JP5204582B2 - アシル化されたシルセスキオキサンの製造方法 - Google Patents
アシル化されたシルセスキオキサンの製造方法 Download PDFInfo
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- JP5204582B2 JP5204582B2 JP2008208739A JP2008208739A JP5204582B2 JP 5204582 B2 JP5204582 B2 JP 5204582B2 JP 2008208739 A JP2008208739 A JP 2008208739A JP 2008208739 A JP2008208739 A JP 2008208739A JP 5204582 B2 JP5204582 B2 JP 5204582B2
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- JP
- Japan
- Prior art keywords
- silsesquioxane
- acylated
- group
- bis
- film
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
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- UUMAFLKWOXKEID-UHFFFAOYSA-N diphenyliodanium;dodecyl benzenesulfonate Chemical compound C=1C=CC=CC=1[I+]C1=CC=CC=C1.CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 UUMAFLKWOXKEID-UHFFFAOYSA-N 0.000 description 1
- OVAZMTZNAIEREQ-UHFFFAOYSA-M diphenyliodanium;pyrene-1-sulfonate Chemical compound C=1C=CC=CC=1[I+]C1=CC=CC=C1.C1=C2C(S(=O)(=O)[O-])=CC=C(C=C3)C2=C2C3=CC=CC2=C1 OVAZMTZNAIEREQ-UHFFFAOYSA-M 0.000 description 1
- SBQIJPBUMNWUKN-UHFFFAOYSA-M diphenyliodanium;trifluoromethanesulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)F.C=1C=CC=CC=1[I+]C1=CC=CC=C1 SBQIJPBUMNWUKN-UHFFFAOYSA-M 0.000 description 1
- ZZTCPWRAHWXWCH-UHFFFAOYSA-N diphenylmethanediamine Chemical compound C=1C=CC=CC=1C(N)(N)C1=CC=CC=C1 ZZTCPWRAHWXWCH-UHFFFAOYSA-N 0.000 description 1
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
- KGGOIDKBHYYNIC-UHFFFAOYSA-N ditert-butyl 4-[3,4-bis(tert-butylperoxycarbonyl)benzoyl]benzene-1,2-dicarboperoxoate Chemical compound C1=C(C(=O)OOC(C)(C)C)C(C(=O)OOC(C)(C)C)=CC=C1C(=O)C1=CC=C(C(=O)OOC(C)(C)C)C(C(=O)OOC(C)(C)C)=C1 KGGOIDKBHYYNIC-UHFFFAOYSA-N 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- BHXIWUJLHYHGSJ-UHFFFAOYSA-N ethyl 3-ethoxypropanoate Chemical compound CCOCCC(=O)OCC BHXIWUJLHYHGSJ-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000002438 flame photometric detection Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 125000003827 glycol group Chemical group 0.000 description 1
- 238000007756 gravure coating Methods 0.000 description 1
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 235000010299 hexamethylene tetramine Nutrition 0.000 description 1
- 239000004312 hexamethylene tetramine Substances 0.000 description 1
- 125000003651 hexanedioyl group Chemical group C(CCCCC(=O)*)(=O)* 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical class I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 239000002563 ionic surfactant Substances 0.000 description 1
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- GKQPCPXONLDCMU-CCEZHUSRSA-N lacidipine Chemical compound CCOC(=O)C1=C(C)NC(C)=C(C(=O)OCC)C1C1=CC=CC=C1\C=C\C(=O)OC(C)(C)C GKQPCPXONLDCMU-CCEZHUSRSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- BDJSOPWXYLFTNW-UHFFFAOYSA-N methyl 3-methoxypropanoate Chemical compound COCCC(=O)OC BDJSOPWXYLFTNW-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- QXLPXWSKPNOQLE-UHFFFAOYSA-N methylpentynol Chemical compound CCC(C)(O)C#C QXLPXWSKPNOQLE-UHFFFAOYSA-N 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- QOHMWDJIBGVPIF-UHFFFAOYSA-N n',n'-diethylpropane-1,3-diamine Chemical compound CCN(CC)CCCN QOHMWDJIBGVPIF-UHFFFAOYSA-N 0.000 description 1
- ZQJAONQEOXOVNR-UHFFFAOYSA-N n,n-di(nonyl)nonan-1-amine Chemical compound CCCCCCCCCN(CCCCCCCCC)CCCCCCCCC ZQJAONQEOXOVNR-UHFFFAOYSA-N 0.000 description 1
- COFKFSSWMQHKMD-UHFFFAOYSA-N n,n-didecyldecan-1-amine Chemical compound CCCCCCCCCCN(CCCCCCCCCC)CCCCCCCCCC COFKFSSWMQHKMD-UHFFFAOYSA-N 0.000 description 1
- DIAIBWNEUYXDNL-UHFFFAOYSA-N n,n-dihexylhexan-1-amine Chemical compound CCCCCCN(CCCCCC)CCCCCC DIAIBWNEUYXDNL-UHFFFAOYSA-N 0.000 description 1
- XTAZYLNFDRKIHJ-UHFFFAOYSA-N n,n-dioctyloctan-1-amine Chemical compound CCCCCCCCN(CCCCCCCC)CCCCCCCC XTAZYLNFDRKIHJ-UHFFFAOYSA-N 0.000 description 1
- OOHAUGDGCWURIT-UHFFFAOYSA-N n,n-dipentylpentan-1-amine Chemical compound CCCCCN(CCCCC)CCCCC OOHAUGDGCWURIT-UHFFFAOYSA-N 0.000 description 1
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 1
- DNYZBFWKVMKMRM-UHFFFAOYSA-N n-benzhydrylidenehydroxylamine Chemical compound C=1C=CC=CC=1C(=NO)C1=CC=CC=C1 DNYZBFWKVMKMRM-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- NJWMENBYMFZACG-UHFFFAOYSA-N n-heptylheptan-1-amine Chemical compound CCCCCCCNCCCCCCC NJWMENBYMFZACG-UHFFFAOYSA-N 0.000 description 1
- NTNWKDHZTDQSST-UHFFFAOYSA-N naphthalene-1,2-diamine Chemical compound C1=CC=CC2=C(N)C(N)=CC=C21 NTNWKDHZTDQSST-UHFFFAOYSA-N 0.000 description 1
- LABYRQOOPPZWDG-UHFFFAOYSA-M naphthalene-1-sulfonate;triphenylsulfanium Chemical compound C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1.C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 LABYRQOOPPZWDG-UHFFFAOYSA-M 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- FJDUDHYHRVPMJZ-UHFFFAOYSA-N nonan-1-amine Chemical compound CCCCCCCCCN FJDUDHYHRVPMJZ-UHFFFAOYSA-N 0.000 description 1
- 238000003199 nucleic acid amplification method Methods 0.000 description 1
- XNTUJOTWIMFEQS-UHFFFAOYSA-N octadecanoyl octadecaneperoxoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCCCCCCCCCC XNTUJOTWIMFEQS-UHFFFAOYSA-N 0.000 description 1
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 1
- SRSFOMHQIATOFV-UHFFFAOYSA-N octanoyl octaneperoxoate Chemical compound CCCCCCCC(=O)OOC(=O)CCCCCCC SRSFOMHQIATOFV-UHFFFAOYSA-N 0.000 description 1
- 239000003002 pH adjusting agent Substances 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
- LYKRPDCJKSXAHS-UHFFFAOYSA-N phenyl-(2,3,4,5-tetrahydroxyphenyl)methanone Chemical class OC1=C(O)C(O)=CC(C(=O)C=2C=CC=CC=2)=C1O LYKRPDCJKSXAHS-UHFFFAOYSA-N 0.000 description 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920002432 poly(vinyl methyl ether) polymer Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920000259 polyoxyethylene lauryl ether Polymers 0.000 description 1
- 229920002503 polyoxyethylene-polyoxypropylene Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- BWJUFXUULUEGMA-UHFFFAOYSA-N propan-2-yl propan-2-yloxycarbonyloxy carbonate Chemical compound CC(C)OC(=O)OOC(=O)OC(C)C BWJUFXUULUEGMA-UHFFFAOYSA-N 0.000 description 1
- YPVDWEHVCUBACK-UHFFFAOYSA-N propoxycarbonyloxy propyl carbonate Chemical compound CCCOC(=O)OOC(=O)OCCC YPVDWEHVCUBACK-UHFFFAOYSA-N 0.000 description 1
- 229940090181 propyl acetate Drugs 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229940079877 pyrogallol Drugs 0.000 description 1
- WVIICGIFSIBFOG-UHFFFAOYSA-N pyrylium Chemical class C1=CC=[O+]C=C1 WVIICGIFSIBFOG-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 1
- 229960001755 resorcinol Drugs 0.000 description 1
- 150000005619 secondary aliphatic amines Chemical class 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 125000005346 substituted cycloalkyl group Chemical group 0.000 description 1
- 229960002317 succinimide Drugs 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 150000003459 sulfonic acid esters Chemical class 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- OPQYOFWUFGEMRZ-UHFFFAOYSA-N tert-butyl 2,2-dimethylpropaneperoxoate Chemical compound CC(C)(C)OOC(=O)C(C)(C)C OPQYOFWUFGEMRZ-UHFFFAOYSA-N 0.000 description 1
- NMOALOSNPWTWRH-UHFFFAOYSA-N tert-butyl 7,7-dimethyloctaneperoxoate Chemical compound CC(C)(C)CCCCCC(=O)OOC(C)(C)C NMOALOSNPWTWRH-UHFFFAOYSA-N 0.000 description 1
- SWAXTRYEYUTSAP-UHFFFAOYSA-N tert-butyl ethaneperoxoate Chemical compound CC(=O)OOC(C)(C)C SWAXTRYEYUTSAP-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- DLSMLZRPNPCXGY-UHFFFAOYSA-N tert-butylperoxy 2-ethylhexyl carbonate Chemical compound CCCCC(CC)COC(=O)OOOC(C)(C)C DLSMLZRPNPCXGY-UHFFFAOYSA-N 0.000 description 1
- XTXFUQOLBKQKJU-UHFFFAOYSA-N tert-butylperoxy(trimethyl)silane Chemical compound CC(C)(C)OO[Si](C)(C)C XTXFUQOLBKQKJU-UHFFFAOYSA-N 0.000 description 1
- 150000003510 tertiary aliphatic amines Chemical class 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- 150000005622 tetraalkylammonium hydroxides Chemical class 0.000 description 1
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- SWZDQOUHBYYPJD-UHFFFAOYSA-N tridodecylamine Chemical compound CCCCCCCCCCCCN(CCCCCCCCCCCC)CCCCCCCCCCCC SWZDQOUHBYYPJD-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 150000004961 triphenylmethanes Chemical class 0.000 description 1
- LZTRCELOJRDYMQ-UHFFFAOYSA-N triphenylmethanol Chemical class C=1C=CC=CC=1C(C=1C=CC=CC=1)(O)C1=CC=CC=C1 LZTRCELOJRDYMQ-UHFFFAOYSA-N 0.000 description 1
- FAYMLNNRGCYLSR-UHFFFAOYSA-M triphenylsulfonium triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F.C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 FAYMLNNRGCYLSR-UHFFFAOYSA-M 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
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Description
すなわち、本発明は、ポリスチレン換算重量平均分子量が2000以下の分子量を有し、狭い範囲の分子量分布を有するシルセスキオキサン、特に好ましくはアルカリ可溶性シルセスキオキサンの製造方法を提供することを目的とするものである。
RSiX3 (1)
(式中、Rは、C1〜C5の脂肪族炭化水素基、シクロヘキシル基、C2〜C5のアルケニル基、又はアリール基を表し、Xは塩素、臭素又は沃素を表す。)
で表されるトリハロシランをアシル化して、アシル化されたトリハロシランを製造し、
(B)層間移動触媒を含有する有機溶媒層と水性溶媒層の二層状態を作り、前記有機溶媒層に前記アシル化されたトリハロシランを滴下し、有機溶媒層及び界面にて制御された反応を行う
ことにより製造されたポリスチレン換算重量平均分子量(Mw)が2000以下のアシル化されたシルセスキオキサン。
RSiX3 (1)
(式中、Rは、C1〜C5の脂肪族炭化水素基、シクロヘキシル基、C2〜C5のアルケニル基、又はアリール基を表し、Xは塩素、臭素又は沃素を表す。)
で表されるトリハロシランをアシル化剤によりアシル化して、アシル化されたトリハロシランを製造し、
(B)層間移動触媒を含有する有機溶媒層と水性溶媒層との二層状態を作り、前記有機溶媒層に前記アシル化されたトリハロシランを滴下し、有機溶媒層及び界面にて制御された反応を行うことを特徴とするアシル化されたシルセスキオキサンの製造方法。
RSiX3 (1)
(式中、Rは、C1〜C5の脂肪族炭化水素基、シクロヘキシル基、C2〜C5のアルケニル基、又はアリール基を表し、Xは塩素、臭素又は沃素を表す。)
で表されるトリハロシランをアシル化することを特徴とするアシル化されたトリハロシランの製造方法。
(A)一般式(1):
RSiX3 (1)
(式中、Rは、C1〜C5の脂肪族炭化水素基、シクロヘキシル基、C2〜C5のアルケニル基、又はアリール基を表し、Xは塩素、臭素又は沃素を表す。)
で表されるトリハロシランをアシル化して、アシル化されたトリハロシランを製造する工程。
(B)層間移動触媒を含有する有機溶媒層と水性溶媒層の二層状態を作り、前記有機溶媒層に前記(A)工程で得られたアシル化されたトリハロシランを滴下し、有機溶媒層及び界面にて制御された反応を行い、アシル化されたシルセスキオキサンを製造する工程。
R1SiX3 (4)
(式中、R1は、アシルC1〜C5の脂肪族炭化水素基、アシルシクロヘキシル基、アシルC2〜C5のアルケニル基、又はアシルアリール基を表す。)
−(R1SiO1.5)n− (5)
の繰り返し単位を有し、末端基(R2)は、水性溶媒として水のみが用いられれば、水酸基となり、水性溶媒にアルコール又はグリコールが用いられれば、該当するアルコール或いはグリコールのエーテルとなる。なお、アシル化の際にRの全てをアシル化する必要はなく、Rの一部が未反応で残っていてもよい。この場合には、得られたシルセスキオキサンは、R1とともに一部Rが存在する下記一般式(6)および(7)の繰り返し単位を有するアシル化シルセスキオキサンとなる。また、一般式(4)で表されるアシル化トリハロシランとともに一般式(1)で表されるトリハロシランを用いることによっても、下記一般式(6)および(7)の繰り返し単位を有するアシル化シルセスキオキサンが得られる。
−(R1SiO1.5)a− (6)
−(RSiO1.5)b− (7)
(式中、R及びR1は、上記で定義したものを表し、aは1以上の整数、bは0又は1以上の整数で、aとbの合計は15以下である。)
アシル化シルセスキオキサンをシリコンウエハ上に2μmの厚さとなるようにスピンコーティングし、その後100℃のホットプレート上で60秒加熱し溶剤を除去する。エリクソメーターで被膜の膜厚測定を行う。次に、この被膜を有するシリコンウエハを2.38%TMAH(水酸化テトラメチルアンモニウム)水溶液に10秒間浸漬した後の膜厚測定を行う。浸漬前との差を浸漬時間(秒)で除し、アルカリ溶解速度を算出する。
また、ネガ型感光性組成物には、必要に応じ界面活性剤が含有されてもよい。界面活性剤としては、ポジ型感光性組成物において例示されたと同様のものが使用できる。
こうして得られた架橋膜は、400℃以上の耐熱性を有し、また膜の光透過率は95%以上、比誘電率も3.3以下である。このため、アクリル系材料にはない光透過率、比誘電率特性を有しており、FPDなどの平坦化膜、低温ポリシリコン用層間絶縁膜あるいはICチップ用バッファーコート膜などとして好適に利用できる。
なお、以下の例では、測定に当たって、次の装置が用いられた。
GPC:SIL10AD(島津製作所製)
FT−IR:FTIR660plus(日本分光社製)
LC−MS:LCQ Adventage Max(サーモフィッシャー社製)
フェニルトリクロロシラン(PhSiCl3)0.1molを500ccのビーカーに仕込み、アセトクロライドを150g加え完全に相溶させた。次に1Lの三つ口フラスコに塩化アルミニウム(AlCl3)30gを投入し、次いでアセトクロライド200gを投入し、塩化アルミニウムを完全に溶解させた。溶解後三つ口フラスコを冷却し、溶液温度を10℃にした。10℃に冷却後、滴下ロートにて前記で作製されたフェニルトリクロロシランを含んだアセトクロライドを所定のスピードで滴下した。全量滴下後30分攪拌し反応を終了させた。ここで得られた反応溶液を、次のシルセスキオキサンの合成に用いた。
3Lの分液ロートに水1Lを仕込んだ。その後18−crown−6ether1.5gを酢酸エチル1Lに溶解させ、この溶液を分液ロートに仕込み、水の層と酢酸エチル層を二層に分離させた。上層に有機層、下層に水の層が来た。実施例1で合成したアシル化したモノマー及び過剰なアセトクロライド(塩化アセチル)の混合溶液全量を有機溶媒層に滴下した。滴下液は有機溶媒中を拡散し、反応が起こり、白色固体が界面に集まった。このようにして作成した白色粉末を回収するため、水の層を分取し、廃棄した。残った有機層と反応精製物に水を多量に加えアセトクロライドの分解でできた酸を洗浄した。洗浄を重ねると精製物は完全に酢酸エチルに溶解した。得られた溶液の酢酸エチルをエバポレーターにより完全に除去し、目的とするアシル化シルセスキオキサンが得られた。得られたアシル化シルセスキオキサンを以下の条件でGPC測定を行った。結果を図1に示す。Mn=550、Mw=650のシングルピークが観測された。
このシルセスキオキサンをスピンコートにてシリコンウエハに成膜し400℃で硬化させたところ、膜厚限界(400℃での膜厚限界)は4.0μmであった。
実施例1で合成したモノマーを用い、水の層をエタノールとの混合液にした以外は実施例2と同様にして合成を実施した。得られたものはGPC測定結果Mn=530、Mw=640であり、単一ピークであった。
また、FT−IR測定結果1600cm-1にアセチル基に起因するピーク、1140cm-1,1100cm-1にシルセスキオキサンのピークに関するSi−Oのピークが観測された。さらに2900cm-1にエトキシ基に起因するピークが観測された。
得られたアセチルシルセスキオキサンのアルカリ溶解速度(2.38%のTMAH水溶液を使用)は、2000Å/secであった。400℃での膜厚限界は4.1μmであった。
実施例2で得られたアシル化シルセスキオキサンをプロピレングリコールモノエチルエーテルアセテート(PGMEA)35wt%に調整し、4,4’−(1−(4−(1−(4−ヒドロキシフェニル)−1−メチルエチル)フェニル)エチリデン)ビスフェノールのジアゾナフトキノン1.5mol変性体をシルセスキオキサンに対して20wt%添加した。また界面活性剤として信越化学工業社製(KS−53)をアシル化シルセスキオキサンに対して0.2wt%加え感光性組成物を得た。
実施例3で得られたアシル化シルセスキオキサンをPGMEA35wt%に調整し、光塩基発生剤としてミドリ化学社製NCB−101を5wt%添加した。この感光性組成物を実施例4と同様に所定のスピードでスピンコートし、膜厚3μmに調整した。この膜をホットプレート上90℃でプリベークし、その後ニコン
FX−604(NA=0.1)のg,h線露光機で露光した。その後2.38%TMAHで現像した結果、3μmのL/Sパターン及びホールパターンが残渣等抜けていることを確認した。これを230℃で硬化した膜は、比誘電率3.2、400nmでの透過率97%であった。
3Lの三つ口フラスコに水1Lを投入し、容器温度を10℃に制御し実施例1で得られたモノマーを静かに滴下した。すぐに白色沈殿が生成した。全量投入後30分攪拌を続け、ろ過を実施し沈殿物を回収した。この沈殿物をPGMEA(プロピレングリコールモノメチルエーテルアセテート)に溶解し、GPCにて分子量を確認したところ、Mn=5,000,MW=27,000であった。ピークも高分子量から低分子量まで幅広く分布しており、種々の構造が混在したものである。これを用いて、参考例4と同様に感光性組成物を作成し、g,h線露光機で露光し、2.38%TMAHで現像してみたが全く現像できなかった。
Claims (2)
- (A)一般式(1):
RSiX3 (1)
(式中、Rは、C1〜C5の脂肪族炭化水素基、シクロヘキシル基、C2〜C5のアルケニル基、又はアリール基を表し、Xは塩素、臭素又は沃素を表す。)
で表されるトリハロシランをアシル化剤によりアシル化して、アシル化されたトリハロシランを製造し、
(B)層間移動触媒を含有する有機溶媒層と水性溶媒層との二層状態を作り、前記有機溶媒層に前記アシル化されたトリハロシランを滴下し、有機溶媒層及び界面にて制御された反応を行うことを特徴とするアシル化されたシルセスキオキサンの製造方法。 - 前記水性溶媒が、水あるいは水とアルコール及び/又はグリコールとの混合溶媒であることを特徴とする請求項1に記載のアシル化されたシルセスキオキサンの製造方法。
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