted or unsubstituted C6-
Any one in the arylamine of C30, the heteroaromatic of substituted or unsubstituted C4-C30.
3. the carbazole analog derivative that a kind of meta phosphine oxygen groups according to claim 1 replace, it is characterised in that described
R is selected from any one in following structure：
Described X is selected from hydrogen, C6-C24 aryl, the aralkyl of C7-C30, the arylamine of C6-C16, the aryl ether of C6-C16, C6-
Any one in the aryl thioethers of C16, the heteroaromatic of C4-C30；
Described Y is selected from carbon or nitrogen；
Described Z is selected from oxygen or sulphur.
4. the carbazole analog derivative that a kind of meta phosphine oxygen groups according to claim 1 replace, it is characterised in that such as formula 1
Shown in~26 any one：
5. a kind of organic luminescent device, including first electrode, second electrode and be placed between two electrodes one or more are organic
Layer, it is characterised in that at least one organic layer includes a kind of meta phosphine oxygen groups substitution a kind of as defined in claim 1
Carbazole analog derivative.
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| CN107602440A (en) * | 2017-10-09 | 2018-01-19 | 长春海谱润斯科技有限公司 | A kind of benzo carbazole class electroluminescent organic material and its organic luminescent device |
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| CN107698486A (en) * | 2017-10-09 | 2018-02-16 | 长春海谱润斯科技有限公司 | A kind of benzo carbazole organic compound and its organic luminescent device |
| CN107698488A (en) * | 2017-10-09 | 2018-02-16 | 长春海谱润斯科技有限公司 | A kind of benzo carbazole analog derivative and its organic luminescent device |
| CN111718357A (en) * | 2019-03-21 | 2020-09-29 | 三星显示有限公司 | Organic electroluminescent device and monoamine compound for organic electroluminescent device |
| US11600781B2 (en) * | 2019-03-21 | 2023-03-07 | Samsung Display Co., Ltd. | Organic electroluminescence device and monoamine compound for organic electroluminescence device |
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