CN101998983A - 用于光电子器件的发射聚合物材料 - Google Patents
用于光电子器件的发射聚合物材料 Download PDFInfo
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- CN101998983A CN101998983A CN2008801225378A CN200880122537A CN101998983A CN 101998983 A CN101998983 A CN 101998983A CN 2008801225378 A CN2008801225378 A CN 2008801225378A CN 200880122537 A CN200880122537 A CN 200880122537A CN 101998983 A CN101998983 A CN 101998983A
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- Prior art keywords
- replacement
- polymkeric substance
- alkyl
- group
- compound
- Prior art date
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- 230000005693 optoelectronics Effects 0.000 title abstract description 11
- 239000000463 material Substances 0.000 title description 28
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 56
- 150000001875 compounds Chemical class 0.000 claims abstract description 28
- -1 phenylimine Chemical compound 0.000 claims abstract description 26
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 21
- 125000003118 aryl group Chemical group 0.000 claims abstract description 21
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 claims abstract description 16
- 125000002877 alkyl aryl group Chemical group 0.000 claims abstract description 16
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 16
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 14
- 239000001257 hydrogen Substances 0.000 claims abstract description 14
- QLPKTAFPRRIFQX-UHFFFAOYSA-N 2-thiophen-2-ylpyridine Chemical compound C1=CSC(C=2N=CC=CC=2)=C1 QLPKTAFPRRIFQX-UHFFFAOYSA-N 0.000 claims abstract description 8
- JVZRCNQLWOELDU-UHFFFAOYSA-N gamma-Phenylpyridine Natural products C1=CC=CC=C1C1=CC=NC=C1 JVZRCNQLWOELDU-UHFFFAOYSA-N 0.000 claims abstract description 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 5
- VIXWGKYSYIBATJ-UHFFFAOYSA-N pyrrol-2-one Chemical compound O=C1C=CC=N1 VIXWGKYSYIBATJ-UHFFFAOYSA-N 0.000 claims abstract description 5
- KAJMDIRNTNSOLE-UHFFFAOYSA-N 2-naphthalen-1-yl-1,3-benzoxazole Chemical compound C1=CC=C2C(C=3OC4=CC=CC=C4N=3)=CC=CC2=C1 KAJMDIRNTNSOLE-UHFFFAOYSA-N 0.000 claims abstract description 4
- XBHOUXSGHYZCNH-UHFFFAOYSA-N 2-phenyl-1,3-benzothiazole Chemical compound C1=CC=CC=C1C1=NC2=CC=CC=C2S1 XBHOUXSGHYZCNH-UHFFFAOYSA-N 0.000 claims abstract description 4
- KLLLJCACIRKBDT-UHFFFAOYSA-N 2-phenyl-1H-indole Chemical compound N1C2=CC=CC=C2C=C1C1=CC=CC=C1 KLLLJCACIRKBDT-UHFFFAOYSA-N 0.000 claims abstract description 4
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 claims abstract description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 3
- 150000002431 hydrogen Chemical class 0.000 claims abstract 7
- 239000000126 substance Substances 0.000 claims description 66
- 229910052760 oxygen Inorganic materials 0.000 claims description 13
- VDULMXJUOWIPGE-UHFFFAOYSA-N 1-phenylisoquinoline quinoline Chemical compound N1=CC=CC2=CC=CC=C12.C1(=CC=CC=C1)C1=NC=CC2=CC=CC=C12 VDULMXJUOWIPGE-UHFFFAOYSA-N 0.000 claims description 11
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 10
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims description 10
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 8
- 125000005259 triarylamine group Chemical group 0.000 claims description 8
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims description 6
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 6
- 150000003222 pyridines Chemical class 0.000 claims description 6
- 125000001118 alkylidene group Chemical group 0.000 claims description 5
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 claims description 3
- SZXUTTGMFUSMCE-UHFFFAOYSA-N 2-(1h-imidazol-2-yl)pyridine Chemical class C1=CNC(C=2N=CC=CC=2)=N1 SZXUTTGMFUSMCE-UHFFFAOYSA-N 0.000 claims description 3
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 125000000950 dibromo group Chemical group Br* 0.000 claims description 2
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 claims description 2
- 125000003983 fluorenyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims 1
- 229920000642 polymer Polymers 0.000 abstract description 12
- 125000002947 alkylene group Chemical group 0.000 abstract 3
- NRSBAUDUBWMTGL-UHFFFAOYSA-N 2-(1-benzothiophen-2-yl)pyridine Chemical compound S1C2=CC=CC=C2C=C1C1=CC=CC=N1 NRSBAUDUBWMTGL-UHFFFAOYSA-N 0.000 abstract 2
- 125000005415 substituted alkoxy group Chemical group 0.000 abstract 2
- 125000000547 substituted alkyl group Chemical group 0.000 abstract 2
- 125000003107 substituted aryl group Chemical group 0.000 abstract 2
- LPCWDYWZIWDTCV-UHFFFAOYSA-N 1-phenylisoquinoline Chemical compound C1=CC=CC=C1C1=NC=CC2=CC=CC=C12 LPCWDYWZIWDTCV-UHFFFAOYSA-N 0.000 abstract 1
- FIISKTXZUZBTRC-UHFFFAOYSA-N 2-phenyl-1,3-benzoxazole Chemical compound C1=CC=CC=C1C1=NC2=CC=CC=C2O1 FIISKTXZUZBTRC-UHFFFAOYSA-N 0.000 abstract 1
- GOLORTLGFDVFDW-UHFFFAOYSA-N 3-(1h-benzimidazol-2-yl)-7-(diethylamino)chromen-2-one Chemical compound C1=CC=C2NC(C3=CC4=CC=C(C=C4OC3=O)N(CC)CC)=NC2=C1 GOLORTLGFDVFDW-UHFFFAOYSA-N 0.000 abstract 1
- VJHVLELNDFVKMS-UHFFFAOYSA-N 3-methoxy-2-phenylpyridine Chemical compound COC1=CC=CN=C1C1=CC=CC=C1 VJHVLELNDFVKMS-UHFFFAOYSA-N 0.000 abstract 1
- 125000001475 halogen functional group Chemical group 0.000 abstract 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical group [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 abstract 1
- 239000010410 layer Substances 0.000 description 65
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
- 239000000243 solution Substances 0.000 description 28
- 229910052757 nitrogen Inorganic materials 0.000 description 20
- 150000002220 fluorenes Chemical class 0.000 description 19
- 238000003756 stirring Methods 0.000 description 19
- 239000000178 monomer Substances 0.000 description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 15
- 229910052799 carbon Inorganic materials 0.000 description 13
- 229910052741 iridium Inorganic materials 0.000 description 13
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 13
- 238000000034 method Methods 0.000 description 13
- 239000000203 mixture Substances 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- 239000003921 oil Substances 0.000 description 10
- 239000001301 oxygen Substances 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 9
- 229910052751 metal Inorganic materials 0.000 description 9
- 239000002184 metal Substances 0.000 description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
- 238000005401 electroluminescence Methods 0.000 description 8
- 238000002347 injection Methods 0.000 description 8
- 239000007924 injection Substances 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 7
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 7
- 230000006798 recombination Effects 0.000 description 7
- 238000005215 recombination Methods 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 239000000975 dye Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 6
- 239000002243 precursor Substances 0.000 description 6
- 230000008569 process Effects 0.000 description 6
- 229960001866 silicon dioxide Drugs 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 239000000758 substrate Substances 0.000 description 6
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 5
- 239000005864 Sulphur Substances 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 150000001721 carbon Chemical group 0.000 description 5
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 5
- 125000000753 cycloalkyl group Chemical group 0.000 description 5
- 238000000151 deposition Methods 0.000 description 5
- 235000019439 ethyl acetate Nutrition 0.000 description 5
- 239000003446 ligand Substances 0.000 description 5
- 239000011777 magnesium Substances 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 229920006395 saturated elastomer Polymers 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-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
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
- 230000008021 deposition Effects 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 125000001188 haloalkyl group Chemical group 0.000 description 4
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 4
- 229910052749 magnesium Inorganic materials 0.000 description 4
- 230000005855 radiation Effects 0.000 description 4
- 229910052710 silicon Inorganic materials 0.000 description 4
- 239000010703 silicon Substances 0.000 description 4
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 4
- 238000012546 transfer Methods 0.000 description 4
- NRWUQWRLIMQGND-UHFFFAOYSA-N (4-hydroxyphenyl)-(1h-pyrrol-2-yl)methanone Chemical class C1=CC(O)=CC=C1C(=O)C1=CC=CN1 NRWUQWRLIMQGND-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- 229910004298 SiO 2 Inorganic materials 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 125000002252 acyl group Chemical group 0.000 description 3
- 239000000956 alloy Substances 0.000 description 3
- 229910045601 alloy Inorganic materials 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- 239000004411 aluminium Substances 0.000 description 3
- 229910052786 argon Inorganic materials 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
- 229910052791 calcium Inorganic materials 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 238000007872 degassing Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 230000032050 esterification Effects 0.000 description 3
- 238000005886 esterification reaction Methods 0.000 description 3
- 230000005281 excited state Effects 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 230000005283 ground state Effects 0.000 description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 3
- NFGGQMYSOLVBLF-UHFFFAOYSA-N phenyl(1h-pyrrol-2-yl)methanone Chemical class C=1C=CC=CC=1C(=O)C1=CC=CN1 NFGGQMYSOLVBLF-UHFFFAOYSA-N 0.000 description 3
- 229910052698 phosphorus Inorganic materials 0.000 description 3
- 239000002861 polymer material Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 150000003233 pyrroles Chemical class 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 241000894007 species Species 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
- KYLUAQBYONVMCP-UHFFFAOYSA-N (2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P KYLUAQBYONVMCP-UHFFFAOYSA-N 0.000 description 2
- UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical compound C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 description 2
- SNTWKPAKVQFCCF-UHFFFAOYSA-N 2,3-dihydro-1h-triazole Chemical compound N1NC=CN1 SNTWKPAKVQFCCF-UHFFFAOYSA-N 0.000 description 2
- YMMGRPLNZPTZBS-UHFFFAOYSA-N 2,3-dihydrothieno[2,3-b][1,4]dioxine Chemical compound O1CCOC2=C1C=CS2 YMMGRPLNZPTZBS-UHFFFAOYSA-N 0.000 description 2
- FYEFHYMUEWRCRF-UHFFFAOYSA-N 2,7-dibromofluoren-1-one Chemical compound BrC1=CC=C2C3=CC=C(Br)C(=O)C3=CC2=C1 FYEFHYMUEWRCRF-UHFFFAOYSA-N 0.000 description 2
- 229940090248 4-hydroxybenzoic acid Drugs 0.000 description 2
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 2
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 238000007605 air drying Methods 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- FFBHFFJDDLITSX-UHFFFAOYSA-N benzyl N-[2-hydroxy-4-(3-oxomorpholin-4-yl)phenyl]carbamate Chemical compound OC1=C(NC(=O)OCC2=CC=CC=C2)C=CC(=C1)N1CCOCC1=O FFBHFFJDDLITSX-UHFFFAOYSA-N 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 230000000903 blocking effect Effects 0.000 description 2
- 230000031709 bromination Effects 0.000 description 2
- 238000005893 bromination reaction Methods 0.000 description 2
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- 150000004985 diamines Chemical class 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- YLQWCDOCJODRMT-UHFFFAOYSA-N fluoren-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C2=C1 YLQWCDOCJODRMT-UHFFFAOYSA-N 0.000 description 2
- 150000002240 furans Chemical class 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical compound C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 description 2
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 2
- 150000002475 indoles Chemical class 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- MILUBEOXRNEUHS-UHFFFAOYSA-N iridium(3+) Chemical compound [Ir+3] MILUBEOXRNEUHS-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 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 2
- 239000012044 organic layer Substances 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- 238000005424 photoluminescence Methods 0.000 description 2
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 150000003217 pyrazoles Chemical class 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229910052709 silver Inorganic materials 0.000 description 2
- 239000011775 sodium fluoride Substances 0.000 description 2
- 235000013024 sodium fluoride Nutrition 0.000 description 2
- 238000004528 spin coating Methods 0.000 description 2
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 2
- 125000003831 tetrazolyl group Chemical group 0.000 description 2
- PFZLGKHSYILJTH-UHFFFAOYSA-N thieno[2,3-c]thiophene Chemical compound S1C=C2SC=CC2=C1 PFZLGKHSYILJTH-UHFFFAOYSA-N 0.000 description 2
- 229930192474 thiophene Natural products 0.000 description 2
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 2
- 238000001291 vacuum drying Methods 0.000 description 2
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- 125000003944 tolyl group Chemical group 0.000 description 1
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- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
- C07F15/0033—Iridium compounds
- C07F15/004—Iridium compounds without a metal-carbon linkage
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/12—Light sources with substantially two-dimensional radiating surfaces
- H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/10—Organic polymers or oligomers
- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/10—Organic polymers or oligomers
- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
- H10K85/115—Polyfluorene; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/14—Macromolecular compounds
- C09K2211/1408—Carbocyclic compounds
- C09K2211/1416—Condensed systems
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/14—Macromolecular compounds
- C09K2211/1408—Carbocyclic compounds
- C09K2211/1425—Non-condensed systems
-
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Abstract
在光电子器件中,可使用包含至少一种衍生自式(I)的化合物的结构单元或包含至少一个式(II)的侧基的聚合物,其中R1、R3、R4和R6独立地为氢、烷基、烷氧基、氧杂烷基、烷基芳基、芳基、芳基烷基、杂芳基、取代的烷基、取代的烷氧基、取代的氧杂烷基、取代的烷基芳基、取代的芳基、取代的芳基烷基或取代的杂芳基;R1a为氢或烷基;R2为亚烷基、取代的亚烷基、氧杂亚烷基、CO或CO2;R2a为亚烷基;R5每次出现时独立地为氢、烷基、烷基芳基、芳基、芳基烷基、烷氧基、羧基、取代的烷基、取代的烷基芳基、取代的芳基、取代的芳基烷基或取代的烷氧基;X为位于2,5-或2,7-位的卤素、三氟甲磺酸根、-B(OR1a)2或式(III);并且L衍生自苯基吡啶、甲苯基吡啶、苯并噻吩基吡啶、苯基异喹啉、二苯并喹喔啉、芴基吡啶、酮基吡咯、2-(1-萘基)苯并噁唑、2-苯基苯并噁唑、2-苯基苯并噻唑、香豆素、噻吩基吡啶、苯基吡啶、苯并噻吩基吡啶、3-甲氧基-2-苯基吡啶、噻吩基吡啶、苯基亚胺、乙烯基吡啶、吡啶基萘、吡啶基吡咯、吡啶基咪唑、苯基吲哚、其衍生物或其组合。
Description
关于联邦资助的研究和开发的声明
本发明按照美国能源部签署的合同DOE NETL DE-FC26-05NT42343在政府支持下产生。政府可拥有本发明的某些权利。
阿明背景
本发明涉及用于光电子器件的具有铱络合物侧基的聚合物。
有机发光器件(OLEDs)利用在受到偏压时发光的薄膜有机材料,有机发光器件预期会成为平板显示技术的越来越受欢迎的形式。可能的应用包括手机、个人数字助理(PDAs)、电脑显示器、交通工具中的信息显示屏、电视监视器和一般照明使用的光源。由于它们的明亮的颜色、宽视角、与全动感视频的相容性、宽温度范围、薄且一致的波形因数、低功率需求和低成本制造过程的可能性,可将OLEDs视为阴极射线管(CRTs)和液晶显示器(LCDs)的未来替代技术。由于它们的高发光效率,OLEDs可替代用于某些类型应用的白炽灯,甚至是荧光灯。
从OLEDs发光一般通过电荧光发生,即,通过跨基态电致发光材料施加偏压形成的单重激发态发光。认为能够通过交替机制(alternate mechanism)电磷光发光(即,通过跨基态电荧光材料施加偏压形成的三重激发态发光)的OLEDs会表现出比主要通过电荧光发光的OLEDs明显更高的量子效率。通过电磷光从OLEDs发光受到限制,因为在大多数发光有机材料中的三重激发态强烈布置为非辐射性弛豫至基态。因此,电磷光材料有望作为OLED器件和相对于该领域现有状态表现出更大效率的其他光电子器件的关键部件。例如,预期能够通过电磷光发光的OLEDs表现出损失到器件内无辐射衰减过程的能量减少(相对于主要由电荧光发光的OLEDs),从而提供在OLED工作期间控制温度的另外措施。
提高的发光效率已通过在有机电致发光器件(如OLED)中加入磷光含铂染料达到(Baldo等人,“Highly Efficient Phosphorescent Emission from Organic Electroluminescent Devices”(从有机电致发光器件高效发射磷光),Nature,vol.395,151-154,1998),并且也已利用磷光含铱染料(US 2003/0096138)。基于酮基吡咯配体的可聚合磷光铱络合物公开于2006年8月14日提交的待审美国专利申请11/504552,所述申请要求2006年7月28日提交的美国临时专利申请60/833935的优先权,其全部内容全文通过引用结合到本文中。尽管有了早先的进展,目前仍对发现这样的新磷光物质相当关注,所述磷光物质提高效率并提供控制OLED发光颜色的更大措施,同时提高器件寿命。
发明概述
现已发现,通过使铱染料以悬垂侧链取代基形式从聚合物主链分开,可防止在固态由共轭效应导致的铱(III)染料发射性质的改变。因此,一方面,本发明涉及式I的化合物和包含至少一种由其衍生的结构单元的聚合物
其中
R1、R3、R4和R6独立地为氢、烷基、烷氧基、氧杂烷基、烷基芳基、芳基、芳基烷基、杂芳基、取代的烷基、取代的烷氧基、取代的氧杂烷基、取代的烷基芳基、取代的芳基、取代的芳基烷基或取代的杂芳基;
R1a为氢或烷基;
R2为亚烷基、取代的亚烷基、氧杂亚烷基、CO或CO2;
R2a为亚烷基;
R5每次出现时独立地为氢、烷基、烷基芳基、芳基、芳基烷基、烷氧基、羧基、取代的烷基、取代的烷基芳基、取代的芳基、取代的芳基烷基或取代的烷氧基;
L衍生自苯基吡啶、甲苯基吡啶、苯并噻吩基吡啶、苯基异喹啉、二苯并喹喔啉(dibenzoquinozaline)、芴基吡啶、酮基吡咯、2-(1-萘基)苯并噁唑、2-苯基苯并噁唑、2-苯基苯并噻唑、香豆素、噻吩基吡啶、苯基吡啶、苯并噻吩基吡啶、3-甲氧基-2-苯基吡啶、噻吩基吡啶、苯基亚胺、乙烯基吡啶、吡啶基萘、吡啶基吡咯、吡啶基咪唑、苯基吲哚、其衍生物或其组合。
另一方面,本发明涉及包含至少一个式II的侧基的聚合物
其中R2、R3、R4、R6和L如对式I所限定。
另一方面,本发明涉及光电子器件,所述光电子器件包含具有至少一种衍生自式I的化合物的结构单元的聚合物或具有至少一个式II的侧基的聚合物。
发明详述
本发明涉及式I的化合物、衍生自这些化合物的聚合物、具有式II的侧基的聚合物和在一个或多个发光层中包含聚合物的光电子器件。
结构单元或侧基可衍生自芴或三芳基胺化合物。从含悬垂Ir络合物的芴单体衍生的结构单元的实例包括
其中R1b为氢、烷基、烷氧基、氧杂烷基、取代的烷基、取代的烷氧基或取代的氧杂烷基;并且
R1c为氢、烷基或取代的烷基。
在很多实施流程中,R2优选为氧杂亚烷基,特别是-CH2CH2O-。
含悬垂Ir络合物的三芳基胺单体的实例包括
其中Z为O、S或直接键。
衍生自式I的化合物或具有式II的侧基的聚合物可另外包含衍生自其他单体(特别是芴单体)的结构单元,如授予Dow的US5,929,194、US 5,948,552、US 6,204,515、US 6,605,373、US6,815,505和US 6,916,902所述。更特别是,所述结构单元可衍生自二溴9,9-二辛基芴单体。聚合物可包含衍生自芴单体的那些单元之外还包含衍生自至少一种三芳基胺单体(特别是TFB)的结构单元,或者聚合物可包含衍生自至少一种三芳基胺单体(特别是TFB)的结构单元来代替衍生自芴单体的那些单元。适合三芳基胺单体和包含衍生自这些单体和芴单体的残基的聚合物描述于同样授予Dow的US 5,708,130、US 6,169,163、US 6,353,083、US 6,255447、US6,255,449、US 6,900,285。例如,除了含铱络合物的残基外,聚合物还可包含式III的结构单元
III
特别是,聚合物可包含式IV的结构单元
其中piq为苯基异喹啉基。更具体地讲,聚合物可包含约95%式III的结构单元和5%式IV的结构单元,如下所示
其中piq为苯基异喹啉基。
在一些实施流程中,式II的侧基具有下式
在这些实施流程的一些中,L为苯基异喹啉基(piq)。
衍生自式I的化合物的结构单元或式II的侧基可以聚合物约0.01%重量至约50%重量,特别是约0.1%重量至约10%重量,更特别是约0.5%重量至约5%重量的量存在于聚合物中。聚合物一般具有由凝胶渗透色谱法测定大于2,000克/摩尔的数均分子量(Mn),特别是大于约5,000克/摩尔,大于约15,000克/摩尔,更特别是大于约25,000克/摩尔。
本发明的光电子器件包含至少一种衍生自式I的化合物或具有式II的侧基的聚合物。所述聚合物可与荧光发光物质混合,如基于芴单体的(共)聚合物,例如F8-TFB;购得的发光聚合物,如ADS131BE、ADS231BE、ADS331BE、ADS431BE、ADS429BE、ADS160BE、ADS329BE、ADS229BE、ADS129BE、ADS180BE,由American Dye Sources提供;和BP105和BP361,购自SumationCompany Ltd。可用于与本发明的聚合物混合的其他物质包括分子型和低聚型物种,如芴三聚体及其衍生物;聚合型或分子型三芳基胺物质,包括US 3,265,496和4,539,507所述的那些物质和从AmericanDye Sources购得的三芳基胺,如ADS254BE、ADS12HTM和ADS04HTM;取代的聚亚苯基聚合物,如购自American Dye Sources的ADS120BE;和具有通过非共轭连接基连接的低聚单元的聚合物,如US 2005/0256290所述。
在本发明的聚合物与其他物质共混时,优选其他物质的最低三重态能级(由光致发光或其他技术测定)大于本发明的聚合物的基于悬垂铱的发射体的三重态能量。具体地讲,聚合物可与一种或多种荧光物质共混,如发蓝光芴(共)聚合物,因为这些通常具有低于本发明的聚合物的最低发射单重态能量的最低三重态能量,并且表现出发蓝光。
本发明的聚合物和/或所述聚合物与发蓝光芴(共)聚合物的混合物可包含在邻近包含一种或多种芴聚合物或共聚物(如BP105或F8-TFB)的另一个发光层布置的器件的发光层中,以形成双层结构。在这些器件中,双层结构可通过数种不同的方法形成,如PCT/US07/68620所述。例如,在沉积第一层后,双层可只通过热处理使其不溶解,或者通过在第一层内包含可交联聚合剂,以使聚合物链连接在一起或形成互穿网络。可通过UV照射或热活化引发聚合。聚合处理可通过加入少量引发剂增强,如购自Sartomer的引发剂或BPO或AIBN。或者,可通过用不溶解第一层的溶剂施加第二层,通过接触层压(Ramsdale等人,J.Appl.Phys,vol 92,4266页(2002))或通过蒸气沉积形成层结构。如果需要,可顺次用这些方法产生多层结构,其中一个或多个层包含一种或多种本发明的聚合物。
本发明的光电子器件可另外包含至少一种与所述聚合物光学偶合的光致发光(“PL”)物质,使得所述磷光体物质吸收一部分由其发射的EM辐射,并发射在第三波长范围的EM辐射。用作PL物质的物质和含PL物质的示例性器件结构描述于US 7,063,900,其全部内容通过引用结合到本文中。
光电子器件(例如有机发光器件)通常包含多层,在最简单的情况下,包含阳极层和相应的阴极层,并且有机电致发光层布置于所述阳极和所述阴极之间。在跨电极施加偏压时,电子通过阴极注入电致发光层,而电子从电致发光层从阳极去除(或者“空穴”从电致发光层从阳极“注入”)。当空穴与电子在电致发光层内结合形成单重态或三重态激子时发光,当单重态激子通过辐射衰减将能量转移到环境时发光。与单重态激子不同,三重态激子通常不能经历辐射衰减,因此不发光,除非在很低温度。理论研究指出,三重态激子的形成概率为单重态激子的约3倍。因此,形成三重态激子表示对通常在环境温度或接近环境温度工作的有机发光器件的效率的基本限制。本发明的聚合物可作为发光、短寿命激发态物种的前体,其以通常无价值的三重态激子所遭遇的形式形成,并且转移能量。
除了阳极、阴极和发光物质外,可在有机发光器件中存在的其他部件包括空穴注入层、电子注入层和电子输送层。在含电子输送层的有机发光器件工作期间,在电子输送层中存在的大部分载流子(即空穴和电子)为电子,并且可通过空穴和电子输送层中存在的电子复合发光。可在有机发光器件中存在的另外部件包括空穴输送层、空穴输送发射层、空穴阻挡层和电子输送发射层。
有机电致发光层为有机发光器件内的层,此层在工作时含显著浓度的电子和空穴两者,并且提供用于激子形成和发光的部位。空穴注入层为通常与阳极接触的层,此层促进空穴从阳极注入OLED的内层,而电子注入层为通常与阴极接触的层,此层促进电子从阴极注入OLED。空穴注入层和电子输送层均不必与阴极接触。通常电子输送层不是有效的空穴输送体,因此用于阻挡空穴向阴极迁移。电子输送层是促进电子从阴极传到电荷复合部位的层。空穴输送层是在OLED工作时促进空穴从阳极传到电荷复合部位并且不必与阳极接触的层。空穴输送发射层是其中在OLED工作时促进空穴传到电荷复合部位、大部分载流子为空穴、并且发射不仅通过与残余电子复合而且通过从器件中别处的电荷复合区域转移能量的层。电子输送发射层是其中在OLED工作时促进电子传到电荷复合部位、大部分载流子为电子、并且发射不仅通过与残余空穴复合而且通过从器件中别处的电荷复合区域转移能量的层。
适合用作阳极的物质包括具有通过四点探针技术测定至少约100欧姆/□的体电导率的物质。氧化锡铟(ITO)常用作阳极,因为它基本上对光透射透明,并因此促进从电活性有机层发射的光逸出。可用作阳极层的其他物质包括氧化锡、氧化铟、氧化锌、氧化锌铟、氧化锡铟锌、氧化锑及其混合物。
适合用作阴极的物质包括可将负载流子(电子)注入OLED的一个或多个内层的零价金属。适合用作阴极的各种零价金属包括K、Li、Na、Cs、Mg、Ca、Sr、Ba、Al、Ag、Au、In、Sn、Zn、Zr、Sc、Y、镧系元素、其合金及其混合物。用作阴极层的适合合金物质包括Ag-Mg、Al-Li、In-Mg、Al-Ca和Al-Au合金。层状的非合金结构也可用于阴极,如由较厚的零价金属(如铝或银)层覆盖的金属(如钙)或金属氟化物(如LiF)的薄层。特别是,阴极可由单一零价金属(尤其是金属铝)构成。
适用于空穴注入层的物质包括3,4-亚乙二氧基噻吩(PEDOT)和PEDOT与以商标购自H.C.Stark,Inc.的聚苯乙烯磺酸盐(PSS)的共混物,以及购自Air Products Corporation的基于噻吩并[3,4b]噻吩(TT)单体的聚合物。
适用于空穴输送层的物质包括1,1-双((二-4-甲苯基氨基)苯基)环己烷、N,N′-双(4-甲基苯基)-N,N′-双(4-乙基苯基)-(1,1′-(3,3′-二甲基)联苯)-4,4′-二胺、四-(3-甲基苯基)-N,N,N′,N′-2,5-苯二胺、苯基-4-N,N-二苯基氨基苯乙烯、对-(二乙基氨基)苯甲醛二苯腙、三苯胺、1-苯基-3-(对-(二乙基氨基)苯乙烯基)-5-(对-(二乙基氨基)苯基)吡唑啉、1,2-反-双(9H-咔唑-9-基)环丁烷、N,N,N′,N′-四(4-甲基苯基)-(1,1′-联苯)-4,4′-二胺、铜酞菁、聚乙烯基咔唑、(苯基甲基)聚硅烷;聚(3,4-亚乙二氧基噻吩)(PEDOT)、聚苯胺、聚乙烯基咔唑、三芳基二胺、四苯基二胺、芳族叔胺、腙衍生物、咔唑衍生物、三唑衍生物、咪唑衍生物、具有氨基的噁二唑衍生物和聚噻吩,如美国专利6,023,371所公开。
适合用作电子输送层的物质包括聚(9,9-二辛基芴)、三(8-羟基喹啉)合铝(Alq3)、2,9-二甲基-4,7-二苯基-1,1-菲咯啉、4,7-二苯基-1,10-菲咯啉、2-(4-联苯基)-5-(4-叔丁基苯基)-1,3,4-噁二唑、3-(4-联苯基)-4-苯基-5-(4-叔丁基苯基)-1,2,4-三唑、含1,3,4-噁二唑的聚合物、含1,3,4-三唑的聚合物、含喹喔啉的聚合物和氰基-PPV。
定义
在本发明的上下文中,烷基旨在包括直链、支链或环状烃结构及其组合,包括低级烷基和高级烷基。优选的烷基为C20或以下的烷基。低级烷基是指1至6个碳原子,优选1至4个碳原子的烷基,包括甲基、乙基、正丙基、异丙基、正丁基、仲丁基和叔丁基。高级烷基是指具有7或更多个碳原子,优选7至20个碳原子的烷基,包括正、仲和叔庚基、辛基和十二烷基。环烷基为烷基的一个子集,包括3至8个碳原子的环烃基。环烷基的实例包括环丙基、环丁基、环戊基和降冰片基。“烯基”和“炔基”是指烷基的两个或更多个氢原子分别由双键或三键代替。
芳基和杂芳基是指含0至3个选自氮、氧或硫的杂原子的5元或6元芳族或杂芳族环;含0至3个选自氮、氧或硫的杂原子的双环9元或10元芳族或杂芳族环系统;或含0至3个选自氮、氧或硫的杂原子的三环13元或14元芳族或杂芳族环系统。芳族6至14元碳环包括例如苯、萘、茚满、萘满和芴;5至10元芳族杂环包括例如咪唑、吡啶、吲哚、噻吩、苯并吡喃酮、噻唑、呋喃、苯并咪唑、喹啉、异喹啉、喹喔啉、嘧啶、吡嗪、四唑和吡唑。
烷氧基是指通过氧连接到母体结构的直链、支链、环状结构及其组合的1至8个碳原子的基团。实例包括甲氧基、乙氧基、丙氧基、异丙氧基、环丙基氧基和环己基氧基。低级烷氧基是指含1至4个碳的基团。
酰基是指通过羰基官能团连接到母体结构的直链、支链、环状结构的、饱和、不饱和和芳族及其组合的1至8个碳原子的基团。酰基残基中的一个或多个碳可由氮、氧或硫代替,只要到母体的连接点保持在羰基。实例包括乙酰基、苯甲酰基、丙酰基、异丁酰基、叔丁氧基羰基和苄基氧基羰基。低级酰基是指含1至4个碳的基团。
杂环是指其中一个或两个碳由杂原子(如氧、氮或硫)代替的环烷基或芳基残基。落在本发明范围内的杂环的实例包括吡咯烷、吡唑、吡咯、吲哚、喹啉、异喹啉、四氢异喹啉、苯并呋喃、苯并二氧杂环己烷、苯并二氧杂环戊烯(在作为取代基出现时,一般称为亚甲二氧基苯基)、四唑、吗啉、噻唑、吡啶、哒嗪、嘧啶、噻吩、呋喃、噁唑、噁唑啉、异噁唑、二氧杂环己烷和四氢呋喃。
取代的(substituted)是指包括但不限于烷基、烷基芳基、芳基、芳基烷基和杂芳基的残基,其中残基的最多3个H原子用低级烷基、取代的烷基、芳基、取代的芳基、卤代烷基、烷氧基、羰基、羧基、羧酰烷氧基(carboxalkoxy)、甲酰氨基、酰基氧基、脒基、硝基、卤素、羟基、OCH(COOH)2、氰基、伯氨基、仲氨基、酰基氨基、烷硫基、亚砜、砜、苯基、苄基、苯氧基、苄氧基、杂芳基或杂芳基氧基代替。
卤代烷基是指其中一个或多个H原子由卤素原子代替的烷基残基,术语卤代烷基包括全卤烷基。落在本发明范围内的卤代烷基的实例包括CH2F、CHF2和CF3。
本文所述的很多化合物可包含一个或多个不对称中心,并且可因此产生对映异构体、非对映异构体和其他立体异构形式,这些形式可按照绝对立体化学限定为(R)-或(S)-。本发明旨在包括所有这些可能的异构体及其外消旋和旋光纯形式。旋光(R)-和(S)-异构体可用手性合成子或手性试剂制备,或用常规技术拆分。在本文所述化合物包含烯型双键或其他几何不对称中心时,除非另外指明,化合物旨在包括E和Z两种几何异构体。同样,也旨在包括所有的互变异构形式。
氧杂烷基是指其中一个或多个碳已由氧代替的烷基残基。它通过烷基残基连接到母体结构。实例包括甲氧基丙氧基、3,6,9-三氧杂癸基等。术语氧杂烷基是指其中氧通过单键连接到其相邻原子(形成醚键)的化合物,它不涉及在羰基中发现的双键氧。类似地,硫杂烷基和氮杂烷基是指其中一个或多个碳已分别由硫或氮代替的烷基残基。实例包括乙基氨基乙基和甲基硫基丙基。
甲硅烷基是指其中一至三个碳由四价硅代替并且通过硅原子连接到母体结构的烷基残基。甲硅烷氧基为其中两个碳由用烷基残基、芳基残基或环烷基残基封端的四价硅代替并且通过氧原子连接到母体结构的烷氧基残基。
二齿配体为能够通过两个部位结合到金属的配体。类似地,三齿配体为能够通过三个部位结合到金属的配体。环金属化配体是指通过碳-金属单键和一个或两个金属-杂原子键结合到金属原子从而形成环状结构的二齿或三齿配体,其中杂原子可以为N、S、P、As或O。
本文所述的任何数值包括以1个单位为增量从较低值到较高值的所有值,其条件为在任何较低值和任何较高值之间相隔至少2个单位。例如,如果述及组分的量或工艺变量(例如,温度、压力、时间等)的数值为例如1至90,优选20至80,更优选30至70,则在本说明书中旨在明确列举例如15至85、22至68、43至51、30至32等的数值。对于小于1的数值,则根据情况将1个单位认为是0.0001、0.001、0.01或0.1。这些只是明确意指的实例,在所列举的最低值和最高值之间的数值的所有可能组合均应认为是在本申请中以类似方式明确陈述。
实施例
制备单体的一般方法
制备2,7-二溴芴酮原料的优选合成路线描述于CN 1634839(流程1)。此方法使用溴水,并且以高转化率将芴酮转化成所需的二溴产物,有很少或没有单溴化物质生成,未知的副产物几乎不存在。在利用甲磺酸中的N-溴琥珀酰亚胺的方法使芴酮溴化时,这些不足溴化和未知产物通常以明显更高量存在。
流程1
在比例放大反应产物的三次结晶后,得到准备用于随后反应的150g高品质2,7-二溴芴酮(>99.8%纯度,LC分析)。分4个步骤(流程2)将一部分2,7-二溴芴酮转化成甲苯磺酸酯化乙二醇9,9’-二取代的芴(5)。
流程2
利用JP 1997255609关于糖基化所述的合成方法,并且略微改进,以明显更短的反应时间(12小时)并且在中性条件下以高转化率(95%)提供所需的芴4。用甲苯磺酸酯化芴(5)制备单体(流程3)以结合到具有共价连接到周边的悬垂苯甲酰基吡咯合铱(III)磷光体的聚芴材料。通过用酚型亲核体代替甲苯磺酰基取代基,苯甲酰基吡咯合铱(III)磷光体共价结合到芴单体(6)。
流程3
实施例1:合成9-(4-己基氧基苯基)-9H-芴-9-醇(2)
通过4-溴苯酚(91.2g,527mmol)与溴己烷(86.0g,520mmol)、K2CO3(80.0g,580mmol)在丙酮(200mL)中回流12小时烷基化,制备溴-(4-己基氧基)-苯。在过滤除去盐后,将反应混合物浓缩至干,得到油。将油溶于EtOAc(100mL),转移到分液漏斗,并用5%NaOH(4×200mL)洗涤。向分液漏斗加入另外200mL体积EtOAc,内含物用NaHCO3(1×200mL)洗涤,最终经MgSO4干燥。除去EtOAc溶剂,得到浅黄色油,无需进一步纯化即可使用该浅黄色油。收率:119g,89%。
1H NMR(500MHz,CD2Cl2,25℃)δ0.91(t,3H),1.34(m,4H),1.45(m,2H),1.76(m,2H),3.92(t,2H),6.79(d,2H),7.36(d,2H).
向250mL干燥三颈烧瓶加入镁屑(2.80g,118mmol),随后加入无水THF(100mL)。加入几粒碘晶体,将不均匀混合物加热回流15分钟,然后冷却到室温。停止搅拌,向反应容器加入1,2-二溴乙烷(0.25mL)。过去5分钟后,发生放热反应,并恢复搅拌20分钟。然后使反应冷却到20℃,经1小时加入溴-(4-己基氧基)苯(27.8g,108mmol),同时保持温度在14-18℃之间。去除冷却浴,在反应温度升至28℃时,搅拌反应另外10分钟。使反应冷却到室温,内含物由移液管转移到利用冷却浴保持在-10℃的搅拌着的2,7-二溴芴酮(30.0g,90.4mmol)在甲苯(250mL)中的悬浮体。去除冷却浴,在室温搅拌反应混合物20分钟,随后用20mL EtOH和饱和NH4Cl溶液(5mL)处理。将反应混合物过滤除去不溶物质,并转移到含EtOAc(100mL)和H2O(100mL)的分液漏斗。使各层分离,有机层用H2O(2×100mL)和盐水(1×100mL)洗涤,并经MgSO4干燥。除去溶剂至干,得到黄色固体粗品(50.8g)。粗物质用己烷/CH2Cl2重结晶,得到产物,为灰白色微晶物质。收率:38.6g,79%。
1H NMR(500MHz,CD2Cl2,25℃)δ0.91(t,3H),1.32(m,4H),1.41(m,2H),1.74(m,2H),2.66(s,1H),3.92(t,2H),6.79(d,2H),7.23(d,2H),7.43(d,2H),7.52(m,4H).
实施例2:合成9-(4-己基氧基苯基)-9’-(4-羟基苯基)-芴(3)
用20滴甲磺酸处理酚(24g,256mmol)和9-(4-己基氧基苯基)-9H-芴-9-醇(2)(30.0g,55.7mmol)的CH2Cl2(75mL)溶液,这使溶液变成紫色。将反应在室温搅拌,直到TLC分析表明原料芴醇被消耗。将反应混合物转移到分液漏斗,用饱和NaHCO3溶液(1×200mL),H2O(3×150mL)洗涤,然后有机相经MgSO4干燥。除去溶剂至干,得到油。使油从CH2Cl2溶液吸附到硅胶上,并除去溶剂至干。将经干燥的硅胶转移到装有填充硅胶水浆(200mL)的玻璃烧结漏斗(500mL),漏斗装配在真空瓶上。通过对瓶施加真空,用H2O冲洗漏斗的内含物,这使酚从硅胶洗脱。在除去过量的酚后,产物用CH3CN从硅胶洗脱。利用45℃的浴,用旋转式蒸发器除去溶剂,这导致形成乳白色溶液,由该溶液形成白色固体。通过过滤收集产物,用水洗涤,并干燥。分离为羟基酚加合物的对和邻异构体的混合物(90∶10)。收率:34.0g,98%。
1H NMR(500MHz,CD2Cl2,25℃)δ0.89(t,3H),1.32(m,4H),1.43(m,2H),1.74(m,2H),3.91(t,2H),4.90(s,1H),6.72(d,2H),6.77(d,2H),7.01(d,2H),7.04(d,2H),7.47(d,2H),7.50(d,2H),7.63(d,2H).
实施例3:合成9-(4-己基氧基苯基)-9’-(4-(2-羟基乙氧基)苯基)-芴(4)
将酚3(33.0g,53.7mmol)溶于二甲苯(30mL),经MgSO4干燥并过滤。在旋转式蒸发器上浓缩溶液,直至烧瓶的内含物重70g。然后在N2惰性气氛下放入3的二甲苯溶液,并用碳酸亚乙酯(3.9mL,59.0mmol)处理,随后加热回流15小时。在此时间过去后,使反应冷却到室温,并除去溶剂,得到黄色油。油通过2L SiO2层析,用CH2Cl2洗脱。在除去溶剂后,分离出无色油状产物。收率:29.1g,82%。
1H NMR(500MHz,CD2Cl2,25℃)δ0.94(t,3H),1.36(m,4H),1.47(m,2H),1.78(m,2H),2.03(t,1H),3.94(m,4H),4.07(t,2H),6.81(d,2H),6.85(d,2H),7.08(d,2H),7.11(d,2H),7.52(d,2H),7.54(d,2H),7.67(d,2H).
实施例4:合成9-(4-己基氧基苯基)-9’-(4-(2-对甲苯磺酰基乙氧基)苯基)-芴(5)
在N2惰性气氛下,用对甲苯磺酰氯(13.3g,69.8mmol)和三乙胺(19.4mL,140mmol)处理乙二醇4(29.1g,44.2mmol)的甲苯溶液(200mL),并在室温搅拌60小时。然后过滤反应混合物,以除去三乙胺盐酸盐,并浓缩至干。将残余物溶于EtOAc,用5%HCl(1×100mL),饱和NaHCO3(2×200mL)洗涤,经MgSO4干燥,并去除溶剂至干。粗油通过1.4L SiO2层析(CH2Cl2∶己烷,1∶1)。在除去溶剂后,分离出白色非晶形固体状的产物。收率:33.0g,92%。
1H NMR(500MHz,CD2Cl2,25℃)δ0.88(t,3H),1.33(m,4H),1.43(m,2H),1.74(m,2H),2.41(s,3H),3.91(t,2H),4.09(t,2H),4.31(t,2H),6.68(d,2H),6.77(d,2H),7.03(m,4H),7.34(d,2H),7.46(d,2H),7.50(d,2H),7.63(d,2H),7.78(d,2H).
实施例5:合成[(piq)2Ir(7)]-芴单体(6)
将固体K2CO3(1.00g,7.24mmol)加入到含甲苯磺酸酯化芴5(3.00g,4.00mmol)和苯甲酰基吡咯合铱络合物7(3.00g,3.8mmol)的搅拌DMF溶液(25mL)。在使此溶液在80℃搅拌1.5小时后,使反应冷却,加入H2O(75mL),声处理生成的红色沉淀,过滤收集,用水、MeOH洗涤,然后在空气中干燥。产物通过SiO2:甲苯层析,在除去溶剂后,分离为红色固体。收率:5.00g,92%。
1H NMR(500MHz,CD2Cl2,25℃)δ0.89(t,3H),1.33(m,4H),1.42(m,2H),1.73(m,2H),3.90(t,2H),4.27(m,2H),4.34(m,2H),6.30(dd,1H),6.41(dd,1H),6.45(dd,1H),6.51(t,1H),6.77(m,6H),7.00(m,8H),7.19(dd,1H),7.32(d,1H),7.43(d,1H),7.47(d,2H),7.50(dd,2H),7.53(d,1H),7.62(d,2H),7.73(m,4H),7.87(m,1H),7.92(m,1H),7.96(d,2H),8.27(d,2H),8.34(d,1H),8.99(m,2H).
实施例6:合成2-(4-羟基苯甲酰基)-吡咯(7)
将三氟乙酸酐(10ml,72.0mmol)加入到冷却到0℃的搅拌着的4-羟基苯甲酸(5.50g,40.0mmol)在CH3CN中的悬浮体中。过去15分钟后,苯甲酸溶解。向0℃的此冷却溶液加入1-(对甲苯磺酰基)吡咯(8.85g,40.0mmol),随后加入足够CH2Cl2,以使所述吡咯在此温度溶解。在快速搅拌下,将另外体积的三氟乙酸酐(10ml,72.0mmol)加入到反应混合物,随后加入H3PO4(2mL,37.0mmol)。在室温搅拌反应混合物12小时后,加入另外的三氟乙酸酐(6mL,43.2mmol)和4-羟基苯甲酸(4.00g,29.0mmol),并继续搅拌12小时。在此时间过去后,除去溶剂至干,使残余物悬浮于5%NaOH(250mL)中,并搅拌过夜。过滤除去悬浮体,滤饼用5%NaOH(250mL)洗涤。向滤液加入饱和NaHCO3溶液(200mL),通过加入浓HCl使溶液的pH为中性。生成粉红色微晶物质,通过过滤收集,用水洗涤,并干燥。收率:3.30g,44%。
1H NMR(500MHz,CD2Cl2,25℃)δ6.35(m,1H),6.90(m,1H),6.94(d,2H),7.14(m,1H),7.87(d,2H),9.70(bs,1H).
实施例7:合成[(piq)2Ir(7)](8)
向含酮基吡咯7(1.20g,6.40mmol)的搅拌冷却(-10℃)的EtOH溶液(100mL)加入固体氢化钠(288mg,12.0mmol),这使溶液从黄色变成橙色。在搅拌此溶液5分钟后,加入[(piq)2Ir(μ-Cl)]2(3.33g,2.56mmol),然后将混合物加热回流10小时。使反应混合物冷却至室温,过滤收集红色沉淀。产物用EtOH洗涤,并在空气中干燥。收率(3.85mg,96%)。
1H NMR(500MHz,CD2Cl2,25℃)δ6.32(dd,1H),6.42(dd,2H),6.45(dd,1H),6.51(t,1H),6.73(m,1H),6.78(m,1H),6.83(d,2H),7.00(m,2H),7.18(dd,1H),7.31(d,1H),7.43(d,1H),7.53(d,1H),7.73(m,4H),7.89(m,4H),8.27(m,2H),8.34(d,1H),8.99(m,2H).
实施例8:制备9,9-二辛基芴-三芳基胺共聚物
化合物 | MW | mmol | Mg | 注解 |
F8双硼酸酯 | 530 | 1.00 | 530 | |
TFB二溴化物 | 459 | 0.95 | 436 | |
铱络合物 | 1405 | 0.05 | 70 | |
Pd(OAc)2 | 224 | 0.031 | 7 | 0.75%官能团 |
三(邻甲苯基)膦 | 304 | 0.105 | 32 | 3.5x[Pd] |
Et4NOH | 147 | 5.0 | 3.7g | 20%水溶液 |
水 | 3.7g | |||
甲苯 | 20ml |
称重前,所有单体在50℃的真空烘箱中干燥至少两小时。向具有到鼓泡器的氮入口和磁力搅拌器的50ml 2颈烧瓶加入所有单体、三(邻甲苯基)膦和15-18ml甲苯。此溶液用氩脱气5-10分钟,然后加入Pd(OAc)2,用剩余的甲苯洗涤称重的漏斗。同时在单独的管形瓶中,用氩使含水组分脱气。在脱气至少15分钟后,将含水组分加入到有机溶液,并将烧瓶浸入70℃油浴。在正氮压力下继续搅拌和加热16-20小时,在此时使溶液达到室温,并加入20mg苯基硼酸。将烧瓶再次浸入加热浴中,并在氮下搅拌另外3小时。使混合物再次冷却,然后用各约10ml的甲苯和水稀释。将混合物转移到分液漏斗,弃去水相,有机相用3×50ml水和1×50ml饱和NaCl洗涤。然后使有机溶液通过含Celite和Drierite的漏斗,并利用胺官能硅胶将经过滤的溶液搅拌至少30分钟。将溶液再次过滤,在旋转式蒸发器上浓缩到20-30ml体积,然后装到甲苯饱和的硅胶柱上(~20-30g二氧化硅/克聚合物-注解6)。利用甲苯(~100ml)从柱洗脱聚合物,将甲苯溶液浓缩到~20ml。在剧烈搅拌下,通过使溶液在10体积甲醇中沉淀分离聚合物。过滤收集聚合物,用甲醇洗涤,并在40-50℃真空烘箱中干燥。在干燥后产量为403mg(55%)。凝胶渗透色谱法表明Mw 92.4K,Mn 23.0K,相对于聚苯乙烯标准物。
实施例9:器件制造
通过在洁净、经UV臭氧处理的2.5cm×2.5cm ITO图案化玻璃基片上旋涂,沉积具有约60nm厚度的PEDOT/PSS(Baytron P VP 8000,聚(3,4-亚乙二氧基噻吩)-聚(苯乙烯磺酸盐),作为溶液购自HCStarck,Inc.)层。然后将经涂覆的基片在热板上在空气中在160℃烘烤30分钟。然后在PEDOT/PSS涂覆的基片顶上旋涂具有约10-20nm厚度的F8-TFB(辛基芴-三芳基胺共聚物,得自Sumation,Inc.)空穴输送层。然后将F8-TFB-PEDOT/PSS涂覆的基片在热板上在氩中在170℃烘烤30分钟。通过用二甲苯溶液旋转流延,在F8-TFB层顶上沉积电致发光聚合物BP104(Sumation)和实施例8的聚合物的1∶1混合物的最终层。此层具有约40-50nm厚度。然后将经涂覆的基片放入钟罩式蒸发器,对该系统泵抽真空,直至达到约1×10-6托压力。然后,通过物理蒸气沉积在经涂覆基片的最终层的顶上沉积约3nm厚氟化钠层(通过校准的石英晶体微量天平测量)。随后,通过蒸气沉积在真空下在氟化钠层的顶上沉积约130nm厚铝金属层,以形成OLED的阴极部件。
对于各器件,用Keithley 236Source Measure装置和连接到皮安计(Keithley)的硅二极管测量亮度和电流-施加电压。通过对照Minolta LS 100亮度计校准硅二极管并通过测定OLED的有效面积,使二极管的电流响应转化成OLED亮度(cd/m2)。亮度(“cd/A”)量度注入的电荷如何有效地转化成眼睛能够看到的光,LPW则是功率功效计量(一定量输入功率发出多少可见光)。LPW数据包括工作电压和电荷两者对可见光转化效率的作用。Cd/A和LPW数据的组合表明包含所述聚合物材料的器件的相对有效工作,并且此物质与器件的低电压工作相容。
各OLED器件样品所发射光的颜色(EL谱)用校准的光谱仪检测,同时使器件在约1mA电流密度在约390nm至约750nm范围工作。产生来自BP 104物质的蓝色发射和来自所述聚合物材料的红色发射。来自该具体器件的发射受红色发射物质支配,表明在LPW和Cd/A曲线图所示的性能表明所述侧臂发射聚合物的性能。
虽然本文只说明和描述了本发明的某些特征,但本领域的技术人员应想到很多修改和变化。因此,应了解,附加权利要求旨在覆盖落在本发明真实精神内的所有这些修改和变化。
Claims (19)
1.一种下式的化合物
其中
R1、R3、R4和R6独立地为氢、烷基、烷氧基、氧杂烷基、烷基芳基、芳基、芳基烷基、杂芳基、取代的烷基、取代的烷氧基、取代的氧杂烷基、取代的烷基芳基、取代的芳基、取代的芳基烷基或取代的杂芳基;
R1a为氢或烷基;
R2为亚烷基、取代的亚烷基、氧杂亚烷基、CO或CO2;
R2a为亚烷基;
R5每次出现时独立地为氢、烷基、烷基芳基、芳基、芳基烷基、烷氧基、羧基、取代的烷基、取代的烷基芳基、取代的芳基、取代的芳基烷基或取代的烷氧基;
L衍生自苯基吡啶、甲苯基吡啶、苯并噻吩基吡啶、苯基异喹啉、二苯并喹喔啉、芴基吡啶、酮基吡咯、2-(1-萘基)苯并噁唑、2-苯基苯并噁唑、2-苯基苯并噻唑、香豆素、噻吩基吡啶、苯基吡啶、苯并噻吩基吡啶、3-甲氧基-2-苯基吡啶、噻吩基吡啶、苯基亚胺、乙烯基吡啶、吡啶基萘、吡啶基吡咯、吡啶基咪唑、苯基吲哚、其衍生物或其组合。
2.权利要求1的化合物,所述化合物具有下式
其中R1b为氢、烷基、烷氧基、氧杂烷基、取代的烷基、取代的烷氧基或取代的氧杂烷基。
3.权利要求2的化合物,其中R2为氧杂亚烷基。
6.一种聚合物,所述聚合物包含至少一种衍生自权利要求1的化合物的结构单元。
8.权利要求7的聚合物,所述聚合物另外包含衍生自至少一种芴单体的结构单元。
9.权利要求7的聚合物,所述聚合物另外包含衍生自二溴9,9-二辛基芴单体的结构单元。
10.权利要求7的聚合物,所述聚合物另外包含衍生自至少一种三芳基胺单体的结构单元。
11.权利要求7的聚合物,其中L衍生自苯基异喹啉。
12.权利要求7的聚合物,其中R2为氧杂亚烷基。
15.权利要求7的聚合物,其中侧基衍生自权利要求1的化合物。
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CN104059631A (zh) * | 2013-03-19 | 2014-09-24 | 宁波大学 | 一种含铱聚合物红光材料及其合成方法 |
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US8048956B2 (en) | 2008-12-05 | 2011-11-01 | General Electric Company | Functionalized polyfluorenes for use in optoelectronic devices |
US8053536B2 (en) | 2008-12-05 | 2011-11-08 | General Electric Company | Functionalized polyfluorenes for use in optoelectronic devices |
US8512879B2 (en) * | 2009-11-10 | 2013-08-20 | General Electric Company | Polymer for optoelectronic device |
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JP4574936B2 (ja) * | 2001-08-31 | 2010-11-04 | 日本放送協会 | 燐光発光性化合物及び燐光発光性組成物 |
US7250512B2 (en) | 2001-11-07 | 2007-07-31 | E. I. Du Pont De Nemours And Company | Electroluminescent iridium compounds having red-orange or red emission and devices made with such compounds |
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US7830081B2 (en) * | 2006-03-22 | 2010-11-09 | General Electric Company | Optoelectronic devices with multilayered structures |
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US7691292B2 (en) | 2006-07-28 | 2010-04-06 | General Electric Company | Organic iridium compositions and their use in electronic devices |
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CN103797086B (zh) * | 2011-08-05 | 2016-06-29 | 剑桥显示技术有限公司 | 发光聚合物和器件 |
CN104059631A (zh) * | 2013-03-19 | 2014-09-24 | 宁波大学 | 一种含铱聚合物红光材料及其合成方法 |
CN104059631B (zh) * | 2013-03-19 | 2016-06-15 | 宁波大学 | 一种含铱聚合物红光材料及其合成方法 |
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