CN112638956B - 聚合物和包含其的有机发光器件 - Google Patents
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- CN112638956B CN112638956B CN201980055692.0A CN201980055692A CN112638956B CN 112638956 B CN112638956 B CN 112638956B CN 201980055692 A CN201980055692 A CN 201980055692A CN 112638956 B CN112638956 B CN 112638956B
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- 229920000642 polymer Polymers 0.000 title claims abstract description 46
- -1 dimethylfluorenyl Chemical group 0.000 claims description 54
- 239000000463 material Substances 0.000 claims description 33
- 239000000126 substance Substances 0.000 claims description 33
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- 238000002347 injection Methods 0.000 claims description 27
- 239000007924 injection Substances 0.000 claims description 27
- 125000003118 aryl group Chemical group 0.000 claims description 23
- 230000005525 hole transport Effects 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 8
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 125000000732 arylene group Chemical group 0.000 claims description 4
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
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- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
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- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
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- 125000000623 heterocyclic group Chemical group 0.000 description 10
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- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 7
- 125000003342 alkenyl group Chemical group 0.000 description 7
- 229910052799 carbon Inorganic materials 0.000 description 7
- 229940125904 compound 1 Drugs 0.000 description 7
- 229940125782 compound 2 Drugs 0.000 description 7
- 125000000753 cycloalkyl group Chemical group 0.000 description 7
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
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- 150000004982 aromatic amines Chemical class 0.000 description 6
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- 229910052751 metal Inorganic materials 0.000 description 6
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- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 6
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- 230000000694 effects Effects 0.000 description 5
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- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
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- 239000010405 anode material Substances 0.000 description 4
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- 125000004185 ester group Chemical group 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 102100029103 3-ketoacyl-CoA thiolase Human genes 0.000 description 3
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 101000841262 Homo sapiens 3-ketoacyl-CoA thiolase Proteins 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 125000002877 alkyl aryl group Chemical group 0.000 description 3
- 229910045601 alloy Inorganic materials 0.000 description 3
- 239000000956 alloy Substances 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- 125000001769 aryl amino group Chemical group 0.000 description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
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- 230000008021 deposition Effects 0.000 description 3
- ISAOCJYIOMOJEB-UHFFFAOYSA-N desyl alcohol Natural products C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 3
- 229910052733 gallium Inorganic materials 0.000 description 3
- 238000004770 highest occupied molecular orbital Methods 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 125000005462 imide group Chemical group 0.000 description 3
- 125000005647 linker group Chemical group 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- LSEFCHWGJNHZNT-UHFFFAOYSA-M methyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C)C1=CC=CC=C1 LSEFCHWGJNHZNT-UHFFFAOYSA-M 0.000 description 3
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 3
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 3
- 229910052709 silver Inorganic materials 0.000 description 3
- 239000004332 silver Substances 0.000 description 3
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
- 238000012546 transfer Methods 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- 125000006681 (C2-C10) alkylene group Chemical group 0.000 description 2
- FYGHSUNMUKGBRK-UHFFFAOYSA-N 1,2,3-trimethylbenzene Chemical compound CC1=CC=CC(C)=C1C FYGHSUNMUKGBRK-UHFFFAOYSA-N 0.000 description 2
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- IHTKIHCDXGNUHG-UHFFFAOYSA-N 1-bromo-4-[4-(4-ethenylphenoxy)butyl]benzene Chemical compound C1(CCCCOC2=CC=C(C=C)C=C2)=CC=C(Br)C=C1 IHTKIHCDXGNUHG-UHFFFAOYSA-N 0.000 description 2
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 2
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- RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- 239000005725 8-Hydroxyquinoline Substances 0.000 description 2
- OZAIFHULBGXAKX-VAWYXSNFSA-N AIBN Substances N#CC(C)(C)\N=N\C(C)(C)C#N OZAIFHULBGXAKX-VAWYXSNFSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
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- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 2
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- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
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- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 229920001774 Perfluoroether Polymers 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- 244000028419 Styrax benzoin Species 0.000 description 2
- 235000000126 Styrax benzoin Nutrition 0.000 description 2
- 235000008411 Sumatra benzointree Nutrition 0.000 description 2
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- 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
- 125000003282 alkyl amino group Chemical group 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
- 125000005264 aryl amine group Chemical group 0.000 description 2
- 125000003943 azolyl group Chemical group 0.000 description 2
- 229960002130 benzoin Drugs 0.000 description 2
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 2
- 239000012965 benzophenone Substances 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
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- XSIFPSYPOVKYCO-UHFFFAOYSA-N butyl benzoate Chemical compound CCCCOC(=O)C1=CC=CC=C1 XSIFPSYPOVKYCO-UHFFFAOYSA-N 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
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- 238000001816 cooling Methods 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- 125000002720 diazolyl group Chemical group 0.000 description 2
- 239000002019 doping agent Substances 0.000 description 2
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- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 2
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- 125000005843 halogen group Chemical group 0.000 description 2
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- 229930195733 hydrocarbon Natural products 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 description 2
- 239000011572 manganese Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- 125000002950 monocyclic group Chemical group 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 2
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 125000005702 oxyalkylene group Chemical group 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 229960003540 oxyquinoline Drugs 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- 238000005240 physical vapour deposition Methods 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229920000553 poly(phenylenevinylene) Polymers 0.000 description 2
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- 125000003367 polycyclic group Chemical group 0.000 description 2
- 239000003505 polymerization initiator Substances 0.000 description 2
- 238000006116 polymerization reaction Methods 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
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 2
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
- 238000012719 thermal polymerization Methods 0.000 description 2
- 125000000335 thiazolyl group Chemical group 0.000 description 2
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- 229910052725 zinc Inorganic materials 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
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- 238000011161 development Methods 0.000 description 1
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- 238000003618 dip coating Methods 0.000 description 1
- VFHVQBAGLAREND-UHFFFAOYSA-N diphenylphosphoryl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 VFHVQBAGLAREND-UHFFFAOYSA-N 0.000 description 1
- 238000005566 electron beam evaporation Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
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- KLKFAASOGCDTDT-UHFFFAOYSA-N ethoxymethoxyethane Chemical compound CCOCOCC KLKFAASOGCDTDT-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
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- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 1
- YLQWCDOCJODRMT-UHFFFAOYSA-N fluoren-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C2=C1 YLQWCDOCJODRMT-UHFFFAOYSA-N 0.000 description 1
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- 125000002541 furyl group Chemical group 0.000 description 1
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 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
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- 230000005283 ground state Effects 0.000 description 1
- 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 1
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- 125000005842 heteroatom Chemical group 0.000 description 1
- FHKSXSQHXQEMOK-UHFFFAOYSA-N hexane-1,2-diol Chemical compound CCCCC(O)CO FHKSXSQHXQEMOK-UHFFFAOYSA-N 0.000 description 1
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- 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 1
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- 238000007641 inkjet printing Methods 0.000 description 1
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- SKEDXQSRJSUMRP-UHFFFAOYSA-N lithium;quinolin-8-ol Chemical compound [Li].C1=CN=C2C(O)=CC=CC2=C1 SKEDXQSRJSUMRP-UHFFFAOYSA-N 0.000 description 1
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- AMTZBMRZYODPHS-UHFFFAOYSA-N manganese;quinolin-8-ol Chemical compound [Mn].C1=CN=C2C(O)=CC=CC2=C1.C1=CN=C2C(O)=CC=CC2=C1 AMTZBMRZYODPHS-UHFFFAOYSA-N 0.000 description 1
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- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical group [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 1
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- 239000001301 oxygen Substances 0.000 description 1
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- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
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- 125000003003 spiro group Chemical group 0.000 description 1
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- 238000006467 substitution reaction Methods 0.000 description 1
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- 150000003462 sulfoxides Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
- MDDUHVRJJAFRAU-YZNNVMRBSA-N tert-butyl-[(1r,3s,5z)-3-[tert-butyl(dimethyl)silyl]oxy-5-(2-diphenylphosphorylethylidene)-4-methylidenecyclohexyl]oxy-dimethylsilane Chemical compound C1[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)C(=C)\C1=C/CP(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 MDDUHVRJJAFRAU-YZNNVMRBSA-N 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000000000 tetracarboxylic acids Chemical class 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- IBBLKSWSCDAPIF-UHFFFAOYSA-N thiopyran Chemical compound S1C=CC=C=C1 IBBLKSWSCDAPIF-UHFFFAOYSA-N 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- LALRXNPLTWZJIJ-UHFFFAOYSA-N triethylborane Chemical group CCB(CC)CC LALRXNPLTWZJIJ-UHFFFAOYSA-N 0.000 description 1
- WXRGABKACDFXMG-UHFFFAOYSA-N trimethylborane Chemical group CB(C)C WXRGABKACDFXMG-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- MXSVLWZRHLXFKH-UHFFFAOYSA-N triphenylborane Chemical group C1=CC=CC=C1B(C=1C=CC=CC=1)C1=CC=CC=C1 MXSVLWZRHLXFKH-UHFFFAOYSA-N 0.000 description 1
- 238000004506 ultrasonic cleaning Methods 0.000 description 1
- 238000005292 vacuum distillation Methods 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
- 238000007740 vapor deposition Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000008096 xylene Substances 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
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F12/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
- C08F12/02—Monomers containing only one unsaturated aliphatic radical
- C08F12/04—Monomers containing only one unsaturated aliphatic radical containing one ring
- C08F12/14—Monomers containing only one unsaturated aliphatic radical containing one ring substituted by hetero atoms or groups containing heteroatoms
- C08F12/26—Nitrogen
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- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/02—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes
- C08G61/04—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes only aliphatic carbon atoms
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F12/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
- C08F12/02—Monomers containing only one unsaturated aliphatic radical
- C08F12/04—Monomers containing only one unsaturated aliphatic radical containing one ring
- C08F12/14—Monomers containing only one unsaturated aliphatic radical containing one ring substituted by hetero atoms or groups containing heteroatoms
- C08F12/22—Oxygen
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F12/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
- C08F12/02—Monomers containing only one unsaturated aliphatic radical
- C08F12/32—Monomers containing only one unsaturated aliphatic radical containing two or more rings
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- C08F12/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
- C08F12/34—Monomers containing two or more unsaturated aliphatic radicals
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- C08L25/00—Compositions of, homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring; Compositions of derivatives of such polymers
- C08L25/18—Homopolymers or copolymers of aromatic monomers containing elements other than carbon and hydrogen
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- C09D125/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring; Coating compositions based on derivatives of such polymers
- C09D125/18—Homopolymers or copolymers of aromatic monomers containing elements other than carbon and hydrogen
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
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- H10K50/14—Carrier transporting layers
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/10—Organic polymers or oligomers
- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
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- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/10—Organic polymers or oligomers
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- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
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- C08G2261/10—Definition of the polymer structure
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- C08G2261/141—Side-chains having aliphatic units
- C08G2261/1414—Unsaturated aliphatic units
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- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/10—Definition of the polymer structure
- C08G2261/14—Side-groups
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Abstract
本发明提供了新的聚合物和包含其的有机发光器件。
Description
技术领域
相关申请的交叉引用
本申请要求于2018年11月13日向韩国知识产权局提交的韩国专利申请第10-2018-0139332号的优先权或权益,其公开内容通过引用整体并入本文。
本发明涉及新的聚合物和包含其的有机发光器件。
背景技术
通常,有机发光现象是指通过利用有机材料将电能转换为光能的现象。利用有机发光现象的有机发光器件具有诸如宽视角,优异的对比度,快速的响应时间,优异的亮度、驱动电压和响应速度的特性,并因此进行了许多研究。
有机发光器件通常具有包括阳极、阴极和介于阳极与阴极之间的有机材料层的结构。有机材料层通常具有包含不同材料的多层结构以提高有机发光器件的效率和稳定性,例如,有机材料层可以由空穴注入层、空穴传输层、发光层、电子传输层、电子注入层等形成。在有机发光器件的结构中,如果在两个电极之间施加电压,则空穴从阳极注入有机材料层,电子从阴极注入有机材料层,当注入的空穴和电子彼此相遇时,形成激子,并且当激子再落至基态时发光。
持续需要开发用于在上述有机发光器件中使用的有机材料的新材料。
同时,近来,为了降低过程成本,代替常规的沉积法已开发了使用溶液法特别是喷墨法的有机发光器件。在开发的初始阶段,已尝试通过经由溶液法涂覆全部的有机发光器件层来开发有机发光器件,但当前技术具有局限性。因此,在层器件结构中仅HIL、HTL和EML通过溶液法加工,并且正在研究利用传统沉积法的混合过程作为后续过程。
因此,本发明提供了能够在用于有机发光器件的同时通过溶液法沉积的用于有机发光器件的新材料。
[现有技术文献]
[专利文献]
(专利文献0001)韩国专利特许公开第10-2000-0051826号
发明内容
技术问题
本发明的目的是提供新的聚合物和包含其的有机发光器件。
技术方案
在本发明的一个方面中,提供了包含由以下化学式1表示的重复单元的聚合物。
[化学式1]
其中,在化学式1中,
L1为C2-10亚烷基、C2-10氧亚烷基、C2-10全氟亚烷基或C2-10全氟氧亚烷基,
L2为单键或者经取代或未经取代的C6-60亚芳基,
Ar1、Ar2和Ar3各自独立地为经取代或未经取代的C6-60芳基,
R1、R2和R3各自独立地为氢或C1-10烷基,
各R4独立地为氢或卤素,
R5和R6为氢或者连接在一起以形成单键,
R7和R8为氢或者连接在一起以形成单键,条件是排除其中R5至R8全部形成单键的情况,以及
o为0至3的整数。
在本发明的另一个方面中,提供了有机发光器件,其包括:第一电极;布置成与第一电极相对的第二电极;和布置在第一电极与第二电极之间的一个或更多个有机材料层,其中有机材料层的一个或更多个层包含上述根据本发明的聚合物。
有益效果
由化学式1表示的聚合物可以用作有机发光器件的空穴传输层或空穴注入层的材料,能够通过溶液法沉积,并且可以在有机发光器件中改善效率,实现低驱动电压和/或改善寿命特性。
附图说明
图1示出了包括基底1、阳极2、发光层3和阴极4的有机发光器件的实例。
图2示出了包括基底1、阳极2、空穴注入层5、空穴传输层6、发光层7、电子传输层8和阴极4的有机发光器件的实例。
具体实施方式
在下文中,将更详细地描述本发明的实施方案以促进理解本发明。
如本文所用,符号或/>意指与另外的取代基连接的键。
如本文所用,术语“经取代或未经取代的”意指未经取代或经选自以下的一个或更多个取代基取代:氘;卤素基团;腈基;硝基;羟基;羰基;酯基;酰亚胺基;氨基;氧化膦基;烷氧基;芳氧基;烷基硫基;芳基硫基;烷基磺酰基;芳基磺酰基;甲硅烷基;硼基;烷基;环烷基;烯基;芳基;芳烷基;芳烯基;烷基芳基;烷基胺基;芳烷基胺基;杂芳基胺基;芳基胺基;芳基膦基;以及包含N、O和S原子中的至少一者的杂环基,或者未经取代或经以上例示的取代基中的两个或更多个取代基连接的取代基取代。例如,“两个或更多个取代基连接的取代基”可以为联苯基。即,联苯基可以被解释为芳基、或两个苯基连接的取代基。
在本说明书中,羰基的碳原子数没有特别限制,但优选为1至40。具体地,羰基可以为具有以下结构式的基团,但不限于此。
在本说明书中,酯基可以具有其中酯基的氧可以被具有1至25个碳原子的直链、支链或环状烷基,或者具有6至25个碳原子的芳基取代的结构。具体地,酯基可以为具有以下结构式的基团,但不限于此。
在本说明书中,酰亚胺基的碳原子数没有特别限制,但优选为1至25。具体地,酰亚胺基可以为具有以下结构式的基团,但不限于此。
在本说明书中,甲硅烷基具体包括三甲基甲硅烷基、三乙基甲硅烷基、叔丁基二甲基甲硅烷基、乙烯基二甲基甲硅烷基、丙基二甲基甲硅烷基、三苯基甲硅烷基、二苯基甲硅烷基、苯基甲硅烷基等,但不限于此。
在本说明书中,硼基具体包括三甲基硼基、三乙基硼基、叔丁基二甲基硼基、三苯基硼基和苯基硼基,但不限于此。
在本说明书中,卤素基团的实例包括氟、氯、溴或碘。
在本说明书中,烷基可以为直链或支链,并且其碳原子数没有特别限制,但优选为1至40。根据一个实施方案,烷基的碳原子数为1至20。根据另一个实施方案,烷基的碳原子数为1至10。根据另一个实施方案,烷基的碳原子数为1至6。烷基的具体实例包括甲基、乙基、丙基、正丙基、异丙基、丁基、正丁基、异丁基、叔丁基、仲丁基、1-甲基-丁基、1-乙基-丁基、戊基、正戊基、异戊基、新戊基、叔戊基、己基、正己基、1-甲基戊基、2-甲基戊基、4-甲基-2-戊基、3,3-二甲基丁基、2-乙基丁基、庚基、正庚基、1-甲基己基、环戊基甲基、环己基甲基、辛基、正辛基、叔辛基、1-甲基庚基、2-乙基己基、2-丙基戊基、正壬基、2,2-二甲基庚基、1-乙基-丙基、1,1-二甲基-丙基、异己基、4-甲基己基、5-甲基己基等,但不限于此。
在本说明书中,烯基可以为直链或支链,并且其碳原子数没有特别限制,但优选为2至40。根据一个实施方案,烯基的碳原子数为2至20。根据另一个实施方案,烯基的碳原子数为2至10。根据又一个实施方案,烯基的碳原子数为2至6。其具体实例包括乙烯基、1-丙烯基、异丙烯基、1-丁烯基、2-丁烯基、3-丁烯基、1-戊烯基、2-戊烯基、3-戊烯基、3-甲基-1-丁烯基、1,3-丁二烯基、烯丙基、1-苯基乙烯基-1-基、2-苯基乙烯基-1-基、2,2-二苯基乙烯基-1-基、2-苯基-2-(萘基-1-基)乙烯基-1-基、2,2-双(二苯基-1-基)乙烯基-1-基、基、苯乙烯基等,但不限于此。
在本说明书中,环烷基没有特别限制,但其碳原子数优选为3至60。根据一个实施方案,环烷基的碳原子数为3至30。根据另一个实施方案,环烷基的碳原子数为3至20。根据又一个实施方案,环烷基的碳原子数为3至6。其具体实例包括环丙基、环丁基、环戊基、3-甲基环戊基、2,3-二甲基环戊基、环己基、3-甲基环己基、4-甲基环己基、2,3-二甲基环己基、3,4,5-三甲基环己基、4-叔丁基环己基、环庚基、环辛基等,但不限于此。
在本说明书中,芳基没有特别限制,但优选具有6至60个碳原子,并且可以为单环芳基或多环芳基。根据一个实施方案,芳基的碳原子数为6至30。根据一个实施方案,芳基的碳原子数为6至20。作为单环芳基,芳基可以为苯基、联苯基、三联苯基等,但不限于此。多环芳基的实例包括萘基、蒽基、菲基、芘基、基、/>基、芴基等,但不限于此。
在本说明书中,芴基可以被取代,并且两个取代基可以彼此连接以形成螺环结构。在芴基被取代的情况下,可以形成等。然而,结构不限于此。
在本说明书中,杂环基为包含O、N、Si和S中的一者或更多者作为杂原子的杂环基,并且其碳原子数没有特别限制,但优选为2至60。杂环基的实例包括噻吩基、呋喃基、吡咯基、咪唑基、噻唑基、唑基、/>二唑基、三唑基、吡啶基、联吡啶基、嘧啶基、三嗪基、三唑基、吖啶基、哒嗪基、吡嗪基、喹啉基、喹唑啉基、喹喔啉基、酞嗪基、吡啶并嘧啶基、吡啶并吡嗪基、吡嗪并吡嗪基、异喹啉基、吲哚基、咔唑基、苯并/>唑基、苯并咪唑基、苯并噻唑基、苯并咔唑基、苯并噻吩基、二苯并噻吩基、苯并呋喃基、菲咯啉基、噻唑基、异/>唑基、/>二唑基、噻二唑基、苯并噻唑基、吩噻嗪基、二苯并呋喃基等,但不限于此。
在本说明书中,芳烷基、芳烯基、烷基芳基和芳基胺基中的芳基与芳基的前述实例相同。在本说明书中,芳烷基、烷基芳基和烷基胺基中的烷基与烷基的前述实例相同。在本说明书中,杂芳基胺基中的杂芳基可以应用杂环基的前述描述。在本说明书中,芳烯基中的烯基与烯基的前述实例相同。在本说明书中,可以应用芳基的前述描述,不同之处在于亚芳基为二价基团。在本说明书中,可以应用杂环基的前述描述,不同之处在于亚杂芳基为二价基团。在本说明书中,可以应用芳基或环烷基的前述描述,不同之处在于烃环不是一价基团而是由两个取代基结合而形成。在本说明书中,可以应用杂环基的前述描述,不同之处在于杂环不是一价基团而是由两个取代基结合而形成。
现有技术中使用的用于溶液法的基于芳基胺的材料具有难以同时确保在溶剂中的溶解度和空穴传输特性的问题。
然而,根据本发明的聚合物在由化学式1表示的重复单元中的主链与基于芳基胺的核之间包含适当的连接基(L1)结构。从而,可以降低与核的空间位阻以实现溶液法中的足够的溶解度以及优异的空穴转移特性。以下将对此进行更详细地描述。
本发明的一个实施方案提供了包含由以下化学式1表示的重复单元的聚合物:
[化学式1]
其中,在化学式1中,
L1为C2-10亚烷基、C2-10氧亚烷基、C2-10全氟亚烷基或C2-10全氟氧亚烷基,
L2为单键或者经取代或未经取代的C6-60亚芳基,
Ar1、Ar2和Ar3各自独立地为经取代或未经取代的C6-60芳基,
R1、R2和R3各自独立地为氢或C1-10烷基,
各R4独立地为氢或卤素,
R5和R6为氢或者连接在一起以形成单键,
R7和R8为氢或者连接在一起以形成单键,条件是排除其中R5至R8全部形成单键的情况,以及
o为0至3的整数。
优选地,由化学式1表示的重复单元可以为选自由以下化学式2至4表示的重复单元中的任一者:
[化学式2]
[化学式3]
[化学式4]
其中,L1、L2、Ar1、Ar2、Ar3、R1、R2、R3、R4和o如化学式1中所限定。
优选地,L1可以为-C4H8-、-C5H10-、-C6H12-、-OC4H8-、-OC5H10-、-OC6H10-、-(OC2H4)2-、-(OC2H4)3-、-(C2H4)O(C3H6)O(C2H4)-、-C4F8-、-C5F10-、-C6F12-、-OC4F8-、-OC5F10-、-OC6F10-、-(OC2F4)2-或-(OC2F4)3-。
优选地,L2可以为单键、亚苯基或亚联苯基,
优选地,Ar1、Ar2和Ar3可以各自独立地为苯基、联苯基、二甲基芴基或二苯基芴基,并且Ar1、Ar2和Ar3可以未经取代或经甲基、乙基、丙基、异丙基、丁基、异丁基或叔丁基取代。
优选地,R1、R2和R3可以各自独立地为氢或甲基。
优选地,R4可以为氢或氟。
优选地,化学式1为选自由以下表示的重复单元中的任一者:
本发明的一个实施方案提供了包含由以下表示的重复单元中的任一者的聚合物:
同时,由化学式1表示的重复单元衍生自由以下化学式1-1表示的单体:
[化学式1-1]
其中,在化学式1-1中,L1、L2、Ar1、Ar2、Ar3、R1、R2、R3、R4、R5、R6、R7、R8和o如化学式1中所限定。
由化学式1-1表示的化合物可以根据以下反应方案1-1或1-2所示的制备方法来制备。
[反应方案1-1]
[反应方案1-2]
在反应方案1-1或1-2中,除了X1之外的剩余取代基如上所限定,以及X1为卤素,优选为溴或氯。反应方案1-1和1-2为胺取代反应,该反应在钯催化剂和碱的存在下进行以产生由化学式1-1表示的化合物。以上制备方法可以在下文描述的制备例中进一步体现。
根据本发明的聚合物可以通过使上述由化学式1-1表示的单体聚合来制备。优选地,根据本发明的聚合物为包含由化学式1表示的重复单元的共聚物。
优选地,聚合物的重均分子量为5,000至500,000,并且更优选为10,000至300,000。
(涂覆组合物)
根据本发明的化合物可以通过溶液法形成有机发光器件的有机材料层,特别是空穴传输层或空穴注入层。为此,本发明的一个实施方案提供了包含上述根据本发明的化合物和溶剂的涂覆组合物。
溶剂没有特别限制,只要其是能够溶解或分散根据本发明的化合物的溶剂即可。作为实例,可以提及基于氯的溶剂,例如氯仿、二氯甲烷、1,2-二氯乙烷、1,1,2-三氯乙烷、氯苯和邻二氯苯;基于醚的溶剂,例如四氢呋喃和二烷;基于芳族烃的溶剂,例如甲苯、二甲苯、三甲基苯和均三甲苯;基于脂族烃的溶剂,例如环己烷、甲基环己烷、正戊烷、正己烷、正庚烷、正辛烷、正壬烷和正癸烷;基于酮的溶剂,例如丙酮、甲基乙基酮和环己酮;基于酯的溶剂,例如乙酸乙酯、乙酸丁酯和乙基溶纤剂乙酸酯;多元醇,例如乙二醇、乙二醇单丁醚、乙二醇单乙醚、乙二醇单甲醚、二甲氧基乙烷、丙二醇、二乙氧基甲烷、三乙二醇单乙醚、甘油和1,2-己二醇,及其衍生物;基于醇的溶剂,例如甲醇、乙醇、丙醇、异丙醇和环己醇;基于亚砜的溶剂,例如二甲基亚砜;基于酰胺的溶剂,例如N-甲基-2-吡咯烷酮和N,N-二甲基甲酰胺;基于苯甲酸酯的溶剂,例如苯甲酸丁酯和苯甲酸甲基-2-甲氧基酯;四氢化萘;3-苯氧基-甲苯;等等。此外,上述溶剂可以单独使用或者两种或更多种溶剂组合使用。
此外,涂覆组合物的粘度优选为1cP至10cP,并且在以上范围内,涂覆是容易的。此外,在涂覆组合物中,根据本发明的化合物的浓度优选为0.1重量/体积%至20重量/体积%。
此外,涂覆组合物还可以包含选自热聚合引发剂和光聚合引发剂的一种或更多种添加剂。
热聚合引发剂的实例可以包括过氧化物,例如甲基乙基酮过氧化物、甲基异丁基酮过氧化物、乙酰丙酮过氧化物、甲基环己酮过氧化物、环己酮过氧化物、异丁酰基过氧化物、2,4-二氯苯甲酰基过氧化物、双-3,5,5-三甲基己酰基过氧化物、月桂基过氧化物、苯甲酰基过氧化物;或偶氮类,例如偶氮二异丁腈、偶氮双二甲基戊腈和偶氮二环己腈,但不限于此。
光聚合引发剂的实例可以包括基于苯乙酮或基于缩酮的光聚合引发剂,例如二乙氧基苯乙酮、2,2-二甲氧基-1,2-二苯基乙-1-酮、1-羟基-环己基-苯基-酮、4-(2-羟基乙氧基)苯基-(2-羟基-2-丙基)酮、2-苄基-2-二甲基氨基-1-(4-吗啉代苯基)丁酮-1,2-羟基-2-甲基-1-苯基丙-1-酮、2-甲基-2-吗啉代(4-甲基硫苯基)丙-1-酮和1-苯基-1,2-丙二酮-2-(邻乙氧基羰基)肟;基于安息香醚的光聚合引发剂,例如安息香、安息香甲醚和安息香乙醚;基于二苯甲酮的光聚合引发剂,例如二苯甲酮、4-羟基二苯甲酮、2-苯甲酰基萘、4-苯甲酰基联苯和4-苯甲酰基苯基醚;基于噻吨酮的光聚合引发剂,例如2-异丙基噻吨酮、2-氯噻吨酮、2,4-二甲基噻吨酮、2,4-二乙基噻吨酮和2,4-二氯噻吨酮;以及其他光聚合引发剂,例如乙基蒽醌、2,4,6-三甲基苯甲酰基二苯基氧化膦、2,4,6-三甲基苯甲酰基苯基乙氧基氧化膦、双(2,4,6-三甲基苯甲酰基)苯基氧化膦和双(2,4-二甲氧基苯甲酰基)-2,4,4-三甲基戊基氧化膦,但不限于此。
此外,具有光聚合促进效果的那些可以单独使用或与光聚合引发剂组合使用。其实例可以包括三乙醇胺、甲基二乙醇胺、4-二甲基氨基苯甲酸乙酯、4-二甲基氨基苯甲酸异戊酯、苯甲酸(2-二甲基氨基)乙基酯、4,4'-二甲基氨基二苯甲酮等,但不限于此。
在本发明的另一个实施方案中,提供了用于使用上述涂覆组合物形成空穴注入层或空穴传输层的方法。具体地,所述方法包括以下步骤:通过溶液法将上述根据本发明的涂覆组合物涂覆在阳极上或者形成在阳极上的发光层上;以及对经涂覆的涂覆组合物进行热处理或光处理。
溶液法使用上述根据本发明的涂覆组合物,并且是指旋涂、浸涂、刮涂、喷墨印刷、丝网印刷、喷洒法、辊涂等,但不限于此。
热处理中的热处理温度优选为150℃至230℃。在另一个实施方案中,热处理时间可以为1分钟至3小时,更优选为10分钟至1小时。在另一个实施方案中,热处理优选在惰性气体气氛例如氩气和氮气中进行。此外,所述方法还可以包括在涂覆步骤与热处理或光处理步骤之间使溶剂蒸发的步骤。
(有机发光器件)
在本发明的另一个方面中,提供了包含上述根据本发明的聚合物的有机发光器件。具体地,本发明提供了这样的有机发光器件,其包括:第一电极;布置成与第一电极相对的第二电极;和布置在第一电极与第二电极之间的一个或更多个有机材料层,其中有机材料层的一个或更多个层包含根据本发明的聚合物。
优选地,聚合物可以包含在有机材料层的空穴传输层或空穴注入层中。
在本发明的又一个方面中,包含上述本发明的聚合物的有机材料层为空穴注入层或空穴传输层。
根据本发明的实施方案的有机发光器件的结构示于图1和图2中。
图1示出了包括基底1、阳极2、发光层3和阴极4的有机发光器件的实例。图2示出了包括基底1、阳极2、空穴注入层5、空穴传输层6、发光层7、电子传输层8和阴极4的有机发光器件的实例。
根据本发明的有机发光器件可以通过本领域已知的材料和方法来制造,不同之处在于空穴传输层或空穴注入层包含根据本发明的聚合物并根据上述方法来制造。
例如,根据本发明的有机发光器件可以通过在基底上顺序地堆叠阳极、有机材料层和阴极来制造。在这种情况下,有机发光器件可以通过以下来制造:使用PVD(物理气相沉积)法例如溅射法或电子束蒸镀法在基底上沉积金属、具有导电性的金属氧化物、或其合金以形成阳极,在阳极上形成包括空穴注入层、空穴传输层、发光层和电子传输层的有机材料层,然后在有机材料层上沉积可以用作阴极的材料。
除了这样的方法之外,有机发光器件还可以通过在基底上顺序地沉积阴极材料、有机材料层和阳极材料来制造(国际公开WO2003/012890)。然而,制造方法不限于此。
作为阳极材料,通常优选使用具有大功函数的材料使得空穴可以顺利地注入有机材料层。阳极材料的具体实例包括:金属,例如钒、铬、铜、锌和金,或其合金;金属氧化物,例如氧化锌、氧化铟、氧化铟锡(ITO)和氧化铟锌(IZO);金属和氧化物的组合,例如ZnO:Al或SnO2:Sb;导电聚合物,例如聚(3-甲基噻吩)、聚[3,4-(亚乙基-1,2-二氧)噻吩](PEDOT)、聚吡咯和聚苯胺;等等,但不限于此。
作为阴极材料,通常优选使用具有小功函数的材料使得电子可以容易地注入有机材料层。阴极材料的具体实例包括:金属,例如镁、钙、钠、钾、钛、铟、钇、锂、钆、铝、银、锡和铅,或其合金;多层结构材料,例如LiF/Al或LiO2/Al;等等,但不限于此。
空穴注入层是用于注入来自电极的空穴的层,并且空穴注入材料优选为这样的化合物:其具有传输空穴的能力,因此具有注入阳极中的空穴的效应和优异的对发光层或发光材料的空穴注入效应,防止发光层中产生的激子移动至电子注入层或电子注入材料,并且形成薄膜的能力还优异。优选地,空穴注入材料的HOMO(最高占据分子轨道)在阳极材料的功函数与周围有机材料层的HOMO之间。空穴注入材料的具体实例包括金属卟啉、低聚噻吩、基于芳基胺的有机材料、基于六腈六氮杂苯并菲的有机材料、基于喹吖啶酮的有机材料、基于的有机材料、蒽醌、基于聚苯胺和基于聚噻吩的导电聚合物等,但不限于此。
发光材料优选为这样的材料:其可以接收分别从空穴传输层和电子传输层传输的空穴和电子,并使空穴和电子结合以发出可见光区域内的光,并且对荧光或磷光具有良好的量子效率。发光材料的具体实例包括8-羟基喹啉铝配合物(Alq3);基于咔唑的化合物;二聚苯乙烯基化合物;BAlq;10-羟基苯并喹啉-金属化合物;基于苯并唑、基于苯并噻唑和基于苯并咪唑的化合物;基于聚(对亚苯基亚乙烯基)(PPV)的聚合物;螺环化合物;聚芴;红荧烯;等等,但不限于此。
发光层可以包含主体材料和掺杂剂材料。主体材料可以为稠合芳族环衍生物、含杂环的化合物等。稠合芳族环衍生物的具体实例包括蒽衍生物、芘衍生物、萘衍生物、并五苯衍生物、菲化合物、荧蒽化合物等。含杂环的化合物的实例包括咔唑衍生物、二苯并呋喃衍生物、梯子型呋喃化合物、嘧啶衍生物等,但不限于此。掺杂剂材料包括芳族胺衍生物、苯乙烯胺化合物、硼配合物、荧蒽化合物、金属配合物等。具体地,芳族胺衍生物为经取代或未经取代的具有芳基氨基的稠合芳族环衍生物,其实例包括具有芳基氨基的芘、蒽、二茚并芘等。苯乙烯胺化合物为其中经取代或未经取代的芳基胺中取代有至少一个芳基乙烯基的化合物,其中选自芳基、甲硅烷基、烷基、环烷基和芳基氨基的一个或两个或更多个取代基为经取代或未经取代的。其具体实例包括苯乙烯胺、苯乙烯二胺、苯乙烯三胺、苯乙烯四胺等,但不限于此。此外,金属配合物包括铱配合物、铂配合物等,但不限于此。
电子传输层是接收来自电子注入层的电子并将电子传输至发光层的层,并且电子传输材料适当地为这样的材料:其可以很好地接收来自阴极的电子并将电子转移至发光层,并且具有大的电子迁移率。电子传输材料的具体实例包括:8-羟基喹啉的Al配合物;包括Alq3的配合物;有机自由基化合物;羟基黄酮-金属配合物;等等,但不限于此。电子传输层可以与如根据相关技术使用的任何期望的阴极材料一起使用。特别地,阴极材料的适当实例为具有低功函数,后接铝层或银层的典型材料。其具体实例包括铯、钡、钙、镱和钐,在每种情况下都后接铝层或银层。
电子注入层是注入来自电极的电子的层,并且优选为这样的化合物:其具有传输电子的能力,具有注入来自阴极的电子的效应和将电子注入发光层或发光材料的优异效应,防止由发光层产生的激子移动至空穴注入层,并且形成薄膜的能力也优异。电子注入层的具体实例包括芴酮、蒽醌二甲烷、联苯醌、噻喃二氧化物、唑、/>二唑、三唑、咪唑、/>四羧酸、亚芴基甲烷、蒽酮等,及其衍生物;金属配合物化合物;含氮5元环衍生物;等等,但不限于此。
金属配合物化合物包括8-羟基喹啉锂、双(8-羟基喹啉)锌、双(8-羟基喹啉)铜、双(8-羟基喹啉)锰、三(8-羟基喹啉)铝、三(2-甲基-8-羟基喹啉)铝、三(8-羟基喹啉)镓、双(10-羟基苯并[h]喹啉)铍、双(10-羟基苯并[h]喹啉)锌、双(2-甲基-8-喹啉)氯镓、双(2-甲基-8-喹啉)(邻甲酚)镓、双(2-甲基-8-喹啉)(1-萘酚)铝、双(2-甲基-8-喹啉)(2-萘酚)镓等,但不限于此。
根据使用的材料,根据本发明的有机发光器件可以为前侧发射型、后侧发射型或双侧发射型。
此外,除了有机发光器件之外,根据本发明的化合物还可以包含在有机太阳能电池或有机晶体管中。
将在以下实施例中详细地描述包含由化学式1表示的重复单元的聚合物和包含其的有机发光器件的制备。然而,这些实施例仅出于说明性目的而呈现,并且不旨在限制本发明的范围。
[实施例]
实施例1:聚合物化合物1(化合物1)的制备
[反应方案1-1]
在氮气气氛下,在500mL圆底烧瓶中,添加Mg(2.06g,84.78mmol)并添加四氢呋喃(THF)(50mL),并将混合物搅拌30分钟。然后将烧瓶置于0℃浴中并搅拌30分钟。将1,4-二溴苯(20g,84.74mmol)溶解在50ml THF中并缓慢添加到烧瓶中。在添加完成之后,添加少量碘(I2)并在室温下搅拌15小时。确定反应溶液变成黑色且Mg溶解。在制备格氏溶液之后,将CuI(0.323g,1.696mmol)和LiBr(0.295g,3.391mmol)添加到另一500ml圆底烧瓶中,添加5ml THF并溶解。然后向烧瓶中添加二溴丁烷(36.61g,169.6mmol)和50ml THF。然后将烧瓶置于0℃浴中并搅拌30分钟。将先前制备的格氏溶液缓慢添加到烧瓶中。在添加完成之后,将温度升至室温并搅拌一天。在反应完成之后,缓慢添加200ml 5重量%NH4Cl溶液。使用EA(50mL×3)萃取有机溶剂并用MgSO4除去剩余的水。将有机层回收,然后浓缩。将浓缩的液体通过真空蒸馏来纯化,并且可以在140℃的蒸气温度和4托下分离和回收化合物1-1(产率:35%)。
[反应方案1-2]
在氮气气氛下,将先前合成的化合物1-1(4g,13.96mmol)、4-羟基苯甲醛(2g,16.44mmol)和K2CO3(3.78g,27.38mmol)添加到250mL圆底烧瓶中,并溶解在45ml丙酮中。将反应混合物加热至70℃并搅拌4小时。随后,从盐水/EA中萃取物质。在将溶剂比率逐渐变为Hex:MC(9:1至4:6)的同时进行柱纯化。然后将所得产物浓缩以获得3.5g浅黄色液体(化合物1-2)(产率:81%)。
[反应方案1-3]
在氮气气氛下,将先前合成的化合物1-2(4-(4-(4-溴苯基)丁氧基)苯甲醛)(3.7g,11.1mmol)和(9-苯基-9H-咔唑-3-基)硼酸(4.145g,14.43mmol)添加到250mL圆底烧瓶中并向其中添加45ml THF,使混合物完全溶解。将烧瓶置于75℃浴中并搅拌30分钟。将K2CO3(4.6g,33.3mmol)溶解在22.5ml DI水中,然后缓慢添加到烧瓶中。向其中添加Pd(P(tBu)3)2(0.17g,0.333mmol)。然后,将所得混合物搅拌2小时。在反应完成之后,从盐水/EA中萃取物质。将溶液浓缩并通过用Hex:MC(2:1)的柱来纯化。然后将所得产物浓缩以得到4.75g浅黄色固体(化合物1-3)(产率:87%)。
[反应方案1-4]
在氮气气氛下,将先前合成的中间体(化合物1-3)(4.8g,9.723mmol)添加到250mL圆底烧瓶中,向其中添加30ml DMF并完全溶解。将NBS(1.82g,10.2mmol)溶解在10ml DMF中并添加30分钟。然后将烧瓶置于40℃浴中并搅拌6小时。通过添加MeOH使所得产物沉淀以回收白色固体(化合物1-4)(4.9g)(产率:95%)。
[反应方案1-5]
在氮气气氛下,将先前合成的中间体(化合物1-4)(4.9g,8.616mmol)和硼酸酯(5.68g,11.2mmol)添加到250mL圆底烧瓶中。向其中添加40ml THF并完全溶解。然后将烧瓶置于75℃浴中并搅拌30分钟。将K2CO3(4.6g,33.3mmol)溶解在22.5ml DI水中,然后缓慢添加到烧瓶中。然后,将混合物搅拌30分钟,并向其中添加Pd(P(tBu)3)2(0.132g,0.258mmol)。然后,将所得混合物搅拌2小时。在反应完成之后,从盐水/EA中萃取物质。将溶液浓缩并通过用Hex:MC(1:1)的柱来纯化。然后将所得产物浓缩以得到7.2g浅黄色固体(化合物1-5)(产率:78%)。
[反应方案1-6]
在氮气气氛下,将甲基三苯基溴化(MTPPB)(9.67g,27.06mmol)和KOtBu(3.04g,27.06mmol)添加到250mL圆底烧瓶中。向其中添加100ml无水THF,将烧瓶置于0℃浴中并搅拌30分钟。然后,将先前合成的化合物1-5(6.2g,7.732mmol)添加到另一烧瓶中以产生氮气气氛。然后,添加50ml THF以使其溶解。将烧瓶置于0℃浴中并搅拌30分钟。然后向其中缓慢添加先前制备的MTPPB溶液。将混合物进一步搅拌30分钟,并添加100ml H2O。将水性层和有机层分离,并将有机层单独回收和浓缩。然后将其用EtOH结晶以得到物质。在Hex:MC(1:1)的条件下进行两次另外的纯化以得到5.6g单体化合物1-6(产率:75%)。
[反应方案1-7]
在氮气气氛下,将1g单体化合物1-6添加到10ml圆底烧瓶中。添加4ml THF并完全溶解。然后,向其中添加0.01当量AIBN。进行氮气鼓泡1小时。然后,将所得混合物置于70℃浴中并搅拌1小时。然后,将粘性凝胶缓慢添加到EA中以获得白色固体。通过过滤来收集固体并进行柱纯化以收集聚合物化合物1。当通过GPC确定分子量时,确定Mn为193KDa,PDI为2.06(产率50%)。
制备例2:化合物2的制备
[反应方案2-1]
在氮气气氛下,将甲基三苯基溴化(MTPPB)(37.5g,105mmol)和KOtBu(11.8g,105mmol)添加到500mL圆底烧瓶中。向其中添加200ml无水THF,将烧瓶置于0℃浴中并搅拌30分钟。然后,将先前合成的化合物1-2(10g,30mmol)添加到另一烧瓶中以产生氮气气氛。然后,添加50ml THF并溶解。将烧瓶置于0℃浴中并搅拌30分钟。然后向其中缓慢添加先前制备的MTPPB溶液。将混合物进一步搅拌30分钟,并添加200ml H2O。将水性层和有机层分离,并将有机层单独回收和浓缩。将其通过用Hex:EA(8:2)的柱来纯化以回收化合物2-1(8.5g,产率:85%)。
[反应方案2-2]
在氮气气氛下,将先前合成的化合物2-1(1-溴-4-(4-(4-乙烯基苯氧基)丁基)苯)(8g,24.15mmol)、咔唑化合物(13.09g,21.73mmol)和NaOtBu(5.8g,60.4mmol)添加到250mL圆底烧瓶中。添加80ml甲苯并完全溶解。然后,将所得混合物置于100℃浴中并搅拌30分钟。然后,将Pd催化剂(0.37g,0.725mmol)溶解在5ml甲苯中,并置于烧瓶中。将混合物进一步搅拌2小时。在冷却至室温之后。将反应溶液用盐水/MC萃取。将经萃取的化合物浓缩,然后使其吸附到100g二氧化硅上并通过用Hex:MC(1:1)的柱来纯化。在柱纯化之后,将其用EtOH沉淀以得到9g白色固体(化合物2-2)(产率:48%)。
[反应方案2-3]
在氮气气氛下,将1g化合物2-2添加到10ml圆底烧瓶中。添加4ml THF并完全溶解。然后,向其中添加0.01当量AIBN。进行氮气鼓泡1小时。然后,将所得混合物置于70℃浴中并搅拌1小时。然后,将粘性凝胶缓慢添加到EA中以获得白色固体。将固体过滤和收集,并通过柱来纯化以回收聚合物化合物2。通过GPC确定分子量显示出Mn为159KDa,PDI为3.01(产率:45%)。
比较例1:比较聚合物化合物1的制备
[反应方案3-1]
使用溴代苯乙烯代替实施例2的反应方案2-2中的化合物2-1来合成单体化合物3-1。此后,由于聚合中的溶解度不好,因此以与化合物2的合成方法中相同的方式合成比较聚合物化合物1,不同之处在于每1g单体化合物3-1使用8ml THF来进行聚合。通过GPC确定分子量显示出Mn为22KDa,PDI为2.35。
比较例2:比较化合物2的制备
[反应方案4-1]
在氮气气氛下,将甲基三苯基溴化(MTPPB)(9.4g,26.3mmol)和KOtBu(2.95g,26.3mmol)添加到200mL圆底烧瓶中。向其中添加50ml无水THF,将烧瓶置于0℃浴中并搅拌30分钟。然后,将先前合成的实施例1的化合物1-4(4.3g,7.5mmol)添加到另一烧瓶中以产生氮气气氛。然后,添加25ml THF并溶解。将烧瓶置于0℃浴中并搅拌30分钟。然后向其中缓慢添加先前制备的MTPPB溶液。将混合物进一步搅拌30分钟,并添加200ml H2O。将水性层和有机层分离,并将有机层单独回收和浓缩。然后将其用EtOH沉淀以回收3.8g白色固体(化合物4-1)(产率:85%)。
[反应方案4-2]
在氮气气氛下,将先前合成的化合物4-1(3.8g,6.63mmol)和硼酸酯(2.1g,5.53mmol)添加到250mL圆底烧瓶中。添加40ml THF并完全溶解。然后将烧瓶置于75℃浴中并搅拌30分钟。将K2CO3(2.8g,19.9mmol)溶解在15ml DI水中,然后缓慢添加到烧瓶中。然后,将混合物搅拌30分钟,并向其中添加Pd(P(tBu)3)2(0.1g,0.199mmol)。然后,将所得混合物搅拌2小时。在反应完成之后,从盐水/EA中萃取物质。将溶液浓缩并通过用Hex:MC(1:1)的柱来纯化。然后将所得产物浓缩以得到3.5g浅黄色固体(化合物4-2)(产率:72%)。
[反应方案4-3]
在氮气气氛下,将先前合成的实施例2的化合物2-1(1-溴-4-(4-(4-乙烯基苯氧基)丁基)苯)(1.6g,4.75mmol)、以上合成的化合物4-2(3.5g,4.75mmol)和NaOtBu(1.37g,14.3mmol)添加到100mL圆底烧瓶中。添加20ml甲苯并完全溶解。然后,将混合物置于100℃浴中并搅拌30分钟。将Pd催化剂(0.08g,0.143mmol)溶解在5ml甲苯中并添加到烧瓶中。将所得混合物进一步搅拌2小时。在冷却至室温之后,将反应溶液用盐水/MC萃取。将经萃取的化合物浓缩,然后使其吸附到20g二氧化硅上并通过用Hex:MC(1:1)的柱来纯化。在柱纯化之后,将其用EtOH沉淀以得到2.8g白色固体(比较化合物2)(产率:60%)。
实验例1:有机发光器件的制造
将其上涂覆有厚度为的ITO(氧化铟锡)作为薄膜的玻璃基底放入其中溶解有清洁剂的蒸馏水中,并进行超声清洗。在这种情况下,使用由Fischer Co.制造的产品作为清洁剂,使用利用由Millipore Co.制造的过滤器过滤两次的蒸馏水作为蒸馏水。在将ITO清洗30分钟之后,使用蒸馏水重复两次超声清洗10分钟。在用蒸馏水清洗完成之后,将基底用异丙醇和丙酮溶剂超声清洗,干燥,然后将基底清洗5分钟,然后转移至手套箱。
将2重量/体积%的化合物1的甲苯涂覆组合物和以下化合物M(重量比为8:2)旋涂(4000rpm)在ITO透明电极上,并在200℃下热处理(固化)30分钟以形成厚度为40nm的空穴注入层。在转移至真空沉积器之后,在空穴注入层上将以下化合物G真空沉积以形成厚度为20nm的空穴传输层。在空穴传输层上将以下化合物H和以下化合物I以92:8的重量比真空沉积至20nm的厚度以形成发光层。在发光层上将以下化合物J真空沉积至35nm的厚度以形成电子注入和传输层。在电子注入和传输层上顺序地沉积LiF(1nm)和铝(100nm)以形成阴极。
在上述过程中,将有机材料的气相沉积速率保持在至/> 将LiF的沉积速率保持在/>将铝的沉积速率保持在/>将沉积期间的真空度保持在2×10-7托至5×10-8托。/>
实验例2、比较实验例1和2
以与实验例1中相同的方式制造有机发光器件,不同之处在于使用下表1所示的聚合物化合物代替聚合物化合物1。
器件评估
对于以上实验例和比较实验例中制造的有机发光器件,在10mA/cm2的电流密度下测量驱动电压、外量子效率(EQE)、亮度和寿命,结果示于下表1中。外量子效率通过(发射的光子数)/(注入的电荷载流子数)来计算。T90意指亮度降低至初始亮度(500尼特)的90%所需的时间。
[表1]
如表1所示,可以确定由于根据本发明的实施方案的聚合物化合物1和化合物2构成包含连接基的聚合物,因此它们与不是如此的比较化合物1相比表现出大大增加的效率和寿命。此外,由于本发明的聚合物因连接基结构而不具有空间位阻,因此其容易合成高分子量聚合物,同时,其在有机溶剂中具有优异的溶解度,从而促进涂覆组合物的制备。特别地,确定与使用比较化合物1的情况相比,由于本发明的聚合物形成均匀涂层并且膜稳定性优异,因此其可以在有机发光器件中表现出优异的性能。
此外,如表1所示,确定与使用具有两个固化基团的比较化合物2的情况相比,根据本发明的实施方案的聚合物在寿命特性方面是显著优异的。当使用单体而不是聚合物时,未聚合的单体可能干扰空穴的转移,并且其可能被引入到发光层中从而导致器件寿命降低。确定本发明的聚合物改善单体的缺点,因此膜的耐溶剂性优异,从而在有机发光器件中显示出优异的性能。
[附图标记说明]
1:基底 2:阳极
3:发光层 4:阴极
5:空穴注入层 6:空穴传输层
7:发光层 8:电子传输层
Claims (10)
1.一种包含由以下化学式1表示的重复单元的聚合物:
[化学式1]
其中,在化学式1中,
L1为-C4H8-、-C5H10-、-C6H12-、-OC4H8-、-OC5H10-、-OC6H12-、-(OC2H4)2-、-(OC2H4)3-、-(C2H4)O(C3H6)O(C2H4)-、-C4F8-、-C5F10-、-C6F12-、-OC4F8-、-OC5F10-、-OC6F12-、-(OC2F4)2-或-(OC2F4)3-,其为直链,
L2为单键或者经取代或未经取代的C6-60亚芳基,
Ar1、Ar2和Ar3各自独立地为经取代或未经取代的C6-60芳基,
R1、R2和R3各自独立地为氢或C1-10烷基,
各R4独立地为氢或卤素,
R5和R6为氢或者连接在一起以形成单键,
R7和R8为氢或者连接在一起以形成单键,条件是排除其中R5至R8全部形成单键的情况,以及
o为0至3的整数。
2.根据权利要求1所述的聚合物,其中
所述聚合物的重均分子量为5,000至500,000。
3.根据权利要求1所述的聚合物,其中
由化学式1表示的所述重复单元为选自由以下化学式2至4表示的重复单元中的任一者:
[化学式2]
[化学式3]
[化学式4]
其中,L1、L2、Ar1、Ar2、Ar3、R1、R2、R3、R4和o如权利要求1中所限定。
4.根据权利要求1所述的聚合物,其中
L2为单键、亚苯基或亚联苯基。
5.根据权利要求1所述的聚合物,其中
Ar1、Ar2和Ar3各自独立地为苯基、联苯基、二甲基芴基或二苯基芴基,并且所述Ar1、所述Ar2和所述Ar3各自独立地未经取代或经甲基、乙基、丙基、异丙基、丁基、异丁基或叔丁基取代。
6.根据权利要求1所述的聚合物,其中
R1、R2和R3各自独立地为氢或甲基。
7.根据权利要求1所述的聚合物,其中
R4为氢或氟。
8.一种包含由以下表示的重复单元中的任一者的聚合物:
9.一种有机发光器件,包括:第一电极;布置成与所述第一电极相对的第二电极;和布置在所述第一电极与所述第二电极之间的一个或更多个有机材料层,其中所述有机材料层的一个或更多个层包含根据权利要求1至8中任一项所述的聚合物。
10.根据权利要求9所述的有机发光器件,其中
包含根据权利要求1至8中任一项所述的聚合物的所述有机材料层为空穴注入层或空穴传输层。
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