TWI704415B - 光硬化性樹脂組成物及使用其之膜形成方法 - Google Patents
光硬化性樹脂組成物及使用其之膜形成方法 Download PDFInfo
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- TWI704415B TWI704415B TW105119752A TW105119752A TWI704415B TW I704415 B TWI704415 B TW I704415B TW 105119752 A TW105119752 A TW 105119752A TW 105119752 A TW105119752 A TW 105119752A TW I704415 B TWI704415 B TW I704415B
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Abstract
本發明提供一種新穎的光硬化性樹脂組成物。
一種光硬化性樹脂組成物，其特徵為含有，具有下述式(1)所表示之結構單位，且末端具有下述式(2)所表示之結構的重量平均分子量1,000至50,000之聚合物、自由基型光聚合起始劑及溶劑。
Description
本發明為有關一種包含導入可進行自由基交聯之部位的聚合物之光硬化性樹脂組成物。
近年來，伴隨攜帶式電話、IC卡片等電子機器之高機能化及小型化，而逐漸尋求半導體裝置的高集積化。該方法為就半導體元件該物品之微細化、半導體元件間以縱向層疊的堆疊(STACK)結構進行研究。堆疊結構的製作中，於半導體元件間的接合為使用黏著劑。但是，已知公知黏著劑的丙烯酸樹脂、環氧樹脂及聚矽氧樹脂，其耐熱性至多僅為250℃左右而已，而會產生無法使用於金屬凸點的電極接合、離子擴散步驟等需要250℃以上的高溫之步驟等問題。
專利文獻1中，為揭示一種含有光半導體用黏著劑所使用之異三聚氰酸環之聚合物，及含有其之組成物之內容。其記載著含有該異三聚氰酸環之聚合物，於鹼金屬化合物之存在下，經由N-單取代三聚異氰酸與二鹵
化合物與進行反應，或經由N,N’,N”-三取代三聚異氰酸與矽烷化合物進行羥基矽烷基化反應而可製得之內容。此外，亦記載著前述組成物，可作為光半導體用黏著劑，於50℃~250℃之烘箱中進行30分鐘~4小時加熱，即可進行黏著之內容等。
另一方面，以液晶顯示器(LCD)、有機EL(OLED)顯示器為代表的薄型顯示器(FPD)的市場亦急速地擴大。液晶顯示器，多使用玻璃基板作為顯示面板之基材，此外，為降低因薄型化、輕量化、可撓化、捲對捲(Roll-to-Roll)製程等之加工費用，而進行使用塑膠基板的可撓式顯示器之開發。但是，已知公知塑膠基板所使用之樹脂材料，例如，PET樹脂、PEN樹脂、PC樹脂等其耐熱性僅至250℃左右而已，對於以往薄膜電晶體(TFT)形成製程所需要的250℃以上之高溫步驟，仍存在有無法使用之問題。
另一方面，專利文獻2為揭示一種可製得高可見光透過率的具有優良耐熱性及耐溶劑性的硬化膜之組成物。此外，同文獻中，亦記載可使用前述組成物作為黏著劑使用等內容。
[專利文獻1] 特開2008-143954號公報
[專利文獻2] 國際公開第2013/035787號公報
專利文獻1所記載之組成物所製得之硬化物，其於470nm的光線透過率評價為90%以上，再進行耐熱性之評估。但，其雖記載有將前述硬化物放置於150℃之烘箱中，放置120小時後的470nm之透過率的測定之內容，但250℃以上之溫度下的耐熱性仍不明瞭。因此，將專利文獻1所記載之組成物使用於需要250℃以上之高溫步的驟時，由該組成物所得之硬化物可能會有不具有高可見光透過率之疑慮。
另一方面，使用專利文獻2所記載之組成物時，欲於基板上形成具有高可見光透過率，且具有優良耐熱性及耐溶劑性的硬化膜時，必須於200℃或其以上之溫度進行例如5分鐘之燒焙。因此，專利文獻2所記載之組成物作為黏著於公知的塑膠基板時，於該組成物燒焙之際，塑膠基板會有產生破損的可能性。
因此，急需尋求一種不需要進行200℃或其以上溫度的加熱步驟，即可形成具有高可見光透過率，及優良耐熱性及耐溶劑性的硬化膜之組成物。
本發明者們，為解決上述問題，經過深入研究結果，對構成組成物的聚合物之末端結構花費極大工
夫，而完成一種不必要進行於上述溫度下的加熱步驟下，即可由該組成物形成具備有所期待之性質的硬化膜。
即，本發明之第一態樣為，一種光硬化性樹脂組成物，其特徵為含有，具有下述式(1)所表示之結構單位，且末端具有下述式(2)所表示之結構的重量平均分子量1,000至50,000之聚合物、自由基型光聚合起始劑及溶劑。
(式中，X表示碳原子數1至6之烷基、乙烯基、烯丙基或縮水甘油基，m及n表示各自獨立之0或1，Q表示碳原子數1至16之二價的烴基，Z表示碳原子數1至4之二價的鍵結基，該二價的鍵結基為與前述式(1)中之-O-基鍵結，R1表示氫原子或甲基)。
前述式(1)中，Q所表示之二價的烴基，例如，表示直鏈狀或支鏈狀之伸烷基、以雙鍵鍵結的含有2個碳原子之基，或主鏈含有至少可具有1個取代基之脂環式烴基或芳香族烴基之基。
前述式(2)中，Z所表示之二價的鍵結基，例如為表示至少可具有1個作為取代基的羥基之直鏈狀或
支鏈狀之伸烷基。
前述光硬化性樹脂組成物，可再含有二官能(甲基)丙烯酸酯及/或多官能硫醇。
前述光硬化性樹脂組成物，可作為黏著劑或透鏡材料使用。
本發明之第二態樣為，一種膜形成方法，其特徵為具有，將本發明之第一態樣的光硬化性樹脂組成物塗佈於基板上之步驟、將塗佈於前述基板上的光硬化性樹脂組成物於50℃至160℃之溫度進行預燒焙之步驟、對前述預燒焙後的形成於前述基板上之塗膜進行曝光之步驟，及使前述塗膜顯影之步驟。
本發明之光硬化性樹脂組成物，因含有末端導入可進行自由基交聯之部位的聚合物及自由基型光聚合起始劑，故不必要進行200℃或其以上之溫度的加熱步驟，即可形成具有高可見光透過率及優良耐熱性及耐溶劑性的硬化膜。該硬化膜適合作為透鏡材料。本發明之光硬化性樹脂組成物所形成的硬化膜，也具有優良的抗透濕性。此外，本發明之光硬化性樹脂組成物，因具有高黏著力，故適合作為有機EL顯示器用及影像感測器用黏著劑使用。
本發明之光硬化性樹脂組成物，為含有具有前述式(1)所表示之結構單位，且末端具有前述式(2)所表示之結構的重量平均分子量1,000至50,000之聚合物。該重量平均分子量，經由後述凝膠滲透層析儀(以下，於本說明書中，亦簡稱為GPC)分析，並基於標準聚苯乙烯換算值，較佳為1,000至20,000。
前述式(1)中，X所表示之碳原子數1至6之烷基，例如，甲基、乙基、n-丙基、i-丙基、n-丁基、i-丁基、s-丁基、t-丁基、n-戊基、1-甲基-n-丁基、2-甲基-n-丁基、3-甲基-n-丁基、1,1-二甲基-n-丙基、1,2-二甲基-n-丙基、2,2-二甲基-n-丙基、1-乙基-n-丙基、n-己基、1-甲基-n-戊基、2-甲基-n-戊基、3-甲基-n-戊基、4-甲基-n-戊基、1,1-二甲基-n-丁基、1,2-二甲基-n-丁基、1,3-二甲基-n-丁基、2,2-二甲基-n-丁基、2,3-二甲基-n-丁基、3,3-二甲基-n-丁基、1-乙基-n-丁基、2-乙基-n-丁基、1,1,2-三甲基-n-丙基、1,2,2-三甲基-n-丙基、1-乙基-1-甲基-n-丙基、1-乙基-2-甲基-n-丙基等。
前述式(1)中，Q所表示之碳原子數1至16之二價的烴基，例如，直鏈狀或支鏈狀之伸烷基、以雙鍵鍵結的含有2個碳原子之基，或主鏈含有至少可具有1個取代基之脂環式烴基或芳香族烴基之基。該些基，可列舉如，下述式(a)至式(m)所表示之基。
前述式(2)中，Z所表示之碳原子數1至4之二價的鍵結基，例如為表示至少可具有1個作為取代基的羥基之直鏈狀或支鏈狀之伸烷基。Z為表示該些伸烷基時，前述式(2)所表示之末端結構，可列舉如，下述式(2-1)及式(2-2)所表示之結構。
前述聚合物，例如，可經由以下過程而合成。將具有三
三酮結構的二環氧化合物，與末端具有羧基或羥基的化合物進行反應，即可製得具有前述式(1)
所表示之結構單位，及末端羧基或羥基的聚合物中間體。隨後，將具有前述末端的聚合物中間體與具有環氧基之(甲基)丙烯酸酯進行反應。
本發明之光硬化性樹脂組成物，為含有自由基型光聚合起始劑。該光聚合起始劑，只要為具有可被光硬化時所使用之光源所吸收之化合物時，並未有特別之限定，例如，tert-丁基過氧化-iso-丁酸酯、2,5-二甲基-2,5-雙(苯甲醯基二氧基)己烷、1,4-雙[α-(tert-丁基二氧基)-iso-丙氧基]苯、二-tert-丁基過氧化物、2,5-二甲基-2,5-雙(tert-丁基二氧基)己烯氫過氧化物、α-(iso-丙基苯基)-iso-丙基氫過氧化物、tert-丁基氫過氧化物、1,1-雙(tert-丁基二氧基)-3,3,5-三甲基環己烷、丁基-4,4-雙(tert-丁基二氧基)戊酸酯(Valerate)、環己酮過氧化物、2,2’,5,5’-四(tert-丁基過氧化羰基)二苯甲酮、3,3’,4,4’-四(tert-丁基過氧化羰基)二苯甲酮、3,3’,4,4’-四(tert-戊基過氧化羰基)二苯甲酮、3,3’,4,4’-四(tert-己基過氧化羰基)二苯甲酮、3,3’-雙(tert-丁基過氧化羰基)-4,4’-二羧基二苯甲酮、tert-丁基過氧化苯甲酸酯、二-tert-丁基二過氧化間苯二甲酸酯等的有機過氧化物；9,10-蒽醌、1-氯蒽醌、2-氯蒽醌、辛基甲基蒽醌、1,2-苯併蒽醌等的醌類；安息香甲酯、安息香乙醚、α-甲基安息香、α-苯基安息香等的安息香衍生物；2,2-二甲氧基-1,2-
二苯基乙烷-1-酮、1-羥基-環己基-苯基-酮、2-羥基-2-甲基-1-苯基-丙烷-1-酮、1-[4-(2-羥基乙氧基)-苯基]-2-羥基-2-甲基-1-丙烷-1-酮、2-羥基-1-[4-{4-(2-羥基-2-甲基-丙醯基)苄基}-苯基]-2-甲基-丙烷-1-酮、苯基乙醛酸(glyoxylic acid)甲酯、2-甲基-1-[4-(甲基硫基)苯基]-2-嗎琳丙烷-1-酮、2-苄基-2-二甲胺基-1-(4-嗎啉苯基)-1-丁酮、2-二甲胺基-2-(4-甲基-苄基)-1-(4-嗎啉-4-基-苯基)-丁烷-1-酮等之烷基苯基酮系化合物；雙(2,4,6-三甲基苯甲醯基)-苯基次膦氧化物、2,4,6-三甲基苯甲醯基-二苯基-次膦氧化物等的醯基次膦氧化物系化合物；2-(O-苯甲醯基肟)-1-[4-(苯基硫基)苯基]-1,2-辛烷二酮、1-(O-乙醯基肟)-1-[9-乙基-6-(2-甲基苯甲醯基)-9H-咔唑-3-基]乙酮等的肟酯系化合物等。
上述自由基型光聚合起始劑，可由市售物品中取得，例如，IRGACURE[註冊商標]651、同184、同2959、同127、同907、同369、同379EG、同819、同819DW、同1800、同1870、同784、同OXE01、同OXE02、同250、同1173、同MBF、同TPO、同4265、同TPO(以上，BASF公司製)、KAYACURE[註冊商標]DETX、同MBP、同DMBI、同EPA、同OA(以上，日本化藥(股)製)、VICURE-10、同55(以上，STAUFFER Co.LTD製)、ESACURE KIP150、同TZT、同1001、同KTO46、同KB1、同KL200、同KS300、同EB3、三
-PMS、三
A、三
B(以上，日本SIBER
HEGNER(股)製)、ADEKA OPTOMERN-1717、同N-1414、同N-1606(以上，(股)ADEKA製)等。該些自由基型光聚合起始劑，可單獨使用亦可、將二種以上組合使用亦可。
本發明之光硬化性樹脂組成物中之自由基型光聚合起始劑的含量，相對於上述聚合物之含量，例如為0.01phr至30phr、較佳為0.1phr至15phr。該含量之比例未達下限值時，無法得到充分之硬化性。其中，per為表示相對於聚合物之質量100g，自由基型光聚合起始劑的質量之意。
本發明之光硬化性樹脂組成物為含有溶劑。該溶劑，只要為可使用於半導體裝置製造步驟中之有機溶劑時，並未有特別之限定，例如，環己酮、甲基異戊酮、2-丁酮、2-庚酮等的酮類；乙二醇、乙二醇單乙酸酯、二乙二醇、二乙二醇單乙酸酯、丙二醇、丙二醇單乙酸酯、二丙二醇或二丙二醇單乙酸酯，及該些單甲醚、單乙醚、單丙醚、單丁醚、單苯醚等的多元醇類及其衍生物；二噁烷等的環式醚類；γ-丁內酯等的內酯類；及乳酸甲酯、乳酸乙酯、乙酸甲酯、乙酸乙酯、乙酸丁酯、丙酮酸甲酯、丙酮酸乙酯、甲氧基丙酸甲酯、乙氧基丙酸乙酯等的酯類。該些有機溶劑可單獨使用亦可、將二種以上混合使用亦可。由本發明之光硬化性樹脂組成物除溶劑所得之成份作為固體成
份時，該光硬化性樹脂組成物中所佔之固體成份的比例，例如為1質量%至80質量%。
本發明之光硬化性樹脂組成物中，必要時可添加二官能(甲基)丙烯酸酯作為交聯性化合物。此處所稱之二官能(甲基)丙烯酸酯，係指分子兩端具有丙烯基或甲基丙烯基的化合物。該化合物，例如，三環癸烷二甲醇二丙烯酸酯、三環癸烷二甲醇二甲基丙烯酸酯、三環癸烷二乙醇二丙烯酸酯，及三環癸烷二乙醇二甲基丙烯酸酯等。
上述二官能(甲基)丙烯酸酯，可由市售物品中取得，例如，A-DCP、DCP(以上，新中村化學工業(股)製)等。該些化合物，可單獨使用亦可、將二種以上組合使用亦可。
本發明之光硬化性樹脂組成物中之二官能(甲基)丙烯酸酯之含量，相對於上述聚合物之含量，例如為5質量%至50質量%、較佳為10質量%至30質量%。
本發明之光硬化性樹脂組成物中，必要時可再添加多官能硫醇作為交聯性化合物。其中，多官能硫醇係指，分子末端具有複數(例如2個、3個或4個)硫醇基之化合物。該化合物，例如，季戊四醇四(3-氫硫基丁酸酯)、1,4-雙(3-氫硫基丁醯氧基)丁烷、1,3,5-三(3-氫硫基丁醯氧基乙基)-1,3,5-三
-2,4,6(1H，3H，5H)-
三酮、三羥甲基丙烷三(3-氫硫基丁酸酯)，及三羥甲基乙烷三(3-氫硫基丁酸酯)等。
上述多官能硫醇，可由市售物品中取得，例如，KARENZ MT[註冊商標]PE1、同BD1、同NR1(以上，昭和電工(股)製)等。該些化合物，可單獨使用亦可、將二種以上組合使用亦可。
本發明之光硬化性樹脂組成物中之多官能硫醇之含量，相對於上述聚合物之含量，例如為0.1質量%至15質量%、較佳為0.5質量%至10質量%。
本發明之光硬化性樹脂組成物中，必要時可再添加含有環氧化合物、光酸產生劑、熱酸產生劑、無機填料、界面活性劑等之添加劑。
本發明之光硬化性樹脂組成物含有環氧化合物時，該環氧化合物，例如，1,4-丁烷二醇二縮水甘油醚、1,2-環氧-4-(環氧乙基)環己烷、甘油三縮水甘油醚、二乙二醇二縮水甘油醚、2,6-二縮水甘油苯基縮水甘油醚、1,1,3-三[p-(2,3-環氧丙氧基)苯基]丙烷、1,2-環己烷二羧酸二縮水甘油酯、4,4’-伸甲基雙(N,N-二縮水甘油苯胺)、3,4-環氧環己基甲基-3,4-環氧環己烷羧酸酯、三羥甲基乙烷三縮水甘油醚、三縮水甘油-p-胺酚、四縮水甘油甲基二甲苯二胺、四縮水甘油二胺基二苯基甲烷、四縮水甘油-1,3-雙胺基甲基環己烷、雙酚-A-二縮水甘油
醚、雙酚-S-二縮水甘油醚、季戊四醇四縮水甘油醚間苯二酚二縮水甘油醚、苯二甲酸二縮水甘油酯、新戊二醇二縮水甘油醚、聚丙二醇二縮水甘油醚、四溴雙酚-A-二縮水甘油醚、雙酚六氟丙酮二縮水甘油醚、季戊四醇二縮水甘油醚、三-(2,3-環氧丙基)異三聚氰酸酯、單烯丙基二縮水甘油異三聚氰酸酯、二甘油聚二縮水甘油醚、季戊四醇聚縮水甘油醚、1,4-雙(2,3-環氧丙氧基全氟異丙基)環己烷、季戊四醇聚縮水甘油醚、三羥甲基丙烷聚縮水甘油醚、間苯二酚二縮水甘油醚、1,6-己烷二醇二縮水甘油醚、聚乙二醇二縮水甘油醚、苯基縮水甘油醚、p-第三-丁基苯基縮水甘油醚、己二酸二縮水甘油醚、o-苯二甲酸二縮水甘油醚、二溴苯基縮水甘油醚、1,2,7,8-二環氧基辛烷、1,6-二羥甲基全氟己烷二縮水甘油醚、4,4’-雙(2,3-環氧丙氧基全氟異丙基)二苯醚、2,2-雙(4-縮水甘油氧苯基)丙烷、3,4-環氧環己基甲基-3’,4’-環氧環己烷羧酸酯、3,4-環氧環己氧基矽烷、2-(3,4-環氧環己基)-3’,4’-環氧-1,3-二噁烷-5-螺環己烷、1,2-乙烯二氧基-雙(3,4-環氧環己基甲烷)、4’,5’-環氧-2’-甲基環己基甲基-4,5-環氧-2-甲基環己烷羧酸酯、乙二醇-雙(3,4-環氧環己烷羧酸酯)、雙-(3,4-環氧環己基甲基)己二酸酯，及雙(2,3-環氧環戊基)醚等。又例如，縮水甘油丙烯酸酯、縮水甘油甲基丙烯酸酯等具有環氧基之(甲基)丙烯酸酯之共聚物，亦可作為上述環氧化合物之例示。
上述環氧化合物，可由市售物品中取得，例
如，EPLITE[註冊商標]GT-401、同GT-403、同GT-301、同GT-302、同PB3600、SEROKISITE[註冊商標]2021P、同2000、同3000、EHPE3150、EHPE3150CE、CYCLOROMO[註冊商標]M100(以上，(股)DAICEL製)、EPICLON[註冊商標]840、同840-S、同N-660、同N-673-80M(以上，DIC(股)製)等。
本發明之光硬化性樹脂組成物含有光酸產生劑時，該光酸產生劑，例如，IRGACURE[註冊商標]PAG103、同PAG108、同PAG121、同PAG203、同CGI725、GSID-26-1(以上，BASF公司製)、WPAG-145、WPAG-170、WPAG-199、WPAG-281、WPAG-336、WPAG-367(以上，和光純藥工業(股)製)、TFE三
、TME-三
、MP-三
、二甲氧基三
、TS-91、TS-01((股)三和化學製)等。
本發明之光硬化性樹脂組成物含有熱酸產生劑時，該熱酸產生劑，例如，K-PURE[註冊商標]TAG-2689、同TAG-2690、同TAG-2700、同CXC-1612、同CXC-1614、同CXC-1615、同CXC-1821(以上，KING INDUSTRIES公司製)等。
本發明之光硬化性樹脂組成物含有無機填料時，該無機填料，例如，二氧化矽、氮化鋁、氮化硼、氧化鋯、氧化鋁等之膠體。
本發明之光硬化性樹脂組成物含有界面活性劑時，該界面活性劑，例如，聚氧乙烯月桂醚、聚氧乙烯
硬脂醚、聚氧乙烯鯨臘醚、聚氧乙烯油醚等的聚氧乙烯烷醚類、聚氧乙烯辛基苯醚、聚氧乙烯壬基苯醚等的聚氧乙烯烷基芳醚類、聚氧乙烯‧聚氧丙烯基嵌段共聚物類、山梨糖醇單月桂酯、山梨糖醇單棕櫚酸酯、山梨糖醇單硬脂酸酯、山梨糖醇單油酸酯、山梨糖醇三油酸酯、山梨糖醇三硬脂酸酯等的山梨糖醇脂肪酸酯類、聚氧乙烯山梨糖醇單月桂酯、聚氧乙烯山梨糖醇單棕櫚酸酯、聚氧乙烯山梨糖醇單硬脂酸酯、聚氧乙烯山梨糖醇三油酸酯、聚氧乙烯山梨糖醇三硬脂酸酯等的聚氧乙烯山梨糖醇脂肪酸酯類等的非離子系界面活性劑等。
上述界面活性劑，可由市售物品中取得，例如，F-TOP[註冊商標]EF301、同EF303、同EF352(以上，三菱金屬電子化成(股)製)、美格氟[註冊商標]F171、同F173、同R-30、同R-30N、同R-40、同R-40-LM(以上，DIC(股)製)、氟拉朵FC430、同FC431(以上，住友3M(股)製)、ASAHIGATE[註冊商標]AG710、沙氟隆[註冊商標]S-382、同SC101、同SC102、同SC103、同SC104、同SC105、同SC106(以上，旭硝子(股)製)等氟系界面活性劑，及有機矽氧烷聚合物KP341(信越化學工業(股)製)等。該些界面活性劑可單獨使用亦可、將二種以上組合使用亦可。
使用本發明之光硬化性樹脂組成物，依以下之步驟，
即，將本發明之光硬化性樹脂組成物塗佈於基板上之步驟、將塗佈於前述基板上的光硬化性樹脂組成物於50℃至160℃之溫度進行預燒焙之步驟、對前述預燒焙後的形成於前述基板上之塗膜進行曝光之步驟，及使前述塗膜顯影之步驟時，即可形成硬化膜。
將本發明之光硬化性樹脂組成物塗佈於基板之方法，例如，旋轉塗佈法、灌注法、浸漬法、流動塗膜法、噴墨法、噴霧法、條狀塗佈法、凹版塗佈法、狹縫塗佈法、滾筒塗佈法、轉印印刷法、刷毛塗佈法、平板塗佈法，及空氣刮刀塗佈法等。
本發明之光硬化性樹脂組成物所塗佈之基板，例如，氧化矽膜、氮化矽膜或氧化氮化矽膜所被覆之矽晶圓、氮化矽基板、石英基板、無鹼玻璃基板、低鹼玻璃基板、結晶化玻璃基板、形成有銦錫氧化物(ITO)膜或銦鋅氧化物(IZO)膜之玻璃基板，及聚乙烯對苯二甲酸酯(PET)、聚乙烯萘酯(PEN)、三乙醯基纖維素(TAC)、聚乙烯(PE)、聚醯亞胺(PI)、聚醯胺(PA)、聚氯乙烯(PVC)、聚環烯烴(PCO)、聚偏氯乙烯(PVDC)、聚乙烯醇(PVA)、聚丙烯(PP)、聚碳酸酯(PC)、聚苯乙烯(PS)、聚丙烯腈(PAN)、乙烯乙酸乙烯基共聚物(EVA)、乙烯乙烯醇共聚物(EVOH)、乙烯甲基丙烯酸共聚物(EMMA)或聚甲基丙烯酸(PMMA)所形成之基板等。
前述預燒焙，為將溶劑由塗佈於前述基板上
的光硬化性樹脂組成物去除之目的所進行者，其結果，將會於前述基板上形成自該組成物失去流動性的塗膜。
於使前述塗膜曝光之步驟之後、該塗膜顯影之步驟之前，必要時可進行例如50℃至160℃之溫度下進行之曝光後燒焙(Post Exposure Bake，亦簡稱為PEB)。
對前述塗膜進行曝光時所使用之光源，例如，g線、h線、i線、ghi線寬頻，及KrF準分子雷射等。
前述塗膜於顯影所使用之顯影液，可列舉如，前述光硬化性樹脂組成物所含之溶劑等。其他，亦可使用作為光微影蝕刻步驟所使用之光阻劑溶液的溶劑之公知的有機溶劑。該有機溶劑，例如，丙二醇1-單甲醚2-乙酸酯、1-甲氧基-2-丙醇、環己酮，及2-丙醇等。該些有機溶劑可單獨使用亦可、將二種以上組合使用亦可。
以下，將以實施例為基礎對本發明作更詳細之說明，但本發明並不受該些實施例所限定。
由以下記載之合成例所製得之聚合物的GPC分析，為使用下述裝置，其測定條件係如以下所示。
裝置：一體型高速GPC系統HLC-8220GPC東曹(股)製
管柱：KF-G，KF804L
管柱溫度：40℃
溶劑：四氫呋喃(THF)
流量：1.0mL/分鐘
標準試料：聚苯乙烯
檢測器：RI
使1,2-環己烷二羧酸80.45g、單烯丙基二縮水甘油三聚異氰酸110.00g，及苄基三乙基銨氯化物4.52g溶解於丙二醇1-單甲醚2-乙酸酯292.46g後，於140℃下進行4小時反應而製得含有聚合物之溶液。冷卻至室溫後，使甲基丙烯酸縮水甘油18.05g及苄基三乙基銨氯化物0.72g溶解於本溶液後，於140℃下進行3小時反應而製得含有聚合物之溶液。對所得聚合物進行GPC分析結果，得知經標準聚苯乙烯換算後之重量平均分子量為2,700。所得之聚合物，為具有下述式(1a)所表示之結構單位及末端具有下述式(2a)所表示之結構之聚合物。
使4-甲基環己烷-1,2-二羧酸酐14.29g、單烯丙基二縮水甘油三聚異氰酸20.00g，及苄基三乙基銨氯化物0.82g溶解於環己酮105.33g後，於140℃下進行4小時反應而製得含有聚合物之溶液。冷卻至室溫後，使甲基丙烯酸縮水甘油3.25g及苄基三乙基銨氯化物0.13g溶解於本溶液後，於140℃下進行3小時反應而製得含有聚合物之溶液。對所得聚合物進行GPC分析結果，得知經標準聚苯乙烯換算後之重量平均分子量為10,900。所得之聚合物，為具有下述式(1b)所表示之結構單位及末端具有下述式(2b)所表示之結構之聚合物。
使2-丙烯-1,2-二羧酸18.24g、單烯丙基二縮水甘油三聚異氰酸33.00g，及乙基三苯基鏻溴化物2.21g溶解於環己酮124.71g後，於140℃下進行4小時反應而製得含有聚合物之溶液。冷卻至室溫後，使甲基丙烯酸縮水甘油4.86g及乙基三苯基鏻溴化物0.30g溶解於本溶液後，於140℃下進行3小時反應而製得含有聚合物之溶液。對所得聚合物進行GPC分析結果，得知經標準聚苯乙烯換算後之重量平均分子量為3,900。所得之聚合物，為具有下述式(1c)所表示之結構單位及末端具有下述式(2c)所表示之結構之聚合物。
使1,4-丁烷二羧酸20.48g、單烯丙基二縮水甘油三聚異氰酸33.00g，及乙基三苯基鏻溴化物2.21g溶解於環己酮129.96g後，於140℃下進行4小時反應而製得含有聚合物之溶液。冷卻至室溫後，使甲基丙烯酸縮水甘油5.07g及乙基三苯基鏻溴化物0.30g溶解於本溶液後，於140℃下進行3小時反應而製得含有聚合物之溶液。對所得聚合物進行GPC分析結果，得知經標準聚苯乙烯換算後之重量平均分子量為4,700。所得之聚合物，為具有下述式(1d)所表示之結構單位及末端具有下述式(2d)所表示之結構之聚合物。
使2,2-雙(4-縮水甘油氧環己基)丙烷25.00g、1,2-環己烷二羧酸11.35g，及苄基三乙基銨氯化物0.64g溶解於環己酮86.31g後，於140℃下進行4小時反應而製得含有聚合物之溶液。冷卻至室溫後，使甲基丙烯酸縮水甘油13.78g及苄基三乙基銨氯化物0.55g溶解於本溶液後，於140℃下進行3小時反應而製得含有聚合物之溶液。對所得聚合物進行GPC分析結果，得知經標準聚苯乙烯換算後之重量平均分子量為3,100。所得之聚合物，為具有下述式(3)所表示之結構單位及末端具有下述式(2e)所表示之結構之聚合物。
使1,4-萘二羧酸22.11g、2,2-雙(4-縮水甘油氧苯基)丙烷32.00g，及苄基三乙基銨氯化物0.99g溶解於丙二醇1-單甲醚2-乙酸酯82.65g後，於140℃下進行4小時反應而製得含有聚合物之溶液。冷卻至室溫後，使甲基丙烯酸縮水甘油6.41g及苄基三乙基銨氯化物0.26g溶解於本溶液後，於140℃下進行3小時反應而製得含有聚合物之溶液。對所得聚合物進行GPC分析結果，得知經標準聚苯乙烯換算後之重量平均分子量為4,400。所得之聚合物，為具有下述式(4)所表示之結構單位及末端具有下述式(2f)所表示之結構之聚合物。
使2,5-吡啶二羧酸12.29g、2,2-雙(4-縮水甘油氧苯基)丙烷23.00g，及苄基三乙基銨氯化物0.71g溶解於環己酮107.99g後，於140℃下進行4小時反應而製得含有聚合物之溶液。冷卻至室溫後，使甲基丙烯酸縮水甘油3.34g及苄基三乙基銨氯化物0.13g溶解於本溶液後，於140℃下進行3小時反應而製得含有聚合物之溶液。對所得聚合物進行GPC分析結果，得知經標準聚苯乙烯換算後之重量平均分子量為6,200。所得之聚合物，為具有下述式(5)所表示之結構單位及末端具有下述式(2g)所表示之結構之聚合物。
使異苯二甲酸14.34g、2,2-雙(4-縮水甘油氧苯基)丙烷27.00g，及苄基三乙基銨氯化物0.84g溶解於丙二醇1-單甲醚2-乙酸酯63.26g後，於140℃下進行4小時反應而製得含有聚合物之溶液。對所得聚合物進行GPC分析結果，得知經標準聚苯乙烯換算後之重量平均分子量為10,200。所得之聚合物，為具有下述式(6)所表示之結構單位，末端未被具有丙烯基或甲基丙烯基之結構所密封之聚合物。
使2,2-雙(4-縮水甘油氧環己基)丙烷28.00g、單烯
丙基三聚異氰酸12.49g，及苄基三乙基銨氯化物0.71g溶解於丙二醇1-單甲醚2-乙酸酯61.81g後，於140℃下進行4小時反應而製得含有聚合物之溶液。對所得聚合物進行GPC分析結果，得知經標準聚苯乙烯換算後之重量平均分子量為4,100。所得之聚合物，為具有下述式(7)所表示之結構單位之聚合物。
使1,2-環己烷二羧酸103.61g、單烯丙基二縮水甘油三聚異氰酸150.00g，及苄基三乙基銨氯化物3.08g溶解於丙二醇1-單甲醚2-乙酸酯256.69g後，於140℃下進行4小時反應而製得含有聚合物之溶液。對所得聚合物進行GPC分析結果，得知經標準聚苯乙烯換算後之重量平均分子量為3,300。所得之聚合物，為具有下述式(1a)所表示之結構單位之聚合物。
使2,2-雙(4-縮水甘油氧環己基)丙烷24.00g、1,4-萘二羧酸13.68g，及苄基三乙基銨氯化物1.23g溶解於丙二醇1-單甲醚2-乙酸酯90.78g後，於140℃下進行4小時反應而製得含有聚合物之溶液。冷卻至室溫後，使甲基丙烯酸縮水甘油3.57g及苄基三乙基銨氯化物0.14g溶解於本溶液後，於140℃下進行3小時反應而製得含有聚合物之溶液。對所得聚合物進行GPC分析結果，得知經標準聚苯乙烯換算後之重量平均分子量為6,400。所得之聚合物，為具有下述式(8)所表示之結構單位及末端具有下述式(2h)所表示之結構之聚合物。
使六氫苯二甲酸二縮水甘油酯15.00g、4-環己烯-1,2-二羧酸9.86g，及苄基三乙基銨氯化物1.12g溶解於丙二醇1-單甲醚2-乙酸酯103.93g後，於140℃下進行4小時反應而製得含有聚合物之溶液。冷卻至室溫後，使甲基丙烯酸縮水甘油2.36g及苄基三乙基銨氯化物0.09g溶解於本溶液後，於140℃下進行3小時反應而製得含有聚合物之溶液。對所得聚合物進行GPC分析結果，得知經標準聚苯乙烯換算後之重量平均分子量為2,300。所得之聚合物，為具有下述式(9)所表示之結構單位及末端具有下述式(2i)所表示之結構之聚合物。
將含有合成例1所得之聚合物的溶液，注入填充有陽離子交換樹脂(15JWET、ORGANO(股))及陰離子交換樹
脂(MONOSPHERE 550A、室町科技(股))之瓶中，進行4小時之攪拌。使攪拌後之溶液20g，與IRGACURE[註冊商標]184(BASF公司製)0.68g、三環癸烷二甲醇二丙烯酸酯(新中村化學工業(股)製)4.08g，及季戊四醇四(3-氫硫基丁酸酯)(昭和電工(股)製)0.34g，溶解於丙二醇1-單甲醚2-乙酸酯8.90g中，而製得組成物。隨後，使用孔徑3μm之聚乙烯製微過濾器過濾，而製得光硬化性樹脂組成物。
將含有合成例2所得之聚合物之溶液，注入填充有陽離子交換樹脂(15JWET、ORGANO(股))及陰離子交換樹脂(MONOSPHERE[註冊商標]550A、室町科技(股))之瓶中，進行4小時之攪拌。使攪拌後之溶液22g，與IRGACURE184(BASF公司製)0.60g、三環癸烷二甲醇二丙烯酸酯(新中村化學工業(股)製)3.62g，及季戊四醇四(3-氫硫基丁酸酯)(昭和電工(股)製)0.30g，溶解於丙二醇1-單甲醚2-乙酸酯3.62g中，而製得組成物。隨後，使用孔徑3μm之聚乙烯製微過濾器過濾，而製得光硬化性樹脂組成物。
將含有合成例3所得之聚合物之溶液，注入填充有陽離子交換樹脂(15JWET、ORGANO(股))及陰離子交換樹
脂(MONOSPHERE 550A、室町科技(股))之瓶中，進行4小時之攪拌。使攪拌後之溶液24g，與IRGACURE184(BASF公司製)0.72g、三環癸烷二甲醇二丙烯酸酯(新中村化學工業(股)製)4.30g，及季戊四醇四(3-氫硫基丁酸酯)(昭和電工(股)製)0.36g，溶解於丙二醇1-單甲醚2-乙酸酯6.48g中，而製得組成物。隨後，使用孔徑3μm之聚乙烯製微過濾器過濾，而製得光硬化性樹脂組成物。
將含有合成例4所得之聚合物之溶液，注入填充有陽離子交換樹脂(15JWET、ORGANO(股))及陰離子交換樹脂(MONOSPHERE 550A、室町科技(股))之瓶中，進行4小時之攪拌。使攪拌後之溶液23g，與IRGACURE184(BASF公司製)0.72g、三環癸烷二甲醇二丙烯酸酯(新中村化學工業(股)製)4.35g，及季戊四醇四(3-氫硫基丁酸酯)(昭和電工(股)製)0.36g，溶解於丙二醇1-單甲醚2-乙酸酯7.78g中，而製得組成物。隨後，使用孔徑3μm之聚乙烯製微過濾器過濾，而製得光硬化性樹脂組成物。
將含有合成例5所得之聚合物之溶液，注入填充有陽離子交換樹脂(15JWET、ORGANO(股))及陰離子交換樹脂(MONOSPHERE 550A、室町科技(股))之瓶中，進行4小時之攪拌。使攪拌後之溶液33g，與IRGACURE184
(BASF公司製)0.93g、三環癸烷二甲醇二丙烯酸酯(新中村化學工業(股)製)2.78g，及季戊四醇四(3-氫硫基丁酸酯)(昭和電工(股)製)0.46g，溶解於環己酮0.69g中，而製得組成物。隨後，使用孔徑3μm之聚乙烯製微過濾器過濾，而製得光硬化性樹脂組成物。
將含有合成例6所得之聚合物之溶液，注入填充有陽離子交換樹脂(15JWET、ORGANO(股))及陰離子交換樹脂(MONOSPHERE 550A、室町科技(股))之瓶中，進行4小時之攪拌。使攪拌後之溶液21g，與IRGACURE184(BASF公司製)0.65g、三環癸烷二甲醇二丙烯酸酯(新中村化學工業(股)製)3.91g，及季戊四醇四(3-氫硫基丁酸酯)(昭和電工(股)製)0.33g，溶解於丙二醇1-單甲醚2-乙酸酯6.67g中，而製得組成物。隨後，使用孔徑3μm之聚乙烯製微過濾器過濾，而製得光硬化性樹脂組成物。
將含有合成例7所得之聚合物之溶液，注入填充有陽離子交換樹脂(15JWET、ORGANO(股))及陰離子交換樹脂(MONOSPHERE 550A、室町科技(股))之瓶中，進行4小時之攪拌。使攪拌後之溶液21g，與IRGACURE184(BASF公司製)0.57g、三環癸烷二甲醇二丙烯酸酯(新中村化學工業(股)製)3.44g，及季戊四醇四(3-氫硫基丁
酸酯)(昭和電工(股)製)0.29g，溶解於丙二醇1-單甲醚2-乙酸酯4.99g中，而製得組成物。隨後，使用孔徑3μm之聚乙烯製微過濾器過濾，而製得光硬化性樹脂組成物。
將含有合成例8所得之聚合物之溶液，注入填充有陽離子交換樹脂(15JWET、ORGANO(股))及陰離子交換樹脂(MONOSPHERE 550A、室町科技(股))之瓶中，進行4小時之攪拌。使攪拌後之溶液22g，與IRGACURE184(BASF公司製)0.71g、三環癸烷二甲醇二丙烯酸酯(新中村化學工業(股)製)4.26g，及季戊四醇四(3-氫硫基丁酸酯)(昭和電工(股)製)0.35g，溶解於丙二醇1-單甲醚2-乙酸酯8.16g中，而製得組成物。隨後，使用孔徑3μm之聚乙烯製微過濾器過濾，而製得光硬化性樹脂組成物。
將含有合成例9所得之聚合物之溶液，注入填充有陽離子交換樹脂(15JWET、ORGANO(股))及陰離子交換樹脂(MONOSPHERE 550A、室町科技(股))之瓶中，進行4小時之攪拌。使攪拌後之溶液22g，與IRGACURE184(BASF公司製)0.67g、三環癸烷二甲醇二丙烯酸酯(新中村化學工業(股)製)4.03g，及季戊四醇四(3-氫硫基丁酸酯)(昭和電工(股)製)0.34g，溶解於丙二醇1-單甲醚
2-乙酸酯6.58g中，而製得組成物。隨後，使用孔徑3μm之聚乙烯製微過濾器過濾，而製得光硬化性樹脂組成物。
將含有合成例10所得之聚合物之溶液，注入填充有陽離子交換樹脂(15JWET、ORGANO(股))及陰離子交換樹脂(MONOSPHERE 550A、室町科技(股))之瓶中，進行4小時之攪拌。使攪拌後之溶液22g，與IRGACURE184(BASF公司製)0.72g、三環癸烷二甲醇二丙烯酸酯(新中村化學工業(股)製)4.29g，及季戊四醇四(3-氫硫基丁酸酯)(昭和電工(股)製)0.36g，溶解於丙二醇1-單甲醚2-乙酸酯8.42g中，而製得組成物。隨後，使用孔徑3μm之聚乙烯製微過濾器過濾，而製得光硬化性樹脂組成物。
將含有合成例11所得之聚合物之溶液，注入填充有陽離子交換樹脂(15JWET、ORGANO(股))及陰離子交換樹脂(MONOSPHERE 550A、室町科技(股))之瓶中，進行4小時之攪拌。使攪拌後之溶液20g，與IRGACURE184(BASF公司製)0.60g、三環癸烷二甲醇二丙烯酸酯(新中村化學工業(股)製)3.58g，及季戊四醇四(3-氫硫基丁酸酯)(昭和電工(股)製)0.30g，溶解於丙二醇1-單甲醚2-乙酸酯5.36g中，而製得組成物。隨後，使用孔徑3μm
之聚乙烯製微過濾器過濾，而製得光硬化性樹脂組成物。
將含有合成例12所得之聚合物之溶液，注入填充有陽離子交換樹脂(15JWET、ORGANO(股))及陰離子交換樹脂(MONOSPHERE 550A、室町科技(股))之瓶中，進行4小時之攪拌。使攪拌後之溶液18g，與IRGACURE184(BASF公司製)0.60g、三環癸烷二甲醇二丙烯酸酯(新中村化學工業(股)製)3.62g，及季戊四醇四(3-氫硫基丁酸酯)(昭和電工(股)製)0.30g，溶解於丙二醇1-單甲醚2-乙酸酯7.67g中，而製得組成物。隨後，使用孔徑3μm之聚乙烯製微過濾器過濾，而製得光硬化性樹脂組成物。
將實施例1至實施例4、比較例2、3、7及8所製得之光硬化性樹脂組成物，使用旋轉塗佈器塗佈於石英基板上，於100℃下進行預燒焙，使用對準儀(PLA-501、佳能(股)製)進行曝光(i線、曝光量：3000mJ/cm2)，再於100℃下進行燒焙後，使用丙二醇1-單甲醚2-乙酸酯及1-甲氧基-2-丙醇混合溶液進行顯影，而形成膜厚10μm之膜。使用紫外線可見分光光度計UV-2550((股)島津製作所製)，測定該膜於波長400nm之透過率。其結果係如表1所示。表1中，透過率為95%以上時標記為○，未達95%時標記為×。此外，前述實施例1至實施例4、比較例
2、3、7及8所製得之光硬化性樹脂組成物所形成之膜，於265℃進行3分鐘燒焙後，測定於波長400nm之透過率。其結果記載於表1之中，相對於前述265℃之3分鐘燒焙前的透過率，該燒焙後之透過率之降低度小於1%以下者標記為○，降低度超過1%者標記為×。下述表1之結果，顯示出由實施例1至實施例4所製得之光硬化性樹脂組成物所形成之膜，相較於由比較例2及比較例3所製得之光硬化性樹脂組成物所形成之膜具有更高之透過率，且較由比較例2、3、7及8所製得之光硬化性樹脂組成物所形成之膜，具有265℃之高耐熱性。
實施例1至實施例4及比較例4至比較例6所製得之光硬化性樹脂組成物，使用旋轉塗佈器塗佈於矽晶圓上，於100℃下進行預燒焙，使用對準儀(PLA-501、佳能(股)製)進行曝光(i線、曝光量：3000mJ/cm2)，再於
100℃下進行燒焙後，使用丙二醇1-單甲醚2-乙酸酯及1-甲氧基-2-丙醇混合溶液進行顯影，而形成膜厚10μm之膜。將該膜於23℃下浸漬於N-甲基2-吡咯啶酮中1分鐘。確認由含有末端具有甲基丙烯酸基之聚合物的實施例1至實施例4所製得之光硬化性樹脂組成物所形成之膜，於浸漬前後之膜厚變化為5%以下，但由含有末端未被具有丙烯基或甲基丙烯基之結構所密封之聚合物的比較例4至比較例6所製得之光硬化性樹脂組成物所形成之膜，於浸漬N-甲基吡咯啶酮後，其浸漬前之膜厚的20%以上為被溶解。
將實施例1、3及比較例1所製得之組成物分別於KAPTON薄膜(東麗杜邦公司製)上形成膜，於100℃進行預燒焙，使用對準儀(PLA-501、佳能(股)製)進行曝光(i線、曝光量：3000mJ/cm2)後，再於100℃下進行燒焙後，使用丙二醇1-單甲醚2-乙酸酯及1-甲氧基-2-丙醇混合溶液進行顯影，得目的之膜。透濕度測定為，將氯化鈣加入透濕度測定圓桶，以薄膜徑為6cm之方式設置所製得之膜。測定初期之全體質量，將其設置於40℃/90%之恆溫恆濕槽中，測定24小時後之全體質量，並算出水的質量増加量，進行膜的透濕度之評估。由實施例1之組成物所製得之膜的透濕度為28g/m2‧day、由實施例3之
組成物所製得之膜的透濕度為35g/m2‧day、由比較例1之組成物所製得之膜的透濕度為77g/m2‧day。其結果得知，實施例1之組成物所製得之膜及實施例3之組成物所製得之膜，相較於比較例1之組成物所製得之膜為具有更優良的抗透濕性。
將實施例1至實施例4所製得之光硬化性樹脂組成物，使用旋轉塗佈器塗佈於4英吋之矽晶圓上，於80℃下浸行3分鐘之燒焙，形成膜厚10μm之膜後，使用貼合裝置(AYUMI工業(股)製、VJ-300)，於真空度10Pa以下，溫度80℃、貼合壓力175kg之條件下黏著於4英吋之玻璃晶圓，使用切割裝置(DISCO(股)製、DAD321)由該晶圓切取1cm四方，而製得黏著力評估樣品。所得之黏著力評估樣品兩面塗佈ARALIDITE[註冊商標]2014(Huntsman Advanced Materials公司製)，並將其兩面黏著於測定黏著力(剪切力)測定用專用模具後，以高壓釜((股)島津製作所製、高壓釜AGS-100NX)評估其黏著力(剪切力)。黏著力以5mm/分鐘之拉伸速度下進行測定。其結果係如下述表2所示。表2中，為評估黏著力之值為2000N以上時，樣品於塗佈ARALIDITE2014之部份是否會產生斷裂，因塗佈實施例1至實施例4所製得之光硬化性樹脂組成物之部份並未產生斷裂，故顯示出本發明之光硬化性樹脂組成物的黏著力具有表中之數值以上之黏
著力。因而確認使用實施例1至實施例4所製得之光硬化性樹所得之樣品，具有充分之黏著性。
Claims (6)
- 一種光硬化性樹脂組成物，其特徵為含有，具有下述式(1)所表示之結構單位，且末端具有下述式(2)所表示之結構的重量平均分子量1,000至50,000之聚合物、相對於前述聚合物含量而言為0.01phr至30phr的自由基型光聚合起始劑及溶劑，固體成份的比例為1質量%至80質量%，
- 如請求項1之光硬化性樹脂組成物，其中，前述式(1)中，Q所表示之二價的烴基，表示直鏈狀或支鏈狀之伸烷基、以雙鍵鍵結的含有2個碳原子之基，或主鏈含有至少可具有1個取代基之脂環式烴基或芳香族烴基之基。
- 如請求項1或請求項2之光硬化性樹脂組成物，其中，前述式(2)中，Z所表示之二價的鍵結基，表示至少可具有1個作為取代基的羥基之直鏈狀或支鏈狀之伸 烷基。
- 如請求項1或請求項2之光硬化性樹脂組成物，其尚含有二官能(甲基)丙烯酸酯及/或多官能硫醇。
- 如請求項1或請求項2之光硬化性樹脂組成物，其係作為黏著劑使用或透鏡材料使用。
- 一種膜形成方法，其特徵為具有，將請求項1至請求項5之任一項所記載之光硬化性樹脂組成物塗佈於基板上之步驟、將塗佈於前述基板上的光硬化性樹脂組成物於50℃至160℃之溫度進行預燒焙之步驟、對前述預燒焙後的形成於前述基板上之塗膜進行曝光之步驟，及使前述塗膜顯影之步驟。
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- 2016-06-15 US US15/739,808 patent/US10866513B2/en active Active
- 2016-06-15 CN CN201680036679.7A patent/CN107709388B/zh active Active
- 2016-06-23 TW TW105119752A patent/TWI704415B/zh active
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| Publication number | Priority date | Publication date | Assignee | Title |
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| TW200815925A (en) * | 2006-06-19 | 2008-04-01 | Nissan Chemical Ind Ltd | Resist underlayer coating forming composition containing hydroxy-containing condensed resin |
| WO2013051615A1 (ja) * | 2011-10-07 | 2013-04-11 | 富士フイルム株式会社 | 半導体発光装置用封止剤、これを用いた半導体発光装置用封止材及び半導体発光装置 |
| TW201332981A (zh) * | 2011-12-30 | 2013-08-16 | Cheil Ind Inc | 三聚氰酸衍生物、包括該等三聚氰酸衍生物之光阻底層組成物以及使用該光阻底層組成物形成圖案的方法 |
| WO2013161402A1 (ja) * | 2012-04-26 | 2013-10-31 | ミネベア株式会社 | 紫外線硬化性樹脂組成物及び摺動部材、並びに摺動部材の製造方法 |
| TW201412874A (zh) * | 2012-05-11 | 2014-04-01 | Nissan Chemical Ind Ltd | 膜形成用組成物 |
Also Published As
| Publication number | Publication date |
|---|---|
| SG11201710797QA (en) | 2018-01-30 |
| US10866513B2 (en) | 2020-12-15 |
| KR20180022667A (ko) | 2018-03-06 |
| CN107709388B (zh) | 2020-07-07 |
| KR102281571B1 (ko) | 2021-07-26 |
| US20180362696A1 (en) | 2018-12-20 |
| TW201715298A (zh) | 2017-05-01 |
| JPWO2016208472A1 (ja) | 2018-04-12 |
| WO2016208472A1 (ja) | 2016-12-29 |
| JP6569875B2 (ja) | 2019-09-04 |
| CN107709388A (zh) | 2018-02-16 |
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