JP2020166254A - 感光性樹脂組成物、感光性樹脂組成物を硬化してなる硬化膜、硬化膜付き基板および硬化膜付き基板の製造方法 - Google Patents
感光性樹脂組成物、感光性樹脂組成物を硬化してなる硬化膜、硬化膜付き基板および硬化膜付き基板の製造方法 Download PDFInfo
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- PXZQEOJJUGGUIB-UHFFFAOYSA-N isoindolin-1-one Chemical compound C1=CC=C2C(=O)NCC2=C1 PXZQEOJJUGGUIB-UHFFFAOYSA-N 0.000 description 1
- GWVMLCQWXVFZCN-UHFFFAOYSA-N isoindoline Chemical compound C1=CC=C2CNCC2=C1 GWVMLCQWXVFZCN-UHFFFAOYSA-N 0.000 description 1
- 125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 description 1
- 150000003951 lactams Chemical class 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 description 1
- 229910052808 lithium carbonate Inorganic materials 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 238000001000 micrograph Methods 0.000 description 1
- GKTNLYAAZKKMTQ-UHFFFAOYSA-N n-[bis(dimethylamino)phosphinimyl]-n-methylmethanamine Chemical compound CN(C)P(=N)(N(C)C)N(C)C GKTNLYAAZKKMTQ-UHFFFAOYSA-N 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- NWAHZAIDMVNENC-UHFFFAOYSA-N octahydro-1h-4,7-methanoinden-5-yl methacrylate Chemical compound C12CCCC2C2CC(OC(=O)C(=C)C)C1C2 NWAHZAIDMVNENC-UHFFFAOYSA-N 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 1
- 238000005192 partition Methods 0.000 description 1
- 238000000059 patterning Methods 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- MIVZUXGHPJSKRI-UHFFFAOYSA-N pentane-1,1,1,2-tetracarboxylic acid Chemical compound CCCC(C(O)=O)C(C(O)=O)(C(O)=O)C(O)=O MIVZUXGHPJSKRI-UHFFFAOYSA-N 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Substances OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
- DGBWPZSGHAXYGK-UHFFFAOYSA-N perinone Chemical compound C12=NC3=CC=CC=C3N2C(=O)C2=CC=C3C4=C2C1=CC=C4C(=O)N1C2=CC=CC=C2N=C13 DGBWPZSGHAXYGK-UHFFFAOYSA-N 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- 150000004714 phosphonium salts Chemical group 0.000 description 1
- 238000000206 photolithography Methods 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920006255 plastic film Polymers 0.000 description 1
- 239000002985 plastic film Substances 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- ZJLMKPKYJBQJNH-UHFFFAOYSA-N propane-1,3-dithiol Chemical compound SCCCS ZJLMKPKYJBQJNH-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 229940079877 pyrogallol Drugs 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- IZMJMCDDWKSTTK-UHFFFAOYSA-N quinoline yellow Chemical compound C1=CC=CC2=NC(C3C(C4=CC=CC=C4C3=O)=O)=CC=C21 IZMJMCDDWKSTTK-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000007261 regionalization Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- NBPUSGBJDWCHKC-UHFFFAOYSA-M sodium 3-hydroxybutyrate Chemical compound [Na+].CC(O)CC([O-])=O NBPUSGBJDWCHKC-UHFFFAOYSA-M 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 230000003746 surface roughness Effects 0.000 description 1
- QJVXKWHHAMZTBY-GCPOEHJPSA-N syringin Chemical compound COC1=CC(\C=C\CO)=CC(OC)=C1O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 QJVXKWHHAMZTBY-GCPOEHJPSA-N 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 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
- 125000001302 tertiary amino group Chemical group 0.000 description 1
- 125000006158 tetracarboxylic acid group Chemical group 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- JOUDBUYBGJYFFP-FOCLMDBBSA-N thioindigo Chemical compound S\1C2=CC=CC=C2C(=O)C/1=C1/C(=O)C2=CC=CC=C2S1 JOUDBUYBGJYFFP-FOCLMDBBSA-N 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- FRGPKMWIYVTFIQ-UHFFFAOYSA-N triethoxy(3-isocyanatopropyl)silane Chemical compound CCO[Si](OCC)(OCC)CCCN=C=O FRGPKMWIYVTFIQ-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 description 1
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 description 1
- 239000011800 void material Substances 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 238000004383 yellowing Methods 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical class O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
-
- 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
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/032—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders
- G03F7/033—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders the binders being polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. vinyl polymers
-
- 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
- G03F7/004—Photosensitive materials
- G03F7/075—Silicon-containing compounds
-
- 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
- G03F7/004—Photosensitive materials
- G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
- G03F7/105—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers having substances, e.g. indicators, for forming visible images
-
- 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
-
- 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
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Engineering & Computer Science (AREA)
- Architecture (AREA)
- Structural Engineering (AREA)
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Materials For Photolithography (AREA)
- Polymerisation Methods In General (AREA)
- Epoxy Resins (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Optical Filters (AREA)
- Exposure And Positioning Against Photoresist Photosensitive Materials (AREA)
Abstract
Description
ピグメント・レッド2、3、4、5、9、12、14、22、23、31、38、112、122、144、146、147、149、166、168、170、175、176、177、178、179、184、185、187、188、202、207、208、209、210、213、214、220、221、242、247、253、254、255、256、257、262、264、266、272、279等
ピグメント・オレンジ5、13、16、34、36、38、43、61、62、64、67、68、71、72、73、74、81等
ピグメント・イエロー1、3、12、13、14、16、17、55、73、74、81、83、93、95、97、109、110、111、117、120、126、127、128、129、130、136、138、139、150、151、153、154、155、173、174、175、176、180、181、183、185、191、194、199、213、214等
ピグメント・グリーン7、36、58等
ピグメント・ブルー15、15:1、15:2、15:3、15:4、15:6、16、60、80等
ピグメント・バイオレット19、23、37等
合成例中で得られた樹脂溶液1gをガラスフィルター〔重量:W0(g)〕に含浸させて秤量し〔W1(g)〕、160℃にて2時間加熱した後の重量〔W2(g)〕から次式より求めた。
固形分濃度(重量%)=100×(W2−W0)/(W1−W0)
樹脂溶液をジオキサンに溶解させた後に臭化テトラエチルアンモニウムの酢酸溶液を加え、電位差滴定装置「COM−1600」(平沼産業株式会社製)を用いて1/10N−過塩素酸溶液で滴定して求めた。
樹脂溶液をジオキサンに溶解させ、電位差滴定装置「COM−1600」(平沼産業株式会社製)を用いて1/10N−KOH水溶液で滴定して求めた。
ゲルパーミュエーションクロマトグラフィー(GPC)「HLC−8220GPC」(東ソー株式会社製、溶媒:テトラヒドロフラン、カラム:TSKgelSuperH−2000(2本)+TSKgelSuper H−3000(1本)+TSKgelSuper H−4000(1本)+TSKgelSuperH−5000(1本)(東ソー株式会社製)、温度:40℃、速度:0.6ml/min)にて測定し、標準ポリスチレン(東ソー株式会社製、PS−オリゴマーキット)換算値として重量平均分子量(Mw)を求めた。
アシルオキシム系光重合開始剤のモル吸光係数は、紫外可視近赤外分光光度計「UH4150」(株式会社日立ハイテクサイエンス製)を用いて測定した。
シリカ粒子の平均粒子径は、動的光散乱法の粒度分布計「粒径アナライザーFPAR−1000」(大塚電子株式会社製)を用い、キュムラント法により測定した。
DCPMA :ジシクロペンタニルメタクリレート
GMA :グリシジルメタクリレート
St :スチレン
AA :アクリル酸
SA :無水コハク酸
BPFE :ビスフェノールフルオレン型エポキシ化合物(9,9−ビス(4−ヒドロキシフェニル)フルオレンとクロロメチルオキシランとの反応物)
BPDA :3,3’,4,4’−ビフェニルテトラカルボン酸二無水物
THPA :テトラヒドロ無水フタル酸
AIBN :アゾビスイソブチロニトリル
TDMAMP:トリスジメチルアミノメチルフェノール
HQ :ハイドロキノン
TEA :トリエチルアミン
TEAB :臭化テトラエチルアンモニウム
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
還留冷却器付き1Lの四つ口フラスコ中に、PGMEA(300g)を入れ、フラスコ系内を窒素置換した後120℃に昇温した。このフラスコ中にモノマー混合物(DCPMA(77.1g、0.35モル)、GMA(49.8g、0.35モル)、St(31.2g、0.30モル)にAIBN(10g)を溶解した混合物を滴下ロートから2時間かけて滴下し、さらに120℃で2時間撹拌し、共重合体溶液を得た。
還留冷却器付き500ml四つ口フラスコ中にBPFE(114.4g、0.23モル)、AA(33.2g、0.46モル)、PGMEA(157.0g)およびTEAB(0.48g)を仕込み、100〜105℃で20時間撹拌して反応させた。次いで、フラスコ内にBPDA(35.3g、0.12モル)、THPA(18.3g、0.12モル)を仕込み、120〜125℃で6時間撹拌し、重合性不飽和基含有アルカリ可溶性樹脂(A)−2を得た。得られた樹脂溶液の固形分濃度は56.1質量%であり、酸価(固形分換算)は103mgKOH/gであり、GPC分析によるMwは3600であった。
(A)−1:上記合成例1で得られた樹脂溶液(固形分濃度46.0質量%)
(A)−2:上記合成例2で得られた樹脂溶液(固形分濃度56.1質量%)
(B):ジペンタエリスリトールペンタアクリレートとヘキサアクリレートとの混合物(DPHA(アクリル当量96〜115)、日本化薬株式会社製)
(C)−1:3’,4’−エポキシシクロヘキシルメチル3’,4’−エポキシシクロヘキサンカルボキシレート(エポキシ当量130、株式会社ダイセル製)
(C)−2:ブタンテトラカルボン酸 テトラ(3,4−エポキシシクロヘキシルメチル)修飾ε−カプロラクトン(エポキシ当量197、株式会社ダイセル製)
(C)−3:HiREM−1(エポキシ当量113、四国化成工業株式会社製)
(C)−4:2,2−ビス(ヒドロキシメチル)−1−ブタノールの1,2−エポキシ−4−(2−オキシラニル)シクロヘキサン付加物(EHPE3150、エポキシ当量180、株式会社ダイセル製)
(C)−5:トリフェニルメタン型エポキシ樹脂(EPPN−501H、エポキシ当量160、日本化薬株式会社製)
(D)−1:オキシムエステル系光重合開始剤(アデカアークルズNCI−831、株式会社ADEKA製、「アデカアークルズ」は同社の登録商標)
(D)−2:ペンタエリスリトールテトラキス(3−メルカプトプロピオネート)
(E)−1:プロピレングリコールモノメチルエーテルアセテート(PGMEA)
(E)−2:ジエチレングリコールエチルメチルエーテル(EDM)
(F)−1:無水トリメリット酸
(F)−2:1,8−ジアザビシクロ[5.4.0]ウンデカ−7−エン(DBU(R)、サンアプロ株式会社製)を2.0質量%含有するPGMEA溶液
(G)−1:樹脂被覆カーボンブラック25.0質量%、高分子分散剤5.0質量%のPGMEA溶剤の顔料分散体(固形分濃度30.0質量%)
(G)−2:カーボンブラック25.0質量%、高分子分散剤2.0質量%、分散樹脂(合成例2のアルカリ可溶性樹脂(A)−2)8.0質量%のPGMEA溶剤の顔料分散体(固形分濃度35.0質量%)
(H)−2:シリカPGMEA分散液「YA050C」(株式会社アドマテックス製、固形分濃度40質量%、平均粒子径50nm)
(H)−3:シリカPGMEA分散液「YC100C」(株式会社アドマテックス製、固形分濃度50質量%、平均粒子径100nm)
(H)−4:中空シリカイソプロパノール分散液(日揮触媒化成株式会社製、固形分濃度20質量%、平均粒子径、75nm、空隙率46体積%)
(I):メガファックF−475(DIC株式会社製、「メガファック」は同社の登録商標)
実施例1〜43、比較例1〜36の感光性樹脂組成物を硬化してなる硬化膜(塗膜)を用いて、以下の評価を行った。評価結果を表8〜13に示す。
表1〜7に示した感光性樹脂組成物を、予め低圧水銀灯で波長254nmの照度1000mJ/cm2の紫外線を照射して表面を洗浄した、125mm×125mmのガラス基板「#1737」(コーニング社製)(以下「ガラス基板」という)上に、加熱硬化処理後の膜厚が1.2μmとなるようにスピンコーターを用いて塗布し、ホットプレートを用いて85℃で1分間プリベークをして硬化膜(塗膜)を作製した。次いで、露光ギャップを100μmに調整し、上記硬化膜(塗膜)上にライン/スペース=10μm/50μmのネガ型フォトマスクを被せ、i線照度30mW/cm2の超高圧水銀ランプで80mJ/cm2の紫外線を照射して、感光部分の光硬化反応を行った。
(パターン線幅)
(評価方法)
本硬化(ポストベーク)後のパターン線幅を測長顕微鏡「XD−20」(株式会社ニコン製)を用いてマスク幅10μmのパターン線幅を測定した。なお、パターン線幅の評価は、BT+10秒の場合とBT+20秒の場合とで行った。
○:パターン線幅が10±2μmの範囲内である
×:パターン線幅が10±2μmの範囲外である
(評価方法)
本硬化(ポストベーク)の10μmマスクパターンを光学顕微鏡を用いて観察した。なお、パターン直線性の評価は、BT+10秒の場合とBT+20秒の場合とで行った。なお、△以上を合格とした。
○:パターンエッジ部分のギザつきが認められない
△:パターンエッジ部分のギザつきが一部に認められる
×:パターンエッジ部分のギザつきが全体にわたって認められる
(評価方法)
本硬化(ポストベーク)後の10μmマスクパターンを光学顕微鏡を用いて観察した。なお、パターン密着性の評価は、BT+20秒の現像条件で行い、△以上を合格とした。
○:パターンに剥離が見られない
△:パターンのごく一部に剥離が見られる
×:パターンの大部分が剥離している
表1〜7に示した感光性樹脂組成物を、予め低圧水銀灯で波長254nmの照度1000mJ/cm2の紫外線を照射して表面を洗浄した、125mm×125mmのガラス基板「#1737」(コーニング社製)(以下「ガラス基板」という)上に、加熱硬化処理後の膜厚が1.2μmとなるようにスピンコーターを用いて塗布し、ホットプレートを用いて85℃で1分間プリベークをして硬化膜(塗膜)を作製した。次いで、露光ギャップを100μmに調整し、上記硬化膜(塗膜)上にライン/スペース=10μm/50μmのネガ型フォトマスクを被せ、i線照度30mW/cm2の超高圧水銀ランプで80mJ/cm2の紫外線を照射して、光硬化反応を行った。
(評価方法)
マクベス透過濃度計を用いて、作製した硬化膜(塗膜)の光学濃度(OD)を評価した。また、基板に形成した硬化膜(塗膜)の膜厚を測定し、光学濃度(OD)の値を膜厚で割った値をOD/μmとした。
光学濃度(OD)=−log10T(1)
(Tは透過率を示す)
(評価方法)
光学濃度(OD)評価用と同様にして作製した硬化膜(塗膜)の表面をPGMEAに浸漬したウエスで連続して20往復擦った。なお、△以上を合格とした。
○:硬化膜(塗膜)の表面に溶解が見られず、傷も付いていない
△:硬化膜(塗膜)の表面のごく一部に溶解が見られ、ごく一部に傷も付いている
×:硬化膜(塗膜)の表面が軟化しており、大部分に傷が付いている
表1〜7に示した感光性樹脂組成物を、予め低圧水銀灯で波長254nmの照度1000mJ/cm2の紫外線を照射して表面を洗浄した、125mm×125mmのガラス基板「#1737」(コーニング社製)(以下「ガラス基板」という)上に、加熱硬化処理後の膜厚が1.2μmとなるようにスピンコーターを用いて塗布し、ホットプレートを用いて85℃で1分間プリベークをして硬化膜(塗膜)を作製した。次いで、熱風乾燥機を用いて85℃で60分間、本硬化(ポストベーク)し、実施例9〜43、比較例9〜36に係る硬化膜付き基板を得た。
(評価方法)
作製した硬化膜(塗膜)付き基板に対して、紫外可視近赤外分光光度「UH4150」(株式会社日立ハイテクサイエンス製)を用いて入射角2°で硬化膜(塗膜)側の反射率を測定した。
Claims (13)
- 耐熱温度が140℃以下の基板上に硬化膜を形成するため使用される感光性樹脂組成物であって、
(A)不飽和基含有アルカリ可溶性樹脂と、
(B)少なくとも2個以上のエチレン性不飽和結合を有する光重合性モノマーと、
(C)3,4−エポキシシクロヘキシル基を2個以上有するエポキシ化合物と、
(D)光重合開始剤と、
(E)溶剤と、
を含み、
(C)成分の含有量は、固形分の全質量に対して、5〜17質量%である、感光性樹脂組成物。 - 前記(A)成分の不飽和基含有アルカリ可溶性樹脂は、一般式(3)で表される不飽和基含有アルカリ可溶性樹脂である、請求項1に記載の感光性樹脂組成物。
- (F)エポキシ化合物の硬化剤および/または硬化促進剤を含み、前記(C)成分と前記(F)成分との合計量は、固形分の全質量に対して、6〜24質量%である、請求項1〜3のいずれか一項に記載の感光性樹脂組成物。
- 前記(F)成分は酸無水物を含む、請求項1〜4のいずれか一項に記載の感光性樹脂組成物。
- 有機顔料または無機顔料からなる群から選択される(G)着色材を含む、請求項1に記載の感光性樹脂組成物。
- 前記(G)着色材は、黒色有機顔料、混色有機顔料または黒色無機顔料からなる群から選択される遮光材である、請求項6に記載の感光性樹脂組成物。
- (H)シリカ粒子を含み、シリカ粒子の平均粒径が1〜95nmである、請求項1に記載の感光性樹脂組成物。
- 前記(D)成分は、365nmにおけるモル吸光係数が10000L/mol・cm以上であるアシルオキシム系光重合開始剤である、請求項1〜8のいずれか一項に記載の感光性樹脂組成物。
- 前記(D)成分は、一般式(5)で表されるアシルオキシム系光重合開始剤である、請求項9に記載の感光性樹脂組成物。
- 請求項1〜10のいずれか一項に記載の感光性樹脂組成物を硬化してなる硬化膜。
- 請求項11に記載の硬化膜を有する硬化膜付き基板。
- 耐熱温度が140℃以下の基板上に硬化膜パターンを形成して硬化膜付き基板を製造する方法であって、請求項1〜10のいずれか一項に記載の感光性樹脂組成物を基板上に塗布し、フォトマスクを介して露光して、現像により未露光部を除去し、140℃以下で加熱して硬化膜パターンを形成する、硬化膜付き基板の製造方法。
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KR20230141486A (ko) | 2022-03-31 | 2023-10-10 | 닛테츠 케미컬 앤드 머티리얼 가부시키가이샤 | 감광성 수지 조성물, 감광성 수지 조성물을 경화해서 이루어지는 경화막, 경화막 부착 기판 및 경화막 부착 기판의 제조 방법 |
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