CN113574116B - Curable composition, cured product, and method for using curable composition - Google Patents
Curable composition, cured product, and method for using curable composition Download PDFInfo
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- CN113574116B CN113574116B CN202080023933.6A CN202080023933A CN113574116B CN 113574116 B CN113574116 B CN 113574116B CN 202080023933 A CN202080023933 A CN 202080023933A CN 113574116 B CN113574116 B CN 113574116B
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- 239000000203 mixture Substances 0.000 title claims abstract description 149
- 238000000034 method Methods 0.000 title claims abstract description 41
- 150000001875 compounds Chemical class 0.000 claims abstract description 88
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 64
- 229920000734 polysilsesquioxane polymer Polymers 0.000 claims abstract description 63
- 230000003287 optical effect Effects 0.000 claims abstract description 45
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 37
- 239000000463 material Substances 0.000 claims abstract description 34
- 239000000853 adhesive Substances 0.000 claims abstract description 23
- 230000001070 adhesive effect Effects 0.000 claims abstract description 23
- 125000003118 aryl group Chemical group 0.000 claims abstract description 14
- 239000003566 sealing material Substances 0.000 claims abstract description 11
- -1 silane compound Chemical class 0.000 claims description 66
- 239000006087 Silane Coupling Agent Substances 0.000 claims description 40
- 229910000077 silane Inorganic materials 0.000 claims description 33
- 239000002904 solvent Substances 0.000 claims description 27
- 239000007787 solid Substances 0.000 claims description 19
- 239000000126 substance Substances 0.000 claims description 16
- 125000001153 fluoro group Chemical group F* 0.000 claims description 8
- 229910052731 fluorine Inorganic materials 0.000 claims description 7
- 125000003107 substituted aryl group Chemical group 0.000 claims description 4
- 229920001296 polysiloxane Polymers 0.000 abstract description 55
- 125000001424 substituent group Chemical group 0.000 abstract description 23
- 239000000047 product Substances 0.000 description 52
- 150000004756 silanes Chemical class 0.000 description 22
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 16
- 229910052710 silicon Inorganic materials 0.000 description 15
- 238000001723 curing Methods 0.000 description 13
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- 150000008065 acid anhydrides Chemical group 0.000 description 12
- 238000010438 heat treatment Methods 0.000 description 12
- 238000004519 manufacturing process Methods 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- 239000003054 catalyst Substances 0.000 description 11
- 230000000052 comparative effect Effects 0.000 description 11
- 229910052757 nitrogen Inorganic materials 0.000 description 11
- 125000004433 nitrogen atom Chemical group N* 0.000 description 11
- 125000003545 alkoxy group Chemical group 0.000 description 10
- 239000003963 antioxidant agent Substances 0.000 description 10
- 238000005259 measurement Methods 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- 238000005481 NMR spectroscopy Methods 0.000 description 9
- 229910052751 metal Inorganic materials 0.000 description 9
- 239000002184 metal Substances 0.000 description 9
- 238000006068 polycondensation reaction Methods 0.000 description 9
- 125000006239 protecting group Chemical group 0.000 description 9
- LIVNPJMFVYWSIS-UHFFFAOYSA-N silicon monoxide Inorganic materials [Si-]#[O+] LIVNPJMFVYWSIS-UHFFFAOYSA-N 0.000 description 9
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 9
- 239000003377 acid catalyst Substances 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 125000005843 halogen group Chemical group 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 238000010899 nucleation Methods 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 5
- 230000003078 antioxidant effect Effects 0.000 description 5
- 239000004202 carbamide Substances 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 239000010419 fine particle Substances 0.000 description 5
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical group OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 5
- 239000004611 light stabiliser Substances 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
- CPUDPFPXCZDNGI-UHFFFAOYSA-N triethoxy(methyl)silane Chemical compound CCO[Si](C)(OCC)OCC CPUDPFPXCZDNGI-UHFFFAOYSA-N 0.000 description 5
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 239000004793 Polystyrene Substances 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 235000011114 ammonium hydroxide Nutrition 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- 238000009826 distribution Methods 0.000 description 4
- 238000005227 gel permeation chromatography Methods 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 238000002329 infrared spectrum Methods 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 239000000178 monomer Substances 0.000 description 4
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 4
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- 229920002223 polystyrene Polymers 0.000 description 4
- 229940090181 propyl acetate Drugs 0.000 description 4
- 239000000523 sample Substances 0.000 description 4
- 238000002834 transmittance Methods 0.000 description 4
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 4
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 4
- VXQBJTKSVGFQOL-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethyl acetate Chemical compound CCCCOCCOCCOC(C)=O VXQBJTKSVGFQOL-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- JDSQBDGCMUXRBM-UHFFFAOYSA-N 2-[2-(2-butoxypropoxy)propoxy]propan-1-ol Chemical compound CCCCOC(C)COC(C)COC(C)CO JDSQBDGCMUXRBM-UHFFFAOYSA-N 0.000 description 3
- ZADOWCXTUZWAKL-UHFFFAOYSA-N 3-(3-trimethoxysilylpropyl)oxolane-2,5-dione Chemical compound CO[Si](OC)(OC)CCCC1CC(=O)OC1=O ZADOWCXTUZWAKL-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- 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
- 150000008064 anhydrides Chemical class 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 125000001309 chloro group Chemical group Cl* 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
- 238000000465 moulding Methods 0.000 description 3
- 125000000962 organic group Chemical group 0.000 description 3
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- 239000011593 sulfur Substances 0.000 description 3
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 2
- AOBIOSPNXBMOAT-UHFFFAOYSA-N 2-[2-(oxiran-2-ylmethoxy)ethoxymethyl]oxirane Chemical compound C1OC1COCCOCC1CO1 AOBIOSPNXBMOAT-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- GXDMUOPCQNLBCZ-UHFFFAOYSA-N 3-(3-triethoxysilylpropyl)oxolane-2,5-dione Chemical compound CCO[Si](OCC)(OCC)CCCC1CC(=O)OC1=O GXDMUOPCQNLBCZ-UHFFFAOYSA-N 0.000 description 2
- OECTYKWYRCHAKR-UHFFFAOYSA-N 4-vinylcyclohexene dioxide Chemical compound C1OC1C1CC2OC2CC1 OECTYKWYRCHAKR-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 229910018557 Si O Inorganic materials 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 125000005370 alkoxysilyl group Chemical group 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 2
- 239000004327 boric acid Substances 0.000 description 2
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 2
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 2
- 239000002131 composite material Substances 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 238000013007 heat curing Methods 0.000 description 2
- 125000001841 imino group Chemical group [H]N=* 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 2
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 2
- 239000001095 magnesium carbonate Substances 0.000 description 2
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 229910000000 metal hydroxide Inorganic materials 0.000 description 2
- 150000004692 metal hydroxides Chemical class 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 229940098779 methanesulfonic acid Drugs 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 2
- 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 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229920003207 poly(ethylene-2,6-naphthalate) Polymers 0.000 description 2
- 239000011112 polyethylene naphthalate Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
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- 239000002994 raw material Substances 0.000 description 2
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- 239000004065 semiconductor Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
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- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
- 239000011877 solvent mixture Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- CVBWTNHDKVVFMI-LBPRGKRZSA-N (2s)-1-[4-[2-[6-amino-8-[(6-bromo-1,3-benzodioxol-5-yl)sulfanyl]purin-9-yl]ethyl]piperidin-1-yl]-2-hydroxypropan-1-one Chemical compound C1CN(C(=O)[C@@H](O)C)CCC1CCN1C2=NC=NC(N)=C2N=C1SC(C(=C1)Br)=CC2=C1OCO2 CVBWTNHDKVVFMI-LBPRGKRZSA-N 0.000 description 1
- GPNCKHDHHBOTBK-UHFFFAOYSA-N 2,2-dichloroethoxy(3,3,3-trifluoropropyl)silane Chemical compound FC(CC[SiH2]OCC(Cl)Cl)(F)F GPNCKHDHHBOTBK-UHFFFAOYSA-N 0.000 description 1
- UXMYUFHUUYBDLL-UHFFFAOYSA-N 2,2-dimethyl-3-(oxiran-2-ylmethoxy)propan-1-ol Chemical compound OCC(C)(C)COCC1CO1 UXMYUFHUUYBDLL-UHFFFAOYSA-N 0.000 description 1
- 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 1
- IVIDDMGBRCPGLJ-UHFFFAOYSA-N 2,3-bis(oxiran-2-ylmethoxy)propan-1-ol Chemical compound C1OC1COC(CO)COCC1CO1 IVIDDMGBRCPGLJ-UHFFFAOYSA-N 0.000 description 1
- SYEWHONLFGZGLK-UHFFFAOYSA-N 2-[1,3-bis(oxiran-2-ylmethoxy)propan-2-yloxymethyl]oxirane Chemical compound C1OC1COCC(OCC1OC1)COCC1CO1 SYEWHONLFGZGLK-UHFFFAOYSA-N 0.000 description 1
- HPILSDOMLLYBQF-UHFFFAOYSA-N 2-[1-(oxiran-2-ylmethoxy)butoxymethyl]oxirane Chemical compound C1OC1COC(CCC)OCC1CO1 HPILSDOMLLYBQF-UHFFFAOYSA-N 0.000 description 1
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- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 239000002530 phenolic antioxidant Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 239000005054 phenyltrichlorosilane Substances 0.000 description 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920001707 polybutylene terephthalate Polymers 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920006393 polyether sulfone Polymers 0.000 description 1
- 229920002530 polyetherether ketone Polymers 0.000 description 1
- 229920001601 polyetherimide Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 229920000306 polymethylpentene Polymers 0.000 description 1
- 239000011116 polymethylpentene Substances 0.000 description 1
- 229920000069 polyphenylene sulfide Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000008213 purified water Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003870 salicylic acids Chemical class 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910052594 sapphire Inorganic materials 0.000 description 1
- 239000010980 sapphire Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- AIFMYMZGQVTROK-UHFFFAOYSA-N silicon tetrabromide Chemical compound Br[Si](Br)(Br)Br AIFMYMZGQVTROK-UHFFFAOYSA-N 0.000 description 1
- FDNAPBUWERUEDA-UHFFFAOYSA-N silicon tetrachloride Chemical compound Cl[Si](Cl)(Cl)Cl FDNAPBUWERUEDA-UHFFFAOYSA-N 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000005361 soda-lime glass Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- LVEOKSIILWWVEO-UHFFFAOYSA-N tetradecyl 3-(3-oxo-3-tetradecoxypropyl)sulfanylpropanoate Chemical compound CCCCCCCCCCCCCCOC(=O)CCSCCC(=O)OCCCCCCCCCCCCCC LVEOKSIILWWVEO-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
- 125000004192 tetrahydrofuran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000004187 tetrahydropyran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- LFQCEHFDDXELDD-UHFFFAOYSA-N tetramethyl orthosilicate Chemical compound CO[Si](OC)(OC)OC LFQCEHFDDXELDD-UHFFFAOYSA-N 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 238000001721 transfer moulding Methods 0.000 description 1
- KVENDAGPVNAYLY-UHFFFAOYSA-N tribromo(ethyl)silane Chemical compound CC[Si](Br)(Br)Br KVENDAGPVNAYLY-UHFFFAOYSA-N 0.000 description 1
- SELBPKHVKHQTIB-UHFFFAOYSA-N trichloro(ethoxy)silane Chemical compound CCO[Si](Cl)(Cl)Cl SELBPKHVKHQTIB-UHFFFAOYSA-N 0.000 description 1
- ZOYFEXPFPVDYIS-UHFFFAOYSA-N trichloro(ethyl)silane Chemical compound CC[Si](Cl)(Cl)Cl ZOYFEXPFPVDYIS-UHFFFAOYSA-N 0.000 description 1
- IORQPMCLCHBYMP-UHFFFAOYSA-N trichloro(methoxy)silane Chemical compound CO[Si](Cl)(Cl)Cl IORQPMCLCHBYMP-UHFFFAOYSA-N 0.000 description 1
- ORVMIVQULIKXCP-UHFFFAOYSA-N trichloro(phenyl)silane Chemical compound Cl[Si](Cl)(Cl)C1=CC=CC=C1 ORVMIVQULIKXCP-UHFFFAOYSA-N 0.000 description 1
- NNWMTCDMYFZDHA-UHFFFAOYSA-N trichloro-(4-methoxyphenyl)silane Chemical compound COC1=CC=C([Si](Cl)(Cl)Cl)C=C1 NNWMTCDMYFZDHA-UHFFFAOYSA-N 0.000 description 1
- ZLGWXNBXAXOQBG-UHFFFAOYSA-N triethoxy(3,3,3-trifluoropropyl)silane Chemical compound CCO[Si](OCC)(OCC)CCC(F)(F)F ZLGWXNBXAXOQBG-UHFFFAOYSA-N 0.000 description 1
- DENFJSAFJTVPJR-UHFFFAOYSA-N triethoxy(ethyl)silane Chemical compound CCO[Si](CC)(OCC)OCC DENFJSAFJTVPJR-UHFFFAOYSA-N 0.000 description 1
- QYBKVVRRGQSGDC-UHFFFAOYSA-N triethyl methyl silicate Chemical compound CCO[Si](OC)(OCC)OCC QYBKVVRRGQSGDC-UHFFFAOYSA-N 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- JLGNHOJUQFHYEZ-UHFFFAOYSA-N trimethoxy(3,3,3-trifluoropropyl)silane Chemical compound CO[Si](OC)(OC)CCC(F)(F)F JLGNHOJUQFHYEZ-UHFFFAOYSA-N 0.000 description 1
- ZNOCGWVLWPVKAO-UHFFFAOYSA-N trimethoxy(phenyl)silane Chemical compound CO[Si](OC)(OC)C1=CC=CC=C1 ZNOCGWVLWPVKAO-UHFFFAOYSA-N 0.000 description 1
- ZESWBFKRPIRQCD-UHFFFAOYSA-N trimethoxy-(4-methoxyphenyl)silane Chemical compound COC1=CC=C([Si](OC)(OC)OC)C=C1 ZESWBFKRPIRQCD-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/54—Silicon-containing compounds
- C08K5/541—Silicon-containing compounds containing oxygen
- C08K5/5415—Silicon-containing compounds containing oxygen containing at least one Si—O bond
- C08K5/5419—Silicon-containing compounds containing oxygen containing at least one Si—O bond containing at least one Si—C bond
-
- 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
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/22—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
- C08G77/24—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen halogen-containing groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/54—Silicon-containing compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
- C08L83/04—Polysiloxanes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
- C09J11/02—Non-macromolecular additives
- C09J11/06—Non-macromolecular additives organic
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J183/00—Adhesives based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Adhesives based on derivatives of such polymers
- C09J183/04—Polysiloxanes
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
- H01L21/04—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer
- H01L21/50—Assembly of semiconductor devices using processes or apparatus not provided for in a single one of the subgroups H01L21/06 - H01L21/326, e.g. sealing of a cap to a base of a container
- H01L21/56—Encapsulations, e.g. encapsulation layers, coatings
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L23/00—Details of semiconductor or other solid state devices
- H01L23/28—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection
- H01L23/29—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection characterised by the material, e.g. carbon
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L23/00—Details of semiconductor or other solid state devices
- H01L23/28—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection
- H01L23/31—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection characterised by the arrangement or shape
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- 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
- H01L33/52—Encapsulations
- H01L33/56—Materials, e.g. epoxy or silicone resin
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Organic Chemistry (AREA)
- Power Engineering (AREA)
- Computer Hardware Design (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Physics & Mathematics (AREA)
- Condensed Matter Physics & Semiconductors (AREA)
- General Physics & Mathematics (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Manufacturing & Machinery (AREA)
- Silicon Polymers (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Adhesives Or Adhesive Processes (AREA)
Abstract
The present invention relates to a curable composition containing the following component (a) and component (B), wherein the content of the component (B) is 1 to 110 parts by mass relative to 100 parts by mass of the component (a), a cured product obtained by curing the curable composition, and a method for using the curable composition as an adhesive for an optical element fixing material or a sealing material for an optical element fixing material. The curable composition of the present invention has good coatability. The refractive index of the cured product of the present invention is low. Component (A): a curable polysilsesquioxane compound having a repeating unit represented by the following formula (a-1) and a mass average molecular weight (Mw) of 4,000 to 20,000,
R 1 at least one selected from the group consisting of an unsubstituted alkyl group having 1 to 10 carbon atoms, an unsubstituted alkyl group having 1 to 10 carbon atoms and having a substituent, an unsubstituted aryl group having 6 to 12 carbon atoms and having a substituent; (B) component (A): a specific silicone oligomer having a repeating unit represented by the following formula (b-1),
Description
Technical Field
The present invention relates to: a curable composition having good coatability even when the curable component is concentrated to a high concentration; a cured product having a low refractive index obtained by curing the curable composition; and a method for using the curable composition as an adhesive for optical element-fixing materials or a sealing material for optical element-fixing materials.
Background
Conventionally, curable compositions have been improved variously depending on the application, and are widely used industrially as a raw material, an adhesive, a coating agent, and the like for optical components or molded articles.
The curable composition has also attracted attention as a composition for an optical element fixing material such as an adhesive for an optical element fixing material and a sealing material for an optical element fixing material.
Examples of the optical element include various laser light such as a semiconductor laser (LD, semiconductor laser), a light emitting element such as a Light Emitting Diode (LED), a light receiving element, a composite optical element, and an optical integrated circuit.
In recent years, optical elements that emit blue or white light having a peak wavelength of light emission of a shorter wavelength have been developed and widely used. The increase in luminance of the light-emitting element having a short peak wavelength of light emission has been dramatically progressed, and the amount of heat generated by the optical element tends to increase further.
However, with the recent increase in brightness of optical elements, there has been a problem that the adhesive strength of a cured product of the composition for an optical element-fixing material is reduced by exposure to light of higher energy or heat of higher temperature generated from the optical element for a long time.
In order to solve this problem, patent documents 1 to 3 propose: a composition for optical element fixing materials, which comprises a polysilsesquioxane compound as a main component.
However, when an optical element or the like is fixed using a curable composition, it is often important to form a cured product having a refractive index that meets a target. In particular, since many conventional curable compositions and cured products thereof have a high refractive index, a curable composition having a lower refractive index is required.
In addition, although a large amount of solvent is contained in a conventional curable composition to improve coatability, when such a curable composition is cured, if drying conditions or curing conditions are not strictly controlled, the solvent remains in the cured product, and there is a possibility that a cured product having desired characteristics cannot be formed.
Documents of the prior art
Patent document
Patent document 1: japanese patent laid-open publication No. 2004-359933;
patent document 2: japanese patent laid-open publication No. 2005-263869;
patent document 3: japanese patent laid-open No. 2006-328231.
Disclosure of Invention
Problems to be solved by the invention
The present invention has been made in view of the above-described actual situation of the conventional art, and an object thereof is to provide: a curable composition having good coatability even when the curable component is concentrated to a high concentration; a cured product having a low refractive index obtained by curing the curable composition; and a method for using the curable composition as an adhesive for optical element-fixing materials or a sealing material for optical element-fixing materials.
Means for solving the problems
In order to solve the above problems, the present inventors have made intensive studies on a curable composition containing a curable polysilsesquioxane compound.
As a result, the following were found: the present inventors have found that a curable composition containing a specific curable polysilsesquioxane compound and a specific silicone oligomer having a methyl group has good coatability even when the curable component is concentrated to a high concentration, and that a cured product having a low refractive index can be obtained by curing the curable composition, thereby completing the present invention.
Thus, the present invention provides the following curable compositions [1] to [8 ]; [9] (ii) a cured product of (1) or (10); and [11] and [12 ].
[1] A curable composition comprising the following component (A) and component (B), wherein the content of component (B) is 1 to 110 parts by mass per 100 parts by mass of component (A),
(A) The components: a curable polysilsesquioxane compound having a repeating unit represented by the following formula (a-1) and a mass average molecular weight (Mw) of 4,000 to 20,000,
[ chemical formula 1]
R 1 At least one selected from the group consisting of an unsubstituted alkyl group having 1 to 10 carbon atoms, an unsubstituted alkyl group having 1 to 10 carbon atoms and having a substituent, an unsubstituted aryl group having 6 to 12 carbon atoms and having a substituent;
(B) The components: an organosilicon oligomer having a repeating unit represented by the following formula (b-1) and satisfying the following requirements 1 to 3,
[ chemical formula 2]
[ element 1]
Contains 50mol% or more of a repeating unit derived from a 3-functional silane compound in the whole repeating units,
[ element 2]
The amount of the repeating unit represented by the formula (b-1) is 80mol% or more in the repeating unit derived from the 3-functional silane compound,
[ element 3]
The mass-average molecular weight (Mw) is 100 to 2,000.
[2] [1]The curable composition, wherein R in the formula (a-1) 1 To selectAt least one selected from an unsubstituted alkyl group having 1 to 10 carbon atoms and an alkyl group having 1 to 10 carbon atoms and having a fluorine atom.
[3] [1] or [2], wherein the amount of the repeating unit represented by the formula (a-1) in the component (A) is 50 to 100mol% based on the total repeating units in the component (A).
[4] The curable composition according to any one of [1] to [3], wherein the component (A) has a refractive index of 1.300 to 1.450.
[5] The curable composition according to any one of [1] to [4], wherein the component (B) has a refractive index of 1.300 to 1.450.
[6] [1] the curable composition according to any one of [1] to [5], wherein the total amount of the component (A) and the component (B) is 30 to 100% by mass in the solid content of the curable composition.
[7] The curable composition according to any one of [1] to [6], further comprising the following component (C),
(C) The components: a silane coupling agent.
[8] The curable composition according to any one of [1] to [7], further comprising a solvent, wherein the solid content concentration is 70% by mass or more and less than 100% by mass.
[9] A cured product obtained by curing the curable composition according to any one of the above [1] to [8 ].
[10] [9] the cured product of the optical element-fixing material.
[11] A method for using the curable composition according to any one of the above [1] to [8] as an adhesive for an optical element-fixing material.
[12] A method for using the curable composition according to any one of the above [1] to [8] as a sealing material for an optical element-fixing material.
Effects of the invention
According to the present invention, there can be provided: a curable composition having good coatability even when the curable component is concentrated to a high concentration; a cured product having a low refractive index obtained by curing the curable composition; and a method for using the curable composition as an adhesive for optical element-fixing materials or a sealing material for optical element-fixing materials.
Detailed Description
The invention is divided into the following: the methods of using 1) the curable composition, 2) the cured product, and 3) the curable composition will be described in detail.
1) Curable composition
The curable composition of the present invention contains the following components (a) and (B):
(A) The components: a curable polysilsesquioxane compound having a repeating unit represented by the formula (a-1) and having a mass average molecular weight (Mw) of 4,000 to 20,000;
(B) The components: and a silicone oligomer having a repeating unit represented by the formula (b-1) and satisfying the requirements 1 to 3.
In the present invention, the "curable polysilsesquioxane compound" refers to a polysilsesquioxane compound that becomes a cured product by itself when predetermined conditions such as heating are satisfied, or a polysilsesquioxane compound that functions as a curable component in a curable composition.
[ (A) component ]
The component (a) constituting the curable composition of the present invention is a curable polysilsesquioxane compound (hereinafter, sometimes referred to as "polysilsesquioxane compound (a)") having a repeating unit represented by the following formula (a-1) and a mass average molecular weight (Mw) of 4,000 to 20,000.
[ chemical formula 3]
In the formula (a-1), R 1 Is at least one selected from the group consisting of an unsubstituted alkyl group having 1 to 10 carbon atoms, an unsubstituted aryl group having 6 to 12 carbon atoms and a substituted aryl group having 6 to 12 carbon atoms.
R 1 The "unsubstituted alkyl group having 1 to 10 carbon atoms" preferably has 1 to 6 carbon atoms, more preferably 1 to 3 carbon atoms.
Examples of the "unsubstituted alkyl group having 1 to 10 carbon atoms" include: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, n-hexyl, n-octyl, n-nonyl, n-decyl, and the like.
R 1 The "alkyl group having 1 to 10 carbon atoms and having a substituent" preferably has 1 to 6 carbon atoms, more preferably 1 to 3 carbon atoms. The number of carbons refers to the number of carbons of the portion (alkyl portion) excluding the substituent. Thus, at R 1 In the case of "alkyl group having 1 to 10 carbon atoms with substituent(s)", R 1 May also exceed 10.
Examples of the "alkyl group having 1 to 10 carbon atoms and a substituent" include: the same contents as those shown as "unsubstituted alkyl group having 1 to 10 carbon atoms".
The number of atoms of the substituent (excluding the number of hydrogen atoms) as the "alkyl group having 1 to 10 carbon atoms as a substituent" is usually 1 to 30, preferably 1 to 20.
Examples of the substituent of the "alkyl group having 1 to 10 carbon atoms and having a substituent" include: a halogen atom such as a fluorine atom, a chlorine atom, a bromine atom, etc.; a cyano group; formula (II): groups represented by OG, and the like.
Here, G represents a protecting group for a hydroxyl group. The protecting group for a hydroxyl group is not particularly limited, and examples thereof include: known protecting groups are known as protecting groups for hydroxyl groups. Examples thereof include: a protecting group of an acyl system; silyl-based protecting groups such as trimethylsilyl, triethylsilyl, t-butyldimethylsilyl and t-butyldiphenylsilyl; acetal-based protecting groups such as methoxymethyl, methoxyethoxymethyl, 1-ethoxyethyl, tetrahydropyran-2-yl and tetrahydrofuran-2-yl; alkoxycarbonyl-based protecting groups such as tert-butoxycarbonyl; and ether-based protecting groups such as methyl, ethyl, tert-butyl, octyl, allyl, triphenylmethyl, benzyl, p-methoxybenzyl, fluorenyl, trityl, and benzhydryl.
R 1 The "unsubstituted aryl group having 6 to 12 carbon atoms" preferably has 6 carbon atoms.
Examples of the "unsubstituted aryl group having 6 to 12 carbon atoms" include: phenyl, 1-naphthyl, 2-naphthyl, and the like.
R 1 The "aryl group having 6 to 12 carbon atoms and having a substituent" preferably has 6 carbon atoms. The number of carbons refers to the number of carbons of a portion (aryl group portion) excluding the substituent. Thus, at R 1 In the case of "aryl group having 6 to 12 carbon atoms with substituent(s)", R 1 May also exceed 12 carbon atoms.
Examples of the "aryl group having 6 to 12 carbon atoms and having a substituent" include: the same contents as those shown as "unsubstituted aryl group having 6 to 12 carbon atoms".
The number of the substituents (excluding the number of hydrogen atoms) of the "aryl group having 6 to 12 carbon atoms as a substituent" is usually 1 to 30, preferably 1 to 20.
Examples of the substituent of the "aryl group having 6 to 12 carbon atoms and having a substituent" include: an alkyl group such as a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, an n-pentyl group, an n-hexyl group, an n-heptyl group, an n-octyl group, and an isooctyl group; a halogen atom such as a fluorine atom, a chlorine atom, a bromine atom, etc.; alkoxy groups such as methoxy and ethoxy.
Among these, as R 1 Preferably, the alkyl group is at least one selected from the group consisting of an unsubstituted alkyl group having 1 to 10 carbon atoms and an alkyl group having 1 to 10 carbon atoms and having a fluorine atom.
By using R 1 The polysilsesquioxane compound (A) which is an unsubstituted alkyl group having 1 to 10 carbon atoms can easily give a curable composition which is a cured product having more excellent heat resistance and adhesiveness.
In the present specification, the term "cured product having excellent adhesiveness" means "cured product having high adhesive strength".
By using R 1 The polysilsesquioxane compound (A) having a fluorine atom-containing alkyl group having 1 to 10 carbon atoms can easily give a curable composition or a cured product having a low refractive index.
Examples of the alkyl group having 1 to 10 carbon atoms and having a fluorine atom include: the composition formula is as follows: c m H (2m-n+1) F n The group (m is a whole number of 1 to 10)The number n is an integer of more than 1 and less than (2m + 1). ). Among these, 3,3,3-trifluoropropyl is preferred.
The repeating unit represented by the above formula (a-1) is a repeating unit represented by the following formula. In this specification, O 1/2 Indicates that the oxygen atom is common to the adjacent repeating units.
[ chemical formula 4]
The polysilsesquioxane compound (A) has, as shown in the formula (a-2), a group (R) in which 3 oxygen atoms are bonded to a silicon atom and 1 other group is bonded thereto, which is generally referred to as a T site (T site) 1 ) And forming a partial structure.
Examples of the T site contained in the polysilsesquioxane compound (a) include: t sites represented by the following formulae (a-3) to (a-5).
[ chemical formula 5]
In the formulae (a-3) to (a-5), R 1 The same meanings as described above. R 2 Represents a hydrogen atom or an alkyl group having 1 to 10 carbon atoms. As R 2 The alkyl group having 1 to 10 carbon atoms of (b) includes: methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, and the like. Plural R 2 May be the same or different from each other. In the above formulae (a-3) to (a-5), a silicon atom is bonded thereto.
The polysilsesquioxane compound (a) is soluble in various organic solvents as follows: ketone solvents such as acetone; aromatic hydrocarbon solvents such as benzene; sulfur-containing solvents such as dimethyl sulfoxide; ether solvents such as tetrahydrofuran; ester solvents such as ethyl acetate; halogen-containing solvents such as chloroform; and a mixed solvent comprising 2 or more of them, and the like, and therefore the polysilsesquioxane compound (A) can be measured using these solvents in a solution state 29 Si-NMR。
By measuring the polysilsesquioxane compound (A) in the state of a solution 29 Si-NMR was carried out to determine the content ratio of the T3 site represented by the above formula (a-3), the T2 site represented by the formula (a-4) and the T1 site represented by the formula (a-5).
From the viewpoint of curability, the polysilsesquioxane compound (a) used in the present invention preferably contains 10 to 50mol%, more preferably 15 to 35mol% of T2 sites. The polysilsesquioxane compound (a) used in the present invention preferably contains 50 to 90mol%, more preferably 60 to 85mol% of T3 sites, from the viewpoint of further improving the balance between molecular weight and curability.
The content ratio of the repeating unit represented by the formula (a-1) in the polysilsesquioxane compound (a) is preferably 50 to 100mol%, more preferably 70 to 100mol%, further preferably 90 to 100mol%, and particularly preferably 100mol% based on the total repeating units.
The polysilsesquioxane compound (A) may have 1R 1 The compound (homopolymer) of (2) or more R may be used 1 The compound (copolymer) of (1).
When the polysilsesquioxane compound (a) is a copolymer, the polysilsesquioxane compound (a) may be any of a random copolymer, a block copolymer, a graft copolymer, an alternating copolymer, and the like, but from the viewpoint of ease of production and the like, a random copolymer is preferred.
The polysilsesquioxane compound (a) may have any structure of a ladder structure, a double-layer structure, a cage structure, a partially split cage structure, a ring structure, and a random structure.
The polysilsesquioxane compound (A) has a mass average molecular weight (Mw) of 4,000 to 20,000, preferably 6,000 to 16,000, and more preferably 8,000 to 13,000. By using the polysilsesquioxane compound (a) having a mass average molecular weight (Mw) within the above range, a curable composition that provides a cured product having more excellent heat resistance and adhesiveness can be easily obtained.
The molecular weight distribution (Mw/Mn) of the polysilsesquioxane compound (A) is not particularly limited, but is usually 1.0 to 10.0, preferably 1.1 to 6.0. By using the polysilsesquioxane compound (a) having a molecular weight distribution (Mw/Mn) within the above range, a curable composition that provides a cured product having more excellent heat resistance and adhesiveness can be easily obtained.
The mass average molecular weight (Mw) and the number average molecular weight (Mn) are determined as standard polystyrene values based on Gel Permeation Chromatography (GPC) using Tetrahydrofuran (THF) as a solvent, for example.
The polysilsesquioxane compound (a) has a refractive index (nD) at 25 ℃ of preferably 1.300 to 1.450, more preferably 1.350 to 1.440, and still more preferably 1.400 to 1.435.
By setting the refractive index (nD) of the polysilsesquioxane compound (A) at 25 ℃ in the range of 1.300 to 1.450, a curable composition or a cured product having a low refractive index can be easily obtained.
The refractive index of the polysilsesquioxane compound (A) may be measured using a pen refractometer.
In the present invention, the polysilsesquioxane compound (a) may be used alone in 1 kind, or in combination with 2 or more kinds.
The method for producing the polysilsesquioxane compound (a) is not particularly limited. For example, the polysilsesquioxane compound (A) can be produced by polycondensing at least one silane compound (1) represented by the following formula (a-6),
[ chemical formula 6]
In the formula, R 1 The same meanings as described above are indicated. R 3 Represents an alkyl group having 1 to 10 carbon atoms, X 1 Represents a halogen atom, and p represents an integer of 0 to 3. Plural R 3 And a plurality of X 1 May be respectively the same as or different from each other.
As R 3 Examples of the alkyl group having 1 to 10 carbon atoms include: and as R 2 The same applies to the alkyl group having 1 to 10 carbon atoms.
As X 1 Examples of the halogen atom of (1) include: chlorine atom and bromine atom, etc.
Specific examples of the silane compound (1) include: alkyltrialkoxysilane compounds such as methyltrimethoxysilane, methyltriethoxysilane, ethyltrimethoxysilane, ethyltriethoxysilane, and ethyltripropoxysilane;
alkylhaloalkoxysilane compounds such as methylchlorodimethoxysilane, methylchlorodiethoxysilane, methyldichlormethoxysilane, methylbromodimethoxysilane, ethylchlorodimethoxysilane, ethylchlorodiethoxysilane, ethyldichloromethoxysilane and ethylbromodimethoxysilane;
alkyltrihalosilane compounds such as methyltrichlorosilane, methyltrtribromosilane, ethyltrichlorosilane, and ethyltribromosilane;
substituted alkyltrialkoxysilane compounds such as 3,3,3-trifluoropropyltrimethoxysilane, 3,3,3-trifluoropropyltriethoxysilane, 2-cyanoethyltrimethoxysilane and 2-cyanoethyltriethoxysilane;
substituted alkylhaloalkoxysilane compounds such as 3,3,3-trifluoropropylchlorodimethoxysilane, 3,3,3-trifluoropropylchlorodiethoxysilane, 3,3,3-trifluoropropyldichloromethoxysilane, 3,3,3-trifluoropropyldichloroethoxysilane, 2-cyanoethylchlorodimethoxysilane, 2-cyanoethylchlorodiethoxysilane, 2-cyanoethyldichloromethoxysilane and 2-cyanoethyldichloroethoxysilane;
substituted alkyltrihalosilane compounds such as 3, 3-trifluoropropyltrichlorosilane and 2-cyanoethyltrichlorosilane;
substituted or unsubstituted phenyltrialkoxysilane compounds such as phenyltrimethoxysilane and 4-methoxyphenyltrimethoxysilane;
phenyl haloalkoxysilane compounds having or not having a substituent such as phenylchlorodimethoxysilane, phenyldichloromethoxysilane, 4-methoxyphenylchlorodimethoxysilane, 4-methoxyphenyldichloromethoxysilane, etc.;
and phenyl trihalosilane compounds having a substituent or having no substituent, such as phenyltrichlorosilane and 4-methoxyphenyltrichlorosilane.
These silane compounds (1) may be used alone in 1 kind, or in combination with 2 or more kinds.
The method for polycondensing the silane compound (1) is not particularly limited. Examples thereof include: a method comprising adding a predetermined amount of a polycondensation catalyst to the silane compound (1) in a solvent or without a solvent and stirring at a predetermined temperature. More specifically, there may be mentioned: (a) A method in which a predetermined amount of an acid catalyst is added to the silane compound (1) and stirring is carried out at a predetermined temperature; (b) A method in which a predetermined amount of an alkali catalyst is added to the silane compound (1) and stirring is carried out at a predetermined temperature; (c) A method in which a predetermined amount of an acid catalyst is added to the silane compound (1), stirring is performed at a predetermined temperature, and then an excess amount of a base catalyst is added to make the reaction system basic, and stirring is performed at a predetermined temperature. Among these, the method (a) or (c) is preferable in terms of efficiently obtaining the objective polysilsesquioxane compound (a).
The polycondensation catalyst used may be any of an acid catalyst and a base catalyst. In addition, although 2 or more kinds of polycondensation catalysts can be used in combination, it is preferable to use at least an acid catalyst.
Examples of the acid catalyst include: inorganic acids such as phosphoric acid, hydrochloric acid, boric acid, sulfuric acid, and nitric acid; and organic acids such as citric acid, acetic acid, methanesulfonic acid, trifluoromethanesulfonic acid, benzenesulfonic acid, and p-toluenesulfonic acid. Among these, at least one selected from phosphoric acid, hydrochloric acid, boric acid, sulfuric acid, citric acid, acetic acid and methanesulfonic acid is preferable.
Examples of the base catalyst include: ammonia water; organic bases such as trimethylamine, triethylamine, lithium diisopropylamide, lithium bis (trimethylsilyl) amide, pyridine, 1, 8-diazabicyclo [5.4.0] -7-undecene, aniline, picoline, 1, 4-diazabicyclo [2.2.2] octane, and imidazole; organic hydroxides such as tetramethylammonium hydroxide and tetraethylammonium hydroxide; metal alkoxides such as sodium methoxide, sodium ethoxide, sodium tert-butoxide, and potassium tert-butoxide; metal hydrides such as sodium hydride and calcium hydride; metal hydroxides such as sodium hydroxide, potassium hydroxide, and calcium hydroxide; metal carbonates such as sodium carbonate, potassium carbonate, and magnesium carbonate; and metal hydrogen carbonates such as sodium hydrogen carbonate and potassium hydrogen carbonate.
The amount of the polycondensation catalyst used is usually in the range of 0.05 to 10mol%, preferably 0.1 to 5mol%, based on the total mole (mol) of the silane compound (1).
When a solvent is used for the polycondensation, the solvent to be used may be appropriately selected depending on the kind of the silane compound (1) and the like. Examples thereof include: water; aromatic hydrocarbons such as benzene, toluene, and xylene; esters such as methyl acetate, ethyl acetate, propyl acetate, butyl acetate, and methyl propionate; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, and cyclohexanone; alcohols such as methanol, ethanol, n-propanol, isopropanol, n-butanol, isobutanol, sec-butanol, and tert-butanol. These solvents may be used alone in 1 kind, or in combination of 2 or more kinds. In the case of the method (c), after the polycondensation reaction is carried out in an aqueous system in the presence of an acid catalyst, an organic solvent and an excess amount of an alkali catalyst (ammonia water or the like) are added to the reaction solution, and the polycondensation reaction is further carried out under an alkaline condition.
The amount of the solvent used is 0.1 liter or more and 10 liters or less, preferably 0.1 liter or more and 2 liters or less, relative to the total molar amount of 1mol of the silane compound (1).
The temperature at which the silane compound (1) is polycondensed is usually in the range of 0 ℃ to the boiling point of the solvent used, and preferably in the range of 20 ℃ to 100 ℃. If the reaction temperature is too low, the progress of the polycondensation reaction may become insufficient. On the other hand, when the reaction temperature is too high, it is difficult to suppress gelation. The reaction is usually completed within 30 minutes to 30 hours.
Depending on the kind of the monomer used, it may be difficult to increase the molecular weight. For example, R 1 Monomers being alkyl radicals having fluorine atoms with R 1 Monomers that are normal alkyl groups tend to be less reactive than monomers that are normal alkyl groups. In such a case, the polysilsesquioxane compound (a) having the target molecular weight can be easily obtained by reducing the amount of the catalyst and by allowing the reaction to proceed under mild conditions for a long period of time.
After the reaction is completed, the objective polysilsesquioxane compound (a) can be obtained by adding an aqueous alkaline solution such as sodium hydrogencarbonate to the reaction solution for neutralization in the case of using an acid catalyst, adding an acid such as hydrochloric acid to the reaction solution for neutralization in the case of using an alkaline catalyst, and removing the salt generated at this time by filtration, washing with water, or the like.
In the case of producing the polysilsesquioxane compound (A) by the above-mentioned method, OR of the silane compound (1) 3 Or X 1 In (4), the portion where dealcoholization or the like does not occur remains in the polysilsesquioxane compound (A). Accordingly, the polysilsesquioxane compound (A) contains, in addition to the repeating unit represented by the formula (a-3), repeating units represented by the formulae (a-4) and (a-5).
[ (B) component ]
The component (B) constituting the curable composition of the present invention is a silicone oligomer (hereinafter, sometimes referred to as "silicone oligomer (B)") having a repeating unit represented by the following formula (B-1) and satisfying the requirements 1 to 3.
[ chemical formula 7]
The silicone oligomer (B) has a repeating unit derived from a 3-functional silane compound.
The 3-functional silane compound is a compound having 1 silicon atom and 3 hydrolyzable groups bonded to the silicon atom. In the present specification, the hydrolyzable group means a group having a hydrolysis/polycondensation property such as an alkoxy group or a halogen atom.
Examples of the 3-functional silane compound include: a silane compound (1) represented by the formula (a-6) shown below as a raw material for producing the polysilsesquioxane compound (A).
The silicone oligomer (B) may or may not have a repeating unit derived from a 4-functional silane compound.
The 4-functional silane compound is a compound having 1 silicon atom and 4 hydrolyzable groups bonded to the silicon atom.
Examples of the 4-functional silane compound include: tetramethoxysilane, tetraethoxysilane, methoxytriethoxysilane, dimethoxydiethoxysilane, trimethoxyethoxysilane, trimethoxychlorosilane, triethoxychlorosilane, dimethoxydichlorosilane, diethoxydichlorosilane, methoxytrichlorosilane, ethoxytrichlorosilane, tetrachlorosilane, tetrabromosilane, and the like.
The amount of the repeating unit derived from the 3-functional silane compound contained in the silicone oligomer (B) is 50mol% or more, preferably 70 to 100mol%, more preferably 90 to 100mol% in all the repeating units.
The compatibility of the silicone oligomer (B) with the polysilsesquioxane compound (a) is improved by making the amount of repeating units derived from the 3-functional silane compound 50mol% or more in the total repeating units.
The amount of the repeating unit represented by the formula (B-1) in the organosilicon oligomer (B) is 80mol% or more, preferably 85 to 100mol%, more preferably 90 to 100mol% in the repeating units derived from the 3-functional silane compound.
When the amount of the repeating unit represented by the formula (b-1) is less than 80mol% in the repeating unit derived from the 3-functional silane compound, it is difficult to obtain a curable composition or a cured product having a low refractive index.
In the case where the organosilicon oligomer (B) contains a repeating unit derived from a 3-functional silane compound other than the repeating unit represented by the formula (B-1), examples of such a repeating unit include: a repeating unit represented by the following formula (b-2).
[ chemical formula 8]
In the formula (b-2), R 4 Is at least one selected from the group consisting of an unsubstituted alkyl group having 2 to 10 carbon atoms, an unsubstituted alkyl group having 1 to 10 carbon atoms, an unsubstituted aryl group having 6 to 12 carbon atoms and a substituted aryl group having 6 to 12 carbon atoms.
As R 4 Specific examples of (b) include: and as R 1 The same contents as those shown in the specific examples of (1).
The kind and content ratio of each repeating unit contained in the silicone oligomer (B) can be determined by the same method as the method described above as the method for determining the structure of the polysilsesquioxane compound (a) (based on the method described above) 29 Si-NMR measurement result).
The silicone oligomer (B) has a mass average molecular weight (Mw) of 100 to 2,000, preferably 200 to 1,800, more preferably 300 to 1,500, still more preferably 400 to 1,200, and particularly preferably 500 to 900. By using the silicone oligomer (B) having a mass average molecular weight (Mw) within the above range, a curable composition having more excellent curability can be easily obtained. Furthermore, a cured product of such a curable composition tends to have excellent adhesiveness.
In the present invention, "excellent curability" means a characteristic that a curable composition is cured in a short time.
The mass average molecular weight (Mw) can be determined as a standard polystyrene conversion value by Gel Permeation Chromatography (GPC) using Tetrahydrofuran (THF) as a solvent, for example.
The refractive index (nD) of the silicone oligomer (B) at 25 ℃ is preferably 1.300 to 1.450, more preferably 1.350 to 1.430, and still more preferably 1.380 to 1.410.
By setting the refractive index (nD) of the silicone oligomer (B) at 25 ℃ in the range of 1.300 to 1.450, a curable composition or cured product having a low refractive index can be easily obtained.
The refractive index of silicone oligomer (B) can be measured using a pen refractometer.
In the present invention, the silicone oligomer (B) may be used alone in 1 kind, or in combination with 2 or more kinds.
The method for producing the silicone oligomer (B) is not particularly limited. The objective silicone oligomer (B) can be produced by appropriately changing the reaction conditions and the like in the same method as described as the method for producing the polysilsesquioxane compound (a).
Further, as the silicone oligomer (B), a commercially available silicone oligomer can be used.
[ curable composition ]
The curable composition of the present invention contains a polysilsesquioxane compound (a) and an organosilicon oligomer (B).
The total amount of the polysilsesquioxane compound (a) and the silicone oligomer (B) is preferably 30 to 100 mass%, more preferably 40 to 95 mass%, even more preferably 50 to 90 mass%, and particularly preferably 55 to 85 mass% in the solid content of the curable composition.
In the present invention, the "solid component" means a component other than the solvent in the curable composition.
The content of the silicone oligomer (B) is 1 to 110 parts by mass, preferably 10 to 80 parts by mass, more preferably 20 to 60 parts by mass, and still more preferably 32 to 45 parts by mass, relative to 100 parts by mass of the polysilsesquioxane compound (a). If the content of the component (B) is too small, it becomes difficult to obtain a curable composition or a cured product having a low refractive index. On the other hand, if the content of the component (B) is too large, it is difficult to form a cured product having excellent adhesiveness.
The curable composition of the present invention may contain a silane coupling agent as the component (C). By using a curable composition containing a silane coupling agent, a cured product having more excellent adhesiveness can be easily formed.
The silane coupling agent is a silane compound having a silicon atom, a functional group, and a hydrolyzable group bonded to the silicon atom.
The functional group is a group reactive with other compounds (mainly organic compounds), and examples thereof include: a group having a nitrogen atom such as an amino group, a substituted amino group, an isocyanate group, or a group having an isocyanurate skeleton; acid anhydride group (acid anhydride structure); a vinyl group; an allyl group; an epoxy group; a (meth) acryloyl group; mercapto groups, and the like.
In the present invention, 1 kind of silane coupling agent may be used alone, or 2 or more kinds may be used in combination.
When the curable composition of the present invention contains a silane coupling agent, the content thereof is not particularly limited and may be appropriately determined according to the purpose.
The silane coupling agent is preferably a silane coupling agent having a nitrogen atom in the molecule or a silane coupling agent having an acid anhydride structure in the molecule.
A curable composition containing a silane coupling agent having a nitrogen atom in the molecule or a silane coupling agent having an acid anhydride structure in the molecule tends to provide a cured product having more excellent heat resistance and adhesiveness.
Examples of the silane coupling agent having a nitrogen atom in the molecule include: trialkoxysilane compounds represented by the following formula (c-1), dialkoxyalkylsilane compounds represented by the following formula (c-2), dialkoxyarylsilane compounds, and the like.
[ chemical formula 9]
In the above formula, R a Represents an alkoxy group having 1 to 6 carbon atoms such as a methoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group, an n-butoxy group, or a tert-butoxy group. Plural R a May be the same or different from each other.
R b An alkyl group having 1 to 6 carbon atoms such as methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, etc.; or an unsubstituted or substituted aryl group such as a phenyl group, 4-chlorophenyl group, 4-methylphenyl group, or 1-naphthyl group.
R c Represents an organic group having 1 to 10 carbon atoms and having a nitrogen atom. In addition, R c May be further bonded with groups containing other silicon atoms.
As R c Specific examples of the organic group having 1 to 10 carbon atoms include: n-2- (aminoethyl) -3-aminopropyl, N- (1, 3-dimethyl-butylene) aminopropyl, 3-ureidopropyl, N-phenyl-aminopropyl and the like.
In the compound represented by the above formula (c-1) or (c-2), R is c In the case of an organic group bonded to a group containing another silicon atom, examples of the compound include: with isocyanurialsA silane coupling agent having an acid ester skeleton (isocyanurate-based silane coupling agent) or a silane coupling agent having a urea skeleton (urea-based silane coupling agent).
Among these, as the silane coupling agent having a nitrogen atom in the molecule, an isocyanurate-based silane coupling agent and a urea-based silane coupling agent are preferable, and a silane coupling agent having 4 or more alkoxy groups bonded to a silicon atom in the molecule is more preferable, from the viewpoint of easily obtaining a cured product having more excellent adhesiveness.
The alkoxy group having 4 or more bonds to a silicon atom means that the total count of the alkoxy groups bonded to the same silicon atom and the alkoxy groups bonded to different silicon atoms is 4 or more.
Examples of the isocyanurate-based silane coupling agent having 4 or more alkoxy groups bonded to silicon atoms include: a compound represented by the following formula (c-3). Examples of the urea-based silane coupling agent having 4 or more alkoxy groups bonded to a silicon atom include: a compound represented by the following formula (c-4).
[ chemical formula 10]
In the formula, R a The same meanings as described above are indicated. t1 to t5 each independently represent an integer of 1 to 10, preferably an integer of 1 to 6, and particularly preferably 3.
Among these, as the silane coupling agent having a nitrogen atom in the molecule, 1,3, 5-N-tris (3-trimethoxysilylpropyl) isocyanurate, 1,3, 5-N-tris (3-triethoxysilylpropyl) isocyanurate (hereinafter, referred to as "isocyanurate compound"), N '-bis (3-trimethoxysilylpropyl) urea, N' -bis (3-triethoxysilylpropyl) urea (hereinafter, referred to as "urea compound") and a combination of the above-mentioned isocyanurate compound and urea compound are preferably used.
When the curable composition of the present invention contains a silane coupling agent having a nitrogen atom in the molecule, the content thereof is not particularly limited, and the amount thereof is the following amount: the composition is prepared by mixing the component (A) and a silane coupling agent having a nitrogen atom in the molecule in a mass ratio of the component (A) to the component (A) (component (A): silane coupling agent having nitrogen atom in the molecule ], preferably 100:0.1 to 100: 90. more preferably 100:0.3 to 100: 60. more preferably 100:1 to 100: 50. more preferably 100:3 to 100: 40. particularly preferably 100:5 to 100:35.
a cured product of the curable composition containing the component (a) and the silane coupling agent having a nitrogen atom in the molecule at such a ratio is more excellent in heat resistance and adhesiveness.
The silane coupling agent having an acid anhydride structure in a molecule is an organosilicon compound having both a group having an acid anhydride structure and a hydrolyzable group in one molecule. Specifically, there may be mentioned: a compound represented by the following formula (c-5).
[ chemical formula 11]
Wherein Q represents a group having an acid anhydride structure, R d R represents an alkyl group having 1 to 6 carbon atoms or a substituted or unsubstituted phenyl group e Represents an alkoxy group having 1 to 6 carbon atoms or a halogen atom, i and k represent an integer of 1 to 3, j represents an integer of 0 to 2, and i + j + k =4. When j is 2, R d May be the same or different from each other. When k is 2 or 3, a plurality of R e May be the same or different from each other. When i is 2 or 3, Q's may be the same or different from each other.
Examples of Q include: a group represented by the following formula, etc.:
[ chemical formula 12]
(in the formula, h represents an integer of 0 to 10), and a group represented by (Q1) is particularly preferable.
Examples of the silane coupling agent having an acid anhydride structure in the molecule include: tri (C1-C6) alkoxysilyl (C2-C8) alkylsuccinic anhydrides such as 2- (trimethoxysilyl) ethylsuccinic anhydride, 2- (triethoxysilyl) ethylsuccinic anhydride, 3- (trimethoxysilyl) propylsuccinic anhydride and 3- (triethoxysilyl) propylsuccinic anhydride;
di (C1-C6) alkoxymethylsilyl (C2-C8) alkylsuccinic anhydride such as 2- (dimethoxymethylsilyl) ethylsuccinic anhydride;
alkoxydimethylsilyl (having 2 to 8 carbon atoms) alkyl succinic anhydrides such as 2- (methoxydimethylsilyl) ethyl succinic anhydride and the like (having 1 to 6 carbon atoms);
trihalosilyl (having 2 to 8 carbon atoms) alkyl succinic anhydrides such as 2- (trichlorosilyl) ethyl succinic anhydride and 2- (tribromosilyl) ethyl succinic anhydride;
dihalomethylsilyl (having 2 to 8 carbon atoms) alkylsuccinic anhydrides such as 2- (dichloromethylsilyl) ethylsuccinic anhydride;
and halogenated dimethylsilyl (having 2 to 8 carbon atoms) alkyl succinic anhydrides such as 2- (chlorodimethylsilyl) ethyl succinic anhydride.
Among these, the silane coupling agent having an acid anhydride structure in the molecule is preferably a tri (carbon number 1 to 6) alkoxysilyl (carbon number 2 to 8) alkyl succinic anhydride, and particularly preferably 3- (trimethoxysilyl) propyl succinic anhydride or 3- (triethoxysilyl) propyl succinic anhydride.
When the curable composition of the present invention contains a silane coupling agent having an acid anhydride structure in the molecule, the content thereof is not particularly limited, and the amount thereof is the following amount: the silane coupling agent is prepared by mixing the component (A) and a silane coupling agent having an acid anhydride structure in the molecule in a mass ratio of the component (A) to the component (A) (component (A): silane coupling agent having an acid anhydride structure in the molecule ], it is preferably 100:0.1 to 100: 30. more preferably 100:0.3 to 100: 20. more preferably 100:0.5 to 100: 15. more preferably 100:1 to 100:10.
a cured product of the curable composition containing the component (a) and the silane coupling agent having an acid anhydride structure in the molecule at such a ratio is more excellent in adhesiveness.
The curable composition of the present invention may contain other components within a range not interfering with the object of the present invention.
Examples of other components include: fine particles, antioxidants, ultraviolet absorbers, light stabilizers, and the like.
When the fine particles are added, a curable composition having excellent workability in a coating step may be obtained. Examples of the material of the fine particles include: a metal; a metal acidified substance; minerals; metal carbonates such as calcium carbonate and magnesium carbonate; metal sulfates such as calcium sulfate and barium sulfate; metal hydroxides such as aluminum hydroxide; metal silicates such as aluminum silicate, calcium silicate, and magnesium silicate; inorganic components such as silica; silicone; organic components such as acrylic polymers.
Alternatively, the particles used may be particles whose surfaces have been modified.
These fine particles can be used alone in 1 kind, or in combination of 2 or more kinds. The content of the fine particles is not particularly limited, and is usually preferably 50% by mass or less, more preferably 40% by mass or less, and still more preferably 35% by mass or less with respect to the component (a).
The antioxidant is added to prevent oxidative deterioration during heating. Examples of the antioxidant include: phosphorus antioxidants, phenol antioxidants, sulfur antioxidants, and the like.
Examples of the phosphorus-based antioxidant include: phosphites, oxaphosphaphenanthrene oxides, and the like. Examples of the phenolic antioxidant include: monophenols, bisphenols, high molecular weight phenols and the like. Examples of the sulfur-based antioxidant include: dilauryl 3,3' -thiodipropionate, dimyristyl 3,3' -thiodipropionate, distearyl 3,3' -thiodipropionate, and the like.
These antioxidants may be used alone in 1 kind, or in combination of 2 or more. The content of the antioxidant is not particularly limited, and is usually 10% by mass or less based on the component (A).
The ultraviolet absorber is added for the purpose of improving the light resistance of the resulting cured product.
Examples of the ultraviolet absorber include: salicylic acids, benzophenones, benzotriazoles, hindered amines, and the like.
The ultraviolet absorber may be used alone in 1 kind, or in combination of 2 or more kinds. The content of the ultraviolet absorber is not particularly limited, and is usually 10% by mass or less relative to the component (a).
The light stabilizer is added for the purpose of improving the light resistance of the resulting cured product.
Examples of the light stabilizer include: poly [ {6- (1, 3, hindered amines such as (tetramethylbutyl) amino-1, 3, 5-triazine-2, 4-diyl } { (2, 6-tetramethyl-4-piperidine) imino } hexamethylene } { (2, 6-tetramethyl-4-piperidine) imino } ], and the like.
These light stabilizers may be used alone in 1 kind, or in combination of 2 or more kinds. The content of the light stabilizer is usually 20% by mass or less relative to the component (A).
The curable composition of the present invention may contain a solvent. The solvent is not particularly limited as long as it can dissolve or disperse the components of the curable composition of the present invention.
Examples of the solvent include: acetates such as diethylene glycol monobutyl ether acetate and 1, 6-hexanediol diacetate; tripropylene glycol n-butyl ether; diglycidyl ethers such as glycerol diglycidyl ether, butanediol diglycidyl ether, diglycidylaniline, neopentyl glycol glycidyl ether, cyclohexanedimethanol diglycidyl ether, alkylene diglycidyl ether, polyethylene glycol diglycidyl ether, and polypropylene glycol diglycidyl ether; triglycidyl ethers such as trimethylolpropane triglycidyl ether and glycerol triglycidyl ether; vinyl hexene oxides such as 4-vinylcyclohexene monooxide, vinylcyclohexene dioxide and methylated vinylcyclohexene dioxide, and the like.
The solvent can be used alone, or in combination of 2 or more.
When the curable composition of the present invention contains a solvent, the content thereof is the following amount: the solid content concentration is preferably 70% by mass or more and less than 100% by mass, more preferably 74 to 98% by mass, and still more preferably 78 to 95% by mass.
The curable composition of the present invention has good coatability even if the curable composition does not contain a large amount of a solvent (i.e., even if the solid content concentration is high) because the component (a) and the component (B) are used in combination.
When a curable composition having a high solid content concentration is used, even if the drying conditions or curing conditions of the coating film are not strictly controlled, the cured product contains almost no solvent, and thus a cured product having certain characteristics can be stably formed.
The curable composition of the present invention contains the component (B), and therefore has a low refractive index.
The refractive index (nD) of the curable composition of the present invention at 25 ℃ is usually less than 1.450, preferably 1.380 to 1.440, more preferably 1.400 to 1.435, and still more preferably 1.410 to 1.430.
The refractive index (nD) of the curable composition can be measured using a pen refractometer.
The curable composition of the present invention can be prepared, for example, by mixing the above-mentioned component (a) and component (B) and, if necessary, other components at a predetermined ratio and defoaming them.
The mixing method and the defoaming method are not particularly limited, and known methods can be used.
2) Cured product
The cured product of the present invention is obtained by curing the curable composition of the present invention.
Examples of the method for curing the curable composition of the present invention include: and (4) heating and curing. The heating temperature at the time of curing is usually 100 to 200 ℃ and the heating time is usually 10 minutes to 20 hours, preferably 30 minutes to 10 hours.
The cured product of the present invention is a cured product having excellent heat resistance and adhesiveness.
The cured product of the present invention has these properties, and can be confirmed, for example, as follows. That is, a predetermined amount of the curable composition of the present invention is applied to the mirror surface of a silicon chip, and the applied surface is placed on an adherend and subjected to pressure bonding and heat treatment to be cured. It is preheated to a prescribed temperature (e.g., 100 deg.C)) On the measuring table of the adhesion tester (bond tester) of (2), 30 seconds from the adherend 100μThe adhesive surface was stressed in the horizontal direction (shear direction) at the position of m height, and the adhesion between the test piece and the adherend was measured.
The adhesion of the cured product of the present invention is preferably 30N/4mm at 100 ℃ 2 Above, more preferably 35N/4mm 2 Above, more preferably 40N/4mm 2 The above.
In this specification, "4mm 2 "means" 2mm square ", that is, 2mm × 2mm (square with 2mm on one side).
The cured product of the present invention has a low refractive index. Therefore, the cured product of the present invention is preferably used as an adhesive layer or the like having a low refractive index.
The refractive index (nD) of the cured product of the present invention at 25 ℃ is usually less than 1.450, preferably 1.380 to 1.440, more preferably 1.400 to 1.435, and still more preferably 1.410 to 1.430.
The refractive index (nD) of the cured product can be measured by the method described in examples.
The cured product of the present invention is preferably used as an optical element-fixing material because of the above-described properties.
3) Method for using curable composition
The method of the present invention is a method of using the curable composition of the present invention as an adhesive for an optical element-fixing material or a sealing material for an optical element-fixing material.
Examples of the optical element include: light emitting elements such as LEDs and LDs, light receiving elements, composite optical elements, and optical integrated circuits.
< adhesive for optical element fixing Material >
The curable composition of the present invention can be suitably used as an adhesive for an optical element-fixing material.
Examples of the method for using the curable composition of the present invention as an adhesive for optical element-fixing materials include: the composition is applied to one or both adhesive surfaces of materials (optical element, substrate thereof, etc.) to be adhered, and then the materials are heated and fixed after being pressedAnd a method of strongly bonding materials to be bonded to each other. The amount of the curable composition of the present invention to be applied is not particularly limited, and may be an amount that can strongly bond materials to be bonded to each other by curing. Usually, the thickness of the coating film of the curable composition is set to 0.5 to 5μm is preferably 1 to 3μThe amount of m.
Examples of the substrate material for bonding the optical element include: glasses such as soda-lime glass and heat-resistant hard glass; a ceramic; sapphire; metals such as iron, copper, aluminum, gold, silver, platinum, chromium, titanium, and alloys of these metals, stainless steel (SUS 302, SUS304L, SUS309, and the like); and synthetic resins such as polyethylene terephthalate, polybutylene terephthalate, polyethylene naphthalate, ethylene-vinyl acetate copolymers, polystyrene, polycarbonate, polymethylpentene, polysulfone, polyetheretherketone, polyethersulfone, polyphenylene sulfide, polyetherimide, polyimide, polyamide, acrylic resins, norbornene resins, cycloolefin resins, and glass epoxy resins.
The heating temperature during the heat curing is usually 100 to 200 ℃ although it depends on the curable composition used, etc. The heating time is usually 10 minutes to 20 hours, preferably 30 minutes to 10 hours.
Sealing material for optical element fixing material
The curable composition of the present invention can be suitably used as a sealing material for an optical element-fixing material.
Examples of the method for using the curable composition of the present invention as a sealing material for an optical element-fixing material include: and a method for producing an optical element sealing body by molding the composition into a desired shape to obtain a molded body enclosing an optical element and then heating and curing the molded body.
The method for molding the curable composition of the present invention into a desired shape is not particularly limited, and a known molding method such as a general transfer molding method or a casting method can be used.
The heating temperature during the heat curing is usually 100 to 200 ℃ although it depends on the curable composition used, etc. The heating time is usually 10 minutes to 20 hours, preferably 30 minutes to 10 hours.
The obtained optical element sealing body is excellent in heat resistance and adhesiveness because the curable composition of the present invention is used.
Examples
The present invention will be described in more detail below with reference to examples. However, the present invention is not limited to the following examples.
(average molecular weight measurement)
The mass average molecular weight (Mw) and the number average molecular weight (Mn) of the curable polysilsesquioxane compound obtained in production example and the silicone oligomer of component B were measured as standard polystyrene conversion values using the following apparatus and conditions.
Device name: HLC-8220GPC, manufactured by Tosoh corporation;
column: a column obtained by connecting TSKgelGMHXL, TSKgelGMHXL and TSKgel2000HXL in this order;
solvent: tetrahydrofuran;
injection amount: 80μl；
Measuring temperature: 40 ℃;
flow rate: 1 ml/min;
a detector: a differential refractometer.
(measurement of IR Spectrum)
The IR Spectrum of the curable polysilsesquioxane compound obtained in production example was measured using a fourier transform infrared spectrophotometer (Spectrum 100, manufactured by PerkinElmer).
( 29 Si-NMR measurement)
To investigate the silane Compound Polymer [ (A) component and (B) component]The repeating units and the amounts thereof of (A) are carried out under the following conditions 29 Si-NMR measurement.
The device comprises the following steps: AV-500 manufactured by Bruker Biospin;
29 Si-NMR resonance frequency: 99.352MHz;
and (3) probe: 5mmφA solution probe;
measuring temperature: room temperature (25 ℃);
sample rotation speed: 20kHz;
the determination method comprises the following steps: an inverse gated decoupling method;
29 the flip angle of Si: 90 degrees;
29 si 90 ° pulse width: 8.0μs；
Repetition time: 5s;
cumulative number of times: 9200 times;
observation width: 30kHz.
( 29 Method for producing Si-NMR sample
To shorten the relaxing time, fe (acac) was added as a relaxing agent 3 And (4) carrying out measurement.
Silane compound polymer concentration: 30 mass%;
Fe(acac) 3 concentration: 0.7 mass%;
and (3) determination of a solvent: acetone;
internal standard: TMS.
(analysis of waveform processing)
For each peak of the spectrum after fourier transform, a chemical shift is obtained from the position of the peak top, and integrated.
Production example 1
71.37g (400 mmol) of methyltriethoxysilane was charged in a 300ml eggplant-shaped flask, and an aqueous solution prepared by dissolving 0.10g of 35 mass% hydrochloric acid (0.25 mol% based on methyltriethoxysilane) in 21.6ml of distilled water was added while stirring, and the whole was stirred at 30 ℃ for 2 hours, and then heated to 70 ℃ and stirred for 5 hours.
While the contents were stirred, 140g of propyl acetate and 0.12g of 28 mass% aqueous ammonia (0.5 mol% based on methyltriethoxysilane) were added thereto, and the mixture was stirred at 70 ℃ for 3 hours.
After the reaction solution was cooled to room temperature, purified water was added thereto to carry out liquid separation treatment, and this operation was repeated until the pH of the water layer reached 7. The organic layer was concentrated by an evaporator, and the concentrate was dried in vacuum, whereby 55.7g of the curable polysilsesquioxane compound (A1) was obtained. This compound had a mass average molecular weight (Mw) of 7,800 and a molecular weight distribution (Mw/Mn) of 4.52.
The IR spectrum data of the curable polysilsesquioxane compound (A1) is as follows.
Si-CH 3 ：1272cm -1 , 1409cm -1 , Si-O：1132cm -1 。
In addition, carry out 29 As a result of Si-NMR spectroscopic measurement, the ratio of the peak integral values of T1, T2 and T3 was 0:24:76.
the refractive index (nD) of the curable polysilsesquioxane compound (A1) at 25 ℃ was 1.427.
Production example 2
After 17.0g (77.7 mmol) of 3, 3-trifluoropropyltrimethoxysilane and 32.33 (181.3 mmol) of methyltriethoxysilane were charged in a 300ml egg plant-shaped flask, an aqueous solution prepared by dissolving 0.0675g of 35 mass% hydrochloric acid (HCl amount 0.65mmol, 0.25mol% based on the total amount of silane compounds) in 14.0g of distilled water was added thereto with stirring, and the whole was stirred at 30 ℃ for 2 hours, then heated to 70 ℃ and stirred for 20 hours.
While the contents were stirred, 0.0394g of 28 mass% aqueous ammonia (NH) was added thereto 3 In an amount of 0.65 mmol) and 46.1g of propyl acetate, the reaction solution was stirred at 70 ℃ for 40 minutes as it was so that the pH of the reaction solution was 6.9.
After the reaction solution was allowed to cool to room temperature, 50g of propyl acetate and 100g of water were added thereto to conduct a liquid separation treatment, thereby obtaining an organic layer containing a reaction product. Magnesium sulfate was added to the organic layer to carry out drying treatment. After magnesium sulfate was removed by filtration, the organic layer was concentrated by an evaporator, and then the obtained concentrate was dried in vacuum, whereby a curable polysilsesquioxane compound (A2) was obtained. The compound had a mass average molecular weight (Mw) of 5,500 and a molecular weight distribution of 3.40.
The IR spectrum data of the curable polysilsesquioxane compound (A2) is as follows.
Si-CH 3 ：1272cm -1 , 1409cm -1 , Si-O：1132cm -1 , C-F：1213cm -1 。
In addition, carry out 29 As a result of Si-NMR spectroscopic measurement, the ratio of peak integral values of T1, T2 and T3 was 2:27:71.
the refractive index (nD) of the curable polysilsesquioxane compound (A2) at 25 ℃ was 1.410.
In examples and comparative examples the compounds used are as follows.
(A component)
Curable polysilsesquioxane compound (A1) [ curable PSQ (A1) ]: the curable polysilsesquioxane compound obtained in production example 1;
curable polysilsesquioxane compound (A2) [ curable PSQ (A2) ]: the curable polysilsesquioxane compound obtained in production example 2.
(component B)
Silicone oligomer (B1): commercially available silicone oligomers
Seed Mass average molecular weight (Mw) 700
CH derived from repeating units of 3-functional silane compounds 3 -SiO 3/2 The proportion of (C) is 100mol%
Seeding refractive index (nD) 1.394 at 25 ℃;
silicone oligomer (B2): commercially available silicone oligomers
Seed Mass average molecular weight (Mw) 900
CH in repeating units derived from 3-functional silane compounds 3 -SiO 3/2 The proportion of (C) is 100mol%
Seeding refractive index (nD) at 25 ℃ of 1.397;
silicone oligomer (B3): commercially available silicone oligomers
Seed Mass average molecular weight (Mw) 1000
CH in repeating units derived from 3-functional silane compounds 3 -SiO 3/2 The proportion of (C) is 100mol%
Refractive index (nD) 1.407 at 25 ℃;
silicone oligomer (B4): commercially available silicone oligomers
Seed Mass average molecular weight (Mw) 1000
CH in repeating units derived from 3-functional silane compounds 3 -SiO 3/2 The proportion of (C) is 100mol%
Seeding refractive index (nD) at 25 ℃ of 1.403;
silicone oligomer (B5): commercially available silicone oligomers
Seed Mass average molecular weight (Mw) 1000
CH in repeating units derived from 3-functional silane compounds 3 -SiO 3/2 In a proportion of 48mol% (PhSiO) 3/2 Is 52 mol%)
Seeding refractive index (nD) at 25 ℃ 1.509;
silicone oligomer (B6): commercially available silicone oligomers
Seed Mass average molecular weight (Mw) 1200
CH derived from repeating units of 3-functional silane compounds 3 -SiO 3/2 Proportion of (3) by mol% (PhSiO) 3/2 Is 53 mol%)
Seeding refractive index (nD) at 25 ℃ 1.529;
silicone oligomer (B7): commercially available Silicone oligomers
Seed Mass average molecular weight (Mw) 1200
CH derived from repeating units of 3-functional silane compounds 3 -SiO 3/2 Proportion of (3) 34mol% (PhSiO) 3/2 Is 64 mol%)
Seeding refractive index (nD) at 25 ℃ 1.525.
(component C)
Silane coupling agent (C1): 1,3,5-N-tris [3- (trimethoxysilyl) propyl ] isocyanurate;
silane coupling agent (C2): 3- (trimethoxysilyl) propylsuccinic anhydride.
The curable compositions obtained in examples and comparative examples were used to carry out the following measurements and tests, respectively.
[ measurement of refractive index (curable composition) ]
The curable composition was discharged onto a horizontal surface, and the refractive index (nD) was measured by pressing the measuring surface of a PEN refractometer (manufactured by ATAGO, inc., PEN-RI) at 25 ℃.
[ measurement of refractive index (cured product) ]
A mold made of polytetrafluoroethylene was placed on the glass subjected to the mold release treatment, and a curable composition was poured into the mold, heated and defoamed, and then cured by heating at 170 ℃ for 2 hours to prepare a cured sheet having a thickness of about 1 mm. The flat surface of the cured sheet was pressed against a prism of an Abbe refractometer (DR-A1, manufactured by ATAGO Co., ltd.) in a standard environment, and a sodium D line (589 nm) was irradiated to the interface between the prism and the cured sheet to measure a refractive index (nD) at 25 ℃.
[ transmittance ]
The curable composition was poured into a mold having a length of 25mm and a width of 20mm to have a thickness of 1mm, and the resultant was heated at 140 ℃ for 6 hours to cure the composition, thereby obtaining a test piece. The transmittance (%) at a wavelength of 450nm was measured with a spectrophotometer (MPC-3100, shimadzu corporation) for the obtained test piece.
[ evaluation of adhesive Strength ]
A square having a length of 2mm on one side (area of 4 mm) 2 ) The curable compositions obtained in examples and comparative examples were applied to the mirror surface of the silicon chip of (1) to a thickness of about 2μm, the coated surface was placed on an adherend (silver-plated copper plate) and press-bonded. Thereafter, the resultant was heat-treated at 130 ℃ for 2 hours to cure it, thereby obtaining an adherend with a test piece. The adherend with the test piece was placed on a measuring table of an adhesion tester (series 4000, manufactured by Daisy Co.) heated to 100 ℃ in advance for 30 seconds, and then the adhesive was moved away from the adherend 100μm height position at speed 200μm/s stress was applied to the adhesive surface in the horizontal direction (shear direction), and the adhesion (N/4 mm) between the test piece and the adherend at 100 ℃ was measured 2 )。
In addition, the adhesive strength exceeds 50N/4mm 2 The same experiment was performed for 40 times in total, and the standard deviation was calculated based on the results, and the degree of deviation of the results was examined.
(example 1)
To 100 parts by mass of the curable polysilsesquioxane compound (A1), 10 parts by mass of the silicone oligomer (B1) was added, and diethylene glycol monobutyl ether acetate: tripropylene glycol n-butyl ether =40:60 The entire contents of the solvent mixture (mass ratio) were stirred to obtain a curable composition having a solid content concentration of 72.9 mass%. The refractive index (nD) of the composition was measured at 25 ℃ to find that it was 1.427.
(example 2)
A curable composition having a solid content concentration of 76.8 mass% was obtained in the same manner as in example 1, except that 35 parts by mass of the silicone oligomer (B1) was used in example 1. The refractive index (nD) of the composition was measured at 25 ℃ to find that it was 1.421.
(example 3)
A curable composition having a solid content concentration of 80.6 mass% was obtained in the same manner as in example 1, except that 70 parts by mass of the silicone oligomer (B1) was used in example 1. The refractive index (nD) of the composition was measured at 25 ℃ to find that it was 1.417.
(example 4)
A curable composition having a solid content concentration of 80.6 mass% was obtained in the same manner as in example 1, except that 70 parts by mass of the silicone oligomer (B2) was used instead of the silicone oligomer (B1) in example 1. The refractive index (nD) of the composition was measured at 25 ℃ and found to be 1.419.
(example 5)
A curable composition having a solid content concentration of 80.6 mass% was obtained in the same manner as in example 1, except that 70 parts by mass of the silicone oligomer (B3) was used instead of the silicone oligomer (B1) in example 1. The refractive index (nD) of the composition was measured at 25 ℃ and found to be 1.422.
(example 6)
A curable composition having a solid content concentration of 80.6 mass% was obtained in the same manner as in example 1, except that 70 parts by mass of the silicone oligomer (B4) was used instead of the silicone oligomer (B1) in example 1. The refractive index (nD) of the composition was measured at 25 ℃ to find that it was 1.420.
Comparative example 1
A curable composition having a solid content concentration of 80.6 mass% was obtained in the same manner as in example 1, except that 70 parts by mass of the silicone oligomer (B5) was used instead of the silicone oligomer (B1) in example 1. The refractive index (nD) of the composition was measured at 25 ℃ to find that it was 1.456.
Comparative example 2
A curable composition having a solid content concentration of 80.6 mass% was obtained in the same manner as in example 1, except that 70 parts by mass of the silicone oligomer (B6) was used instead of the silicone oligomer (B1) in example 1. The refractive index (nD) of the composition was measured at 25 ℃ and found to be 1.462.
Comparative example 3
A curable composition having a solid content concentration of 80.6 mass% was obtained in the same manner as in example 1, except that 70 parts by mass of the silicone oligomer (B7) was used instead of the silicone oligomer (B1) in example 1. The refractive index (nD) of the composition was measured at 25 ℃ to find that it was 1.461.
(example 7)
To 100 parts by mass of the curable polysilsesquioxane compound (A1), 10 parts by mass of the silicone oligomer (B1) was added, and diethylene glycol monobutyl ether acetate: tripropylene glycol n-butyl ether =40:60 (mass ratio) of the solvent mixture, and the whole was stirred. After the mixture was dispersed with a three-roll mill, 10 parts by mass of the silane coupling agent (C1) and 3 parts by mass of the silane coupling agent (C2) were added thereto, and the whole was sufficiently mixed and defoamed to obtain a curable composition.
(examples 8 to 19 and comparative examples 4 to 10)
A curable composition was obtained in the same manner as in example 1, except that the components in example 1 were changed to those shown in table 1.
Using the curable compositions obtained in examples and comparative examples, refractive index measurement, transmittance measurement, and adhesion strength evaluation of cured products were performed. The results are shown in table 2.
[ Table 1]
[ Table 2]
The following can be understood from the above examples and comparative examples.
The curable compositions of examples 1 to 6 have a low refractive index because they contain the component (B).
On the other hand, the curable compositions of comparative examples 1 to 3 have high refractive indices because they contain silicone oligomers which do not satisfy the requirement of the component (B).
The cured products obtained in examples 7 to 19 had a low refractive index and high light transmittance. Moreover, the adhesive has sufficient adhesive strength and has small variation.
On the other hand, the cured products obtained in comparative examples 4 to 10 did not satisfy both low refractive index and high adhesive strength. Therefore, at least one of these cured products has poor properties.
The curable compositions of examples 7 to 19 had good coatability, although the solid content concentration was as high as 74.9 to 86.1 mass%.
Claims (13)
1. A curable composition comprising the following component (A) and component (B), wherein the content of component (B) is 1 to 110 parts by mass per 100 parts by mass of component (A),
(A) The components: a curable polysilsesquioxane compound having a repeating unit represented by the following formula (a-1) and a mass average molecular weight (Mw) of 4,000 to 20,000,
[ chemical formula 1]
R 1 Is selected from the group consisting of an unsubstituted alkyl group having 1 to 10 carbon atoms and a substituentAt least one of an unsubstituted aryl group having 6 to 12 carbon atoms and a substituted aryl group having 6 to 12 carbon atoms;
(B) The components: an organosilicon oligomer having a repeating unit represented by the following formula (b-1) and satisfying the following requirements 1 to 3,
[ chemical formula 2]
[ element 1]
Contains 50mol% or more of the repeating units derived from the 3-functional silane compound in the total repeating units,
[ element 2]
The amount of the repeating unit represented by the formula (b-1) is 80mol% or more in the repeating unit derived from the 3-functional silane compound,
[ element 3]
The mass-average molecular weight (Mw) is 100 to 2,000.
2. The curable composition according to claim 1, wherein R in the formula (a-1) 1 Is at least one selected from the group consisting of an unsubstituted alkyl group having 1 to 10 carbon atoms and an alkyl group having 1 to 10 carbon atoms and having a fluorine atom.
3. The curable composition according to claim 1 or 2, wherein the amount of the repeating unit represented by the formula (a-1) in the component (A) is 50 to 100mol% based on the total repeating units in the component (A).
4. The curable composition according to claim 1 or 2, wherein the component (B) comprises 90 to 100mol% of the total repeating units of the repeating units derived from the 3-functional silane compound.
5. The curable composition according to claim 1 or 2, wherein the refractive index of the component (A) is 1.300 to 1.450.
6. The curable composition according to claim 1 or 2, wherein the refractive index of the component (B) is 1.300 to 1.450.
7. The curable composition according to claim 1 or 2, wherein the total amount of the component (A) and the component (B) in the solid content of the curable composition is 30 to 100% by mass.
8. The curable composition according to claim 1 or 2, further comprising the following component (C),
(C) The components: a silane coupling agent.
9. The curable composition according to claim 1 or 2, further comprising a solvent, wherein the solid content concentration is 70% by mass or more and less than 100% by mass.
10. A cured product obtained by curing the curable composition according to any one of claims 1 to 9.
11. The cured product according to claim 10, which is an optical element-fixing material.
12. A method for using the curable composition according to any one of claims 1 to 9 as an adhesive for an optical element-fixing material.
13. A method for using the curable composition according to any one of claims 1 to 9 as a sealing material for an optical element-fixing material.
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| JP2005263869A (en) | 2004-03-16 | 2005-09-29 | Nagase Chemtex Corp | Resin composition for sealing optical semiconductor |
| JP2006328231A (en) | 2005-05-26 | 2006-12-07 | Nagase Chemtex Corp | Resin composition for encapsulating optical element |
| DE102013217221A1 (en) | 2013-08-28 | 2015-03-05 | Wacker Chemie Ag | Crosslinkable compositions based on organosilicon compounds and molded articles produced therefrom |
| JP6625326B2 (en) | 2015-02-09 | 2019-12-25 | 住友化学株式会社 | Semiconductor light emitting device manufacturing method and semiconductor light emitting device |
| KR20180099736A (en) | 2015-12-21 | 2018-09-05 | 스미또모 가가꾸 가부시키가이샤 | Silicone resin composition and its use |
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| JPH02279779A (en) * | 1989-04-20 | 1990-11-15 | Showa Denko Kk | Coating composition |
| JPH04306274A (en) * | 1991-04-03 | 1992-10-29 | Toshiba Silicone Co Ltd | Surface-treating agent |
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| CN113574116A (en) | 2021-10-29 |
| JP7487175B2 (en) | 2024-05-20 |
| TW202043370A (en) | 2020-12-01 |
| KR20210145119A (en) | 2021-12-01 |
| TWI841716B (en) | 2024-05-11 |
| WO2020196704A1 (en) | 2020-10-01 |
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