CN107406673B - 着色树脂组合物、着色膜、装饰基板及触摸面板 - Google Patents
着色树脂组合物、着色膜、装饰基板及触摸面板 Download PDFInfo
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- CN107406673B CN107406673B CN201680016918.2A CN201680016918A CN107406673B CN 107406673 B CN107406673 B CN 107406673B CN 201680016918 A CN201680016918 A CN 201680016918A CN 107406673 B CN107406673 B CN 107406673B
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- 239000011787 zinc oxide Substances 0.000 description 1
- 235000014692 zinc oxide Nutrition 0.000 description 1
- DRDVZXDWVBGGMH-UHFFFAOYSA-N zinc;sulfide Chemical compound [S-2].[Zn+2] DRDVZXDWVBGGMH-UHFFFAOYSA-N 0.000 description 1
- 229910052845 zircon Inorganic materials 0.000 description 1
- GFQYVLUOOAAOGM-UHFFFAOYSA-N zirconium(iv) silicate Chemical compound [Zr+4].[O-][Si]([O-])([O-])[O-] GFQYVLUOOAAOGM-UHFFFAOYSA-N 0.000 description 1
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Abstract
本发明提供一种着色树脂组合物,所述着色树脂组合物通过含有具有特定结构的聚酰亚胺树脂从而达成显著的耐热性,而且通过使着色材料高度稳定分散由此可形成可靠性优异的着色膜。本发明的着色树脂组合物含有:(A)碱溶性聚酰亚胺树脂,其具有包含酚式羟基、磺酸基或硫醇基的结构单元;(B)着色材料;(C)高分子分散剂;及(D)有机溶剂。由本发明的组合物得到的经图案化的着色层在装饰基板、触摸面板、有机EL显示装置等中有用。
Description
技术领域
本发明涉及着色树脂组合物、着色膜、装饰基板及触摸面板。
背景技术
近年来,智能手机、平板PC等使用了投影型静电电容式触摸面板的移动设备正快速普及。对于投影型静电电容式触摸面板而言,通常,在画面区域形成ITO(Indium TinOxide,氧化铟锡)膜的图案,在其周边部进一步形成有钼等金属布线部。而且,为了隐藏这样的金属布线部,常常在投影型静电电容式触摸面板的保护玻璃(cover glass)的内侧形成有黑色或白色等的遮光图案。
触摸面板的方式大致分为在保护玻璃与液晶面板之间形成触摸面板层的Out-cell型、在液晶面板上形成触摸面板层的On-cell型、在液晶面板的内部形成触摸面板层的In-cell型、及保护玻璃上直接形成有触摸面板层的OGS(One Glass Solution,单片式触控面板)型,与以往类型的Out-cell型相比,从谋求薄型化及轻量化方面考虑,OGS型的触摸面板的开发逐渐盛行(专利文献1)。
对于OGS型的触摸面板而言,由于在保护玻璃上形成遮光图案后,在高热下形成ITO电极等,因而对遮光图案要求高耐热性,进而,同时还要求ITO电极的图案形成工序中的耐化学药品性。
已知有多种利用使用了含有Cardo树脂的感光性树脂组合物的光刻法形成耐热性及耐化学药品性优异的黑色的遮光图案的技术(专利文献2及3),但进一步要求耐热性等。另一方面,为了得到耐热性及耐化学药品性更优异的遮光图案,还进行了得到在聚酰亚胺树脂中分散着色材料而成的组合物的尝试(专利文献4及5)。
现有技术文献
专利文献
专利文献1:日本特开2009-301767号公报
专利文献2:日本特开2012-145699号公报
专利文献3:日本特开2014-099159号公报
专利文献4:日本特开2005-162905号公报
专利文献5:日本特开2009-051891号公报
发明内容
发明所要解决的课题
然而,能溶解聚酰亚胺树脂的有机溶剂限于N-甲基吡咯烷酮、γ-丁内酯等高极性溶剂,着色材料尤其是经表面处理或经树脂被覆的有机颜料或炭黑在这样的高极性溶剂中的稳定分散非常困难,无法控制形成的遮光图案的颜色特性、绝缘性,这被视为问题。
因此,本发明的目的在于提供一种着色树脂组合物,所述着色树脂组合物通过含有具有特定结构的聚酰亚胺树脂从而达成显著的耐热性,而且,通过使着色材料高度稳定分散从而可形成可靠性优异的着色膜。
用于解决课题的手段
本发明人等进行了深入研究,结果发现,在具有特定结构的聚酰亚胺树脂、高分子分散剂及有机溶剂的混合物中分散着色材料而成的着色树脂组合物对于解决上述课题非常有效,从而完成了本发明。
即,本发明具有以下的构成。
本发明提供
(1)一种着色树脂组合物,其含有:
(A)碱溶性聚酰亚胺树脂,其具有下述通式(1)表示的结构单元;
(B)着色材料;
(C)高分子分散剂;和
(D)有机溶剂。
(通式(1)中,R1表示4~10价的有机基团,R2表示2~8价的有机基团,R3及R4各自独立地表示酚式羟基、磺酸基、硫醇基或羧基,p及q各自独立地表示0~6的整数,p与q之和为1以上。)。
另外,包括以下的本发明的优选方式。
(2)根据(1)所述的着色树脂组合物,其中,前述(C)高分子分散剂不具有酸值,具有胺值。
(3)根据(1)或(2)的着色树脂组合物,其中,前述(C)高分子分散剂具有作为碱性官能团的叔氨基或含氮杂环。
(4)根据(1)~(3)中任一项所述的着色树脂组合物,其中,前述(D)有机溶剂以乙酸酯系溶剂为主成分。
(5)根据(1)~(4)中任一项所述的着色树脂组合物,其中,前述(B)着色材料为有机颜料及/或无机颜料。
另外,作为着色膜,包括以下的方式。
(6)一种着色膜,其是前述中任一项所述的着色树脂组合物的固化物。
而且,作为利用了前述着色膜的优点的制品,包括以下的制品。
(7)一种装饰基板,其具有前述着色膜。
(8)一种触摸面板,其具有前述装饰基板。
(9)一种有机EL显示装置,其中,在驱动电路上的平坦化层和第一电极上的绝缘层中的至少一层上具有前述着色膜。
发明的效果
通过本发明的着色树脂组合物,可形成由于着色材料高度稳定分散从而提高了可靠性的、具有显著的耐热性的着色膜。
具体实施方式
本发明的着色树脂组合物的特征在于,含有:(A)碱溶性聚酰亚胺树脂,其具有特定的结构单元;(B)着色剂;(C)高分子分散剂;和(D)有机溶剂。
本发明的着色树脂组合物含有(A)碱溶性聚酰亚胺树脂,所述碱溶性聚酰亚胺树脂具有下述通式(1)表示的结构单元。
(通式(1)中,R1表示4~10价的有机基团,R2表示2~8价的有机基团,R3及R4各自独立地表示酚式羟基、磺酸基或硫醇基,p及q各自独立地表示0~6的整数。)
作为碱溶性聚酰亚胺树脂,优选在氢氧化钾等无机碱及四甲基氢氧化铵(TMAH)等有机碱中,在规定的时间内溶解。具体而言,通常优选的是,于23℃将树脂浸渍于足量的0.05%KOH水溶液或足量的2.38%TMAH水溶液中时、在2分钟以内溶解的树脂。
需要说明的是,对于本发明中使用的碱溶性聚酰亚胺树脂而言,不需要完全进行酰亚胺化,例如也包含10%以下未进行酰亚胺化的碱溶性聚酰亚胺树脂。
通式(1)中,R1-(R3)p表示作为原料的酸二酐进行了酰亚胺化后的残基。R1为4~10价的有机基团,优选为具有芳香族环或环状脂肪族基的碳原子数为5~40的有机基团。
作为酸二酐,可举出例如以下物质、及它们的芳香族环或环状脂肪族基的1~6个氢被R3取代而得到的物质。
均苯四甲酸二酐、3,3’,4,4’-联苯四羧酸二酐、3,3’,4,4’-二苯甲酮四羧酸二酐、双(3,4-二羧基苯基)砜二酐、双(3,4-二羧基苯基)醚二酐或2,2-双(3,4-二羧基苯基)六氟丙烷二酐等芳香族四羧酸二酐;
丁烷四羧酸二酐、1,2,3,4-环戊烷四羧酸二酐、双环[2.2.2]辛-7-烯-四羧酸二酐或双环[2.2.2]辛烷四羧酸二酐等脂肪族四羧酸二酐。
为了提高着色树脂组合物的保存稳定性,优选双(3,4-二羧基苯基)醚二酐、2,2-双(3,4-二羧基苯基)六氟丙烷二酐、双环[2.2.2]辛-7-烯-四羧酸二酐、双环[2.2.2]辛烷四羧酸二酐。
通式(2)表示的酸二酐。
以及它们的氢的一部分或全部被R3取代而得到的产物。
(通式(2)中,R5表示单键、氧原子、硫原子、CH2、C(CF3)2、C(CH3)2、SO2或二苯基环戊烷,R6及R7各自独立地表示氢原子、羟基或硫醇基。)
若以其他形式来表现R1,则优选为以苯、联苯、二苯基烷烃、二苯甲酮、二苯基砜、二苯基醚、碳原子数为5~8的环烷烃、以及从通式(2)的化合物中除去酸酐基而得到的结构为骨架的官能团。另外,该官能团具有多个苯环的情况下,优选2个酸酐基键合于不同的苯环。
通式(1)中,R2-(R4)q表示二胺进行酰亚胺化反应后的残基,R2为2~8价的有机基团,优选为具有芳香族环或环状脂肪族基的碳原子数为5~40的有机基团。
作为二胺,可举出例如间苯二胺、对苯二胺、1,4-双(4-氨基苯氧基)苯、1,3-双(4-氨基苯氧基)苯、1,3-双(3-氨基苯氧基)苯、双[4-(4-氨基苯氧基)苯基]砜、双[4-(4-氨基苯氧基)苯基]丙烷、双[4-(4-氨基苯氧基)苯基]六氟丙烷、双[4-(3-氨基苯氧基)苯基]砜、9,9-双(4-氨基苯基)芴、2,5-双(氨基甲基)双环[2.2.1]庚烷、2,6-双(氨基甲基)双环[2.2.1]庚烷、二氨基二苯基醚、二氨基二苯基砜、二氨基二苯基甲烷、二氨基二苯基丙烷、二氨基二苯基六氟丙烷、二氨基二苯基硫醚、联苯胺或2,2’-双三氟联苯胺、或下述通式(3)或(4)表示的二胺及它们的取代物。
(通式(3)及(4)中,R5表示单键、氧原子、硫原子、CH2、C(CF3)2、C(CH3)2、SO2或二苯基环戊烷,R6及R7各自独立地表示氢原子、羟基或硫醇基。)
若以其他形式来表现R2,则优选为以苯、联苯、芴、二苯基烷烃、二苯甲酮、二苯基砜、二苯基醚、二苯基硫醚、碳原子数为5~8的环烷烃、以及从通式(3)及(4)的化合物中除去氨基而得到的化合物为骨架的官能团。另外,该官能团具有多个苯环的情况下,优选2个氨基键合于不同的苯环。
具有通式(1)表示的结构单元的碱溶性聚酰亚胺树脂优选在主链末端具有选自羧基、酚式羟基、磺酸基及硫醇基中的具有活性氢的极性基团。这些具有活性氢的极性基团向主链末端的导入可通过使用含有具有活性氢的极性基团的封端剂而达成。作为这样的封端剂,可举出例如单胺、酸酐、单羧酸、单酰氯化合物或单活性酯化合物。
作为用作封端剂的单胺,可举出以下的物质。
5-氨基-8-羟基喹啉、1-羟基-7-氨基萘、1-羟基-6-氨基萘、1-羟基-5-氨基萘、1-羟基-4-氨基萘、2-羟基-7-氨基萘、2-羟基-6-氨基萘、2-羟基-5-氨基萘、1-羧基-7-氨基萘、1-羧基-6-氨基萘、1-羧基-5-氨基萘、2-羧基-7-氨基萘、2-羧基-6-氨基萘、2-羧基-5-氨基萘、2-氨基苯甲酸、3-氨基苯甲酸、4-氨基苯甲酸、4-氨基水杨酸、5-氨基水杨酸、6-氨基水杨酸、2-氨基苯磺酸、3-氨基苯磺酸、4-氨基苯磺酸、3-氨基-4,6-二羟基嘧啶、2-氨基苯酚、3-氨基苯酚、4-氨基苯酚、2-氨基苯硫酚、3-氨基苯硫酚或4-氨基苯硫酚。
作为用作封端剂的酸酐、单羧酸、单酰氯化合物及单活性酯化合物,可举出以下的物质。
作为酸酐,可举出苯二甲酸酐、马来酸酐、纳迪克酸、环己烷二甲酸酐或3-羟基苯二甲酸酐等酸酐。
作为单羧酸,可举出3-羧基苯酚、4-羧基苯酚、3-羧基苯硫酚、4-羧基苯硫酚、1-羟基-7-羧基萘、1-羟基-6-羧基萘、1-羟基-5-羧基萘、1-巯基-7-羧基萘、1-巯基-6-羧基萘、1-巯基-5-羧基萘、3-羧基苯磺酸、4-羧基苯磺酸等。
作为单酰氯化合物,可举出上述单羧酸的羧基进行了酰氯化而得到的产物。
作为单酰氯化合物,可举出对苯二甲酸、邻苯二甲酸、马来酸、环己烷二甲酸、1,5-二羧基萘、1,6-二羧基萘、1,7-二羧基萘或2,6-二羧基萘等二羧酸类中的仅1个羧基进行了酰氯化而得到的产物。
作为活性酯化合物,可举出通过上述单酰氯化合物与N-羟基苯并三唑或N-羟基-5-降冰片烯-2,3-二羧基酰亚胺的反应而得到的产物。
对于用作封端剂的单胺的比例而言,相对于全部胺成分,优选为0.1~60摩尔%,更优选为1~40摩尔%。对于用作封端剂的酸酐、单羧酸、单酰氯化合物或单活性酯化合物的比例而言,相对于二胺成分,优选为0.1~100摩尔%,更优选为5~90摩尔%。
此外,为了提高使本发明的着色树脂组合物固化而成的着色膜与基板等的密合性,可在不使耐热性下降的范围内,使R2或R5为具有硅氧烷结构的脂肪族的取代基。作为这样的碱溶性聚酰亚胺树脂,例如,可举出下述碱溶性聚酰亚胺树脂:作为二胺成分,包含1~10摩尔%的双(3-氨基丙基)四甲基二硅氧烷或双(对氨基苯基)八甲基五硅氧烷。
作为本发明的着色树脂组合物,除了通式(1)表示的碱溶性聚酰亚胺树脂以外,还可添加其他碱溶性树脂。作为其他碱溶性树脂,没有特别限制,可举出聚酰亚胺树脂、丙烯酸树脂、硅氧烷树脂、Cardo树脂等。作为通式(1)表示的碱溶性聚酰亚胺树脂在碱溶性树脂中所占的比例,根据所期望的耐热性、分散稳定性等适当确定即可,优选为10质量%以上,更进一步优选为50质量%以上。
作为碱溶性聚酰亚胺树脂的制造方法,可举出以下的方法。
首先,利用例如以下的方法得到聚酰亚胺前体的工序。
(a)在低温下使四羧酸二酐与二胺化合物(其一部分被置换成单胺化合物)反应的方法。
(b)在低温下使四羧酸二酐(其一部分被置换成酸酐、单酰氯化合物或单活性酯化合物)与二胺化合物反应的方法。
(c)使四羧酸二酐与醇反应而得到二酯化合物,然后在缩合剂的存在下使二酯化合物与二胺(其一部分被置换成单胺化合物)反应的方法。
(d)使四羧酸二酐与醇反应而得到二酯。然后,使在反应物中残留的二羧酸进行酰氯化。而后,使其生成物与二胺化合物(其一部分被置换成单胺化合物。)进行反应的方法。
进而,利用以下的方法得到聚酰亚胺树脂的工序。
(a)利用公知的方法使得到的聚酰亚胺前体完全酰亚胺化的方法。
(b)在使得到的聚酰亚胺前体进一步进行酰亚胺化的反应的中途,停止酰亚胺化反应,从而导入未反应成酰亚胺的结构的方法,
(c)混合经完全酰亚胺化的聚酰亚胺树脂,从而导入一部分酰亚胺结构的方法。
此外,可利用在高温下使四羧酸二酐与二异氰酸酯化合物进行反应,利用脱羧反应制造聚酰亚胺的方法。
对于碱溶性聚酰亚胺树脂的重均分子量而言,为了提高将本发明的着色树脂组合物固化而形成的着色膜的耐化学药品性、在碱显影液中的溶解性,优选为5000~100000,更优选为10000~70000。
本发明的着色树脂组合物含有(B)着色材料。所谓(B)着色材料,是指在电子信息材料的领域中通常可使用的有机颜料、无机颜料或染料。为了提高将本发明的着色树脂组合物固化而形成的着色膜的耐热性、可靠性,优选有机颜料或无机颜料。
作为有机颜料,可举出以下的物质。
二酮吡咯并吡咯系颜料、偶氮、双偶氮、多偶氮等偶氮系颜料;
铜酞菁、卤化铜酞菁、无金属酞菁等酞菁系颜料;
氨基蒽醌、二氨基二蒽醌、蒽嘧啶、黄烷士酮、蒽嵌蒽醌、阴丹酮、皮蒽酮、蒽酮紫等蒽醌系颜料;
以及,喹吖啶酮系颜料、二噁嗪系颜料、芘酮(perinone)系颜料、苝系颜料、硫靛系颜料、异吲哚啉系颜料、异吲哚啉酮系颜料、喹酞酮系颜料、士林系颜料或金属络合物系颜料。
作为无机颜料,可举出以下的物质。
氧化钛、锌白、硫化锌、铅白、碳酸钙、沉降性硫酸钡、白炭、矾土白、高岭土、滑石、膨润土、黑色氧化铁、镉红、铁丹(bengala)、钼红、钼橙(molybdate orange)、铬朱红(chrome vermillion)、铬黄、镉黄、黄色氧化铁、钛黄、氧化铬、铬绿、钛钴绿、钴绿、钴铬绿、维多利亚绿、群青、普鲁士蓝、钴蓝、青天蓝、钴二氧化硅蓝、钴锌二氧化硅蓝、锰紫、钴紫。
作为染料,可举出偶氮染料、蒽醌染料、稠合多环芳香族羰基染料、靛类染料、碳鎓染料、酞菁染料、次甲基染料、聚次甲基染料。
作为红色的颜料,可举出例如颜料红9、48、97、122、123、144、149、166、168、177、179、180、192、209、215、216、217、220、223、224、226、227、228、240、254(数值均为染料索引(color index)(以下,记为“CI”编号))。
作为橙色的颜料,可举出例如颜料橙13、36、38、43、51、55、59、61、64、65、71。
作为黄色的颜料,可举出例如颜料黄12、13、17、20、24、83、86、93、95、109、110、117、125、129、137、138、139、147、148、150、153、154、166、168、185(数值均为CI编号)。
作为紫色的颜料,可举出颜料紫19、23、29、30、32、37、40、50(数值均为CI编号)。
作为蓝色的颜料,可举出颜料蓝15、15:3、15:4、15:6、22、60、64(数值均为CI编号)。
作为绿色的颜料,可举出例如颜料绿7、10、36或58(数值均为CI编号)。
作为黑色的颜料,可举出例如黑色有机颜料、混色有机颜料或无机颜料等。作为黑色有机颜料,可举出例如炭黑、苝黑、苯胺黑、苯并呋喃酮系颜料。作为混色有机颜料,可举出将具有红、蓝、绿、紫、黄色、品红色(magenta)或蓝绿色(cyan)的颜色的2种以上的颜料混合而进行拟黑色化而得到的产物。
作为无机颜料,可举出以下的物质。
石墨;
钛、铜、铁、锰、钴、铬、镍、锌、钙、银等金属的微粒;上述金属的氧化物、复合氧化物、硫化物、氮化物及氮氧化物。其中,优选具有高遮光性的炭黑及钛氮化物。
作为白色的颜料,可举出例如二氧化钛、碳酸钡、氧化锆、碳酸钙、硫酸钡、氧化铝白、二氧化硅。
作为染料,可举出以下的物质。
直接红2、4、9、23、26、28、31、39、62、63、72、75、76、79、80、81、83、84、89、92、95、111、173、184、207、211、212、214、218、221、223、224、225、226、227、232、233、240、241、242、243、247;
酸性红35、42、51、52、57、62、80、82、111、114、118、119、127、128、131、143、145、151、154、157、158、211、249、254、257、261、263、266、289、299、301、305、319、336、337、361、396、397;
活性红3、13、17、19、21、22、23、24、29、35、37、40、41、43、45、49、55;
碱性红12、13、14、15、18、22、23、24、25、27、29、35、36、38、39、45、46;
直接紫7、9、47、48、51、66、90、93、94、95、98、100、101;
酸性紫5、9、11、34、43、47、48、51、75、90、103、126;
活性紫1、3、4、5、6、7、8、9、16、17、22、23、24、26、27、33、34;
碱性紫1、2、3、7、10、15、16、20、21、25、27、28、35、37、39、40、48;
直接黄8、9、11、12、27、28、29、33、35、39、41、44、50、53、58、59、68、87、93、95、96、98、100、106、108、109、110、130、142、144、161、163;
酸性黄17、19、23、25、39、40、42、44、49、50、61、64、76、79、110、127、135、143、151、159、169、174、190、195、196、197、199、218、219、222、227;
活性黄2、3、13、14、15、17、18、23、24、25、26、27、29、35、37、41、42;
碱性黄1、2、4、11、13、14、15、19、21、23、24、25、28、29、32、36、39、40;
酸性绿16;酸性蓝9、45、80、83、90、185;碱性橙21、23(数值均为CI编号)。
本发明的着色材料树脂组合物所含有的着色材料/树脂成分的质量比优选为90/10~20/80,更优选为90/10~40/60。此处所谓树脂成分,是指包含碱溶性聚酰亚胺树脂及高分子分散剂等添加剂、以及根据情况进一步添加的高分子化合物在内的树脂成分。树脂成分过少时,有时着色材料的分散稳定性变得不充分。另一方面,着色材料过少时,将本发明的着色树脂组合物固化而形成的着色膜的着色有时变得不充分。
本发明的着色树脂组合物含有(C)高分子分散剂。通过含有(C)高分子分散剂,从而能将着色材料均匀并且稳定地分散于树脂组合物中。作为(C)高分子分散剂,可举出例如聚酯系高分子分散剂、丙烯酸系高分子分散剂、聚氨酯系高分子分散剂、聚烯丙基胺系高分子分散剂或碳二亚胺系分散剂。
作为高分子分散剂,优选主链由多胺、聚醚、聚酯、聚氨酯、聚(甲基)丙烯酸酯等形成、在侧链上具有选自胺、羧酸、磷酸、胺盐、羧酸盐、磷酸盐等中的具有极性的官能团的聚合物。认为位于侧链的极性的官能团吸附颜料、聚合物的主链由于空间位阻效应而妨碍着色剂彼此的接触,结果,使着色剂的分散稳定化。
作为具有极性的官能团的聚合物,包括仅具有胺值的聚合物、仅具有酸值的聚合物、具有胺值及酸值的聚合物、以及既不具有胺值也不具有酸值的聚合物。作为本发明的高分子分散剂,优选具有胺值。高分子分散剂虽然也可以具有酸值,但优选不具有酸值仅具有胺值的高分子分散剂。需要说明的是,作为高分子分散剂的胺值,优选为10mgKOH/g以上100mgKOH/g以下,更优选为10mgKOH/g以上60mgKOH/g以下。胺值低时,存在不易得到稳定分散效果的倾向,胺值高时,存在感光性树脂组合物在碱显影液中的溶解性下降、图案加工性变差的倾向。
作为仅具有胺值的分散剂的具体例,可举出以下的物质。
“DISPERBYK”(商品名)102、160、161、162、2163、164、2164、166、167、168、2000、2050、2150、2155、9075、9077;
BYK-LP N6919、BYK-LP N21116或BYK-LP N21234(以上均为ビックケミー社制);
“EFKA”(商品名)4015、4020、4046、4047、4050、4055、4060、4080、4300、4330、4340、4400、4401、4402、4403、4800(以上均为BASF社制);
“アジスパー”(注册商标)PB711(味の素ファインテクノ社制);
“SOLSPERSE”(注册商标)13240、13940、20000、71000或76500(以上均为ルーブリゾール社制)。
在仅具有胺值的分散剂中,优选具有叔氨基或吡啶、嘧啶、吡嗪、异氰脲酸酯等含氮杂环等碱性官能团的高分子分散剂。作为具有作为碱性官能团的叔氨基或含氮杂环的高分子分散剂,可举出以下的物质。
可举出“DISPERBYK”164、167,BYK-LP N6919;BYK-LP N21116;“SOLSPERSE”20000。
作为具有胺值及酸值的高分子分散剂,可举出例如“DISPERBYK”(商品名)142、145、2001、2010、2020、2025或9076、Anti-Terra-205(以上均为ビックケミー社制)、“ソルスパース”(注册商标)24000(ルーブリゾール社制)、アジスパー(注册商标)PB821、PB880或PB881(以上均为味の素ファインテクノ社制)或“SOLSPERSE”(注册商标)9000、11200、13650、24000SC、24000GR、32000、32500、32550、326000、33000、34750、35100、35200、37500、39000或56000(ルーブリゾール社制)。
作为高分子分散剂的量,为了在维持耐热性的同时提高分散稳定性,作为在树脂成分中所占的比例,优选在可能的范围内少的比率,具体而言,相对于树脂成分的总量,优选为1~50质量%,更优选为1~30质量%。另一方面,相对于着色材料的总量,优选为1~100质量%,更优选为3~30质量%。另外,作为该高分子分散剂的重均分子量,优选为1000以上100000以下,更优选为3000以上50000以下。在分子量低的情况下,得不到充分的稳定分散的效果,在分子量高的情况下,产生在碱显影液中的溶解性下降的问题。
本发明的着色树脂组合物含有(D)有机溶剂。作为(D)有机溶剂,可举出例如醚类、乙酸酯类、酯类、酮类、芳香族烃类、酰胺类或醇类的化合物。
更具体而言,可举出以下的物质。
乙二醇单甲基醚、乙二醇单乙基醚、乙二醇单正丙基醚、乙二醇单正丁基醚、二乙二醇单甲基醚、二乙二醇单乙基醚、二乙二醇单正丙基醚、二乙二醇单正丁基醚、三乙二醇单甲基醚、三乙二醇单乙基醚、丙二醇单甲基醚、丙二醇单乙基醚、丙二醇单正丙基醚、丙二醇单正丁基醚、二丙二醇单甲基醚、二丙二醇单乙基醚、二丙二醇单正丙基醚、二丙二醇单正丁基醚、二丙二醇二甲基醚、二丙二醇甲基正丁基醚、三丙二醇单甲基醚、三丙二醇单乙基醚、二乙二醇二甲基醚、二乙二醇甲基乙基醚、二乙二醇二乙基醚及四氢呋喃等醚类。
也可使用以下的酯化合物。
乙酸丁酯、乙二醇单甲基醚乙酸酯、乙二醇单乙基醚乙酸酯、丙二醇单甲基醚乙酸酯、乙酸3-甲氧基丁酯、乙二醇单丁基醚乙酸酯、二乙二醇单甲基醚乙酸酯、二乙二醇单乙基醚乙酸酯、二乙二醇单丁基醚乙酸酯、环己醇乙酸酯、丙二醇二乙酸酯、丙二醇单甲基醚乙酸酯、丙二醇单乙基醚乙酸酯(以下记为“PGMEA”)、二丙二醇甲基醚乙酸酯、乙酸3-甲氧基-3-甲基-1-丁酯、1,4-丁二醇二乙酸酯、1,3-丁二醇二乙酸酯或1,6-己二醇二乙酸酯等乙酸酯。
甲基乙基酮、环己酮、2-庚酮或3-庚酮等酮类。2-羟基丙酸甲酯、2-羟基丙酸乙酯等乳酸烷基酯类。
2-羟基-2-甲基丙酸乙酯、3-甲氧基丙酸甲酯、3-甲氧基丙酸乙酯、3-乙氧基丙酸甲酯、3-乙氧基丙酸乙酯、乙氧基乙酸乙酯、羟基乙酸乙酯、2-羟基-3-甲基丁酸甲酯、乙酸3-甲氧基丁酯、乙酸3-甲基-3-甲氧基丁酯、丙酸3-甲基-3-甲氧基丁酯、乙酸乙酯、乙酸正丙酯、乙酸异丙酯、乙酸正丁酯、乙酸异丁酯、甲酸正戊酯、乙酸异戊酯、丙酸正丁酯、丁酸乙酯、丁酸正丙酯、丁酸异丙酯、丁酸正丁酯、丙酮酸甲酯、丙酮酸乙酯、丙酮酸正丙酯、乙酰乙酸甲酯、乙酰乙酸乙酯或2-氧代丁酸乙酯等。
此外,还可使用以下的溶剂。
甲苯、二甲苯等芳香族烃类。
N-甲基吡咯烷酮、N,N-二甲基甲酰胺及N,N-二甲基乙酰胺等酰胺类。
丁醇、异丁醇、戊醇、4-甲基-2-戊醇、3-甲基-2-丁醇、3-甲基-3-甲氧基丁醇及二丙酮醇等醇类。
需要说明的是,为了使高分子分散剂与颜料的相互作用更有效,优选使有机溶剂的溶解性参数SP值为合适的范围。作为SP值,优选为7.5以上10.0以下,更优选为8.5以上10.0以下,优选在溶剂中包含50质量%以上、进而70质量%以上的这样的溶剂。SP值低的情况下,高分子分散剂、碱溶性树脂难以溶解,分散变得困难,SP值高的情况下,存在由高分子分散剂带来的稳定分散的效果变小的倾向。
其中,为了使着色材料分散更稳定,优选使用乙酸酯类。具体而言,乙酸酯类的化合物在本发明的着色树脂组合物所含有的全部(D)有机溶剂中所占的比例优选为50~100质量%,更优选为70~100质量%。
伴随着形成着色膜的基板的大型化,利用模涂(die coating)装置进行的涂布逐渐成为主流。为了实现该涂布方法中的合适的挥发性及干燥性,(D)有机溶剂优选为将两种以上化合物混合而得到的溶剂。为了使本发明的着色树脂组合物的涂布膜的膜厚均匀,使表面的平滑性及粘合性良好,相对于全部(D)有机溶剂,沸点为150~200℃的有机溶剂的比例优选为30~75质量%。
对于(D)有机溶剂相对于本发明的着色树脂组合物的全部固态成分的比例而言,相对于全部固态成分100质量份,优选为20~800质量份,更优选为30~500质量份。
通过使本发明的着色树脂组合物含有(E)光聚合性化合物及(F)光聚合引发剂,从而可向着色树脂组合物赋予感光性。
作为(E)光聚合性化合物,可举出例如多官能团或单官能团的单体或低聚物。此处所谓官能团,是指聚合性基团,优选碳-碳双键。
作为多官能团单体及多官能团低聚物,可举出以下的物质。
作为(甲基)丙烯酸系化合物,可举出双酚A二缩水甘油基醚(甲基)丙烯酸酯、聚(甲基)丙烯酸酯氨基甲酸酯、改性双酚A环氧(甲基)丙烯酸酯、己二酸1,6-己二醇(甲基)丙烯酸酯、邻苯二甲酸酐环氧丙烷(甲基)丙烯酸酯、偏苯三甲酸二乙二醇(甲基)丙烯酸酯、松香改性环氧二(甲基)丙烯酸酯、醇酸改性(甲基)丙烯酸酯、芴二丙烯酸酯系低聚物、三丙二醇二(甲基)丙烯酸酯、1,6-己二醇二(甲基)丙烯酸酯、双酚A二缩水甘油基醚二(甲基)丙烯酸酯、三羟甲基丙烷三(甲基)丙烯酸酯、季戊四醇三(甲基)丙烯酸酯、1,3,5-三丙烯酰基六氢-1,3,5-三嗪(triacrylformal)、季戊四醇四(甲基)丙烯酸酯或其酸改性物、二季戊四醇六(甲基)丙烯酸酯或其酸改性物、二季戊四醇五(甲基)丙烯酸酯及其酸改性物、2,2-双[4-(3-丙烯酰氧基-2-羟基丙氧基)苯基]丙烷、双[4-(3-丙烯酰氧基-2-羟基丙氧基)苯基]甲烷、双[4-(3-丙烯酰氧基-2-羟基丙氧基)苯基]砜、双[4-(3-丙烯酰氧基-2-羟基丙氧基)苯基]醚、4,4’-双[4-(3-丙烯酰氧基-2-羟基丙氧基)苯基]环己烷、9,9-双[4-(3-丙烯酰氧基-2-羟基丙氧基)苯基]芴、9,9-双[3-甲基-4-(3-丙烯酰氧基-2-羟基丙氧基)苯基]芴、9,9-双[3-氯-4-(3-丙烯酰氧基-2-羟基丙氧基)苯基]芴、双苯氧基乙醇芴二丙烯酸酯、双苯氧基乙醇芴二甲基丙烯酸酯、双甲酚芴二丙烯酸酯或双甲酚芴二甲基丙烯酸酯、二季戊四醇五(甲基)丙烯酸酯与二季戊四醇六(甲基)丙烯酸酯的缩聚物。
通过适当选择这些多官能团单体、单官能团单体、低聚物并进行组合,可调节得到的感光性的着色树脂组合物的敏感度或加工性等特性。其中,为了提高敏感度,优选具有3个以上聚合性基团的化合物,进一步更优选具有5个以上聚合性基团的化合物。进一步优选二季戊四醇六(甲基)丙烯酸酯或二季戊四醇五(甲基)丙烯酸酯或其酸改性物。另外,为了提高显影性及加工性,还优选使具有2个缩水甘油基醚基的环氧化合物与甲基丙烯酸的反应物与多元羧酸或其酸酐反应而得到的含有不饱和基团的碱溶性单体。此外,为了对显影时的图案形状进行控制,并用在分子中具有多个芳香环、并且具有对斥水性有很大贡献的芴环的(甲基)丙烯酸酯也是有用的。
作为光聚合性化合物的量,相对于树脂成分的总量,优选为1~70质量%,更优选为20~50质量%。添加量少的情况下,得不到充分的感光特性,加工变得困难,添加量多的情况下,形成的膜的固化收缩变大,由于膜应力而导致与基材的密合性下降,或在膜上产生褶皱,因而不理想。
作为(F)光自由基聚合引发剂,优选烷基苯酮系光聚合引发剂或肟酯系光聚合引发剂。
作为烷基苯酮系光聚合引发剂,可举出例如α-氨基烷基苯酮系光聚合引发剂或α-羟基烷基苯酮系光聚合引发剂。为了进一步提高敏感度,优选α-氨基烷基苯酮系光聚合引发剂。作为α-氨基烷基苯酮系光聚合引发剂,可举出例如2,2-二乙氧基苯乙酮、2-甲基-1-(4-甲基硫基苯基)-2-吗啉代(morpholino)丙烷-1-酮、作为“イルガキュア”(注册商标)369的2-苄基-2-二甲基氨基-1-(4-吗啉代苯基)-丁酮及作为“イルガキュア”(注册商标)379的2-(二甲基氨基)-2-[(4-甲基苯基)甲基]-1-[4-(4-吗啉基)苯基]-1-丁酮、1-羟基环己基苯基酮(以上均为BASF(株)制)、及2-羟基-2-甲基-1-苯基丙烷-1-酮。
作为肟酯系光聚合引发剂,可举出例如作为“イルガキュア”(注册商标)OXE01的1-[4-(苯硫基)苯基]-1,2-辛烷二酮2-(O-苯甲酰肟)及作为“イルガキュア”(注册商标)OXE02的1-[9-乙基-6-(2-甲基苯甲酰基)-9H-咔唑-3-基]乙酮1-(O-乙酰肟);及“アデカ”(注册商标)オプトマーN-1818、N-1919及“アデカアークルズ”NCI-831(以上均为ADEKA(株)制)。
除了这些光聚合引发剂之外,还可并用二苯甲酮系化合物、噻吨酮系化合物、咪唑系化合物、苯并噻唑系化合物、苯并噁唑系化合物、咔唑系化合物、三嗪系化合物及磷系化合物、以及钛酸酯等无机系光聚合引发剂等。作为这样的光聚合引发剂,可举出以下的物质。
二苯甲酮、N,N’-四乙基-4,4’-二氨基二苯甲酮、4-甲氧基-4’-二甲基氨基二苯甲酮、苯偶姻、苯偶姻甲基醚、苯偶姻异丁基醚、苯偶酰二甲基缩酮、α-羟基异丁基苯酮、噻吨酮、2-氯噻吨酮、叔丁基蒽醌、1-氯蒽醌、2,3-二氯蒽醌、3-氯-2-甲基蒽醌、2-乙基蒽醌、1,4-萘醌、9,10-菲醌、1,2-苯并蒽醌、1,4-二甲基蒽醌、2-苯基蒽醌、2-(邻氯苯基)-4,5-二苯基咪唑二聚物、2-巯基苯并噻唑、2-巯基苯并噁唑及4-(对甲氧基苯基)-2,6-二-(三氯甲基)均三嗪。
作为光聚合引发剂的量,相对于树脂成分的总量,优选为0.1~40质量%,在将两种以上的光聚合引发剂混合使用的情况下,优选总和为0.2~60质量%。
对于本发明的着色树脂组合物而言,为了提高使本发明的着色树脂组合物固化而形成的着色膜的可靠性、耐化学药品性,优选含有热交联性化合物。作为具有1个热交联性基团的热交联性化合物,可举出以下的物质。
可举出ML-26X、ML-24X、ML-236TMP、4-羟甲基3M6C、ML-MC或ML-TBC(以上均为本州化学工业(株)制)及P-a型苯并噁嗪(四国化成工业(株)制)。
作为具有2个热交联性基团的热交联性化合物,可举出以下的物质。
DM-BI25X-F、46DMOC、46DMOIPP或46DMOEP(以上均为旭有机材工业(株)制);
DML-MBPC、DML-MBOC、DML-OCHP、DML-PC、DML-PCHP、DML-PTBP、DML-34X、DML-EP、DML-POP、DML-OC、二羟甲基-Bis-C、二羟甲基-BisOC-P、DML-BisOC-Z、DML-BisOCHP-Z、DML-PFP、DML-PSBP、DML-MB25、DML-MTrisPC、DML-Bis25X-34XL或DML-Bis25X-PCHP(以上均为本州化学工业(株)制);
ニカラックMX-290((株)三和ケミカル制);
B-a型苯并噁嗪或B-m型苯并噁嗪(以上均为四国化成工业(株)制);
2,6-二甲氧基甲基-4-叔丁基苯酚、2,6-二甲氧基甲基-对甲酚或2,6-二乙酰氧基甲基-对甲酚。
作为具有3个热交联性基团的热交联性化合物,可举出以下的物质。
TriML-P、TriML-35XL或TriML-TrisCR-HAP(以上均为本州化学工业(株)制)。
作为具有4个热交联性基团的热交联性化合物,可举出以下的物质。
TM-BIP-A(旭有机材工业(株)制);
TML-BP、TML-HQ、TML-pp-BPF、TML-BPA或TMOM-BP(以上均为本州化学工业(株)制);
“ニカラック”MX-280、“ニカラック”MX-270(以上均为(株)三和ケミカル制)。
作为具有6个热交联性基团的热交联性化合物,可举出以下的物质。
HML-TPPHBA、HML-TPHAP(以上均为本州化学工业(株)制);
“ニカラック”MW-390、“ニカラック”MW-100LM(以上均为(株)三和ケミカル制)。
其中,优选具有2个以上热交联性基团的热交联性化合物,优选作为脂环式系的化合物的“ニカラック”MX-280或“ニカラック”MX-270或B-a型苯并噁嗪或B-m型苯并噁嗪、具有6个热交联性基团的“ニカラック”MW-390、“ニカラック”MW-100LM。
对于本发明的着色树脂组合物而言,为了控制其碱显影性,可含有具有酚式羟基的化合物。需要说明的是,此处所谓的具有酚式羟基的化合物,与通式(1)表示的聚酰胺相区别。
作为具有酚式羟基的化合物,可举出以下的物质。
Bis-Z、BisOC-Z、BisOPP-Z、BisP-CP、Bis26X-Z、BisOTBP-Z、BisOCHP-Z、BisOCR-CP、BisP-MZ、BisP-EZ、Bis26X-CP、BisP-PZ、BisP-IPZ、BisCR-IPZ、BisOCP-IPZ、BisOIPP-CP、Bis26X-IPZ、BisOTBP-CP、TekP-4HBPA(四P-DO-BPA)、TrisP-HAP、TrisP-PA、BisOFP-Z、BisRS-2P、BisPG-26X、BisRS-3P、BisOC-OCHP、BisPC-OCHP、Bis25X-OCHP、Bis26X-OCHP、BisOCHP-OC、Bis236T-OCHP、亚甲基三-FR-CR、BisRS-26X或BisRS-OCHP(以上均为本州化学工业(株)制);
BIR-OC、BIP-PC、BIR-PC、BIR-PTBP、BIR-PCHP、BIP-BIOC-F、4PC、BIR-BIPC-F、TEP-BIP-A(以上均为旭有机材工业(株)制)。
其中,优选Bis-Z、BisP-EZ、TekP-4HBPA、TrisP-HAP、TrisP-PA、BisOCHP-Z、BisP-MZ、BisP-PZ、BisP-IPZ、BisOCP-IPZ、BisP-CP、BisRS-2P、BisRS-3P、BisP-OCHP、亚甲基三-FR-CR、BisRS-26X、BIP-PC、BIR-PC、BIR-PTBP或BIR-BIPC-F。进而优选Bis-Z、TekP-4HBPA、TrisP-HAP、TrisP-PA、BisRS-2P、BisRS-3P、BIR-PC、BIR-PTBP或BIR-BIPC-F。
对于具有酚式羟基的化合物相对于树脂成分的比例而言,相对于树脂成分100质量份,优选为1~60质量份,更优选为3~50质量份。
对于本发明的着色树脂组合物而言,为了提高使本发明的着色树脂组合物固化而形成的着色膜与基板的密合性,可含有密合性改良剂。作为密合性改良剂,优选硅烷偶联剂。作为硅烷偶联剂,可举出例如具有乙烯基、环氧基、苯乙烯基、甲基丙烯酰氧基、丙烯酰氧基或氨基等官能团的烃基及烷氧基等水解性基团键合于硅原子而得到的物质。可举出以下的物质。3-环氧丙氧基丙基三甲氧基硅烷、3-环氧丙氧基丙基三乙氧基硅烷、3-环氧丙氧基丙基甲基二甲氧基硅烷、3-环氧丙氧基丙基甲基二乙氧基硅烷、2-(3,4-环氧环己基)乙基三甲氧基硅烷、3-氯丙基甲基二甲氧基硅烷、3-氯丙基三甲氧基硅烷、乙烯基三甲氧基硅烷、乙烯基三乙氧基硅烷、乙烯基三(2-甲氧基乙氧基)硅烷、N-(2-氨基乙基)-3-氨基丙基甲基二甲氧基硅烷、N-(2-氨基乙基)-3-氨基丙基三甲氧基硅烷、3-甲基丙烯酰氧基丙基三甲氧基硅烷、3-丙烯酰氧基丙基三甲氧基硅烷、3-氨基丙基三甲氧基硅烷、3-氨基丙基三乙氧基硅烷、3-三乙氧基甲硅烷基-N-(1,3-二甲基-亚丁基)丙基胺、3-巯基丙基三甲氧基硅烷、3-脲丙基三乙氧基硅烷、3-异氰酸酯基丙基三乙氧基硅烷或对苯乙烯基三甲氧基硅烷。
对于本发明的着色树脂组合物而言,为了提高其涂布性、涂布膜的表面的平滑性,或者防止贝纳德漩涡(Benard cell),可含有表面活性剂。表面活性剂相对于颜料的比例优选为0.001~10质量%,更优选为0.01~1质量%。作为表面活性剂,可举出以下的物质。
可举出月桂基硫酸铵、聚氧乙烯烷基醚硫酸三乙醇胺等阴离子表面活性剂;
硬脂基胺乙酸酯、月桂基三甲基氯化铵等阳离子表面活性剂;
月桂基二甲基氧化胺、月桂基羧甲基羟基乙基咪唑鎓甜菜碱等两性表面活性剂、聚氧乙烯月桂基醚、聚氧乙烯硬脂基醚或山梨糖醇酐单硬脂酸酯等非离子表面活性剂、以聚二甲基硅氧烷等为主骨架的聚硅氧烷系表面活性剂或氟系表面活性剂。
作为本发明的着色材料树脂组合物的制造方法,可举出例如使用分散机、使着色材料分散于碱溶性聚酰亚胺树脂的溶液中的方法。
作为分散机,可举出球磨机、珠磨机、砂磨机、三辊磨或高速冲击磨。从分散效率及微分散化方面考虑,优选珠磨机。作为珠磨机,可举出共球磨机(coball mill)、篮式珠磨机、销棒粉碎机或戴诺磨。作为珠磨机的珠,可举出例如氧化钛珠、二氧化锆珠或锆石珠。作为珠磨机的珠直径,优选为0.01~5.0mm,更优选为0.03~1.0mm。在着色材料的一次粒径及一次粒子凝集而形成的二次粒子的粒径小的情况下,优选0.03~0.10mm的微小的珠。这种情况下,优选具有可通过离心分离方式将微小的珠与分散液分离的分离器的珠磨机。另一方面,在使包含亚微米程度的粗大的粒子的着色材料分散的情况下,为了得到充分的粉碎力,优选0.10mm以上的珠。
接下来,对使本发明的着色树脂组合物固化而形成耐着色膜的方法,以负型的感光性的着色树脂组合物为例进行说明。
将感光性的着色树脂组合物涂布于基板上,得到涂布膜。作为基板,可举出例如钠钙玻璃、无碱玻璃或石英玻璃等透明基板、硅晶圆、陶瓷类的基板或砷化镓基板。作为涂布着色树脂组合物的方法,可举出例如使用了旋涂器(spinner)的旋转涂布、喷涂模涂或辊涂。涂布膜的膜厚根据涂布方法等适当确定即可,通常使得干燥后的膜厚成为1~150μm。
将得到的涂布膜干燥,得到干燥膜。对于干燥而言,通常通过利用烘箱或加热板进行的加热干燥、风干、减压干燥、或红外线照射等,于50~150℃进行1分钟~数小时(例如5小时)。
隔着具有所期望的图案的掩模,向得到的干燥膜照射化学射线,进行曝光,得到曝光膜。作为照射的化学射线,可举出例如紫外线、可见光线、电子束或X射线。优选对本发明的着色树脂组合物照射汞灯的i线(365nm)、h线(405nm)或g线(436nm)。
用碱性显影液等将得到的曝光膜显影,将未曝光部除去,得到图案。作为碱性显影液,可使用下文列举的碱性化合物的水溶液。
氢氧化钠、氢氧化钾、碳酸钠、碳酸钾、硅酸钠、偏硅酸钠、氨水等无机碱类;
乙基胺、正丙基胺等伯胺;
二乙基胺、二正丙基胺等仲胺;
三乙基胺、甲基二乙基胺等叔胺;
四甲基氢氧化铵(TMAH)等四烷基氢氧化铵类;
胆碱等季铵盐;
三乙醇胺、二乙醇胺、单乙醇胺、二甲基氨基乙醇、二乙基氨基乙醇等醇胺类;
吡咯、哌啶、1,8-二氮杂双环[5,4,0]-7-十一碳烯、1,5-二氮杂双环[4,3,0]-5-壬烷、吗啉等环状胺类。
碱性显影液中的碱性化合物的浓度通常为0.01~50质量%,优选为0.02~10质量%,更优选为0.02~1质量%。另外,为了使显影后的图案形状更良好,可添加0.1~5质量%的非离子系表面活性剂等表面活性剂。此外,在显影液为碱水溶液的情况下,可向显影液中添加乙醇、γ-丁内酯、二甲基甲酰胺或N-甲基-2-吡咯烷酮等水溶性有机溶剂。
作为显影的方法,可举出浸渍法、喷雾法、旋覆浸没法。可利用纯水等对得到的图案进行漂洗。
通过对得到的图案进行加热处理(后烘烤),可得到进行了图案形成的着色膜。对于该加热处理而言,通常,在空气或氮气气氛下或真空状态下,于150~300℃,连续或阶段性地进行0.25~5小时。
本发明的着色树脂组合物中含有黑色的着色材料时可合适地用于形成液晶显示装置等所具有的滤色器的黑色矩阵等遮光图像、有机EL显示器内部的着色分隔壁、或触摸面板所具有的装饰基板的着色膜。
此外,由于将本发明的着色树脂组合物固化而得到的固化膜具有高耐热性,因此,可作为依次具有形成有TFT的基板、驱动电路上的平坦化层、第一电极上的绝缘层及显示元件的显示装置的平坦化层、绝缘层而合适地使用。作为所述构成的显示装置,可举出液晶显示装置、有机EL显示装置等,可更合适地应用于对平坦化层、绝缘层要求更高的耐热性、更低的脱气(outgas)性的有机EL显示装置。
实施例
以下,针对本发明,举出其实施例及比较例进行详细说明,但本发明不受它们的限制。
(合成例1聚酰亚胺树脂(P-1)的合成)
在干燥氮气流下,将30.03g的2,2-双(3-氨基-4-羟基苯基)六氟丙烷(0.082摩尔)、1.24g的1,3-双(3-氨基丙基)四甲基二硅氧烷(0.005摩尔)、及作为封端剂的2.73g的3-氨基苯酚(0.025摩尔)溶解于100g的N-甲基-2-吡咯烷酮(以下、“NMP”),向其中添加31.02g的双(3,4-二羧基苯基)醚二酐(0.10摩尔)及30g的NMP,于20℃进行1小时搅拌,进而一边将水除去一边于180℃进行4小时搅拌。反应结束后,将反应液投入至2L的水中,利用过滤收集生成的沉淀物,用水洗涤3次,用80℃的真空干燥机进行20小时干燥,得到聚酰亚胺树脂(P-1)。
(合成例2聚酰亚胺前体(P-2)的合成)
将138.2g的4,4’-二氨基苯基醚(0.30摩尔)、161.7g的对苯二胺(0.65摩尔)、及28.6g的双(3-氨基丙基)四甲基二硅氧烷(0.05摩尔)与2082.6g的γ-丁内酯及2082.6g的NMP混合,向其中添加711.7g的3,3’,4,4’-氧双邻苯二甲酸酐(0.9975摩尔),于80℃进行3小时搅拌。向其中添加1.1g的马来酸酐(0.02摩尔),进而于80℃进行1小时搅拌,得到固态成分浓度为20质量%的聚酰亚胺前体(P-2)溶液。
(合成例3丙烯酸树脂(P-3)的合成)
合成甲基丙烯酸甲酯/甲基丙烯酸/苯乙烯的共聚物(质量比30/40/30)。相对于该共聚物100质量份,加成甲基丙烯酸缩水甘油酯40质量份。这是甲基丙烯酸的羧基与甲基丙烯酸缩水甘油酯的环氧基的反应。用纯化水使反应物进行再沉淀,进行过滤及干燥,由此得到重均分子量(Mw)为15,000、酸值为110(mgKOH/g)的丙烯酸树脂(P-3)。
(实施例1)
将利用磺酸基对表面进行了修饰的175g的炭黑(TPK1227;キャボット制)、57.5g的聚酰亚胺树脂(P-1)、33.7g的DISPERBYK-167及733.8g的丙二醇单甲基醚乙酸酯(以下“PGMEA”)混合,用均质混合器(プライミクス制)进行20分钟搅拌,得到预分散液。向具有填充了75%的氧化锆珠(YTZ球;ネツレン制)的离心分离器的ウルトラアペックスミル(寿工业制)供给得到的预分散液,以8m/s的旋转速度进行3小时分散,得到固态成分浓度为25质量%、着色材料/树脂(质量比)=70/30的炭黑分散液(Bk-1)。需要说明的是,高分子剂DISPERBYK-167的胺值为mgKOH/g,不存在酸值,作为颜料吸附基团,具有异氰脲酸酯环。另外,PGMEA的SP值为8.7。
向514.3g的炭黑分散液(Bk-1)中添加将71.1g的聚酰亚胺树脂(P-1)及3.0g的BYK333(聚硅氧烷系表面活性剂;ビックケミー社制)PGMEA溶液(10质量%)溶解于411.6g的PGMEA中而得到的溶液,得到全部固态成分浓度为20质量%、着色材料/树脂成分(质量比)=45/55的黑色树脂组合物1。
用旋涂器(1H-DS;ミカサ(株)制)将得到的黑色树脂组合物1涂布于无碱玻璃基板(AN100)上,于100℃对涂布膜进行2分钟预烘烤,然后,于230℃进行30分钟后烘烤,形成膜厚为1.0μm的黑色膜1。针对该黑色膜1,进行以下的各评价。将结果示于表1。
[遮光性]
使用光密度计(361TVisual;X-Rite社制),分别测定黑色膜1的入射光及透射光的强度,利用以下的式(X)算出遮光性OD值。
OD值=log10(I0/I)···式(X)
I0:入射光强度
I:透射光强度。
[绝缘性]
使用高电阻电阻率计(“ハイレスタ”(注册商标)UP;三菱化学制),测定黑色膜1的表面电阻率(Ω/□)。
[表面粗糙度]
使用接触式膜厚计(“DEKTAK”(注册商标)150;アルバック社销售),以5mg的触针压力测定黑色膜1的表面粗糙度(nm)。
[耐热性]
削取约10mg黑色膜1将其作为试样,测定加热减量率(%)。更具体而言,使用热重测定装置(TGA-50;岛津制作所社制),一边以50mL/分钟用氮气进行吹扫(purge),一边以10℃/分钟的升温速度达到300℃温度,分别测定于300℃保持30分钟时的达到300℃时的试样的质量、300℃保持结束时的试样的质量,由它们的值算出加热减量率(%)。
(实施例2)
使用56.2g的BYK-LP N6919代替“ディスパービック”BYK-167,使PGMEA的质量为711.3g,除此之外,与实施例1同样地操作,得到固态成分浓度为25质量%、着色材料/树脂成分(质量比)=70/30的炭黑分散液(Bk-2)。需要说明的是,高分子分散剂BYK-LP N6919的胺值为72mgKOH/g,不存在酸值,具有叔胺作为颜料吸附基团。
使用了炭黑分散液(Bk-2),除此之外,与实施例1同样地操作,得到黑色树脂组合物2。使用得到的黑色树脂组合物2,进行与实施例1同样的评价。将结果示于表1。
(实施例3)
使用43.8g的BYK-LP N21116代替“ディスパービック”BYK-167,使PGMEA的质量为723.7g,除此之外,与实施例1同样地操作,得到固态成分浓度为25质量%、着色材料/树脂成分(质量比)=70/30的炭黑分散液(Bk-3)。高分子分散剂BYK-LP N21116的胺值为32mgKOH/g,不存在酸值,具有叔胺和季铵盐作为颜料吸附基团。
使用了炭黑分散液(Bk-3),除此之外,与实施例1同样地操作,得到黑色树脂组合物3。使用得到的黑色树脂组合物3,进行与实施例1同样的评价。将结果示于表1。
(实施例4)
使用38.1g的“ディスパービック”BYK-2001代替“ディスパービック”BYK-167,使PGMEA的质量为729.4g,除此之外,与实施例1同样地操作,得到固态成分浓度为25质量%、着色材料/树脂成分(质量比)=70/30的炭黑分散液(Bk-4)。需要说明的是,高分子分散剂“ディスパービック”BYK-2001的胺值为29mgKOH/g,酸值为19mg/KOH,具有季铵盐作为颜料吸附基团。
使用了炭黑分散液(Bk-4),除此之外,与实施例1同样地操作,得到黑色树脂组合物4。使用得到的黑色树脂组合物4,进行与实施例1同样的评价。将结果示于表1。
(实施例5)
在有机黑“Irgaphor”BlackS0100CF(BASF社制)150.0g中混合聚酰亚胺树脂(P-1)75.0g、“SOLSPERSE”20000(ルーブリゾール社制)25.0g、及乙酸3-甲氧基丁酯(以下“MBA”)750g,除此之外,与实施例1同样地操作,得到固态成分浓度为25质量%、着色材料/树脂成分(质量比)=60/40的有机黑分散液(Bk-5)。需要说明的是,高分子分散剂“SOLSPERSE”20000的胺值为29mgKOH/g,不存在酸值,具有叔胺作为颜料吸附基团。另外,MBA的SP值为8.7。
在有机黑分散液(Bk-5)400g中溶解聚酰亚胺树脂(P-1)100g及BYK333(聚硅氧烷系表面活性剂;ビックケミー社制)PGMEA溶液(10质量%)3.0g及PGMEA 497g,得到全部固态成分浓度为20质量%、着色材料/树脂成分(质量比)=30/70的黑色树脂组合物5。使用得到的黑色树脂组合物5,进行与实施例1同样的评价。将结果示于表1。
(比较例1)
使聚酰亚胺树脂(P-1)的质量为91.2g,未添加高分子分散剂(“DISPERBYK”-167),除此之外,与实施例1同样地操作,想要得到炭黑分散液,但在使用ウルトラアペックスミル进行分散期间,炭黑凝集,粘度过度上升,因而未能得到炭黑分散液。
(比较例2)
分别地,使用375g的聚酰亚胺前体(P-2)溶液代替聚酰亚胺树脂(P-1),使用450g的NMP代替PGMEA,除此之外,与实施例1同样地操作,得到固态成分浓度为25质量%、着色材料/树脂成分(质量比)=70/30的炭黑分散液(Bk-7)。需要说明的是,NMP的SP值为11.0。
向257.1g的炭黑分散液(Bk-4)中添加178.6g的聚酰亚胺前体(P-2)溶液、563.3g的NMP及作为表面活性剂的1g的LC951(楠本化成制),得到全部固态成分浓度为10质量%、颜料/树脂成分(质量比)=45/55的黑色树脂组合物7。
使用得到的黑色树脂组合物7,进行与实施例1同样的评价。将结果示于表1。
(比较例3)
使用375g的聚酰亚胺前体(P-2)溶液代替聚酰亚胺树脂(P-1),使PGMEA的质量为450g,此外,未添加高分子分散剂(“DISPERBYK”-167),除此之外,与实施例1同样地操作,想要得到炭黑分散液,但利用均质混合器进行搅拌期间,树脂成分析出,未能得到炭黑分散液。
(比较例4)
使用57.5g的丙烯酸系聚合物(P-3)代替聚酰亚胺树脂(P-1),除此之外,与实施例1同样地操作,得到固态成分浓度为25质量%、着色材料/树脂成分(质量比)=70/30的炭黑分散液(Bk-8)。
使用了炭黑分散液(Bk-8),除此之外,与实施例1同样地操作,得到黑色树脂组合物8。使用得到的黑色树脂组合物8,进行与实施例1同样的评价。将结果示于表1。
(比较例5)
使用101.8g的具有芴骨架的环氧丙烯酸酯的酸酐缩聚物的PGMEA溶液(P-4)(固态成分浓度56.5质量%;V259ME;新日铁化学(株)制)代替聚酰亚胺树脂(P-1),使PGMEA的质量为689.5g,除此之外,与实施例1同样地操作,得到固态成分浓度为25质量%、着色材料/树脂成分(质量比)=70/30的炭黑分散液(Bk-9)。
使用了炭黑分散液(Bk-9),除此之外,与实施例1同样地操作,得到黑色树脂组合物9。使用得到的黑色树脂组合物9,进行与实施例1同样的评价。将结果示于表1。
(实施例6)
向499.5g的炭黑分散液(Bk-1)中添加将19.2g的聚酰亚胺树脂(P-1)、47.9g的二季戊四醇六丙烯酸酯、作为光自由基聚合引发剂的5.8g的“アデカクルーズ”NCI-831(ADEKA(株)制)、作为密合性改良剂的2.0的KBM503(信越化学(株)制)及2.0g的BYK333溶解于425.4g的PGMEA中而得到的溶液,得到固态成分浓度为20质量%、颜料/树脂(质量比)=45/55的感光性的黑色树脂组合物10。
用旋涂器将得到的感光性的黑色树脂组合物10涂布于无碱玻璃基板上,于100℃对涂布膜进行2分钟预干燥,然后,使用掩模对准器PEM-6M(ユニオン光学(株)制)介由光掩模进行曝光(200mJ/cm2)。使用0.045质量%KOH水溶液对其进行显影,接下来进行纯水洗涤,于230℃进行30分钟后烘烤,形成膜厚为1.0μm的黑色膜10。针对该黑色膜10,进行与实施例1同样的评价。将结果示于表1。
使实施例中记载的黑色性组合物及10固化而形成的黑色膜的遮光性、绝缘性及表面的平滑性(表面粗糙度)优异,可知组合物中的颜料的分散状态非常良好。此外,加热减量率(%)也非常低,从涂布膜脱除的气体非常少,可知形成了耐热性优异的着色膜。
【表1】
产业上的可利用性
本发明的着色树脂组合物可合适地应用于触摸面板所具有的装饰基板的着色膜、及有机EL显示装置的着色绝缘层的形成。
Claims (8)
1.一种着色树脂组合物,其含有:
(A)碱溶性聚酰亚胺树脂,其包含下述通式(1)表示的结构单元,
(B)着色材料,
(C)高分子分散剂,和
(D)有机溶剂,
所述(B)着色材料与包含(A)碱溶性聚酰亚胺树脂和(C)高分子分散剂在内的树脂成分的质量比为90/10~20/80,
所述(C)高分子分散剂具有选自多胺、聚醚、聚酯、聚氨酯及聚(甲基)丙烯酸酯的主链、且侧链具有选自胺和胺盐中的具有极性的官能团,并且所述(C)高分子分散剂具有胺值,
所述(D)有机溶剂含有70~100质量%的乙酸酯系溶剂,并且乙酸酯系溶剂的SP值为8.5~10。
通式(1)中,R1表示4~10价的有机基团,R2表示2~8价的有机基团,R3及R4各自独立地表示酚式羟基、磺酸基或硫醇基,p及q各自独立地表示0~6的整数,p与q之和为1以上。
2.根据权利要求1所述的着色树脂组合物,其中,所述(C)高分子分散剂不具有酸值。
3.根据权利要求1所述的着色树脂组合物,其中,所述(C)高分子分散剂具有作为碱性官能团的叔氨基或含氮杂环。
4.根据权利要求1所述的着色树脂组合物,其中,所述(B)着色材料为有机颜料及/或无机颜料。
5.一种着色膜,其是权利要求1~4中任一项所述的着色树脂组合物的固化物。
6.一种装饰基板,其具有权利要求5所述的着色膜。
7.一种触摸面板,其具有权利要求6所述的装饰基板。
8.一种有机EL显示装置,其中,在驱动电路上的平坦化层及第一电极上的绝缘层中的至少一层上具有权利要求5所述的着色膜。
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JP7234631B2 (ja) | 2017-03-29 | 2023-03-08 | 東レ株式会社 | ネガ型感光性樹脂組成物、硬化膜、硬化膜を具備する素子及び有機elディスプレイ、並びにその製造方法 |
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CN111164512A (zh) | 2017-09-29 | 2020-05-15 | 东丽株式会社 | 感光性树脂组合物、固化膜、具备固化膜的元件和有机el显示器及有机el显示器的制造方法 |
US20210191264A1 (en) * | 2017-10-31 | 2021-06-24 | Toray Industries, Inc. | Negative photosensitive resin composition, cured film, and organic el display and manufacturing method therefor |
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CN107406673A (zh) | 2017-11-28 |
WO2016158672A1 (ja) | 2016-10-06 |
US20180039176A1 (en) | 2018-02-08 |
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