CN115745906A - Compound containing heterocycle and organic electroluminescent device thereof - Google Patents
Compound containing heterocycle and organic electroluminescent device thereof Download PDFInfo
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- CN115745906A CN115745906A CN202211090863.3A CN202211090863A CN115745906A CN 115745906 A CN115745906 A CN 115745906A CN 202211090863 A CN202211090863 A CN 202211090863A CN 115745906 A CN115745906 A CN 115745906A
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- substituted
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- compound
- deuterium
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 127
- 125000000623 heterocyclic group Chemical group 0.000 title claims description 26
- 239000010410 layer Substances 0.000 claims description 84
- -1 dibenzofuranyl Chemical group 0.000 claims description 66
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 39
- 229910052805 deuterium Inorganic materials 0.000 claims description 39
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 32
- 125000003118 aryl group Chemical group 0.000 claims description 27
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 25
- 125000001424 substituent group Chemical group 0.000 claims description 25
- 150000002431 hydrogen Chemical class 0.000 claims description 24
- 229910052739 hydrogen Inorganic materials 0.000 claims description 24
- 239000001257 hydrogen Substances 0.000 claims description 24
- 239000012044 organic layer Substances 0.000 claims description 23
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 22
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 21
- 125000001072 heteroaryl group Chemical group 0.000 claims description 19
- 125000001624 naphthyl group Chemical group 0.000 claims description 19
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 19
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 17
- 230000000903 blocking effect Effects 0.000 claims description 17
- DMEGYFMYUHOHGS-UHFFFAOYSA-N cycloheptane Chemical compound C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 claims description 17
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 17
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 17
- 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 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
- 125000004076 pyridyl group Chemical group 0.000 claims description 16
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 16
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 16
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 16
- 235000010290 biphenyl Nutrition 0.000 claims description 15
- 239000004305 biphenyl Substances 0.000 claims description 15
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 15
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 14
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 14
- 125000005561 phenanthryl group Chemical group 0.000 claims description 13
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 claims description 11
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 11
- 125000005956 isoquinolyl group Chemical group 0.000 claims description 11
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 claims description 11
- 125000005493 quinolyl group Chemical group 0.000 claims description 11
- 125000005580 triphenylene group Chemical group 0.000 claims description 11
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 9
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 claims description 8
- PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical compound C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 125000003003 spiro group Chemical group 0.000 claims description 7
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- UMIVXZPTRXBADB-UHFFFAOYSA-N benzocyclobutene Chemical compound C1=CC=C2CCC2=C1 UMIVXZPTRXBADB-UHFFFAOYSA-N 0.000 claims description 6
- 125000005593 norbornanyl group Chemical group 0.000 claims description 6
- PMPVIKIVABFJJI-UHFFFAOYSA-N Cyclobutane Chemical compound C1CCC1 PMPVIKIVABFJJI-UHFFFAOYSA-N 0.000 claims description 5
- LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 claims description 5
- 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 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 5
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 5
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 5
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 5
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 4
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 4
- 230000004927 fusion Effects 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- AMSMVCOBCOZLEE-UHFFFAOYSA-N 1,3,5-Norcaratriene Chemical compound C1=CC=C2CC2=C1 AMSMVCOBCOZLEE-UHFFFAOYSA-N 0.000 claims description 2
- 239000000463 material Substances 0.000 abstract description 43
- 150000002391 heterocyclic compounds Chemical class 0.000 abstract description 11
- 230000009477 glass transition Effects 0.000 abstract description 8
- 238000000605 extraction Methods 0.000 abstract description 7
- 230000005540 biological transmission Effects 0.000 abstract description 4
- 230000002035 prolonged effect Effects 0.000 abstract description 4
- 239000002346 layers by function Substances 0.000 abstract description 3
- 239000000543 intermediate Substances 0.000 description 60
- 238000002360 preparation method Methods 0.000 description 55
- 239000007858 starting material Substances 0.000 description 43
- 238000001819 mass spectrum Methods 0.000 description 38
- 238000004128 high performance liquid chromatography Methods 0.000 description 37
- 238000000034 method Methods 0.000 description 37
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 31
- 239000007787 solid Substances 0.000 description 25
- 125000004432 carbon atom Chemical group C* 0.000 description 23
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 20
- 238000002347 injection Methods 0.000 description 19
- 239000007924 injection Substances 0.000 description 19
- 230000000052 comparative effect Effects 0.000 description 16
- 239000002994 raw material Substances 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 14
- 229940125904 compound 1 Drugs 0.000 description 14
- 238000012360 testing method Methods 0.000 description 14
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- ZOCHARZZJNPSEU-UHFFFAOYSA-N diboron Chemical compound B#B ZOCHARZZJNPSEU-UHFFFAOYSA-N 0.000 description 11
- 239000012153 distilled water Substances 0.000 description 10
- 238000001704 evaporation Methods 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- 229910052757 nitrogen Inorganic materials 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 230000005525 hole transport Effects 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 8
- 238000004140 cleaning Methods 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 8
- 230000008020 evaporation Effects 0.000 description 7
- IUSARDYWEPUTPN-OZBXUNDUSA-N (2r)-n-[(2s,3r)-4-[[(4s)-6-(2,2-dimethylpropyl)spiro[3,4-dihydropyrano[2,3-b]pyridine-2,1'-cyclobutane]-4-yl]amino]-3-hydroxy-1-[3-(1,3-thiazol-2-yl)phenyl]butan-2-yl]-2-methoxypropanamide Chemical compound C([C@H](NC(=O)[C@@H](C)OC)[C@H](O)CN[C@@H]1C2=CC(CC(C)(C)C)=CN=C2OC2(CCC2)C1)C(C=1)=CC=CC=1C1=NC=CS1 IUSARDYWEPUTPN-OZBXUNDUSA-N 0.000 description 6
- MINMDCMSHDBHKG-UHFFFAOYSA-N 4-[4-[[6-methoxy-2-(2-methoxyimidazo[2,1-b][1,3,4]thiadiazol-6-yl)-1-benzofuran-4-yl]oxymethyl]-5-methyl-1,3-thiazol-2-yl]morpholine Chemical compound N1=C2SC(OC)=NN2C=C1C(OC1=CC(OC)=C2)=CC1=C2OCC(=C(S1)C)N=C1N1CCOCC1 MINMDCMSHDBHKG-UHFFFAOYSA-N 0.000 description 6
- IJRKLHTZAIFUTB-UHFFFAOYSA-N 5-nitro-2-(2-phenylethylamino)benzoic acid Chemical compound OC(=O)C1=CC([N+]([O-])=O)=CC=C1NCCC1=CC=CC=C1 IJRKLHTZAIFUTB-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 229940125807 compound 37 Drugs 0.000 description 6
- JPGQOUSTVILISH-UHFFFAOYSA-N enflurane Chemical compound FC(F)OC(F)(F)C(F)Cl JPGQOUSTVILISH-UHFFFAOYSA-N 0.000 description 6
- 239000000758 substrate Substances 0.000 description 6
- VCUXVXLUOHDHKK-UHFFFAOYSA-N 2-(2-aminopyrimidin-4-yl)-4-(2-chloro-4-methoxyphenyl)-1,3-thiazole-5-carboxamide Chemical compound ClC1=CC(OC)=CC=C1C1=C(C(N)=O)SC(C=2N=C(N)N=CC=2)=N1 VCUXVXLUOHDHKK-UHFFFAOYSA-N 0.000 description 5
- LNUFLCYMSVYYNW-ZPJMAFJPSA-N [(2r,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[[(3s,5s,8r,9s,10s,13r,14s,17r)-10,13-dimethyl-17-[(2r)-6-methylheptan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-3-yl]oxy]-4,5-disulfo Chemical compound O([C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1C[C@@H]2CC[C@H]3[C@@H]4CC[C@@H]([C@]4(CC[C@@H]3[C@@]2(C)CC1)C)[C@H](C)CCCC(C)C)[C@H]1O[C@H](COS(O)(=O)=O)[C@@H](OS(O)(=O)=O)[C@H](OS(O)(=O)=O)[C@H]1OS(O)(=O)=O LNUFLCYMSVYYNW-ZPJMAFJPSA-N 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 5
- 150000001924 cycloalkanes Chemical class 0.000 description 5
- 239000011777 magnesium Substances 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- 229940127573 compound 38 Drugs 0.000 description 4
- 150000001925 cycloalkenes Chemical class 0.000 description 4
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 4
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 description 4
- PIDFDZJZLOTZTM-KHVQSSSXSA-N ombitasvir Chemical compound COC(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@H]1C(=O)NC1=CC=C([C@H]2N([C@@H](CC2)C=2C=CC(NC(=O)[C@H]3N(CCC3)C(=O)[C@@H](NC(=O)OC)C(C)C)=CC=2)C=2C=CC(=CC=2)C(C)(C)C)C=C1 PIDFDZJZLOTZTM-KHVQSSSXSA-N 0.000 description 4
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 3
- 150000001721 carbon Chemical group 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 125000000753 cycloalkyl group Chemical group 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 239000012065 filter cake Substances 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- 238000002390 rotary evaporation Methods 0.000 description 3
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- 239000002356 single layer Substances 0.000 description 3
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- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
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- DMEVMYSQZPJFOK-UHFFFAOYSA-N 3,4,5,6,9,10-hexazatetracyclo[12.4.0.02,7.08,13]octadeca-1(18),2(7),3,5,8(13),9,11,14,16-nonaene Chemical class N1=NN=C2C3=CC=CC=C3C3=CC=NN=C3C2=N1 DMEVMYSQZPJFOK-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
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- 239000004215 Carbon black (E152) Substances 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
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- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical class N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 description 2
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- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 2
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- UNXISIRQWPTTSN-UHFFFAOYSA-N boron;2,3-dimethylbutane-2,3-diol Chemical compound [B].[B].CC(C)(O)C(C)(C)O UNXISIRQWPTTSN-UHFFFAOYSA-N 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
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- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 2
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 2
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- 239000011737 fluorine Substances 0.000 description 2
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- 125000002541 furyl group Chemical group 0.000 description 2
- 230000005283 ground state Effects 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000005549 heteroarylene group Chemical group 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 125000001041 indolyl group Chemical group 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 125000002950 monocyclic group Chemical group 0.000 description 2
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
- 150000005041 phenanthrolines Chemical class 0.000 description 2
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 2
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- 229920000767 polyaniline Polymers 0.000 description 2
- 125000003367 polycyclic group Chemical group 0.000 description 2
- 229920000123 polythiophene Polymers 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 2
- 150000003220 pyrenes Chemical class 0.000 description 2
- 125000001725 pyrenyl group Chemical group 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000006798 recombination Effects 0.000 description 2
- 238000005215 recombination Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 239000010703 silicon Substances 0.000 description 2
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
- 230000003595 spectral effect Effects 0.000 description 2
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical class C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 2
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical group C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 2
- 125000001544 thienyl group Chemical group 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- 125000005259 triarylamine group Chemical group 0.000 description 2
- 125000004306 triazinyl group Chemical group 0.000 description 2
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 description 1
- 125000006710 (C2-C12) alkenyl group Chemical group 0.000 description 1
- WYSBZCPNRXECEW-UHFFFAOYSA-N 1-diazo-2H-anthracene Chemical class C1=CC=C2C=C3C(=[N+]=[N-])CC=CC3=CC2=C1 WYSBZCPNRXECEW-UHFFFAOYSA-N 0.000 description 1
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
- BMIBJCFFZPYJHF-UHFFFAOYSA-N 2-methoxy-5-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine Chemical compound COC1=NC=C(C)C=C1B1OC(C)(C)C(C)(C)O1 BMIBJCFFZPYJHF-UHFFFAOYSA-N 0.000 description 1
- UDQLIWBWHVOIIF-UHFFFAOYSA-N 3-phenylbenzene-1,2-diamine Chemical class NC1=CC=CC(C=2C=CC=CC=2)=C1N UDQLIWBWHVOIIF-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 229910001148 Al-Li alloy Inorganic materials 0.000 description 1
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 101100030361 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) pph-3 gene Proteins 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 1
- JHYLKGDXMUDNEO-UHFFFAOYSA-N [Mg].[In] Chemical compound [Mg].[In] JHYLKGDXMUDNEO-UHFFFAOYSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 229910001508 alkali metal halide Inorganic materials 0.000 description 1
- 150000008045 alkali metal halides Chemical class 0.000 description 1
- 229910000272 alkali metal oxide Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910001615 alkaline earth metal halide Inorganic materials 0.000 description 1
- 229910000287 alkaline earth metal oxide Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 229940058303 antinematodal benzimidazole derivative Drugs 0.000 description 1
- 229940027991 antiseptic and disinfectant quinoline derivative Drugs 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 125000001769 aryl amino group Chemical group 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 150000001538 azepines Chemical class 0.000 description 1
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 description 1
- 150000001555 benzenes Chemical group 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 125000002837 carbocyclic group Chemical group 0.000 description 1
- RWWUBXBYBPQIJI-UHFFFAOYSA-N cesium;quinolin-8-ol Chemical compound [Cs].C1=CN=C2C(O)=CC=CC2=C1 RWWUBXBYBPQIJI-UHFFFAOYSA-N 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 229920001940 conductive polymer Polymers 0.000 description 1
- 230000021615 conjugation Effects 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- CFBGXYDUODCMNS-UHFFFAOYSA-N cyclobutene Chemical compound C1CC=C1 CFBGXYDUODCMNS-UHFFFAOYSA-N 0.000 description 1
- 125000001047 cyclobutenyl group Chemical group C1(=CCC1)* 0.000 description 1
- ZXIJMRYMVAMXQP-UHFFFAOYSA-N cycloheptene Chemical compound C1CCC=CCC1 ZXIJMRYMVAMXQP-UHFFFAOYSA-N 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000003678 cyclohexadienyl group Chemical group C1(=CC=CCC1)* 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 description 1
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
- 125000000298 cyclopropenyl group Chemical group [H]C1=C([H])C1([H])* 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 238000003818 flash chromatography Methods 0.000 description 1
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 description 1
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000004770 highest occupied molecular orbital Methods 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 150000002503 iridium Chemical class 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
- 230000000155 isotopic effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- SJCKRGFTWFGHGZ-UHFFFAOYSA-N magnesium silver Chemical compound [Mg].[Ag] SJCKRGFTWFGHGZ-UHFFFAOYSA-N 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004626 naphthothienyl group Chemical group C1(=CSC2=C1C1=CC=CC=C1C=C2)* 0.000 description 1
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 150000002907 osmium Chemical class 0.000 description 1
- 150000007978 oxazole derivatives Chemical class 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 0.000 description 1
- 125000004437 phosphorous atom Chemical group 0.000 description 1
- 229910052698 phosphorus Inorganic materials 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
- 150000003057 platinum Chemical class 0.000 description 1
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- 150000002910 rare earth metals Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 150000003283 rhodium Chemical class 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 125000005346 substituted cycloalkyl group Chemical group 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 125000004627 thianthrenyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3SC12)* 0.000 description 1
- 150000007979 thiazole derivatives Chemical class 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
Landscapes
- Pyridine Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
The invention provides a heterocyclic compound and an organic electroluminescent device thereof, relating to the technical field of organic electroluminescent materials. The invention provides a compound with high electron mobility, high three-linear-state energy level and wide energy gap, and an organic electroluminescent device with low driving voltage, high luminous efficiency and long service life can be obtained. The organic electroluminescent device is easy to transmit electrons, so that the transmission of holes and electrons can be balanced, the luminous efficiency of the device is further improved, the exciton can be prevented from diffusing to an adjacent functional layer, the driving voltage and the luminous efficiency of the organic electroluminescent device are effectively improved, and the service life of the device is further prolonged; meanwhile, the heterocyclic compound provided by the invention has higher glass transition temperature, can improve the film forming property and the thermal stability of the material, and prolongs the service life of a device; in addition, the heterocyclic compound also has higher refractive index, and can effectively improve the light extraction efficiency, thereby improving the luminous efficiency of the device.
Description
Technical Field
The invention relates to the technical field of organic electroluminescent materials, in particular to a heterocyclic compound and an organic electroluminescent device thereof.
Background
With the rise of 8K, 5G, AI, AR/VR and other technologies, new display technology paths are diversified, and are continuously developing toward the aspects of miniaturization, high definition, low power consumption and flexibility. Organic Light Emitting Diodes (OLEDs) are considered to be a very potential new generation display technology due to their advantages of self-luminescence, wide viewing angle, fast response speed, high definition, high brightness, and good flexibility, and are widely used in the fields of flat panel display and solid state lighting.
The organic electroluminescent diode is a carrier double injection type device for converting electric energy into optical energy. The light emitting process is that under the action of an external electric field, holes generated by an anode material and electrons generated by a cathode material are respectively injected into an OLED device, the holes are transmitted on a HOMO energy level after being injected, and the electrons are transmitted on a LUMO energy level after being injected; after the hole and the electron enter the organic light-emitting layer through transmission, the hole and the electron are combined to form an exciton; the excitons transfer energy to organic light-emitting molecules in the light-emitting layer, which are transferred from a ground state to an excited state by gaining energy; molecules in the excited state are unstable and return to the ground state by radiative transitions, during which energy is released in the form of light energy, producing electroluminescence. Organic electroluminescent diodes have been developed to date, and have been applied to single-layer, double-layer and multi-layer structures, and at present, typical devices mostly adopt a multi-layer structure composed of an anode, a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, a cathode, and the like.
In recent years, the development of OLED devices has shown a rapidly increasing trend. Meanwhile, the requirements on the performance of the OLED product are also increasing, and a great deal of work needs to be done to further improve the performance of the OLED device and the basic research related to the performance. In the existing organic materials, the hole mobility of the hole transport material is better than the electron mobility of the electron transport material, and the hole injection is easier than the electron injection, so that electrons and holes injected from two sides of the electrode can be compounded at a position closer to a cathode interface, and a metal cathode can generate a quenching effect on nearby excitons, so that the efficiency of the device is greatly reduced; the unbalanced transmission of two current carriers, namely electrons and holes, can cause the reduction of exciton recombination probability, and also influence the photoelectric performance of the device. Therefore, in order to better balance carriers, improve light extraction efficiency and optimize device performance, a new material is urgently needed to be designed, and the new material is required to have good electron mobility and enable electrons to be transmitted to a light emitting layer; preventing the holes from escaping from the light-emitting layer and enabling the carriers to be recombined in the center of the light-emitting layer; the light extraction efficiency is improved, thereby improving the luminous efficiency and the service life of the device.
Disclosure of Invention
In view of the above problems in the prior art, the present invention provides a compound containing a heterocycle and an organic electroluminescent device thereof, which solve the problems of high driving voltage, low luminous efficiency, short lifetime, etc. of the organic electroluminescent device. Specifically, the technical scheme of the invention is as follows:
the invention provides a heterocyclic ring-containing compound, which has a structure shown in a formula I:
in the formula I, E is selected from any one of substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene and substituted or unsubstituted anthryl;
a is selected from the group shown in the following formula I-1 or formula I-2:
the R is 1 、R 2 Independently selected from any one of hydrogen, deuterium, cyano, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C2-C30 heteroaryl; or R 1 、R 2 Either of which may be directly bonded to L; or R 1 、R 2 Can combine with each other to form a substituted or unsubstituted spiro ring;
the R is 3 Independently selected from any one of hydrogen, deuterium, cyano, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C2-C30 heteroaryl; or two adjacent R 3 Can combine with each other to form a substituted or unsubstituted ring;
a is a mentioned 0 Independently selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8;
z is independently selected from any one of a single bond, O, S, C (Rx) (Ry) and N (Rz);
rx, ry and Rz are independently any one of hydrogen, deuterium, cyano, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C2-C30 heteroaryl;
the L is independently selected from a single bond or any one of the following groups:
x is independently selected from C (R) 4 ) Or an N atom;
said R is 4 Independently selected from any one of hydrogen, deuterium, cyano, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, or two adjacent R 4 Can combine with each other to form a substituted or unsubstituted ring;
n is 1 、n 2 Independently selected from 0 or 1;
the Y is selected from any one of O, S.
The invention also provides an organic electroluminescent device which comprises an anode, an organic layer and a cathode, wherein the organic layer is positioned between the anode and the cathode or positioned outside at least one electrode of the anode and the cathode, and the organic layer comprises any one or more of the heterocyclic ring-containing compounds.
Advantageous effects
The heterocyclic compound provided by the invention contains a condensed group with large conjugation, so that the heterocyclic compound has high electron mobility, is easy to transmit electrons, can balance the transmission of holes and electrons, and further improves the luminous efficiency of a device; meanwhile, the compound has high triplet state energy level and wide energy gap, when the compound is applied to an electron transport layer/a hole blocking layer, the diffusion of excitons to an adjacent functional layer is minimized, the driving voltage and the luminous efficiency of an organic electroluminescent device can be improved, and the service life of the device is further prolonged. The heterocyclic compound has higher glass transition temperature, can improve the film forming property and the thermal stability of materials, can prolong the service life of a device when being applied to an organic electroluminescent device, and can effectively improve the light extraction efficiency when being applied to a covering layer of the organic electroluminescent device, thereby improving the luminous efficiency of the device.
Detailed Description
The following will clearly and completely describe the technical solutions of the specific embodiments of the present invention, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the scope of protection of the present invention.
In the compounds of the present invention, any atom not designated as a particular isotope is included as any stable isotope of that atom and includes atoms in both their natural isotopic abundance and unnatural abundance.
In the present specification, "+" means a moiety linked to another substituent. "" may be attached to any optional position of the attached group/fragment. According to the invention
Can represent
And so on.
In the present specification, when a bond at a substituent or attachment site is present throughout two or more rings, it is indicated that it may be attached to either of the two or two rings, in particular to either of the corresponding alternative sites of the rings. For example,
can represent
Can represent
And so on.
Examples of halogen atoms described herein may include fluorine, chlorine, bromine, and iodine.
The alkyl group in the present invention refers to a monovalent group obtained by removing one hydrogen atom from an alkane molecule, and may be a straight-chain or branched-chain alkyl group, preferably having 1 to 15 carbon atoms, more preferably 1 to 12 carbon atoms, and particularly preferably 1 to 6 carbon atoms. The alkyl group may be substituted or unsubstituted. Specific examples may include methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, undecyl, dodecyl, isopropyl, isobutyl, sec-butyl, tert-butyl, isopentyl, and the like, but are not limited thereto.
The cycloalkyl group in the present invention means a monovalent group obtained by removing one hydrogen atom from a cyclic alkane molecule, and preferably has 3 to 18 carbon atoms, more preferably 3 to 12 carbon atoms, and particularly preferably 3 to 6 carbon atoms. Cycloalkyl groups may be substituted or unsubstituted. Specific examples may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, and the like, but are not limited thereto.
The aryl group in the present invention refers to a monovalent group obtained by removing one hydrogen atom from an aromatic core carbon of an aromatic compound molecule, and may be a monocyclic aryl group, a polycyclic aryl group or a fused ring aryl group, and preferably has 6 to 60 carbon atoms, more preferably 6 to 30 carbon atoms, particularly preferably 6 to 18 carbon atoms, and most preferably 6 to 12 carbon atoms. The aryl group includes monocyclic aryl groups, polycyclic aryl groups, fused ring aryl groups, and the like. The aryl group may be substituted or unsubstituted. Specific examples may include phenyl, biphenyl, terphenyl, quaterphenyl, 1-phenylnaphthyl, 2-phenylnaphthyl, naphthyl, anthryl, phenanthryl, pyrenyl, perylenyl, fluorenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, 9-methyl-9-phenylfluorenyl, benzofluorenyl, triphenylenyl, fluoranthenyl, 9,9' -spirobifluorenyl, and the like, but are not limited thereto.
The heteroaryl group in the present invention refers to a general term of a group obtained by replacing one or more aromatic core carbon atoms in an aryl group with a heteroatom, including but not limited to oxygen, sulfur, nitrogen, silicon or phosphorus atom, preferably having 2 to 60 carbon atoms, more preferably 2 to 30 carbon atoms, particularly preferably 2 to 18 carbon atoms, and most preferably 2 to 12 carbon atoms. The linking site of the heteroaryl can be positioned on a ring-forming carbon atom or a ring-forming heteroatom, and the heteroaryl can be monocyclic heteroaryl, polycyclic heteroaryl or fused ring heteroaryl, and the like. Heteroaryl groups may be substituted or unsubstituted. Specific examples may include, but are not limited to, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, furyl, thienyl, pyrrolyl, oxazolyl, thiazolyl, imidazolyl, bipyridyl, phenylpyridyl, quinolyl, isoquinolyl, benzoquinolyl, benzisoquinolyl, quinazolinyl, quinoxalinyl, benzoquinazolinyl, benzoquinoxalinyl, phenanthrolinyl, naphthyridinyl, indolyl, benzothienyl, benzofuranyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, naphthofuranyl, phenanthrbenzofuranyl, naphthothienyl, phenanthrothiophenyl, naphthooxazolyl, naphthoimidazolyl, naphthothiazolyl, phenanthroxazolyl, phenanthrothiazolyl, phenanthroimidazolyl, carbazolyl, benzocarbazolyl, acridinyl, 9,10-dihydroacridinyl, phenoxazinyl, phenothiazinyl, phenoxathixenyl, spirofluorene xanthenyl, spirofluorene thianthrenyl, and the like.
The alicyclic ring in the present invention refers to a cyclic hydrocarbon having an aliphatic nature, and contains a closed carbon ring in a molecule, and preferably has 3 to 60 carbon atoms, more preferably 3 to 30 carbon atoms, further preferably 3 to 18 carbon atoms, more preferably 3 to 12 carbon atoms, and most preferably 3 to 7 carbon atoms. It may form monocyclic hydrocarbon or polycyclic hydrocarbon, may be completely unsaturated or partially unsaturated, may further be C3-30 cycloalkane, preferably C3-18 cycloalkane, more preferably C3-12 cycloalkane, most preferably C3-7 cycloalkane, may further be C3-30 cycloalkene, preferably C3-18 cycloalkene, more preferably C3-12 cycloalkene, most preferably C3-7 cycloalkene, may further be C3-30 cycloalkyne, preferably C3-18 cycloalkyne, more preferably C3-C12 cycloalkyne, most preferably C3-7 cycloalkyne, aliphatic ring may be substituted or unsubstituted, and specific examples may include cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclobutene, cyclopentene, cyclohexene, cycloheptene, and the like, but are not limited thereto. Multiple monocyclic hydrocarbons can also be linked in a variety of ways: two rings in the molecule can share one carbon atom to form a spiro ring; two carbon atoms on the ring can be connected by a carbon bridge to form a bridged ring; several rings may also be interconnected to form a cage-like structure.
The term arylene as used herein refers to an aryl group having 2 binding sites or divalent groups. The above description of the aryl group can be applied to them except that they are each a divalent group.
By heteroarylene as used herein is meant a heteroaryl group having 2 binding sites, i.e., a divalent radical. The above description of heteroaryl groups applies in addition to divalent groups.
The term "substituted … …" such as "substituted alkyl, substituted cycloalkyl, substituted aryl, substituted heteroaryl, substituted arylene, substituted heteroarylene" as used herein means independently mono-or poly-substituted with: deuterium, a cyano group, a nitro group, a halogen atom, a substituted or unsubstituted C1-C12 alkyl group, a substituted or unsubstituted C2-C12 alkenyl group, a substituted or unsubstituted C3-C12 cycloalkyl group, a substituted or unsubstituted C2-C12 heterocycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, a substituted or unsubstituted C1-C12 alkoxy group, a substituted or unsubstituted C1-C12 alkylthio group, a substituted or unsubstituted C1-C12 alkylamino group, a substituted or unsubstituted C6-C30 aryloxy group, a substituted or unsubstituted C6-C30 arylamino group, and the like, but are not limited thereto, or two adjacent substituents may be linked to each other to form a ring. Preferably mono-or polysubstituted with the following groups: deuterium, fluorine, chlorine, bromine, iodine, cyano, nitro, methyl, ethyl, isopropyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropenyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cyclopentadienyl, cyclohexadienyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, triphenylene, perylenyl, pyrenyl, benzyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, 9-methyl-9-phenylfluorenyl, 9,9' -spirobifluorenyl, dianilinyl, pyridyl, pyrimidyl, triazinyl, carbazolyl, acridinyl, furanyl, thienyl, benzofuranyl, benzothienyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, dibenzofuranyl, dibenzothienyl, phenothiazinyl, phenoxazinyl, indolyl, and the like, but is not limited thereto.
The "spiro ring structure" according to the present invention refers to a structure in which two carbocyclic rings share one carbon atom, and preferably has 15 to 60 carbon atoms, more preferably 15 to 30 carbon atoms. In particular, the spiro structure may comprise any of the groups of the following structural formulae, substituted or unsubstituted:
for example, when the spiro structure is combined with fluorene, any of the substituted or unsubstituted groups of the following structural formula may be formed:
the term "linked to form a ring" as used herein means that two groups are linked to each other by a chemical bond and optionally aromatized. As exemplified below:
in the present invention, the ring to be connected may be an aromatic ring system, an aliphatic ring system, or a ring system formed by a fusion of the two, and the ring to be connected may be a three-membered ring, a four-membered ring, a five-membered ring, a six-membered ring, or a fused ring, such as benzene, naphthalene, indene, cyclopentene, cyclopentane, cyclopentobenzene, cyclohexene, cyclohexane, cyclohexan, fluorene, pyridine, quinoline, isoquinoline, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, phenanthrene, or pyrene, but not limited thereto.
The invention provides a heterocyclic ring-containing compound, which has a structure shown in a formula I:
in the formula I, E is selected from any one of substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene and substituted or unsubstituted anthryl;
a is selected from the group shown in the following formula I-1 or formula I-2:
the R is 1 、R 2 Independently selected from any one of hydrogen, deuterium, cyano, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C2-C30 heteroaryl; or R 1 、R 2 Either of which may be directly bonded to L; or R 1 、R 2 Can combine with each other to form a substituted or unsubstituted spiro ring;
the R is 3 Independently selected from any one of hydrogen, deuterium, cyano, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C2-C30 heteroaryl; or two adjacent R 3 Can combine with each other to form a substituted or unsubstituted ring;
a is a 0 Independently selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8;
z is independently selected from any one of a single bond, O, S, C (Rx) (Ry) and N (Rz);
rx, ry and Rz are independently any one of hydrogen, deuterium, cyano, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C2-C30 heteroaryl;
the L is independently selected from a single bond or any one of the following groups:
x is independently selected from C (R) 4 ) Or an N atom;
the R is 4 Independently selected from any one of hydrogen, deuterium, cyano, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, or two adjacent R 4 Can combine with each other to form a substituted or unsubstituted ring;
n is 1 、n 2 Independently selected from 0 or 1;
the Y is selected from any one of O, S.
Preferably, E is selected from any one of the following groups:
the R is 5 Independently selected from any one of hydrogen, deuterium, cyano, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C2-C30 heteroaryl;
m is 1 Independently selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8, said m 2 Independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10;
* The fusion site is indicated.
Preferably, the
Any one selected from the following groups:
preferably, said R 5 Independently selected from hydrogen, deuterium, cyano, or the following substituted or unsubstituted groups: methyl, ethyl, n-butylAny one of propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropylalkyl, cyclobutylalkyl, cyclopentylalkyl, cyclohexylalkyl, cycloheptylalkyl, adamantyl, norbornanyl, phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, benzocyclopropylalkyl, benzocyclobutylalkyl, benzocyclopentylalkyl, benzocyclocyclohexylalkyl, fluorenyl, dibenzofuranyl, dibenzothienyl, carbazolyl, pyridyl, phenyl-pyridyl, pyrimidinyl, phenyl-pyrimidinyl, pyrazinyl, phenyl-pyrazinyl, pyridazinyl, quinolyl, isoquinolyl, quinoxalinyl, and quinazolinyl;
the substituted group is any one or more than one of deuterium, cyano, substituted or unsubstituted C1-C12 alkyl and substituted or unsubstituted C3-C12 cycloalkyl; when a plurality of substituents are present, the plurality of substituents may be the same as or different from each other;
m is 1 Independently selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8, said m 2 Independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10.
Preferably, said R 1 、R 2 Independently selected from hydrogen, deuterium, or the following substituted or unsubstituted groups: any one of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropylalkyl, cyclobutylalkyl, cyclopentylalkyl, cyclohexylalkyl, cycloheptylalkyl, adamantyl, norbornanyl, phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, benzocyclopropylalkyl, benzocyclobutylalkyl, benzocyclopentylalkyl, benzocyclocyclohexylalkyl, fluorenyl, dibenzofuranyl, dibenzothienyl, carbazolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, quinolyl, isoquinolyl, quinoxalyl, quinazolinyl;
the "substituted" group is any one or more selected from deuterium, cyano, substituted or unsubstituted C1-C12 alkyl, and substituted or unsubstituted C3-C12 cycloalkyl, and when a plurality of substituents are present, the plurality of substituents are the same as or different from each other;
or R 1 、R 2 In (1)Either may be directly bonded to L; or R 1 、R 2 Can be combined with each other to form any one of the following structures:
the R is 6 Independently selected from deuterium, cyano, or the following substituted or unsubstituted groups: any one of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropylalkyl, cyclobutylalkyl, cyclopentylalkyl, cyclohexylalkyl, cycloheptylalkyl, adamantyl, norbornanyl, phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, benzocyclopropylalkyl, benzocyclobutylalkyl, benzocyclopentylalkyl, benzocyclohexylalkyl, fluorenyl, dibenzofuranyl, dibenzothienyl, carbazolyl, pyridyl, pyrimidinyl, quinolyl, isoquinolyl, quinoxalinyl, and quinazolinyl;
the "substituted" group is any one or more selected from deuterium, a substituted or unsubstituted C1-C12 alkyl group, and a substituted or unsubstituted C3-C12 cycloalkyl group, and when a plurality of substituents are present, the plurality of substituents are the same as or different from each other;
a is a mentioned 1 Independently selected from 0, 1, 2, 3 or 4, said a 2 Independently selected from 0, 1, 2, 3, 4, 5 or 6, said a 3 Independently selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8, said a 4 Independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10, said a 5 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9,10, 11 or 12; a is a 6 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9,10, 11, 12, 13 or 14. A is a 7 Selected from 0, 1 or 2.
Preferably, said R 3 Independently selected from hydrogen, deuterium, cyano, or the following substituted or unsubstituted group: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantyl, norbornyl, phenyl, biphenylAny one of phenyl, terphenyl, naphthyl, phenanthryl, triphenylene, benzocyclopropyl, benzocyclobutane, benzocyclopentyl, benzocyclocyclohexane, fluorenyl, dibenzofuranyl, dibenzothienyl, carbazolyl, pyridyl, pyrimidinyl, quinolyl, isoquinolyl, quinoxalinyl, and quinazolinyl; or two adjacent R 3 Can be mutually combined to form any one of substituted or unsubstituted benzene ring, naphthalene ring and C3-C7 aliphatic ring;
the "substituted" group is any one or more selected from deuterium, a substituted or unsubstituted C1-C12 alkyl group, and a substituted or unsubstituted C3-C12 cycloalkyl group, and when a plurality of substituents are present, the plurality of substituents may be the same as or different from each other.
Still preferably, a is independently selected from any one of the following groups:
the R is 3 Independently selected from the group consisting of hydrogen, deuterium, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, benzocyclobutane, benzocyclopentane, benzocyclohexane, pyridinyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, deuterium substituted: <xnotran> , , , , , , , , , , , , , , , , , , , , , , , , , , </xnotran>Any one of isoquinolinyl, quinoxalinyl and quinazolinyl;
said R is 6 Independently selected from any one of hydrogen, deuterium, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, benzocyclopropyl, benzocyclobutane, benzocyclopentane, benzocyclohexane, pyridyl, pyrimidinyl, quinolyl, isoquinolyl, quinoxalyl, and quinazolinyl;
a is a 0 Independently selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8, said a 1 Independently selected from 0, 1, 2, 3 or 4, said a 2 Independently selected from 0, 1, 2, 3, 4, 5 or 6, said a 3 Independently selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8, said a 4 Independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10, said a 5 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9,10, 11 or 12; a is a mentioned 6 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9,10, 11, 12, 13 or 14, said a 7 Selected from 0, 1 or 2, said a 8 Independently selected from 0, 1, 2, 3, 4, 5, 6 or 7, said a 9 Independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9,10, 11, 12 or 13, said a 10 Independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9, said a 11 Independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9,10 or 11, said a 12 Independently selected from 0, 1, 2, 3, 4 or 5.
Preferably, rx, ry are independently selected from any one of hydrogen, deuterium, cyano, methyl, deuterated methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, deuterated tert-butyl, adamantyl, norbornyl, cyclopropylalkyl, cyclobutylyl, cyclopentanyl, cyclohexylalkyl, phenyl, biphenyl, terphenyl, deuterated phenyl, deuterated biphenyl, naphthyl, deuterated naphthyl, methyl-substituted phenyl, tert-butyl-substituted phenyl, adamantyl-substituted phenyl, benzocyclopropyl, benzocyclobutenyl, benzocyclopentyl, benzocyclohexanyl, pyridyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl.
Preferably, rz is independently selected from any one of phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclocyclohexane, deuterated phenyl, deuterated biphenyl, deuterated naphthyl, methyl-substituted phenyl, tert-butyl-substituted phenyl, adamantyl-substituted phenyl, pyridyl, pyrimidyl, quinolyl, isoquinolyl, quinazolinyl, and quinoxalyl.
Preferably, the L is independently selected from a single bond or any one of the following substituted or unsubstituted groups:
the substituted group is any one or more of deuterium, methyl, ethyl, n-propyl, isopropyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl and norbornyl; when a plurality of substituents are present, the plurality of substituents may be the same as or different from each other.
Most preferably, the heterocycle-containing compound is selected from any one of the following structures:
while specific structural forms of the compounds of formula I of the present invention have been illustrated above, the present invention is not limited to these specific structures, and any substituent group defined above based on the structure of formula I is intended to be included.
The invention also provides an organic electroluminescent device which comprises an anode, an organic layer and a cathode, wherein the organic layer is positioned between the anode and the cathode or positioned outside at least one of the anode and the cathode, and the organic layer is characterized by comprising any one or more of the heterocyclic compounds.
Preferably, the organic electroluminescent device according to the present invention may include one or more organic layers, the organic layers may include a light emitting layer, a hole injection layer, a hole transport layer, an electron injection layer, a hole blocking layer, an electron blocking layer, a capping layer, and the like, and specifically, the organic layer between the anode and the cathode may include a light emitting layer, a hole injection layer, a hole transport layer, an electron injection layer, a hole blocking layer, an electron blocking layer, and the like, and the organic layer outside at least one of the anode and the cathode may include a capping layer and the like.
Preferably, the organic layer is located between the anode and the cathode, the organic layer includes at least one of an electron transport layer or a hole blocking layer, and the at least one of the electron transport layer or the hole blocking layer includes any one or more of the heterocyclic ring-containing compounds according to the present invention.
Still preferably, the organic layer includes an electron transport layer including any one or more of the heterocyclic ring-containing compounds of the present invention.
Still preferably, the organic layer includes a hole blocking layer including any one or more of the heterocyclic ring-containing compounds of the present invention.
Preferably, the organic layer is located outside at least one or more of the anode and the cathode, and the organic layer includes a covering layer including any one or more of the heterocyclic ring-containing compounds of the present invention.
The material of each layer of the thin film in the organic electroluminescent device of the present invention is not particularly limited, and those known in the art can be used. The organic functional layers of the above-mentioned organic electroluminescent device and the electrodes on both sides of the device are described below:
as the anode material of the present invention, a material having a high work function is preferable. The anode may be a transmissive electrode, a reflective electrode, or a semi-transmissive electrode. When the anode is a transmissive electrodeIn this case, the material for forming the anode may be selected from Indium Tin Oxide (ITO), indium Zinc Oxide (IZO), tin oxide (SnO) 2 ) Zinc oxide (ZnO), or any combination thereof; when the anode is a semi-transmissive electrode or a reflective electrode, a material for forming the anode may be selected from magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), or any combination thereof. The anode may have a single layer structure or a multi-layer structure including two or more layers, for example, the anode may have a single layer structure of Al or a triple layer structure of ITO/Ag/ITO, but the structure of the anode is not limited thereto.
As the hole injection layer material of the present invention, a material having a high work function is preferable, and may be selected from any one or more of the following structures: metalloporphyrin, oligothiophene, arylamine derivatives, perylene derivatives, hexanitrile hexaazabenzophenanthrene compounds, quinacridone compounds, anthraquinone compounds, polyaniline-based and polythiophene-based conductive polymers, and the like, but are not limited thereto.
As the hole transport layer material described in the present invention, a material having a high hole mobility is preferable, and specific examples may include carbazole derivatives, triarylamine derivatives, biphenyldiamine derivatives, fluorene derivatives, stilbene derivatives, phthalocyanine compounds, hexanitrile hexaazabenzophenanthrene compounds, quinacridone compounds, anthraquinone compounds, polyaniline, polythiophene, polyvinylcarbazole, and the like, but are not limited thereto.
The light-emitting layer material of the present invention can be a red, green or blue light-emitting material, and usually contains a guest (dopant) material and a host material, wherein the guest material can be a pure fluorescent material or a phosphorescent material, or a combination of fluorescent and phosphorescent materials. The host material of the light-emitting layer needs to have not only a bipolar charge transport property but also an appropriate energy level to efficiently transfer excitation energy to the guest light-emitting material, and examples of such materials include distyrylaryl derivatives, stilbene derivatives, carbazole derivatives, triarylamine derivatives, anthracene derivatives, pyrene derivatives, and the like. The guest material may be selected from any one or more of the following structures: metal complexes (e.g., iridium complexes, platinum complexes, osmium complexes, rhodium complexes, etc.), anthracene derivatives, pyrene derivatives, perylene derivatives, etc., but are not limited thereto.
As the electron transport layer material of the present invention, a material having high electron mobility is preferred, and in addition to the heterocycle-containing material provided by the present invention, the material may be selected from any one or more of the following structures: metal chelates, oxazoie derivatives, thiazole derivatives, triazole derivatives, azepine derivatives, diazoanthracene derivatives, silicon-containing heterocycles, boron-containing heterocycles, cyano compounds, quinoline derivatives, phenanthroline derivatives, benzimidazole derivatives, and the like, but are not limited thereto.
As the hole blocking layer material of the present invention, a material having a lower energy level, a wider band gap, and a hole blocking capability is preferred, and in addition to the heterocyclic ring-containing compound provided by the present invention, the hole blocking layer material may be selected from any one or more of the following structures: phenanthroline derivatives, rare earth derivatives, oxazole derivatives, triazole derivatives, triazine derivatives, and the like, but are not limited thereto.
As the electron injection layer material of the present invention, a material having a low work function is preferable, and specific examples may include: metals, alkali metals, alkaline earth metals, alkali metal halides, alkaline earth metal halides, alkali metal oxides, alkaline earth metal oxides, alkali metal salts, alkaline earth metal salts, metal complexes, and other substances having high electron-injecting properties. Examples include Li, ca, sr, liF, csF, caF 2 、BaO、Li 2 CO 3 、CaCO 3 、Li 2 C 2 O 4 、Cs 2 C 2 O 4 、CsAlF 4 LiOx, yb, tb, cesium 8-hydroxyquinoline, aluminum tris (8-hydroxyquinoline), and the like, but are not limited thereto.
As the cathode material according to the present invention, a material having a low work function is preferable, and the cathode may be selected from a transmissive electrode, a semi-reflective electrode, or a reflective electrode. When the cathode electrode is a transmissive electrode, the material for forming the cathode electrode may be selected from transparent metal oxides (e.g., ITO, IZO, etc.); when the cathode is a semi-reflective electrode or a reflective electrode, the material for forming the cathode may be selected from Ag, mg, cu, al, pt, pd, au, ni, nd, ir, cr, li, ca, liF/Al, mo, ti, a compound including the same, or a mixture thereof (e.g., a mixture of Ag and Mg), but is not limited thereto.
The invention also provides a preparation method of the compound shown in the formula I, but the preparation method is not limited to the preparation method. The core structure of the compounds of formula I can be prepared by the reaction schemes shown below, the substituents can be bonded by methods known in the art, and the type and position of the substituents or the number of substituents can be varied according to techniques known in the art.
[ synthetic route of Compound of formula I ]
Xa, xb, xc and Xd are independently selected from any one of I, br and Cl.
Description of raw materials, reagents and characterization equipment:
the present invention is not particularly limited to the starting materials and sources of reagents used in the following examples, and they may be commercially available products or prepared by methods known to those skilled in the art.
The mass spectrum uses a British Watts G2-Si quadrupole rod series flight time high resolution mass spectrometer, and chloroform is used as a solvent;
the element analysis was carried out using a Vario EL cube type organic element analyzer of Elementar, germany, and the sample mass was 5 to 10mg;
synthesis example 1: preparation of Compound 1
Preparation of intermediate c-1:
the starting material d-1 (21.92g, 100mmol) was added to a reaction flask, and DMF solution (100 mL) was added to dissolve it, to which CBr was then added 4 (36.5g，110mmol) and sodium tert-butoxide (38.4 g, 400mmol), the mixture is stirred at room temperature for 30 minutes, after the reaction has ended, the solution is poured into distilled water and then extracted with dichloromethane, the organic phase is washed with distilled water and with anhydrous MgSO 4 Dried, filtered and concentrated under reduced pressure. The crude product was purified by flash chromatography (petroleum ether: ethyl acetate = 30) to afford intermediate c-1 (26.83g, 90%). The HPLC purity is more than or equal to 99.77 percent. Mass spectrum m/z:296.9760 (theoretical value: 296.9789).
Preparation of compound 1:
(1) Preparation of intermediate A-1:
under the protection of nitrogen, raw materials a-1 (24.59g, 90.00mmol), pinacol diboron (22.85g, 90.00mmol) and Pd (PPh) are sequentially added into a reaction bottle 3 ) 4 (1.29g，1.12mmol)、K 2 CO 3 (18.66g, 135.00mmol), DMF (550 mL), then heated to react for 2 hours, after the reaction was complete, cooled to room temperature, distilled water was added thereto, then extracted with ethyl acetate, the organic layer was dried over anhydrous magnesium sulfate, the solvent was removed by rotary evaporation, and then the reaction mixture was cooled with toluene: ethanol =5:1 to obtain an intermediate A-1 (24.50 g, yield 85%) with HPLC purity more than or equal to 99.57%. Mass spectrum m/z:320.1933 (theoretical value: 320.1948).
(2) Preparation of intermediate B-1:
under the protection of nitrogen, the intermediate A-1 (21.14g, 66.00mmol), the raw material b-1 (12.64g, 66.00mmol) and Pd (PPh) are added into a reaction flask in sequence 3 ) 4 (0.76g，0.66mmol)、K 2 CO 3 (13.68g, 99.00mmol) and 350mL of a toluene/ethanol/water (2: ethanol =10:1 to obtain an intermediate B-1 (16.70 g, yield 83%) with HPLC purity more than or equal to 99.77%. Mass spectrum m/z:304.1028 (theoretical value: 304.1019).
(3) Preparation of intermediate C-1:
under the protection of nitrogen, the intermediate B-1 (12.80g, 42.00mmol) and the pinacol ester diboron (1) are added into a reaction bottle in sequence0.67g，42.00mmol)，Pd(dppf)Cl 2 (0.31g, 0.42mmol), KOAc (6.18g, 63.00mmol), 1,4-dioxane (150 mL), was heated to reflux temperature for 4 hours, and after completion of the reaction, it was cooled to room temperature, distilled water was added thereto, followed by extraction with ethyl acetate, the organic layer was dried over anhydrous magnesium sulfate, the solvent was removed by rotary evaporation, and then toluene: ethanol =20:1 to obtain an intermediate C-1 (13.32 g, yield 80%) with HPLC purity more than or equal to 99.85 percent. Mass spectrum m/z:396.2274 (theoretical value: 396.2261).
(4) Preparation of compound 1:
under the protection of nitrogen, the intermediates C-1 (11.10g, 28.00mmol), C-1 (8.35g, 28.00mmol) and K are sequentially added into a reaction bottle 2 CO 3 (6.19g, 44.80mmol) and 220mL of a toluene solvent, and after replacing air with nitrogen gas for 2 times, pd was added thereto 2 (dba) 3 (0.31g，0.34mmol)、P(t-Bu) 3 (0.23g, 1.13mmol), stirring the mixture, replacing air with nitrogen for 1 time, heating and refluxing the reactant system for 5 hours, cooling to room temperature after the reaction is finished, performing suction filtration to obtain a filter cake, washing the filter cake with a small amount of toluene, and finally recrystallizing the filter cake with toluene to obtain the compound 1 (10.65 g, yield 78%) with HPLC purity of more than or equal to 99.90%. Mass spectrum m/z:487.1947 (theoretical value: 487.1936). Theoretical element content (%) C 36 H 25 NO: c,88.68; h,5.17; and N,2.87. Measured elemental content (%): c,88.64; h,5.19; and N,2.86.
Synthesis example 2: preparation of Compound 18
According to the method of example 1, the raw material d-1 was replaced by equimolar d-18, the raw material a-1 was replaced by equimolar a-18, the raw material b-1 was replaced by equimolar b-18, and the intermediate c-1 was replaced by equimolar c-18, so as to obtain compound 18 (12.15 g), which has a solid purity of 99.91% or more by HPLC. Mass spectrum m/z:570.2677 (theoretical value: 570.2689). Theoretical element content (%) C 42 H 22 D 7 NO: c,88.39; h,6.36; and N,2.45. Actual measurement elementContent (%) of elements: c,88.42; h,6.32; and N,2.43.
Synthetic example 3: preparation of Compound 37
Preparation of intermediate b-37:
(1) Preparation of intermediate E-37:
under the protection of nitrogen, f-37 (18.77g, 96.00mmol), pinacol diboron (24.38g, 96.00mmol) and Pd (dppf) Cl are added into a reaction bottle in sequence 2 (0.70g, 0.96mmol), KOAc (14.13g, 144.00mmol), 1,4-dioxane (350 mL) were heated to react for 2.5 hours, after the reaction was completed, distilled water was added, extraction was performed with methylene chloride, liquid separation was performed, the organic phase was washed three times with distilled water, dried over anhydrous magnesium sulfate, the solvent was concentrated by rotary evaporation, crystallized at a reduced temperature, suction-filtered, and the resulting solid was purified with toluene: ethanol =20:5 recrystallization to give intermediate E-37 (20.26 g, 87% yield); HPLC purity 99.61%. Mass spectrum m/z:242.1167 (theoretical value: 242.1183).
(2) Preparation of intermediate b-37:
under the protection of nitrogen, the intermediate E-37 (19.40g, 80.00mmol), the raw material g-37 (26.64g, 80.00mmol) and Pd (PPh 3) are added into a reaction bottle in sequence 4 (0.92g,0.80mmol)、K 2 CO 3 (16.58g, 120.00mmol), 300mL of a toluene/ethanol/water (2. After the reaction was completed, the reaction mixture was cooled to room temperature, toluene was added to separate each phase, the toluene phase was washed three times with distilled water, dried over anhydrous magnesium sulfate, concentrated in a rotary evaporator, crystallized by cooling, suction-filtered, and the resulting solid was recrystallized from toluene to obtain intermediate b-37 (22.13 g, yield 86%). HPLC purity 99.64%. Mass spectrum m/z:319.9895 (theoretical value: 319.9905).
(4) Preparation of compound 37:
according to the method of example 1, the starting material d-1 was replaced with equimolar d-37, the starting material a-1 was replaced with equimolar a-37, the starting material b-1 was replaced with equimolar b-37, and the intermediate c-1 was replaced with equimolarCompound 37 (14.81 g) was obtained according to (c-37) above, and the purity of the solid was ≧ 99.96% by HPLC. Mass spectrum m/z:744.3069 (theoretical value: 744.3079). Theoretical element content (%) C 55 H 32 D 4 N 2 O: c,88.68; h,5.41; and N,3.76. Measured elemental content (%): c,88.64; h,5.43; n,3.77.
Synthetic example 4: preparation of Compound 38
According to the method of example 1, the starting material a-1 was replaced with an equal mole of a-38 and the starting material b-1 was replaced with an equal mole of b-38 to obtain 38 (12.90 g) as a compound having a solid purity ≧ 99.95% by HPLC. Mass spectrum m/z:639.2553 (theoretical value: 639.2562). Theoretical element content (%) C 48 H 33 NO: c,90.11; h,5.20; and N,2.19. Measured elemental content (%): c,90.15; h,5.18; and N,2.16.
Synthesis example 5: preparation of Compound 43
Preparation of intermediate b-43:
according to the method of example 3, the starting material f-37 was replaced by equimolar of f-43 and the starting material g-37 was replaced by equimolar of g-43 to give intermediate b-43 (18.83 g) having a purity of 99.83% by HPLC. Mass spectrum m/z:267.9420 (theoretical value: 267.9403).
Preparation of compound 43:
according to the method of example 1, the starting material a-1 was replaced with an equimolar amount of a-43, the intermediate b-1 was replaced with an equimolar amount of b-43, and the intermediate c-1 was replaced with an equimolar amount of c-43, to obtain compound 43 (12.20 g), which was purified by HPLC to a solid content of 99.90% or more. Mass spectrum m/z:565.2168 (theoretical value: 565.2154). Theoretical element content (%) C 40 H 27 N 3 O: c,84.93; h,4.81; and N,7.43. Measured elemental content (%): c,84.88; h,4.83; and N,7.45.
Synthetic example 6: preparation of Compound 52
According to the method of example 1, intermediate c-1 was replaced with equimolar c-52 to give compound 52 (10.32 g) with a solid purity ≧ 99.88% by HPLC. Mass spectrum m/z:487.1917 (theoretical value: 487.1936). Theoretical element content (%) C 36 H 25 NO: c,88.68; h,5.17; and N,2.87. Measured elemental content (%): c,88.69; h,5.14; n,2.83.
Synthetic example 7: preparation of Compound 77
According to the method of example 1, the starting material a-1 was replaced with an equal mole of a-77 and the starting material b-1 was replaced with an equal mole of b-77 to obtain 77 (14.06 g) having a solid purity ≧ 99.94% by HPLC. Mass spectrum m/z:687.2549 (theoretical value: 687.2562). Theoretical element content (%) C 52 H 33 NO: c,90.80; h,4.84; and N,2.04. Measured elemental content (%): c,90.83; h,4.80; and N,2.06.
Synthesis example 8: preparation of Compound 143
Preparation of intermediate b-143:
according to the method of example 3, the starting material f-37 was replaced with equimolar f-143 to give intermediate b-143 (21.41 g), and the purity of the solid was ≧ 99.85% by HPLC. Mass spectrum m/z:316.9592 (theoretical value: 316.9607).
Preparation of compound 143:
according to the method of example 1, the starting material a-1 was replaced with an equimolar amount of a-143, the intermediate b-1 was replaced with an equimolar amount of b-143, and the intermediate c-1 was replaced with an equimolar amount of c-52, to obtain compound 143 (15.68 g) having a solid purity of 99.96% or more by HPLC. Mass spectrum m/z:788.2837 (theoretical value: 788.2828). Theory of thingsArgument content (%) C 59 H 36 N 2 O: c,89.82; h,4.60; and N,3.55. Measured elemental content (%): c,89.86; h,4.58; and N,3.52.
Synthetic example 9: preparation of Compound 166
According to the method of example 1, the raw material a-1 was replaced with an equal mole of a-166, the raw material b-1 was replaced with an equal mole of b-166, and the intermediate c-1 was replaced with an equal mole of c-52, to obtain compound 166 (12.80 g) with a solid purity ≧ 99.92% by HPLC. Mass spectrum m/z:609.2085 (theoretical value: 609.2093). Theoretical element content (%) C 46 H 27 NO: c,90.62; h,4.46; and N,2.30. Measured elemental content (%): c,90.66; h,4.43; and N,2.32.
Synthesis example 10: preparation of Compound 192
Preparation of intermediate b-192:
according to the method of example 3, the raw material g-37 was replaced with equimolar g-192 to obtain intermediate b-192 (20.58 g), and the purity of solid was ≧ 99.81% by HPLC. Mass spectrum m/z:319.9929 (theoretical value: 319.9905).
Preparation of compound 192:
according to the method of example 1, the starting material a-1 was replaced with an equal mole of a-192, the intermediate b-1 was replaced with an equal mole of b-192, and the intermediate c-1 was replaced with an equal mole of c-192, to give 192 (16.46 g) as a compound having a purity of 99.98% or more by HPLC. Mass spectrum m/z:851.4049 (theoretical value: 851.4065). Theoretical element content (%) C 64 H 45 D 4 NO: c,90.21; h,6.27; n,1.64. Measured elemental content (%): c,90.25; h,6.26; n,1.62.
Synthetic example 11: preparation of Compound 237
According to the method of example 1, the raw material a-1 was replaced with an equimolar amount of a-237, the raw material b-1 was replaced with an equimolar amount of f-143, and the intermediate c-1 was replaced with an equimolar amount of c-192, to obtain 237 (13.04 g), which was purified by HPLC analysis to have a solid purity of 99.92% or more. Mass spectrum m/z:612.2214 (theoretical value: 612.2202). Theoretical element content (%) C 45 H 28 N 2 O: c,88.21; h,4.61; and N,4.57. Measured elemental content (%): c,88.24; h,4.57; and N,4.59.
Synthetic example 12: preparation of Compound 250
Preparation of intermediate b-250:
according to the method of example 3, the starting material f-37 was replaced by an equimolar amount of b-166 and the starting material g-37 was replaced by an equimolar amount of g-250 to obtain intermediate b-250 (19.12 g), which was purified by HPLC to a purity of 99.93% or more. Mass spectrum m/z:269.9737 (theoretical value: 269.9749).
Preparation of compound 250:
according to the method of example 1, the starting material a-1 was replaced with an equivalent mole of a-250, the intermediate b-1 was replaced with an equivalent mole of b-250, and the intermediate c-1 was replaced with an equivalent mole of c-250, to give 250 (13.98 g) of compound with a purity of 99.94% by HPLC. Mass spectrum m/z:683.3142 (theoretical value: 683.3126). Theoretical element content (%) C 51 H 33 D 4 NO: c,89.57; h,6.04; and N,2.05. Measured elemental content (%): c,89.62; h,6.01; and N,2.04.
Synthetic example 13: preparation of Compound 262
According to the method of example 1, the starting material d-1 was replaced with equimolar d-262, the starting material a-1 was replaced with equimolar a-262, the starting material b-1 was replaced with equimolar b-262 and the intermediate c-1 was replaced with equimolar c-262, obtaining compound 262 (13.02 g) with a solid purity ≧ 99.92% by HPLC. Mass spectrum m/z:619.2866 (theoretical value: 619.2875). Theoretical element content (%) C 46 H 37 NO: c,89.14; h,6.02; and N,2.26. Measured elemental content (%): c,89.17; h,5.98; and N,2.24.
Synthesis example 14: preparation of Compound 265
According to the method of example 1, the starting material a-1 was replaced with an equimolar amount of a-265, the starting material b-1 was replaced with an equimolar amount of b-265, and the intermediate c-1 was replaced with an equimolar amount of c-192, to obtain 265 (15.43 g) with a solid purity of 99.96% or more by HPLC. Mass spectrum m/z:775.2528 (theoretical value: 775.2511). Theoretical element content (%) C 58 H 33 NO 2 : c,89.78; h,4.29; n,1.81. Measured elemental content (%): c,89.74; h,4.31; n,1.79.
Synthetic example 15: preparation of Compound 266
According to the method of example 1, the starting material a-1 was replaced with an equal mole of a-266 and the starting material b-1 was replaced with an equal mole of b-266 to obtain 266 (15.25 g) of compound with a solid purity ≧ 99.97% by HPLC. Mass spectrum m/z:775.2679 (theoretical value: 777.2668). Theoretical element content (%) C 58 H 35 NO 2 : c,89.55; h,4.54; and N,1.80. Measured elemental content (%): c,89.50; h,4.56; n,1.79.
Synthetic example 16: preparation of Compound 304
Preparation of intermediate b-304:
according to the method of example 3, the starting material f-37 was replaced with an equivalent mole of f-304, and the starting material g-37 was replaced with an equivalent mole of g-304, to give intermediate b-304 (18.11 g), which was purified by HPLC to a solid purity of 99.88% or more. Mass spectrum m/z:267.9415 (theoretical value: 267.9403).
Preparation of compound 304:
according to the method of example 1, the raw material a-1 was replaced by an equal mole of a-304, the intermediate b-1 was replaced by an equal mole of b-304, the intermediate c-1 was replaced by an equal mole of c-304, and the raw material d-1 was replaced by an equal mole of d-304, to obtain compound 304 (14.71 g), which had a solid purity of 99.95% or more by HPLC. Mass spectrum m/z:729.2794 (theoretical value: 729.2780). Theoretical element content (%) C 53 H 35 N 3 O: c,87.22; h,4.83; and N,5.76. Measured elemental content (%): c,87.24; h,4.79; n,5.77.
Synthetic example 17: preparation of Compound 311
Preparation of intermediate b-311:
according to the method of example 3, the starting material f-37 was replaced by an equimolar amount of f-304 and the starting material g-37 was replaced by an equimolar amount of g-311 to give intermediate b-311 (22.46 g) having a purity of 99.82% or more by HPLC. Mass spectrum m/z:320.9901 (theoretical value: 320.9920).
Preparation of compound 311:
according to the method of example 1, starting material a-1 was replaced with equimolar a-311, intermediate b-1 was replaced with equimolar b-311, intermediate c-1 was replaced with equimolar c-311, and starting material d-1 was replaced with equimolar d-311 to give compound 311 (15.05 g) with a solid purity of 99.96% or more by HPLC. Mass spectrum m/z:756.2766 (theoretical value: 756.2777). Theoretical element content (%) C 55 H 36 N 2 O 2 : c,87.28; h,4.79; and N,3.70. Measured elemental content (%): c,87.24; h,4.78; n,3.73.
Synthetic example 18: preparation of Compound 313
Preparation of intermediate b-313:
according to the method of example 3, the starting material f-37 was replaced with an equimolar amount of f-313, and the starting material g-37 was replaced with an equimolar amount of g-43, to obtain intermediate b-313 (21.87 g), which was purified by HPLC to a solid purity of 99.86% or more. Mass spectrum m/z:319.9985 (theoretical value: 319.9967).
Preparation of compound 313:
according to the method of example 1, the starting material a-1 was replaced with an equimolar amount of a-313, the intermediate b-1 was replaced with an equimolar amount of b-313, and the intermediate c-1 was replaced with an equimolar amount of c-52, to obtain compound 313 (15.13 g) having a purity of 99.97% or more by HPLC. Mass spectrum m/z:771.2607 (theoretical value: 771.2596). Theoretical element content (%) C 56 H 37 NOS: c,87.13; h,4.83; n,1.81. Measured elemental content (%): c,87.08; h,4.85; n,1.82.
Synthetic example 19: preparation of Compound 347
According to the method of example 1, the starting material a-1 was replaced with an equivalent mole of a-347, the starting material b-1 was replaced with an equivalent mole of b-347, and the intermediate c-1 was replaced with an equivalent mole of c-347, to obtain compound 347 (13.77 g) with a solid purity ≧ 99.86% by HPLC. Mass spectrum m/z:655.2069 (theoretical value: 655.2082). Theoretical element content (%) C 46 H 29 N 3 S: c,84.25; h,4.46; and N,6.41. Measured elemental content (%): c,84.21; h,4.45; and N,6.38.
Synthesis example 20: preparation of Compound 382
According to the method of example 1, starting material a-1 was replaced with an equal mole of a-382, starting material b-1 was replaced with an equal mole of b-382, and intermediate c-1 was replaced with an equal mole of c-347, to give compound 382 (15.22 g) with a solid purity ≧ 99.95% by HPLC. Mass spectrum m/z:754.2452 (theoretical value: 754.2443). Theoretical element content(％)C 55 H 34 N 2 S: c,87.50; h,4.54; n,3.71. Measured elemental content (%): c,87.54; h,4.52; and N,3.68.
Synthetic example 21: preparation of Compound 419
According to the method of example 1, the starting material a-1 was replaced with an equimolar amount of a-419, the starting material b-1 was replaced with an equimolar amount of b-382, and the intermediate c-1 was replaced with an equimolar amount of c-419, to obtain compound 419 (15.74 g) with a solid purity of 99.98% or more by HPLC. Mass spectrum m/z:802.2430 (theoretical value: 802.2443). Theoretical element content (%) C 59 H 34 N 2 S: c,88.25; h,4.27; and N,3.49. Measured elemental content (%): c,88.29; h,4.25; and N,3.46.
Synthetic example 22: preparation of Compound 438
Preparation of intermediate b-438:
according to the method of example 3, the starting material f-37 was replaced with an equimolar amount of b-1, and the starting material g-37 was replaced with an equimolar amount of g-250, to obtain intermediate b-438 (18.90 g), which was purified by HPLC to a solid purity of 99.95% or more. Mass spectrum m/z:269.9763 (theoretical value: 269.9749).
Preparation of compound 438:
according to the method of example 1, the starting material a-1 was replaced with an equal mole of a-438, the intermediate b-1 was replaced with an equal mole of b-438, and the intermediate c-1 was replaced with an equal mole of c-438, to obtain 438 (14.02 g), which was greater than or equal to 99.94% purity by HPLC. Mass spectrum m/z:685.2751 (theoretical value: 685.2741). Theoretical element content (%) C 50 H 31 D 4 And NS: c,87.55; h,5.73; n,2,04. Measured elemental content (%): c,87.51; h,5.71; and N,2.06.
Synthetic example 23: preparation of Compound 468
According to the method of example 1, the raw material a-1 was replaced with an equal mole of a-468, the raw material b-1 was replaced with an equal mole of b-468, and the intermediate c-1 was replaced with an equal mole of c-347, to give compound 468 (16.29 g) in a purity of 99.98% by HPLC. Mass spectrum m/z:842.2744 (theoretical value: 842.2756). Theoretical element content (%) C 62 H 38 N 2 S: c,88.33; h,4.54; n,3.32. Measured elemental content (%): c,88.36; h,4.50; and N,3.30.
Example 24: measurement of glass transition temperature
Test samples: the compounds prepared in the synthesis examples of the present invention and comparative compounds 1 to 2.
Testing an instrument: DSC 25 type differential scanning calorimeter (TA, USA);
and (3) testing conditions: the test atmosphere is nitrogen, and the flow rate of the nitrogen is 50mL/min; the heating rate is 10 ℃/min, and the temperature range is 50-350 ℃. The glass transition temperature (Tg) test results are shown in table 1:
table 1:
| compound (I) | Glass transition temperature (. Degree. C.) | Compound (I) | Glass transition temperature (. Degree. C.) |
| Compound 1 | 115.8 | Compound 265 | 119.3 |
| Compound 18 | 116.0 | Compound 266 | 118.9 |
| Compound 37 | 119.5 | Compound 304 | 117.8 |
| Compound 38 | 116.2 | Compound 311 | 118.8 |
| Compound 43 | 116.4 | Compound 313 | 118.5 |
| Compound 52 | 116.1 | Compound 347 | 117.9 |
| Compound 77 | 116.3 | Compound 382 | 117.0 |
| Compound 143 | 117.1 | Compound 419 | 118.2 |
| Compound 166 | 117.3 | Compound 438 | 116.7 |
| Compound 192 | 117.5 | Compound 468 | 118.0 |
| Compound 237 | 116.5 | Comparative Compound 1 | 102.5 |
| Compound 250 | 119.6 | Comparative Compound 2 | 111.7 |
| Compound 262 | 118.4 |
As can be seen from Table 1, the compound of the present invention has a higher glass transition temperature, and the thermal stability and film forming property of the material are improved compared with those of comparative compounds 1 and 2, and the service life of the device can be prolonged when the compound is applied to an organic electroluminescent device.
Device example 1
Firstly, putting a glass substrate evaporated with ITO/Ag/ITO into distilled water for cleaning for 2 times, ultrasonically cleaning for 30 minutes, repeatedly cleaning for 2 times by using distilled water, ultrasonically cleaning for 10 minutes, after the cleaning of the distilled water is finished, ultrasonically cleaning by using solvents of isopropanol, acetone and methanol in sequence, drying on a hot plate heated to 120 ℃, transferring the dried substrate into a plasma cleaning machine, and transferring the substrate into an evaporation machine after 5 minutes of cleaning.
Then, a mixture of P-1 and HI-1 (mass ratio HI-1:P-1= 97) was evaporated on an ITO/Ag/ITO substrate that had been cleaned as a hole injection layer to an evaporation thickness of 15nm, HI-1 was evaporated on the hole injection layer as a hole transport layer to an evaporation thickness of 80nm, then a mixture of BH-1 and BD-1 (mass ratio BH-1-BD-1 = 92) was vacuum evaporated on the hole transport layer to form a light emitting layer, the evaporation thickness was 42nm, the mixture of inventive compound 1 and Liq (doping ratio 1:1) was evaporated on the light emitting layer as an electron transport layer to an evaporation thickness of 30nm, and the mixture was evaporated on the electron transport layer as an electron injection layer to an evaporation thickness of 1nm, then Mg: ag (mass ratio Mg: ag = 1:9) was evaporated on the electron injection layer as a cathode to a thickness of 13nm, then LiF was vacuum evaporated on the cathode capping layer to a thickness of 65, and an organic electroluminescent device was prepared as an organic electroluminescent device by evaporation process as follows (hereinafter, or an organic electroluminescent device) was prepared as an organic electroluminescent device.
Device examples 2 to 23
Organic electroluminescent devices 2 to 23 were prepared by using compound 18, compound 37, compound 38, compound 43, compound 52, compound 77, compound 143, compound 166, compound 192, compound 237, compound 250, compound 262, compound 265, compound 266, compound 304, compound 311, compound 313, compound 347, compound 382, compound 419, compound 438, and compound 468 of the present invention as an electron transporting layer in place of compound 1 in device example 1, and the other preparation steps were the same as in device example 1.
Device example 24
A mixture of P-1 and HI-1 (mass ratio HI-1:P-1= -97) was evaporated on an ITO/Ag/ITO substrate that had been cleaned as a hole injection layer, the thickness was 15nm, HI-1 of the compound of the present invention was evaporated on the hole injection layer as a hole transport layer, the thickness was 80nm, then a mixture of BH-1 and BD-1 (mass ratio BH-1.
Device examples 25 to 46
Organic electroluminescent devices 25 to 46 were prepared by using compound 18, compound 37, compound 38, compound 43, compound 52, compound 77, compound 143, compound 166, compound 192, compound 237, compound 250, compound 262, compound 265, compound 266, compound 304, compound 311, compound 313, compound 347, compound 382, compound 419, compound 438, and compound 468 of the present invention instead of compound 1 in device example 24 as a hole-blocking layer, and the other preparation steps were the same as in device example 24.
Comparative device examples 1 to 2
Comparative compounds 1 and 2 were used as electron transport layers instead of compound 1 in device example 1, and comparative devices 1 to 2 were prepared in the same manner as in device example 1 except for the preparation steps.
Comparative device examples 3 to 4
Comparative compounds 3 to 4 were prepared by using comparative compound 1 and comparative compound 2 as hole blocking layers instead of compound 1 in device example 24, and by the same procedure as in device example 24.
The driving voltage and the luminous efficiency of the organic electroluminescent device were tested by combining test software, a computer, a K2400 digital source manufactured by Keithley, usa, and a PR788 spectral scanning luminance meter manufactured by Photo Research, usa, into a combined IVL test system. The lifetime was measured using the M6000OLED lifetime test system from McScience. The environment for testing is atmospheric environment, and the temperature is room temperature. The results of testing the light emitting characteristics of the organic electroluminescent devices obtained in the devices 1 to 46 of the present invention and the comparative examples 1 to 4 are shown in table 2 below.
Table 2:
the results in table 2 show that when the heterocyclic compound provided by the invention is used in an electron transport layer or a hole blocking layer of an organic electroluminescent device, the heterocyclic compound has high electron mobility and high three-linear-state energy levels, and can effectively transport electrons and block holes from escaping to one side of the electron transport layer, so that the recombination probability of the electrons and the holes in a light emitting layer is improved, the driving voltage of the organic electroluminescent device can be reduced, the light emitting efficiency of the device is improved, and the service life of the device is prolonged.
Device example 47
Evaporating HI-2 as a hole injection layer to a thickness of 15nm on a cleaned ITO/Ag/ITO substrate, evaporating HT-2 as a hole transport layer to a thickness of 120nm on the hole injection layer, then vacuum evaporating GH-1 and GH-2 as host materials, GD-1 as a dopant material, and (g-1.
Device examples 48 to 56
Organic electroluminescent devices 48 to 56 were produced in the same manner as in device example 47 except that compound 37, compound 52, compound 77, compound 166, compound 237, compound 266, compound 313, compound 347 and compound 419 of the present invention were used as a capping layer in place of compound 1 in device example 47.
[ comparative example 5]
Comparative device 5 was prepared by the same procedure as in device example 47 except that comparative compound 3 was used as a cap layer instead of compound 1 in device example 47.
The test software, computer, K2400 digital source meter manufactured by Keithley corporation, usa, and PR788 spectral scanning luminance meter manufactured by Photo Research corporation, usa were combined into a combined IVL test system to test the luminous efficiency of the organic electroluminescent device. The lifetime was measured using the M6000OLED lifetime test system from McScience. The environment for testing is atmospheric environment, and the temperature is room temperature. The results of the light emission characteristic tests of the devices 48 to 56 in the device example of the present invention and the organic electroluminescent device obtained in comparative example 5 are shown in table 3 below.
Table 3:
as can be seen from the results in table 3, the heterocyclic compound provided by the present invention has a high refractive index and a high glass transition temperature, and when it is applied to a capping layer of an organic electroluminescent device, it can effectively improve the light extraction efficiency of the organic electroluminescent device, and further improve the light emission efficiency of the device, and prolong the service life of the device.
It should be noted that while the invention has been particularly described in terms of particular embodiments, it will be apparent to those skilled in the art that numerous changes and modifications can be made without departing from the principles of the invention, and it is intended to cover such changes and modifications as fall within the scope of the invention.
Claims (10)
1. A heterocycle-containing compound having the structure shown in formula I:
in formula I, E is selected from any one of substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene and substituted or unsubstituted anthryl;
a is selected from the group shown in the following formula I-1 or formula I-2:
said R is 1 、R 2 Independently selected from any one of hydrogen, deuterium, cyano, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C2-C30 heteroaryl; or R 1 、R 2 Either of which may be directly bonded to L; or R 1 、R 2 Can combine with each other to form a substituted or unsubstituted spiro ring;
the R is 3 Independently selected from hydrogen, deuterium, cyano, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroarylAny one of the above; or two adjacent R 3 Can combine with each other to form a substituted or unsubstituted ring;
a is a 0 Independently selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8;
z is independently selected from any one of a single bond, O, S, C (Rx) (Ry) and N (Rz);
rx, ry and Rz are independently any one of hydrogen, deuterium, cyano, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C2-C30 heteroaryl;
the L is independently selected from a single bond or any one of the following groups:
x is independently selected from C (R) 4 ) Or an N atom;
the R is 4 Independently selected from any one of hydrogen, deuterium, cyano, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, or two adjacent R 4 Can combine with each other to form a substituted or unsubstituted ring;
n is said 1 、n 2 Independently selected from 0 or 1;
the Y is selected from any one of O, S.
2. A heterocycle-containing compound according to claim 1 wherein E is selected from any one of the following groups:
said R is 5 Independently selected from any one of hydrogen, deuterium, cyano, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C2-C30 heteroaryl;
m is 1 Independently selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8, said m 2 Independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10;
* Indicates the fusion site.
3. A heterocycle-containing compound as claimed in claim 1, wherein said compound
Any one selected from the following groups:
said R is 5 Independently selected from hydrogen, deuterium, cyano, or the following substituted or unsubstituted groups: any one of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropylalkyl, cyclobutylalkyl, cyclopentylalkyl, cyclohexylalkyl, cycloheptylalkyl, adamantyl, norbornanyl, phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, benzocyclopropylalkyl, benzocyclobutylalkyl, benzocyclopentylalkyl, benzocyclocyclohexylalkyl, fluorenyl, dibenzofuranyl, dibenzothienyl, carbazolyl, pyridyl, phenyl-pyridyl, pyrimidinyl, phenyl-pyrimidinyl, pyrazinyl, phenyl-pyrazinyl, pyridazinyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl;
the substituted group is selected from any one or more of deuterium, cyano-group, substituted or unsubstituted C1-C12 alkyl and substituted or unsubstituted C3-C12 cycloalkyl; when a plurality of substituents are present, the plurality of substituents may be the same as or different from each other;
m is 1 Independently selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8, said m 2 Independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10.
4. A heterocycle-containing compound according to claim 1, wherein R is 1 、R 2 Independently selected from hydrogen, deuterium, or the following substituted or unsubstituted groups: any one of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropylalkyl, cyclobutylalkyl, cyclopentylalkyl, cyclohexylalkyl, cycloheptylalkyl, adamantyl, norbornanyl, phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, benzocyclopropylalkyl, benzocyclobutylalkyl, benzocyclopentylalkyl, benzocyclocyclohexylalkyl, fluorenyl, dibenzofuranyl, dibenzothienyl, carbazolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, quinolyl, isoquinolyl, quinoxalyl, quinazolinyl;
the "substituted" group is any one or more selected from deuterium, cyano, substituted or unsubstituted C1-C12 alkyl, and substituted or unsubstituted C3-C12 cycloalkyl, and when a plurality of substituents are present, the plurality of substituents are the same as or different from each other;
or R 1 、R 2 Either of which may be directly bonded to L; or R 1 、R 2 Can be combined with each other to form any one of the following structures:
the R is 6 Independently selected from deuterium, cyano, or the following substituted or unsubstituted groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropylalkyl, cyclobutylalkyl, cyclopentylalkyl cyclohexane, cycloheptane, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl,Any one of phenanthryl, triphenylene, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclocyclohexane, fluorenyl, dibenzofuranyl, dibenzothienyl, carbazolyl, pyridyl, pyrimidinyl, quinolyl, isoquinolyl, quinoxalinyl, and quinazolinyl;
the "substituted" group is any one or more selected from deuterium, a substituted or unsubstituted C1-C12 alkyl group, and a substituted or unsubstituted C3-C12 cycloalkyl group, and when a plurality of substituents are present, the plurality of substituents are the same as or different from each other;
a is a mentioned 1 Independently selected from 0, 1, 2, 3 or 4, said a 2 Independently selected from 0, 1, 2, 3, 4, 5 or 6, said a 3 Independently selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8, said a 4 Independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10, said a 5 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9,10, 11 or 12; a is a mentioned 6 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9,10, 11, 12, 13 or 14; a is a mentioned 7 Selected from 0, 1 or 2.
5. A heterocycle-containing compound according to claim 1 wherein a is independently selected from any one of the following groups:
the R is 3 Independently selected from hydrogen, deuterium, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropylAlkyl, cyclopropylalkyl, cyclobutylalkyl, cyclopentylalkyl, cyclohexylalkyl, cycloheptylalkyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, benzocyclopropylalkyl, benzocyclobutylalkyl, benzocyclopentylalkyl, benzocyclohexylalkyl, pyridyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, deuterium substituted of the following groups: any one of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropylalkyl, cyclobutylalkyl, cyclopentylalkyl, cyclohexylalkyl, cycloheptylalkyl, adamantyl, norbornanyl, phenyl, biphenyl, terphenyl, naphthyl, benzocyclopropylalkyl, benzocyclobutylalkyl, benzocyclopentylalkyl, benzocyclohexylalkyl, pyridyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl;
the R is 6 Any one independently selected from hydrogen, deuterium, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentyl, cyclohexane, cycloheptane, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, benzocyclobutane, benzocyclopentyl, benzocyclocyclohexane, pyridyl, pyrimidinyl, quinolyl, isoquinolyl, quinoxalinyl and quinazolinyl;
a is a 0 Independently selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8, said a 1 Independently selected from 0, 1, 2, 3 or 4, said a 2 Independently selected from 0, 1, 2, 3, 4, 5 or 6, said a 3 Independently selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8, said a 4 Independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10, said a 5 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9,10, 11 or 12; a is a 6 Selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9,10, 11, 12, 13 or 14, said a 7 Selected from 0, 1 or 2, said a 8 Independently selected from 0, 1, 2, 3, 4, 5, 6 or 7, said a 9 Independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9,10, 11, 12 or 13, said a 10 Independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9, said a 11 Independently selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9,10 or 11, said a 12 Independently selected from 0, 1, 2, 3, 4 or 5.
6. A heterocycle-containing compound according to claim 1 wherein L is independently selected from the group consisting of a single bond and any one of the following substituted or unsubstituted groups:
the substituted group is any one or more of deuterium, methyl, ethyl, n-propyl, isopropyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl and norbornyl; when a plurality of substituents are present, the plurality of substituents may be the same as or different from each other.
7. The heterocycle-containing compound of claim 1, wherein the heterocycle-containing compound is selected from any one of the following structures:
8. an organic electroluminescent device comprising an anode, an organic layer, and a cathode, wherein the organic layer is located between the anode and the cathode or outside at least one of the anode and the cathode, and wherein the organic layer comprises any one or more of the heterocyclic ring-containing compounds according to any one of claims 1 to 7.
9. The organic electroluminescent device according to claim 8, wherein the organic layer comprises at least one of an electron transport layer or a hole blocking layer, and the at least one of the electron transport layer or the hole blocking layer comprises any one or more of the heterocyclic ring-containing compounds according to any one of claims 1 to 7.
10. The organic electroluminescent device according to claim 8, wherein the organic layer comprises a capping layer comprising any one or more of the heterocyclic ring-containing compounds according to any one of claims 1 to 7.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN116063267A (en) * | 2022-09-28 | 2023-05-05 | 上海钥熠电子科技有限公司 | Spiro compound and application thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20150136033A (en) * | 2014-05-26 | 2015-12-04 | 주식회사 엘지화학 | Nitrogen-containing heterocyclic compounds and organic electronic device using the same |
| CN113717153A (en) * | 2021-09-18 | 2021-11-30 | 长春海谱润斯科技股份有限公司 | Spiro compound and organic light-emitting device thereof |
| CN114773286A (en) * | 2022-05-10 | 2022-07-22 | 长春海谱润斯科技股份有限公司 | Nitrogen-containing heterocyclic organic compound and organic light-emitting device thereof |
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20150136033A (en) * | 2014-05-26 | 2015-12-04 | 주식회사 엘지화학 | Nitrogen-containing heterocyclic compounds and organic electronic device using the same |
| CN113717153A (en) * | 2021-09-18 | 2021-11-30 | 长春海谱润斯科技股份有限公司 | Spiro compound and organic light-emitting device thereof |
| CN114773286A (en) * | 2022-05-10 | 2022-07-22 | 长春海谱润斯科技股份有限公司 | Nitrogen-containing heterocyclic organic compound and organic light-emitting device thereof |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN116063267A (en) * | 2022-09-28 | 2023-05-05 | 上海钥熠电子科技有限公司 | Spiro compound and application thereof |
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