JP6572769B2 - ネガ型感光性樹脂組成物、それを硬化させてなる硬化膜およびその製造方法ならびにそれを具備する光学デバイスおよび裏面照射型cmosイメージセンサ - Google Patents
ネガ型感光性樹脂組成物、それを硬化させてなる硬化膜およびその製造方法ならびにそれを具備する光学デバイスおよび裏面照射型cmosイメージセンサ Download PDFInfo
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- JP6572769B2 JP6572769B2 JP2015504792A JP2015504792A JP6572769B2 JP 6572769 B2 JP6572769 B2 JP 6572769B2 JP 2015504792 A JP2015504792 A JP 2015504792A JP 2015504792 A JP2015504792 A JP 2015504792A JP 6572769 B2 JP6572769 B2 JP 6572769B2
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- 125000001931 aliphatic group Chemical group 0.000 claims description 28
- 125000003118 aryl group Chemical group 0.000 claims description 18
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- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
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- 125000004430 oxygen atom Chemical group O* 0.000 claims description 14
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- 125000002252 acyl group Chemical group 0.000 claims description 12
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- 239000003999 initiator Substances 0.000 claims description 10
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- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 2
- 125000003368 amide group Chemical group 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
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- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 36
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- FMLYSTGQBVZCGN-UHFFFAOYSA-N oxosilicon(2+) oxygen(2-) titanium(4+) Chemical compound [O-2].[Ti+4].[Si+2]=O.[O-2].[O-2] FMLYSTGQBVZCGN-UHFFFAOYSA-N 0.000 description 11
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- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 10
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- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 6
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
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- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 5
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- 238000005192 partition Methods 0.000 description 5
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 5
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- XQUPVDVFXZDTLT-UHFFFAOYSA-N 1-[4-[[4-(2,5-dioxopyrrol-1-yl)phenyl]methyl]phenyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C(C=C1)=CC=C1CC1=CC=C(N2C(C=CC2=O)=O)C=C1 XQUPVDVFXZDTLT-UHFFFAOYSA-N 0.000 description 4
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- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 4
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- LFQCEHFDDXELDD-UHFFFAOYSA-N tetramethyl orthosilicate Chemical compound CO[Si](OC)(OC)OC LFQCEHFDDXELDD-UHFFFAOYSA-N 0.000 description 4
- ZSOVVFMGSCDMIF-UHFFFAOYSA-N trimethoxy(naphthalen-1-yl)silane Chemical compound C1=CC=C2C([Si](OC)(OC)OC)=CC=CC2=C1 ZSOVVFMGSCDMIF-UHFFFAOYSA-N 0.000 description 4
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- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/16—Coating processes; Apparatus therefor
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/16—Coating processes; Apparatus therefor
- G03F7/168—Finishing the coated layer, e.g. drying, baking, soaking
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/20—Exposure; Apparatus therefor
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/20—Exposure; Apparatus therefor
- G03F7/2002—Exposure; Apparatus therefor with visible light or UV light, through an original having an opaque pattern on a transparent support, e.g. film printing, projection printing; by reflection of visible or UV light from an original such as a printed image
- G03F7/2012—Exposure; Apparatus therefor with visible light or UV light, through an original having an opaque pattern on a transparent support, e.g. film printing, projection printing; by reflection of visible or UV light from an original such as a printed image using liquid photohardening compositions, e.g. for the production of reliefs such as flexographic plates or stamps
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/26—Processing photosensitive materials; Apparatus therefor
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L27/00—Devices consisting of a plurality of semiconductor or other solid-state components formed in or on a common substrate
- H01L27/14—Devices consisting of a plurality of semiconductor or other solid-state components formed in or on a common substrate including semiconductor components sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation and specially adapted either for the conversion of the energy of such radiation into electrical energy or for the control of electrical energy by such radiation
- H01L27/144—Devices controlled by radiation
- H01L27/146—Imager structures
- H01L27/14601—Structural or functional details thereof
- H01L27/14609—Pixel-elements with integrated switching, control, storage or amplification elements
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L27/00—Devices consisting of a plurality of semiconductor or other solid-state components formed in or on a common substrate
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- H01L27/144—Devices controlled by radiation
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- H01L27/14601—Structural or functional details thereof
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- H01L27/144—Devices controlled by radiation
- H01L27/146—Imager structures
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- H01L27/144—Devices controlled by radiation
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- H01L27/14685—Process for coatings or optical elements
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- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
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Description
以下の(a)〜(d)を含有するネガ型感光性樹脂組成物であって、
(a)金属化合物粒子
(b)ポリシロキサン化合物
(c)α,β−不飽和カルボン酸エステル構造を含む基を1つ以上有する化合物
(d)光重合開始剤
さらに(e)マレイミド基を有する化合物を含有することを特徴とするネガ型感光性組成物である。
(a)金属化合物粒子、
(b)ポリシロキサン化合物、
(c)α,β−不飽和カルボン酸エステル構造を含む基を1つ以上有する化合物、
(d)光重合開始剤
さらに(e)マレイミド基を有する化合物を含有することを特徴とするネガ型感光性組成物である。
R1としては、3−コハク酸無水物プロピル基、3−コハク酸無水物プロピル基、プロピオン酸基、3−マレイン酸プロピル基、3−フタル酸プロピル基、3−無水ナフタル酸プロピル基、3−(p−安息香酸)プロピル基、3−(m−安息香酸)プロピル基、3−(o−安息香酸)プロピル基、などが挙げられる。
なお、単結合とは、R15、R16またはR17が、結合基としては存在せず、R15、R16またはR17が、結合しうる位置に、Si原子が直接結合していることを示す。
R4としては、前述の一般式(1)におけるR2とに記載した基から選ばれる基を用いることができる。このとき、一般式(1)におけるR2と一般式(3)におけるR4とは、同じ基であってもよいし、異なる基であってもよい。
なお、単結合とは、R5が、結合基としては存在せず、R5が、結合しうる位置に、O原子が直接結合していることを示す(以降についても同様である)。また、「複数のR5」および「複数のR6」とあるのは、上記においてi+j=2である場合について示したものである(以降についても同様である)。
一般式(6)で表される化合物としては1−ナフチルアクリレート、1−ナフチルメタクリレート、2−ナフチルアクリレート、2−ナフチルメタクリレート、1,4−ナフチルジアクリレート、9,9-ビス [4-(2-アクリロイルオキシエトキシ)フェニル]フルオレン、1,4−エチレンオキシドジメタクリレートナフタレンが挙げられる。
化合物(7)で表される化合物としては、9,9−ビス[4−(2−アクリロイルオキシエトキシ)フェニル]フルオレン、9,9−ビス[4−(2−メタクリロイルオキシエトキシ)フェニル]フルオレン、9,9−ビス[4−(2−メタクリロイルオキシエトキシ)−3−メチルフェニル]フルオレン、9,9−ビス[4−(2−アクリロイルオキシエトキシ)−3、5−ジメチルフェニル]フルオレン、9,9−ビス[4−(2−メタクリロイルオキシエトキシ)−3、5−ジメチルフェニル]フルオレンが挙げられる。なお、一般式(7)では、2つあるフェニレン基にそれぞれ1つのR11が、記されているが、1つのフェニレン基に複数のR11が、結合していてもよい。
一般式(8)で表される化合物としてはノルボルネンモノアクリレート、ノルボルネンジアクリレート、ノルボルネンエチレンオキシドアクリレート、ノルボルネンオキシドジアクリレートが挙げられる。
一般式(9)で表される化合物としてはアダマンタンモノアクリレート、アダマンタンジアクリレート、アダマンタンエチレンオキシドアクリレート、アダマンタンエチレンオキシドジアクリレートが挙げられる。
一般式(10)で表される化合物としては、N−アクリロイルオキシエチルヘキサヒドロフタルイミドが挙げられる。
透過率=exp(−4πkt/λ)
なお、作製した硬化膜の膜厚が1μmからはずれた際には、以下の式にて計算できる。
膜厚が1μmあたりの透過率={(透過率/100)^ (1/t)}*100にて計算できる。
ただし、kは消衰係数、tは膜厚、λは測定波長、を表す。
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
DAA:ジアセトンアルコール
ポリシロキサン化合物の溶液の固形分濃度は、以下の方法により求めた。アルミカップにポリシロキサン化合物の溶液を1.5g秤取し、ホットプレートを用いて250℃で30分間加熱して液分を蒸発させた。加熱後のアルミカップに残った固形分を秤量して、ポリシロキサン化合物の溶液の固形分濃度を求めた。
300mlのナスフラスコにp−アミノ安息香酸を23.23g、PGMEAを209.05g仕込み、室温にて30分間撹拌してp−アミノ安息香酸を溶解させた。得られた溶液に、イソシアネートプロピルトリエトキシシランを46.53g、ジラウリン酸ジブチルスズを1.19g仕込み、70℃のオイルバスで1時間撹拌した。その後室温まで放冷し、析出した固体をガラスフィルターにて濾取、乾燥させ、カルボキシル基含有シラン化合物(A)を得た。収量は46.7gだった。
300mlのナスフラスコにp−ヒドロキシ安息香酸を23.39g、PGMEAを210.5g仕込み、室温にて30分間撹拌してp−ヒドロキシ安息香酸を溶解させた。得られた溶液に、イソシアネートプロピルトリエトキシシランを46.53g、ジラウリン酸ジブチルスズを1.19g仕込み、40℃のオイルバスで3時間撹拌した。その後室温まで放冷し、析出した固体をガラスフィルターにて濾取、乾燥させ、カルボキシル基含有シラン化合物(B)を得た。収量は42.4gだった。
500mlの三口フラスコに3−アクリロキシプロピルトリメトキシシランを7.03g(0.03mol)、カルボキシル基含有シラン化合物(A)を15.37g(0.04mol)、1−ナフチルトリメトキシシラン7.45g(0.03mol)、酸化チタン−酸化ケイ素複合粒子のメタノール分散液(20.6重量%)である“オプトレイク” (登録商標)TR−527(商品名、日揮触媒化成(株)製、数平均粒子径は15nm)を156g(オルガノシランが完全縮合した場合の重量(22.3g)100重量部に対して、粒子含有量150重量部)、DAAを83.84g仕込み、室温で撹拌しながら水5.4gにリン酸0.217gを溶かしたリン酸水溶液を10分間かけて添加した。なお前記数平均粒子径はダイナミック光散乱高度計DLS−8000(大塚電子(株)製)を用いて、動的光散乱法により測定した。
500mlの三口フラスコに3−アクリロキシプロピルトリメトキシシランを5.86g(0.025mol)、カルボキシル基含有シラン化合物(B)を19.26g(0.05mol)、1−ナフチルトリメトキシシラン6.21g(0.025mol)、酸化チタン粒子のプロピレングリコールモノメチルエーテルアセテート分散液(20.2重量%)(登録商標)NOD−7771GTB(商品名、ナガセケムテックス(株)製、数平均粒子径は25nm)を181.4g(オルガノシランが完全縮合した場合の重量(24.4g)100重量部に対して、粒子含有量150重量部)、DAAを89.12g仕込み、室温で撹拌しながら水5.4gにリン酸0.157gを溶かしたリン酸水溶液を10分間かけて添加した。その後、調製例1と同様に加熱撹拌して(a)金属化合物粒子として酸化チタン粒子が分散した(b)ポリシロキサン化合物の溶液を得た。得られた溶液の固形分濃度を35重量%になるようにDAAにて希釈した。なお、実施例での組成において、本調製例2にて得た溶液に含まれる(a)金属化合物粒子と(b)ポリシロキサン化合物とを総称して「PS−02」と記す。
500mlの三口フラスコにp−スチリルトリメトキシシラン5.61g(0.025mol)、カルボキシル基含有シラン化合物(B)を19.21g(0.05mol)、1−アントラセニルトリメトキシシラン7.45g(0.025mol)、酸化チタン−酸化ケイ素複合粒子のメタノール分散液(20.6重量%)である(登録商標)“オプトレイク”TR−550(商品名、日揮触媒化成(株)製、数平均粒子径は20nm)を175.7g(オルガノシランが完全縮合した場合の重量(24.1g)100重量部に対して、粒子含有量150重量部)、DAAを88.03g仕込み、室温で撹拌しながら水5.4gにリン酸0.155gを溶かしたリン酸水溶液を10分間かけて添加した。その後、調製例1と同様に加熱撹拌して(a)金属化合物粒子として酸化チタン−酸化ケイ素複合粒子が分散した(b)ポリシロキサン化合物の溶液を得た。得られた溶液の固形分濃度を35重量%になるようにDAAにて希釈した。なお、実施例での組成において、本調製例3にて得た溶液に含まれる(a)金属化合物粒子と(b)ポリシロキサン化合物とを総称して「PS−03」と記す。
500mlの三口フラスコにp−スチリルトリメトキシシラン11.22g(0.05mol)、3−トリメトキシシリルプロピルコハク酸を6.56g(0.025mol)、1−ナフチルシランを6.21g(0.025mol)、23.4%の酸化チタン分散液である“ナノユース”(登録商標)OZ−30M(酸化チタン粒子、日産化学工業(株)製、数平均粒子径は7nm)112.38g(オルガノシランが完全縮合した場合の重量(17.5g)100重量部に対して、粒子含有量150重量部)、DAAを64.63g仕込み、室温で撹拌しながら水5.85gにリン酸0.120gを溶かしたリン酸水溶液を10分間かけて添加した。その後、調製例1と同様に加熱撹拌して(a)金属化合物粒子として酸化チタン粒子が分散した(b)ポリシロキサン化合物の溶液を得た。得られた溶液の固形分濃度を35重量%になるようにDAAにて希釈した。なお、実施例での組成において、本調製例4にて得た溶液に含まれる(a)金属化合物粒子と(b)ポリシロキサン化合物とを総称して「PS−04」と記す。
500mlの三口フラスコにp−スチリルトリメトキシシラン11.22g(0.05mol)、3−トリメトキシシリルプロピルコハク酸を6.56g(0.025mol)、1−ナフチルシランを6.21g(0.025mol)、23.4%の酸化チタン分散液である“ナノユース”(登録商標)OZ−30M(酸化チタン粒子、日産化学工業(株)製、数平均粒子径は7nm)112.38g(オルガノシランが完全縮合した場合の重量(18.9g)100重量部に対して、粒子含有量150重量部)、DAAを64.63g仕込み、室温で撹拌しながら水5.85gにリン酸0.120gを溶かしたリン酸水溶液を10分間かけて添加した。その後、調製例1と同様に加熱撹拌して(a)金属化合物粒子として酸化チタン粒子が分散した(b)ポリシロキサン化合物の溶液を得た。得られた溶液の固形分濃度を35重量%になるようにDAAにて希釈した。なお、実施例での組成において、本調製例5にて得た溶液に含まれる(a)金属化合物粒子と(b)ポリシロキサン化合物とを総称して「PS−05」と記す。
3−メタクリロキシプロピリトリメトキシシラン13.02g(0.05モル)、3−トリメトキシシリルプロピルコハク酸を6.56g(0.025mol)、1−アントラセニルトリメトキシシランを7.45g(0.025mol)、20.6重量%の酸化チタン−酸化ケイ素複合粒子メタノール分散液である“オプトレイク” (登録商標)TR−550(商品名、日揮触媒化成(株)製、数平均粒子径は20nm)を149.86g(オルガノシランが完全縮合した場合の重量(20.6g)100重量部に対して、粒子含有量150重量部)、DAAを75.89g仕込み、室温で撹拌しながら水5.85gにリン酸0.135gを溶かしたリン酸水溶液を10分間かけて添加した。その後、調製例1と同様に加熱撹拌して(a)金属化合物粒子として酸化チタン−酸化ケイ素複合粒子が分散した(b)ポリシロキサン化合物の溶液を得た。得られた溶液の固形分濃度を35重量%になるようにDAAにて希釈した。なお、実施例での組成において、本調製例6にて得た溶液に含まれる(a)金属化合物粒子と(b)ポリシロキサン化合物とを総称して「PS−06」と記す。
500mlの三口フラスコにメチルトリメトキシシランを5.45g(0.04mol)、フェニルトリメトキシシランを9.9g(0.05mol)、3−トリメトキシシリルプロピルコハク酸を2.6g(0.01mol)、22.0重量%の酸化チタン−酸化ケイ素複合粒子メタノール分散液である“オプトレイク” (登録商標)TR−527(商品名、日揮触媒化成(株)製、数平均粒子径は20nm)を76.9g(オルガノシランが完全縮合した場合の重量(20.5g)100重量部に対して、粒子含有量150重量部)、DAAを40.7g仕込み、室温で撹拌しながら水5.6gにリン酸0.09gを溶かしたリン酸水溶液を10分間かけて添加した。その後、調製例1と同様に加熱撹拌して(a)金属化合物粒子として酸化チタン−酸化ケイ素複合粒子が分散した(b)ポリシロキサン化合物の溶液を得た。得られた溶液の固形分濃度を35重量%になるようにDAAにて希釈した。なお、実施例での組成において、本調製例7にて得た溶液に含まれる(a)金属化合物粒子と(b)ポリシロキサン化合物とを総称して「PS−07」と記す。
500mlの三口フラスコにメチルトリメトキシシランを5.45g(0.04mol)、3−トリメトキシシリルプロピルコハク酸を5.25g(0.02mol)、1−ナフチルトリメトキシシランを9.93g(0.04mol)、20.6重量%の酸化チタン−酸化ケイ素複合粒子メタノール分散液である“オプトレイク” (登録商標)TR−550(商品名、日揮触媒化成(株)製、数平均粒子径は20nm)を102.6g(オルガノシランが完全縮合した場合の重量(14.1g)100重量部に対して、粒子含有量150重量部)、DAAを52.3g仕込み、室温で撹拌しながら水5.76gにリン酸0.103g(仕込みモノマーに対して0.50重量%)を溶かしたリン酸水溶液を10分間かけて添加した。その後、調製例1と同様に加熱撹拌して(a)金属化合物粒子として酸化チタン−酸化ケイ素複合粒子が分散した(b)ポリシロキサン化合物の溶液を得た。得られた溶液の固形分濃度を35重量%になるようにDAAにて希釈した。なお、実施例での組成において、本調製例8にて得た溶液に含まれる(a)金属化合物粒子と(b)ポリシロキサン化合物とを総称して「PS−08」と記す。
500mlの三口フラスコに3−アクリロキシプロピルトリメトキシシランを5.86g(0.025mol)、カルボキシル基含有シラン化合物(B)を19.26g(0.05mol)、フェニルトリメトキシシラン4.96g(0.025g)、酸化チタン粒子のプロピレングリコールモノメチルエーテルアセテート分散液(20.2重量%)(登録商標)NOD−7771GTB(商品名、ナガセケムテックス(株)製、数平均粒子径は25nm)を172.1g(オルガノシランが完全縮合した場合の重量(23.2g)100重量部に対して、粒子含有量150重量部)、DAAを89.12g仕込み、室温で撹拌しながら水5.4gにリン酸0.157gを溶かしたリン酸水溶液を10分間かけて添加した。その後、調製例1と同様に加熱撹拌して(a)金属化合物粒子として酸化チタン粒子が分散した(b)ポリシロキサン化合物の溶液を得た。得られた溶液の固形分濃度を35重量%になるようにDAAにて希釈した。なお、実施例での組成において、本調製例10にて得た溶液に含まれる(a)金属化合物粒子と(b)ポリシロキサン化合物とを総称して「PS−09」と記す。
ラムダエースSTM−602(商品名、大日本スクリーン製)を用いて、屈折率1.70でプリベーク膜の膜厚、現像後膜の露光部膜厚および硬化膜の膜厚を測定した。
残膜率は以下の式に従って算出した。
残膜率(%)=現像後膜の露光部膜厚÷プリベーク膜の膜厚×100
(3)感光感度の算出
得られたプリベーク膜をPLA(キヤノン(株)製PLA−501F)を用いて、超高圧水銀灯により、感度測定用のグレースケールマスク(Opto−Line製 Multi density Resolution Mask)を介してパターン露光した。設計寸法100μmの正方形パターンが現像後に剥がれず、残って形成される最小露光量を感光感度とした。
得られた現像後膜について、全ての露光量での正方形パターンを観察し、最小パターン寸法を現像後解像度とした。同様に得られた硬化膜について、全ての正方形パターンを観察し、最小パターン寸法をキュア後解像度として観察を行った。
得られた硬化膜について、大塚電子(株)製分光エリプソメータFE5000を用いて、22℃での550nmにおける屈折率を測定した。
得られた硬化膜の400nm波長による消衰係数を大塚電子(株)製分光エリプソメータFE5000により測定し、下記式により400nm波長における膜厚1μm換算での光透過率(%)を求めた。
光透過率=exp(−4πkt/λ)
ただし、kは消衰係数、tは膜厚(μm)、λは測定波長(nm)を表す。なお、作製した硬化膜の膜厚が1μmからはずれた際には、以下の式にて計算した。
膜厚が1μmあたりの透過率={(透過率/100)^ (1/t)}*100。
得られた硬化膜について、PGMEA溶剤に25℃2分間浸漬し、その前後での残膜率が99%以上のときにきわめて良好(A)、95%以上であるとき良好(B)、95%未満であるとき不良(D)であると判定した。なお残膜率は以下の式に従って算出した。
残膜率(%)=PGMEA溶剤浸漬後膜厚÷PGMEA溶剤浸漬前膜厚×100
膜厚については、上記(1)膜厚測定に記載の方法で測定した。
1.5μm角の市松模様のマスクを用いて露光後、パタ。ーニングして得られた硬化膜についてそれぞれの露光量での断面SEM写真からパターンの断面のテーパー角度を求めた。すべての露光量にて1.5μmのパターンが解像していない場合はD、すべての露光量のうちで一番高いテーパー角度が45°〜60°の場合をC、60°〜75°をB、75°〜90°をAと表記した。
表1の組成物1の比率となるよう調合し、フッ素系界面活性剤として、DFX−18((株)ネオス製)を30ppm添加し、黄色灯下で混合、撹拌して均一溶液とした後、0.20μmのフィルターで濾過して組成物1を調製した。
組成物の成分を表1〜6に示すとおりに変更したほかは実施例1と同様にして組成物2〜35を調製した。得られた各組成物を用いて、実施例1と同様にしてプリベーク膜、現像後膜、硬化膜を作製し、評価を行った。評価結果を表7〜9に示す。
Claims (16)
- 以下の(a)〜(d)を含有するネガ型感光性樹脂組成物であって、
(a)金属化合物粒子
(b)ポリシロキサン化合物
(c)α,β−不飽和カルボン酸エステル構造を含む基を1つ以上有する化合物
(d)光重合開始剤
さらに(e)マレイミド基を有する化合物を含有し、かつ、
前記(a)金属化合物粒子と前記(b)ポリシロキサン化合物が部分結合していることを特徴とするネガ型感光性組成物。 - 以下の(a)〜(d)を含有するネガ型感光性樹脂組成物であって、
(a)金属化合物粒子
(b)ポリシロキサン化合物
(c)α,β−不飽和カルボン酸エステル構造を含む基を1つ以上有する化合物
(d)光重合開始剤
さらに(e)マレイミド基を有する化合物を含有し、かつ、
前記(c)α,β−不飽和カルボン酸エステル構造を含む基を1つ以上有する化合物が、下記一般式(5)〜(10)から選ばれる化合物であることを特徴とするネガ型感光性組成物。
- R3が、アリル基、ビニル基、(メタ)アクリロイル基またはスチリル基である請求項4に記載のネガ型感光性樹脂組成物。
- 前記(b)ポリシロキサン化合物のR1が下記一般式(11)〜(13)のいずれかで表されるジカルボン酸無水物を有する有機基である請求項3〜5のいずれかに記載のネガ型感光性樹脂組成物。
- (b)ポリシロキサン化合物のSi原子モル数に対する、当該ポリシロキサン化合物を構成する一般式(1)および/または(2)で示される構造単位中のSi原子モルの比が、5モル%以上30モル%以下である請求項3〜6のいずれかに記載のネガ型感光性樹脂組成物。
- 前記(a)金属化合物粒子がアルミニウム化合物粒子、スズ化合物粒子、チタン化合物粒子およびジルコニウム化合物粒子から選ばれる1以上の金属化合物粒子またはアルミニウム化合物、スズ化合物、チタン化合物およびジルコニウム化合物から選ばれる1以上の金属化合物とケイ素化合物との複合粒子である請求項1〜7のいずれかに記載のネガ型感光性樹脂組成物。
- 前記(a)金属化合物粒子と前記(b)ポリシロキサン化合物が部分結合している請求項2〜8のいずれかに記載のネガ型感光性樹脂組成物。
- 前記(a)金属化合物粒子の数平均粒子径が、1nm〜400nmである請求項1〜9のいずれかに記載のネガ型感光性樹脂組成物。
- 前記(a)金属化合物粒子が、(b)ポリシロキサン化合物100重量部に対して、10重量部以上500重量部以下である請求項1〜10のいずれかに記載のネガ型感光性樹脂組成物。
- 請求項1〜11のいずれかに記載のネガ型感光性樹脂組成物を硬化させてなる硬化膜。
- 請求項1〜11のいずれかに記載のネガ型感光性樹脂組成物を基板上に塗布し、露光した後に現像し、次いで熱硬化させる硬化膜の製造方法。
- 請求項12に記載の硬化膜を具備するLED照明。
- 請求項12に記載の硬化膜を具備するイメージセンサ。
- 少なくとも、光電変換層、カラーフィルターおよび平坦化層を順に有する裏面照射型CMOSイメージセンサであって、前記カラーフィルターは、請求項1〜11のいずれかに記載のネガ型感光性樹脂組成物から得られるパターンによって着色画素が区分されており、前記平坦化層の屈折率が前記パターンの屈折率よりも小さい、CMOSイメージセンサ。
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KR20160113155A (ko) | 2016-09-28 |
TWI666511B (zh) | 2019-07-21 |
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US9977329B2 (en) | 2018-05-22 |
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