CN104119274A - 有机电致发光器件 - Google Patents
有机电致发光器件 Download PDFInfo
- Publication number
- CN104119274A CN104119274A CN201410169455.6A CN201410169455A CN104119274A CN 104119274 A CN104119274 A CN 104119274A CN 201410169455 A CN201410169455 A CN 201410169455A CN 104119274 A CN104119274 A CN 104119274A
- Authority
- CN
- China
- Prior art keywords
- unsubstituted
- substituent
- alkyl
- layer
- organic electroluminescence
- 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.)
- Granted
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- 239000000463 material Substances 0.000 claims abstract description 46
- 238000005401 electroluminescence Methods 0.000 claims abstract description 35
- 239000012044 organic layer Substances 0.000 claims abstract description 15
- 239000010410 layer Substances 0.000 claims description 100
- 125000001424 substituent group Chemical group 0.000 claims description 50
- 150000001875 compounds Chemical class 0.000 claims description 31
- 125000003118 aryl group Chemical group 0.000 claims description 28
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 26
- -1 n-octyl Chemical group 0.000 claims description 23
- 230000005540 biological transmission Effects 0.000 claims description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- 239000001257 hydrogen Substances 0.000 claims description 20
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 20
- 125000003545 alkoxy group Chemical group 0.000 claims description 16
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 14
- 238000002347 injection Methods 0.000 claims description 14
- 239000007924 injection Substances 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- 230000027756 respiratory electron transport chain Effects 0.000 claims description 11
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000001624 naphthyl group Chemical group 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 238000004528 spin coating Methods 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- 238000010025 steaming Methods 0.000 claims description 5
- 125000003368 amide group Chemical group 0.000 claims description 4
- 150000001412 amines Chemical class 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
- 229910052805 deuterium Inorganic materials 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 4
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 claims description 4
- 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 4
- 239000000203 mixture Substances 0.000 claims description 4
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims 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 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 239000000377 silicon dioxide Substances 0.000 claims description 4
- 230000000903 blocking effect Effects 0.000 claims description 3
- 239000003205 fragrance Substances 0.000 claims description 3
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 2
- 238000006579 Tsuji-Trost allylation reaction Methods 0.000 claims description 2
- 125000005110 aryl thio group Chemical group 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- 229910052796 boron Inorganic materials 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 125000003944 tolyl group Chemical group 0.000 claims description 2
- 229920002554 vinyl polymer Polymers 0.000 claims description 2
- 239000000126 substance Substances 0.000 abstract description 3
- 239000011368 organic material Substances 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 239000008367 deionised water Substances 0.000 description 10
- 229910021641 deionized water Inorganic materials 0.000 description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 229940125782 compound 2 Drugs 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 6
- 239000011521 glass Substances 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 239000000758 substrate Substances 0.000 description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
- 239000003599 detergent Substances 0.000 description 5
- 239000001301 oxygen Substances 0.000 description 5
- 238000009832 plasma treatment Methods 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 238000004440 column chromatography Methods 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 230000006837 decompression Effects 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- ZEEBGORNQSEQBE-UHFFFAOYSA-N [2-(3-phenylphenoxy)-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound C1(=CC(=CC=C1)OC1=NC(=CC(=C1)CN)C(F)(F)F)C1=CC=CC=C1 ZEEBGORNQSEQBE-UHFFFAOYSA-N 0.000 description 2
- SAHIZENKTPRYSN-UHFFFAOYSA-N [2-[3-(phenoxymethyl)phenoxy]-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound O(C1=CC=CC=C1)CC=1C=C(OC2=NC(=CC(=C2)CN)C(F)(F)F)C=CC=1 SAHIZENKTPRYSN-UHFFFAOYSA-N 0.000 description 2
- ABRVLXLNVJHDRQ-UHFFFAOYSA-N [2-pyridin-3-yl-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound FC(C1=CC(=CC(=N1)C=1C=NC=CC=1)CN)(F)F ABRVLXLNVJHDRQ-UHFFFAOYSA-N 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 150000001342 alkaline earth metals Chemical class 0.000 description 2
- 229910052792 caesium Inorganic materials 0.000 description 2
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 2
- 238000000151 deposition Methods 0.000 description 2
- 230000008021 deposition Effects 0.000 description 2
- 150000002220 fluorenes Chemical class 0.000 description 2
- 230000005525 hole transport Effects 0.000 description 2
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 2
- 238000007639 printing Methods 0.000 description 2
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 2
- 150000003248 quinolines Chemical class 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- 230000003245 working effect Effects 0.000 description 2
- OIRHKGBNGGSCGS-UHFFFAOYSA-N 1-bromo-2-iodobenzene Chemical compound BrC1=CC=CC=C1I OIRHKGBNGGSCGS-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
- DMEVMYSQZPJFOK-UHFFFAOYSA-N 3,4,5,6,9,10-hexazatetracyclo[12.4.0.02,7.08,13]octadeca-1(18),2(7),3,5,8(13),9,11,14,16-nonaene Chemical group N1=NN=C2C3=CC=CC=C3C3=CC=NN=C3C2=N1 DMEVMYSQZPJFOK-UHFFFAOYSA-N 0.000 description 1
- BWCDLEQTELFBAW-UHFFFAOYSA-N 3h-dioxazole Chemical compound N1OOC=C1 BWCDLEQTELFBAW-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 229910021595 Copper(I) iodide Inorganic materials 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- VAMXMNNIEUEQDV-UHFFFAOYSA-N Methyl anthranilate Natural products COC(=O)C1=CC=CC=C1N VAMXMNNIEUEQDV-UHFFFAOYSA-N 0.000 description 1
- IIRVBNFPODABQL-UHFFFAOYSA-N N,N-diphenylaniline ethene Chemical group C1(=CC=CC=C1)N(C1=CC=CC=C1)C1=CC=CC=C1.C=C IIRVBNFPODABQL-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- HHRFWSALGNYPHA-UHFFFAOYSA-N [N].C1CNCCN1 Chemical class [N].C1CNCCN1 HHRFWSALGNYPHA-UHFFFAOYSA-N 0.000 description 1
- 150000001339 alkali metal compounds Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001454 anthracenes Chemical class 0.000 description 1
- BBEAQIROQSPTKN-UHFFFAOYSA-N antipyrene Natural products C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 1
- 229940111121 antirheumatic drug quinolines Drugs 0.000 description 1
- YCOXTKKNXUZSKD-UHFFFAOYSA-N as-o-xylenol Natural products CC1=CC=C(O)C=C1C YCOXTKKNXUZSKD-UHFFFAOYSA-N 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 229910052728 basic metal Inorganic materials 0.000 description 1
- 150000003818 basic metals Chemical class 0.000 description 1
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-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
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 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
- 239000013522 chelant Substances 0.000 description 1
- 150000004697 chelate complex Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 1
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000011982 device technology Methods 0.000 description 1
- 239000012776 electronic material Substances 0.000 description 1
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 1
- 238000000119 electrospray ionisation mass spectrum Methods 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000012065 filter cake Substances 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
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- SNHMUERNLJLMHN-UHFFFAOYSA-N iodobenzene Chemical compound IC1=CC=CC=C1 SNHMUERNLJLMHN-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
- 229920002521 macromolecule Polymers 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 235000014380 magnesium carbonate Nutrition 0.000 description 1
- 229960001708 magnesium carbonate Drugs 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
- NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- AZQWKYJCGOJGHM-UHFFFAOYSA-N para-benzoquinone Natural products O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 1
- 150000002964 pentacenes Chemical class 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- 150000005041 phenanthrolines Chemical class 0.000 description 1
- 150000002988 phenazines Chemical class 0.000 description 1
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920006389 polyphenyl polymer Polymers 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D219/00—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems
- C07D219/04—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
- C07D219/08—Nitrogen atoms
-
- 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
- C07D401/14—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 three or more hetero 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
- C07D405/14—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 three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- 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
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/12—Light sources with substantially two-dimensional radiating surfaces
- H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
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Abstract
本发明涉及有机电致发光器件,包含阳极,阴极和一层或多层有机层,有机层至少包含一种具有如下化学式I所述结构式的材料,采用该有机发光材料制作的有机电致发光器件具有电致发光效率良好和色纯度优异以及寿命长的优点。化学式I。
Description
技术领域
本发明涉及新型的有机电子材料,可以通过真空蒸渡沉积或者旋涂成薄膜,应用在有机电致发光二极管上,属于有机电致发光器件领域。
背景技术
有机电致发光器件作为一种新型的显示技术,具有自发光、宽视角、低能耗、效率高、薄、色彩丰富、响应速度快、适用温度范围广、低驱动电压、可制作柔性可弯曲与透明的显示面板以及环境友好等独特优点,因此,有机电致发光器件技术可以应用在平板显示器和新一代照明上,也可以作为LCD的背光源。
有机电致发光器件为在两个金属电极之间通过旋涂或者真空蒸渡沉积一层有机材料而制备的器件,一个经典的三层有机电致发光器件包含空穴传输层,发光层和电子传输层。由阳极产生的空穴经空穴传输层跟由阴极产生的电子经电子传输层结合在发光层形成激子,而后发光。有机电致发光器件可以通过改变发光层的材料来发射红光,绿光和蓝光。也可以通过在发光层进行材料搭配,使器件发射白光。
可是,现在的OLED器件由于效率低,使用寿命短等因素制约其应用,因此要改善这些条件的限制。其中,降低空穴注入/传输材料与发光材料之间的能垒和提到空穴传输材料的热稳定性有助于改善OLED器件的效率和提高使用寿命。另外,由于小分子的空穴注入/传输材料的溶解性比较差,只能通过蒸渡来制备器件,不利于商品化使用,因此发展良好溶解性的高空穴迁移率的材料实现旋涂或者喷墨打印有利于大面积应用。
已有使用的空穴注入材料copper phthalocyanine(CuPc),其降解慢,制备耗能高,不利于环境保护。而常见的空穴传输材料为TPD和NPB,尽管具有很好的空穴迁移率,分别是1.0*10-3和5.1*10-4cm2V-1S-1,但是这两个材料的玻璃化温度分别为65℃和98℃,其稳定性还是远远不能满足oled的应用需求。因而,需要发展高效和稳定性的有机电致发光材料,才能制备高效稳定的有机电致发光器件。
发明内容
本发明就是克服上面化合物的缺陷,提供一系列具有较好热稳定性,高空穴迁移率和良好溶解性的空穴传输、注入材料,并通过这些材料制备制具有电致发光效率良好和色纯度优异以及寿命长的有机电致发光器件。
本发明提供的有机电致发光器件,该器件包含阳极,阴极和一层或多层有机层。所述有机层可以包括空穴注入层,空穴传输层,发光层,空穴阻挡层,电子传输层和电子注入层。需要特别指出,上述有机层可以根据需要,不必每层都存在。
一种有机电致发光器件,包含阳极,阴极和一层或多层有机层,有机层中至少有一层包含一种具有如下化学式I所述结构式的材料:
其中,R1-R3独立地表示为氢,氘原子,卤素,氰基,硝基,胺基,C1-C8烷基、C1-C8烷氧基,C6-C30的含一个或者多个取代基R或者未取代的芳基,C3-C30的含一个或者多个取代基R或者未取代的含有一个或者多个的杂原子芳基,C2-C8的含一个或者多个取代基R或者未取代的烯烷基,C2-C8的含一个或者多个取代基R取代或者未取代的炔烷基,C8-C30的含一个或者多个取代基R取代或者未取代的二芳乙烯基,C8-C30的含一个或者多个取代基R取代或者未取代的二芳乙炔基,三烷基硅,C6-C30的含一个或者多个取代基R或者未取代的三芳香硅基,C6-C30的含一个或者多个取代基R或者未取代的二芳香氧磷基、C6-C30的含一个或者多个取代基R或者未取代的芳香羰基、C6-C30的含一个或者多个取代基R或者未取代的芳硫基,C6-C30的含一个或者多个取代基R或者未取代的芳香稠环基,C6-C30的含杂原子的取代或者未取代的芳香稠环基,C6-C30含一个或者多个取代基R或者未取代的咔唑基,C6-C30的含一个或者多个取代基R或者未取代的二芳香胺基,或者两个R2基团之间形成螺结构,所述杂原子为B,O,S,N,Se;
Ar1-Ar2独立地表示为C6-C30的含有一个或者多个取代基R的芳基,含一个或者多个取代基R或者未取代的芳香稠环基,C6-C30的含一个或者多个取代基R或者未取代的咔唑基,C6-C30的含一个或者多个取代基R或者未取代的三芳香胺基,
其中R独立地表示烷基,五元或六元环的芳基,烷氧基,氘,卤素,氰基,硝基,胺基。
进一步优选:其中R1-R3独立地选自氢,卤素、C1-C8烷基,C6-C30的含有一个或者多个取代基R或者未取代的苯基,含有一个或者多个取代基R或者未取代的二芳香胺基,C6-C30的含有一个或者多个取代基R或者未取代的芳香稠环基,C6-C30的含一个或者多个取代基R或者未取代的咔唑基,或者两个R2形成螺芴结构;Ar1-Ar2独立地表示为含有一个或者多个取代基R的芳基,C6-C30的含一个或者多个取代基R或者未取代的芳香稠环基,C6-C30的含一个或者多个取代基R或者未取代的咔唑基,C6-C30的含一个或者多个取代基R或者未取代的三芳香胺基,其中R独立地表示烷基,五元或六元环的芳基,烷氧基,卤素。
更进一步优选:其中R1-R3独立地选自氢,C1-C8烷基,一个或者多个C1-C3烷基、C1-C3烷氧基、芳香基取代的或者未取代的苯基,一个或者多个C1-C3烷基、C1-C3烷氧基、芳香基取代的或者未取代的萘基,一个或者多个C1-C3烷基、C1-C3烷氧基、芳香基取代的或者未取代的二芳香胺基,含有一个或者多个C1-C3烷基、C1-C3烷氧基、芳香基取代或者未取代的咔唑基,或者两个R2基团之间形成螺结构。
更优选:其中R1,R2独立地选自氢,甲基,乙基,丙基,异丙基,丁基,叔丁基,正戊基,异戊基,正己基,异己基,环己基,正辛基,异辛基,C1-C3烷基取代或未取代的苯基,C1-C3烷氧基取代或未取代的苯基,萘基,或者两个R2基团之间形成螺结构,一个或者多个甲基、苯基取代或者未取代的二芳香胺基,一个或者多个甲基、苯基取代或者未取代的咔唑基,R3独立地选自氢,C1-C8的烷基,C1-C3取代或者未取代的苯基。
更优选:其中R1,R2独立地选自氢,甲基,乙基,丙基,异丙基,丁基,叔丁基,正戊基,异戊基,正己基,异己基,环己基,正辛基,异辛基,苯基,甲苯基,其中R3独立地选自氢,C1-C3烷基,C1-C3烷基取代或未取代的苯基。
最优选:其中R3优选为氢,甲基,苯基,R1、R2独立地选自氢,甲基,叔丁基,苯基或者两个R2基团之间形成螺结构,Ar1-Ar2独立的表示为下列表中任一基团。
如上面提到的,本发明的具体实施例如下,但是不限于这些:
最优选:其中R1、R2、R3独立地选自氢,甲基,苯基,Ar1-Ar2独立的表示苯基、萘基或联苯基。
所述一层或多层有机层分别为空穴注入层,空穴传输层,发光层,空穴阻挡层和电子传输层中一种或多层。
所述式(I)所述的材料应用于空穴注入层,空穴传输层和/或发光层中。
所述式(I)所述的材料作为空穴注入材料或者空穴传输材料时,可以单一材料作为一层,也可以多种材料搭配组成一层。
所述式(I)所述的材料作为发光层时,可以作为单一发光层或者掺杂其他材料作为发光层。
所述有机层可以通过蒸渡或旋涂制备成薄膜。
本发明的有机电致发光器件至少包含一层如结构式I所述有机材料作为空穴传输层或者空穴注入层。可以单独以一层形式存在,也可以跟其他化学组分混合使用。
本发明的有机电致发光器件可以包含有一层发光层,该发光层至少包含一个具有结构式I的化合物。该发光层的发光区域在380-740nm范围内,覆盖整个白光区域。优选本发明范围在380-550nm,更优选发射蓝光,范围在440-490nm。
结构式I化合物作为发光层时,可以作为无掺杂单一发光层或掺杂发光层。
所述掺杂发光层包括主体材料和客体材料,结构式I化合物根据需要可以是主体材料或者客体材料。包括同时使用结构式I的两个化合物分别作主体材料和客体材料。
当结构式I化合物作为主体材料时,其浓度为整个发光层重量的20-99.9%,优选80-99%,更优选为90-99%。结构式I化合物作为客体材料时,其浓度为这个发光层重量的0.01-80%,优选1-20%,更优选为1-10%。
本发明中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有机发光层上。除了上述具有结构式I所述材料外,还可以包括小分子和高分子有机材料,可以包含如下,但是不限于这些,三芳香胺化合物,联苯二胺化合物,噻唑化合物,恶唑化合物,咪唑类化合物,芴类化合物,酞菁类化合物,六氰基六杂三苯(hexanitrile hexaazatriphenylene),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,聚苯磺酸。
本发明的有机电致发光层,除含有本发明的化合物外,还可以含有如下化合物,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,屈类化合物,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。
本发明的有机电子器件使用的有机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,可以选择如下化合物,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,氟取代苯类化合物。
本发明的有机电子器件根据需要,可以加入一层电子注入层,该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,可以选择如下化合物,但是不限于此,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。
本发明的电子器件有机层的总厚度为1-1000nm,优选1-500nm,更优选50-300nm。
本发明的有机电致发光器件中的每一层,可以通过蒸渡或者旋涂的方式,或者喷墨打印等方式制备。本发明使用蒸渡方式制备是,是通过真空蒸渡,真空度为小于10-5bar,优选小于10-6bar。
器件实验表明,本发明如式(I)所述的有机发光材料,具有较好热稳定性,高空穴迁移率,高发光效率,高发光纯度。采用该有机发光材料制作的有机电致发光器件具有电致发光效率良好和色纯度优异以及寿命长的优点。
附图说明
图1为本发明的器件结构图,10代表为玻璃基板,20代表为阳极,30代表为空穴注入层,40代表为空穴传输层,50代表为发光层,60代表为电子传输层,70代表为电子注入层,80代表为阴极。
图2为本发明的实施例3,实施例5,比较例1器件的电流密度与电压图
图3为本发明的实施例3,实施例5,比较例1器件的发光效率与电流密度图
图4为本发明的实施例1的化合物2的电喷雾离子化质谱图
具体实施方式
为了更详细叙述本发明,特举以下例子,但是不限于此。
实施例1
化合物2的合成
中间体1-1的合成
在1L的三口烧瓶中加入化合物邻氨基苯甲酸甲酯和对溴碘苯,碘化亚铜,和碳酸钾,邻二氯苯,氮气保护下,加热到180度24小时,冷却至100度,过滤,滤液减压除去溶剂,然后用柱层析过柱子分离得到化合物1-1。收率92%,HPLC纯度96%
中间体1-2的合成
在1L的三口烧瓶中,加入化合物1-1,和四氢呋喃,氮气保护下,冷却至0度,然后滴加甲基溴化镁试剂,滴完,缓慢升温至室温,过夜反应,然后加入1N的盐酸水溶液中,用乙酸乙酯萃取,干燥,浓缩,而后用柱层析过柱分离得到化合物1-2。收率83%,HPLC纯度93%。中间体1-3的合成
在1L的三口烧瓶中,加入化合物1-2,磷酸,搅拌,反应完全,加入水中,过滤,滤饼用甲醇洗涤2遍,得到中间体1-3。收率80%HPLC含量90%
中间体1-4的合成
在1L的三口烧瓶中加入化合物1-3和碘苯,叔丁醇钾,三叔丁基磷,二甲苯,氮气保护下,加热到120度24小时,冷却至室温,过滤,滤液减压除去溶剂,然后用柱层析过柱子分离得到化合物1-4。
化合物2的合成
在1L的三口烧瓶中加入化合物1-4和联苯二胺,叔丁醇钾,三叔丁基磷,二甲苯,氮气保护下,加热到120度24小时,冷却至100度,过滤,滤液减压除去溶剂,然后用柱层析过柱子分离得到化合物2。ESI-MS m/z902.4.
实施例2
有机电致发光器件的制备
使用本发明的有机电致发光材料制备OLED
首先,将透明导电ITO玻璃基板10(上面带有阳极20)依次经:洗涤剂溶液和去离子水,乙醇,丙酮,去离子水洗净,再用氧等离子处理30秒。
然后,在ITO上蒸渡10nm厚的化合物2作为空穴注入层30。
然后,蒸渡化合物NPB,形成60nm厚的空穴传输层40。
然后,在空穴传输层上蒸渡50nm厚的化合物Alq3作为发光层50。
然后,在发光层上蒸渡10nm厚的Alq3作为电子传输层60。
最后,蒸渡1nm Liq为电子注入层70和100nm Al作为器件阴极80。
实施例3
有机电致发光器件的制备
使用本发明的有机电致发光材料制备OLED
首先,将透明导电ITO玻璃基板10(上面带有阳极20)依次经:洗涤剂溶液和去离子水,乙醇,丙酮,去离子水洗净,再用氧等离子处理30秒。
然后,在ITO上蒸渡20nm厚的化合物2作为空穴注入层30。
然后,蒸渡化合物NPB,形成60nm厚的空穴传输层40。
然后,在空穴传输层上蒸渡50nm厚的化合物Alq3作为发光层50。
然后,在发光层上蒸渡10nm厚的Alq3作为电子传输层60。
最后,蒸渡1nm Liq为电子注入层70和100nm Al作为器件阴极80。
实施例4
有机电致发光器件的制备
使用本发明的有机电致发光材料制备OLED
首先,将透明导电ITO玻璃基板10(上面带有阳极20)依次经:洗涤剂溶液和去离子水,乙醇,丙酮,去离子水洗净,再用氧等离子处理30秒。
然后,在ITO上蒸渡30nm厚的化合物2作为空穴注入层30。
然后,蒸渡化合物NPB,形成60nm厚的空穴传输层40。
然后,在空穴传输层上蒸渡50nm厚的化合物Alq3作为发光层50。
然后,在发光层上蒸渡10nm厚的Alq3作为电子传输层60。
最后,蒸渡1nm Liq为电子注入层70和100nm Al作为器件阴极80。
实施例5
有机电致发光器件的制备
使用本发明的有机电致发光材料制备OLED
首先,将透明导电ITO玻璃基板10(上面带有阳极20)依次经:洗涤剂溶液和去离子水,乙醇,丙酮,去离子水洗净,再用氧等离子处理30秒。
然后,在ITO上蒸渡40nm厚的化合物2作为空穴注入层30。
然后,蒸渡化合物NPB,形成60nm厚的空穴传输层40。
然后,在空穴传输层上蒸渡50nm厚的化合物Alq3作为发光层50。
然后,在发光层上蒸渡10nm厚的Alq3作为电子传输层60。
最后,蒸渡1nm Liq为电子注入层70和100nm Al作为器件阴极80。
比较例1
有机电致发光器件的制备
使用本发明的有机电致发光材料制备OLED
首先,将透明导电ITO玻璃基板10(上面带有阳极20)依次经:洗涤剂溶液和去离子水,乙醇,丙酮,去离子水洗净,再用氧等离子处理30秒。
然后,在ITO上蒸渡化合物NPB,形成60nm厚的空穴传输层40。
然后,在空穴传输层上蒸渡50nm厚的化合物Alq3作为发光层50。
然后,在发光层上蒸渡10nm厚的Alq3作为电子传输层60。
最后,蒸渡1nm Liq为电子注入层70和100nm Al作为器件阴极80。
器件中所述结构式
器件发光数据检测如表1
表1为本发明的实施例2-5器件的CIE坐标
CIEx,CIEy | ||
化合物2,0nm | 比较例1 | 0.35,0.53 |
化合物2,10nm | 实施例2 | 0.35,0.53 |
化合物2,20nm | 实施例3 | 0.33,0.53 |
化合物2,30nm | 实施例4 | 0.33,0.53 |
化合物2,40nm | 实施例5 | 0.32,0.54 |
比较例1在没有本发明如式(I)所述的有机发光材料作为空穴注入材料,发光效率只有2.7cd/A,但加入作为空穴注入材料后,效果明显提升。在实施例5采用本发明如式(I)所述的有机发光材料作为40nm厚空穴注入材料,发光效率与比较例1相比增加超过37%达到3.7cd/A。
器件实验表明,本发明如式(I)所述的有机发光材料,具有较好热稳定性,高空穴迁移率,高发光效率,高发光纯度。采用该有机发光材料制作的有机电致发光器件具有电致发光效率良好和色纯度优异以及寿命长的优点。
Claims (13)
1.一种有机电致发光器件,包含阳极,阴极和一层或多层有机层,有机层中至少有一层包含一种具有如下化学式I所述结构式的材料:
其中,R1-R3独立地表示为氢,氘原子,卤素,氰基,硝基,胺基,C1-C8烷基、C1-C8烷氧基,C6-C30的含一个或者多个取代基R或者未取代的芳基,C3-C30的含一个或者多个取代基R或者未取代的含有一个或者多个的杂原子芳基,C2-C8的含一个或者多个取代基R或者未取代的烯烷基,C2-C8的含一个或者多个取代基R取代或者未取代的炔烷基,C8-C30的含一个或者多个取代基R取代或者未取代的二芳乙烯基,C8-C30的含一个或者多个取代基R取代或者未取代的二芳乙炔基,三烷基硅,C6-C30的含一个或者多个取代基R或者未取代的三芳香硅基,C6-C30的含一个或者多个取代基R或者未取代的二芳香氧磷基、C6-C30的含一个或者多个取代基R或者未取代的芳香羰基、C6-C30的含一个或者多个取代基R或者未取代的芳硫基,C6-C30的含一个或者多个取代基R或者未取代的芳香稠环基,C6-C30的含杂原子的取代或者未取代的芳香稠环基,C6-C30含一个或者多个取代基R或者未取代的咔唑基,C6-C30的含一个或者多个取代基R或者未取代的二芳香胺基,或者两个R2基团之间形成螺结构,所述杂原子为B,O,S,N,Se;
Ar1-Ar2独立地表示为C6-C30的含有一个或者多个取代基R的芳基,含一个或者多个取代基R或者未取代的芳香稠环基,C6-C30的含一个或者多个取代基R或者未取代的咔唑基,C6-C30的含一个或者多个取代基R或者未取代的三芳香胺基,
其中R独立地表示烷基,五元或六元环的芳基,烷氧基,氘,卤素,氰基,硝基,胺基。
2.根据权利要求1所述的有机电致发光器件,其中R1-R3独立地选自氢,卤素、C1-C8烷基,C6-C30的含有一个或者多个取代基R或者未取代的苯基,含有一个或者多个取代基R或者未取代的二芳香胺基,C6-C30的含有一个或者多个取代基R或者未取代的芳香稠环基,C6-C30的含一个或者多个取代基R或者未取代的咔唑基,或者两个R2形成螺芴结构;Ar1-Ar2独立地表示为含有一个或者多个取代基R的芳基,C6-C30的含一个或者多个取代基R或者未取代的芳香稠环基,C6-C30的含一个或者多个取代基R或者未取代的咔唑基,C6-C30的含一个或者多个取代基R或者未取代的三芳香胺基,其中R独立地表示烷基,五元或六元环的芳基,烷氧基,卤素。
3.根据权利要求2所述的有机电致发光器件,其中R1-R3独立地选自氢,C1-C8烷基,一个或者多个C1-C3烷基、C1-C3烷氧基、芳香基取代的或者未取代的苯基,一个或者多个C1-C3烷基、C1-C3烷氧基、芳香基取代的或者未取代的萘基,一个或者多个C1-C3烷基、C1-C3烷氧基、芳香基取代的或者未取代的二芳香胺基,含有一个或者多个C1-C3烷基、C1-C3烷氧基、芳香基取代或者未取代的咔唑基,或者两个R2基团之间形成螺结构。
4.根据权利要求3所述的有机电致发光器件,其中R1,R2独立地选自氢,甲基,乙基,丙基,异丙基,丁基,叔丁基,正戊基,异戊基,正己基,异己基,环己基,正辛基,异辛基,C1-C3烷基取代或未取代的苯基,C1-C3烷氧基取代或未取代的苯基,萘基,或者两个R2基团之间形成螺结构,一个或者多个甲基、苯基取代或者未取代的二芳香胺基,一个或者多个甲基、苯基取代或者未取代的咔唑基,R3独立地选自氢,C1-C8的烷基,C1-C3取代或者未取代的苯基。
5.根据权利要求4所述的有机电致发光器件,其中R1,R2独立地选自氢,甲基,乙基,丙基,异丙基,丁基,叔丁基,正戊基,异戊基,正己基,异己基,环己基,正辛基,异辛基,苯基,甲苯基,其中R3独立地选自氢,C1-C3烷基,C1-C3烷基取代或未取代的苯基。
6.根据权利要求5所述的有机电致发光器件,其中R3优选为氢,甲基,苯基,R1、R2独立地选自氢,甲基,叔丁基,苯基或者两个R2基团之间形成螺结构,Ar1-Ar2独立的表示为下列表中任一基团。
7.根据权利要求6所述的有机电致发光器件,其中式I所述的化合物具有如下结构:
8.根据权利要求7所述的有机电致发光器件,其中R1、R2、R3独立地选自氢,甲基,苯基,Ar1-Ar2独立的表示苯基、萘基或联苯基。
9.根据权利要求1-8任一所述的有机电致发光器件,所述一层或多层有机层分别为空穴注入层,空穴传输层,发光层,空穴阻挡层和电子传输层中一种或多层。
10.根据权利要求9所述的有机电致发光器件,所述式(I)所述的材料应用于空穴注入层,空穴传输层和/或发光层中。
11.根据权利要求10所述的有机电致发光器件,所述式(I)所述的材料作为空穴注入材料或者空穴传输材料时,可以单一材料作为一层,也可以多种材料搭配组成一层。
12.根据权利要求10所述的有机电致发光器件,所述式(I)所述的材料作为发光层时,可以作为单一发光层或者掺杂其他材料作为发光层。
13.根据权利要求1-12所述的有机电致发光器件,所述有机层可以通过蒸渡或旋涂制备成薄膜。
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CN106866499A (zh) * | 2016-12-26 | 2017-06-20 | 广东阿格蕾雅光电材料有限公司 | 有机空穴传输材料 |
WO2018120974A1 (zh) * | 2016-12-26 | 2018-07-05 | 广东阿格蕾雅光电材料有限公司 | 基于非对称有机空穴传输材料的仅空穴半导体二极管器件 |
WO2018120975A1 (zh) * | 2016-12-26 | 2018-07-05 | 广东阿格蕾雅光电材料有限公司 | 有机空穴传输材料 |
CN106848060B (zh) * | 2016-12-26 | 2019-05-14 | 广东阿格蕾雅光电材料有限公司 | 基于非对称有机空穴传输材料的仅空穴半导体二极管器件 |
CN106866499B (zh) * | 2016-12-26 | 2020-01-10 | 广东阿格蕾雅光电材料有限公司 | 有机空穴传输材料 |
CN108863918A (zh) * | 2018-06-19 | 2018-11-23 | 长春海谱润斯科技有限公司 | 一种芳胺衍生物及其有机电致发光器件 |
US11424417B2 (en) | 2018-11-16 | 2022-08-23 | Samsung Display Co., Ltd. | Organic electroluminescence device and compound for organic electroluminescence device |
CN111320636A (zh) * | 2018-12-17 | 2020-06-23 | 广东阿格蕾雅光电材料有限公司 | 一种有机电致发光材料及其应用 |
US11985893B2 (en) | 2019-11-08 | 2024-05-14 | Samsung Display Co., Ltd. | Organic electroluminescence device and aromatic compound for organic electroluminescence device |
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TWI541323B (zh) | 2016-07-11 |
CN104119274B (zh) | 2017-01-25 |
KR20160030877A (ko) | 2016-03-21 |
JP6133494B2 (ja) | 2017-05-24 |
HK1200825A1 (zh) | 2015-08-14 |
JP2016520253A (ja) | 2016-07-11 |
KR101831270B1 (ko) | 2018-04-04 |
TW201441340A (zh) | 2014-11-01 |
US20160111652A1 (en) | 2016-04-21 |
WO2014173323A1 (zh) | 2014-10-30 |
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