JP5591713B2 - 光電子デバイス用発光性ポリマー材料 - Google Patents
光電子デバイス用発光性ポリマー材料 Download PDFInfo
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- JP5591713B2 JP5591713B2 JP2010538001A JP2010538001A JP5591713B2 JP 5591713 B2 JP5591713 B2 JP 5591713B2 JP 2010538001 A JP2010538001 A JP 2010538001A JP 2010538001 A JP2010538001 A JP 2010538001A JP 5591713 B2 JP5591713 B2 JP 5591713B2
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- alkyl
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- 230000005693 optoelectronics Effects 0.000 title description 8
- 239000002861 polymer material Substances 0.000 title description 3
- 229920000642 polymer Polymers 0.000 claims description 53
- 125000000217 alkyl group Chemical group 0.000 claims description 32
- -1 phenylimine Chemical compound 0.000 claims description 30
- 150000001875 compounds Chemical class 0.000 claims description 20
- 125000003118 aryl group Chemical group 0.000 claims description 17
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 12
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 12
- 229910052760 oxygen Inorganic materials 0.000 claims description 12
- 125000001072 heteroaryl group Chemical group 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 9
- 125000002947 alkylene group Chemical group 0.000 claims description 8
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 7
- 125000005415 substituted alkoxy group Chemical group 0.000 claims description 7
- NRSBAUDUBWMTGL-UHFFFAOYSA-N 2-(1-benzothiophen-2-yl)pyridine Chemical compound S1C2=CC=CC=C2C=C1C1=CC=CC=N1 NRSBAUDUBWMTGL-UHFFFAOYSA-N 0.000 claims description 6
- QLPKTAFPRRIFQX-UHFFFAOYSA-N 2-thiophen-2-ylpyridine Chemical compound C1=CSC(C=2N=CC=CC=2)=C1 QLPKTAFPRRIFQX-UHFFFAOYSA-N 0.000 claims description 6
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 6
- JVZRCNQLWOELDU-UHFFFAOYSA-N gamma-Phenylpyridine Natural products C1=CC=CC=C1C1=CC=NC=C1 JVZRCNQLWOELDU-UHFFFAOYSA-N 0.000 claims description 6
- 125000003107 substituted aryl group Chemical group 0.000 claims description 6
- VIXWGKYSYIBATJ-UHFFFAOYSA-N pyrrol-2-one Chemical compound O=C1C=CC=N1 VIXWGKYSYIBATJ-UHFFFAOYSA-N 0.000 claims description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 4
- LPCWDYWZIWDTCV-UHFFFAOYSA-N 1-phenylisoquinoline Chemical compound C1=CC=CC=C1C1=NC=CC2=CC=CC=C12 LPCWDYWZIWDTCV-UHFFFAOYSA-N 0.000 claims description 3
- 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 description 3
- XBHOUXSGHYZCNH-UHFFFAOYSA-N 2-phenyl-1,3-benzothiazole Chemical compound C1=CC=CC=C1C1=NC2=CC=CC=C2S1 XBHOUXSGHYZCNH-UHFFFAOYSA-N 0.000 claims description 3
- FIISKTXZUZBTRC-UHFFFAOYSA-N 2-phenyl-1,3-benzoxazole Chemical compound C1=CC=CC=C1C1=NC2=CC=CC=C2O1 FIISKTXZUZBTRC-UHFFFAOYSA-N 0.000 claims description 3
- KLLLJCACIRKBDT-UHFFFAOYSA-N 2-phenyl-1H-indole Chemical compound N1C2=CC=CC=C2C=C1C1=CC=CC=C1 KLLLJCACIRKBDT-UHFFFAOYSA-N 0.000 claims description 3
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 claims description 3
- 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 claims description 3
- VJHVLELNDFVKMS-UHFFFAOYSA-N 3-methoxy-2-phenylpyridine Chemical compound COC1=CC=CN=C1C1=CC=CC=C1 VJHVLELNDFVKMS-UHFFFAOYSA-N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical group [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 5
- 125000001475 halogen functional group Chemical group 0.000 claims 1
- 239000010410 layer Substances 0.000 description 68
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 51
- 239000000243 solution Substances 0.000 description 38
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- 239000000463 material Substances 0.000 description 27
- 239000000178 monomer Substances 0.000 description 16
- 229910052757 nitrogen Inorganic materials 0.000 description 16
- 125000004432 carbon atom Chemical group C* 0.000 description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 13
- 239000002904 solvent Substances 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 229910052741 iridium Inorganic materials 0.000 description 9
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 239000001301 oxygen Chemical group 0.000 description 9
- 230000006798 recombination Effects 0.000 description 9
- 238000005215 recombination Methods 0.000 description 9
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 8
- 238000002347 injection Methods 0.000 description 8
- 239000007924 injection Substances 0.000 description 8
- 229910052751 metal Inorganic materials 0.000 description 8
- 239000002184 metal Substances 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 239000003921 oil Substances 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 8
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 7
- 239000000975 dye Substances 0.000 description 7
- 238000001914 filtration Methods 0.000 description 7
- 230000005525 hole transport Effects 0.000 description 7
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 7
- 239000003446 ligand Substances 0.000 description 7
- 239000000741 silica gel Substances 0.000 description 7
- 229910002027 silica gel Inorganic materials 0.000 description 7
- 229910052710 silicon Inorganic materials 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 6
- 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
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
- 229920001577 copolymer Polymers 0.000 description 6
- 125000000753 cycloalkyl group Chemical group 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 6
- 239000011970 polystyrene sulfonate Substances 0.000 description 6
- 229960002796 polystyrene sulfonate Drugs 0.000 description 6
- 239000010703 silicon Substances 0.000 description 6
- 239000000758 substrate Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 5
- 235000019439 ethyl acetate Nutrition 0.000 description 5
- 125000005842 heteroatom Chemical group 0.000 description 5
- 229920006395 saturated elastomer Polymers 0.000 description 5
- 239000011593 sulfur Chemical group 0.000 description 5
- NRWUQWRLIMQGND-UHFFFAOYSA-N (4-hydroxyphenyl)-(1h-pyrrol-2-yl)methanone Chemical compound C1=CC(O)=CC=C1C(=O)C1=CC=CN1 NRWUQWRLIMQGND-UHFFFAOYSA-N 0.000 description 4
- AVXFJPFSWLMKSG-UHFFFAOYSA-N 2,7-dibromo-9h-fluorene Chemical compound BrC1=CC=C2C3=CC=C(Br)C=C3CC2=C1 AVXFJPFSWLMKSG-UHFFFAOYSA-N 0.000 description 4
- WXJDHNPDHFZZJL-UHFFFAOYSA-N 9-(4-hexoxyphenyl)fluoren-9-ol Chemical compound C1=CC(OCCCCCC)=CC=C1C1(O)C2=CC=CC=C2C2=CC=CC=C21 WXJDHNPDHFZZJL-UHFFFAOYSA-N 0.000 description 4
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-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
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
- 229910045601 alloy Inorganic materials 0.000 description 4
- 239000000956 alloy Substances 0.000 description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 4
- 239000002800 charge carrier Substances 0.000 description 4
- 230000005281 excited state Effects 0.000 description 4
- 238000005227 gel permeation chromatography 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
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 4
- 125000005259 triarylamine group Chemical group 0.000 description 4
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 4
- 229940090248 4-hydroxybenzoic acid Drugs 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-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
- 125000002252 acyl group Chemical group 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
- 238000001816 cooling Methods 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 230000009849 deactivation Effects 0.000 description 3
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- 125000005843 halogen group Chemical group 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 125000000623 heterocyclic group Chemical group 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 3
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- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical compound C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 description 2
- XOMJMGUMUWCXQJ-UHFFFAOYSA-N 1-bromo-2-hexan-3-yloxybenzene Chemical compound CCCC(CC)OC1=CC=CC=C1Br XOMJMGUMUWCXQJ-UHFFFAOYSA-N 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
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- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical group [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
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 2
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- 238000004458 analytical method Methods 0.000 description 2
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- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
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- 239000003999 initiator Substances 0.000 description 2
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- NFGGQMYSOLVBLF-UHFFFAOYSA-N phenyl(1h-pyrrol-2-yl)methanone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CN1 NFGGQMYSOLVBLF-UHFFFAOYSA-N 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
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- 239000011775 sodium fluoride Substances 0.000 description 2
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- 239000007858 starting material Substances 0.000 description 2
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- KLLYGDXCCNXESW-UHFFFAOYSA-N (2-fluoroacetyl) 2-fluoroacetate Chemical compound FCC(=O)OC(=O)CF KLLYGDXCCNXESW-UHFFFAOYSA-N 0.000 description 1
- VYPADSNDNHLCFA-UHFFFAOYSA-N 1,2-dibromo-9,9-dioctylfluorene Chemical compound C1=C(Br)C(Br)=C2C(CCCCCCCC)(CCCCCCCC)C3=CC=CC=C3C2=C1 VYPADSNDNHLCFA-UHFFFAOYSA-N 0.000 description 1
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 1
- FKASFBLJDCHBNZ-UHFFFAOYSA-N 1,3,4-oxadiazole Chemical compound C1=NN=CO1 FKASFBLJDCHBNZ-UHFFFAOYSA-N 0.000 description 1
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- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
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- MNDIARAMWBIKFW-UHFFFAOYSA-N 1-bromohexane Chemical compound CCCCCCBr MNDIARAMWBIKFW-UHFFFAOYSA-N 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- GKWLILHTTGWKLQ-UHFFFAOYSA-N 2,3-dihydrothieno[3,4-b][1,4]dioxine Chemical compound O1CCOC2=CSC=C21 GKWLILHTTGWKLQ-UHFFFAOYSA-N 0.000 description 1
- KFDDOSKBEZKAMI-UHFFFAOYSA-N 2,9-dimethyl-4,7-diphenylbenzo[h]quinoline Chemical compound C=12C=CC3=C(C=4C=CC=CC=4)C=C(C)N=C3C2=CC(C)=CC=1C1=CC=CC=C1 KFDDOSKBEZKAMI-UHFFFAOYSA-N 0.000 description 1
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- 229910052744 lithium Inorganic materials 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
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- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- 125000006513 pyridinyl methyl group Chemical group 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 229910052706 scandium Inorganic materials 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
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- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000007725 thermal activation Methods 0.000 description 1
- PFZLGKHSYILJTH-UHFFFAOYSA-N thieno[2,3-c]thiophene Chemical compound S1C=C2SC=CC2=C1 PFZLGKHSYILJTH-UHFFFAOYSA-N 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 1
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 229910052727 yttrium Inorganic materials 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
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- 229910006400 μ-Cl Inorganic materials 0.000 description 1
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
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Description
R1aは水素又はアルキルであり、
R2はアルキレン、置換アルキレン、オキサアルキレン基、CO又はCO2であり、
R2aはアルキレン基であり、
R5はそれぞれ独立に水素、アルキル、アルキルアリール、アリール、アリールアルキル、アルコキシ、カルボキシ、置換アルキル、置換アルキルアリール、置換アリール、置換アリールアルキル又は置換アルコキシ基であり、
Xは2,5−位又は2,7−位に位置するハロ、トリフレート、−B(OR1a)2、又は次式の基であり、
R1cは水素、アルキル又は置換アルキル基である。
本発明の文脈では、アルキルは低級アルキル及び高級アルキルなどの直鎖状、分枝状又は環状炭化水素構造及びこれらの組合せを含む。アルキル基はC20以下のものが好ましい。低級アルキルは、炭素原子数1〜6、好ましくは炭素原子数1〜4のアルキル基を指し、例えばメチル、エチル、n−プロピル、イソプロピル、n−、s−及びt−ブチルである。高級アルキルは、炭素原子数7以上、好ましくは炭素原子数7〜20のアルキル基を指し、例えば、n−、s−及びt−ヘプチル、オクチル及びドデシルである。シクロアルキルは、アルキルの一部であり、例えば炭素原子数3〜8の環状炭化水素基である。シクロアルキル基の例には、シクロプロピル、シクロブチル、シクロペンチル及びノルボルニルがある。アルケニル及びアルキニルはそれぞれ2つ以上の水素原子が二重結合又は三重結合によって置換されたアルキル基を指す。
出発材料である2,7−ジブロモフルオレンの製造に好ましい合成経路はCN1634839(スキーム1)に記載されている。この方法では水中で臭素を用いてフルオレンを所望のジブロモ生成物に高率で転化し、モノブロモ化種の形成はほとんど又は全くなく、未知の副生成物はほとんど存在しない。メタンスルホン酸中でN−ブロモスクシンイミドを用いる方法でフルオレンをブロモ化すると、これらの不十分なブロモ化生成物や未知の生成物が通常著しく多量に存在する。
9−(4−ヘキシルオキシフェニル)−9H−フルオレン−9−オール[2]の合成
4−ブロモフェノール(91.2g、527mmol)をブロモヘキサン(86.0g、520mmol)及びK2CO3(80.0g、580mmol)とアセトン(200mL)中で12時間還流してアルキル化することによりブロモ(4−ヘキシルオキシ)ベンゼンを製造した。濾過により塩を除去した後、反応混合物を濃縮・乾固し、油状物を得た。油状物をEtOAc(100mL)に溶解し、分液ロートに移し、各200mLの5%NaOH溶液で4回洗浄した。さらに200mLのEtOAcを分液ロートに加え、200mLのNaHCO3溶液で1回洗い、最後にMgSO4で乾燥した。EtOAc溶媒を除去して淡黄色油状物を得、これ以上精製せずに次工程に使用した。収量119g、89%。1H NMR(500MHz,CD2Cl2,25℃)d0.91(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)。乾燥した250mlの三つ口フラスコに細い削り状Mg(2.80g、118mmol)、次いで無水THF(100mL)を装入した。少量のヨウ素結晶を添加し、均一な混合物を15分間加熱還流し、その後室温まで冷却した。撹拌を止め、1,2−ジブロモエタン(0.25mL)を反応容器に加えた。5分間経過後、発熱反応が起こり、再び撹拌を20分間続けた。その後、反応溶液を20℃まで冷却し、ブロモ(4−ヘキシルオキシ)ベンゼン(27.8g、108mmol)を14〜18℃の温度に保ちながら、1時間かけて添加した。冷却槽を外し、反応溶液をさらに10分間撹拌し、この間に反応温度が28℃に上昇した。反応溶液を室温まで冷却し、トルエン(250mL)中の2,7−ジブロモフルオレン(30.0g、90.4mmol)懸濁液を冷却槽で−10℃に維持しながら撹拌し、そこにフラスコの中身をピペットで移した。冷却槽を外し、反応混合物を室温で20分間撹拌し、その後EtOH(20mL)とNH4Cl飽和溶液(5mL)とで処理した。反応混合物を濾過して不溶物を除去し、EtOAc(100mL)とH2O(100mL)とを入れた分液ロートに移した。2層が分離し、有機層を各100mLのH2Oで2回、100mLのブラインで1回洗い、MgSO4で乾燥した。溶媒を除去・乾固して粗製黄色固体(50.8g)を得た。この粗製材料をヘキサン/CH2Cl2から再結晶して生成物をオフホワイトの微結晶材料として得た。収量:38.6g、79%。1H NMR(500MHz,CD2Cl2,25℃)d0.91(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)。
9−(4−ヘキシルオキシフェニル)−9’−(4−ヒドロキシフェニル)フルオレン[3]の合成
フェノール(24g、256mmol)と9−(4−ヘキシルオキシフェニル)−9H−フルオレン−9−オール(2)(30.0g、55.7mmol)のCH2Cl2(75mL)溶液を20滴のメタンスルホン酸で処理して溶液の色を紫に変化させた。出発材料のフルオレノールが消費されたことをTLC分析が示すまで、反応溶液を室温で撹拌した。反応混合物を分液ロートに移し、200mLのNaHCO3飽和溶液で1回、各150mLのH2Oで3回洗浄し、その後有機層をMgSO4で乾燥した。溶媒を除去・乾固して油状物を得た。油状物をCH2Cl2溶液からシリカゲルに吸着させ、溶媒を乾燥除去した。真空フラスコに取り付けた、シリカゲルのH2Oスラリー(200mL)を充填したガラス濾過器(フリットガラス付きロート)(500mL)に乾燥したシリカゲルを移した。フラスコに真空をかけることにより濾過器の中身をH2Oで洗い流し、シリカゲルからフェノールを溶出した。余分なフェノールを除去した後、生成物をシリカゲルからCH3CNで溶出した。45℃の浴を備えたロータリーエバポレーターを用いて溶媒を除去すると白濁溶液が形成し、この溶液から白色固体が形成した。濾過により生成物を回収し、水で洗浄し、乾燥した。ヒドロキシフェノール付加体のパラ、オルト異性体の混合物(90:10)として単離した。収量:34.0g、98%。1H NMR(500MHz,CD2Cl2,25℃)d0.89(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)。
9−(4−ヘキシルオキシフェニル)−9’−(4−(2−ヒドロキシエトキシ)フェニル)フルオレン[4]の合成
フェノール[3](33.0g、53.7mmol)をキシレン(30mL)に溶解し、MgSO4で乾燥し、濾過した。フラスコの中身が70gになるまで、溶液をロータリーエバポレーターで濃縮した。その後、フェノール[3]のキシレン溶液をN2の不活性雰囲気下に置き、エチレンカーボネート(3.9mL、59.0mmol)で処理し、その後15時間加熱還流した。15時間経過後、反応溶液を室温まで冷却し、溶媒を除去し、黄色油状物を得た。油状物を2LのSiO2のクロマトグラフィーに通してCH2Cl2で溶出した。溶媒除去後、生成物を無色油状物として単離した。収量:29.1g、82%。1H NMR(500MHz,CD2Cl2,25℃)d0.94(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)。
9−(4−ヘキシルオキシフェニル)−9’−(4−(2−p−トルエンスルホニルエトキシ)フェニル)フルオレン[5]の合成
エチレングリコール[4](29.1g、44.2mmol)のトルエン溶液(200mL)をp−トルエンスルホニルクロリド(13.3g、69.8mmol)及びトリエチルアミン(19.4mL、140mmol)で処理し、N2の不活性雰囲気下室温で60時間撹拌した。その後、反応混合物を濾過してトリエチルアミン塩酸塩を除去し、濃縮・乾固した。残留物をEtOAcに溶解し、100mLの5%HClで1回、各200mLのNaHCO3飽和溶液で2回洗浄し、MgSO4で乾燥し、溶媒を除去・乾固した。粗製油状物を1.4LのSiO2(CH2Cl2:ヘキサン、1:1)のクロマトグラフに通した。溶媒を除去後、生成物を白色無定形固体として単離した。収量:33.0g、92%。1H NMR(500MHz,CD2Cl2,25℃)d0.88(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)。
[(piq) 2 Ir(7)]フルオレンモノマー[6]の合成
トシル化フルオレン[5](3.00g、4.00mmol)及びベンゾイルピロールイリジウム錯体[7](3.00g、3.8mmol)を含有するDMF溶液(25mL)を撹拌しながら、そこに固体のK2CO3(1.00g、7.24mmol)を添加した。この溶液を80℃で1.5時間撹拌した後、反応溶液を冷却し、H2O(75mL)を添加し、形成した赤色析出物を超音波処理し、濾過により回収し、水、MeOHで洗浄し、その後空気中で乾燥した。生成物をSiO2:トルエンのクロマトグラフに通し、溶媒を除去後、生成物を赤色固体として単離した。収量:5.00g、92%。1H NMR(500MHz,CD2Cl2,25℃)d0.89(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)。
2−(4−ヒドロキシベンゾイル)ピロール[7]の合成
0℃に冷却したCH3CN中の4−ヒドロキシ安息香酸(5.50g、40.0mmol)の懸濁液を撹拌しながら、そこにトリフルオロ酢酸無水物(10mL、72.0mmol)を添加した。15分間経過後、4−ヒドロキシ安息香酸が溶解した。0℃に冷却したこの溶液に1−(p−トリルスルホニル)ピロール(8.85g、40.0mmol)、次いでこの温度でピロールを溶解するのに十分なCH2Cl2を添加した。高速撹拌している反応混合物に追加のトリフルオロ酢酸無水物(10mL、72.0mmol)、次いでH3PO4(2mL、37.0mmol)を添加した。反応混合物を室温で12時間撹拌後、さらに、トリフルオロ酢酸無水物(6mL、43.2mmol)及び4−ヒドロキシ安息香酸(4.00g、29.0mmol)を添加し、12時間撹拌し続けた。12時間経過後、溶媒を除去・乾固し、残留物を5%NaOH溶液(250mL)に懸濁し、一晩撹拌した。濾過により懸濁物を除去し、フィルターケークを5%NaOH溶液(250mL)で洗浄した。濾液にNaHCO3飽和溶液(200mL)を添加し、溶液のpHを濃HClを添加することにより中性にした。ピンクの微結晶材料が形成し、これを濾過により回収し、水で洗浄し、乾燥した。収量:3.30g、44%。1H NMR(500MHz,CD2Cl2,25℃)d6.35(m,1H),6.90(m,1H),6.94(d,2H),7.14(m,1H),7.87(d,2H),9.70(bs,1H)。
[(piq) 2 Ir(7)][8]の合成
ケトピロール[7](1.20g、6.40mmol)を含有するEtOH溶液(100mL)を冷却(−10℃)、撹拌しながら、そこに固体の水素化ナトリウム(288mg、12.0mmol)を添加したところ、溶液の色が黄色からオレンジに変化した。この溶液を5分間撹拌した後、[(piq)2Ir(μ−Cl)]2(3.33g、2.56mmol)を添加し、その後、混合物を10時間加熱還流した。反応混合物を室温まで冷却し、濾過により赤色析出物を回収した。生成物をEtOHで洗浄し、空気中で乾燥した。収量:3.85mg、96%。1H NMR(500MHz,CD2Cl2,25℃)d6.32(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)。
9,9−ジオクチルフルオレン−トリアリールアミンコポリマーの合成
デバイス製造
厚さが約60nmのPEDOT/PSS(Baytron P VP 8000、ポリ−(3,4−エチレンジオキシチオフェン)/ポリスチレンスルホネート、HC Starck社から溶液として入手)層を、清浄なUV−オゾン処理した2.5cm×2.5cmのITOパターン付ガラス基板上にスピンコートにより成膜した。その後、被覆基板をホットプレート上で空気中160℃で30分間ベークした。その後、PEDOT/PSS被覆基板の上に、F8−TFB(オクチルフルオレン−トリアリールアミンコポリマー、Sumation社から入手)の正孔輸送層を厚さ約10〜20nmにスピンコートした。次いで、F8−TFB及びPEDOT/PSS被覆基板をホットプレート上でアルゴン中170℃で30分間ベークした。F8−TFB層の上にエレクトロルミネセントポリマーであるBP104(Sumation社から入手)及び実施例8のポリマーの1:1ブレンドの最終層をキシレン溶液でスピンキャストすることにより成膜した。この層の厚さは約40〜50nmであった。次いで、被覆基板をベルジャーエバポレータに入れ、圧力が約1×10−6torrになるまで系をポンプで引いた。被覆基板の最終層の上に厚さが約3nmのフッ化ナトリウム層(較正済み水晶天秤(QCM=quartz crystal microbalance)により測定)を物理蒸着により成膜した。その後、フッ化ナトリウム層の上に厚さが約130nmのアルミニウム金属層を真空下の蒸着により成膜して、OLEDのカソード部分を形成した。
Claims (9)
- 次式の化合物。
R1aは水素又はアルキルであり、
R2はアルキレン、置換アルキレン、オキサアルキレン基、CO又はCO2であり、
R2aはアルキレン基であり、
R5はそれぞれ独立に水素、アルキル、アルキルアリール、アリール、アリールアルキル、アルコキシ、カルボキシ、置換アルキル、置換アルキルアリール、置換アリール、置換アリールアルキル又は置換アルコキシ基であり、
Xは2,5−位又は2,7−位に位置するハロ、トリフレート、−B(OR1a)2、又は次式の基であり、
- 次式で表される、請求項1記載の化合物。
- R2がオキサアルキレン基を示す、請求項2記載の化合物。
- 次式で表される、請求項1記載の化合物。
- 次式で表される請求項1記載の化合物。
- 請求項1記載の化合物に由来する構造単位を少なくとも1つ含むポリマー。
- 次式の側基を少なくとも1つ含むポリマーであって、
R3、R4及びR6は独立に水素、アルキル、アルコキシ、アルキルアリール、アリール、アリールアルキル、ヘテロアリール、置換アルキル、置換アルコキシ、置換アルキルアリール、置換アリール、置換アリールアルキル又は置換ヘテロアリール基であり、
Lはフェニルピリジン、トリルピリジン、ベンゾチエニルピリジン、フェニルイソキノリン、ジベンゾキノザリン、フルオレニルピリジン、ケトピロール、2−(1−ナフチル)ベンゾオキサゾール、2−フェニルベンゾオキサゾール、2−フェニルベンゾチアゾール、クマリン、チエニルピリジン、フェニルピリジン、ベンゾチエニルピリジン、3−メトキシ−2−フェニルピリジン、チエニルピリジン、フェニルイミン、ビニルピリジン、ピリジルナフタレン、ピリジルピロール、ピリジルイミダゾール又はフェニルインドールに由来する。)
側基が請求項1記載の化合物又は下記から選択される化合物に由来する、ポリマー。
- さらに、次式の構造単位を含む、請求項7記載のポリマー。
- 次式の構造単位を含む、
次式の構造単位を含む、請求項7記載のポリマー。
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PCT/US2008/073627 WO2009079039A1 (en) | 2007-12-17 | 2008-08-20 | Emissive polymeric materials for optoelectronic devices |
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US8048956B2 (en) | 2008-12-05 | 2011-11-01 | General Electric Company | Functionalized polyfluorenes for use in optoelectronic devices |
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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 |
GB201113563D0 (en) * | 2011-08-05 | 2011-09-21 | Cambridge Display Tech Ltd | Light emitting polymers and devices |
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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WO2009079039A1 (en) | 2009-06-25 |
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CN101998983B (zh) | 2015-01-14 |
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