WO2022237407A1 - 一种有机化合物、有机电致发光材料及其装置 - Google Patents
一种有机化合物、有机电致发光材料及其装置 Download PDFInfo
- Publication number
- WO2022237407A1 WO2022237407A1 PCT/CN2022/085681 CN2022085681W WO2022237407A1 WO 2022237407 A1 WO2022237407 A1 WO 2022237407A1 CN 2022085681 W CN2022085681 W CN 2022085681W WO 2022237407 A1 WO2022237407 A1 WO 2022237407A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- groups
- aromatic
- atom
- group
- carbon atoms
- Prior art date
Links
- 150000002894 organic compounds Chemical class 0.000 title claims abstract description 15
- 239000000463 material Substances 0.000 title claims description 33
- 150000001875 compounds Chemical class 0.000 claims abstract description 84
- 125000003118 aryl group Chemical group 0.000 claims abstract description 49
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 34
- 229910052805 deuterium Inorganic materials 0.000 claims abstract description 23
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 23
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 22
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 14
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 10
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims abstract description 9
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 9
- 239000001257 hydrogen Substances 0.000 claims abstract description 9
- 239000010410 layer Substances 0.000 claims description 92
- 238000002360 preparation method Methods 0.000 claims description 37
- -1 NR 11 Inorganic materials 0.000 claims description 25
- 229910052799 carbon Inorganic materials 0.000 claims description 21
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 21
- 125000002560 nitrile group Chemical group 0.000 claims description 19
- 125000005843 halogen group Chemical group 0.000 claims description 17
- 238000002347 injection Methods 0.000 claims description 16
- 239000007924 injection Substances 0.000 claims description 16
- 150000001975 deuterium Chemical group 0.000 claims description 14
- 230000000903 blocking effect Effects 0.000 claims description 13
- 229910052757 nitrogen Inorganic materials 0.000 claims description 13
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 12
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 12
- 125000003342 alkenyl group Chemical group 0.000 claims description 9
- 125000004122 cyclic group Chemical group 0.000 claims description 9
- 239000002019 doping agent Substances 0.000 claims description 9
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 claims description 9
- 125000002950 monocyclic group Chemical group 0.000 claims description 9
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 8
- 125000000304 alkynyl group Chemical group 0.000 claims description 8
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 8
- 230000005525 hole transport Effects 0.000 claims description 8
- 239000012044 organic layer Substances 0.000 claims description 8
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 7
- 125000004104 aryloxy group Chemical group 0.000 claims description 6
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 6
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 claims description 6
- 125000004431 deuterium atom Chemical group 0.000 claims description 5
- 229910052698 phosphorus Inorganic materials 0.000 claims description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 239000011593 sulfur Substances 0.000 claims description 4
- DXBHBZVCASKNBY-UHFFFAOYSA-N 1,2-Benz(a)anthracene Chemical compound C1=CC=C2C3=CC4=CC=CC=C4C=C3C=CC2=C1 DXBHBZVCASKNBY-UHFFFAOYSA-N 0.000 claims description 3
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims description 3
- SLIUAWYAILUBJU-UHFFFAOYSA-N pentacene Chemical compound C1=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C21 SLIUAWYAILUBJU-UHFFFAOYSA-N 0.000 claims description 3
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 claims description 3
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 claims description 3
- 125000004437 phosphorous atom Chemical group 0.000 claims description 3
- 125000003367 polycyclic group Chemical group 0.000 claims description 2
- 125000006165 cyclic alkyl group Chemical group 0.000 abstract 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 238000000034 method Methods 0.000 description 15
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 239000012074 organic phase Substances 0.000 description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
- 239000000741 silica gel Substances 0.000 description 11
- 229910002027 silica gel Inorganic materials 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 8
- 239000000706 filtrate Substances 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- 239000000203 mixture Substances 0.000 description 7
- 238000007639 printing Methods 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 6
- 238000010189 synthetic method Methods 0.000 description 6
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 4
- 238000005401 electroluminescence Methods 0.000 description 4
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 4
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 4
- 238000011056 performance test Methods 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- 238000007740 vapor deposition Methods 0.000 description 4
- 229910021595 Copper(I) iodide Inorganic materials 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 235000010290 biphenyl Nutrition 0.000 description 3
- 239000004305 biphenyl Substances 0.000 description 3
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000004528 spin coating Methods 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
- 238000012546 transfer Methods 0.000 description 3
- BFIMMTCNYPIMRN-UHFFFAOYSA-N 1,2,3,5-tetramethylbenzene Chemical compound CC1=CC(C)=C(C)C(C)=C1 BFIMMTCNYPIMRN-UHFFFAOYSA-N 0.000 description 2
- IVSZLXZYQVIEFR-UHFFFAOYSA-N 1,3-Dimethylbenzene Natural products CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 2
- 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 2
- CHLICZRVGGXEOD-UHFFFAOYSA-N 1-Methoxy-4-methylbenzene Chemical compound COC1=CC=C(C)C=C1 CHLICZRVGGXEOD-UHFFFAOYSA-N 0.000 description 2
- LTLVZQZDXQWLHU-UHFFFAOYSA-N 1-bromo-4-ethynylbenzene Chemical group BrC1=CC=C(C#C)C=C1 LTLVZQZDXQWLHU-UHFFFAOYSA-N 0.000 description 2
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 2
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 2
- TZMSYXZUNZXBOL-UHFFFAOYSA-N 10H-phenoxazine Chemical compound C1=CC=C2NC3=CC=CC=C3OC2=C1 TZMSYXZUNZXBOL-UHFFFAOYSA-N 0.000 description 2
- DXYYSGDWQCSKKO-UHFFFAOYSA-N 2-methylbenzothiazole Chemical compound C1=CC=C2SC(C)=NC2=C1 DXYYSGDWQCSKKO-UHFFFAOYSA-N 0.000 description 2
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 2
- ZFBBPVJBVIJQCE-UHFFFAOYSA-N 9-ethylanthracene Chemical compound C1=CC=C2C(CC)=C(C=CC=C3)C3=CC2=C1 ZFBBPVJBVIJQCE-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LTEQMZWBSYACLV-UHFFFAOYSA-N Hexylbenzene Chemical compound CCCCCCC1=CC=CC=C1 LTEQMZWBSYACLV-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 2
- 101150003085 Pdcl gene Proteins 0.000 description 2
- PWATWSYOIIXYMA-UHFFFAOYSA-N Pentylbenzene Chemical compound CCCCCC1=CC=CC=C1 PWATWSYOIIXYMA-UHFFFAOYSA-N 0.000 description 2
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 2
- 125000004414 alkyl thio group Chemical group 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 230000004888 barrier function Effects 0.000 description 2
- 125000005605 benzo group Chemical group 0.000 description 2
- XSIFPSYPOVKYCO-UHFFFAOYSA-N butyl benzoate Chemical compound CCCCOC(=O)C1=CC=CC=C1 XSIFPSYPOVKYCO-UHFFFAOYSA-N 0.000 description 2
- 239000012159 carrier gas Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 2
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 2
- MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical compound C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 description 2
- SQNZJJAZBFDUTD-UHFFFAOYSA-N durene Chemical compound CC1=CC(C)=C(C)C=C1C SQNZJJAZBFDUTD-UHFFFAOYSA-N 0.000 description 2
- MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 description 2
- 239000012065 filter cake Substances 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical compound C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229940095102 methyl benzoate Drugs 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N o-dimethylbenzene Natural products CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- HFPZCAJZSCWRBC-UHFFFAOYSA-N p-cymene Chemical compound CC(C)C1=CC=C(C)C=C1 HFPZCAJZSCWRBC-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- RDOWQLZANAYVLL-UHFFFAOYSA-N phenanthridine Chemical compound C1=CC=C2C3=CC=CC=C3C=NC2=C1 RDOWQLZANAYVLL-UHFFFAOYSA-N 0.000 description 2
- 229950000688 phenothiazine Drugs 0.000 description 2
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000000859 sublimation Methods 0.000 description 2
- 230000008022 sublimation Effects 0.000 description 2
- 238000005092 sublimation method Methods 0.000 description 2
- ZUHZGEOKBKGPSW-UHFFFAOYSA-N tetraglyme Chemical compound COCCOCCOCCOCCOC ZUHZGEOKBKGPSW-UHFFFAOYSA-N 0.000 description 2
- 229930192474 thiophene Natural products 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- ABDKAPXRBAPSQN-UHFFFAOYSA-N veratrole Chemical compound COC1=CC=CC=C1OC ABDKAPXRBAPSQN-UHFFFAOYSA-N 0.000 description 2
- LHXDLQBQYFFVNW-OIBJUYFYSA-N (-)-Fenchone Chemical compound C1C[C@@]2(C)C(=O)C(C)(C)[C@@H]1C2 LHXDLQBQYFFVNW-OIBJUYFYSA-N 0.000 description 1
- 229930006729 (1R,4S)-fenchone Natural products 0.000 description 1
- WUOACPNHFRMFPN-SECBINFHSA-N (S)-(-)-alpha-terpineol Chemical compound CC1=CC[C@@H](C(C)(C)O)CC1 WUOACPNHFRMFPN-SECBINFHSA-N 0.000 description 1
- ICPSWZFVWAPUKF-UHFFFAOYSA-N 1,1'-spirobi[fluorene] Chemical compound C1=CC=C2C=C3C4(C=5C(C6=CC=CC=C6C=5)=CC=C4)C=CC=C3C2=C1 ICPSWZFVWAPUKF-UHFFFAOYSA-N 0.000 description 1
- FIARMZDBEGVMLV-UHFFFAOYSA-N 1,1,2,2,2-pentafluoroethanolate Chemical group [O-]C(F)(F)C(F)(F)F FIARMZDBEGVMLV-UHFFFAOYSA-N 0.000 description 1
- HQDYNFWTFJFEPR-UHFFFAOYSA-N 1,2,3,3a-tetrahydropyrene Chemical compound C1=C2CCCC(C=C3)C2=C2C3=CC=CC2=C1 HQDYNFWTFJFEPR-UHFFFAOYSA-N 0.000 description 1
- ZFXBERJDEUDDMX-UHFFFAOYSA-N 1,2,3,5-tetrazine Chemical compound C1=NC=NN=N1 ZFXBERJDEUDDMX-UHFFFAOYSA-N 0.000 description 1
- FNQJDLTXOVEEFB-UHFFFAOYSA-N 1,2,3-benzothiadiazole Chemical compound C1=CC=C2SN=NC2=C1 FNQJDLTXOVEEFB-UHFFFAOYSA-N 0.000 description 1
- UGUHFDPGDQDVGX-UHFFFAOYSA-N 1,2,3-thiadiazole Chemical compound C1=CSN=N1 UGUHFDPGDQDVGX-UHFFFAOYSA-N 0.000 description 1
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- HTJMXYRLEDBSLT-UHFFFAOYSA-N 1,2,4,5-tetrazine Chemical compound C1=NN=CN=N1 HTJMXYRLEDBSLT-UHFFFAOYSA-N 0.000 description 1
- BBVIDBNAYOIXOE-UHFFFAOYSA-N 1,2,4-oxadiazole Chemical compound C=1N=CON=1 BBVIDBNAYOIXOE-UHFFFAOYSA-N 0.000 description 1
- YGTAZGSLCXNBQL-UHFFFAOYSA-N 1,2,4-thiadiazole Chemical compound C=1N=CSN=1 YGTAZGSLCXNBQL-UHFFFAOYSA-N 0.000 description 1
- FYADHXFMURLYQI-UHFFFAOYSA-N 1,2,4-triazine Chemical compound C1=CN=NC=N1 FYADHXFMURLYQI-UHFFFAOYSA-N 0.000 description 1
- UDGKZGLPXCRRAM-UHFFFAOYSA-N 1,2,5-thiadiazole Chemical compound C=1C=NSN=1 UDGKZGLPXCRRAM-UHFFFAOYSA-N 0.000 description 1
- UUSUFQUCLACDTA-UHFFFAOYSA-N 1,2-dihydropyrene Chemical compound C1=CC=C2C=CC3=CCCC4=CC=C1C2=C43 UUSUFQUCLACDTA-UHFFFAOYSA-N 0.000 description 1
- FKASFBLJDCHBNZ-UHFFFAOYSA-N 1,3,4-oxadiazole Chemical compound C1=NN=CO1 FKASFBLJDCHBNZ-UHFFFAOYSA-N 0.000 description 1
- MBIZXFATKUQOOA-UHFFFAOYSA-N 1,3,4-thiadiazole Chemical compound C1=NN=CS1 MBIZXFATKUQOOA-UHFFFAOYSA-N 0.000 description 1
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 description 1
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- SPPWGCYEYAMHDT-UHFFFAOYSA-N 1,4-di(propan-2-yl)benzene Chemical compound CC(C)C1=CC=C(C(C)C)C=C1 SPPWGCYEYAMHDT-UHFFFAOYSA-N 0.000 description 1
- FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical compound N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 description 1
- OSIGJGFTADMDOB-UHFFFAOYSA-N 1-Methoxy-3-methylbenzene Chemical compound COC1=CC=CC(C)=C1 OSIGJGFTADMDOB-UHFFFAOYSA-N 0.000 description 1
- LBNXAWYDQUGHGX-UHFFFAOYSA-N 1-Phenylheptane Chemical compound CCCCCCCC1=CC=CC=C1 LBNXAWYDQUGHGX-UHFFFAOYSA-N 0.000 description 1
- HYLLZXPMJRMUHH-UHFFFAOYSA-N 1-[2-(2-methoxyethoxy)ethoxy]butane Chemical compound CCCCOCCOCCOC HYLLZXPMJRMUHH-UHFFFAOYSA-N 0.000 description 1
- SNAQINZKMQFYFV-UHFFFAOYSA-N 1-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]butane Chemical compound CCCCOCCOCCOCCOC SNAQINZKMQFYFV-UHFFFAOYSA-N 0.000 description 1
- WUYYVOWEBMOELQ-UHFFFAOYSA-N 1-bromodibenzofuran Chemical compound O1C2=CC=CC=C2C2=C1C=CC=C2Br WUYYVOWEBMOELQ-UHFFFAOYSA-N 0.000 description 1
- UFOVULIWACVAAC-UHFFFAOYSA-N 1-ethynyl-2-methoxybenzene Chemical group COC1=CC=CC=C1C#C UFOVULIWACVAAC-UHFFFAOYSA-N 0.000 description 1
- RERATEUBWLKDFE-UHFFFAOYSA-N 1-methoxy-2-[2-(2-methoxypropoxy)propoxy]propane Chemical compound COCC(C)OCC(C)OCC(C)OC RERATEUBWLKDFE-UHFFFAOYSA-N 0.000 description 1
- JCHJBEZBHANKGA-UHFFFAOYSA-N 1-methoxy-3,5-dimethylbenzene Chemical compound COC1=CC(C)=CC(C)=C1 JCHJBEZBHANKGA-UHFFFAOYSA-N 0.000 description 1
- WCOYPFBMFKXWBM-UHFFFAOYSA-N 1-methyl-2-phenoxybenzene Chemical compound CC1=CC=CC=C1OC1=CC=CC=C1 WCOYPFBMFKXWBM-UHFFFAOYSA-N 0.000 description 1
- UDONPJKEOAWFGI-UHFFFAOYSA-N 1-methyl-3-phenoxybenzene Chemical compound CC1=CC=CC(OC=2C=CC=CC=2)=C1 UDONPJKEOAWFGI-UHFFFAOYSA-N 0.000 description 1
- SPDPTFAJSFKAMT-UHFFFAOYSA-N 1-n-[4-[4-(n-[4-(3-methyl-n-(3-methylphenyl)anilino)phenyl]anilino)phenyl]phenyl]-4-n,4-n-bis(3-methylphenyl)-1-n-phenylbenzene-1,4-diamine Chemical compound CC1=CC=CC(N(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=CC(=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=CC(=CC=2)N(C=2C=C(C)C=CC=2)C=2C=C(C)C=CC=2)C=2C=C(C)C=CC=2)=C1 SPDPTFAJSFKAMT-UHFFFAOYSA-N 0.000 description 1
- QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical compound C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 description 1
- USYCQABRSUEURP-UHFFFAOYSA-N 1h-benzo[f]benzimidazole Chemical compound C1=CC=C2C=C(NC=N3)C3=CC2=C1 USYCQABRSUEURP-UHFFFAOYSA-N 0.000 description 1
- ZKAMEFMDQNTDFK-UHFFFAOYSA-N 1h-imidazo[4,5-b]pyrazine Chemical compound C1=CN=C2NC=NC2=N1 ZKAMEFMDQNTDFK-UHFFFAOYSA-N 0.000 description 1
- FCTIZUUFUMDWEH-UHFFFAOYSA-N 1h-imidazo[4,5-b]quinoxaline Chemical compound C1=CC=C2N=C(NC=N3)C3=NC2=C1 FCTIZUUFUMDWEH-UHFFFAOYSA-N 0.000 description 1
- GZPPANJXLZUWHT-UHFFFAOYSA-N 1h-naphtho[2,1-e]benzimidazole Chemical compound C1=CC2=CC=CC=C2C2=C1C(N=CN1)=C1C=C2 GZPPANJXLZUWHT-UHFFFAOYSA-N 0.000 description 1
- 125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 description 1
- VEPOHXYIFQMVHW-XOZOLZJESA-N 2,3-dihydroxybutanedioic acid (2S,3S)-3,4-dimethyl-2-phenylmorpholine Chemical compound OC(C(O)C(O)=O)C(O)=O.C[C@H]1[C@@H](OCCN1C)c1ccccc1 VEPOHXYIFQMVHW-XOZOLZJESA-N 0.000 description 1
- GEQBRULPNIVQPP-UHFFFAOYSA-N 2-[3,5-bis(1-phenylbenzimidazol-2-yl)phenyl]-1-phenylbenzimidazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2N=C1C1=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=C1 GEQBRULPNIVQPP-UHFFFAOYSA-N 0.000 description 1
- UXGVMFHEKMGWMA-UHFFFAOYSA-N 2-benzofuran Chemical compound C1=CC=CC2=COC=C21 UXGVMFHEKMGWMA-UHFFFAOYSA-N 0.000 description 1
- LYTMVABTDYMBQK-UHFFFAOYSA-N 2-benzothiophene Chemical compound C1=CC=CC2=CSC=C21 LYTMVABTDYMBQK-UHFFFAOYSA-N 0.000 description 1
- DDGPPAMADXTGTN-UHFFFAOYSA-N 2-chloro-4,6-diphenyl-1,3,5-triazine Chemical compound N=1C(Cl)=NC(C=2C=CC=CC=2)=NC=1C1=CC=CC=C1 DDGPPAMADXTGTN-UHFFFAOYSA-N 0.000 description 1
- KQDJTBPASNJQFQ-UHFFFAOYSA-N 2-iodophenol Chemical compound OC1=CC=CC=C1I KQDJTBPASNJQFQ-UHFFFAOYSA-N 0.000 description 1
- CRWNQZTZTZWPOF-UHFFFAOYSA-N 2-methyl-4-phenylpyridine Chemical compound C1=NC(C)=CC(C=2C=CC=CC=2)=C1 CRWNQZTZTZWPOF-UHFFFAOYSA-N 0.000 description 1
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
- JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 description 1
- QCDWFXQBSFUVSP-UHFFFAOYSA-N 2-phenoxyethanol Chemical compound OCCOC1=CC=CC=C1 QCDWFXQBSFUVSP-UHFFFAOYSA-N 0.000 description 1
- TVYVQNHYIHAJTD-UHFFFAOYSA-N 2-propan-2-ylnaphthalene Chemical compound C1=CC=CC2=CC(C(C)C)=CC=C21 TVYVQNHYIHAJTD-UHFFFAOYSA-N 0.000 description 1
- VHMICKWLTGFITH-UHFFFAOYSA-N 2H-isoindole Chemical compound C1=CC=CC2=CNC=C21 VHMICKWLTGFITH-UHFFFAOYSA-N 0.000 description 1
- DMEVMYSQZPJFOK-UHFFFAOYSA-N 3,4,5,6,9,10-hexazatetracyclo[12.4.0.02,7.08,13]octadeca-1(18),2(7),3,5,8(13),9,11,14,16-nonaene Chemical group N1=NN=C2C3=CC=CC=C3C3=CC=NN=C3C2=N1 DMEVMYSQZPJFOK-UHFFFAOYSA-N 0.000 description 1
- CPDDXQJCPYHULE-UHFFFAOYSA-N 4,5,14,16-tetrazapentacyclo[9.7.1.12,6.015,19.010,20]icosa-1(18),2,4,6,8,10(20),11(19),12,14,16-decaene Chemical group C1=CC(C2=CC=CC=3C2=C2C=NN=3)=C3C2=CC=NC3=N1 CPDDXQJCPYHULE-UHFFFAOYSA-N 0.000 description 1
- NCSVCMFDHINRJE-UHFFFAOYSA-N 4-[1-(3,4-dimethylphenyl)ethyl]-1,2-dimethylbenzene Chemical compound C=1C=C(C)C(C)=CC=1C(C)C1=CC=C(C)C(C)=C1 NCSVCMFDHINRJE-UHFFFAOYSA-N 0.000 description 1
- GAMYYCRTACQSBR-UHFFFAOYSA-N 4-azabenzimidazole Chemical compound C1=CC=C2NC=NC2=N1 GAMYYCRTACQSBR-UHFFFAOYSA-N 0.000 description 1
- ACEYZYYNAMWIIE-UHFFFAOYSA-N 4-iododibenzofuran Chemical compound O1C2=CC=CC=C2C2=C1C(I)=CC=C2 ACEYZYYNAMWIIE-UHFFFAOYSA-N 0.000 description 1
- LVUBSVWMOWKPDJ-UHFFFAOYSA-N 4-methoxy-1,2-dimethylbenzene Chemical compound COC1=CC=C(C)C(C)=C1 LVUBSVWMOWKPDJ-UHFFFAOYSA-N 0.000 description 1
- 229940077398 4-methyl anisole Drugs 0.000 description 1
- RHPVVNRNAHRJOQ-UHFFFAOYSA-N 4-methyl-n-(4-methylphenyl)aniline Chemical compound C1=CC(C)=CC=C1NC1=CC=C(C)C=C1 RHPVVNRNAHRJOQ-UHFFFAOYSA-N 0.000 description 1
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 1
- IUKNPBPXZUWMNO-UHFFFAOYSA-N 5,12-diazatetracyclo[6.6.2.04,16.011,15]hexadeca-1(15),2,4,6,8(16),9,11,13-octaene Chemical compound N1=CC=C2C=CC3=NC=CC4=CC=C1C2=C43 IUKNPBPXZUWMNO-UHFFFAOYSA-N 0.000 description 1
- NHWJSCHQRMCCAD-UHFFFAOYSA-N 5,14-diazatetracyclo[6.6.2.04,16.011,15]hexadeca-1(14),2,4,6,8(16),9,11(15),12-octaene Chemical compound C1=CN=C2C=CC3=NC=CC4=CC=C1C2=C43 NHWJSCHQRMCCAD-UHFFFAOYSA-N 0.000 description 1
- PODJSIAAYWCBDV-UHFFFAOYSA-N 5,6-diazatetracyclo[6.6.2.04,16.011,15]hexadeca-1(14),2,4(16),5,7,9,11(15),12-octaene Chemical compound C1=NN=C2C=CC3=CC=CC4=CC=C1C2=C43 PODJSIAAYWCBDV-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- SNFCXVRWFNAHQX-UHFFFAOYSA-N 9,9'-spirobi[fluorene] Chemical compound C12=CC=CC=C2C2=CC=CC=C2C21C1=CC=CC=C1C1=CC=CC=C21 SNFCXVRWFNAHQX-UHFFFAOYSA-N 0.000 description 1
- WSZBYXQREMPYLP-UHFFFAOYSA-N 9-ethynylanthracene Chemical compound C1=CC=C2C(C#C)=C(C=CC=C3)C3=CC2=C1 WSZBYXQREMPYLP-UHFFFAOYSA-N 0.000 description 1
- BPMFPOGUJAAYHL-UHFFFAOYSA-N 9H-Pyrido[2,3-b]indole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=N1 BPMFPOGUJAAYHL-UHFFFAOYSA-N 0.000 description 1
- 239000005964 Acibenzolar-S-methyl Substances 0.000 description 1
- FMMWHPNWAFZXNH-UHFFFAOYSA-N Benz[a]pyrene Chemical compound C1=C2C3=CC=CC=C3C=C(C=C3)C2=C2C3=CC=CC2=C1 FMMWHPNWAFZXNH-UHFFFAOYSA-N 0.000 description 1
- ZPIPUFJBRZFYKJ-UHFFFAOYSA-N C1=NC=C2C=CC3=CN=CC4=CC=C1C2=C34 Chemical compound C1=NC=C2C=CC3=CN=CC4=CC=C1C2=C34 ZPIPUFJBRZFYKJ-UHFFFAOYSA-N 0.000 description 1
- IGZZMBOJOUYRAV-UHFFFAOYSA-N CC1=CC=CC=C1.C(C)(C)(C)[P] Chemical compound CC1=CC=CC=C1.C(C)(C)(C)[P] IGZZMBOJOUYRAV-UHFFFAOYSA-N 0.000 description 1
- KZJVGPOAAWFOIH-UHFFFAOYSA-N CCCCOC(C(C)OC)(C(OCC)(OCCC)OC(C)C)OOCC(C)C Chemical compound CCCCOC(C(C)OC)(C(OCC)(OCCC)OC(C)C)OOCC(C)C KZJVGPOAAWFOIH-UHFFFAOYSA-N 0.000 description 1
- QZRGKCOWNLSUDK-UHFFFAOYSA-N Iodochlorine Chemical compound ICl QZRGKCOWNLSUDK-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- YEVNBILBHBIAHR-UHFFFAOYSA-N N1=CC=C2C=NC3=CC=CC4=CC=C1C2=C34 Chemical compound N1=CC=C2C=NC3=CC=CC4=CC=C1C2=C34 YEVNBILBHBIAHR-UHFFFAOYSA-N 0.000 description 1
- NTWBOMMQBKGLPJ-UHFFFAOYSA-N O1C=NC=C1.C1=CC=CC=2C3=CC=CC=C3C=CC12 Chemical compound O1C=NC=C1.C1=CC=CC=2C3=CC=CC=C3C=CC12 NTWBOMMQBKGLPJ-UHFFFAOYSA-N 0.000 description 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- XBDYBAVJXHJMNQ-UHFFFAOYSA-N Tetrahydroanthracene Natural products C1=CC=C2C=C(CCCC3)C3=CC2=C1 XBDYBAVJXHJMNQ-UHFFFAOYSA-N 0.000 description 1
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 1
- DPOPAJRDYZGTIR-UHFFFAOYSA-N Tetrazine Chemical compound C1=CN=NN=N1 DPOPAJRDYZGTIR-UHFFFAOYSA-N 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- 229940008309 acetone / ethanol Drugs 0.000 description 1
- OVKDFILSBMEKLT-UHFFFAOYSA-N alpha-Terpineol Natural products CC(=C)C1(O)CCC(C)=CC1 OVKDFILSBMEKLT-UHFFFAOYSA-N 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- LHXDLQBQYFFVNW-UHFFFAOYSA-N alpha-fenchone Natural products C1CC2(C)C(=O)C(C)(C)C1C2 LHXDLQBQYFFVNW-UHFFFAOYSA-N 0.000 description 1
- 229940088601 alpha-terpineol Drugs 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 description 1
- WMUIZUWOEIQJEH-UHFFFAOYSA-N benzo[e][1,3]benzoxazole Chemical compound C1=CC=C2C(N=CO3)=C3C=CC2=C1 WMUIZUWOEIQJEH-UHFFFAOYSA-N 0.000 description 1
- WZJYKHNJTSNBHV-UHFFFAOYSA-N benzo[h]quinoline Chemical compound C1=CN=C2C3=CC=CC=C3C=CC2=C1 WZJYKHNJTSNBHV-UHFFFAOYSA-N 0.000 description 1
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 1
- 239000012964 benzotriazole Substances 0.000 description 1
- 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- LNAMMBFJMYMQTO-FNEBRGMMSA-N chloroform;(1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].ClC(Cl)Cl.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 LNAMMBFJMYMQTO-FNEBRGMMSA-N 0.000 description 1
- WCZVZNOTHYJIEI-UHFFFAOYSA-N cinnoline Chemical compound N1=NC=CC2=CC=CC=C21 WCZVZNOTHYJIEI-UHFFFAOYSA-N 0.000 description 1
- 239000012459 cleaning agent Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000000392 cycloalkenyl group Chemical group 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000001047 cyclobutenyl group Chemical group C1(=CCC1)* 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001162 cycloheptenyl group Chemical group C1(=CCCCCC1)* 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- HHNHBFLGXIUXCM-GFCCVEGCSA-N cyclohexylbenzene Chemical compound [CH]1CCCC[C@@H]1C1=CC=CC=C1 HHNHBFLGXIUXCM-GFCCVEGCSA-N 0.000 description 1
- 125000000522 cyclooctenyl group Chemical group C1(=CCCCCCC1)* 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 239000000412 dendrimer Substances 0.000 description 1
- 229920000736 dendritic polymer Polymers 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 150000001987 diarylethers Chemical class 0.000 description 1
- 229940028356 diethylene glycol monobutyl ether Drugs 0.000 description 1
- XXPBFNVKTVJZKF-UHFFFAOYSA-N dihydrophenanthrene Natural products C1=CC=C2CCC3=CC=CC=C3C2=C1 XXPBFNVKTVJZKF-UHFFFAOYSA-N 0.000 description 1
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical class C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 1
- BFMYDTVEBKDAKJ-UHFFFAOYSA-L disodium;(2',7'-dibromo-3',6'-dioxido-3-oxospiro[2-benzofuran-1,9'-xanthene]-4'-yl)mercury;hydrate Chemical compound O.[Na+].[Na+].O1C(=O)C2=CC=CC=C2C21C1=CC(Br)=C([O-])C([Hg])=C1OC1=C2C=C(Br)C([O-])=C1 BFMYDTVEBKDAKJ-UHFFFAOYSA-L 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- KWKXNDCHNDYVRT-UHFFFAOYSA-N dodecylbenzene Chemical compound CCCCCCCCCCCCC1=CC=CC=C1 KWKXNDCHNDYVRT-UHFFFAOYSA-N 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- JKFAIQOWCVVSKC-UHFFFAOYSA-N furazan Chemical compound C=1C=NON=1 JKFAIQOWCVVSKC-UHFFFAOYSA-N 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 125000005980 hexynyl group Chemical group 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- WUNJCKOTXFSWBK-UHFFFAOYSA-N indeno[2,1-a]carbazole Chemical compound C1=CC=C2C=C3C4=NC5=CC=CC=C5C4=CC=C3C2=C1 WUNJCKOTXFSWBK-UHFFFAOYSA-N 0.000 description 1
- PJULCNAVAGQLAT-UHFFFAOYSA-N indeno[2,1-a]fluorene Chemical compound C1=CC=C2C=C3C4=CC5=CC=CC=C5C4=CC=C3C2=C1 PJULCNAVAGQLAT-UHFFFAOYSA-N 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- HOBCFUWDNJPFHB-UHFFFAOYSA-N indolizine Chemical compound C1=CC=CN2C=CC=C21 HOBCFUWDNJPFHB-UHFFFAOYSA-N 0.000 description 1
- VVVPGLRKXQSQSZ-UHFFFAOYSA-N indolo[3,2-c]carbazole Chemical compound C1=CC=CC2=NC3=C4C5=CC=CC=C5N=C4C=CC3=C21 VVVPGLRKXQSQSZ-UHFFFAOYSA-N 0.000 description 1
- 229960005544 indolocarbazole Drugs 0.000 description 1
- 239000011229 interlayer Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 238000010884 ion-beam technique Methods 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 description 1
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 238000001459 lithography Methods 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 150000002739 metals Chemical class 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000005244 neohexyl group Chemical group [H]C([H])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 description 1
- VXNSQGRKHCZUSU-UHFFFAOYSA-N octylbenzene Chemical compound [CH2]CCCCCCCC1=CC=CC=C1 VXNSQGRKHCZUSU-UHFFFAOYSA-N 0.000 description 1
- 125000005069 octynyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C#C* 0.000 description 1
- 239000005416 organic matter Substances 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- JCGNDDUYTRNOFT-UHFFFAOYSA-N oxolane-2,4-dione Chemical compound O=C1COC(=O)C1 JCGNDDUYTRNOFT-UHFFFAOYSA-N 0.000 description 1
- GNWXVOQHLPBSSR-UHFFFAOYSA-N oxolane;toluene Chemical compound C1CCOC1.CC1=CC=CC=C1 GNWXVOQHLPBSSR-UHFFFAOYSA-N 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
- 125000005981 pentynyl group Chemical group 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- DLRJIFUOBPOJNS-UHFFFAOYSA-N phenetole Chemical compound CCOC1=CC=CC=C1 DLRJIFUOBPOJNS-UHFFFAOYSA-N 0.000 description 1
- 229960005323 phenoxyethanol Drugs 0.000 description 1
- CLSUSRZJUQMOHH-UHFFFAOYSA-L platinum dichloride Chemical compound Cl[Pt]Cl CLSUSRZJUQMOHH-UHFFFAOYSA-L 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- CPNGPNLZQNNVQM-UHFFFAOYSA-N pteridine Chemical compound N1=CN=CC2=NC=CN=C21 CPNGPNLZQNNVQM-UHFFFAOYSA-N 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 238000006862 quantum yield reaction Methods 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- 238000001931 thermography Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 description 1
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 1
- CWMFRHBXRUITQE-UHFFFAOYSA-N trimethylsilylacetylene Chemical group C[Si](C)(C)C#C CWMFRHBXRUITQE-UHFFFAOYSA-N 0.000 description 1
- 238000002061 vacuum sublimation Methods 0.000 description 1
- 238000005019 vapor deposition process Methods 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
-
- 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
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
-
- 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
-
- 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
- H10K50/80—Constructional details
- H10K50/85—Arrangements for extracting light from the devices
- H10K50/858—Arrangements for extracting light from the devices comprising refractive means, e.g. lenses
-
- 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
-
- 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
-
- 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
- H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
-
- 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
-
- 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
- H10K85/636—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
-
- 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
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
-
- 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
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
-
- 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
- H10K85/649—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
-
- 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
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
-
- 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
- H10K85/649—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
-
- 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
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1011—Condensed systems
-
- 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
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1014—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
-
- 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
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1022—Heterocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
-
- 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
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
-
- 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
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
-
- 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
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms
-
- 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
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
-
- 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
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1092—Heterocyclic compounds characterised by ligands containing sulfur as the only heteroatom
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
Definitions
- the invention relates to the technical field of organic electroluminescence. More specifically, it relates to an organic compound, an organic electroluminescent material containing the compound, an organic electroluminescent device containing the compound, and its application in the organic electroluminescent material.
- organic electroluminescent elements are pure organic substances or organometallic complexes that form complexes between organic substances and metals. According to the application, they can be divided into hole injectors, hole transporters, luminescent substances, and electron transporters. , electron injectants, etc.
- organic substances with relatively low ionization energy are mainly used as hole injectors or hole transporters
- organic substances with relatively high electronegativity are mainly used as electron injectors or electron transporters.
- the substance used as the luminescence assisting layer preferably satisfies the following characteristics.
- the materials used in organic electroluminescent elements need to have good thermal stability. The reason is that Joule heat occurs within the organic electroluminescent element due to the migration of charges.
- the materials used as hole transport layers are usually The glass transition temperature of the material is low, so there is a phenomenon that the luminous efficiency decreases due to crystallization when driven at low temperature.
- the organic matter adjacent to the cathode and anode needs to be designed with a small charge injection barrier and a high charge mobility.
- the light-emitting layer is composed of two substances, a host emitter and a dopant.
- the dopant needs to have high quantum efficiency, and the host emitter needs to have a larger energy gap than the dopant so that energy transfer to the dopant can easily occur.
- Displays for TVs, mobile devices, etc. achieve full color based on the three primary colors of red, green, and blue.
- Doping composition At present, blue light materials still have the problems of low luminous quantum efficiency and poor color purity. The main reason for this situation is that blue light comes from the transition between energy levels with a wide energy gap, and organic compounds with wide band gaps have certain difficulties in molecular design, and secondly, there are strong blue light materials in the system.
- the ⁇ - ⁇ bond interaction has strong charge transfer characteristics, so that there are more non-radiative relaxation channels in the wide band gap, which intensifies the fluorescence quenching between molecules and reduces the quantum yield of the blue light system. Therefore, designing and synthesizing blue-light materials with excellent comprehensive properties will become an important topic in the research of organic electroluminescent materials.
- the first object of the present invention is to provide an organic compound that emits blue to deep blue light and has high luminous efficiency.
- the second object of the present invention is to provide an organic electroluminescent device.
- the third object of the present invention is to provide the application of the compound described in the first object above in the preparation of an organic electroluminescent device.
- the fourth object of the present invention is to provide an organic electroluminescent material.
- the fifth object of the present invention is to provide the application of the compound described in the first object above in the preparation of organic electroluminescent materials.
- R 1 to R 10 are each independently selected from hydrogen, deuterium, straight chain alkyl having C 1 -C 40 , straight chain heteroalkyl having C 1 -C 40 , branched chain or ring having C 3 -C 40 -like alkyl, branched or cyclic heteroalkyl with C 3 -C 40 , alkenyl or alkynyl with C 2 -C 40 , aromatic ring system or heteroaryl with 5 to 60 carbon atoms Groups of ring systems, each of the aforementioned groups may be substituted by one or more groups R;
- Ar 1 and Ar 2 are identical or different from each other and are selected from hydrogen, deuterium, aromatic or heteroaromatic ring systems with 5 to 30 carbon atoms, and the ring systems may be substituted by one or more groups R;
- Ar 3 is identically or differently at each occurrence an aromatic or heteroaromatic ring system having 5 to 30 carbon atoms, which ring system may be substituted by one or more non-aromatic groups R 12 ; here Two groups Ar3 bonded to the same nitrogen atom or phosphorus atom may also be bridged to each other by a single bond or a bridging group selected from N( R12 ), C( R12 ) 2 , oxygen or sulfur;
- R 12 is selected from a hydrogen atom, a deuterium atom, a fluorine atom, a nitrile group, an aliphatic hydrocarbon group with C 1 -C 20 , an aromatic ring or a heteroaromatic ring system with 5 to 30 carbon atoms, one or more of which A hydrogen atom can be replaced by a deuterium atom, a halogen atom or a nitrile group, wherein two or more adjacent substituents R 12 can form with one another a monocyclic or polycyclic aliphatic, aromatic or heteroaromatic ring system.
- Aryl in the sense of the present invention contains 6 to 60 carbon atoms
- heteroaryl in the sense of the present invention contains 2 to 60 carbon atoms and at least one heteroatom, with the proviso that the sum of carbon atoms and heteroatoms is at least 5 ; the heteroatom is preferably selected from N, O or S.
- aryl or heteroaryl is taken to mean simple aromatic rings, i.e. benzene, naphthalene, etc., or simple heteroaromatic rings, such as pyridine, pyrimidine, thiophene, etc., or fused aryl or heteroaryl Groups, such as anthracene, phenanthrene, quinoline, isoquinoline, etc.
- Aromatic rings connected to one another via single bonds, such as biphenyl are conversely not referred to as aryl or heteroaryl, but as aromatic ring systems.
- An aromatic or heteroaromatic ring system in the sense of the present invention is intended to be taken to mean a system which does not necessarily contain only aryl or heteroaryl groups, but in which multiple aryl or heteroaryl groups can also be formed by non-aromatic units For example C, N, O or S atom linkages.
- aryl or heteroaryl groups can also be formed by non-aromatic units For example C, N, O or S atom linkages.
- two or more aryl groups are linked by, for example, short alkyl groups such as fluorene, 9,9'-spirobifluorene, 9,9-diarylfluorene, triarylamine
- Systems of diaryl ethers etc. are also taken to mean aromatic ring systems in the sense of the present invention.
- Aliphatic hydrocarbon radicals or alkyl or alkenyl or alkynyl radicals containing 1 to 40 carbon atoms in the sense of the present invention and in which individual hydrogen atoms or -CH2- radicals may also be substituted by the aforementioned radicals are preferably considered to be Refers to the following groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, Neopentyl, cyclopentyl, n-hexyl, neohexyl, cyclohexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, 2-ethylhexyl, cyclohexenyl, heptenyl, cyclohepty
- Alkoxy preferably having 1 to 40 carbon atoms is taken to mean methoxy, trifluoromethoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy radical, sec-butoxy, tert-butoxy, n-pentyloxy, sec-pentyloxy, 2-methylbutoxy, n-hexyloxy, cyclohexyloxy, n-heptyloxy, cycloheptyloxy, n- Octyloxy, cyclooctyloxy, 2-ethylhexyloxy, pentafluoroethoxy and 2,2,2-trifluoroethoxy.
- Heteroalkyl preferably alkyl having 1 to 40 carbon atoms, means a group in which individual hydrogen atoms or -CH2- groups may be replaced by oxygen, sulfur, halogen atoms, is taken to mean alkoxy, Alkylthio, fluorinated alkoxy, fluorinated alkylthio, especially methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butyl Oxygen, tert-butoxy, methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, isobutylthio, sec-butylthio, tert-butylthio, trifluoromethylthio group, trifluoromethoxy, pentafluoroethoxy, pentafluoroethylthio, 2,2,2-trifluoroethoxy, 2,2,2-trifluoro
- cycloalkyl, cycloalkenyl can be cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptyl , cycloheptenyl, wherein one or more -CH 2 - groups can be replaced by the above groups; in addition, one or more hydrogen atoms can also be replaced by deuterium atoms, halogen atoms or nitrile groups.
- R 1 to R 10 are each independently selected from the group consisting of hydrogen, deuterium, an aromatic ring system or a heteroaromatic ring system having 5 to 60 carbon atoms, and each of the aforementioned groups can be One or more groups R are substituted.
- T 1 or T 2 are each independently selected from O, S or C(R) 2 ;
- Ar 1 and Ar 2 are the same or different from each other and are selected from hydrogen, deuterium, aromatic or heteroaromatic ring systems with 5 to 30 carbon atoms, and the ring systems can be surrounded by one or more groups R replaced.
- the compounds represented by the formula I mainly include structures represented by the following formulas CJHB481 ⁇ CJHB690:
- the present invention provides an application of the compound described in the above-mentioned first object in the preparation of an organic electroluminescent material.
- the present invention provides an organic electroluminescent material prepared from the compound described in the above first object.
- the organic electroluminescent material may be composed of the compound of the present invention alone, or may contain other compounds together.
- the compound of the present invention contained in the organic electroluminescence material of the present invention can be used as, but not limited to, a light-emitting layer material, a carrier transport layer material, or a photorefractive layer material.
- the present invention provides an organic electroluminescence device, which comprises a first electrode, a second electrode, and an electrode placed between the first electrode and the second electrode.
- One or more organic layers comprising one or more of the compounds described in the first object above.
- the organic electroluminescent device comprises a cathode, an anode and at least one light-emitting layer. Besides these layers it may also contain further layers, for example in each case one or more hole-injection layers, hole-transport layers, hole-blocking layers, electron-transport layers, electron-injection layers, excitation layers, sub-blocking layer, electron blocking layer and/or charge generating layer. Interlayers having, for example, an exciton-blocking function can likewise be introduced between two emitting layers. It should be noted, however, that not every one of these layers is required to be present.
- the organic electroluminescent device described herein may comprise one light-emitting layer, or it may comprise a plurality of light-emitting layers.
- various light-emitting compounds capable of emitting light are used in the light-emitting layer.
- Particular preference is given to systems with three emitting layers, the three layers being able to exhibit blue, green and red emission. If more than one emitting layer is present, according to the invention at least one of these layers comprises a compound according to the invention.
- the organic electroluminescent device does not comprise a separate hole injection layer and/or hole transport layer and/or hole blocking layer and/or electron transport layer, i.e. the light emitting layer and the hole injection layer or The anode is directly adjacent, and/or the emissive layer is directly adjacent to the electron transport or electron injection layer or the cathode.
- organic electroluminescent devices in which one or more layers are applied by means of a sublimation method by vapor deposition in a vacuum sublimation device at an initial pressure below 10 ⁇ 5 Pa, preferably below 10 ⁇ 6 Pa to apply the material.
- the initial pressure may also be even lower, for example below 10 ⁇ 7 Pa.
- a particular example of this method is the organic vapor jet printing method, in which the material is applied directly via a nozzle and is thus structured.
- organic electroluminescent devices which, from solution, for example by spin coating, or by means of any desired printing method such as screen printing, flexographic printing, lithography, photoinduced thermography, thermal transfer, spray Ink printing or nozzle printing to produce one or more layers.
- Soluble compounds for example obtained by appropriately substituting the compounds represented by formula I. These methods are also particularly suitable for oligomers, dendrimers and polymers. Also possible are hybrid methods in which, for example, one or more layers are applied from solution and one or more further layers are applied by vapor deposition.
- the invention therefore also relates to a method for producing an organic electroluminescent device according to the invention, applying at least one layer by means of a sublimation method and/or applying at least one layer by means of an organic vapor deposition method or by means of sublimation of a carrier gas , and/or apply at least one layer from solution by spin coating or by means of a printing method.
- the present invention relates to compounds comprising at least one of the above indicated compounds of the invention.
- the compounds can preferably also comprise further compounds.
- the processing of the compounds according to the invention from the liquid phase requires the formulation of the compounds according to the invention. These formulations may, for example, be solutions, dispersions or emulsions. For this purpose, mixtures of two or more solvents may preferably be used.
- Suitable and preferred solvents are, for example, toluene, anisole, o-, m- or p-xylene, methyl benzoate, mesitylene, tetralin, o-dimethoxybenzene, tetrahydrofuran, methyltetrahydrofuran, Tetrahydropyran, chlorobenzene, dioxane, phenoxytoluene, especially 3-phenoxytoluene, (-)-fenchone, 1,2,3,5-tetramethylbenzene, 1,2, 4,5-tetramethylbenzene, 1-methylnaphthalene, 2-methylbenzothiazole, 2-phenoxyethanol, 2-pyrrolidone, 3-methylanisole, 4-methylanisole, 3,4-Dimethylanisole, 3,5-Dimethylanisole, Acetophenone, ⁇ -Terpineol, Benzothiazole, Butyl Benzoate, Cumene, Cyclohexanol, Cyclo
- the organic layer is selected from more than one of an electron injection layer, an electron transport layer, a hole blocking layer, an electron blocking layer, a hole transport layer, a hole injection layer, a light emitting layer, and a photorefractive layer.
- the light-emitting layer includes the compound described in the first objective as the main light emitter, and a compound selected from naphthalene, anthracene, pyrene, perylene, phenanthrene, fluoranthene, One or more of benzanthracene and pentacene and their derivatives are used as dopants.
- the mass ratio of the dopant to the main light emitter is 1:99 ⁇ 50:50.
- the present invention provides an application of the compound described in the first objective above in the preparation of an organic electroluminescent device.
- the raw materials used in the present invention can be commercially available, and any range described in the present invention includes the end value and any numerical value between the end value and the end value or any numerical value between the end value. any subrange of .
- the organic compound provided by the present invention is a series of novel organic electroluminescent compounds with condensed ring structures of benzofuran and benzothiophene derivatives, which increase the molecular conjugated surface on the basis of benzofuran and benzothiophene, Enhance the electron density, adjust the substituent group to increase the steric hindrance of the molecule, weaken the ⁇ - ⁇ interaction between the molecules, improve the internal quantum efficiency of the molecule, and have a shorter luminescent wavelength than the previous compounds.
- the compound hinders the generation of exci-exciplexes between organic molecules, increases the internal electron density and stability, thereby improving the efficiency and lifespan of the organic electroluminescent device containing the compound; in addition, the compound improves the resistance to the solution Solubility solves the problems of productivity and cost in the process of conventional blue light materials, and it can also be used to prepare the light-emitting layer in the solution process instead of the vapor deposition process in the original process.
- FIG. 1 shows a schematic diagram of an example of bottom emission of the organic electroluminescent device of the present invention.
- FIG. 2 shows a schematic diagram of an example of top emission of the organic electroluminescence device of the present invention.
- the preparation methods are conventional methods unless otherwise specified.
- the raw materials used can be obtained from open commercial channels unless otherwise specified, and the percentages are all mass percentages unless otherwise specified.
- a series of novel organic compounds provided by the present invention all reactions are carried out under well-known suitable conditions, some involve simple organic preparation, for example, the preparation of N,N-diphenylamine derivatives can be synthesized by skilled operation skills , not described in detail in the present invention.
- Luminance and chromaticity coordinates tested using spectral scanner PhotoResearch PR-715;
- Life test use LTS-1004AC life test device.
- the preparation method of intermediate A1 comprises the steps:
- the second step the preparation of compound Int.-2
- intermediate Int.-3 20.5g (50.0mmol) of intermediate Int.-3 was dissolved in 100mL of dry tetrahydrofuran, and 50.0mL of triethylamine, 11.0g (55.0mmol) of 9-ethynyl anthracene, 1.0g ( 10.0mmol) of cuprous iodide and 3.5g (5.0mmol) of PdCl 2 (PPh 3 ) 2 catalysts, stirred at room temperature for 8 hours, filtered, and the filtrate was concentrated under reduced pressure to dryness, separated and purified with a silica gel column to obtain the intermediate Int. -4, yield 96%.
- the preparation method of intermediate A5 comprises the steps:
- the first step preparation of compound Int.-6
- the preparation method of intermediate B1 comprises the steps:
- the preparation method of compound CJHB652 comprises the following steps:
- a kind of OLED element, as shown in Figure 1, the preparation method of above-mentioned OLED element comprises the steps:
- the glass substrate coated with the ITO conductive layer is ultrasonically treated in a cleaning agent for 30 minutes, rinsed in deionized water, ultrasonicated in acetone/ethanol mixed solvent for 30 minutes, and baked in a clean environment until completely dry, Irradiate with a UV light cleaner for 10 minutes and bombard the surface with a low-energy positive ion beam.
- the organic electroluminescent device of the present invention can be used in wall-mounted TVs, flat panel displays, planar light emitters for lighting, backlights for copiers, printers, liquid crystal displays, or light sources for measuring instruments, display panels, and sign lights.
Landscapes
- Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
本发明涉及一种如式I所示的有机化合物,其中,Ar1、Ar2是在分子的外侧引入芳族环或杂芳族环等基团,R1至R10彼此相同或不同地选自氢、氘、具有C1~C40的直链烷基、具有C3~C40的支链或环状的烷基、具有5~60个碳原子的芳族环系或杂芳族环系组成的组。T1、T2彼此相同或不同地选自O、S、SO、SO2、PR、POR、CR7R8、SiR7R8、BR等。本发明还保护此类化合物在有机电致发光元件中的应用。
Description
本发明涉及有机电致发光技术领域。更具体地,涉及一种有机化合物、含有该化合物的有机电致发光材料,含有该化合物的有机电致发光装置,及其在有机电致发光材料中的应用。
有机电致发光元件所使用的物质大部分为纯有机物或有机物与金属形成络合物的有机金属络合物,根据用途可区分为空穴注入物、空穴输送物、发光物、电子输送物、电子注入物等。在此,作为空穴注入物或空穴输送物主要使用离子化能相对较小的有机物,作为电子注入物或电子输送物主要使用电负性较大的有机物。此外,作为发光辅助层所使用的物质最好能满足如下特性。
第一、有机电致发光元件中所使用的物质需较好的热稳定性,其原因是在有机电致发光元件内部因电荷的迁移而发生焦耳热,目前,作为空穴输送层通常所使用的材料的玻璃化温度低,因此在低温下驱动时出现因发生结晶化而引起发光效率降低的现象。第二、为了降低驱动电压,需要与阴极和阳极邻接的有机物设计成电荷注入势垒较小,电荷迁移率高。第三、电极和有机层的界面、有机层和有机层的界面上一直存在能量壁垒而不可避免地累积一些电荷,因此需要使用电化学稳定性优异的物质。
发光层由主发光体和掺杂物这两种物质构成,掺杂物需要量子效率高,与掺杂物相比主发光体需要能隙大而容易发生向掺杂物的能量转移。用于电视、移动设备等的显示器根据红色、绿色、蓝色这三原色实现全彩色,发光层分别由红色主发光体/掺杂物、绿色主发光体/掺杂物以及蓝色主发光体/掺杂物构成。目前蓝光材料仍然存在发光量子效率低、色纯度差的问题。造成这种状况的主要原因是因为蓝光来自于能隙较宽的能级间的跃迁,而宽禁带的有机化合物在进行分子设计时存在一定的困难,其次蓝光材料的体系中存在着较强的π-π键相互作用,有着很强的电荷转移特性,从而使宽带隙中存在更多的无辐射弛豫通道,加剧了分子之间荧光淬灭,降低了蓝光体系的量子产率。因此设计合成综合性能优良的蓝光材料,将成为有机电致发光材料研究的重要课题。
发明内容
基于以上事实,本发明的第一个目的在于提供一种有机化合物,其发光为蓝色至深蓝色且发光效率高。
本发明的第二个目的在于提供一种有机电致发光装置。
本发明的第三个目的在于提供如上第一个目的所述的化合物在制备有机电致发光装置中的应用。
本发明的第四个目的在于提供一种有机电致发光材料。
本发明的第五个目的在于提供如上第一个目的所述的化合物在制备有机电致发光材料中的应用。
为达到上述第一个目的,本发明采用下述技术方案:
一种有机化合物,其结构通式如式I所示:
其中:
R
1~R
10各自独立地选自氢、氘、具有C
1-C
40的直链烷基、具有C
1-C
40的直链杂烷基、具有C
3-C
40的支链或环状的烷基、具有C
3-C
40的支链或环状的杂烷基、具有C
2-C
40的烯基或炔基、具有5~60个碳原子的芳族环系或杂芳族环系组成的组,前述基团中的每个可被一个或多个基团R取代;
T
1、T
2各自独立地选自O、S、SO、SO
2、C(R)
2、BR、PR、P(=O)R或Si(R)
2;
Ar
1、Ar
2彼此相同或不同地选自氢、氘、具有5~30个碳原子的芳族或杂芳族环系,所述环系可被一个或多个基团R取代;
所述R在每次出现时相同或不同地选自氢原子、氘原子、卤素原子、腈基、硝基、N(Ar
3)
2、N(R
11)
2、C(=O)Ar
3、C(=O)R
11、P(=O)(Ar
3)
2、具有C
1-C
40的直链烷基、具有C
1-C
40的直链杂烷基、具有C
3-C
40的支链或环状的烷基、具有C
3-C
40的支链或环状的杂烷基、具有C
2-C
40的烯基或炔基、具有5至80个、优选5至60个碳原子的芳族环或杂芳族环系、具有5至60个碳原子的芳氧基或杂芳氧基组成的组,所述基团中的每个可被一个或多个基团R
11取代,或这些体系的组合,其中一个或多个非相邻的-CH
2-基团可被R
11C=CR
11、C≡C、Si(R
11)
2、Ge(R
11)
2、Sn(R
11)
2、C=O、C=S、C=Se、C=NR
11、P(=O)(R
11)、SO、SO
2、NR
11、O、S或CONR
11代替,并且其中一个或多个氢原子可被氘原子、卤素原子、腈基或硝基代替,其中两个或更多个相邻的R可以任选地接合或稠合形成单环或多环的脂族、芳族或杂芳族环系,所述环系可被一个或多个基团R
11取代;
R
11在每次出现时相同或不同地选自氢原子、氘原子、卤素原子、腈基、硝基、N(Ar
3)
2、N(R
12)
2、C(=O)Ar
3、C(=O)R
12、P(=O)(Ar
3)
2、具有C
1-C
40的直链烷基、具有C
1-C
40的直链杂烷基、具有C
3-C
40的支链或环状的烷基、具有C
3-C
40的支链或环状的杂烷基、具有C
2-C
40的烯基或炔基、具有5至60个碳原子的芳族环或杂芳族环系、具有5至60个碳原子的芳氧基或杂芳氧基组成的组,所述基团中的每个可被一个或多个基团R
12取代,或这些体系的组合,其中一个或多个非相邻的-CH
2-基团可被R
12C=CR
12、C≡C、Si(R
12)
2、Ge(R
12)
2、Sn(R
12)
2、C=O、C=S、C=Se、C=NR
12、P(=O)(R
12)、SO、SO
2、NR
12、O、S或CONR
12代替,并且其中一个或多个氢原子可被氘原子、卤素原子、腈基或硝基代替,其中两个或更多个相邻的取代基R可以任选地接合或稠合形成单环或多环的脂族、芳族或杂芳族环系, 所述环系可被一个或多个基团R
12取代;
Ar
3在每次出现时相同或不同地是具有5~30个碳原子的芳族或杂芳族环系,所述环系可被一个或多个非芳族基团R
12取代;此处键合至同一氮原子或磷原子的两个基团Ar
3也可通过单键或选自N(R
12)、C(R
12)
2、氧或硫的桥连基彼此桥连;
R
12选自氢原子、氘原子、氟原子、腈基、具有C
1-C
20的脂族烃基、具有5~30个碳原子的芳族环或杂芳族环系,其中一个或多个氢原子可被氘原子、卤素原子或腈基代替,其中两个或更多个相邻的取代基R
12可彼此形成单环或多环的脂族、芳族或杂芳族环系。
本发明意义上的芳基含有6-60个碳原子,在本发明意义上的杂芳基含有2-60个碳原子和至少一个杂原子,其条件是碳原子和杂原子的总和至少是5;所述杂原子优选选自N、O或S。此处的芳基或杂芳基被认为是指简单的芳族环,即苯、萘等,或简单的杂芳族环,如吡啶、嘧啶、噻吩等,或稠合的芳基或杂芳基,如蒽、菲、喹啉、异喹啉等。通过单键彼此连接的芳族环,例如联苯,相反地不被称为芳基或杂芳基,而是称为芳族环系。
在本发明意义上的芳族或杂芳族环系旨在被认为是指不必仅含有芳基或杂芳基的体系,而是其中多个芳基或杂芳基还可以由非芳族单元例如C、N、O或S原子连接。因此,例如,和其中两个或更多个芳基被例如短的烷基连接的体系一样,诸如芴、9,9’-螺二芴、9,9-二芳基芴、三芳基胺、二芳基醚等的体系也被认为是指在本发明意义上的芳族环系。
对于本发明意义上的含有1~40个碳原子并且其中单独的氢原子或-CH
2-基团还可被上述基团取代的脂族烃基或者烷基或者烯基或炔基优选被认为是指如下基团:甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、2-甲基丁基、正戊基、仲戊基、新戊基、环戊基、正己基、新己基、环己基、正庚基、环庚基、正辛基、环辛基、2-乙基己基、环己烯基、庚烯基、环庚烯基、辛烯基、环辛烯基、乙炔基、丙炔基、丁炔基、戊炔基、己炔基、庚炔基或辛炔基。烷氧基优选具有1-40个碳原子的烷氧基被认为是指甲氧基、三氟甲氧基、乙氧基、正丙氧基、异丙氧基、正丁氧基、异丁氧基、仲丁氧基、叔丁氧基、正戊氧基、仲戊氧基、2-甲基丁氧基、正己氧基、环己氧基、正庚氧基、环庚氧基、正辛氧基、环辛氧基、2-乙基己氧基、五氟乙氧基和2,2,2-三氟乙氧基。杂烷基优选具有1-40个碳原子的烷基,是指其中单独的氢原子或-CH
2-基团可被氧、硫、卤素原子取代的基团,被认为是指烷氧基、烷硫基、氟代的烷氧基、氟代的烷硫基,特别是指甲氧基、乙氧基、正丙氧基、异丙氧基、正丁氧基、异丁氧基、仲丁氧基、叔丁氧基、甲硫基、乙硫基、正丙硫基、异丙硫基、正丁硫基、异丁硫基、仲丁硫基、叔丁硫基、三氟甲硫基、三氟甲氧基、五氟乙氧基、五氟乙硫基、2,2,2-三氟乙氧基、2,2,2-三氟乙硫基、乙烯氧基、乙烯硫基、丙烯氧基、丙烯硫基、丁烯硫基、丁烯氧基、戊烯氧基、戊烯硫基、环戊烯氧基、环戊烯硫基、己烯氧基、己烯硫基、环己烯氧基、环己烯硫基、乙炔氧基、乙炔硫基、丙炔氧基、丙炔硫基、丁炔氧基、丁炔硫基、戊炔氧基、戊炔硫基、己炔氧基、己炔硫基。
一般来说,根据本发明的环烷基、环烯基可为环丙基、环丁基、环戊基、环己基、环丁烯基、环戊烯基、环己烯基、环庚基、环庚烯基,其中一个或多个-CH
2-基团可被上述基团代替;此外,一个或多个氢原子还可被氘原子、卤素原子或腈基代替。
根据本发明的芳族或杂芳族环原子,在每种情况下还可被上述基团R
12取代的芳族或杂芳族环系,特别是指衍生自如下物质的基团:苯、萘、蒽、苯并蒽、菲、芘、
苝、 荧蒽、并四苯、并五苯、苯并芘、联苯、偶苯、三联苯、三聚苯、芴、螺二芴、二氢菲、二氢芘、四氢芘、顺式或反式茚并芴、顺式或反式茚并咔唑、顺式或反式吲哚并咔唑、三聚茚、异三聚茚、螺三聚茚、螺异三聚茚、呋喃、苯并呋喃、异苯并呋喃、二苯并呋喃、噻吩、苯并噻吩、异苯并噻吩、二苯并噻吩、吡咯、吲哚、异吲哚、咔唑、吡啶、喹啉、异喹啉、吖啶、菲啶、苯并[5,6]喹啉、苯并[6,7]喹啉、苯并[7,8]喹啉、吩噻嗪、吩噁嗪、吡唑、吲唑、咪唑、苯并咪唑、萘并咪唑、菲并咪唑、吡啶并咪唑、吡嗪并咪唑、喹喔啉并咪唑、噁唑、苯并噁唑、萘并噁唑、蒽并噁唑、菲并噁唑、异噁唑、1,2-噻唑、1,3-噻唑、苯并噻唑、哒嗪、六氮杂苯并菲、苯并哒嗪、嘧啶、苯并嘧啶、喹喔啉、1,5-二氮杂蒽、2,7-二氮杂芘、2,3-二氮杂芘、1,6-二氮杂芘、1,8-二氮杂芘、4,5-二氮杂芘,4,5,9,10-四氮杂苝、吡嗪、吩嗪、吩噁嗪、吩噻嗪、荧红环、萘啶、氮杂咔唑、苯并咔啉、咔啉、菲咯啉、1,2,3-三唑、1,2,4-三唑、苯并三唑、1,2,3-噁二唑、1,2,4-噁二唑、1,2,5-噁二唑、1,3,4-噁二唑、1,2,3-噻二唑、1,2,4-噻二唑、1,2,5-噻二唑、1,3,4-噻二唑、1,3,5-三嗪、1,2,4-三嗪、1,2,3-三嗪、四唑、1,2,4,5-四嗪、1,2,3,4-四嗪、1,2,3,5-四嗪、嘌呤、蝶啶、吲嗪和苯并噻二唑或者衍生自这些体系的组合的基团。
进一步地,所述R
1~R
10各自独立地选自氢、氘、具有5~60个碳原子的芳族环系或杂芳族环系组成的组,前述基团中的每个可被一个或多个基团R取代。
进一步地,所述T
1或T
2各自独立地选自O、S或C(R)
2;
进一步地,所述Ar
1、Ar
2彼此相同或不同地选自氢、氘、具有5~30个碳原子的芳族或杂芳族环系,所述环系可被一个或多个基团R取代。
进一步地,所述式I所示的化合物主要包括以下式CJHB481~CJHB690所示的结构:
为达到上述第二个目的,本发明提供一种如上第一个目的所述的化合物在制备有机电致发光材料中的应用。
为达到上述第三个目的,本发明提供有机电致发光材料,所述材料由如上第一个目的所述的化合物制备得到。
有机电致发光材料可以单独使用本发明的化合物构成,也可以同时含有其他化合物。
本发明的有机电致发光材料中所含有的本发明的化合物可以用作但不限于发光层材料、载流子传输层材料或光折射层材料。
为达到上述第四个目的,本发明提供一种有机电致发光装置,所述有机电致发光装置包括第一电极、第二电极和置于所述第一电极、所述第二电极之间的一个或多个有机层,所述一个或多个有机层包含如上第一个目的所述的化合物中的一种或多种。
所述有机电致发光装置包含阴极、阳极和至少一个发光层。除了这些层之外,它还可以包含其它的层,例如在每种情况下,包含一个或多个空穴注入层、空穴传输层、空穴阻挡层、电子传输层、电子注入层、激子阻挡层、电子阻挡层和/或电荷产生层。具有例如激子阻挡功能的中间层同样可引入两个发光层之间。然而,应当指出,这些层中的每个并非必须都存在。此处所述有机电致发光装置可包含一个发光层,或者它可包含多个发光层。即,将能够发光的多种发光化合物用于所述发光层中。特别优选具有三个发光层的体系,其中所述三个层可显示蓝色、绿色和红色发光。如果存在多于一个的发光层,则根据本发明,这些层中的至少一个层包含本发明的化合物。
进一步地,根据本发明的有机电致发光装置不包含单独的空穴注入层和/或空穴传输层 和/或空穴阻挡层和/或电子传输层,即发光层与空穴注入层或阳极直接相邻,和/或发光层与电子传输层或电子注入层或阴极直接相邻。
在根据本发明的有机电致发光装置的其它层中,特别是在空穴注入和空穴传输层中以及在电子注入和电子传输层中,所有材料可以按照根据现有技术通常所使用的方式来使用。本领域普通技术人员因此将能够在不付出创造性劳动的情况下与根据本发明的发光层组合使用关于有机电致发光元件所知的所有材料。
此外优选如下的有机电致发光装置,其借助于升华方法施加一个或多个层,其中在真空升华装置中在低于10
-5Pa、优选低于10
-6Pa的初压下通过气相沉积来施加所述材料。然而,所述初压还可能甚至更低,例如低于10
-7Pa。
同样优选如下的有机电致发光器件,其借助于有机气相沉积方法或借助于载气升华来施加一个或多个层,其中,在10
-5Pa至1Pa之间的压力下施加所述材料。该方法的特别的例子是有机蒸气喷印方法,其中所述材料通过喷嘴直接施加,并且因此是结构化的。
此外优选如下的有机电致发光装置,从溶液中,例如通过旋涂,或借助于任何所希望的印刷方法例如丝网印刷、柔性版印刷、平版印刷、光引发热成像、热转印、喷墨印刷或喷嘴印刷,来产生一个或多个层。可溶性化合物,例如通过适当的取代式I所示的化合物获得可溶性化合物。这些方法也特别适于低聚物、树枝状大分子和聚合物。此外可行的是混合方法,其中例如从溶液中施加一个或多个层并且通过气相沉积施加一个或多个另外的层。
这些方法是本领域普通技术人员通常已知的,并且他们可以在不付出创造性劳动的情况下将其应用于包含根据本发明的化合物的有机电致发光元件。
因此,本发明还涉及制造根据本发明的有机电致发光装置的方法,其借助于升华方法来施加至少一个层,和/或借助于有机气相沉积方法或借助于载气升华来施加至少一个层,和/或从溶液中通过旋涂或借助于印刷方法来施加至少一个层。
此外,本发明涉及包含至少一种上文指出的本发明的化合物。如上文关于有机电致发光装置指出的相同优选情况适用于所述本发明的化合物。特别是,所述化合物此外还可优选包含其它化合物。从液相处理根据本发明的化合物,例如通过旋涂或通过印刷方法进行处理,需要根据本发明的化合物的制剂。这些制剂可以例如是溶液、分散体或乳液。出于这个目的,可优选使用两种或更多种溶剂的混合物。合适并且优选的溶剂例如是甲苯、苯甲醚、邻二甲苯、间二甲苯或对二甲苯、苯甲酸甲酯、均三甲苯、萘满、邻二甲氧基苯、四氢呋喃、甲基四氢呋喃、四氢吡喃、氯苯、二噁烷、苯氧基甲苯、特别是3-苯氧基甲苯、(-)-葑酮、1,2,3,5-四甲基苯、1,2,4,5-四甲基苯、1-甲基萘、2-甲基苯并噻唑、2-苯氧基乙醇、2-吡咯烷酮、3-甲基苯甲醚、4-甲基苯甲醚、3,4-二甲基苯甲醚、3,5-二甲基苯甲醚、苯乙酮、α-萜品醇、苯并噻唑、苯甲酸丁酯、异丙苯、环己醇、环己酮、环己基苯、十氢化萘、十二烷基苯、苯甲酸乙酯、茚满、苯甲酸甲酯、1-甲基吡咯烷酮、对甲基异丙基苯、苯乙醚、1,4-二异丙基苯、二苄醚、二乙二醇丁基甲基醚、三乙二醇丁基甲基醚、二乙二醇二丁基醚、三乙二醇二甲基醚、二乙二醇单丁基醚、三丙二醇二甲基醚、四乙二醇二甲基醚、2-异丙基萘、戊苯、己苯、庚苯、辛苯、1,1-双(3,4-二甲基苯基)乙烷,或这些溶剂的混合物。
进一步地,所述有机层选自电子注入层、电子输送层、空穴阻挡层、电子阻挡层、空穴输送层、空穴注入层、发光层、光折射层的一种以上。
进一步地,所述掺杂物与主发光体的质量比为1:99~50:50。
为达到上述第五个目的,本发明提供一种如上第一个目的所述的化合物在制备有机电致发光装置中的应用。
如无特殊说明,本发明中所用原料均可通过市售商购获得,本发明所记载的任何范围包括端值以及端值之间的任何数值以及端值或者端值之间的任意数值所构成的任意子范围。
本发明的有益效果如下:
本发明提供的有机化合物是一系列具有苯并呋喃、苯并噻吩衍生物的稠环结构的新型有机电致发光化合物,是在苯并呋喃、苯并噻吩的基础上增大分子共轭面,增强电子密度,同时调整取代基团增大分子位阻、减弱分子间的π-π相互作用,提高分子的内量子效率,并且具有与以住的化合物相比更短的发光波长。同时,该化合物阻碍有机分子间激-激复合物的生成、增加内部电子密度和稳定性,由此得以提高包含该化合物的有机电致发光器件的效率、寿命;此外,该化合物改善对溶液的溶解度而解决以往蓝光材料所具有的工序的生产性以及费用问题,并且在原有的工序中不是其蒸镀工序而是在其溶液工序中也可以用于制备发光层。
下面结合附图对本发明的具体实施方式作进一步详细的说明。
图1示出本发明的有机电致发光装置的一个底部发光例子的示意图。
图2示出本发明的有机电致发光装置的一个顶部发光例子的示意图。
其中,1-基板、2-阳极、3-空穴注入层、4-空穴传输层/电子阻挡层、5-发光层、6-空穴阻挡/电子传输层、7-电子注入层、8-阴极。
为了更清楚地说明本发明,下面结合优选实施例和附图对本发明做进一步的说明。附图中相似的部件以相同的附图标记进行表示。本领域技术人员应当理解,下面所具体描述的内容是说明性的而非限制性的,不应以此限制本发明的保护范围。
本发明中,制备方法如无特殊说明则均为常规方法。所用的原料如无特别说明均可从公开的商业途径获得,所述百分比如无特殊说明均为质量百分比。本发明提供的一系列新型有机化合物,所有的反应都是在众所周知的适合条件下进行,有些涉及到简单的有机制备,例如N,N-二苯胺衍生物的制备均能通过熟练的操作技能合成,在本发明中没有详细描述。
下述实施例对OLED材料及元件进行性能测试的测试仪器及方法如下:
OLED元件性能检测条件:
亮度和色度坐标:使用光谱扫描仪PhotoResearch PR-715测试;
电流密度和起亮电压:使用数字源表Keithley 2420测试;
功率效率:使用NEWPORT 1931-C测试;
寿命测试:使用LTS-1004AC寿命测试装置。
实施例1
中间体A1的制备:
中间体A1的制备方法,包括如下步骤:
第一步:化合物Int.-1的制备
在氮气保护下,29.5g(100.0mmol)的4-碘二苯并呋喃溶于100mL干燥的四氢呋喃中,加入50.0mL的三乙胺、11.8g(120.0mmol)的三甲基硅基乙炔、2.0g(10.0mmol)的碘化亚铜和0.7g(1.0mmol)的PdCl
2(PPh
3)
2催化剂,室温搅拌反应8小时,过滤,滤液减压浓缩干,用硅胶柱分离纯化,得到中间体Int.-1,收率98%。
第二步:化合物Int.-2的制备
在氮气保护下,13.2g(50.0mmol)第一步制备的Int.-1溶解于50mL的DMF中,加入22.0g(100.0mmol)的邻碘苯酚,4.2g的无水氯化锂和5.5g的无水碳酸钠,升温到100℃,搅拌反应24小时,降到室温,将反应液倒入250mL的水中,用乙酸乙酯萃取,收集有机相,用饱和盐水洗、水洗,收集有机相干燥,过滤,滤液减压浓缩干,用硅胶柱分离纯化,得到Int.-2,收率76%。
第三步:化合物Int.-3的制备
取17.8g(50.0mmol)第二步制备的中间体Int.-2溶解于120mL的二氯甲烷中,在氮气保护下,降温至-78℃,加入8.5g(50.0mmol)的氯化碘,搅拌反应1小时,加入100mL的亚硫酸氢钠水溶液,分出有机相,水相再用二氯甲烷萃取,收集有机相用水洗,有机相干燥过滤,滤液减压浓缩干,用硅胶柱分离纯化,得到Int.-3,收率90%。
第四步:化合物Int.-4的制备
在氮气保护下,20.5g(50.0mmol)的中间体Int.-3溶于100mL干燥的四氢呋喃中,加入50.0mL的三乙胺、11.0g(55.0mmol)的9-乙炔基蒽、1.0g(10.0mmol)的碘化亚铜和3.5g(5.0mmol)的PdCl
2(PPh
3)
2催化剂,室温搅拌反应8小时,过滤,滤液减压浓缩干,用硅胶柱分离纯化,得到中间体Int.-4,收率96%。
第五步:化合物Int.-5的制备
在氮气保护下,9.7g(20.0mmol)的中间体Int.-4溶于120mL干燥的甲苯中,加入530.0mg(2.0mmol)的氯化铂,升温回流搅拌反应12小时,减压浓缩干,用硅胶柱分离纯化,得到中间体Int.-5,收率76.5%。
第六步:中间体A1的制备
20.0g(41.2mmol)的中间体Int.-5溶于120mL的二氯甲烷中,冰水浴降温至0℃,加入780.0mg(4.1mmol)的对甲苯磺酸,分批加入7.5g(42.0mmol)的NBS,搅拌反应2小时,加入100mL的10%碳酸氢钠水溶液,分出有机相,用水洗,收集有机相,干燥,过滤,滤液减压浓缩干,用硅胶柱分离纯化,得到中间体A1,收率95%。
参照上述的合成方法,制备以下化合物:
实施例2
中间体A5的制备:
中间体A5的制备方法,包括如下步骤:
第一步:化合物Int.-6的制备
参照实施例1第四步的制备方法,仅将实施例1第四步中的9-乙基蒽替换为对溴苯基乙炔,制备中间体Int.-6,收率92%。
第二步:中间体A5的制备
参照实施例1第五步的制备方法,仅将实施例1第五步中的Int.-4替换为上步的中间体Int.-6,制备中间体A5,收率42%。
参照上述的合成方法,制备以下化合物:
实施例3
中间体B1的制备:
中间体B1的制备方法,包括如下步骤:
第一步:化合物Int.-7的制备
在氮气保护下,5.0g(37.8mmol)的2-甲氧基苯乙炔溶于50mL的三乙胺中,加入11.2g(45.5mmol)的1-溴二苯并呋喃、760.0mg(4.0mmol)的碘化亚铜、0.9g(4.0mmol)的醋酸钯和2.1g(8.0mmol)的三苯基磷,升温回流搅拌反应6小时,减压浓缩干,用硅胶柱分离纯化,得到中间体Int.-7,收率92%。
第二步:化合物Int.-8的制备
在氮气保护下,10.0g(33.5mmol)的中间体Int.-7溶于60mL的二氯甲烷中,加入8.5g(33.5mmol)的碘,于室温搅拌反应20小时,加入20mL的饱和硫代硫酸钠水溶液,分出有机相用1N稀盐酸水洗,水洗,干燥,过滤,滤液减压浓缩干,用硅胶柱分离纯化,得到中间体Int.-8,收率89%。
第三步:化合物Int.-9的制备
参照实施例1第四步的制备方法,仅将实施例1第四步中的9-乙基蒽替换为对溴苯基乙炔,制备中间体Int.-9,收率95%。
第四步:中间体B1的制备
参照实施例1第五步的制备方法,仅将实施例1第五步中的Int.-4替换为上步的中间体Int.-9,制备中间体B1,收率38%。
参照上述的合成方法,制备以下化合物:
实施例4
化合物CJHB481的制备:
取15.0mmol中间体A1与60mL的甲苯混合,在氮气保护下,加入18.0mmol的苯硼酸、54.0mmol的无水碳酸钠和173.0mg的Pd(PPh
3)
4催化剂,再加入30mL的乙醇和 30mL的水,升温至回流搅拌反应12小时,冷却到室温,过滤,滤饼用水洗、乙醇洗,用硅胶柱分离纯化,得到白色固体CJHB481,收率84%。
参照上述的合成方法,制备以下化合物:
实施例5
化合物CJHB652的制备方法,包括如下步骤:
第一步:化合物Int.-10的制备
在氮气保护下,23.0g(50.0mmol)的A5溶解于120mL干燥的THF中,降温到-78℃,滴加入24mL的2.5M正丁基锂正己烷溶液,搅拌反应30分钟,滴加入7.8g(75.0mmol)的硼酸三甲酯,搅拌反应30分钟,升到室温反应1小时,滴加入50mL的2N稀盐酸水溶液,搅拌30分钟,分出有机相,水相用乙酸乙酯萃取,收集有机相,干燥,过滤,滤液减压浓缩干,加入石油醚分散,过滤,得到白色固体Int.-10,收率83%。
第二步:化合物CJHB652的制备
取12.0mmol中间体Int.-10与60mL的甲苯混合,在氮气保护下,加入10.0mmol的 2-氯-4,6-二苯基-1,3,5-三嗪、48.0mmol的无水碳酸钠和115.0mg的Pd(PPh
3)
4催化剂,再加入30mL的乙醇和30mL的水,升温至回流搅拌反应12小时,冷却到室温,过滤,滤饼用水洗、乙醇洗,用硅胶柱分离纯化,得到白色固体CJHB652,收率77%。
参照上述的合成方法,制备以下化合物:
实施例6
化合物CJHB530的制备:
将10.0mmol的中间体A1分散在80mL的甲苯中,加入12.0mmol的4,4’-二甲基二苯胺,再加入2.0g(20.0mmol)的叔丁醇钠、55.0mg(0.05mmol)的Pd
2(dba)
3CHCl
3催化剂和0.01mL的10%叔丁基磷甲苯溶液,升温至90℃搅拌反应12小时,反应结束后,加入50mL的水,分出有机相,水相用乙酸乙酯-THF萃取,收集有机相干燥,过滤,滤液减压浓缩干,用硅胶柱分离纯化,再用THF-甲苯重结晶,得到CJHB530,黄色固体,收率43%。
参照上述的合成方法,制备以下化合物:
实施例7
一种OLED元件,如图1所示,上述OLED元件的制备方法包括如下步骤:
1)将涂布了ITO导电层的玻璃基片在清洗剂中超声处理30分钟,在去离子水中冲洗,在丙酮/乙醇混合溶剂中超声30分钟,在洁净的环境下烘烤至完全干燥,用紫外光清洗机照射10分钟,并用低能阳离子束轰击表面。
2)把上述处理好的ITO玻璃基片置于真空腔内,抽真空至1×10
-5~9×10
-3Pa,在上述阳极层膜上继续分别蒸镀化合物DNTPD作为空穴注入层,蒸镀膜厚为
在上述空穴注入层膜上继续蒸镀NPD为空穴传输层,蒸镀膜厚为
4)在电子阻挡层上继续蒸镀一层本发明的式I所示的化合物和BD017作为有机发光层,其中,BD017为掺杂材料和本发明的式I所示的化合物为主体材料,式I所示的化合物在BD017中的掺杂浓度为10%,蒸镀膜厚为
上述实施例7中使用的化合物结构如下:
实施例8
参照实施例7相同的步骤,不同之处在于使用化合物CJHB481作为式I所示的化合物。
实施例9
参照实施例7相同的步骤,不同之处在于使用化合物CJHB494作为式I所示的化合物。
实施例10
参照实施例7相同的步骤,不同之处在于使用化合物CJHB546作为式I所示的化合物。
实施例11
参照实施例7相同的步骤,不同之处在于使用化合物CJHB573作为式I所示的化合物。
实施例12
参照实施例7相同的步骤,不同之处在于使用化合物CJHB619作为式I所示的化合物。
实施例13
参照实施例7相同的步骤,不同之处在于使用化合物CJHB628作为式I所示的化合物。
实施例14
参照实施例7相同的步骤,不同之处在于使用化合物CJHB639作为式I所示的化合物。
比较例1
参照实施例7相同的步骤,不同之处在于使用化合物α,β-ADN代替式I所示的化合物。
化合物α,β-ADN的结构为:
所得有机发光元件的性能检测结果示于下表1中:
表1性能检测结果
上述表中,在电流密度为10mA/cm
2条件下的驱动电压、半峰宽FWHM、电流效率以及在亮度为1000cd/m
2初始条件下的器件寿命LT90%的数据是针对比较例1归一化。
结论:从性能测试结果表1可以看到,本发明的化合物作为蓝光染料获得了深蓝光有机电致发光器件,相较于采用α,β-ADN作为蓝光主体材料的有机电致发光器件,元件的电流效率更高、驱动电压降低,而且器件初始亮度在1000cd/m
2的条件下,器件的LT90%寿命也有了很大的改善。
产业上的应用可能性
本发明的有机电致发光装置可以在壁挂电视、平板显示器、照明等的平面发光体、复印机、打印机、液晶显示器的背光源或计量仪器类等的光源,显示板、标识灯等中应用。
显然,本发明的上述实施例仅仅是为清楚地说明本发明所作的举例,而并非是对本发明的实施方式的限定,对于所属领域的普通技术人员来说,在上述说明的基础上还可以做出其它不同形式的变化或变动,这里无法对所有的实施方式予以穷举,凡是属于本发明的 技术方案所引伸出的显而易见的变化或变动仍处于本发明的保护范围之列。
Claims (10)
- 一种有机化合物,其特征在于,所述化合物的结构通式如式I所示:其中:R 1~R 10各自独立地选自氢、氘、具有C 1-C 40的直链烷基、具有C 1-C 40的直链杂烷基、具有C 3-C 40的支链或环状的烷基、具有C 3-C 40的支链或环状的杂烷基、具有C 2-C 40的烯基或炔基、具有5~60个碳原子的芳族环系或杂芳族环系组成的组,前述基团中的每个可被一个或多个基团R取代;T 1、T 2各自独立地选自O、S、SO、SO 2、C(R) 2、BR、PR、P(=O)R或Si(R) 2;Ar 1、Ar 2彼此相同或不同地选自氢、氘、具有5~30个碳原子的芳族或杂芳族环系,所述环系可被一个或多个基团R取代;所述R在每次出现时相同或不同地选自氢原子、氘原子、卤素原子、腈基、硝基、N(Ar 3) 2、N(R 11) 2、C(=O)Ar 3、C(=O)R 11、P(=O)(Ar 3) 2、具有C 1-C 40的直链烷基、具有C 1-C 40的直链杂烷基、具有C 3-C 40的支链或环状的烷基、具有C 3-C 40的支链或环状的杂烷基、具有C 2-C 40的烯基或炔基、具有5至80个、优选5至60个碳原子的芳族环或杂芳族环系、具有5至60个碳原子的芳氧基或杂芳氧基组成的组,所述基团中的每个可被一个或多个基团R 11取代,或这些体系的组合,其中一个或多个非相邻的-CH 2-基团可被R 11C=CR 11、C≡C、Si(R 11) 2、Ge(R 11) 2、Sn(R 11) 2、C=O、C=S、C=Se、C=NR 11、P(=O)(R 11)、SO、SO 2、NR 11、O、S或CONR 11代替,并且其中一个或多个氢原子或被氘原子、卤素原子、腈基或硝基代替,其中两个或更多个相邻的R可以任选地接合或稠合形成单环或多环的脂族、芳族或杂芳族环系,所述环系可被一个或多个基团R 11取代;R 11在每次出现时相同或不同地选自氢原子、氘原子、卤素原子、腈基、硝基、N(Ar 3) 2、N(R 12) 2、C(=O)Ar 3、C(=O)R 12、P(=O)(Ar 3) 2、具有C 1-C 40的直链烷基、具有C 1-C 40的直链杂烷基、具有C 3-C 40的支链或环状的烷基、具有C 3-C 40的支链或环状的杂烷基、具有C 2-C 40的烯基或炔基、具有5至60个碳原子的芳族环或杂芳族环系、具有5至60个碳原子的芳氧基或杂芳氧基组成的组,所述基团中的每个可被一个或多个基团R 12取代,或这些体系的组合,其中一个或多个非相邻的-CH 2-基团可被R 12C=CR 12、C≡C、Si(R 12) 2、Ge(R 12) 2、Sn(R 12) 2、C=O、C=S、C=Se、C=NR 12、P(=O)(R 12)、SO、SO 2、NR 12、O、S或CONR 12代替,并且其中一个或多个氢原子可被氘原子、卤素原子、腈基或硝基代替,其中两个或更多个相邻的取代基R可以任选地接合或稠合形成单环或多环的脂族、芳族或杂芳族环系,所述环系可被一个或多个基团R 12取代;Ar 3在每次出现时相同或不同地是具有5~30个碳原子的芳族或杂芳族环系,所述环系 可被一个或多个非芳族基团R 12取代;此处键合至同一氮原子或磷原子的两个基团Ar 3也可通过单键或选自N(R 12)、C(R 12) 2、氧或硫的桥连基彼此桥连;R 12选自氢原子、氘原子、氟原子、腈基、具有C 1-C 20的脂族烃基、具有5~30个碳原子的芳族环或杂芳族环系,其中一个或多个氢原子可被氘原子、卤素原子、或腈基代替,其中两个或更多个相邻的取代基R 12可彼此形成单环或多环的脂族、芳族或杂芳族环系。
- 根据权利要求1所述的化合物,其特征在于,所述R 1~R 10各自独立地选自氢、氘、具有5~60个碳原子的芳族环系或杂芳族环系组成的组,前述基团中的每个可被一个或多个基团R取代;T 1、T 2各自独立地选自O、S或C(R) 2;Ar 1、Ar 2彼此相同或不同地选自氢、氘、具有5~30个碳原子的芳族或杂芳族环系,所述环系可被一个或多个基团R取代。
- 根据权利要求1所述的化合物,其特征在于,所述R在每次出现时相同或不同地选自氢原子、氘原子、卤素原子、腈基、硝基、N(Ar 3) 2、N(R 11) 2、C(=O)Ar 3、C(=O)R 11、P(=O)(Ar 3) 2、具有C 1-C 40的直链烷基、具有C 1-C 40的直链杂烷基、具有C 3-C 40的支链或环状的烷基、具有C 3-C 40的支链或环状的杂烷基、具有C 2-C 40的烯基或炔基、具有5至80个、优选5至60个碳原子的芳族环或杂芳族环系、具有5至60个碳原子的芳氧基或杂芳氧基组成的组,所述基团中的每个可被一个或多个基团R 11取代,或这些体系的组合,其中一个或多个非相邻的-CH 2-基团可被R 11C=CR 11、C≡C、Si(R 11) 2、Ge(R 11) 2、Sn(R 11) 2、C=O、C=S、C=Se、C=NR 11、P(=O)(R 11)、SO、SO 2、NR 11、O、S或CONR 11代替,并且其中一个或多个氢原子可被氘原子、卤素原子、腈基或硝基代替,其中两个或更多个相邻的R可以任选地接合或稠合形成单环或多环的脂族、芳族或杂芳族环系,所述环系可被一个或多个基团R 11取代;R 11在每次出现时相同或不同地选自氢原子、氘原子、卤素原子、腈基、硝基、N(Ar 3) 2、N(R 12) 2、C(=O)Ar 3、C(=O)R 12、P(=O)(Ar 3) 2、具有C 1-C 40的直链烷基、具有C 1-C 40的直链杂烷基、具有C 3-C 40的支链或环状的烷基、具有C 3-C 40的支链或环状的杂烷基、具有C 2-C 40的烯基或炔基、具有5至60个碳原子的芳族环或杂芳族环系、具有5至60个碳原子的芳氧基或杂芳氧基组成的组,所述基团中的每个可被一个或多个基团R 12取代,或这些体系的组合,其中一个或多个非相邻的-CH 2-基团可被R 12C=CR 12、C≡C、Si(R 12) 2、Ge(R 12) 2、Sn(R 12) 2、C=O、C=S、C=Se、C=NR 12、P(=O)(R 12)、SO、SO 2、NR 12、O、S或CONR 12代替,并且其中一个或多个氢原子可被氘原子、卤素原子、腈基或硝基代替,其中两个或更多个相邻的取代基R可以任选地接合或稠合形成单环或多环的脂族、芳族或杂芳族环系,所述环系可被一个或多个基团R 12取代;Ar 3在每次出现时相同或不同地是具有5~30个碳原子的芳族或杂芳族环系,所述环系可被一个或多个非芳族基团R 12取代;此处键合至同一氮原子或磷原子的两个基团Ar 3也可通过单键或选自N(R 12)、C(R 12) 2、氧或硫的桥连基彼此桥连;R 12选自氢原子、氘原子、氟原子、腈基、具有C 1-C 20的脂族烃基、具有5~30个碳原子的芳族环或杂芳族环系,其中一个或多个氢原子可被氘原子、卤素原子或腈基代替,其中两个或更多个相邻的取代基R 12可彼此形成单环或多环的脂族、芳族或杂芳族环系。
- 一种如权利要求1所述的有机化合物在制备有机电致发光材料中的应用。
- 一种有机电致发光材料,其特征在于,所述材料由如权利要求1所述的有机化合物制备得到。
- 一种有机电致发光装置,其特征在于,所述有机电致发光装置包括第一电极、第二电极和置于所述第一电极、所述第二电极之间的一个或多个有机层,所述一个或多个有机层包含权利要求1所述的有机化合物中的一种或多种。
- 根据权利要求7所述的有机电致发光装置,其特征在于,所述有机层选自电子注入层、电子输送层、空穴阻挡层、电子阻挡层、空穴输送层、空穴注入层、发光层的一种及以上。
- 一种如权利要求1至4任一项所述的有机化合物在制备有机电致发光装置中的应用。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN202110527453.XA CN113264944B (zh) | 2021-05-14 | 2021-05-14 | 一种有机化合物、有机电致发光材料及其装置 |
CN202110527453.X | 2021-05-14 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2022237407A1 true WO2022237407A1 (zh) | 2022-11-17 |
Family
ID=77230971
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/CN2022/085681 WO2022237407A1 (zh) | 2021-05-14 | 2022-04-08 | 一种有机化合物、有机电致发光材料及其装置 |
Country Status (2)
Country | Link |
---|---|
CN (1) | CN113264944B (zh) |
WO (1) | WO2022237407A1 (zh) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN113264944B (zh) * | 2021-05-14 | 2022-11-29 | 北京八亿时空液晶科技股份有限公司 | 一种有机化合物、有机电致发光材料及其装置 |
CN113429385B (zh) * | 2021-08-27 | 2021-11-16 | 北京八亿时空液晶科技股份有限公司 | 噻吨衍生物及其应用 |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN112694479A (zh) * | 2019-10-22 | 2021-04-23 | 罗门哈斯电子材料韩国有限公司 | 有机电致发光化合物以及包含其的有机电致发光装置 |
CN113072560A (zh) * | 2021-04-09 | 2021-07-06 | 北京八亿时空液晶科技股份有限公司 | 一种咔唑衍生物及其应用 |
CN113264944A (zh) * | 2021-05-14 | 2021-08-17 | 北京八亿时空液晶科技股份有限公司 | 一种有机化合物、有机电致发光材料及其装置 |
-
2021
- 2021-05-14 CN CN202110527453.XA patent/CN113264944B/zh active Active
-
2022
- 2022-04-08 WO PCT/CN2022/085681 patent/WO2022237407A1/zh active Application Filing
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN112694479A (zh) * | 2019-10-22 | 2021-04-23 | 罗门哈斯电子材料韩国有限公司 | 有机电致发光化合物以及包含其的有机电致发光装置 |
CN113072560A (zh) * | 2021-04-09 | 2021-07-06 | 北京八亿时空液晶科技股份有限公司 | 一种咔唑衍生物及其应用 |
CN113264944A (zh) * | 2021-05-14 | 2021-08-17 | 北京八亿时空液晶科技股份有限公司 | 一种有机化合物、有机电致发光材料及其装置 |
Non-Patent Citations (2)
Title |
---|
SHIN YONGWOO, LIN XI: "Deliberate Charge Conjugation Symmetry Breaking for π-Conjugated Electron Acceptor Design", THE JOURNAL OF PHYSICAL CHEMISTRY C, vol. 119, no. 23, 11 June 2015 (2015-06-11), US , pages 12808 - 12814, XP093005439, ISSN: 1932-7447, DOI: 10.1021/acs.jpcc.5b01340 * |
TEDJAMULIA MARVIN L., KUDO HIROTAKA, CASTLE RAYMOND N., LEE MILTON L.: "Angular polycyclic thiophenes containing two thiophene rings. Part II", JOURNAL OF HETEROCYCLIC CHEMISTRY, vol. 21, no. 2, 1 March 1984 (1984-03-01), US , pages 321 - 325, XP093005430, ISSN: 0022-152X, DOI: 10.1002/jhet.5570210210 * |
Also Published As
Publication number | Publication date |
---|---|
CN113264944A (zh) | 2021-08-17 |
CN113264944B (zh) | 2022-11-29 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP2019512476A (ja) | 有機エレクトロルミネッセンスデバイスのための材料 | |
WO2022088910A1 (zh) | 一种咔唑衍生物及其应用 | |
CN113801151B (zh) | 一种稠环芳香族化合物及其应用 | |
WO2022257584A1 (zh) | 化合物和包含该化合物的有机电致发光装置和电子设备 | |
WO2022237407A1 (zh) | 一种有机化合物、有机电致发光材料及其装置 | |
WO2024012522A1 (zh) | 一种咔唑衍生物及其在oled中的应用 | |
WO2024012469A1 (zh) | 一种咔唑衍生物及其在有机发光元件中的应用 | |
CN113429302B (zh) | 一种萘并芴衍生物、发光材料、发光元件及消费型产品 | |
CN113072560B (zh) | 一种咔唑衍生物及其应用 | |
WO2024012512A1 (zh) | 一种咔唑衍生物及包含它的有机发光元件 | |
WO2023065996A1 (zh) | 蒽衍生物、有机电致发光材料、发光装置及消费型产品 | |
TWI808518B (zh) | 一種苯並菲衍生物及其應用 | |
CN114044785A (zh) | 一种含硼化合物和有机电致发光元件、有机电致发光材料 | |
CN112876498B (zh) | 多环芳族化合物和含有该多环芳族化合物的有机电致发光元件 | |
CN113024444A (zh) | 一种化合物以及含有该化合物的有机电致发光元件用材料、有机电致发光装置和电子设备 | |
CN113563344B (zh) | 咔唑衍生物、有机电致发光材料、发光元件及消费型产品 | |
CN112794804B (zh) | 螺芴衍生物及其应用 | |
CN112830902B (zh) | 杂环螺芴化合物及其应用 | |
TW201835075A (zh) | 用於有機電致發光裝置之材料 | |
CN112812023B (zh) | 有机化合物、有机电致发光器件用材料、有机电致发光器件 | |
CN112812086B (zh) | 有机金属络合物的辅助配体以及包括其的装置和调配物 | |
CN114349798A (zh) | 一种金属配合物与应用及消费型产品 | |
CN113387821A (zh) | 芴类化合物、有机电致发光元件及消费型产品 | |
CN113429393A (zh) | 蒽并吲哚衍生物、有机电致发光元件用材料、发光元件及消费型产品 | |
CN112812108B (zh) | 化合物及包含该化合物的有机电致发光装置 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
121 | Ep: the epo has been informed by wipo that ep was designated in this application |
Ref document number: 22806377 Country of ref document: EP Kind code of ref document: A1 |
|
NENP | Non-entry into the national phase |
Ref country code: DE |
|
122 | Ep: pct application non-entry in european phase |
Ref document number: 22806377 Country of ref document: EP Kind code of ref document: A1 |