JP2007243199A - 有機エレクトロルミネッセンス素子 - Google Patents
有機エレクトロルミネッセンス素子 Download PDFInfo
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- JP2007243199A JP2007243199A JP2007083981A JP2007083981A JP2007243199A JP 2007243199 A JP2007243199 A JP 2007243199A JP 2007083981 A JP2007083981 A JP 2007083981A JP 2007083981 A JP2007083981 A JP 2007083981A JP 2007243199 A JP2007243199 A JP 2007243199A
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- 150000001875 compounds Chemical class 0.000 claims abstract description 94
- 239000010410 layer Substances 0.000 claims abstract description 78
- 229920000642 polymer Polymers 0.000 claims abstract description 55
- 239000010409 thin film Substances 0.000 claims abstract description 22
- 150000002894 organic compounds Chemical class 0.000 claims abstract description 15
- 125000004122 cyclic group Chemical group 0.000 claims abstract description 8
- 239000002356 single layer Substances 0.000 claims abstract description 5
- 125000001424 substituent group Chemical group 0.000 claims description 33
- 229910052757 nitrogen Inorganic materials 0.000 claims description 23
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 21
- 238000006243 chemical reaction Methods 0.000 claims description 11
- 238000005401 electroluminescence Methods 0.000 claims description 11
- 125000005647 linker group Chemical group 0.000 claims description 11
- 239000000178 monomer Substances 0.000 claims description 11
- 239000007850 fluorescent dye Substances 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 229920001577 copolymer Polymers 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 238000006482 condensation reaction Methods 0.000 claims description 2
- 238000010559 graft polymerization reaction Methods 0.000 claims description 2
- 238000004020 luminiscence type Methods 0.000 claims description 2
- 239000002365 multiple layer Substances 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 29
- 238000002347 injection Methods 0.000 description 44
- 239000007924 injection Substances 0.000 description 44
- 239000000463 material Substances 0.000 description 42
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
- -1 methacryloyl group Chemical group 0.000 description 33
- 239000000203 mixture Substances 0.000 description 26
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 24
- 230000015572 biosynthetic process Effects 0.000 description 20
- 239000000243 solution Substances 0.000 description 20
- 238000003786 synthesis reaction Methods 0.000 description 19
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 17
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- 240000009038 Viola odorata Species 0.000 description 16
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- 238000007740 vapor deposition Methods 0.000 description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
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- 239000011777 magnesium Substances 0.000 description 9
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- 238000006116 polymerization reaction Methods 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
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- 238000001819 mass spectrum Methods 0.000 description 8
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
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- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 7
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- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
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- 239000002904 solvent Substances 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
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- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-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
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- 238000005266 casting Methods 0.000 description 4
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- 229910052738 indium Inorganic materials 0.000 description 4
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- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- 238000001771 vacuum deposition Methods 0.000 description 4
- 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 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 101000864684 Danio rerio Homeobox protein Dlx1a Proteins 0.000 description 3
- 102000004648 Distal-less homeobox proteins Human genes 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 3
- 101150111781 PGL1 gene Proteins 0.000 description 3
- 101710095911 Protein yippee-like 1 Proteins 0.000 description 3
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 3
- 238000004220 aggregation Methods 0.000 description 3
- 230000002776 aggregation Effects 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- XSCHRSMBECNVNS-UHFFFAOYSA-N benzopyrazine Natural products N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 3
- 238000007334 copolymerization reaction Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 125000001072 heteroaryl group Chemical group 0.000 description 3
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 3
- 150000004866 oxadiazoles Chemical class 0.000 description 3
- 238000012545 processing Methods 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- 238000004544 sputter deposition Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 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 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- WMIYIVSGJBEUEM-UHFFFAOYSA-N 3-(2-methylprop-2-enoyl)azepan-2-one Chemical compound CC(=C)C(=O)C1CCCCNC1=O WMIYIVSGJBEUEM-UHFFFAOYSA-N 0.000 description 2
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 2
- OZAIFHULBGXAKX-VAWYXSNFSA-N AIBN Substances N#CC(C)(C)\N=N\C(C)(C)C#N OZAIFHULBGXAKX-VAWYXSNFSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 2
- HAUGRYOERYOXHX-UHFFFAOYSA-N Alloxazine Chemical compound C1=CC=C2N=C(C(=O)NC(=O)N3)C3=NC2=C1 HAUGRYOERYOXHX-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 2
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
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- AUNGANRZJHBGPY-SCRDCRAPSA-N Riboflavin Chemical compound OC[C@@H](O)[C@@H](O)[C@@H](O)CN1C=2C=C(C)C(C)=CC=2N=C2C1=NC(=O)NC2=O AUNGANRZJHBGPY-SCRDCRAPSA-N 0.000 description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
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- 239000007983 Tris buffer Substances 0.000 description 2
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- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 2
- 125000004104 aryloxy group Chemical group 0.000 description 2
- CUFNKYGDVFVPHO-UHFFFAOYSA-N azulene Chemical compound C1=CC=CC2=CC=CC2=C1 CUFNKYGDVFVPHO-UHFFFAOYSA-N 0.000 description 2
- 230000004888 barrier function Effects 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 239000007810 chemical reaction solvent Substances 0.000 description 2
- WDECIBYCCFPHNR-UHFFFAOYSA-N chrysene Chemical compound C1=CC=CC2=CC=C3C4=CC=CC=C4C=CC3=C21 WDECIBYCCFPHNR-UHFFFAOYSA-N 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
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- 239000010949 copper Substances 0.000 description 2
- VPUGDVKSAQVFFS-UHFFFAOYSA-N coronene Chemical compound C1=C(C2=C34)C=CC3=CC=C(C=C3)C4=C4C3=CC=C(C=C3)C4=C2C3=C1 VPUGDVKSAQVFFS-UHFFFAOYSA-N 0.000 description 2
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- 239000006081 fluorescent whitening agent Substances 0.000 description 2
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- 239000003999 initiator Substances 0.000 description 2
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- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
- 150000002596 lactones Chemical class 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- VAMXMNNIEUEQDV-UHFFFAOYSA-N methyl anthranilate Chemical compound COC(=O)C1=CC=CC=C1N VAMXMNNIEUEQDV-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 2
- 238000000059 patterning Methods 0.000 description 2
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 2
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- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
- RDOWQLZANAYVLL-UHFFFAOYSA-N phenanthridine Chemical compound C1=CC=C2C3=CC=CC=C3C=NC2=C1 RDOWQLZANAYVLL-UHFFFAOYSA-N 0.000 description 2
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- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
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- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 2
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 description 2
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- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical class C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
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- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- 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 2
- 125000005580 triphenylene group Chemical group 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
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- XHUSGUDNNQOOPJ-HYXAFXHYSA-N (z)-4-(methylamino)-3-(methylaminomethyl)-4-oxobut-2-enoic acid Chemical compound CNC\C(=C\C(O)=O)C(O)=NC XHUSGUDNNQOOPJ-HYXAFXHYSA-N 0.000 description 1
- NGQSLSMAEVWNPU-YTEMWHBBSA-N 1,2-bis[(e)-2-phenylethenyl]benzene Chemical compound C=1C=CC=CC=1/C=C/C1=CC=CC=C1\C=C\C1=CC=CC=C1 NGQSLSMAEVWNPU-YTEMWHBBSA-N 0.000 description 1
- TXVWTOBHDDIASC-UHFFFAOYSA-N 1,2-diphenylethene-1,2-diamine Chemical compound C=1C=CC=CC=1C(N)=C(N)C1=CC=CC=C1 TXVWTOBHDDIASC-UHFFFAOYSA-N 0.000 description 1
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 1
- YNGDWRXWKFWCJY-UHFFFAOYSA-N 1,4-Dihydropyridine Chemical compound C1C=CNC=C1 YNGDWRXWKFWCJY-UHFFFAOYSA-N 0.000 description 1
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Abstract
Description
更に、一般式(1)で表される化合物又はその重合体、付加反応体、縮合反応体を少なくとも1種含有してなる蛍光性薄膜もその一態様である。
アントラニル酸メチルエステル90.6gをキシレン中、含水ヒドラジン54mlと共に加熱・還流下9.5時間反応させた。その後、溶媒を減圧・溜去し、少量のエタノールを加えて粗結晶を得た。更にエタノールで再結晶すると中間体(a)が64.9g(収率72%)で得られた。
化合物(Q−1)1.31g(5.0mmol)を、ジメチルアセトアミド中炭酸カリウム1.48g(14mmol)及びエピクロルヒドリン0.43ml(5.5mmol)と共に3時間50℃で反応させた。その後、水中にあけ1mol/L塩酸で中和した。生成物を濾取し、アセトニトリルで再結晶することで化合物(E−1)が0.92g(収率58%)得られた。
重合開始剤として無水塩化鉄(III)100mgを三つ口フラスコに入れ、減圧下で加熱して完全に脱水した後、乾燥窒素ガスを封入する。窒素気流下でE−1の0.63g(2mmol)と、脱水DMF10mlを添加し、3時間100℃で反応させた。その後、反応溶媒を大過剰のメタノールに注いで淡黄色沈澱を得た。この沈澱を少量のテトラヒドロフラン(以下THFと略称)に溶解させ、大過剰のヘキサンに注いで、0.38g(収率60%)の白色沈澱(PE−1)を得た。
ヨード酢酸−3−ブテニル6.0g(25mmol)と蒸留水2.5リットルを、4リットル四つ口フラスコに入れ、乾燥アルゴンでフラスコ内を置換した。撹拌しながら、トリエチルボランの1mol/Lメタノール溶液2.5ml(2.5mmol)を滴下した。滴下終了後、5時間室温で撹拌した後、酢酸エチルで抽出した。酢酸エチルを留去して得た組成物を、シリカゲルカラムクロマトグラフィーにより精製し、3.3g(収率55%)の3−ヨードメチル−δラクトン(L−0)を得た。
化合物Q−1の1.31g(5.0mmol)を、ジメチルアセトアミド中炭酸カリウム1.48g(14mmol)及びL−0の3.4g(5.5mmol)と共に3時間50℃で反応させた。その後、水中にあけ、1mol/L塩酸で中和した。生成物を濾取しアセトニトリルで再結晶することで、化合物(L−1)が1.02g(収率55%)得られた。
トリエチルアルミニウムを脱水トルエンに溶解させて3%溶液とし、この溶液を開始剤とした。又、脱水THF2リットルに対し、蒸溜水を0.2ml添加した反応溶媒18mlを、50ml三つ口フラスコに注ぎ、更に化合物L−1の0.93g(2.5mmol)と、前記トリエチルアルミニウムの3%トルエン溶液を0.4ml(0.1mmol:4.0mol%)を0℃にて添加した。その後、THFを4日間還流した。反応終了後、反応溶液を大量のジエチルエーテル中に注ぎ、沈澱してくる白色固体を濾別し、0.1mol/L塩酸溶液で洗浄後、クロロホルムに溶解させ、大量のヘキサンに注いで再沈澱を行い、0.41g(収率44%)の白色沈澱(PL−1)を得た。
化合物Q−1の1.31g(5.0mmol)をジメチルアセトアミド中、炭酸カリウム1.48g(14mmol)及び4−クロロメチルノルボルネン0.78g(5.5mmol)と共に3時間50℃で反応させた。その後、水中にあけ、1mol/L塩酸で中和した。生成物を濾取し、アセトニトリルで再結晶することで、化合物(N−1)が0.85g(収率46%)得られた。
化合物N−1の0.74g(2.0mmol)と、塩化イリジウム(III)3水和物71mg(0.02mmol,1.0mol%)を20mlのi−プロパノールに溶解させ、8時間還流を行ったところ、不溶物として灰色の不溶物が析出した。この組成物を濾別し、アセトンで洗浄後、熱トルエンに溶解させ、大過剰のメタノールで再沈澱を行い、0.43g(収率58%)の淡灰色の重合体(PN−1)を得た。
化合物Q−1の1.31g(5.0mmol)を、ジメチルアセトアミド中で二塩化スクシニル0.78g(5.0mmol)、トリエチルアミン1.5ml(11mmol)と共に3時間室温で反応させた。放冷後、エチレンイミン0.3ml(5.5mmol)のジエチルエーテル溶液(3ml)を添加し、50℃で5時間反応させた。放冷後、沈澱したトリエチルアミンの塩酸塩を濾別し、溶液に炭酸カリウム1.48g(14mmol)を添加し、3時間50℃で反応させた。その後、水中にあけ、1mol/L塩酸で中和した。生成物を濾取し、アセトニトリルで再結晶することで、化合物(X−1)が1.20g(収率61%)得られた。
重合開始剤として、p−クロロフェニルオキサゾリニウム過塩素酸塩の2%アセトニトリル溶液を調整しておく。化合物X−1の0.77g(2.0mmol)をジメチルアセトアミド10mlに溶解させ、窒素雰囲気下で0.1mlを加え、120℃で18時間反応させた。反応終了後、溶液を大過剰のメタノールに注ぎ、白色の沈澱物を得た。この白色固体を再びTHFに溶解させ、大過剰のジエチルエーテルに再沈澱を行い、白色固体(PX−1)を0.59g(77%)得た。
化合物Q−1の1.31g(5.0mmol)を、ジメチルアセトアミド中で4−ヨード安息香酸クロリド1.47g(5.5mmol)、トリエチルアミン0.8ml(6.0mmol)と共に3時間室温で反応させた。放冷後、沈澱したトリエチルアミンの塩酸塩を濾別後、溶液を酢酸エチルで分液し、有機層を硫酸ナトリウムで脱水し、溶媒を溜去して粗成物を得た。アセトニトリルで再結晶することで、白色固体(F−0)が2.26g(収率91%)得られた。
上記化合物F−0の1.96g(4.0mmol)を、ジメチルホルムアミド中で酢酸パラジウム(II)22.4mg(0.01mmol、2.5mol%)、トリフェニルホスフィン26.2mg(0.01mmol、2.5mol%)、塩化ブチルアンモニウム0.43g(4.0mmol)及び酢酸カリウム1.18g(12mmol)と共に24時間80℃で反応させた。放冷後、溶液を酢酸エチルで分液し、有機層を硫酸ナトリウムで脱水し、溶媒を溜去して白色粗成物を得た。組成物をアセトニトリルで再結晶することで、化合物(F−1)が1.26g(収率73%)得られた。
化合物F−1の0.86g(2.0mmol)を、ジメチルアセトアミド中ヘキサフルオロアンチモン酸・4−メトキシ−2−オキソ−2,2,6,6−テトラメチルピペリジニウム8.4mg(0.02mmol、1.0%)を窒素下で添加し、室温で4時間反応させた。得られた反応溶液を大過剰のメタノールに再沈澱させ、白色固体(PF−1)0.61g(収率71%)を得た。
化合物Q−1の1.31g(5.0mmol)のメタノール溶液をメタノール/ナトリウムメトキシド28%溶液中に滴下し、室温で3時間反応させた後、溶媒を溜去した。得られた灰色の固形物を再びメタノール30ml中に溶解させ、0℃で0.8ml(5.5mmol)の4−クロロメチルスチレンを溶解させたTHF溶液5mlを滴下した。3時間撹拌後、溶媒を溜去して、白色の固体を1.48g(140mmol)及びエピクロルヒドリン0.51gと共に3時間100℃で反応させた。その後、水中にあけ、1mol/L塩酸で中和した。生成物を濾取し、アセトニトリルで再結晶することで、化合物(V−1)が1.73g(収率92%)得られた。
上記化合物V−1の0.75g(2.0mmol)をTHF中に溶解させ、窒素雰囲気下でアゾビスイソブチロニトリル(AIBN、0.1mmol、5mol%)を0℃で添加した後、10時間還流を行った。放冷後、反応溶液を大過剰のメタノール中に沈澱させて白色固体(PV−1)を0.66g(収率88%)得た。
前記化合物X−1の0.39g(1.0mmol)をDMF中に溶解させ、窒素雰囲気下でγ−プロピオラクトンの1.0%DMF溶液6.3ml(1.0mmol)を0℃で添加した後、10時間100℃で反応を行った。放冷後、反応溶液を大過剰のメタノール中に沈澱させて白色固体(PLX−1)を0.40g(収率87%)得た。
(L−1のグラフト共重合)
J.Polymer Sci.34,309(1959)に従って、スチレンとメタクリロイルカプロラクタムをAIBNにより重合し、ポリ(メタクリロイルカプロラクタム)とポリ(スチレン)の共重合体(PMS)を得た(収率27%)。この重合体をGPCにより測定したところ、数平均分子量約13万程度のポリマーであることを確認した。この重合体1.0gと前記化合物L−1の1.0gを、トルエン中、95℃にて重合開始剤にカプロラクトンナトリウムを用いてグラフト重合を行った。反応中にゲル化が起こったので、放冷後、濾過、洗浄し、乾燥することで白色固体PGL−1を1.42g(収率71%)得た。
(有機EL素子の作製)
陽極として、ガラス上にITO(前出)を150nm成膜した基板(NHテクノグラス社製:NA−45)にパターニングを行った後、このITO透明電極を設けた透明支持基板をi−プロピルアルコールで超音波洗浄し、乾燥窒素ガスで乾燥し、UVオゾン洗浄を5分間行った。この透明支持基板上に、ポリマーPE−1の20mgをTHF3mlに溶解させ、1000rpm、3secの条件下スピンコートした。精製した有機薄膜の膜厚は、約100nmであった。
実施例1において、PE−1の代わりに、それぞれPL−1、PN−1、PX−1、PF−1、PV−1、PLX−1及びPGL−1を用いて100nmの厚さにスピンコートし発光層とした以外は実施例1と全く同じ方法で、有機EL素子DL−1、DN−1、DX−1、DF−1、DV−1、DLX−1及びDGL−1を作製した。
実施例1において、スピンコートするポリマーPE−1の20mg、THF3ml溶液に、4−ジシアノメチレン−2−メチル−6−(4−ジメチルアミノスチリル)−4H−ピラン(DCM1)0.2mgを溶解させ、1000rpm、3secの条件下でスピンコートした以外は全く同じ方法で、有機EL素子DD−1を作製した。
陽極としてガラス上にITOを150nm成膜した基板(NA−45:前出)にパターニングを行った後、このITO透明電極を設けた透明支持基板をi−プロピルアルコールで超音波洗浄し、乾燥窒素ガスで乾燥し、UVオゾン洗浄を5分間行った。
比較例1において、TPDの代わりに化合物Q−1を用いて正孔輸送層兼発光層とした以外は実施例1と全く同じ方法で、有機EL素子DQ−1を作製した。
東陽テクニカ社製ソースメジャーユニット2400型を用いて、有機EL素子DE−1、DL−1、DN−1、DX−1、DF−1、DV−1、DLX−1、DGL−1、DD−1及び比較用の有機EL素子DT−1、DQ−1に素子のITO電極を陽極、リチウムとアルミニウムからなる対向電極を陰極として直流10Vを印加し発光させ、その輝度をトプコン社製の輝度計BM−8、発光波長を浜松フォトニクス社製スペクトルアナライザーPMA−11を用いて測定した。
Claims (4)
- 互いに対向する陽極と陰極間に、単層又は複数層の有機化合物薄膜により成る発光層を挟持した有機エレクトロルミネッセンス素子において、該有機化合物薄膜の少なくとも1層が、下記一般式(5)で表される重合性環状構造を有する化合物、又はその重合体を少なくとも一種含有することを特徴とする有機エレクトロルミネッセンス素子。
- 請求項1または2記載の有機エレクトロルミネッセンス素子において、前記一般式(5)で表される化合物から選ばれる少なくとも1種の化合物をモノマーとして含む共重合体を少なくとも1種含有する有機化合物薄膜を少なくとも1層有することを特徴とする有機エレクトロルミネッセンス素子。
- 請求項1〜3のいずれか1項に記載の有機エレクトロルミネッセンス素子において、前記一般式(5)で表される化合物から選ばれる少なくとも1種の化合物と、反応性基を有する高分子とを付加反応、縮合反応あるいはグラフト重合させて得られた高分子化合物を少なくとも1種含有する有機化合物薄膜を少なくとも1層有することを特徴とする有機エレクトロルミネッセンス素子。
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JP2000063818A (ja) * | 1998-08-18 | 2000-02-29 | Fuji Photo Film Co Ltd | 有機エレクトロルミネツセンス素子材料およびそれを使用した有機エレクトロルミネツセンス素子 |
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