JP7088010B2 - 赤外発光led - Google Patents
赤外発光led Download PDFInfo
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- JP7088010B2 JP7088010B2 JP2018527629A JP2018527629A JP7088010B2 JP 7088010 B2 JP7088010 B2 JP 7088010B2 JP 2018527629 A JP2018527629 A JP 2018527629A JP 2018527629 A JP2018527629 A JP 2018527629A JP 7088010 B2 JP7088010 B2 JP 7088010B2
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- -1 cyclic olefin Chemical class 0.000 claims description 133
- 230000005855 radiation Effects 0.000 claims description 104
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- 239000000178 monomer Substances 0.000 claims description 42
- 239000003431 cross linking reagent Substances 0.000 claims description 28
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 22
- 229920000642 polymer Polymers 0.000 claims description 14
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- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
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- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 4
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- 229910052717 sulfur Inorganic materials 0.000 description 4
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 4
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 3
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- WTQZSMDDRMKJRI-UHFFFAOYSA-N 4-diazoniophenolate Chemical class [O-]C1=CC=C([N+]#N)C=C1 WTQZSMDDRMKJRI-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 229910001218 Gallium arsenide Inorganic materials 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
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- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
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- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
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- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000007983 Tris buffer Substances 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 125000002723 alicyclic group Chemical group 0.000 description 3
- 125000002521 alkyl halide group Chemical group 0.000 description 3
- 125000002947 alkylene group Chemical group 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
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- 229920001577 copolymer Polymers 0.000 description 3
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- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
- 238000009826 distribution Methods 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 238000005227 gel permeation chromatography Methods 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
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- 239000003607 modifier Substances 0.000 description 3
- JFNLZVQOOSMTJK-UHFFFAOYSA-N norbornene Chemical compound C1C2CCC1C=C2 JFNLZVQOOSMTJK-UHFFFAOYSA-N 0.000 description 3
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- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical class O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 3
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 2
- QYGBYAQGBVHMDD-XQRVVYSFSA-N (z)-2-cyano-3-thiophen-2-ylprop-2-enoic acid Chemical compound OC(=O)C(\C#N)=C/C1=CC=CS1 QYGBYAQGBVHMDD-XQRVVYSFSA-N 0.000 description 2
- PRBHEGAFLDMLAL-UHFFFAOYSA-N 1,5-Hexadiene Natural products CC=CCC=C PRBHEGAFLDMLAL-UHFFFAOYSA-N 0.000 description 2
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- 125000006218 1-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 2
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- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 2
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- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
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- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 2
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- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 2
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- 125000005843 halogen group Chemical group 0.000 description 2
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- PYGSKMBEVAICCR-UHFFFAOYSA-N hexa-1,5-diene Chemical compound C=CCCC=C PYGSKMBEVAICCR-UHFFFAOYSA-N 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 125000004464 hydroxyphenyl group Chemical group 0.000 description 2
- 229910003437 indium oxide Inorganic materials 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
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 2
- CPJRRXSHAYUTGL-UHFFFAOYSA-N isopentenyl alcohol Chemical compound CC(=C)CCO CPJRRXSHAYUTGL-UHFFFAOYSA-N 0.000 description 2
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- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 2
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- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 150000001469 hydantoins Chemical class 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229910052743 krypton Inorganic materials 0.000 description 1
- DNNSSWSSYDEUBZ-UHFFFAOYSA-N krypton atom Chemical compound [Kr] DNNSSWSSYDEUBZ-UHFFFAOYSA-N 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- HNEGQIOMVPPMNR-NSCUHMNNSA-N mesaconic acid Chemical compound OC(=O)C(/C)=C/C(O)=O HNEGQIOMVPPMNR-NSCUHMNNSA-N 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000005649 metathesis reaction Methods 0.000 description 1
- 229940057867 methyl lactate Drugs 0.000 description 1
- 229940017219 methyl propionate Drugs 0.000 description 1
- ARLYLDLNVQPCQY-UHFFFAOYSA-N methyl tricyclo[5.2.1.02,6]dec-8-ene-2-carboxylate Chemical compound COC(=O)C12C3C=CC(C2CCC1)C3 ARLYLDLNVQPCQY-UHFFFAOYSA-N 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- HNEGQIOMVPPMNR-UHFFFAOYSA-N methylfumaric acid Natural products OC(=O)C(C)=CC(O)=O HNEGQIOMVPPMNR-UHFFFAOYSA-N 0.000 description 1
- 238000006011 modification reaction Methods 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- UUIQMZJEGPQKFD-UHFFFAOYSA-N n-butyric acid methyl ester Natural products CCCC(=O)OC UUIQMZJEGPQKFD-UHFFFAOYSA-N 0.000 description 1
- GNVRJGIVDSQCOP-UHFFFAOYSA-N n-ethyl-n-methylethanamine Chemical compound CCN(C)CC GNVRJGIVDSQCOP-UHFFFAOYSA-N 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229910052754 neon Inorganic materials 0.000 description 1
- GKAOGPIIYCISHV-UHFFFAOYSA-N neon atom Chemical compound [Ne] GKAOGPIIYCISHV-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 1
- YWXLSHOWXZUMSR-UHFFFAOYSA-N octan-4-one Chemical compound CCCCC(=O)CCC YWXLSHOWXZUMSR-UHFFFAOYSA-N 0.000 description 1
- 229920002114 octoxynol-9 Polymers 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 150000002896 organic halogen compounds Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 1
- AZQWKYJCGOJGHM-UHFFFAOYSA-N para-benzoquinone Natural products O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 1
- LQAVWYMTUMSFBE-UHFFFAOYSA-N pent-4-en-1-ol Chemical compound OCCCC=C LQAVWYMTUMSFBE-UHFFFAOYSA-N 0.000 description 1
- WNBDFALPKHFDJO-UHFFFAOYSA-N pentadec-3-ene Chemical compound CCCCCCCCCCCC=CCC WNBDFALPKHFDJO-UHFFFAOYSA-N 0.000 description 1
- OHVKVVAUWQFKQY-UHFFFAOYSA-N pentadeca-2,7,9,11-tetraene Chemical compound CCCC=CC=CC=CCCCC=CC OHVKVVAUWQFKQY-UHFFFAOYSA-N 0.000 description 1
- LTBKJTHWKYUMTA-UHFFFAOYSA-N pentadeca-3,10-diene Chemical compound CCCCC=CCCCCCC=CCC LTBKJTHWKYUMTA-UHFFFAOYSA-N 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
- 125000005003 perfluorobutyl group Chemical group FC(F)(F)C(F)(F)C(F)(F)C(F)(F)* 0.000 description 1
- 125000005008 perfluoropentyl group Chemical group FC(C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)(F)* 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 239000002530 phenolic antioxidant Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 150000004714 phosphonium salts Chemical class 0.000 description 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
- DOIRQSBPFJWKBE-UHFFFAOYSA-N phthalic acid di-n-butyl ester Natural products CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 230000037048 polymerization activity Effects 0.000 description 1
- 239000002685 polymerization catalyst Substances 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920000259 polyoxyethylene lauryl ether Polymers 0.000 description 1
- 150000008442 polyphenolic compounds Chemical class 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- ASUAYTHWZCLXAN-UHFFFAOYSA-N prenol Chemical compound CC(C)=CCO ASUAYTHWZCLXAN-UHFFFAOYSA-N 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- KCTAWXVAICEBSD-UHFFFAOYSA-N prop-2-enoyloxy prop-2-eneperoxoate Chemical compound C=CC(=O)OOOC(=O)C=C KCTAWXVAICEBSD-UHFFFAOYSA-N 0.000 description 1
- YGEZYTLOABCHSH-UHFFFAOYSA-N propyl 5-methylbicyclo[2.2.1]hept-2-ene-5-carboxylate Chemical compound C1C2C(C(=O)OCCC)(C)CC1C=C2 YGEZYTLOABCHSH-UHFFFAOYSA-N 0.000 description 1
- 229940090181 propyl acetate Drugs 0.000 description 1
- LKKVMVMKNLULSL-UHFFFAOYSA-N propyl bicyclo[2.2.1]hept-2-ene-5-carboxylate Chemical compound C1C2C(C(=O)OCCC)CC1C=C2 LKKVMVMKNLULSL-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- QMTZQLNTTKDRKC-UHFFFAOYSA-N propyl tricyclo[5.2.1.02,6]dec-8-ene-2-carboxylate Chemical compound C(CC)OC(=O)C12C3C=CC(C2CCC1)C3 QMTZQLNTTKDRKC-UHFFFAOYSA-N 0.000 description 1
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 230000002285 radioactive effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000007152 ring opening metathesis polymerisation reaction Methods 0.000 description 1
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 1
- 239000012487 rinsing solution Substances 0.000 description 1
- 229960001860 salicylate Drugs 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- 125000005624 silicic acid group Chemical class 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000019795 sodium metasilicate Nutrition 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 230000007480 spreading Effects 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- XBFJAVXCNXDMBH-UHFFFAOYSA-N tetracyclo[6.2.1.1(3,6).0(2,7)]dodec-4-ene Chemical compound C1C(C23)C=CC1C3C1CC2CC1 XBFJAVXCNXDMBH-UHFFFAOYSA-N 0.000 description 1
- PVJHFVMRMWVWAX-UHFFFAOYSA-N tetradeca-2,7,9,11-tetraene Chemical compound CCC=CC=CC=CCCCC=CC PVJHFVMRMWVWAX-UHFFFAOYSA-N 0.000 description 1
- 229940073455 tetraethylammonium hydroxide Drugs 0.000 description 1
- LRGJRHZIDJQFCL-UHFFFAOYSA-M tetraethylazanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CC LRGJRHZIDJQFCL-UHFFFAOYSA-M 0.000 description 1
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 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
- 229910052719 titanium Inorganic materials 0.000 description 1
- 125000005409 triarylsulfonium group Chemical group 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- YOKZJDRCZXTECO-UHFFFAOYSA-N tricyclo[5.2.1.02,6]deca-3,8-diene-2-carboxylic acid Chemical compound C1=CC2CC1C1(C(=O)O)C2CC=C1 YOKZJDRCZXTECO-UHFFFAOYSA-N 0.000 description 1
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-UHFFFAOYSA-N 0.000 description 1
- 229910021642 ultra pure water Inorganic materials 0.000 description 1
- 239000012498 ultrapure water Substances 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 238000000927 vapour-phase epitaxy Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
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- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L33/00—Semiconductor devices having potential barriers specially adapted for light emission; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof
- H01L33/44—Semiconductor devices having potential barriers specially adapted for light emission; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof characterised by the coatings, e.g. passivation layer or anti-reflective coating
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- C—CHEMISTRY; METALLURGY
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- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L65/00—Compositions of macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain; Compositions of derivatives of such polymers
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- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B3/00—Simple or compound lenses
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
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- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
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- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/022—Quinonediazides
- G03F7/023—Macromolecular quinonediazides; Macromolecular additives, e.g. binders
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- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
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- H01L33/48—Semiconductor devices having potential barriers specially adapted for light emission; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof characterised by the semiconductor body packages
- H01L33/52—Encapsulations
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- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L33/00—Semiconductor devices having potential barriers specially adapted for light emission; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof
- H01L33/48—Semiconductor devices having potential barriers specially adapted for light emission; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof characterised by the semiconductor body packages
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Description
〔1〕素子上に形成された絶縁膜と、前記絶縁膜上に形成されたマイクロレンズとを備える赤外発光LEDであって、前記絶縁膜及び前記マイクロレンズが、プロトン性極性基を有する環状オレフィン重合体(A)、感放射線化合物(B)及び架橋剤(C)を含有する感放射線樹脂組成物を用いて形成されたことを特徴とする赤外発光LED、
〔2〕前記絶縁膜の厚みが1~10μmであり、前記マイクロレンズの厚みが0.5~5μmである前記〔1〕に記載の赤外発光LED、
〔3〕前記絶縁膜の厚みと、前記マイクロレンズの厚みとの比率が、「絶縁膜の厚み:マイクロレンズの厚み」で1:1~10:1である前記〔1〕又は〔2〕に記載の赤外発光LED、
〔4〕前記絶縁膜の屈折率と、前記マイクロレンズの屈折率の差が0.1以下である前記〔1〕~〔3〕のいずれかに記載の赤外発光LED、
〔5〕前記絶縁膜と前記マイクロレンズとが、前記環状オレフィン重合体(A)として、同じ重合体を含有する感放射線樹脂組成物をそれぞれ用いて形成されたものである前記〔1〕~〔4〕のいずれかに記載の赤外発光LED、
〔6〕前記絶縁膜と前記マイクロレンズとが、全て同じ成分から構成される感放射線樹脂組成物をそれぞれ用いて形成されたものである前記〔5〕に記載の赤外発光LED、ならびに、
〔7〕前記絶縁膜と前記マイクロレンズとが、全て同じ成分を同じ含有割合で含有する感放射線樹脂組成物をそれぞれ用いて形成されたものである前記〔6〕に記載の赤外発光LED、
が提供される。
以下、図1に示す本発明の一実施形態に係る赤外発光LED10を例示して、本発明について詳細に説明する。ただし、本発明は、図1に示す態様に特に限定されるものではない。
次いで、保護絶縁膜50及びマイクロレンズ60を形成するための感放射線樹脂組成物について、説明する。
保護絶縁膜50及びマイクロレンズ60を形成するための感放射線樹脂組成物は、プロトン性極性基を有する環状オレフィン重合体(A)、感放射線化合物(B)及び架橋剤(C)を含有する感放射線性の樹脂組成物である。
本発明において、プロトン性極性基を有する環状オレフィン重合体に結合しているプロトン性極性基の数に特に限定はなく、また、相異なる種類のプロトン性極性基が含まれていてもよい。
これら単量体(b2)は、それぞれ単独で用いてもよく、2種以上を組み合わせて用いてもよい。
これら単量体(b3)は、それぞれ単独で用いてもよく、2種以上を組み合わせて用いてもよい。
プロトン性極性基を有しない重合体は、上述した単量体(b1)及び(b2)のうち少なくとも一種と、必要に応じて単量体(b3)とを任意に組み合わせて重合することによって得ることができる。
このような化合物の具体例としては、アクリル酸、メタクリル酸、アンゲリカ酸、チグリン酸、オレイン酸、エライジン酸、エルカ酸、ブラシジン酸、マレイン酸、フマル酸、シトラコン酸、メサコン酸、イタコン酸、アトロパ酸、ケイ皮酸等の不飽和カルボン酸;アリルアルコール、メチルビニルメタノール、クロチルアルコール、メタリルアルコール、1-フェニルエテン-1-オール、2-プロペン-1-オール、3-ブテン-1-オール、3-ブテン-2-オール、3-メチル-3-ブテン-1-オール、3-メチル-2-ブテン-1-オール、2-メチル-3-ブテン-2-オール、2-メチル-3-ブテン-1-オール、4-ペンテン-1-オール、4-メチル-4-ぺンテン-1-オール、2-ヘキセン-1-オール等の不飽和アルコール;等が挙げられる。
これら変性剤を用いた重合体の変性反応は、常法に従えばよく、通常、ラジカル発生剤の存在下で行われる。
また、環状オレフィン重合体(A)の分子量分布は、重量平均分子量/数平均分子量(Mw/Mn)比で、通常、4以下、好ましくは3以下、より好ましくは2.5以下である。
環状オレフィン重合体(A)の重量平均分子量(Mw)や分子量分布(Mw/Mn)は、テトラヒドロフラン等の溶媒を溶離液としたゲル・パーミエーション・クロマトグラフィー(GPC)により、ポリスチレン換算値として求められる値である。
これらの感放射線化合物は、それぞれ単独で、又は2種以上を組み合わせて用いることができる。
なお、架橋剤(C)の重量平均分子量はゲルパーミエーションクロマトグラフィーを用いてポリスチレン換算で測定を行うなどの常法に従い分析することができる。
架橋剤(C)は、それぞれ単独で又は2種以上を組み合わせて用いることができる。
リン系酸化防止剤としては、亜リン酸トリフェニル、亜リン酸トリス( ノニルフェニル)、イオウ系酸化防止剤としては、チオジプロピオン酸ジラウリル等が挙げられる。
混合の方法は特に限定されないが、感放射線樹脂組成物を構成する各成分を溶剤に溶解又は分散して得られる溶液又は分散液を混合するのが好ましい。これにより、感放射線樹脂組成物は、溶液又は分散液の形態で得られる。
次いで、上述した感放射線樹脂組成物を用いて、本発明の赤外発光LEDを形成する、絶縁膜及びマイクロレンズを形成するための方法について、図1に示す本発明の一実施形態に係る赤外発光LED10を例示して、説明する。
潜像パターンを有する樹脂膜に現像液を接触させる方法としては、例えば、パドル法、スプレー法、ディッピング法等の方法が用いられる。現像は、通常、0~100℃、好ましくは5~55℃、より好ましくは10~30℃の範囲で、通常、30~180秒間の範囲で適宜選択される。
さらに、必要に応じて、感放射線樹脂組成物に含有させた感放射線化合物(B)を失活させるために、電子部品全面に、活性放射線を照射することもできる。活性放射線の照射には、上記潜像パターンの形成に例示した方法を利用できる。照射と同時に、又は照射後にマイクロレンズ用樹脂膜を加熱してもよい。加熱方法としては、例えば、電子部品をホットプレートやオーブン内で加熱する方法が挙げられる。温度は、通常、80~300℃、好ましくは100~200℃の範囲である。
<環状オレフィン重合体(A-1)の調製>
N-フェニル-ビシクロ[2.2.1]ヘプト-5-エン-2,3-ジカルボキシイミド(NBPI)40モル%、及び4-ヒドロキシカルボニルテトラシクロ[6.2.1.13,6.02,7]ドデカ-9-エン(TCDC)60モル%からなる単量体混合物100部、1,5-ヘキサジエン2.0部、(1,3-ジメシチルイミダゾリン-2-イリデン)(トリシクロヘキシルホスフィン)ベンジリデンルテニウムジクロリド(Org.Lett.,第1巻,953頁,1999年 に記載された方法で合成した)0.02部、及びジエチレングリコールエチルメチルエーテル200部を、窒素置換したガラス製耐圧反応器に仕込み、攪拌しつつ80℃にて4時間反応させて重合反応液を得た。
環状オレフィン重合体(A)として、合成例1で得られた環状オレフィン重合体(A-1)の重合体溶液291部(環状オレフィン重合体(A-1)として100部)、感放射線化合物(B)として、1,1,3-トリス(2,5-ジメチル-4-ヒドロキシフェニル)-3-フェニルプロパンと1,2-ナフトキノンジアジド-5-スルホン酸クロライドとの縮合物35部、架橋剤(C)として、エポキシ化ブタンテトラカルボン酸テトラキス(3-シクロヘキセニルメチル)修飾ε-カプロラクトン50部、溶剤として、ジエチレングリコールエチルメチルエーテル600部を混合し、溶解させた後、孔径0.45μmのポリテトラフルオロエチレン製フィルターでろ過して感放射線樹脂組成物を調製した。
上記にて得られた感放射線樹脂組成物をガラス基板上にスピンコートし、ホットプレートを用いて110℃で120秒間乾燥し、乾燥後の膜厚が3.0μmになるように成膜した。この樹脂膜に1,000mW/cm2の紫外線を照射してブリーチ(感放射線化合物(B)の失活処理)した後、窒素雰囲気下で230℃、60分間焼成することで、透過率評価用ガラス基板サンプルを作製した。そして、得られたガラス基板サンプルを用いて、紫外可視近赤外分光光度計(「LAMBDA900」、PerklnElmer社製)により赤外波長域の透過率を測定した。測定結果を図2に示す。図2には、SiNxからなる無機絶縁膜が形成されたガラス基板サンプルの結果も併せて示した。なお、SiNxからなる無機絶縁膜が形成されたガラス基板サンプルは、上記と同様のガラス基板を用い、スパッタンリング法により、SiNxからなる無機絶縁膜を形成することにより製造した。
一方、SiNxからなる無機絶縁膜は、850nmにおける透過率は92%であり、また、940nmにおける透過率が90%であり、いずれも透過性に劣るものであった。
上記の透過率評価用ガラス基板サンプル作製と同様の方法で膜厚3.0μmの熱硬化性樹脂膜が成膜されたシリコンウエハー基板上に、さらに上記にて得られた感放射線性樹脂組成物をスピンコートし、ホットプレートを用いて110℃で120秒間乾燥し、乾燥後の膜厚が3.0μm(先に作製した熱硬化性樹脂膜と合わせた合計の膜厚は6.0μm)になるように成膜した。この樹脂膜に、3.5μmドット、1.5μmスペースのパターンのマスクを介して、光強度が10mW/cm2(Wは、J/sに相当)である紫外線を空気中で30秒間照射した。次いで、テトラメチルアンモニウムヒドロキシド0.4%溶液を用いて23℃で100秒間現像処理を行った後、超純水で30秒間リンス処理し、ポジ型の3.5μmのドットパターン化樹脂膜を形成した。
〔評価基準〕
優:パターンが半球体形状で、(a-b)が0.5μm以下である。
良:パターンが半球体形状で、(a-b)が0.5μmを超え、1μm以下である。
可:パターンが半球体形状で、(a-b)が1μmを超え、1.5μm以下である。
不可:パターンが完全に溶融し、隣接パターンと融着している。
以上の結果より、プロトン性極性基を有する環状オレフィン重合体(A)、感放射線化合物(B)及び架橋剤(C)を含有する感放射線樹脂組成物を用いることで、700~1500nmの波長域、特に、850nm及び940nmにおける透過性に優れる保護絶縁膜50、及び、このような波長域において透過性に優れ、しかも、耐熱形状保持性に優れたマイクロレンズ60を形成可能であることが確認できる。特に、700~1500nmの波長域において、透過率が98%以上であり、さらには、赤外発光LEDにおいて通常用いられる850nm及び940nmにおける透過率が、いずれも99%以上であることから、保護絶縁膜50の厚みt1を3~5μmと比較的厚くし、かつ、マイクロレンズ60の厚みt2を2~3μmとした場合でも、優れた透過性を実現することができ、さらには、保護絶縁膜50の厚みを厚くできることで、優れた透過性を実現しながら、保護絶縁膜50による絶縁性能を十分に確保できるものである。また、耐熱形状保持性に優れたマイクロレンズ60を形成可能であることから、得られる赤外LED10を、信頼性に優れたものとすることができるものである。
以上より、本発明によれば、高輝度かつ信頼性の高い赤外発光LEDを適切に提供できるものである。
20…エピタキシャルウエハ
21…AlGaAs基板
22…エピタキシャル層
23…透明導電膜
30…nドット電極
40…pパッド電極
50…保護絶縁膜
60…マイクロレンズ
Claims (6)
- 素子上に形成された絶縁膜と、前記絶縁膜上に形成されたマイクロレンズとを備える赤外発光LEDであって、
前記絶縁膜及び前記マイクロレンズが、プロトン性極性基を有する環状オレフィン重合体(A)、感放射線化合物(B)及び架橋剤(C)を含有する感放射線樹脂組成物を用いて形成され、
前記プロトン性極性基を有する環状オレフィン重合体(A)が、カルボキシ基含有環状オレフィン単量体の単位と、N-置換イミド基を有する環状オレフィンの単位とを含む重合体であり、
前記感放射線化合物(B)が、アジド化合物であり、
前記架橋剤(C)が、2以上のエポキシ基を有する化合物であり、
前記感放射線樹脂組成物中における、前記環状オレフィン重合体(A)100重量部に対する、前記感放射線化合物(B)の含有量が20~100重量部であり、前記架橋剤(C)の含有量が5~80重量部であり、
前記絶縁膜の厚みが1~10μmであり、前記マイクロレンズの厚みが0.5~5μmである赤外発光LED。 - 前記絶縁膜の厚みと、前記マイクロレンズの厚みとの比率が、「樹脂膜の厚み:マイクロレンズの厚み」で1:1~10:1である請求項1に記載の赤外発光LED。
- 前記絶縁膜の屈折率と、前記マイクロレンズの屈折率の差が0.1以下である請求項1または2に記載の赤外発光LED。
- 前記絶縁膜と前記マイクロレンズとが、前記環状オレフィン重合体(A)として、同じ重合体を含有する感放射線樹脂組成物をそれぞれ用いて形成されたものである請求項1~3のいずれかに記載の赤外発光LED。
- 前記絶縁膜と前記マイクロレンズとが、全て同じ成分から構成される感放射線樹脂組成物をそれぞれ用いて形成されたものである請求項4に記載の赤外発光LED。
- 前記絶縁膜と前記マイクロレンズとが、全て同じ成分を同じ含有割合で含有する感放射線樹脂組成物をそれぞれ用いて形成されたものである請求項5に記載の赤外発光LED。
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