CN117466852A - Organic compound, organic electroluminescent device and electronic apparatus - Google Patents
Organic compound, organic electroluminescent device and electronic apparatus Download PDFInfo
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- CN117466852A CN117466852A CN202310252328.1A CN202310252328A CN117466852A CN 117466852 A CN117466852 A CN 117466852A CN 202310252328 A CN202310252328 A CN 202310252328A CN 117466852 A CN117466852 A CN 117466852A
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- 150000002894 organic compounds Chemical class 0.000 title claims abstract description 18
- -1 aromatic amine organic compound Chemical class 0.000 claims abstract description 40
- 125000004432 carbon atom Chemical group C* 0.000 claims description 169
- 125000003118 aryl group Chemical group 0.000 claims description 87
- 239000010410 layer Substances 0.000 claims description 79
- 150000001875 compounds Chemical class 0.000 claims description 76
- 125000001424 substituent group Chemical group 0.000 claims description 63
- 125000001072 heteroaryl group Chemical group 0.000 claims description 44
- 125000000217 alkyl group Chemical group 0.000 claims description 39
- 229910052805 deuterium Inorganic materials 0.000 claims description 30
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 28
- 230000005525 hole transport Effects 0.000 claims description 23
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 23
- 125000001624 naphthyl group Chemical group 0.000 claims description 20
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 16
- 125000001188 haloalkyl group Chemical group 0.000 claims description 16
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical class C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 14
- 239000002346 layers by function Substances 0.000 claims description 14
- 229910052736 halogen Inorganic materials 0.000 claims description 13
- 150000002367 halogens Chemical class 0.000 claims description 13
- 125000005549 heteroarylene group Chemical group 0.000 claims description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- 229920006395 saturated elastomer Polymers 0.000 claims description 11
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 11
- 125000000732 arylene group Chemical group 0.000 claims description 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 10
- 125000004665 trialkylsilyl group Chemical group 0.000 claims description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 9
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 9
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 9
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 7
- 235000010290 biphenyl Nutrition 0.000 claims description 7
- 239000004305 biphenyl Substances 0.000 claims description 7
- 239000011737 fluorine Substances 0.000 claims description 7
- 229910052731 fluorine Inorganic materials 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000004414 alkyl thio group Chemical group 0.000 claims description 6
- 125000005110 aryl thio group Chemical group 0.000 claims description 6
- 125000004104 aryloxy group Chemical group 0.000 claims description 6
- 125000005345 deuteroalkyl group Chemical group 0.000 claims description 6
- 238000000605 extraction Methods 0.000 claims description 6
- 125000005561 phenanthryl group Chemical group 0.000 claims description 6
- 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 claims description 5
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 5
- 125000001153 fluoro group Chemical group F* 0.000 claims description 5
- 125000003106 haloaryl group Chemical group 0.000 claims description 5
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
- 125000005580 triphenylene group Chemical group 0.000 claims description 4
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 claims description 3
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims description 3
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical group C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 claims description 2
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 claims description 2
- IYYZUPMFVPLQIF-ALWQSETLSA-N dibenzothiophene Chemical group C1=CC=CC=2[34S]C3=C(C=21)C=CC=C3 IYYZUPMFVPLQIF-ALWQSETLSA-N 0.000 claims description 2
- 125000004957 naphthylene group Chemical group 0.000 claims description 2
- 125000005562 phenanthrylene group Chemical group 0.000 claims description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 2
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 claims 1
- 239000000463 material Substances 0.000 abstract description 39
- 239000000543 intermediate Substances 0.000 description 77
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
- 238000006243 chemical reaction Methods 0.000 description 33
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- 238000002347 injection Methods 0.000 description 16
- 239000007924 injection Substances 0.000 description 16
- 239000000243 solution Substances 0.000 description 16
- 230000015572 biosynthetic process Effects 0.000 description 15
- 238000003786 synthesis reaction Methods 0.000 description 14
- 239000012074 organic phase Substances 0.000 description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- 239000007787 solid Substances 0.000 description 12
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 239000007858 starting material Substances 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 9
- 239000002994 raw material Substances 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 229940125782 compound 2 Drugs 0.000 description 8
- 238000001035 drying Methods 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 238000005406 washing Methods 0.000 description 8
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
- 230000000903 blocking effect Effects 0.000 description 6
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 6
- 238000001704 evaporation Methods 0.000 description 6
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 239000000758 substrate Substances 0.000 description 6
- CWRYPZZKDGJXCA-UHFFFAOYSA-N acenaphthalene Natural products C1=CC(CC2)=C3C2=CC=CC3=C1 CWRYPZZKDGJXCA-UHFFFAOYSA-N 0.000 description 5
- 125000004429 atom Chemical group 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 230000007935 neutral effect Effects 0.000 description 5
- 238000000967 suction filtration Methods 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 4
- LULAYUGMBFYYEX-UHFFFAOYSA-N 3-chlorobenzoic acid Chemical compound OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 description 4
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 4
- BGGALFIXXQOTPY-NRFANRHFSA-N C1(=C(C2=C(C=C1)N(C(C#N)=C2)C[C@@H](N1CCN(CC1)S(=O)(=O)C)C)C)CN1CCC(CC1)NC1=NC(=NC2=C1C=C(S2)CC(F)(F)F)NC Chemical compound C1(=C(C2=C(C=C1)N(C(C#N)=C2)C[C@@H](N1CCN(CC1)S(=O)(=O)C)C)C)CN1CCC(CC1)NC1=NC(=NC2=C1C=C(S2)CC(F)(F)F)NC BGGALFIXXQOTPY-NRFANRHFSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 125000004062 acenaphthenyl group Chemical group C1(CC2=CC=CC3=CC=CC1=C23)* 0.000 description 4
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 125000004122 cyclic group Chemical group 0.000 description 4
- 239000002019 doping agent Substances 0.000 description 4
- 125000005843 halogen group Chemical group 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 239000011777 magnesium Substances 0.000 description 4
- 125000002950 monocyclic group Chemical group 0.000 description 4
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 4
- 238000001308 synthesis method Methods 0.000 description 4
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].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 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 3
- NHDODQWIKUYWMW-UHFFFAOYSA-N 1-bromo-4-chlorobenzene Chemical compound ClC1=CC=C(Br)C=C1 NHDODQWIKUYWMW-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 3
- HXGDTGSAIMULJN-UHFFFAOYSA-N acetnaphthylene Natural products C1=CC(C=C2)=C3C2=CC=CC3=C1 HXGDTGSAIMULJN-UHFFFAOYSA-N 0.000 description 3
- 150000004982 aromatic amines Chemical class 0.000 description 3
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- 238000001819 mass spectrum Methods 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 3
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- 125000006413 ring segment Chemical group 0.000 description 3
- 229910052709 silver Inorganic materials 0.000 description 3
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- 125000003107 substituted aryl group Chemical group 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 3
- 125000001544 thienyl group Chemical group 0.000 description 3
- PKJBWOWQJHHAHG-UHFFFAOYSA-N 1-bromo-4-phenylbenzene Chemical group C1=CC(Br)=CC=C1C1=CC=CC=C1 PKJBWOWQJHHAHG-UHFFFAOYSA-N 0.000 description 2
- QENGPZGAWFQWCZ-UHFFFAOYSA-N 3-Methylthiophene Chemical compound CC=1C=CSC=1 QENGPZGAWFQWCZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical compound C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 239000010405 anode material Substances 0.000 description 2
- UHOVQNZJYSORNB-MZWXYZOWSA-N benzene-d6 Chemical compound [2H]C1=C([2H])C([2H])=C([2H])C([2H])=C1[2H] UHOVQNZJYSORNB-MZWXYZOWSA-N 0.000 description 2
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 2
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 2
- 125000002619 bicyclic group Chemical group 0.000 description 2
- 229910052796 boron Inorganic materials 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 150000001975 deuterium Chemical group 0.000 description 2
- 125000005509 dibenzothiophenyl group Chemical group 0.000 description 2
- DKHNGUNXLDCATP-UHFFFAOYSA-N dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile Chemical compound C12=NC(C#N)=C(C#N)N=C2C2=NC(C#N)=C(C#N)N=C2C2=C1N=C(C#N)C(C#N)=N2 DKHNGUNXLDCATP-UHFFFAOYSA-N 0.000 description 2
- 230000005684 electric field Effects 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 125000002541 furyl group Chemical group 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 150000004866 oxadiazoles Chemical class 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- IVDFJHOHABJVEH-UHFFFAOYSA-N pinacol Chemical compound CC(C)(O)C(C)(C)O IVDFJHOHABJVEH-UHFFFAOYSA-N 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- 125000004076 pyridyl group Chemical group 0.000 description 2
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- GLGNXYJARSMNGJ-VKTIVEEGSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[(1-ethyl-6-methoxy-2-oxo-4,5-dihydro-3h-1-benzazepin-7-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound CCN1C(=O)CCCC2=C(OC)C(NC=3N=C(C(=CN=3)Cl)N[C@H]3[C@H]([C@@]4([H])C[C@@]3(C=C4)[H])C(N)=O)=CC=C21 GLGNXYJARSMNGJ-VKTIVEEGSA-N 0.000 description 1
- SZUVGFMDDVSKSI-WIFOCOSTSA-N (1s,2s,3s,5r)-1-(carboxymethyl)-3,5-bis[(4-phenoxyphenyl)methyl-propylcarbamoyl]cyclopentane-1,2-dicarboxylic acid Chemical compound O=C([C@@H]1[C@@H]([C@](CC(O)=O)([C@H](C(=O)N(CCC)CC=2C=CC(OC=3C=CC=CC=3)=CC=2)C1)C(O)=O)C(O)=O)N(CCC)CC(C=C1)=CC=C1OC1=CC=CC=C1 SZUVGFMDDVSKSI-WIFOCOSTSA-N 0.000 description 1
- SDEAGACSNFSZCU-UHFFFAOYSA-N (3-chlorophenyl)boronic acid Chemical compound OB(O)C1=CC=CC(Cl)=C1 SDEAGACSNFSZCU-UHFFFAOYSA-N 0.000 description 1
- YQOLEILXOBUDMU-KRWDZBQOSA-N (4R)-5-[(6-bromo-3-methyl-2-pyrrolidin-1-ylquinoline-4-carbonyl)amino]-4-(2-chlorophenyl)pentanoic acid Chemical compound CC1=C(C2=C(C=CC(=C2)Br)N=C1N3CCCC3)C(=O)NC[C@H](CCC(=O)O)C4=CC=CC=C4Cl YQOLEILXOBUDMU-KRWDZBQOSA-N 0.000 description 1
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- 229910016036 BaF 2 Inorganic materials 0.000 description 1
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- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ISMDILRWKSYCOD-GNKBHMEESA-N C(C1=CC=CC=C1)[C@@H]1NC(OCCCCCCCCCCCNC([C@@H](NC(C[C@@H]1O)=O)C(C)C)=O)=O Chemical compound C(C1=CC=CC=C1)[C@@H]1NC(OCCCCCCCCCCCNC([C@@H](NC(C[C@@H]1O)=O)C(C)C)=O)=O ISMDILRWKSYCOD-GNKBHMEESA-N 0.000 description 1
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- 229940126639 Compound 33 Drugs 0.000 description 1
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- 229910052688 Gadolinium Inorganic materials 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
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- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
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- 229910052782 aluminium Inorganic materials 0.000 description 1
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- 125000005577 anthracene group Chemical group 0.000 description 1
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- 239000002585 base Substances 0.000 description 1
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical class C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 1
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- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
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- 125000001041 indolyl group Chemical group 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 230000002452 interceptive effect Effects 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 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
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 1
- 229940011051 isopropyl acetate Drugs 0.000 description 1
- 230000000155 isotopic effect Effects 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-M isovalerate Chemical compound CC(C)CC([O-])=O GWYFCOCPABKNJV-UHFFFAOYSA-M 0.000 description 1
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- 239000011133 lead Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
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- 150000004706 metal oxides Chemical class 0.000 description 1
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- IOMMMLWIABWRKL-WUTDNEBXSA-N nazartinib Chemical compound C1N(C(=O)/C=C/CN(C)C)CCCC[C@H]1N1C2=C(Cl)C=CC=C2N=C1NC(=O)C1=CC=NC(C)=C1 IOMMMLWIABWRKL-WUTDNEBXSA-N 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
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- YRMHIELITJAHGD-UHFFFAOYSA-K nitromethane;trichloroalumane Chemical compound [Al+3].[Cl-].[Cl-].[Cl-].C[N+]([O-])=O YRMHIELITJAHGD-UHFFFAOYSA-K 0.000 description 1
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- 238000011056 performance test Methods 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
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- ANRQGKOBLBYXFM-UHFFFAOYSA-M phenylmagnesium bromide Chemical compound Br[Mg]C1=CC=CC=C1 ANRQGKOBLBYXFM-UHFFFAOYSA-M 0.000 description 1
- 238000000206 photolithography Methods 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
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- 229920000128 polypyrrole Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
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- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
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- 239000002356 single layer Substances 0.000 description 1
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- 239000011734 sodium Substances 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
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- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 1
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- 229930192474 thiophene Natural products 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
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- 238000007738 vacuum evaporation Methods 0.000 description 1
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- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
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- 229910052725 zinc Inorganic materials 0.000 description 1
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- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/54—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to two or three six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
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Abstract
The invention relates to the technical field of organic electroluminescent materials, and provides an organic compound, an organic electroluminescent device and an electronic device.The organic compound has the structure shown in the formula 1, and the aromatic amine organic compound can be applied to an organic electroluminescent device, so that the performance of the device can be obviously improved.
Description
Technical Field
The invention relates to the technical field of organic electroluminescent materials, and an organic compound, an organic electroluminescent device and an electronic device containing the same.
Background
Along with the development of electronic technology and the progress of material science, the application range of electronic components for realizing electroluminescence or photoelectric conversion is becoming wider and wider. An organic electroluminescent device (OLED) generally includes a cathode and an anode disposed opposite each other, and a functional layer disposed between the cathode and the anode. The functional layer is composed of a plurality of organic or inorganic film layers, and generally includes an organic light emitting layer, a hole transporting layer, an electron transporting layer, and the like. When voltage is applied to the cathode and the anode, the two electrodes generate an electric field, electrons at the cathode side move to the electroluminescent layer under the action of the electric field, holes at the anode side also move to the luminescent layer, the electrons and the holes are combined in the electroluminescent layer to form excitons, and the excitons are in an excited state to release energy outwards, so that the electroluminescent layer emits light outwards.
In the existing organic electroluminescent devices, the most important problems are represented by the service life and efficiency, and along with the large area of the display, the driving voltage is also improved, and the luminous efficiency and the current efficiency are also required to be improved, so that it is necessary to continuously develop novel materials to further improve the performance of the organic electroluminescent devices.
Disclosure of Invention
In view of the foregoing problems of the prior art, it is an object of the present invention to provide an organic compound, which is used in an organic electroluminescent device and can improve the performance of the device, and an organic electroluminescent device and an electronic apparatus including the same.
According to a first aspect of the present invention, there is provided a compound having a structure represented by formula 1:
wherein R is 1 、R 2 、R 3 And R is 4 The same or different, are respectively and independently selected from substituted or unsubstituted aryl with 6-24 carbon atoms and substituted or unsubstituted alkyl with 1-10 carbon atoms;
L、L 1 and L 2 The same or different, are respectively and independently selected from single bond, substituted or unsubstituted arylene with 6-30 carbon atoms and substituted or unsubstituted heteroarylene with 3-30 carbon atoms;
Ar 1 and Ar is a group 2 The same or different, each independently selected from a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 40 carbon atoms;
R 1 、R 2 、R 3 And R is 4 The substituents in (a) are the same or different and are each independently selected from deuterium, cyano, halogen, alkyl with 1-10 carbon atoms, haloalkyl with 1-10 carbon atoms, deuterated alkyl with 1-10 carbon atoms, aryl with 6-15 carbon atoms, halogenated aryl with 6-15 carbon atoms, deuterated aryl with 6-15 carbon atoms and heteroaryl with 3-12 carbon atoms;
Ar 1 、Ar 2 、L、L 1 and L 2 The substituents in (a) are the same or different and are each independently selected from deuterium, cyano, halogen, alkyl having 1 to 10 carbon atoms, haloalkyl having 1 to 10 carbon atoms, deuteroalkyl having 1 to 10 carbon atoms, trialkylsilyl having 3 to 12 carbon atoms, aryl having 6 to 20 carbon atoms, halogenated aryl having 6 to 20 carbon atoms, deuteroaryl having 6 to 20 carbon atoms, heteroaryl having 3 to 20 carbon atoms, cycloalkyl having 3 to 10 carbon atoms, alkoxy having 1 to 10 carbon atoms, alkylthio having 1 to 10 carbon atoms, aryloxy having 6 to 20 carbon atoms or arylthio having 6 to 20 carbon atoms. Optionally Ar 1 、Ar 2 、L、L 1 And L 2 Any two adjacent substituents of (a) may form a saturated or unsaturated 3-to 15-membered ring.
Each R is 5 Independently selected from deuterium, cyano, halogen, alkyl with 1-10 carbon atoms, deuterated alkyl with 1-10 carbon atoms, halogenated alkyl with 1-10 carbon atoms, aryl with 6-20 carbon atoms a halogenated aryl group having 6 to 20 carbon atoms, a deuterated aryl group having 6 to 20 carbon atoms, a heteroaryl group having 3 to 20 carbon atoms, a deuterated heteroaryl group having 3 to 20 carbon atoms,A halogenated heteroaryl group having 3 to 20 carbon atoms; n is n 5 Is R 5 Number n of (2) 5 Selected from 0, 1,2, 3, 4, 5 or 6.
According to a second aspect of the present invention, there is provided an organic electroluminescent device comprising an anode and a cathode disposed opposite each other, and a functional layer disposed between the anode and the cathode; the functional layer comprises the organic compound.
According to a third aspect of the present invention, there is provided an electronic device comprising the organic electroluminescent device of the second aspect.
The invention provides an acenaphthene derivative group with aryl or alkyl substitution in an organic compound. In the organic compound, active hydrogen on 1, 2-position of acenaphthene is substituted by alkyl or aryl, so that the chemical stability of molecules is effectively improved, the hole mobility of materials can be effectively improved based on the conjugation of the acenaphthene derivative group and arylamine, and the organic compound is suitable for a hole transport layer of an organic electroluminescent device, so that the organic electroluminescent device prepared from the organic compound has the characteristics of low voltage and high efficiency. In addition, at least one aryl or alkyl is introduced on the acenaphthene derivative group to form a structure containing multiple substituents, and the substituents are distributed on two sides of the acenaphthene plane, so that the stacking among molecules is spatially reduced, the amorphous state of the material during film formation is improved, and the material has better stability when used for an organic electroluminescent device. When the organic compound is used as a second hole transport layer material in an organic electroluminescent device, a device product with low voltage, high efficiency and long service life can be prepared.
Drawings
The accompanying drawings are included to provide a further understanding of the invention, and are incorporated in and constitute a part of this specification, illustrate the invention and together with the description serve to explain, without limitation, the invention.
Fig. 1 is a schematic structural view of an organic electroluminescent device according to an embodiment of the present invention.
Fig. 2 is a schematic structural diagram of an electronic device according to an embodiment of the present invention.
Reference numerals
100. Anode 200, cathode 300, functional layer 310, and hole injection layer
321. First hole transport layer 322, second hole transport layer 330, organic light emitting layer 331, and hole blocking layer
340. Electron transport layer 350, electron injection layer 400, and electronic device
Detailed Description
Exemplary embodiments will now be described more fully with reference to the accompanying drawings. However, the exemplary embodiments may be embodied in many forms and should not be construed as limited to the examples set forth herein; rather, these embodiments are provided so that this disclosure will be thorough and complete, and will fully convey the concept of the exemplary embodiments to those skilled in the art. The described features, structures, or characteristics may be combined in any suitable manner in one or more embodiments. In the following description, numerous specific details are provided to give a thorough understanding of embodiments of the invention.
In a first aspect, the present invention provides a compound having the structure of formula 1:
wherein R is 1 、R 2 、R 3 And R is 4 And are the same or different and are each independently selected from a substituted or unsubstituted aryl group having 6 to 24 carbon atoms and a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.
L、L 1 And L 2 And are the same or different and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms.
Ar 1 And Ar is a group 2 And are the same or different and are each independently selected from a substituted or unsubstituted aryl group having 6 to 40 carbon atoms and a substituted or unsubstituted heteroaryl group having 3 to 40 carbon atoms.
R 1 、R 2 、R 3 And R is 4 The substituents in (a) are the same or different and are each independently selected from deuterium, cyano, halogen, alkyl having 1 to 10 carbon atoms, haloalkyl having 1 to 10 carbon atoms, deuterated alkyl having 1 to 10 carbon atoms, aryl having 6 to 15 carbon atoms, halogenated aryl having 6 to 15 carbon atoms, deuterated aryl having 6 to 15 carbon atoms and heteroaryl having 3 to 12 carbon atoms.
Ar 1 、Ar 2 、L、L 1 And L 2 The substituents in (a) are the same or different and are each independently selected from deuterium, cyano, halogen, alkyl having 1 to 10 carbon atoms, haloalkyl having 1 to 10 carbon atoms, deuteroalkyl having 1 to 10 carbon atoms, trialkylsilyl having 3 to 12 carbon atoms, aryl having 6 to 20 carbon atoms, halogenated aryl having 6 to 20 carbon atoms, deuteroaryl having 6 to 20 carbon atoms, heteroaryl having 3 to 20 carbon atoms, cycloalkyl having 3 to 10 carbon atoms, alkoxy having 1 to 10 carbon atoms, alkylthio having 1 to 10 carbon atoms, aryloxy having 6 to 20 carbon atoms or arylthio having 6 to 20 carbon atoms. Optionally Ar 1 、Ar 2 、L、L 1 And L 2 Any two adjacent substituents of (a) may form a saturated or unsaturated 3-to 15-membered ring.
Each R is 5 Independently selected from deuterium, cyano, halogen, alkyl of 1 to 10 carbon atoms, deuterated alkyl of 1 to 10 carbon atoms, haloalkyl of 1 to 10 carbon atoms, aryl of 6 to 20 carbon atoms, haloaryl of 6 to 20 carbon atoms, deuterated aryl of 6 to 20 carbon atoms, heteroaryl of 3 to 20 carbon atoms, deuterated heteroaryl of 3 to 20 carbon atoms, halogenated heteroaryl of 3 to 20 carbon atoms; n is n 5 Is R 5 Number n of (2) 5 Selected from 0, 1, 2, 3, 4, 5 or 6.
In the present invention, in formula 1, brackets "[]"means that the group L may be attached to the structureAny R in (3) 1 、R 2 、R 3 、R 4 And naphthalene ring, i.e.L may be attached +.>Any of positions 1, 2, 3, 4, 5, a, b, c, d, e. Specifically, & gt>The structure of (2) may include the following connection means:
in the present invention, the site number of acenaphthene is
In the present invention, the terms "optional," "optionally," and "optionally" mean that the subsequently described event or circumstance may or may not occur, and that the description includes instances where the event or circumstance occurs or does not. For example, "optionally, any two adjacent substituents form a ring" means that the two substituents may or may not form a ring, i.e., include: a scenario in which two adjacent substituents form a ring and a scenario in which two adjacent substituents do not form a ring. As another example, "Ar 1 、Ar 2 、L、L 1 And L 2 Any two adjacent substituents form a saturated or unsaturated 3-15 membered ring ", ar is 1 、Ar 2 、L、L 1 And L 2 Any two adjacent substituents of (a) are linked to form a ring, or Ar 1 、Ar 2 、L、L 1 And L 2 Any two adjacent substituents of (a) may be present independently of each other.
In the invention, in the "any two adjacent substituents form a ring", any two adjacent may include two substituents on the same atom, and may include two adjacent atoms each having one substituent; wherein when the same sourceWhen two substituents are present on a child, the two substituents may form a saturated or unsaturated ring with the atom to which they are commonly attached; when two adjacent atoms each have a substituent, the two substituents may be fused into a ring. For example, when Ar 1 With 2 or more substituents, any adjacent substituent forms a ring, a saturated or unsaturated cyclic group is formed, for example: benzene ring, naphthalene ring, phenanthrene ring, anthracene ring, fluorene ring, cyclopentane, cyclohexane, adamantane, and the like.
In the present invention, the descriptions of "… …" and "… …" and "… …" are used independently and interchangeably, and should be understood in a broad sense, which may mean that specific options expressed between the same symbols in different groups do not affect each other, or that specific options expressed between the same symbols in the same groups do not affect each other. For example, the number of the cells to be processed, Wherein each q is independently 0, 1, 2 or 3, and each R "is independently selected from hydrogen, deuterium, fluorine, chlorine", with the meaning: the formula Q-1 represents Q substituent groups R ' on the benzene ring, wherein R ' can be the same or different, and the options of each R ' are not mutually influenced; the formula Q-2 represents that each benzene ring of the biphenyl has Q substituent groups R ', the number Q of the substituent groups R' on two benzene rings can be the same or different, each R 'can be the same or different, and the options of each R' are not influenced each other.
In the present invention, such terms as "substituted or unsubstituted" mean that the functional group described later in the term may or may not have a substituent (hereinafter, for convenience of description, substituents are collectively referred to as Rc). For example, "substituted or unsubstituted aryl" refers to aryl having a substituent Rc or unsubstituted aryl. Wherein the substituent Rc may be, for example, deuterium, a halogen group, cyano, alkyl, cycloalkyl, aryl, heteroaryl, deuterated aryl, halogenated aryl, trialkylsilyl, haloalkyl, deuterated alkyl, alkoxy, alkylthio, aryloxy, arylthio, or the like. The number of substitutions may be 1 or more.
In the present invention, "a plurality of" means 2 or more, for example, 2, 3, 4, 5, 6, etc.
The hydrogen atoms in the structures of the compounds of the present invention include various isotopic atoms of the hydrogen element, such as hydrogen (H), deuterium (D), or tritium (T).
In the present invention, the number of carbon atoms of the substituted or unsubstituted functional group refers to all the numbers of carbon atoms. For example, if L 1 Is a substituted arylene group having 12 carbon atoms, then the arylene group and all of the substituents thereon have 12 carbon atoms.
In the present invention, mention is made of a saturated or unsaturated ring, for example a saturated or unsaturated 3-to 15-membered ring, including saturated carbocycles, saturated heterocycles, partially unsaturated carbocycles, partially unsaturated heterocycles, aromatic carbocycles, aromatic heterocycles; when n-membered is used as a prefix of a ring, n is an integer, and the number of ring atoms of the ring is n. For example, a 3-15 membered ring means a ring having 3 to 15 ring atoms, including rings of 3, 4, 5, 6, 7, 8, 9,10, 11, 12, 13, 14, 15 ring atoms.
In the present invention, aryl refers to an optional functional group or substituent derived from an aromatic carbocyclic ring. The aryl group may be a monocyclic aryl group (e.g., phenyl) or a polycyclic aryl group, in other words, the aryl group may be a monocyclic aryl group, a condensed ring aryl group, two or more monocyclic aryl groups connected by a carbon-carbon bond conjugate, a monocyclic aryl group and a condensed ring aryl group connected by a carbon-carbon bond conjugate, two or more condensed ring aryl groups connected by a carbon-carbon bond conjugate. That is, two or more aromatic groups conjugated through carbon-carbon bonds may also be considered as aryl groups of the present invention unless otherwise indicated. Among them, the condensed ring aryl group may include, for example, a bicyclic condensed aryl group (e.g., naphthyl group), a tricyclic condensed aryl group (e.g., phenanthryl group, fluorenyl group, anthracenyl group), and the like. The aryl group does not contain hetero atoms such as B, N, O, S, P, se, si and the like. Examples of aryl groups may include, but are not limited to, phenyl, naphthyl, fluorenyl, spirobifluorenyl, anthracenyl, phenanthryl, biphenyl, terphenyl, triphenylene, perylenyl, benzo [9,10 ] ]Phenanthryl, pyrenyl, benzofluoranthenyl,A base, etc.
In the present invention, arylene groups are defined as divalent groups formed by further loss of one or more hydrogen atoms from an aryl group.
In the present invention, the terphenyl group includes
In the present invention, the substituted aryl group may be one in which one or two or more hydrogen atoms in the aryl group are substituted with a group such as deuterium atom, halogen group, cyano group, aryl group, heteroaryl group, trialkylsilyl group, alkyl group, cycloalkyl group, haloalkyl group, deuterated alkyl group, halogenated aryl group, deuterated aryl group, aryloxy group, arylthio group, alkoxy group, alkylthio group, or the like. It is understood that the number of carbon atoms of a substituted aryl refers to the total number of carbon atoms of the aryl and substituents on the aryl, e.g., a substituted aryl having 18 carbon atoms refers to the total number of carbon atoms of the aryl and substituents being 18.
In the present invention, the substituted or unsubstituted aryl (or arylene) group may have 6, 8, 10, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 28, 30, 31, 33, 34, 35, 36, 38, 40 or the like. .
In the present invention, the fluorenyl group may be substituted with 1 or more substituents. In the case where the above fluorenyl group is substituted, the substituted fluorenyl group may be: And the like, but is not limited thereto.
In the present invention, aryl groups as substituents are exemplified by, but not limited to, phenyl, naphthyl, phenanthryl, biphenyl, fluorenyl, dimethylfluorenyl, anthracenyl,Group, triphenylene group, terphenyl group, and the like.
In the present invention, heteroaryl means a monovalent aromatic ring containing 1, 2, 3, 4, 5, 6 or 7 heteroatoms in the ring or derivatives thereof, which may be one or more of B, O, N, P, si, se and S. Heteroaryl groups may be monocyclic heteroaryl or polycyclic heteroaryl, in other words, heteroaryl groups may be a single aromatic ring system or multiple aromatic ring systems that are conjugated through carbon-carbon bonds, with either aromatic ring system being an aromatic monocyclic ring or an aromatic fused ring. Illustratively, heteroaryl groups may include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, indolyl, carbazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothiophenyl, thiophenyl, benzofuranyl, phenanthrolinyl, isoxazolyl, thiadiazolyl, phenothiazinyl, silafluorenyl, dibenzofuranyl, and N-phenylcarbazolyl, N-pyridylcarbazolyl, N-methylcarbazolyl, and the like, without limitation thereto. Wherein thienyl, furyl, phenanthroline and the like are heteroaryl groups of a single aromatic ring system type, and N-phenylcarbazolyl and N-pyridylcarbazolyl are heteroaryl groups of a polycyclic ring system type which are conjugated and connected through carbon-carbon bonds.
In the present invention, the heteroarylene group refers to a divalent group formed by further losing one or more hydrogen atoms.
In the present invention, the substituted heteroaryl (or heteroarylene) may be one in which one or more hydrogen atoms in the heteroaryl (or heteroarylene) are substituted with a group such as deuterium atom, halogen group, cyano, aryl, heteroaryl, trialkylsilyl, alkyl, cycloalkyl, haloalkyl, deuteroalkyl, haloaryl, deuteroaryl, aryloxy, arylthio, alkoxy, alkylthio, or the like. It is to be understood that in the present invention, the number of carbon atoms of the substituted heteroaryl (or heteroarylene) refers to the total number of carbon atoms of the heteroaryl and substituents on the heteroaryl, e.g., substituted heteroaryl having 18 carbon atoms refers to the total number of carbon atoms of the heteroaryl and substituents being 18.
In the present invention, the number of carbon atoms of the substituted or unsubstituted heteroaryl (or heteroarylene) group may be selected from 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, or the like.
In the present invention, heteroaryl groups as substituents are exemplified by, but not limited to, pyridyl, carbazolyl, quinolinyl, isoquinolinyl, phenanthroline, benzoxazolyl, benzothiazolyl, benzimidazolyl, dibenzothiophenyl, dibenzofuranyl, N-phenylcarbazolyl, and the like.
In the present invention, the alkyl group having 1 to 10 carbon atoms may include a straight chain alkyl group having 1 to 10 carbon atoms and a branched alkyl group having 3 to 10 carbon atoms. The number of carbon atoms of the alkyl group may be, for example, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, and specific examples of the alkyl group include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, and the like.
In the present invention, the halogen group may be, for example, fluorine, chlorine, bromine, or iodine.
In the present invention, specific examples of haloalkyl groups include, but are not limited to, trifluoromethyl.
In the present invention, specific examples of deuterated alkyl groups include, but are not limited to, tridentate methyl.
Specific examples of deuterated aryl groups in the present invention include, but are not limited to, deuterated benzene.
Specific examples of halogenated aryl groups in the present invention include, but are not limited to, fluorobenzene.
In the present invention, the cycloalkyl group has 3 to 10 carbon atoms, and may be, for example, 3, 4, 5, 6, 7, 8 or 10. Specific examples of cycloalkyl groups include, but are not limited to, cyclopentyl, cyclohexyl, adamantyl, and the like.
In the present invention, the trialkylsilyl group has 3 to 12 carbon atoms, and may be, for example, 3, 6, 7, 8, 9, or the like. Specific examples of trialkylsilyl groups include, but are not limited to, trimethylsilyl, ethyldimethylsilyl, triethylsilyl, and the like.
In the present invention, a heteroarylene group having 3 to 20 carbon atoms means a heteroarylene group having 3 to 20 carbon atoms and containing at least 1 nitrogen atom, oxygen atom or sulfur atom.
In the present invention, the connection key is not positioned in relation to a single bond extending from the ring systemIt means that one end of the bond can be attached to any position in the ring system through which the bond extends, and the other end is attached to the remainder of the compound molecule.
For example, as shown in the following formula (f), the naphthyl group represented by the formula (f) is linked to other positions of the molecule through two non-positional linkages penetrating through the bicyclic ring, and the meaning of the linkage includes any one of the possible linkages shown in the formulas (f-1) to (f-10).
As another example, as shown in the following formula (X '), the dibenzofuranyl group represented by the formula (X') is linked to the other position of the molecule through an unoositioned linkage extending from the middle of one benzene ring, and the meaning represented by this linkage includes any possible linkage as shown in the formulas (X '-1) to (X' -4).
By an off-site substituent in the context of the present invention is meant a substituent attached by a single bond extending from the center of the ring system, which means that the substituent may be attached at any possible position in the ring system. For example, as shown in the following formula (Y), the substituent R' represented by the formula (Y) is linked to the quinoline ring through an unoositioned linkage, and the meaning represented by the same includes any one of possible linkages as shown in the formulae (Y-1) to (Y-7).
In some embodiments, ar 1 And Ar is a group 2 And are the same or different and are each independently selected from a substituted or unsubstituted aryl group having 6 to 25 carbon atoms and a substituted or unsubstituted heteroaryl group having 12 to 24 carbon atoms.
In some embodiments, ar 1 And Ar is a group 2 Each independently selected from substituted or unsubstituted aryl groups having 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, or 25 carbon atoms, and substituted or unsubstituted heteroaryl groups having 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, or 24 carbon atoms.
In some embodiments, ar 1 And Ar is a group 2 Each of the substituents (1) is independently selected from deuterium, cyano, halogen, alkyl having 1 to 4 carbon atoms, haloalkyl having 1 to 4 carbon atoms, deuteroalkyl having 1 to 4 carbon atoms, trialkylsilyl having 3 to 8 carbon atoms, aryl having 6 to 12 carbon atoms, haloaryl having 6 to 12 carbon atoms, deuteroaryl having 6 to 12 carbon atoms, heteroaryl having 5 to 12 carbon atoms, cycloalkyl having 5 to 6 carbon atoms; optionally Ar 1 And Ar is a group 2 Any two adjacent substituents form a saturated or unsaturated 5-13 membered ring.
In some embodiments, ar 1 And Ar is a group 2 And are each independently selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted anthracenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted cyclopentane spirofluorenyl, and substituted or unsubstituted cyclohexane spirofluorenyl.
Alternatively, ar 1 And Ar is a group 2 Is taken from (a)The substituents are the same or different and are each independently selected from deuterium, fluoro, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, tridentate methyl, phenyl, naphthyl, cyclopentyl or cyclohexenyl.
In some embodiments, ar 1 And Ar is a group 2 Identical or different and are each independently selected from the group consisting of substituted or unsubstituted groups Q selected from the group consisting of:
wherein the substituted group Q has one or more substituents which are the same or different and are each independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuteromethyl, trimethylsilyl, phenyl, naphthyl, cyclopentyl or cyclohexenyl.
In some embodiments, ar 1 And Ar is a group 2 The same or different, each independently selected from the following groups:
in some embodiments, L, L 1 And L 2 Each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 18 carbon atoms, and a substituted or unsubstituted heteroarylene group having 12 to 18 carbon atoms.
In some embodiments, L, L 1 And L 2 The same or different and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17 or 18 carbon atoms, a substituted or unsubstituted arylene group having 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17 or 18 carbon atomsSubstituted heteroarylenes.
Optionally L, L 1 And L 2 The substituents of (a) are the same or different and are each independently selected from deuterium, cyano, halogen, alkyl having 1 to 4 carbon atoms, haloalkyl having 1 to 4 carbon atoms, deuterated alkyl having 1 to 4 carbon atoms, aryl having 6 to 12 carbon atoms, halogenated aryl having 6 to 12 carbon atoms, deuterated aryl having 6 to 12 carbon atoms and heteroaryl having 5 to 12 carbon atoms.
In some embodiments, L, L 1 And L 2 Each independently selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted phenanthrylene group, a substituted or unsubstituted dibenzothiophene group, a substituted or unsubstituted dibenzofuran group, a substituted or unsubstituted carbazole group.
Optionally L, L 1 And L 2 And are each independently selected from deuterium, fluoro, cyano, methyl, ethyl, isopropyl, t-butyl, trifluoromethyl, tridentate methyl, phenyl or naphthyl.
In some embodiments, L, L 1 And L 2 Identical or different, and are each independently selected from a single bond, a substituted or unsubstituted group V selected from the group consisting of:
wherein the substituted group V has one or more substituents thereon, each substituent being the same or different and each being independently selected from deuterium, fluoro, cyano, methyl, ethyl, isopropyl, t-butyl, trifluoromethyl, tridentate methyl, phenyl or naphthyl.
In some embodiments, L is selected from a single bond, a substituted or unsubstituted group V 1 The unsubstituted group V 1 Selected from the group consisting of:
wherein the substituted group V 1 Having one or more substituents thereon, each substituent being the same or different and each being independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, t-butyl, trifluoromethyl, tridentate methyl, phenyl or naphthyl.
In some embodiments, L is selected from the group consisting of a single bond or:
In some embodiments, L 1 And L 2 Each independently selected from single bond, substituted or unsubstituted group V 2 The unsubstituted group V 2 Selected from the group consisting of:
wherein the substituted group V 2 Having one or more substituents thereon, each substituent being the same or different and each being independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, t-butyl, trifluoromethyl, tridentate methyl, phenyl or naphthyl.
In some embodiments, L 1 And L 2 Each independently selected from the group consisting of a single bond or:
in some embodiments of the present invention, in some embodiments,each independently selected from the following groups:
in some embodiments of the invention, each R 1 、R 2 、R 3 And R is 4 The same or different, each independently selected from a substituted or unsubstituted methyl group, a substituted or unsubstituted tertiary butyl group, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted naphthyl group;
R 1 、R 2 、R 3 and R is 4 The substituents in (2) are the same or different and are each independently selected from deuterium or fluorine.
In some alternative embodiments, each R 1 、R 2 、R 3 And R is 4 The same or different are each independently selected from methyl or phenyl.
In some embodiments of the invention, each R 5 Independently selected from deuterium, cyano, fluoro, methyl, t-butyl, phenyl, biphenyl, or naphthyl.
In some embodiments, the compound of formula 1 is selected from structures represented by formulas 2-1, 2-2, or 2-3:
in some embodiments, the compound of formula 1 is selected from the structures of formulas 3-1, 3-2, 3-3, 3-4, 3-5, 3-6, 3-7, 3-8, 3-9, 3-10, 3-11, or 3-12:
in some alternative embodiments, the compound of formula 1 is selected from structures represented by formulas 3-3, 3-6, 3-9, 3-11, or 3-12.
Alternatively, the compound is selected from the group consisting of the compounds shown below.
In a second aspect of the present invention, there is provided an organic electroluminescent device comprising an anode, a cathode, and a functional layer disposed between the anode and the cathode; wherein the functional layer comprises a compound according to the first aspect of the present invention.
The compound provided by the invention can be used for forming at least one organic film layer in the functional layers so as to improve the luminous efficiency, the service life and other characteristics of the organic electroluminescent device.
Optionally, the functional layer includes an organic light emitting layer including the compound. The organic light-emitting layer may be composed of the compound provided by the present invention or may be composed of the compound provided by the present invention and other materials.
According to a specific embodiment, the organic electroluminescent device may include an anode 100, a hole injection layer 310, a first hole transport layer 321, a second hole transport layer (hole auxiliary layer) 322, an organic light emitting layer 330, a hole blocking layer 331, an electron transport layer 340, an electron injection layer 350, and a cathode 200, which are sequentially stacked as shown in fig. 1.
In the present invention, the anode 100 includes an anode material, which is preferably a material having a large work function that facilitates hole injection into the functional layer. Specific examples of the anode material include metals such as nickel, platinum, vanadium, chromium, copper, zinc and gold or alloys thereof; metal oxides such as zinc oxide, indium Tin Oxide (ITO), and Indium Zinc Oxide (IZO); combined metal and oxide such as ZnO, al or SnO 2 Sb; or conductive polymers such as poly (3-methylthiophene) and poly [3,4- (ethylene-1, 2-dioxy) thiophene](PEDT), polypyrrole, and polyaniline, but not limited thereto. It is preferable to include a transparent electrode containing Indium Tin Oxide (ITO) as an anode.
In the present invention, the hole transport layer may include one or more hole transport materials, and the hole transport layer material may be selected from carbazole multimers, carbazole-linked triarylamine compounds, or other types of compounds, and may specifically be selected from the compounds shown below or any combination thereof:
those skilled in the art can choose from the prior art, and the present invention is not particularly limited thereto.
In one embodiment, the first hole transport layer 321 may be composed of HT-11.
In one embodiment, the second hole transport layer 322 is an organic compound of the present invention.
Optionally, a hole injection layer 310 is further provided between the anode 100 and the first hole transport layer 321 to enhance the ability to inject holes into the first hole transport layer 321. The hole injection layer 310 may be selected from benzidine derivatives, starburst arylamine compounds, phthalocyanine derivatives, and other materials, which are not particularly limited in the present invention. The material of the hole injection layer 310 may be selected from, for example, the following compounds or any combination thereof;
in one embodiment, hole injection layer 310 is comprised of HAT-CN.
In the present invention, the organic light emitting layer 330 may be composed of a single light emitting material, and may include a host material and a guest material. Alternatively, the organic light emitting layer 330 is composed of a host material and a guest material, and holes injected into the organic light emitting layer 330 and electrons injected into the organic light emitting layer 330 may be recombined at the organic light emitting layer 330 to form excitons, which transfer energy to the host material, which transfers energy to the guest material, thereby enabling the guest material to emit light.
The host material of the organic light emitting layer 330 may include a metal chelating compound, a bisstyryl derivative, an aromatic amine derivative, a dibenzofuran derivative, or other types of materials.
In some embodiments of the present invention, the host materials of the organic light emitting layer 330 are GH-1 and a compound GH-2.
The guest material of the organic light emitting layer 330 may be a compound having a condensed aryl ring or a derivative thereof, a compound having a heteroaryl ring or a derivative thereof, an aromatic amine derivative, or other materials, which are not particularly limited in the present invention. Guest materials are also known as doping materials or dopants. Fluorescent dopants and phosphorescent dopants can be classified according to the type of luminescence. Specific examples of phosphorescent dopants include but are not limited to,
in some embodiments of the present invention, the host material of the organic light emitting layer 330 is GH-1 and the compound GH-2, and the guest material is GD-1.
The hole blocking layer 331 is a layer that blocks holes from reaching the cathode, and in general, may be formed under the same conditions as the hole injection layer 310. Specifically, the present invention contrast is not particularly limited, and is not limited thereto, including oxadiazole derivatives or triazole derivatives, phenanthroline derivatives, aluminum complexes, and the like.
In some embodiments of the present invention, the hole blocking layer 331 is formed from HB-1.
The electron transport layer 340 may have a single-layer structure or a multi-layer structure, and may include one or more electron transport materials selected from, but not limited to, BTB, liQ, benzimidazole derivatives, oxadiazole derivatives, quinoxaline derivatives, or other electron transport materials, and the present invention is not particularly limited by comparison. The materials of the electron transport layer 340 include, but are not limited to, the following compounds:
In one embodiment of the present invention, electron transport layer 340 may be composed of BTB and LiQ, or ET-1 and LiQ.
In the present invention, the cathode 200 may include a cathode material, which is a material having a small work function that facilitates electron injection into the functional layer. Specific examples of cathode materialsIncluding, but not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; or a multi-layer material such as LiF/Al, liq/Al, liO 2 Al, liF/Ca, liF/Al and BaF 2 and/Ca. Optionally, a metal electrode comprising magnesium and silver is included as a cathode.
Optionally, an electron injection layer 350 is further provided between the cathode 200 and the electron transport layer 340 to enhance the ability to inject electrons into the electron transport layer 340. The electron injection layer 350 may include an inorganic material such as an alkali metal sulfide, an alkali metal halide, or may include a complex of an alkali metal and an organic substance. In one embodiment of the present invention, the electron injection layer 350 may include ytterbium (Yb).
A third aspect of the invention provides an electronic device comprising an organic electroluminescent device according to the second aspect of the invention.
According to one embodiment, as shown in fig. 2, an electronic device 400 is provided, which includes the organic electroluminescent device described above. The electronic device 400 may be, for example, a display device, a lighting device, an optical communication device, or other type of electronic device, which may include, for example, but is not limited to, a computer screen, a cell phone screen, a television, an electronic paper, an emergency light, an optical module, etc.
The synthetic methods of the compounds of the present invention are specifically described below in connection with synthetic examples, but the present disclosure is not limited thereto.
Synthetic examples
Those skilled in the art will recognize that the chemical reactions described herein can be used to suitably prepare many of the organic compounds of the present invention, and that other methods for preparing the compounds of the present invention are considered to be within the scope of the present invention. For example, the synthesis of those non-exemplified compounds according to the invention can be successfully accomplished by modification methods, such as appropriate protection of interfering groups, by use of other known reagents in addition to those described herein, or by some conventional modification of the reaction conditions, by those skilled in the art. All compounds of the synthesis process not mentioned in the present invention are commercially available starting products.
Preparation of intermediates
Preparation of I-A-1#
At N 2 Into a 2L three-necked flask, 3-dimethyl-2- (1-naphthyl) -butanol (76.0 g,332.84 mmol) and 600mL of methylene Chloride (CH) were charged under protection 2 Cl 2 ) Stirring is started, after the raw materials are dissolved, 100g of aluminum trichloride-nitromethane solution (AlCl) is slowly added dropwise 3 /CH 3 NO 2 ,AlCl 3 And the mass fraction is 47 percent), and stirring for 6 hours at room temperature after the dripping is finished. After the reaction was completed, the reaction solution was poured into 800mL of deionized water, followed by addition of 600mL of methylene chloride, extraction was performed, and after washing the organic phase obtained by extraction with water to neutrality, 50g of anhydrous magnesium sulfate was added, standing for 30min, drying and dehydration were performed, and filtration was performed again, and the filtrate was concentrated to obtain a crude pale yellow oil, and the crude was purified on an alumina column with mobile phase methylene chloride/petroleum ether (V: v=1:6), to obtain a white solid, intermediate I-a-1# (55.72 g, yield 79.6%).
Preparation of I-A
To a 1L single-necked flask, intermediate I-A-1# (55 g,261.51 mmol) and 600mL of methylene chloride were charged, and the mixture was stirred at room temperature for 30 minutes to completely dissolve the starting material, N-bromosuccinimide (NBS, 46.54g,261.51 mmol) was added in portions, and the mixture was stirred overnight. After the reaction was completed, the reaction solution was repeatedly washed with water three times, 500mL of water each time. After washing with water, the organic phases were combined and dried by adding 30g of anhydrous magnesium sulfate, standing for 30min, and the solvent was distilled off under reduced pressure to give a yellow solid, intermediate I-A (59.45 g, yield 78.6%).
Preparation of I-N-1
At N 2 Under the protection, 4-bromodiphenyl (20 g,85.80 mmol), 2-amino-9, 9-dimethylfluorene (18.32 g,87.51 mmol) and 160mL toluene are put into a 500mL three-neck flask, the temperature is raised to 110 ℃, after the raw materials are dissolved, the temperature is lowered to about 70 ℃, tris (dibenzylideneacetone) dipalladium (0.79 g,0.86 mmol) and 2-dicyclohexylphosphine-2 ',4',6' -triisopropylbiphenyl (0.82 g,1.72 mmol) are sequentially added, sodium tert-butoxide (12.37 g,128.69 mmol) are heated to reflux for 2h, and then the temperature is lowered to room temperature. The product solution is washed for 3 times, then 10g of anhydrous magnesium sulfate is added for standing for 30min to dry and remove water, and the product solution is concentrated after suction filtration. The concentrate was purified by column chromatography to give intermediate I-N-1 (20.03 g, yield 64.59%).
The same synthesis as for intermediate I-N-1 was used, using the starting materials Ar-NH listed in Table 1, respectively 2 Instead of 2-amino-9'9-dimethylfluorene, the starting material Ar-X was used instead of 4-bromobiphenyl, and the corresponding intermediates in Table 1 were prepared by synthesis under otherwise unchanged conditions: I-N-2, I-N-3, I-N-4, I-N-5, I-N-6, I-N-7, I-N-8, I-N-9, I-N-10, I-N-11, I-N-12, I-N-13, I-N-14, I-N-15, and the specific raw materials and yields are shown in Table 1.
Table 1: intermediates I-N-2 to I-N-15
Preparation of I-A-L1
To a 500mL three-necked flask under nitrogen protection were charged intermediate I-A (20 g,69.15 mmol), m-chlorobenzeneboronic acid (12.98 g,82.98 mmol), tetrabutylammonium bromide (4.46 g,13.83 mmol), potassium carbonate (21.95 g,159.05 mmol), toluene (160 mL), ethanol (60 mL) and water (40 mL), stirring was started and nitrogen protection was applied, and the temperature was raised to 50℃to 60℃and tetrakis (triphenylphosphine) palladium (3.99 g,3.46 mmol) was rapidly added. After the addition, continuously heating to 70-75 ℃ for reflux reaction for 8 hours, cooling to room temperature after the reaction is finished, extracting the reaction solution with toluene to obtain an organic phase, washing the obtained organic phase with water to be neutral, and then drying, filtering and concentrating to obtain concentrated solution. The resulting concentrate was recrystallized from ethyl acetate to LC >99% and dried to give intermediate I-a-L1 (16.9 g, yield 76.16%) as a white solid.
The same synthesis as for intermediate I-A-L1 was used, starting material 1 in Table 2 was used instead of m-chlorobenzoic acid, respectively, and the corresponding intermediate in Table 2 was prepared under the same conditions: I-A-L2, I-A-L3, I-A-L4, I-A-L5, I-A-L6, I-A-L7, and the specific raw materials and yields are shown in Table 2.
Table 2: intermediates I-A-L2 to I-A-L7
Intermediate I-B-1#
At N 2 Under the protection, adding sodium hydride (14.27 g,594.53 mmol) and 150mL tetrahydrofuran into a 500mL three-neck flask, controlling the temperature at-5 ℃ to 5 ℃, stirring for 30min, dropwise adding a tetrahydrofuran solution of acenaphthenone (20 g,118.91 mmol), after the dropwise adding is finished, keeping the temperature at-5 ℃ to 5 ℃ and stirring for 1h, then dropwise adding methyl iodide (50.47 g,355.57 mmol), and after the dropwise adding is finished, keeping the temperature at-5 ℃ to 5 ℃ and reacting for 1h. After the reaction, the reaction solution is poured into an ice saturated ammonium chloride solution, then 500mL of methylene dichloride is added for extraction, after the organic phase is washed to be neutral, 200g of anhydrous magnesium sulfate is added for drying, standing is carried out for 30min, and suction filtration is carried outAfter concentration, intermediate I-B-1# (21.71 g, 93.05% yield) was obtained.
Intermediate I-B-2#
At N 2 Under the protection, an intermediate I-B-1# (20 g,101.91 mmol) and tetrahydrofuran (200 mL) were put into a 500mL three-necked flask, stirred at normal temperature for 30min, then phenylmagnesium bromide (18.48 g,101.91 mmol) was added dropwise, and after the addition was completed, the reaction was carried out at normal temperature for 3h. After the reaction was completed, 2mol/L of diluted hydrochloric acid was added to the reaction mixture until the reaction system became weakly acidic, then 500mL of methylene chloride was added for extraction, the obtained organic phases were combined and washed with water to neutrality, dried over anhydrous magnesium sulfate, and then the drying agent was suction-filtered off, and the obtained filtrate was distilled off under reduced pressure to remove the solvent, whereby a white solid was obtained as intermediate I-B-2# (23.71 g, yield 84.80%).
Intermediate I-B-3#
At N 2 Under the protection, an intermediate I-B-2# (23 g,83.83 mmol) and benzene (200 mL) are put into a 500mL three-neck flask, stirred at normal temperature for 30min, then trifluoromethanesulfonic acid (37.74 g,251.49 mmol) is directly added, the temperature of the reaction system is rapidly increased, and the reaction system is heated at the moment, and the reaction is performed under reflux timing. After the reaction was completed for 3 hours, the reaction mixture was cooled to room temperature and washed with water to neutrality, and then 20g of anhydrous magnesium sulfate was added and left to stand for 30 minutes to dry and remove water, and the organic phase was concentrated after suction filtration to give a white solid as intermediate I-B-3# (26.21 g, yield 93.51%).
Intermediates I-B1 and I-B2
To a 500mL single-necked flask, intermediate I-B-3# (25 g,74.76 mmol) and methylene chloride (250 mL) were charged at room temperature, and the mixture was stirred at room temperature for 30 minutes to allow the raw materials to be sufficiently dissolved, N-bromosuccinimide (NBS) (12.92 g,72.57 mmol) was added in portions, and after the NBS was completely added, the mixture was stirred and reacted for 3 hours. After the reaction, the reaction solution was repeatedly washed three times with 300mL of water each, the washed organic phases were combined and added with 15g of anhydrous magnesium sulfate to stand for 30min, water removal and drying were performed, then the solvent was distilled off under reduced pressure to obtain a yellow oil, and the obtained yellow oil was separated by column chromatography (cyclohexane as eluent) to obtain intermediate I-B1 (11.03 g, 35.69%) and intermediate I-B2 (9.03 g, yield 29.22%)
Intermediate I-B1-L1
To a 250mL three-necked flask under nitrogen protection was charged intermediate I-B1 (10 g,24.19 mmol), orthochlorophenylboronic acid (4.54 g,29.03 mmol), tetrabutylammonium bromide (1.56 g,4.84 mmol), potassium carbonate (7.68 g,55.64 mmol), toluene (80 mL), ethanol (30 mL) and water (20 mL), stirring was started and nitrogen protection was applied, heating was raised to 50℃to 60℃and tetrakis (triphenylphosphine) palladium (1.4 g,1.21 mmol) was rapidly added. After the addition, the temperature is continuously raised to 70-75 ℃ for reflux reaction for 6h. After the reaction, cooling to room temperature, extracting with toluene to obtain an organic phase, washing the obtained organic phase with water to be neutral, drying, filtering, concentrating to obtain yellow solid powder, and boiling and washing the obtained yellow solid powder with ethanol at room temperature until LC is more than 99%. Then, oven-dried to obtain yellow solid: intermediate I-B1-L1 (7.91 g, yield 73.48%).
The intermediates I-B1-L2, I-B2-L1 and I-B2-L2 are prepared by adopting the same synthesis method as the intermediates I-B1-L1, except that: the intermediate I-B1 was replaced with the intermediate I-x shown in Table 3, and the m-chlorobenzoic acid was replaced with the raw material 2, and the corresponding intermediates I-B1-L2, I-B2-L1 and I-B2-L2 were synthesized under the same conditions, with the specific raw materials and yields shown in Table 3 below.
TABLE 3 Table 3
Intermediate I-C-1#
At N 2 Under the protection, adding p-chlorobromobenzene (16 g,83.57 mmol) and tetrahydrofuran (120 mL) into a 500mL three-neck flask, cooling to-80 ℃ to-90 ℃, dropwise adding n-butyllithium (6.42 g,100.28 mmol) at the temperature of-80 ℃ to-90 ℃, and keeping the temperature for 1h after the dropwise adding is finished; then tetrahydrofuran solution (150 mL) dissolved with intermediate I-B-1# (19.68 g,100.28 mmol) is added dropwise, and after the addition, the temperature is kept between-80 ℃ and-90 ℃ for 2h, and then the temperature is naturally raised to room temperature. After the temperature is stabilized, dilute hydrochloric acid is added into the reaction solution until the reaction solution is weak acid (pH is between 5.0 and 6.0), then 300mL of dichloromethane is added for organic phase extraction, after the organic phases are combined and washed to be neutral by water, 20g of anhydrous magnesium sulfate is added for standing for 30min for drying and dewatering, and after suction filtration, concentration is carried out, white solid which is intermediate I-C-1# (12.45 g, yield is 40.2%) is obtained.
Intermediate I-C
At N 2 Under the protection, an intermediate I-C-1# (12 g,38.86 mmol) and benzene (120 mL) are put into a 250mL three-neck flask, and after stirring for 30min at normal temperature, trifluoromethanesulfonic acid (17.49 g,116.57 mmol) is directly added, then the reaction system is rapidly heated, and at the moment, the reaction system is heated, and a reflux timing reaction is carried out. After the reaction was completed for 3 hours, the reaction mixture was cooled to room temperature and washed with water to neutrality, 10g of anhydrous magnesium sulfate was added and left to stand for 30 minutes to dry and remove water, and then concentrated after suction filtration to give a white solid as intermediate I-C (10.16 g, yield 70.90%).
Intermediate I-C-L-1#
Intermediate I-C (20.00 g,54.22 mmol), pinacol biborate (16.52 g,65.06 mmol), tris (dibenzylideneacetone) dipalladium (0.99 g,1.08 mmol), 2-dicyclohexylphosphine-2 ',4',6' -triisopropylbiphenyl (1.03 g,2.17 mmol) and potassium acetate (7.98 g,81.32 mmol) were added to isopropyl acetate (200 mL), heated to 85℃to 90℃under nitrogen and stirred for 24h; cooling to room temperature, separating out the product, filtering, washing the product to neutrality, dissolving the obtained product with toluene, purifying with silica gel chromatographic column, and recrystallizing with toluene to obtain intermediate I-C-L-1# (16.45 g, yield 65.91%).
Intermediate I-C-L
To a 250mL three-necked flask was charged intermediate I-C-L1-1# (15.0 g,43.44 mmol), p-chlorobromobenzene (9.98 g,52.12 mmol), tetrabutylammonium bromide (0.56 g,1.74 mmol), potassium carbonate (8.99 g,65.16 mmol), toluene (120 mL), ethanol (45 mL) and water (30 mL), stirring was turned on and nitrogen protection was applied, heating was raised to 50℃to 60℃and tetrakis (triphenylphosphine) palladium (1.00 g,0.87 mmol) was rapidly added. After the addition, continuously heating to 70-75 ℃ for reflux reaction for 12 hours, cooling to room temperature after the reaction is finished, extracting with dichloromethane, washing an organic phase to be neutral, drying, filtering and concentrating. Recrystallizing with mixed solvent of toluene and n-heptane. Oven dried to give intermediate I-C-L as a white solid (14.22 g, yield 73.56%).
Intermediate I-D-1#
The intermediate I-D-1# is prepared by adopting the same synthesis method as the intermediate I-C-1#, and the difference is that: and replacing p-chlorobromobenzene with m-chlorobromobenzene.
Intermediate I-D
The same synthesis as for intermediate I-C was used to prepare intermediate I-D (I-D (8.93 g, yield 72.11%)) with the difference that: I-D-1# is used to replace I-C-1#.
Intermediate I-D-L-1#.
The intermediate I-D-L-1# is prepared by adopting the same synthesis method as the intermediate I-C-L-1#, and the difference is that: I-D is used instead of I-C.
Intermediate I-D-L
The intermediate I-D-L is prepared by adopting the same synthesis method as the intermediate I-C-L, except that: I-D-L-1# is used to replace I-C-L-1#.
Preparation of Compound 2
At N 2 To a 500mL three-necked flask under protection, intermediate I-A (15 g,51.86 mmol), intermediate I-N-1 (18.82 g,52.07 mmol) and toluene (150 mL) were charged, the temperature was raised until the raw materials were dissolved, the temperature was lowered to 70℃and tris (dibenzylideneacetone) dipalladium (0.48 g,0.52 mmol), 2-dicyclohexylphosphine-2 ',6' -dimethoxybiphenyl (0.43 g,1.04 mmol) and sodium t-butoxide (7.51 g,78.11 mmol) were successively added, the temperature was raised and refluxed for 2 hours, and the reaction was then cooled to room temperature. Washing the reaction solution for 3 times, adding 10g of anhydrous magnesium sulfate, standing for 30min for drying and dewatering, removing the catalyst from the dewatered solution through column chromatography, and concentrating to obtain a crude product. The crude product was recrystallized from toluene/n-heptane to give white solid powder as compound 2 (13.99 g, yield 47.34%), mass spectrum (m/z=570.3 [ m+h) ] + )。
Preparation of Compound 11
Compound 11 was synthesized by the same method as compound 2, except that: the intermediate I-A was replaced by intermediate I-A-L1, and the other starting materials were unchanged to give Compound 11 (7 g, yield 44.68%), mass spectrum (m/z=646.34 [ M+H)] + )。
Synthetic compound: synthesis of Compound 14, compound 15, compound 31, compound 33, compound 34, compound 46, compound 47, compound 56, compound 57, compound 70, compound 76, compound 78, compound 88, compound 232
The compounds in table 4 were prepared using the same synthesis as that of compound 11, except that: the intermediate I-A-X is used for replacing the intermediate I-A-L1, the intermediate I-N-N is used for replacing the intermediate I-N-1, and the selected raw materials and the structure of the compounds are shown in Table 4.
TABLE 4 Synthesis of the compounds of the invention
Preparation of Compound 103
Compound 103 was synthesized by the same method as that for compound 2, except that: the intermediate I-B1-L1 was used instead of intermediate I-A, and the other starting material was unchanged to give compound 103 (7.3 g, yield 56.24%) (m/z=770.4 [ M+H)] + )。
Synthetic compound: synthesis of Compound 116, compound 118, compound 136, compound 139
The compounds in the following table were prepared using the same synthesis as compound 103, except that: intermediate I-B1-L1 was replaced with starting material 3 and intermediate I-N-1 was replaced with starting material 4, respectively, in Table 5. Specific starting materials and yields are shown in table 5 below.
TABLE 5 Synthesis of the compounds of the invention
Preparation of Compound 151
Compound 151 was synthesized by the same method as compound 2, except that: intermediate I-C is used for replacing intermediate I-A, and intermediate I-N-2 benzene is used for replacing intermediate I-N-1. Compound 151 (10.71 g, yield 60.41%) was obtained, mass spectrum (m/z=654.31 [ m+h] + )。
Synthetic compound: synthesis of Compound 154, compound 171, compound 173, compound 191, compound 194, compound 211
The compounds in the following table were prepared using the same synthesis as that of compound 151, except that: intermediate I-N-N replaces intermediate I-N-2 and intermediate I-N replaces intermediate I-C. Specific starting materials and yields are shown in table 6 below.
TABLE 6 Compounds of the invention
The nuclear magnetic data of the compounds are shown in table 7:
TABLE 7
Fabrication and evaluation examples of organic electroluminescent device
Example 1: organic electroluminescent device
The anode was prepared by the following procedure: the ITO thickness is equal toIs cut into a size of 40mm (length) ×40mm (width) ×0.7mm (thickness), and is prepared into an experimental substrate having cathode, anode and insulating layer patterns by photolithography process, and ultraviolet ozone and O can be used 2 :N 2 The plasma is used for surface treatment to increase the work function of the anode, and an organic solvent can be used for cleaning the surface of the ITO substrate to remove impurities and greasy dirt on the surface of the ITO substrate. It should be noted that the ITO substrate may be cut into other dimensions according to actual needs, and the size of the ITO substrate in the present disclosure is not particularly limited herein.
Vacuum evaporating compound HAT-CN on the above experimental substrate (anode) to form a film having a thickness ofIs then vacuum evaporated on the hole injection layer to form a compound HT-11 having a thickness +.>Is a first hole transport layer (HTL-1).
Vacuum evaporating compound 2 on the first hole transport layer to form a film having a thickness ofAnd a second hole transport layer (HTL-2).
On the second hole transport layer, compound GH-1 and compound GH-2 were mixed in 45%: mixing the mixture with 55% by weight to obtain a mixed main material, and vacuum evaporating the mixed main material and the compound GD-1 at a film thickness ratio of 100:5 to obtain a film with a thickness ofAn organic light emitting layer (EML).
Vacuum vapor deposition of a compound on a light-emitting layerHB-1 to form a thickness ofA hole blocking layer (EBL). Then, on the hole blocking layer, the compounds ET-1 and LiQ are mixed in a weight ratio of 1:1 and evaporated to form a film with a thickness of +.>Vacuum-evaporating Yb on Electron Transport Layer (ETL) to give a thickness +.>Then co-evaporating magnesium (Mg) and silver (Ag) on the electron injection layer at an evaporation rate of 1:9 to form a film having a thickness of +.>Is provided.
In addition, the thickness of the vacuum evaporation on the cathode is The compound CP-1 is used as a Cathode Protection Layer (CPL), thereby completing the manufacture of the green organic electroluminescent device.
Examples 2 to 39:
an organic electroluminescent device was fabricated in the same manner as in example 1, except that the compound 2 used in example 1 was replaced with the compound in table 8, respectively, when the second hole transport layer was formed.
Comparative examples 1 to 4:
an organic electroluminescent device was fabricated in the same manner as in example 1, except that compound a, compound B, compound C, and compound D, respectively, were substituted for compound 2 used in example 1 when forming the second hole transport layer.
For example 1Performance test was conducted on the organic electroluminescent devices obtained by 39 and comparative examples 1 to 4, specifically at 10mA/cm 2 IVL performance of the device was tested under the conditions of T95 device lifetime at 20mA/cm 2 The test was conducted under the conditions of (2) and the test results are shown in Table 8.
TABLE 8 organic electroluminescent device Performance test results
Referring to the above table, examples 1 to 39, using the compound of the present invention as the second hole transport layer material, the green organic electroluminescent device prepared has the characteristics of low voltage, high efficiency and long lifetime.
Specifically, the efficiency of examples 1 to 39 was improved by at least 15.7% and the life was improved by at least 18.6% as compared with comparative examples 1 to 4. Examples 1 to 39, which are directed to the compounds of the present invention, each have a driving voltage superior to that of comparative examples 1 to 4. Therefore, the organic compound of the present invention is used as a second hole transport layer of an organic electroluminescent device, and device performance can be significantly improved.
Other embodiments of the invention will be apparent to those skilled in the art from consideration of the specification and practice of the invention disclosed herein. This invention is intended to cover any variations, uses, or adaptations of the invention following, in general, the principles of the invention and including such departures from the present disclosure as come within known or customary practice within the art to which the invention pertains.
Claims (12)
1. An organic compound having a structure represented by formula 1:
wherein R is 1 、R 2 、R 3 And R is 4 The same or different, are respectively and independently selected from substituted or unsubstituted aryl with 6-24 carbon atoms and substituted or unsubstituted alkyl with 1-10 carbon atoms;
L、L 1 and L 2 The same or different, are respectively and independently selected from single bond, substituted or unsubstituted arylene with 6-30 carbon atoms and substituted or unsubstituted heteroarylene with 3-30 carbon atoms;
Ar 1 and Ar is a group 2 The same or different, each independently selected from a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 40 carbon atoms;
R 1 、R 2 、R 3 and R is 4 The substituents in (a) are the same or different and are each independently selected from deuterium, cyano, halogen, alkyl with 1-10 carbon atoms, haloalkyl with 1-10 carbon atoms, deuterated alkyl with 1-10 carbon atoms, aryl with 6-15 carbon atoms, halogenated aryl with 6-15 carbon atoms, deuterated aryl with 6-15 carbon atoms and heteroaryl with 3-12 carbon atoms;
Ar 1 、Ar 2 、L、L 1 And L 2 The substituents in (a) are the same or different and are each independently selected from deuterium, cyano, halogen, alkyl having 1 to 10 carbon atoms, haloalkyl having 1 to 10 carbon atoms, deuteroalkyl having 1 to 10 carbon atoms, trialkylsilyl having 3 to 12 carbon atoms, aryl having 6 to 20 carbon atoms, halogenated aryl having 6 to 20 carbon atoms, deuteroaryl having 6 to 20 carbon atoms, heteroaryl having 3 to 20 carbon atoms, cycloalkyl having 3 to 10 carbon atoms, alkoxy having 1 to 10 carbon atoms, alkylthio having 1 to 10 carbon atoms, aryloxy having 6 to 20 carbon atoms or arylthio having 6 to 20 carbon atoms. Optionally Ar 1 、Ar 2 、L、L 1 And L 2 Any two adjacent substituents can form a saturated or unsaturated 3-15 membered ring;
each R is 5 Independently selected from deuterium, cyano, halogen, alkyl of 1 to 10 carbon atoms, deuterated alkyl of 1 to 10 carbon atoms, haloalkyl of 1 to 10 carbon atoms, aryl of 6 to 20 carbon atoms, haloaryl of 6 to 20 carbon atoms, deuterated aryl of 6 to 20 carbon atoms, heteroaryl of 3 to 20 carbon atoms, deuterated heteroaryl of 3 to 20 carbon atoms, halogenated heteroaryl of 3 to 20 carbon atoms; n is n 5 Is R 5 Number n of (2) 5 Selected from 0, 1, 2, 3, 4, 5 or 6.
2. The compound of claim 1, wherein Ar 1 And Ar is a group 2 The same or different, each independently selected from a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, a substituted or unsubstituted heteroaryl group having 12 to 24 carbon atoms;
alternatively, ar 1 And Ar is a group 2 The substituents of (a) are the same or different and are each independently selected from deuterium, cyano, halogen, alkyl having 1 to 4 carbon atoms, haloalkyl having 1 to 4 carbon atoms, deuteroalkyl having 1 to 4 carbon atoms, trialkylsilyl having 3 to 8 carbon atoms, aryl having 6 to 12 carbon atoms, haloaryl having 6 to 12 carbon atoms, deuteroaryl having 6 to 12 carbon atoms, heteroaryl having 5 to 12 carbon atoms and cycloalkyl having 5 to 6 carbon atoms; optionally Ar 1 And Ar is a group 2 Any two adjacent substituents form a saturated or unsaturated 5-13 membered ring.
3. The compound of claim 1, wherein Ar 1 And Ar is a group 2 The same or different, each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted anthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted spirobifluorenyl, and extraction Substituted or unsubstituted cyclopentane spirofluorenyl, substituted or unsubstituted cyclohexane spirofluorenyl;
alternatively, ar 1 And Ar is a group 2 And are each independently selected from deuterium, fluoro, cyano, methyl, ethyl, isopropyl, t-butyl, trifluoromethyl, tridentate methyl, trimethylsilyl, phenyl, naphthyl, cyclopentyl or cyclohexenyl.
4. The compound of claim 1, wherein L, L 1 And L 2 Each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 18 carbon atoms, and a substituted or unsubstituted heteroarylene group having 12 to 18 carbon atoms;
optionally, each L, L 1 And L 2 The substituents of (a) are the same or different and are each independently selected from deuterium, cyano, halogen, alkyl having 1 to 4 carbon atoms, haloalkyl having 1 to 4 carbon atoms, deuterated alkyl having 1 to 4 carbon atoms, aryl having 6 to 12 carbon atoms, halogenated aryl having 6 to 12 carbon atoms, deuterated aryl having 6 to 12 carbon atoms and heteroaryl having 5 to 12 carbon atoms.
5. The compound of claim 1, wherein L, L 1 And L 2 Each independently selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted phenanthrylene group, a substituted or unsubstituted dibenzothiophene group, a substituted or unsubstituted dibenzofuran group, a substituted or unsubstituted carbazole group;
Optionally, each L, L 1 And L 2 And are each independently selected from deuterium, fluoro, cyano, methyl, ethyl, isopropyl, t-butyl, trifluoromethyl, tridentate methyl, phenyl or naphthyl.
6. The compound according to claim 1, wherein,each independently selected from the following groups:
7. the compound of claim 1, wherein each R 1 、R 2 、R 3 And R is 4 The same or different, each independently selected from a substituted or unsubstituted methyl group, a substituted or unsubstituted tertiary butyl group, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted naphthyl group;
R 1 、R 2 、R 3 and R is 4 The substituents in (2) are the same or different and are each independently selected from deuterium or fluorine.
8. The compound of claim 1, wherein each R 5 Independently selected from deuterium, cyano, fluoro, methyl, t-butyl, phenyl, biphenyl, or naphthyl.
9. A compound according to claim 1, wherein the compound of formula 1 is selected from the structures of formulae 2-1, 2-2 or 2-3:
10. the compound of claim 1, wherein the compound is selected from the following structures:
11. the organic electroluminescent device comprises an anode and a cathode which are oppositely arranged, and a functional layer arranged between the anode and the cathode; characterized in that the functional layer comprises the organic compound according to any one of claims 1 to 10;
Optionally, the functional layer includes a second hole transport layer, the second hole transport layer including the organic compound;
preferably, the organic electroluminescent device is a green organic electroluminescent device.
12. An electronic device comprising the organic electroluminescent device as claimed in claim 11.
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