CN114773286B - 一种含氮杂环有机化合物及其有机发光器件 - Google Patents
一种含氮杂环有机化合物及其有机发光器件 Download PDFInfo
- Publication number
- CN114773286B CN114773286B CN202210509454.6A CN202210509454A CN114773286B CN 114773286 B CN114773286 B CN 114773286B CN 202210509454 A CN202210509454 A CN 202210509454A CN 114773286 B CN114773286 B CN 114773286B
- Authority
- CN
- China
- Prior art keywords
- compound
- group
- substituted
- deuterium
- nitrogen
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- -1 Nitrogen-containing heterocyclic organic compound Chemical class 0.000 title claims abstract description 79
- 230000000903 blocking effect Effects 0.000 claims abstract description 16
- 239000010410 layer Substances 0.000 claims description 68
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 38
- 229910052805 deuterium Inorganic materials 0.000 claims description 38
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 21
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- 239000001257 hydrogen Substances 0.000 claims description 18
- 239000012044 organic layer Substances 0.000 claims description 18
- 238000006467 substitution reaction Methods 0.000 claims description 14
- 229910052757 nitrogen Inorganic materials 0.000 claims description 13
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 9
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 61
- 238000000034 method Methods 0.000 abstract description 32
- 238000002347 injection Methods 0.000 abstract description 12
- 239000007924 injection Substances 0.000 abstract description 12
- 125000000217 alkyl group Chemical group 0.000 abstract description 10
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 abstract description 4
- 230000005012 migration Effects 0.000 abstract description 4
- 238000013508 migration Methods 0.000 abstract description 4
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 abstract description 3
- 230000002708 enhancing effect Effects 0.000 abstract description 2
- 230000002349 favourable effect Effects 0.000 abstract description 2
- 125000002883 imidazolyl group Chemical group 0.000 abstract description 2
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 abstract 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 abstract 1
- 125000002723 alicyclic group Chemical group 0.000 abstract 1
- 125000000732 arylene group Chemical group 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 description 54
- 238000003786 synthesis reaction Methods 0.000 description 53
- 239000000463 material Substances 0.000 description 36
- 125000004432 carbon atom Chemical group C* 0.000 description 32
- 238000001819 mass spectrum Methods 0.000 description 32
- 238000004128 high performance liquid chromatography Methods 0.000 description 30
- 125000003118 aryl group Chemical group 0.000 description 29
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- 230000000052 comparative effect Effects 0.000 description 26
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical group [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 description 24
- 229910052722 tritium Chemical group 0.000 description 24
- 239000000543 intermediate Substances 0.000 description 23
- 239000007787 solid Substances 0.000 description 22
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 19
- 150000002431 hydrogen Chemical group 0.000 description 17
- 125000001424 substituent group Chemical group 0.000 description 17
- 125000001072 heteroaryl group Chemical group 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 15
- 238000001704 evaporation Methods 0.000 description 15
- 125000001624 naphthyl group Chemical group 0.000 description 15
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 14
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 14
- 238000012360 testing method Methods 0.000 description 14
- 125000001931 aliphatic group Chemical group 0.000 description 13
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 13
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 13
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 12
- 238000002360 preparation method Methods 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 11
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 11
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 239000004305 biphenyl Substances 0.000 description 9
- 239000000758 substrate Substances 0.000 description 9
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 8
- 125000003342 alkenyl group Chemical group 0.000 description 8
- 235000010290 biphenyl Nutrition 0.000 description 8
- 230000005525 hole transport Effects 0.000 description 8
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 8
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 8
- 239000012153 distilled water Substances 0.000 description 7
- 239000010408 film Substances 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 7
- 239000002994 raw material Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- 238000005516 engineering process Methods 0.000 description 6
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 6
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 6
- 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 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 125000000753 cycloalkyl group Chemical group 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 5
- 125000005561 phenanthryl group Chemical group 0.000 description 5
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- 229910052783 alkali metal Inorganic materials 0.000 description 4
- 150000001340 alkali metals Chemical class 0.000 description 4
- 229910045601 alloy Inorganic materials 0.000 description 4
- 239000000956 alloy Substances 0.000 description 4
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 4
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 4
- 125000004369 butenyl group Chemical group C(=CCC)* 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
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 4
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 4
- 125000000592 heterocycloalkyl group Chemical group 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- 125000002632 imidazolidinyl group Chemical group 0.000 description 4
- 125000002757 morpholinyl group Chemical group 0.000 description 4
- 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 4
- 125000000160 oxazolidinyl group Chemical group 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
- IVDFJHOHABJVEH-UHFFFAOYSA-N pinacol Chemical compound CC(C)(O)C(C)(C)O IVDFJHOHABJVEH-UHFFFAOYSA-N 0.000 description 4
- 125000004193 piperazinyl group Chemical group 0.000 description 4
- 125000003386 piperidinyl group Chemical group 0.000 description 4
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 4
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 238000011160 research Methods 0.000 description 4
- 125000003003 spiro group Chemical group 0.000 description 4
- 125000001984 thiazolidinyl group Chemical group 0.000 description 4
- 125000004568 thiomorpholinyl group Chemical group 0.000 description 4
- 125000003944 tolyl group Chemical group 0.000 description 4
- 238000007738 vacuum evaporation Methods 0.000 description 4
- 229910000838 Al alloy Inorganic materials 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 3
- 229910052784 alkaline earth metal Chemical class 0.000 description 3
- 150000001342 alkaline earth metals Chemical class 0.000 description 3
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 3
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 150000001721 carbon Chemical group 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 229940125904 compound 1 Drugs 0.000 description 3
- 125000004093 cyano group Chemical group *C#N 0.000 description 3
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 description 3
- 239000012065 filter cake Substances 0.000 description 3
- 125000002541 furyl group Chemical group 0.000 description 3
- 150000004820 halides Chemical class 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 3
- 125000002347 octyl 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])[H] 0.000 description 3
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 3
- 125000001725 pyrenyl group Chemical group 0.000 description 3
- 125000000714 pyrimidinyl group Chemical group 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 125000001544 thienyl group Chemical group 0.000 description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 2
- XOYZGLGJSAZOAG-UHFFFAOYSA-N 1-n,1-n,4-n-triphenyl-4-n-[4-[4-(n-[4-(n-phenylanilino)phenyl]anilino)phenyl]phenyl]benzene-1,4-diamine Chemical compound C1=CC=CC=C1N(C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC(=CC=1)C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 XOYZGLGJSAZOAG-UHFFFAOYSA-N 0.000 description 2
- SKMKJBYBPYBDMN-RYUDHWBXSA-N 3-(difluoromethoxy)-5-[2-(3,3-difluoropyrrolidin-1-yl)-6-[(1s,4s)-2-oxa-5-azabicyclo[2.2.1]heptan-5-yl]pyrimidin-4-yl]pyridin-2-amine Chemical compound C1=C(OC(F)F)C(N)=NC=C1C1=CC(N2[C@H]3C[C@H](OC3)C2)=NC(N2CC(F)(F)CC2)=N1 SKMKJBYBPYBDMN-RYUDHWBXSA-N 0.000 description 2
- TZZDVPMABRWKIZ-MFTLXVFQSA-N 3-[6-[4-[[1-[4-[(1R,2S)-6-hydroxy-2-phenyl-1,2,3,4-tetrahydronaphthalen-1-yl]phenyl]piperidin-4-yl]methyl]piperazin-1-yl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound OC=1C=C2CC[C@@H]([C@@H](C2=CC=1)C1=CC=C(C=C1)N1CCC(CC1)CN1CCN(CC1)C=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O)C1=CC=CC=C1 TZZDVPMABRWKIZ-MFTLXVFQSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- 229910001316 Ag alloy Inorganic materials 0.000 description 2
- 125000000739 C2-C30 alkenyl group Chemical group 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 229910000846 In alloy Inorganic materials 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- AVYVHIKSFXVDBG-UHFFFAOYSA-N N-benzyl-N-hydroxy-2,2-dimethylbutanamide Chemical compound C(C1=CC=CC=C1)N(C(C(CC)(C)C)=O)O AVYVHIKSFXVDBG-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 description 2
- LJOOWESTVASNOG-UFJKPHDISA-N [(1s,3r,4ar,7s,8s,8as)-3-hydroxy-8-[2-[(4r)-4-hydroxy-6-oxooxan-2-yl]ethyl]-7-methyl-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-yl] (2s)-2-methylbutanoate Chemical compound C([C@H]1[C@@H](C)C=C[C@H]2C[C@@H](O)C[C@@H]([C@H]12)OC(=O)[C@@H](C)CC)CC1C[C@@H](O)CC(=O)O1 LJOOWESTVASNOG-UFJKPHDISA-N 0.000 description 2
- JHYLKGDXMUDNEO-UHFFFAOYSA-N [Mg].[In] Chemical compound [Mg].[In] JHYLKGDXMUDNEO-UHFFFAOYSA-N 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 125000002393 azetidinyl group Chemical group 0.000 description 2
- 125000004069 aziridinyl group Chemical group 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 238000005885 boration reaction Methods 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- CRPUJAZIXJMDBK-UHFFFAOYSA-N camphene Chemical compound C1CC2C(=C)C(C)(C)C1C2 CRPUJAZIXJMDBK-UHFFFAOYSA-N 0.000 description 2
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 229940127204 compound 29 Drugs 0.000 description 2
- 125000001047 cyclobutenyl group Chemical group C1(=CCC1)* 0.000 description 2
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 2
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 2
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 2
- 239000002019 doping agent Substances 0.000 description 2
- DFBKLUNHFCTMDC-GKRDHZSOSA-N endrin Chemical compound C([C@@H]1[C@H]2[C@@]3(Cl)C(Cl)=C([C@]([C@H]22)(Cl)C3(Cl)Cl)Cl)[C@@H]2[C@H]2[C@@H]1O2 DFBKLUNHFCTMDC-GKRDHZSOSA-N 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 229910002804 graphite Inorganic materials 0.000 description 2
- 239000010439 graphite Substances 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002366 halogen compounds Chemical class 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000006038 hexenyl group Chemical group 0.000 description 2
- 150000002430 hydrocarbons 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
- 239000002346 layers by function Substances 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- SJCKRGFTWFGHGZ-UHFFFAOYSA-N magnesium silver Chemical compound [Mg].[Ag] SJCKRGFTWFGHGZ-UHFFFAOYSA-N 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- BLFVVZKSHYCRDR-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-2-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-2-amine Chemical compound C1=CC=CC=C1N(C=1C=C2C=CC=CC2=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C3C=CC=CC3=CC=2)C=C1 BLFVVZKSHYCRDR-UHFFFAOYSA-N 0.000 description 2
- YGBMCLDVRUGXOV-UHFFFAOYSA-N n-[6-[6-chloro-5-[(4-fluorophenyl)sulfonylamino]pyridin-3-yl]-1,3-benzothiazol-2-yl]acetamide Chemical compound C1=C2SC(NC(=O)C)=NC2=CC=C1C(C=1)=CN=C(Cl)C=1NS(=O)(=O)C1=CC=C(F)C=C1 YGBMCLDVRUGXOV-UHFFFAOYSA-N 0.000 description 2
- 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 2
- IOMMMLWIABWRKL-WUTDNEBXSA-N nazartinib Chemical compound C1N(C(=O)/C=C/CN(C)C)CCCC[C@H]1N1C2=C(Cl)C=CC=C2N=C1NC(=O)C1=CC=NC(C)=C1 IOMMMLWIABWRKL-WUTDNEBXSA-N 0.000 description 2
- 125000002255 pentenyl group Chemical group C(=CCCC)* 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
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 125000003367 polycyclic group Chemical group 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 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
- 125000004076 pyridyl group Chemical group 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000007789 sealing Methods 0.000 description 2
- 239000010703 silicon Substances 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 229910052709 silver Inorganic materials 0.000 description 2
- 239000004332 silver Substances 0.000 description 2
- 230000003595 spectral effect Effects 0.000 description 2
- 238000004544 sputter deposition Methods 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- 238000002207 thermal evaporation Methods 0.000 description 2
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 2
- 125000004306 triazinyl group Chemical group 0.000 description 2
- 125000005580 triphenylene group Chemical group 0.000 description 2
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 2
- 238000007740 vapor deposition Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- SZUVGFMDDVSKSI-WIFOCOSTSA-N (1s,2s,3s,5r)-1-(carboxymethyl)-3,5-bis[(4-phenoxyphenyl)methyl-propylcarbamoyl]cyclopentane-1,2-dicarboxylic acid Chemical compound O=C([C@@H]1[C@@H]([C@](CC(O)=O)([C@H](C(=O)N(CCC)CC=2C=CC(OC=3C=CC=CC=3)=CC=2)C1)C(O)=O)C(O)=O)N(CCC)CC(C=C1)=CC=C1OC1=CC=CC=C1 SZUVGFMDDVSKSI-WIFOCOSTSA-N 0.000 description 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 1
- 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 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 125000004973 1-butenyl group Chemical group C(=CCC)* 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
- 125000006039 1-hexenyl group Chemical group 0.000 description 1
- 125000006023 1-pentenyl group Chemical group 0.000 description 1
- 125000006017 1-propenyl group Chemical group 0.000 description 1
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 1
- IXHWGNYCZPISET-UHFFFAOYSA-N 2-[4-(dicyanomethylidene)-2,3,5,6-tetrafluorocyclohexa-2,5-dien-1-ylidene]propanedinitrile Chemical compound FC1=C(F)C(=C(C#N)C#N)C(F)=C(F)C1=C(C#N)C#N IXHWGNYCZPISET-UHFFFAOYSA-N 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- 125000006040 2-hexenyl group Chemical group 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
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
- 125000006024 2-pentenyl group Chemical group 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
- 125000006041 3-hexenyl group Chemical group 0.000 description 1
- UDQLIWBWHVOIIF-UHFFFAOYSA-N 3-phenylbenzene-1,2-diamine Chemical compound NC1=CC=CC(C=2C=CC=CC=2)=C1N UDQLIWBWHVOIIF-UHFFFAOYSA-N 0.000 description 1
- WDBQJSCPCGTAFG-QHCPKHFHSA-N 4,4-difluoro-N-[(1S)-3-[4-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)piperidin-1-yl]-1-pyridin-3-ylpropyl]cyclohexane-1-carboxamide Chemical compound FC1(CCC(CC1)C(=O)N[C@@H](CCN1CCC(CC1)N1C(=NN=C1C)C(C)C)C=1C=NC=CC=1)F WDBQJSCPCGTAFG-QHCPKHFHSA-N 0.000 description 1
- 125000006042 4-hexenyl group Chemical group 0.000 description 1
- 125000006043 5-hexenyl group Chemical group 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 229920003026 Acene Polymers 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
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 229910052684 Cerium Inorganic materials 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- PMPVIKIVABFJJI-UHFFFAOYSA-N Cyclobutane Chemical compound C1CCC1 PMPVIKIVABFJJI-UHFFFAOYSA-N 0.000 description 1
- LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 229910052693 Europium Inorganic materials 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 229910000861 Mg alloy Inorganic materials 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- PXRCIOIWVGAZEP-UHFFFAOYSA-N Primaeres Camphenhydrat Natural products C1CC2C(O)(C)C(C)(C)C1C2 PXRCIOIWVGAZEP-UHFFFAOYSA-N 0.000 description 1
- 229910052772 Samarium Inorganic materials 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 238000006069 Suzuki reaction reaction Methods 0.000 description 1
- 229910052771 Terbium Inorganic materials 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 229910052769 Ytterbium Inorganic materials 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 1
- ULGYAEQHFNJYML-UHFFFAOYSA-N [AlH3].[Ca] Chemical compound [AlH3].[Ca] ULGYAEQHFNJYML-UHFFFAOYSA-N 0.000 description 1
- JFBZPFYRPYOZCQ-UHFFFAOYSA-N [Li].[Al] Chemical compound [Li].[Al] JFBZPFYRPYOZCQ-UHFFFAOYSA-N 0.000 description 1
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 1
- 125000003670 adamantan-2-yl group Chemical group [H]C1([H])C(C2([H])[H])([H])C([H])([H])C3([H])C([*])([H])C1([H])C([H])([H])C2([H])C3([H])[H] 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 150000001339 alkali metal compounds Chemical class 0.000 description 1
- 229910001508 alkali metal halide Inorganic materials 0.000 description 1
- 229910000272 alkali metal oxide Inorganic materials 0.000 description 1
- 150000001341 alkaline earth metal compounds 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
- 150000001336 alkenes Chemical class 0.000 description 1
- XCPQUQHBVVXMRQ-UHFFFAOYSA-N alpha-Fenchene Natural products C1CC2C(=C)CC1C2(C)C XCPQUQHBVVXMRQ-UHFFFAOYSA-N 0.000 description 1
- SNAAJJQQZSMGQD-UHFFFAOYSA-N aluminum magnesium Chemical compound [Mg].[Al] SNAAJJQQZSMGQD-UHFFFAOYSA-N 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 125000000748 anthracen-2-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C([H])=C([*])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 1
- 150000001454 anthracenes Chemical class 0.000 description 1
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 125000003725 azepanyl group Chemical group 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 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
- 229910052790 beryllium Inorganic materials 0.000 description 1
- ATBAMAFKBVZNFJ-UHFFFAOYSA-N beryllium atom Chemical compound [Be] ATBAMAFKBVZNFJ-UHFFFAOYSA-N 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 1
- 229910000024 caesium carbonate Inorganic materials 0.000 description 1
- WUKWITHWXAAZEY-UHFFFAOYSA-L calcium difluoride Chemical compound [F-].[F-].[Ca+2] WUKWITHWXAAZEY-UHFFFAOYSA-L 0.000 description 1
- 229910001634 calcium fluoride Inorganic materials 0.000 description 1
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
- 239000000292 calcium oxide Substances 0.000 description 1
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
- 229930006739 camphene Natural products 0.000 description 1
- ZYPYEBYNXWUCEA-UHFFFAOYSA-N camphenilone Natural products C1CC2C(=O)C(C)(C)C1C2 ZYPYEBYNXWUCEA-UHFFFAOYSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000010406 cathode material Substances 0.000 description 1
- ZMIGMASIKSOYAM-UHFFFAOYSA-N cerium Chemical compound [Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce] ZMIGMASIKSOYAM-UHFFFAOYSA-N 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
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 229940126543 compound 14 Drugs 0.000 description 1
- 229940125898 compound 5 Drugs 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- ZXIJMRYMVAMXQP-UHFFFAOYSA-N cycloheptene Chemical compound C1CCC=CCC1 ZXIJMRYMVAMXQP-UHFFFAOYSA-N 0.000 description 1
- 125000003678 cyclohexadienyl group Chemical group C1(=CC=CCC1)* 0.000 description 1
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 125000004987 dibenzofuryl group Chemical group C1(=CC=CC=2OC3=C(C21)C=CC=C3)* 0.000 description 1
- 125000005509 dibenzothiophenyl group Chemical group 0.000 description 1
- 125000005046 dihydronaphthyl group Chemical group 0.000 description 1
- PPSZHCXTGRHULJ-UHFFFAOYSA-N dioxazine Chemical compound O1ON=CC=C1 PPSZHCXTGRHULJ-UHFFFAOYSA-N 0.000 description 1
- 238000003618 dip coating Methods 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
- 238000000921 elemental analysis Methods 0.000 description 1
- ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 1
- 238000004134 energy conservation Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- OGPBJKLSAFTDLK-UHFFFAOYSA-N europium atom Chemical compound [Eu] OGPBJKLSAFTDLK-UHFFFAOYSA-N 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 150000002219 fluoranthenes Chemical class 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
- 150000002220 fluorenes Chemical class 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 238000011010 flushing procedure Methods 0.000 description 1
- 150000002240 furans Chemical class 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- LHJOPRPDWDXEIY-UHFFFAOYSA-N indium lithium Chemical compound [Li].[In] LHJOPRPDWDXEIY-UHFFFAOYSA-N 0.000 description 1
- YZASAXHKAQYPEH-UHFFFAOYSA-N indium silver Chemical compound [Ag].[In] YZASAXHKAQYPEH-UHFFFAOYSA-N 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- 239000011229 interlayer Substances 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- GCICAPWZNUIIDV-UHFFFAOYSA-N lithium magnesium Chemical compound [Li].[Mg] GCICAPWZNUIIDV-UHFFFAOYSA-N 0.000 description 1
- IDBFBDSKYCUNPW-UHFFFAOYSA-N lithium nitride Chemical compound [Li]N([Li])[Li] IDBFBDSKYCUNPW-UHFFFAOYSA-N 0.000 description 1
- FUJCRWPEOMXPAD-UHFFFAOYSA-N lithium oxide Chemical compound [Li+].[Li+].[O-2] FUJCRWPEOMXPAD-UHFFFAOYSA-N 0.000 description 1
- 229910001947 lithium oxide Inorganic materials 0.000 description 1
- SKEDXQSRJSUMRP-UHFFFAOYSA-N lithium;quinolin-8-ol Chemical compound [Li].C1=CN=C2C(O)=CC=CC2=C1 SKEDXQSRJSUMRP-UHFFFAOYSA-N 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- ORUIBWPALBXDOA-UHFFFAOYSA-L magnesium fluoride Chemical compound [F-].[F-].[Mg+2] ORUIBWPALBXDOA-UHFFFAOYSA-L 0.000 description 1
- 229910001635 magnesium fluoride Inorganic materials 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 239000007769 metal material Substances 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 150000002964 pentacenes Chemical class 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 150000002987 phenanthrenes Chemical class 0.000 description 1
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 1
- 150000005041 phenanthrolines Chemical class 0.000 description 1
- 125000004437 phosphorous atom Chemical group 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 108091008695 photoreceptors Proteins 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound 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
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920006254 polymer film Polymers 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 150000003220 pyrenes Chemical class 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000001567 quinoxalinyl group Chemical class N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- 229910001404 rare earth metal oxide Inorganic materials 0.000 description 1
- 150000002910 rare earth metals Chemical class 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229910052701 rubidium Inorganic materials 0.000 description 1
- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 description 1
- KZUNJOHGWZRPMI-UHFFFAOYSA-N samarium atom Chemical compound [Sm] KZUNJOHGWZRPMI-UHFFFAOYSA-N 0.000 description 1
- 229910052706 scandium Inorganic materials 0.000 description 1
- SIXSYDAISGFNSX-UHFFFAOYSA-N scandium atom Chemical compound [Sc] SIXSYDAISGFNSX-UHFFFAOYSA-N 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- 125000005017 substituted alkenyl group Chemical group 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
- GZCRRIHWUXGPOV-UHFFFAOYSA-N terbium atom Chemical compound [Tb] GZCRRIHWUXGPOV-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- 150000003557 thiazoles Chemical class 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 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
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
- C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
- C07D263/56—Benzoxazoles; Hydrogenated benzoxazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
- C07D263/57—Aryl or substituted aryl radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B59/00—Introduction of isotopes of elements into organic compounds ; Labelled organic compounds per se
- C07B59/002—Heterocyclic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/18—Benzimidazoles; Hydrogenated benzimidazoles with aryl radicals directly attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
- C07D263/60—Naphthoxazoles; Hydrogenated naphthoxazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/64—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2
- C07D277/66—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2 with aromatic rings or ring systems directly attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/10—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
- H10K50/16—Electron transporting layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/18—Carrier blocking layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/624—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing six or more rings
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/05—Isotopically modified compounds, e.g. labelled
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1011—Condensed systems
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
- C09K2211/1033—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with oxygen
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
- C09K2211/1037—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with sulfur
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
- C09K2211/1048—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms with oxygen
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
- C09K2211/1051—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms with sulfur
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms
- C09K2211/1062—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms with oxygen
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1092—Heterocyclic compounds characterised by ligands containing sulfur as the only heteroatom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
本发明提供一种含氮杂环有机化合物及其有机发光器件。本发明化合物以含有烷基或稠合脂环的亚芳基作为桥连,一侧连接芴类基团,另一侧连接噁唑类、噻唑类或咪唑类基团。该类化合物具有合适的LUMO值,与相邻层级间具有合适的能级水平,有利于电子的注入和迁移,能够有效降低驱动电压,同时具有较高的电子迁移速率,能够在有机发光器件中实现良好的发光效率。本发明化合物应用于电子传输层和/或空穴阻挡层中,可以提高器件的发光效率,并且可以提高器件的使用寿命,从而增强器件的耐久性。可广泛应用于信息显示技术领域,如手机、平板电脑、电视、可穿戴设备、VR、车辆显示器和车尾灯等。
Description
技术领域
本发明涉及有机光电材料技术领域,尤其涉及一种含氮杂环有机化合物及其有机发光器件。
背景技术
有机发光二极管(Organic Light-Emitting Diodes,OLEDs)又称为有机发光半导体,是新一代的全固态平板显示技术,目前已经逐步进入日常的生活之中,如智能手机,智能手表,便携式笔记本等等,均已经采用了OLED显示技术。与其它显示技术相比,OLED显示技术具有节能、响应速度快、颜色稳定、环境适应性强、无辐射、质量轻、厚度薄、器件制程相对简单等特点。OLED较以往显示技术更显著的特点是可以制造弯折或卷曲的显示屏幕,所以开发合适的有机薄膜材料一直是OLED行业的研究重点。
目前对OLED的研究已经十分深入,通常的OLED的器件结构是在阳极和阴极间加入有机功能层,这些功能层包括空穴注入层,空穴传输层,发光区,电子传输层,电子注入层,覆盖层。有时为了平衡电子或空穴的传输速率,还会空穴传输层与发光层之间加入电子阻挡层,或在电子传输层与发光层间加入空穴阻挡层。通过一定的能级搭配,可以使空穴和电子聚集于发光主体层内发生碰撞,使发光材料激发发光。
在OLED材料中,一般电子的迁移率要比空穴迁移率低2-3个数量级,在OLED发光主体层内空穴的数量远远大于电子的数量。因此,发展高效的电子传输材料对提高有机发光器件的发光效率是非常重要的。理想的电子传输材料应具有较高的电子迁移率,合适的LUMO值,相对较高的电子亲和能力等条件。为了满足市场应用的要求,OLED器件的发光效率、驱动电压、使用寿命等性能还需要进一步加强和改进。
发明内容
本发明的目的在于,在现有技术的基础上,以产业化为目标,提供一种含氮杂环有机化合物及其有机发光器件,使用该含氮杂环有机化合物制备的有机发光器件,应用于电子传输层或空穴阻挡层来开发具有高效率和长寿命的有机发光器件,其分子结构通式如式Ⅰ所示:
其中,L选自如下基团中的一种:
所述至少一个R选自取代或未取代的C1~C12的烷基、取代或未取代的C2~C30的烯基中的任意一种,或者相邻的两个R之间可以相互结合形成取代或未取代的三至八元的脂族环;其余R选自氢、氘、氚;
所述X相同或不同的选自CR'或N,且至少一个X选自N;
R'选自氢、氘、氚;
所述q1选自0、1、2、3或4;所述q2选自0、1、2、3、4、5或6;
所述Z选自O、S或N(Ry)中的任意一种;所述Ry选自氢、氘、取代或未取代的C1~C12的烷基、取代或未取代的C3~C12的环烷基、取代或未取代的C6~C30的芳基、取代或未取代的C2~C30的杂芳基中的任意一种;
所述Y相同或不同的选自CH或N;
所述R1、R2相互独立地选自氢、氘、氚、取代或未取代的C1~C12的烷基、取代或未取代的C3~C12的环烷基、取代或未取代的C6~C30的芳基、取代或未取代的C6~C30的芳香族环与C3~C30的脂肪族环的稠环基、取代或未取代的C2~C30的杂芳基中的任意一种,或R1、R2之间可以相互结合形成取代或未取代的螺环;R1、R2中的任意一者可以直接与桥连L键合;
所述Ra、Rb独立地选自氢、氘、氚、氰基、卤素原子、取代或未取代的C1~C12的烷基、取代或未取代的C3~C12的环烷基、取代或未取代的C3~C12的杂环烷基、取代或未取代的C6~C30的芳基、取代或未取代的C2~C30的杂芳基中的任意一种;或相邻的两个Ra之间可以连接形成取代或未取代的芳环或脂族环;或相邻的两个Rb之间可以连接形成取代或未取代的芳环或脂族环;
所述a1选自0、1、2、3或4;所述a2选自0、1、2、3或4;所述b选自0、1、2、3或4。
本发明提供一种有机发光器件,包括阳极、阴极、有机物层,所述有机物层位于所述阳极与所述阴极之间,所述有机物层包含电子传输层,所述电子传输层中含有本发明所述的含氮杂环有机化合物中的任意一种或至少两种的组合。
本发明还提供一种有机发光器件,所述有机物层包含空穴阻挡层,所述空穴阻挡层中含有本发明所述的含氮杂环有机化合物中的任意一种或至少两种的组合。
本发明的有益效果:
本发明提供一种含氮杂环有机化合物及其有机发光器件,本发明化合物以含有烷基或稠合有脂环的亚芳基作为桥连,一侧连接芴类基团,另一侧连接噁唑类、噻唑类或咪唑类基团。一方面该类化合物含有烷基基团,增强了化合物的溶解性,利于成膜,具有良好的成膜性和热稳定性。另一方面该类化合物具有合适的LUMO值,与相邻层级间具有合适的能级水平,有利于电子的注入和迁移,能够有效降低驱动电压,同时具有较高的电子迁移速率,能够在有机发光器件中实现良好的发光效率。本发明化合物应用于电子传输层和/或空穴阻挡层中,可以提高器件的发光效率,并且可以提高器件的使用寿命,从而增强器件的耐久性。
具体实施方式
下面将结合本发明实施例的技术方案进行清楚、完整地描述,显然,所描述的实施例仅仅是本发明一部分实施例,而不是全部的实施例。基于本发明中的实施例,本领域技术人员在没有做出创造性劳动前提下所获得的所有其他实施例,都属于本发明的保护范围。
在本说明书中,当取代基在芳香环上的位置不固定时,表示其可连接于所述芳香环的相应可选位点中的任一个。例如,可表示/>以此类推。
在本说明书中,当取代基或连接位点所在键贯穿于两个或多个环时,表明其可连接于所述两个或两个环的任一个,具体可连接于所述环的相应可选位点中的任一个。例如,可表示/> 可表示/>以此类推。
本发明所述的卤素是指氟、氯、溴和碘。
本发明所述的烷基是指烷烃分子中少掉一个氢原子而成的烃基,其可以为直链烷基、支链烷基,优选具有1至15个碳原子,更优选1至12个碳原子,特别优选1至6个碳原子。所述直链烷基包括甲基、乙基、正丙基、正丁基、正戊基、正己基、正庚基、正辛基、正壬基、正癸基、十一烷基、十二烷基等,但不限于此;所述支链烷基包括异丙基、异丁基、仲丁基、叔丁基、正戊基的异构基团、正己基的异构基团、正庚基的异构基团、正辛基的异构基团、正壬基的异构基团、正癸基的异构基团等,但不限于此。上述烷基优选为甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基。
本发明所述的碳原子数大于三的链状烷基包括其异构体,例如,丙基包括正丙基、异丙基,丁基包括正丁基、仲丁基、异丁基、叔丁基。以此类推。
本发明所述的环烷基是指环烷烃分子中少掉一个氢原子而成的烃基,优选具有3至15个碳原子,更优选3至12个碳原子,特别优选3至6个碳原子,实例可包括环丙基、环丁基、环戊基、环己基、金刚烷基、莰烷基、降冰片烷基等,但不限于此。上述环烷基优选为环戊基、环己基、1-金刚烷基、2-金刚烷基、降冰片烷基。
本发明所述的杂环烷基是指环烷基中的至少一个母核碳原子被杂原子取代的一价基团。所述杂原子包括但不限于如下所述原子,N、O、S、Si、B、P等。优选具有3至30个碳原子,进一步优选为3至15个碳原子,还优选为3至10个碳原子。所述杂环烷基的实例包括但不限于如下所述的基团,氮丙啶基、氮杂环丁烷基、吡咯烷基、哌啶基、氮杂环庚烷基、高哌啶基、吗啉基、硫代吗啉基、哌嗪基、噁唑烷基、噻唑烷基、咪唑烷基等。
本发明所述的芳基是指芳香族化合物分子的芳核碳上去掉一个氢原子后,剩下一价基团的总称,其可以为单环芳基、多环芳基或者稠环芳基,优选具有6至25个碳原子,更优选6至20个碳原子,特别优选6至14个碳原子,最优选6至12个碳原子。所述单环芳基是指分子中只有一个芳香环的芳基,例如,苯基等,但不限于此;所述多环芳基是指分子中含有两个或者两个以上独立芳香环的芳基,例如,联苯基、三联苯基等,但不限于此;所述稠环芳基是指分子中含有两个或者多个芳香环且彼此间通过共用两个相邻碳原子稠合而成的芳基,例如,萘基、蒽基、菲基、芘基、苝基、芴基、苯并芴基、三亚苯基、荧蒽基、螺二芴基等,但不限于此。上述芳基优选为苯基、联苯基、三联苯基、萘基(优选2-萘基)、蒽基(优选2-蒽基)、菲基、芘基、苝基、芴基、苯并芴基、三亚苯基、螺二芴基。
本发明所述的杂芳基是指芳基中的一个或多个芳核碳原子被杂原子替代得到的基团的总称,所述杂原子包括但不限于氧、硫、氮或者磷原子,优选具有1至25个碳原子,更优选2至20个碳原子,特别优选3至15个碳原子,最优选3至12个碳原子,所述杂芳基的连接位点可以位于成环碳原子上,也可以位于成环氮原子上,所述杂芳基可以为单环杂芳基、多环杂芳基或者稠环杂芳基。所述单环杂芳基包括吡啶基、嘧啶基、三嗪基、呋喃基、噻吩基、吡咯基、咪唑基等,但不限于此;所述多环杂芳基包括联吡啶基、联嘧啶基、苯基吡啶基等,但不限于此;所述稠环杂芳基包括喹啉基、异喹啉基、吲哚基、苯并噻吩基、苯并呋喃基、苯并噁唑基、苯并咪唑基、苯并噻唑基、二苯并呋喃基、苯并二苯并呋喃基、二苯并噻吩基、苯并二苯并噻吩基、咔唑基、苯并咔唑基、吖啶基、9,10-二氢吖啶基、吩噁嗪基、吩噻嗪基、吩噁噻基等,但不限于此。上述杂芳基优选为吡啶基、嘧啶基、噻吩基、呋喃基、苯并噻吩基、苯并呋喃基、苯并噁唑基、苯并咪唑基、苯并噻唑基、二苯并呋喃基、二苯并噻吩基、苯并二苯并噻吩基、苯并二苯并呋喃基、咔唑基、吖啶基、吩噁嗪基、吩噻嗪基、吩噁噻基。
本发明所述的烯基是指烯烃分子中去掉一个氢原子得到的一价基团,所述烯基包括单烯基、二烯基、多烯基等。优选具有2至60个碳原子,更优选2至30个碳原子,特别优选2至15个碳原子,最优选2至6个碳原子。所述烯基的实例包括乙烯基、丁二烯基等,但不限于此。上述烯基优选为乙烯基。
本发明所述的碳原子数大于三的烯基包括其异构体,例如,丙烯基包括1-丙烯基或2-丙烯基,丁烯基包括1-丁烯基、2-丁烯基、或3-丁烯基,戊烯基包括1-戊烯基、2-戊烯基、3-戊烯基、4-戊烯基,己烯基包括1-己烯基、2-己烯基、3-己烯基、4-己烯基、5-己烯基。以此类推。
本发明所述“取代的…”诸如取代的烷基、取代的环烷基、取代的杂环烷基、取代的烯基、取代的芳基、取代的杂芳基等是指被独立地选自氘基、取代或未取代的C1~C6烷基、取代或未取代的C3~C6环烷基、取代或未取代的C6~C20芳基、取代或未取代的C2~C15杂芳基、取代或未取代的胺基等但不限于此的基团单取代或多取代,优选被选自氘、氚、甲基、乙基、异丙基、叔丁基、苯基、联苯基、三联苯基、萘基、蒽基、菲基、苯并菲基、苝基、芘基、苯甲基、甲苯基、芴基、9,9-二甲基芴基、9,9-二苯基芴基、9-甲基-9-苯基芴基、二苯胺基、二甲胺基、咔唑基、9-苯基咔唑基、吖啶基、呋喃基、噻吩基、苯并呋喃基、苯并噻吩基、苯并噁唑基、苯并咪唑基、苯并噻唑基、二苯并呋喃基、二苯并噻吩基、吩噻嗪基、吩噁嗪基、吲哚基的基团单取代或多取代。另外,上述取代基还可被一个或多个氘、氚、卤原子、氰基、烷基、环烷基、芳基所述的取代基取代。
本发明所述的脂族是指具有1至60个碳原子的脂族烃,可以是完全不饱和或者部分不饱和。
本发明所述的脂族环是指具有脂肪族性质的环烃,分子中含有闭合的碳环,可以是3-18个优选3-12个、更优选3-7个碳原子形成的单环烃或多环烃,可以是完全饱和或者部分饱和,例如环丙烷、环丁烷、环戊烷、环己烷、环庚烷、环戊烯、环己烯、环庚烯等,但不限于此。多个单环烃还可用多种方式连接:分子中两个环可以共用一个碳原子形成螺环;环上两个碳原子之间可以用碳桥连接形成桥环;几个环也可以互相连接形成笼状结构。
除非另有说明,否则本文所用的术语“环”是指由具有3至60个碳原子的脂族环或具有6至60个碳原子的芳族环或具有2至60个碳原子的杂环或其组合组成的稠合环,它包含饱和或不饱和环。
本发明所述的键合起来形成环状结构是指两个基团通过化学键彼此连接并任选地进行芳构化。如下所示例:
本发明中,连接形成的环可以为五元环或六元环或者稠合环,例如苯、萘、芴、环戊烯、环戊烷、环己烷、环己烯、环己烷并苯、喹啉、异喹啉、二苯并噻吩、菲或芘,但不限于此。
本发明提供了一种含氮杂环有机化合物,其分子结构通式如式Ⅰ所示:
本发明的目的在于,在现有技术的基础上,以产业化为目标,提供一种含氮杂环有机化合物及其有机发光器件,使用该含氮杂环有机化合物制备的有机发光器件,应用于电子传输层或空穴阻挡层来开发具有高效率和长寿命的有机发光器件,其分子结构通式如式Ⅰ所示:
其中,L选自如下基团中的一种:
所述至少一个R选自取代或未取代的C1~C12的烷基、取代或未取代的C2~C30的烯基中的任意一种,或者相邻的两个R之间可以相互结合形成取代或未取代的三至八元的脂族环;其余R选自氢、氘、氚;
所述X相同或不同的选自CR'或N,且至少一个X选自N;
R'选自氢、氘、氚;
所述q1选自0、1、2、3或4;所述q2选自0、1、2、3、4、5或6;
所述Z选自O、S或N(Ry)中的任意一种;所述Ry选自氢、氘、取代或未取代的C1~C12的烷基、取代或未取代的C3~C12的环烷基、取代或未取代的C6~C30的芳基、取代或未取代的C2~C30的杂芳基中的任意一种;
所述Y相同或不同的选自CH或N;
所述R1、R2相互独立地选自氢、氘、氚、取代或未取代的C1~C12的烷基、取代或未取代的C3~C12的环烷基、取代或未取代的C6~C30的芳基、取代或未取代的C6~C30的芳香族环与C3~C30的脂肪族环的稠环基、取代或未取代的C2~C30的杂芳基中的任意一种,或R1、R2之间可以相互结合形成取代或未取代的螺环;R1、R2中的任意一者可以直接与桥连L键合;
所述Ra、Rb独立地选自氢、氘、氚、氰基、卤素原子、取代或未取代的C1~C12的烷基、取代或未取代的C3~C12的环烷基、取代或未取代的C3~C12的杂环烷基、取代或未取代的C6~C30的芳基、取代或未取代的C2~C30的杂芳基中的任意一种;或相邻的两个Ra之间可以连接形成取代或未取代的芳环或脂族环;或相邻的两个Rb之间可以连接形成取代或未取代的芳环或脂族环;
所述a1选自0、1、2、3或4;所述a2选自0、1、2、3或4;所述b选自0、1、2、3或4。
优选的,所述L选自下示基团中的一种:
所述至少一个R选自取代或未取代的如下基团中的一种:甲基、乙基、丙基、丁基、戊基、己基、庚基、辛基、乙烯基、丙烯基、丁烯基、戊烯基、己烯基、环丁烯基、环戊烯基、环己烯基、丁二烯基、环戊二烯基、环已二烯基;其余R选自氢、氘、氚中的一种或多种,R在被多个取代基取代的情况下,多个取代基彼此相同或不同;
所述q0选自0、1或2;所述q1选自0、1、2、3或4;所述q2选自0、1、2、3、4、5或6;所述q3选自0、1、2或3;
所述s1选自0、1或2;s2选自0、1、2、3或4;s3选自0、1、2、3、4、5或6;s4选自0、1、2、3、4、5、6、7或8;s5选自0、1、2、3、4、5、6、7、8、9或10;s6选自0、1、2、3、4、5、6、7、8、9、10、11或12。
优选的,所述至少一个R选自取代或未取代的如下基团中的一种:甲基、乙基、丙基、丁基、戊基、己基、庚基、乙烯基、丙烯基、丁烯基、环丁烯基、环戊烯基、环己烯基;其余R选自氢、氘、氚中的一种或多种,其中所述“取代或未取代的”中的取代基选自氘、氚、甲基、乙基、丙基、丁基、戊基、己基、庚基中的一种或多种,R在被多个取代基取代的情况下,多个取代基彼此相同或不同。
更优选的,所述至少一个R选自取代或未取代的如下基团中的一种:甲基、乙基、丙基、丁基、戊基、己基、庚基、乙烯基、丙烯基、丁烯基;其余R选自氢、氘、氚中的一种或多种;其中所述“取代或未取代的”中的取代基选自氘或氚。
优选的,所述“至少一个”包括一个、两个、三个、四个、五个、六个、七个、八个、九个、十个、十一个或十二个。
优选的,所述“至少一个”包括至少一个、至少两个、至少三个、至少四个、至少五个或至少六个。
优选的,所述“至少一个”包括至多七个、至多八个、至多九个、至多十个、至多十一个或至多十二个。
优选的,所述中Rb彼此相同或不同,并且独立地选自氢、氘、氚或者取代或未取代的如下基团中的一种:甲基、乙基、丙基、丁基、戊基、己基、庚基、辛基、环丙基、环丁基、环戊基、环己基、环庚基、环辛基、金刚烷基、坎烷基、降冰片烷基、苯基、联苯基、萘基、蒽基、菲基、三亚苯基、氰基、氟基、吡啶基、嘧啶基、哒嗪基、吡嗪基、三嗪基、苯并环戊烷基、苯并环己烷基、苯并环戊烯基、苯并环己烯基、氮丙啶基、氮杂环丁烷基、吡咯烷基、哌啶基、吗啉基、硫代吗啉基、哌嗪基、恶唑烷基、噻唑烷基、咪唑烷基中的一种;或相邻的两个Rb之间可以连接形成苯环、萘环或三至八元的脂族环;其中所述“取代或未取代的”中的取代基选自氘、氚、甲基、乙基、丙基、异丙基、丁基、叔丁基、戊基、己基、庚基、辛基、环丙基、环丁基、环戊基、环己基、环庚基、环辛基、金刚烷基、坎烷基、降冰片烷基、苯基、联苯基、萘基中的一种或多种,在被多个取代基取代的情况下,多个取代基彼此相同或不同。
更优选的,所述选自如下所示基团中的任意一种:
/>
优选的,所述R1、R2独立地选自氢、氘、氚、取代或未取代的下列基团中的任意一种:C1~C6的烷基,C3~C6的环烷基,金刚烷基,降冰片烷基、C6~C12的芳基、C2~C12的杂芳基、苯并环戊烷基、苯并环己烷基、苯并环戊烯基、苯并环己烯基、萘并环戊烷基、萘并环己烷基、萘并环戊烯基、萘并环己烯基;所述“取代或未取代的”取代基团可以为氘、氚、C1~C12的烷基、C3~C12的环烷基中的任意一种或一种以上;
或者所述R1、R2可以形成下列螺环结构中的任意一种:
所述Rp选自氢、氘、氚或取代或未取代的如下基团:甲基、乙基、正丙基、正丁基、异丙基、叔丁基、环己基、环戊基、环丁基、环丙基、金刚烷基、降冰片烷基、坎烷基、苯基、萘基、联苯基、三联苯基、蒽基、菲基、三亚苯基、二苯并呋喃基、二苯并噻吩基、9,9-二甲基芴基、9,9-二苯基芴基、螺芴基、9-苯基咔唑基,取代基为氘、氚、甲基、乙基、正丙基、正丁基、正戊基、正己基、异丙基、叔丁基、环己基、环戊基、环丁基、环丙基、金刚烷基、降冰片烷基、苯基、萘基、甲苯基、联苯基、三联苯基、氘代异丙基、氘代叔丁基、氘代环己基、氘代环戊基、氘代环丁基、氘代环丙基、氘代金刚烷基、氘代降冰片烷基、氘代苯基、氘代萘基、氘代联苯基中的一个或多个取代,或者相邻Rp可以键合起来形成苯环或萘环;
所述Ar选自异丙基、叔丁基、环己基、环戊基、苯基、萘基、甲苯基、联苯基、三联苯基、氘代苯基、氘代萘基、氘代联苯基、氘代三联苯基中的一种;
所述p1选自0、1或2;p2选自0、1、2、3或4;p3选自0、1、2、3、4、5或6;p4选自0、1、2、3、4、5、6、7或8;p5选自0、1、2、3、4、5、6、7、8、9或10;p6选自0、1、2、3、4、5、6、7、8、9、10、11或12;p7选自0、1、2、3、4、5、6、7、8、9、10、11、12、13或14。
优选的,所述选自如下所示基团中的任意一种:
/>
所述a选自0、1、2或3;b选自0、1、2、3或4;c选自0、1、2、3、4或5;e选自0、1、2、3、4、5或6;d选自0、1、2、3、4、5、6或7;f选自0、1、2、3、4、5、6、7、8或9;g选自0、1、2、3、4、5、6、7、8、9或10;h选自0、1、2、3、4、5、6、7或8;i选自0、1、2、3、4、5、6、7、8、9、10或11。
优选的,所述Ra、Rb独立地选自氘、氚、甲基、乙基、正丙基、正丁基、异丙基、叔丁基、环己基、环戊基、环丁基、环丙基、金刚烷基、降冰片烷基、苯基、萘基、蒽基、菲基、三亚苯基、二苯并呋喃基、二苯并噻吩基、9,9-二甲基芴基、9,9-二苯基芴基、螺芴基、9-苯基咔唑基、四氢萘基、二氢萘基、茚满基、茚基、吡咯烷基、哌啶基、吗啉基、硫代吗啉基、哌嗪基、恶唑烷基、噻唑烷基、咪唑烷基,并且以上基团还可被氘、氚、甲基、乙基、正丙基、正丁基、异丙基、叔丁基、环己基、环戊基、环丁基、环丙基、金刚烷基、降冰片烷基、苯基、萘基、甲苯基、联苯基、三联苯基、氘代异丙基、氘代叔丁基、氘代环己基、氘代环戊基、氘代环丁基、氘代环丙基、氘代金刚烷基、氘代降冰片烷基、氘代苯基、氘代萘基、氘代联苯基、吡咯烷基、哌啶基、吗啉基、硫代吗啉基、哌嗪基、恶唑烷基、噻唑烷基、咪唑烷基中的一个或多个取代。
优选的,所述Ra、Rb独立地选自氢、氘、氚、甲基、乙基、正丙基、正丁基、异丙基、叔丁基、环己基、环戊基、环丁基、环丙基、金刚烷基、降冰片烷基、氘代异丙基、氘代叔丁基、氘代环己基、氘代环戊基、氘代环丁基、氘代环丙基、氘代金刚烷基、氘代降冰片烷基或如下所示基团中的一种:
最优选的,所述含氮杂环有机化合物选自如下所示化学结构中的任意一种:
/>
/>
/>
/>
/>
/>
/>
/>
/>
/>
/>
本发明式I所述的含氮杂环有机化合物的制备方法,可通过本领域常规的偶联反应即可制备得到,例如可通过如下合成路线制备得到,但本发明不限于此:
在氮气气氛下,卤素化合物a与联硼酸頻那醇脂通过Miyaura硼化反应反应得到中间体A,中间体A与双卤素化合物b通过Suzuki反应得到中间体B,再与联硼酸頻那醇脂通过Miyaura硼化反应反应得到中间体C,中间体C再与卤素化合物c反应,并在相应的催化剂、有机碱、配体、溶液以及相应温度下反应获得式Ⅰ相应化合物,其中X0、X1、X2、X3选自Cl、Br或I。
本发明对上述各类反应中所采用的原料的来源没有特别的限制,可以使用市售产品原料或采用本领域技术人员所熟知的制备方法得到。本发明对上述反应没有特殊的限制,采用本领域技术人员所熟知的常规反应即可。本发明所述化合物合成步骤少、方法简单,有利于工业化生产。
本发明还提供一种有机发光器件,包括阳极、阴极、有机物层,所述有机物层位于所述阳极与所述阴极之间,所述有机物层包含电子传输层,所述电子传输层中含有本发明所述的含氮杂环有机化合物中的任意一种或至少两种的组合。
优选的,所述有机物层包含空穴阻挡层,所述空穴阻挡层中含有本发明所述的含氮杂环有机化合物中的任意一种或至少两种的组合。
本发明的发光器件通常在基板上形成。上述基板只要在形成电极、形成有机物层时不发生变化即可,例如,玻璃、塑料、高分子薄膜、硅等的基板。当基板不透明时,与其相对的电极优选为透明或者半透明的。
本发明有机发光器件的阳极可以通过在基板上溅射或者沉积用作第一电极的材料的方式来形成。阳极可以采用铟锡氧(ITO)、铟锌氧(IZO)、二氧化锡(SnO2)、氧化锌(ZnO)等氧化物透明导电材料和它们的任意组合。第一电极作为阴极时,可以采用镁(Mg)、银(Ag)、铝(Al)、铝-锂(Al-Li)、钙(Ca)、镁-铟(Mg-In)、镁-银(Mg-Ag)等金属或合金以及它们之间的任意组合。
本发明有机发光器件的空穴传输层和空穴注入层,所需材料具有很好的空穴传输性能,能够有效地把空穴从阳极传输到发光层上。可以包括其他小分子和高分子有机化合物,包括但不限于咔唑类化合物、三芳香胺化合物、联苯二胺化合物、芴类化合物、酞菁类化合物、六氰基六杂三苯、2,3,5,6-四氟-7,7',8,8'-四氰二甲基对苯醌(F4-TCNQ)、聚乙烯基咔唑、聚噻吩、聚乙烯或聚苯磺酸。
本发明的有机发光器件的发光层,具有很好的发光特性,可以根据需要调节可见光的范围。可以选择如下化合物,但是不限于此,萘类化合物,芘类化合物,芴类化合物,菲类化合物,类化合物,荧蒽类化合物,蒽类化合物,并五苯类化合物,苝类化合物,二芳乙烯类化合物,三苯胺乙烯类化合物,胺类化合物,苯并咪唑类化合物,呋喃类化合物,有机金属螯合物。关于本发明有机发光器件的发光层,发光材料可使用红色发光材料、绿色发光材料、或蓝色发光材料,如果需要,也可将两种或更多种发光材料进行混合使用。此外,作为发光材料,可以仅为主体材料,也可以是主体材料和掺杂材料的混合物,优选发光层由主体材料和掺杂材料混合使用。
本发明有机发光器件的电子传输材料要求具有很好的电子传输性能,能够有效地把电子从阴极传输到发光层中,具有很大的电子迁移率。除本发明的具有结构式I化合物外,还可以含有如下化合物,但是不限于此,氧杂恶唑、噻唑类化合物、三氮唑类化合物、三氮嗪类化合物、三氮杂苯类化合物、喔啉类化合物、二氮蒽类化合物、含硅杂环类化合物、喹啉类化合物、菲啰啉类化合物、金属螯合物(如Alq3)、氟取代苯类化合物、苯并咪唑类化合物。
本发明有机发光器件的电子注入层,可以有效的把电子从阴极注入到有机层中,主要选自碱金属或者碱金属的化合物,或选自碱土金属或者碱土金属的化合物或者碱金属络合物,可以选择如下化合物,但是不限于此,碱金属、碱土金属、稀土金属、碱金属的氧化物或者卤化物、碱土金属的氧化物或者卤化物、稀土金属的氧化物或者卤化物、碱金属或者碱土金属的有机络合物;优选为锂、氟化锂、氧化锂、氮化锂、8-羟基喹啉锂、铯、碳酸铯、8-羟基喹啉铯、钙、氟化钙、氧化钙、镁、氟化镁、碳酸镁、氧化镁,这些化合物可以单独使用也可以混合物使用,也可以跟其他有机电致发光材料配合使用。
本发明有机发光器件的阴极材料,为了将电子注入到电子注入/输送层或者发光层,通常优选功函数小的金属材料。可以使用例如,锂、钠、钾、铷、铯、铍、镁、钙、锶、钡、铝、钪、钒、锌、钇、铟、铈、钐、铕、铽、镱等金属以及它们中的2种以上形成的合金、或者它们中的1种以上与金、银、铂、铜、锰、钛、钴、镍、钨、锡中的1种以上形成的合金、石墨或者石墨层间化合物等。作为合金,可举出镁-银合金、镁-铟合金、镁-铝合金、铟-银合金、锂-铝合金、锂-镁合金、锂-铟合金、钙-铝合金等。
本发明有机发光器件的覆盖层材料是为了减少OLED器件中的全发射损失和波导损失,提高光取出效率。本发明的覆盖层材料可采用Alq3、TPBi等本领域技术人员所熟知的常规的覆盖层材料或本发明所述的所述的含氮杂环有机化合物任意一种或至少两种的组合。
作为空穴传输层和电子传输层的膜厚,其最佳可根据所用的材料而不同,只要按照能使驱动电压和发光效率达到适度的值的条件来选择即可,但是必须至少不会导致发生针孔的厚度,如果过厚,则器件的驱动电压提高,是不理想的。因此该空穴传输层和电子传输层的膜厚例如为1nm~1um,优选为2nm~500nm,更优选为5nm~200nm。本发明的有机发光器件有机层的总厚度为1~1000nm,优选为50~500nm。
本发明的有机发光器件中有机层的每一层,可以通过真空蒸镀法、分子束蒸镀法、溶于溶剂的浸涂法、旋涂法、棒涂法或者喷墨打印等方式制备。对于金属电机可以使用蒸镀法或者溅射法进行制备,在本发明中优选采用真空蒸镀的方法。
本发明的有机发光器件可广泛应用于信息显示技术、照明光源、柔性OLED、电子纸、有机太阳能电池、有机感光体或有机薄膜晶体管、指示牌、信号灯等领域。信息显示方面被广泛应用于各种信息显示,如手机、平板电脑、电视、可穿戴设备、VR、智能手表、数码相机、车辆显示器和车尾灯等。
通过以下实施例,更详尽地解释本发明,但不希望因此限制本发明。在该描述的基础上,本领域普通技术人员将能够在不付出创造性劳动的情况下,在所公开的整个范围内实施本发明和制备根据本发明的其他化合物和器件。
原料、试剂以及表征设备的说明:
本发明对以下实施例中所采用的原料来源没有特别的限制,可以为市售产品或采用本领域技术人员所熟知的制备方法制备得到。
质谱使用英国沃特斯G2-Si四极杆串联飞行时间高分辨质谱仪,氯仿为溶剂;
元素分析使用德国Elementar公司的Vario EL cube型有机元素分析仪,样品质量为5~10mg。
中间体的合成
中间体b-1的制备
合成中间体M-1
在氮气保护下,向反应瓶中加入m-1(22.60g,110mmol),联硼酸频那醇酯(27.93g,110mmol),Pd(PPh3)4(1.27g,1.10mmol)、K2CO3(23.49g,170.00mmol),DMF(500mL),加热反应2小时,反应结束后,加入蒸馏水,用二氯甲烷萃取,分液,用蒸馏水洗涤有机相三次,无水硫酸镁干燥,旋转蒸发浓缩溶剂,降温析晶,抽滤,将所得固体用甲苯:乙醇=4:1重结晶,得到中间体M-1(21.11g,收率76%);HPLC纯度≥98.85%。质谱m/z:252.1075(理论值:252.1088)。
合成中间体b-1
在氮气保护下,向反应瓶中依次加入中间体M-1(18.94g,75mmol)、原料n-1(21.22g,75mmol)、碳酸钾(16.58g,120mmol)、Pd(PPh3)4(1.04g,0.90mmol),加入400mL甲苯/乙醇/水(2:1:1)混合溶剂,搅拌混合物,将上述反应物体系加热回流2小时。反应结束后,冷却至室温,加入甲苯并分离各相,用蒸馏水洗涤甲苯相三次,无水硫酸镁干燥,旋转蒸发浓缩溶剂,降温析晶,抽滤,将所得固体用甲苯:乙醇=20:3重结晶,得到中间体b-1(15.84g,产率75%)。HPLC纯度≥99.53%。质谱m/z:279.9666(理论值:279.9654)。
根据上述方法,将原料m和原料n进行等摩尔的替换,合成了下列中间体b:
/>
[实施例1]化合物1的合成
中间体A-1的制备:
在氮气保护下,向反应瓶中依次加入原料a-1(31.79g,80.00mmol),联硼酸频那醇酯(20.32g,80.00mmol),Pd(PPh3)4(1.15g,1.00mmol)、K2CO3(23.49g,170.00mmol),DMF(400mL),然后加热反应3.5小时,反应结束后,冷却至室温,向其中加入500mL水,然后用乙酸乙酯(500mL×3)萃取,有机层用无水硫酸镁干燥,旋转蒸发除去溶剂,然后用甲苯:乙醇=20:1重结晶,干燥得到中间体A-1(29.51g,收率83%);HPLC纯度≥98.72%。质谱m/z:444.2277(理论值:444.2261)。
中间体B-1的制备:
在氮气保护下,向反应瓶中依次加入中间体A-1(24.44g,55.00mmol)、原料b-1(15.49g,55.00mmol)、Pd(PPh3)4(0.69g,0.60mmol)、K2CO3(11.06g,80.00mmol)以及300mL甲苯、100mL乙醇、100mL水,搅拌混合物,将上述体系加热回流反应3小时;反应结束后,冷却至室温,抽滤得滤饼,并用乙醇冲洗滤饼,最后将滤饼用甲苯重结晶,得到中间体B-1(21.70g,收率76%);HPLC纯度≥99.41%。质谱m/z:518.1819(理论值:518.1801)。
中间体C-1的制备:
在氮气保护下,向反应瓶中依次加入中间体B-1(20.76g,40.00mmol),联硼酸频那醇酯(10.16g,40.00mmol),KOAc(8.83g,90.00mmol),Pd(dppf)Cl2(0.73g,1.00mmol),1,4-二氧六环(350mL),然后加热到回流温度反应4小时,反应结束后,冷却至室温,向其中加入350mL水,然后用乙酸乙酯(500mL×3)萃取,有机层用无水MgSO4干燥,旋蒸除掉乙酸乙酯,然后再使用甲苯重结晶,干燥得到中间体C-1(19.54g,收率80%);HPLC纯度≥99.69%。质谱m/z:610.3032(理论值:610.3043)。
化合物1的制备:
在氮气保护下,向反应瓶中依次加入中间体C-1(15.27g,25.00mmol)、原料c-1(4.95g,25.00mmol)、Pd2(dba)3(0.27g,0.30mmol)、P(t-Bu)3(0.20g,1.00mmol),K2CO3(5.53g,40.00mmol)以及四氢呋喃150mL,搅拌混合物,将上述反应物体系加热回流5小时;反应结束后,冷却至室温,加入水,用二氯甲烷萃取,有机层用无水硫酸镁干燥,过滤,减压除去溶剂,用甲苯重结晶,得到化合物1(11.28g,收率75%);HPLC纯度≥99.89%。质谱m/z:601.2420(理论值:601.2406)。理论元素含量(%)C45H31NO:C,89.82;H,5.19;N,2.33。实测元素含量(%):C,89.87;H,5.13;N,2.35。
[实施例2]化合物5的合成
使用与合成实施例1相同的方法,用等摩尔的a-5替换a-1,等摩尔的b-5替换b-1,合成化合物5(8.82g),HPLC检测固体纯度≧99.90%。质谱m/z:415.1945(理论值:415.1936)。理论元素含量(%)C30H25NO:C,86.71;H,6.06;N,3.37。实测元素含量(%):C,86.74;H,6.02;N,3.40。
[实施例3]化合物14的合成
使用与合成实施例1相同的方法,用等摩尔的a-14替换a-1,等摩尔的b-14替换b-1,等摩尔的c-14替换c-1,合成化合物14(10.28g),HPLC检测固体纯度≧99.78%。质谱m/z:527.2257(理论值:527.2249)。理论元素含量(%)C39H29NO:C,88.77;H,5.54;N,2.65。实测元素含量(%):C,88.82;H,5.50;N,2.69。
[实施例4]化合物29的合成
使用与合成实施例1相同的方法,用等摩尔的a-29替换a-1,等摩尔的b-29替换b-1,等摩尔的c-29替换c-1,合成化合物29(10.66g),HPLC检测固体纯度≧99.83%。质谱m/z:490.3014(理论值:490.3002)。理论元素含量(%)C35H26D7NO:C,85.67;H,8.21;N,2.85。实测元素含量(%):C,85.72;H,8.17;N,2.88。
[实施例5]化合物47的合成
使用与合成实施例1相同的方法,用等摩尔的a-47替换a-1,等摩尔的b-47替换b-1,合成化合物47(12.31g),HPLC检测固体纯度≧99.76%。质谱m/z:648.3180(理论值:648.3189)。理论元素含量(%)C48H32D5NO:C,88.85;H,6.52;N,2.16。实测元素含量(%):C,88.81;H,6.55;N,2.13。
[实施例6]化合物82的合成
使用与合成实施例1相同的方法,用等摩尔的a-82替换a-1,等摩尔的b-29替换b-1,合成化合物82(11.26g),HPLC检测固体纯度≧99.94%。质谱m/z:549.2110(理论值:549.2093)。理论元素含量(%)C41H27NO:C,89.59;H,4.95;N,2.55。实测元素含量(%):C,89.64;H,4.90;N,2.52。
[实施例7]化合物85的合成
使用与合成实施例1相同的方法,用等摩尔的a-85替换a-1,等摩尔的b-85替换b-1,合成化合物85(11.24g),HPLC检测固体纯度≧99.73%。质谱m/z:671.3197(理论值:671.3188)。理论元素含量(%)C50H41NO:C,89.38;H,6.15;N,2.08。实测元素含量(%):C,89.42;H,6.17;N,2.02。
[实施例8]化合物92的合成
使用与合成实施例1相同的方法,用等摩尔的a-92替换a-1,等摩尔的b-92替换b-1,等摩尔的c-92替换c-1,合成化合物92(11.58g),HPLC检测固体纯度≧99.84%。质谱m/z:634.2678(理论值:634.2669)。理论元素含量(%)C46H26D5NO2:C,91.98;H,6.57;N,1.45。实测元素含量(%):C,92.04;H,6.53;N,1.51。
[实施例9]化合物141的合成
使用与合成实施例1相同的方法,用等摩尔的a-141替换a-1,合成化合物141(11.67g),HPLC检测固体纯度≧99.66%。质谱m/z:657.3024(理论值:657.3032)。理论元素含量(%)C49H39NO:C,89.46;H,5.98;N,2.13。实测元素含量(%):C,89.50;H,5.92;N,2.16。
[实施例10]化合物269的合成
使用与合成实施例1相同的方法,用等摩尔的a-269替换a-1,等摩尔的b-269替换b-1,合成化合物269(10.15g),HPLC检测固体纯度≧99.56%。质谱m/z:605.2711(理论值:605.2719)。理论元素含量(%)C45H35NO:C,89.22;H,5.82;N,2.31。实测元素含量(%):C,89.26;H,5.80;N,2.28。
[实施例11]化合物279的合成
使用与合成实施例1相同的方法,用等摩尔的a-279替换a-1,等摩尔的b-279替换b-1,等摩尔的c-279替换c-1,合成化合物279(11.40g),HPLC检测固体纯度≧99.59%。质谱m/z:701.2167(理论值:701.2179)。理论元素含量(%)C53H35NO:C,90.70;H,5.03;N,2.00。实测元素含量(%):C,90.74;H,5.00;N,2.05。
[实施例12]化合物339的合成
使用与合成实施例1相同的方法,用等摩尔的a-339替换a-1,用等摩尔的b-339替换b-1,等摩尔的c-339替换c-1,合成化合物339(11.90g),HPLC检测固体纯度≧99.69%。质谱m/z:670.2996(理论值:670.2984)。理论元素含量(%)C49H38N2O:C,87.73;H,5.71;N,4.18。实测元素含量(%):C,87.78;H,5.66;N,4.15。
[实施例13]化合物341的合成
使用与合成实施例1相同的方法,用等摩尔的a-341替换a-1,等摩尔的b-341替换b-1,合成化合物341(14.00g),HPLC检测固体纯度≧99.91%。质谱m/z:781.4240(理论值:781.4222)。理论元素含量(%)C58H47D4NO:C,89.08;H,7.09;N,1.79。实测元素含量(%):89.12;H,7.05;N,1.81。
[实施例14]化合物394的合成
使用与合成实施例1相同的方法,用等摩尔的a-394替换a-1,等摩尔的b-394替换b-1,等摩尔的c-394替换c-1,合成化合物394(11.65g),HPLC检测固体纯度≧99.73%。质谱m/z:582.2688(理论值:582.2671)。理论元素含量(%)C42H34N2O:C,86.57;H,5.88;N,4.81。实测元素含量(%):C,86.62;H,5.82;N,4.83。
[实施例15]化合物413的合成
使用与合成实施例1相同的方法,用等摩尔的a-413替换a-1,等摩尔的b-413替换b-1,合成化合物413(13.07g),HPLC检测固体纯度≧99.81%。质谱m/z:661.3182(理论值:661.3190)。理论元素含量(%)C49H23D10NO:C,88.92;H,6.55;N,2.12。实测元素含量(%):C,88.96;H,6.51;N,2.10。
[实施例16]化合物461的合成
使用与合成实施例1相同的方法,用等摩尔的a-461替换a-1,等摩尔的b-461替换b-1,等摩尔的c-461替换c-1,合成化合物461(14.91g),HPLC检测固体纯度≧99.87%。质谱m/z:805.3353(理论值:805.3345)。理论元素含量(%)C61H43NO:C,90.90;H,5.38;N,1.74。实测元素含量(%):C,90.95;H,5.34;N,1.72。
[实施例17]化合物477的合成
使用与合成实施例1相同的方法,用等摩尔的a-477替换a-1,等摩尔的b-477替换b-1,合成化合物477(11.46g),HPLC检测固体纯度≧99.85%。质谱m/z:587.3069(理论值:587.3064)。理论元素含量(%)C43H25D8NO:C,87.87;H,7.03;N,2.38。实测元素含量(%):C,87.80;H,7.08;N,2.35。
[实施例18]化合物491的合成
使用与合成实施例1相同的方法,用等摩尔的a-491替换a-1,等摩尔的b-491替换b-1,合成化合物491(11.94g),HPLC检测固体纯度≧99.69%。质谱m/z:604.2462(理论值:604.2453)。理论元素含量(%)C44H24D4N2O:C,87.39;H,5.33;N,4.63。实测元素含量(%):C,87.33;H,5.36;N,4.66。
[实施例19]化合物509的合成
使用与合成实施例1相同的方法,用等摩尔的a-509替换a-1,等摩尔的b-509替换b-1,合成化合物509(13.06g),HPLC检测固体纯度≧99.72%。质谱m/z:705.2789(理论值:705.2780)。理论元素含量(%)C51H35N3O:C,86.78;H,5.00;N,5.95。实测元素含量(%):C,86.82;H,5.02;N,5.89。
[实施例20]化合物522的合成
使用与合成实施例1相同的方法,用等摩尔的a-522替换a-1,等摩尔的b-522替换b-1,等摩尔的c-522替换c-1,合成化合物522(10.59g),HPLC检测固体纯度≧99.92%。质谱m/z:605.2478(理论值:605.2467)。理论元素含量(%)C43H31N3O:C,85.26;H,5.16;N,6.94。实测元素含量(%):C,85.29;H,5.12;N,6.98。
[实施例21]化合物526的合成
使用与合成实施例1相同的方法,用等摩尔的a-526替换a-1,等摩尔的b-526替换b-1,等摩尔的c-526替换c-1,合成化合物526(12.10g),HPLC检测固体纯度≧99.93%。质谱m/z:653.3405(理论值:653.3393)。理论元素含量(%)C47H27D9N2O:C,86.33;H,6.93;N,4.28。实测元素含量(%):C,86.37;H,6.90;N,4.24。
[实施例22]化合物529的合成
使用与合成实施例1相同的方法,用等摩尔的a-529替换a-1,等摩尔的b-529替换b-1,等摩尔的c-529替换c-1,合成化合物529(11.25g),HPLC检测固体纯度≧99.86%。质谱m/z:725.2913(理论值:725.2905)。理论元素含量(%)C50H38F3NO:C,82.74;H,5.28;N,1.93。实测元素含量(%):C,82.78;H,5.23;N,1.97。
[实施例23]化合物550的合成
使用与合成实施例1相同的方法,用等摩尔的a-550替换a-1,等摩尔的b-550替换b-1,等摩尔的c-550替换c-1,合成化合物550(10.64g),HPLC检测固体纯度≧99.63%。质谱m/z:664.2895(理论值:664.2878)。理论元素含量(%)C50H36N2:C,90.33;H,5.46;N,4.21。实测元素含量(%):C,90.38;H,5.42;N,4.25。
[实施例24]化合物569的合成
使用与合成实施例1相同的方法,用等摩尔的a-569替换a-1,等摩尔的b-569替换b-1,等摩尔的c-569替换c-1,合成化合物569(11.17g),HPLC检测固体纯度≧99.74%。质谱m/z:657.2478(理论值:657.2490)。理论元素含量(%)C48H35NS:C,87.63;H,5.36;N,2.13。实测元素含量(%):C,87.67;H,5.32;N,2.10。
[实施例25]化合物666的合成
使用与合成实施例1相同的方法,用等摩尔的a-666替换a-1,等摩尔的b-14替换b-1,等摩尔的c-666替换c-1,合成化合物666(9.71g),HPLC检测固体纯度≧99.64%。质谱m/z:554.2368(理论值:554.2358)。理论元素含量(%)C40H30N2O:C,86.61;H,5.45;N,5.05。实测元素含量(%):C,86.66;H,5.42;N,5.00。
[实施例26]化合物670的合成
使用与合成实施例1相同的方法,用等摩尔的a-670替换a-1,等摩尔的b-14替换b-1,等摩尔的c-670替换c-1,合成化合物670(10.97g),HPLC检测固体纯度≧99.70%。质谱m/z:707.3177(理论值:707.3188)。理论元素含量(%)C53H41NO:C,89.92;H,5.84;N,1.98。实测元素含量(%):C,89.88;H,5.89;N,1.95。
红色有机发光器件(电子传输层)
[对比实施例1-4]器件制备实施例:
对比实施例1:利用真空热蒸镀的方法制备有机发光器件。实验步骤为:将ITO基板放在蒸馏水中清洗3次,超声波洗涤15分钟,蒸馏水清洗结束后,异丙醇、丙酮、甲醇等溶剂按顺序超声波洗涤以后,120℃烘干干燥,送到蒸镀机里。
在已经准备好的ITO透明电极上以逐层真空蒸镀的方式蒸镀空穴注入层NPNPB/45nm、蒸镀空穴传输层β-NPB/28nm、蒸镀主体m-CBP:掺杂Ir(piq)2acac(质量含量97%:3%混合)/26nm、然后蒸镀电子传输层ET-1/27nm、电子注入层LiF/1.1nm、阴极Al/136nm。并将该器件密封于手套箱中,从而制备了有机发光器件。按照上述步骤完成有机发光器件的制作后,测量器件的光电性能,相关材料的分子结构式如下所示:
对比实施例2:将对比实施例1中的电子传输层材料ET-1换成ET-2,用与对比实施例1相同的方式来制造对比实施例2的有机发光器件。
对比实施例3:将对比实施例1中的电子传输层材料ET-1换成ET-3,用与对比实施例1相同的方式来制造对比实施例3的有机发光器件。
对比实施例4:将对比实施例1中的电子传输层材料ET-1换成ET-4,用与对比实施例1相同的方式来制造对比实施例4的有机发光器件。
[实施例1-26]
实施例1-26:将有机发光器件的电子传输层材料ET-1依次换成本发明的化合物1、5、14、29、47、82、85、92、141、269、279、339、341、394、413、461、477、491、509、522、526、529、550、569、666、670,其他步骤均与对比实施例1相同。
将测试软件、计算机、美国Keithley公司生产的K2400数字源表和美国PhotoResearch公司的PR788光谱扫描亮度计组成一个联合IVL测试***来测试有机发光器件的发光效率。寿命的测试采用McScience公司的M6000 OLED寿命测试***。测试的环境为大气环境,温度为室温。所得有机发光器件的发光特性测试结果见表1所示。表1为本发明实施例制备的化合物以及比较物质制备的发光器件的发光特性测试结果。
[表1]发光器件的发光特性测试
/>
注:T95指的是在电流密度为10mA/cm2情况下,器件亮度衰减到95%所用的时间;
由表1的结果可以看出,本发明的含氮杂环有机化合物应用于有机发光器件中,作为电子传输层材料,与比较实施例1-4相比,表现出发光效率高、使用寿命长的优点,是性能良好的有机发光器件电子传输材料。
绿色有机发光器件(空穴阻挡层)
[对比实施例5]器件制备实施例:
对比实施例5:利用真空热蒸镀的方法制备有机发光器件。实验步骤为:将ITO透明基板放在蒸馏水中清洗3次,超声波洗涤15分钟,蒸馏水清洗结束后,异丙醇、丙酮、甲醇等溶剂按顺序超声波洗涤以后,120℃烘干干燥,送到蒸镀机里。
在已经准备好的ITO透明基板电极上以逐层真空蒸镀的方式蒸镀空穴注入层在已经准备好的ITO透明基板电极上以逐层真空蒸镀的方式蒸镀空穴注入层NPNPB/50nm、蒸镀空穴传输层β-NPB/29nm、蒸镀主体m-CBP:掺杂Ir(ppy)3(质量含量95%:5%混合)/32nm、然后蒸镀空穴阻挡层ET-1/29nm,蒸镀电子传输层TMPYPB/25nm、电子注入层LiF/1nm、阴极Al/134nm。并将该器件密封于手套箱中,从而制备了有机发光器件。按照上述步骤完成有机发光器件的制作后,测量器件的光电性能,相关材料的分子结构式如下所示:
对比实施例6:将对比实施例1中的空穴阻挡层材料ET-1换成ET-2,用与对比实施例1相同的方式来制造对比实施例6的有机发光器件。
[实施例27-49]
实施例27-49:将有机发光器件的空穴阻挡层材料ET-1依次换成本发明的化合物1、5、14、29、47、85、92、141、269、279、339、341、394、413、461、477、491、509、522、526、529、550、569,其他步骤均与对比实施例5相同。
将测试软件、计算机、美国Keithley公司生产的K2400数字源表和美国PhotoResearch公司的PR788光谱扫描亮度计组成一个联合IVL测试***来测试有机发光器件的发光效率。寿命的测试采用McScience公司的M6000 OLED寿命测试***。测试的环境为大气环境,温度为室温。所得有机发光器件的发光特性测试结果见表2所示。表2为本发明实施例制备的化合物以及比较物质制备的发光器件的发光特性测试结果。
[表2]发光器件的发光特性测试
/>
由表2的结果可以看出,本发明的含氮杂环有机化合物应用于有机发光器件中,尤其是作为空穴阻挡层材料,与对比实施例5-6相比,显著改善了有机发光器件的发光效率和使用寿命,是性能良好的有机发光材料。
应当指出,本发明用个别实施方案进行了特别描述,但在不脱离本发明原理的前提下,本领域普通技术人可对本发明进行各种形式或细节上的改进,这些改进也落入本发明的保护范围内。
Claims (7)
1.一种含氮杂环有机化合物,其特征在于,分子结构如式Ⅰ所示:
所述L选自下示基团中的一种:
R'选自氢、氘中的一种或多种;
所述q1a选自0、1、2、3或4;
所述X相同或不同的选自CR'或N,且一个X选自N;
所述选自如下所示基团中的任意一种:
所述Z选自O、S或N(Ry)中的任意一种;所述Ry选自取代或未取代的苯基中的任意一种;所述“取代的…”是指被选自氘的基团单取代或多取代;
所述选自如下所示基团中的任意一种:
所述a选自0、1、2或3;b选自0、1、2、3或4;e选自0、1、2、3、4、5或6;
所述Ra选自氘;
所述Ra1独立地选自氘、叔丁基、苯基,并且所述叔丁基、苯基还可被氘中的一个或多个取代,当Ra1选自叔丁基、苯基时,b选自1;
所述Ra2独立地选自氘、叔丁基,并且所述叔丁基还可被氘中的一个或多个取代,当Ra2选自叔丁基时,b选自1。
2.根据权利要求1所述的一种含氮杂环有机化合物,其特征在于,所述L选自下示基团中的一种:
3.根据权利要求1所述的一种含氮杂环有机化合物,其特征在于,所述选自如下所示基团中的任意一种:
所述Z选自O、S或N(Ry)中的任意一种;所述Ry选自取代或未取代的苯基中的任意一种;所述“取代的…”是指被选自氘的基团单取代或多取代。
4.根据权利要求1所述的一种含氮杂环有机化合物,其特征在于,所述选自如下所示基团中的任意一种:
所述Ra选自氘;
所述Ra1选自氘;
所述Ra2选自氘。
5.一种含氮杂环有机化合物,其特征在于,所述含氮杂环有机化合物选自如下所示化学结构中的任意一种:
6.一种有机发光器件,包括阳极、阴极、有机物层,所述有机物层位于所述阳极与所述阴极之间,其特征在于,所述有机物层包含电子传输层,所述电子传输层中含有权利要求1~5任一项所述的含氮杂环有机化合物中的任意一种或至少两种的组合。
7.根据权利要求6所述的一种有机发光器件,其特征在于,所述有机物层包含空穴阻挡层,所述空穴阻挡层中含有权利要求1~5任一项所述的含氮杂环有机化合物中的任意一种或至少两种的组合。
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN202210509454.6A CN114773286B (zh) | 2022-05-10 | 2022-05-10 | 一种含氮杂环有机化合物及其有机发光器件 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN202210509454.6A CN114773286B (zh) | 2022-05-10 | 2022-05-10 | 一种含氮杂环有机化合物及其有机发光器件 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN114773286A CN114773286A (zh) | 2022-07-22 |
CN114773286B true CN114773286B (zh) | 2024-02-20 |
Family
ID=82437632
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN202210509454.6A Active CN114773286B (zh) | 2022-05-10 | 2022-05-10 | 一种含氮杂环有机化合物及其有机发光器件 |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN114773286B (zh) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN115745906A (zh) * | 2022-09-07 | 2023-03-07 | 长春海谱润斯科技股份有限公司 | 一种包含杂环的化合物及其有机电致发光器件 |
CN115819351A (zh) * | 2022-12-22 | 2023-03-21 | 吉林奥来德光电材料股份有限公司 | 一种有机稠环化合物及其制备方法和应用 |
Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2016133342A1 (ko) * | 2015-02-16 | 2016-08-25 | 주식회사 엘지화학 | 이중스피로형 화합물 및 이를 포함하는 유기 발광 소자 |
WO2016197353A1 (en) * | 2015-06-11 | 2016-12-15 | Dow Global Technologies Llc | Organic electroluminescent compound and organic electroluminescent device comprising the same |
CN107431143A (zh) * | 2015-09-09 | 2017-12-01 | 株式会社Lg化学 | 有机电致发光元件 |
CN108884060A (zh) * | 2016-04-12 | 2018-11-23 | 株式会社Lg化学 | 化合物和包含其的有机电子元件 |
CN113527181A (zh) * | 2021-08-12 | 2021-10-22 | 长春海谱润斯科技股份有限公司 | 一种含氮杂环类有机化合物及其有机发光器件 |
CN113651785A (zh) * | 2021-09-17 | 2021-11-16 | 长春海谱润斯科技股份有限公司 | 一种杂环化合物及其有机发光器件 |
-
2022
- 2022-05-10 CN CN202210509454.6A patent/CN114773286B/zh active Active
Patent Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2016133342A1 (ko) * | 2015-02-16 | 2016-08-25 | 주식회사 엘지화학 | 이중스피로형 화합물 및 이를 포함하는 유기 발광 소자 |
CN107250101A (zh) * | 2015-02-16 | 2017-10-13 | 株式会社Lg化学 | 双螺环型化合物和包含其的有机发光器件 |
WO2016197353A1 (en) * | 2015-06-11 | 2016-12-15 | Dow Global Technologies Llc | Organic electroluminescent compound and organic electroluminescent device comprising the same |
CN107431143A (zh) * | 2015-09-09 | 2017-12-01 | 株式会社Lg化学 | 有机电致发光元件 |
CN108884060A (zh) * | 2016-04-12 | 2018-11-23 | 株式会社Lg化学 | 化合物和包含其的有机电子元件 |
CN113527181A (zh) * | 2021-08-12 | 2021-10-22 | 长春海谱润斯科技股份有限公司 | 一种含氮杂环类有机化合物及其有机发光器件 |
CN113651785A (zh) * | 2021-09-17 | 2021-11-16 | 长春海谱润斯科技股份有限公司 | 一种杂环化合物及其有机发光器件 |
Also Published As
Publication number | Publication date |
---|---|
CN114773286A (zh) | 2022-07-22 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
EP3757110A1 (en) | Heterocyclic compound and organic light-emitting device comprising same | |
KR101982715B1 (ko) | 신규한 화합물 및 이를 포함하는 유기 발광 소자 | |
CN112789273A (zh) | 新型化合物及包含其的有机发光器件 | |
CN114773286B (zh) | 一种含氮杂环有机化合物及其有机发光器件 | |
JP7105388B1 (ja) | 窒素含有化合物、電子部品及び電子装置 | |
JP2020510652A (ja) | 新規な化合物およびこれを用いた有機発光素子 | |
KR102546269B1 (ko) | 신규한 화합물 및 이를 이용한 유기 발광 소자 | |
CN113861044A (zh) | 有机化合物及包含其的电子元件和电子装置 | |
EP3369731B1 (en) | Heterocyclic compound and organic light emitting element comprising same | |
KR102546268B1 (ko) | 신규한 화합물 및 이를 이용한 유기 발광 소자 | |
CN112789272B (zh) | 化合物及包含其的有机发光器件 | |
CN116836193A (zh) | 一种有机化合物及其应用以及包含其的有机电致发光器件 | |
CN116261347A (zh) | 一种有机电致发光器件 | |
CN112334472A (zh) | 新型化合物及包含其的有机发光器件 | |
CN116143739A (zh) | 一种双胺化合物及其有机发光器件 | |
KR102495828B1 (ko) | 신규한 화합물 및 이를 이용한 유기 발광 소자 | |
CN115368294A (zh) | 有机化合物及包含其的电子元件和电子装置 | |
CN111212829B (zh) | 螺环化合物及包含其的有机发光装置 | |
CN115968591A (zh) | 包含有机化合物的有机发光器件 | |
CN114497424B (zh) | 有机电致发光器件及包括其的电子装置 | |
CN115521214B (zh) | 有机化合物及包含其的电子元件和电子装置 | |
KR102486519B1 (ko) | 신규한 화합물 및 이를 이용한 유기발광 소자 | |
CN113735893B (zh) | 一种有机化合物以及使用其的电子元件和电子装置 | |
CN115073440B (zh) | 一种具有苯并唑环的化合物及其有机电致发光器件 | |
CN114181166B (zh) | 有机化合物及包含其的电子元件和电子装置 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PB01 | Publication | ||
PB01 | Publication | ||
SE01 | Entry into force of request for substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
GR01 | Patent grant | ||
GR01 | Patent grant |