JP6464566B2 - 感光性樹脂組成物、感光性エレメント及びガラス基板の加工方法 - Google Patents
感光性樹脂組成物、感光性エレメント及びガラス基板の加工方法 Download PDFInfo
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- JP6464566B2 JP6464566B2 JP2014081151A JP2014081151A JP6464566B2 JP 6464566 B2 JP6464566 B2 JP 6464566B2 JP 2014081151 A JP2014081151 A JP 2014081151A JP 2014081151 A JP2014081151 A JP 2014081151A JP 6464566 B2 JP6464566 B2 JP 6464566B2
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- 229920006267 polyester film Polymers 0.000 description 1
- 229940051841 polyoxyethylene ether Drugs 0.000 description 1
- 229920000056 polyoxyethylene ether Polymers 0.000 description 1
- 229920005651 polypropylene glycol dimethacrylate Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 1
- WHMDPDGBKYUEMW-UHFFFAOYSA-N pyridine-2-thiol Chemical compound SC1=CC=CC=N1 WHMDPDGBKYUEMW-UHFFFAOYSA-N 0.000 description 1
- HBCQSNAFLVXVAY-UHFFFAOYSA-N pyrimidine-2-thiol Chemical compound SC1=NC=CC=N1 HBCQSNAFLVXVAY-UHFFFAOYSA-N 0.000 description 1
- 239000007870 radical polymerization initiator Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000002787 reinforcement Effects 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 239000010802 sludge Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000005728 strengthening Methods 0.000 description 1
- 238000005496 tempering Methods 0.000 description 1
- XZHNPVKXBNDGJD-UHFFFAOYSA-N tetradecyl prop-2-enoate Chemical compound CCCCCCCCCCCCCCOC(=O)C=C XZHNPVKXBNDGJD-UHFFFAOYSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- NJRXVEJTAYWCQJ-UHFFFAOYSA-N thiomalic acid Chemical compound OC(=O)CC(S)C(O)=O NJRXVEJTAYWCQJ-UHFFFAOYSA-N 0.000 description 1
- NBOMNTLFRHMDEZ-UHFFFAOYSA-N thiosalicylic acid Chemical compound OC(=O)C1=CC=CC=C1S NBOMNTLFRHMDEZ-UHFFFAOYSA-N 0.000 description 1
- 229940103494 thiosalicylic acid Drugs 0.000 description 1
- LMYRWZFENFIFIT-UHFFFAOYSA-N toluene-4-sulfonamide Chemical compound CC1=CC=C(S(N)(=O)=O)C=C1 LMYRWZFENFIFIT-UHFFFAOYSA-N 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
- QQQSFSZALRVCSZ-UHFFFAOYSA-N triethoxysilane Chemical compound CCO[SiH](OCC)OCC QQQSFSZALRVCSZ-UHFFFAOYSA-N 0.000 description 1
- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-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
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C03—GLASS; MINERAL OR SLAG WOOL
- C03C—CHEMICAL COMPOSITION OF GLASSES, GLAZES OR VITREOUS ENAMELS; SURFACE TREATMENT OF GLASS; SURFACE TREATMENT OF FIBRES OR FILAMENTS MADE FROM GLASS, MINERALS OR SLAGS; JOINING GLASS TO GLASS OR OTHER MATERIALS
- C03C15/00—Surface treatment of glass, not in the form of fibres or filaments, by etching
-
- 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
-
- 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
-
- 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
- G03F7/26—Processing photosensitive materials; Apparatus therefor
- G03F7/40—Treatment after imagewise removal, e.g. baking
-
- 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
- G03F7/42—Stripping or agents therefor
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/02—Details
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/02—Details
- H05B33/04—Sealing arrangements, e.g. against humidity
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Spectroscopy & Molecular Physics (AREA)
- General Chemical & Material Sciences (AREA)
- Geochemistry & Mineralogy (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Materials For Photolithography (AREA)
- Photosensitive Polymer And Photoresist Processing (AREA)
- Electroluminescent Light Sources (AREA)
- Surface Treatment Of Glass (AREA)
Description
(合成例)
[バインダーポリマーの合成]
撹拌機、還流冷却器、温度計、滴下ロート及び窒素ガス導入管を備えたフラスコに、質量比3:2であるメチルセロソルブ及びトルエンの配合物(以下、「配合物(a)」という)500gを加え、窒素ガスを吹き込みながら撹拌して、85℃まで加熱した。一方、重合性単量体としてメタクリル酸150g、メタクリル酸メチルエステル110g、アクリル酸エチルエステル65g、メタクリル酸ブチルエステル50g及びスチレン125gと、アゾビスイソブチロニトリル2.5gとを混合した溶液(以下、「溶液(b)」という)を用意した。
(GPC測定条件)
ポンプ:日立 L−6000型(株式会社日立製作所製、商品名)
カラム:以下の計3本(カラム仕様:10.7mmφ×300mm)
Gelpack GL−R420
Gelpack GL−R430
Gelpack GL−R440(以上、日立化成株式会社製、商品名)
溶離溶解液:テトラヒドロフラン
試料濃度:固形分の濃度が43質量%のバインダーポリマーを120mg採取し、5mLのテトラヒドロフランに溶解して試料を調製した。
測定温度:室温
流量:2.05mL/分
検出器:日立 L−3300型RI(株式会社日立製作所製、商品名)
[感光性樹脂組成物の調製]
表1に示す各成分の配合量(質量部)と、溶剤として、アセトン4質量部、トルエン12質量部及びプロピレングリコールモノメチルエーテル2質量部とを混合することにより、感光性樹脂組成物を得た。表1中の配合量は不揮発分の質量(固形分量)である。なお、「−」は未配合を意味する。
FA−323M;EO変性ビスフェノールAジメタクリレート(1分子中にエチレンオキサイド基を平均30モル付加させたもの、日立化成株式会社製、商品名)。(B)成分に該当。
FA−321M;EO変性ビスフェノールAジメタクリレート(1分子中にエチレンオキサイド基を平均10モル付加させたもの、日立化成株式会社製、商品名)。(B)成分に該当。
FA−324A;EO変性ビスフェノールAジアクリレート(1分子中にエチレンオキサイド基を平均4モル付加させたもの、日立化成株式会社製、商品名)。(B)成分に該当。
FA−240A;ポリエチレングリコールジアクリレート(1分子中にエチレンオキサイド基を平均9モル付加させたもの、日立化成株式会社製、商品名)。(B)成分に該当。
FA−P240M;ポリプロピレングリコールジメタクリレート(1分子中にプロピレンオキサイド基を平均7モル付加させたもの、日立化成株式会社製、商品名)。(B)成分に該当。
FA−137M;トリメチロールプロパンポリオキシエチレンエーテルトリメタクリレート(1分子中にエチレンオキサイド基を平均21モル付加させたもの、日立化成株式会社製、商品名)。(B)成分に該当。
M−215;イソシアヌル酸EO変性ジアクリレート(東亜合成株式会社製、商品名)
FA−MECH;(2−ヒドロキシ−3−クロロ)プロピル−2−メタクリロイルオキシエチルフタレート(日立化成株式会社製、商品名)。(B)成分に該当。
SR454;ポリオキシエチレントリメチロールプロパントリアクリレート(1分子中にエチレンオキサイド基を平均3モル付加させたもの、日本化薬株式会社製、商品名)。(B)成分に該当。
FA−126AS;1,6−ヘキサンジオールジアクリレート(日立化成株式会社製、商品名)。(B)成分に該当。
B−CIM;2−(2−クロロフェニル)−1−[2−(2−クロロフェニル)−4,5−ジフェニル−1,3−ジアゾール−2−イル]−4,5−ジフェニルイミダゾール(保土ヶ谷化学工業株式会社製、商品名)。(C)成分に該当。
EAB;N,N,N´,N´−テトラエチル−4,4´−ジアミノベンゾフェノン(保土ヶ谷化学工業株式会社製、商品名)。(C)成分に該当。
KBE−503;3−メタクリロキシプロピルトリエトキシシラン(信越シリコーン株式会社製、商品名)。(D)成分に該当し、かつ(B)成分にも該当。
2−メルカプトベンゾイミダゾール;2−メルカプトベンゾイミダゾール(東京化成工業株式会社製、商品名)。(E)成分に該当。
上述した方法で得られた感光性樹脂組成物を、それぞれ16μm厚のポリエチレンテレフタレートフィルム(帝人デュポンフィルム株式会社製、商品名「G2−16」)(支持体)上に厚みが均一になるように塗布し、90℃の熱風対流式乾燥機で5分間乾燥し、乾燥後の膜厚が50μmである感光層を形成した。次いで、ポリエチレンフィルム(タマポリ株式会社製、商品名「NF−15」)(保護層)を感光層上に貼り合わせ、支持体と、感光層と、保護層とがこの順に積層された感光性エレメントを得た。
上述した方法で作製した評価サンプルの光硬化物パターンを、顕微鏡を用いて倍率50倍で拡大して観察し、以下の基準で現像性を評価した。レジスト残渣が観察されず、光硬化物パターンを形成できた場合を「○」、レジスト残渣が観察された、又は、光硬化物パターンを形成できなかった場合を「×」とした。
上記評価サンプルを、23℃のふっ化水素酸(株式会社ジェイ・エス・ピー製、商品名「FSW」)に浸漬し、光硬化物パターンが剥離したことを目視で確認できた時間(G)を測定し、ガラスの彫り速度(H)との積(G×H)をガラスの彫れ量として、耐ふっ化水素酸性を評価した。なお、ガラスの彫り速度は4μm/分とし、ガラス彫れ量は小数点以下第1位を四捨五入した値とした。ガラス彫れ量が50μm以下を「×」、51〜100μmを「△」、101〜150μmを「○」、151μm以上を「◎」とした。ガラス彫れ量が多いほど、耐ふっ化水素酸性が良好であることを意味する。
液温50℃の15質量%テトラメチルアンモニウム水溶液に上記評価サンプルを浸漬し、光硬化物パターンが剥離したことを目視で確認できた時間を測定し、剥離性を評価した。60分以下で剥離した場合を「○」、剥離に61分以上の時間を有した場合「×」で評価した。
Claims (6)
- ふっ化水素酸を含有する溶液によってガラス基板をエッチングするときのマスクとしてのレジストを形成するために用いられる感光性樹脂組成物であって、
当該感光性樹脂組成物が、(A)バインダーポリマー、(B)光重合性化合物及び(C)光重合開始剤を含有し、
前記(A)バインダーポリマーが、(メタ)アクリル酸エステルを単量体単位として含むポリマーであるアクリル樹脂であり、
当該感光性樹脂組成物が、エチレンオキサイド基及び/又はプロピレンオキサイド基を有する化合物を含有し、
前記エチレンオキサイド基及び前記プロピレンオキサイド基が、前記エチレンオキサイド基及び/又はプロピレンオキサイド基を有する化合物を、X1−(OC2H4)a−(OC3H6)b−X2(a及びbは、それぞれ独立に0〜40の整数を示し、a+bは1以上であり、X1は、X3−C(=O)−又はHで表され、X2は、−O−X4又は−NX5X6又は−SiX7X8X9のいずれかで表され、X3、X4、X5、X6、X7、X8及びX9は、一価の基を表す)で表したときに、それぞれ、−(OC2H4)a−の部分における−OC2H4−で表される基、及び、−(OC3H6)b−の部分における−OC3H6−で表される基であり、
当該感光性樹脂組成物中の前記エチレンオキサイド基及び/又はプロピレンオキサイド基を有する化合物の少なくとも1種が、前記(B)光重合性化合物に含まれ、
前記(B)光重合性化合物に含まれる前記エチレンオキサイド基及び/又はプロピレンオキサイド基を有する化合物が、エチレンオキサイド変性ビスフェノールAジ(メタ)アクリレート化合物、プロピレンオキサイド変性ビスフェノールAジ(メタ)アクリレート化合物、エチレンオキサイド・プロピレンオキサイド変性ビスフェノールAジ(メタ)アクリレート化合物、イソシアヌル酸エチレンオキサイド変性(メタ)アクリレート、イソシアヌル酸プロピレンオキサイド変性(メタ)アクリレート、イソシアヌル酸エチレンオキサイド・プロピレンオキサイド変性(メタ)アクリレート、芳香族カルボン酸(メタ)アクリロイルオキシアルキルエステル、エチレンオキサイド変性トリメチロールプロパントリ(メタ)アクリレート、プロピレンオキサイド変性トリメチロールプロパントリ(メタ)アクリレート、及びエチレンオキサイド・プロピレンオキサイド変性トリメチロールプロパントリ(メタ)アクリレートからなる群より選択される少なくとも1種の化合物を含み、
前記エチレンオキサイド基及び前記プロピレンオキサイド基の合計の含有率が、当該感光性樹脂組成物中の固形分の総量を基準として14質量%以下である、感光性樹脂組成物。 - (D)シラン化合物を更に含有する、請求項1に記載の感光性樹脂組成物。
- 前記感光性樹脂組成物中の前記エチレンオキサイド基及び/又はプロピレンオキサイド基を有する化合物の少なくとも1種が、前記(B)光重合性化合物及び前記(D)シラン化合物に含まれる、請求項2に記載の感光性樹脂組成物。
- 支持体と、該支持体上に設けられた感光層とを備える感光性エレメントであって、
前記感光層が請求項1〜3のいずれか一項に記載の感光性樹脂組成物を用いて形成される層である、感光性エレメント。 - 請求項1〜3のいずれか一項に記載の感光性樹脂組成物を用いて感光層をガラス基板上に形成する工程と、
前記感光層に活性光線を照射し、前記感光層の一部を除去して、前記ガラス基板の一部を露出させるパターンを有するレジストを形成する工程と、 前記レジストを熱処理する工程と、
熱処理後の前記レジストをマスクとしてふっ化水素酸により前記ガラス基板をエッチングする工程と、を含む、ガラス基板の加工方法。 - 前記ガラス基板をエッチングする工程の後、前記レジストを前記ガラス基板から剥離する工程を更に含む、請求項5に記載のガラス基板の加工方法。
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PCT/JP2015/060882 WO2015156292A1 (ja) | 2014-04-10 | 2015-04-07 | 感光性樹脂組成物、感光性エレメント及び加工ガラス基板を製造する方法 |
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