TWI712631B - 光硬化性樹脂組成物及使用其之光硬化性乾膜 - Google Patents
光硬化性樹脂組成物及使用其之光硬化性乾膜 Download PDFInfo
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- TWI712631B TWI712631B TW105117971A TW105117971A TWI712631B TW I712631 B TWI712631 B TW I712631B TW 105117971 A TW105117971 A TW 105117971A TW 105117971 A TW105117971 A TW 105117971A TW I712631 B TWI712631 B TW I712631B
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- 238000012552 review Methods 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- BDDWSAASCFBVBK-UHFFFAOYSA-N rhodium;triphenylphosphane Chemical compound [Rh].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 BDDWSAASCFBVBK-UHFFFAOYSA-N 0.000 description 1
- QBERHIJABFXGRZ-UHFFFAOYSA-M rhodium;triphenylphosphane;chloride Chemical compound [Cl-].[Rh].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 QBERHIJABFXGRZ-UHFFFAOYSA-M 0.000 description 1
- BHRZNVHARXXAHW-UHFFFAOYSA-N sec-butylamine Chemical compound CCC(C)N BHRZNVHARXXAHW-UHFFFAOYSA-N 0.000 description 1
- 230000001568 sexual effect Effects 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 229920005573 silicon-containing polymer Polymers 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000679 solder Inorganic materials 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229960002317 succinimide Drugs 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
- GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 229940066771 systemic antihistamines piperazine derivative Drugs 0.000 description 1
- PTSAQPIPJAFBDO-UHFFFAOYSA-N tert-butyl 2-[ethyl-[2-[(2-methylpropan-2-yl)oxycarbonyloxy]ethyl]amino]ethyl carbonate Chemical compound CC(C)(C)OC(=O)OCCN(CC)CCOC(=O)OC(C)(C)C PTSAQPIPJAFBDO-UHFFFAOYSA-N 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-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
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 1
- 150000007979 thiazole derivatives Chemical class 0.000 description 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- ABVVEAHYODGCLZ-UHFFFAOYSA-N tridecan-1-amine Chemical compound CCCCCCCCCCCCCN ABVVEAHYODGCLZ-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 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
- AANIRNIRVXARSN-UHFFFAOYSA-M trifluoromethanesulfonate;trimethylsulfanium Chemical compound C[S+](C)C.[O-]S(=O)(=O)C(F)(F)F AANIRNIRVXARSN-UHFFFAOYSA-M 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- RKBCYCFRFCNLTO-UHFFFAOYSA-N triisopropylamine Chemical compound CC(C)N(C(C)C)C(C)C RKBCYCFRFCNLTO-UHFFFAOYSA-N 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- WLOQLWBIJZDHET-UHFFFAOYSA-N triphenylsulfonium Chemical compound C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 WLOQLWBIJZDHET-UHFFFAOYSA-N 0.000 description 1
- 239000012953 triphenylsulfonium Substances 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
- 239000011995 wilkinson's catalyst Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
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- 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
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3467—Heterocyclic compounds having nitrogen in the ring having more than two nitrogen atoms in the ring
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D183/00—Coating compositions 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; Coating compositions based on derivatives of such polymers
- C09D183/14—Coating compositions 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; Coating compositions based on derivatives of such polymers in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms
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Abstract
Description
本發明係關於光硬化性樹脂組成物及使用其之光硬化性乾薄膜。
隨著個人電腦、數位照相機、手機等種種電子機器的小型化或高性能化,對於半導體元件之進一步小型化、薄型化及高密度化之要求急速增高。因此,對於可對應生產性提高中之基板面積的增大,且對於所謂晶片尺寸封裝或者晶片規模封裝(CSP)或三次元層合之高密度施行技術,欲於基板上具有微細且縱橫比高的凸塊,必須對應結構體之感光性絕緣材料的開發受到期待。
作為如上述之感光性絕緣材料,藉由在半導體元件製造步驟中常用的旋轉塗布法可達成廣範圍的膜厚之塗布,且對於廣範圍的波長區域亦可形成微細圖型形成,藉由低溫之後硬化,賦予具有優良可撓性、耐熱性、電氣特性、密著性、信賴性及藥品耐性之電氣.電子零件保護用皮膜的光硬化性樹脂組成物已被提案(專利文獻1)。該旋轉塗布法為具有於基板上可簡便地成膜的優
點。
另一方面,形成上述電氣.電子零件保護用皮膜之光硬化性樹脂組成物為於基板上使用1~100μm膜厚者,自膜厚超過30μm的附近,藉由該光硬化性樹脂組成物的黏度變得非常高,藉由旋轉塗布法之對於基板上的成膜在實際極限上成為困難。
又,將上述光硬化性樹脂組成物藉由上述旋轉塗布法於表面對具有凸塊之基板進行塗布時,幾乎均勻地包覆上述基板上具有困難度。因此,於基板上的段差部分容易產生光硬化性樹脂層之隙間,期待平坦性或段差包覆性的進一步改善。又,作為取代上述旋轉塗布法的其他塗布方法,已有噴霧法被提案(專利文獻2)。然而,來自該原理上基板之凸塊的高低差或者在圖型邊緣之膜破裂及所謂凹部底面針孔之缺陷容易產生,有關平坦性或段差包覆性的問題尚未充分地被解決。
且於近年來,對於所謂晶片尺寸封裝或者晶片規模封裝(CSP)或三次元層合之高密度實裝技術,於基板上形成超過100μm的超厚膜之圖型,藉由對所得之圖型層合銅等金屬,可自晶片施予再配線的材料要求極強烈。得到微細圖型之方法在光刻技術上為一般,其中亦以化學增幅型負型抗蝕材料可得到微細圖型而較佳。又,使用於再配線之圖型,永久地存在裝置晶片、晶片間,雖具有硬化之特徵,但作為具有優良可撓性、耐熱性、電氣特性、密著性、信賴性及藥品耐性之電氣.電子零件保護用
皮膜而作用為必要,故得到圖型之抗蝕材料以負型為佳。
[專利文獻1]日本特開2008-184571號公報
[專利文獻2]日本特開2009-200315號公報
本發明係有鑑於上述問題點所成者,以提供一種使用於圖型形成時,在高膜厚亦可使微細圖型形成容易進行的光硬化性樹脂組成物及使用其之光硬化性乾薄膜為目的。
欲達成上述目的,本發明為提供含有(A)~(D)之光硬化性樹脂組成物為目的,
〔式中,a、b為正數,R1、R2、R3、R4各為氫原子或碳數1~4的烷基或者烷氧基,可彼此相異或相同;r獨立為0、1或2;R5~R8獨立為氫原子或碳數1~10的一價烴基;R9為碳數1~10的二價烴基;n為0或1,k為0、1、2中任一者;R10、R11各為碳數1~4的烷基或烷氧基,彼此可相異或相同;Z為選自
(式中,R12、R13、R14、R15為可相同或可相異的碳數1~10的一價烴基;m為1~100的正數。)
前述一般式(1)中之環氧基(J)與前述一般式(2)中之酚性羥基(K)的比率為0.05≦(J)/((J)+(K))≦0.95。〕
(B)藉由波長190~500nm的光進行分解而產生酸的光酸產生劑、
(C)選自藉由甲醛或甲醛-醇進行改性的胺基縮合物、於1分子中平均具有2個以上羥甲基或烷氧基羥甲基之酚化合物、及將多價酚的羥基取代為環氧丙氧基之化合物的1種或2種以上之化合物、
(D)選自具有3個以上羥基的多價酚之1種或2種以上的化合物。
依據如此光硬化性樹脂組成物,使用於圖型形成時,在高膜厚下可容易進行微細圖型形成。
又,進一步含有(E)鹼性化合物者為佳。
藉由將如此鹼性化合物添加於光硬化性樹脂組成物中,可使由該光硬化性樹脂組成物所成的光硬化性樹脂層之解像度提高,抑制曝光後的感度變化,減少基板
或環境依賴性,可改善曝光幅度或圖型形狀等。
且,本發明為提供一種光硬化姓乾薄膜,其為具有將上述光硬化性樹脂組成物經薄膜化的光硬化性樹脂層,該光硬化性樹脂層之厚度為100μm~300μm。
若為如此光硬化性乾薄膜,使用於圖型形成時,在高膜厚可容易進行微細圖型形成。
依據本發明,藉由使用特定聚矽氧高分子化合物、光酸產生劑等,可得到使用在高膜厚,特別在100μm~300μm之高膜厚下進行微細圖型形成時的光硬化性樹脂組成物。
上述光硬化性樹脂組成物為藉由光進行圖型形成後,藉由進行250℃以下的低溫加熱處理,可容易形成對於使用於電子零件或半導體元件、迴路基板的基板之密著性優良,機械特性及電氣絕緣性優良,作為該絕緣保護膜之信賴性,進一步可防止保護膜之裂紋發生,對藥品耐性亦優良的皮膜,可適用於迴路基板、半導體元件、顯示元件等各種電氣.電子零件保護用皮膜之形成、及基板貼合用途上。
以下藉由本發明做詳細說明。
如上述,使用於圖型形成時,在高膜厚可容
易進行微細圖型形成之光硬化性樹脂組成物及使用其之光硬化性乾薄膜被要求。
本發明者們進欲達成上述目的進行詳細檢討。其結果發現含有下述(A)~(D)成分之光硬化性樹脂組成物及使用其之光硬化性乾薄膜可達成上述課題,而完成本發明。
以下對於本發明之實施的形態做具體說明,但本發明並未限定於此等者。
本發明之光硬化性樹脂組成物含有下述者,
〔式中,a、b為正數,R1、R2、R3、R4各為氫原子或碳數1~4的烷基或者烷氧基,可彼此相異或相同;r獨立為0、1或2;R5~R8獨立為氫原子或碳數1~10的一價烴基;R9為碳數1~10的二價烴基;n為0或1,k為0、1、2中任一者;R10、R11各為碳數1~4的烷基或烷氧基,彼此可相異或相同;Z為選自
(式中,R12、R13、R14、R15為可相同或可相異的碳數1~10的一價烴基;m為1~100的正數。)
前述一般式(1)中之環氧基(J)與前述一般式(2)中之酚性羥基(K)的比率為0.05≦(J)/((J)+(K))≦0.95〕
(B)藉由波長190~500nm的光進行分解而產生酸
的光酸產生劑、
(C)選自藉由甲醛或甲醛-醇進行改性的胺基縮合物、於1分子中平均具有2個以上羥甲基或烷氧基羥甲基之酚化合物、及將多價酚的羥基取代為環氧丙氧基之化合物的1種或2種以上之化合物、
(D)選自具有3個以上羥基的多價酚之1種或2種以上的化合物。
依據如此光硬化性樹脂組成物,使用於圖型形成時,可在高膜厚容易進行微細圖型形成。又,即使在低溫之後硬化,可賦予各種薄膜特性,特別對於使用於迴路基板的基材的密著性,作為電氣.電子零件之信賴性、藥品耐性優良,且信賴性高之皮膜。
以下對於本發明之光硬化性樹脂組成物的各成分做說明。
(A)成分為具有作為重複單位的下述一般式(1)所示含有環氧基之成分及下述一般式(2)所示含有酚性羥基之成分,重量平均分子量為3000~500000的聚矽氧高分子化合物。
〔式中,a、b為正數,R1、R2、R3、R4各為氫原子或碳數1~4的烷基或者烷氧基,可彼此相異或相同;r獨立為0、1或2;R5~R8獨立為氫原子或碳數1~10的一價烴基;R9為碳數1~10的二價烴基;n為0或1,k為0、1、2中任一者;R10、R11各為碳數1~4的烷基或烷氧基,彼此可相異或相同;Z為選自
(式中,R12、R13、R14、R15為可相同或可相異的碳數1~10的一價烴基;m為1~100的正數)。
前述一般式(1)中之環氧基(J)與前述一般式(2)中之酚性羥基(K)的比率為0.05≦(J)/((J)+(K))≦0.95〕
上述一般式(1)的R1~R4各為氫原子或碳數1~4的烷基或者烷氧基。這些可相互相異或相同。作為碳數1~4的烷基或烷氧基的具體例子,可舉出甲基、乙基、異丙基、tert-丁基、甲氧基、乙氧基、異丙基氧基等。
上述一般式(1)的R5~R8獨立為氫原子或碳數1~10的一價烴基;作為碳數1~10的一價烴基之具體例子,可舉出甲基、乙基、丙基、異丙基、丁基、異丁基、辛基、環己基等的直鏈、分支或環狀烷基、苯基、甲苯基、萘基等芳基。這些中以原料獲得之觀點來看以甲基為佳。
上述一般式(1)的R9為碳數1~10的二價烴基;作為R9的具體例子,可舉出伸甲基、伸乙基、伸丙基、伸丁基、伸戊基、戊烷基、環戊烷基、伸庚基、伸辛基、伸壬基、伸癸基等的直鏈、分支或環狀伸烷基、伸苯基、亞甲苯基、亞萘基等伸芳基。其中,由原料獲得之觀點來看,以伸苯基為佳。
上述一般式(2)的R10、R11各為碳數1~4的烷基或烷氧基。這些可相異或相同。作為R10、R11的具
體例子,可舉出甲基、乙基、異丙基、tert-丁基、甲氧基、乙氧基、異丙基氧基等。
上述一般式(4)的R12~R15為可相同或可相異的碳數1~10的一價烴基;R12~R15以碳數1~8的一價烴基為佳,較佳為碳數1~6的一價烴基。作為R12~R15的具體例子,可舉出甲基、乙基、丙基、異丙基、n-丁基、tert-丁基、異丁基、辛基、環己基等的直鏈狀、支鏈狀或環狀的烷基、乙烯基、烯丙基、丙烯基、丁烯基、己烯基、環己烯基等的直鏈狀、支鏈狀或環狀烯基、苯基、甲苯基、萘基等的芳基、苯甲基、苯基乙基等的芳烷基等。這些中亦由原料獲得之觀點來看以甲基為佳。
又,由與後述(B)~(D)成分的相溶性及光硬化性之觀點來看,上述一般式(4)的m為1~100,較佳為1~80的正數。
上述一般式(1)的a、上述一般式(2)的b為正數,較佳為0<a<1、0<b<1且a+b=1,更佳為0.05≦a≦0.8、0.2≦b≦0.95,特佳為0.2≦a≦0.8、0.2≦b≦0.8。
上述一般式(1)中之環氧基(J)與上述一般式(2)中之酚性羥基(K)的比率(莫耳比)為0.05≦(J)/((J)+(K))≦0.95。該比率以0.10≦(J)/((J)+(K))≦0.90為佳,較佳為0.10≦(J)/((J)+(K))≦0.85。環氧基(J)若過少時,與基板的密著性會降低,若環氧基(J)過多時,圖型解像性會
降低。
上述聚矽氧高分子化合物的重量平均分子量為3000~500000,以3000~300000為佳,較佳為5000~250000。將含有該聚矽氧高分子化合物之光硬化性樹脂組成物及該光硬化性樹脂組成物使用於光硬化性樹脂層的乾薄膜之光硬化性或經該光硬化性樹脂層進行硬化所得之硬化皮膜的機械的特性之觀點來看,以如此分子量為佳。且,重量平均分子量係藉由凝膠滲透層析法(GPC)所得之聚苯乙烯換算值者(以下相同)。
作為上述一般式(1)所示含有環氧基之成分的具體例子,可舉出下述所示者。
如此(A)成分的聚矽氧高分子化合物,例如可藉由以下所示方法製造。
首先,製造出下述一般式(5)所示化合物。
(式中,R1~R9及r與上述相同)
(式中,R為對應R1~R4的基。R與上述相同)
所示烯丙基化合物與下述一般式(7)HSiR5R6-R9-SiR7R8H (7)
(式中,R5~R9與上述相同)
所示矽素化合物經矽氫加成聚合反應可得到上述一般式(5)所示化合物。
(式中,R及r與上述相同)
(式中,R1~R9及r與上述相同)
所示化合物後,將該一般式(9)所示化合物與環氧氯丙烷進行反應後可得到上述一般式(5)所示化合物。
(式中,n、k、R10、R11及Z與上述相同)
(式中,R12~R15及m與上述相同)
所示二氫有機矽氧烷在觸媒存在下,進行矽氫加成聚合反應後,製造出(A)成分的聚矽氧高分子化合物。
此時,將上述一般式(5)所示化合物與上述一般式(10)所示烯丙基化合物調配成滿足(A)成分中環氧基(J)與酚性羥基(K)的比率。
且,對於(A)成分的聚矽氧高分子化合物,上述一般式(1)所示含有環氧基的成分及上述一般式(2)所示含有酚性羥基的成分可在嵌段、無規中任一結構下導入。
對於上述聚合反應,作為觸媒,例如可舉出鉑(含有鉑黑)、銠、鈀等鉑族金屬單體;H2PtCl4.xH2O、H2PtCl6.xH2O、NaHPtCl6.xH2O、KHPtCl6.xH2O、Na2PtCl6.xH2O、K2PtCl4.xH2O、PtCl4.xH2O、PtCl2、Na2HPtCl4.xH2O(式中,x以0~6的整數為佳,特別以0或6為佳)等氯化鉑、氯化鉑酸及氯化鉑酸鹽;醇改性氯化鉑酸(美國專利第3,220,972號公報);氯化鉑酸與烯烴之錯體(美國專利第3,159,601號公報、美國專利第3,159,662號公報、美國專利第
3,775,452號公報);將鉑黑或鈀等鉑族金屬載持於氧化鋁、二氧化矽、碳等載體者;銠-烯烴錯體;氯參(三苯基次膦)銠(所謂威爾金森觸媒);氯化鉑、氯化鉑酸或氯化鉑酸鹽與含有乙烯基的矽氧烷(特別為含有乙烯基的環狀矽氧烷)之錯體等。該使用量為觸媒量,通常對於作為鉑族金屬之反應聚合物總量為0.001~0.1質量%者為佳。
對於上述聚合反應,視必要可使用溶劑。作為溶劑,例如以甲苯、二甲苯等烴系溶劑為佳。
作為上述聚合條件,由不會使觸媒失活,且可在短時間完成聚合的觀點來看,聚合溫度例如為40~150℃,特佳為60~120℃。
又,聚合時間雖取決於聚合物的種類及量,欲可防止聚合系中之濕氣的介入,約0.5~100小時,特佳為0.5~30小時以內結束為佳。完成如此聚合反應後,使用溶劑時可藉由餾去此,得到(A)成分的聚矽氧高分子化合物。
(B)成分為藉由波長190~500nm的光進行分解而產生酸的光酸產生劑。作為(B)光酸產生劑,藉由波長190~500nm之光照射產生酸,可使用此成為硬化觸媒者。上述(A)成分因與光酸產生劑具有優良相溶性,故可使用種種種類的光酸產生劑。作為上述光酸產生劑,例
如可舉出鎓鹽、二偶氮甲烷衍生物、乙二肟衍生物、β-酮碸衍生物、二碸衍生物、硝基苯甲基磺酸鹽衍生物、磺酸酯衍生物、醯亞胺-基-磺酸鹽衍生物、肟磺酸鹽衍生物、亞胺磺酸鹽衍生物、三嗪衍生物等。
作為上述鎓鹽,例如可舉出下述一般式(13)所示化合物。
(R16)jM+K- (13)
(式中,R16表示可具有取代基之碳數1~12的直鏈狀、支鏈狀或環狀的烷基、碳數6~12的芳基或碳數7~12的芳烷基,M+表示碘鎓離子或硫鎓離子,K-表示非求核性對向離子,j表示2或3)
對於上述R16,作為烷基,例如可舉出甲基、乙基、丙基、丁基、環己基、2-氧代環己基、降冰片基、金剛烷基等。作為芳基,例如可舉出苯基;o-、m-或p-甲氧基苯基、乙氧基苯基、m-或p-tert-丁氧基苯基等的烷氧基苯基;2-、3-或4-甲基苯基、乙基苯基、4-tert-丁基苯基、4-丁基苯基、二甲基苯基等的烷基苯基等。作為芳烷基,例如可舉出苯甲基、苯基乙基等。
作為K-的非求核性對向離子,可舉出氯化物離子、溴化物離子等鹵化物離子;三氟甲磺酸酯、1,1,1-三氟乙烷磺酸鹽、九氟丁烷磺酸鹽等氟烷基磺酸鹽;甲苯磺酸酯、苯磺酸鹽、4-氟苯磺酸鹽、1,2,3,4,5-五氟苯磺酸鹽等的芳基磺酸鹽;甲磺酸酯、丁烷磺酸鹽等的烷基磺酸鹽等。
作為二偶氮甲烷衍生物,可舉出下述一般式(14)所示化合物。
(式中,R17可相同或相異,碳數1~12的直鏈狀、支鏈狀或者環狀的烷基或者鹵素化烷基、碳數6~12的芳基或者鹵素化芳基、或碳數7~12的芳烷基)
對於上述R17,作為烷基,例如可舉出甲基、乙基、丙基、丁基、戊基、環戊基、環己基、降冰片基、金剛烷基等。作為鹵素化烷基,例如可舉出三氟甲基、1,1,1-三氟乙基、1,1,1-三氯乙基、九氟丁基等。作為芳基,例如可舉出苯基;o-、m-或p-甲氧基苯基、乙氧基苯基、m-或p-tert-丁氧基苯基等的烷氧基苯基;2-、3-或4-甲基苯基、乙基苯基、4-tert-丁基苯基、4-丁基苯基、二甲基苯基等的烷基苯基等。作為鹵素化芳基,例如可舉出氟苯基、氯苯基、1,2,3,4,5-五氟苯基等。作為芳烷基,例如可舉出苯甲基、苯基乙基等。
作為具體光酸產生劑,例如可舉出三氟甲磺酸二苯基碘鎓、三氟甲磺酸(p-tert-丁氧基苯基)苯基碘鎓、p-甲苯磺酸二苯基碘鎓、p-甲苯磺酸(p-tert-丁氧基苯基)苯基碘鎓、三氟甲磺酸三苯基硫鎓、三氟甲磺酸(p-tert-丁氧基苯基)二苯基硫鎓、三氟甲磺酸雙(p-tert-丁氧基苯基)苯基硫鎓、三氟甲磺酸參(p-tert-丁氧
基苯基)硫鎓、p-甲苯磺酸三苯基硫鎓、p-甲苯磺酸(p-tert-丁氧基苯基)二苯基硫鎓、p-甲苯磺酸雙(p-tert-丁氧基苯基)苯基硫鎓、p-甲苯磺酸參(p-tert-丁氧基苯基)硫鎓、九氟丁烷磺酸三苯基硫鎓、丁烷磺酸三苯基硫鎓、三氟甲磺酸三甲基硫鎓、p-甲苯磺酸三甲基硫鎓、三氟甲磺酸環己基甲基(2-氧代環己基)硫鎓、p-甲苯磺酸環己基甲基(2-氧代環己基)硫鎓、三氟甲磺酸二甲基苯基硫鎓、p-甲苯磺酸二甲基苯基硫鎓、三氟甲磺酸二環己基苯基硫鎓、p-甲苯磺酸二環己基苯基硫鎓、二苯基(4-硫苯氧基苯基)硫鎓六氟銻酸鹽等鎓鹽;雙(苯磺醯基)二偶氮甲烷、雙(p-甲苯磺醯基)二偶氮甲烷、雙(二甲苯磺醯基)二偶氮甲烷、雙(環己基磺醯基)二偶氮甲烷、雙(環戊基磺醯基)二偶氮甲烷、雙(n-丁基磺醯基)二偶氮甲烷、雙(異丁基磺醯基)二偶氮甲烷、雙(sec-丁基磺醯基)二偶氮甲烷、雙(n-丙基磺醯基)二偶氮甲烷、雙(異丙基磺醯基)二偶氮甲烷、雙(tert-丁基磺醯基)二偶氮甲烷、雙(n-戊基磺醯基)二偶氮甲烷、雙(異戊基磺醯基)二偶氮甲烷、雙(sec-戊基磺醯基)二偶氮甲烷、雙(tert-戊基磺醯基)二偶氮甲烷、1-環己基磺醯基-1-(tert-丁基磺醯基)二偶氮甲烷、1-環己基磺醯基-1-(tert-戊基磺醯基)二偶氮甲烷、1-tert-戊基磺醯基-1-(tert-丁基磺醯基)二偶氮甲烷等二偶氮甲烷衍生物;雙-o-(p-甲苯磺醯基)-α-二甲基乙二肟、雙-o-(p-甲苯磺醯基)-α-二苯基乙二肟、雙-o-(p-甲苯磺醯
基)-α-二環己基乙二肟、雙-o-(p-甲苯磺醯基)-2,3-戊烷二酮乙二肟、雙-(p-甲苯磺醯基)-2-甲基-3,4-戊烷二酮乙二肟、雙-o-(n-丁烷磺醯基)-α-二甲基乙二肟、雙-o-(n-丁烷磺醯基)-α-二苯基乙二肟、雙-o-(n-丁烷磺醯基)-α-二環己基乙二肟、雙-o-(n-丁烷磺醯基)-2,3-戊烷二酮乙二肟、雙-o-(n-丁烷磺醯基)-2-甲基-3,4-戊烷二酮乙二肟、雙-o-(甲烷磺醯基)-α-二甲基乙二肟、雙-o-(三氟甲烷磺醯基)-α-二甲基乙二肟、雙-o-(1,1,1-三氟乙烷磺醯基)-α-二甲基乙二肟、雙-o-(tert-丁烷磺醯基)-α-二甲基乙二肟、雙-o-(全氟辛烷磺醯基)-α-二甲基乙二肟、雙-o-(環己烷磺醯基)-α-二甲基乙二肟、雙-o-(苯磺醯基)-α-二甲基乙二肟、雙-o-(p-氟苯磺醯基)-α-二甲基乙二肟、雙-o-(p-tert-丁基苯磺醯基)-α-二甲基乙二肟、雙-o-(二甲苯磺醯基)-α-二甲基乙二肟、雙-o-(樟腦磺醯基)-α-二甲基乙二肟等乙二肟衍生物;α-(苯硫鎓氧基亞胺)-4-甲基苯基乙腈等肟磺酸鹽衍生物;2-環己基羰基-2-(p-甲苯磺醯基)丙烷、2-異丙基羰基-2-(p-甲苯磺醯基)丙烷等β-酮碸衍生物;二苯基二碸、二環己基二碸等的二碸衍生物;p-甲苯磺酸2,6-二硝基苯甲基、p-甲苯磺酸2,4-二硝基苯甲基等硝基苯甲基磺酸鹽衍生物;1,2,3-參(甲烷磺醯氧基)苯、1,2,3-參(三氟甲烷磺醯氧基)苯、1,2,3-參(p-甲苯磺醯氧基)苯等磺酸酯衍生物;鄰苯二甲醯亞胺-基-三氟甲磺酸酯、鄰苯二甲醯亞胺-基-甲苯磺酸酯、5-降冰片烯2,3-二羧基
醯亞胺-基-三氟甲磺酸酯、5-降冰片烯2,3-二羧基醯亞胺-基-甲苯磺酸酯、5-降冰片烯2,3-二羧基醯亞胺-基-n-丁基磺酸鹽、n-三氟甲基磺醯氧基萘醯亞胺等醯亞胺-基-磺酸鹽衍生物;(5-(4-甲基苯基)磺醯氧基亞胺-5H-噻吩-2-亞基)-(2-甲基苯基)乙腈、(5-(4-(4-甲基苯基磺醯氧基)苯基磺醯氧基亞胺)-5H-噻吩-2-亞基)-(2-甲基苯基)-乙腈等亞胺磺酸鹽衍生物、2-甲基-2〔(4-甲基苯基)磺醯基〕-1-〔(4-甲基硫基)苯基〕-1-丙烷等。這些中亦可適用醯亞胺-基-磺酸鹽衍生物、亞胺磺酸鹽衍生物、肟磺酸鹽衍生物等。
上述(B)成分的光酸產生劑可單獨使用1種或可混合2種以上使用。
上述(B)成分的光酸產生劑之配合量由在光酸產生劑本身的光吸收及厚膜之光硬化性觀點來看,對於(A)成分的聚矽氧高分子化合物100質量份為0.05~20質量份,特佳為0.2~5質量份。配合量若在0.05質量份以上時,產生的酸會不足而無法圖型形成的情況不容易產生。配合量若在20質量份以下時,酸會過多而擴散於未曝光部,難以產生硬化之情況。
(C)成分為選自藉由甲醛或甲醛-醇進行改性的胺基縮合物、於1分子中平均具有2個以上羥甲基或烷氧基羥甲基之酚化合物、及將多價酚的羥基取代為環氧丙氧基之
化合物的1種或2種以上之化合物。
作為上述藉由甲醛或甲醛-醇進行改性的胺基縮合物,例如可舉出藉由甲醛或甲醛-醇經改性的三聚氰胺縮合物、或藉由甲醛或甲醛-醇經改性的尿素縮合物。上述經甲醛或甲醛-醇改性的三聚氰胺縮合物之合成例如有首先依據公知方法將三聚氰胺單體以甲醛進行羥甲基化而改性、或將此進一步以醇進行烷氧基化而改性,作為下述一般式(15)所示改性三聚氰胺。且,作為上述醇,以低級醇,例如以碳數1~4的醇為佳。
(式中,R18可相同或相異,羥甲基、有碳數1~4的烷氧基的烷氧基甲基或氫原子,但至少1個為羥甲基或上述烷氧基甲基)
作為上述R18,例如可舉出羥甲基、甲氧基甲基、乙氧基甲基等的烷氧基甲基及氫原子等。
作為上述一般式(15)的改性三聚氰胺,具體可舉出三甲氧基甲基單羥甲基三聚氰胺、二甲氧基甲基單羥甲基三聚氰胺、三羥甲基三聚氰胺、六羥甲基三聚氰
胺、六甲氧基羥甲基三聚氰胺等。
其次,將一般式(15)的改性三聚氰胺或該多聚物(例如二聚物、三聚物等寡聚物體)依據常法,與甲醛加成縮聚合至所望分子量,得到經甲醛或甲醛-醇進行改性的三聚氰胺縮合物。
又,藉由上述甲醛或甲醛-醇經改性的尿素縮合物之合成,例如可依據公知方法,將所望分子量的尿素縮合物以甲醛進行羥甲基化後使其改性,或可將此進一步以醇進行烷氧基化而改性。
作為上述藉由甲醛或甲醛-醇經改性的尿素縮合物,例如可舉出甲氧基甲基化尿素縮合物、乙氧基甲基化尿素縮合物、丙氧基甲基化尿素縮合物等。且,這些藉由甲醛或甲醛-醇經改性的尿素縮合物可單獨使用1種或混合2種以上後使用。
其次,作為於1分子中平均具有2個以上羥甲基或烷氧基羥甲基之酚化合物,例如可舉出(2-羥基-5-甲基)-1,3-苯二甲醇、2,2’,6,6’-四甲氧基甲基雙酚A等。這些酚化合物可單獨使用1種或混合2種以上後使用。
另一方面,作為將多價酚的羥基取代為環氧丙氧基之化合物,可舉雙酚A、參(4-羥基苯基)甲烷、將1,1,1-參(4-羥基苯基)乙烷的羥基在鹼存在下與環氧氯丙烷進行反應所得之1,1’-二環氧丙氧基雙酚A、參(4-環氧丙氧基苯基)甲烷、1,1,1-參(4-環氧丙氧基苯基)
乙烷等。將這些多價酚的羥基取代為環氧丙氧基之化合物可單獨使用1種或混合2種以上後使用。
上述(C)成分為單獨使用1種或組合2種以上後使用。
(D)成分為選自具有3個以上羥基的多價酚之1種或2種以上的化合物。作為上述(D)成分,可舉出將酚或雙酚A、p-tert-丁基酚、辛基酚、p-異丙苯酚等的烷基酚、p-苯基酚、甲酚等作為原料所合成的甲階酚醛型酚樹脂、酚醛清漆型酚樹脂等可舉出。進一步可舉出參(4-羥基苯基)甲烷、1,1,1-參(4-羥基苯基)乙烷等。
上述(D)成分為單獨使用1種或組合2種以上後使用。
上述(C)成分、(D)成分可作為交聯劑使用。
上述(C)成分及(D)成分與上述(A)成分的聚矽氧高分子化合物會引起硬化反應,與可容易獲得圖型形成的成分同時進一步提高硬化物強度之成分。如此(C)成分、(D)成分的重量平均分子量由光硬化性及耐熱性之觀點來看以150~10000為佳,特佳為200~300。
上述(C)成分及(D)成分的配合量由作為經過光硬化性及後硬化的電氣.電子零件保護用皮膜之信
賴性的觀點來看,對於上述(A)成分的聚矽氧高分子化合物100質量份而言,(C)成分及(D)成分之合計為0.5~50質量份,特別以1~30質量份為佳。又,(C)成分及(D)成分皆不會成為0質量份。具體為(C)/(D)(質量比)=1/99~99/1,以30/70~70/30為佳。若為如此配合量,與圖型間相關的解像度降低之問題難以產生。
且,本發明之光硬化性樹脂組成物視必要,可含有(E)鹼性化合物。作為上述鹼性化合物,以藉由光酸產生劑所產生的酸擴散至抗蝕皮膜內時的擴散速度可受到抑制的化合物為佳。而藉由上述鹼性化合物之配合,可提高解像度,可抑制曝光後的感度變化,減少基板依賴性或環境依賴性,可改善曝光幅度或圖型形狀等。
作為上述鹼性化合物,可舉出第一級、第二級、第三級脂肪族胺類、混成胺類、芳香族胺類、雜環胺類、具有羧基的含氮化合物、具有磺醯基的含氮化合物、具有羥基的含氮化合物、具有羥基苯基的含氮化合物、醇性含氮化合物、醯胺衍生物、醯亞胺衍生物等。
具體而言,作為第一級脂肪族胺類,可例示出氨、甲基胺、乙基胺、n-丙基胺、異丙基胺、n-丁基胺、異丁基胺、sec-丁基胺、tert-丁基胺、戊基胺、tert-戊基胺、環戊基胺、己基胺、環己基胺、庚基胺、辛基
胺、壬基胺、癸基胺、十二烷基胺、十六胺、伸甲基二胺、乙二胺、四伸乙基五胺等。
作為第二級脂肪族胺類,可舉出二甲基胺、二乙基胺、二-n-丙基胺、二異丙基胺、二-n-丁基胺、二異丁基胺、二-sec-丁基胺、二戊基胺、二環戊基胺、二己基胺、二環己基胺、二庚基胺、二辛基胺、二壬基胺、二癸基胺、雙十二烷基胺、雙十六胺、N,N-二甲基伸甲基二胺、N,N-二甲基乙二胺、N,N-二甲基四伸乙基五胺等。
作為第三級脂肪族胺類,可舉出三甲基胺、三乙基胺、三-n-丙基胺、三異丙基胺、三-n-丁基胺、三異丁基胺、三-sec-丁基胺、三戊基胺、三乙醇胺、tert-丁基二乙醇胺、三環戊基胺、三己基胺、三環己基胺、三庚基胺、三辛基胺、三壬基胺、十三烷基胺、參十二烷基胺、參十六胺、N,N,N’,N’-四甲基伸甲基二胺、N,N,N’,N’-四甲基乙二胺、N,N,N’,N’-四甲基四伸乙基五胺等。
又,作為混成胺類,例如可例示二甲基乙基胺、甲基乙基丙基胺、苯甲基胺、苯基乙基胺、苯甲基二甲基胺等。
作為芳香族胺類及雜環胺類的具體例子,可舉出苯胺衍生物(例如苯胺、N-甲基苯胺、N-乙基苯胺、N-丙基苯胺、N,N-二甲基苯胺、2-甲基苯胺、3-甲基苯胺、4-甲基苯胺、乙基苯胺、丙基苯胺、三甲基苯胺、2-硝基苯胺、3-硝基苯胺、4-硝基苯胺、2,4-二硝基苯胺、
2,6-二硝基苯胺、3,5-二硝基苯胺、N,N-二甲基甲苯胺等)、二苯基(p-甲苯基)胺、甲基二苯基胺、三苯基胺、伸苯基二胺、萘胺、二胺基萘、吡咯衍生物(例如吡咯、2H-吡咯、1-甲基吡咯、2,4-二甲基吡咯、2,5-二甲基吡咯、N-甲基吡咯等)、噁唑衍生物(例如噁唑、異噁唑等)、噻唑衍生物(例如噻唑、異噻唑等)、咪唑衍生物(例如咪唑、4-甲基咪唑、4-甲基-2-苯基咪唑等)、吡唑衍生物、呋咱衍生物、吡咯啉衍生物(例如吡咯啉、2-甲基-1-吡咯啉等)、吡咯烷衍生物(例如吡咯烷、N-甲基吡咯烷、吡咯烷酮、N-甲基吡咯啶酮等)、咪唑啉衍生物、咪唑烷衍生物、吡啶衍生物(例如吡啶、甲基吡啶、乙基吡啶、丙基吡啶、丁基吡啶、4-(1-丁基戊基)吡啶、二甲基吡啶、三甲基吡啶、三乙基吡啶、苯基吡啶、3-甲基-2-苯基吡啶、4-tert-丁基吡啶、二苯基吡啶、苯甲基吡啶、甲氧基吡啶、丁氧基吡啶、二甲氧基吡啶、1-甲基-2-吡啶、4-吡咯並吡啶、1-甲基-4-苯基吡啶、2-(1-乙基丙基)吡啶、胺基吡啶、二甲基胺基吡啶等)、噠嗪衍生物、嘧啶衍生物、吡嗪衍生物、吡唑啉衍生物、吡唑烷衍生物、哌啶衍生物、哌嗪衍生物、嗎啉衍生物、吲哚衍生物、異吲哚衍生物、1H-吲唑衍生物、吲哚啉衍生物、喹啉衍生物(例如喹啉、3-喹啉甲腈等)、異喹啉衍生物、噌啉衍生物、喹唑啉衍生物、喹喔啉衍生物、酞嗪衍生物、嘌呤衍生物、蝶啶衍生物、咔唑衍生物、菲啶衍生物、吖啶衍生物、吩嗪衍生物、1,10-菲咯啉衍生物、腺嘌
呤衍生物、腺苷衍生物、鳥嘌呤衍生物、鳥嘌呤核苷衍生物、尿嘧啶衍生物、尿苷衍生物等。
進一步作為具有羧基的含氮化合物,例如可例示出胺基安息香酸、吲哚羧酸、胺基酸衍生物(例如菸鹼酸、丙胺酸、精胺酸、天冬胺酸、谷胺酸、甘胺酸、組胺酸、異亮胺酸、甘胺醯基亮胺酸、亮胺酸、蛋胺酸、苯基丙胺酸、蘇胺酸、賴胺酸、3-胺基吡嗪-2-羧酸、甲氧基丙胺酸等)等。
作為具有磺醯基的含氮化合物,可例示出3-吡啶磺酸、p-甲苯磺酸吡啶鎓等。
作為具有羥基的含氮化合物、具有羥基苯基的含氮化合物、醇性含氮化合物,可例示2-羥基吡啶、胺基甲酚、2,4-喹啉二醇、3-吲哚甲醇水合物、單乙醇胺、二乙醇胺、三乙醇胺、N-乙基二乙醇胺、N,N-二乙基乙醇胺、三異丙醇胺、2,2’-亞胺二乙醇、2-胺基乙醇、3-胺基-1-丙醇、4-胺基-1-丁醇、4-(2-羥基乙基)嗎啉、2-(2-羥基乙基)吡啶、1-(2-羥基乙基)哌嗪、1-〔2-(2-羥基乙氧基)乙基〕哌嗪、哌啶乙醇、1-(2-羥基乙基)吡咯烷、1-(2-羥基乙基)-2-吡咯烷酮、3-哌啶-1,2-丙烷二醇、3-吡咯並-1,2-丙烷二醇、8-羥基吡咯烷、3-喹啉醇、3-托品醇、1-甲基-2-吡咯烷乙醇、1-氮雜環丙烷乙醇、N-(2-羥基乙基)鄰苯二甲醯亞胺、N-(2-羥基乙基)異菸鹼醯胺等。
作為醯胺衍生物,可例示甲醯胺、N-甲基甲
醯胺、N,N-二甲基甲醯胺、乙醯胺、N-甲基乙醯胺、N,N-二甲基乙醯胺、丙醯胺、苯甲醯胺等。
作為醯亞胺衍生物,可例示出鄰苯二甲醯亞胺、琥珀醯醯亞胺、馬來醯亞胺等。
可進一步添加選自下述一般式(16)所示鹼性化合物的1種或2種以上。
N(α)q(β)3-q (16)
(式中,q=1、2或3。側鏈α表示可相同或相異,下述一般式(17)~(19)所示中任一取代基。側鏈β表示可相同或相異之氫原子、或直鏈狀、支鏈狀或者環狀碳數1~20的烷基,醚鍵或者亦可含有羥基。又,側鏈α彼此可結合形成環)
其中,上述式中R300、R302、R305為碳數1~4
的直鏈狀或支鏈狀伸烷基,R301、R304為氫原子、或碳數1~20的直鏈狀、支鏈狀或者環狀的烷基,可含有羥基、醚鍵、酯鍵、內酯環中任1個或複數個。R303為單鍵、或碳數1~4的直鏈狀或者支鏈狀伸烷基,R306為碳數1~20的直鏈狀、支鏈狀或者環狀的烷基,可含有羥基、醚鍵、酯鍵、內酯環之1個或複數個。
作為上述一般式(16)所示化合物,具體可例示下述者。即,可例示參〔2-(甲氧基甲氧基)乙基〕胺、參〔2-(2-甲氧基乙氧基)乙基〕胺、參〔2-(2-甲氧基乙氧基甲氧基)乙基〕胺、參〔2-(1-甲氧基乙氧基)乙基〕胺、參〔2-(1-乙氧基乙氧基)乙基〕胺、參〔2-(1-乙氧基丙氧基)乙基〕胺、參〔2-{2-(2-羥基乙氧基)乙氧基}乙基〕胺、4,7,13,16,21,24-六氧雜-1,10-二氮雜雙環〔8.8.8〕二十六烷、4,7,13,18-四氧雜-1,10-二氮雜雙環〔8.5.5〕二十一烷、1,4,10,13-四氧雜-7,16-二氮雜雙環十八烷、1-氮雜-12-冠-4、1-氮雜-15-冠-5、1-氮雜-18-冠-6、參(2-甲醯氧基乙基)胺、參(2-乙醯氧基乙基)胺、參(2-丙醯基氧基乙基)胺、參(2-丁醯基氧基乙基)胺、參(2-異丁醯基氧基乙基)胺、參(2-香草基氧基乙基)胺、參(2-戊醯氧基乙基)胺、N,N-雙(2-乙醯氧基乙基)2-(乙醯氧基乙醯氧基)乙基胺、參(2-甲氧基羰基氧基乙基)胺、參(2-tert-丁氧基羰基氧基乙基)胺、參〔2-(2-氧代丙氧基)乙基〕胺、參〔2-(甲氧基羰基甲基)氧基乙基〕胺、參〔2-(tert-丁氧基羰基
甲基氧基)乙基〕胺、參〔2-(環己基氧羰基甲基氧基)乙基〕胺、參(2-甲氧基羰基乙基)胺、參(2-乙氧基羰基乙基)胺、N,N-雙(2-羥基乙基)2-(甲氧基羰基)乙基胺、N,N-雙(2-乙醯氧基乙基)2-(甲氧基羰基)乙基胺、N,N-雙(2-羥基乙基)2-(乙氧基羰基)乙基胺、N,N-雙(2-乙醯氧基乙基)2-(乙氧基羰基)乙基胺、N,N-雙(2-羥基乙基)2-(2-甲氧基乙氧基羰基)乙基胺、N,N-雙(2-乙醯氧基乙基)2-(2-甲氧基乙氧基羰基)乙基胺、N,N-雙(2-羥基乙基)2-(2-羥基乙氧基羰基)乙基胺、N,N-雙(2-乙醯氧基乙基)2-(2-乙醯氧基乙氧基羰基)乙基胺、N,N-雙(2-羥基乙基)2-〔(甲氧基羰基)甲氧基羰基〕乙基胺、N,N-雙(2-乙醯氧基乙基)2-〔(甲氧基羰基)甲氧基羰基〕乙基胺、N,N-雙(2-羥基乙基)2-(2-氧代丙氧基羰基)乙基胺、N,N-雙(2-乙醯氧基乙基)2-(2-氧代丙氧基羰基)乙基胺、N,N-雙(2-羥基乙基)2-(四氫糠基氧羰基)乙基胺、N,N-雙(2-乙醯氧基乙基)2-(四氫糠基氧羰基)乙基胺、N,N-雙(2-羥基乙基)2-〔(2-氧代四氫呋喃-3-基)氧羰基〕乙基胺、N,N-雙(2-乙醯氧基乙基)2-〔(2-氧代四氫呋喃-3-基)氧羰基〕乙基胺、N,N-雙(2-羥基乙基)2-(4-羥基丁氧基羰基)乙基胺、N,N-雙(2-甲醯氧基乙基)2-(4-甲醯氧基丁氧基羰基)乙基胺、N,N-雙(2-甲醯氧基乙基)2-(2-甲醯氧基乙氧基羰基)乙基胺、N,N-雙(2-甲氧基乙基)2-(甲氧基羰基)乙基胺、
N-(2-羥基乙基)雙〔2-(甲氧基羰基)乙基〕胺、N-(2-乙醯氧基乙基)雙〔2-(甲氧基羰基)乙基〕胺、N-(2-羥基乙基)雙〔2-(乙氧基羰基)乙基〕胺、N-(2-乙醯氧基乙基)雙〔2-(乙氧基羰基)乙基〕胺、N-(3-羥基-1-丙基)雙〔2-(甲氧基羰基)乙基〕胺、N-(3-乙醯氧基-1-丙基)雙〔2-(甲氧基羰基)乙基〕胺、N-(2-甲氧基乙基)雙〔2-(甲氧基羰基)乙基〕胺、N-丁基雙〔2-(甲氧基羰基)乙基〕胺、N-丁基雙〔2-(2-甲氧基乙氧基羰基)乙基〕胺、N-甲基雙(2-乙醯氧基乙基)胺、N-乙基雙(2-乙醯氧基乙基)胺、N-甲基雙(2-戊醯氧基乙基)胺、N-乙基雙〔2-(甲氧基羰基氧基)乙基〕胺、N-乙基雙〔2-(tert-丁氧基羰基氧基)乙基〕胺、參(甲氧基羰基甲基)胺、參(乙氧基羰基甲基)胺、N-丁基雙(甲氧基羰基甲基)胺、N-己基雙(甲氧基羰基甲基)胺、β-(二乙基胺基)-δ-戊內酯,但並未限定此等。
上述(E)成分的鹼性化合物為單獨使用1種或組合2種以上後使用。
上述(E)成分的鹼性化合物之配合量由感度的觀點來看,以對於上述(A)成分的聚矽氧高分子化合物100質量份而言0~3質量份為佳,以0.01~1質量份為特佳。若為如此配合量,不會使解像性變差,不容易產生引起圖型劣化之情況。
本發明之光硬化性樹脂組成物可進一步含有硬化促進劑(F)。上述硬化促進劑(F)為在硬化具有環氧基之化合物時,具有可促進硬化速度之功能的化合物。可舉出三級胺類或其鹽、咪唑類等。
作為被市售者,例如可舉出四國化成(股)製的2MZ-A、2MZ-OK、2PHZ、2P4BHZ、2P4MHZ-PW(皆為咪唑系化合物之商品名)、san-apro(股)製之U-CAT3503N、U-CAT3502T(皆為二甲基胺的嵌段異氰酸酯化合物之商品名)、DBU、DBN、U-CATSA102、U-CAT5002(皆為二環式脒化合物及其鹽的商品名)等。
上述(F)成分的硬化促進劑之配合量由感度的觀點來看,對於上述(A)成分的聚矽氧高分子化合物100質量份以0~3質量份為佳,以0~1質量份為特佳。若為如此配合量,不會使解像性變差,不容易產生引起圖型劣化之情況。且,添加時對於上述(A)成分的聚矽氧高分子化合物100質量份以0.05質量份以上者為佳。
於本發明之光硬化性樹脂組成物中,視必要可添加溶劑。作為溶劑,可選擇可溶解上述各成分的溶劑。其中,亦以有機溶劑對上述各成分的溶解性優良為佳。
作為上述有機溶劑,例如可舉出環己酮、環戊酮、甲基-2-n-戊基酮等酮類;3-甲氧基丁醇、3-甲基-3-甲氧基丁醇、1-甲氧基-2-丙醇、1-乙氧基-2-丙醇等醇類;丙二醇單甲基醚、乙二醇單甲基醚、丙二醇單乙基
醚、乙二醇單乙基醚、丙二醇二甲基醚、二乙二醇二甲基醚等醚類;丙二醇單甲基醚乙酸酯、丙二醇單乙基醚乙酸酯、乳酸乙酯、丙酮酸乙基、乙酸丁酯、3-甲氧基丙酸甲基、3-乙氧基丙酸乙基、乙酸tert-丁基、丙酸tert-丁基、丙二醇-單-tert-丁基醚乙酸酯、γ-丁內酯等酯類等,這些可單獨使用1種或混合2種以上使用。特別以光酸產生劑之溶解性最優的乳酸乙酯、環己酮、環戊酮、丙二醇單甲基醚乙酸酯、γ-丁內酯及其混合溶劑為佳。
上述溶劑的配合量由光硬化性樹脂組成物之相溶性、黏度及塗布性之觀點來看,對於上述(A)~(D)成分的配合量之合計100質量份而言為50~2000質量份,特別以50~1000質量份為佳。
於本發明之光硬化性樹脂組成物中,除上述各成分以外,可進一步添加添加劑。作為添加劑,例如可添加欲使塗布性提高而慣用的界面活性劑。作為上述界面活性劑,以非離子性者為佳,例如氟系界面活性劑,具體可舉出全氟烷基聚氧乙烯乙醇、氟化烷基酯、全氟烷基胺氧化物、含氟有機矽氧烷系化合物等。
這些可使用被市售者,例如舉出FLUORAD「FC-4430」(住友3M(股)製)、Surflon「S-141」及「S-145」(皆為旭硝子(股)製)、Unidyne「DS-401」、「DS-4031」及「DS-451」(皆為大金工業(股)製)、Megafac「F-8151」(大日本油墨工業(股)製)、「X-70-093」(信越化學工業(股)製)等。這些
中亦以FLUORAD「FC-4430」(住友3M(股)製)及「X-70-093」(信越化學工業(股)製)為佳。
又,作為其他添加劑,可添加欲提高光酸產生劑的光吸收效率之吸光劑。作為如此吸光劑,例如可舉出二芳基亞碸、二芳基碸、9,10-二甲基蒽、9-芴酮等。
調製上述光硬化性樹脂組成物的方法並無特別限定。例如可將上述各成分進行攪拌混合,其後藉由濾器等進行過濾後可調製出光硬化性樹脂組成物。
其次,對於本發明之光硬化性乾薄膜做說明。
本發明之光硬化性乾薄膜具有將上述光硬化性樹脂組成物經薄膜化的光硬化性樹脂層,其為該光硬化性樹脂層之厚度100μm~300μm者。又,該光硬化性樹脂層的硬化後之彈性率為0.1~2GPa,且拉伸強度以1~80MPa為佳。
通常本發明之光硬化性乾薄膜為具有以下結構者,該結構為將上述光硬化性樹脂組成物於支持薄膜上進行塗布.乾燥等所得之光硬化性樹脂層以支持薄膜及保護薄膜夾住者。
藉由使用該光硬化性乾薄膜之型形成方法所得之厚度100μm~300μm的硬化皮膜具有優良的與基板之密著性、耐熱性、電氣絕緣性、作為絕緣保護膜的信賴性、藥品耐性,可成為使用於貼合基板的用途之皮膜。
本發明之光硬化性乾薄膜的光硬化性樹脂層
可含有溶劑。作為溶劑,可舉出與上述有機溶劑之相同者。溶劑的含有量對於光硬化性乾薄膜的光硬化性樹脂層100質量份而言以0~30質量份為佳,以0~15質量份為特佳。
其次,對於使用於本發明之光硬化性乾薄膜的支持薄膜可為單一亦可為層合複數聚合物薄膜的多層薄膜。作為材質可舉出聚乙烯、聚丙烯、聚碳酸酯、聚乙烯對苯二甲酸乙二醇酯等合成樹脂薄膜等,以具有適度可撓性、機械的強度及耐熱性之聚乙烯對苯二甲酸乙二醇酯為佳。又,對於這些薄膜,可為進行電暈處理或剝離劑塗布的各種處理者。這些可使用市售品,例如可舉出SeraphilWZ(RX)、SeraphilBX8(R)(以上為Toray薄膜加工(股)製)、E7302、E7304(以上為東洋紡績(股)製)、PurexG31、PurexG71T1(以上為帝人DuPont薄膜(股)製)、PET38×1-A3、PET38×1-V8、PET38×1-X08(以上為Nipper(股)製)等。
對於本發明之光硬化性乾薄膜所使用的保護薄膜可使用與上述支持薄膜的相同者,以具有適度可撓性的聚乙烯對苯二甲酸乙二醇酯及聚乙烯為佳。這些可使用市售品,作為聚乙烯對苯二甲酸乙二醇酯可舉出已經例示者,作為聚乙烯,例如可舉出GF-8(Tamapoly(股)製)、PE薄膜0類型(Nipper(股)製)。
上述支持薄膜及保護薄膜之厚度由光硬化性乾薄膜製造之安定性及對捲芯的捲性適度,所謂彎曲防止
的觀點來看,皆以10~100μm為佳,特佳為25~75μm。
其次,對於本發明之光硬化性乾薄膜的製造方法做說明。上述光硬化性乾薄膜之製造裝置為可使用一般製造黏著劑製品時的薄膜塗布機。作為上述薄膜塗布機,例如可舉出缺角輪塗布機、點逆向塗布機、複合塗布機、模具塗布機、唇形塗布機、唇型逆向塗布機、直接凹印塗布機、偏移凹印塗布機、3根底層逆向塗布機、4根底層逆向塗布機等。
將支持薄膜由薄膜塗布機的捲出軸進行捲出,通過薄膜塗布機之塗布頭時,於支持薄膜上將本發明之光硬化性樹脂組成物以所定厚度進行塗布而形成光硬化性樹脂層後,以所定溫度與所定時間通過熱風循環烤箱,將在上述支持薄膜上進行乾燥的光硬化性樹脂層與在薄膜塗布機的另一捲出軸所捲出的保護薄膜共同地,通過所定壓力之層合輥,與上述支持薄膜上的上述光硬化性樹脂層進行貼合後,藉由於薄膜塗布機的捲取軸進行捲取而製造。此時,作為熱風循環烤箱之溫度,以25~150℃為佳,作為通過時間以1~100分鐘為佳,作為層合輥的壓力以0.01~5MPa為佳。
所得之光硬化性乾薄膜為剝離保護薄膜,貼合於電氣.電子零件後可使用。
次使用如上述所製造的光硬化性乾薄膜對於圖型形成方法做說明。
作為使用上述光硬化性乾薄膜的圖型形成方
法,可舉出含有下述步驟的方法。
(i)使用上述光硬化性乾薄膜,於基板上形成光硬化性樹脂層的步驟、(ii)介著光罩以波長190~500nm的光進行曝光的步驟、(iii)進行曝光後的加熱處理(曝後烤(Post Exposure Bake,PEB))後以顯像液進行顯像的步驟。
以下對於各步驟進行詳細說明。
在步驟(i)中,自光硬化性乾薄膜剝離保護薄膜後,將剝離保護薄膜的光硬化性乾薄膜使用薄膜貼合裝置密著於基板。藉此於基板上形成光硬化性樹脂層。
作為上述基板,例如可舉出矽晶圓、貫通電極用矽晶圓、於裏面研磨使其薄膜化的矽晶圓、塑質或陶瓷基板、藉由離子濺鍍法或鍍敷法等於基板全面或基板的一部分形成Ni、Au等金屬層的基板等。
作為上述薄膜貼合裝置,以真空層合體為佳。剝離上述光硬化性乾薄膜的保護薄膜,將露出的上述光硬化性樹脂層對於所定真空度的真空室內,使用所定壓力之貼合輥,在所定溫度桌子上密著於基板。且,作為桌子的溫度以50~120℃為佳,作為貼合輥的壓力以0~5.0MPa為佳,作為真空室的真空度以50~500Pa為佳。
此時欲得到必要厚度之光硬化性樹脂層,視必要可複數次貼合薄膜。
欲有效率地進行上述光硬化性樹脂層之光硬
化反應,及欲提高光硬化性樹脂層與基板的密著性,視必要可進行預備加熱(預烘烤)。預烘烤例如在40~140℃下進行1分鐘~1小時程度。
且,光硬化性乾薄膜之支持薄膜可配合製程於預烘烤前或PEB前進行機械性剝離等方法而除去。
其次,在步驟(ii)中,介著光罩以波長190~500nm的光進行曝光。上述光罩例如可挖空為所望圖型者。且,光罩的材質以可遮蔽上述波長190~500nm之光者為佳,例如可使用鉻等,但並未限定於此。
作為上述波長190~500nm的光,例如可舉出藉由放射線產生裝置所產生的種種波長的光,例如可舉出g線、h線、i線等紫外線光、遠紫外線光(248nm、193nm)等,較佳為波長248~436nm。曝光量以10~5000mJ/cm2為佳。
其次,在步驟(iii)中首先欲提高顯像感度而進行PEB。上述曝光後之加熱處理以在40~140℃進行0.5~30分鐘者為佳。
上述PEB後以顯像液進行顯像。作為顯像液,以作為溶劑所使用的有機溶劑系,例如異丙醇(IPA)等醇類或環己酮等酮類為佳,更佳為丙二醇單甲基醚等甘醇類、丙二醇單甲基醚乙酸酯等酯類等,可使用在光硬化性樹脂組成物所使用的溶劑。上述顯像方法可舉出一般方法,例如將經圖型形成的基板浸漬於上述顯像液等。其後視必要可進行洗淨、沖洗、乾燥等,得到具有所
望圖型之光硬化性樹脂層的皮膜。藉此顯像,未曝光部被溶解,藉由曝光經交聯的部分以圖型方式殘存。
然而,若無須形成圖型時,例如在僅要形成均勻皮膜的情況時,採用無介在上述光罩而在波長190~500nm之光下進行曝光的步驟,此外僅進行與上述方法的相同皮膜形成即可。
又,作為上述步驟(iii)之後的步驟(iv),將所得之圖型(或皮膜)使用烤箱或加熱板等,在溫度100~250℃,較佳為150~220℃進行後硬化為佳。若後硬化溫度在100~250℃,可提高光硬化性樹脂層之交聯密度,可除去殘存之揮發成分,由對基板的密著力、耐熱性或強度,以及電特性的觀點來看為佳。而後硬化時間可設定為10分鐘~10小時。
使用本發明之光硬化性樹脂組成物或光硬化性乾薄膜形成圖型(或皮膜),進行如上述的後硬化所得之硬化皮膜其具有優良的耐熱性、可撓性、電氣絕緣性、機械特性及與基板的密著性,可適用於半導體元件等電氣.電子零件保護用皮膜。
特別為該保護用皮膜由該耐熱性、藥品耐性、絕緣性及可撓性來看,含有再配線用之半導體元件用絕緣膜、多層印刷基板用絕緣膜、焊接光罩、TSV之貫通電極用絕緣膜、覆蓋薄膜以外,可使用於貼合基板之用途等者。
且,於基板的貼合用途上使用本發明之光硬
化性樹脂組成物或光硬化性乾薄膜時,與上述步驟(i)同樣地,於一方基板上形成光硬化性樹脂層,在此貼合另一方基板即可。
以下表示實施例及比較例對本發明做更具體說明,但本發明並未限定於下述實施例者。且,對於下述例,份表示質量份。首先對於本發明之合成例所使用的化合物(M-1)~(M-6)的化學結構式如以下所示。
具備氮氣導入管、溫度計、Dimroth型凝結器及滴入漏斗的1L可分離燒瓶中,裝入式(M-2)所示不飽和基含有化合物215g(0.5mol)、甲苯500g、碳載持鉑觸媒(5質量%)0.10g,在75℃將式(M-4)所示1,4-雙(二甲基矽基)苯48.5g(0.25mol)慢慢滴入。於該滴下需要10分鐘。滴入終了後,在75℃繼續進行10小時熟成。熟成終了後,進行氣體層析分析,確認1,4-雙(二甲基矽基)苯殘存量成為2%以下。將所得之溶液以濾器藉由加壓過濾而取出鉑觸媒。且對於所得之溶液使用旋轉蒸發器,在80℃/0.6kPa進行減壓濃縮後,得到褐色固體250g。對於所得之褐色固體,進行紅外線吸收光譜分析及、1H核磁共振光譜分析,確認得到具有含烯丙基之酚性羥基的芴結構於兩末端具有的矽亞苯基化合物。
其次於具備氮氣導入管、溫度計、Dimroth型凝結器及滴入漏斗的1L可分離燒瓶中,裝入上述所得之具有含有烯丙基的酚性羥基之芴結構於兩末端具有的矽亞苯基化合物210.8g(0.2mol),將此溶解於環氧氯丙烷
278g(3.0mol),再加入四甲基銨氯化物0.44g,在100℃進行5小時攪拌。其次,在減壓下(20kPa)於70℃將40%氫氧化鈉水溶液44g經3小時滴入。其間將所生成的水藉由與環氧氯丙烷之共沸除去至系統外,餾出之環氧氯丙烷則回到系統內。滴下終了後,進一步繼續進行30分鐘反應。其後藉由過濾取出生成的鹽類,進一步進行水洗後,餾去環氧氯丙烷後,得到褐色固體180g。對於所得之褐色固體,進行紅外線吸收光譜分析及1H核磁共振光譜分析,確認得到具有於末端具有烯丙基與環氧基的芴結構之含有矽亞苯基骨架的化合物(M-1)。
於具備攪拌機、溫度計、氮取代裝置及迴流冷卻器之5L燒瓶內,加入化合物(M-1)256.0g、化合物(M-2)53.8g,將此溶解於甲苯1300g後,於60℃加溫。其後將碳載持鉑觸媒(5質量%)1.6g,化合物(M-4)53.5g與化合物(M-5)151.0g之混合物經1小時滴入於燒瓶內。此時的燒瓶內溫度上升至78℃。滴入終了後,進一步在90℃下進行5小時熟成後,冷卻至室溫,加入甲基異丁基酮1000g,將本反應溶液以濾器進行加壓過濾後除去鉑觸媒。進一步於所得之高分子化合物溶液中加入純水500g並攪拌、靜置分液,除去下層的水層。該分液水洗操作重複6次,除去高分子化合物溶液中之微量酸成分。將該高分子化合物溶液中之溶劑在減壓餾去之同時,添加環戊酮
330g,得到固體成分濃度60質量%的環戊酮作為主溶劑之聚矽氧高分子化合物溶液(A-1)。將該高分子化合物溶液中之高分子化合物的分子量藉由GPC進行測定後,聚苯乙烯換算為重量平均分子量45000。又,由原料之莫耳比算出(A)成分的聚矽氧高分子化合物中之式(1)的a為0.615、式(2)的b為0.385。
於具備攪拌機、溫度計、氮取代裝置及迴流冷卻器之5L燒瓶內,加入化合物(M-1)170.6g、化合物(M-2)35.9g,將此溶解於甲苯1300g後,於60℃加溫。其後將碳載持鉑觸媒(5質量%)1.6g,化合物(M-4)6.5g與化合物(M-6)296.0g的混合物經1小時滴入於燒瓶內。此時的燒瓶內溫度上升至75℃。滴入終了後再於90℃下進行3小時熟成後冷卻至室溫,加入甲基異丁基酮1000g,將本反應溶液以濾器進行加壓過濾後除去鉑觸媒。進一步於所得之高分子化合物溶液中加入純水500g並攪拌、靜置分液,除去下層的水層。該分液水洗操作重複6次,除去高分子化合物溶液中之微量酸成分。將該高分子化合物溶液中之溶劑進行減壓餾去之同時,添加環戊酮320g,得到固體成分濃度60質量%之環戊酮作為主溶劑的聚矽氧高分子化合物溶液(A-2)。將該高分子化合物溶液中之高分子化合物的分子量藉由GPC進行測定後,聚苯乙烯換算為重量平均分子量32000。又,藉由原料的莫耳比
算出(A)成分的聚矽氧高分子化合物中之式(1)的a為0.615,式(2)的b為0.385。
於具備攪拌機、溫度計、氮取代裝置及迴流冷卻器之5L燒瓶內,加入化合物(M-1)93.3g、化合物(M-2)26.9g,將此溶解於甲苯1300g後,於60℃加溫。其後將碳載持鉑觸媒(5質量%)1.6g,化合物(M-5)409.0g經1小時滴入燒瓶內。此時的燒瓶內溫度升溫至76℃。滴入終了後進一步在90℃進行18小時熟成後,冷卻至室溫,加入甲基異丁基酮1000g,將本反應溶液以濾器進行加壓過濾後除去鉑觸媒。進一步於所得之高分子化合物溶液中加入純水500g並攪拌、靜置分液,除去下層的水層。該分液水洗操作重複6次,除去高分子化合物溶液中之微量酸成分。將該高分子化合物溶液中之溶劑進行減壓餾去之同時,添加環戊酮340g,得到固體成分濃度60質量%之環戊酮作為主溶劑的聚矽氧高分子化合物溶液(A-3)。將該高分子化合物溶液中之高分子化合物的分子量藉由GPC進行測定後,聚苯乙烯換算為重量平均分子量250000。又,由原料的莫耳比算出(A)成分的聚矽氧高分子化合物中的式(1)的a為0.538,式(2)的b為0.462。
於具備攪拌機、溫度計、氮取代裝置及迴流冷卻器之5L燒瓶內,加入化合物(M-1)128.0g、化合物(M-3)41.1g,將此溶解於甲苯1300g後,於60℃加溫。其後將碳載持鉑觸媒(5質量%)1.6g,化合物(M-4)19.5g與化合物(M-5)402.7g之混合物經1小時滴入於燒瓶內。此時的燒瓶內溫度上升至74℃。滴入終了後,再以90℃進行8小時熟成後,冷卻至室溫,加入甲基異丁基酮1000g,將本反應溶液以濾器進行加壓過濾後除去鉑觸媒。進一步於所得之高分子化合物溶液中加入純水500g並攪拌、靜置分液,除去下層的水層。該分液水洗操作重複6次,除去高分子化合物溶液中之微量酸成分。將該高分子化合物溶液中之溶劑進行減壓餾去之同時,添加環戊酮380g,得到將固體成分濃度60質量%之環戊酮作為主溶劑的聚矽氧高分子化合物溶液(A-4)。將該高分子化合物溶液中之高分子化合物的分子量藉由GPC進行測定後,聚苯乙烯換算為重量平均分子量75000。又,藉由原料之莫耳比算出(A)成分的聚矽氧高分子化合物中的式(1)之a為0.429,式(2)的b為0.571。
於具備攪拌機、溫度計、氮取代裝置及迴流冷卻器之5L燒瓶內,加入化合物(M-1)64.0g、化合物(M-3)96.9g,將此溶解於甲苯1300g後,於60℃加溫。其後投入碳載持鉑觸媒(5質量%)1.6g,將化合物(M-4)
34.0g與化合物(M-5)302.0g之混合物經1小時滴入於燒瓶內。此時的燒瓶內溫度上升至79℃。滴入終了後,進一步在90℃下進行5小時熟成後,冷卻至室溫,加入甲基異丁基酮1000g,將本反應溶液以濾器進行加壓過濾後除去鉑觸媒。進一步於所得之高分子化合物溶液中加入純水500g並攪拌、靜置分液,除去下層的水層。該分液水洗操作重複6次,除去高分子化合物溶液中之微量酸成分。將該高分子化合物溶液中之溶劑進行減壓餾去之同時,添加環戊酮320g,得到將固體成分濃度60質量%之環戊酮作為主溶劑的聚矽氧高分子化合物溶液(A-5)。將該高分子化合物溶液中之高分子化合物的分子量藉由GPC進行測定後,聚苯乙烯換算為重量平均分子量43000。又,由原料的莫耳比算出(A)成分的聚矽氧高分子化合物中之式(1)的a為0.182,式(2)的b為0.818。
於具備攪拌機、溫度計、氮取代裝置及迴流冷卻器之5L燒瓶內,加入化合物(M-1)352.0g,將此溶解於甲苯1300g後,於60℃加溫。其後將碳載持鉑觸媒(5質量%)1.6g,化合物(M-4)34.0g與化合物(M-5)302.0g之混合物經1小時滴入於燒瓶內。此時的燒瓶內溫度上升至78℃。滴入終了後,進一步在90℃下進行5小時熟成後,冷卻至室溫,加入甲基異丁基酮1000g,將本反應溶
液以濾器進行加壓過濾後除去鉑觸媒。進一步於所得之高分子化合物溶液中加入純水500g並攪拌、靜置分液,除去下層的水層。該分液水洗操作重複6次,除去高分子化合物溶液中之微量酸成分。將該高分子化合物溶液中之溶劑進行減壓餾去之同時,添加環戊酮410g,得到將固體成分濃度60質量%的環戊酮作為主溶劑之聚矽氧高分子化合物溶液(B-1)。將該高分子化合物溶液中之高分子化合物的分子量藉由GPC進行測定後聚苯乙烯換算為重量平均分子量45000。
依據表1記載之配合量,添加聚矽氧高分子化合物溶液((A)成分)、光酸產生劑((B)成分)、交聯劑((C)成分、(D)成分)、鹼性化合物((E)成分)、其他添加劑及溶劑,其後在常溫進行攪拌、混合、溶解後,進行以鐵氟龍(註冊商標)製1.0μm濾器之精密過濾,得到實施例1~10及比較例1之光硬化性樹脂組成物。
且作為薄膜塗布機使用模具塗布,作為支持薄膜使用聚乙烯對苯二甲酸乙二醇酯薄膜(厚度50μm),將實施例1~10及比較例1之光硬化性樹脂組成物各塗布於上述支持薄膜上。其次將設定在100℃之熱風循環烤箱(長度4m)通過8分鐘後,在支持薄膜上形成光硬化性樹脂層。由上述光硬化性樹脂層上面,作為保
護薄膜使用聚乙烯薄膜(厚度50μm),將上述保護薄膜與層合輥以壓力1MPa進行貼合,製作出光硬化性乾薄膜。各光硬化性樹脂層之膜厚如表1所記載。且,膜厚藉由接觸式厚膜測定器測定。
實施例1~10及比較例1之光硬化性乾薄膜為剝離保護薄膜,使用真空層合體TEAM-100RF(Takatori公司製),設定為真空室內之真空度80Pa,將支持薄膜上的光硬化性樹脂層密著於矽基板。將溫度條件設定於110℃。恢復常壓後,將上述基板由真空層合體取出,剝離支持薄膜。其次,欲提高與基板之密著性,藉由加熱板進行在130℃之5分鐘預烘烤。對於所得之光硬化性樹脂層介著光罩,在405nm的曝光條件下使用接觸對準型曝光裝置,以1500mJ/cm2進行曝光,形成圖型。光照射後藉由加熱板在130℃進行5分鐘PEB後冷卻,將述基板以PGMEA(丙二醇單甲基醚乙酸酯)以噴霧顯像方式進行600秒顯像。
將藉由上述方法形成圖型的基板上之光硬化性樹脂層,使用烤箱在180℃下進行2小時的邊吹氮氣邊進行後硬化。對於所得之膜厚將孔洞圖型之解像性藉由掃描型電子顯微鏡(SEM)測定。且,將在25℃之光硬化性樹脂層的硬化後之彈性率藉由動態黏彈性測定裝置(DMA)進行測定。拉伸強度為依據JIS K 7127進行測定。結果如表1所記載。
又,使用於本發明之實施例的表1所記載的
光酸產生劑如以下所示。
又,於本發明之實施例所使用的表1所記載的交聯劑((C)成分)如以下所示。
又,於本發明之實施例所使用的表1所記載的多價酚化合物((D)成分)如以下所示。
MEH-8000H(明和化成(股)製商品名)
於表1所記載的鹼性化合物如以下所示。
如表1所記載的U-CAT5002為san-apro(股)製之硬化促進劑。
又,對於在合成例1~7所得的各溶液中之高分子化合物中的環氧基與酚性羥基之莫耳比(環氧基/(環氧基+酚性羥基))經計算後導出。計算結果如表2所示。
如表1、2所示,若為使用含有(A)~(D)成分等光硬化性樹脂組成物所製作的光硬化性乾薄膜(實施例1~10),在使用於圖型形成時,在高膜厚可容易進行微細圖型形成。另一方面,對於(A)成分未滿足本發明之要件的比較例1中,無法形成圖型。
且,本發明非限定於上述實施形態者。上述實施形態僅為例示,若具有與本發明之申請專利範圍所記載的技術思想為實質上相同的構成,且可達成相同效果者皆包含於本發明之技術範圍中。
Claims (3)
- 一種光硬化性樹脂組成物,其特徵為含有(A)具有作為重複單位的下述一般式(1)所示含有環氧基的成分,及下述一般式(2)所示含有酚性羥基的成分,重量平均分子量為3000~500000者;
- 如請求項1之光硬化性樹脂組成物,其為進一步含有(E)鹼性化合物者。
- 一種光硬化性乾薄膜,其特徵為具有將如請求項1或請求項2之光硬化性樹脂組成物進行薄膜化的光硬化性樹脂層,該光硬化性樹脂層的厚度為100μm~300μm者。
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