CN101248156A - 用于有机电致发光器件的新材料 - Google Patents
用于有机电致发光器件的新材料 Download PDFInfo
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- CN101248156A CN101248156A CNA2006800309818A CN200680030981A CN101248156A CN 101248156 A CN101248156 A CN 101248156A CN A2006800309818 A CNA2006800309818 A CN A2006800309818A CN 200680030981 A CN200680030981 A CN 200680030981A CN 101248156 A CN101248156 A CN 101248156A
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- 239000000463 material Substances 0.000 title claims abstract description 53
- 150000001875 compounds Chemical class 0.000 claims abstract description 97
- 239000002019 doping agent Substances 0.000 claims abstract description 13
- 125000003118 aryl group Chemical group 0.000 claims description 64
- 125000001072 heteroaryl group Chemical group 0.000 claims description 40
- 229910052799 carbon Inorganic materials 0.000 claims description 22
- 125000004432 carbon atom Chemical group C* 0.000 claims description 20
- 239000000203 mixture Substances 0.000 claims description 19
- 229910052760 oxygen Inorganic materials 0.000 claims description 19
- 239000000758 substrate Substances 0.000 claims description 17
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 14
- 238000005401 electroluminescence Methods 0.000 claims description 14
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 13
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 12
- 229920000642 polymer Polymers 0.000 claims description 11
- 229910052717 sulfur Inorganic materials 0.000 claims description 11
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 10
- 238000002347 injection Methods 0.000 claims description 10
- 239000007924 injection Substances 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 229910052794 bromium Inorganic materials 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 150000003254 radicals Chemical class 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 7
- 125000001424 substituent group Chemical group 0.000 claims description 7
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims description 6
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 6
- 230000005540 biological transmission Effects 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 125000001624 naphthyl group Chemical group 0.000 claims description 6
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims description 6
- 229930192474 thiophene Natural products 0.000 claims description 6
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 150000002576 ketones Chemical class 0.000 claims description 5
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 229910052740 iodine Inorganic materials 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 4
- 125000005309 thioalkoxy group Chemical group 0.000 claims description 4
- 125000005259 triarylamine group Chemical group 0.000 claims description 4
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-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
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 3
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 claims description 3
- 239000012964 benzotriazole Substances 0.000 claims description 3
- 230000021615 conjugation Effects 0.000 claims description 3
- XXPBFNVKTVJZKF-UHFFFAOYSA-N dihydrophenanthrene Natural products C1=CC=C2CCC3=CC=CC=C3C2=C1 XXPBFNVKTVJZKF-UHFFFAOYSA-N 0.000 claims description 3
- OBISXEJSEGNNKL-UHFFFAOYSA-N dinitrogen-n-sulfide Chemical compound [N-]=[N+]=S OBISXEJSEGNNKL-UHFFFAOYSA-N 0.000 claims description 3
- 150000002475 indoles Chemical class 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 3
- 230000027756 respiratory electron transport chain Effects 0.000 claims description 3
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 230000005669 field effect Effects 0.000 claims description 2
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 2
- 230000010354 integration Effects 0.000 claims description 2
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims description 2
- 238000010791 quenching Methods 0.000 claims description 2
- 230000000171 quenching effect Effects 0.000 claims description 2
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 230000005525 hole transport Effects 0.000 abstract description 2
- 239000010410 layer Substances 0.000 description 43
- -1 aryl pyrene Chemical compound 0.000 description 29
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 22
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 14
- 238000010586 diagram Methods 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 150000001412 amines Chemical class 0.000 description 11
- BBEAQIROQSPTKN-UHFFFAOYSA-N antipyrene Natural products C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 11
- 125000004122 cyclic group Chemical group 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 150000001454 anthracenes Chemical class 0.000 description 8
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 8
- JQQSUOJIMKJQHS-UHFFFAOYSA-N pentaphene Chemical compound C1=CC=C2C=C3C4=CC5=CC=CC=C5C=C4C=CC3=CC2=C1 JQQSUOJIMKJQHS-UHFFFAOYSA-N 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 230000031709 bromination Effects 0.000 description 7
- 238000005893 bromination reaction Methods 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 230000008030 elimination Effects 0.000 description 7
- 238000003379 elimination reaction Methods 0.000 description 7
- 125000005842 heteroatom Chemical group 0.000 description 7
- 150000002790 naphthalenes Chemical class 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 125000005504 styryl group Chemical group 0.000 description 6
- 239000011159 matrix material Substances 0.000 description 5
- AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 230000007704 transition Effects 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 125000005605 benzo group Chemical group 0.000 description 4
- 239000003205 fragrance Substances 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 230000002194 synthesizing effect Effects 0.000 description 4
- 229920002554 vinyl polymer Polymers 0.000 description 4
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 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
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000004305 biphenyl Substances 0.000 description 3
- 235000010290 biphenyl Nutrition 0.000 description 3
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 150000004696 coordination complex Chemical class 0.000 description 3
- 238000000151 deposition Methods 0.000 description 3
- 230000008021 deposition Effects 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 238000003786 synthesis reaction 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
- KEQFAIKLHXZWIW-UHFFFAOYSA-N 1,2,2-triphenylethenamine Chemical compound C=1C=CC=CC=1C(N)=C(C=1C=CC=CC=1)C1=CC=CC=C1 KEQFAIKLHXZWIW-UHFFFAOYSA-N 0.000 description 2
- OVFJHQBWUUTRFT-UHFFFAOYSA-N 1,2,3,4-tetrahydrotetrazine Chemical compound C1=CNNNN1 OVFJHQBWUUTRFT-UHFFFAOYSA-N 0.000 description 2
- UHXOHPVVEHBKKT-UHFFFAOYSA-N 1-(2,2-diphenylethenyl)-4-[4-(2,2-diphenylethenyl)phenyl]benzene Chemical compound C=1C=C(C=2C=CC(C=C(C=3C=CC=CC=3)C=3C=CC=CC=3)=CC=2)C=CC=1C=C(C=1C=CC=CC=1)C1=CC=CC=C1 UHXOHPVVEHBKKT-UHFFFAOYSA-N 0.000 description 2
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-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
- VEUMBMHMMCOFAG-UHFFFAOYSA-N 2,3-dihydrooxadiazole Chemical compound N1NC=CO1 VEUMBMHMMCOFAG-UHFFFAOYSA-N 0.000 description 2
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 2
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- 238000006443 Buchwald-Hartwig cross coupling reaction Methods 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
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- PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 description 2
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- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 2
- 238000007171 acid catalysis Methods 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 239000004327 boric acid Substances 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- WDECIBYCCFPHNR-UHFFFAOYSA-N chrysene Chemical compound C1=CC=CC2=CC=C3C4=CC=CC=C4C=CC3=C21 WDECIBYCCFPHNR-UHFFFAOYSA-N 0.000 description 2
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- SKOWZLGOFVSKLB-UHFFFAOYSA-N hypodiboric acid Chemical compound OB(O)B(O)O SKOWZLGOFVSKLB-UHFFFAOYSA-N 0.000 description 2
- 150000002460 imidazoles Chemical class 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 229910052741 iridium Inorganic materials 0.000 description 2
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 2
- 238000004020 luminiscence type Methods 0.000 description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 2
- 238000005457 optimization Methods 0.000 description 2
- 238000007243 oxidative cyclization reaction Methods 0.000 description 2
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 2
- 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 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 238000007639 printing Methods 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000004065 semiconductor Substances 0.000 description 2
- 235000021286 stilbenes Nutrition 0.000 description 2
- 238000000859 sublimation Methods 0.000 description 2
- 230000008022 sublimation Effects 0.000 description 2
- 150000003462 sulfoxides Chemical class 0.000 description 2
- 150000003509 tertiary alcohols Chemical class 0.000 description 2
- JLZUZNKTTIRERF-UHFFFAOYSA-N tetraphenylethylene Chemical group C1=CC=CC=C1C(C=1C=CC=CC=1)=C(C=1C=CC=CC=1)C1=CC=CC=C1 JLZUZNKTTIRERF-UHFFFAOYSA-N 0.000 description 2
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 2
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
- FIDRAVVQGKNYQK-UHFFFAOYSA-N 1,2,3,4-tetrahydrotriazine Chemical compound C1NNNC=C1 FIDRAVVQGKNYQK-UHFFFAOYSA-N 0.000 description 1
- UUSUFQUCLACDTA-UHFFFAOYSA-N 1,2-dihydropyrene Chemical compound C1=CC=C2C=CC3=CCCC4=CC=C1C2=C43 UUSUFQUCLACDTA-UHFFFAOYSA-N 0.000 description 1
- RJXNZBKNKLNXLX-UHFFFAOYSA-N 1,2-oxazole;1,3-oxazole Chemical compound C=1C=NOC=1.C1=COC=N1 RJXNZBKNKLNXLX-UHFFFAOYSA-N 0.000 description 1
- 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 1
- VOIVTTPPKHORBL-UHFFFAOYSA-N 1-naphthalen-1-ylanthracene Chemical compound C1=CC=C2C(C=3C4=CC5=CC=CC=C5C=C4C=CC=3)=CC=CC2=C1 VOIVTTPPKHORBL-UHFFFAOYSA-N 0.000 description 1
- KMQPLEYEXDZOJF-UHFFFAOYSA-N 1-naphthalen-2-ylanthracene Chemical class C1=CC=C2C=C3C(C4=CC5=CC=CC=C5C=C4)=CC=CC3=CC2=C1 KMQPLEYEXDZOJF-UHFFFAOYSA-N 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 description 1
- KIIGEOHDCOLSHI-UHFFFAOYSA-N 1h-imidazole;naphthalene Chemical class C1=CNC=N1.C1=CC=CC2=CC=CC=C21 KIIGEOHDCOLSHI-UHFFFAOYSA-N 0.000 description 1
- JUUZQMUWOVDZSD-UHFFFAOYSA-N 1h-imidazole;pyrazine Chemical class C1=CNC=N1.C1=CN=CC=N1 JUUZQMUWOVDZSD-UHFFFAOYSA-N 0.000 description 1
- SBPIDKODQVLBGV-UHFFFAOYSA-N 1h-imidazole;pyridine Chemical class C1=CNC=N1.C1=CC=NC=C1 SBPIDKODQVLBGV-UHFFFAOYSA-N 0.000 description 1
- IGHOZKDBCCFNNC-UHFFFAOYSA-N 1h-imidazole;quinoxaline Chemical class C1=CNC=N1.N1=CC=NC2=CC=CC=C21 IGHOZKDBCCFNNC-UHFFFAOYSA-N 0.000 description 1
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
- PFRPMHBYYJIARU-UHFFFAOYSA-N 2,3-diazatetracyclo[6.6.2.04,16.011,15]hexadeca-1(14),2,4,6,8(16),9,11(15),12-octaene Chemical compound C1=CC=C2N=NC3=CC=CC4=CC=C1C2=C43 PFRPMHBYYJIARU-UHFFFAOYSA-N 0.000 description 1
- SNTWKPAKVQFCCF-UHFFFAOYSA-N 2,3-dihydro-1h-triazole Chemical compound N1NC=CN1 SNTWKPAKVQFCCF-UHFFFAOYSA-N 0.000 description 1
- UPUWMQZUXFAUCJ-UHFFFAOYSA-N 2,5-dihydro-1,2-thiazole Chemical compound C1SNC=C1 UPUWMQZUXFAUCJ-UHFFFAOYSA-N 0.000 description 1
- SYOANZBNGDEJFH-UHFFFAOYSA-N 2,5-dihydro-1h-triazole Chemical compound C1NNN=C1 SYOANZBNGDEJFH-UHFFFAOYSA-N 0.000 description 1
- RLFZYIUUQBHRNV-UHFFFAOYSA-N 2,5-dihydrooxadiazole Chemical compound C1ONN=C1 RLFZYIUUQBHRNV-UHFFFAOYSA-N 0.000 description 1
- UXGVMFHEKMGWMA-UHFFFAOYSA-N 2-benzofuran Chemical compound C1=CC=CC2=COC=C21 UXGVMFHEKMGWMA-UHFFFAOYSA-N 0.000 description 1
- LAXBNTIAOJWAOP-UHFFFAOYSA-N 2-chlorobiphenyl Chemical group ClC1=CC=CC=C1C1=CC=CC=C1 LAXBNTIAOJWAOP-UHFFFAOYSA-N 0.000 description 1
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
- VHMICKWLTGFITH-UHFFFAOYSA-N 2H-isoindole Chemical compound C1=CC=CC2=CNC=C21 VHMICKWLTGFITH-UHFFFAOYSA-N 0.000 description 1
- BJGKVCKGUBYULR-UHFFFAOYSA-N 3-bromo-2-methylbenzoic acid Chemical compound CC1=C(Br)C=CC=C1C(O)=O BJGKVCKGUBYULR-UHFFFAOYSA-N 0.000 description 1
- NVHCZCHIPIQMRT-UHFFFAOYSA-N 4,5-dihydroxy-6-oxo-1H-pyridine-2,3-dicarboxylic acid Chemical compound OC(=O)C=1NC(=O)C(O)=C(O)C=1C(O)=O NVHCZCHIPIQMRT-UHFFFAOYSA-N 0.000 description 1
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- 101000801643 Homo sapiens Retinal-specific phospholipid-transporting ATPase ABCA4 Proteins 0.000 description 1
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- 241001597008 Nomeidae Species 0.000 description 1
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- 102100033617 Retinal-specific phospholipid-transporting ATPase ABCA4 Human genes 0.000 description 1
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- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- REDXJYDRNCIFBQ-UHFFFAOYSA-N aluminium(3+) Chemical compound [Al+3] REDXJYDRNCIFBQ-UHFFFAOYSA-N 0.000 description 1
- DNEHKUCSURWDGO-UHFFFAOYSA-N aluminum sodium Chemical compound [Na].[Al] DNEHKUCSURWDGO-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
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- 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 description 1
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- 239000002800 charge carrier Substances 0.000 description 1
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- WCZVZNOTHYJIEI-UHFFFAOYSA-N cinnoline Chemical compound N1=NC=CC2=CC=CC=C21 WCZVZNOTHYJIEI-UHFFFAOYSA-N 0.000 description 1
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- 125000001162 cycloheptenyl group Chemical group C1(=CCCCCC1)* 0.000 description 1
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- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- HOBCFUWDNJPFHB-UHFFFAOYSA-N indolizine Chemical compound C1=CC=CN2C=CC=C21 HOBCFUWDNJPFHB-UHFFFAOYSA-N 0.000 description 1
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- 239000000178 monomer Substances 0.000 description 1
- FGGAOQTXQHKQOW-UHFFFAOYSA-N n,n-diphenylnaphthalen-1-amine Chemical compound C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=CC=C1 FGGAOQTXQHKQOW-UHFFFAOYSA-N 0.000 description 1
- 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
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- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 1
- 125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 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
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N pentanoic acid group Chemical group C(CCCC)(=O)O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
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- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
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- CPNGPNLZQNNVQM-UHFFFAOYSA-N pteridine Chemical compound N1=CN=CC2=NC=CN=C21 CPNGPNLZQNNVQM-UHFFFAOYSA-N 0.000 description 1
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- 150000003220 pyrenes Chemical class 0.000 description 1
- 150000003233 pyrroles Chemical class 0.000 description 1
- OWECKHSCCDVJCN-UHFFFAOYSA-N quinazoline;quinoxaline Chemical compound N1=CN=CC2=CC=CC=C21.N1=CC=NC2=CC=CC=C21 OWECKHSCCDVJCN-UHFFFAOYSA-N 0.000 description 1
- GJAWHXHKYYXBSV-UHFFFAOYSA-N quinolinic acid Chemical compound OC(=O)C1=CC=CN=C1C(O)=O GJAWHXHKYYXBSV-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
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- 238000006722 reduction reaction Methods 0.000 description 1
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- 229910052702 rhenium Inorganic materials 0.000 description 1
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 description 1
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- 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
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 150000003413 spiro compounds Chemical class 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 238000005092 sublimation method Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 125000006836 terphenylene group Chemical group 0.000 description 1
- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 238000001931 thermography Methods 0.000 description 1
- 238000010023 transfer printing Methods 0.000 description 1
- 125000005039 triarylmethyl group Chemical group 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 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 1
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 1
- 229910000404 tripotassium phosphate Inorganic materials 0.000 description 1
- 235000019798 tripotassium phosphate Nutrition 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
- 238000009834 vaporization Methods 0.000 description 1
- 238000001947 vapour-phase growth Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/26—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings condensed with carbocyclic rings or ring systems
- C07D237/30—Phthalazines
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
- C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
- C07C13/32—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings
- C07C13/62—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with more than three condensed rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
- C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
- C07C13/32—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings
- C07C13/72—Spiro hydrocarbons
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
- C07C17/10—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms
- C07C17/12—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms in the ring of aromatic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
- C07C211/61—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton with at least one of the condensed ring systems formed by three or more rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C25/00—Compounds containing at least one halogen atom bound to a six-membered aromatic ring
- C07C25/18—Polycyclic aromatic halogenated hydrocarbons
- C07C25/22—Polycyclic aromatic halogenated hydrocarbons with condensed rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/14—Sulfones; Sulfoxides having sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
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Abstract
本发明涉及式(1)的化合物及其在有机电致发光器件中的使用。使用式(1)的化合物作为发射层中的基质材料或掺杂剂和/或作为空穴传输材料和/或作为电子传输材料。
Description
技术领域
背景技术
有机半导体被开发以用于在最广意义上可以归于电子工业的许多不同应用。例如在US4539507、US5151629、EP0676461和WO98/27136中描述了使用这些有机半导体作为功能材料的有机电致发光器件(OLED)的结构。但是这些器件仍然表现出相当多的问题,迫切需要改进。
1.操作寿命仍然短,特别是在蓝色发光的情况中,意味着目前商业上仅可以实现简单的应用。
2.使用的一些化合物不仅不易溶解在合成中提纯它们的普通有机溶剂中,而且使得在有机电子器件的生产中工厂的清洁更困难。
3.使用的一些在OLED中表现出良好性能的化合物没有充分高的玻璃化转变温度。
在荧光OLED中,依据现有技术使用各种稠合芳香族化合物,特别是蒽或芘衍生物,作为基质材料,尤其用于蓝色发光电致发光器件,例如9,10-双(2-萘基)蒽(US5935721)。WO03/095445和CN1362464描述了用于用在OLED中的9,10-双(1-萘基)蒽衍生物。另外的适合用作基质材料的蒽衍生物描述在WO01/076323、WO01/021729、WO04/013073、WO04/018588、WO03/087023或WO04/018587中。基于芳基取代的芘和屈(chrysene)的基质材料描述在WO04/016575中。对于高质量的应用需要改进可利用的基质材料。
在蓝色发光化合物的情况中,可以提及的现有技术是Idemitsu对一些芳基乙烯基胺的使用(例如WO04/013073、WO04/016575、WO04/018587)。其提供了具有暗蓝色发光的很长的寿命。但是,这些结果高度依赖于使用的基质材料,意味着所提供的寿命不能与绝对值相比较,而总是仅用于在优化系统中的使用。而且,这些化合物热不稳定,不能不分解地蒸发,因此对于OLED的生产需要高的技术复杂性,因而代表着显著的技术缺点。另外的缺点是这些化合物的发光颜色。尽管Idemitsu提供了暗蓝色发光(CIE y坐标在0.15~0.18范围中),但是依据现有技术在简单的器件中不能再现这些颜色坐标。相反,这里得到绿-蓝色发光。用这些化合物实际上可以生产何种蓝色发光不是显而易见的。对于高质量应用需要改进可利用的发光体,特别是关于器件和升华稳定性。
在磷光OLED中使用的基体材料常常是4,4’-双(N-咔唑基)联苯(CBP)。缺点尤其是用其生产的器件的寿命短和通常较高的操作电压,这导致低的功率效率。另外,CBP玻璃化转变温度不够高。而且,已经发现CBP不适合蓝色发光电致发光器件,其产生差的效率。另外,由于必须额外地使用空穴阻挡层和电子传输层,所以如果使用CBP作为基体材料,该器件的结构复杂。WO04/093207描述了基于螺二芴的酮化合物的改进的三重基体材料。但是,对于该文献描述的基体材料,最好,合成中需要有毒的无机氰化物,意味着这些材料的制备在生态上不可接受。该文献中描述的那些其它基体材料的玻璃化转变温度仍不满意。
有机电致发光器件中使用的电子传输化合物通常是AlQ3(三羟基喹啉酸铝)(US4539507)。这具有许多缺点:由于它在升华温度下部分分解,所以它不能没有残余物地被气相沉积,这代表主要问题,特别是用于生产工厂。另外的缺点是AlQ3的强吸湿性以及低的电子迁移率,导致较高的电压,从而较低的功率效率。为了在显示器中防止短路,需要增加层厚度;用AlQ3这是不可能的,这是由于低的电荷载体迁移率和得到的电压增加。而且,AlQ3的内在颜色(固体中的黄色),精确地说在蓝色OLED的情况中由于重复吸收和弱的重复发光而会导致颜色偏移,证实非常不利。这里仅可以生产蓝色OLED,效率损失和颜色位置损害相当大。尽管存在所述缺点,目前AlQ3仍然代表对OLED中电子传输材料的多种要求的最好折衷。
因此,仍需要改进的材料,特别是用于蓝色荧光发光体的基质材料和用于三重发光体的基质材料,而且对于发光体,在有机电子器件中导致良好的效率和同时长的寿命的空穴传输材料和电子传输材料在器件的生产和操作中给出可重复的结果并容易合成。
发明内容
令人吃惊地,已经发现,与现有技术相比,含有下述的新结构单元的化合物具有显著的改进。使用这些材料,与根据现有技术的材料相比,可以增加有机电子器件的效率和寿命。而且,由于这些材料具有高的玻璃化转变温度,所以它们非常适合用在有机电子器件中。因此,本发明涉及这些材料和它们在有机电子器件中的应用。
本发明涉及式(1)的化合物
其中下列说明适用使用的符号和标记:
Y在每种情况中相同地或不同地是CR1或N;或(Y-Y)或(Y=Y)(即两个相邻的Y)代表NR1、S或O;前提条件是各环是五元环或六元环;
Z如果桥X键合到基团Z,Z等于C,如果没有桥X键合到基团Z,Z等于Y;
R1在每种情况中相同地或不同地是H、F、Cl、Br、I、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、具有1~40个碳原子的直链烷基、烷氧基或硫代烷氧基或具有3~40个碳原子的支链或环状烷基、烷氧基或硫代烷氧基,在每种情况中它们可以用一个或多个基团R2取代,其中一个或多个非相邻的CH2可以用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代替,且其中一个或多个H原子可以用F、Cl、Br、I、CN或NO2或每种情况中可以被一个或多个基团R2取代的具有5~40个芳环原子的芳环或杂芳环体系、或可以被一个或多个基团R2取代的具有5~40个芳环原子的芳氧基或杂芳氧基、或这些体系的组合代替;这里两个或更多个相邻取代基R1相互也可以形成单环或多环的脂环或芳环体系,其中芳环体系仅可以在X上形成;
Ar在每种情况中相同地或不同地是具有5~30个芳环原子的芳环或杂芳环体系,它们可以被一个或多个非芳基R1取代;相同氮原子上的两个基团Ar也可以通过单键或桥X相互连接;
R2在每种情况中相同地或不同地是H或具有1~20个碳原子的脂肪族、芳香族或杂芳香族烃基团;这里两个或更多个相邻取代基R2也可以相互形成单环或多环的脂环或芳环体系;
X在每种情况中相同地或不同地是选自下列的二价桥:B(R1)、C(R1)2、Si(R1)2、C=O、C=NR1、C=C(R1)2、O、S、S=O、SO2、N(R1)、P(R1)、P(=O)R1、P(=S)R1或这些体系中2、3或4个的组合;
n、m、p、o 在每种情况中相同地或不同地是0或1,前提条件是m+p=1或2,n+o=1或2,其中在每种情况中n=0且m=0且p=0且o=0是指不存在相应的桥X;
所述化合物的特征在于存在至少一个含有至少一个芳基或杂芳基的取代基R1。
式(1)的化合物的玻璃化转变温度Tg优选大于70℃,特别优选大于100℃,更特别优选大于130℃。
为了本发明的目的,芳基含有6~40个碳原子;为了本发明的目的,杂芳基含有2~40个碳原子和至少1个杂原子,前提条件是碳原子和杂原子之和为至少5。杂原子优先选自N、O和/或S。这里用芳基或杂芳基指简单的芳环即苯或简单的杂芳环,例如吡啶、嘧啶、噻吩等,或下列定义意义的稠合芳基或杂芳基。
为了本发明的目的,芳环体系在环体系中含有6~40个碳原子。为了本发明的目的,杂芳环体系在环体系中含有2~40个碳原子和至少1个杂原子,前提条件是碳原子和杂原子之和为至少5。杂原子优先选自N、O和/或S。为了本发明的目的,芳环或杂芳环体系是指不必仅含有芳基或杂芳基、而相反其中多个芳基或杂芳基也可以被短的非芳族单元(优选小于10%的非H原子)如sp3杂化的C、N或O原子中断的体系。因此,例如,也用如9,9’-螺二芴、9,9-二芳基芴、三芳基胺、二芳基醚等体系指用于本发明目的的芳环体系。部分芳环或杂芳环体系也可以是下列定义意义上的稠合基团。
为了本发明的目的,稠合芳基是指具有10~40个芳环原子的环体系,其中至少两个芳环相互“稠合”,即相互缩合,即具有至少一个共同边和一个共同的芳香π-电子体系。为了本发明的目的,稠合的杂芳基是指具有8~40个芳环原子的环体系,其中至少两个芳环或杂芳环相互稠合,其中至少一个是杂芳环。这些环体系可以被取代或不被取代。稠合芳基或杂芳基的例子是萘、喹啉、苯并噻吩、蒽、菲、邻菲咯啉、芘、二萘嵌苯、屈、吖啶等,但是例如联苯不是稠合芳基,这是由于在这两个环体系之间没有共同的边。例如芴同样也不是稠合的芳环体系,这是由于其中两个苯基单元没有形成共同的芳环体系。
为了本发明的目的,特别优选其中单个的H原子或CH2基团也可以被上面提及的基团取代的C1-~C40-烷基是指: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、2,2,2-三氟乙基、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、环辛烯基、乙炔基、丙炔基、丁炔基、戊炔基、己炔基或辛炔基。特别优选C1-~C40-烷氧基是指甲氧基、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2-甲基丁氧基。在每种情况中也可以被上面提及的基团R取代和可以通过任何需要的位置连接到芳环或杂芳环的具有5~40个芳环原子的芳环或杂芳环体系特别是指衍生自下列的基团:苯、萘、蒽、菲、芘、屈、二萘嵌苯、荧蒽、并四苯、并五苯、苯并芘、联苯、亚联苯基、三联苯、三亚苯基(terphenylene)、芴、螺二芴、二氢菲、二氢芘、四氢芘、顺或反-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、二苯并噻吩、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、萘咪唑、菲咪唑、吡啶咪唑、吡嗪咪唑、喹噁啉咪唑、噁唑、苯并噁唑、萘噁唑、蒽噁唑、菲噁唑、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、喹噁啉、1,5-二氮杂蒽、2,7-二氮杂芘、2,3-二氮杂芘、1,6-二氮杂芘、1,8-二氮杂芘、4,5-二氮杂芘、4,5,9,10-四氮杂二萘嵌苯、吡嗪、吩嗪、吩噁嗪、吩噻嗪、fluorubine、萘啶、氮杂咔唑、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。
优选这样的式(1)化合物,其在两个外部的非稠合芳基或杂芳基中各自含有0、1、2或3个相同或不同的杂原子且在每种情况中可以被一个或两个R1基团取代。特别优选这样的式(1)化合物,其中两个外部的非稠合芳基或杂芳基各自相同或不同地代表各自可以被一个或两个R1基团取代的苯、吡啶、嘧啶、吡嗪、哒嗪或噻吩,特别是代表可以被一个或两个R1基团,特别是被一个R1基团取代的苯。
更优选这样的式(1)化合物,其中中心稠合芳基或杂芳基在每种情况中相同地或不同地代表各自可以被一个或两个R1基团取代的萘基或具有1或2个杂原子的稠合杂芳基。所述中心稠合芳基或杂芳基特别优选代表萘、喹噁啉、喹啉、异喹啉、苯并嘧啶、苯并噻二唑、苯并噁二唑、苯并噻吩、苯并三唑、苯并呋喃或吲哚,更特别优选代表萘、喹啉、异喹啉或喹噁啉,特别是萘,在每种情况中可以被一个或两个R1基团取代。
而且优选式(1)中n+o=1和m+p=1的结构。
特别优选式(2)、(3)或(4)的结构
式中符号X和Y具有如上述的相同意义,中心的萘基可以被一个或多个R1基团取代。
更特别地优选式(2a)、(3a)或(4a)的结构
式中符号X和R1具有如上述的相同意义,萘基可以被一个或多个R1基团取代。
在式(2a)、(3a)或(4a)的结构中,特别优选两个R1都不等于氢。而且在这些结构中优选中心萘基是未取代的。
而且优选这样的式(1)、(2)、(3)和(4)或(2a)、(3a)或(4a)的化合物,其中符号R1在每种情况中相同或不同地代表H、F、C(=O)Ar、P(=O)(Ar)2、CR2=CR2Ar、具有1~5个碳原子的直链烷基或具有3~5个碳原子的支链烷基,其中一个或多个非相邻CH2可以被-R2C=CR2-、-C≡C-或-O-代替,且其中一个或多个H原子可以被F或每种情况中可以被一个或多个R2基团取代的具有6~16个碳原子的芳基或具有2~16个碳原子的杂芳基或螺二芴基团或这些体系中两个或三个的组合代替。在混入到聚合物、低聚物或树枝状聚合物中时,也优选具有至多10个碳原子的直链或支链烷基链。
而且优选这样的式(1)、(2)、(3)和(4)或(2a)、(3a)或(4a)的化合物,其中符号R1在每种情况中相同或不同地代表式(5)或(6)的N(Ar)2基团
式中R2具有上面指出的意义,并且:
E代表单键、O、S、N(R2)或C(R2)2;
Ar1在每种情况中相同或不同地为具有5~20个芳环原子的芳基或杂芳基、或具有15~30个芳环原子的三芳基氨基,在每种情况中它们可以被一个或多个R2基团取代,优选为具有6~14个芳环原子的芳基或杂芳基、或具有18~22个芳环原子的三芳基氨基,在每种情况中它们可以被一个或多个R2基团取代。
a在每种情况中相同地或不同地为0或1。
Ar1特别优选相同地或不同地代表苯基、邻-、间-或对-甲苯基、对-氟苯基、1-萘基、2-萘基、三苯基胺、萘基二苯基胺或二萘基苯基胺。
而且优选这样的式(1)、(2)、(3)和(4)或(2a)、(3a)和(4a)的化合物,其中符号X在每种情况中相同或不同地为选自C(R1)2、C=O、C=NR1、O、S、S=O、SO2、N(R1)、P(R1)、P(=O)R1、C(R1)2-C(R1)2、C(R1)2-C(R1)2-C(R1)2、C(R1)2-O和C(R1)2-O-C(R1)2的二价桥。特别优选这样的式(1)、(2)和(3)或(2a)和(3a)的化合物,其中符号X在每种情况中相同或不同地选自C(R1)2、N(R1)、P(R1)和P(=O)(R1),更特别地优选C(R1)2和N(R1),特别C(R1)2。这里应再次明确地指出,许多相邻R1基团这里也可以相互形成芳环或脂环体系。如果C(R1)2上许多R1基团相互形成环体系,那么这产生螺结构。通过在C(R1)2上两个R1基团之间形成环体系而形成这种螺结构是本发明的更优选的实施方案。这特别地适用于如果R1代表取代的或未取代的苯基和两个苯基与桥X一起形成环体系的情况。
而且优选对称的且对称取代的化合物,即式(1)、(2)和(3)或(2a)和(3a)的其中两个外部非稠合芳基或杂芳基相同和其中符号X相同的化合物。而且优选选择使得结构(2a)、(3a)和(4a)中的取代基R1相同。
式(1)的化合物的例子是下面描绘的结构(1)~(56)。
根据本发明的上述化合物,特别是被反应性离去基团如溴、碘、硼酸或硼酸盐取代的化合物,例如结构17、18、39、40、41、42和53的化合物,也可以用作用于制备相应的共轭、部分共轭或非共轭聚合物、低聚物的共聚单体,或也可以用作树枝状聚合物的核。优选通过卤素官能度或硼酸官能度进行聚合。
因此,本发明还涉及包含一种或多种式(1)的化合物的共轭、部分共轭和非共轭聚合物、低聚物或树枝状聚合物,式中一个或多个R1基团表示从式(1)的化合物到聚合物或树枝状聚合物的键。
如上述的相同优选适用聚合物、低聚物或树枝状聚合物中式(1)的重复单元。
式(1)的重复单元优选与另外的共聚单体共聚。合适且优选的共聚单体选自芴(例如根据EP842208或WO00/22026)、螺二芴(例如根据EP707020、EP894107或EP04028865.6)、对苯撑(例如根据WO92/18552)、咔唑(例如根据WO04/070772或WO04/113468)、噻吩(例如根据EP1028136)、二氢菲(例如根据WO05/014689)、顺和反式-茚并芴(例如根据WO04/041901或WO04/113412)、酮(例如根据WO05/040302)、菲(例如根据WO05/104264或还没有公开的申请DE102005037734.3)或这些单元中的许多种。这些聚合物通常也包含另外的单元,例如发光(荧光或磷光)单元,例如乙烯基三芳基胺(例如,根据还没有公开的申请DE102005060473.0)或磷光金属络合物(例如根据WO06/003000),和/或电荷传输单元,特别是基于三芳基胺的那些。
根据本发明的化合物可以根据本领域技术人员知道的合成步骤制备,例如溴化、Suzuki偶合、Hartwig-Buchwald偶合、酰化、烷基化、氧化环化等。
具有苯并[rst]戊芬-5,8-二酮骨架的化合物可以例如通过1,4-二苯酰基萘在共晶氯化铝/氯化钠熔体中的氧化环化制备(图解1)。
图解1
随后用Wolf-Kishner或Huang-Minlon方法使用肼水合物还原得到的苯并[rst]戊芬-5,8-二酮骨架,接着甲基化,最后溴化,生产出合成子3,10-二溴-5,5,8,8-四甲基苯并[rst]戊芬(图解2)。
图解2:
然后,3,10-二溴-5,5,8,8-四甲基苯并[rst]戊芬可以例如用芳基硼酸和芳基硼酸衍生物通过Suzuki偶合转化成扩展的芳烃,通过Buchwald偶合到二芳基胺转化成三芳基胺衍生物或通过锂化和与亲电子试剂如苄腈反应、然后酸性水解而转化成酮,或与氯二苯基膦反应,接着氧化以给出膦氧化物(图解3)。
图解3:
溴化当然也可以在苯并[rst]戊芬-5,8-二酮骨架上进行。随后与二苯基-2-溴化镁反应,并酸催化环化中间体三芳基甲醇,给出苯并[rst]戊芬的相应螺化合物(图解4),它可以如图解3地进一步官能化。
图解4:
苯[c]茚并[2,1-a]芴-13,14-二酮可以如Bulletin Chem.Soc.Jpn.1977,50(1),273中所述地制备。在无水氯化铁(III)存在下使用元素态溴可以溴化(类似图解2)。以这种方式得到的2,11-二溴苯[c]茚并[2,1-a]芴-13,14-二酮可以类似于图解2、3和4地进一步官能化。
该骨架的备选结构可以自1,4-双(2-甲氧基羰基苯基)萘开始,如图解5所示。该物质与有机金属试剂反应以给出相应的叔醇,用酸催化环化叔醇。形成的异构体的比例依赖于取代基和具体的合成条件。可以如上述地进行进一步的官能化。
图解5:
另外,溴化的化合物可以直接或在转化成硼酸衍生物之后用作用于聚合物、低聚物或树枝状聚合物的单体。
在合成中,根据合成条件,5元环/5元环衍生物以及6元环/6元环衍生物、5元环/6元环衍生物或这些化合物的化合物均可以形成。这些可以作为纯化合物分离和进一步处理或也以混合物使用。
式(1)的化合物非常高度地适合用在有机电致发光器件(OLED、PLED)中。根据取代基,该化合物在OLED中以各种功能使用。
因此,本发明还涉及式(1)的化合物在有机电子器件中的使用,特别是在有机电致发光器件中。
本发明另外还涉及包含至少一种式(1)的化合物的有机电子器件,特别是包含阳极、阴极和至少一层发光层的有机电致发光器件,特征在于至少一层有机层包含至少一种式(1)的化合物。
除了阴极、阳极和发光层,有机电致发光器件也可以包含另外的层。这些例如可以为:空穴注射层、空穴传输层、电子传输层、电子注射层和/或电荷产生层(IDMC2003,Taiwan;Session21 OLED(5),T.Matsumoto,T.Nakada,J.Endo,K.Mori,N.Kawamura,A.Yokoi,J.Kido,Multiphoton Organic EL Device Having Charge Generation Layer)。但是,应指出这些层各自都不是必需地存在的。
在本发明的进一步优选的实施方案中,有机电致发光器件包含许多发光层,其中至少一层包含至少一种式(1)的化合物。这些发光层特别优选在380nm和750nm之间总计具有多个发光最大值,使得在发光层中使用整体白色发光结果即可以发荧光或磷光和发光黄色、橙色或红色光的各种发光化合物。特别优选三层体系,其中这些层中至少一层包含至少一种式(1)的化合物,且其中这三层表现出蓝色、绿色和橙色或红色发光(对于基本结构,参见例如WO05/011013)。具有宽发光谱带和因此表现出白色发光的发光体同样适合白色发光。
在式(1)的化合物用作用于荧光掺杂剂的基质时,优选选自下列的一个或多个R1取代基:单或稠合的芳基或杂芳基,特别是苯基、邻-、间-或对-联苯基、1-或2-萘基、蒽基,特别是苯基蒽基或1-或2-萘基蒽基、2-芴基和2-螺二芴基,它们每个都可以被一个或多个R2基团取代。这特别适于式(2a)、(3a)和(4a)的结构上的R1基团。
包含基质和掺杂剂的体系中基质材料用来指在该体系中以较高比例存在的组分。在包含一种基质和许多掺杂剂的体系中,基质用来指在该混合物中比例最高的组分。
式(1)的基质材料在发光层中的比例为50.0重量%~99.9重量%,优选80.0重量%~99.5重量%,特别优选90.0重量%~99.0重量%。掺杂剂的比例相应为0.1重量%~50.0重量%,优选0.5重量%~20.0重量%,特别优选1.0重量%~10.0重量%。
在荧光器件中,掺杂剂优选选自一苯乙烯胺、二苯乙烯胺、三苯乙烯胺、四苯乙烯胺和芳胺的类别。一苯乙烯胺用来指包含一个苯乙烯基和至少一个胺的化合物,所述胺优选为芳族。二苯乙烯胺用来指含有两个苯乙烯基和至少一个胺的化合物,所述胺优选为芳族。三苯乙烯胺用来指含有三个苯乙烯基和至少一个胺的化合物,所述胺优选为芳族。四苯乙烯胺用来指含有四个苯乙烯基和至少一个胺的化合物,所述胺优选为芳族。为了本发明的目的,芳胺或芳族胺用来指含有直接键合到氮上的三个芳环或杂芳环体系的化合物,其中这些中的至少一个优选是具有至少14个芳环原子的稠环体系。苯乙烯基特别优选为在双键或芳环上也可以进一步取代的芪。这种掺杂剂的例子是取代的或未取代的三芪胺或另外的掺杂剂,例如描述在WO06/000388和还没有公开的专利申请DE102004031000.9、EP04028407.7和EP05001891.0中。另外,优选根据DE102005023437.2的化合物。
在式(1)的化合物用作用于磷光掺杂剂的基质时,一个或多个R1取代基优选含有至少一个C=O、P(=O)(R2)和/或SO2基团。特别优选这些基团直接键合到本发明的中心单元上,而且特别优选含有一个另外的芳族取代基,或在氧化膦的情况中含有两个另外的芳族取代基。这特别适于在式(2a)、(3a)和(4a)的结构上的R1基团。
在磷光器件中,掺杂剂优先选自含有至少一种原子数大于20,优选大于38且小于84,特别优选大于56且小于80的元素的金属络合物的类别。使用的磷光发光体优选为含有钼、钨、铼、钌、锇、铑、铱、钯、铂、银、金或铕,特别是铱或铂的金属络合物。如根据现有技术使用的磷光材料一般适合该目的。
而且,如果至少一个R1取代基含有至少一个乙烯基芳基单元、至少一个苯乙烯基单元和/或至少一个芳基氨基单元,优选使用式(1)的化合物作为发光材料。这特别适合在式(2a)、(3a)和(4a)的结构上的R1基团。
式(1)的化合物在发光层的混合物中的比例为0.1重量%~50.0重量%,优选0.5重量%~20.0重量%,特别优选1.0重量%~10.0重量%。基质材料的比例相应为50.0重量%~99.9重量%,优选80.0重量%~99.5重量%,特别优选90.0重量%~99.0重量%。
那么,合适的基质材料是各种类别的物质。优选的基质材料选自低聚芳烃的类别(例如根据EP676461的2,2’,7,7’-四苯基螺二芴,或二萘基蒽),特别是含有稠合的芳族基团的低聚芳烃、低聚芳烃乙烯基(例如根据EP676464的DPVBi或螺DPVBi)、多足配体金属络合物(例如根据WO04/081017)、空穴传导化合物(例如根据WO04/058911)、电子传导化合物,特别是酮、氧化膦、亚砜等(例如根据WO05/084081和WO05/084082)、阻转异构体(例如根据还没有公开的申请EP04026402.0)或硼酸衍生物(例如根据还没有公开的申请EP05009643.7)。另外,合适的基质材料是根据本发明的上述化合物。除了根据本发明的化合物,特别优选的基质材料选自含有萘、蒽和/或芘或这些化合物的阻转异构体的低聚芳烃、低聚芳烃乙烯基、酮、氧化膦和亚砜的类别。除根据本发明的化合物外,更特别优选的基质材料选自含有蒽和/或芘或这些化合物的阻转异构体的低聚芳烃、氧化膦和亚砜的类别。为了本发明的目的,低聚芳烃用来指至少三个芳基或亚芳基相互键合的化合物。
仍在本发明的另外的实施方案中,使用式(1)的化合物作为空穴传输材料或空穴注射材料。然后优选化合物被至少一个N(Ar)2基团,优选两个N(Ar)2基团取代。这特别适合在式(2a)、(3a)和(4a)的结构上的R1基团。该化合物优选用在空穴传输层或空穴注射层中。为了本发明的目的,空穴注射层是与阳极直接相邻的层。为了本发明的目的,空穴传输层是位于空穴注射层和发光层之间的层。如果使用式(1)的化合物作为空穴传输材料或空穴注射材料,可以优选用电子受体化合物掺杂它们,例如用F4-TCNQ或用EP1476881或EP1596445描述的化合物。
而且,优选式(1)的化合物用作电子传输材料。这里可以优选一个或多个R1取代基含有至少一个基团C=O、P(=O)(R2)和/或SO2。特别优选这些基团直接键合到根据本发明的中心单元上,而且特别优选还含有一个另外的芳族取代基,或在氧化膦的情况中含有两个另外的芳族取代基。而且,可以优选用电子给体化合物掺杂该化合物。这特别适合在式(2a)、(3a)和(4a)的结构上的R1基团。而且,可以优选用电子给体化合物掺杂该化合物。
式(1)的化合物也可以用在聚合物中作为聚合物骨架、作为发光单元和/或作为空穴传输单元。这里优选的取代方式对应于上述那些。
而且,优选特征在于利用升华方法涂布一层或多层的有机电致发光器件。在这种方法中,在真空升华单元中在低于10-5mbar,优选低于10-6mbar,特别优选低于10-7mbar的压力下,气相沉积所述材料。
同样优选如下有机电致发光器件,其特征在于利用OVPD(有机气相沉积)过程或在载气升华辅助下涂布一层或多层。这里在10-5mbar~1bar压力下应用所述材料。
而且,优选如下有机电致发光器件,其特征在于例如用旋涂或利用任何所需的印刷过程,例如丝网印刷、柔性版印刷或胶版印刷,但是优选LITI(光诱导热成像、热转印)或喷墨印刷,由溶液生产一层或多层。为了该目的,需要可溶性的式(1)的化合物。通过化合物的合适取代可以得到高溶解度。
根据本发明的化合物在用在有机电致发光器件中时具有高的效率和高的稳定性,特别是从长的寿命看这是明显的。另外,所述化合物具有高的玻璃化转变温度。
本申请上下文涉及根据本发明的化合物与OLED和PLED和相应显示器相关的使用。尽管受说明书限制,在无需进一步创造性劳动情况下,本领域的技术人员也可以使用根据本发明的化合物进一步用于其它电子器件中,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-SC)、有机场猝熄器件(O-FQD)、发光电化学电池(LEC)、有机激光二极管(O-激光器)或有机感光体。
本发明同样涉及根据本发明的化合物在相应器件中的应用和这些器件本身。
在不希望被下列实施例限制本发明情况下,用下列实施例更详细地解释本发明。
实施例:
除另外指出,在保护性气氛下进行下列合成。原料从ALDRICH或ABCR购买。如Journal of Organic Chemistry 2000,65(13),3952-3960所述地合成1,4-萘二硼酸。
实施例1:4,10-四甲基-4H-10H-芴并[4,3,2-de]蒽和5,8-四甲基-5,8-二氢苯并[rst]戊芬的合成
a)1,4-双(2-甲氧基羰基苯基)萘
将1.55g(0.1mmol)Pd(PPh3)4加到21.6g(7.1mmol)2-溴苯甲酸甲酯、10.1g(28mmol)1,4-萘二硼酸和18.9g(6.6mmol)磷酸三钾在350ml水与350ml THF的混合物中的剧烈搅拌、脱气的悬浮液中,回流该混合物60h。冷却后,分离去有机相,用200ml水洗涤三次,用200ml饱和氯化钠溶液洗涤一次,随后用硫酸镁干燥。在旋转蒸发器中在减压下蒸发该有机相至干燥。用二噁烷重结晶以这种方式得到的灰色残余物。抽吸滤去沉积的晶体,用50ml乙醇洗涤,随后在减压下干燥。产量:13g,理论值的82%。
b)1,4-双(2-甲醇-α,α-二甲基苯基)萘
起初在氮气下将30g(75mmol)1,4-双(2-甲氧基羰基苯基)萘引入在2000ml THF中,冷却至-78℃,逐滴加入175ml(378mmol)2.2M甲基锂溶液。随后在-78℃下搅拌该混合物16h。使该混合物达到室温过夜。在使用125ml饱和NH4Cl溶液水解之后,抽吸滤去沉淀物,用乙酸乙酯洗涤。滤液用水萃取两次,用Na2SO4干燥有机相。用色谱法(甲苯/乙酸乙酯6∶4)提纯蒸发溶剂后的残余物。产量:27g,理论值的93%。
c)4,10-四甲基-4H-10H-芴并[4,3,2-de]蒽和5,8-四甲基-5,8-二氢苯并[rst]戊芬
起初引入200g多磷酸。随后加入25g(63.05mmol)1,4-双((2-甲醇-α,α-二甲基)苯基)萘。在室温下搅拌该混合物20h。然后将冰水慢慢加到该混合物中。抽吸滤去沉淀的固体,在干燥箱中干燥,用乙酸乙酯重结晶。
收率:
4,10-四甲基-4H-10H-芴并[4,3,2-de]蒽(1):90.9g(理论值的45%)5,8-四甲基-5,8-二氢苯并[rst]戊芬(2):6.6g(理论值的30%)
实施例2:5,8-四(对-叔丁基苯基)-5,8-二氢苯并[rst]戊芬和4,10-四(对-叔丁基苯基)-4H-10H-芴并[4,3,2-de]蒽的合成
a)1,4-双[2-甲醇-α,α-二(对-叔丁基苯基)苯基]萘
起初在氮气下将8.5g(40mmol)1-溴-4-叔丁基苯引入在50mlTHF中,冷却至-75℃,逐滴加入25ml(40mmol)1.6M正丁基锂溶液,在该温度下搅拌该混合物2h。随后以使得温度不超过-65℃的速率逐滴加入溶解在50ml THF中的3.56g(9mmol)1,4-双(2-甲氧基羰基苯基)萘(如实施例1a中所述合成)。使该混合物达到室温过夜。在使用200ml水水解之后,抽吸滤去沉淀物。用乙醇漂洗,用乙酸乙酯重结晶。收率:15.8g,理论值的85%。
b)5,8-四(对-叔丁基苯基)-5,8-二氢苯并[rst]戊芬和4,10-四(对-叔丁基苯基)-4H-10H-芴并[4,3,2-de]蒽
起初将9.7g(11.2mmol)1,4-双[2-甲醇-α,α-二(对-叔丁基苯基)苯基]萘引入120ml冰乙酸中,搅拌该混合物10分钟。随后加入0.5ml HCl(浓),将该混合物回流1h。然后将冰水慢慢加到混合物中。抽吸滤去沉淀的固体,在干燥箱中干燥,用甲苯重结晶。
收率:
5,8-四(对-叔丁基苯基)-5,8-二氢苯并[rst]戊芬(3):5.8g,理论值的50%
4,10-四(对-叔丁基苯基)-4H-10H-芴并[4,3,2-de]蒽(4):2.8g,理论值的30%
实施例3:胺D1的合成
a)化合物(1)的溴化
起初在避光下将9.0g(25mmol)4,10-四甲基-4H-10H-芴并[4,3,2-de]蒽(1)引入300ml二氯甲烷中,冷却至5℃。用15分钟的时间逐滴加入25ml二氯甲烷中的2.7ml(50mmol)溴,再在5℃下搅拌该混合物7h。当转化完成时,加入15ml乙醇终止该反应,在抽吸下滤去产物,用乙醇洗涤多次,随后用NMP重结晶两次,给出11.2g(理论值的86%)浅黄色固体,根据HPLC,具有>99.7%的纯度。
b)胺D1的合成
将11.2g(22mmol)来自实施例3a的溴化合物和9.7g(58mmol)二苯胺悬浮在250ml无水甲苯中。随后加入190mg(0.9mmol)三叔丁基膦和107mg(0.5mmol)Pd(OAc)2和6.3g(66mmol)NaOtBu,将该反应混合物回流4h。当反应完成时,加入150ml水,抽吸滤去固体,用乙醇洗涤并干燥。用NMP重结晶5次,用沸腾的乙醇萃取2次,随后升华2次(330℃,2×10-5mbar),给出11.8g(77%)浅黄色固体,根据HPLC,具有>99.9%的纯度。
实施例4~6:胺D2、D3和D4的合成
类似实施例3,通过溴化和Hartwig-Buchwald偶合,由化合物(2)、(3)和(4)(如实施例1和2中所述地合成)合成相应的双(二苯基胺)衍生物。D2、D3和D4的结构描绘如下:
实施例7:OLED的制备
如WO04/058911中所述的通用过程生产OLED,在个体情况下针对特定情形进行适应性调整(例如,为了获得最佳的效率或颜色而改变层厚度)。
各种OLED的结果表示在下列实施例中。为了更好的可比性,除了发光层和空穴注射层,使用的基本结构、材料和层厚度相同。类似上面提及的通用过程生产具有下列结构的OLED:
空穴注射层(HIL) 0nm或20nmHIL1,见表1
空穴传输层(HTL) 40nm或20nmNPB(气相沉积;N-萘基-N-苯基
-4,4’-二氨基联苯)
发光层(EML) 材料、浓度和层厚度见表1
电子导体(ETL) 20nm AlQ3(从SynTec购买;三喹啉酸铝(III))
LiF/Al(阴极) 1nmLiF,顶端150nmAl
用标准方法表征这些OLED。为了该目的,确定电致发光光谱、效率(以cd/A测定)、由电流/电压/亮度特征线(IUL特征线)计算的作为亮度函数的功率效率(以Im/W测定)和寿命。寿命定义为1000cd/m2的初始亮度降至一半后的时间。
表1表示一些OLED(实施例8~11)的结果,每种情况中也表示了EML和HTL的组成,包括层厚度。这里OLED包含根据本发明的化合物作为空穴注射材料(D3在实施例9和11中的应用)、作为发光层中的基质材料((3)在实施例8和9中的应用)和/或作为发光层中掺杂剂(D3在实施例10和11中的应用)。基质材料H1和掺杂剂D5的结构显示如下:
表1
实施例 | HIL | HTL2 | EML | 最大效率(cd/A) | 1000cd/m2下的U(V) | CIEa | 寿命(h)b |
8 | - | NPB(40nm) | (3):D5(5%)(30nm) | 3.8 | 6.8 | x=0.15y=0.11 | 700 |
9 | D3(20nm) | NPB(20nm) | (3):D5(5%)(30nm) | 4.0 | 6.0 | x=0.15y=0.11 | 2200 |
10 | - | NPB(40nm) | H1:D3(5%)(30nm) | 9.0 | 5.6 | x=0.18y=0.24 | 5500 |
11 | D3(20nm) | NPB(20nm) | H1:D3(5%)(30nm) | 11.0 | 5.8 | x=0.18y=0.24 | 8000 |
a:CIE坐标:the Commission Internationale de l’Eclairage 1931的颜色坐标。
b寿命:亮度降至初始亮度的50%时的时间,在1000cd/m2的初始亮度下测定。
概括地,可以说,如表1可以容易地看到的,包含式(1)的化合物的OLED具有非常长的寿命和良好的效率。因此这些化合物非常适合用在OLED中。
Claims (14)
1.式(1)的化合物
式(1)
其中下列说明适用于使用的符号和标记:
Y在每种情况中相同地或不同地是CR1或N;或(Y-Y)或(Y=Y)(即两个相邻的Y)代表NR1、S或O;前提条件是各个环是五元环或六元环;
Z如果桥基X键合到基团Z,Z等于C,如果没有桥基X键合到基团Z,Z等于Y:
R1在每种情况中相同地或不同地是H、F、Cl、Br、I、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、具有1~40个碳原子的直链烷基、烷氧基或硫代烷氧基或具有3~40个碳原予的支链或环状烷基、烷氧基或硫代烷氧基,在各情况中它们可以被一个或多个基团R2取代,其中一个或多个非相邻的CH2可以被-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-代替,且其中一个或多个H原子可以被F、Cl、Br、I、CN或NO2或各情况中可以被一个或多个基团R2取代的具有5~40个芳环原子的芳环或杂芳环体系、或可以被一个或多个基团R2取代的具有5~40个芳环原子的芳氧基或杂芳氧基、或这些体系的组合代替;这里两个或更多个相邻取代基R1也可以相互形成单环或多环的脂环或芳环体系,其中芳环体系仅可以在X上形成;
Ar在每种情况中是具有5~30个芳环原子的芳环或杂芳环体系,它们可以被一个或多个非芳基R1取代;相同氮原子上的两个基团Ar也可以通过单键或桥基X相互连接;
R2在每种情况中相同地或不同地是H或具有1~20个碳原子的脂肪族、芳香族或杂芳香族烃基团;这里两个或更多个相邻取代基R2也可以相互形成单环或多环的脂环或芳环体系;
X在每种情况中相同地或不同地是选自下列的二价桥基团:B(R1)、C(R1)2、Si(R1)2、C=O、C=NR1、C=C(R1)2、O、S、S=O、SO2、N(R1)、P(R1)、P(=O)R1、P(=S)R1或这些体系中2、3或4个的组合;
n、m、p、o在每种情况中相同地或不同地是0或1,前提条件是m+p=1或2,n+o=1或2,其中在每种情况中n=0且m=0且p=0且o=0是指不存在相应的桥基X;
所述化合物的特征在于存在至少一个含有至少一个芳基或杂芳基的取代基R1。
2.如权利要求1所述的化合物,其特征在于两个外部的非稠合芳基或杂芳基在每种情况中相同或不同地代表苯基或选自吡啶、嘧啶、吡嗪、哒嗪和噻吩的杂芳基。
3.如权利要求1或2所述的化合物,其特征在于中心稠合芳基或杂芳基在每种情况中相同地或不同地代表萘、喹噁啉、喹啉、异喹啉、苯并嘧啶、苯并噻二唑、苯并噁二唑、苯并噻吩、苯并三唑、苯并呋喃或吲哚。
5.如权利要求4所述的式(2a)、(3a)或(4a)的化合物
式(2a) 式(3a)
式(4a)
式中符号X和R1具有如权利要求1所述的相同含义,且萘基可以被一个或多个R1基团取代。
6.如前述权利要求中至少一项所述的化合物,其特征在于符号R1在每种情况中相同或不同地代表H、F、C(=O)Ar、P(=O)(Ar)2、CR2=CR2Ar、具有1~5个碳原子的直链烷基或具有3~5个碳原子的支链烷基,其中一个或多个非相邻CH2可以被-R2C=CR2-、-C≡C-或-O-代替,且其中一个或多个H原子可以被F、或各情况中可以被一个或多个R2基团取代的具有6~16个碳原子的芳基或具有2~16个碳原子的杂芳基或螺二芴基团、或这些体系中两个或三个的组合代替,或其特征在于符号R1在每种情况中相同或不同地代表式(5)或(6)的基团
式(5) 式(6)
式中R2具有上面指出的含义,并且:
E代表单键、O、S、N(R2)或C(R2)2;
Ar1在每种情况中相同或不同地为具有5~20个芳环原子的芳基或杂芳基或具有15~30个芳环原子的三芳基氨基,在每种情况中它们可以被一个或多个R2基团取代,优选为具有6~14个芳环原子的芳基或杂芳基或具有18~22个芳环原子的三芳基氨基,在每种情况中它们可以被一个或多个R2基团取代;
a在每种情况中相同地或不同地为0或1。
7.如前述权利要求中至少一项所述的化合物,其特征在于符号X在每种情况中相同或不同地为选自C(R1)2、C=O、C=NR1、O、S、S=O、SO2、N(R1)、P(R1)、P(=O)R1、C(R1)2-C(R1)2、C(R1)2-C(R1)2-C(R1)2、C(R1)2-O和C(R1)2-O-C(R1)2的二价桥基团。
8.包含一种或多种式(1)的化合物的共轭、部分共轭或非共轭聚合物、低聚物或树枝状聚合物,其中一个或多个R1或R2基团表示从根据权利要求1所述的化合物到所述聚合物、低聚物或树枝状聚合物的键。
9.如权利要求8所述的聚合物、低聚物或树枝状聚合物,其特征在于另外的重复单元选自芴、螺二芴、对苯撑、咔唑、噻吩、二氢菲、顺式和反式-茚并芴、酮、荧光或磷光发光体、三芳基胺或多个这些单元。
10.如权利要求1~9中至少一项所述的化合物在有机电子器件中的应用。
11.包含如权利要求1~9中至少一项所述的至少一种化合物的有机电子器件。
12.如权利权利要求11所述的有机电子器件,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)、有机场猝熄器件(O-FQD)、发光电化学电池(LEC)、有机激光二极管(O-激光器)和有机感光体。
13.包含阳极、阴极和至少一层发光层的有机电致发光器件,其特征在于在发光层中使用如权利要求1~9中至少一项所述的至少一种化合物作为与至少一种荧光或磷光掺杂剂的混合物,和/或其特征在于在发光层中使用如权利要求1~9中至少一项所述的至少一种化合物作为与至少一种基质材料的混合物。
14.如权利要求11~13中一项或多项所述的有机电子器件,其特征在于使用如权利要求1~9中至少一项所述的化合物作为空穴传输层和/或空穴注射层中的空穴传输材料,和/或其特征在于使用如权利要求1~9中至少一项所述的化合物作为电子传输层中的电子传输材料。
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US9728728B2 (en) | 2011-06-27 | 2017-08-08 | Lg Chem, Ltd. | Compound and organic light-emitting device using same |
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US9373793B2 (en) | 2011-06-27 | 2016-06-21 | Lg Chem, Ltd. | Compound and organic light-emitting device using same |
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Also Published As
Publication number | Publication date |
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DE102005040411A1 (de) | 2007-03-01 |
US8748010B2 (en) | 2014-06-10 |
US20080193797A1 (en) | 2008-08-14 |
EP3211058A1 (de) | 2017-08-30 |
KR101951073B1 (ko) | 2019-02-21 |
JP2009505995A (ja) | 2009-02-12 |
JP5399070B2 (ja) | 2014-01-29 |
KR20130052663A (ko) | 2013-05-22 |
WO2007022845A1 (de) | 2007-03-01 |
TW200726736A (en) | 2007-07-16 |
KR20080049770A (ko) | 2008-06-04 |
KR102193244B1 (ko) | 2020-12-22 |
EP1917323A1 (de) | 2008-05-07 |
EP3211058B1 (de) | 2023-08-23 |
KR101578588B1 (ko) | 2015-12-17 |
EP1917323B1 (de) | 2019-12-18 |
KR20170036122A (ko) | 2017-03-31 |
CN101248156B (zh) | 2012-02-29 |
KR20150103340A (ko) | 2015-09-09 |
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