CN101415795A - 用于有机电致发光器件的材料 - Google Patents
用于有机电致发光器件的材料 Download PDFInfo
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- CN101415795A CN101415795A CNA2007800116985A CN200780011698A CN101415795A CN 101415795 A CN101415795 A CN 101415795A CN A2007800116985 A CNA2007800116985 A CN A2007800116985A CN 200780011698 A CN200780011698 A CN 200780011698A CN 101415795 A CN101415795 A CN 101415795A
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- aromatic ring
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- 239000000463 material Substances 0.000 title claims description 47
- 150000001875 compounds Chemical class 0.000 claims abstract description 101
- 125000003118 aryl group Chemical group 0.000 claims description 56
- 239000010410 layer Substances 0.000 claims description 53
- 239000000203 mixture Substances 0.000 claims description 21
- 229910052799 carbon Inorganic materials 0.000 claims description 19
- 125000001072 heteroaryl group Chemical group 0.000 claims description 19
- 125000004432 carbon atom Chemical group C* 0.000 claims description 18
- 238000005401 electroluminescence Methods 0.000 claims description 18
- 239000003205 fragrance Substances 0.000 claims description 17
- 239000000758 substrate Substances 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 229910052731 fluorine Inorganic materials 0.000 claims description 11
- 229910052757 nitrogen Inorganic materials 0.000 claims description 11
- 229910052794 bromium Inorganic materials 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- 238000002347 injection Methods 0.000 claims description 8
- 239000007924 injection Substances 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- 239000000460 chlorine Substances 0.000 claims description 7
- 125000003367 polycyclic group Chemical group 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 230000005540 biological transmission Effects 0.000 claims description 6
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical class OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
- 238000006069 Suzuki reaction reaction Methods 0.000 claims description 5
- 229910052740 iodine Inorganic materials 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- 229910052698 phosphorus Inorganic materials 0.000 claims description 5
- 229920000642 polymer Polymers 0.000 claims description 5
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- 230000005525 hole transport Effects 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000012044 organic layer Substances 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 125000005309 thioalkoxy group Chemical group 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- 230000027756 respiratory electron transport chain Effects 0.000 claims description 3
- 125000003003 spiro group Chemical group 0.000 claims description 3
- 229910052785 arsenic Inorganic materials 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 230000004888 barrier function Effects 0.000 claims description 2
- 230000000903 blocking effect Effects 0.000 claims description 2
- 230000005669 field effect Effects 0.000 claims description 2
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 2
- 230000010354 integration Effects 0.000 claims description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 2
- 238000004246 ligand exchange chromatography Methods 0.000 claims description 2
- 238000010791 quenching Methods 0.000 claims description 2
- 230000000171 quenching effect Effects 0.000 claims description 2
- 230000036647 reaction Effects 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 2
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims description 2
- 125000005259 triarylamine group Chemical group 0.000 abstract 1
- -1 stilbene amine Chemical class 0.000 description 28
- 150000002220 fluorenes Chemical class 0.000 description 18
- 150000001412 amines Chemical class 0.000 description 17
- 150000003254 radicals Chemical class 0.000 description 16
- PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 description 11
- 235000021286 stilbenes Nutrition 0.000 description 11
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 10
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- QPJORFLSOJAUNL-UHFFFAOYSA-N dibenzo[a,d][7]annulene Chemical compound C1=CC2=CC=CC=C2CC2=CC=CC=C21 QPJORFLSOJAUNL-UHFFFAOYSA-N 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 7
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 7
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 7
- ATYBXHSAIOKLMG-UHFFFAOYSA-N oxepin Chemical compound O1C=CC=CC=C1 ATYBXHSAIOKLMG-UHFFFAOYSA-N 0.000 description 7
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 6
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000004821 distillation Methods 0.000 description 6
- 238000004128 high performance liquid chromatography Methods 0.000 description 6
- 239000002304 perfume Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 125000000623 heterocyclic group Chemical group 0.000 description 5
- 238000006384 oligomerization reaction Methods 0.000 description 5
- 238000001953 recrystallisation Methods 0.000 description 5
- 238000000967 suction filtration Methods 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- 229960000583 acetic acid Drugs 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
- 239000004305 biphenyl Substances 0.000 description 4
- 235000010290 biphenyl Nutrition 0.000 description 4
- 125000004122 cyclic group Chemical group 0.000 description 4
- 238000010586 diagram Methods 0.000 description 4
- PJQCANLCUDUPRF-UHFFFAOYSA-N dibenzocycloheptene Chemical compound C1CC2=CC=CC=C2CC2=CC=CC=C12 PJQCANLCUDUPRF-UHFFFAOYSA-N 0.000 description 4
- 239000012362 glacial acetic acid Substances 0.000 description 4
- USKZHEQYENVSMH-UHFFFAOYSA-N hepta-1,3,5-triene Chemical compound CC=CC=CC=C USKZHEQYENVSMH-UHFFFAOYSA-N 0.000 description 4
- 230000000977 initiatory effect Effects 0.000 description 4
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 4
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 3
- KTADSLDAUJLZGL-UHFFFAOYSA-N 1-bromo-2-phenylbenzene Chemical group BrC1=CC=CC=C1C1=CC=CC=C1 KTADSLDAUJLZGL-UHFFFAOYSA-N 0.000 description 3
- 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 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000004982 aromatic amines Chemical class 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- XXPBFNVKTVJZKF-UHFFFAOYSA-N dihydrophenanthrene Natural products C1=CC=C2CCC3=CC=CC=C3C2=C1 XXPBFNVKTVJZKF-UHFFFAOYSA-N 0.000 description 3
- 150000002460 imidazoles Chemical class 0.000 description 3
- PJULCNAVAGQLAT-UHFFFAOYSA-N indeno[2,1-a]fluorene Chemical compound C1=CC=C2C=C3C4=CC5=CC=CC=C5C4=CC=C3C2=C1 PJULCNAVAGQLAT-UHFFFAOYSA-N 0.000 description 3
- 239000011159 matrix material Substances 0.000 description 3
- 238000005649 metathesis reaction Methods 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 229930192474 thiophene Natural products 0.000 description 3
- OVFJHQBWUUTRFT-UHFFFAOYSA-N 1,2,3,4-tetrahydrotetrazine Chemical compound C1=CNNNN1 OVFJHQBWUUTRFT-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-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
- VEUMBMHMMCOFAG-UHFFFAOYSA-N 2,3-dihydrooxadiazole Chemical compound N1NC=CO1 VEUMBMHMMCOFAG-UHFFFAOYSA-N 0.000 description 2
- WDFQBORIUYODSI-UHFFFAOYSA-N 4-bromoaniline Chemical compound NC1=CC=C(Br)C=C1 WDFQBORIUYODSI-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
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-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
- 238000005865 alkene metathesis reaction Methods 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
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 230000021615 conjugation Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 150000004696 coordination complex Chemical class 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- 230000006378 damage Effects 0.000 description 2
- 238000000151 deposition Methods 0.000 description 2
- 230000008021 deposition Effects 0.000 description 2
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
- 238000006317 isomerization reaction Methods 0.000 description 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 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
- 238000007639 printing Methods 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical class C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 2
- 238000000859 sublimation Methods 0.000 description 2
- 230000008022 sublimation Effects 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 238000002061 vacuum sublimation Methods 0.000 description 2
- FCTALLDRCBVIQN-UHFFFAOYSA-N 1,1'-biphenyl;naphthalen-1-amine Chemical class C1=CC=C2C(N)=CC=CC2=C1.C1=CC=CC=C1C1=CC=CC=C1 FCTALLDRCBVIQN-UHFFFAOYSA-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
- TXVWTOBHDDIASC-UHFFFAOYSA-N 1,2-diphenylethene-1,2-diamine Chemical compound C=1C=CC=CC=1C(N)=C(N)C1=CC=CC=C1 TXVWTOBHDDIASC-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
- OSEKAOVKCSZPNM-UHFFFAOYSA-N 1,3-benzoxazole;1,3-oxazole Chemical compound C1=COC=N1.C1=CC=C2OC=NC2=C1 OSEKAOVKCSZPNM-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 1
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 1
- TZMSYXZUNZXBOL-UHFFFAOYSA-N 10H-phenoxazine Chemical compound C1=CC=C2NC3=CC=CC=C3OC2=C1 TZMSYXZUNZXBOL-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
- 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
- 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
- HCCNHYWZYYIOFM-UHFFFAOYSA-N 3h-benzo[e]benzimidazole Chemical class C1=CC=C2C(N=CN3)=C3C=CC2=C1 HCCNHYWZYYIOFM-UHFFFAOYSA-N 0.000 description 1
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- FMMWHPNWAFZXNH-UHFFFAOYSA-N Benz[a]pyrene Chemical compound C1=C2C3=CC=CC=C3C=C(C=C3)C2=C2C3=CC=CC2=C1 FMMWHPNWAFZXNH-UHFFFAOYSA-N 0.000 description 1
- 229910004261 CaF 2 Inorganic materials 0.000 description 1
- 101100394073 Caenorhabditis elegans hil-1 gene Proteins 0.000 description 1
- 241000790917 Dioxys <bee> Species 0.000 description 1
- 239000007818 Grignard reagent Substances 0.000 description 1
- 101000801643 Homo sapiens Retinal-specific phospholipid-transporting ATPase ABCA4 Proteins 0.000 description 1
- 206010023126 Jaundice Diseases 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical class CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 1
- UKRQQTUHXSUNPV-UHFFFAOYSA-N N1NNN=CC1 Chemical compound N1NNN=CC1 UKRQQTUHXSUNPV-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
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- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
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- C07C209/06—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of halogen atoms
- C07C209/10—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of halogen atoms with formation of amino groups bound to carbon atoms of six-membered aromatic rings or from amines having nitrogen atoms bound to carbon atoms of six-membered aromatic rings
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- C07C211/54—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 two or three six-membered aromatic rings
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- C07C225/22—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
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- C07D223/18—Dibenzazepines; Hydrogenated dibenzazepines
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- C07D313/10—Seven-membered rings condensed with carbocyclic rings or ring systems condensed with two six-membered rings
- C07D313/14—[b,f]-condensed
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- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
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- C07F9/65527—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms the oxygen atom being part of a seven-(or more) membered ring condensed with carbocyclic rings or carbocyclic ring systems
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- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
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- C07F9/65683—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus atoms as the only ring hetero atoms the ring phosphorus atom being part of a phosphine
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- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
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- C07F9/65685—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus atoms as the only ring hetero atoms the ring phosphorus atom being part of a phosphine oxide or thioxide
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- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
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Abstract
本发明涉及被限定的基团取代的三芳香基胺。这些化合物能用于制造有机电致发光器件。
Description
本发明涉及芳香胺,涉及其用于制造有机电致发光器件的用途,以及涉及包括这些化合物的有机电致发光器件。
能够在可见光谱区发光并包含半导体有机化合物的有机电致发光器件的一般结构描述在例如US 4539507、US 5151629、EP 0676461和WO 98/27136中。然而,对于在高品质显示器中使用,这些器件仍存在相当大的需要迫切改进的问题。使用寿命仍不够,特别在发蓝色光的情况下,意谓着它至今仅可以实现简单的工业应用。另外,通常使用的蓝色发光体不具有足够的热稳定性。
JP 04-184892描述了二芪胺、三芪胺和其他芪衍生物作为OLEDs的发光化合物。包括所建议化合物的器件没有令人满意的寿命。另外,这些化合物在通过真空升华制造器件期间的热稳定性不够。分解产物导致沾污电致发光器件,因此导致差的电子特性。另外,其他的如现有技术使用的芪胺(例如根据JP 08-239655或EP 1167488),仅具有不充分的热稳定性。
WO 06/000388描述了芳基取代的三芪胺作为OLEDs的发光化合物。包括所建议化合物的器件表现出淡蓝色而不是深蓝色的发光。
通常,在芪胺情况下,注意到如在纯化材料的升华作用期间和在器件制造期间(示意图1),在高温下它们表现出不希望的副反应。因此,这些化合物表现出热引发的顺/反异构化。顺式的芪胺能够在分子内的闭环反应中进一步反应得到相应的二氢菲,而且在氧化剂例如残余的氧气存在情况下,得到相应的菲。这导致在OLED中不均匀的材料混合物,使得器件的再生变得更困难。而且,通常观察到热引发的烯烃复分解反应。在一方面,这导致低分子量化合物,导致沾污OLED,另一方面,由于在分子中有多个芪基团的情况下复分解反应引起材料的交联,导致高分子量的树脂化残余物。在许多材料的情况下,该树脂化残余物导致材料相当大的损失。另外,由烯烃复分解形成的相对高分子量的气相沉积的材料导致更长波的发光,因为这些化合物具有更广延伸的π电子体系。
示意图1:
1)热诱导的顺/反异构
2)二氢菲和菲的形成
3)烯烃的复分解反应
二氨基茋 茋
因此,本发明的目标是提供为了该目的的改进,特别是提供具有改进的寿命,同时具有改进的深蓝色色坐标以及高的热稳定性的化合物。
令人惊讶的是已经发现与现有技术相比较,在发光层中包含三芳香基胺衍生物的那些有机电致发光器件表现出明显的改进,所述三芳香基胺衍生物被二苯并环庚烯、二苯并氧杂环庚三烯、二苯并氮杂环庚三烯或这些化合物的衍生物取代。使用这些材料,得到改进的寿命,同时得到深蓝色的发光颜色和良好的效率。此外,与根据现有技术用作蓝色发光化合物的芪胺相比较,这些具有更高的热稳定性。因此,本发明涉及这些化合物和涉及其特别是在OLEDs发光层中的用途。
本发明涉及通式(1)的化合物:
通式(1)
其中适用以下使用的符号和标记:
Z每一次出现相同或者不同,是N、P、As或P=O;
X,Y每一次出现相同或者不同,是CR2、C=O、O、S、NR、SiR2、PR、P(=O)R、S(=O)或SO2;
A每一次出现相同或者不同,是CR或N;
AR1每一次出现相同或者不同,是具有5~40个芳环原子的一价芳族或杂芳族环系,它们可被一个或多个基团R取代;
Ar2每一次出现相同或者不同,是具有5~40个芳环原子的二价芳族或杂芳族环系,它们可被一个或多个基团R取代;
R每一次出现相同或者不同,是H、F、Cl、Br、I、CN、NO2、Si(R1)3、N(R1)2、B(OR1)2,具有1~40个碳原子的直链烷基、烷氧基或硫代烷氧基,或者具有3~40个碳原子的支链或者环状烷基、烷氧基或硫代烷氧基,它们每个可被一个或多个基团R1取代,其中一个或多个非相邻的CH2基团可以被-R1C=CR1-、-C≡C-、Si(R1)2、Ge(R1)2、Sn(R1)2、C=O、C=S、C=Se、C=NR1、-O-、-S-、-N(R1)-或-CONR1-替代,并且其中一个或多个H原子可以被F、Cl、Br、I、CN或NO2取代,或者是具有5~40个芳环原子的芳香或者杂芳环系,它们可被一个或多个基团R1取代,或者是具有5~24个芳环原子的芳氧基或杂芳氧基,它们可被一个或多个基团R1取代,或者这些体系的两个、三个、四个或者五个的组合;此处的两个或多个取代基R彼此也可以形成单环或者多环的、脂肪或者芳香环系;
R1每一次出现相同或者不同,是H或具有1~20个碳原子的烃基,其可以是脂肪族或芳香族或脂肪族和芳香族的组合;此处一个或多个H原子也可以被F取代;此处两个或多个基团R1也可以彼此形成单环或多环的脂肪或芳香环系;
n是0、1、2或3;
m每一次出现相同或者不同,是0或1,其中m=0意思是不存在基团Y,而是基团R结合在这些位置。
为了本发明的目的,芳基或者杂芳基认为是指具有共同的芳香π电子体系的芳香基团或者杂芳基团。为了本发明的目的,这可以是简单的碳环或者杂环,例如苯、吡啶、噻吩等,或者它可以是稠合的芳香环系,其中至少两个芳香或者杂芳族环,例如苯环,是彼此“合并”的,即通过环把一个稠合在另一个上,即具有至少一个共同的边缘,因此同样是共同的芳香π电子体系。这些芳基或者杂芳基可被取代或者不被取代;同样,任何存在的取代基可以形成另外的环系。因此,为了本发明的目的,例如体系比如萘、蒽、菲、芘等被认为是芳基基团,喹啉、吖啶、苯并噻吩、咔唑等被认为是杂芳基基团,而例如,联苯、芴、螺二芴等不代表芳基基团,因为它们包括分离的芳香π电子体系。
为了本发明的目的,芳香环系在环系中包含6~30个碳原子。为了本发明的目的,杂芳环系在环系中包含2~30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。为了本发明的目的,芳香或杂芳环系认为是指不必仅包括芳香基或杂芳基的体系,但相反其中多个芳基或杂芳基也可以被短的非芳香族单元间断(优选小于10%的非H原子),比如sp3-杂化的C、N或O原子,或其中一个或多个芳香基或杂芳基稠合在非芳香环基团上。因此,例如,多个相互连接的芳烃,例如联苯,或还有这样的体系,例如9,9′-螺二芴、9,9-二芳基芴、三芳胺、二芳醚等,为了本发明目的同样认为是芳香环系。同样,为了本发明的目的,如下的体系,例如二苯并环庚烯、二苯并氧杂环庚三烯、二苯并氮杂环庚三烯等也是指芳香环系。
为了本发明的目的,环烷基意味着不仅是单环的而且是双环和多环的烷基。
为了本发明的目的,其中另外单个H原子或CH2基团也可以被上述基团取代的C1~C40烷基特别优选如下的基团: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、金刚烷基、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、环已烯基、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、己炔基或者辛炔基。C1~C40烷氧基特别优选指甲氧基、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5~40个芳环原子,它们在每一情况下也可以被上述基团R或R1取代以及可以通过任何希望的位置与芳香或杂芳化合物连接的芳烃或杂芳族环系特别是指来源于如下的基团:苯、萘、蒽、菲、芘、屈、苝、荧蒽、丁省、戊省、苯并芘、联苯、联苯烯、三联苯、三联苯烯、芴、螺二芴、三聚茚、异三聚茚、二氢菲、二氢芘、四氢芘、顺式或反式的茚并芴、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、吡嗪、吩嗪、萘啶、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、苯并噻二唑、三苯胺、二苯基萘胺、二萘基苯胺、二苯醚、二苯并环庚烯、二苯并氧杂环庚三烯、二苯并氮杂环庚三烯和这些体系组合。
通式(1)化合物优选实施方案描述如下。
在本发明优选的实施方案中,符号Z,每一次出现相同或者不同,代表N或P=O。在本发明特别优选的实施方式中,符号Z代表N。
在本发明优选的实施方案中,在每一芳环中最多一个符号A代表N,在该芳环中其他的符号A代表CR。在本发明特别优选的实施方式中,符号A代表CR。
在本发明优选的实施方案中,至少一个基团Ar1代表通式(2)的基团:
通式(2)
其中符号和标记具有如上所述相同的含义,虚线键表示与基团Z的连接。此处优选在每一芳环中最多一个符号A代表N,在该芳环中其他的符号A代表CR;符号A特别优选代表CR。
特别优选通式(1a)的化合物:
通式(1a)
其中符号和标记具有如上所述的相同的含义。
此外优选这样的通式(1)和(1a)的化合物,其中符号X,每一次出现相同或者不同,代表CR2、O、NR或SiR2。特别优选这样的通式(1)或(1a)的化合物,其中符号X,每一次出现相同或者不同,代表CR2或O。
如果符号X代表通式CR2的基团,则在单元CR2中的R,每一次出现相同或者不同,优选代表具有1~4个碳原子的直链烷基,或具有3或4个碳原子的支链烷基,其中在每一情况下一个或多个H原子可被F取代,或代表具有5~10个芳环原子的芳香或杂芳基,或这些体系两个或三个的组合;此处在基团CR2中的两个基团R也可以彼此形成单环或多环的脂肪或芳香环系,因此能构造螺环系。特别优选的基团R是甲基、叔丁基、苯基、邻甲苯基、对甲苯基、或对叔丁基苯基。此处两个苯基在各自情况下还能彼此形成环系,因此构造螺环系,如通式(3)所示的二苯并环庚烯的骨架:
通式(3)
此外优选这样的通式(1)和(1a)的化合物,其中符号Y,每一次出现相同或者不同,代表CR2、O、NR或SiR2。特别优选这样的通式(1)或(1a)的化合物,其中符号Y,每一次出现相同或者不同,代表CR2或O。
此外优选这样的通式(1)和(1a)的化合物,其中符号R不与基团X结合,每一次出现相同或者不同,代表H、F、Si(R1)3、B(OR1)2、具有1~6个碳原子的直链烷基或者烷氧基、具有3~10个碳原子的支链、环状烷基或者烷氧基,其中在每一情况下一个或多个非相邻的CH2基团可被-R1C=CR1-、Si(R1)2、-O-、-S-或-N(R2)-替代,并且其中一个或多个H原子可以被F取代,或者代表具有5~14个芳环原子的芳香或者杂芳基,或者这些体系的两个或三个的组合;在这里两个或多个相邻的基团R彼此也可以形成单环或多环的、脂肪或者芳香环系。特别优选的基团R选自H、F、Si(R1)3、B(OR1)2、具有1~4个碳原子的直链烷基、具有3~5个碳原子的支链烷基或具有5~10个碳原子的环烷基,其中在每一情况下一个或多个H原子可以被F取代,或为具有6~10个芳环原子的一价芳香或杂芳基,或这些体系两个的组合。
此外优选如下的通式(1b)的化合物:
通式(1b)
其中符号和标记具有如上所述的相同的含义。
此外优选如下的通式(1)和(1a)和(1b)的化合物,其中符号Ar2,每一次出现相同或者不同,代表具有6~24个芳环原子的芳香或杂芳环系。符号Ar2,每一次出现相同或者不同,特别优选代表具有6~16个芳环原子的芳基、杂芳基或二芳基,或代表R取代的或未取代的芴、螺二芴或茚并芴。
此外优选如下通式(1)和(1a)和(1b)的化合物,其中符号n代表0、1或2,特别优选0或1,非常特别优选0。
此外,优选如下通式(1)和(1a)和(1b)的化合物,其中在通式(2)的每个单元上最多一个符号m等于1。特别优选如下通式(1)和(1a)的化合物,其中所有的标记m等于0。
因此特别优选通式(1c)的化合物:
通式(1c)
其中符号具有如上所述的相同的含义,其中符号Ar1优选代表如上通式(2)描述的基团。
此外优选如下通式(1)和(1a)~(1c)的化合物,其中选择所有的基团X相同,以及所有的基团Y,如果存在,也相同,其中在每一情况下所述基团还能被相同地取代,即对称化合物。特别优选n=0,具有三重对称轴的化合物。
通式(1)和(1a)~(1c)优选的化合物的实例是如下描述的化合物(1)~(33)。
上面描述的本发明的化合物,例如也可以用作共聚单体,用于制备相应的共轭、部分共轭或非共轭低聚物、聚合物或者作为树枝状聚合物的核。卤代化合物特别适合本目的,在这样情况下优选经由卤素官能团进行聚合。
因此,本发明还涉及包括一种或多种通式(1)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,其中一个或多个基团R代表通式(1)化合物与该聚合物或树枝状聚合物的结合。
这些聚合物可以包括另外的重复单元。这些另外的重复单元选自芴(例如根据EP 842208或WO 00/22026)、螺二芴(例如根据EP 707020、EP 894107或WO 06/061181)、三芳香基胺、对亚苯基(例如根据WO 92/18552)、咔唑(例如根据WO 04/070772和WO 04/113468)、噻吩(例如根据EP 1028136)、二氢菲(例如根据WO 05/014689)、茚并芴(例如根据WO 04/041901和WO 04/113412)、芳香酮(例如根据WO 05/040302)、菲(例如根据WO 05/104264)和/或金属络合物,特别是邻金属化的铱络合物。此处应该特别指出聚合物也可以具有选自上述的一种或多种、多个不同的重复单元。
该化合物通过本领域普通技术人员所熟知的有机化学方法合成。因此,能通过文献方法合成例如二苯并环庚烯(Schmuck et al.,Synthesis2002,5,655)、5,5′-二甲基二苯并环庚烯(Vinatoruet al.,Org.Prep.Proced.Int.1975,7(2),98)、二苯并氧杂环庚三烯(Hess et al.,J.Am.Chem.Soc.1967,89(11),2746)和N-甲基二苯并氮杂环庚三烯(Ohta etal.,Chem.Pharm Bull.1981,29(5),1221)和相应取代的衍生物。在文献中已经描述了上述母体结构不计其数的其他衍生物,特别是作为药用中间体起作用。这些化合物然后例如在Heck偶联中与三芳香基胺反应,所述的三芳香基胺在至少一个芳基上被氯、溴、碘或别的离去基团例如磺酸酯取代,例如三(对溴苯基)胺(示意图2)。
或者,将溴加成到双键上,随后消除HBr,随后使乙烯基溴转化为相应的硼酸,最后进行Suzuki偶联,这是可能的(示意图3)。优选不分离此处的硼酸,而是相反原位制备并直接用于Suzuki偶联。用于此处Suzuki偶联中钯的适当的配体特别是三(1-呋喃基)膦。
因此,本发明还涉及制备通式(1)化合物的方法,特征在于通式(4)的硼酸衍生物在Suzuki偶联中与通式(1)化合物的中心单元反应:
通式(4)
其中符号具有以上给出的含义,所述通式(1)化合物的中心单元包含作为活性基团的氯、溴、碘、三氟甲磺酸酯、甲苯磺酸酯或OSO2R1,其中R1具有如上所述的的相同含义。
通式(1)的化合物能用于有机电子器件,特别是有机电致发光器件中。
因此,本发明还涉及通式(1)的化合物在有机电子器件,特别是在有机电致发光器件中的用途。
本发明还涉及包括至少一个有机层有机电子器件,特征在于该有机层包括至少一种通式(1)的化合物。
该有机电子器件优选选自有机电致发光器(OLEDs,PLEDs)、有机场效应晶体管(O-FETs)、有机薄膜晶体管(O-TFTs)、有机发光晶体管(O-LETs)、有机集成电路(O-ICs)、有机太阳能电池(O-SCs)、有机场猝熄器件(O-FQDs)、有机光感受器、发光电化学电池(LECs)和有机激光器二极管(O-lasers)。特别优选有机电致发光器件(OLEDs、PLEDs)。
该有机电致发光器件包括阳极、阴极和至少一个发光层。除这些层之外,它可以包含其他的层,特别是选自空穴注入层、空穴传输层、空穴阻挡层、电子传输层、电子注入层和/或电荷产生层(T.Matsumotoet al.,Multiphoton Organic EL Device Having Charge Generation Layer,IDMC 2003,台湾;Session 21 OLED(5))。这些层的每一个不必必须存在。适合的空穴注入和空穴传输材料例如是现有技术通常使用的芳香胺,它们也可以是p型掺杂的。如在WO 05/084081和WO 05/084082中描述的适合的电子传输材料例如是金属螯合物,例如AlQ3,基于缺电子杂环的化合物,例如三嗪衍生物,或包含芳香羰基或氧化膦的化合物,它们每个在每一情况下也可以是n型掺杂的。适当的电子注入材料特别是碱金属和碱土金属的氟化物和氧化物例如NaF、BaF2、CaF2、LiF或Li2O。
通式(1)的化合物能以各种各样的功能用于有机电子器件中。
在本发明优选的实施方案中,通式(1)的化合物用作发光层中的发光化合物。如果符号Z代表N,并且符号X和Y,如果存在的话,代表CR2、O、NR和/或SiR2,通式(1)的化合物特别适合于该功能。
优选该化合物以与基质材料混合物的形式使用。基质材料是指在包括基质和掺杂物的体系(二元体系)中以较高比例存在的组分。在包括基质和多个掺杂物(三元和更多元体系)的体系中,基质材料认为是在该混合物中比例最高的组分。适当的基质材料是各种各样类别的物质,如通常现有技术中用作荧光有机电致发光器件基质材料的物质。优选的基质材料选自如下类别:寡聚芳烃(例如描述于EP676461中的2,2′,7,7′-四苯基螺二芴,或二萘蒽),特别是含稠合芳基的寡聚芳烃、寡聚芳烃苯乙烯(例如描述于EP676461中的DPVBi(双二苯基乙烯基二苯)或螺DPVBi,如);多配体的金属络合物(例如如描述于WO 04/081017中);空穴导电化合物(例如描述于WO 04/058911中),特别是三芳香基胺衍生物和咔唑衍生物;电子导电化合物,特别是酮、氧化膦和亚砜(例如描述于WO 05/084081或WO 05/084082中);阻转异构体(例如,如描述于WO 06/048268中);把手化合物(例如WO 06/097208中描述的);环烷基苯基蒽(例如在未公开申请DE102005026651.7中描述的)或硼酸衍生物(例如描述于WO 06/117052中)。特别优选的基质材料选自如下的类别:含萘、蒽、芘和/或苝的寡聚芳烃,或者这些化合物的阻转异构体,酮,氧化膦,亚砜和硼酸衍生物。非常特别优选的基质材料选自如下的类别:含蒽和/或芘的寡聚芳烃,或者这些化合物的阻转异构体,和氧化膦。
通式(1)化合物在所述混合物中的比例为0.1~99.0重量%,优选0.5~50.0重量%,特别优选1.0~20.0重量%,特别是1.0~10.0重量%。对应的,在所述混合物中基质材料的比例为1.0~99.9重量%,优选为50.0~99.5重量%,特别优选为80.0~99.0重量%,特别是90.0~99.0重量%。
在本发明另外的实施方式中,该有机电致发光器件具有多个发光层,其中这些层的至少一个包括至少一种通式(1)的化合物,所述的通式(1)的化合物优选与基质材料结合。这些发光层特别优选总计有多个峰值在380nm~750nm之间的发光,导致总的白色发光,即,在另外的发光层中,也可使用至少一种另外的能够发荧光或者发磷光以及发黄色光、发橙色光或者发红色光的发光化合物。特别优选三层体系,其中这些层的至少一个包括通式(1)的化合物,优选通式(1)的化合物与基质材料结合,其中该三个层表现出蓝色、绿色和橙色或者红色发光(对于基本结构,例如见WO 05/011013)。
在本发明别的实施方式中,通式(1)的化合物用作空穴传输和/或空穴注入材料。如果符号Z代表N或P,特别是代表N,并且符号X和Y,如果存在的话,代表CR2、O、NR和/或SiR2,特别适用。因而,该化合物优选用于空穴传输层和/或空穴注入层中。为了本发明的目的,空穴注入层是与阳极直接邻接的层。为了本发明的目的,空穴传输层是位于空穴注入层和发光层之间的层。如果通式(1)的化合物用作空穴传递或空穴注入材料,对于它们优选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所描述的化合物。如果通式(1)的化合物用作空穴传输层和/或空穴注入层中的空穴传输和/或空穴注入材料,也可以优选使用100%的比例,即使用该化合物作为纯的材料。
还优选使用通式(1)的化合物作为荧光和磷光OLEDs的电子传递材料和/或作为空穴阻挡材料,和/或作为磷光OLEDs的三重态基体材料。这特别适用于如下的化合物,其中基团Z代表P=O和/或基团X和Y,如果存在的话,代表C=O、P=O、S=O或SO2。
还优选这样的有机电致发光器件,特征在于通过升华方法涂敷一个或多个层,其中在真空升华装置中,在小于10-5毫巴、优选小于10-6毫巴、特别优选小于10-7毫巴压力下气相沉积该材料。
同样优选的有机电致发光器件,特征在于通过OVPD(有机气相沉积)方法或者在载气升华作用的帮助下涂敷一个或多个层,其中,在10-5毫巴~1巴之间的压力下施用所述材料。
进一步优选的有机电致发光器件,特征在于比如通过旋涂,或者通过任何希望的印刷方法比如丝网印刷、柔版印刷或者胶版印刷由溶液产生一个或多个层,但是特别优选LITI(光致热成像,热转移印刷)或者喷墨印刷。为了该目的,可溶的通式(1)的化合物是必要的。通过适当取代该化合物实现高的溶解性。
因此,本发明还涉及包括至少一种通式(1)的化合物和至少一种基质材料的混合物。
本发明的有机电致发光器件相对于现有技术具有以下令人惊讶的优点:
1.与现有技术的体系相比较,器件的稳定性变得更高,特别是从明显更长的寿命显而易见。
2.该化合物与现有技术用作蓝色发光体的芪胺相比较具有更高的热稳定性。特别是,在这些化合物情况下,既没有观察到热引发的顺/反异构化,也没有观察到热引发的复分解反应。因此,这些化合物实际上能无损失地升华,不会导致器件的沾污,能够可重复地制造器件。
3.该化合物当用于OLEDs中表现出深蓝色的发光颜色。
通过以下实施例更详细地阐明本发明,而不希望将本发明限制于此。
实施例:
除非另外指出,以下合成在保护气体气氛下进行。该原料购买自ALDRICH或ABCR(2-溴代联苯、乙酸钯(II)、三-1-呋喃基膦、无机物、溶剂)。10-溴代-5H-二苯并[a,d]环庚-5-酮的合成描述于文献(B.Taljaard et al.,Eur.J.Org.Chem.2005,12,2607)中,其中5H-二苯并[a,d]环庚烯描述于文献(C.Schmuck et al.,Synthesis 2002,5,655)中,其中10-溴二苯[b,f]氧杂环庚三烯描述于文献(M.Nogradi et al.,ActaChimica Academiae Scientiarum Hungaricae 1978,96(4),393)中。
实施例1:三(4-(10-二苯并[a,d]环庚烯-5-螺-9-二芴)苯基)胺
A)10-溴代二苯并[a,d]环庚烯-5-螺-9-二芴
从在400ml THF中的49.0ml(284mmol)的2-溴代联苯和4.3ml(55mmol)的1,2-二氯乙烷混合物与8.1g(333mmol)的镁制备相应的格氏试剂。77.0g(270mmol)的10-溴代-5H-二苯并[a,d]环庚-5-酮在400mlTHF中的溶液在强烈搅拌下迅速地加入到该溶液中,该混合物在室温下另外搅拌16小时。将20ml的EtOH加入到该溶液中,在真空中完全除去溶剂,残余物溶解在1000ml的冰醋酸中,加入5ml的浓盐酸,回流该混合物3h,然后加入200ml的甲苯,在搅拌下冷却该混合物,抽滤掉晶状沉淀,用冰醋酸洗涤三次,每次100ml,用100ml的乙醇洗涤三次,然后在真空中干燥。产率:102.0g(理论值的89.6%),根据NMR纯度约98%。
B)三(4-(10-二苯并[a,d]环庚烯-5-螺-9-二芴)苯基)胺
26.0ml(65mmol)正丁基锂(在正己烷中,2.5M)逐滴地加入到冷却至-78℃的25.3g(60mmol)10-溴代-5H-二苯并[a,d]环庚烯-5-螺-9-二芴在600mlTHF的溶液中,该混合物在-78℃下另外搅拌2小时。然后,加入8.0ml(72mmol)硼酸三甲酯,该混合物在-78℃下另外搅拌30分钟,并在温水浴中温热到0℃,加入600ml二氧六环、180ml 1.0M的碳酸钠溶液、8.7g(18mmol)三(4-溴苯基)胺、135mg(0.6mmol)的乙酸钯(II)和1.4g(6mmol)三-2-呋喃基膦,回流该混合物16小时。冷却之后,抽滤掉沉淀,用200ml的水洗涤三次,用100ml的乙醇洗涤三次,干燥,由二氧六环重结晶五次(约40ml/g),然后在T=365℃、p=5 x 10-5毫巴下升华。Yield:9.8g(理论值的43.2%),根据HPLC纯度为99.9%。
实施例2:三(4-(10-二苯并[a,d]环庚烯-5-螺-9-(2,7-二叔丁基)二芴)苯基)胺
类似于实施例1的步骤,其中用98.1g(284mmol)的2-溴代-4,4′-二叔丁基联苯代替2-溴代联苯。在T=360℃、p=5 x 10-5毫巴下升华。产率:16.4g(理论值的56.7%),根据HPLC纯度为99.9%。
实施例3:联苯基-(4-(10-二苯并[a,d]环庚烯-5-螺-9-二芴)苯基)胺
类似于实施例1的步骤,其中用17.8g(55mmol)的二苯基-(4-溴苯基)胺代替三(4-溴苯基)胺。由甲苯/乙腈重结晶。在T=315℃、p=5 x 10-5毫巴下升华。产率:22.9g(理论值的71.0%),根据HPLC纯度为99.9%。
其他的实施例:
从列出的溴代芳香胺开始类似实施例3制备以下的化合物。
实施例10:三(4-(10-(5-二甲基)二苯并[a,d]环庚烯)苯基)胺
A)5-二甲基二苯并[a,d]环庚烯
在10℃将12.3g(110mmol)叔丁醇钾加入19.2g(100mmol)的5H-二苯并[a,d]环庚烯在300ml DMSO的溶液中,搅拌该混合物10分钟,然后加入7.2ml(115mmol)的甲基碘,另外搅拌该混合物30分钟。随后在10℃下加入12.3g(110mmol)的叔丁醇钾,搅拌该混合物10分钟,然后加入7.2ml(115mmol)的甲基碘,另外搅拌该混合物30分钟。加入500ml的水,抽滤掉固体,由丁醇重结晶三次。产率:14.8g(理论值的67.1%),根据NMR纯度为95%。
B)10-溴代-5-二甲基二苯并[a,d]环庚烯
将38.4ml(750mmol)的溴逐滴加入到110.2g(500mmol)的5-二甲基二苯并[a,d]环庚烯在1000ml冰醋酸的悬浮液中,在室温下搅拌该混合物16小时。抽滤掉结晶固体,用少许冰醋酸和乙醇洗涤,干燥。
以这种方法得到的固体在50℃于强烈搅拌下加入到60g(1.5mol)氢氧化钠在3000ml甲醇的溶液中,回流该混合物1.5h,然后蒸馏掉1500ml的甲醇,加入相同量的水,使该混合物冷却,抽滤掉结晶固体,用水洗涤三次,每次200ml,用甲醇洗涤三次,每次200ml,在真空中干燥。产率:132.4g(理论值的88.5%),根据NMR纯度为98%。
C)三(4-(10-(5-二甲基)二苯并[a,d]环庚烯)苯基)胺
类似于实施例1B的步骤,其中用18.0g(60mmol)10-溴代-5-二甲基二苯并[a,d]环庚烯代替10-溴代-5H-二苯并[a,d]环庚烯-5-螺-9-二芴。由DMF重结晶。在T=320℃、p=5 x 10-5毫巴下升华。产率:8.7g(理论值的53.8%),根据HPLC纯度为99.9%。
实施例11:三(4-(10-二苯并[b,f]氧杂环庚三烯)苯基)胺
类似于实施例1B的步骤,其中用16.4g(60mmol)的10-溴代二苯并[b,f]氧杂环庚三烯代替10-溴代-5H-二苯并[a,d]环庚烯-5-螺-9-二芴。由NMP重结晶。在T=310℃、p=5 x 10-5毫巴下升华。产率:6.9g(理论值的46.5%),根据HPLC纯度为99.9%。
实施例12:热稳定性的比较
为比较本发明实施例1、2、3、10和11的化合物与现有技术的开链苯乙烯化合物三(4-芪)胺[114869-94-2]的热稳定性,在每一情况下,在真空中将100mg的根据HPLC纯度为99.9%的这些化合物在安瓿瓶中熔融,然后在280℃下储存100小时。
HPLC-MS分析显示本发明实施例1、2、3、10和11的化合物具有良好的热稳定性,显示没有显著的变化。相反,比较的化合物三(4-芪)胺经历了相当大的分解;在描述的条件下,在100小时之后发现仅约25%的三(4-芪)胺。除低聚部分以外,主要形成4,4′-二叔丁基芪。
实施例13:制造OLEDs
通过如WO 04/058911描述的一般方法制造OLEDs,在个别情况进行改造以适应特定的环境(例如为实现最佳效率或色彩的层厚度变化)。
在以下实施例14~21中列出各种各样OLEDs的结果。涂有结构化ITO(氧化锡铟)的玻璃板形成OLEDs的基材。为了更好的处理加工,将PEDOT(由水旋转涂敷;购买自H.C.Starck,Goslar,德国;聚(3,4-亚乙基二氧基-2,5-噻吩))直接施用于基材。OLEDs总是由以下层序列组成:基材/PEDOT 20nm/空穴注入层(HIL 1)20nm/空穴传输层(HTM1)20nm/发光层(EML)30nm/电子传输层(ETM 1)20nm和最后为阴极。除PEDOT以外,材料在真空室中热气相沉积。此处EML总是由基质材料(主体)和掺杂物(客体)组成,所述的客体通过共蒸发与主体混合。该使用的基质材料是基质H1。该阴极是由1nm薄的LiF层和在它上面沉积的150nm的Al层形成的。表1显示用于构造OLEDs的材料的化学结构。
这些OLEDs通过标准方法表征;为此目的确定电致发光光谱、效率(以cd/A测定)、作为明亮度函数由电流/电压/发光率特性(IUL特性线)计算的功率(以1m/W测定)以及寿命。寿命定义为初始亮度从1000cd/m2下降到一半的时间。
表2显示一些OLEDs的结果(实施例14-21)。
表1-使用的材料
表2- 一些OLEDs的结果
实施例 | EML | 最大效率(cd/A) | 在1000cd/m2时的电压(V) | CIE | 在1000cd/m2下的寿命(h) |
14 | H1+5%D1 | 6.5 | 5.6 | x=0.17/y=0.19 | 2200 |
15 | H1+3%D1 | 6.3 | 5.7 | x=0.16/y=0.18 | 1800 |
16 | H1+5%D4 | 10.5 | 5.5 | x=0.18/y=0.21 | 2400 |
17 | H1+3%D4 | 3.8 | 5.8 | x=0.18/y=0.20 | 2000 |
18 | H1+5%D10 | 6.2 | 5.5 | x=0.17/y=0.18 | 2300 |
19 | H1+3%D10 | 6.1 | 5.7 | x=0.16/y=0.18 | 2100 |
20 | H1+5%D11 | 12.5 | 5.4 | x=0.18/y=0.45 | 8100 |
21 | H1+7%D11 | 13.5 | 5.3 | x=0.18/y=0.46 | 8500 |
Claims (20)
1.通式(1)的化合物
通式(1)
其中适用以下使用的符号和标记:
Z 每一次出现相同或者不同,是N、P、As或P=O;
X,Y 每一次出现相同或者不同,是CR2、C=O、O、S、NR、SiR2、PR、P(=O)R、S(=O)或SO2;
A 每一次出现相同或者不同,是CR或N;
Ar1每一次出现相同或者不同,是具有5~40个芳环原子的一价芳香或杂芳环系,它们可被一个或多个基团R取代;
Ar2每一次出现相同或者不同,是具有5~40个芳环原子的二价芳香或杂芳环系,它们可被一个或多个基团R取代;
R 每一次出现相同或者不同,是H、F、Cl、Br、I、CN、NO2、Si(R1)3、N(R1)2、B(OR1)2,具有1~40个碳原子的直链烷基、烷氧基或硫代烷氧基,或者具有3~40个碳原子的支链或者环状烷基、烷氧基或硫代烷氧基,它们每个可被一个或多个基团R1取代,其中一个或多个非相邻的CH2基团可以被-R1C=CR1-、-C≡C-、Si(R1)2、Ge(R1)2、Sn(R1)2、C=O、C=S、C=Se、C=NR1、-O-、-S-、-N(R1)-或-CONR1-替代,并且其中一个或多个H原子可以被F、Cl、Br、I、CN或NO2取代,或者是可被一个或多个基团R1取代的具有5~40个芳环原子的芳香或者杂芳环系,或者是可被一个或多个基团R1取代的具有5~24个芳环原子的芳氧基或杂芳氧基,或者这些体系的两个、三个、四个或者五个的组合;此处的两个或多个取代基R也可以彼此形成单环或者多环的、脂肪或者芳香环系;
R1 每一次出现相同或者不同,是H或具有1~20个碳原子的烃基,它们可以是脂肪族或芳香族或脂肪族和芳香族的组合;此处一个或多个H原子也可以被F取代;此处两个或多个基团R1也可以彼此形成单环或多环的脂肪或芳香环系;
n是0、1、2或3;
m每一次出现相同或者不同,是0或1,其中m=0意思是不存在基团Y,而是基团R结合在这些位置。
2.如权利要求1所述的化合物,其特征在于符号Z,每一次出现相同或者不同,代表N或P=O。
3.如权利要求1或2所述的化合物,其特征在于在每一个芳环中最多一个符号A代表N,在该芳环中其他的符号A代表CR。
4.如权利要求1~3一项或多项所述的化合物,其特征在于至少一个基团Ar1代表通式(2)的基团
通式(2)
其中符号和标记具有如权利要求1所述相同的含义,虚线键表示与基团Z的连接。
6.如权利要求1~5一项或多项所述的化合物,其特征在于符号X,每一次出现相同或者不同,代表CR2、O、NR或SiR2。
7.如权利要求1~6一项或多项所述的化合物,其特征在于如果符号X代表通式CR2的基团,则在该基团X中的R,每一次出现相同或者不同,优选代表具有1~4个碳原子的直链烷基,或具有3或4个碳原子的支链烷基,其中在每一情况下一个或多个H原子可被F取代,或代表具有5~10个芳环原子的芳香或杂芳基,或这些体系两个或三个的组合;此处在基团CR2中的两个基团R也可以彼此形成单环或多环的脂肪的或芳香环系,因此能构造螺环系。
8.如权利要求1~7一项或多项所述的化合物,其特征在于符号Y,每一次出现相同或者不同,代表CR2、O、NR或SiR2。
10.如权利要求1~9一项或多项所述的化合物,其特征在于符号n代表0、1或2,优选代表0或1。
11.如权利要求1~10一项或多项所述的化合物,其特征在于符号m等于0。
12.如权利要求1~11一项或多项所述的化合物,其特征在于它们具有三重对称轴。
13.包括权利要求1~12一项或多项所述的一种或多种化合物的聚合物、低聚物或树枝状聚合物,其中一个或多个基团R代表从化合物到聚合物、低聚物或树枝状聚合物的结合。
14.一种制备权利要求1~12一项或多项所述的化合物的方法,其特征在于通式(4)的硼酸衍生物在Suzuki偶联中与通式(1)化合物的中心单元反应:
通式(4)
其中符号具有权利要求1给出的含义,所述的通式(1)化合物中心单元包含作为活性基团的氯、溴、碘、三氟甲磺酸酯、甲苯磺酸酯或OSO2R1,其中R1具有如权利要求1所述的的相同含义。
15.如权利要求1~13一项或多项所述的化合物在有机电子器件中的用途。
16.一种包括至少一个有机层的有机电子器件,其特征在于该有机层包括至少一种权利要求1~13一项或多项所述的化合物。
17.如权利要求16所述的有机电子器件,选自有机电致发光器件(OLEDs、PLEDs)、有机场效应晶体管(O-FETs)、有机薄膜晶体管(O-TFTs)、有机发光晶体管(O-LETs)、有机集成电路(O-ICs)、有机太阳能电池(O-SCs)、有机场猝熄器件(O-FQDs)、有机光感受器、发光电化学电池(LECs)和有机激光器二极管(O-lasers)。
18.如权利要求17所述的有机电致发光器件,包括阳极、阴极和至少一个发光层,以及任选的另外的层,所述另外的层选自空穴注入层、空穴传输层、空穴阻挡层、电子传输层、电子注入层和/或电荷产生层。
19.如权利要求17或18所述的有机电致发光器件,特征在于权利要求1~13一项或多项所述的化合物在发光层中用作发光化合物,优选与基质材料结合,和/或作为空穴传输或空穴注入材料,优选在空穴传输或空穴注入层中,和/或作为荧光或磷光OLEDs的电子传输材料和/或空穴阻挡材料,和/或作为磷光OLEDs的三重态基体材料。
20.如权利要求1~13一项或多项所述的至少一种化合物和至少一种基质材料的混合物。
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CN102260257A (zh) * | 2010-07-08 | 2011-11-30 | 中国科学院理化技术研究所 | 吡唑并[3,4-b]吡啶衍生物及其在白光有机电致发光器件中的应用 |
CN102260257B (zh) * | 2010-07-08 | 2013-05-01 | 中国科学院理化技术研究所 | 吡唑并[3,4-b]吡啶衍生物及其在白光有机电致发光器件中的应用 |
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JP2009532396A (ja) | 2009-09-10 |
WO2007115610A1 (de) | 2007-10-18 |
CN101415795B (zh) | 2012-12-12 |
JP5405297B2 (ja) | 2014-02-05 |
EP2001972B1 (de) | 2011-05-04 |
DE502007007129D1 (de) | 2011-06-16 |
ATE508176T1 (de) | 2011-05-15 |
US8039126B2 (en) | 2011-10-18 |
US20090058289A1 (en) | 2009-03-05 |
EP2001972A1 (de) | 2008-12-17 |
DE102006015183A1 (de) | 2007-10-04 |
TW200804559A (en) | 2008-01-16 |
KR101473015B1 (ko) | 2014-12-15 |
KR20080108329A (ko) | 2008-12-12 |
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