CN107546339A - A kind of organic electroluminescence device - Google Patents
A kind of organic electroluminescence device Download PDFInfo
- Publication number
- CN107546339A CN107546339A CN201710818081.XA CN201710818081A CN107546339A CN 107546339 A CN107546339 A CN 107546339A CN 201710818081 A CN201710818081 A CN 201710818081A CN 107546339 A CN107546339 A CN 107546339A
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- CN
- China
- Prior art keywords
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- organic electroluminescence
- electroluminescence device
- formula
- substituted
- Prior art date
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- 238000005401 electroluminescence Methods 0.000 title claims abstract description 48
- 239000000463 material Substances 0.000 claims abstract description 60
- 150000001875 compounds Chemical class 0.000 claims abstract description 36
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical class C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims abstract description 11
- 239000001257 hydrogen Substances 0.000 claims abstract description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 11
- -1 hydrogen iso-indoles Chemical class 0.000 claims abstract description 11
- 125000000217 alkyl group Chemical group 0.000 claims abstract 2
- 230000005540 biological transmission Effects 0.000 claims description 17
- 239000000758 substrate Substances 0.000 claims description 12
- 230000027756 respiratory electron transport chain Effects 0.000 claims description 10
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical class C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 8
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical class C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims description 6
- 238000006467 substitution reaction Methods 0.000 claims description 6
- 238000004020 luminiscence type Methods 0.000 claims description 5
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Chemical class C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 2
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims description 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical class C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 2
- 150000001556 benzimidazoles Chemical class 0.000 claims description 2
- 125000001797 benzyl group Chemical class [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000005956 isoquinolyl group Chemical group 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 150000003230 pyrimidines Chemical class 0.000 claims description 2
- 125000005493 quinolyl group Chemical group 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 2
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical class C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract description 17
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract description 15
- 150000001539 azetidines Chemical class 0.000 abstract description 2
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 239000010410 layer Substances 0.000 description 56
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 42
- 238000010189 synthetic method Methods 0.000 description 19
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- 238000001704 evaporation Methods 0.000 description 17
- 230000008020 evaporation Effects 0.000 description 17
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- 238000007738 vacuum evaporation Methods 0.000 description 14
- 239000011368 organic material Substances 0.000 description 12
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 11
- 239000000543 intermediate Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 239000011521 glass Substances 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 238000010828 elution Methods 0.000 description 7
- 238000000926 separation method Methods 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000000975 dye Substances 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 239000003208 petroleum Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 230000005311 nuclear magnetism Effects 0.000 description 5
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 5
- GEQBRULPNIVQPP-UHFFFAOYSA-N 2-[3,5-bis(1-phenylbenzimidazol-2-yl)phenyl]-1-phenylbenzimidazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2N=C1C1=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=C1 GEQBRULPNIVQPP-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 230000008859 change Effects 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 239000012312 sodium hydride Substances 0.000 description 4
- 229910000104 sodium hydride Inorganic materials 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 150000001768 cations Chemical class 0.000 description 3
- 239000008367 deionised water Substances 0.000 description 3
- 229910021641 deionized water Inorganic materials 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 238000004770 highest occupied molecular orbital Methods 0.000 description 3
- 239000012046 mixed solvent Substances 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000004065 semiconductor Substances 0.000 description 3
- 238000010898 silica gel chromatography Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- MEYZYGMYMLNUHJ-UHFFFAOYSA-N tunicamycin Natural products CC(C)CCCCCCCCCC=CC(=O)NC1C(O)C(O)C(CC(O)C2OC(C(O)C2O)N3C=CC(=O)NC3=O)OC1OC4OC(CO)C(O)C(O)C4NC(=O)C MEYZYGMYMLNUHJ-UHFFFAOYSA-N 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- QCKHDUGSFBCWFL-UHFFFAOYSA-N CC(C)(c1c-2ccc(-c3cnccc3)c1)[n]1c-2c(C)c2c1ccc(-c1cnccc1)c2 Chemical compound CC(C)(c1c-2ccc(-c3cnccc3)c1)[n]1c-2c(C)c2c1ccc(-c1cnccc1)c2 QCKHDUGSFBCWFL-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000010405 anode material Substances 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000003810 ethyl acetate extraction Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000007850 fluorescent dye Substances 0.000 description 2
- 238000007306 functionalization reaction Methods 0.000 description 2
- 210000004209 hair Anatomy 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 150000002475 indoles Chemical class 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 230000002441 reversible effect Effects 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 2
- 125000005259 triarylamine group Chemical group 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Substances C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- LVEYOSJUKRVCCF-UHFFFAOYSA-N 1,3-Bis(diphenylphosphino)propane Substances C=1C=CC=CC=1P(C=1C=CC=CC=1)CCCP(C=1C=CC=CC=1)C1=CC=CC=C1 LVEYOSJUKRVCCF-UHFFFAOYSA-N 0.000 description 1
- 150000005759 2-chloropyridine Chemical class 0.000 description 1
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 1
- MUVBWKOIQZPFAW-UHFFFAOYSA-N C(C1=CC=CC=C1)Cl.[I] Chemical group C(C1=CC=CC=C1)Cl.[I] MUVBWKOIQZPFAW-UHFFFAOYSA-N 0.000 description 1
- 0 C*(C)(c1c-2ccc(-c3ncccc3)c1)[n]1c-2c(C)c2c1ccc(-c1ncccc1)c2 Chemical compound C*(C)(c1c-2ccc(-c3ncccc3)c1)[n]1c-2c(C)c2c1ccc(-c1ncccc1)c2 0.000 description 1
- YXHFFOSHBSELDN-UHFFFAOYSA-N CC(C)(c1c-2ccc(-c3ccc(-c4cc(-c5cc(-c(cc6)ccc6-c(cc6)cc7c6[n](C(C)(C)c6c-8ccc(-c9ccc(-c%10cnccc%10)cc9)c6)c-8c7C)cnc5)ccc4)nc3)c1)[n]1c-2c(C)c2cc(-c3ccc(-c4ccccc4)nc3)ccc12 Chemical compound CC(C)(c1c-2ccc(-c3ccc(-c4cc(-c5cc(-c(cc6)ccc6-c(cc6)cc7c6[n](C(C)(C)c6c-8ccc(-c9ccc(-c%10cnccc%10)cc9)c6)c-8c7C)cnc5)ccc4)nc3)c1)[n]1c-2c(C)c2cc(-c3ccc(-c4ccccc4)nc3)ccc12 YXHFFOSHBSELDN-UHFFFAOYSA-N 0.000 description 1
- SFECZXYCFNVFCU-UHFFFAOYSA-N CC(C)(c1c-2ccc(-c3nc(cccc4)c4cc3)c1)[n]1c-2c(C)c2cc(-c3nc(cccc4)c4cc3)ccc12 Chemical compound CC(C)(c1c-2ccc(-c3nc(cccc4)c4cc3)c1)[n]1c-2c(C)c2cc(-c3nc(cccc4)c4cc3)ccc12 SFECZXYCFNVFCU-UHFFFAOYSA-N 0.000 description 1
- RHMDQOCAXFPUHY-UHFFFAOYSA-O CC(C)(c1cc(-c(cc2)ccc2-c2nc3ccccc3[n]2-c2ccccc2)ccc1-1)[n]2c-1c(C)c1cc(-c(cc3)ccc3-c3[nH+]c4ccccc4[n]3-c3ccccc3)ccc21 Chemical compound CC(C)(c1cc(-c(cc2)ccc2-c2nc3ccccc3[n]2-c2ccccc2)ccc1-1)[n]2c-1c(C)c1cc(-c(cc3)ccc3-c3[nH+]c4ccccc4[n]3-c3ccccc3)ccc21 RHMDQOCAXFPUHY-UHFFFAOYSA-O 0.000 description 1
- PPXACLKGPJZUSX-UHFFFAOYSA-N Cc(c1c2)c(-c(cc3)c(C4(c5ccc(C)cc5)c5ccc(C)cc5)cc3-c3ccc(-c5ccccc5)nc3)[n]4c1ccc2-c1ccc(-c2ccccc2)nc1 Chemical compound Cc(c1c2)c(-c(cc3)c(C4(c5ccc(C)cc5)c5ccc(C)cc5)cc3-c3ccc(-c5ccccc5)nc3)[n]4c1ccc2-c1ccc(-c2ccccc2)nc1 PPXACLKGPJZUSX-UHFFFAOYSA-N 0.000 description 1
- FTBZPEFUPJJFHQ-UHFFFAOYSA-N Cc1c(-c(cc2)c(C3(C4CCCCC4)C4CCCCC4)cc2-c2nc(-c4ccccc4)nc(-c4ccccc4)n2)[n]3c(cc2)c1cc2-c1nc(-c2ccccc2)nc(-c2ccccc2)n1 Chemical compound Cc1c(-c(cc2)c(C3(C4CCCCC4)C4CCCCC4)cc2-c2nc(-c4ccccc4)nc(-c4ccccc4)n2)[n]3c(cc2)c1cc2-c1nc(-c2ccccc2)nc(-c2ccccc2)n1 FTBZPEFUPJJFHQ-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 229920002565 Polyethylene Glycol 400 Polymers 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical class C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- 125000001246 bromo group Chemical class Br* 0.000 description 1
- ANUZKYYBDVLEEI-UHFFFAOYSA-N butane;hexane;lithium Chemical compound [Li]CCCC.CCCCCC ANUZKYYBDVLEEI-UHFFFAOYSA-N 0.000 description 1
- QNEFNFIKZWUAEQ-UHFFFAOYSA-N carbonic acid;potassium Chemical compound [K].OC(O)=O QNEFNFIKZWUAEQ-UHFFFAOYSA-N 0.000 description 1
- 239000010406 cathode material Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical class ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 238000000295 emission spectrum Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000005283 ground state Effects 0.000 description 1
- 230000005525 hole transport Effects 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- ZEWMZYKTKNUFEF-UHFFFAOYSA-N indium;oxozinc Chemical compound [In].[Zn]=O ZEWMZYKTKNUFEF-UHFFFAOYSA-N 0.000 description 1
- 150000008424 iodobenzenes Chemical class 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- CECAIMUJVYQLKA-UHFFFAOYSA-N iridium 1-phenylisoquinoline Chemical compound [Ir].C1=CC=CC=C1C1=NC=CC2=CC=CC=C12.C1=CC=CC=C1C1=NC=CC2=CC=CC=C12.C1=CC=CC=C1C1=NC=CC2=CC=CC=C12 CECAIMUJVYQLKA-UHFFFAOYSA-N 0.000 description 1
- 230000009191 jumping Effects 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 150000002916 oxazoles Chemical class 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- JLFNLZLINWHATN-UHFFFAOYSA-N pentaethylene glycol Chemical compound OCCOCCOCCOCCOCCO JLFNLZLINWHATN-UHFFFAOYSA-N 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229940068918 polyethylene glycol 400 Drugs 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000005036 potential barrier Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- ZFRKQXVRDFCRJG-UHFFFAOYSA-N skatole Chemical compound C1=CC=C2C(C)=CNC2=C1 ZFRKQXVRDFCRJG-UHFFFAOYSA-N 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- NHDIQVFFNDKAQU-UHFFFAOYSA-N tripropan-2-yl borate Chemical class CC(C)OB(OC(C)C)OC(C)C NHDIQVFFNDKAQU-UHFFFAOYSA-N 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- 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
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Abstract
The invention discloses a kind of 6 hydrogen iso-indoles simultaneously [2,1 a] Benzazole compounds, there is the structural formula as shown in formula (1), wherein, X represents alkyl or aryl, R1Selected from selected from C5‑C30Nitrogen heterocyclic ring, substituted azetidine or thick nitrogen heterocyclic ring aromatic hydrocarbons.The compound can be used as electron transport material, green or the red phosphorescent material of main part of organic electroluminescence device, and the brightness and luminous efficiency that can make organic electroluminescence device improve, and reduce its driving voltage.
Description
The application is divisional application.Original application is Chinese patent application, application number：201310456007.X the applying date:
On September 29th, 2013, denomination of invention：Simultaneously [2,1-a] Benzazole compounds and its application of 6- hydrogen iso-indoles.
Technical field
The present invention relates to a kind of organic compound, more particularly, to organic electroluminescence device luminescent layer material of main part
Compound；The invention further relates to application of the compound in organic electroluminescence device.
Background technology
Electro optical phenomenon most early in 20th century the '30s be found, initial luminescent material is ZnS powder, is thus sent out
LED technology has been put on display, has been widely applied to now on energy-conserving light source.And organic electroluminescent phenomenon is Pope in 1963 et al.
Find earliest, they have found that the single layer crystal of anthracene under the driving of more than 100V voltages, can send faint blue light.Until
Bi-layer devices are made in organic fluorescent dye by doctor Deng Qingyun of Kodak in 1987 et al. in a manner of vacuum evaporation, are being driven
Under voltage of the voltage less than 10 volts, external quantum efficiency has reached 1% so that electroluminescent organic material and device are provided with reality
With the possibility of property, the research of OLED material and device has been promoted significantly from this.
Relative to phosphor, electroluminescent organic material has advantages below：1. organic material processing characteristics is good,
Can be by evaporation or the method for spin coating, the film forming on any substrate；2. the diversity of organic molecular structure can cause can
By the method for Molecular Design and modification, to adjust the heat endurance of organic material, engineering properties, luminous and electric conductivity
Can so that material is significantly improved space.
The principle of luminosity of organic electroluminescent diode is similar with inorganic light-emitting diode.When element is spread out by direct current
During raw forward bias voltage drop, voltage energy will drive electronics (Electron) with hole (Hole) respectively by negative electrode and anode in addition outside
Injection element, when both meet in luminescent layer, combine, that is, the compound exciton of so-called electron-hole is formed, exciton passes through luminous
The form of relaxation returns to ground state, so as to reach luminous purpose.
What the generation of organic electroluminescent was leaned on is the carrier (electronics and hole) transmitted in organic semiconducting materials
Restructuring, it is well known that the electric conductivity of organic material is very poor, unlike inorganic semiconductor, does not continue in organic semiconductor
Energy band, the transmission of carrier conventional jump theory describes, i.e., under the driving of an electric field, electronics is being excited or is being injected into
In the lumo energy of molecule, the purpose of electric charge transmission is reached via the lumo energy for jumping to another molecule.In order to make
Organic electroluminescence device reaches breakthrough in application aspect, it is necessary to overcome organic material electric charge inject and transmittability difference it is tired
It is difficult.Scientists make different organic layers by the adjustment of device architecture, such as the number of increase device organic material layer
Play the part of different roles, such as the functional material having helps electronics to be injected from negative electrode and hole from anode, some materials help
The transmission of electric charge, the material played the role of, which then plays, stops electronics and hole transport, most important certainly in organic electroluminescent
The luminescent material of a variety of colors also to reach the purpose to match with adjacent functional material, excellent in efficiency long lifespan it is organic
Electroluminescent device is typically the result of the optimization collocation of device architecture and various organic materials, and this is just designed for chemists
The functionalization material for developing various structures provides greatly opportunities and challenges.
Common functionalization organic material has：Hole-injecting material, hole mobile material, hole barrier materials, electronics note
Enter material, electron transport material, electron-blocking materials and light emitting host material and light-emitting guest (dyestuff) etc..
Hole-injecting material (HIM) requires its HOMO energy level between anode and hole transmission layer, is advantageous to increase boundary
Hole injection between face.
Hole mobile material (HTM), it is desirable to there is high heat endurance (high Tg), with anode or hole-injecting material
There is less potential barrier, higher cavity transmission ability can vacuum evaporation formation pin-hole free films.Conventional HTM is that fragrance is more
Aminated compounds, mainly derivative of tri-arylamine group.
It is reversible and sufficiently high that electron transport material (Electron transport Material, ETM) requires that ETM has
Electrochemical reduction current potential, suitable HOMO and LUMO can rank value electronics is preferably injected, and be preferably provided with sky
Cave blocking capability；Higher electron transport ability, the film forming having had and heat endurance.ETM is typically electron deficient knot
The aromatic compound of the conjugate planes of structure.
Luminescent layer material of main part (host) needs to have following characteristics：Reversible electrochemical redox current potential is and adjacent
Hole and the electron transfer layer HOMO that matches and LUMO can rank, good and the hole to match and electron transport ability are good
Good high heat endurance and film forming, and suitable singlet or triplet state energy gap are used for controlling exciton in luminescent layer,
Also energy transfer good between corresponding fluorescent dye or phosphorescent coloring.
The luminescent material of luminescent layer needs to have had the special feature that：With high fluorescence or phosphorescence quantum efficiency；Dyestuff
Absorption spectrum has had overlapping with the emission spectrum of main body, i.e., main body is adapted to dyestuff energy, can be effectively from main body to dyestuff
Energy transmission；Red, green, blue emission peak is as narrow as possible, with the excitation obtained；Stability is good, can be deposited etc..
Up to the present, new electroluminescent organic material is still among continuous research and development, it has been found that Yi Leixin
Organic material, as shown in formula (1)：
It was found that this material may be used as material of main part in organic electroluminescence device, electric transmission material is also used as
Material, has more excellent efficiency and brightness.
The content of the invention
The technical problems to be solved by the invention are the provision of a kind of new different Yin of 6- hydrogen for organic electroluminescent
Diindyl simultaneously [2,1-a] Benzazole compounds, this compound is as shown in formula (1)：
Wherein：X is selected from C1-C20Alkyl, C6-C20Aromatic radical, substitute C6-C20Aromatic radical.R1Selected from C5-C30It is nitrogenous
Heterocycle, substituted azetidine or thick nitrogen heterocyclic ring aromatic hydrocarbons.
Preferably, described X is methyl, ethyl, propyl group, isopropyl, normal-butyl, isobutyl group, amyl group, isopentyl, ring penta
Base, alkyl-substituted cyclopenta, n-hexyl, cyclohexyl, alkyl-substituted cyclohexyl, phenyl, alkyl-substituted phenyl, benzyl.
Preferably, the R1 be selected from pyridine radicals, substituted pyridinyl, pyridinylphenyl, benzimidazole, substituted benzimidazole,
Benzothiazole, substitution benzothiazole, oxazole, substituted oxazole, pyrimidine, substituted pyrimidines, pyrazine, substitution pyrazine, triazine, substitution three
Piperazine, quinolyl or isoquinolyl.
It is furthermore preferred that the compound is selected from following structural formula：
The luminescent layer material of main part of a kind of organic electroluminescence device, it is characterised in that its described material of main part can use
6- hydrogen iso-indoles of the present invention simultaneously [2,1-a] Benzazole compounds.
Also, a kind of organic electroluminescence device, including substrate, and sequentially form anode layer on the substrate,
Several luminescence unit layers and cathode layer；
Described luminescence unit layer includes hole transmission layer, organic luminous layer and electron transfer layer, the luminescent layer
Material of main part uses 6- hydrogen iso-indoles of the present invention simultaneously [2,1-a] Benzazole compounds
Also, simultaneously [2,1-a] Benzazole compounds may be used as red phosphorescent and light 6- hydrogen iso-indoles of the present invention
The material of main part of layer, can also be as the material of main part of green phosphorescent luminescent layer.
Also, simultaneously [2,1-a] Benzazole compounds may be used as electron transfer layer material to 6- hydrogen iso-indoles of the present invention
Material.
Also, simultaneously [2,1-a] Benzazole compounds can be used for organic electroluminescent to 6- hydrogen iso-indoles of the present invention
Device.
Brief description of the drawings
Fig. 1 is the nuclear-magnetism figure of the compound (M1) of the embodiment of the present invention 1.
Fig. 2 is the nuclear-magnetism figure of the compound (M7) of the embodiment of the present invention 7.
Fig. 3 is the nuclear-magnetism figure of the compound (P2) of the embodiment of the present invention 10.
Fig. 4 is the nuclear-magnetism figure of the compound (P1) of the embodiment of the present invention 18.
Fig. 5 is the nuclear-magnetism figure of the compound (P14) of the embodiment of the present invention 22.
Embodiment
Below will the invention will be further described by specific embodiment.
Embodiment 1
Intermediate shown in the present embodiment formula (M1)：
Synthetic method is as follows：
(1) synthesis of 1- (2- iodine benzyl) -3- Methyl-1H-indoles
1000 milliliters of there-necked flasks, nitrogen protection is lower to add 700 milliliters of dimethyl sulfoxide (DMSO)s, 52 grams of potassium hydroxide, 26.2 grams of 3-
Methyl indol, after 30 points of kinds are stirred at room temperature, add 50.5 grams of adjacent iodine benzyl chlorides.Then it is stirred at room temperature 3 hours, is poured into 2000 milliliters of water
In, ethyl acetate extraction, it is washed to neutrality, silica gel post separation, petroleum ether：Ethyl acetate volume ratio=10：1 elution, is produced
55.1 grams of product, MS (m/e)：347.
(2) synthesis of 11- methyl -6H- iso-indoles simultaneously [2,1-a] indoles
1000 milliliters of there-necked flasks, nitrogen protection, mechanical agitation, add 34.7 grams of 1- (2- iodine benzyl) -3- methyl isophthalic acid H- Yin
Diindyl, 1 gram of copper powder, 30 grams of potassium carbonate, 600 milliliters of PEG400 (polyethylene glycol 400), 180 degree is to slowly warm up to, reacted 24 hours,
Cooling, is poured into 2000 milliliters of water, dichloromethane extraction, after dichloromethane layer is dried with magnesium sulfate, silica gel column chromatography separation, and stone
Oily ether：Ethyl acetate：Methylene chloride volume ratio=10：1：1 elution, obtains 10.2 grams of product, MS (m/e)：219.
(3) M1 synthesis
500 milliliters of there-necked flasks, add 9 grams of 11- methyl -6H- iso-indoles simultaneously [2,1-a] indoles, 300 milliliters of dichloromethane,
0-5 DEG C is cooled to, is slowly added dropwise 20 milliliters of dichloromethane solutions of 14.5 grams of bromines, drop finishes that to be to slowly warm up to 20 DEG C of reactions 2 small
When, add solution of sodium bisulfite washing, washing, dichloromethane layer silica gel post separation, petroleum ether：Ethyl acetate：Dichloromethane
Volume ratio=10：1：1 elution, obtains 12.1 grams of product, MS (m/e)：377, product M1 nuclear magnetic spectrogram (1H) are shown in the institute of accompanying drawing 1
Show.
Embodiment 2
Intermediate shown in the present embodiment formula (M2)：
Synthetic method is as follows：
500 milliliters of there-necked flasks, under nitrogen protection, 3.8 grams of M1 are added, 300 milliliters of DMSO, are slowly added to 1.6 grams of contents
60% sodium hydride, after stirring 30 minutes, 4.3 grams of iodomethane are added, reacts at room temperature 12 hours, it is not anti-to add a small amount of Methanol Decomposition
After the sodium hydride answered, reaction solution is poured into 900 milliliters of water, dichloromethane extraction, washing, dichloromethane layer silica gel post separation,
Petroleum ether：Ethyl acetate：Methylene chloride volume ratio=10：1：1 elution, obtains 3.0g grams of product, MS (m/e)：405.
3-embodiment of embodiment 6
With reference to the method for embodiment 2, intermediate M3-M6 totally 4 intermediates are prepared for, specific data are as follows：
Embodiment 7
Intermediate shown in the present embodiment formula (M7)：
Synthetic method is as follows：
500 milliliters of there-necked flasks, nitrogen protection add 3.8 grams of M1,300 milliliters of DMSO, are slowly added to 1.6 grams of contents 60%
Sodium hydride, after stirring 30 minutes, 6.0 grams of iodobenzenes are added, 0.6 gram of Pd (dppp) Cl2, are to slowly warm up to 50 DEG C, are reacted 24 hours,
After adding the unreacted sodium hydride of a small amount of Methanol Decomposition, reaction solution is poured into 900 milliliters of water, dichloromethane extraction, washing, two
Chloromethanes layer silica gel post separation, petroleum ether：Ethyl acetate：Methylene chloride volume ratio=10：1：1 elution, obtains 1.5g grams of product,
MS(m/e)：529, product M7 nuclear magnetic spectrogram (1H) are as shown in accompanying drawing 2.
8-embodiment of embodiment 9
According to the method for embodiment 7, intermediate M8 and M9 totally 2 intermediates are prepared for, specific data are as follows：
Embodiment 10
Shown in compound manufactured in the present embodiment such as formula (P2)：
Synthetic method is as follows：
250 milliliters of there-necked flasks, add 4.0g M2,2.7g pyridine -3- boric acid, 0.6g tetra-triphenylphosphine palladiums, 9.1g carbonic acid
Potassium, 80 milliliters of toluene, 50 milliliters of ethanol, 30 milliliters of water, under nitrogen protection, heating reflux reaction 8 hours, cool, filtering, solid
After drying, silica gel column chromatography separation, petroleum ether：Ethyl acetate：Methylene chloride volume ratio=10：1：3 elutions, obtain product 3.1g
Gram, MS (m/e)：401, compound P2 nuclear magnetic spectrogram (1H) are as shown in accompanying drawing 3.
11-embodiment of embodiment 17
According to the method for embodiment 10, using intermediate M2 and corresponding acid reaction, following 7 products have been synthesized,
Specific data are as follows：
Embodiment 18
Shown in compound manufactured in the present embodiment such as formula (P1)：
Synthetic method is as follows：
500 milliliters of there-necked flasks, 4.0g M2 are added, 300 milliliters of tetrahydrofurans, -78 DEG C is cooled to, is slowly added dropwise 10 milliliters
2.4M butyl lithium hexane solution, finish and be incubated 1 hour in -78 DEG C, add 5.6g triisopropyl borate esters, be warmed to room temperature naturally
Reaction 2 hours, is poured into aqueous ammonium chloride solution, ethyl acetate extraction organic layer, after organic layer magnesium sulfate is dried, is concentrated into
It is dry, it is directly added into 80 milliliters of toluene, 50 milliliters of ethanol, 30 milliliters of water, 1.13g 2- chloropyridines, 0.4g tetra-triphenylphosphine palladiums, nitrogen
Under gas shielded, heating reflux reaction 8 hours, cool, filtering, after solid is dried, silica gel column chromatography separation, petroleum ether：Acetic acid second
Ester：Methylene chloride volume ratio=10：1：3 elutions, obtain 1.4g grams of product, MS (m/e)：401, compound P1 nuclear magnetic spectrogram
Shown in (1H) as accompanying drawing 4.
19-embodiment of embodiment 21
According to the method for embodiment 18, reacted using intermediate M2 and corresponding chloro thing, synthesized following 3 productions
Product, specific data are as follows：
Embodiment 22
Shown in compound manufactured in the present embodiment such as formula (P14)：
The same P11 of synthetic method, simply changes M2 into M7, obtains 6.1g grams of product, MS (m/e)：857, compound P14 core
Magnetic spectrum figure (1H) is as shown in accompanying drawing 5.
Embodiment 23
Shown in compound manufactured in the present embodiment such as formula (P15)：
The same P2 of synthetic method, simply changes M2 into M7, obtains 4.1g grams of product, MS (m/e)：525.
Embodiment 24
Shown in compound manufactured in the present embodiment such as formula (P16)：
The same P7 of synthetic method, simply changes M2 into M3, obtains 6.7g grams of product, MS (m/e)：919.
Embodiment 25
Shown in compound manufactured in the present embodiment such as formula (P17)：
The same P13 of synthetic method, simply changes M2 into M3, obtains 3.3g grams of product, MS (m/e)：845.
Embodiment 26
Shown in compound manufactured in the present embodiment such as formula (P18)：
The same P3 of synthetic method, simply changes M2 into M4, obtains 5.7g grams of product, MS (m/e)：693.
Embodiment 27
Shown in compound manufactured in the present embodiment such as formula (P19)：
The same P2 of synthetic method, simply changes M2 into M4, obtains 4.1g grams of product, MS (m/e)：541.
Embodiment 28
Shown in compound manufactured in the present embodiment such as formula (P21)：
The same P8 of synthetic method, simply changes M2 into M5, obtains 5.6g grams of product, MS (m/e)：733.
Embodiment 29
Shown in compound manufactured in the present embodiment such as formula (P22)：
The same P3 of synthetic method, simply changes M2 into M5, obtains 6.1g grams of product, MS (m/e)：773.
Embodiment 30
Shown in compound manufactured in the present embodiment such as formula (P23)：
The same P12 of synthetic method, simply changes M2 into M8, obtains 2.1g grams of product, MS (m/e)：707.
Embodiment 31
Shown in compound manufactured in the present embodiment such as formula (P24)：
The same P3 of synthetic method, simply changes M2 into M8, obtains 2.1g grams of product, MS (m/e)：705.
Embodiment 32
Shown in compound manufactured in the present embodiment such as formula (P25)：
The same P1 of synthetic method, simply changes M2 into M9, obtains 3.0g grams of product, MS (m/e)：843.
Embodiment 33
Shown in compound manufactured in the present embodiment such as formula (P26)：
The same P3 of synthetic method, simply changes M2 into M9, obtains 5.6g grams of product, MS (m/e)：841.
Embodiment 34
Shown in compound manufactured in the present embodiment such as formula (P27)：
The same P2 of synthetic method, simply changes M2 into M6, obtains 5.0g grams of product, MS (m/e)：553.
Embodiment 35
Shown in compound manufactured in the present embodiment such as formula (P28)：
The same P3 of synthetic method, simply changes M2 into M6, obtains 5.2g grams of product, MS (m/e)：705.
It is the Application Example of the compounds of this invention below：
The typical structure of OLED organic electroluminescence devices is：
Substrate/anode/hole transmission layer (HTL)/organic luminous layer (EL)/electron transfer layer (ETL)/negative electrode
Substrate can use the substrate in conventional organic luminescence organic electroluminescence device, such as：Glass or plastics.Anode
Material can use transparent high conductivity material, such as indium tin oxygen (ITO), indium zinc oxygen (IZO), tin ash (SnO2), oxygen
Change zinc (ZnO) etc..Glass substrate is selected in the organic electroluminescence device of the present invention makes, ITO makees anode material.
Hole transmission layer can use N, N '-two (3- tolyls)-N, N '-diphenyl-[1,1- xenyls] -4,4 '-two
Amine (TPD) or N, N ' the tri-arylamine group material such as-diphenyl-N, N '-two (1- naphthyls)-(1,1 '-xenyl) -4,4 '-diamines (NPB)
Material.Wherein NPB is conventional hole mobile material, and selected hole passes in the organic electroluminescence device of the present invention makes
Defeated material selection NPB.
Organic electroluminescence device structure can be that single-shot photosphere can also be multi-luminescent layer structure.
Electron transfer layer either TAZ or TPBi or is derived from any two kinds of collocation of these three materials using Alq3.
Selected cathode material is LiF/Al in the organic electroluminescence device of the present invention makes.
The different materials concrete structure used in the present invention is seen below：
Embodiment 36：
The present embodiment prepares 16 organic electroluminescence devices altogether, and its structure is：ITO/NPB(40nm)/EM1(30nm)/
ETL materials (20nm)/LiF (0.5nm)/Al (150nm)；
One of contrast organic electroluminescence device, electron transport material select Bphen, remaining 15 organic electroluminescence hair
Material of the optical device from the present invention.
Organic electroluminescence device preparation process is as follows in the present embodiment：
The glass plate for being coated with transparent conductive layer is ultrasonically treated in commercial detergent, rinsed in deionized water,
In acetone：Ultrasonic oil removing in alcohol mixed solvent, it is baked under clean environment and removes moisture content completely, it is clear with ultraviolet light and ozone
Wash, and with low energy cation beam bombarded surface；
The above-mentioned glass substrate with anode is placed in vacuum chamber, is evacuated to 1 × 10-5~9 × 10-3Pa, above-mentioned
Anode tunic vacuum evaporation NPB is 50nm as hole transmission layer, evaporation rate 0.1nm/s, evaporation thickness；
Luminescent layers of the vacuum evaporation EM1 as device on hole transmission layer, evaporation rate 0.1nm/s, evaporation are total
Thickness is 30nm；
The electricity of one layer of vacuum evaporation compound or Bphen of the invention as organic electroluminescence device on luminescent layer
Sub- transport layer, its evaporation rate are 0.1nm/s, and evaporation total film thickness is 50nm；
Vacuum evaporation 0.5nm LiF is as electron injecting layer on electron transfer layer (ETL), and 150nm Al is as cloudy
Pole.
Organic electroluminescence device performance see the table below：
By upper table, it can be seen that, organic material of the invention may be used as electron transfer layer in organic electroluminescence device
Materials'use.
Embodiment 37：
The compound of the present invention is as the material of main part in red phosphorescent OLED organic electroluminescence devices：
7 organic electroluminescence devices are prepared altogether, and organic electroluminescence device structure is：
ITO/NPB (20nm)/feux rouges material of main part (30nm)：Ir (piq) 3 [5%]/TPBI (10nm)/Alq3 (15nm)/
LiF(0.5nm)/Al(150nm)。
One of them is contrast organic electroluminescence device, and feux rouges material of main part selects CBP, other 6 organic electroluminescences hairs
Material of the optical device from the present invention.
Organic electroluminescence device preparation process is as follows：The glass plate for being coated with transparent conductive layer is cleaned in commercialization
It is ultrasonically treated in agent, rinses in deionized water, in acetone：Ultrasonic oil removing in alcohol mixed solvent, is toasted under clean environment
Moisture content is removed to complete, with ultraviolet light and ozone clean, and with low energy cation beam bombarded surface；
The above-mentioned glass substrate with anode is placed in vacuum chamber, is evacuated to 1 × 10-5~9 × 10-3Pa,
Vacuum evaporation hole transmission layer NPB on above-mentioned anode tunic, evaporation rate 0.1nm/s, evaporation thickness are 20nm；
Vacuum evaporation light emitting host material and dyestuff on hole transmission layer, as the luminous of organic electroluminescence device
Layer, evaporation rate 0.1nm/s, evaporation total film thickness is 30nm；
Vacuum evaporation electron transfer layer TPBI and Alq3, its evaporation rate are 0.1nm/s successively on luminescent layer, are steamed
It is respectively 10nm and 15nm to plate thickness；
Vacuum evaporation 0.5nm LiF on the electron transport layer, 150nm Al are as negative electrode.
Organic electroluminescence device performance see the table below：
By upper table it can be seen that, using chemical combination of the present invention as phosphorescence host organic electroluminescence device relative to use
CBP obtains preferable effect as the organic electroluminescence device of main body, obtains higher current efficiency and relatively low drive
Dynamic voltage.
Embodiment 38：
The compound of the present invention is as the material of main part in green phosphorescent OLED organic electroluminescence devices：
8 organic electroluminescence devices are prepared altogether, and organic electroluminescence device structure is：
ITO/NPB (20nm)/green glow material of main part (30nm)：Ir (ppy) 3 [7%]/TPBI (10nm)/Alq3 (15nm)/
LiF(0.5nm)/Al(150nm)。
One of them is contrast organic electroluminescence device, and green glow material of main part selects CBP, other 7 organic electroluminescences
Material of the luminescent device from the present invention.
Organic electroluminescence device preparation process is as follows：The glass plate for being coated with transparent conductive layer is cleaned in commercialization
It is ultrasonically treated in agent, rinses in deionized water, in acetone：Ultrasonic oil removing in alcohol mixed solvent, is toasted under clean environment
Moisture content is removed to complete, with ultraviolet light and ozone clean, and with low energy cation beam bombarded surface；
The above-mentioned glass substrate with anode is placed in vacuum chamber, is evacuated to 1 × 10-5~9 × 10-3Pa,
Vacuum evaporation hole transmission layer NPB on above-mentioned anode tunic, evaporation rate 0.1nm/s, evaporation thickness are 20nm；
Vacuum evaporation light emitting host material and dyestuff on hole transmission layer, as the luminous of organic electroluminescence device
Layer, evaporation rate 0.1nm/s, evaporation total film thickness is 30nm；
Vacuum evaporation electron transfer layer TPBI and Alq3, its evaporation rate are 0.1nm/s successively on luminescent layer, are steamed
It is respectively 10nm and 15nm to plate thickness；
Vacuum evaporation 0.5nm LiF on the electron transport layer, 150nm Al are as electron injecting layer and negative electrode.
Organic electroluminescence device performance see the table below：
By upper table it can be seen that, using chemical combination of the present invention as phosphorescence host organic electroluminescence device relative to use
CBP obtains preferable effect as the organic electroluminescence device of main body, obtains higher current efficiency and relatively low drive
Dynamic voltage.
Obviously, above-described embodiment is only intended to clearly illustrate example, and is not the restriction to embodiment.It is right
For those of ordinary skill in the art, can also make on the basis of the above description it is other it is various forms of change or
Change.There is no necessity and possibility to exhaust all the enbodiments.And the obvious change thus extended out or
Among changing still in the protection domain of the invention.
Claims (4)
1. a kind of organic electroluminescence device, contain simultaneously [2, the 1-a] Benzazole compounds of 6- hydrogen iso-indoles shown in formula (1)：
Wherein：X is selected from methyl, ethyl, propyl group, isopropyl, normal-butyl, isobutyl group, amyl group, isopentyl, cyclopenta, alkyl substitution
Cyclopenta, n-hexyl, cyclohexyl, alkyl-substituted cyclohexyl, phenyl, alkyl-substituted phenyl, benzyl；
R1 is selected from pyridine radicals, substituted pyridinyl, pyridinylphenyl, benzimidazole, substituted benzimidazole, benzothiazole, substituted benzene
And thiazole, pyrimidine, substituted pyrimidines, pyrazine, substitution pyrazine, substitution triazine, quinolyl or isoquinolyl；
The organic electroluminescence device is Green organic light emitting diode.
2. organic electroluminescence device according to claim 1, it is characterised in that the different Yin of 6- hydrogen shown in formula (1) therein
Simultaneously [2,1-a] Benzazole compounds are selected from following structure to diindyl：
3. organic electroluminescence device according to claim 1, it is characterised in that including substrate, and be sequentially formed at institute
State anode layer, several luminescence unit layers and the cathode layer on substrate；
Described luminescence unit layer includes hole transmission layer, luminescent layer and electron transfer layer；
The luminescent layer is green light emitting layer；
The material of main part of the green light emitting layer is 6- hydrogen iso-indoles simultaneously [2,1-a] Benzazole compounds described in formula (1).
4. organic electroluminescence device according to claim 3, it is characterised in that：
The material of main part of the green light emitting layer is selected from following compound：
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| CN201710818055.7A Withdrawn CN107556321A (en) | 2013-09-29 | 2013-09-29 | A kind of organic electroluminescence device |
| CN201710814416.0A Withdrawn CN107602562A (en) | 2013-09-29 | 2013-09-29 | The synthetic method of 6 hydrogen iso-indoles simultaneously [2,1 a] Benzazole compounds |
| CN201710818081.XA Active CN107546339B (en) | 2013-09-29 | 2013-09-29 | A kind of organic electroluminescence device |
| CN201310456007.XA Active CN104513244B (en) | 2013-09-29 | 2013-09-29 | Simultaneously [2,1 a] Benzazole compounds and its application of 6 hydrogen iso-indoles |
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| CN201710818055.7A Withdrawn CN107556321A (en) | 2013-09-29 | 2013-09-29 | A kind of organic electroluminescence device |
| CN201710814416.0A Withdrawn CN107602562A (en) | 2013-09-29 | 2013-09-29 | The synthetic method of 6 hydrogen iso-indoles simultaneously [2,1 a] Benzazole compounds |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1395454A (en) * | 2002-06-05 | 2003-02-05 | 谢爽 | organic electroluminescent device |
| US20030228487A1 (en) * | 2002-05-14 | 2003-12-11 | Lightronik Technology Inc., | Organic electroluminescence element |
| WO2012040923A1 (en) * | 2010-09-29 | 2012-04-05 | Merck Sharp & Dohme Corp. | Tetracyclic indole derivatives and methods of use thereof for the treatment of viral diseases |
| WO2012050848A1 (en) * | 2010-09-29 | 2012-04-19 | Schering Corporation | Fused tetracycle derivatives and methods of use thereof for the treatment of viral diseases |
-
2013
- 2013-09-29 CN CN201710819240.8A patent/CN107573927B/en active Active
- 2013-09-29 CN CN201710818055.7A patent/CN107556321A/en not_active Withdrawn
- 2013-09-29 CN CN201710814416.0A patent/CN107602562A/en not_active Withdrawn
- 2013-09-29 CN CN201710818081.XA patent/CN107546339B/en active Active
- 2013-09-29 CN CN201310456007.XA patent/CN104513244B/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20030228487A1 (en) * | 2002-05-14 | 2003-12-11 | Lightronik Technology Inc., | Organic electroluminescence element |
| CN1395454A (en) * | 2002-06-05 | 2003-02-05 | 谢爽 | organic electroluminescent device |
| WO2012040923A1 (en) * | 2010-09-29 | 2012-04-05 | Merck Sharp & Dohme Corp. | Tetracyclic indole derivatives and methods of use thereof for the treatment of viral diseases |
| WO2012050848A1 (en) * | 2010-09-29 | 2012-04-19 | Schering Corporation | Fused tetracycle derivatives and methods of use thereof for the treatment of viral diseases |
Also Published As
| Publication number | Publication date |
|---|---|
| CN107573927A (en) | 2018-01-12 |
| CN107602562A (en) | 2018-01-19 |
| CN107573927B (en) | 2019-10-15 |
| CN104513244A (en) | 2015-04-15 |
| CN104513244B (en) | 2017-12-08 |
| CN107556321A (en) | 2018-01-09 |
| CN107546339B (en) | 2019-02-05 |
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