TWI776133B - 一種新的二芳醯基咔唑化合物及其作為增感劑的應用 - Google Patents

一種新的二芳醯基咔唑化合物及其作為增感劑的應用 Download PDF

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TWI776133B
TWI776133B TW109109042A TW109109042A TWI776133B TW I776133 B TWI776133 B TW I776133B TW 109109042 A TW109109042 A TW 109109042A TW 109109042 A TW109109042 A TW 109109042A TW I776133 B TWI776133 B TW I776133B
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substituted
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TW202100510A (zh
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趙文超
李家齊
麻忠利
王辰龍
王永林
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中國大陸商艾堅蒙（安慶）科技發展有限公司
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Abstract

本發明提供一種新的二芳醯基咔唑化合物，其與咔唑基肟酯光引發劑一起使用在光刻膠組合物中顯示了顯著的協同引發作用，當二芳醯基咔唑化合物與咔唑基肟酯光引發劑的摩爾比在0.1-1.4之間顯示了最佳的增感效果。

Description

一種新的二芳醯基咔唑化合物及其作為增感劑的應用
本發明係屬於有機化學及光固化技術領域，具體涉及一種新的二芳醯基咔唑化合物，其作為高活性增感劑與咔唑基肟酯一起構成光引發劑組合物，應用在光固化組合物中，尤其是用於製造光刻膠，顯示出高感度特性。
光固化技術自70年代出現後得到了廣泛應用，例如在塗料、印刷油墨、電子器件製造領域普遍採用了UV光固化技術，其中，影響固化效率的關鍵因素是光引發劑及與之配合使用的助引發劑成分，例如增感劑。咔唑基肟酯是肟酯類光引發劑中的重要一類，由於其具有相對較高的感度被本領域的技術人員所熟知和研究及使用，如專利公開號或公告號為CN1922142A(三菱化學)、CN100528838C(02)、CN101528694A(831)、CN101528693A、CN101508744A(304)、CN103153952A(03)、CN103492948A、CN107793502A的專利申請檔公開了具有各種不同取代基的咔唑基肟酯化合物，用在彩色濾光片、黑色矩陣、光間隔物、液晶分割取向等材料或器件方面。為提高色彩飽和度或遮蓋力的需要，光固化配方中的顏料含量越來越高，尤其是高顏料含量的黑色光刻膠，固化 過程中的光能利用率也因顏料的吸收而變小，需要開發有更高感度的光引發劑或光引發劑組合物，對現有光引發劑的增感也是提高感度的方法之一。現有技術中描述的增感劑如專利CN100528838C中公開的有二苯甲酮及其衍生物、硫雜蒽酮及其衍生物、蒽醌及其衍生物、香豆素衍生物、樟腦醌、吩噻嗪及其衍生物、3-(芳醯基亞甲基)噻唑啉、繞丹寧及其衍生物、曙紅、羅丹明、吖啶、花青素、部花青染料、叔胺化合物；其中優選了二苯甲酮及其衍生物、硫雜蒽酮及其衍生物、蒽醌及其衍生物、香豆素衍生物。實驗證明，這些增感劑在與咔唑基肟酯的混合使用時，並沒有表現出令人滿意的增感效果，有的化合物因含有酚羥基或苯胺基基團例如曙紅、花青素、吩噻嗪而使光固化組合物配方光固化效率降低；在優選的四類化合物中，雖然它們自身也是光引發劑，但與咔唑基肟酯化合物比，光引發效率要低許多，與咔唑基肟酯混合使用時也沒有表現出協同增感作用。所以實際上現有技術中並沒有較理想的增感劑。
但是技術人員對提高曝光感度、解像力、熱穩定性等性能的追求永遠沒有止境，現有產品和配方技術不斷面臨著新的挑戰。
發明人合成出如式I和式Ⅱ所示的一類新的二芳醯基咔唑化合物，意外發現，它們在與咔唑基肟酯例如Irgacure® OXE 03按特定比例一起使用時可以起到顯著的增感作用，增感效率顯著高於現有技術所公開的那些化合物，由此提出一種含有上述二芳醯基 咔唑化合物和咔唑基肟酯的光引發劑組合物及該光引發劑組合物在光固化組合物中的應用，特別是在光刻膠中的應用。
第一方面，提供一種二芳醯基咔唑化合物，結構如式I或式Ⅱ所示，
Figure 109109042-A0305-02-0004-2
Figure 109109042-A0305-02-0004-3
其中，R1，R8，R11，R18各自獨立地是H，鹵素原子，C1-C8烷基，C1-C8烷氧基，CN；R2，R3，R4，R5，R6，R7，R12，R13，R14，R15，R16，R17各自獨立地是H，F，Cl，COOR20，C1-C12直鏈或支鏈烷基，C1-C12直鏈或支鏈烷氧基，其中所述C1-C12直鏈或支鏈烷基未經取代或經一個或多個以下基團取代：苯基、C3-C6環烷基、C3-C6雜環基、F、Cl、COOR21、OR21、SR21、PO(OCnH2n+1)2、Si(CnH2n+1)3，n為1-4的整數；條件是，每個苯甲醯基的苯環上至少有一個取代基是氟原子或含有氟代烷基的基團；R9，R19各自獨立地是C1-C12直鏈或支鏈烷基，C2-C12烯基，C3-C12烯基烷基，其中的碳原子上的氫未經取代或經一個或多個以下基團取代：苯基、C3-C6環烷基、C3-C6雜環基、鹵素、COOR20、OR20、SR20、PO(OCnH2n+1)2、Si(CnH2n+1)3，n 為1-4的整數；或者C3-C12烯基烷基被一個或多個O、S、SO、SO2、CO、COO間隔；或R9，R19各自獨立地是C3-C12烷基，其烷基鏈經一個或多個O、S、SO、SO2、CO間隔；或R9，R19各自獨立地是苯基，苯基未經取代或經一個或多個C1-C8烷基、鹵素原子、OR20、SR20、COR20、CN、COOH取代；或R9可與取代基R1一起，或R9可與取代基R8一起構成C4-C6雜環結構；或R19可與取代基R11一起，或R19可與取代基R18一起構成C4-C6雜環結構；R20是C1-C12烷基或苯基，其未經取代或經一個或多個以下基團取代：苯基、C3-C6環烷基、C3-C6雜環基、F、Cl、OR21、SR21；R21是C1-C12烷基。
實施時，式I所示的化合物選自如式I-A和式I-B所示化合物；式Ⅱ所示的化合物選自如Ⅱ-A和Ⅱ-B所示化合物：
Figure 109109042-A0305-02-0005-4
Figure 109109042-A0305-02-0005-5
Figure 109109042-A0305-02-0006-6
Figure 109109042-A0305-02-0006-7
其中，R2，R3，R4，R5，R6，R7，R12，R13，R14，R15，R16，R17各自獨立地是H，F，Cl，COOR20，C1-C12直鏈或支鏈烷基，C1-C12直鏈或支鏈烷氧基，其中C1-C12直鏈或支鏈烷基未經取代或經一個或多個以下基團取代：苯基、C3-C6環烷基、C3-C6雜環基、F、Cl、COOR21、OR21、SR21、PO(OCnH2n+1)2、Si(CnH2n+1)3，n為1-4的整數；條件是，每個苯甲醯基的苯環上至少有一個取代基是氟原子或含有氟代烷基的基團；R9，R19的定義如上所述。Y1，Y2各自獨立地是C2-C8直鏈或支鏈烷基，鏈可以被O、S、NR21或羰基***，或碳上的氫被OH、鹵素原子取代。
實施時，式I-A和I-B所示的二芳醯基咔唑化合物的實例有：
Figure 109109042-A0305-02-0007-9
Figure 109109042-A0305-02-0007-10
Figure 109109042-A0305-02-0007-11
Figure 109109042-A0305-02-0007-12
Figure 109109042-A0305-02-0007-8
Figure 109109042-A0305-02-0008-13
Figure 109109042-A0305-02-0008-14
Figure 109109042-A0305-02-0008-15
Figure 109109042-A0305-02-0008-16
Figure 109109042-A0305-02-0009-18
Figure 109109042-A0305-02-0009-17
第二方面，提供式I或式Ⅱ所示的二芳醯基咔唑化合物的製備方法：以式Ⅲ-A或式Ⅲ-B所示的化合物為原料，與對應的醯基化試劑如取代芳醯氯或酸酐經一步或兩步傅克醯基化反應得到對稱或不對稱的二芳醯基化合物；如任一芳基上含有羧基或含有具有再被取代活性的鹵素原子時，可再與R20OH醇類化合物進行酯化反應或者醚化反應，得到式I或式Ⅱ所示的二芳醯基咔唑化合物。
Figure 109109042-A0305-02-0009-19
其中的R1，R8，R9，R11，R18，R19定義如上所述。
第三方面，本發明還提供了一種光引發劑組合物，包含至少一種上述二芳醯基咔唑化合物和至少一種咔唑基肟酯光引發劑，其中所述咔唑基肟酯光引發劑是指至少一個肟酯基團
Figure 109109042-A0305-02-0010-20
直接或通過一個羰基連接在N-取代咔唑母體結構上；其中R22為C1-C12烷基，其未經取代或經一個或多個以下基團取代：鹵素原子、OR24、SR24、C3-C8環烷基、苯基、C4-C20雜芳基、COOR24；或R22為C6-C20芳基或C4-C20雜芳基，其各自未經取代或經一個或多個以下基團取代：鹵素原子、C1-C20烷基、被一個或多個氟原子取代的C1-C8烷基、CN、OR24、SR24、NR25R26；或R22為C6-C20芳醯基，C4-C20雜芳醯基；R23選自C1-C12烷基，C6-C20芳基，C1-C4烷氧基；R24為H，C1-C8烷基，任意被一個或多個C3-C8雜環基、F、乙醯氧基取代的C1-C8烷基，苯基，C1-C20烷基苯基；R25，R26各自為C1-C4烷基，經OR24取代的C2-C4烷基，或NR25R26為環狀結構
Figure 109109042-A0305-02-0010-21
，
Figure 109109042-A0305-02-0010-22
，
Figure 109109042-A0305-02-0010-23
，
Figure 109109042-A0305-02-0010-24
；所述咔唑母體結構選自咔唑、苯並咔唑、二苯並咔唑，母體結構上氫原子除被上述肟酯基團或連接著肟酯基團的羰基取代基外，還可以被以下一個或多個基團取代：C1-C20烷基，鹵素，NO2，CN，OR27，C6-C20芳醯基，C4-C20雜芳醯基，4,5-二苯基咪唑-2基，母體結構上的取代基在空間上相鄰時可以構成新的五元到七元環狀結構；其中的C1-C20烷基未經取代或被以下一個或多個基團取代：鹵素、C3-C8環烷基、C3-C8雜環烷基、苯基、COOR27、OR27、PO(OCnH2n+1)2、Si(CnH2n+1)3，n為1-4的整數，或者碳原子數大於3時被一個或多個氧原子***；R27為C1-C8烷基，被C3-C8雜環烷基取代的C1-C8烷基；C6-C20芳醯基，C4-C20雜芳醯 基中的芳基或雜芳基未經取代或被以下一個或多個基團取代：鹵素原子，CN，
Figure 109109042-A0305-02-0011-25
，R24’，OR24’，SR24’，NR25’R26’，COOR24’，R24’SO2；R22’，R23’，R24’，NR25’R26’的定義與對應的R22，R23，R24，NR25R26相同。
實施時，所述咔唑基肟酯光引發劑選自以下化合物或者它們的任意混合物：
Figure 109109042-A0305-02-0011-26
Figure 109109042-A0305-02-0012-27
Figure 109109042-A0305-02-0013-28
Figure 109109042-A0305-02-0014-30
Figure 109109042-A0305-02-0015-31
咔唑基肟酯的製備方法之一是以相應的醯基咔唑母體化合物為原料，經過肟化、酯化得到咔唑基肟酯，與此有關的現有技術很多可以參考，例如CN103153952A。
實施時，光引發劑組合物的製備方法包括：取一種增感劑化合物例如式I-1化合物0.1摩爾量，取一種咔唑基肟酯例如式Ⅳ-22化合物0.1摩爾量，混合均勻即得到光引發劑組合物。或者在光固化組合物製備中直接將一種或多種增感劑化合物和一種或多種咔唑基肟酯與其他組分混合，但增感劑的合計摩爾量與咔唑基肟酯的合計摩爾量之比不大於2：1，優選0.1：1~1.4：1，更優選為0.22：1~1.16：1。
第四方面，本發明還提供一種光固化組合物，含有：
a.光引發劑組合物，含有至少一種式I、式Ⅱ A和Ⅱ B所示的增感劑和至少一種式Ⅳ 1-Ⅳ 37所示的咔唑基肟酯化合物；可選地，組分a的品質占配方全部固體品質的比例為1-10%，優選1-8%。
b.至少一種可自由基聚合的化合物，可選地，所述可自由基聚合的化合物選自丙烯酸酯類化合物，甲基丙烯酸酯類化合物、含有丙烯酸酯基團或甲基丙烯酸酯基團的樹脂或它們的任意混合物。
可自由基聚合的化合物中，低分子量的化合物實例有丙烯酸烷基酯、丙烯酸環烷基酯、丙烯酸羥基烷基酯、二烷基氨基烷基丙烯酸酯、甲基丙烯酸烷基酯、甲基丙烯酸環烷基酯、甲基丙烯酸羥基烷基酯、二烷基氨基烷基甲基丙烯酸酯，例如丙烯酸甲酯、丙烯酸丁酯、丙烯酸環己酯、丙烯酸2-羥乙酯、丙烯酸異冰片酯、甲基丙烯酸乙酯、聚矽氧烷丙烯酸酯；其他實例有丙烯腈、乙酸乙烯酯、乙烯基醚、苯乙烯、N-乙烯基吡咯烷酮。含有兩個或更多雙鍵的化合物實例有乙二醇、聚乙二醇、丙二醇、新戊二醇、1,6-己二醇的二 丙烯酸酯，三羥基甲烷三丙烯酸酯、季戊四醇四丙烯酸酯、二季戊四醇六丙烯酸酯、丙烯酸乙烯酯、疫氰脲酸三烯丙酯等。較高分子量的雙鍵化合物實例有通稱為低聚物的一大類物質，例如丙烯酸化的環氧樹脂、丙烯酸化的聚酯樹脂不飽和聚酯樹脂、丙烯酸化的聚醚樹脂、丙烯酸化的聚氨酯樹脂，一般分子量在500-3000。
第五方面，本發明還提供一種油墨或塗料，除含有上述光固化組合物外，還可根據油墨顏色，印刷用途等性能要求添加其他必要成分。該油墨或塗料可以用於圖案印刷，3D列印、PCB阻焊層，液體或幹膜抗蝕材料，基材保護塗層等。
第六方面，本發明還提供一種黏合劑，除含有上述光固化組合物外，還可根據黏合劑的性能要求添加其他必要成分。該黏合劑可以用於黏合玻璃、塑膠、金屬構件等。
除此處舉例外，本領域技術人員很容易根據現有技術和光固化組合物的用途需要添加其它必要成分，例如穩定劑、表面活性劑、流平劑、分散劑。
第七方面，本發明還提供一種光刻膠，含有：a.至少一種上述光引發劑組合物，可選地，其品質占配方全部固體品質的比例為0.2-10%，優選1-8%；b.至少一種可自由基聚合的化合物，例如多官能丙烯酸酯單體；c.鹼溶性樹脂；d.顏料；e.溶劑。
組分b中的多官能丙烯酸酯的實例有二季戊四醇六丙烯酸酯，季戊四醇丙烯酸酯；組分c鹼溶性樹脂的實例是具有羧酸基團的聚丙烯酸酯，例如甲基丙烯酸、衣康酸、馬來酸等與常見單體按需要比例進行共聚得到的共聚物，常見單體例如丙烯酸甲酯、甲基丙烯酸丁酯、丙烯酸苄酯、丙烯酸羥乙酯、苯乙烯、丁二烯、馬來酸酐等；共聚物的實例優選為甲基丙烯酸甲酯和甲基丙烯酸共聚物、甲基丙烯酸苄酯和甲基丙烯酸共聚物、甲基丙烯酸甲酯和甲基丙烯酸丁酯及甲基丙烯酸與苯乙烯共聚物。
組分d的顏料實例如C.I.顏料紅177、C.I.顏料綠7、C.I.顏料藍15：6、溶劑藍25、炭黑、鈦黑、C.I.顏料黑1。
有關組分b，組分c，組分d和組分e的現有文獻很多例如CN103153952A，本領域技術人員可以根據需要選擇。
除組分a作為光引發劑外，還可以加入其它現有商品化或現有技術中已有的光引發劑或助引發劑，只要有利於光固化組合物尤其是光刻膠的性能。例如Omnirad BDK、Omnirad 369、Omnirad 379、Omnirad 389、Omnirad TPO、Omnirad 819、Omnirad ITX、Omnirad DETX、Omnirad 784。Omnirad為IGM樹脂公司商品。
除上述組分外，還可添加其他樹脂的實例有聚甲基丙烯酸烷基酯、乙基纖維素、羧甲基纖維素、線型酚醛樹脂、聚乙烯醇縮丁醛、聚醋酸乙烯酯、聚酯、聚醯亞胺。
第八方面，提供一種黑色光刻膠，當上述光刻膠中顏料是經良好分散的黑色顏料例如碳黑或鈦黑時，就成為一種黑色光 刻膠。用黑色光刻膠可以製造黑色矩陣、單元間隔(Cell gap)的間隔物、微透鏡。
第九方面，使用本發明的光刻膠和/或黑色光刻膠為原料經由彩色濾光片的加工過程可以得到彩色濾光片器件，是彩色顯示幕的重要部件。
使用含有本發明的光引發劑組合物的任一材料例如油墨、塗料、黏合劑、光刻膠、黑色光刻膠作為原料，經必要工序加工得到的任何物品例如彩色濾光片、彩色顯示幕。
為進一步了解本發明，以下舉較佳之實施例，配合圖式、圖號，將本發明之具體構成內容及其所達成的功效詳細說明如下。
以下實施例和對比例能更詳細地闡述本發明。光源設備：365nm LED面光源，藍天特燈發展有限公司；測試設備：體視顯微鏡，COVS-50G，廣州市明美光電技術有限公司，線寬單位為um。實驗材料：式I-1化合物：來自化合物製備例1；式Ⅱ-2化合物：來自化合物製備例2；Omnirad DETX：IGM樹脂公司光引發劑產品；Esacure 3644：IGM樹脂公司光引發劑產品；Omnirad EMK：IGM樹脂公司光引發劑產品； OXE 02：式Ⅳ-1化合物，BASF公司光引發劑產品；OXE 03：式Ⅳ-22化合物，BASF公司光引發劑產品；NCI 831：式Ⅳ-9化合物，日本ADEKA株式會社產品；PBG 304：式Ⅳ-2化合物，常州強力電子新材料股份有限公司產品；Photomer 6010：脂肪族聚氨酯三丙烯酸酯，IGM樹脂公司產品；DPHA：二季戊四醇五、六丙烯酸酯，天津天驕化工有限公司產品；HPMA：聚馬來酸，美國阿拉丁工業公司產品。
化合物製備例：二芳醯基咔唑化合物的製備。
製備例1：9-乙基-3,6-二[4-(2,2,3,3-四氟丙氧基)苯甲醯基]咔唑的製備(式I-1化合物)的製備
1a.製備9-乙基-3,6-二(4-氟苯甲醯基)咔唑
將N-乙基咔唑19.5g，加入250ml二氯乙烷中溶解，再加入34g三氯化鋁，保持0~-5℃，向溶液中滴加對氟苯甲醯氯40g，然後保持反應液0-5℃反應15小時。將反應液分批加入0℃的100ml 10%HCl溶液中，加完攪拌30min。靜置30分鐘後分液，二氯乙烷相用50ml 2%氫氧化鈉溶液洗滌30min，分出二氯乙烷相。減壓蒸餾二氯乙烷溶液並回收二氯乙烷，剩餘物中加入80ml乙酸乙酯結晶，得產物30.5g，白色粉末含量98.5%，收率69.5%。
1b.製備9-乙基-3,6-二[4-(2,2,3,3-四氟丙氧基)苯甲醯基]咔唑
將步驟1a製備的9-乙基-3,6-二(4-氟苯甲醯基)咔唑30g，2,2,3,3-四氟丙醇25g，氫氧化鈉8g，溶入200ml吡啶中，70℃反應18h。減壓蒸餾，蒸出吡啶及多餘的2,2,3,3-四氟丙醇。剩餘物中 加入100ml水，250ml二氯乙烷，攪拌1h。分離水相，二氯乙烷溶液用100ml水洗滌2次。減壓蒸餾回收二氯乙烷，在剩餘物中加入150ml乙酸乙酯和2g活性炭，加熱回流1小時，過濾活性炭，濾液被減壓蒸餾去除約100ml乙酸乙酯後，降溫結晶，過濾後乾燥濾餅得27.8g，淺黃色粉末，含量98.5%，收率61.4%。經1H-NMR(CDCl3)證實該結構，δ[ppm]：1.512(t,3H)，4.425-4.483(m,6H)，5.949-6.277(m,2H)，7.016-7.045(m,4H)，7.496-7.517(d,2H)，7.844-7.868(d,4H)，7.990-8.011(d,2H)，8.534(s,2H)。
製備例2：11-(2-乙基己基)-5,8二[4-(2,2,3,3-四氟丙氧基)苯甲醯基]-11H-苯並[a]咔唑(式Ⅱ-2化合物)的製備。
2a.製備11-(2-乙基己基)-5,8二(4-氟苯甲醯基)-11H-苯並[a]咔唑
在50ml單口瓶中加入B03D 2.0g，加入二氯乙烷20ml溶解，加入氯化鋅0.2g，鄰氟苯甲醯氯2.3g，80℃攪拌反應10小時。降溫後反應液用20ml水洗滌兩次，將二氯乙烷溶液減壓濃縮至幹，得到棕色黏稠狀物4.0g，不經純化用於2b的反應中。
2b.製備11-(2-乙基己基)-5,8二[4-(2,2,3,3-四氟丙氧基)苯甲醯基]-11H-苯並[a]咔唑
將步驟2a的產物11-(2-乙基己基)-5,8二(4-氟苯甲醯基)-11H-苯並[a]咔唑4.0g用吡啶20ml溶解在50ml單口瓶中，再加入四氟丙醇2.2g，氫氧化鈉1.2g，升溫至80℃攪拌5小時。將反應液滴加到100ml水中，然後用100ml二氯乙烷攪拌1h後靜置分層。分出的二 氯乙烷溶液被減壓濃縮至幹，得到咖啡色固體4.7g。此固體用20ml乙酸乙酯和20ml乙醇混合溶劑加熱溶解，加入0.25g活性炭回流1小時，熱過濾，濾液降溫後析出黃色結晶，乾燥後稱重2.5g，兩步反應合計收率51.3%，含量98.51%。經1H-NMR(CDCl3)證實該結構，δ[ppm]：0.754-0.789(m,6H)，1.126-1.328(m,8H)，2.113(s,1H)，4.369-4.452(t,2H)，4.513-4.599(t,2H)，4.928(m,2H)，4.994-5.342(m,1H)，5.537-5.885(m,1H)，7.251-7.272(m,4H)，7.430-7.455(d,1H)，7.566-7.811(m,6H)，7.950-7.979(d,1H)，8.430(s,1H)，8.571(s,1H)，8.668-8.695(d,1H)，8.736-8.764(d,1H)。
光引發劑組合物製備
組合物製備例1：
取式Ⅱ-2所示化合物12g、OXE-02 28g放入研缽中研磨混合，得到40g組合物，醯基咔唑化合物與咔唑基肟酯光引發劑的摩爾比為0.22。
組合物製備例2：
取式I-1所示化合物12g、OXE-02 28g放入研缽中研磨混合，得到40g組合物，醯基咔唑化合物與咔唑基肟酯光引發劑的摩爾比為0.27。
組合物製備例3：
取式I-1所示化合物12g、OXE-03 12g放入研缽中研磨混合，得到24g組合物，醯基咔唑化合物物與咔唑基肟酯光引發劑的摩爾比為1.16。
組合物製備例4：
取式Ⅱ-2所示化合物12g、OXE-03 28g放入研缽中研磨混合，得到40g組合物，醯基咔唑化合物與咔唑基肟酯光引發劑的摩爾比為0.41。
鹼溶性樹脂製備
在1L將甲基丙烯酸芐酯18g、甲基丙烯酸6g、甲基丙烯酸羥乙酯6g、偶氮二異丁腈1.5g、十二硫醇0.6g、甲苯200ml放入恒壓滴液漏斗，在500ml四口瓶中放入100ml甲苯，氮氣置換，升溫至80℃，滴加漏斗中溶液，反應6h後降溫濾出，得到24g白色鹼溶性樹脂。
光刻膠組合物實施例及對比例
按表1~4中所述各組分配製各實施例及對比例。引發劑和增感劑可使用組合物製備例中的組合物或按表中比例混合在溶解於PMA中，再將組合物溶液與黑色色漿按比例混合。將各組分混合均勻後，使用10μm線棒在載玻片上塗膜，90℃烘箱烘乾5min，使用365nm光源配合120μm掩膜板進行固化，使用1% NaOH溶液25℃進行顯影，並用純淨水浸泡清洗10s，90℃烘箱烘乾30min後測量顯影圖像線寬，線寬單位為μm。
Figure 109109042-A0305-02-0023-32
Figure 109109042-A0305-02-0024-33
Figure 109109042-A0305-02-0024-34
Figure 109109042-A0305-02-0024-35
Figure 109109042-A0305-02-0025-36
Figure 109109042-A0305-02-0025-37
表1、表2及表4中實施例及對比例經過塗布、固化、顯影、測量，資料如表5、表6、表7、表8所示，結果顯示：在使用I-1作為增感劑搭配多種不同咔唑基肟酯，其使用比例在本發明要求的範圍內的實施例顯影效果明顯好於未使用增感劑、單獨使用增感劑或增感劑用量在本發明要求範圍值以外的對比例，特別是對比例2的結果表明，式I-1所示化合物單獨不能形成顯影圖案，幾乎沒有引 發聚合的作用。對比表4配方和表8資料顯示，使用I-1作為增感劑其增感效果明顯優於硫雜蒽酮、香豆素、四乙基米氏酮，後三者的顯影線寬甚至小於單用肟酯對比例1配方。
表3中實施例及對比例經過塗布、固化、顯影、測量，資料如表7所示，結果顯示：在使用Ⅱ-2作為增感劑搭配多種不同咔唑基肟酯，其使用比例在本發明要求的範圍內的實施例顯影效果明顯好於未使用增感劑、單獨使用增感劑或增感劑用量在本發明要求範圍值以外的對比例，特別是對比例9的結果表明，式Ⅱ-2所示化合物單獨使用不能形成顯影圖案，幾乎沒有引發聚合的作用。對比表4配方和表8資料顯示，使用Ⅱ-2作為增感劑的增感效果顯著高於硫雜蒽酮、香豆素、四乙基米氏酮。
Figure 109109042-A0305-02-0026-38
Figure 109109042-A0305-02-0026-39
表7
Figure 109109042-A0305-02-0027-40
Figure 109109042-A0305-02-0027-41
黏合劑實施例
按表9各組分配製各實施例及對比例，將各組分混合均勻後，使用50μm線棒在載玻片上塗膜，使用365nm光源配合掩膜板進行固化，固化後測量膜重，然後在室溫下的丙酮中浸泡36h後再次測量膜重，計算凝膠轉化率。
Figure 109109042-A0305-02-0027-42
表9對比例與實施例測試資料如表10所示。由資料可見，實施例10和實施例11使用本發明提供的光固化組合物的黏合劑光照雙鍵凝 膠轉化率明顯高於單獨使用肟酯光引發劑的對比例13。
Figure 109109042-A0305-02-0028-43
綜上所述，本發明提供的新型二芳醯基咔唑化合物與咔唑基肟酯光引發劑一起使用在光刻膠組合物或黏合劑中顯示了顯著的增感作用，當二芳醯基咔唑化合物與咔唑基肟酯光引發劑的摩爾比在0.1-1.4之間顯示出了最佳的增感效果。
以上所述乃是本發明之具體實施例及所運用之技術手段，根據本文的揭露或教導可衍生推導出許多的變更與修正，仍可視為本發明之構想所作之等效改變，其所產生之作用仍未超出說明書及圖式所涵蓋之實質精神，均應視為在本發明之技術範疇之內，合先陳明。
綜上所述，依上文所揭示之內容，本發明確可達到發明之預期目的，提供一種新的二芳醯基咔唑化合物及其作為增感劑的應用，極具產業上利用之價值，爰依法提出發明專利申請。
Figure 109109042-A0305-02-0001-1

Claims (19)

  1. 一種二芳醯基咔唑化合物，結構如式I-1至I-4、I-6和I-7任一所示或如式Ⅱ所示：
    Figure 109109042-A0305-02-0029-44
    Figure 109109042-A0305-02-0029-45
    Figure 109109042-A0305-02-0029-46
    Figure 109109042-A0305-02-0029-47
    Figure 109109042-A0305-02-0030-48
    Figure 109109042-A0305-02-0030-49
    Figure 109109042-A0305-02-0030-50
     其中，R11，R18各自獨立地是H，鹵素原子，C1-C8烷基，C1-C8烷氧基，CN；R12，R13，R14，R15，R16，R17各自獨立地是H，F，Cl，COOR20，C1-C12直鏈或支鏈烷基，C1-C12直鏈或支鏈烷氧基，其中所述C1-C12直鏈或支鏈烷基未經取代或經一個或多個以下基團取代：苯基、C3-C6環烷基、F、Cl、COOR21、OR21、SR21、RO(OCH2n+1)2、Si(CnH2n+1)3，n為1-4的整數；條件是，每個苯甲醯基的苯環上至少有一個取代基是氟原子或含有氟代烷基的基團； R19是C1-C12直鏈或支鏈烷基，C2-C12烯基，C3-C12烯基烷基，其中的碳原子上的氫未經取代或經一個或多個以下基團取代：苯基、C5-C6環烷基、C3-C6雜環基、鹵素、COOR20、OR20、SR20、PO(OCnH2n+1)2、Si(CnH2n+1)3，n為1-4的整數；或者C3-C12烯基烷基被一個或多個O、S、SO、SO2、CO、COO間隔；或R19各自獨立地是C3-C12烷基，其烷基鏈經一個或多個O、S、SO、SO2、CO間隔；或R19是苯基，苯基未經取代或經一個或多個C1-C8烷基、鹵素原子、OR20、SR20、COR20、CN、COOH取代；或R19可與取代基R11一起，或R19可與取代基R18一起構成C4-C6雜環結構；R20是C1-C12烷基或苯基，其未經取代或經一個或多個以下基團取代：苯基、C3-C6環烷基、F、Cl、OR21、SR21；R21是C1-C12烷基。
  2. 如申請專利範圍第1項所述之二芳醯基咔唑化合物，其中式Ⅱ所示的化合物選自如式Ⅱ-A和式Ⅱ-B所示化合物：
    Figure 109109042-A0305-02-0031-51
    Figure 109109042-A0305-02-0032-52
     其中，R12，R13，R14，R15，R16，R17各自獨立地是H，F，Cl，COOR20，C1-C12直鏈或支鏈烷基，C1-C12直鏈或支鏈烷氧基，其中C1-C12直鏈或支鏈烷基未經取代或經一個或多個以下基團取代：苯基、C3-C6環烷基、C3-C6雜環基、F、Cl、COOR21、OR21、SR21、PO(OCH2n+1)2、Si(CnH2n+1)3，n為1-4的整數；條件是，每個苯甲醯基的苯環上至少有一個取代基是氟原子或含有氟代烷基的基團；R19是C1-C12直鏈或支鏈烷基，C2-C12烯基，C3-C12烯基烷基，其中的碳原子上的氫未經取代或經一個或多個以下基團取代：苯基、C5-C6環烷基、C3-C6雜環基、鹵素、COOR20、OR20、SR20、PO(OCnH2n+1)2、Si(CnH2n+1)3，n為1-4的整數；或者C3-C12烯基烷基被一個或多個O、S、SO、SO2、CO、COO間隔；或R19是C3-C12烷基，其烷基鏈經一個或多個O、S、SO、SO2、CO間隔； 或R19是苯基，苯基未經取代或經一個或多個C1-C8烷基、鹵素原子、OR20、SR20、COR20、CN、COOH取代；R20是C1-C12烷基，其未經取代或經一個或多個以下基團取代：苯基、C3-C6環烷基、C3-C6雜環基、F、Cl、OR21、SR21；R21是C1-C12烷基；Y2是C2-C8直鏈或支鏈烷基，鏈可以被O、S、NR21或羰基***，或碳上的氫被OH、鹵素原子取代。
  3. 如申請專利範圍第1項所述之二芳醯基咔唑化合物，其中式Ⅱ所示的化合物係選自以下化合物之一或者它們的任意混合物：
    Figure 109109042-A0305-02-0033-53
    Figure 109109042-A0305-02-0033-54
    Figure 109109042-A0305-02-0034-55
    Figure 109109042-A0305-02-0034-56
  4. 一種如申請專利範圍第1項所述之二芳醯基咔唑化合物的製備方法，其中以式Ⅲ-A或式Ⅲ-B所示的化合物為原料，用對應的取代芳醯氯或酸酐經一步或兩步傅克醯基化反應得到對稱或不對稱的二芳醯基化合物；如任一芳基上含有羧基或含有鹵素原子時，再與R20OH醇類化合物進行酯化反應或者醚化反應，得到式I-1至I-4、I-6、I-7或式Ⅱ所示的二芳醯基咔唑化合物，
    Figure 109109042-A0305-02-0034-57
     其中，當製備如式I-1至I-4、I-6所示的化合物時，R1和R8是H，且R9是乙基；當製備如式I-7所示的化合物時，R1是H，R8和R9一起為2,2-二 甲基-1,3-亞丙基；當製備如式Ⅱ所示的化合物時，R11，R18，R19定義同如申請專利範圍第1項所述。
  5. 一種光引發劑組合物，含有至少一種申請專利範圍第1項所述的二芳醯基咔唑化合物和至少一種咔唑基肟酯光引發劑，其中該咔唑基肟酯光引發劑是指至少一個肟酯基團
    Figure 109109042-A0305-02-0035-58
    直接或通過一個羰基連接在N-取代咔唑母體結構上；其中R22為C1-C12烷基，其未經取代或經一個或多個以下基團取代：鹵素原子、OR24、SR24、C3-C8環烷基、苯基、C4-C20雜芳基、COOR24；或R22為C6-C20芳基或C4-C20雜芳基，其各自未經取代或經一個或多個以下基團取代：鹵素原子、C1-C20烷基、被一個或多個氟原子取代的C1-C8烷基、CN、OR24、SR24、NR25R26；或R22為C6-C20芳醯基，C4-C20雜芳醯基；R23選自C1-C12烷基，C6-C20芳基，C1-C4烷氧基；R24為H，C1-C8烷基，任意被一個或多個C3-C8雜環基、F、乙醯氧基取代的C1-C8烷基，苯基，C1-C20烷基苯基；R25，R26各自為C1-C4烷基，經OR24取代的C2-C4烷基，或NR25R26為環狀結構
    Figure 109109042-A0305-02-0035-59
    ，
    Figure 109109042-A0305-02-0035-60
    ，
    Figure 109109042-A0305-02-0035-61
    ，
    Figure 109109042-A0305-02-0035-62
    ；所述咔唑母體結構選自咔唑、苯並咔唑、二苯並咔唑，母體結構上氫原子除被上述肟酯基團或連接著肟酯基團的羰基取代基外，還可以被以下一個或多個基團取代：C1-C20烷基，鹵素， NO2，CN，OR27，C6-C20芳醯基，C4-C20雜芳醯基，4,5-二苯基咪唑-2基，母體結構上的取代基在空間上相鄰時可以構成新的五元到七元環狀結構；其中的C1-C20烷基未經取代或被以下一個或多個基團取代：鹵素、C3-C8環烷基、C3-C8雜環基、苯基、COOR27、OR27、PO(OCnH2n+1)2、Si(CnH2n+1)3，n為1-4的整數，或者碳原子數大於3時被一個或多個氧原子***；R27為C1-C8烷基，被C3-C8雜環烷基取代的C1-C8烷基；C6-C20芳醯基，C4-C20雜芳醯基中的芳基或雜芳基未經取代或被以下一個或多個基團取代：鹵素原子，CN，
    Figure 109109042-A0305-02-0036-63
    ，R24’，OR24’，SR24’，NR25’R26’，COOR24’，R24’SO2；R22’，R23’，R24’，NR25’R26’的定義與對應的R22，R23，R24，NR25R26相同。
  6. 如申請專利範圍第5項所述之光引發劑組合物，其中該咔唑基肟酯光引發劑選自以下化合物或者它們的任意混合物：
    Figure 109109042-A0305-02-0036-64
    Figure 109109042-A0305-02-0037-65
    Figure 109109042-A0305-02-0038-66
    Figure 109109042-A0305-02-0039-67
    Figure 109109042-A0305-02-0040-69
    Figure 109109042-A0305-02-0041-70
  7. 如申請專利範圍第5項所述之光引發劑組合物，其中所述申請專利範圍第1項的二芳醯基咔唑化合物與所述咔唑基肟酯光引發劑的摩爾比為0.1：1~1.4：1。
  8. 如申請專利範圍第7項所述之光引發劑組合物，其中所述申請專利範圍第1項的二芳醯基咔唑化合物與所述咔唑基肟酯光引發劑的摩爾比為0.22：1~1.16：1。
  9. 一種光固化組合物，包括：a.至少一種申請專利範圍第5項的光引發劑組合物，b.至少一種可自由基聚合的化合物。
  10. 如申請專利範圍第9項所述之光固化組合物，其中該可自由基聚合的化合物選自丙烯酸酯類化合物、甲基丙烯酸酯類化合物、含有丙烯酸酯或甲基丙烯酸酯基團的樹脂或它們的任意混合物。
  11. 如申請專利範圍第9項所述之光固化組合物，其中a組分在全部固體份中的質量占比為1-10%。
  12. 一種含有申請專利範圍第9、10或11項中任一項所述的光固化組合物的油墨。
  13. 一種含有申請專利範圍第9、10或11項中任一項所述的光固化組合物的塗料。
  14. 一種含有申請專利範圍第9、10或11項中任一項所述的光固化組合物的黏合劑。
  15. 一種光刻膠，包含有：a.至少一種申請專利範圍第5項所述的光引發劑組合物；b.多官能丙烯酸酯單體；c.鹼溶性樹脂；d.顏料；e.溶劑。
  16. 一種黑色光刻膠，根據申請專利範圍第15項所述的光刻膠，其中顏料是經良好分散的碳黑或鈦黑。
  17. 一種黑色矩陣，其特徵為使用申請專利範圍第16項所述的黑色光刻膠製造。
  18. 一種光間隔物，其特徵為使用申請專利範圍第16項所述的黑色光刻膠製造。
  19. 一種彩色濾光片器件，使用申請專利範圍第15項所述的光刻膠和申請專利範圍第16項所述的黑色光刻膠為光刻膠原料經由濾光片的加工過程得到的濾光片器件。
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