JPWO2019188475A1 - トリアジン環含有重合体、樹脂組成物、硬化膜および固体撮像素子 - Google Patents
トリアジン環含有重合体、樹脂組成物、硬化膜および固体撮像素子 Download PDFInfo
- Publication number
- JPWO2019188475A1 JPWO2019188475A1 JP2019516269A JP2019516269A JPWO2019188475A1 JP WO2019188475 A1 JPWO2019188475 A1 JP WO2019188475A1 JP 2019516269 A JP2019516269 A JP 2019516269A JP 2019516269 A JP2019516269 A JP 2019516269A JP WO2019188475 A1 JPWO2019188475 A1 JP WO2019188475A1
- Authority
- JP
- Japan
- Prior art keywords
- group
- triazine ring
- hydrogen atom
- containing polymer
- triazine
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 229920000642 polymer Polymers 0.000 title claims abstract description 78
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 title claims abstract description 75
- 239000011342 resin composition Substances 0.000 title claims description 12
- -1 hydroxysilyl group Chemical group 0.000 claims description 94
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 21
- 125000000962 organic group Chemical group 0.000 claims description 18
- 125000001424 substituent group Chemical group 0.000 claims description 18
- 125000003118 aryl group Chemical group 0.000 claims description 13
- 125000000623 heterocyclic group Chemical group 0.000 claims description 11
- 125000001931 aliphatic group Chemical group 0.000 claims description 6
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 239000004215 Carbon black (E152) Substances 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 229930195733 hydrocarbon Natural products 0.000 claims description 2
- 150000002430 hydrocarbons Chemical class 0.000 claims description 2
- 125000005647 linker group Chemical group 0.000 claims description 2
- 239000000203 mixture Substances 0.000 abstract description 70
- 239000000126 substance Substances 0.000 abstract description 23
- 230000015572 biosynthetic process Effects 0.000 abstract description 20
- 229910044991 metal oxide Inorganic materials 0.000 abstract description 6
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- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
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- 229920001187 thermosetting polymer Polymers 0.000 description 4
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- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 3
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- QPRQEDXDYOZYLA-UHFFFAOYSA-N 2-methylbutan-1-ol Chemical compound CCC(C)CO QPRQEDXDYOZYLA-UHFFFAOYSA-N 0.000 description 3
- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 3
- LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical compound NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
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- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 3
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- CATWEXRJGNBIJD-UHFFFAOYSA-N n-tert-butyl-2-methylpropan-2-amine Chemical compound CC(C)(C)NC(C)(C)C CATWEXRJGNBIJD-UHFFFAOYSA-N 0.000 description 1
- MFPKYHCHDTUVAY-UHFFFAOYSA-N naphthalene-1,3,5-triamine Chemical compound C1=CC=C(N)C2=CC(N)=CC(N)=C21 MFPKYHCHDTUVAY-UHFFFAOYSA-N 0.000 description 1
- JOJOPWYLFLOFAE-UHFFFAOYSA-N naphthalene-1,3,7-triamine Chemical compound C1=C(N)C=C(N)C2=CC(N)=CC=C21 JOJOPWYLFLOFAE-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- WSGCRAOTEDLMFQ-UHFFFAOYSA-N nonan-5-one Chemical compound CCCCC(=O)CCCC WSGCRAOTEDLMFQ-UHFFFAOYSA-N 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- VMPITZXILSNTON-UHFFFAOYSA-N o-anisidine Chemical compound COC1=CC=CC=C1N VMPITZXILSNTON-UHFFFAOYSA-N 0.000 description 1
- 229940078552 o-xylene Drugs 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 125000005375 organosiloxane group Chemical group 0.000 description 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
- 125000003566 oxetanyl group Chemical group 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- LRTFPLFDLJYEKT-UHFFFAOYSA-N para-isopropylaniline Chemical compound CC(C)C1=CC=C(N)C=C1 LRTFPLFDLJYEKT-UHFFFAOYSA-N 0.000 description 1
- 238000000059 patterning Methods 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 150000003053 piperidines Chemical class 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003207 poly(ethylene-2,6-naphthalate) Polymers 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 239000004631 polybutylene succinate Substances 0.000 description 1
- 229920002961 polybutylene succinate Polymers 0.000 description 1
- 229920001707 polybutylene terephthalate Polymers 0.000 description 1
- 239000004632 polycaprolactone Substances 0.000 description 1
- 229920001610 polycaprolactone Polymers 0.000 description 1
- 229920005668 polycarbonate resin Polymers 0.000 description 1
- 239000004431 polycarbonate resin Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 239000011112 polyethylene naphthalate Substances 0.000 description 1
- 229920013716 polyethylene resin Polymers 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 239000009719 polyimide resin Substances 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920005672 polyolefin resin Polymers 0.000 description 1
- 229920000259 polyoxyethylene lauryl ether Polymers 0.000 description 1
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
- 239000000249 polyoxyethylene sorbitan monopalmitate Substances 0.000 description 1
- 235000010483 polyoxyethylene sorbitan monopalmitate Nutrition 0.000 description 1
- 239000001818 polyoxyethylene sorbitan monostearate Substances 0.000 description 1
- 235000010989 polyoxyethylene sorbitan monostearate Nutrition 0.000 description 1
- 239000001816 polyoxyethylene sorbitan tristearate Substances 0.000 description 1
- 235000010988 polyoxyethylene sorbitan tristearate Nutrition 0.000 description 1
- 229920006324 polyoxymethylene Polymers 0.000 description 1
- 229920000069 polyphenylene sulfide Polymers 0.000 description 1
- 229920005990 polystyrene resin Polymers 0.000 description 1
- 229920005749 polyurethane resin Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- SCUZVMOVTVSBLE-UHFFFAOYSA-N prop-2-enenitrile;styrene Chemical compound C=CC#N.C=CC1=CC=CC=C1 SCUZVMOVTVSBLE-UHFFFAOYSA-N 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 229940090181 propyl acetate Drugs 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
- MFUFBSLEAGDECJ-UHFFFAOYSA-N pyren-2-ylamine Natural products C1=CC=C2C=CC3=CC(N)=CC4=CC=C1C2=C43 MFUFBSLEAGDECJ-UHFFFAOYSA-N 0.000 description 1
- APXBXAJWVZTKSE-UHFFFAOYSA-N pyridine-2,3,4-triamine Chemical compound NC1=CC=NC(N)=C1N APXBXAJWVZTKSE-UHFFFAOYSA-N 0.000 description 1
- UIQHHOMREHEPJX-UHFFFAOYSA-N pyridine-3,4,5-triamine Chemical compound NC1=CN=CC(N)=C1N UIQHHOMREHEPJX-UHFFFAOYSA-N 0.000 description 1
- 239000002096 quantum dot Substances 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- KQAOOAMWHFLFSY-UHFFFAOYSA-N quinoline-2,4,5-triamine Chemical compound Nc1cc(N)c2c(N)cccc2n1 KQAOOAMWHFLFSY-UHFFFAOYSA-N 0.000 description 1
- HPSCQLNGARXBPM-UHFFFAOYSA-N quinoline-2,4,6-triamine Chemical compound Nc1ccc2nc(N)cc(N)c2c1 HPSCQLNGARXBPM-UHFFFAOYSA-N 0.000 description 1
- MFKYUAQPIDWMKE-UHFFFAOYSA-N quinoline-2,4,7-triamine Chemical compound Nc1ccc2c(N)cc(N)nc2c1 MFKYUAQPIDWMKE-UHFFFAOYSA-N 0.000 description 1
- GCLOSLMAMSATTC-UHFFFAOYSA-N quinoline-2,4,8-triamine Chemical compound Nc1cc(N)c2cccc(N)c2n1 GCLOSLMAMSATTC-UHFFFAOYSA-N 0.000 description 1
- JHTNARIVBMZFRV-UHFFFAOYSA-N quinoline-3,5,7-triamine Chemical compound Nc1cnc2cc(N)cc(N)c2c1 JHTNARIVBMZFRV-UHFFFAOYSA-N 0.000 description 1
- BJLZOXGVPKYQKG-UHFFFAOYSA-N quinoline-3,6,8-triamine Chemical compound NC=1C=NC2=C(C=C(C=C2C1)N)N BJLZOXGVPKYQKG-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 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
- 230000008313 sensitization Effects 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical group [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 229940035044 sorbitan monolaurate Drugs 0.000 description 1
- 239000001593 sorbitan monooleate Substances 0.000 description 1
- 235000011069 sorbitan monooleate Nutrition 0.000 description 1
- 229940035049 sorbitan monooleate Drugs 0.000 description 1
- 239000001570 sorbitan monopalmitate Substances 0.000 description 1
- 235000011071 sorbitan monopalmitate Nutrition 0.000 description 1
- 229940031953 sorbitan monopalmitate Drugs 0.000 description 1
- 239000001587 sorbitan monostearate Substances 0.000 description 1
- 235000011076 sorbitan monostearate Nutrition 0.000 description 1
- 229940035048 sorbitan monostearate Drugs 0.000 description 1
- 239000001589 sorbitan tristearate Substances 0.000 description 1
- 235000011078 sorbitan tristearate Nutrition 0.000 description 1
- 229960004129 sorbitan tristearate Drugs 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 229940014800 succinic anhydride Drugs 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
- 150000003512 tertiary amines Chemical class 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
- 125000003698 tetramethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 238000010023 transfer printing Methods 0.000 description 1
- INUOIYMEJLOQFN-UHFFFAOYSA-N tributoxy(phenyl)silane Chemical compound CCCCO[Si](OCCCC)(OCCCC)C1=CC=CC=C1 INUOIYMEJLOQFN-UHFFFAOYSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1
- RKBCYCFRFCNLTO-UHFFFAOYSA-N triisopropylamine Chemical compound CC(C)N(C(C)C)C(C)C RKBCYCFRFCNLTO-UHFFFAOYSA-N 0.000 description 1
- TWQULNDIKKJZPH-UHFFFAOYSA-K trilithium;phosphate Chemical compound [Li+].[Li+].[Li+].[O-]P([O-])([O-])=O TWQULNDIKKJZPH-UHFFFAOYSA-K 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
- 229910000404 tripotassium phosphate Inorganic materials 0.000 description 1
- 235000019798 tripotassium phosphate Nutrition 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 229910000406 trisodium phosphate Inorganic materials 0.000 description 1
- 235000019801 trisodium phosphate Nutrition 0.000 description 1
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 1
- 229920006337 unsaturated polyester resin Polymers 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/0622—Polycondensates containing six-membered rings, not condensed with other rings, with nitrogen atoms as the only ring hetero atoms
- C08G73/0638—Polycondensates containing six-membered rings, not condensed with other rings, with nitrogen atoms as the only ring hetero atoms with at least three nitrogen atoms in the ring
- C08G73/0644—Poly(1,3,5)triazines
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L79/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen or carbon only, not provided for in groups C08L61/00 - C08L77/00
- C08L79/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L27/00—Devices consisting of a plurality of semiconductor or other solid-state components formed in or on a common substrate
- H01L27/14—Devices consisting of a plurality of semiconductor or other solid-state components formed in or on a common substrate including semiconductor components sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation and specially adapted either for the conversion of the energy of such radiation into electrical energy or for the control of electrical energy by such radiation
- H01L27/144—Devices controlled by radiation
- H01L27/146—Imager structures
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L31/00—Semiconductor devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation and specially adapted either for the conversion of the energy of such radiation into electrical energy or for the control of electrical energy by such radiation; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof
- H01L31/02—Details
- H01L31/0232—Optical elements or arrangements associated with the device
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- Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- Power Engineering (AREA)
- Engineering & Computer Science (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Electromagnetism (AREA)
- Medicinal Chemistry (AREA)
- Condensed Matter Physics & Semiconductors (AREA)
- General Physics & Mathematics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Computer Hardware Design (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
Description
W4は、単結合、−S−、−SO2−、−O−、−NR3−、−(CO)−NH−、−NH−(CO)−、−(CO)−O−、−(CO)−、−O−(CO)−及び−NH−(CO)−NH−を表し、W5およびW6は、互いに独立して、単結合、−CR70R71−(R70およびR71は、互いに独立して、水または有機基を表す。)、−(CO)−、−O−、−S−、−(SO)−、−SO2−を表す。W7〜9は単結合、−O−、−S−または−NR72−であり、R72は水素原子または有機基である。W10はNもしくは下記一般式(11)で示される基である。
なお、これらの化合物は、ポリマーの末端処理に用いる場合は少なくとも1個の架橋形成置換基を有していればよく、ポリマー同士の架橋処理に用いる場合は少なくとも2個の架橋形成置換基を有する必要がある。
なお、上記その他の成分は、本発明の組成物を調製する際の任意の工程で添加することができる。
(メタ)アクリレート化合物の例としては、メチル(メタ)アクリレート、エチル(メタ)アクリレート、エチレングリコールジ(メタ)アクリレート、テトラエチレングリコールジ(メタ)アクリレート、ポリエチレングリコールジ(メタ)アクリレート、プロピレングリコールジ(メタ)アクリレート、ポリプロピレングリコールジ(メタ)アクリレート、1,4−ブタンジオールジ(メタ)アクリレート、1,6−ヘキサンジオールジ(メタ)アクリレート、ネオペンチルグリコールジ(メタ)アクリレート、トリメチロールプロパントリオキシエチル(メタ)アクリレート、トリシクロデカンジメタノールジ(メタ)アクリレート、トリシクロデカニルジ(メタ)アクリレート、トリメチロールプロパントリオキシプロピル(メタ)アクリレート、トリス−2−ヒドロキシエチルイソシアヌレートトリ(メタ)アクリレート、トリス−2−ヒドロキシエチルイソシアヌレートジ(メタ)アクリレート、1,9−ノナンジオールジ(メタ)アクリレート、ペンタエリスリトールジ(メタ)アクリレート、グリセリンメタクリレートアクリレート、ペンタエリスリトールトリ(メタ)アクリレート、トリメチロールプロパントリメタクリレート、(メタ)アクリル酸アリル、(メタ)アクリル酸ビニル、エポキシ(メタ)アクリレート、ポリエステル(メタ)アクリレート、ウレタン(メタ)アクリレート等が挙げられる。
光ラジカル重合開始剤としては、例えば、アセトフェノン類、ベンゾフェノン類、ミヒラーのベンゾイルベンゾエート、アミロキシムエステル、テトラメチルチウラムモノサルファイドおよびチオキサントン類等が挙げられる。
マイクロレンズの形成方法の一形態としてマイクロレンズアレイの形成工程の一例について説明する。必要により、素子の表面の凹凸を、透明樹脂をスピンコートすることで埋め込み、平坦化しておく。平坦化した表面にレンズ材料を均一に塗布する。レンズ材料の上にレジストを均一に塗布する。ステッパ装置を用いて、レチクルをマスクとしてレジストに紫外線を照射し、レンズ間スペースの部分を露光する。感光した部分を現像液で分解除去しパターン形成する。半球状のパターンを加熱することで得る。このときレジストは溶融し液相となり、半球状態になった後、固相に変化する。その後、ドライエッチングによりレンズ材料の層をエッチングする。このようにして半球状のレンズが配列されたレンズアレイを形成することができる。
本発明の好ましい実施形態に係る固体撮像素子は、本発明のトリアジン樹脂組成物の硬化物からなるマイクロレンズを有する。固体撮像素子は、半導体受光素子上にマイクロレンズアレイを有し、マイクロレンズアレイとカラーフィルタが隣接するように組み込まれる。固体撮像素子は、受光素子を有する基板上に、基板側からカラーフィルタ、マイクロレンズを順に形成されて製造される。受光素子は、透明樹脂膜、レンズ、及びカラーフィルタの順に通過して到達する光を受光し、イメージセンサーとして機能する。具体的には、透明樹脂膜が反射防止膜として機能し、マイクロレンズの集光効率を向上させ、マイクロレンズによって効率的に集められた光がカラーフィルタを介して受光素子に検知される。これらがRGBそれぞれに対応する光を検知する受光素子の画素の全般に渡って機能する。そのため、受光素子の画素とマイクロレンズの個々のレンズとが高密度に配列されている場合でも、極めて鮮明な画像を得ることができる。上記のレンズやRGBの画素配列に介在させる透明画素として本発明のトリアジン樹脂組成物の硬化物を好適に利用することができる。
以下に略号を示す。
NMP:N−メチルピロリドン
TAPOB:1,3,5−トリス(4−アミノフェノキシ)ベンゼン
TADE:5−(4−アミノフェノキシ)ベンゼン−1,3−ジアミン
3,3’−DDS:3,3’−ジアミノジフェニルスルホン
TABA: 3,5−ジアミノ−N−(4−アミノフェニル)ベンズアミド)
TCT:シアヌル酸クロリド
DMSO:ジメチルスルホキシド
MDM:ジエチレングリコールジメチルエーテル。
GPC装置 HLC−8220GPC(東ソー(株)製)を用い、テトラヒドロフラン溶液にて、ポリスチレン換算の分子量を測定した。
500mL四口フラスコに、Z1の成分としてm−アニシジン(12.24g、99.41mmol、東京化成工業(株)製)、Z2の成分としてTAPOB(13.24g、33mmol、セイカ(株)製)、トリエチルアミン(22.01g、205.45mmol)を入れ、NMP(90g)に溶解して、オイルバスで40℃に加熱した。その後、トリアジン成分としてNMP49gに溶解したTCT(12.22g、66.28mmol、東京化成工業(株)製)の溶液を30分かけて滴下した。滴下終了から1時間拡拌した後、さらに130℃で1時間加熱し、室温まで冷却した。得られた反応溶液をろ過し、沈殿物を除去してろ液を回収した。ろ液を5%炭酸ナトリウム水溶液に滴下して生成物を再沈殿精製した。得られた沈殿物をろ過し、減圧乾燥機で120℃、6時間乾燥し、目的とするトリアジン重合体P−1を25.5g得た。GPC測定によるポリスチレン換算の分子量はMw=6800であった。
500mL四口フラスコに、Z1の成分としてm−アニシジン(14.69g、119.3mmol、東京化成工業(株)製)、Z2の成分としてTAPOB(10.59g、26.51mmol、セイカ(株)製)、トリエチルアミン(20.78g、205.45mmol)を入れ、NMP(90g)に溶解して、オイルバスで40℃に加熱した。その後、トリアジン成分としてNMP49gに溶解したTCT(12.22g、66.28mmol、東京化成工業(株)製)の溶液を30分かけて滴下した。滴下終了から1時間拡拌した後、さらに130℃で1時間加熱し、室温まで冷却した。得られた反応溶液をろ過し、沈殿物を除去してろ液を回収した。ろ液を5%炭酸ナトリウム水溶液に滴下して生成物を再沈殿精製した。得られた沈殿物をろ過し、減圧乾燥機で120℃、6時間乾燥し、目的とするトリアジン重合体P−2を23.2g得た。GPC測定によるポリスチレン換算の分子量はMw=1800であった。
500mL四口フラスコに、Z1の成分としてm−アニシジン(9.8g、79.53mmol、東京化成工業(株)製)、Z2の成分としてTAPOB(15.89g、39.77mmol、セイカ(株)製)、トリエチルアミン(20.78g、205.45mmol)を入れ、NMP(90g)に溶解して、オイルバスで40℃に加熱した。その後、トリアジン成分としてNMP49gに溶解したTCT(12.22g、66.28mmol、東京化成工業(株)製)の溶液を30分かけて滴下した。滴下終了から1時間拡拌した後、さらに130℃で1時間加熱し、室温まで冷却した。得られた反応溶液をろ過し、沈殿物を除去してろ液を回収した。ろ液を5%炭酸ナトリウム水溶液に滴下して生成物を再沈殿精製した。得られた沈殿物をろ過し、減圧乾燥機で120℃、6時間乾燥し、目的とするトリアジン重合体P−3を25.7g得た。GPC測定によるポリスチレン換算の分子量はMw=28200であった。
合成例1のTAPOB(13.33g、33mmol、セイカ(株)製)をTADE(7.13g、33mmol、セイカ(株)製)に変更した以外は同様の手法にてトリアジン重合体P−4(25.4g)を合成した。GPC測定によるポリスチレン換算の分子量はMw=4400であった。
合成例1のTAPOB(13.33g、33mmol、セイカ(株)製)をTABA(8.03g、33mmol、日本純良薬品(株)製)に変更した以外は同様の手法にてトリアジン重合体P−5(25.5g)を合成した。GPC測定によるポリスチレン換算の分子量はMw=5300であった。
500mL四口フラスコに、Z1の成分としてm−アニシジン(11.43g、92.79mmol、東京化成工業(株)製)、3,3’−DDS(13.17g、53.02mmol、セイカ(株)製)、トリエチルアミン(20.78g、205.45mmol)を入れ、NMP(90g)に溶解して、オイルバスで40℃に加熱した。その後、NMP49gに溶解したTCT(12.22g、66.28mmol、東京化成工業(株)製)の溶液を30分かけて滴下した。滴下終了から1時間拡拌した後、さらに130℃で1時間加熱し、室温まで冷却した。得られた反応溶液をろ過し、沈殿物を除去してろ液を回収した。ろ液を5%炭酸ナトリウム水溶液に滴下して生成物を再沈殿精製した。得られた沈殿物をろ過し、減圧乾燥機で120℃、6時間乾燥し、目的とするトリアジン重合体P−6を26.5g得た。GPC測定によるポリスチレン換算の分子量はMw=7100であった。
500mL四口フラスコに、Z1の成分として3−メチルチオアニリン(16.61g、119.3mmol、東京化成工業(株)製)、Z2の成分としてTAPOB(10.59g、26.5mmol、セイカ(株)製)を入れ、NMP(90g)に溶解して、オイルバスで40℃に加熱した。その後、トリアジン成分としてNMP49gに溶解したTCT(12.22g、66.28mmol、東京化成工業(株)製)の溶液を30分かけて滴下した。滴下終了から1時間拡拌した後、さらに130℃で1時間加熱し、室温まで冷却した。得られた反応溶液をろ過し、沈殿物を除去してろ液を回収した。ろ液を5%炭酸ナトリウム水溶液に滴下して生成物を再沈殿精製した。得られた沈殿物をろ過し、減圧乾燥機で120℃、6時間乾燥し、目的とするトリアジン重合体P−1を28g得た。GPC測定によるポリスチレン換算の分子量はMw=2100であった。
500mL四口フラスコに、Z1の成分として3−メチルチオアニリン(15.69g、112.68mmol、東京化成工業(株)製)、末端または側鎖のシリル基を有する成分としてアミノプロピルトリエトキシシラン(1.47g、6.6mmol、信越化学性)Z2の成分としてTAPOB(10.59g、26.5mmol、セイカ(株)製)を入れ、NMP(90g)に溶解して、オイルバスで40℃に加熱した。その後、トリアジン成分としてNMP49gに溶解したTCT(12.22g、66.28mmol、東京化成工業(株)製)の溶液を30分かけて滴下した。滴下終了から1時間拡拌した後、さらに130℃で1時間加熱し、室温まで冷却した。得られた反応溶液をろ過し、沈殿物を除去してろ液を回収した。ろ液を5%炭酸ナトリウム水溶液に滴下して生成物を再沈殿精製した。得られた沈殿物をろ過し、減圧乾燥機で120℃、6時間乾燥し、目的とするトリアジン重合体P−1を28g得た。GPC測定によるポリスチレン換算の分子量はMw=2300であった。
500mL四口フラスコに、Z1の成分として3−メチルチオアニリン(15.69g、112.68mmol、東京化成工業(株)製)、末端または側鎖のシリル基を有する成分としてm−アミノフェニルトリメトキシシラン(1.41g、6.6mmol、Gelest社製)Z2の成分としてTAPOB(10.59g、26.5mmol、セイカ(株)製)を入れ、NMP(90g)に溶解して、オイルバスで40℃に加熱した。その後、トリアジン成分としてNMP49gに溶解したTCT(12.22g、66.28mmol、東京化成工業(株)製)の溶液を30分かけて滴下した。滴下終了から1時間拡拌した後、さらに130℃で1時間加熱し、室温まで冷却した。得られた反応溶液をろ過し、沈殿物を除去してろ液を回収した。ろ液を5%炭酸ナトリウム水溶液に滴下して生成物を再沈殿精製した。得られた沈殿物をろ過し、減圧乾燥機で120℃、6時間乾燥し、目的とするトリアジン重合体P−1を28g得た。GPC測定によるポリスチレン換算の分子量はMw=2200であった。
合成例1で得られたトリアジン重合体P−1を5g、DMSOを4g、MDMを16g混合し、振とう撹拌した後0.45μm径のフィルタで濾過して組成物1を得た。得られた組成物に対し、下記の方法にて硬化膜作製、屈折率測定、透過率測定、高温高湿度試験、密着性試験を実施した。組成を表2に、評価結果を表3に示す。
シリコンウェハおよび5cm角のガラス基板(AGCテクノグラス(株)製、厚み0.5mm)上に実施例の組成物をスピナーによりキュア後の膜厚0.5μmとなるように塗布した。その後、ホットプレートで100℃5分間プリベークし、さらに熱風オーブン中230℃で60分間のベークを経て、試験基板を得た。膜厚はラムダエースSTM−602(商品名、大日本スクリーン製)を用いて、屈折率1.70で測定した。
シリコンウェハの試験基板について、ラムダエースSTM−602(商品名、大日本スクリーン製)を用いて、屈折率1.70でプリベーク膜および硬化膜の厚さを測定した。
シリコンウェハの試験基板について、メトリコン社製屈折率測定装置プリズムカプラPC−2000を用いて、23℃において、波長633nmにおける屈折率を測定した。
5cm角のガラスの試験基板について、紫外−可視分光光度計「UV−260」(島津製作所(株)製)を用いて、波長400〜800nmにおいて測定した。バックグラウンド測定として、ガラス基板のみの透過率を測定し、試験基板の透過率からガラス基板の透過率を差し引くことにより、組成物の透過率を算出した。測定した値について、400nmの値および450〜800nmの平均値を比較した。
小型加速試験機SH−222(エスペック(株)製)にて、試験基板を85℃85%下で200時間保持した後、屈折率測定、透過率測定を行った。
5cm角のガラスの試験基板について、IJIS「K5600−5−6(制定年月日1999年4月20日)」に準じて接着性を評価した。具体的には、硬化膜の表面に、カッターナイフでガラス板の素地に到達するように、直交する縦横11本ずつの平行な直線を1mm間隔で引いて、1mm×1mmのマス目を100個作製した。切られた硬化膜表面にセロハン粘着テープ(幅=18mm、粘着力=3.7N/10mm)を張り付け、消しゴム(JIS S6050合格品)で擦って密着させ、テープの一端を持ち、板に直角を保ち瞬間的に剥離した際のマス目の残存数を目視によって評価した。マス目の剥離面積により以下のように判定し、3以上を合格とした。
5:剥離面積=0%
4:剥離面積=<5%
3:剥離面積=5〜14%
2:剥離面積=15〜34%
1:剥離面積=35%〜64%
0:剥離面積=65%〜100%。
実施例1で用いたトリアジン重合体P−1をP−2に変更した以外は同様の手法により組成物2を得た。得られた組成物に対し、試験基板作製、膜厚測定、屈折率測定、透過率測定、高温高湿度試験、密着性試験を実施した。組成を表2に、評価結果を表3に示す。
実施例1で用いたトリアジン重合体P−1をP−3に変更した以外は同様の手法により組成物3を得た。得られた組成物に対し、試験基板作製、膜厚測定、屈折率測定、透過率測定、高温高湿度試験、密着性試験を実施した。組成を表2に、評価結果を表3に示す。
実施例1で用いたトリアジン重合体P−1をP−4に変更した以外は同様の手法により組成物4を得た。得られた組成物に対し、試験基板作製、膜厚測定、屈折率測定、透過率測定、高温高湿度試験、密着性試験を実施した。組成を表2に、評価結果を表3に示す。
実施例1で用いたトリアジン重合体P−1をP−5に変更した以外は同様の手法により組成物5を得た。得られた組成物に対し、試験基板作製、膜厚測定、屈折率測定、透過率測定、高温高湿度試験、密着性試験を実施した。組成を表2に、評価結果を表3に示す。
合成例3で得られたトリアジン重合体P−3を4.75g、MW−100LM(三和ケミカル製)を0.25g、DMSOを4g、MDMを16g混合し、振とう撹拌した後0.45μm径のフィルタで濾過して組成物1を得た。得られた組成物に対し、下記の方法にて試験基板作製、屈折率測定、透過率測定、高温高湿度試験、密着性試験を実施した。組成を表2に、評価結果を表3に示す。
合成例3で得られたトリアジン重合体P−3を4.75g、VG−3101L(プリンテック製)を0.25g、DMSOを4g、MDMを16g混合し、振とう撹拌した後0.45μm径のフィルタで濾過して組成物1を得た。得られた組成物に対し、下記の方法にて試験基板作製、屈折率測定、透過率測定、高温高湿度試験、密着性試験を実施した。組成を表2に、評価結果を表3に示す。
合成例3で得られたトリアジン重合体P−3を4.5g、MW−100LM(三和ケミカル製)を0.25g、VG−3101L(プリンテック製)を0.25g、DMSOを4g、MDMを16g混合し、振とう撹拌した後0.45μm径のフィルタで濾過して組成物1を得た。得られた組成物に対し、下記の方法にて試験基板作製、屈折率測定、透過率測定、高温高湿度試験、密着性試験を実施した。組成を表2に、評価結果を表3に示す。
実施例1で用いたトリアジン重合体P−1をP−7に変更した以外は同様の手法により組成物2を得た。得られた組成物に対し、試験基板作製、膜厚測定、屈折率測定、透過率測定、高温高湿度試験、密着性試験を実施した。組成を表2に、評価結果を表3に示す。
実施例1で用いたトリアジン重合体P−1をP−8に変更した以外は同様の手法により組成物2を得た。得られた組成物に対し、試験基板作製、膜厚測定、屈折率測定、透過率測定、高温高湿度試験、密着性試験を実施した。組成を表2に、評価結果を表3に示す。
実施例1で用いたトリアジン重合体P−1をP−9に変更した以外は同様の手法により組成物2を得た。得られた組成物に対し、試験基板作製、膜厚測定、屈折率測定、透過率測定、高温高湿度試験、密着性試験を実施した。組成を表2に、評価結果を表3に示す。
実施例1で用いたトリアジン重合体P−1をP−6に変更した以外は同様の手法により比較組成物1を得た。得られた組成物に対し、試験基板作製、膜厚測定、屈折率測定、透過率測定、高温高湿度試験、密着性試験を実施した。組成を表2に、評価結果を表3に示す。
実施例6で用いたトリアジン重合体P−3をP−6に変更した以外は同様の手法により比較組成物2を得た。得られた組成物に対し、試験基板作製、膜厚測定、屈折率測定、透過率測定、高温高湿度試験、密着性試験を実施した。組成を表2に、評価結果を表3に示す。
実施例7で用いたトリアジン重合体P−3をP−6に変更した以外は同様の手法により比較組成物3を得た。得られた組成物に対し、試験基板作製、膜厚測定、屈折率測定、透過率測定、高温高湿度試験、密着性試験を実施した。組成を表2に、評価結果を表3に示す。
実施例8で用いたトリアジン重合体P−3をP−6に変更した以外は同様の手法により比較組成物4を得た。得られた組成物に対し、試験基板作製、膜厚測定、屈折率測定、透過率測定、高温高湿度試験、密着性試験を実施した。組成を表2に、評価結果を表3に示す。
Claims (7)
- 下記式(1)で表される繰り返し単位構造を含むことを特徴とするトリアジン環含有重合体。
- 前記Z2が下記一般式(2)〜(10)で示される群から選ばれる少なくとも1種を表す請求項1記載のトリアジン環含有重合体。
- 請求項1〜4いずれかに記載のトリアジン環含有重合体を含む樹脂組成物。
- 請求項5に記載の樹脂組成物から得られる硬化膜。
- 請求項6に記載の硬化膜を含む固体撮像素子。
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- 2019-03-18 JP JP2019516269A patent/JP7205466B2/ja active Active
- 2019-03-18 WO PCT/JP2019/011083 patent/WO2019188475A1/ja active Application Filing
- 2019-03-18 KR KR1020207022759A patent/KR20200135941A/ko unknown
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Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
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JPH0222328A (ja) * | 1988-07-12 | 1990-01-25 | Central Glass Co Ltd | 窒化炭素およびその製造方法 |
WO2014136871A1 (ja) * | 2013-03-08 | 2014-09-12 | 日産化学工業株式会社 | 膜形成用組成物 |
WO2016035321A1 (ja) * | 2014-09-01 | 2016-03-10 | 国立大学法人 東京大学 | 共有結合性有機構造体を含む導電性ハイブリッド材料 |
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TW201942193A (zh) | 2019-11-01 |
WO2019188475A1 (ja) | 2019-10-03 |
JP7205466B2 (ja) | 2023-01-17 |
KR20200135941A (ko) | 2020-12-04 |
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