CN105906546B - 用于有机电致发光器件的氟衍生物 - Google Patents
用于有机电致发光器件的氟衍生物 Download PDFInfo
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- CN105906546B CN105906546B CN201610236009.1A CN201610236009A CN105906546B CN 105906546 B CN105906546 B CN 105906546B CN 201610236009 A CN201610236009 A CN 201610236009A CN 105906546 B CN105906546 B CN 105906546B
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- compound
- phenyl
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- aromatics
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- 238000005401 electroluminescence Methods 0.000 title claims abstract description 24
- 125000001153 fluoro group Chemical class F* 0.000 title abstract description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 136
- 239000000463 material Substances 0.000 claims abstract description 68
- -1 phenyl anthryl Chemical group 0.000 claims description 55
- 125000003118 aryl group Chemical group 0.000 claims description 47
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 37
- 239000000203 mixture Substances 0.000 claims description 34
- 229910052799 carbon Inorganic materials 0.000 claims description 28
- 125000004432 carbon atom Chemical group C* 0.000 claims description 24
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 21
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthene Chemical compound C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 claims description 20
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 229910052731 fluorine Inorganic materials 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 150000002576 ketones Chemical class 0.000 claims description 7
- 125000001931 aliphatic group Chemical group 0.000 claims description 6
- 230000004888 barrier function Effects 0.000 claims description 6
- 229910052744 lithium Inorganic materials 0.000 claims description 6
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 claims description 5
- 125000004429 atom Chemical group 0.000 claims description 5
- XNCMQRWVMWLODV-UHFFFAOYSA-N 1-phenylbenzimidazole Chemical group C1=NC2=CC=CC=C2N1C1=CC=CC=C1 XNCMQRWVMWLODV-UHFFFAOYSA-N 0.000 claims description 3
- RICKKZXCGCSLIU-UHFFFAOYSA-N 2-[2-[carboxymethyl-[[3-hydroxy-5-(hydroxymethyl)-2-methylpyridin-4-yl]methyl]amino]ethyl-[[3-hydroxy-5-(hydroxymethyl)-2-methylpyridin-4-yl]methyl]amino]acetic acid Chemical compound CC1=NC=C(CO)C(CN(CCN(CC(O)=O)CC=2C(=C(C)N=CC=2CO)O)CC(O)=O)=C1O RICKKZXCGCSLIU-UHFFFAOYSA-N 0.000 claims description 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 3
- 229910052805 deuterium Inorganic materials 0.000 claims description 3
- 125000001725 pyrenyl group Chemical group 0.000 claims description 3
- ZLGVZKQXZYQJSM-UHFFFAOYSA-N 1,2-diphenylbenzimidazole Chemical group C1=CC=CC=C1C1=NC2=CC=CC=C2N1C1=CC=CC=C1 ZLGVZKQXZYQJSM-UHFFFAOYSA-N 0.000 claims description 2
- 230000005669 field effect Effects 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 238000010791 quenching Methods 0.000 claims description 2
- 239000010409 thin film Substances 0.000 claims description 2
- ZDZHCHYQNPQSGG-UHFFFAOYSA-N binaphthyl group Chemical group C1(=CC=CC2=CC=CC=C12)C1=CC=CC2=CC=CC=C12 ZDZHCHYQNPQSGG-UHFFFAOYSA-N 0.000 claims 2
- OTEKOJQFKOIXMU-UHFFFAOYSA-N 1,4-bis(trichloromethyl)benzene Chemical compound ClC(Cl)(Cl)C1=CC=C(C(Cl)(Cl)Cl)C=C1 OTEKOJQFKOIXMU-UHFFFAOYSA-N 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 230000000903 blocking effect Effects 0.000 abstract description 7
- 125000003983 fluorenyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 abstract 1
- 239000010410 layer Substances 0.000 description 54
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 33
- 150000002220 fluorenes Chemical class 0.000 description 30
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 26
- 150000001412 amines Chemical class 0.000 description 23
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- 239000002585 base Substances 0.000 description 21
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 20
- 239000000243 solution Substances 0.000 description 19
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- 125000001072 heteroaryl group Chemical group 0.000 description 18
- 229920000642 polymer Polymers 0.000 description 17
- 239000002019 doping agent Substances 0.000 description 15
- 239000007787 solid Substances 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 235000019441 ethanol Nutrition 0.000 description 13
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 13
- 230000015572 biosynthetic process Effects 0.000 description 12
- 238000005406 washing Methods 0.000 description 12
- 238000003756 stirring Methods 0.000 description 11
- 238000003786 synthesis reaction Methods 0.000 description 11
- 239000013638 trimer Substances 0.000 description 11
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 10
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 10
- 239000000539 dimer Substances 0.000 description 10
- 238000004128 high performance liquid chromatography Methods 0.000 description 10
- 229910052757 nitrogen Inorganic materials 0.000 description 10
- 229910052760 oxygen Inorganic materials 0.000 description 10
- 125000001424 substituent group Chemical group 0.000 description 10
- 238000006467 substitution reaction Methods 0.000 description 10
- 238000001816 cooling Methods 0.000 description 9
- 239000003205 fragrance Substances 0.000 description 9
- 230000005525 hole transport Effects 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 229910052717 sulfur Inorganic materials 0.000 description 9
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 8
- 239000000412 dendrimer Substances 0.000 description 8
- 229920000736 dendritic polymer Polymers 0.000 description 8
- 239000000725 suspension Substances 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 7
- 229910052794 bromium Inorganic materials 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 6
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 6
- 238000002347 injection Methods 0.000 description 6
- 239000007924 injection Substances 0.000 description 6
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- KQIXXSOPMLEPAX-UHFFFAOYSA-N 1,2-bis(3,5-dibromophenyl)-9H-fluorene Chemical class BrC=1C=C(C=C(C=1)Br)C1=C(C=2CC3=CC=CC=C3C=2C=C1)C1=CC(=CC(=C1)Br)Br KQIXXSOPMLEPAX-UHFFFAOYSA-N 0.000 description 5
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Natural products P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 5
- 125000005605 benzo group Chemical group 0.000 description 5
- 238000004587 chromatography analysis Methods 0.000 description 5
- 125000004986 diarylamino group Chemical group 0.000 description 5
- 125000005842 heteroatom Chemical group 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 239000011159 matrix material Substances 0.000 description 5
- 238000007639 printing Methods 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 125000004122 cyclic group Chemical group 0.000 description 4
- 230000009477 glass transition Effects 0.000 description 4
- 230000003760 hair shine Effects 0.000 description 4
- 150000002460 imidazoles Chemical class 0.000 description 4
- 229910052740 iodine Inorganic materials 0.000 description 4
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 4
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
- 235000019341 magnesium sulphate Nutrition 0.000 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- 230000003287 optical effect Effects 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 150000003233 pyrroles Chemical group 0.000 description 4
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 125000005504 styryl group Chemical group 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- 229930192474 thiophene Natural products 0.000 description 4
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 4
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 3
- BKQXUNGELBDWLS-UHFFFAOYSA-N 9,9-diphenylfluorene Chemical class C1=CC=CC=C1C1(C=2C=CC=CC=2)C2=CC=CC=C2C2=CC=CC=C21 BKQXUNGELBDWLS-UHFFFAOYSA-N 0.000 description 3
- CYSPWCARDHRYJX-UHFFFAOYSA-N 9h-fluoren-1-amine Chemical compound C12=CC=CC=C2CC2=C1C=CC=C2N CYSPWCARDHRYJX-UHFFFAOYSA-N 0.000 description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
- 125000000304 alkynyl group Chemical group 0.000 description 3
- 150000004982 aromatic amines Chemical class 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 230000005540 biological transmission Effects 0.000 description 3
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 3
- 239000004327 boric acid Substances 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 238000006555 catalytic reaction Methods 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 230000005611 electricity Effects 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 3
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 3
- 229910052741 iridium Inorganic materials 0.000 description 3
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 3
- 229910052697 platinum Inorganic materials 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 230000001376 precipitating effect Effects 0.000 description 3
- 230000003252 repetitive effect Effects 0.000 description 3
- 239000004065 semiconductor Substances 0.000 description 3
- 235000021286 stilbenes Nutrition 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 125000005259 triarylamine group Chemical group 0.000 description 3
- 238000010792 warming Methods 0.000 description 3
- UWRZIZXBOLBCON-VOTSOKGWSA-N (e)-2-phenylethenamine Chemical compound N\C=C\C1=CC=CC=C1 UWRZIZXBOLBCON-VOTSOKGWSA-N 0.000 description 2
- WQONPSCCEXUXTQ-UHFFFAOYSA-N 1,2-dibromobenzene Chemical compound BrC1=CC=CC=C1Br WQONPSCCEXUXTQ-UHFFFAOYSA-N 0.000 description 2
- XKSAUBOAJBASKR-UHFFFAOYSA-N 1,3-diphenyl-2h-benzimidazole Chemical compound C1N(C=2C=CC=CC=2)C2=CC=CC=C2N1C1=CC=CC=C1 XKSAUBOAJBASKR-UHFFFAOYSA-N 0.000 description 2
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
- KTADSLDAUJLZGL-UHFFFAOYSA-N 1-bromo-2-phenylbenzene Chemical group BrC1=CC=CC=C1C1=CC=CC=C1 KTADSLDAUJLZGL-UHFFFAOYSA-N 0.000 description 2
- TZMSYXZUNZXBOL-UHFFFAOYSA-N 10H-phenoxazine Chemical compound C1=CC=C2NC3=CC=CC=C3OC2=C1 TZMSYXZUNZXBOL-UHFFFAOYSA-N 0.000 description 2
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 2
- BOSJLNBBNRZUCL-UHFFFAOYSA-N 3-(2-bromophenyl)-9-phenylcarbazole Chemical compound BrC1=CC=CC=C1C1=CC=C(N(C=2C=CC=CC=2)C=2C3=CC=CC=2)C3=C1 BOSJLNBBNRZUCL-UHFFFAOYSA-N 0.000 description 2
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 2
- HHIVQZMLSTXDCO-UHFFFAOYSA-N 9,9-bis(3,5-dibromophenyl)fluorene Chemical class BrC1=CC(Br)=CC(C2(C3=CC=CC=C3C3=CC=CC=C32)C=2C=C(Br)C=C(Br)C=2)=C1 HHIVQZMLSTXDCO-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N N-phenyl aniline Natural products C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 description 2
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 2
- MKYQPGPNVYRMHI-UHFFFAOYSA-N Triphenylethylene Chemical group C=1C=CC=CC=1C=C(C=1C=CC=CC=1)C1=CC=CC=C1 MKYQPGPNVYRMHI-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
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- YUENFNPLGJCNRB-UHFFFAOYSA-N anthracen-1-amine Chemical compound C1=CC=C2C=C3C(N)=CC=CC3=CC2=C1 YUENFNPLGJCNRB-UHFFFAOYSA-N 0.000 description 2
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- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- JAUCCASEHMVMPM-UHFFFAOYSA-N naphtho[2,1-e][1,3]benzoxazole Chemical compound C1=CC2=CC=CC=C2C2=C1C(N=CO1)=C1C=C2 JAUCCASEHMVMPM-UHFFFAOYSA-N 0.000 description 1
- QQTOBDXDQYCGMA-UHFFFAOYSA-N naphtho[2,3-e][1,3]benzoxazole Chemical compound C1=CC=C2C=C3C(N=CO4)=C4C=CC3=CC2=C1 QQTOBDXDQYCGMA-UHFFFAOYSA-N 0.000 description 1
- 125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 description 1
- 125000005069 octynyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C#C* 0.000 description 1
- XSXHWVKGUXMUQE-UHFFFAOYSA-N osmium dioxide Inorganic materials O=[Os]=O XSXHWVKGUXMUQE-UHFFFAOYSA-N 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 description 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- SLIUAWYAILUBJU-UHFFFAOYSA-N pentacene Chemical compound C1=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C21 SLIUAWYAILUBJU-UHFFFAOYSA-N 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 125000005981 pentynyl group Chemical group 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 150000005053 phenanthridines Chemical class 0.000 description 1
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 125000004437 phosphorous atom Chemical group 0.000 description 1
- 238000005424 photoluminescence Methods 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- CPNGPNLZQNNVQM-UHFFFAOYSA-N pteridine Chemical compound N1=CN=CC2=NC=CN=C21 CPNGPNLZQNNVQM-UHFFFAOYSA-N 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 238000005092 sublimation method Methods 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 150000003455 sulfinic acids Chemical class 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 238000001931 thermography Methods 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 238000010023 transfer printing Methods 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 238000005829 trimerization reaction Methods 0.000 description 1
- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 238000002061 vacuum sublimation Methods 0.000 description 1
- 238000001947 vapour-phase growth Methods 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 150000003752 zinc compounds Chemical class 0.000 description 1
- GTLDTDOJJJZVBW-UHFFFAOYSA-N zinc cyanide Chemical compound [Zn+2].N#[C-].N#[C-] GTLDTDOJJJZVBW-UHFFFAOYSA-N 0.000 description 1
Classifications
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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- C07C255/50—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton to carbon atoms of non-condensed six-membered aromatic rings
- C07C255/51—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton to carbon atoms of non-condensed six-membered aromatic rings containing at least two cyano groups bound to the carbon skeleton
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- C07C13/54—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with three condensed rings
- C07C13/547—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with three condensed rings at least one ring not being six-membered, the other rings being at the most six-membered
- C07C13/567—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with three condensed rings at least one ring not being six-membered, the other rings being at the most six-membered with a fluorene or hydrogenated fluorene ring system
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Abstract
本发明涉及用于有机电致发光器件的氟衍生物。特别地,本发明涉及芴衍生物和有机电子器件,其中所述的化合物用作发光层中的基质材料,和/或用作空穴传输材料,和/或用作电子阻挡或激子阻挡材料,和/或用作电子传输材料。
Description
本发明是申请日为2009年3月11日、申请号为201410490593.4、发明名称为“用于有机电致发光器件的氟衍生物”的中国发明专利申请的分案申请。上述中国发明专利申请201410490593.4本身是申请号为200980111846.X的中国发明专利申请的分案申请,并且在该中国发明专利申请201410490593.4的第一次审查意见通知书中指出了存在缺乏单一性的问题。
技术领域
本发明涉及用于有机电致发光器件的氟衍生物。特别地,本发明涉及有机半导体和其在有机电子器件中的用途。
背景技术
正在开发用于许多不同类型的电子应用的有机半导体。例如在US 4539507、US5151629、EP 0676461和WO 98/27136中描述了其中这些有机半导体用作功能材料的有机电致发光器件(OLED)的构造。然而,为了这些器件用于高质量和长寿命的显示器,仍然希望进一步改进。因此,目前需要改进,特别是,发蓝色光有机电致发光器件的寿命和效率。此外需要化合物具有高的热稳定性和高的玻璃化转变温度,而且它们能够在不分解的情况下升华。特别是对于高温应用,为了实现长寿命,高的玻璃化转变温度是必要的。
仍旧需要改进的材料,例如用于荧光和磷光发光体的主体材料,但是同样希望进一步改进,特别是,在电荷传输材料的情况下,即,空穴和电子传输材料和电荷阻挡材料。特别是这些材料的性能通常限制有机电致发光器件的寿命和效率。
意想不到的,已经发现在两个苯基每一个的3'-和5'-位被取代的9,9-二苯基芴衍生物,非常适用于有机电致发光器件中,其中它们相对于现有技术产生明显的改进。如果使用9,10-二氢蒽衍生物或相应的杂环衍生物而不是芴,这同样适用。因此,本发明涉及这些化合物和其在有机电子器件中的用途。取决于在苯基上的取代,本发明的化合物特别适合作为空穴传输材料、电子或激子阻挡材料、用于荧光或磷光化合物的基质材料、空穴阻挡材料和电子传输材料。与现有技术的材料相比较,本发明的材料对于有机电子器件的相同或改善的寿命,能够增加效率。此外,这些化合物具有高的热稳定性。通常,因为它们具有高的玻璃化转变温度,因此这些材料非常适合用于有机电子器件中。相应的扩展结构,特别是茚并芴结构和茚并咔唑结构,同样具有良好的性能。
作为最接近的现有技术,可以提到US 5,698,740、JP 2005/085599和JP 2007/049055。US 5,698,740和JP 2005/085588公开了在两个苯基每一个上被至少一个氨基或单或二取代的氨基取代的9,9-二苯基芴衍生物。仅明确地公开了在苯基每一个4'-位被氨基取代的结构,即与芴连接的对位。没有公开在一个苯基上被多个氨基取代的结构。JP 2007/049055公开了在两个苯基的至少一个上被至少一个取代或未取代的吡咯或苯并咪唑基团取代的9,9-二苯基芴衍生物。仅明确地公开了在每一个苯基的4-位被氨基取代的结构,即与芴连接的对位。没有公开在一个苯基上被多个吡咯或苯并咪唑基团取代的结构。然而,在这些申请中公开的取代方式没有产生在用于有机电子器件中时具有足够良好性能的化合物。意想不到的,已经发现特定的在苯基的3'-和5'-位的每一个均同时取代是本发明化合物良好性能的成因。
此外,WO 05/053055公开了在每一个三嗪基团的3,5-位载带苯基的9,9-双(三嗪基)芴,作为磷光电致发光器件中的空穴阻挡材料。然而,该化合物的效果归因于在分子中存在的三嗪基团。在三嗪的3,5-位存在的取代基没有给予任何重要性。
为了清楚起见,9,9-二苯基芴的结构和编号显示如下:
发明内容
因此,本发明涉及通式(1)的化合物
其中以下适用使用的符号:
X在每一次出现中相同或者不同地是CR1或N,其中在每一个环中最多3个基团X代表N;
或两个直接相邻的基团X代表以下通式(7)的单元
其中,虚线键表示所述单元与相邻的C或N原子的连接;
Y在每一次出现中相同或者不同地是单键或选自如下的基团:BR1、C(R1)2、C(=O)、C(=NR1)、C(=C(R1)2)、Si(R1)2、NR1、PR1、P(=O)R1、O、S、S(=O)、S(=O)2、C(R1)2-C(R1)2、C(R1)2-NR1或CR1=CR1;
Z在每一次出现中相同或者不同地是CR1或N,其中在每一个环中最多两个符号Z代表N;
R在每一次出现中相同或者不同地是Cl、Br、I、三氟甲烷磺酸酯、B(OR2)2、B(R2)2、B(N(R2)2)2、NAr2、N(R2)2、SiAr3、Si(R2)3、C(=O)Ar、C(=O)R2、OAr、OR2、SAr、SR2、S(=O)Ar、S(=O)R2、S(=O)2Ar、S(=O)2R2、PAr2、P(R2)2、P(=O)Ar2、P(=O)(R2)2或具有5-60个芳族环原子的芳族或杂芳族环体系,它们可以被一个或多个基团R1取代;
Ar在每一次出现中相同或者不同地是具有5-30个芳族环原子的芳族或杂芳族环体系,它们可被一个或多个非芳基R1取代;此处结合到同一氮或磷原子上的两个基团Ar也可以通过单键或选自如下的桥连基彼此连接:B(R2)、C(R2)2、Si(R2)2、C=O、C=NR2、C=C(R2)2、O、S、S=O、SO2、N(R2)、P(R2)和P(=O)R2;
R1在每一次出现中相同或者不同地是H、D、F、Cl、Br、I、CHO、N(R2)2、N(Ar)2、C(=O)Ar、P(=O)(Ar)2、S(=O)Ar、S(=O)2Ar、CR2=CR2Ar、CN、NO2、Si(R2)3、B(OR2)2、B(R2)2、B(N(R2)2)2、OSO2R2、具有1-40个碳原子的直链烷基、链烯基、炔基、烷氧基或者硫代烷氧基、或者具有3-40个碳原子的支链或者环状的烷基、链烯基、炔基、烷氧基或者硫代烷氧基,它们每个可被一个或多个基团R2取代,其中一个或多个非相邻的CH2基团可被R2C=CR2、C≡C、Si(R2)2、Ge(R2)2、Sn(R2)2、C=O、C=S、C=Se、C=NR2、P(=O)(R2)、SO、SO2、NR2、O、S或CONR2替代,和其中一个或多个H原子可被F、Cl、Br、I、CN或NO2替代,或具有5-60个芳族环原子的芳族或杂芳族环体系,它们在每一情况下可以被一个或多个基团R2取代,或具有5-60个芳族环原子的芳氧基或杂芳氧基,它们可被一个或多个基团R2取代,或这些体系的组合;此处两个或多个相邻的取代基R1也可以彼此形成单或多环的、脂肪族或芳族环体系;
R2在每一次出现中相同或者不同地是H、D、或具有1-20个碳原子的脂肪族、芳族和/或杂芳族烃基,其中,另外,H原子可被F替代;此处的两个或多个相邻的取代基R2也可以彼此形成单或多环的、脂肪族或芳族环体系;
n是1或2;
本发明不包括以下化合物:
具体实施方式
通式(1)的化合物优选的玻璃化转变温度TG大于70℃,特别优选大于100℃,非常特别优选大于110℃。
如从通式(1)显而易见的,n=2是指在3,5-位取代的两个芳基在芴的9,9-位结合,或在化合物相应衍生物的9,9-位结合,而n=1是指存在一个这样的芳基和另外一个基团R1。
对于本发明的目的,芳基包含6-60个碳原子;对于本发明的目的,杂芳基包含2-60个碳原子和至少一个杂原子,条件是碳原子和杂原子的总和至少为5。杂原子优选选自N、O、和/或S。本发明的芳基或者杂芳基认为是指单芳族环,即苯,或者单杂芳族环,例如吡啶、嘧啶、噻吩等,或者稠合的芳基或者杂芳基,例如萘、蒽、嵌二萘、喹啉、异喹啉等。
对于本发明的目的,芳族环体系在环体系中包含6-60个碳原子。对于本发明的目的,杂芳族环体系在环体系中包含2-60个碳原子和至少一个杂原子,条件是碳原子和杂原子的总数至少为5。杂原子优选选自N、O、和/或S。对于本发明的目的,芳族或杂芳族环体系意指不一定仅包括芳基或杂芳基的体系,而是其中多个芳基或杂芳基也可以被短的非芳族单元间断(优选<10%的非H原子),比如sp3-杂化的C、N或O原子。因此,比如9,9'-螺二芴、9,9-二芳基芴、三芳胺、二芳基醚、芪、二苯甲酮等体系,对于本发明目的同样意指芳族环体系。芳族或杂芳族环体系同样认为是指其中多个芳基或杂芳基基团通过单键彼此连接的体系,例如联苯、三联苯或二吡啶。
对于本发明的目的,其中另外单个H原子或CH2基团可以被上述提到基团取代的C1-C40烷基,特别优选认为是指如下的基团:甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、2-甲基丁基、正戊基、仲戊基、环戊基、正己基、环己基、正庚基、环庚基、正辛基、环辛基、2-乙基己基、三氟甲基、五氟乙基和2,2,2-三氟乙基。对于本发明的目的,链烯基认为是指,特别是乙烯基、丙烯基、丁烯基、戊烯基、环戊烯基、己烯基、环己烯基、庚烯基、环庚烯基、辛烯基或环辛烯基。对于本发明的目的,炔基认为是指,特别是乙炔基、丙炔基、丁炔基、戊炔基、己炔基、庚炔基或辛炔基。C1-到C40烷氧基特别优选认为是指甲氧基、三氟甲氧基、乙氧基、正丙氧基、异丙氧基、正丁氧基、异丁氧基、仲丁氧基、叔丁氧基或者2-甲基丁氧基。具有5-60个芳族环原子,它们在每一情况下也可以被上述提到的基团R取代以及可以通过任何希望的位置与芳族或杂芳族环体系连接的芳族或杂芳族环体系特别是指来源于如下的基团:苯、萘、蒽、菲、苯并蒽、嵌二萘、二萘嵌苯、荧蒽、并四苯、并五苯、苯并芘、联苯、亚联苯、三联苯、亚三联苯、芴、螺二芴、二氢菲、二氢芘、四氢芘、顺式的或者反式的茚并芴、三聚茚、异三聚茚、螺三聚茚、螺异三聚茚、呋喃、苯并呋喃、异苯并呋喃、二苯并呋喃、噻吩、苯并噻吩、异苯并噻吩、硫(杂)芴、吡咯、吲哚、异吲哚、咔唑、吡啶、喹啉、异喹啉、吖啶、菲啶、苯并-5,6-喹啉、苯并-6,7-喹啉、苯并-7,8-喹啉、吩噻嗪、吩噁嗪、吡唑、吲唑、咪唑、苯并咪唑、萘并咪唑、菲并咪唑、吡啶并咪唑、吡嗪并咪唑、喹喔啉并咪唑、噁唑、苯并噁唑、萘并噁唑、蒽并噁唑、菲并噁唑、异噁唑、1,2-噻唑、1,3-噻唑、苯并噻唑、哒嗪、苯并哒嗪、嘧啶、苯并嘧啶、喹喔啉、1,5-二氮蒽、2,7-二氮芘、2,3-二氮芘、1,6-二氮芘、1,8-二氮芘、4,5-二氮芘、4,5,9,10-四氮苝、吡嗪、吩嗪、吩噁嗪、吩噻嗪、荧红环、1.5-二氮杂萘、氮咔唑、苯并咔啉、菲咯啉、1,2,3-三唑、1,2,4-三唑、苯并三唑、1,2,3-噁二唑、1,2,4-噁二唑、1,2,5-噁二唑、1,3,4-噁二唑、1,2,3-噻二唑、1,2,4-噻二唑、1,2,5-噻二唑、1,3,4-噻二唑、1,3,5-三嗪、1,2,4-三嗪、1,2,3-三嗪、四唑、1,2,4,5-四嗪、1,2,3,4-四嗪、1,2,3,5-四嗪、嘌呤、蝶啶、中氮茚和苯并噻二唑。
在本发明的优选实施方案中,符号X在每一次出现中相同或者不同地代表CR1或N,其中在芴单元中的每个环中最多一个符号X代表N,和其中或者在芴单元9-位的取代基中所有的符号X都代表CR1,或所有的符号X都代表N。在本发明另外的优选实施方式中,准确地说是两个相邻的基团X代表上述提到的通式(7)的单元。因此,在芴的9-位上的取代基优选代表3,5-取代的苯基或三嗪。如果中心单元不代表芴,而是代表通式(1)包括的其他衍生物之一,则适用相应的情形。符号X特别优选代表CR1。
通式(7)单元中的符号Z优选代表CR1。
通式(1)化合物的优选实施方案是通式(2)、(3)、(8)、(9)、(10)和(11)的化合物:
其中使用的符号和标记具有以上指出的含义。
在本发明的优选实施方案中,在通式(1)、(2)、(3)、(8)、(9)、(10)或(11)化合物的六员环中的符号Y代表单键或选自C(R1)2、O或NR1的基团,特别优选单键,和在五员环中,优选代表选自C(R1)2、O、或NR1的基团,特别优选C(R1)2或N,非常特别优选C(R1)2。
因此,优选通式(2a)、(3a)、(8a)、(8b)、(9a)、(9b)、(10a)、(10b)、(11a)和(11b)的化合物:
其中使用的符号和标记具有如上提及的含义。
在本发明的优选实施方案中,n=2。
通式(1)化合物的另外的优选实施方案是通式(4a)和(4b)的化合物:
其中使用的符号具有以上指出的含义。
本发明特别优选的实施方案是以下通式(4c)、(4d)、(8c)、(8d)、(9c)、(9d)、(10c)、(10d)、(11c)和(11d)的化合物:
其中使用的符号和标记具有如上提及的的含义。
在本发明另外的优选实施方式中,上述提及的通式化合物中的符号R在每一次出现中相同或者不同地代表NAr2、C(=O)Ar、P(=O)Ar2或具有5-30个芳族环原子的芳族或杂芳族环体系,它们可被一个或多个非芳基R1取代。如果R与苯基结合,则R特别优选,在每一次出现中相同或者不同地代表,优选在每一次出现中相同地代表NAr2或C(=O)Ar,非常特别优选代表NAr2。如果R与三嗪基团结合,则R特别优选代表具有5-10个芳族环原子的芳基或杂芳基。此外优选的取代基R是Cl、Br、I和三氟甲烷磺酸酯,特别是Br,因为这些是在合成本发明另外的化合物中有价值的中间体。
在本发明另外的优选实施方式中,上述提到的通式化合物中所有的符号R选择为相同。这种优选可解释为所述化合物更容易的合成易得性。
如果基团R或R1代表基团N(Ar)2,则该基团优选选自通式(5)或通式(6)的基团:
其中R2具有以上指出的含义,和此外:
E代表单键、O、S、N(R2)或C(R2)2;
Ar1在每一次出现中相同或者不同地是具有5-20个芳族环原子的芳族或杂芳族环体系,或具有15-30个芳族环原子的三芳基胺基团,它们每个可被一个或多个基团R2取代,优选具有6-14个芳族环原子的芳基或杂芳基,或具有18-30个芳族环原子、优选具有18-22个芳族环原子的三芳基胺基团,它们每个可被一个或多个基团R2取代;
p在每一次出现中相同或者不同地是0或1。
Ar1特别优选在每一次出现中相同或者不同地代表苯基、联苯基、1-萘基、2-萘基、2-、3-或4-三苯胺、1-或2-萘基二苯基胺,它们每个可以通过萘基或苯基结合,或1-或2-二萘基苯胺,它们每个可以通过萘基或苯基结合,N-咔唑基、或N-苯基-2-咔唑基或N-苯基-3-咔唑基。这些基团每一个可以被一个或多个具有1-4个碳原子的烷基或氟取代。
如果基团R或R1代表芳族或杂芳族环体系,则它优选选自具有5-30个芳族环原子、特别是具有6-20个芳族环原子的芳族或杂芳族环体系,非常特别优选苯基、1-萘基、2-萘基、蒽基、苯基蒽基、1-或2-萘基蒽基、联萘、芘基、荧蒽基、2-,3-,4-,5-,6-或7-苯并蒽基、N-苯并咪唑基、苯基-N-苯并咪唑基、N-苯基苯并咪唑基和苯基-N-苯基苯并咪唑基。
在本发明另外的优选实施方式中,在上述提到的通式化合物中的符号R1在每一次出现中相同或者不同地代表H、F、N(Ar)2、C(=O)Ar、P(=O)(Ar)2、S(=O)Ar、S(=O)2Ar、CR2=CR2Ar、具有1-10个碳原子的直链烷基、或具有3-10个碳原子的支链或环状的烷基,它们每个可被一个或多个基团R2取代,其中一个或多个非相邻的CH2基团可被R2C=CR2或O替代,和其中一个或多个H原子可被F替代,或具有5-20个芳族环原子的芳族或杂芳族环体系,在每一情况下它们可以被一个或多个基团R2取代,或这些体系的组合;此处两个或多个相邻的取代基R1也可以彼此形成单或者多环的、脂肪族或芳族环体系。在本发明的特别优选实施方案中,在上述提到的通式化合物中的符号R1在每一次出现中相同或者不同地代表H、F、N(Ar)2、具有1-6个碳原子的直链烷基、或具有3-6个碳原子的支链或环状的烷基,它们每个可被一个或多个基团R2取代,其中一个或多个H原子可被F替代,或具有5-14个芳族环原子的芳族或杂芳族环体系,在每一情况下它们可以被一个或多个基团R2取代;此处两个或多个相邻的取代基R1也可以彼此形成单或者多环的、脂肪族或芳族环体系。特别是,R1在每一次出现中相同或者不同地代表H、F、甲基、乙基、异丙基或叔丁基,特别是H。在化合物从溶液中加工的情况下,具有最高达10个碳原子的直链或支链烷基链同样是优选的。
对于相应的Y的选择,存在于桥连基Y中优选的基团R1在每一次出现中是相同或不同的,并且优选选自H、具有1-6个碳原子的直链烷基或具有3-6个碳原子的支链烷基,其中一个或多个非相邻的CH2基团可被-R2C=CR2-、-C≡C-或-O-替代,和其中一个或多个H原子可被F替代,或具有6-20个碳原子的芳基或具有2-20个碳原子的杂芳基,它们每个可被一个或多个基团R2取代,或这些体系的两个或三个的组合;此处两个都与Y结合的两个基团R1也可以彼此形成环体系,并因此形成螺体系。与桥连基Y结合的特别优选的基团R1在每一次出现中是相同或不同的,并选自甲基、乙基、异丙基、叔丁基,其中在每一情况下一个或多个H原子可被F替代,或具有6-14个碳原子的芳基,它们可被一个或多个基团R2取代;此处两个基团R1也可以彼此形成环体系。在化合物从溶液中加工的情况下,具有最高达10个碳原子的直链或支链烷基链同样是优选的。如果桥连基Y是基团NR1,同样基团R1特别优选选自具有5-20个芳族环原子的芳族或杂芳族环体系。
优选的通式(1)-(4)化合物的例子是以下描述的结构(1)-(276)。
本发明通式(1)的化合物能够通过本领域普通技术人员已知的一般性合成步骤制备。用于本发明对称性取代的化合物的原料化合物例如能够是3,3',5,5'-四溴二苯甲酮(Eur.J.Org.Chem.(欧洲有机化学期刊)2006,2523-2529)。这能够例如根据方案1,通过与取代或未取代的2-联苯基锂、2-锂二苯基醚、2-锂二苯基硫醚、2-(2-苯基锂)-2-苯基-1,3-二氧戊环或2-锂苯基二苯基胺反应转化为相应的三芳基甲醇,然后在酸性条件下,例如在有乙酸和无机酸,例如溴化氢存在的情况下进行环化。该反应需要的有机锂化合物能够,使用烷基锂化合物例如正丁基锂,通过相应的芳基溴化物(2-溴联苯、2-溴二苯基醚、2-溴二苯基硫醚、2-(2-溴苯基)-2-苯基-1,3-二氧戊环、2-溴苯基二苯基胺等等)的金属转移制备。当然,使用类似相应的格氏化合物也是可能的。
方案1
以这种方法制造的四溴化物能够通过本领域普通技术人员已知的方法进一步转化。与硼酸的钯催化反应(Suzuki偶合)或与有机锌化合物的钯催化反应(Negishi偶合)产生本发明的芳族或杂芳族化合物(方案2)。
方案2
与胺的钯催化反应(Hartwig-Buchwald偶合)产生本发明的芳族或杂芳族胺(方案3)。
方案3
溴官能团能够使用有机锂化合物或格氏化合物通过金属转移转化为亲电子基团,然后与多种亲电子试剂例如芳基硼卤化物、醛、酮、腈、酯、卤代酯、二氧化碳、芳基膦卤化物、卤代亚磺酸、卤代芳基磺酸等偶合,其中以这种方法得到的化合物可以是本发明的最后产物,或能够进一步反应的中间体。这参考制备本发明酮、氧化膦和苯并咪唑的实施例举例描述(方案4)。
方案4
本发明非对称取代的化合物能够通过方案5根据如下顺序得到,从芴酮和类似的芳基酮开始,通过在羰基官能团上加成芳基金属化合物,例如1-锂-3,5-二溴苯,通过如上提及的方法之一转化溴化的芳族化合物,形成一个官能团并随后通过在1,3-二溴苯上酸催化的Friedel-Crafts芳基化引入其他的官能团,并且通过如上提及的方法之一转化溴化的芳族化合物(例如见Org.Lett.(有机快报)2001,3(15),2285)。
方案5
相应地能够合成通式(1)的相应茚并芴衍生物、茚并咔唑衍生物和其他的衍生物。
本发明此外涉及制备通式(1)化合物的方法,包括使双(3,5-二溴)二苯甲酮与取代或未取代的2-联苯基锂、2-锂二苯基醚、2-锂二苯基硫醚、2-(2-苯基锂)-2-苯基-1,3-二氧戊环、2-锂苯基二苯基胺或相应的格氏化合物反应,得到三芳基甲醇,随后在酸性条件下环化,并任选随后溴基团的进一步反应。
上面描述的本发明的化合物,特别是被反应性离去基团,例如溴、碘、三氟甲烷磺酸酯、甲苯磺酸酯、硼酸或硼酸酯取代的化合物,能用作为制造相应的二聚物、三聚物、四聚物、五聚物、低聚物、聚合物的单体,或能作为树枝状高分子的核。此处,低聚或聚合优选通过卤素官能团或硼酸官能团进行。这特别适用于通式(4)的化合物,其中每一个基团R1代表反应性离去基团,特别是选自如上提及的基团。
从而,本发明此外涉及包括一个或多个通式(1)化合物的二聚物、三聚物、四聚物、五聚物、低聚物、聚合物或树枝状高分子,其中一个或多个基团R1或R2代表在二聚物、三聚物、四聚物或五聚物中通式(1)化合物之间的结合,或代表从通式(1)的化合物到聚合物、低聚物或树枝状高分子的结合,或其中在基团R上通过取代基发生该结合。对于本发明的目的,低聚物认为是指具有至少六个通式(1)单元的化合物。该聚合物、低聚物或树枝状高分子可以是共轭的、部分共轭或非共轭的。该三聚物、四聚物、五聚物、低聚物或聚合物可以是线性的或支化的。在线性的连接结构中,通式(1)的单元可以彼此直接连接,或彼此通过二价基团,例如通过取代或未取代的亚烷基连接,通过杂原子连接,或通过二价芳族或杂芳族基团连接。在支化结构中,例如通式(1)的三个或更多个单元可以通过三价或多价基团连接,例如通过三价或多价的芳族或杂芳族基团连接,得到支化的三聚物、四聚物、五聚物、低聚物或聚合物。
对于在二聚物、三聚物、四聚物、五聚物、低聚物和聚合物中的通式(1)的重复单元,适用与上述相同的优选。因此,此处优选的重复单元同样是如上提及的通式单元。
对于低聚物或聚合物的制备,本发明的单体可与其他单体均聚或共聚。适当的和优选的共聚单体选自芴(例如根据EP 842208或WO 00/22026)、螺二芴(例如根据EP707020、EP 894107或WO 06/061181)、对亚苯基(例如根据WO 92/18552)、咔唑(例如根据WO04/070772或WO 04/113468)、噻吩(例如根据EP 1028136)、二氢菲(例如根据WO 05/014689)、顺式的和反式的茚并芴(例如根据WO 04/041901或WO 04/113412)、酮(例如根据WO 05/040302)、菲(例如根据WO 05/104264或WO 07/017066)或同样多个这些单元。聚合物、低聚物和树枝状高分子通常同样包含其他的单元,例如发光(荧光或磷光)单元,例如乙烯基三芳胺(例如,根据WO 07/068325),或磷光金属配合物(例如,根据WO 06/003000),和/或电荷传输单元。如果一个或多个基团R代表NAr2,则此处本发明的重复单元特别适合作为空穴的电荷传输单元。
本发明还涉及包括至少一种通式(1)的化合物,或相应的二聚物、三聚物、四聚物、五聚物、低聚物或聚合物和至少一种其他化合物的混合物。如果通式(1)的化合物用作基质材料,则其他的化合物例如可以是荧光或磷光的掺杂物。以下提到的与有机电致发光器件有关的适合的荧光和磷光掺杂物,同样对于本发明的混合物是优选的。如果通式(1)的化合物是空穴传输或电子传输化合物,其他的化合物也可以是掺杂物。下面提到与有机电致发光器件有关的适合的掺杂物。
本发明此外仍涉及包括至少一种通式(1)化合物,或相应的二聚物、三聚物、四聚物、五聚物、低聚物或聚合物和至少一种有机溶剂的溶液。对于例如通过旋涂或印刷方法从溶液中制造有机电子器件,需要该类型的溶液。
本发明通式(1)的化合物和相应的二聚物、三聚物、四聚物、五聚物、低聚物、聚合物或树枝状高分子适合用于电子器件中,特别是用于有机电致发光器件(OLED、PLED)中。取决于取代的情况,该化合物能用于不同的功能和层中。此处优选实施方式符合如上提及的的通式。
因此,本发明还涉及通式(1)的化合物或相应的二聚物、三聚物、四聚物、五聚物、低聚物、聚合物、或树枝状高分子在电子器件、特别是在有机电致发光器件中的用途。
此外本发明还涉及如下的有机电子器件,其包括至少一种通式(1)的化合物或相应的二聚物、三聚物、四聚物、五聚物、低聚物、聚合物或树枝状高分子,特别是涉及包括阳极、阴极和至少一个发光层的有机电致发光器件,其特征在于至少一个有机层,它可以是发光层或另外的层,包括至少一种通式(1)的化合物或相应的二聚物、三聚物、四聚物、五聚物、低聚物、聚合物或树枝状高分子。
除了阴极、阳极和发光层,所述有机电致发光器件也可以包含另外的层。这些例如是在每一情况下选自一个或多个空穴注入层、空穴传输层、空穴阻挡层、电子传输层、电子注入层、电子阻挡层、激子阻挡层、电荷产生层(IDMC 2003,Taiwan(台湾);Session 21OLED(5),T.Matsumoto,T.Nakada,J.Endo,K.Mori,N.Kawamura,A.Yokoi,J.Kido,MultiphotonOrganic EL Device Having Charge Generation Layer(具有电荷产生层的多光子有机EL器件))和/或有机的或无机的p/n结。此外,所述的层,特别是电荷传输层,也可以被掺杂。所述层的掺杂对于改进电荷传输可能是有利的。然而,此处应该指出无需这些层的每一个都必须存在,层的选择常常取决于使用的化合物,特别是还取决于器件是否是荧光或磷光电致发光器件。
在本发明另外的优选实施方式中,有机电致发光器件包括多个发光层,其中至少一个有机层包括至少一种通式(1)的化合物。这些发光层特别优选总计具有多个在380nm和750nm之间的发光峰值,产生总体的白色发光,即,能发荧光或发磷光及发蓝色、黄色、橙色或红色光的不同的发光化合物可用于发光层中。特别优选三层体系,即,体系具有三个发光层,其中这些层的至少一个包括至少一种通式(1)的化合物,和其中三个层显示蓝色、绿色和橙色或者红色发光(对于基本结构,例如见WO 05/011013)。具有宽带发射带并因此显示白色发光的发光体同样适合于白色发光。
在本发明的优选实施方案中,通式(1)的化合物用作发光层中荧光或磷光化合物的基质材料。在磷光化合物基质材料的情况下,一个或多个基团R和/或R1优选代表C(=O)Ar、N(Ar)2、S(=O)Ar、S(=O)2Ar或P(=O)Ar2。相同的优选适用于在通式(2)、(3)和(4)结构中的基团R和R1。在用于荧光化合物的基质材料的情况下,一个或多个基团R和/或R1优选代表芳族或杂芳族环体系,特别是代表包括蒽的芳族环体系。相同的优选适用于如上提及的通式结构中的基团R和R1。
在包括基质和掺杂物的体系中,基质材料认为是指以较高的比例存在于体系中的组分。在包括一种基质和多个掺杂物的体系中,基质认为是指在混合物中比例最高的组分。
在本发明的优选实施方案中,使用的基质是混合物,其中该混合物的至少一种组分是通式(1)的化合物。优选该混合物的一种组分是空穴传输化合物和另一组分是电子传输化合物。优选的空穴传输化合物是芳香胺和咔唑衍生物。优选的电子传输化合物是芳香酮。
如果通式(1)的化合物用作发光层中的发光化合物的基质材料,则它能够以与一种或多种发磷光材料(三线态发光体)结合方式使用。对于本发明的目的,磷光认为是指从具有相对高自旋多重性的受激态发光,即,自旋态>1,特别是从激发的三重态发光。对于本发明的目的,所有的,特别是发光的铱、铂、锇、金和铜化合物均称为发磷光材料。则包括通式(1)化合物和发光化合物的混合物,基于包括发光体和基质材料的混合物整体,包括99-1wt%、优选98-10wt%、特别优选97-60wt%、特别是95-85wt%的通式(1)的化合物。相应地,该混合物基于包括发光体和基质材料的混合物整体,包括1-99wt%、优选2-90wt%、特别优选3-40wt%、特别是5-15wt%的发光体。
适当的磷光化合物(=三线态发光体)特别是这样的的化合物,其在适当激发下发光,优选在可见区发光,并另外包含至少一个原子序数大于20、优选大于38但小于84、特别优选大于56但小于80的原子。使用的磷光发光体优选是包含铜、钼、钨、铼、钌、锇、铑、铱、钯、铂、银、金或者铕的化合物,特别是包含铱或者铂的化合物。
通过申请WO 00/70655、WO 01/41512、WO 02/02714、WO 02/15645、EP 1191613、EP1191612、EP 1191614和WO 05/033244公开了上面描述的发光体的例子。此外本发明如上提及的化合物适合作为发光体。一般说来,所有如现有技术中用于磷光OLED的和如在有机电致发光领域中的本领域普通技术人员已知的磷光配合物都是适当的,本领域普通技术人员在不付出创造性劳动的情况下能够使用其他的磷光配合物。
如果通式(1)的化合物用作荧光化合物的基质材料,则在发光层中的基质材料比例在50.0-99.9wt%之间,优选在80.0-99.5wt%之间,特别优选在90.0-99.0wt%之间。相应地,掺杂物的比例为0.1-50.0wt%、优选为0.1-20.0wt%、特别优选为0.5-15wt%、非常特别优选为1.0-10.0wt%。
优选的掺杂物选自单苯乙烯基胺、二苯乙烯基胺、三苯乙烯基胺、四苯乙烯基胺、苯乙烯基膦、苯乙烯基醚和芳基胺类。单苯乙烯基胺认为是指包含一个取代或未取代的苯乙烯基和至少一种胺、优选芳香胺的化合物。二苯乙烯基胺认为是指包含两个取代或未取代的苯乙烯基和至少一种胺、优选芳香胺的化合物。三苯乙烯基胺认为是指包含三个取代或未取代的苯乙烯基和至少一种胺、优选芳香胺的化合物。四苯乙烯基胺认为是指包含四个取代或未取代的苯乙烯基和至少一种胺、优选芳香胺的化合物。苯乙烯基特别优选是芪,它们也可以被进一步取代。类似胺,定义相应的膦和醚。对于本发明的目的,芳基胺或芳香胺认为是指包含三个直接与氮结合的取代或未取代的芳族或者杂芳族环体系的化合物。优选,这些芳族或者杂芳族环体系的至少一个是稠环体系,优选具有至少14个芳族环原子。其优选的例子是芳香蒽胺、芳香蒽二胺、芳香芘胺、芳香芘二胺、芳香胺或者芳香二胺。芳香蒽胺认为是指其中二芳氨基直接与蒽基团优选在9-位结合的化合物。芳香蒽二胺认为是指其中两个二芳氨基直接与蒽基团优选在9,10-位结合的化合物。类似地,定义芳香芘胺、芘二胺、胺和二胺,其中二芳氨基优选与芘在1-位或在1,6-位结合。其他优选的掺杂物选自茚并芴胺或者茚并芴二胺,例如根据WO 06/122630,苯并茚并芴胺或者苯并茚并芴二胺,例如根据WO 08/006449,和二苯并茚并芴胺或者二苯并茚并芴二胺,例如根据WO 07/140847。来自苯乙烯胺类的掺杂物的例子是取代或者未取代的三芪胺,或者公开于WO 06/000388、WO 06/058737、WO 06/000389、WO 07/065549和WO 07/115610中的掺杂物。
在本发明的另外的实施方式中,通式(1)的化合物用作空穴传输材料或用作空穴注入材料或用作电子阻挡材料或用作激子阻挡材料。该化合物然后优选被至少一个基团N(Ar)2取代,优选被至少两个基团N(Ar)2取代,和/或包含其他的改进空穴传输的基团。对于所有的基团R此处特别优选的是代表N(Ar)2。基团N(Ar)2优选选自上面描述的通式(5)和(6)。这特别适用于在如上提及的通式结构上的基团R。其他优选的改进空穴传输的基团例如是N(R1)、S或O,特别是N(R1),作为桥连基Y或富电子杂芳族基团,特别是噻吩、吡咯或呋喃作为基团R或R1。该化合物优选用于空穴传输层、或空穴注入层、或电子阻挡层或激子阻挡层。对于本发明的目的,空穴注入层是与阳极直接邻接的层。对于本发明的目的,空穴传输层是位于空穴注入层和发光层之间的层。对于本发明的目的,电子阻挡或激子阻挡层是与在阳极侧上的发光层直接邻接的层。如果通式(1)的化合物用作空穴传输或空穴注入材料,对于它们,优选可掺杂有电子受体化合物,例如掺杂有F4-TCNQ,或掺杂有如EP 1476881或EP 1596445中描述的化合物。
在本发明的又一其他实施方式中,通式(1)的化合物在电子传输层或空穴阻挡层中用作电子传输材料或空穴阻挡材料。此处优选基团Y代表C=O、P(=O)、SO或SO2和/或,至少一个取代基R和/或R1代表杂芳基,所述的杂芳基表示缺电子杂环,例如咪唑、吡唑、噻唑、苯并咪唑、苯并噻唑、三唑、噁二唑、苯并噻二唑、菲咯啉等,或C(=O)Ar、P(=O)Ar2、S(=O)Ar或S(O)2Ar。此外优选该化合物用电子供体化合物掺杂。对于本发明的目的,空穴阻挡层是在发光层和电子传输层之间并与发光层直接邻接的层。如果通式⑴的化合物用作电子传输材料,则可优选它与其他化合物作为混合物使用。优选的混合物成分是碱金属化合物,优选锂化合物,特别优选Liq(8-羟基喹啉锂)或Liq衍生物。
通式(1)的重复单元同样能够在聚合物中或者用作聚合物骨架、用作空穴传输单元和/或用作电子传输单元。此处优选的取代方式对应于上面描述的那些。
还优选有机电致发光器件,其特征在于通过升华方法施加一个或多个层,其中在真空升华设备中,在低于10-5毫巴、优选低于10-6毫巴的压力下气相沉积所述的材料。然而,应当指出压力也可以甚至更低,例如低于10-7毫巴。
同样优选有机电致发光器件,其特征在于通过OVPD(有机气相沉积)方法或者借助于载气升华施加一个或多个层,其中,在10-5毫巴-1巴之间的压力下施加所述材料。该方法中的具体情况是OVJP(有机蒸气喷印)方法,其中通过喷嘴直接施加材料,并因此结构化(例如M.S.Arnold等,Appl.Phys.Lett.(应用物理快报)2008,92,053301)。
还优选如下的有机电致发光器件,其特征在于从溶液中产生一个或多个层,比如通过旋涂,或者通过任何希望的印刷方法,比如丝网印刷,柔性版印刷或者平版印刷,但是特别优选LITI(光引发热成像,热转移印刷)或者喷墨印刷。对于该目的需要可溶性化合物。通过适当取代所述化合物能够实现高溶解度。此处,不仅可施加单一物料的溶液,而且可施加包括多种化合物例如基质材料和掺杂物的溶液。
当用于有机电致发光器件中时,相对于现有技术本发明的化合物具有以下意想不到的优点:
1.本发明的化合物具有高的热稳定性,并且能够在不分解的情况下升华。
2.本发明的化合物,特别是那些包含二芳氨基取代基作为基团R的化合物,当用于磷光电致发光器件中的电子/激子阻挡层中时,与现有技术的材料相比较产生相当大的效率提高。
3.本发明的化合物,特别是被二芳氨基取代和/或包含单键或S、O或N(R1)作为基团Y,和/或被富电子杂芳族基团取代的那些化合物,非常适于用作空穴注入和空穴传输材料,并导致工作电压降低。
4.利用本发明化合物制造的OLED通常具有非常长的寿命。
5.利用本发明化合物制造的OLED通常具有非常高的量子效率。
本申请文本涉及本发明化合物在OLED和PLED和相应显示器中的用途。尽管受说明书的限制,但本领域普通技术人员可以在不需要其他创造性劳动的情况下,还将本发明化合物用于其它的电子器件,例如用于有机场效应晶体管(O-FET)、有机薄膜晶体管(O-TFT)、有机发光晶体管(O-LET)、有机集成电路(O-IC)、有机太阳能电池(O-C)、有机场猝灭器件(O-FQD)、发光电化学电池(LEC)、有机激光二极管(O-laser)、或有机光感受器。
本发明同样涉及本发明的化合物在相应的器件中的用途和这些器件本身。
通过以下实施例更加详细地描述本发明,但不希望局限于此。本领域普通技术人员在不需要创造性劳动的情况下,将能制备本发明其他的化合物,并在有机电子器件中使用它们。
实施例:
除非另外指出,以下合成在干燥溶剂中保护气体气氛下进行。溶剂和试剂购买自ALDRICH或ABCR。如在Eur.J.Org.Chem.2006,2523-2529中描述的制备前体3,3',5,5'-四溴二苯甲酮。
实施例1:合成9,9-双(3,5-二溴苯基)芴
从144.5g(620mmol)的2-溴联苯和15.3g(580mmol)的镁在500ml四氢呋喃和250ml的乙二醇二甲醚混合物中制备相应的格氏化合物。然后在室温下加入224.0g(450mmol)的双(3,5-二溴苯基)酮在1000ml四氢呋喃中的悬浮液,该混合物另外搅拌十二小时。在真空中除去溶剂,1000ml的冰醋酸和5ml的溴化氢加入到残余物中,该混合物搅拌一小时。悬浮液在回流下加热半小时,在室温下搅拌12小时。用抽吸过滤去固体,用300ml的乙醇洗涤三次,并从甲苯中重结晶两次。得率:183.2g(289mmol),64.3%,纯度约99.8%(高压液相色谱法)。
类似实施例1,从相应的溴化物(实施例2和3)得到本发明的以下化合物:
实施例4:合成9,9-双(3,5-二苯基苯基)芴
1.0g(3.3mmol)的三邻甲苯基膦和0.5g(2.2mmol)的乙酸钯(II)加入到充分搅拌的30.4g(48mmol)的9,9-双(3,5-二溴苯基)芴、35.4g(290mmol)苯基硼酸和121.0g(570mmol)磷酸三钾在300ml甲苯、300ml的1,4-二氧六环和300ml水的混合物的悬浮液中,该混合物随后在回流下加热3小时。冷却之后,分离去有机相,每一次用150ml水洗涤三次,通过硅胶过滤。在真空中除去溶剂,残余物溶解在200ml的乙醇中,利用抽吸滤出,用100ml的乙醇洗涤三次。从氯苯中重结晶三次固体,干燥之后,在真空中升华两次(p=1×10-5毫巴、T=320℃)。得率:
11.1g(18mmol),37.1%,纯度约99.9%(高压液相色谱法)。
类似实施例4,从相应的硼酸(实施例5-7)得到本发明的以下化合物:
实施例8:合成9,9-双(3,5-二苯基氨基苯基)芴
101mg(0.50mmol)的三叔丁基膦和56mg(0.25mmol)的乙酸钯(II)加入到充分搅拌的25.4g(40mmol)的9,9-双(3,5-二溴苯基)芴、33.8g(200mmol)的二苯胺和21.1g(220mmol)的[缺项]在500ml甲苯的悬浮液中,该混合物在回流下加热5小时。冷却之后,通过硅胶过滤溶液,随后在真空中蒸发至干。残余物在60℃下在乙醇和水的1:1的600ml混合物中搅拌1小时,用抽吸滤出,用250ml的乙醇洗涤五次,在真空中干燥。米色固体从二甲基甲酰胺中重结晶五次及从氯苯中重结晶三次,在真空中干燥,随后升华两次(p=1×10-5毫巴、T=350℃)。得率:10.2g(10mmol),25.0%,纯度99.9%(高压液相色谱法),Tg=99.8℃。
类似实施例8,从相应的胺和相应的芴(实施例9-13)得到本发明的以下化合物:
实施例14:合成9,9-双(3,5-二咔唑-N-基)芴
50.7g(80mmol)的9,9-双(3,5-二溴苯基)芴、78.6g(470mmol)的咔唑和201.7g(950mmol)的磷酸三钾的悬浮液,在1000ml的对二甲苯中用500g的玻璃珠剧烈地搅拌。1.62g(8.0mmol)的三叔丁基膦和894mg(4.0mmol)的乙酸钯(II)加入到悬浮液中,然后在回流下加热5天。冷却之后,加入1000ml的水,搅拌混合物12小时,然后过滤。分离出有机相,用200ml水洗涤三次,随后在真空中蒸发得到粘性油。在用300ml乙醇搅拌时,形成结晶固体,其用抽吸滤出,用250ml的乙醇洗涤三次。逐滴地将固体在350ml二甲基甲酰胺中的溶液加入到1500ml的沸腾的乙醇中。冷却之后,用抽吸滤出固体,从氯苯中重结晶三次,在真空中干燥,然后在真空中升华两次(p=1x 10-5毫巴,T=370℃)。得率:33.2g(34mmol),42.4%,纯度99.8%(高压液相色谱法)。
类似实施例14,从相应的咔唑衍生物(实施例15-16)得到本发明的以下化合物:
实施例17:合成9,9-双((3,5-双苯甲酰基)苯基)芴
67.5ml的正丁基锂(在己烷中2.5M)逐滴地加入到冷却到-78℃、25.4g(40mmol)的9,9-双(3,5-二溴苯基)芴在1000ml四氢呋喃的溶液中,该混合物随后在-78℃下搅拌30分钟。然后迅速地加入18.6g(180mmol)的苄腈和50ml四氢呋喃的混合物,该混合物在-78℃下搅拌另外1h,然后放置温热到室温,加入100ml的5N盐酸,该混合物在回流下煮沸5小时。冷却之后,在真空中在旋转蒸发器中除去四氢呋喃,残余物溶解在500ml的二氯甲烷中,用水和饱和的碳酸氢钠溶液洗涤直到中性,用硫酸镁干燥,然后通过含有硅胶的短柱滤出。在真空下在旋转蒸发器中将溶剂蒸发到约50ml,加入300ml的甲醇,利用抽吸滤出沉淀的固体,用100ml的甲醇洗涤一次。干燥之后,从二甲基甲酰胺中重结晶五次米色固体,在真空中干燥,随后升华两次(p=1x 10-5毫巴,T=360℃)。得率:14.3g(19mmol),48.6%,纯度99.9%(高压液相色谱法)。
类似实施例17,从相应的腈(实施例18和19)得到本发明的以下化合物:
实施例20:合成9,9-双((3,5-双联苯基膦基)苯基)芴
67.5ml的正丁基锂(在己烷中2.5M)逐滴地加入到冷却到-78℃、25.4g(40mmol)的9,9-双(3,5-二溴苯基)芴在1000ml四氢呋喃的溶液中,该混合物随后在-78℃下搅拌30分钟。然后迅速地加入39.7g(180mmol)的氯代联苯基膦和50ml四氢呋喃的混合物,该混合物在-78℃下搅拌另外1h,然后放置温热到室温,在真空下在旋转蒸发器中完全除去四氢呋喃,残余物溶解在500ml的乙酸乙酯中,在强烈搅拌下逐滴地加入150ml 10%的过氧化氢,混合物搅拌另外16h,分离出水相,在真空下在旋转蒸发器中将溶剂蒸发到约50ml,加入300ml的甲醇,用抽吸滤出沉淀的固体,用100ml的甲醇洗涤一次。干燥之后,从氯苯中重结晶五次米色固体,在真空中干燥,随后升华两次(p=1x 10-5毫巴,T=390℃)。得率:12.0g(11mmol),26.8%,纯度99.9%(高压液相色谱法)。
类似实施例20,从相应的氯膦(实施例21)得到本发明的以下化合物:
实施例22:合成9,9-双((3,5-双-N-苯基苯并咪唑-2-基)苯基)芴
a)9,9-双(3,5-二氰基苯基)芴
63.4g(100mmol)的9,9-双(3,5-二溴苯基)芴、58.7g(500mmol)的氰化锌、3.3g(50mmol)的锌和11.6g(10mmol)的四(三苯基膦)钯(0)在1000ml二甲基乙酰胺中的悬浮液在140℃下搅拌60小时。冷却之后,加入1000ml的浓氨溶液,混合物搅拌另外1h,用抽吸滤出,用500ml的水洗涤固体,用100ml的乙醇洗涤三次,在真空下干燥。得率:39.8g(95mmol),95.1%,根据1H-NMR测定的纯度98%。
b)9,9-双(3,5-二羧基苯基)芴
39.8g(95mmol)的9,9-双(3,5-二氰基苯基)芴在40g氢氧化钠的300ml乙醇和100ml水的混合物的溶液中的悬浮液,在回流下加热,直到形成清液(约10h)。冷却之后,通过添加5N盐酸调整pH至1。利用抽吸滤出沉淀的固体,用水洗涤直到流出母液的pH=4-5,抽吸干燥,然后用甲苯共沸干燥。得率:44.5g(90mmol),94.8%,根据1H-NMR测定的纯度98%。
c)9,9-双((3,5-双-N-苯基苯并咪唑-2-基)苯基)芴
44.5g(90mmol)的9,9-双(3,5-二羧基苯基)芴悬浮在150ml亚硫酰氯中,将一滴DMF加入到该悬浮液中,其随后在60℃下温热直到完成气体的放出。然后在真空下除去过量的亚硫酰氯,残余物溶解在500ml的二氯甲烷中,随后逐滴地加入66.3g(360mmol)的N-苯基-邻苯二胺在200ml二氯甲烷和150ml三乙胺混合物中的溶液。当放热反应减弱时,在室温下搅拌混合物另外16小时。用500ml的1N NaOH洗涤反应混合物,然后用500ml水洗涤两次,用硫酸镁干燥,然后用二氯甲烷在氧化铝(碱性的,活性等级1)上进行色谱分离。最后,产品从氯苯中重结晶三次,在真空下干燥,然后升华两次(p=1x 10-5毫巴,T=410℃)。得率:33.8g(31mmol),31.0%,纯度99.9%(HPLC)。
实施例23:合成9,9-双(4,6-二苯基三嗪-2-基)芴
将7.2g(300mmol)的氢化钠加入到16.6g(100mmol)芴在500ml四氢呋喃的溶液中。在加入0.5ml的二异丙基胺之后,该混合物在室温下搅拌1h,随后逐滴地加入58.9g(220mmol)的2-氯代-4,6-联苯基-1,3,5-三嗪的溶液,该混合物然后在50℃下搅拌16小时。冷却之后,通过添加5ml水骤冷混合物,在真空下脱去四氢呋喃,残余物溶解在二氯甲烷中,用水洗涤有机相,然后用硫酸镁干燥。在除去二氯甲烷之后,残余物从DMF中重结晶四次,在真空下干燥,然后升华两次(p=1x 10-5毫巴,T=340℃)。得率:17.0g(27mmol),27.0%,纯度99.9%(HPLC)。
实施例24:合成10-苯基-12,12-双[1,1';3,1”]三联苯-5'-基-10,12-二氢-10-氮杂茚并[2,1-b]芴
a)3-(2-溴苯基)-N-苯基咔唑
1.1g(1mmol)的四(三苯基膦)钯(0)加入到28.7g(100mmol)的N-苯基咔唑-3-硼酸、36.1ml(300mmol)的1,2-二溴苯在150ml的二氧六环、100ml的2-乙氧基乙醇和250ml的2N碳酸钠溶液的混合物中,该混合物在回流下加热16小时。冷却之后,分离出有机相,加入500ml的甲苯,用500ml水洗涤三次混合物,用硫酸镁干燥,通过硅胶过滤,然后在真空下除去甲苯和过量的1,2-二溴苯。用热乙醇通过搅拌洗涤残余物三次。得率:26.7g(67mmol),67.1%,根据1H-NMR测定的纯度97%。
b)12,12-双(3,5-二溴苯基)-10-苯基-10,12-二氢-10-氮杂-茚并[2,1-b]芴
将24.0ml(60mmol)的正丁基锂(在己烷中2.5N)逐滴地加入到冷却到-78℃、23.9g(60mmol)3-(2-溴苯基)-N-苯基咔唑在500ml四氢呋喃中的溶液中,该混合物随后在-78℃下搅拌另外30分钟,然后逐滴地加入38.0g(60mmol)的9,9-双-(3,5-二溴苯基)芴在100ml四氢呋喃中的溶液。当加入完成时,混合物放置温热到室温,在真空下除去四氢呋喃,残余物溶解在500ml的冰醋酸中,加入5ml的溴化氢,该悬浮液在回流下加热半小时。冷却之后,用抽吸滤出固体,用300ml的乙醇洗涤三次,从甲苯/乙醇中重结晶一次。得率:36.2g(45mmol),75.3%,纯度约97%(HPLC)。
c)10-苯基-12,12-双[1,1';3,1”]三联苯-5'-基-10,12-二氢-10-氮杂-茚并[2,1-b]芴
制备类似于实施例4。代替30.4g(48mmol)的9,9-双(3,5-二溴苯基)芴,使用36.0g(45mmol)的12,12-双(3,5-二溴苯基)-10-苯基-10,12-二氢-10-氮杂茚并[2,1-b]芴。固体从NMP中重结晶三次,干燥之后,在真空下升华两次(p=1x 10-5毫巴,T=400℃)。得率:15.0g(19mmol),42.3%,纯度约99.9%(HPLC)。
实施例25:制造和表征包括本发明化合物的有机电致发光器件
本发明的电致发光器件可如例如WO 05/003253中所述制造。此处比较各种各样的OLED的结果。为了更好的可比较性,基本结构、使用的材料、掺杂程度和它们的层厚度是相同的。第一器件实施例描述了现有技术的比较标准,其中发光层由主体材料双(9,9'-螺二芴-2-基)酮和客体材料(掺杂物)Ir(ppy)3组成。此外,描述了各种各样设计的OLED,其中在每一情况下客体材料(掺杂物)是Ir(ppy)3。类似如上提及的一般的方法,制造具有以下结构的OLED:
为了清楚起见,以下描述了Ir(ppy)3、螺-酮(SK)和胺1的结构。此处的胺1是根据最接近现有技术的比较化合物(JP 2005/085599):
以下描述本发明的化合物1-7:
这些仍未优化的OLED通过标准方法表征;为此目的,确定电致发光光谱、作为亮度函数的、由电流-电压-亮度特性线(IUL特性线)计算的效率(以cd/A测定)和寿命。
对于根据上面描述的结构和材料制造的OLED,其中所述材料作为比较试验,用NPB作为空穴传输材料,在上面描述的条件下,通常得到的最大效率为约30cd/A,CIE的彩色坐标:x=0.38,y=0.57。对于1000cd/m2的参照发光密度,需要4.4V的电压。在1000cd/m2的初始发光密度下寿命是约7700h。(见表1,实施例26)。对于在胺1作为空穴传输材料,其他方面相同的器件结构(见表1,实施例27),在41cd/A区域得到更好的最大效率,但是对于1000cd/m2的参照发光密度需要5.3V的电压,寿命仅为约5600小时。
相比之下,使用本发明的电子阻挡材料(化合物1)制造的本发明的OLED,呈现显著增加的47cd/A的最大效率,CIE彩色坐标:x=0.38,y=0.58,其中对于1000cd/m2的参照发光密度,需要的电压是4.4V(见表1,实施例28)。与比较例26相比较,在1000cd/m2的初始发光密度下的寿命为7400h(见表1,实施例28)。
与比较试验相比,使用主体材料(化合物2)代替螺-酮制造的其他方面结构相同的本发明的OLED,呈现35cd/A的最大效率,改进的CIE彩色坐标:x=0.31,y=0.62,其中对于1000cd/m2的参照发光密度需要的电压是5.2V(见表1,实施例29)。在1000cd/m2的初始发光密度下6900h的寿命与当使用螺-酮时的寿命是可比的(见表1,实施例29)。
如果化合物1用作电子阻挡材料和化合物3用作电子传输材料代替Alq,则得到54cd/A的最大效率,CIE彩色坐标:x=0.37,y=0.59,其中对于1000cd/m2的参照发光密度需要的电压是4.1V(见表1,实施例30)。在1000cd/m2的初始发光密度下7200h的寿命与参照材料Alq的寿命是可比的,4.1V电压比参照材料Alq更低(见表1,实施例22)。
如果本发明的化合物4、5和7用作基质材料,则得到非常好的效率,同时得到良好的寿命。化合物6尤其适合作为电子导体,它在低压下给出良好的效率和寿命。
表1:对于本发明的化合物用Ir(ppy)3作为掺杂物的器件结果
Claims (14)
1.通式(2)或(3)的化合物
其中以下适用于使用的符号和标记:
Y是单键;
R在每一次出现中相同或者不同地是C(=O)Ar、P(=O)Ar2或具有5-30个芳族环原子的芳族或杂芳族环体系,它们可被一个或多个非芳基R1取代;
Ar在每一次出现中相同或者不同地是具有5-30个芳族环原子的芳族或杂芳族环体系,它们可被一个或多个非芳基R1取代;
R1在每一次出现中相同或者不同地是H、F、具有1-6个碳原子的直链烷基或具有3-6个碳原子的支链或环状的烷基,它们每个可被一个或多个基团R2取代,其中一个或多个H原子可被F替代,或具有5-14个芳族环原子的芳族或杂芳族环体系,在每一情况下它们可以被一个或多个基团R2取代;
R2在每一次出现中相同或者不同地是H、D或具有1-20个碳原子的脂肪族、芳族和/或杂芳族烃基,其中,另外,H原子可被F替代;
n是2;
本发明不包括以下化合物:
2.通式(4a)或(4b)的根据权利要求1所述的化合物:
其中使用的符号具有在权利要求1中指出的含义。
3.根据权利要求1或2所述的化合物,其特征在于符号R在每一次出现中相同或者不同地代表C(=O)Ar或P(=O)Ar2。
4.根据权利要求1或2所述的化合物,其特征在于符号R在每一次出现中相同或者不同地代表具有5-30个芳族环原子的芳族或杂芳族环体系,它们可被一个或多个非芳基R1取代。
5.根据权利要求1或2所述的化合物,其特征在于如果R基代表芳族或杂芳族环体系,则它选自苯基、1-萘基、2-萘基、蒽基、苯基蒽基、1-或2-萘基蒽基、联萘基、芘基、荧蒽基、2-,3-,4-,5-,6-或7-苯并蒽基、N-苯并咪唑基、苯基-N-苯并咪唑基、N-苯基苯并咪唑基、或苯基-N-苯基苯并咪唑基。
6.根据权利要求1所述的化合物,其特征在于R1是H。
7.根据权利要求1所述的化合物,其特征在于如果R代表芳族或杂芳族环体系,则它选自苯基、1-萘基、2-萘基、蒽基、苯基蒽基、1-或2-萘基蒽基、联萘基、芘基、荧蒽基、2-,3-,4-,5-,6-或7-苯并蒽基、N-苯并咪唑基、苯基-N-苯并咪唑基、N-苯基苯并咪唑基、或苯基-N-苯基苯并咪唑基;并且R1是H。
8.制备根据权利要求1-7中任一项所述的化合物的方法,包括使双(3,5-二溴)二苯甲酮与取代或未取代的2-联苯基锂、2-锂二苯基醚、2-锂二苯基硫醚、2-(2-苯基锂)-2-苯基-1,3-二氧戊环、2-苯基锂二苯基胺或相应的格氏化合物反应,得到三芳基甲醇,随后在酸性条件下环化。
9.混合物,包括权利要求1-7中任一项所述的至少一种化合物和至少一种其他化合物。
10.溶液,包括权利要求1-7中任一项所述的至少一种化合物和至少一种有机溶剂。
11.权利要求1-7中任一项所述的化合物在电子器件中的用途。
12.一种包括权利要求1-7中任一项所述的至少一种化合物的电子器件。
13.根据权利要求12所述的电子器件,其特征在于所述电子器件选自有机电致发光器件(OLED、PLED)、有机场效应晶体管(O-FET)、有机薄膜晶体管(O-TFT)、有机发光晶体管(O-LET)、有机集成电路(O-IC)、有机太阳能电池(O-SC)、有机场猝灭器件(O-FQD)、发光电化学电池(LEC)、有机激光二极管(O-laser)或有机光感受器。
14.根据权利要求13所述的有机电致发光器件,其特征在于权利要求1-7中任一项所述的化合物用作荧光或磷光化合物的基质材料,用作空穴传输材料,用作空穴注入材料,用作电子阻挡材料,用作激子阻挡材料,用作电子传输材料或用作空穴阻挡材料。
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- 2009-03-11 CN CN200980111846XA patent/CN101983190A/zh active Pending
- 2009-03-11 EP EP09730490A patent/EP2260023B1/de active Active
- 2009-03-11 CN CN201610236009.1A patent/CN105906546B/zh active Active
- 2009-03-11 US US12/936,644 patent/US8361638B2/en active Active
- 2009-03-11 KR KR1020107024955A patent/KR101578570B1/ko active IP Right Grant
- 2009-03-11 AT AT09730490T patent/ATE555092T1/de active
- 2009-03-11 CN CN201410490593.4A patent/CN104327003B/zh active Active
- 2009-03-11 WO PCT/EP2009/001736 patent/WO2009124627A1/de active Application Filing
- 2009-04-02 TW TW098111009A patent/TW201004904A/zh unknown
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Also Published As
Publication number | Publication date |
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CN101983190A (zh) | 2011-03-02 |
EP2260023B1 (de) | 2012-04-25 |
CN104327003B (zh) | 2017-10-24 |
ATE555092T1 (de) | 2012-05-15 |
JP5653902B2 (ja) | 2015-01-14 |
WO2009124627A1 (de) | 2009-10-15 |
DE102008017591A1 (de) | 2009-10-08 |
EP2260023A1 (de) | 2010-12-15 |
TW201004904A (en) | 2010-02-01 |
US8361638B2 (en) | 2013-01-29 |
JP2011521894A (ja) | 2011-07-28 |
KR20100133467A (ko) | 2010-12-21 |
CN105906546A (zh) | 2016-08-31 |
US20110037027A1 (en) | 2011-02-17 |
KR101578570B1 (ko) | 2015-12-28 |
CN104327003A (zh) | 2015-02-04 |
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