CN101687893B - 含有吩噻嗪s-氧化物或吩噻嗪s,s-二氧化物基团的硅烷及其在oled中的用途 - Google Patents
含有吩噻嗪s-氧化物或吩噻嗪s,s-二氧化物基团的硅烷及其在oled中的用途 Download PDFInfo
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- CN101687893B CN101687893B CN200880022144.XA CN200880022144A CN101687893B CN 101687893 B CN101687893 B CN 101687893B CN 200880022144 A CN200880022144 A CN 200880022144A CN 101687893 B CN101687893 B CN 101687893B
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- DSAFSORWJPSMQS-UHFFFAOYSA-N 10H-phenothiazine 5-oxide Chemical compound C1=CC=C2S(=O)C3=CC=CC=C3NC2=C1 DSAFSORWJPSMQS-UHFFFAOYSA-N 0.000 title abstract description 24
- ZAYUOSICZWFJSW-UHFFFAOYSA-N 10h-phenothiazine 5,5-dioxide Chemical group C1=CC=C2S(=O)(=O)C3=CC=CC=C3NC2=C1 ZAYUOSICZWFJSW-UHFFFAOYSA-N 0.000 title abstract description 3
- 150000004756 silanes Chemical class 0.000 title abstract 6
- 239000000463 material Substances 0.000 claims abstract description 149
- 150000001875 compounds Chemical class 0.000 claims description 118
- 125000003118 aryl group Chemical group 0.000 claims description 82
- 239000000758 substrate Substances 0.000 claims description 63
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 26
- 229910052760 oxygen Inorganic materials 0.000 claims description 26
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 20
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
- 230000000007 visual effect Effects 0.000 claims description 8
- 229910021529 ammonia Inorganic materials 0.000 claims description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- VIJYEGDOKCKUOL-UHFFFAOYSA-N 9-phenylcarbazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2C2=CC=CC=C21 VIJYEGDOKCKUOL-UHFFFAOYSA-N 0.000 claims description 3
- 239000011159 matrix material Substances 0.000 abstract description 12
- 238000004519 manufacturing process Methods 0.000 abstract description 2
- 239000010410 layer Substances 0.000 description 120
- 125000000217 alkyl group Chemical group 0.000 description 54
- -1 aryl-carbonyl oxygen Chemical compound 0.000 description 52
- 229910052739 hydrogen Inorganic materials 0.000 description 37
- 229910000077 silane Inorganic materials 0.000 description 34
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 33
- 229910052751 metal Inorganic materials 0.000 description 33
- 239000000203 mixture Substances 0.000 description 33
- 125000001072 heteroaryl group Chemical group 0.000 description 32
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 31
- 239000000243 solution Substances 0.000 description 31
- 238000000034 method Methods 0.000 description 30
- 239000001257 hydrogen Substances 0.000 description 29
- 239000002184 metal Substances 0.000 description 28
- 238000003756 stirring Methods 0.000 description 26
- 239000002585 base Substances 0.000 description 24
- 150000002431 hydrogen Chemical group 0.000 description 22
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- 125000003545 alkoxy group Chemical group 0.000 description 21
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 20
- 229910052757 nitrogen Inorganic materials 0.000 description 20
- 150000002990 phenothiazines Chemical class 0.000 description 20
- 230000005540 biological transmission Effects 0.000 description 18
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical class [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 description 18
- 238000002156 mixing Methods 0.000 description 18
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 17
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 17
- 239000001301 oxygen Substances 0.000 description 16
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 16
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
- 229910052736 halogen Inorganic materials 0.000 description 15
- 150000002367 halogens Chemical class 0.000 description 15
- 125000001424 substituent group Chemical group 0.000 description 15
- 125000004104 aryloxy group Chemical group 0.000 description 14
- 239000000460 chlorine Substances 0.000 description 14
- 150000003254 radicals Chemical class 0.000 description 13
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 12
- 125000003368 amide group Chemical group 0.000 description 12
- 229910052741 iridium Inorganic materials 0.000 description 12
- 239000003446 ligand Substances 0.000 description 12
- 238000002360 preparation method Methods 0.000 description 12
- 238000005160 1H NMR spectroscopy Methods 0.000 description 11
- 238000000151 deposition Methods 0.000 description 11
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 11
- 229910052799 carbon Inorganic materials 0.000 description 10
- 229910052801 chlorine Inorganic materials 0.000 description 10
- 230000008021 deposition Effects 0.000 description 10
- 229910052731 fluorine Inorganic materials 0.000 description 10
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 10
- 229910052717 sulfur Inorganic materials 0.000 description 10
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 9
- LULAYUGMBFYYEX-UHFFFAOYSA-N metachloroperbenzoic acid Natural products OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 description 9
- 125000005296 thioaryloxy group Chemical group 0.000 description 9
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 9
- 229920002554 vinyl polymer Polymers 0.000 description 9
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 8
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 8
- 229910052794 bromium Inorganic materials 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 238000004440 column chromatography Methods 0.000 description 8
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- 230000027756 respiratory electron transport chain Effects 0.000 description 8
- 229910000104 sodium hydride Inorganic materials 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 125000002521 alkyl halide group Chemical group 0.000 description 7
- 238000006254 arylation reaction Methods 0.000 description 7
- 125000000753 cycloalkyl group Chemical group 0.000 description 7
- 125000005842 heteroatom Chemical group 0.000 description 7
- 230000005525 hole transport Effects 0.000 description 7
- 238000001556 precipitation Methods 0.000 description 7
- 238000006862 quantum yield reaction Methods 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 125000001118 alkylidene group Chemical group 0.000 description 6
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 6
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 6
- 125000001188 haloalkyl group Chemical group 0.000 description 6
- 238000002347 injection Methods 0.000 description 6
- 239000007924 injection Substances 0.000 description 6
- 230000003647 oxidation Effects 0.000 description 6
- 238000007254 oxidation reaction Methods 0.000 description 6
- 239000012071 phase Substances 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 238000006467 substitution reaction Methods 0.000 description 6
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 5
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 5
- 239000003513 alkali Substances 0.000 description 5
- 125000003277 amino group Chemical group 0.000 description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 5
- 230000000903 blocking effect Effects 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- NZZIMKJIVMHWJC-UHFFFAOYSA-N dibenzoylmethane Chemical compound C=1C=CC=CC=1C(=O)CC(=O)C1=CC=CC=C1 NZZIMKJIVMHWJC-UHFFFAOYSA-N 0.000 description 5
- RRXYBJYIUHTJTO-UHFFFAOYSA-N europium;1,10-phenanthroline Chemical compound [Eu].C1=CN=C2C3=NC=CC=C3C=CC2=C1 RRXYBJYIUHTJTO-UHFFFAOYSA-N 0.000 description 5
- 238000000605 extraction Methods 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 5
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- TZMFJUDUGYTVRY-UHFFFAOYSA-N pentane-2,3-dione Chemical compound CCC(=O)C(C)=O TZMFJUDUGYTVRY-UHFFFAOYSA-N 0.000 description 5
- 239000012312 sodium hydride Substances 0.000 description 5
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 description 5
- 229940124530 sulfonamide Drugs 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Natural products CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- 238000007126 N-alkylation reaction Methods 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 4
- 229910052786 argon Inorganic materials 0.000 description 4
- 150000003818 basic metals Chemical class 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000004305 biphenyl Substances 0.000 description 4
- 239000002981 blocking agent Substances 0.000 description 4
- 238000004891 communication Methods 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 4
- 230000001815 facial effect Effects 0.000 description 4
- 239000011737 fluorine Substances 0.000 description 4
- 125000005843 halogen group Chemical group 0.000 description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 4
- 125000004646 sulfenyl group Chemical group S(*)* 0.000 description 4
- 125000005309 thioalkoxy group Chemical group 0.000 description 4
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 4
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 239000005662 Paraffin oil Substances 0.000 description 3
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 238000013019 agitation Methods 0.000 description 3
- 150000001335 aliphatic alkanes Chemical class 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 150000001450 anions Chemical class 0.000 description 3
- 229910052728 basic metal Inorganic materials 0.000 description 3
- 235000010290 biphenyl Nutrition 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 125000004185 ester group Chemical group 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- YUCFVHQCAFKDQG-UHFFFAOYSA-N fluoromethane Chemical compound F[CH] YUCFVHQCAFKDQG-UHFFFAOYSA-N 0.000 description 3
- 230000006870 function Effects 0.000 description 3
- 125000000623 heterocyclic group Chemical group 0.000 description 3
- 238000004770 highest occupied molecular orbital Methods 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 125000001624 naphthyl group Chemical group 0.000 description 3
- 239000011368 organic material Substances 0.000 description 3
- 230000001590 oxidative effect Effects 0.000 description 3
- 230000000737 periodic effect Effects 0.000 description 3
- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical compound OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Substances [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 229910000108 silver(I,III) oxide Inorganic materials 0.000 description 3
- YPYBVYAVVFLHDN-UHFFFAOYSA-N 1,10-phenanthrolin-2-amine Chemical compound C1=CN=C2C3=NC(N)=CC=C3C=CC2=C1 YPYBVYAVVFLHDN-UHFFFAOYSA-N 0.000 description 2
- VDULMXJUOWIPGE-UHFFFAOYSA-N 1-phenylisoquinoline quinoline Chemical compound N1=CC=CC2=CC=CC=C12.C1(=CC=CC=C1)C1=NC=CC2=CC=CC=C12 VDULMXJUOWIPGE-UHFFFAOYSA-N 0.000 description 2
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 2
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- 229910052693 Europium Inorganic materials 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical group NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- 229910004298 SiO 2 Inorganic materials 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 2
- KJLPWIOVCYTBQS-UHFFFAOYSA-N [NH+]1=CNC=C1.I(=O)(=O)[O-] Chemical class [NH+]1=CNC=C1.I(=O)(=O)[O-] KJLPWIOVCYTBQS-UHFFFAOYSA-N 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- 239000004411 aluminium Substances 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 239000000010 aprotic solvent Substances 0.000 description 2
- 150000001502 aryl halides Chemical class 0.000 description 2
- 229910052788 barium Inorganic materials 0.000 description 2
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 2
- 239000004327 boric acid Substances 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000002800 charge carrier Substances 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 239000002772 conduction electron Substances 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- ORBBTCHHNMWMCP-UHFFFAOYSA-K cycloocta-1,5-diene trichloroiridium Chemical compound [Ir](Cl)(Cl)Cl.C1=CCCC=CCC1 ORBBTCHHNMWMCP-UHFFFAOYSA-K 0.000 description 2
- 239000000539 dimer Substances 0.000 description 2
- LIKFHECYJZWXFJ-UHFFFAOYSA-N dimethyldichlorosilane Chemical compound C[Si](C)(Cl)Cl LIKFHECYJZWXFJ-UHFFFAOYSA-N 0.000 description 2
- 238000001194 electroluminescence spectrum Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- OGPBJKLSAFTDLK-UHFFFAOYSA-N europium atom Chemical compound [Eu] OGPBJKLSAFTDLK-UHFFFAOYSA-N 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000005286 illumination Methods 0.000 description 2
- 150000002460 imidazoles Chemical class 0.000 description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- KUBBZTZQWIGHFH-UHFFFAOYSA-N methyl 4-imidazol-1-ylbenzoate Chemical class C1=CC(C(=O)OC)=CC=C1N1C=NC=C1 KUBBZTZQWIGHFH-UHFFFAOYSA-N 0.000 description 2
- 239000002480 mineral oil Substances 0.000 description 2
- 235000010446 mineral oil Nutrition 0.000 description 2
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- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 125000005499 phosphonyl group Chemical group 0.000 description 1
- 125000004574 piperidin-2-yl group Chemical group N1C(CCCC1)* 0.000 description 1
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 description 1
- NJBFOOCLYDNZJN-UHFFFAOYSA-N pipobroman Chemical compound BrCCC(=O)N1CCN(C(=O)CCBr)CC1 NJBFOOCLYDNZJN-UHFFFAOYSA-N 0.000 description 1
- 239000003880 polar aprotic solvent Substances 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 150000004032 porphyrins Chemical class 0.000 description 1
- IUBQJLUDMLPAGT-UHFFFAOYSA-N potassium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([K])[Si](C)(C)C IUBQJLUDMLPAGT-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- DNXIASIHZYFFRO-UHFFFAOYSA-N pyrazoline Chemical compound C1CN=NC1 DNXIASIHZYFFRO-UHFFFAOYSA-N 0.000 description 1
- 150000003233 pyrroles Chemical class 0.000 description 1
- 230000005610 quantum mechanics Effects 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- KZUNJOHGWZRPMI-UHFFFAOYSA-N samarium atom Chemical compound [Sm] KZUNJOHGWZRPMI-UHFFFAOYSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000007493 shaping process Methods 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- YKLJGMBLPUQQOI-UHFFFAOYSA-M sodium;oxidooxy(oxo)borane Chemical compound [Na+].[O-]OB=O YKLJGMBLPUQQOI-UHFFFAOYSA-M 0.000 description 1
- 239000008234 soft water Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- GZCRRIHWUXGPOV-UHFFFAOYSA-N terbium atom Chemical compound [Tb] GZCRRIHWUXGPOV-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical group 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 230000008646 thermal stress Effects 0.000 description 1
- 125000000101 thioether group Chemical group 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- UORVGPXVDQYIDP-UHFFFAOYSA-N trihydridoboron Chemical group B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 1
- BJAARRARQJZURR-UHFFFAOYSA-N trimethylazanium;hydroxide Chemical compound O.CN(C)C BJAARRARQJZURR-UHFFFAOYSA-N 0.000 description 1
- 229910006400 μ-Cl Inorganic materials 0.000 description 1
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Abstract
本发明涉及含有吩噻嗪S-氧化物或吩噻嗪S,S-二氧化物基团的硅烷,含有所述硅烷的有机发光二极管,以及含有至少一种所述硅烷和至少一种三线态发射体的发光层。本发明还涉及生产本发明硅烷的方法及所述硅烷在有机发光二极管中优选作为基质材料和/或三线态发射体的阻断剂材料的用途。
Description
本发明涉及包含吩噻嗪S-氧化物或吩噻嗪S,S-二氧化物基团的硅烷,包含本发明硅烷的有机发光二极管,包含至少一种本发明硅烷和至少一种三线态发射体的发光层,包含至少一种本发明硅烷的阻断剂层,制备本发明硅烷的方法及本发明硅烷在有机发光二极管中优选作为基质材料和/或三线态发射体的阻断剂材料的用途。
有机发光二极管(OLED)利用了材料在受到电流激发时发光的特性。OLED作为用于生产平板显示单元的阴极射线管和液晶显示器的替代品尤其受到关注。包含OLED的器件由于非常紧凑的设计和固有的低功耗而尤其适合于移动应用如用于移动电话、便携式电脑等以及照明。
OLED作用方式的基本原理和合适的OLED构造(层)对本领域熟练技术人员已知并且例如描述于WO2005/113704中,在此引用该文献。除了荧光材料(荧光发射体)外,所用发光材料(发射体)还可以为磷光材料(磷光发射体)。磷光发射体通常为有机金属配合物,其与显示出单线态发射的荧光发射体相比而显示出三线态发射(三线态发射体)(M.A.Baldow等,Appl.Phys.Lett.1999,75,4-6)。因为量子力学原因,当使用三线态发射体(磷光发射体)时,高达四倍量子效率、能量效率和功率系数是可能的。为了实现有机金属三线态发射体(磷光发射体)在实践中的使用优点,必需提供操作寿命长、对热应力稳定性高及使用电压和操作电压低的器件组件。
这类器件组件例如可以包含基质材料,其中实际发光体以分布形式存在。此外,所述器件组件可以包含阻断剂材料,并且空穴阻断剂、激子阻断剂和/或电子阻断剂可以在所述器件组件中存在。基质材料和所用阻断剂材料的选择尤其对OLED的发光度和量子产率有显著影响。
现有技术提出用于OLED的许多不同材料。在所提出的材料中,还有包含取代的,尤其是芳基取代的硅烷的那些。
例如,US2005/0214572A1涉及包含至少一种芳基硅烷优选作为发光层中基质材料的OLED。所述芳基硅烷具有至少两个被含氮杂原子取代的芳基。US2005/0214572A1中没有公开具有吩噻嗪S-氧化物或吩噻嗪S,S-二氧化物取代基的芳基硅烷的用途。
WO2004/095598A2涉及其发光层包含具有至少3.2eV的大的能带宽度的基质材料的OLED。WO2004/095598A2中提及的基质材料包括芳基硅烷。然而,WO2004/095598A2中没有提及吩噻嗪S-氧化物或吩噻嗪S,S-二氧化物取代的芳基硅烷的用途。
JP2005/220088A2涉及其芳基带有含氮取代基的芳基硅烷。根据JP2005/220088A2的化合物的能带宽度大于3.0eV。根据JP2005/220088A2,提及的芳基硅烷用作OLED中的空穴传输材料。JP2005/220088A2中没有提及作为基质材料或在OLED中的用途。此外,JP2005/220088A2没有公开其芳基带有吩噻嗪S-氧化物或吩噻嗪S,S-二氧化物取代基的芳基硅烷。
JP2002/308837A2涉及具有空穴传输特性的化合物。根据JP2002/308837A2,这些化合物可为其芳基被氮杂环取代的芳基硅烷。在JP2002/308837A2中未提及芳基被吩噻嗪S-氧化物或吩噻嗪S,S-二氧化物取代基取代。此外,根据JP2002/308837A2的化合物用作空穴传输材料。在JP2002/308837A2中未提及所述化合物作为发光层中基质材料和/或阻断剂材料的用途。
WO03/017732A1涉及包含其中存在发光材料的可聚合无定形基质的OLED。形成可聚合基质的基本结构包含其芳基可尤其被杂芳基取代的芳基硅烷单元。WO03/017732A1中没有提及芳基被吩噻嗪S-氧化物或吩噻嗪S,S-二氧化物基团取代。此外,根据WO03/017732A1的基质为可聚合无定形基质。
US6,194,089B1公开了具有包含连续有机介质AxByCz的有机发光层的OLED。在该介质中,A为电子传输材料,B为空穴传输材料并且C为空穴注入材料。材料A、B和C可以在连续有机介质内的不同浓度梯度存在于所述介质中。在其它化合物中,组分B可为其芳基可被芳族叔氨基取代的芳基硅烷。在US6,194,089B1中没有提及其芳基被吩噻嗪S-氧化物或 吩噻嗪S,S-二氧化物取代基取代的芳基硅烷。
EP0774883A2公开了具有包含在混合物中的2种或更多种空穴传输材料的空穴传输层的OLED。所用空穴传输材料可为芳基硅烷并且芳基可被叔胺单元取代。关于其芳基被吩噻嗪S-氧化物或吩噻嗪S,S-二氧化物单元取代的芳基硅烷的用途,EP0774883A2没有给出任何信息。此外,根据EP0774883A2的芳基硅烷用作空穴传输层中的空穴传输材料,而不用作发光层中的基质材料和/或不用作阻断剂材料。
因此,本申请相对于现有技术的目的是提供在OLED中,尤其在OLED的发光层中使用的新颖基质材料和新颖阻断剂材料,其优选用作基质材料和/或三线态发射体的阻断剂材料。所述材料应易于获得并且在与发射体结合时在OLED中带来良好的发光度和量子产率。
该目的通过提供通式I的化合物实现:
其中
X为SO2或SO,优选SO2;
R1在每种情况下独立地为任选取代的芳基、任选取代的杂芳基或任选取代的烷基;
R2、R3在每种情况下独立地为任选取代的烷基,任选取代的芳基,任选取代的杂芳基或具有给体或受体作用的取代基,例如烷氧基、芳氧基、芳基羰氧基(-C=O(OR))、-C=O(SR)、杂芳基、羟基、氨基、卤素、-C=O(R)、-OC=O(R)、-SC=O(R)、酰氨基(-C=O(NR))、-NRC=O(R)、磺酰基、磺酰胺、乙烯基、CN、硝基、硫代烷氧基、硫代芳氧基或SiR3,其中R在每种情况下独立地为氢、烷基或芳基;
m为1、2、3或4,优选2、3或4;
n为1或2;
o、p各自独立地为0、1、2、3或4,优选0、1或2,更优选0;
L为选自以下基团的桥接基团:
-CH2-(B)j-和任选取代的杂亚芳基;R4、R5、R6在每种情况下独立地为任选取代的烷基,任选取代的芳基,任选取代的杂芳基或具有给体或受体作用的取代基;例如烷氧基、芳氧基、芳基羰氧基(-C=O(OR))、-C=O(SR)、杂芳基、羟基、氨基、卤素、-C=O(R)、-OC=O(R)、-SC=O(R)、酰氨基(-C=O(NR))、-NRC=O(R)、磺酰基、磺酰胺、乙烯基、CN、硝基、硫代烷氧基、硫代芳氧基或SiR3,其中R在每种情况下独立地为氢、烷基或芳基;
q、r、s各自独立地为0、1、2、3或4,优选0、1或2,更优选0;
B为亚烷基-CkH2k-CH2-,其中-CkH2k-单元的一个或多个非相邻基团CH2可以被氧或NR7代替;
R7为芳基或烷基;
k为1、2、3、4、5、6、7或8;及
j为0或1。
本发明的式I化合物尤其适合作为基质材料和/或阻断剂材料用于OLED中。它们优选作为基质材料与实际发射体一起用于发光层中。与基质材料一起用于OLED发光层中的发射体更优选为三线态发射体。在另一实施方案中,式(I)化合物用作空穴/光子-激子阻断剂。
式I化合物易于获得,并且在作为基质材料与实际发射体结合使用时和在作为阻断剂材料与实际发射体结合使用时,在OLED中使用时具有良好的发光度和量子产率。
取决于其取代方式,式(I)化合物可用作电子传导基质和/或空穴/激子阻断剂或用作空穴传导或双极基质和/或电子/激子阻断剂。
电子传导基质和/或空穴/激子阻断剂
没有任何给电子取代基R2、R3、R4、R5、R6(即具有+I和/或+M效应 的取代基)的式I化合物基本上仅能传导电子并由此通常用作电子传导基质和/或空穴/激子阻断剂。
双极基质和/或空穴/激子阻断剂或电子/激子阻断剂
具有给电子取代基R2、R3、R4、R5、R6的式I化合物可传导电子或空穴。因此,它们可用作电子和空穴传导基质(双极基质)。取决于***(OLED结构),它们可用作空穴/激子阻断剂或电子/激子阻断剂。通常,在式I化合物中存在给电子取代基越多,式I化合物作为空穴传导基质和/或电子/激子阻断剂的适用性就越好。
术语给电子取代基(+I和/或+M效应)和吸电子取代基(-I和/或-M效应)以本领域熟练技术人员已知的常规方式用于本申请中。合适的给电子和吸电子取代基例如为氨基、烷氧基、卤素取代基、芳氧基、芳基羰氧基、杂芳基、羟基、-C=O(R)、-OC=O(R)、-SC=O(R)、酰氨基、-NRC=O(R)、砜基团、磺酰胺基团、乙烯基、CN、硝基、硫代烷氧基、硫代芳氧基或SiR3,其中R在每种情况下独立地为氢、烷基或芳基,或者卤代烷基如CF3。
优选式(I)化合物用作电子传导基质和/或空穴-激子阻断剂。在优选的实施方案中,这意味着本发明涉及没有任何给电子取代基R2、R3、R4、R5、R6的式(I)化合物。
根据本申请,烷基以及烷氧基的烷基可以为直链或支化或环状的和/或任选被选自芳基、烷氧基和卤素的取代基取代。合适的芳基取代基如下所述。合适烷基的实例为甲基、乙基、丙基、丁基、戊基、己基、庚基和辛基以及被芳基、烷氧基和/或卤素,尤其是F取代的所述烷基的衍生物如CF3。还包括这些基团的正异构体和支化异构体如异丙基、异丁基、异戊基、仲丁基、叔丁基、新戊基、3,3-二甲基丁基、2-乙基己基等。优选的烷基为甲基、乙基、叔丁基和CF3。
根据本申请,环烷基可任选被选自芳基、烷氧基和卤素的取代基取代。环烷基优选未被取代。合适的芳基取代基如下所述。合适环烷基的实例为环丙基、环丁基、环戊基、环己基、环庚基、环辛基、环壬基和环癸基。合适的话,环烷基也可以为多环体系如十氢萘基、降冰片基、冰片基或金刚烷基。环烷基可未被取代或任选被一个或多个其它基团,尤其是烷基、 芳基、烷氧基和/或卤素取代。
就本发明而言,合适的卤素取代基为氟、氯、溴和碘,优选氟、氯和溴,更优选氟和氯。
合适的烷氧基和硫代烷氧基相应地由上文定义的烷基产生。在这里,实例包括OCH3、OC2H5、OC3H7、OC4H9和OC8H17以及SCH3、SC2H5、SC3H7、SC4H9和SC8H17。C3H7、C4H9和C8H17包括正异构体和支化异构体如异丙基、异丁基、仲丁基、叔丁基和2-乙基己基。特别优选甲氧基、乙氧基、正辛氧基、2-乙基己氧基和SCH3。
在本发明中,芳基指由不包含任何环杂原子的单环、双环或三环芳族化合物衍生的基团。当它们不是单环体系时,对于术语“芳基”在第二个环情况下也可以为饱和形式(全氢化形式)或部分饱和形式(例如二氢形式或四氢形式),只要所述特定形式已知且稳定。这意味着本发明中术语“芳基”例如也包括其中两个或三个基团均为芳族的双环或三环基团,或者其中仅一个环为芳族的双环或三环基团,以及其中两个环为芳族的三环基团。芳基实例为:苯基、萘基、2,3-二氢化茚基、1,2-二氢萘次甲基、1,4-二氢萘次甲基、茚基、蒽基、菲基或1,2,3,4-四氢萘基。芳基更优选为苯基或萘基,最优选苯基。
芳基可未被取代或被一个或多个其它基团取代。合适的其它基团选自烷基、芳基或具有给体或受体作用的取代基,例如烷氧基、芳氧基、芳基羰氧基、杂芳基、羟基、氨基、卤素、-C=O(R)、-OC=O(R)、-SC=O(R)、酰氨基(-C=O(NR))、-NRC=O(R)、砜、磺酰胺、乙烯基、CN、硝基、硫代烷氧基、硫代芳氧基或SiR3,其中R在每种情况下独立地为氢、烷基或芳基。烷基优选未被取代或者被一个或多个烷氧基、氰基或CF3或F取代。芳基更优选为未取代的苯基、4-烷基苯基、4-烷氧基苯基、2,4,6-三烷基苯基、2,4,6-三烷氧基苯基或N,N-二芳基氨基苯基,优选4-甲基苯基、4-甲氧基苯基、2,4,6-三甲基苯基、2,4,6-三甲氧基苯基、9-苯基咔唑基,以及相应的苯并稠合基。
合适的芳氧基、芳硫基和芳基羰氧基相应地由上文定义的芳基衍生。特别优选苯氧基、苯基硫基和苯基羰氧基。
合适的氨基具有通式-NR’R”,其中R’和R”各自独立地为烷基或芳 基。可任选取代的各个合适烷基和芳基如上所述。合适氨基的实例为二芳基氨基如二苯基氨基,和二烷基氨基如二甲基氨基、二乙基氨基,芳烷基氨基如苯基甲基氨基。
杂芳基应理解为指的是可通过用杂原子代替芳基基本骨架中的至少一个碳原子部分地由上述芳基产生的单环、双环或三环杂芳族化合物。优选的杂原子为N、O和S。所述基本骨架特别优选选自诸如吡啶和5元杂芳族化合物如噻吩、吡咯、咪唑或呋喃的体系。这些基本骨架可任选稠合一个或两个6元芳族基团。合适的体系为咔唑基、苯并咪唑基、苯并呋喃基、氧芴基或硫芴基。所述基本骨架可在一个、超过一个或所有可取代位置被取代,此时合适取代基与已在芳基定义下描述的取代基相同。然而,杂芳基优选未被取代。在这里应特别提及吡啶-2-基、吡啶-3-基、吡啶-4-基、噻吩-2-基、噻吩-3-基、吡咯-2-基、吡咯-3-基、呋喃-2-基、呋喃-3-基和咪唑-2-基以及对应的苯并稠合基,尤其是苯并咪唑基、苯并呋喃基、氧芴基或硫芴基。
杂环烷基应理解为指与上述环烷基的区别在于环烷基的基本骨架中至少一个碳原子已被杂原子代替的基团。优选的杂原子为N、O和S。所述基本骨架可在一个、超过一个或所有可取代位置被取代,此时合适取代基与已在芳基定义下描述的取代基相同。在这里应特别提及含氮基团:吡咯烷-2-基、吡咯烷-3-基、哌啶-2-基、哌啶-3-基、哌啶-4-基。
就本申请而言,具有给体或受体作用的基团应理解为指的是下列基团:
具有给体作用的基团应理解为指的是具有+I和/或+M效应的基团,而具有受体作用的基团应理解为指的是具有-I和/或-M效应的基团。合适的具有给体或受体作用的基团为卤素基团,优选F、Cl、Br、I,更优选F、Cl,卤代烷基如CF3,烷氧基,芳氧基,羰基,酯基,氧羰基和羰氧基如芳基羰氧基,胺基,酰胺基,-NR(=OCR),基团CH2F,基团CF3,基团CN,硫基,硫代烷氧基,硫代芳氧基,磺酸基团,硫羰基,羰硫基,磺酸酯基团,硼酸基团,硼酸酯基团,膦酸基团,膦酸酯基团,膦基,亚砜基团,磺酰基,磺酰胺基团,硫化物基团,硝基,OCN,硼烷基团,甲硅烷基,锡酸酯基团,亚氨基,肼基,酰肼(hydrazole)基,肟基,亚硝基,重氮基团,基团SiR3,氧化膦基团,羟基,乙烯基,杂芳基或基团SCN。优 选的具有给体或受体作用的基团为烷氧基、芳氧基、烷基羰氧基((-C=O(OR))、羰硫基(-C=O(SR)、杂芳基、羟基、氨基、卤素、羰基(-C=O(R))、氧羰基(-OC=O(R))、硫羰基(-SC=O(R))、酰氨基(-C=O(NR))、-NRC=O(R)、磺酰基、磺酰胺基团、乙烯基、硫代烷氧基、硫代芳氧基或SiR3,其中R在每种情况下独立地为氢、烷基或芳基。非常特别优选F、Cl、CN、芳氧基、烷氧基和卤代烷基如CF3。
磺酰胺基团应理解为指的是-SO2NHR,其R为氢、烷基或芳基,优选氢、C1-C6烷基、苯基或苄基。
磺酰基理解为指的是-S(O)2R,其中R为氢、烷基、芳基或氨基,优选氢、C1-C6烷基、苯基、苄基或-NR’2,其中R’每种情况下独立地为氢、烷基或芳基,优选氢、C1-C6烷基或苄基。
亚烷基桥B的-CkH2k-单元应理解为指的尤其是线性亚烷基链-CH2-、-(CH2)2-、-(CH2)3-、-(CH2)4-、-(CH2)5-、-(CH2)6-、-(CH2)7-和-(CH2)8-。然而,它们还可以为支化的,使得它们例如还可以为-CH(CH3)-、-C(CH3)2-、-CH2-CH(CH3)-、-CH(CH3)-CH(CH3)-、-C(CH3)2-C(CH3)2-、-CH(CH3)-CH2-CH(CH3)-、-CH(CH3)-(CH2)2-CH(CH3)-、-CH(CH3)-(CH2)3-CH(CH3)-、-CH(CH3)-(CH2)4-CH(CH3)-、-C(CH3)2-CH2-C(CH3)2-或-C(CH3)2-(CH2)2-C(CH3)2-链。此外,在亚烷基桥B的-CkH2k-单元中,一个或多个非相邻基团CH2可以被氢或NR代替。其实例尤其为-O-C2H4-O-、-O-(C2H4-O-)2、-NR-C2H4-NR-或-NR-(C2H4-NR-)2,其中R尤其为烷基如甲基、乙基、丙基、异丙基、丁基、仲丁基或叔丁基,或者芳基如苯基。
式I化合物中的R1在每种情况下独立地选自任选取代的芳基、任选取代的杂芳基和任选取代的烷基,其中合适的芳基、杂芳基和烷基和合适的取代基已在上文描述。R1优选为烷基,尤其是甲基、乙基或丙基,更优选甲基,或者未取代或取代的芳基,优选未取代或取代的苯基,此时苯基上的取代基为优选被卤素取代的烷基,烷氧基,CN或氨基取代基如CF3、OCH3、CN或二芳基氨基。芳基优选被1-3个氨基取代基,更优选二芳基氨基取代基,尤其是二苯基氨基取代;杂芳基,优选N-咔唑基及其衍生物。基团R1最优选各自独立地为苯基、甲基、9-苯基咔唑基或4-N,N-二苯基氨基苯基。
式I化合物包含0、1、2或至多3个基团R1。这意味着式I化合物中的m可以为1、2、3或4;m优选为2、3或4。当m为4时,式I化合物不包含任何基团R1。
式I中R2和R3各自独立地为任选取代的烷基、任选取代的芳基或任选取代的杂芳基,其中合适的烷基、芳基和杂芳基和合适的取代基已在上文描述,或者具有受体或给体作用的取代基。合适的具有受体或给体作用的取代基已在上文描述。优选的具有受体或给体作用的取代基为:卤代烷基如CF3、烷氧基、芳氧基、芳基羰氧基(-C=O(OR))、-C=O(SR)、杂芳基、羟基、氨基、卤素、-C=O(R)、-OC=O(R)、-SC=O(R)、酰氨基(-C=O(NR))、-NRC=O(R)、磺酰基、磺酰胺、乙烯基、CN、硝基、硫代烷氧基、硫代芳氧基或SiR3,其中R在每种情况下独立地为氢、烷基或芳基。
式I中o和p各自独立地为0、1、2、3或4,优选0、1或2,更优选0。当o或p分别为0时,在式I化合物中不存在基团R2或R3,即吩噻嗪S-氧化物或吩噻嗪S,S-二氧化物基团的所有可取代位置均被氢原子取代。
所述桥接基团L为选自以下基团的基团:
-CH2-(B)j-和任选取代的杂亚芳基,其中基团R4、R5和R6在每种情况下独立地为任选取代的烷基,任选取代的芳基,任选取代的杂芳基或具有给体或受体作用的取代基。合适的烷基、芳基、杂芳基和具有给体或受体作用的基团已在上文描述。
q、r、s可各自独立地为0、1、2、3或4,优选0、1或2,更优选0。当q、r或s为0时,所述桥接基团L不包含任何取代基R4、R5或R6,即桥接基团L的所有可取代位置均带有氢原子。
在桥接基团L为基团-CH2-(B)j-的情况下,B为亚烷基-CkH2k-CH2-,其中-CkH2k-单元的一个或多个非相邻基团CH2可以被氧或NR7代替。
R7为芳基或烷基,其中合适的烷基已在上文描述。特别优选的烷基为甲基或乙基。芳基优选为苯基。
亚烷基B中的k为1、2、3、4、5、6、7或8。j为0或1。
在优选的实施方案中,基团B为其中-CkH2k-单元均未被氧或NR7代替的亚烷基。所述亚烷基由此优选为通式-(CH2)1-9-的亚烷基。所述桥接基团L由此可以为由1-10个基团CH2形成的亚烷基。
优选作为基团L使用的任选取代的杂亚芳基具有下式之一:
其中
R7和R8各自独立地为任选取代的烷基、任选取代的杂芳基或具有给体或受体作用的取代基,其中合适的烷基、芳基、杂芳基和具有给体或受体作用的基团已在上文描述;及
Y为NR’、PR’、S、O,其中R’为烷基或芳基并且合适的烷基和芳基已在上文描述;
Z为N
t为0、1或2;及
u为0、1、2或3,
其中当t或u为0时,所有可取代位置均带有氢原子。
在优选的实施方案中,基团L为选自以下基团的桥接基团:
桥接基团L更优选为
最优选
基团R4、R5和R6及指数q、j各自如上面所定义。在特别优选的实施方案中,q、r和s各自为0,即上述桥接基团L的可取代位置均带有氢原子。
本发明优选涉及式I化合物,其中:
X为SO2;
m为2、3或4;
o、p各自为0、1或2,优选为0;
q为0、1或2,优选为0。
在另一优选的实施方案中,本发明涉及式I化合物,其中与Si结合的基团L或R1中至少两个为芳族基团。
在优选的实施方案中,本发明涉及式(I)化合物,其中:
R2、R3各自为氢;
o、p各自为0;
n为1或2;
L为1,4-亚苯基或1,2-亚乙基;
m为1、2、3或4;及
R1相同或不同且为CH3、Ph、
特别优选的式I化合物的实例如下所述:
除了所述化合物外,基团L和指数n和m的其它变型也是可以的。例如,式(I)化合物可以额外具有三个吩噻嗪S,S-二氧化物基团和一个基团R1。
本发明的式I化合物可通过本领域熟练技术人员已知的所有合适方法制备。优选通过包括以下步骤的方法制备式I化合物:
(i)通过使式(III)的吩噻嗪或吩噻嗪衍生物与式(IV)的双官能化合物反应而制备吩噻嗪衍生物(II):
其中
R2、R3在每种情况下独立地为任选取代的烷基,任选取代的芳基,任选取代的杂芳基或具有给体或受体作用的取代基;例如烷氧基、芳氧基、芳基羰氧基(-C=O(OR))、-C=O(SR)、杂芳基、羟基、氨基、卤素、-C=O(R)、-OC=O(R)、-SC=O(R)、酰氨基(-C=O(NR))、-NRC=O(R)、磺酰基、磺 酰胺、乙烯基、CN、硝基、硫代烷氧基、硫代芳氧基或SiR3,其中R在每种情况下独立地为氢、烷基、芳基或卤代烷基;
o、p各自独立地为0、1、2、3或4,优选0、1或2,更优选0;
L为选自以下基团的桥接基团:
-CH2-(B)j-和任选取代的杂亚芳基;R4、R5、R6在每种情况下独立地为任选取代的烷基,任选取代的芳基,任选取代的杂芳基或具有给体或受体作用的基团;例如烷氧基、芳氧基、芳基羰氧基(-C=O(OR))、羰硫基(-C=O(SR))、杂芳基、羟基、氨基、卤素、羰基(-C=O(R))、-NRC=O(R)、磺酰基、磺酰胺基团、乙烯基、硫代烷氧基、硫代芳氧基或SiR3,其中R在每种情况下独立地为氢、烷基、卤代烷基或芳基;
q、r、s各自独立地为0、1、2、3或4,优选0、1或2,更优选0;
B为亚烷基桥-CkH2k-CH2-,其中-CkH2k-单元的一个或多个非相邻基团CH2可以被氧或NR7代替;
R7为氢或烷基;
k为1、2、3、4、5、6、7或8;及
j为0或1;及
Y为卤素,优选选自Cl和Br,更优选为Br;
其中R2、R3、o和p各自如上面所定义,
Z-L-Y (IV)
其中L和Y各自如上面所定义,及
z为碘、氟、溴或甲苯磺酰基;
(ii)通过使吩噻嗪衍生物(II)与通式(VIa)的卤烷基/芳基硅烷或通式(VIb)的 烷氧基硅烷反应而制备式(V)的吩噻嗪衍生物:
其中各符号和指数各自如上面所定义,及
m为1、2、3或4,优选2、3或4,及
n为1或2,
(R8)tSi(Hal)4-t (VIa)
(R8)tSi(OR9)4-t (VIb)
其中
R8为任选取代的芳基、任选取代的杂芳基或任选取代的烷基;
Hal为卤素,优选Cl;及
t为1、2或3;及
R9为烷基,优选乙基或甲基;
(iii)通过使式(V)的吩噻嗪衍生物与氧化剂反应而制备式(I)的吩噻嗪S-氧化物或S,S-二氧化物衍生物。
本发明方法中所用化合物的合适优选基团对应于上文就式I化合物所描述的优选基团。
步骤(i)
用于制备式(II)的吩噻嗪衍生物的式(III)的吩噻嗪或吩噻嗪衍生物可市购或可通过本领域熟练技术人员已知的方法制备。与式(III)的吩噻嗪或吩噻嗪衍生物反应的式(IV)的双官能化合物同样可市购或可通过本领域熟练技术人员已知的方法制备。
在本发明方法的步骤(i)中用式(IV)的双官能化合物取代式(III)的吩噻嗪或吩噻嗪衍生物的氮原子(N-烷基化或N-芳基化)优选在本领域熟练技术人员已知的碱存在下进行。所述碱优选为碱金属或碱土金属氢氧化物如 NaOH、KOH、Ca(OH)2,碱金属氢化物如NaH、KH,碱金属氨化物如NaNH2,碱金属或碱土金属碳酸盐如K2CO3,或者碱金属醇盐如NaOMe、NaOEt。此外,上述碱的混合物是合适的。特别优选NaOH、KOH或NaH。特别优选的碱为NaH和K2CO3。
N-烷基化(例如描述于M.Tosa等,Heterocycl.Communications,第7卷,第3期,2001,第277-282页中)或N-芳基化(例如描述于H.Gilman和D.A.Shirley,J.Am.Chem.Soc.66(1944)888;D.Li等,Dyes and Pigments49(2001)181-186中)优选在溶剂中进行。合适的溶剂例如为极性非质子溶剂如二甲亚砜、二甲基甲酰胺或醇。同样可以使用过量烷基卤或芳基卤作为溶剂,优选使用过量烷基碘或芳基碘。当存在相转移催化剂如四正丁基硫酸氢铵时,反应可额外在非极性非质子溶剂如甲苯中进行(例如如I.Gozlan等,J.Heterocycl.Chem.21(1984)613-614所公开)。
但是,N-芳基化也可通过铜催化偶联式(III)化合物与芳基卤,优选芳基碘而进行(Ullmann反应)。在青铜存在下使吩噻嗪N-芳基化的合适方法例如公开于H.Gilman等,J.Am.Chem.Soc.66(1944)888-893中。
式(III)化合物与式(IV)的双官能化合物的摩尔比通常为1∶1-1∶2,优选1∶1-1∶1.5。
N-烷基化或N-芳基化通常在标准压力下和在0至220℃或0至所用溶剂沸点的温度范围内进行。反应时间通常在0.5-48小时内变化。
使式(III)化合物N-烷基化或N-芳基化的合适条件每种情况下可通过本领域熟练技术人员毫无问题地在初级试验中确定。例如,N-烷基化或N-芳基化的过程可用分析法如通过IR光谱法监测。
所得粗产物通常通过本领域熟练技术人员已知的方法后处理。
步骤(ii)
在步骤(ii)中,式(V)的吩噻嗪衍生物通过使在步骤(i)中制备的式(II)的吩噻嗪衍生物与式(VIa)的卤烷基/芳基硅烷或式(VIb)的烷氧基硅烷反应而制备。式(VIa)的卤烷基/芳基硅烷和式(VIb)的烷氧基硅烷通常可市购或可通过本领域熟练技术人员已知的方法制备。合适的卤烷基/芳基硅烷为卤烷基硅烷、卤芳基硅烷或混合的卤烷基/芳基硅烷。所用合适的卤烷基/芳基硅 烷例如可为二氯二甲基硅烷、二氯二苯基硅烷、二氯甲基苯基硅烷或四氯硅烷。
式(III)的吩噻嗪或吩噻嗪衍生物通常在金属或金属盐如镁或BuLi(正、仲、叔)存在下与式(VIa)的卤烷基/芳基硅烷或者烷氧基硅烷(Wb)反应。本发明方法步骤(ii)中反应的合适反应条件对本领域熟练技术人员已知或可通过本领域熟练技术人员容易地确定。
通常,步骤(ii)中方法在标准压力下进行。温度通常为-78℃至+100℃。反应时间通常为1-24小时。
所得粗产物通常通过本领域熟练技术人员已知的方法后处理。
步骤(iii)
在本发明方法的步骤(iii)中,本发明的式(I)的吩噻嗪S-氧化物或S,S-二氧化物衍生物由在步骤(ii)中制备的式(V)的吩噻嗪衍生物制备。本发明的式(I)的吩噻嗪S-氧化物或S,S-二氧化物衍生物通过使式(V)的吩噻嗪衍生物与氧化剂反应而获得。合适的氧化剂取决于如何制备吩噻嗪S-氧化物或S,S-二氧化物衍生物。适合于制备特定衍生物的氧化剂对本领域熟练技术人员已知。合适的氧化剂的实例在下文描述。
将吩噻嗪氧化成本发明所用吩噻嗪S-氧化物或吩噻嗪S,S-二氧化物的合适方法对本领域熟练技术人员已知并且例如描述于M.Tosa等,Heterocyclic Communications,第7卷,第3期,2001,第277-282页中。
吩噻嗪S-氧化物衍生物的氧化例如借助H2O2在乙醇、乙醇-丙酮混合物或草酸中,借助过硫酸铵、硝酸、亚硝酸、无机氮氧化物,合适的话与(大气)氧气、NO+BF4 -/O2、CrO3一起在吡啶、臭氧、四甲基环氧乙烷、全氟烷基哑嗪(oxaziridine)中或者借助电化学方法进行。此外,相应官能化的式V的吩噻嗪向相应的式(I)的吩噻嗪S-氧化物衍生物的氧化可借助间氯过苯甲酸在CH2Cl2中在0-5℃的温度下或借助发烟硝酸和冰乙酸的混合物在CCl4中进行(例如参见M.Tosa等,Heterocyclic Communications,第7卷,第3期,2001,第277-282页、)。
吩噻嗪S,S-二氧化物衍生物的氧化例如借助过酸如过乙酸(例如可由H2O2和AcOH获得),或者间氯过苯甲酸,过硼酸钠,NaOCl或重金属体 系如KMnO4/H2O、Et3PhN+MnO4 -在无机介质中,OsO4/N-甲基吗啉N-氧化物进行。例如,相应官能化的式(V)的吩噻嗪向相应的式(I)的吩噻嗪S,S-二氧化物衍生物的氧化可借助KMnO4水溶液和C16H35N(CH3)3 +Cl-在CHCl3中在室温下,或者借助间氯过苯甲酸在CH2Cl2中在室温下进行(例如参见M.Tosa等,Heterocyclic Communications,第7卷,第3期,2001,第277-282页)。
为了制备吩噻嗪S,S-二氧化物衍生物,式(V)的吩噻嗪衍生物和氧化剂,优选间氯过苯甲酸以通常1∶1.8-1∶4,优选1∶1.9-1∶3.5,更优选1∶1.9-1∶3的摩尔比使用。
为了制备吩噻嗪S-氧化物衍生物,式(V)的吩噻嗪衍生物和氧化剂以通常1∶0.8-1∶1.5,优选1∶1-1∶1.3的摩尔比使用。没有用来进一步氧化成吩噻嗪S,S-二氧化物衍生物的氧化剂如H2O2可以相比于上文就吩噻嗪衍生物所描述的更大过量使用。
氧化通常在溶剂,优选在选自卤代烃和双极性非质子溶剂的溶剂中进行。前者和后者的实例分别为二氯甲烷,以及乙腈和环丁砜。
取决于氧化剂,氧化成吩噻嗪S-氧化物衍生物通常在标准压力和-10℃至+50℃的温度下进行,并且氧化成吩噻嗪S,S-二氧化物衍生物通常在标准压力和0至+100℃的温度下进行。氧化的反应时间通常为0.25-4小时。
但是,将特定吩噻嗪衍生物氧化成相应吩噻嗪S-氧化物或吩噻嗪S,S-二氧化物衍生物的合适条件每种情况下可通过本领域熟练技术人员毫无问题地在初级试验中确定。例如,氧化过程可用分析法如通过IR光谱法监测。
在优选的变型中,式(I)的吩噻嗪S-氧化物衍生物通过在CH2Cl2中在0-20℃下用间氯过苯甲酸作为氧化剂氧化相应的式V的吩噻嗪衍生物而制备。
式(I)的吩噻嗪S,S-二氧化物衍生物通过在CH2Cl2中在0-40℃下用间氯过苯甲酸作为氧化剂氧化相应的式V的吩噻嗪衍生物而制备。
将所得吩噻嗪S-氧化物和吩噻嗪S,S-二氧化物通过本领域熟练技术人员已知的方法分离和后处理。
本发明的式I化合物可借助本发明方法以高纯度和良好产率获得。合适的话,高纯度通过提纯如通过重结晶在本发明方法中获得的产物而获得。
式(I)化合物特别适合用作有机发光二极管中的基质材料。它们尤其适合用作OLED的发光层中的基质材料,此时所述发光层包含优选一种或多重三线态发射体作为发射体化合物。
此外,式(I)化合物适合作为阻断剂材料,尤其是OLED中的阻断剂材料,其中优选将它们用作三线态发射体的阻断剂材料。取决于其取代方式,式(I)化合物可用作空穴/激子阻断剂或电子/激子阻断剂,如上文所述。
因此,本发明进一步提供包含至少一种式(I)化合物的OLED。在一个实施方案中,优选将式(I)化合物用作基质材料,此时所述基质材料更优选与三线态发射体一起使用。在另一实施方案中,式(I)化合物优选用作阻断剂材料,更优选用作三线态发射体的阻断剂材料。
此外,式(I)化合物可在OLED中用作基质材料和阻断剂材料。此时,基质材料和阻断剂材料可以为相同或不同的式(I)化合物。
本发明进一步提供包含至少一种本发明的式(I)化合物和至少一种发射体化合物的发光层,此时所述发射体化合物优选为三线态发射体。
在又一实施方案中,本发明涉及式(I)化合物在OLED中作为阻断剂材料的用途。此外,OLED可包含式(I)化合物作为基质材料和阻断剂材料。
本发明进一步涉及本发明的式(I)化合物在OLED中优选作为基质材料,尤其是作为发射体化合物的基质材料的用途,此时所述发射体化合物更优选为三线态发射体。
本发明的式(I)化合物在OLED的发光层中作为基质材料的用途同样构成本发明主题的另一部分。
在本文中,使用式I化合物作为基质材料和/或阻断剂材料不应排除这些化合物本身也发光。然而,在用作OLED中的发射体的化合物的情况下,根据本发明使用的基质材料和/或阻断剂材料当嵌入其它常规基质材料中或OLED包含式(I)化合物作为阻断剂材料时,与这些常规基质材料和/或阻断剂材料相比,其发光度和量子产率增加。
使用的许多发射体化合物基于金属配合物,尤其是金属Ru、Rh、Ir、 Pd和Pt的配合物,Ir的配合物尤其具有重要意义。根据本发明使用的式I化合物特别适合作为基于这类金属配合物的发射体的基质材料和/或阻断剂材料。尤其是,它们作为基质材料和/或阻断剂材料适合与Ru、Rh、Ir、Pd和Pt的配合物一起使用,更优选与Ir的配合物一起使用。
与作为OLED中的基质材料和/或阻断剂材料的式I化合物一起使用的合适金属配合物例如描述在文献WO02/60910A1、US2001/0015432A1、US2001/0019782A1、US2002/0055014A1、US2002/0024293A1、US2002/0048689A1、EP1191612A2、EP1191613A2、EP1211257A2、US2002/0094453A1、WO02/02714A2、WO00/70655A2、WO01/41512A1、WO02/15645A1、WO2005/019373A2、WO2005/113704A2、WO2006/115301A1、WO2006/067074A1和WO2006/056418中。
其它合适的金属配合物为可市购金属配合物:三(2-苯基吡啶)铱(III)、三(2-(4-甲苯基)吡啶基-N,C2’)铱(III)、三(1-苯基异喹啉)铱(III)、双(2-(2’-苯并噻吩基)吡啶基-N,C3’)(乙酰丙酮基)铱(III)、双(2-(4,6-二氟苯基)吡啶基-N,C2’)吡啶甲酸铱(III)、双(1-苯基异喹啉)(乙酰丙酮)铱(III)、双(二苯并[f,h]喹喔啉)(乙酰丙酮)铱(III)、双(2-甲基二苯并[f,h]喹喔啉)(乙酰丙酮)铱(III)和三(3-甲基-1-苯基-4-三甲基乙酰基-5-吡唑啉)铽(III)。
此外,下列可市购材料是合适的:三(二苯甲酰基乙酰丙酮基)单(菲咯啉)铕(III)、三(二苯甲酰基甲烷)单(菲咯啉)铕(III)、三(二苯甲酰基甲烷)单(5-氨基菲咯啉)铕(III)、三(二-2-萘甲酰基甲烷)单(菲咯啉)铕(III)、三(4-溴苯甲酰基甲烷)单(菲咯啉)铕(III)、三(二(联苯基甲烷))单(菲咯啉)铕(III)、三(二苯甲酰基甲烷)单(4,7-二苯基菲咯啉)铕(III)、三(二苯甲酰基甲烷)单(4,7-二甲基菲咯啉)铕(III)、三(二苯甲酰基甲烷)单(4,7-二甲基菲咯啉二磺酸)铕(III)二钠盐、三[二(4-(2-(2-乙氧基乙氧基)乙氧基)苯甲酰基甲烷)单(菲咯啉)铕(III)和三[二(4-(2-(2-乙氧基乙氧基)乙氧基)苯甲酰基甲烷)单(5-氨基菲咯啉)铕(III)。
在本发明的优选实施方案中,本发明的式I化合物作为基质材料与作为三线态发射体的碳烯配合物一起用于发光层中,即特别优选的三线态发射体为碳烯配合物。合适的碳烯配合物对本领域熟练技术人员已知且在一 些上述申请中和下文描述。在另一实施方案中,本发明的式(I)化合物作为阻断剂材料与作为三线态发射体的碳烯配合物一起使用。此外,本发明化合物可作为基质材料和阻断剂材料与作为三线态发射体的碳烯配合物一起使用。
因此,与作为OLED中的基质材料和/或阻断剂材料的式I化合物一起使用的合适金属配合物还例如是描述在WO2005/019373A2、WO2006/056418A2和WO2005/113704,以及欧洲在先申请EP06112228.9和EP06112198.4(其在本申请的优选权日尚未公布)中的碳烯配合物。具体参考上述WO和EP申请的公开内容,并且这些公开内容应并入本申请的内容中。尤其是,与作为OLED中的基质材料和/或阻断剂材料的式I化合物一起使用的合适金属配合物包括尤其是在WO2005/019373A2(下文所用各变量的定义取自申请WO2005/019373A2;关于各变量的更详细定义,具体参考该申请)中公开的具有下列结构的碳烯配体:
其中:
*表示配体与金属中心的连接位点;
z、z′相同或不同且各自为CH或N;
R12、R12′相同或不同,并且各自为烷基、芳基、杂芳基或链烯基,优选烷基或芳基,或者在每种情况下2个基团R12或R12’一起形成可以任选包含至少一个杂原子,优选N的稠合环;优选在每种情况下2个基团R12或R12’一起形成稠合的芳族C6环,其中一个或多个其它芳族环可以任何可想象得到的稠合与该优选的六元芳族环稠合,并且所述稠合基团又可以被取代;或者R12或R12’是具有给体或受体作用的基团,其优选选自卤素基团,优选F、Cl、Br,更优选F;烷氧基,芳氧基,羰基,酯,氨基,酰胺基,CHF2,CH2F,CF3,CN,硫基和SCN;
t和t′相同或不同,优选相同,且各自为0-3,其中当t或t′>1时,基团R12或R12′可以相同或不同;t或t′优选是0或1;并且当t或t′是1时,基团R12或R12′位于与相邻于碳烯碳原子的氮原子的连接点的邻、间或对位;
R4、R5、R6、R7、R8、R9和R11各自为氢、烷基、芳基、杂芳基、链烯基或具有给体或受体作用的取代基,其优选选自卤素基团,优选F、Cl、Br,更优选F,烷氧基,芳氧基,羰基,酯基,胺基,酰胺基,基团CH2F,基团CHF2,基团CF3,基团CN,硫基和基团SCN,优选氢、烷基、杂芳基或芳基,
R10为烷基、芳基、杂芳基或链烯基,优选烷基、杂芳基或芳基,或者在每种情况下2个基团R10一起形成可以任选包含至少一个杂原子,优选氮的稠合环;优选在每种情况下2个基团R10一起形成稠合的芳族C6环,其中一个或多个其它芳族环可以任选以任何可想象得到的稠合与该优选的六元芳族环稠合,并且所述稠合基团又可以被取代;或者R10是具有给体或受体作用的基团,其优选选自卤素基团,优选F、Cl、Br,更优选F;烷氧基,芳氧基,羰基,酯,氨基,酰胺基、CHF2,CH2F,CF3,CN,硫基和SCN,
v为0-4,优选0、1或2,最优选0,其中当v是0时,式c中芳基的任选被R10取代的4个碳原子带有氢原子。
尤其是,与作为OLED中的基质材料和/或阻断剂材料的式I化合物一起使用的合适金属配合物包含在WO2005/019373A2中公开的具有下列结 构的Ir-碳烯配合物:
其中各变量各自如上面所定义。
与作为OLED中的基质材料和/或阻断剂材料的式I化合物一起使用的其它合适金属配合物还尤其是在WO2006/056418A2(下文所用各变量的定义取自申请WO2006/056418A2;关于各变量的更准确定义,具体参考该申请)中公开的下列结构:
其中M为Ru(III)、Rh(III)、Ir(III)、Pd(II)或Pt(II),n值对于Ru(III)、Rh(III)和Ir(III)为3,而对于Pd(II)和Pt(II)为2,并且Y2和Y3各自为氢、甲基、乙基、正丙基、异丙基或叔丁基。M优选为Ir(III),其中n=3。Y3优选为甲基、乙基、正丙基、异丙基或叔丁基。
与作为OLED中的基质材料和/或阻断剂材料的式I化合物一起使用的其它合适金属配合物还尤其是:
其中M为Ru(III)、Rh(III)、Ir(III)、Pd(II)或Pt(II),n值对于Ru(III)、Rh(III)和Ir(III)为3,而对于Pd(II)和Pt(II)为2,并且Y3为氢、甲基、乙基、正丙基、异丙基或叔丁基。M优选为Ir(III),其中n=3。Y3优选为甲基、乙基、正丙基、异丙基或叔丁基。
与作为OLED中的基质材料和/或阻断剂材料的式I化合物一起使用的其它合适金属配合物还尤其是:
其中M为Ru(III)、Rh(III),尤其为Ir(III)、Pd(II)或Pt(II),n值对于Ru(III)、Rh(III)和Ir(III)为3,而对于Pd(Ⅱ)和Pt(II)为2。
与作为OLED中的基质材料和/或阻断剂材料的式I化合物一起使用的其它合适金属配合物还尤其是:
其中M为Ru(III)、Rh(III),尤其是Ir(III)、Pd(II)或Pt(II),n值对于Ru(III)、Rh(III)和Ir(III)为3,而对于Pd(II)和Pt(II)为2。
另外,具有不同的碳烯配体和/或具有单阴离子或双阴离子配体且可以为单齿或二齿的配合物也是有用的。
参考下表,示意性地指出了具有三价金属中心和不同碳烯配体L′和L″的配合物ML′(L″)2:
L′ | L″ | L′ | L″ | L′ | L″ | L′ | L″ |
L1 | L2 | L3 | L4 | L7 | L5 | L5 | L3 |
L1 | L3 | L3 | L5 | L7 | L4 | L5 | L2 |
L1 | L4 | L3 | L6 | L7 | L3 | L5 | L1 |
L1 | L5 | L3 | L7 | L7 | L2 | L4 | L3 |
L1 | L6 | L4 | L5 | L7 | L1 | L4 | L2 |
L1 | L7 | L4 | L6 | L6 | L5 | L4 | L1 |
L2 | L3 | L4 | L7 | L6 | L4 | L3 | L2 |
L2 | L4 | L5 | L6 | L6 | L3 | L3 | L1 |
L2 | L5 | L5 | L7 | L6 | L2 | L2 | L1 |
L2 | L6 | L6 | L7 | L6 | L1 | ||
L2 | L7 | L7 | L6 | L5 | L4 |
其中M为例如Ru(III)、Rh(III)或Ir(III),尤其是Ir(III),并且L′和L″例如为选自下组配体L1-L7的配体:
Y2为氢、甲基、乙基、正丙基、异丙基或叔丁基,并且Y3为甲基、乙基、正丙基、异丙基或叔丁基。
具有不同碳烯配体的这些配合物的一个代表(当Y2=氢且Y3=甲基时,L′=L4;当Y2=氢且Y3=甲基时,L″=L2)例如是:
应理解的是,在作为基质材料中的发射体使用和/或与三价金属中心(例如对于Ru(III)、Rh(III)或Ir(III)的情况)的配合物一起使用的配合物中,所有三个碳烯配体可以彼此不同,其中所述三价金属中心的配合物与式I的阻断剂材料一起使用。
具有配体L(此处为单阴离子的二齿配体)作为″旁观者配体″的三价金属中心M的配合物的实例是:LML′L″、LM(L′)2和L2ML′,其中M是例如Ru(III)、Rh(III)或Ir(III),尤其是Ir(III),并且L′和L″各自如上面所定义。对于配合物LML′L″中的L′和L″的组合,这得到:
L′ | L″ | L′ | L″ |
L1 | L2 | L3 | L4 |
L1 | L3 | L3 | L5 |
L1 | L4 | L3 | L6 |
L1 | L5 | L3 | L7 |
L1 | L6 | L4 | L5 |
L1 | L7 | L4 | L6 |
L2 | L3 | L4 | L7 |
L2 | L4 | L5 | L6 |
L2 | L5 | L5 | L7 |
L2 | L6 | L6 | L7 |
L2 | L7 |
有用的配体L尤其是乙酰丙酮酸根及其衍生物,吡啶甲酸根,Schiff碱,氨基酸和WO02/15645A1中描述的二齿单阴离子配体;尤其感兴趣 的是乙酰丙酮酸根和吡啶甲酸根。在配合物L2ML′的情况下,配体L可以相同或不同。
具有不同碳烯配体的这些配合物的一个代表(当Y2=氢且Y3=甲基时,L′=L4;当Y2=氢且Y3=甲基时,L″=L2)例如是:
其中如下符号中的z1和z2
代表配体L的两个“齿”。Y3为氢、甲基、乙基、正丙基、异丙基或叔丁基,尤其是甲基、乙基、正丙基或异丙基。
尤其适合作为发射体化合物与OLED中作为基质材料的式I化合物一起使用的其它金属配合物为:
其中R为氢,烷基或芳基,优选甲基、乙基、正丙基、异丙基、叔丁基或 苯基,
以及
其中M为Ru(III)、Rh(III)、Ir(III)、Pd(II)或Pt(II),n值对于Ru(III)、Rh(III)和Ir(III)为3,而对于Pd(II)和Pt(II)为2,并且Y2和Y3各自为氢、甲基、乙基、正丙基、异丙基或叔丁基。M优选为Ir(III),其中n=3。Y3优选为甲基、乙基、正丙基、异丙基或叔丁基。
此外,下列特定金属配合物适合于在OLED中尤其是作为基质材料与作为基质材料的式I化合物一起使用:
上述碳烯配合物通过本领域熟练技术人员已知的方法制备。化学计量和反应条件可通过本领域熟练技术人员基于与碳烯配合物及其制备方法有关的上述专利申请而毫无问题地确定。此外,在本申请的实施例部分,描述了制备一些上述碳烯配合物的方法。没有在实施例中具体描述的碳烯配合物可类似于在实施例部分描述的方法制备。
当至少一种本发明的式(I)化合物与发射体化合物,优选与三线态发射体一起用于特别优选的OLED发光层时,至少一种式(I)化合物在发光层中的比例通常为10-99重量%,优选50-99重量%,更优选70-97重量%。发射体化合物在发光层中的比例通常为1-90重量%,优选1-50重量%,更优选3-30重量%,其中至少一种式(I)化合物和至少一种发射体化合物的比例加起来至多为100重量%。然而,除了至少一种式(I)化合物和至少一种发射体化合物外,发光层还可以包含其它材料如其它的稀释材料,其中合适的稀释材料在下文描述。
有机发光二极管(OLED)原则上由多层组成,例如:
1.阳极
2.空穴传输层
3.发光层
4.电子传输层
5.阴极
与上述结构不同的层序也是可以的,这对于本领域技术人员是已知的。例如,OLED可以不具有所有的所述层;例如,包含层(1)(阳极)、(3)(发光层)和(5)(阴极)的OLED同样也是合适的,其中层(2)(空穴传输层)和(4)(电 子传输层)的功能通过相邻层来实现。具有层(1)、(2)、(3)和(5)或具有层(1)、(3)、(4)和(5)的OLED同样也是合适的。
式I化合物可以用作电荷传输材料,尤其是电子传输材料,但是它们也优选用作发光层中的基质材料或用作空穴/激子阻断剂层。此外,用给电子取代基取代的式(I)化合物可用作电子/激子阻断剂层。
本发明的式I化合物可以在发光层中作为唯一的基质材料存在,不含其它添加物。然而,除了根据本发明使用的式I化合物以外,其它化合物同样也可以存在于发光层中。例如,可以存在荧光染料,以改变所存在的发射体分子的发射色。此外,还可以使用稀释材料。该稀释材料可以是聚合物,例如聚(N-乙烯基咔唑)或聚硅烷。然而,稀释材料同样可以是小分子,例如4,4’-N,N’-二咔唑联苯(CBP=CDP)或芳族叔胺。当使用稀释材料时,根据本发明使用的式I化合物在发光层中的比例基于式I化合物与稀释剂的总重量通常仍总是为至少40重量%,优选50-100重量%。
上文对于OLED所述的各个层又可由两层或更多层形成。例如,空穴传输层可以由一层空穴从电极注入其中的层和一层将空穴从空穴注入层传输到发光层的层形成。电子传输层同样可由多层构成,例如由一层电子借助电极注入其中的层和一层从电子注入层接收电子并将它们传输到发光层中的层构成。这些层每种情况下根据因素如能级、耐热性和电荷载体的迁移率以及所述层和有机层或金属电极之间的能量差进行选择。本领域熟练技术人员能够选择OLED的结构,使得它与根据本发明作为发射体物质使用的有机化合物最优匹配。
为了获得特别有效的OLED,空穴传输层的HOMO(最高占据分子轨道)应该与阳极的功函匹配,并且电子传输层的LUMO(最低非占据分子轨道)应该与阴极的功函匹配。
阳极(1)是提供正电荷载体的电极。它例如可以由包含金属、不同金属的混合物、金属合金、金属氧化物或不同金属氧化物的混合物的材料构成。或者,阳极可以是导电性聚合物。合适的金属包括元素周期表中第Ib、IVb、Va和VIa族的金属以及第VIIIa族的过渡金属。当阳极需要透明时,通常使用元素周期表(老IUPAC版)中第IIb、IIIb和IVb族金属的混合氧化物, 例如铟锡氧化物(ITO)。阳极(1)同样可以包含有机材料,例如聚苯胺,例如如Nature(自然),第357卷,第477-479页(1992年6月11日)所述。阳极或阴极中的至少一个应该至少是部分透明的,以能够发射所产生的光。
用于本发明OLED的层(2)的合适空穴传输材料例如公开在Kirk-Othmer Encyclopedia of Chemical Technology(化学技术百科全书),第4辑,第18卷,第837-860页,1996中。空穴传输分子和聚合物都可以用作空穴传输材料。经常使用的空穴传输分子选自三[N-(1-萘基)-N-(苯基氨基)]三苯基胺(1-NaphDATA)、4,4’-双[N-(1-萘基)-N-苯基氨基]联苯(α-NPD)、N,N’-二苯基-N,N’-双(3-甲基苯基)-[1,1’-联苯]-4,4’-二胺(TPD)、1,1-双[(二-4-甲苯基氨基)苯基]环己烷(TAPC)、N,N’-双(4-甲基苯基)-N,N’-双(4-乙基苯基)[1,1’-(3,3’-二甲基)联苯]-4,4’-二胺](ETPD)、四(3-甲基苯基)-N,N,N’,N’-2,5-苯二胺(PDA)、α-苯基-4-N,N-二苯基氨基苯乙烯(TPS)、对-(二乙基氨基)苯甲醛二苯基腙(DEH)、三苯基胺(TPA)、双[4-(N,N-二乙基氨基)-2-甲基苯基]-(4-甲基苯基)甲烷(MPMP)、1-苯基-3-[对-(二乙基氨基)苯乙烯基]-5-[对-(二乙基氨基)苯基]吡唑啉(PPR或DEASP)、1,2-反式-双(9H-咔唑9-基)环丁烷(DCZB)、N,N,N’,N’-四(4-甲基苯基)-(1,1’-联苯)-4,4’-二胺(TTB)、4,4’,4”-三(N,N-二苯基氨基)三苯基胺(TDTA)、卟啉类化合物以及酞菁如铜酞菁。常常使用的空穴传输聚合物选自聚乙烯基咔唑,(苯基甲基)聚硅烷以及聚苯胺。同样还可通过用空穴传输分子掺杂到聚合物如聚苯乙烯和聚碳酸酯中来获得空穴传输聚合物。合适的空穴传输分子为上文已经提及的分子。
此外,上文所述作为发射体材料的碳烯配合物还可以用作空穴传输材料,此时至少一种空穴传输材料的带隙通常大于所用发射体材料的带隙。就本申请而言,带隙应理解为指的是三线态能量。
用于本发明OLED的层(4)的合适电子传输材料包括与下列化合物螯合的金属:oxinoid化合物,例如2,2’,2”-(1,3,5-亚苯基)三(1-苯基-1H-苯并咪唑)(TPBI)、三(8-羟基喹啉)铝(Alq3),基于菲咯啉的化合物,例如2,9-二甲基-4,7-二苯基-1,10-菲咯啉(DDPA=BCP)或4,7-二苯基-1,10-菲咯啉(DPA)以及唑类化合物,例如2-(4-联苯基)-5-(4-叔丁基苯基)-1,3,4-二唑(PBD) 和3-(4-联苯基)-4-苯基-5-(4-叔丁基苯基)-1,2,4-***(TAZ)。层(4)可以有助于电子传输或用作缓冲层或用作阻断层,以防止激子在OLED各层界面处淬灭。层(4)优选改进电子的迁移率和降低激子的淬灭。
在上文作为空穴传输材料和电子传输材料提及的材料中,一些可以发挥多种功能。例如,一些电子传输材料在具有低HOMO时,它们同时为空穴阻断材料。
如上所述,本发明的式(I)化合物同样可用作电荷传输或阻断剂材料,优选用作阻断剂材料。
电荷传输层也可以电子掺杂,以改进所用材料的传输特性,以首先使层厚度可以更大(避免针孔/短路),其次将器件的操作电压降至最低。例如,空穴传输材料可以掺杂有电子受体;例如酞菁或芳基胺如TPD或者TDTA可以掺杂有四氟四氰基醌二甲烷(F4-TCNQ)。电子传输材料可以例如掺杂有碱金属,例如Alq3可以掺杂有锂。电子掺杂对本领域熟练技术人员是已知的,并且公开于例如W.Gao,A.Kahn,J.Appl.Phys.,第94卷,第1期,2003年7月1日(p-掺杂的有机层);A.G.Werner,F.Li,K.Harada,M.Pfeiffer,T.Fritz,K.Leo,Appl.Phys.Lett.,第82卷,第25期,2003年6月23日和Pfeiffer等,Organic Electronics2003,4,89-103中。
阴极(5)是用于引入电子或负电荷载体的电极。用于阴极的合适材料选自元素周期表(老IUPAC版)第Ia族的碱金属,例如Li、Cs,第IIa族的碱土金属如钙、钡或镁以及第IIb族金属,包括镧系金属和锕系金属,例如钐。另外,还可以使用金属如铝或铟,以及所有所提及金属的结合。另外,含锂的有机金属化合物或LiF可应用于有机层和阴极之间,以降低操作电压。
本发明的OLED可额外包含本领域熟练技术人员已知的其它层。例如,有助于正电荷的传输和/或使各层的带隙相互匹配的层可以应用于层(2)和发光层(3)之间。或者,该额外层可用作保护层。以类似方式,在发光层(3)和(4)之间可以存在额外的层,以有助于负电荷的传输和/或使各层的带隙相互匹配。或者,该层可用作保护层。
在优选实施方案中,本发明的OLED除了层(1)-(5)外,包含下列其它 层中的至少一层:
-阳极(1)和空穴传输层(2)之间的空穴注入层;
-空穴传输层(2)和发光层(3)之间的电子阻断层;
-发光层(3)和电子传输层(4)之间的空穴阻断层;
-电子传输层(4)和阴极(5)之间的电子注入层。
取决于其取代方式,本发明的式(I)化合物可在电子阻断层中用作阻断剂材料或在空穴阻断层中用作阻断剂材料。
然而,OLED也可以不具有所有的所述层(1)-(5);例如,包含层(1)(阳极)、(3)(发光层)和(5)(阴极)的OLED同样也是合适的,其中层(2)(空穴传输层)和(4)(电子传输层)的功能通过相邻层来实现。具有层(1)、(2)、(3)和(5)或具有层(1)、(3)、(4)和(5)的OLED同样也是合适的。
本领域熟练技术人员应当知道如何选择合适的材料(例如基于电化学研究)。用于各层的合适材料对本领域熟练技术人员是已知的,并且例如公开于WO00/70655中。
此外,本发明OLED的所述层中的每一层可以由两层或更多层构成。另外,层(1)、(2)、(3)、(4)和(5)中的一部分或全部也可以进行表面处理,以增加电荷载体传输的效率。用于所述层中每一层的材料的选择优选由获得具有高效率和寿命的OLED来确定。
本发明OLED可以通过本领域熟练技术人员已知的方法来生产。通常而言,本发明OLED通过在合适的基底上依次地气相沉积各层来生产。合适的基底优选为例如玻璃或聚合物膜。对于气相沉积,可以使用常规技术如热气化、化学气相沉积和其它技术进行。在可供选择的方法中,各有机层可由在合适的溶剂中的溶液或分散体涂覆,在这种情况下,采用本领域熟练技术人员已知的涂覆技术。
通常而言,各层具有下列厚度:阳极(1)优选空穴传输层(2)优选发光层(3)优选 电子传输层(4)优选阴极(5)优选本发明OLED中的空穴和电子的重组区的位置以及由此OLED的发射光谱可受到各层的相对厚度的影响。这意味着,电子传输层 的厚度应该优选经选择,使得电子/空穴的重组区位于发光层中。OLED中各层的层厚度的比例取决于所用材料。使用的任何额外层的层厚度对本领域熟练技术人员是已知的。
通过将本发明的式I化合物用作本发明OLED的发光层中的基质材料可以获得具有高效率的OLED。本发明OLED的效率可以额外通过优化其它层来得到改进。例如,可以使用高效率的阴极如Ca或Ba,合适的话与LiF的中间体层相结合。导致操作电压降低或量子效率增加的成形基底和新颖空穴传输材料同样可以用于本发明OLED中。此外,额外的层也可以存在于OLED中,以调节不同层的能级和助于电致发光。
本发明OLED可以用于其中使用电致发光的所有器件中。合适的器件优选选自固定和移动的可视显示单元和照明单元。固定的可视显示单元例如是计算机、电视的可视显示单元,打印机、厨房用具和广告板中的可视显示单元,照明和信息板。移动的可视显示单元例如是移动电话、手提电脑、数码相机、交通工具及公共汽车和火车上的目的地显示器中的可视显示单元。
另外,本发明的式I化合物还可以用于具有反转结构的OLED中。在这些反转OLED中,优选将根据本发明使用的式I化合物再次用作发光层中的基质材料。反转OLED的结构和其中常使用的材料对本领域熟练技术人员是已知的。
下列实施例额外地阐述本发明。
实施例
A:制备本发明的式(I)化合物
将吩噻嗪(31.4g,157mmol)、1-溴-4-碘苯(50.0g,173mmol)、碳酸钾(32.9g,238mmol)和铜粉(2.0g,31mmol)加热到170℃并在该温度下搅拌 7h。将反应熔体冷却至130℃,与乙酸乙酯(80ml)掺混并在回流下搅拌30分钟。将所得悬浮液转移到索格利特萃取器中并在回流下萃取16小时。使萃取溶液在搅拌下冷却到室温。蒸除四分之三溶剂,用乙醇(30ml)沉淀有价值产物并过滤。获得26.7g(48%的理论值)熔点为132-137℃的无色晶体。
向镁(0.56g,22.6mmol)和干燥THF(6ml)的混合物中加入10-(4-溴苯基)吩噻嗪(8.0g,22.6mmol)在干燥THF(24ml)中的溶液。在回流2h之后,加入SiMe2Cl2(1.46g,11.3mmol)。在回流2h之后,将溶液冷却、过滤并与冰和二***掺混。取出有机相并浓缩。残余物在DMF中结晶。获得3.00g(44%的理论值)根据元素分析为纯的无色晶体。
将二甲基双(4-苯基-10-吩噻嗪)硅烷(2.97g,4.90mmol)溶解于二氯甲烷(280ml)中。在室温下搅拌15分钟之后,分批加入77%的间氯过苯甲酸(5.80g,23.4mmol)。反应溶液在室温下搅拌24h。有机相用10%氢氧化钠溶液(50ml)、5%盐酸(50ml)和饱和碳酸氢钠溶液(50ml)洗涤并浓缩。残余物在DMF中结晶。获得2.8g(85%的理论值)熔点为293-298℃的无色晶体。
在-78℃下,向10-(4-溴苯基)吩噻嗪(8.0g,22.6mmol)在干燥THF(120ml)中的溶液中加入nBuLi(14.8ml,1.6M,在己烷中)。在搅拌1h之后,加入在干燥THF(12ml)中的SiCl4(0.93g,5.4mmol)。在-78℃下2h之后,将溶液加热至室温并搅拌过夜。过滤沉淀并用饱和氯化铵溶液和软水洗涤残余物。残余物在DMF中结晶。获得3.44g(57%的理论值)目标化合物。
将四(4-苯基吩噻嗪)硅烷(3.47g,3.08mmol)悬浮于二氯甲烷(1500ml)中。在室温下搅拌15分钟之后,分批加入77%的间氯过苯甲酸(7.30g,29.6mmol)。将所得溶液在室温下搅拌20h。有机相用10%氢氧化钠溶液 (3×30ml)、5%盐酸(30ml)和饱和碳酸氢钠溶液(30ml)洗涤并浓缩。残余物在二氯甲烷/丙酮中结晶。获得1.74g(45%的理论值)无色晶体。
将氢化钠(石蜡油中60%分散体)(28.0g,700.0mmol)与干燥DMF(700ml)在N2下混合。在搅拌下,在10分钟内加入吩噻嗪(140.7g,700.0mmol)。在放出氢气完成(20分钟)之后,在15分钟内加入DMF(70ml)中的1-溴-3,5-二氟苯(68.95g,350.0mmol)。在100℃下搅拌该混合物18h。加入氢化钠(石蜡油中60%分散体)(4.0g,100.0mmol)并在100℃下继续搅拌该混合物5h。加入氢化钠(石蜡油中60%分散体)(4.0g,100.0mmol)并在100℃下继续搅拌该混合物18h。将该混合物冷却至室温,过滤并用DMF洗涤。残余物与环己烷/乙酸乙酯(5∶2,500ml)掺混并滤出。获得38.9g(20%的理论值)的浅黄色固体(6)。
在-78℃下,向(4-溴苯基)二苯基胺(8.40g,25.20mmol)在干燥THF(105ml)中的溶液中逐滴加入nBuLi(16.8ml,26.6mmol,1.6M,在己烷中)。在-78℃下搅拌60分钟之后,将该溶液逐滴加入二氯二甲基硅烷(3.47g,26.6mmol)在-78℃下THF(140ml)中的溶液中。在40分钟内将该反应混合物加热至0℃并在0℃下搅拌1h。将该混合物再冷却至-78℃并加入3,5-双(10-吩噻嗪)-1-苯酚锂(来自(6)(14.0g,25.2mmol))和nBuLi(16.8ml,26.6mmol,1.6M,在己烷中)在THF(105ml)中的溶液。在 -78℃下搅拌1h之后,将该混合物加热至室温并搅拌过夜。将该混合物与饱和氯化铵溶液(70ml)掺混并过滤。有机相用水洗涤并干燥(Na2SO4)。在柱色谱法(SiO2,40∶1己烷/乙酸乙酯)和在乙酸乙酯中重结晶之后,获得2.88g(14%的理论值)目标产物(7)。
将(7)(2.8g,3.6mmol)溶解于二氯甲烷(100ml)中。在室温下搅拌15分钟之后,在0-5℃下缓慢逐滴加入二氯甲烷(40ml)中的77%间氯过苯甲酸。在0-5℃下搅拌所得溶液20h。有机相用10%氢氧化钠溶液(3×20ml)、5%盐酸(30ml)和饱和碳酸氢钠溶液(30ml)洗涤,干燥(Na2SO4)并浓缩。在柱色谱法(SiO2,CH2Cl2)之后,获得1.1g(38%的理论值)目标产物(8)。
B:使用实施例:生产OLED
B1:使用化合物(3)作为基质材料
首先将用作阳极的ITO基底使用用于LCD生产的市购清洗剂(20NS和中和剂)清洁,然后将其在超声浴中在丙酮/异丙醇混合物中清洁。为了除去可能的有机残余物,进一步将基底在臭氧箱中暴露于连续的臭氧流中25分钟。这种处理还改进了ITO的空穴注入特性。
随后,在约10-9毫巴下以约0.5-5nm/min的速率通过气相沉积而在清洁基底上施用下文所述的有机材料。在基底上施用的空穴导电剂和激子阻断剂为具有20nm厚度的Ir(dpbic)3(V1)。
(关于制备,参见申请WO2005/019373A2中的Ir配合物(7)。)
随后,通过气相沉积以20nm的厚度施用16重量%的化合物CN-PMBIC(V2)和84重量%的化合物二甲基双(4-苯基吩噻嗪S,S-二氧化物)硅烷(3)的混合物,其中前者用作发射体,而后者用作基质材料。
(关于制备,参见WO2006/056418A2中的实施例3。)
随后,通过气相沉积以10nm厚度施用材料mPTO2(1,3-亚苯基-10,10’-双(吩噻嗪)5,5’-二氧化物(V3))作为激子和空穴阻断剂。
然后通过气相沉积施用65nm厚的电子传输材料TPBI(1,3,5-三(N-苯基苯并咪唑-2-基)苯),0.75nm厚的氟化锂层以及最后110nm厚的Al电极。
为了表征OLED,在不同电流和电压下记录电致发光谱。此外,测量电流-电压特征以及发射光的发光功率。可通过用亮度计校准将发光功率转化成光度参数。
对于所述OLED,获得下列电光数据:
最大发射 | 455nm |
CIE(x、y) | 0.17;0.13 |
光度效率,在3V下 | 6.0cd/A |
功率系数,在3V下 | 6.3lm/W |
外部量子产率,在3V下 | 5.4% |
发光度,在10V下 | 400cd/m2 |
B2:使用化合物(3)作为激子和空穴阻断剂
首先将用作阳极的ITO基底使用用于LCD生产的市购清洗剂(20NS和中和剂)清洁,然后将其在超声浴中在丙酮/异丙醇混合物中清洁。为了除去可能的有机残余物,进一步将基底在臭氧箱中暴露于连续的臭氧流中25分钟。这种处理还改进了ITO的空穴注入特性。
随后,在约10-9毫巴下以约0.5-5nm/min的速率通过气相沉积而在清洁基底上施用下文所述的有机材料。在基底上施用的空穴导电剂和激子阻断剂为具有30nm厚度的Ir(dpbic)3(V1)。
(关于制备,参见申请WO2005/019373中的Ir配合物(7)。)
(关于制备,参见WO2006/056418A2中的实施例3。)
随后,通过气相沉积以20nm的厚度施用30重量%的化合物CN-PMBIC和70重量%的化合物(V4)的混合物,其中前者用作发射体,而后者用作基质材料。
随后,通过气相沉积施用10nm厚的化合物(3)作为激子和空穴阻断剂。
然后,通过气相沉积施用40nm厚的电子传输材料TPBI(1,3,5-三(N-苯基苯并咪唑-2-基)苯),0.75nm厚的氟化锂层以及最后110nm厚的Al电极。
为了表征OLED,在不同电流和电压下记录电致发光谱。此外,测量电流-电压特征以及发射光的发光功率。可通过用亮度计校准将发光功率转化成光度参数。
最大发射 | 455nm |
阻断剂 | |
CIE(x、y) | 0.16;0.12 |
光度效率,在4.5V下 | 8.8cd/A |
功率系数,在4.5V下 | 6.1lm/W |
外部量子产率,在4.5V下 | 8.8% |
C:制备所选碳烯配合物的方法
Ir(DBF-MIC)3(V5)
将3.48g(9.2mmol)碘化咪唑和1.07g(4.6mmol)氧化银悬浮于60ml乙腈中并在室温下搅拌过夜。然后,将该悬浮液浓缩至干燥,用100ml1,4-二烷吸收并在半小时内计量加入0.62g(0.92mmol)[(μ-Cl)(η4-1,5-cod)Ir]2和60ml1,4-二烷的溶液中。随后,将该混合物在室温下搅拌1小时,在70℃下搅拌2小时并在回流下搅拌18小时。冷却之后,将反应混合物浓缩至干燥,用二氯甲烷萃取并将萃取液通过柱色谱法进行提纯(洗脱液:1.2∶1二氯甲烷∶环己烷用于分离异构体混合物并且2.1∶1乙酸乙酯∶环己烷用于分离各异构体,反应混合物中各异构体比例:子午线式/面式为约3/1)。以浅黄色粉末得到约0.61g(35%)子午线式异构体和0.1g(6%)面式异构体。
子午线式异构体:
1H-NMR:(DMSO,500MHz):8.40(d,J=2.0Hz,1H,CH),8.34(d,J=2.1Hz,1H,CH),8.22(d,J=2.1Hz,1H,CH),7.90-7.85(m,1H,CH),7.69-7.65(m,1H,CH),7.43-7.13(m,16H,CH),6.75(d,3JH,H=7.5Hz,1H,CH),6.68(d,3JH,H=7.7Hz,1H,CH),6.56(d,3JH,H=7.6Hz,1H,CH),3.13(s,3H,CH3),3.05(s,3H,CH3),2.99(s,3H,CH3)。
面式异构体:
1H-NMR:(DMSO,500MHz):8.28(d,J=1.95Hz,3H,CH),7.88-7.89(m,3H,CH),7.67-7.68(m,3H,CH),7.43-7.12(m,12H,CH),6.50(d, 3JH,H=7.5Hz,3H,CH),3.14(s,9H,CH3)。
[(PMIC)2IrCl]2(V6)
将4.29g(18.5mmol)氧化银、9.47g(33.1mmol)碘化咪唑和3.56g(10.1mmol)三水合三氯化铱悬浮于350ml2-甲氧基乙醇中并在120℃下在暗处搅拌15h。然后,在减压下除去溶剂并用二氯甲烷萃取残余物。将萃取液浓缩至其体积的约四分之一并与甲醇掺混。过滤出沉淀的固体并干燥。获得1.7g[(PMIC)2IrCl]2(31%)。
1H-NMR:(CD2Cl2,500MHz):δ=7.59(d,J=2.3Hz,4H,CH),7.17(d,J=1.7Hz,4H,CH),6.99(d,3JH,H=7.2Hz,4H,CH),6.73(pt,3JH,H=7.5Hz,4H,CH),6.45(pt,3JH,H=7.9Hz,4H,CH),6.09(d,3JH,H=7.3Hz,4H,CH),3.91(s,12H,CH3)。
(PMIC)2Irpic(V7)
在10分钟内将0.41g(3.32mmol)吡啶甲酸在甲氧基乙醇(30ml)中的溶液与3.32ml氢氧化钠溶液(1M,3.32mmol)掺混并在室温下搅拌15分钟。然后,在10分钟内将反应混合物加入0.9g(0.83mmol)[(PMIC)2IrCl]2在甲氧基乙醇(80ml)中的悬浮液中。将该混合物在室温下搅拌15分钟,然后在回流下加热21h。冷却之后,将该反应混合物与水(300ml)掺混。过滤出形成的沉淀,干燥并通过柱色谱法进行提纯(洗脱液∶乙酸乙酯/甲醇=1/0.25)。得到0.64g(PMIC)2IrPic(61%)。
1H-NMR:(CD2Cl2,500MHz):δ=3.00(s,3H,CH3),3.86(s,3H, CH3),6.31-6.33(m,1H,CH),6.42-6.44(m,1H,CH),6.59-6.63(m,2H,CH),6.83-6.88(m,2H,CH),6.90-6.91(m,1H,CH),6.98-6.99(m,1H,CH),7.08(d,J=7.8Hz,2H,CH),7.21-7.24(m,1H,CH),7.46-7.47(m,2H,CH),7.80-7.83(dt,J=7.7Hz,J=1.5Hz,1H,CH),7.92-7.93(m,1H,CH),8.13-8.15(m,1H,CH)。
(PMIC)2IrPicOMe(V8)
在10分钟内将0.68g(4.44mmol)4-甲氧基吡啶甲酸在70ml2-甲氧基乙醇中的悬浮液与4.44ml氢氧化钠溶液(1M,4.44mm0l)掺混。将该混合物在室温下搅拌15分钟,然后将该混合物缓慢加入1.2g(1.11mmol)[(PMIC)2IrCl]2和80ml2-甲氧基乙醇的悬浮液中。将该混合物在室温下搅拌15分钟,然后在回流下加热21h。冷却之后,将该反应混合物与水(600ml)掺混。过滤出形成的沉淀,干燥并通过柱色谱法进行提纯(洗脱液∶乙酸乙酯/甲醇=1/0.25)。得到0.93g(PMIC)2IrPicOMe(64%)。
1H-NMR:(CD2Cl2,500MHz):δ=3.07(s,3H,CH3),3.85(s,3H,CH3),3.91(s,3H,CH3),6.33(dd,J=7.3Hz,J=1.4Hz,1H,CH),6.42(dd,J=7.4Hz,J=1.4Hz,1H,CH),6.57-6.61(m,2H,CH),6.74(dd,J=6.3Hz,J=2.9Hz,1H,CH),6.81-6.86(m,2H,CH),6.92(d,J=2.1Hz,1H,CH),6.98(d,J=2.1Hz,1H,CH),7.07(dd,J=4.8Hz,J=1.3Hz,1H,CH),7.08(dd,J=4.6Hz,J=1.3Hz,1H,CH),7.46(dd,J=4.1Hz,J=2.1Hz,2H,CH),7.65(d,J=6.2Hz,1H,CH),7.72(d,J=2.5Hz,1H,CH)。
(PMIC)2Ir(acac-F6)(V9)
将0.22g(0.2mmol)[(PMIC)2IrCl]2在60ml二氯甲烷中的溶液与0.17g(0.4mmol)(cod)Ag(acac-F6)在30ml二氯甲烷中溶液掺混。将该混合物在回流下搅拌2h并在室温下搅拌18h。然后在减压下除去溶剂并通过柱色谱法提纯残余物(洗脱液:CH2Cl2)。得到0.28g(96%)红色粉末。
1H-NMR:(CD2C12,500MHz):δ=7.50(s,2H),7.11(s,2H),7.03(m,2H),6.81(m,2H),6.56(m,2H),6.19(m,2H),5.98(s,1H),3.79(s,6H)。子午线式三[1-(4’-苯基磺酰基苯基)-3-甲基苯并咪唑-2-亚基-C2,C2’]-铱(III)(V10)
1-(4’-苯基磺酰基苯基)-苯并咪唑
在室温下在氮气下向苯并咪唑(11.8g,0.10mol)在DMF(500ml)中的溶液中加入氢化钠(60%,在矿物油中,4.4g,0.11mol)并将该混合物搅拌10分钟。将该混合物与4-氯苯基苯基砜(26.1g,0.10mol)掺混并在100℃下搅拌16h。在室温下再加入氢化钠(60%,在矿物油中,2.0g,0.05mol)并将该混合物在130℃下搅拌16h。冷却至室温之后,将该混合物加入冰水中。过滤出沉淀的产物并用水洗涤。产率:91%。
1H-NMR(d6-DMSO,400MHz):δ=7.35(mc,2H),7.64-7.82(m,5H),7.98(d,2H),8.06(d,2H),8.20(d,2H),8.67(s,1H)。
1-(4’-苯基磺酰基苯基)-3-甲基苯并咪唑四氟硼酸盐
在-10℃下,将1-(4’-苯基磺酰基苯基)苯并咪唑(6.7g,20mmol)在二氯甲烷(100ml)中的溶液与三甲基氧四氟硼酸盐(3.3g,22mmol)掺混并在氩气下搅拌16h。加入甲醇之后,过滤出形成的沉淀并用冷石油醚洗涤。产率:80%。
1H-NMR(d6-DMSO,400MHz):δ=4.17(s,3H),7.67-7.83(m,5H),7.94(d,1H),8.04-8.12(m,4H),8.15(d,1H),8.36(d,2H),10.14(s,1H)。子午线式三[1-(4’-苯基磺酰基苯基)-3-甲基苯并咪唑-2-亚基-C2,C2’]-铱(III)(V11)
在室温下,在氩气下将1-(4’-苯基磺酰基苯基)-3-甲基苯并咪唑四氟硼酸盐(4.4g,10mmol)在二烷(100ml)中的悬浮液与KHMDS(0.5M在甲苯中,20ml,10mmol)掺混并搅拌15分钟。加入1,5-环辛二烯-氯化铱(I)二聚体(0.7g,1mmol)之后,将该混合物在室温下搅拌16h。冷却至室温之后,过滤出沉淀并用甲基叔丁基醚洗涤。将合并的滤液浓缩至干燥并通过柱色谱法提纯(氧化铝、二氯甲烷、丁酮)。产率:56%。
1H-NMR(d6-DMSO,400MHz):δ=2.82(s,3H),2.99(s,3H),3.15(s,3H),6.61(d,1H),6.98(d,1H),7.01(d,1H),7.30-7.72(m,27H),8.09-8.16(m,3H),8.35-8.44(m,3H)。
三[1-(4’-甲氧基羰基苯基)-3-甲基苯并咪唑-2-亚基-C2,C2’]-铱(III)
1-(4’-甲氧基羰基苯基)咪唑
将咪唑(132g,1.9mol)、4-氟苯甲酸甲酯(170ml,1.3mol)和碳酸钾(357g,2.6mol)在DMSO(200ml)中的混合物在120℃下搅拌3h。冷却至室温之后,将该混合物加入冰水中。过滤出沉淀产物并用水洗涤。产率:59%。
1H-NMR(d6-DMSO,400MHz):δ=3.89(s,3H),7.17(mc,1H),7.86(d, 2H),7.90(mc,1H),8.08(d,2H),8.44(mc,1H)。
将1-(4’-甲氧基羰基苯基)咪唑(153g,0.76mol)在1∶1THF/甲醇(600ml)中的溶液与甲基碘(196ml,2.27mol)掺混并在氩气下在室温下搅拌16h。在溶液浓缩之后,过滤出沉淀产物并用THF洗涤。产率:59%。
1H-NMR(d6-DMSO,400MHz):δ=3.90(s,3H),3.95(s,3H),7.94(d,2H),7.98(mc,1H),8.21(d,2H),8.38(mc,1H),9.89(s,1H)。
三[1-(4’-甲氧基羰基苯基)-3-甲基苯并咪唑-2-亚基-C2,C2’]-铱(III)
在室温下,在氩气下将1-(4’-甲氧基羰基苯基)-3-甲基咪唑碘化物(148.0g,431mmol)和氧化银(I)(50.4g,216mmol)在二烷(400ml)中的悬浮液搅拌16h。将该混合物与1,5-环辛二烯-氯化铱(I)二聚体(33.2g,43mmol)掺混并在回流下搅拌16h。冷却至室温之后,过滤出沉淀并用二氯甲烷洗涤。将合并的滤液浓缩至干燥并通过柱色谱法提纯(氧化铝,1∶1乙酸乙酯/甲醇)。将包含作为子午线式异构体和面式异构体的产物的混合馏分浓缩至干燥并溶解于1∶1丙酮/甲醇中。将该溶液与1M盐酸掺混并在回流下搅拌16h。过滤出沉淀子午线式异构体。并用少量丙酮洗涤。产率:45%。
子午线式异构体:1H-NMR(d6-DMSO,400MHz):δ=2.89(s,3H),2.96(s,3H),2.99(s,3H),3.60(s,3H),3.67(s,3H),3.69(s,3H),7.12(s,1H),7.18(s,1H),7.24(s,1H),7.27(s,1H),7.29(s,1H),7.31(s,1H),7.38-7.49(m,6H),7.98(s,1H),8.04(s,1H),8.06(s,1H)。
面式异构体:1H-NMR(d6-DMSO,400MHz):δ=3.00(s,9H),3.60(s,9H),7.06(d,3H),7.21(d,3H),7.43-7.51(m,6H),7.99(d,3H)。
双[(2-苯基)-2-吡唑啉基-N,C2)](1-苯基-3-甲基咪唑啉-2-亚基-C,C2]-铱(III)(V12)
类似于US2005/0260441A1中实施例3制备化合物(V12),不同之处在于使用[(ppz)2IrCl]2,而不是[(F2ppz)2IrCl]2。
Claims (11)
2.根据权利要求1的化合物,其中:
X为SO2;
m为2、3或4;
o、p各自为0、1或2;
L为及
q为0、1或2。
3.根据权利要求1或2的化合物,其中与Si结合的基团L或R1中至少两个为芳族基团。
4.根据权利要求1的化合物,其中:
L为及
o、p和q各自为0。
5.包含至少一种根据权利要求1或2的化合物的OLED。
6.根据权利要求5的OLED,其中所述至少一种根据权利要求1或2的化合物用作基质材料和/或阻断剂材料。
7.根据权利要求6的OLED,其中所述基质材料和/或阻断剂材料与三线态发射体一起使用。
8.包含至少一种根据权利要求1或2的化合物和至少一种三线态发射体的发光层。
9.包含至少一种根据权利要求1或2的化合物的空穴和/或激子阻断剂层。
10.根据权利要求1或2的化合物在OLED中的用途。
11.一种选自固定的可视显示单元,移动的可视显示单元和照明单元的器件,其包含至少一种根据权利要求5或6的有机发光二极管。
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ATE550342T1 (de) * | 2006-04-05 | 2012-04-15 | Basf Se | Heteroleptische übergangsmetall-carben-komplexe und deren verwendung in organischen leuchtdioden (oleds) |
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DE502008002309D1 (de) | 2011-02-24 |
JP2010525017A (ja) | 2010-07-22 |
EP2150556B1 (de) | 2011-01-12 |
KR101502187B1 (ko) | 2015-03-16 |
CN101687893A (zh) | 2010-03-31 |
US20100187980A1 (en) | 2010-07-29 |
WO2008132085A1 (de) | 2008-11-06 |
EP2150556A1 (de) | 2010-02-10 |
KR20100017417A (ko) | 2010-02-16 |
US7989091B2 (en) | 2011-08-02 |
JP5677836B2 (ja) | 2015-02-25 |
ATE495181T1 (de) | 2011-01-15 |
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