CN101848882A - 电致发光器件 - Google Patents
电致发光器件 Download PDFInfo
- Publication number
- CN101848882A CN101848882A CN200880108109A CN200880108109A CN101848882A CN 101848882 A CN101848882 A CN 101848882A CN 200880108109 A CN200880108109 A CN 200880108109A CN 200880108109 A CN200880108109 A CN 200880108109A CN 101848882 A CN101848882 A CN 101848882A
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- Prior art keywords
- alkyl
- aryl
- compound
- separate
- replaced
- Prior art date
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- Granted
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- 239000000463 material Substances 0.000 claims abstract description 140
- 150000001875 compounds Chemical class 0.000 claims abstract description 134
- -1 xenyl Chemical group 0.000 claims description 94
- 239000002585 base Substances 0.000 claims description 49
- 229910052757 nitrogen Inorganic materials 0.000 claims description 45
- 229910052799 carbon Inorganic materials 0.000 claims description 42
- 229910052739 hydrogen Inorganic materials 0.000 claims description 31
- 125000003545 alkoxy group Chemical group 0.000 claims description 30
- 125000000217 alkyl group Chemical group 0.000 claims description 28
- 239000000758 substrate Substances 0.000 claims description 25
- 125000001072 heteroaryl group Chemical group 0.000 claims description 24
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 19
- 229910052736 halogen Inorganic materials 0.000 claims description 18
- 150000002367 halogens Chemical group 0.000 claims description 18
- 229910052760 oxygen Inorganic materials 0.000 claims description 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
- 229910052786 argon Inorganic materials 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- 229910052731 fluorine Inorganic materials 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 11
- 125000004122 cyclic group Chemical group 0.000 claims description 10
- 125000001624 naphthyl group Chemical group 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 9
- 230000007812 deficiency Effects 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 8
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 7
- 229910052794 bromium Inorganic materials 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 claims description 3
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 3
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 claims description 3
- 125000005561 phenanthryl group Chemical group 0.000 claims description 3
- 239000003513 alkali Substances 0.000 claims description 2
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 claims description 2
- 101000766096 Halorubrum sodomense Archaerhodopsin-3 Proteins 0.000 claims 5
- 108091008695 photoreceptors Proteins 0.000 claims 1
- 230000003595 spectral effect Effects 0.000 abstract description 5
- 239000010410 layer Substances 0.000 description 96
- 239000000047 product Substances 0.000 description 44
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 39
- 125000003118 aryl group Chemical group 0.000 description 36
- 239000011159 matrix material Substances 0.000 description 34
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 25
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 22
- 230000005540 biological transmission Effects 0.000 description 18
- 239000012044 organic layer Substances 0.000 description 18
- 239000011541 reaction mixture Substances 0.000 description 17
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 16
- 125000004093 cyano group Chemical group *C#N 0.000 description 16
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- 230000004888 barrier function Effects 0.000 description 15
- 229910052741 iridium Inorganic materials 0.000 description 15
- 239000000243 solution Substances 0.000 description 15
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 14
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 13
- 238000002360 preparation method Methods 0.000 description 13
- 230000027756 respiratory electron transport chain Effects 0.000 description 13
- 229910052751 metal Inorganic materials 0.000 description 12
- 239000002184 metal Substances 0.000 description 12
- 239000000203 mixture Substances 0.000 description 12
- 239000007789 gas Substances 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- KLFRPGNCEJNEKU-FDGPNNRMSA-L (z)-4-oxopent-2-en-2-olate;platinum(2+) Chemical compound [Pt+2].C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O KLFRPGNCEJNEKU-FDGPNNRMSA-L 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 9
- 150000004646 arylidenes Chemical group 0.000 description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 9
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 9
- 125000005259 triarylamine group Chemical group 0.000 description 9
- 229910052782 aluminium Inorganic materials 0.000 description 8
- 239000004411 aluminium Substances 0.000 description 8
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 8
- 125000000753 cycloalkyl group Chemical group 0.000 description 8
- 125000000623 heterocyclic group Chemical group 0.000 description 8
- 238000004770 highest occupied molecular orbital Methods 0.000 description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 8
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 8
- 229960003540 oxyquinoline Drugs 0.000 description 8
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 8
- SLGBZMMZGDRARJ-UHFFFAOYSA-N triphenylene Chemical class C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 150000001412 amines Chemical class 0.000 description 7
- 125000003710 aryl alkyl group Chemical group 0.000 description 7
- 125000004429 atom Chemical group 0.000 description 7
- 238000000151 deposition Methods 0.000 description 7
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 7
- 239000010408 film Substances 0.000 description 7
- 238000002347 injection Methods 0.000 description 7
- 239000007924 injection Substances 0.000 description 7
- 239000000741 silica gel Substances 0.000 description 7
- 229910002027 silica gel Inorganic materials 0.000 description 7
- 125000001544 thienyl group Chemical group 0.000 description 7
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 125000003342 alkenyl group Chemical group 0.000 description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 6
- 150000001721 carbon Chemical group 0.000 description 6
- 230000008021 deposition Effects 0.000 description 6
- 230000006872 improvement Effects 0.000 description 6
- 150000004880 oxines Chemical class 0.000 description 6
- 239000001301 oxygen Substances 0.000 description 6
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 6
- 150000003254 radicals Chemical class 0.000 description 6
- OINTWKQEZMOIHS-UHFFFAOYSA-N BrC1=CC=CC2=C1C1=C(C(=C(C(=C1C=1C=CC=CC21)C2=CC=CC=C2)C2=CC=CC=C2)C2=CC=CC=C2)C2=CC=CC=C2 Chemical compound BrC1=CC=CC2=C1C1=C(C(=C(C(=C1C=1C=CC=CC21)C2=CC=CC=C2)C2=CC=CC=C2)C2=CC=CC=C2)C2=CC=CC=C2 OINTWKQEZMOIHS-UHFFFAOYSA-N 0.000 description 5
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
- REDXJYDRNCIFBQ-UHFFFAOYSA-N aluminium(3+) Chemical compound [Al+3] REDXJYDRNCIFBQ-UHFFFAOYSA-N 0.000 description 5
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 239000010406 cathode material Substances 0.000 description 5
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 5
- 239000002019 doping agent Substances 0.000 description 5
- 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 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- 230000009467 reduction Effects 0.000 description 5
- 239000010409 thin film Substances 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 150000004982 aromatic amines Chemical class 0.000 description 4
- 239000004305 biphenyl Substances 0.000 description 4
- 235000010290 biphenyl Nutrition 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 238000004440 column chromatography Methods 0.000 description 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 4
- 238000005538 encapsulation Methods 0.000 description 4
- 238000000605 extraction Methods 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 125000005843 halogen group Chemical group 0.000 description 4
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 230000005525 hole transport Effects 0.000 description 4
- MILUBEOXRNEUHS-UHFFFAOYSA-N iridium(3+) Chemical compound [Ir+3] MILUBEOXRNEUHS-UHFFFAOYSA-N 0.000 description 4
- GIFAOSNIDJTPNL-UHFFFAOYSA-N n-phenyl-n-(2-phenylphenyl)naphthalen-1-amine Chemical group C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=CC=C1C1=CC=CC=C1 GIFAOSNIDJTPNL-UHFFFAOYSA-N 0.000 description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 4
- 230000002441 reversible effect Effects 0.000 description 4
- 150000003384 small molecules Chemical class 0.000 description 4
- 239000007787 solid Substances 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
- LPCWDYWZIWDTCV-UHFFFAOYSA-N 1-phenylisoquinoline Chemical compound C1=CC=CC=C1C1=NC=CC2=CC=CC=C12 LPCWDYWZIWDTCV-UHFFFAOYSA-N 0.000 description 3
- NBYLBWHHTUWMER-UHFFFAOYSA-N 2-Methylquinolin-8-ol Chemical compound C1=CC=C(O)C2=NC(C)=CC=C21 NBYLBWHHTUWMER-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
- GEQBRULPNIVQPP-UHFFFAOYSA-N 2-[3,5-bis(1-phenylbenzimidazol-2-yl)phenyl]-1-phenylbenzimidazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2N=C1C1=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=C1 GEQBRULPNIVQPP-UHFFFAOYSA-N 0.000 description 3
- XSUNFLLNZQIJJG-UHFFFAOYSA-N 2-n-naphthalen-2-yl-1-n,1-n,2-n-triphenylbenzene-1,2-diamine Chemical compound C1=CC=CC=C1N(C=1C(=CC=CC=1)N(C=1C=CC=CC=1)C=1C=C2C=CC=CC2=CC=1)C1=CC=CC=C1 XSUNFLLNZQIJJG-UHFFFAOYSA-N 0.000 description 3
- 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 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 3
- UJOBWOGCFQCDNV-UHFFFAOYSA-N Carbazole Natural products C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 3
- RAASUWZPTOJQAY-UHFFFAOYSA-N Dibenz[a,c]anthracene Chemical group C1=CC=C2C3=CC4=CC=CC=C4C=C3C3=CC=CC=C3C2=C1 RAASUWZPTOJQAY-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 3
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 3
- 125000000304 alkynyl group Chemical group 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 3
- 125000004104 aryloxy group Chemical group 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 3
- 238000005229 chemical vapour deposition Methods 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 239000004020 conductor Substances 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical compound I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 0.000 description 3
- 238000005401 electroluminescence Methods 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 229910052738 indium Inorganic materials 0.000 description 3
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 239000011630 iodine Substances 0.000 description 3
- 239000003446 ligand Substances 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical group C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 3
- 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 3
- 150000002790 naphthalenes Chemical class 0.000 description 3
- 239000011368 organic material Substances 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- HRGDZIGMBDGFTC-UHFFFAOYSA-N platinum(2+) Chemical compound [Pt+2] HRGDZIGMBDGFTC-UHFFFAOYSA-N 0.000 description 3
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 3
- 238000007639 printing Methods 0.000 description 3
- 125000000714 pyrimidinyl group Chemical group 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- 230000003245 working effect Effects 0.000 description 3
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 2
- ZSYMVHGRKPBJCQ-UHFFFAOYSA-N 1,1'-biphenyl;9h-carbazole Chemical group C1=CC=CC=C1C1=CC=CC=C1.C1=CC=C2C3=CC=CC=C3NC2=C1 ZSYMVHGRKPBJCQ-UHFFFAOYSA-N 0.000 description 2
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 2
- STTGYIUESPWXOW-UHFFFAOYSA-N 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline Chemical compound C=12C=CC3=C(C=4C=CC=CC=4)C=C(C)N=C3C2=NC(C)=CC=1C1=CC=CC=C1 STTGYIUESPWXOW-UHFFFAOYSA-N 0.000 description 2
- RUKISNQKOIKZGT-UHFFFAOYSA-N 2-nitrodiphenylamine Chemical compound [O-][N+](=O)C1=CC=CC=C1NC1=CC=CC=C1 RUKISNQKOIKZGT-UHFFFAOYSA-N 0.000 description 2
- GJCOSYZMQJWQCA-UHFFFAOYSA-N 9H-xanthene Chemical compound C1=CC=C2CC3=CC=CC=C3OC2=C1 GJCOSYZMQJWQCA-UHFFFAOYSA-N 0.000 description 2
- OMPQIGDBPROUPN-UHFFFAOYSA-N C1(=CC=CC2=CC=C3C=C4C=CC=CC4=CC3=C12)C1=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C1=2 Chemical compound C1(=CC=CC2=CC=C3C=C4C=CC=CC4=CC3=C12)C1=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C1=2 OMPQIGDBPROUPN-UHFFFAOYSA-N 0.000 description 2
- UEXCJVNBTNXOEH-UHFFFAOYSA-N Ethynylbenzene Chemical compound C#CC1=CC=CC=C1 UEXCJVNBTNXOEH-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
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- HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 241000894007 species Species 0.000 description 1
- VNFWTIYUKDMAOP-UHFFFAOYSA-N sphos Chemical compound COC1=CC=CC(OC)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 VNFWTIYUKDMAOP-UHFFFAOYSA-N 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 125000004079 stearyl 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])C([H])([H])C([H])([H])C([H])([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
- 238000003756 stirring Methods 0.000 description 1
- 238000012360 testing method Methods 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
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000004627 thianthrenyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3SC12)* 0.000 description 1
- 125000002769 thiazolinyl group Chemical group 0.000 description 1
- 125000005309 thioalkoxy group Chemical group 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- RPVGLMKJGQMQSN-UHFFFAOYSA-N tiliquinol Chemical compound C1=CC=C2C(C)=CC=C(O)C2=N1 RPVGLMKJGQMQSN-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- 125000002889 tridecyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- DRDVZXDWVBGGMH-UHFFFAOYSA-N zinc;sulfide Chemical compound [S-2].[Zn+2] DRDVZXDWVBGGMH-UHFFFAOYSA-N 0.000 description 1
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Abstract
本发明涉及一种电子器件,尤其是电致发光器件,所述器件包含式(I)化合物,尤其作为磷光化合物的基质。所述基质可与磷光材料一起作用以提供电致发光器件的改善的效率、稳定性、可制造性或光谱特征。
Description
JP2007223921涉及式化合物;Q=(R1-R6=H,R1-R6=Q中的Q≥1;X1-X5=H、C1-10烷基、芳基,X1-X5=SiRaRbRc中的SiRaRbRc≥1;Ra、Rb、Rc=H、OH、C1-10烷基、烷氧基、芳基),其用作有机电致发光器件的电子传输层、基质材料等。
KR2006107720涉及一种具有高玻璃态转化温度且热稳定性优良的苯并菲衍生物,和一种含有所述苯并菲衍生物作为空穴注入材料、空穴转移材料或发光层材料的有机发光二极管。所述苯并菲衍生物由式表示,其中R1和R2为取代或未取代的C6-C14芳基。
JP11092420涉及式的苯并菲衍生物,其中Ar1-Ar6各自为芳基等;R11-R16各自为式(R1-R3各自例如为H);R21-R26各自例如为烷基;m1-m6各自为0或1;n1-n6各自为0、1或2;其用作液晶材料。明确公开了下列化合物:
JP11251063公开了由式表示的苯并菲化合物,例如所述苯并菲化合物用作有机EL元件的组分材料。在所述式中,R1-R12各自独立代表氢原子、卤素原子、羟基、取代或未取代的氨基、硝基、氰基、取代或未取代的烷基、取代或未取代的链烯基、取代或未取代的环烷基、取代或未取代的烷氧基、取代或未取代的芳族烃基、取代或未取代的芳族杂环基团、取代或未取代的芳烷基、取代或未取代的芳氧基、取代或未取代的烷氧羰基或羧基。R1-R12可从其中形成2个环。
JP2005259472涉及一种有机电致发光元件,其具有含有相邻发光层与在电极对之间的阻隔层的有机层,在发光层中含有磷光材料以及在阻隔层中含有苯并菲化合物。
US6492041涉及一种有机电致发光(EL)器件,所述器件含有阳极、阴极和至少一层位于所述阳极与所述阴极之间的有机薄膜层,所述一层或一层以上有机薄膜层含有发光层,所述一层以上有机薄膜层中的所述一层或至少一层含有由通式[1]所表示的化合物:(1),其中R1-R12各自独立代表氢原子、卤素原子、羟基、取代或未取代的氨基、硝基、氰基、取代或未取代的烷基、取代或未取代的链烯基、取代或未取代的环烷基、取代或未取代的烷氧基、取代或未取代的芳烃、取代或未取代的芳族杂环基团、取代或未取代的芳烷基、取代或未取代的芳氧基、取代或未取代的烷氧羰基或羧基,其中R1-R12各自可为由2个所述原子和基团形成的环,R1-R12中至少一个为由-NAr1Ar2表示的二芳基氨基,其中Ar1和Ar2各自独立代表具有6-20个碳原子的芳基,Ar1和Ar2之一具有取代或未取代的苯乙烯基作为取代基,Ar1和Ar2中的另一个不具有取代或未取代的苯乙烯基作为取代基。通式[1]的化合物用作空穴传输材料。
WO2006038709公开了由通式表示的化合物,其中R1-R6各自独立为氢或由通式-C≡CSiRaRbRc表示的取代基,条件是R1-R6中的至少一个为由通式-C≡CSiRaRbRc表示的取代基,其中Ra、Rb、Rc各自独立为C1-C10脂族烃基或芳族烃基。所述化合物通过使卤代苯并菲化合物(X1-X6各自独立为H、Br或碘,条件是X1-X6中的至少一个为Br或碘)与通式HC≡CSiRaRbRc(Ra、Rb、Rc与上述相同)的甲硅烷基乙炔偶合而制备。还公开了含有发光层的有机电致发光器件,所述发光层含有式化合物中的至少一种和磷光掺杂剂。明确公开了出式化合物,其中X1-X6各自为Br。
US2005025993涉及电致发光器件,所述器件含有阳极;阴极;位于所述阳极与所述阴极之间的第一有机层,其中所述第一有机层含有当在阳极与阴极间施加电压时产生磷光发射的材料;和位于第一有机层与阴极之间的第二有机层,其中所述第二有机层直接与第一有机层接触,且其中所述第二有机层含有非杂环芳烃材料,例如
JP2006104124涉及由通式(I)表示的化合物,其中R1-R6各自独立为氢或由通式-C≡CSiRaRbRc表示的取代基,条件是R1-R6中的至少一个为由通式-C≡CSiRaRbRc表示的取代基,其中Ra、Rb、Rc各自独立为C1-10脂族烃基或芳族烃基。还公开了一种具有发光层的有机电致发光器件,所述发光层含有化合物I中的至少一种和磷光掺杂剂。
WO2006047119(US2006/0088728)涉及一种器件,所述器件含有:阳极;阴极;位于阳极与阴极之间的发射层,其中所述发射层含有基质和掺杂剂,其中所述基质材料选自:
其中各R代表无取代、单-、二-或三取代,其中所述取代基相同或不同,且各自选自烷基、链烯基、炔基、芳基、硫代烷氧基、卤基、卤代烷基、氰基、羰基、羧基、杂芳基和取代芳基,且其中各化合物I、II、III或IV的至少一个R包括咔唑基团。如下化合物明确公开于WO2006047119中:和
WO2006130598涉及一种含有磷光材料和具有下式的苯并菲化合物的发射层:
其中R1、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11和R12各自独立为H或选自芳基、取代芳基、杂芳基、取代杂芳基、烷基、芳烷基、杂烷基、链烯基和炔基的取代基;且其中所述苯并菲化合物具有至少2个取代基且分子量为小于1400。在优选且通过实施例明确公开的化合物中,R9和R12中的至少一个为氢。
US2007087223涉及在二苯并[a,c]蒽骨架的9位和14位中的至少一处被氨基化合物基团取代且由下式(1)或(2)表示的二苯并蒽衍生物:
X1、X2和X各自独立代表取代或未取代的亚芳基或取代或未取代的二价杂环基团;
A、B、D和D’各自独立代表取代或未取代的烷基、取代或未取代的芳基或取代或未取代的杂环基团,且在相邻基团之间可稠合在一起以形成环;和
Y1-Y12和R1各自独立代表氢原子、卤素原子、取代或未取代的烷基、烷氧基、取代或未取代的芳基或取代或未取代的杂环基团;且当Y1-Y12和R1不为氢原子或卤素原子时,Y1-Y12和R1可在相邻基团之间稠合在一起以形成环。所述二苯并蒽衍生物用作发光材料。
尽管存在这些进展,但仍然需要含有新型基质材料的EL器件,尤其是与磷光材料一起作用以提供电致发光器件的改善的效率、稳定性、可制造性和/或光谱特征的基质。
R1和R2相互独立为可任选被取代的C6-C24芳基或C2-C30杂芳基,
R3和R4相互独立为氢、可任选被取代的C1-C25烷基、C6-C24芳基或C2-C30杂芳基,
Ar和Ar’相互独立为C6-C14芳基,例如苯基或萘基,其可任选被1个或多个选自可任选间隔有-O-的C1-C25烷基或C1-C25烷氧基的基团取代,
R5和R6相互独立为卤素或有机取代基,或
彼此相邻的R5和R6一起形成可任选被取代的芳族或杂芳族环或环体系,
A1、A2、A1’和A2’相互独立为可任选被取代的C6-C24芳基、C2-C30杂芳基,或
A4、A4’、A6、A7、A8、A5、A5’、A6’、A7’和A8’相互独立为可任选被取代的C6-C24芳基或C2-C30杂芳基,
m1在每次出现时可相同或不同且为0、1、2、3或4,尤其是0、1或2,非常尤其为0或1,
R119和R120相互独立为C1-C18烷基、被E取代和/或间隔有D的C1-C18烷基、C6-C24芳基、被G取代的C6-C24芳基、C2-C20杂芳基、被G取代的C2-C20杂芳基、C2-C18链烯基、C2-C18炔基、C1-C18烷氧基、被E取代和/或间隔有D的C1-C18烷氧基或C7-C25芳烷基,或
R119和R120一起形成式=CR121R122的基团,其中:
R121和R122相互独立为H、C1-C18烷基、被E取代和/或间隔有D的C1-C18烷基、C6-C24芳基、被G取代的C6-C24芳基、C2-C20杂芳基或被G取代的C2-C20杂芳基,或
R119和R120一起形成五或六元环,所述环可任选被C1-C18烷基、被E取代和/或间隔有D的C1-C18烷基、C6-C24芳基、被G取代的C6-C24芳基、C2-C20杂芳基、被G取代的C2-C20杂芳基、C2-C18链烯基、C2-C18炔基、C1-C18烷氧基、被E取代和/或间隔有D的C1-C18烷氧基、C7-C25芳烷基或-C(=O)-R127取代,和
R127为H、C6-C18芳基、被C1-C18烷基或C1-C18烷氧基取代的C6-C18芳基、C1-C18烷基或间隔有-O-的C1-C18烷基,
D为-CO-、-COO-、-S-、-SO-、-SO2-、-O-、-NR65-、-SiR70R71-、-POR72-、-CR63=CR64-或-C≡C-,和
E为-OR69、-SR69、-NR65R66、-COR68、-COOR67、-CONR65R66、-CN或卤素,
G为E或C1-C18烷基,
R63和R64相互独立为C6-C18芳基;被C1-C18烷基、C1-C18烷氧基取代的C6-C18芳基;C1-C18烷基;或间隔有-O-的C1-C18烷基;或
R65、R65’和R66相互独立为C6-C18芳基;被C1-C18烷基、C1-C18烷氧基取代的C6-C18芳基;C1-C18烷基;或间隔有-O-的C1-C18烷基;或
R65和R66一起形成五或六元环,
R67为C6-C18芳基;被C1-C18烷基或C1-C18烷氧基取代的C6-C18芳基;C1-C18烷基;或间隔有-O-的C1-C18烷基,
R68为H;C6-C18芳基;被C1-C18烷基或C1-C18烷氧基取代的C6-C18芳基;C1-C18烷基;或间隔有-O-的C1-C18烷基,
R69为C6-C18芳基;被C1-C18烷基、C1-C18烷氧基取代的C6-C18芳基;C1-C18烷基;或间隔有-O-的C1-C18烷基,
R70和R71相互独立为C1-C18烷基、C6-C18芳基或被C1-C18烷基取代的C6-C18芳基;和
R72为C1-C18烷基、C6-C18芳基或被C1-C18烷基取代的C6-C18芳基;
R41在每次出现时可相同或不同且为Cl,F,CN,NR45R45’,C1-C25烷基,C4-C18环烷基,C1-C25烷氧基,其中1个或多个彼此不相邻的碳原子可被-NR45-、-O-、-S-、-C(=O)-O-或-O-C(=O)-O-替换,和/或其中1个或多个氢原子可被F替换,C6-C24芳基或C6-C24芳氧基,其中1个或多个碳原子可被O、S或N替换,和/或其可被1个或多个非芳族基团R41取代,或2个或更多个基团R41形成环体系;
R45和R45’相互独立为C1-C25烷基,C4-C18环烷基,其中1个或多个彼此不相邻的碳原子可被-NR45”-、-O-、-S-、-C(=O)-O-或-O-C(=O)-O-替换,和/或其中1个或多个氢原子可被F替换,C6-C24芳基或C6-C24芳氧基,其中1个或多个碳原子可被O、S或N替换,和/或其可被1个或多个非芳族基团R41取代,
R45”为C1-C25烷基或C4-C18环烷基,和
m在每次出现时可相同或不同且为0、1、2或3,尤其是0、1或2,非常尤其为0或1。
本发明化合物在固态倾向于为无定形,因此,可通过升华或由溶液处理。
本发明电子器件优选为电致发光(EL)器件。式I化合物可作为磷光化合物的基质用于有机发光二极管(OLED)中。因此,本发明还提供了含有式I化合物的电致发光器件,尤其是含有阴极、阳极和在此之间的发光层的电致发光器件,所述发光层含有基质材料和磷光发光材料,其中所述基质材料为式I化合物。另外,式I化合物可用作空穴或电子阻隔材料和/或空穴或电子传输材料。
优选式I化合物为下式化合物:
本发明化合物的特征在于R1和R2为可任选被取代的C6-C24芳基或C2-C30杂芳基。优选R1和R2为可任选被取代的C6-C24芳基,例如或其中R7、R8和R9相互独立为H、C1-C18烷基、C1-C18烷氧基或间隔有O的C1-C18烷基。
在本发明优选的实施方案中,R1和R2为可任选被取代的C6-C24芳基,R3为氢,R4为可任选被取代的C1-C25烷基或C6-C24芳基,或R3和R4为可任选被取代的C6-C24芳基。可任选被取代的C6-C24芳基的实例为或其中R7、R8和R9如上定义。
在本发明其它优选的实施方案中,R1和R2为可任选取代的C2-C30杂芳基,R3为氢,R4为可任选被取代的C2-C30杂芳基;或R3和R4为可任选被取代的C2-C30杂芳基。可任选被取代的C2-C30杂芳基的实例为式化合物,其中R7、R8和R9如上定义。
L1和L2的实例为单键、-(CR47=CR48)m2-、-(Ar3)m3-、-[Ar3(Y1)m5]m4-、-[(Y1)m5Ar3]m4-或-[Ar3(Y2)m5Ar4]m4-,其中Y1、Y2、R47、R48、Ar3、Ar4、m2、m3、m4和m5如下定义。优选L1和L2为单键或式 或的桥接单元BU。
-L1-X1和-L2-X2的实例为,其中R200为可任选间隔有-O-的C1-C25烷基、C1-C25烷氧基、和其中R116和R117如下定义。-L1-X1优选为基团或-NA1A1’。-L2-X2优选为基团或-NA2A2’。X1和X2可不同,但优选相同。
在优选实施方案中,-L1-X1和-L2-X2相互独立为式的基团,-NA1A1’,或基团其中A1、A1’、A3和A3’相互独立为可任选被取代的C6-C24芳基或C2-C30杂芳基,尤其是可任选被取代的苯基、萘基、蒽基、联苯基、2-芴基、菲基或苝基,例如 和或A1和A1’或A3和A3’与其连接的氮原子一起形成杂芳族环或环体系,例如或m’为0、1或2;
m1在每次出现时可相同或不同且为0、1、2、3或4,尤其是0、1或2,非常尤其为0或1;
R116、R117和R117’相互独立为H、卤素、-CN、C1-C18烷基、被E取代和/或间隔有D的C1-C18烷基、C6-C24芳基、被G取代的C6-C24芳基、C2-C20杂芳基、被G取代的C2-C20杂芳基、C2-C18链烯基、C2-C18炔基、C1-C18烷氧基、被E取代和/或间隔有D的C1-C18烷氧基、C7-C25芳烷基、-C(=O)-R127、-C(=O)OR127或-C(=O)NR127R126,或
彼此相邻的取代基R116、R117和R117’可形成环,
R119和R120如上定义,
R126和R127相互独立为H;C6-C18芳基;被C1-C18烷基或C1-C18烷氧基取代的C6-C18芳基;C1-C18烷基;或间隔有-O-的C1-C18烷基,
R116、R116’、R117和R117’相互独立为H、卤素、-CN、C1-C18烷基、被E取代和/或间隔有D的C1-C18烷基、C6-C24芳基、被G取代的C6-C24芳基、C2-C20杂芳基、被G取代的C2-C20杂芳基、C2-C18链烯基、C2-C18炔基、C1-C18烷氧基、被E取代和/或间隔有D的C1-C18烷氧基、C7-C25芳烷基、-C(=O)-R127、-C(=O)OR127或-C(=O)NR127R126,或彼此相邻的取代基R116、R116’、R117和R117’可形成环,
R126和R127相互独立为H;C6-C18芳基;被C1-C18烷基或C1-C18烷氧基取代的C6-C18芳基;C1-C18烷基;或间隔有-O-的C1-C18烷基,和
其中R116、R117和R117’如上定义。
R116和R117相互独立为可任选间隔有-O-的C1-C25烷基,或C1-C25烷氧基;
优选R116、R116’、R117和R117’相互独立为H,C1-C12烷基,例如甲基、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、异戊基、正己基、2-乙基己基或正庚基,被E取代和/或间隔有D的C1-C12烷基,例如-CH2OCH3、-CH2OCH2CH3、-CH2OCH2CH2OCH3或-CH2OCH2CH2OCH2CH3,C6-C14芳基,例如苯基、萘基或联苯基,C5-C12环烷基,例如环己基,被G取代的C6-C14芳基,例如-C6H4OCH3、-C6H4OCH2CH3、-C6H3(OCH3)2或-C6H3(OCH2CH3)2、-C6H4CH3、-C6H3(CH3)2、-C6H2(CH3)3或-C6H4tBu。
优选R119和R120相互独立为C1-C12烷基,例如甲基、乙基、正丙基、异丙基、正丁基、仲丁基、己基、辛基或2-乙基己基,被E取代和/或间隔有D的C1-C12烷基,例如-CH2(OCH2CH2)wOCH3,w=1、2、3或4,C6-C14芳基,例如苯基、萘基或联苯基,被G取代的C6-C14芳基,例如-C6H4OCH3、-C6H4OCH2CH3、-C6H3(OCH3)2、-C6H3(OCH2CH3)2、-C6H4CH3、-C6H3(CH3)2、-C6H2(CH3)3或-C6H4tBu,或R119和R120一起形成4-8元环,特别是5或6元环,例如可任选被C1-C8烷基取代的环己基或环戊基。
D优选为-CO-、-COO-、-S-、-SO-、-SO2-、-O-、-NR65-,其中R65为C1-C12烷基,例如甲基、乙基、正丙基、异丙基、正丁基、异丁基或仲丁基,或C6-C14芳基,例如苯基、萘基或联苯基。
E优选为-OR69、-SR69、-NR65R65、-COR68、-COOR67、-CONR65R65或-CN;其中R65、R67、R68和R69相互独立为C1-C12烷基,例如甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基、己基、辛基或2-乙基己基,或C6-C14芳基,例如苯基、萘基或联苯基,其可任选被取代。
G具有与E相同的优选,或为C1-C18烷基,尤其是C1-C12烷基,例如甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基、己基、辛基或2-乙基己基。
在本发明其它优选的实施方案中,X1和X2为缺电子的杂芳基。
术语“缺电子的杂芳基”指其中孤立(未连接)的缺电子杂芳基单元的HOMO为-5.3eV或更低的基团。优选X1和X2中的至少一个,更优选X1和X2均为缺电子的杂芳基。
已以几种方式估计待用于OLED中的有机材料的HOMO和LUMO能级。用于估计HOMO能级的2种常见方法为溶液电化学和紫外线光电子光谱(UPS)。用于测量氧化和还原电位的最常见方法为循环伏安法,而用高浓度电解质溶解与该基团相应的分析物或化合物。插入电极并在正或负方向(取决于进行氧化或还原)上扫描电压。通过流经电池的电流表明氧化还原反应的存在。然后,反向电压扫描并使氧化还原反应反向。如果两个氧化还原波的面积相同,则该过程可逆。这些事件发生时的电位给出了相对于参照的还原或氧化电位值。参照可为外部参照如Ag/AgCl或SCE,或其可为内部参照如具有已知氧化电位的二茂铁。
虽然这是一种与固态OLED相反的溶液方法,且可能难以调整所述参照以给出相对于真空的值,但该方法有利于给出相对值。可来自电化学测量的一个有用参数为带电体间隙(carrier gap)。如果还原和氧化均可逆,则可确定空穴与电子之间的能量差异。该值对由良好定义的HOMO能量确定LUMO能量是重要的。
在固态估计HOMO能量的优选方法为UPS。这是一种其中用UV光子照射固体的光电测量法。逐渐增加光子能量直至释放产生光的电子。喷出电子的启动给出HOMO能量。用来测量HOMO能量的最高程度地认可的方法为UPS,其以eV给出相对于真空的值。这为电子结合能。
如果其在常规能级图上较低,则认为第一能级(HOMO或LUMO)“小于”或“低于”第二能级,这意味着第一能级具有比第二能级更负的值。
其中:
X3代表O、S或N-R121’,尤其是N-R121’;
X9代表O、S或N-R121’,尤其是O;
Q1和Q2代表形成碳环芳族或杂环芳族环所需要的原子,其可任选与其它环稠合以形成稠环和/或可任选被G取代;
R116和R117如上述定义;
R121’为H;C6-C18芳基;或C2-C20杂芳基;其可任选被C1-C18烷基、C1-C18全氟烷基或C1-C18烷氧基取代;C1-C18烷基;或间隔有-O-的C1-C18烷基;
R120’、R123、R124和R125相互独立为H、C1-C18烷基、被E取代和/或间隔有D的C1-C18烷基、C1-C18全氟烷基、可任选被G取代的C6-C24芳基、可任选被G取代的C2-C20杂芳基、C2-C18链烯基、C2-C18炔基、C1-C18烷氧基、被E取代和/或间隔有D的C1-C18烷氧基或C7-C25芳烷基;
R128和R128’相互独立为H、CN、C1-C18烷基、被E取代和/或间隔有D的C1-C18烷基、C1-C18全氟烷基、可任选被G取代的C6-C24芳基、可任选被G取代的C2-C20杂芳基、C2-C18链烯基、C2-C18炔基、C1-C18烷氧基、被E取代和/或间隔有D的C1-C18烷氧基或C7-C25芳烷基;
L1为单键、-(CR47=CR48)m2-、-(Ar3)m3-、-[Ar3(Y1)m5]m4-、-[(Y1)m5Ar3]m4-或-[Ar3(Y2)m5Ar4]m4-,其中:
Y1为-(CR47=CR48)-,
Y2为NR49、O、S、C=O、C(=O)O,其中R49为可任选被C1-C18烷基或C1-C18烷氧基取代的C6-C18芳基;C1-C18烷基;或间隔有-O-的C1-C18烷基;
R47和R48相互独立为氢、可任选被G取代的C1-C20烷基或C6-C24芳基;
m5为1-10的整数,m2为1-10的整数,m3为1-5的整数,m4为1-5的整数;
Ar3和Ar4相互独立为可任选被取代的亚芳基或亚杂芳基。
X4、X5和X6相互独立为N或CH,条件是取代基X4、X5和X6中的至少一个,优选至少两个为N,和
Ar1和Ar2相互独立为可任选被G取代的C6-C24芳基,或可任选被G取代的C2-C20杂芳基,其中D、E和G如上述定义。
R128和R128’优选相互独立为H、CN、C1-C18烷基、被E取代和/或间隔有D的C1-C18烷基、C1-C18全氟烷基、可任选被G取代的C6-C24芳基、可任选被G取代的C2-C20杂芳基,或C7-C25芳烷基。
R120’、R123、R124和R125优选相互独立为H、C1-C18烷基、被E取代和/或间隔有D的C1-C18烷基、C1-C18全氟烷基、可任选被G取代的C6-C24芳基,或可任选被G取代的C2-C20杂芳基。
由Q1或Q2形成的芳族杂环的具体实例包括吡啶、吡嗪、嘧啶、哒嗪和三嗪。优选为吡啶、吡嗪、嘧啶和哒嗪,其中更优选吡啶和吡嗪,仍更优选吡啶。由Q1或Q2形成的(6元)芳族杂环可与其它环稠合以形成稠环,或可具有取代基G。
在本发明这一方面中,基团-L1-X1和-L1-X2的更具体实例为如下基团:
m6为0或1-3的整数,
m7为0、1或2,
R116和R117如上定义,
R123、Ar1和Ar2相互独立为苯基或1-或2-萘基,其可被C1-C18烷基、可任选间隔有O的C1-C18烷基或可任选间隔有O的C1-C18烷氧基取代1-3次,
R129在每次出现时可相同或不同且为F、-CN、C1-C18烷基、被E取代和/或间隔有D的C1-C18烷基、C6-C24芳基、被G取代的C6-C24芳基、C2-C20杂芳基、被G取代的C2-C20杂芳基、C2-C18链烯基、C2-C18炔基、C1-C18烷氧基、被E取代和/或间隔有D的C1-C18烷氧基、C7-C25芳烷基、-C(=O)-R130、-C(=O)OR130’或-C(=O)NR131R131’;或彼此相邻的取代基R129可形成环,
R131和R131’相互独立为H;C6-C18芳基;或C2-C20杂芳基;其可任选被C1-C18烷基、C1-C18全氟烷基或C1-C18烷氧基取代;C1-C18烷基;或间隔有-O-的C1-C18烷基;
R130和R130’相互独立为H;C6-C18芳基;被C1-C18烷基或C1-C18烷氧基取代的C6-C18芳基;C1-C18烷基;或间隔有-O-的C1-C18烷基,
X7和X8相互独立为N或CR127”,其中R127”具有R126的含义,且R120’、R124、R125、X3、X4、X5、X6、X9和L1如上定义。
在以上基团-L1-X1和-L2-X2中,甚至更优选如下基团:
R41在每次出现时可相同或不同且为F,CN,N(R45)2,C1-C25烷基,C4-C18环烷基,C1-C25烷氧基,其中1个或多个彼此不相邻的碳原子可被-NR45-、-O-、-S-、-C(=O)-O-或-O-C(=O)-O-替换,和/或其中1个或多个氢原子可被F替换,C6-C24芳基或C6-C24芳氧基,其中1个或多个碳原子可被O、S或N替换,和/或其可被1个或多个非芳族基团R41取代,或2个或更多个基团R41形成环体系;
R45为C1-C25烷基,C4-C18环烷基,其中1个或多个彼此不相邻的碳原子可被-NR45”-、-O-、-S-、-C(=O)-O-或-O-C(=O)-O-替换,和/或其中1个或多个氢原子可被F替换,C6-C24芳基或C6-C24芳氧基,其中1个或多个碳原子可被O、S或N替换,和/或其可被1个或多个非芳族基团R41取代,且R45”为C1-C25烷基或C4-C18环烷基;
n1为0或1-3的整数,和
R47、R48、R119和R120如上定义。
在本发明特别优选的实施方案中,-L1-X1和-L2-X2相互独立为基团
在本发明其它优选的实施方案中,-L1-X1和-L2-X2相互独立为基团
R116、R116’、R117和R117’相互独立为H、卤素、-CN、C1-C18烷基、被E取代和/或间隔有D的C1-C18烷基、C6-C24芳基、被G取代的C6-C24芳基、C2-C20杂芳基、被G取代的C2-C20杂芳基、C2-C18链烯基、C2-C18炔基、C1-C18烷氧基、被E取代和/或间隔有D的C1-C18烷氧基、C7-C25芳烷基、-C(=O)-R127’、-C(=O)OR127’或-C(=O)NR127’R126’,或彼此相邻的取代基R116、R116’、R117和R117’可形成环,
R126’和R127’相互独立为H;C6-C18芳基;被C1-C18烷基或C1-C18烷氧基取代C6-C18芳基;C1-C18烷基,或间隔有-O-的C1-C18烷基,
D、E和G如上定义。
优选R116、R116’、R117和R117’相互独立为H、F、-CN、C1-C18烷基、被E取代和/或间隔有D的C1-C18烷基、C1-C18烷氧基、被E取代和/或间隔有D的C1-C18烷氧基、C6-C24芳基、被G取代的C6-C24芳基,
D为-O-;-NR65-;和
E为-OR69;-NR65R66,-CN或F;
G为E、C1-C18烷基、间隔有O的C1-C18烷基、C1-C18烷氧基或间隔有O的C1-C18烷氧基,其中:
R65和R66相互独立为C6-C18芳基;被C1-C18烷基或C1-C18烷氧基取代的C6-C18芳基;C1-C18烷基;或间隔有-O-的C1-C18烷基;或
R65和R66一起形成五或六元环;和
R69为C6-C18芳基;被C1-C18烷基或C1-C18烷氧基取代的C6-C18芳基;
C1-C18烷基;或间隔有-O-的C1-C18烷基。
特别优选的化合物的实例为权利要求7所示化合物A1-A21、B1-B21、C1-C21和D1-D21。
其中-L1-X1和-L2-X2相互独立为-NA1A1’、或的式I化合物可例如根据如下方法制备,所述方法包括使式(XX)化合物,其中X10代表卤素如溴或碘,与式HNA1A1’、或化合物在碱如氢化钠、碳酸钾或碳酸钠,和催化剂如铜(0)或铜(I)(例如铜、铜-青铜、溴化碘化铜或溴化铜)存在下,在溶剂如甲苯、二甲基甲酰胺或二甲亚砜中反应,其中A1、A1’、L1、L2、R1、R2、R3、R4、R5、R6、R41、m1和m如上定义。
此反应(称作Ullmann缩合)为Yamamoto & Kurata,Chem.andIndustry,737-738(1981)、J.Mater.Chem.14(2004)2516、H.B.Goodbrand等,J.Org.Chem.64(1999)670和K.D.Bellfield等,J.Org.Chem.65(2000)4475所描述,其中使用铜作为催化剂。另外,钯催化剂可用于将芳基卤素化合物与胺偶合,如M.D.Charles等,Organic Lett.7(2005)3965、A.F.Littke等,Angew.Chem.Int.Ed.41(2002)4176和其中所引用的文献所述。
式XX化合物由WO08/012250已知,或可根据或类似于其中所述方法制备。
卤素为氟、氯、溴和碘。
C1-C25烷基通常为线性或如果可能支化的。实例为甲基、乙基、正丙基、异丙基、正丁基、仲丁基、异丁基、叔丁基、正戊基、2-戊基、3-戊基、2,2-二甲基丙基、1,1,3,3-四甲基戊基、正己基、1-甲基己基、1,1,3,3,5,5-六甲基己基、正庚基、异庚基、1,1,3,3-四甲基丁基、1-甲基庚基、3-甲基庚基、正辛基、1,1,3,3-四甲基丁基和2-乙基己基、正壬基、癸基、十一烷基、十二烷基、十三烷基、十四烷基、十五烷基、十六烷基、十七烷基、十八烷基、二十烷基、二十一烷基、二十二烷基、二十四烷基或二十五烷基。C1-C8烷基通常为甲基、乙基、正丙基、异丙基、正丁基、仲丁基、异丁基、叔丁基、正戊基、2-戊基、3-戊基、2,2-二甲基丙基、正己基、正庚基、正辛基、1,1,3,3-四甲基丁基和2-乙基己基。C1-C4烷基通常为甲基、乙基、正丙基、异丙基、正丁基、仲丁基、异丁基、叔丁基。
C1-C25烷氧基为直链或支化烷氧基,例如甲氧基、乙氧基、正丙氧基、异丙氧基、正丁氧基、仲丁氧基、叔丁氧基、戊氧基、异戊氧基或叔戊氧基、庚氧基、辛氧基、异辛氧基、壬氧基、癸氧基、十一烷氧基、十二烷氧基、十四烷氧基、十五烷氧基、十六烷基基、十七烷氧基和十八烷氧基。C1-C8烷氧基的实例为甲氧基、乙氧基、正丙氧基、异丙氧基、正丁氧基、仲丁氧基、异丁氧基、叔丁氧基、正戊氧基、2-戊氧基、3-戊氧基、2,2-二甲基丙氧基、正己氧基、正庚氧基、正辛氧基、1,1,3,3-四甲基丁氧基和2-乙基己氧基,优选C1-C4烷氧基,例如通常为甲氧基、乙氧基、正丙氧基、异丙氧基、正丁氧基、仲丁氧基、异丁氧基、叔丁氧基。术语“烷硫基”指与烷氧基相同的基团,不同之处在于醚键的氧原子被硫原子替换。
C2-C25链烯基为直链或支化链烯基,例如乙烯基、烯丙基、甲基烯丙基、异丙烯基、2-丁烯基、3-丁烯基、异丁烯基、正戊-2,4-二烯基、3-甲基-丁-2-烯基、正辛-2-烯基、正十二-2-烯基、异十二烯基、正十二-2-烯基或正十八-4-烯基。
C2-24炔基为直链或支化的,优选C2-8炔基,其可为未取代或取代的,例如乙炔基、1-丙炔-3-基、1-丁炔-4-基、1-戊炔-5-基、2-甲基-3-丁炔-2-基、1,4-戊二炔-3-基、1,3-戊二炔-5-基、1-己炔-6-基、顺-3-甲基-2-戊烯-4-炔-1-基、反-3-甲基-2-戊烯-4-炔-1-基、1,3-己二炔-5-基、1-辛炔-8-基、1-壬炔-9-基、1-癸炔-10-基或1-二十四炔-24-基。
C1-C18全氟烷基,尤其是C1-C4全氟烷基为支化或未支化的基团,例如-CF3、-CF2CF3、-CF2CF2CF3、-CF(CF3)2、-(CF2)3CF3和-C(CF3)3。
术语“卤代烷基、卤代链烯基和卤代炔基”指通过用卤素部分或完全取代上述烷基、链烯基和炔基得到的基团,例如三氟甲基等。“醛基、酮基、酯基、氨基甲酰基和氨基”包括被烷基、环烷基、芳基、芳烷基或杂环基团取代的那些,其中烷基、环烷基、芳基、芳烷基和杂环基团可为未取代或取代的。术语“甲硅烷基”指式-SiR62’R63’64’的基团,其中R62’、R63’和64’相互独立为C1-C8烷基,特别是C1-C4烷基,C6-C24芳基或C7-C12芳烷基,例如三甲基甲硅烷基。术语“硅氧烷基”指式-O-SiR62’R63’64’的基团,其中R62’、R63’和64’如上定义,例如三甲基硅氧烷基。
术语“环烷基”通常为C5-C12环烷基,例如环戊基、环己基、环庚基、环辛基、环壬基、环癸基、环十一烷基、环十二烷基,优选环戊基、环己基、环庚基或环辛基,其可为未取代或取代的。术语“环烯基”指含有1个或多个双键的不饱和脂环烃基,例如环戊烯基、环戊二烯基、环己烯基等,其可为未取代或取代的。环烷基,特别是环己基,可与可用C1-C4烷基、卤素和氰基取代1-3次的苯基稠合1次或2次。此类稠合环己基的实例为:或特别是或其中R51、R52、R53、R54、R55和R56相互独立为C1-C8烷基、C1-C8烷氧基、卤素和氰基,特别是氢。
芳基通常为可任选被取代的C6-C30芳基,优选C6-C24芳基,例如苯基、4-甲基苯基、4-甲氧基苯基、萘基,尤其是1-萘基或2-萘基、联苯基、三联苯基、芘基、2-或9-芴基、菲基、蒽基、四环(tetracyl)、五环(pentacyl)、六环(hexacyl)或四联苯基,其可为未取代或取代的。
术语“芳烷基”通常为C7-C24芳烷基,例如苄基、2-苄基-2-丙基、β-苯基乙基、α,α-二甲基苄基、ω-苯基丁基、ω,ω-二甲基-ω-苯基丁基、ω-苯基十二烷基、ω-苯基十八烷基、ω-苯基二十烷基或ω-苯基-二十二烷基,优选C7-C18芳烷基,例如苄基、2-苄基-2-丙基、β-苯基乙基、α,α-二甲基苄基、ω-苯基丁基、ω,ω-二甲基-ω-苯基丁基、ω-苯基十二烷基或ω-苯基十八烷基,特别优选C7-C12芳烷基,例如苄基、2-苄基-2-丙基、β-苯基乙基、α,α-二甲基苄基、ω-苯基丁基、ω,ω-二甲基-ω-苯基丁基,其中脂族烃基和芳族烃基均可为未取代或取代的。
术语“芳基醚基团”通常为C6-24芳氧基,即O-C6-24芳基,例如苯氧基或4-甲氧基苯基。术语“芳基硫醚基团”通常为C6-24芳硫基,即S-C6-24芳基,例如苯硫基或4-甲氧基苯硫基。术语“氨基甲酰基”通常为C1-18氨基甲酰基,优选C1-8氨基甲酰基,其可为未取代或取代的,例如氨基甲酰基、甲基氨基甲酰基、乙基氨基甲酰基、正丁基氨基甲酰基、叔丁基氨基甲酰基、二甲基氨基甲酰氧基、吗啉代氨基甲酰基或吡咯烷氨基甲酰基。
烷基氨基、二烷基氨基、烷基芳基氨基、芳基氨基和二芳基中的术语“芳基”和“烷基”通常分别为C1-C25烷基和C6-C24芳基。
烷基芳基指烷基取代的芳基,尤其是C7-C12烷基芳基。实例为甲苯基,例如3-甲基-或4-甲基苯基;或二甲苯基,例如3,4-二甲基苯基或3,5-二甲基苯基。
杂芳基通常为C2-C26杂芳基,即具有5-7个环原子的环或稠环体系,其中氮、氧或硫为可能的杂原子,通常为具有5-30个原子且具有至少6个共轭π电子的不饱和杂环基团,例如噻吩基、苯并[b]噻吩基、二苯并[b,d]噻吩基、噻蒽基、呋喃基、糠基、2H-吡喃基、苯并呋喃基、异苯并呋喃基、二苯并呋喃基、苯氧基噻吩基、吡咯基、咪唑基、吡唑基、吡啶基、联吡啶基、三嗪基、嘧啶基、吡嗪基、哒嗪基、中氮茚基、异吲哚基、吲哚基、吲唑基、嘌呤基、喹嗪基、喹啉基、异喹啉基、酞嗪基、萘啶基、喹噁啉基、喹唑啉基、噌啉基、蝶啶基、咔唑基、咔啉基、苯并三唑基、苯并噁唑基、菲啶基、吖啶基、嘧啶基、菲咯啉基、吩嗪基、异噻唑基、吩噻嗪基、异噁唑基、呋咱基或吩噁嗪基,其可为未取代或取代的。
上述基团的可能取代基为C1-C8烷基、羟基、巯基、C1-C8烷氧基、C1-C8烷硫基、卤素、卤代-C1-C8烷基、氰基、醛基、酮基、羧基、酯基、氨基甲酰基、氨基、硝基或甲硅烷基,其中优选C1-C8烷基、C1-C8烷氧基、氰基或甲硅烷基。
如果取代基如R6在基团中出现一次以上时,则其在每次出现时可不同。
措词“被G取代”指可存在1个或多个,尤其是1-3个取代基G。
如上所述,前述基团可被E取代和/或如果需要间隔有D。当然,间隔仅仅在含有至少2个通过单键相互连接的碳原子的基团情况下才是可能的;C6-C18芳基未间隔;间隔的芳烷基或烷基芳基在烷基部分中含有单元D。被1个或多个E取代和/或间隔有1个或多个单元D的C1-C18烷基为例如(CH2CH3O)1-9-Rx,其中Rx为H或C1-C10烷基或C2-C10烷酰基(例如CO-CH(C2H5)C4H9),CH2-CH(ORy’)-CH2-O-Ry,其中Ry为C1-C18烷基、C5-C12环烷基、苯基、C7-C15苯基烷基,Ry’包括与Ry相同的定义或为H;C1-C8亚烷基-COO-Rz,例如CH2COORz,CH(CH3)2COORz,C(CH3)2COORz,其中Rz为H,C1-C18烷基,(CH2CH2O)1-9-Rx,Rx包括上文所示定义;CH2CH2-O-CO-CH=CH2;CH2CH(OH)CH2-O-CO-C(CH3)=CH2。
优选的亚芳基为1,4-亚苯基、2,5-亚甲苯基、1,4-亚萘基、1,9-亚蒽基、2,7-亚菲基和2,7-亚二氢菲基。
优选的亚杂芳基为2,5-亚吡嗪基、3,6-亚哒嗪基、2,5-亚吡啶基、2,5-亚嘧啶基、1,3,4-噻二唑-2,5-亚基、1,3-噻唑-2,4-亚基、1,3-噻唑-2,5-亚基、2,4-亚噻吩基、2,5-亚噻吩基、1,3-噁唑-2,4-亚基、1,3-噁唑-2,5-亚基和1,3,4-噁二唑-2,5-亚基、2,5-亚茚基和2,6-亚茚基。
本发明电子器件优选为电致发光(EL)器件。式I化合物可在有机发光二极管(OLED)中用作磷光化合物的基质。因此,本发明还涉及一种含有式I化合物的电致发光器件。在优选的实施方案中,电致发光器件含有阴极、阳极和在此之间含有基质材料和磷光发光材料的发光层,其中所述基质材料为式I化合物。
OLED器件的发光层合适地含有基质材料和1种或多种用于发光的客体材料。基质材料中的至少一种为包含式I化合物的化合物。发光客体材料通常以小于基质材料量的量存在,存在量通常为基质的至多15重量%,更通常为基质的0.1-10重量%,常为基质的2-8%。为简便起见,在本发明中可将磷光络合物客体材料称作磷光材料。发射层可含有结合了传输和发射性能的单一材料。不论发射材料为掺杂剂还是主要组分,发射层均可含有其它材料,例如调整发射层发射的掺杂剂。发射层可含有多种能组合发射所需光谱光的发射材料。
磷光材料的其它基质材料
用于本发明的基质材料可单独或与其它基质材料组合使用。应对其它基质材料进行选择从而可将三重态激子有效地从基质材料转移至磷光材料。适合的基质材料描述于WO00/70655;01/39234;01/93642;02/074015;02/15645和US20020117662中。适合的基质包括某些芳基胺、三唑、吲哚和咔唑化合物。基质的实例为4,4’-N,N’-二咔唑联苯(CBP)、2,2’-二甲基-4,4’-N,N’-二咔唑联苯、间-(N,N’-二咔唑)苯和聚(N-乙烯基咔唑),其中包括其衍生物。
理想的基质材料能形成连续膜。发光层可含有一种以上基质材料,以改善器件的膜形态、电性能、发光效率和使用寿命。发光层可含有具有良好空穴传输性能的第一基质材料和具有良好电子传输性能的第二基质材料。
磷光材料
在相同或不同层中,磷光材料可单独使用,或在某些情况下相互组合使用。磷光剂和相关材料的实例描述于WO00/57676、WO00/70655、WO01/41512、WO02/15645、US2003/0017361、WO01/93642、WO01/39234、US6,458,475、WO02/071813、US6,573,651、US2002/0197511、WO02/074015、US6,451,455、US2003/0072964、US2003/0068528、US6,413,656、6,515,298、6,451,415、6,097,147、US2003/0124381、US2003/0059646、US2003/0054198、EP1239526、EP1238981、EP1244155、US2002/0100906、US2003/0068526、US2003/0068535、JP2003073387、JP2003073388、US2003/0141809、US2003/0040627、JP2003059667、JP2003073665和US2002/0121638中。
IrL3和IrL2L’类型的环金属化Ir(III)络合物,例如发绿光的面-三(2-苯基吡啶-N,C2’)铱(III)和双(2-苯基吡啶-N,C2’)铱(III)(乙酰丙酮化物)的发射波长可通过在环金属化配体L上的适当位置取代给电子或吸电子基团,或通过选择环金属化配体L的不同杂环而移动。发射波长也可通过选择辅助配体L’而移动。红光发射剂的实例为双(1-(苯基)异喹啉)铱(III)乙酰丙酮化物、(乙酰丙酮)双-(2,3,5-三苯基吡嗪)铱(III)、双(2-(2’-苯并噻吩基)吡啶-N,C3’)铱(III)-(乙酰丙酮化物)和三(1-苯基异喹啉-N,C)铱(III)。发蓝光的实例为双(2-(4,6-二氟苯基)吡啶-N,C2’)铱(III)(甲基吡啶)。
已报告红色电致磷光,其中使用双(2-(2’-苯并[4,5-a]噻吩基)吡啶-N,C3)铱(乙酰丙酮化物)[Btp2Ir(acac)]作为磷光材料(Adachi,C.,Lamansky,S.,Baldo,M.A.,Kwong,R.C.,Thompson,M.E.和Forrest,S.R.,App.Phys.Lett.,78,1622 1624(2001))。
其它重要的磷光材料包括环金属化Pt(II)络合物如顺-双(2-苯基吡啶-N,C2’)铂(II)、顺-双(2-(2’-噻吩基)吡啶-N,C3’)铂(II)、顺-双(2-(2’-噻吩基)喹啉-N,C3’)铂(II)或(2-(4,6-二氟苯基)吡啶-NC2’)铂(II)乙酰丙酮化物。Pt(II)卟啉络合物如2,3,7,8,12,13,17,18-八乙基-21H,23H-卟吩铂(H)也为有用的磷光材料。
有用的磷光材料的其它实例还包括三价镧系元素如Th3+和Eu3+的配位络合物(J.Kido等,Appl.Phys.Lett.,65,2124(1994))。
其它重要的磷光材料描述于WO06/000544和PCT/EP2008/051702中。
磷光材料的实例为化合物A-1至B-234、B-1至B-234、C-1至C-44和D-1至D-234,其描述于PCT/EP2008/051702中:
化合物 | R2 | R3 | R6 |
A-1 | H | H | H |
A-2 | H | H | OCH3 |
A-3 | H | H | OCH2CH3 |
A-4 | H | H | O-正丁基 |
A-5 | H | H | O-异丁基 |
A-6 | H | H | O-2-丁基 |
化合物 | R2 | R3 | R6 |
A-7 | H | H | O-2-乙基己基 |
A-8 | H | H | N(CH3)2 |
A-9 | H | H | NPh2 |
A-10 | H | CF3 | H |
A-11 | CF3 | H | H |
A-12 | H | CF3 | OCH3 |
A-13 | CF3 | H | OCH3 |
A-14 | H | CF3 | OCH2CH3 |
A-15 | CF3 | H | OCH2CH3 |
A-16 | H | CF3 | O-正丁基 |
A-17 | CF3 | H | O-正丁基 |
A-18 | H | CF3 | O-异丁基 |
A-19 | CF3 | H | O-异丁基 |
A-20 | H | CF3 | O-2-丁基 |
A-21 | CF3 | H | O-2-丁基 |
A-22 | H | CF3 | O-2-乙基己基 |
A-23 | CF3 | H | O-2-乙基己基 |
A-24 | H | CF3 | N(CH3)2 |
A-25 | CF3 | H | N(CH3)2 |
A-26 | H | CF3 | NPh2 |
化合物 | R2 | R3 | R6 |
A-27 | CF3 | H | NPh2 |
A-28 | H | CN | H |
A-29 | CN | H | H |
A-30 | H | CN | OCH3 |
A-31 | CN | H | OCH2CH3 |
A-32 | H | CN | OCH2CH3 |
A-33 | CN | H | O-正丁基 |
A-34 | H | CN | O-正丁基 |
A-35 | CN | H | O-异丁基 |
A-36 | H | CN | O-异丁基 |
A-37 | CN | H | O-2-丁基 |
A-38 | H | CN | O-2-丁基 |
A-39 | CN | H | O-2-乙基己基 |
A-40 | H | CN | O-2-乙基己基 |
A-41 | CN | H | N(CH3)2 |
A-42 | H | CN | N(CH3)2 |
A-43 | CN | H | NPh2 |
A-44 | H | CN | NPh2 |
化合物 | L′ | R2 | R3 | R6 |
B-1 | A1) | H | H | H |
B-2 | A1) | H | H | OCH3 |
B-3 | A1) | H | H | OCH2CH3 |
B-4 | A1) | H | H | O-正丁基 |
B-5 | A1) | H | H | O-异丁基 |
B-6 | A1) | H | H | O-2-丁基 |
B-7 | A1) | H | H | O-2-乙基己基 |
B-8 | A1) | H | H | N(CH3)2 |
B-9 | A1) | H | H | NPh2 |
B-10 | A1) | H | CF3 | H |
B-11 | A1) | CF3 | H | H |
B-12 | A1) | H | CF3 | OCH3 |
B-13 | A1) | CF3 | H | OCH3 |
B-14 | A1) | H | CF3 | OCH2CH3 |
B-15 | A1) | CF3 | H | OCH2CH3 |
B-16 | A1) | H | CF3 | O-正丁基 |
化合物 | L′ | R2 | R3 | R6 |
B-17 | A1) | CF3 | H | O-正丁基 |
B-18 | A1) | H | CF3 | O-异丁基 |
B-19 | A1) | CF3 | H | O-异丁基 |
B-20 | A1) | H | CF3 | O-2-丁基 |
化合物 | L′ | R2 | R3 | R6 |
B-21 | A1) | CF3 | H | O-2-丁基 |
B-22 | A1) | H | CF3 | O-2-乙基己基 |
B-23 | A1) | CF3 | H | O-2-乙基己基 |
B-24 | A1) | H | CF3 | N(CH3)2 |
B-25 | A1) | CF3 | H | N(CH3)2 |
B-26 | A1) | H | CF3 | NPh2 |
B-27 | A1) | CF3 | H | NPh2 |
B-28 | A1) | H | CN | H |
B-29 | A1) | CN | H | H |
B-30 | A1) | CN | H | OCH3 |
B-31 | A1) | H | CN | OCH3 |
B-32 | A1) | CN | H | OCH2CH3 |
B-33 | A1) | H | CN | OCH2CH3 |
B-34 | A1) | CN | H | O-正丁基 |
B-35 | A1) | H | CN | O-正丁基 |
B-36 | A1) | CN | H | O-异丁基 |
B-37 | A1) | H | CN | O-异丁基 |
B-38 | A1) | CN | H | O-2-丁基 |
B-39 | A1) | H | CN | O-2-丁基 |
B-40 | A1) | CN | H | O-2-乙基己基 |
化合物 | L′ | R2 | R3 | R6 |
B-41 | A1) | H | CN | O-2-乙基己基 |
B-42 | A1) | CN | H | N(CH3)2 |
B-43 | A1) | H | CN | N(CH3)2 |
B-44 | A1) | CN | H | NPh2 |
B-45 | A1) | H | CN | NPh2 |
B-46 | B1) | H | H | H |
B-47 | B1) | H | H | OCH3 |
B-48 | B1) | H | H | OCH2CH3 |
B-49 | B1) | H | H | O-正丁基 |
B-50 | B1) | H | H | O-异丁基 |
B-51 | B1) | H | H | O-2-丁基 |
B-52 | B1) | H | H | O-2-乙基己基 |
B-53 | B1) | H | H | N(CH3)2 |
B-54 | B1) | H | H | NPh2 |
B-55 | B1) | H | CF3 | H |
B-56 | B1) | CF3 | H | H |
B-57 | B1) | H | CF3 | OCH3 |
B-58 | B1) | CF3 | H | OCH3 |
B-59 | B1) | H | CF3 | OCH2CH3 |
B-60 | B1) | CF3 | H | OCH2CH3 |
化合物 | L′ | R2 | R3 | R6 |
B-61 | B1) | H | CF3 | O-正丁基 |
B-62 | B1) | CF3 | H | O-正丁基 |
B-63 | B1) | H | CF3 | O-异丁基 |
B-64 | B1) | CF3 | H | O-异丁基 |
B-65 | B1) | H | CF3 | O-2-丁基 |
B-66 | B1) | CF3 | H | O-2-丁基 |
B-67 | B1) | H | CF3 | O-2-乙基己基 |
B-68 | B1) | CF3 | H | O-2-乙基己基 |
B-69 | B1) | H | CF3 | N(CH3)2 |
B-70 | B1) | CF3 | H | N(CH3)2 |
B-71 | B1) | H | CF3 | NPh2 |
B-72 | B1) | CF3 | H | NPh2 |
B-73 | B1) | H | CN | H |
B-74 | B1) | CN | H | H |
B-75 | B1) | CN | H | OCH3 |
B-76 | B1) | H | CN | OCH3 |
B-77 | B1) | CN | H | OCH2CH3 |
B-78 | B1) | H | CN | OCH2CH3 |
B-79 | B1) | CN | H | O-正丁基 |
B-80 | B1) | H | CN | O-正丁基 |
化合物 | L′ | R2 | R3 | R6 |
B-81 | B1) | CN | H | O-异丁基 |
B-82 | B1) | H | CN | O-异丁基 |
B-83 | B1) | CN | H | O-2-丁基 |
B-84 | B1) | H | CN | O-2-丁基 |
B-85 | B1) | CN | H | O-2-乙基己基 |
B-86 | B1) | H | CN | O-2-乙基己基 |
B-87 | B1) | CN | H | N(CH3)2 |
B-88 | B1) | H | CN | N(CH3)2 |
B-89 | B1) | CN | H | NPh2 |
B-99 | B1) | H | CN | NPh2 |
B-100 | C1) | H | H | H |
B-101 | C1) | H | H | OCH3 |
B-102 | C1) | H | H | OCH2CH3 |
B-103 | C1) | H | H | O-正丁基 |
B-104 | C1) | H | H | O-异丁基 |
B-105 | C1) | H | H | O-2-丁基 |
B-106 | C1) | H | H | O-2-乙基己基 |
B-107 | C1) | H | H | N(CH3)2 |
B-108 | C1) | H | H | NPh2 |
化合物 | L′ | R2 | R3 | R6 |
B-109 | C1) | H | CF3 | H |
B-110 | C1) | CF3 | H | H |
B-111 | C1) | H | CF3 | OCH3 |
B-112 | C1) | CF3 | H | OCH3 |
B-113 | C1) | H | CF3 | OCH2CH3 |
B-114 | C1) | CF3 | H | OCH2CH3 |
B-115 | C1) | H | CF3 | O-正丁基 |
B-116 | C1) | CF3 | H | O-正丁基 |
B-117 | C1) | H | CF3 | O-异丁基 |
B-118 | C1) | CF3 | H | O-异丁基 |
B-119 | C1) | H | CF3 | O-2-丁基 |
B-120 | C1) | CF3 | H | O-2-丁基 |
B-121 | C1) | H | CF3 | O-2-乙基己基 |
B-122 | C1) | CF3 | H | O-2-乙基己基 |
B-123 | C1) | H | CF3 | N(CH3)2 |
B-124 | C1) | CF3 | H | N(CH3)2 |
B-125 | C1) | H | CF3 | NPh2 |
B-126 | C1) | CF3 | H | NPh2 |
B-127 | C1) | H | CN | H |
B-128 | C1) | CN | H | H |
化合物 | L′ | R2 | R3 | R6 |
B-129 | C1) | CN | H | OCH3 |
B-130 | C1) | H | CN | OCH3 |
B-131 | C1) | CN | H | OCH2CH3 |
B-132 | C1) | H | CN | OCH2CH3 |
B-133 | C1) | CN | H | O-正丁基 |
B-134 | C1) | H | CN | O-正丁基 |
B-135 | C1) | CN | H | O-异丁基 |
B-136 | C1) | H | CN | O-异丁基 |
B-137 | C1) | CN | H | O-2-丁基 |
B-138 | C1) | H | CN | O-2-丁基 |
B-139 | C1) | CN | H | O-2-乙基己基 |
B-140 | C1) | H | CN | O-2-乙基己基 |
B-141 | C1) | CN | H | N(CH3)2 |
B-142 | C1) | H | CN | N(CH3)2 |
B-143 | C1) | H | CN | NPh2 |
B-144 | C1) | CN | H | NPh2 |
B-145 | D1) | H | H | H |
B-146 | D1) | H | H | OCH3 |
B-147 | D1) | H | H | OCH2CH3 |
B-148 | D1) | H | H | O-正丁基 |
化合物 | L′ | R2 | R3 | R6 |
B-149 | D1) | H | H | O-异丁基 |
B-150 | D1) | H | H | O-2-丁基 |
B-151 | D1) | H | H | O-2-乙基己基 |
B-152 | D1) | H | H | N(CH3)2 |
B-153 | D1) | H | H | NPh2 |
B-154 | D1) | H | CF3 | H |
B-155 | D1) | CF3 | H | H |
B-156 | D1) | H | CF3 | OCH3 |
B-157 | D1) | CF3 | H | OCH3 |
B-158 | D1) | H | CF3 | OCH2CH3 |
B-159 | D1) | CF3 | H | OCH2CH3 |
B-160 | D1) | H | CF3 | O-正丁基 |
B-161 | D1) | CF3 | H | O-正丁基 |
B-162 | D1) | H | CF3 | O-异丁基 |
B-163 | D1) | CF3 | H | O-异丁基 |
B-164 | D1) | H | CF3 | O-2-丁基 |
B-165 | D1) | CF3 | H | O-2-丁基 |
B-166 | D1) | H | CF3 | O-2-乙基己基 |
B-167 | D1) | CF3 | H | O-2-乙基己基 |
B-168 | D1) | H | CF3 | N(CH3)2 |
化合物 | L′ | R2 | R3 | R6 |
B-169 | D1) | CF3 | H | N(CH3)2 |
B-170 | D1) | H | CF3 | NPh2 |
B-171 | D1) | CF3 | H | NPh2 |
B-172 | D1) | H | CN | H |
B-173 | D1) | CN | H | H |
B-174 | D1) | CN | H | OCH3 |
B-175 | D1) | H | CN | OCH3 |
B-176 | D1) | CN | H | OCH2CH3 |
B-177 | D1) | H | CN | OCH2CH3 |
B-178 | D1) | CN | H | O-正丁基 |
B-179 | D1) | H | CN | O-正丁基 |
B-180 | D1) | CN | H | O-异丁基 |
B-181 | D1) | H | CN | O-异丁基 |
B-182 | D1) | CN | H | O-2-丁基 |
B-183 | D1) | H | CN | O-2-丁基 |
B-184 | D1) | CN | H | O-2-乙基己基 |
B-185 | D1) | H | CN | O-2-乙基己基 |
B-186 | D1) | CN | H | N(CH3)2 |
B-187 | D1) | H | CN | N(CH3)2 |
B-188 | D1) | CN | H | NPh2 |
化合物 | L′ | R2 | R3 | R6 |
B-189 | D1) | H | CN | NPh2 |
B-190 | E1) | H | H | H |
B-191 | E1) | H | H | OCH3 |
B-192 | E1) | H | H | OCH2CH3 |
B-193 | E1) | H | H | O-正丁基 |
B-194 | E1) | H | H | O-异丁基 |
B-195 | E1) | H | H | O-2-丁基 |
B-196 | E1) | H | H | O-2-乙基己基 |
B-197 | E1) | H | H | N(CH3)2 |
B-198 | E1) | H | H | NPh2 |
B-199 | E1) | H | CF3 | H |
B-200 | E1) | CF3 | H | H |
B-201 | E1) | H | CF3 | OCH3 |
B-202 | E1) | CF3 | H | OCH3 |
B-203 | E1) | H | CF3 | OCH2CH3 |
B-204 | E1) | CF3 | H | OCH2CH3 |
B-205 | E1) | H | CF3 | O-正丁基 |
B-206 | E1) | CF3 | H | O-正丁基 |
B-207 | E1) | H | CF3 | O-异丁基 |
B-208 | E1) | CF3 | H | O-异丁基 |
化合物 | L′ | R2 | R3 | R6 |
B-209 | E1) | H | CF3 | O-2-丁基 |
B-210 | E1) | CF3 | H | O-2-丁基 |
B-211 | E1) | H | CF3 | O-2-乙基己基 |
B-212 | E1) | CF3 | H | O-2-乙基己基 |
B-213 | E1) | H | CF3 | N(CH3)2 |
B-214 | E1) | CF3 | H | N(CH3)2 |
B-215 | E1) | H | CF3 | NPh2 |
B-216 | E1) | CF3 | H | NPh2 |
B-217 | E1) | H | CN | H |
B-218 | E1) | CN | H | H |
B-219 | E1) | CN | H | OCH3 |
B-220 | E1) | H | CN | OCH3 |
B-221 | E1) | CN | H | OCH2CH3 |
B-222 | E1) | H | CN | OCH2CH3 |
B-223 | E1) | CN | H | O-正丁基 |
B-224 | E1) | H | CN | O-正丁基 |
B-225 | E1) | CN | H | O-异丁基 |
B-226 | E1) | H | CN | O-异丁基 |
B-227 | E1) | CN | H | O-2-丁基 |
B-228 | E1) | H | CN | O-2-丁基 |
B-229 | E1) | CN | H | O-2-乙基己基 |
B-230 | E1) | H | CN | O-2-乙基己基 |
B-231 | E1) | CN | H | N(CH3)2 |
B-232 | E1) | H | CN | N(CH3)2 |
B-233 | E1) | CN | H | NPh2 |
B-234 | E1) | H | CN | NPh2 |
化合物 | R2 | R3 | R6 |
C-1 | H | H | H |
化合物 | R2 | R3 | R6 |
C-2 | H | H | OCH3 |
C-3 | H | H | OCH2CH3 |
C-4 | H | H | O-正丁基 |
C-5 | H | H | O-异丁基 |
C-6 | H | H | O-2-丁基 |
C-7 | H | H | O-2-乙基己基 |
C-8 | H | H | N(CH3)2 |
C-9 | H | H | NPh2 |
C-10 | H | CF3 | H |
C-11 | CF3 | H | H |
C-12 | H | CF3 | OCH3 |
C-13 | CF3 | H | OCH3 |
C-14 | H | CF3 | OCH2CH3 |
C-15 | CF3 | H | OCH2CH3 |
C-16 | H | CF3 | O-正丁基 |
C-17 | CF3 | H | O-正丁基 |
C-18 | H | CF3 | O-异丁基 |
C-19 | CF3 | H | O-异丁基 |
C-20 | H | CF3 | O-2-丁基 |
C-21 | CF3 | H | O-2-丁基 |
化合物 | R2 | R3 | R6 |
C-22 | H | CF3 | O-2-乙基己基 |
C-23 | CF3 | H | O-2-乙基己基 |
C-24 | H | CF3 | N(CH3)2 |
C-25 | CF3 | H | N(CH3)2 |
C-26 | H | CF3 | NPh2 |
C-27 | CF3 | H | NPh2 |
C-28 | H | CN | H |
C-29 | CN | H | H |
C-30 | H | CN | OCH3 |
C-31 | CN | H | OCH2CH3 |
C-32 | H | CN | OCH2CH3 |
C-33 | CN | H | O-正丁基 |
C-34 | H | CN | O-正丁基 |
C-35 | CN | H | O-异丁基 |
C-36 | H | CN | O-异丁基 |
C-37 | CN | H | O-2-丁基 |
C-38 | H | CN | O-2-丁基 |
C-39 | CN | H | O-2-乙基己基 |
C-40 | H | CN | O-2-乙基己基 |
C-41 | CN | H | N(CH3)2 |
化合物 | R2 | R3 | R6 |
C-42 | H | CN | N(CH3)2 |
C-43 | CN | H | NPh2 |
C-44 | H | CN | NPh2 |
化合物 | L′ | R2 | R3 | R6 |
D-1 | A1) | H | H | H |
D-2 | A1) | H | H | OCH3 |
D-3 | A1) | H | H | OCH2CH3 |
D-4 | A1) | H | H | O-正丁基 |
D-5 | A1) | H | H | O-异丁基 |
D-6 | A1) | H | H | O-2-丁基 |
D-7 | A1) | H | H | O-2-乙基己基 |
D-8 | A1) | H | H | N(CH3)2 |
D-9 | A1) | H | H | NPh2 |
D-10 | A1) | H | CF3 | H |
化合物 | L′ | R2 | R3 | R6 |
D-11 | A1) | CF3 | H | H |
D-12 | A1) | H | CF3 | OCH3 |
D-13 | A1) | CF3 | H | OCH3 |
D-14 | A1) | H | CF3 | OCH2CH3 |
D-15 | A1) | CF3 | H | OCH2CH3 |
D-16 | A1) | H | CF3 | O-正丁基 |
D-17 | A1) | CF3 | H | O-正丁基 |
D-18 | A1) | H | CF3 | O-异丁基 |
D-19 | A1) | CF3 | H | O-异丁基 |
D-20 | A1) | H | CF3 | O-2-丁基 |
D-21 | A1) | CF3 | H | O-2-丁基 |
D-22 | A1) | H | CF3 | O-2-乙基己基 |
D-23 | A1) | CF3 | H | O-2-乙基己基 |
D-24 | A1) | H | CF3 | N(CH3)2 |
D-25 | A1) | CF3 | H | N(CH3)2 |
D-26 | A1) | H | CF3 | NPh2 |
D-27 | A1) | CF3 | H | NPh2 |
D-28 | A1) | H | CN | H |
D-29 | A1) | CN | H | H |
D-30 | A1) | CN | H | OCH3 |
化合物 | L′ | R2 | R3 | R6 |
D-31 | A1) | H | CN | OCH3 |
D-32 | A1) | CN | H | OCH2CH3 |
D-33 | A1) | H | CN | OCH2CH3 |
D-34 | A1) | CN | H | O-正丁基 |
D-35 | A1) | H | CN | O-正丁基 |
D-36 | A1) | CN | H | O-异丁基 |
D-37 | A1) | H | CN | O-异丁基 |
D-38 | A1) | CN | H | O-2-丁基 |
D-39 | A1) | H | CN | O-2-丁基 |
D-40 | A1) | CN | H | O-2-乙基己基 |
D-41 | A1) | H | CN | O-2-乙基己基 |
D-42 | A1) | CN | H | N(CH3)2 |
D-43 | A1) | H | CN | N(CH3)2 |
D-44 | A1) | CN | H | NPh2 |
D-45 | A1) | H | CN | NPh2 |
D-46 | B1) | H | H | H |
D-47 | B1) | H | H | OCH3 |
D-48 | B1) | H | H | OCH2CH3 |
D-49 | B1) | H | H | O-正丁基 |
D-50 | B1) | H | H | O-异丁基 |
化合物 | L′ | R2 | R3 | R6 |
D-51 | B1) | H | H | O-2-丁基 |
D-52 | B1) | H | H | O-2-乙基己基 |
D-53 | B1) | H | H | N(CH3)2 |
D-54 | B1) | H | H | NPh2 |
D-55 | B1) | H | CF3 | H |
D-56 | B1) | CF3 | H | H |
D-57 | B1) | H | CF3 | OCH3 |
D-58 | B1) | CF3 | H | OCH3 |
D-59 | B1) | H | CF3 | OCH2CH3 |
D-60 | B1) | CF3 | H | OCH2CH3 |
D-61 | B1) | H | CF3 | O-正丁基 |
D-62 | B1) | CF3 | H | O-正丁基 |
D-63 | B1) | H | CF3 | O-异丁基 |
D-64 | B1) | CF3 | H | O-异丁基 |
D-65 | B1) | H | CF3 | O-2-丁基 |
D-66 | B1) | CF3 | H | O-2-丁基 |
D-67 | B1) | H | CF3 | O-2-乙基己基 |
D-68 | B1) | CF3 | H | O-2-乙基己基 |
D-69 | B1) | H | CF3 | N(CH3)2 |
D-70 | B1) | CF3 | H | N(CH3)2 |
化合物 | L′ | R2 | R3 | R6 |
D-71 | B1) | H | CF3 | NPh2 |
D-72 | B1) | CF3 | H | NPh2 |
D-73 | B1) | H | CN | H |
D-74 | B1) | CN | H | H |
D-75 | B1) | CN | H | OCH3 |
D-76 | B1) | H | CN | OCH3 |
D-77 | B1) | CN | H | OCH2CH3 |
D-78 | B1) | H | CN | OCH2CH3 |
D-79 | B1) | CN | H | O-正丁基 |
D-80 | B1) | H | CN | O-正丁基 |
D-81 | B1) | CN | H | O-异丁基 |
D-82 | B1) | H | CN | O-异丁基 |
D-83 | B1) | CN | H | O-2-丁基 |
D-84 | B1) | H | CN | O-2-丁基 |
D-85 | B1) | CN | H | O-2-乙基己基 |
D-86 | B1) | H | CN | O-2-乙基己基 |
D-87 | B1) | CN | H | N(CH3)2 |
D-88 | B1) | H | CN | N(CH3)2 |
D-89 | B1) | CN | H | NPh2 |
D-99 | B1) | H | CN | NPh2 |
化合物 | L′ | R2 | R3 | R6 |
D-100 | C1) | H | H | H |
D-101 | C1) | H | H | OCH3 |
D-102 | C1) | H | H | OCH2CH3 |
D-103 | C1) | H | H | O-正丁基 |
D-104 | C1) | H | H | O-异丁基 |
D-105 | C1) | H | H | O-2-丁基 |
D-106 | C1) | H | H | O-2-乙基己基 |
D-107 | C1) | H | H | N(CH3)2 |
D-108 | C1) | H | H | NPh2 |
D-109 | C1) | H | CF3 | H |
D-110 | C1) | CF3 | H | H |
D-111 | C1) | H | CF3 | OCH3 |
D-112 | C1) | CF3 | H | OCH3 |
D-113 | C1) | H | CF3 | OCH2CH3 |
D-114 | C1) | CF3 | H | OCH2CH3 |
D-115 | C1) | H | CF3 | O-正丁基 |
D-116 | C1) | CF3 | H | O-正丁基 |
D-117 | C1) | H | CF3 | O-异丁基 |
D-118 | C1) | CF3 | H | O-异丁基 |
化合物 | L′ | R2 | R3 | R6 |
D-119 | C1) | H | CF3 | O-2-丁基 |
D-120 | C1) | CF3 | H | O-2-丁基 |
D-121 | C1) | H | CF3 | O-2-乙基己基 |
D-122 | C1) | CF3 | H | O-2-乙基己基 |
D-123 | C1) | H | CF3 | N(CH3)2 |
D-124 | C1) | CF3 | H | N(CH3)2 |
D-125 | C1) | H | CF3 | NPh2 |
D-126 | C1) | CF3 | H | NPh2 |
D-127 | C1) | H | CN | H |
D-128 | C1) | CN | H | H |
D-129 | C1) | CN | H | OCH3 |
D-130 | C1) | H | CN | OCH3 |
D-131 | C1) | CN | H | OCH2CH3 |
D-132 | C1) | H | CN | OCH2CH3 |
D-133 | C1) | CN | H | O-正丁基 |
D-134 | C1) | H | CN | O-正丁基 |
D-135 | C1) | CN | H | O-异丁基 |
D-136 | C1) | H | CN | O-异丁基 |
D-137 | C1) | CN | H | O-2-丁基 |
化合物 | L′ | R2 | R3 | R6 |
D-138 | C1) | H | CN | O-2-丁基 |
D-139 | C1) | CN | H | O-2-乙基己基 |
D-140 | C1) | H | CN | O-2-乙基己基 |
D-141 | C1) | CN | H | N(CH3)2 |
D-142 | C1) | H | CN | N(CH3)2 |
D-143 | C1) | H | CN | NPh2 |
D-144 | C1) | CN | H | NPh2 |
D-145 | D1) | H | H | H |
D-146 | D1) | H | H | OCH3 |
D-147 | D1) | H | H | OCH2CH3 |
D-148 | D1) | H | H | O-正丁基 |
D-149 | D1) | H | H | O-异丁基 |
D-150 | D1) | H | H | O-2-丁基 |
D-151 | D1) | H | H | O-2-乙基己基 |
D-152 | D1) | H | H | N(CH3)2 |
D-153 | D1) | H | H | NPh2 |
D-154 | D1) | H | CF3 | H |
D-155 | D1) | CF3 | H | H |
D-156 | D1) | H | CF3 | OCH3 |
化合物 | L′ | R2 | R3 | R6 |
D-157 | D1) | CF3 | H | OCH3 |
D-158 | D1) | H | CF3 | OCH2CH3 |
D-159 | D1) | CF3 | H | OCH2CH3 |
D-160 | D1) | H | CF3 | O-正丁基 |
D-161 | D1) | CF3 | H | O-正丁基 |
D-162 | D1) | H | CF3 | O-异丁基 |
D-163 | D1) | CF3 | H | O-异丁基 |
D-164 | D1) | H | CF3 | O-2-丁基 |
D-165 | D1) | CF3 | H | O-2-丁基 |
D-166 | D1) | H | CF3 | O-2-乙基己基 |
D-167 | D1) | CF3 | H | O-2-乙基己基 |
D-168 | D1) | H | CF3 | N(CH3)2 |
D-169 | D1) | CF3 | H | N(CH3)2 |
D-170 | D1) | H | CF3 | NPh2 |
D-171 | D1) | CF3 | H | NPh2 |
D-172 | D1) | H | CN | H |
D-173 | D1) | CN | H | H |
D-174 | D1) | CN | H | OCH3 |
D-175 | D1) | H | CN | OCH3 |
D-176 | D1) | CN | H | OCH2CH3 |
化合物 | L′ | R2 | R3 | R6 |
D-177 | D1) | H | CN | OCH2CH3 |
D-178 | D1) | CN | H | O-正丁基 |
D-179 | D1) | H | CN | O-正丁基 |
D-180 | D1) | CN | H | O-异丁基 |
D-181 | D1) | H | CN | O-异丁基 |
D-182 | D1) | CN | H | O-2-丁基 |
D-183 | D1) | H | CN | O-2-丁基 |
D-184 | D1) | CN | H | O-2-乙基己基 |
D-185 | D1) | H | CN | O-2-乙基己基 |
D-186 | D1) | CN | H | N(CH3)2 |
D-187 | D1) | H | CN | N(CH3)2 |
D-188 | D1) | CN | H | NPh2 |
D-189 | D1) | H | CN | NPh2 |
D-190 | F1) | H | H | H |
D-191 | F1) | H | H | OCH3 |
D-192 | F1) | H | H | OCH2CH3 |
D-193 | F1) | H | H | O-正丁基 |
D-194 | F1) | H | H | O-异丁基 |
D-195 | F1) | H | H | O-2-丁基 |
D-196 | F1) | H | H | O-2-乙基己基 |
化合物 | L′ | R2 | R3 | R6 |
D-197 | F1) | H | H | N(CH3)2 |
D-198 | F1) | H | H | NPh2 |
D-199 | F1) | H | CF3 | H |
D-200 | F1) | CF3 | H | H |
D-201 | F1) | H | CF3 | OCH3 |
D-202 | F1) | CF3 | H | OCH3 |
D-203 | F1) | H | CF3 | OCH2CH3 |
D-204 | F1) | CF3 | H | OCH2CH3 |
D-205 | F1) | H | CF3 | O-正丁基 |
D-206 | F1) | CF3 | H | O-正丁基 |
D-207 | F1) | H | CF3 | O-异丁基 |
D-208 | F1) | CF3 | H | O-异丁基 |
D-209 | F1) | H | CF3 | O-2-丁基 |
D-210 | F1) | CF3 | H | O-2-丁基 |
D-211 | F1) | H | CF3 | O-2-乙基己基 |
D-212 | F1) | CF3 | H | O-2-乙基己基 |
D-213 | F1) | H | CF3 | N(CH3)2 |
D-214 | F1) | CF3 | H | N(CH3)2 |
D-215 | F1) | H | CF3 | NPh2 |
D-216 | F1) | CF3 | H | NPh2 |
化合物 | L′ | R2 | R3 | R6 |
D-217 | F1) | H | CN | H |
D-218 | F1) | CN | H | H |
D-219 | F1) | CN | H | OCH3 |
D-220 | F1) | H | CN | OCH3 |
D-221 | F1) | CN | H | OCH2CH3 |
D-222 | F1) | H | CN | OCH2CH3 |
D-223 | F1) | CN | H | O-正丁基 |
D-224 | F1) | H | CN | O-正丁基 |
D-225 | F1) | CN | H | O-异丁基 |
D-226 | F1) | H | CN | O-异丁基 |
D-227 | F1) | CN | H | O-2-丁基 |
D-228 | F1) | H | CN | O-2-丁基 |
D-229 | F1) | CN | H | O-2-乙基己基 |
D-230 | F1) | H | CN | O-2-乙基己基 |
D-231 | F1) | CN | H | N(CH3)2 |
D-232 | F1) | H | CN | N(CH3)2 |
D-233 | F1) | CN | H | NPh2 |
D-234 | F1) | H | CN | NPh2 |
D-235 | E1) | H | H | H |
D-236 | E1) | H | H | OCH3 |
化合物 | L′ | R2 | R3 | R6 |
D-237 | E1) | H | H | OCH2CH3 |
D-238 | E1) | H | H | O-正丁基 |
D-239 | E1) | H | H | O-异丁基 |
D-240 | E1) | H | H | O-2-丁基 |
D-241 | E1) | H | H | O-2-乙基己基 |
D-242 | E1) | H | H | N(CH3)2 |
D-243 | E1) | H | H | NPh2 |
D-244 | E1) | H | CF3 | H |
D-245 | E1) | CF3 | H | H |
D-246 | E1) | H | CF3 | OCH3 |
D-247 | E1) | CF3 | H | OCH3 |
D-248 | E1) | H | CF3 | OCH2CH3 |
D-249 | E1) | CF3 | H | OCH2CH3 |
D-250 | E1) | H | CF3 | O-正丁基 |
D-251 | E1) | CF3 | H | O-正丁基 |
D-252 | E1) | H | CF3 | O-异丁基 |
D-253 | E1) | CF3 | H | O-异丁基 |
D-254 | E1) | H | CF3 | O-2-丁基 |
D-255 | E1) | CF3 | H | O-2-丁基 |
D-256 | E1) | H | CF3 | O-2-乙基己基 |
化合物 | L′ | R2 | R3 | R6 |
D-257 | E1) | CF3 | H | O-2-乙基己基 |
D-258 | E1) | H | CF3 | N(CH3)2 |
D-259 | E1) | CF3 | H | N(CH3)2 |
D-260 | E1) | H | CF3 | NPh2 |
D-261 | E1) | CF3 | H | NPh2 |
D-262 | E1) | H | CN | H |
D-263 | E1) | CN | H | H |
D-264 | E1) | CN | H | OCH3 |
D-265 | E1) | H | CN | OCH3 |
D-266 | E1) | CN | H | OCH2CH3 |
D-267 | E1) | H | CN | OCH2CH3 |
D-268 | E1) | CN | H | O-正丁基 |
D-269 | E1) | H | CN | O-正丁基 |
D-270 | E1) | CN | H | O-异丁基 |
D-271 | E1) | H | CN | O-异丁基 |
D-272 | E1) | CN | H | O-2-丁基 |
D-273 | E1) | H | CN | O-2-丁基 |
D-274 | E1) | CN | H | O-2-乙基己基 |
D-275 | E1) | H | CN | O-2-乙基己基 |
D-276 | E1) | CN | H | N(CH3)2 |
化合物 | L′ | R2 | R3 | R6 |
D-277 | E1) | H | CN | N(CH3)2 |
D-278 | E1) | CN | H | NPh2 |
D-279 | E1) | H | CN | NPh2 |
阻隔层
除了合适的基质外,使用磷光材料的OLED器件通常需要至少一层激子或空穴阻隔层,以帮助将激子或电子空穴重组中心限制在含有基质和磷光材料的发光层,或减少电荷载体(电子或空穴)的数目。在一个实施方案中,将这种阻隔层置于电子传输层与发光层之间。此时,阻隔层的电离电位应使存在着用于防止空穴从基质迁移进入电子传输层的能垒,同时电子亲和力应使电子更容易从电子传输层进入含有基质和磷光材料的发光层。还需要,但并非绝对需要,阻挡材料的三重态能量大于磷光材料。合适的空穴阻挡材料描述于WO00/70655和WO01/93642中。有用材料的实例为(1,3,5-三(1-苯基-1H-苯并咪唑-2-基)苯)(TPBI)、浴铜灵(BCP)和双(2-甲基-8-喹啉醇)(4-苯基苯酚)铝(III)(BAlq)。如US20030068528所述,还已知除Balq外的金属络合物阻隔空穴和激子。US20030175553描述了在电子/激子阻隔层中使用面-三(1-苯基吡唑-N,C2)铱(III)(Irppz)。
本发明实施方案可提供有利特征,例如操作效率、更高亮度、色调、低驱动电压和改善的操作稳定性。在本发明中有用的有机金属化合物的实施方案可提供宽的色调范围,包括在发射白光(直接或通过滤光器以提供多色显示)中有用的那些。
通用器件架构
本发明化合物可用于许多使用小分子材料、低聚材料、聚合材料或其组合的OLED器件构造中。这些包括含有单独阳极和阴极的非常简单的结构至更复杂的器件,例如由阳极和阴极的正交阵列组成以形成像素的无源矩阵显示器,和其中例如用薄膜晶体管(TFT)独立控制各像素的有源矩阵显示器。
存在大量有机层构造。OLED的基本要求为阳极、阴极和位于阳极与阴极之间的有机发光层。可使用的其它层如下文更完整所述。
典型结构,尤其是对小分子器件有用的结构,由基材、阳极、空穴注入层、空穴传输层、发光层、空穴或激子阻隔层、电子传输层和阴极组成。下文详细描述这些层。要注意的是基材或者可位于阴极附近,或基材可实际上构成阳极或阴极。将在阳极与阴极之间的有机层简称作有机EL元件。同时,有机层的总结合厚度理想地为小于500nm。
基材
基材可取决于意欲的发光方向为透光或不透明的。就通过基材来看EL发射而言,透光性能是理想的。此时,通常使用透明的玻璃或塑料。基材可为含有多层材料的复合结构。就其中在OLED层下提供TFT的有源矩阵基材而言情况通常如此。仍然需要基材,至少在发射像素化区域,由非常透明的材料如玻璃或聚合物组成。就其中通过顶部电极来看EL发射的应用而言,底部支撑物的透射特征不重要,并因此可为透光、吸光或反光的。此时所用基材包括,但不限于玻璃、塑料、半导体材料、硅、陶瓷和电路板材料。此外,基材可为含有多层材料的复合结构,例如在有源矩阵TFT设计中发现的结构。需要在这些器件构造中提供透光的顶部电极。
阳极
当通过阳极来看需要的电致发光光发射(EL)时,阳极应对所关注的发射透明或基本透明。用于本发明的常见透明阳极材料为氧化铟锡(ITO)、氧化铟锌(IZO)和氧化锡,但可工作的其它金属氧化物包括但不限于铝或铟掺杂的氧化锌、氧化镁铟和氧化镍钨。除这些氧化物外,金属氮化物如氮化镓、金属硒化物如硒化锌和金属硫化物如硫化锌可用作阳极。对其中仅通过阴极来看EL发射的应用而言,阳极的透射特征不重要,并可使用任何透明、不透明或反光的导电材料。此应用的导体的实例包括但不限于金、铱、钼、钯和铂。想要的阳极材料通常通过任何合适的方法沉积,例如蒸发、溅射、化学气相沉积或电化学方法。阳极可使用熟知的光刻法图案化。任选,阳极可在应用其它层以前抛光以降低表面粗糙度,进而减少短路或提高反射率。
阴极
当只是通过阳极来看发光时,用于本发明中的阴极可由几乎任何导电材料组成。想要的材料具有好的成膜性能,以确保与在下层有机层的良好接触、促进在低电压下注入电子和具有良好稳定性。有用的阴极材料通常含有低功函数的金属(<4.0eV)或金属合金。如US-A-4,885,221所述,一种有用的阴极材料由Mg:Ag合金组成,其中银的百分比为1-20%。其它合适种类的阴极材料包括双层,所述双层含有阴极和与用较厚导电金属层覆盖的有机层(例如电子传输层(ETL))接触的薄电子注入层(EIL)。在本发明中,EIL优选含有低功函数金属或金属盐,如果如此,则较厚覆盖层不需要具有低功函数。如US-A-5,677,572所述,一种此类阴极由薄LiF层接着较厚Al层组成。用碱金属掺杂的ETL材料如Li掺杂的Alq为有用EIL的其它实例。其它有用的阴极材料组包括但不限于公开于US-A-5,059,861、5,059,862和6,140,763中的那些。
当通过阴极来看发光时,阴极必须透明或几乎透明。对此类应用来说,金属必须薄或必须使用透明的导电氧化物或这些材料的组合。光学透明的阴极已更详细地描述于US-A-4,885,211、5,247,190、JP 3,234,963、U.S.专利号5,703,436、5,608,287、5,837,391、5,677,572、5,776,622、5,776,623、5,714,838、5,969,474、5,739,545、5,981,306、6,137,223、6,140,763、6,172,459、EP1076368、US-A-6,278,236和6,284,3936中。阴极材料通常通过任何合适的方法沉积,例如蒸发、溅射或化学气相沉积。当需要时,可通过许多熟知的方法实现图案化,包括但不限于完全掩模(through-mask)沉积、如US-A-5,276,380和EP0732868所述的整合阴影掩模、激光烧蚀和选择性化学气相沉积。
空穴注入层(HIL)
可在阳极与空穴传输层之间提供空穴注入层。空穴注入材料可用于改善随后的有机层的成膜性能并促进空穴注入空穴传输层中。适用于空穴注入层的材料包括但不限于如US-A-4,720,432所述的卟啉类化合物、如US-A-6,208,075所述的等离子体沉积的碳氟化合物聚合物和一些芳族胺如间-MTDATA(4,4′,4″-三[(3-甲基苯基)苯基氨基]三苯基胺)。据报导在有机EL器件中有用的其它空穴注入材料描述于EP0891121和EP1029909中。可有利地使用(酞菁铜络合物)(CuPC)和(4,4′,4″-三(N-(萘-2-基)-N-苯基氨基)三苯基胺)(2-TNATA)。
空穴传输层(HTL)
有机EL器件的空穴传输层含有至少一种空穴传输化合物如芳族叔胺,其中将后者理解为含有至少一个仅与碳原子连接的三价氮原子的化合物,所述碳原子中的至少一个为芳环的成员。在一种形式中,芳族叔胺可为芳基胺,例如单芳基胺、二芳基胺、三芳基胺或聚合芳基胺。示例性的单体三芳基胺阐述于US-A-3,180,730中。用1个或多个乙烯基取代和/或含有至少一个含活性氢基团的其它合适的三芳基胺公开于US-A-3,567,450和3,658,520中。如US-A-4,720,432和5,061,569所述,更优选种类的芳族叔胺为含有至少两个芳族叔胺部分的那些。这种化合物包括由结构式(A)表示的那些,其中Q1和Q2为独立选择的芳族叔胺部分,G为连接基团如碳碳连接的亚芳基、亚环烷基或亚烷基。在一个实施方案中,Q1或Q2中的至少一个含有多环稠环结构如萘。当G为芳基时,其便利地为亚苯基、亚联苯基或亚萘基部分。
满足结构式(A)且含有两个三芳基胺部分的有用种类三芳基胺由结构式(B)表示,其中Q3和Q4各自独立表示氢原子、芳基或烷基,或Q3和Q4一起表示完成环烷基的原子;Q5和Q6各自独立表示芳基,所述芳基又被如结构式(C)所示的二芳基取代的氨基取代,其中Q7和Q8为独立选择的芳基。在一个实施方案中,Q7或Q8中的至少一个含有多环稠合环结构如萘。
另一种芳族叔胺为四芳基二胺。理想的四芳基二胺含有两个通过亚芳基连结的例如如式(C)所示的二芳基氨基。有用的四芳基二胺包括由式(D)表示的那些,其中各Are为独立选择的亚芳基,例如亚苯基或蒽部分,n为1-4的整数,Ar、Q9、Q10和Q11为独立选择的芳基。在典型的实施方案中,Ar、Q9、Q10和Q11中的至少一个为多环稠环结构如萘。前述结构式(A)、(B)、(C)、(D)的各种烷基、亚烷基、芳基和亚芳基部分又可各自被取代。典型的取代基包括烷基、烷氧基、芳基、芳氧基和卤素如氟化物、氯化物和溴化物。各种烷基和亚烷基部分通常含有约1-6个碳原子。环烷基部分可含有3-约10个碳原子,但是通常含有5、6或7个环碳原子,例如环戊基、环己基和环庚基环结构。芳基和亚芳基部分通常为苯基和亚苯基部分。
空穴传输层可由单一芳族叔胺化合物或其混合物形成。具体而言,可使用三芳基胺如满足式(B)的三芳基胺与例如如式(D)所示的四芳基二胺的组合。当三芳基胺与四芳基二胺组合使用时,后者作为插在三芳基胺与电子注入和传输层之间的层配置。示例性的有用芳族叔胺如下:1,1-双(4-二对甲苯基氨基苯基)环己烷、1,1-双(4-二对甲苯基氨基苯基)-4-苯基环己烷、N,N,N′,N′-四苯基-4,4′″-二氨基-1,1′:4′,1″:4″,1′″-四苯基双(4-二甲基氨基-2-甲基苯基)苯基甲烷、1,4-双[2-[4-[N,N-二(对甲苯基)氨基]苯基]乙烯基]苯(BDTAPVB)、N,N,N′,N′-四对甲苯基-4,4′-二氨基联苯、N,N,N′,N′-四苯基-4,4′-二氨基联苯、N,N,N′,N′-四-1-萘基-4,4′-二氨基联苯、N,N,N′,N′-四-2-萘基-4,4′-二氨基联苯、N-苯基咔唑、4,4′-双[N-(1-萘基)-N-苯基氨基]联苯(NPB)、4,4′-双[N-(1-萘基)-N-(2-萘基)氨基]联苯(TNB)、4,4′-双[N-(1-萘基)-N-苯基氨基]对三联苯、4,4′-双[N-(2-萘基)-N-苯基氨基]联苯、4,4′-双[N-(3-苊基)-N-苯基氨基]联苯、1,5-双[N-(1-萘基)-N-苯基氨基]萘、4,4′-双[N-(9-蒽基)-N-苯基氨基]联苯、4,4′-双[N-(1-蒽基)-N-苯基氨基]-对三联苯、4,4′-双[N-(2-菲基)-N-苯基氨基]联苯、4,4′-双[N-(8-荧蒽基)-N-苯基氨基]联苯、4,4′-双[N-(2-芘基)-N-苯基氨基]联苯、4,4′-双[N-(2-并四苯基)-N-苯基氨基]联苯、4,4′-双[N-(2-苝基)-N-苯基氨基]联苯、4,4′-双[N-(1-六苯并苯基)-N-苯基氨基]联苯、2,6-双(二对甲苯基氨基)萘、2,6-双[二(1-萘基)氨基]萘、2,6-双[N-(1-萘基)-N-(2-萘基)氨基]萘、N,N,N′,N′-四(2-萘基)-4,4″-二氨基-对三联苯、4,4′-双{N-苯基-N-[4-(1-萘基)苯基]氨基}联苯、2,6-双[N,N-二(2-萘基)氨基]氟、4,4′,4″-三[(3-甲基苯基)苯基氨基]三苯基胺(MTDATA)和4,4′-双[N-(3-甲基苯基)-N-苯基氨基]联苯(TPD)。可使用空穴传输层以提高导电率。NPD和TPD为本征空穴传输层的实例。如US6,337,102或DE10058578所公开,p掺杂的空穴传输层的实例为用F4-TCNQ以50∶1的摩尔比掺杂的间MTDATA。
如EP1009041所述,另一类有用的空穴传输材料包括多环芳族化合物。可使用具有2个以上胺基团的芳族叔胺,其中包括低聚材料。另外,可使用聚合空穴传输材料如聚(N-乙烯基咔唑)(PVK)、聚噻吩、聚吡咯、聚苯胺和共聚物如也称作PEDOT/PSS的聚(3,4-亚乙基二氧基噻吩)/聚(4-苯乙烯磺酸盐)。
荧光发光材料和层(LEL)
除磷光材料外,其它发光材料可用于OLED器件中,包括荧光材料。虽然术语“荧光”通常用于描述任何发光材料,但此时我们指从单重态激发状发光的材料。荧光材料可用于与磷光材料相同的层中、在相邻层中、在相邻像素中或任何组合。必须小心以不选择将不利影响磷光材料性能的材料。本领域技术人员应当理解的是必需适当设定在与磷光材料相同的层或相邻层中的材料的三重态激发态能量以防止不需要的猝灭。如US-A-4,769,292和5,935,721更完整所述,有机EL元件的发光层(LEL)含有发光荧光或磷光材料,其中由于在此区域中的电子空穴对重组产生电致发光。发光层可由单一材料组成,但是更通常由用客体发射材料掺杂的基质材料或其中发光主要来自发射材料的材料组成,且可为任何颜色。发光层中的基质材料可为如下定义的电子传输材料、如上定义的空穴传输材料或支持空穴电子重组的其它材料或材料的组合。通常以基质材料的0.01-10重量%结合荧光发射材料。基质和发射材料可为小的非聚合分子或聚合材料如聚芴和聚乙烯基亚芳基(例如聚(对亚苯基亚乙烯基),PPV)。在聚合物的情况下,小分子发射材料可分子分散在聚合基质中,或发射材料可通过将少量组分共聚到基质聚合物中而加入。可将基质材料混合在一起,以改善成膜、电性能、发光效率、使用寿命或可制造性。基质可含有具有良好空穴传输性能的材料和具有良好电子传输性能的材料。
已知有用的基质和发射材料包括但不限于US-A-4,768,292、5,141,671、5,150,006、5,151,629、5,405,709、5,484,922、5,593,788、5,645,948、5,683,823、5,755,999、5,928,802、5,935,720、5,935,721和6,020,078公开的那些。
8-羟基喹啉和类似衍生物的金属络合物(式E)构成一类能支持电致发光的有用基质化合物,且特别合适于波长长于500nm如绿光、黄光、橙色光和红光的光发射,其中M代表金属;v为1-4的整数;ZZ在每次出现时独立代表完成具有至少2个稠合芳环的核的原子。从上文明显的是金属可为单价、二价、三价或四价金属。金属可例如为碱金属如锂、钠或钾;碱土金属如镁或钙;土金属如铝或镓;或过渡金属如锌或锆。通常可使用已知为有用的螯合金属的任何单价、二价、三价或四价金属。ZZ完成含有至少2个稠合芳环的杂环核,其至少一个为唑或吖嗪环。其它环,包括脂族和芳族环,如果需要可与所述2个所需环稠合。为避免增加分子大小而没有改善功能,环原子数通常保持在18或更少。
示例性的有用螯合喔星类化合物如下:
CO-1:铝三喔星[别名,三(8-喹啉醇)铝(III)]
CO-2:镁二喔星[别名,双(8-喹啉醇)镁(II)]
CO-3:双[苯并{f}-8-喹啉醇]锌(II)
CO-4:双(2-甲基-8-喹啉醇)铝(III)-μ-氧代-双(2-甲基-8-喹啉醇)铝(III)
CO-5:铟三喔星[别名,三(8-喹啉醇)铟]
CO-6:铝三(5-甲基喔星)[别名,三(5-甲基-8-喹啉醇)铝(III)]
CO-7:锂喔星[别名,(8-喹啉醇)锂(I)]
CO-8:镓喔星[别名,三(8-喹啉醇)镓(III)]
CO-9:锆喔星[别名,四(8-喹啉醇)锆(IV)]
有用的荧光发射材料包括但不限于蒽、并四苯、呫吨(xanthene)、花、红萤烯、香豆素、若丹明和喹吖啶酮的衍生物、二氰基亚甲基吡喃化合物、噻喃化合物、聚甲川(polymethine)化合物、吡啶鎓(pyrilium)和硫吡啶鎓(thiapyrilium)化合物、芴衍生物、二茚并苝(periflanthene)衍生物、茚并苝衍生物、双(吖嗪基)胺硼化合物、双(吖嗪基)甲烷化合物和羰苯乙烯基(carbostyryl)化合物。有用材料的示例性实例包括但不限于US7,090,930B2所述的化合物L1-L52。
电子传输层(ETL)
优选用于形成本发明有机EL器件的电子传输层的成薄膜材料为金属螯合的喔星类化合物,包括喔星本身(也通常称作8-喹啉醇或8-羟基喹啉)的螯合物。这种化合物有助于注入和传输电子,表现出两种高水平性能,且易于以薄膜形式制备。示例性的所关注喔星类化合物为满足前述结构式(E)的那些。其它电子传输材料包括如US4,356,429所公开的各种丁二烯衍生物和如US4,539,507所述的各种杂环荧光增白剂。满足结构式(G)的苯并唑也为有用的电子传输材料。还已知三嗪可用作电子传输材料。可使用掺杂以增强导电度性。Alq3为本征电子传输层的实例。如US6,337,102所公开,n掺杂的电子传输层的实例为用Li以1∶1的摩尔比掺杂的BPhen。
有机层的沉积
上述有机材料合适地通过任何适于形成有机材料的方法沉积。在小分子的情况下,它们便利地通过热蒸发沉积,但可通过其它方法如从具有改善成膜的任选粘合剂的溶剂中沉积。如果材料可溶或为低聚/聚合形式,则通常优选溶液处理,例如旋涂、喷墨印刷。可使用树状物替代物以增强小分子进行溶液处理的能力。可使用阴影掩模、整合阴影掩模(US5,294,870)、从供料板(donor sheet)的空间限定的热染料转移(US5,688,551、5,851,709和6,066,357)和喷墨方法(US6,066,357)实现图案化沉积。
封装
大部分OLED器件对湿气或氧气或二者敏感,所以它们通常与干燥剂如氧化铝、铝土矿、硫酸钙、粘土、硅胶、沸石、碱金属氧化物、碱土金属氧化物、硫酸盐或金属卤化物和过氯酸盐一起封装在惰性气氛如氮气或氩气中。用来封装和干燥的方法包括但不限于US6,226,890所述的那些。另外,本领域已知阻隔层如SiOx、特氟隆和其它无机/聚合层用于封装。
根据本发明的实施方案制造的器件可结合到各种消耗品中,包括平板显示器、计算机监视器、电视、广告牌、内部或外部照明和/或发信号用的灯、完全透明的显示器、挠性显示器、激光打印机、手机、个人数字助理(PDA)、膝上型计算机、数码照相机、可携式摄像机、取景器、微显示器、车辆、电影院或体育场屏幕或标志。可使用各种控制机制来控制根据本发明制造的器件,包括无源矩阵和有源矩阵。
在下列实施例中进一步阐明本发明的各种特征和方面。尽管提供这些实施例以向本领域技术人员说明如何在本发明范围内操作,但它们不对本发明范围的构成限制,其中该范围仅在权利要求中限定。除非另有说明,否则在如下实施例和说明书其它地方和权利要求中,所有份和百分比均为重量份和重量百分比,温度为摄氏度,压力在或接近大气压下。
实施例
实施例1
可如PCT/EP2007/057408实施例1所述制备6,11-二溴-1,2,3,4-四苯基苯并菲。将1.80g(2.61mmol)6,11-二溴-1,2,3,4-四苯基苯并菲和540mg(5.60mmol)叔丁醇钠溶于40ml甲苯中。用氩气使反应混合物脱气并加入29mg(0.13mmol)乙酸钯(II)。然后加入105mg(0.520mmol)三叔丁基膦。加入1.77g(8.08mmol)萘-1-基-苯基胺在15ml甲苯中的脱气溶液,并在90℃下将反应混合物加热3小时。将20毫升1%的氰化钠溶液加入反应混合物中并使反应混合物回流1小时。将反应混合物依次用乙醚和二氯甲烷萃取。将有机相用硫酸镁干燥。在真空中除去溶剂。通过层析在硅胶上用甲苯/环己烷(1/4)将产物提纯。1H-NMR 300MHz(CDCl3)δ=6.50-6.90(m,22H),7.00-7.50(m,20H),7.65-7.25(m,4H),8.85(d,J=8.1Hz,2H),8.18(d,J=8.8Hz,2H)。
实施例2
a.)将4.44g(43.5mmol)乙炔基苯、280mg(1.45mmol)碘化铜(I)和340mg(0.29mmol)四(三苯膦)钯(0)加入在200ml哌啶中的10.0g(14.5mmol)6,11-二溴-1,2,3,4-四苯基苯并菲中。在130℃下和氩气中将反应混合物搅拌22小时。过滤出固体。滤液包含目标产物和单偶合产物。将2.96g(26.6mmol)乙炔基苯、130mg(0.725mmol)碘化铜(I)和170mg(0.145mmol)四(三苯膦)钯(0)加入在哌啶中的滤液中,在130℃下和氩气中将反应混合物搅拌48小时。过滤出固体。在真空中除去溶剂并用正己烷将产物煎煮2次。
b)将3.00g(4.09mmol)实施例2a的产物与16.6g(65.5mmol)碘的混合物溶于50ml的二甲亚砜(DMSO)中。在160℃下将反应混合物搅拌21小时,倒入水中并用二氯甲烷萃取水相。用10%硫代硫酸钠溶液洗涤有机相。将有机相用硫酸钠干燥并在真空中除去溶剂。通过柱层析在硅胶上用甲苯分离产物。
c)将540mg(5.00mmol)苯-1,2-二胺加入在80ml乙醇和40ml氯仿中的2.00g(2.51mmol)实施例2b的产物中。加入12滴硫酸并使反应混合物回流4天。将产物过滤,用乙醇和20%盐酸洗涤并用氯仿进行Soxhlet萃取。熔点:288℃
实施例3
将3.00g(4.35mmol)6,11-二溴-1,2,3,4-四苯基苯并菲和3.90g(9.56mmol)2,3-二苯基-6-(4,4,5,5-四甲基-1,3,2-二杂氧戊硼烷-2-基)喹喔啉(PCT/EP2008/053251的实施例5b)溶于20ml二噁烷与80ml甲苯的混合物中。将溶液用氩气脱气。加入107mg(0.261mmol)二环己基-(2′,6′-二甲氧基联苯-2-基)膦(phosphane)和9.8mg(0.043mmol)乙酸钯(II)。将溶液用氩气脱气。加入5.27g(21.7mmol)磷酸三钾单水合物(K3PO4*H2O)在16ml水中的脱气溶液。在氩气中和90℃下将反应混合物搅拌18小时。将产物过滤,用甲苯洗涤,溶于二氯甲烷中并在硅胶上过滤。熔点:367℃
实施例4
将20ml二噁烷与80ml甲苯的混合物加入3.00g(4.35mmol)6,11-二溴-1,2,3,4-四苯基苯并菲和1.89g(9.56mmol)3-联苯硼酸中。将混合物用氩气脱气。加入107mg(0.261mmol)二环己基-(2’,6’-二甲氧基联苯-2-基)膦和9.8mg(0.043mmol)乙酸钯(II)。将溶液用氩气脱气。加入5.27g(21.7mmol)磷酸三钾单水合物(K3PO4*H2O)在16ml水中的脱气溶液。在氩气中和90℃下将反应混合物搅拌18小时。过滤出产物,用甲苯洗涤并用二氯甲烷进行Soxhlet萃取。熔点:334℃
实施例5
实施例5的产物类似于实施例1的产物制备。使用二甲苯代替甲苯作为溶剂。熔点:336℃。
实施例6
实施例6的产物类似于实施例4的产物制备。玻璃态转化点:211℃。1H-NMR 300MHz(CDCl3)δ=8.74(d,J=8.3Hz,2H),7.98-8.21(m,18H),7.81(dd,J=8.2,1.7Hz,2H),7.10-7.28(m,H+CHCl3),6.83-6.93(m,6H),6.67-6.70(m,4H)
实施例7
a.)在氩气中将5.00g(7.24mmol)6,11-二溴-1,2,3,4-四苯基苯并菲溶于30ml无水THF(四氢呋喃)中。在-78℃下将6.4ml(15.9mmol)正丁基锂溶液(2.5M,在己烷中)缓慢加入此混合物中。在加入正丁基锂溶液以后,将反应混合物搅拌10分钟。加入5.29g(72.4mmol)DMF(N,N-二甲基甲酰胺)。将反应混合物在-78℃下搅拌10分钟,然后将其温热至25℃。将反应混合物倒入水中并用二氯甲烷萃取水相。用硫酸钠干燥有机相并在真空中除去溶剂。在硅胶上用1/1的甲苯/己烷柱层析以后产物得到了分离。
b.)在氩气下将800mg(3.74mmol)(2-硝基苯基)苯基胺和1.77g(10.2mmol)连二亚硫酸钠加入在40ml乙醇中的1.00g(1.70mmol)实施例7a的产物中。将反应混合物在氩气下回流48小时,倒入水中并用二氯甲烷萃取水相。在真空中除去溶剂。干燥的产物含有目标产物与单苯并咪唑中间体的混合物。在氩气下将400mg(1.87mmol)(2-硝基苯基)苯基胺和900mg(5.1mmol)连二亚硫酸钠加入在40ml乙醇中的粗产物中。在氩气下将反应混合物回流48小时,冷却至25℃,过滤出产物并在硅胶上用6/1的甲苯/乙醇柱层析以后分离。熔点:361℃
实施例8
可根据PCT/EP2007/057408的实施例1制备6,11-二溴-1,2,3,4-四苯基苯并菲。实施例8的产物类似于实施例5的产物制备。熔点:375℃
比较实施例1
a)在25℃和氮气下将在30ml磷酸三甲酯中的21.0g(0.131mol)溴加入在150ml磷酸三甲酯中的10g(43.8mmol)苯并菲中。将反应混合物在85℃和氮气下搅拌5小时,冷却至25℃并过滤出固体。将滤液静置在25℃下过夜。过滤出所形成的沉淀物。沉淀物含有大部分双溴化物(异构体的混合物)B和较少量的单溴化物A。
b)使比较实施例1a的产物与咔唑类似于实施例5反应。将此实施例的产物在硅胶上用8/2的正己烷/甲苯柱层析分离。将产物A作为单一异构体分离。产物B为不可分离的异构体混合物。产物A的熔点:217℃。
从下表明显的是,本发明化合物的玻璃态转化点高于现有技术化合物玻璃态转化点,此事实表明本发明化合物具有比现有技术化合物更高的器件稳定性(使用寿命)。
实施例 | Tg |
实施例5 | 193℃ |
实施例8 | 202℃ |
比较实施例1产物A | 91℃ |
比较实施例1产物B | 129℃ |
器件制造和应用实施例
通过在高真空(<10-6毫巴)中热蒸发制造器件。阳极由约1200先前沉积在玻璃基材上的氧化铟锡(ITO)组成。阴极由10的LiF接着1000的Al组成。在制备后,在没有封装的情况下立即在手套箱的氮气气氛(<1ppm的H2O和O2)中测试全部器件。所用全部材料皆为经升华品质。
应用实施例1
有机堆层从ITO表面开始依次由作为空穴注入层(HIL)的600的2-TNATA(4,4’,4″-三(N-(萘-2-基)-N-苯基氨基)三苯基胺)、作为空穴传输层的300的4,4’-双[N-(1-萘基)-N-苯基氨基]联苯(α-NPD)组成。发射层由300分别来自实施例5、实施例8、产物A和产物B的材料(作为基质,下表中的应用实施例1a、1b、1c和1d),在所有情况下都用10%红光发射剂双(1-(苯基)异喹啉)铱(III)乙酰丙酮化物(缩写:Ir(piq)2(acac),客体)掺杂,接着作为空穴阻隔层的10nm TPBI(1,3,5-三(1-苯基-1H-苯并咪唑-2-基)苯)和作为电子传输层的30nm Alq3(三(8-羟基喹啉)铝)组成。
对如上制备的器件测量的电流效率,以及开始电压(C,在1000cd/m2下)、CIE值和最大亮度在下表中报告:
应用实施例 | 基质 | 电流效率/1000cd/m2 | V/1000cd/m2 | CIE(x,y) | 最大亮度/cd/m2 |
1a | 实施例5的化合物 | 1.8 | 10.2 | 0.67,0.31 | 2600 |
1b | 实施例8的化合物 | 5.6 | 8.3 | 0.67,0.31 | 8900 |
1c | 产物A | 3.4 | 9.9 | 0.67,0.31 | 3100 |
1d | 产物B | 0.2 | 17.0 | 0.67,0.31 | 300 |
如上表所报告,相对于含有比较产物A和B的应用实施例1c和1d的器件,含有实施例5和8的化合物的应用实施例1a和1b的器件表现出改善的电流效率。特别地,含有实施例8的化合物的应用实施例1b的器件的开始电压仅为8.3V,其为相当低的值,类似器件建造的使用比较产物A和B的应用实施例1c和1d的器件无法与其相比。
应用实施例2
有机堆层从ITO表面开始依次由作为空穴注入层(HIL)的6002-TNATA(4,4′,4″-三(N-(萘-2-基)-N-苯基氨基)三苯基胺)、作为空穴传输层的3004,4’-双[N-(1-萘基)-N-苯基氨基]联苯(α-NPD)组成。发射层由300分别来自实施例5、实施例8、产物A和产物B的材料(作为基质,下表中的应用实施例2a、2b、2c和2d),在所有情况下都用10%红光发射剂(乙酰丙酮)双(2,3,5-三苯基吡嗪)铱(III)(缩写:Ir(tppr)2(acac);客体)掺杂,接着作为空穴阻隔层的10nm的TPBI(1,3,5-三(1-苯基-1H-苯并咪唑-2-基)苯)和作为电子传输层的30nm的Alq3(三(8-羟基喹啉)铝)组成。
对如上制备的器件测量的电流效率,以及开始电压(C,在1000cd/m2下)、CIE值和最大亮度在下表中报告:
应用实施例 | 基质 | 电流效率,在1000cd/m2下 | V,在1000cd/m2下 | CIE(x,y) | 最大亮度/cd/m2 |
2a | 实施例5的化合物 | 4.9 | 9.4 | 0.64,0.34 | 5300 |
应用实施例 | 基质 | 电流效率,在1000cd/m2下 | V,在1000cd/m2下 | CIE(x,y) | 最大亮度/cd/m2 |
2b | 实施例8的化合物 | 6.1 | 8.7 | 0.64,0.34 | 7800 |
2c | 产物A | 4 | 10.0 | 0.64,0.34 | 3000 |
2d | 产物B | 0.7 | 14.2 | 0.64,0.34 | 850 |
如上表所报告,相对于含有比较产物A和B的应用实施例2c和2d的器件,含有实施例5和8的化合物的应用实施例2a和2b的器件表现出改善的电流效率和最大亮度。特别地,分别含有实施例5和8的化合物的应用实施例2a和2b的器件的开始电压大大低于含有比较产物A和B的应用实施例2c和2d的器件。
应用实施例3
有机堆层从ITO表面开始依次由作为空穴注入层(HIL)的100CuPC(酞菁铜络合物)、作为空穴传输层的3004,4’-双[N-(1-萘基)-N-苯基氨基]联苯(α-NPD)组成。发射层由300分别来自实施例5、实施例8和产物A的材料(作为基质,在下表中的应用实施例3a、3b和3c),在所有情况下都用6%绿光发射剂三(2-苯基吡啶基)铱络合物(客体)掺杂,接着作为空穴阻隔层的10nm的BAlq(双(2-甲基-8-喹啉醇)-4-(苯基苯酚)铝-(III)和作为电子传输层的30nm的Alq3(三(8-羟基喹啉)铝)组成。
对如上制备的器件测量的电流效率,以及开始电压(C,在1000cd/m2下)、CIE值和最大亮度在下表中报告:
应用实施例 | 基质 | 电流效率,在1000cd/m2下 | V,在1000cd/m2下 | CIE(x,y) | 最大亮度/cd/m2 |
3a | 实施例5的化合物 | 14.8 | 9.8 | 0.32,0.60 | 3100 |
3b | 实施例8的化合物 | 5.1 | 8.0 | 0.32,0.60 | 7500 |
3c | 产物A | 2.5 | 10.4 | 0.32,0.60 | 3000 |
如上表所报导,相对于含有比较产物A的应用实施例3c的器件,含有来自实施例5和8的材料的应用实施例3a和3b的器件表现出改善的电流效率和最大亮度以及较低的开始电压。特别地,含有实施例5的化合物的应用实施例3a的器件在1000Cd/m2下表现出14.8Cd/A的电流效率,其明显高于含有比较产物A的应用实施例3c的器件的电流效率。
Claims (11)
R1和R2相互独立为可任选被取代的C6-C24芳基或C2-C30杂芳基,
R3和R4相互独立为氢、可任选被取代的C1-C25烷基、C6-C24芳基或C2-C30杂芳基,
Ar和Ar’相互独立为C6-C14芳基,例如苯基或萘基,其可任选被1个或多个选自可任选间隔有-O-的C1-C25烷基或C1-C25烷氧基的基团取代,
R5和R6相互独立为卤素或有机取代基,或
彼此相邻的R5和R6一起形成可任选被取代的芳族或杂芳族环或环体系,
A1、A2、A1’和A2’相互独立为可任选被取代的C6-C24芳基、C2-C30杂芳基,或
A4、A4’、A6、A7、A8、A5、A5’、A6’、A7’和A8’相互独立为可任选被取代的C6-C24芳基或C2-C30杂芳基,
m1在每次出现时可相同或不同且为0、1、2、3或4,尤其是0、1或2,非常尤其为0或1;
R119和R120相互独立为C1-C18烷基、被E取代和/或间隔有D的C1-C18烷基、C6-C24芳基、被G取代的C6-C24芳基、C2-C20杂芳基、被G取代的C2-C20杂芳基、C2-C18链烯基、C2-C18炔基、C1-C18烷氧基、被E取代和/或间隔有D的C1-C18烷氧基或C7-C25芳烷基,或
R119和R120一起形成式=CR121R122的基团,其中:
R121和R122相互独立为H、C1-C18烷基、被E取代和/或间隔有D的C1-C18烷基、C6-C24芳基、被G取代的C6-C24芳基、C2-C20杂芳基或被G取代的C2-C20杂芳基;或
R119和R120一起形成五或六元环,所述环可任选被C1-C18烷基、被E取代和/或间隔有D的C1-C18烷基、C6-C24芳基、被G取代的C6-C24芳基、C2-C20杂芳基、被G取代的C2-C20杂芳基、C2-C18链烯基、C2-C18炔基、C1-C18烷氧基、被E取代和/或间隔有D的C1-C18烷氧基、C7-C25芳烷基或-C(=O)-R127取代,和
R127为H、C6-C18芳基、被C1-C18烷基或C1-C18烷氧基取代的C6-C18芳基、C1-C18烷基或间隔有-O-的C1-C18烷基,
D为-CO-、-COO-、-S-、-SO-、-SO2-、-O-、-NR65-、-SiR70R71-、-POR72-、-CR63=CR64-或-C≡C-,和
E为-OR69、-SR69、-NR65R66、-COR68、-COOR67、-CONR65R66、-CN或卤素,
G为E或C1-C18烷基,
R63和R64相互独立为C6-C18芳基;被C1-C18烷基、C1-C18烷氧基取代的C6-C18芳基;C1-C18烷基;或间隔有-O-的C1-C18烷基;或
R65、R65’和R66相互独立为C6-C18芳基;被C1-C18烷基、C1-C18烷氧基取代的C6-C18芳基;C1-C18烷基;或间隔有-O-的C1-C18烷基;或
R65和R66一起形成五或六元环,
R67为C6-C18芳基、被C1-C18烷基或C1-C18烷氧基取代的C6-C18芳基、C1-C18烷基或间隔有-O-的C1-C18烷基,
R68为H、C6-C18芳基、被C1-C18烷基或C1-C18烷氧基取代的C6-C18芳基、C1-C18烷基或间隔有-O-的C1-C18烷基,
R69为C6-C18芳基;被C1-C18烷基、C1-C18烷氧基取代的C6-C18芳基;C1-C18烷基;或间隔有-O-的C1-C18烷基,
R70和R71相互独立为C1-C18烷基、C6-C18芳基或被C1-C18烷基取代的C6-C18芳基;和
R72为C1-C18烷基、C6-C18芳基或被C1-C18烷基取代的C6-C18芳基;
R41在每次出现时可相同或不同且为Cl,F,CN,NR45R45’,C1-C25烷基,C4-C18环烷基,C1-C25烷氧基,其中1个或多个彼此不相邻的碳原子可被-NR45-、-O-、-S-、-C(=O)-O-或-O-C(=O)-O-替换,和/或其中1个或多个氢原子可被F替换,C6-C24芳基或C6-C24芳氧基,其中1个或多个碳原子可被O、S或N替换,和/或其可被1个或多个非芳族基团R41取代,或2个或更多个基团R41形成环体系;
R45和R45’相互独立为C1-C25烷基,C4-C18环烷基,其中1个或多个彼此不相邻的碳原子可被-NR45”-、-O-、-S-、-C(=O)-O-或-O-C(=O)-O-替换,和/或其中1个或多个氢原子可被F替换,C6-C24芳基或C6-C24芳氧基,其中1个或多个碳原子可被O、S或N替换,和/或其可被1个或多个非芳族基团R41取代,
R45”为C1-C25烷基或C4-C18环烷基,和
m在每次出现时可相同或不同且为0、1、2或3,尤其是0、1或2,非常尤其为0或1。
2.电子器件,其中所述电子器件为电致发光(EL)器件。
3.根据权利要求2的EL器件,所述EL器件含有式I化合物,其中
R1和R2相互独立为可任选被取代的C6-C24芳基或C2-C30杂芳基;和R3为氢,R4为可任选被取代的C1-C25烷基、C6-C24芳基或C2-C30杂芳基,或R3和R4相互独立为可任选被取代的C1-C25烷基、C6-C24芳基或C2-C30杂芳基。
5.根据权利要求2-4中任一项的EL器件,所述EL器件含有式I化合物,其中:
A1、A1’、A3和A3’相互独立为可任选被取代的C6-C24芳基或C2-C30杂芳基,尤其是可任选取代的苯基、萘基、蒽基、联苯基、2-芴基、菲基或苝基,例如
m1在每次出现时可相同或不同且为0、1、2、3或4,尤其是0、1或2,非常尤其为0或1;
R116、R117和R117’相互独立为H,卤素,尤其是F,-CN,C1-C18烷基,被E取代和/或间隔有D的C1-C18烷基,C6-C24芳基,被G取代的C6-C24芳基,C2-C20杂芳基,被G取代的C2-C20杂芳基,C2-C18链烯基,C2-C18炔基,C1-C18烷氧基,被E取代和/或间隔有D的C1-C18烷氧基,C7-C25芳烷基,-C(=O)-R127,-C(=O)OR127或-C(=O)NR127R126,或
彼此相邻的取代基R116、R117和R117’可形成环,
R119和R120如权利要求1所定义,
R126和R127相互独立为H、C6-C18芳基、被C1-C18烷基或C1-C18烷氧基取代的C6-C18芳基、C1-C18烷基或间隔有-O-的C1-C18烷基,
R41如权利要求1所定义且m1如上所定义;或
R116、R116’、R117和R117’如上所定义;
D、E和G如权利要求1所定义;或
其中R116、R117和R117’如上所定义。
7.根据权利要求2-6中任一项的EL器件,所述EL器件含有选自如下的化合物:
8.根据权利要求2-7中任一项的电致发光器件,所述电致发光器件含有阴极、阳极和在此之间的含有基质材料与磷光发光材料的发光层,其中所述基质材料为式I化合物。
10.根据权利要求9的式I化合物在电子照相感光器、光电转换器、太阳能电池、影像感应器、染料激光和电致发光器件中的用途。
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- 2008-09-10 JP JP2010525302A patent/JP5669580B2/ja active Active
- 2008-09-10 AT AT08832623T patent/ATE552227T1/de active
- 2008-09-10 KR KR1020107008467A patent/KR101625235B1/ko active IP Right Grant
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- 2008-09-10 CN CN200880108109.XA patent/CN101848882B/zh active Active
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CN106279229A (zh) * | 2010-10-15 | 2017-01-04 | 默克专利有限公司 | 用于有机电致发光器件的基于苯并菲的材料 |
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Also Published As
Publication number | Publication date |
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TW200926474A (en) | 2009-06-16 |
US8628862B2 (en) | 2014-01-14 |
KR20100070357A (ko) | 2010-06-25 |
CN101848882B (zh) | 2015-04-29 |
WO2009037155A1 (en) | 2009-03-26 |
ATE552227T1 (de) | 2012-04-15 |
EP2193112B1 (en) | 2012-04-04 |
KR101625235B1 (ko) | 2016-05-27 |
US20100277060A1 (en) | 2010-11-04 |
EP2193112A1 (en) | 2010-06-09 |
JP2010539718A (ja) | 2010-12-16 |
JP5669580B2 (ja) | 2015-02-12 |
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