CN114502677A - 黑色粒子、黑色涂料、涂膜及滤色器用黑色矩阵 - Google Patents
黑色粒子、黑色涂料、涂膜及滤色器用黑色矩阵 Download PDFInfo
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- CN114502677A CN114502677A CN202080070184.2A CN202080070184A CN114502677A CN 114502677 A CN114502677 A CN 114502677A CN 202080070184 A CN202080070184 A CN 202080070184A CN 114502677 A CN114502677 A CN 114502677A
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- Prior art keywords
- black
- meth
- pyrrole
- acrylate
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Abstract
本发明提供电绝缘性高、且在可见光区域中能够实现高的黑色度的黑色粒子、包含该黑色粒子的黑色涂料、涂膜及滤色器用黑色矩阵。本发明是一种黑色粒子,其包含共聚物,所述共聚物具有来自于吡咯化合物的结构单元和来自于醌化合物的结构单元,所述黑色粒子的水分散体个数平均粒径为100nm以下,所述黑色粒子的Zeta电位为‑5mV以下。
Description
技术领域
本发明涉及电绝缘性高、且在可见光区域能够实现高的黑色度的黑色粒子、包含该黑色粒子的黑色涂料、涂膜及滤色器用黑色矩阵。
背景技术
液晶彩色显示器等图像显示装置中设置有用于显示彩色图像的滤色器,在这样的滤色器中,为了防止彩色抗蚀剂彼此的混色、防止黑色显示时的漏光,需要被称为黑色矩阵的遮光构件。
作为黑色矩阵的材料,使用铬等金属薄膜,但金属薄膜存在透光率高、且环境负荷大的问题。因此,作为黑色矩阵的材料,将钛黑、炭黑等黑色颜料分散于树脂中的树脂组合物成为主流。
然而,钛黑的比重比较大,为3以上,在用作树脂组合物的情况下存在易于引起沉降的问题。另外,由于通过将带隙大的氧化钛的一部分进行氮化而得到,因此存在接近褐色的多,黑色度不充分的问题。
另外,炭黑本来是具有导电性的材料,制成涂膜时难以发挥充分的绝缘性,存在黑色矩阵导通,成为显示不良的原因的问题。此外,为了提高碳粒子的着色性,而增大粒径,但粒径大的碳粒子在配合于涂料的情况下,存在易于引起沉降,引起分散性、流动性降低的问题。另外,就炭黑这样的碳粒子而言,存在单分散性不充分,易于引起聚集的问题。
针对此,专利文献1中记载了一种黑色粒子,该黑色粒子含有来自于噁嗪树脂所含有的碳的无定形碳,且该黑色粒子的比重为1.8g/cm3以下,Zeta电位为-70~+80mV,在波长400~800nm下测定的总光线反射率的平均值为5%以下,G能带与D能带的峰强度比为1.2以上。
另外,非专利文献1中记载了在甲磺酸溶液中使吡咯和对苯醌反应而得的球状形态的产物,记载了在不存在酸或高酸浓度下制备的产物是非导电性的。
现有技术文献
专利文献
专利文献1:国际公开第2017/142087号
非专利文献
非专利文献1:New J.Chem.,2018,42,10167-10176“Oxidation of pyrrole withp-benzoquinone to semiconducting products and their application inelectrorheology”
发明内容
发明要解决的课题
然而,专利文献1的黑色粒子虽然粒子自身的黑色度高,但存在:在将粒子干燥保存的情况下,粒子会粘合,或为了制作涂膜而再次分散液化时粒子会聚集,再分散性差的问题。另外,使用这样的粒子得到的涂膜存在产生不均,总透光率高,黑色度不充分的问题。
另外,非专利文献1所记载的球状形态的产物存在电绝缘性低、或在干燥时产生粘合、或再次溶液化时产生聚集等,在制成黑色矩阵的材料的情况下,不能充分地防止混色、导通的问题。
本发明鉴于上述现状,其目的在于,提供电绝缘性高、且在可见光区域中能够实现高的黑色度的黑色粒子、包含该黑色粒子的黑色涂料、涂膜及滤色器用黑色矩阵。
用于解决课题的手段
本发明是一种黑色粒子,其包含共聚物,所述共聚物具有来自于吡咯化合物的结构单元和来自于醌化合物的结构单元,所述黑色粒子的水分散体个数平均粒径为100nm以下,Zeta电位为-5mV以下。
以下,对本发明进行详述。
本发明人等进行了深入研究,结果发现,通过制成一种包含共聚物,所述共聚物具有来自于吡咯化合物的结构单元和来自于醌化合物的结构单元,且水分散体具有规定的平均粒径,Zeta电位为规定的范围的黑色粒子,可得到电绝缘性高、且黑色度高的涂膜,从而完成本发明。
本发明的黑色粒子包含共聚物,所述共聚物具有来自于吡咯化合物的结构单元和来自于醌化合物的结构单元。另外,本发明的黑色粒子优选包含如下共聚物,所述共聚物具有来自于吡咯的结构单元和来自于苯醌的结构单元。
通过包含上述共聚物,能够得到电绝缘性高、且黑色度高的涂膜。
上述吡咯化合物意指吡咯及吡咯环的氢原子被取代基取代的吡咯衍生物。
作为上述吡咯化合物,例如可举出下述式(1)所示的化合物。
[化1]
上述式(1)中,R1、R2、R3、R4及R5各自独立,表示氢原子、羟基、羧基、卤素、氨基、硝基、氰基、醛基、异氰酸酯基、碳原子数6~18的芳基磺酰基、甲苯磺酰基、甲硅烷基、呋喃基、吡咯基、巯基、磺酸基、酰肼基、酰卤基、酰胺基、磺酰胺基、碳原子数1~18的直链状或支链状烷基、碳原子数2~18的直链状或支链状烯基、碳原子数6~18的芳基、碳原子数7~20的芳基烷基、碳原子数7~20的烷基芳基、碳原子数2~10的酰基、碳原子数1~6的烷氧基、碳原子数2~10的烷氧基羰基、或碳原子数3~10的烷氧基羰基烷基。
另外,上述烷基、烯基、芳基、芳基烷基、烷基芳基、酰基、烷氧基及烷氧基羰基的至少1个氢原子可以被羟基、羧基、卤素、氨基、硝基、氰基、醛基、异氰酸酯基、碳原子数6~18的芳基磺酰基、甲苯磺酰基、甲硅烷基、呋喃基、吡咯基、巯基、磺酸基、酰肼基、酰卤基、酰胺基或磺酰胺基取代。
此外,上述R2、R3、R4及R5中的相邻2个可以键合而形成环结构。
作为上述R2、R3、R4及R5中的相邻2个键合而形成的环结构,可举出苯环等芳香族烃环、饱和或不饱和的脂肪族烃环、形成这些环的至少1个碳原子被氧、氮、硫等杂原子取代的杂环等。
这些环结构优选为4~10元环,更优选为5~8元环。
作为具有上述环结构的多环的吡咯化合物,可举出吲哚等吡咯环与芳香族环的稠合化合物、噻吩并吡咯等吡咯环与其他杂环的稠合化合物、吡咯环与吡咯环的稠合化合物等。
上述R2及R5优选为氢原子。
另外,上述R3及R4优选为氢原子、卤素、氨基、碳原子数1~3的直链状烷基、碳原子数3~5的支链状烷基、苯基、甲基苯基或乙酰基。
另外,上述吡咯化合物更优选为单环的化合物。
作为上述吡咯化合物,例如可举出:吡咯;3-乙酰基吡咯、3-乙酰基-1-甲基吡咯、吡咯-3-甲酸、3-乙酰基-1-甲苯磺酰基吡咯等在吡咯环的3位具有取代基的化合物;1-甲基吡咯、1-乙基吡咯、1-(2-氰基乙基)吡咯、1-苯基吡咯、1-甲苯磺酰基吡咯、1-(2-羟乙基)吡咯、1-(3-羟丙基)吡咯、1-(三异丙基甲硅烷基)吡咯、1-(苯基磺酰基)吡咯、1-(4-氯苯基)-1H吡咯、1-(4-碘苯基)吡咯、4-(1H-吡咯-1-基)苯酚、1-{3-(溴甲基)苯基}-1H-吡咯、1-{4-(溴甲基)苯基}-1H-吡咯、1-(3-异氰酸苯基)-1H-吡咯、3-(1H-吡咯-1-基)苯胺、4-(1H-吡咯-1-基)苯胺、4-(1H-吡咯-1-基)苯甲醛、2-(1H-吡咯-1-基)苯甲酸、3-(1H-吡咯-1-基)苯甲酸、4-(1H-吡咯-1-基)苄胺、{2-(1H-吡咯-1-基)苯基}甲醇、{4-(1H-吡咯-1-基)苯基}甲醇、N-糠基吡咯等在吡咯环的1位具有取代基的化合物;2-乙基吡咯、2,4-二甲基吡咯、2-乙酰基吡咯、2-丙酰基吡咯、3-乙酰基-2,4-二甲基吡咯、吡咯-2-甲腈、N-甲基吡咯-2-甲醛、吡咯-2-羧酸、1-甲基吡咯-2-甲酸、2-乙酰基-1-甲基吡咯、1-(2-氨基苯基)吡咯、1,5-二甲基-2-吡咯甲腈、2,4-二甲基吡咯-3,5二甲酸乙酯、3,5-二甲基-1H-吡咯甲酸乙酯、1-(4-氯苯基)-1H-吡咯-2-甲醛、1H-吡咯-2-碳酰肼等在吡咯环的2位具有取代基的化合物等。此外,还能够举出:吲哚;4-甲基-4H-噻吩并{3,2-b}吡咯-5-甲醛、6H-噻吩并{2,3-b}吡咯-5-甲酸甲酯、4-甲基-4H-噻吩并{3,2-b}吡咯-5-甲酸、4H-噻吩并{3,2-b}吡咯-5-甲酸、{4-甲基-4H-噻吩并{3,2-b}吡咯-5-基}甲醇等噻吩并吡咯;聚吡咯等吡咯环稠合多环芳香族化合物。另外,也可以为具有杂环的吡咯化合物。
其中,优选为吡咯、在1位具有取代基的化合物、在3位具有取代基的化合物,更优选为吡咯、3-乙酰基吡咯、3-乙酰基-1-甲基吡咯、3-乙酰基-1-甲苯磺酰基吡咯、1-(2-氰基乙基)吡咯、1-苯基吡咯、1-甲苯磺酰基吡咯、1-(三异丙基甲硅烷基)吡咯、1-(苯基磺酰基)吡咯、1-(4-氯苯基)-1H-吡咯、1-{3-(溴甲基)苯基}-1H-吡咯、1-{4-(溴甲基)苯基}-1H-吡咯、1-(3-异氰酸苯基)-1H-吡咯等,进一步优选为吡咯。
上述吡咯化合物可以单独使用1种,也可以组合使用两种以上。
上述醌化合物是具有2个羰基的芳香族化合物,优选为由苯环衍生的六元环结构。
另外,上述芳香族化合物中,除了羰基以外的碳原子可以具有1个或多个取代基。
作为上述取代基,可举出卤素原子、杂环基、氨基、硝基、甲酰基、氰基、羟基、碳原子数1~18的直链状或支链状烷基、碳原子数2~18的直链状或支链状烯基、碳原子数1~6的烷氧基、巯基、烷硫基、烷基羰基、芳基羰基、烷基磺酰基或芳基磺酰基。
上述六元环结构的醌化合物所具有的2个羰基彼此可以存在于邻位、对位中的任一者,更优选存在于对位。
作为上述六元环结构的醌化合物,例如可举出下述式(2-1)及(2-2)所示的化合物。
[化2]
上述式(2-1)中的R6、R7、R8及R9、以及上述式(2-2)中的R10、R11、R12及R13彼此独立,并且表示氢原子、卤素原子、杂环基、氨基、硝基、甲酰基、氰基、羟基、碳原子数1~18的直链状或支链状烷基、碳原子数2~18的直链状或支链状烯基、碳原子数1~6的烷氧基、巯基、烷硫基、烷基羰基、芳基羰基、烷基磺酰基或芳基磺酰基。
作为上述醌化合物,具体而言,可举出:对苯醌、2-乙基-对苯醌、2-叔丁基-对苯醌、2-异戊基-对苯醌、2,6-二乙基-对苯醌、2,6-二叔丁基-对苯醌、2-溴-对苯醌、2,6-二溴-对苯醌、2-氯-对苯醌、2,6-二氯-对苯醌、2-羟基-对苯醌、2,6-二羟基-对苯醌、2-甲氧基-对苯醌、2,6-二甲氧基-对苯醌等对苯醌衍生物、邻苯醌、3-乙基-邻苯醌、3-叔丁基-邻苯醌、3-异戊基-邻苯醌、3,6-二乙基-邻苯醌、3-溴-邻苯醌、3,6-二溴-邻苯醌、3-氯-邻苯醌、3,6-二氯-邻苯醌、3-羟基-邻苯醌、3,6-二羟基-邻苯醌、3-甲氧基-邻苯醌等邻苯醌衍生物等。
上述具有来自于吡咯化合物的结构单元和来自于醌化合物的结构单元的共聚物是使上述吡咯化合物与上述醌化合物进行氧化聚合而得到的。即,上述具有来自于吡咯化合物的结构单元和来自于醌化合物的结构单元的共聚物是吡咯化合物和醌化合物的共聚物。
上述氧化聚合中,上述吡咯化合物与上述醌化合物的摩尔比(吡咯化合物/醌化合物)优选为1/4以上,更优选为1/2以上,且优选为3/2以下,更优选为1/1以下。
若为上述范围外,则会有反应效率变差且收率降低,或者不会成为球状粒子的情况。
上述氧化聚合的温度优选为0℃以上,且优选为50℃以下。若为上述范围外,则有水分散体个数平均粒径变大的情况。
另外,上述聚合反应后,需要进一步提高分散液温度。在不提高分散液温度的情况下,粒子形状不稳定,或者粒子彼此之间粘合,有无法得到期望的粒子的担心。上述温度优选为60℃以上,且优选为100℃以下。
需要说明的是,上述聚合反应在确认残留在反应液中的单体的量时,将单体的70重量%以上进行反应而聚合的情况判断为反应结束。
另外,上述残留的单体的量例如能够通过以下方式确认:将反应液加热至上述吡咯化合物及上述醌化合物的挥发温度以上进行干燥,测量残留固体成分的量;或者通过利用气相色谱法的定量分析来进行测定。
上述氧化聚合中,优选为添加添加剂。
作为上述添加剂,例如可举出:碘、溴、氯等卤素化合物;硫酸、盐酸、硝酸、高氯酸、氟硼酸、次膦酸等质子酸;这些质子酸的各种盐;三氯化铝、三氯化铁、氯化钼、氯化锑、五氟化砷、五氟化锑等路易斯酸;乙酸、三氟乙酸、聚丙烯酸(日文:ポリエチレンカルボン酸)、甲酸、苯甲酸、柠檬酸等有机羧酸;这些有机羧酸的各种盐;苯酚、硝基苯酚、氰基苯酚等苯酚类;这些苯酚类的各种盐;二-2-乙基己基磺基琥珀酸、磺基琥珀酸等磺基琥珀酸类;磺基琥珀酸类的盐;聚丙烯酸等高分子酸;磷酸丙酯、磷酸丁酯、磷酸己酯等磷酸烷基酯;聚环氧乙烷十二烷基醚磷酸酯、聚环氧乙烷烷基醚磷酸酯等聚环氧烷磷酸酯;烷基磷酸酯、聚环氧烷磷酸酯的各种盐;硫酸月桂酯、硫酸鲸蜡酯、硫酸硬脂酯、月桂基醚硫酸酯等硫酸酯;这些硫酸酯的各种盐等。
上述氧化聚合中,通过添加如上所述的氧化力弱的添加剂,可以制作能够得到电绝缘性高、且黑色度高的涂膜的黑色粒子。
上述具有来自于吡咯化合物的结构单元和来自于醌化合物的结构单元的共聚物的重均分子量优选为1×106以上,更优选为1×107以上,且优选为1×1015以下,更优选为1×1013以下。
上述重均分子量例如能够通过动态光散射法而确认。
上述具有来自于吡咯化合物的结构单元和来自于醌化合物的结构单元的共聚物中的氮原子及碳原子的含量比(氮原子的含量/碳原子的含量)优选为1/115以上,更优选为1/12以上,且优选为1/6以下,更优选为1/7以下。
另外,氮原子和碳原子的合计含量优选为总原子的75%以上。若小于75%,则会有通过其他的元素表现出导电性,或者产生对于电子设备的腐蚀作用的情况。
此外,上述具有来自于吡咯化合物的结构单元和来自于醌化合物的结构单元的共聚物中的氮原子及氧原子的含量比(氮原子的含量/氧原子的含量)优选为1/15以上,更优选为1/10以上,且优选为20以下,更优选为10以下。
上述含量比例如能够通过X射线光电分光法来确认。
本发明的黑色粒子的Zeta电位(表面电位)为-5mV以下。
通过设为上述范围内,能够制成粒径的均匀性优异、且溶剂中的分散性良好的黑色粒子。
上述Zeta电位的优选下限为-80mV,优选上限为-20mV。
需要说明的是,上述Zeta电位例如能够通过以下方式求出:使用显微镜电泳方式Zeta电位测定装置,将分散有黑色粒子的溶液注入测定用容器中,一边利用显微镜观察一边施加电压,测定粒子不动(静止)时的电位。
本发明的黑色粒子优选在波长400~800nm下测定的粒子的固体成分45wt%、厚度1μm的涂膜的总透光率的平均值为30%以下。通过设为上述范围内,大部分可见光被黑色粒子吸收,因此能够在可见光区域中显示出高的黑色度。
上述总透光率的平均值更优选为25%以下。
上述总透光率的平均值的下限没有特别限定,越低越好,优选的下限为0%。另外,测定值的标准偏差优选为10%以下。若为10%以下,则涂膜的不均少,成为优选的涂膜。
需要说明的是,针对本发明的黑色粒子,在波长400~800nm下测定总透光率的情况下,优选未检测到总透光率显示极大值的峰。
上述总透光率例如能够使用带积分球的分光光度计来测定。
本发明的黑色粒子的一次粒径的优选下限为0.005μm,优选的上限为50μm。通过将上述一次粒径设为从0.005μm至50μm的范围内,能够得到充分的黑色度和高的分散性。更优选的下限为0.01μm,更优选的上限为40μm。
上述一次粒径能够通过针对制作黑色粒子的反应溶液,使用粒径分布测定装置来进行测定而求出。
本发明的黑色粒子的水分散体个数平均粒径为100nm以下。
若上述水分散体个数平均粒径为100nm以下,则能够充分地提高所得到的涂膜的黑色度。
上述水分散体个数平均粒径优选为20nm以上,且优选为80nm以下。
需要说明的是,上述水分散体个数平均粒径能够通过以下方式求出:以成为浓度0.1重量%的方式将黑色粒子的干燥粉体添加至水中,针对使用超声波而分散的水分散体,使用粒径分布测定装置进行测定。
本发明的黑色粒子的粒径的变异系数(CV值)优选为20%以下。若上述粒径的CV值为20%以下,则黑色粒子的单分散性良好,用作黑色颜料的情况下易于将粒子最密填充。其结果,能够提高对于可见光的遮蔽效果。上述粒径的CV值的更优选的上限为15%。需要说明的是,针对下限没有特别限定,优选为0.5%。
粒径的CV值(%)是将标准偏差除以平均粒径而得的值用百分率表示而得的数值,是通过下述式求出的数值。CV值越小,意味着粒径的偏差越小。
粒径的CV值(%)=(粒径的标准偏差/水分散体个数平均粒径)×100
平均粒径及标准偏差例如能够使用FE-SEM进行测定。
本发明的黑色粒子的平均球形度优选为90%以上。
由此,能够提高本发明的效果。上述平均球形度的更优选的下限为95%。
需要说明的是,球形度(短径/长径)能够通过以下方式测定:使用图像分析装置,针对使用FE-SEM拍摄的电子显微镜照片进行分析处理;平均球形度能够通过以下方式算出:针对在电子显微镜照片中任意选取的例如100个粒子,求出球形度的平均值。
本发明的黑色粒子的比重为1.80g/cm3以下。通过使比重为1.80g/cm3以下,能够得到高的分散性。上述比重的优选的下限为1.20g/cm3,优选的上限为1.70g/cm3。
上述比重例如能够使用电子比重计(Alfamirage Company制,ED-120T)等进行测定。
本发明的黑色粒子的体积电阻率优选为1.0×107Ω·cm以上。通过使体积电阻率为1.0×107Ω·cm以上,能够确保高的绝缘性。更优选为1.0×108Ω·cm以上,进一步优选为1.0×1011Ω·cm以上。另外,优选为1.0×1018Ω·cm以下。
上述体积电阻率例如能够使用粉体电阻测定系统(三菱化学Analytech公司制)进行测定。
作为制作本发明的黑色粒子的方法,例如可举出将吡咯化合物、醌化合物、添加剂进行混合并反应的方法等。
具体而言,可举出:制备包含吡咯化合物和添加剂的吡咯化合物水溶液,进一步滴加将醌化合物添加至乙醇、水等溶剂而制备的醌化合物溶液并使其反应的方法。
上述吡咯化合物水溶液中的吡咯化合物的含量相对于水100重量份优选为0.1重量份以上,且优选为2重量份以下。
上述吡咯化合物水溶液中的添加剂的含量相对于吡咯化合物100重量份优选为0.01重量份以上,且优选为1重量份以下。
上述醌化合物的添加量相对于上述吡咯化合物1摩尔优选为0.7摩尔以上,且优选为4摩尔以下。
上述反应时的温度优选为0℃以上,且优选为50℃以下。
另外,反应时间优选为4小时以上,且优选为48小时以下。
反应的结束意味着单体的70重量%以上进行了反应。
上述反应的结束例如能够通过以下方式确认:将粒子分散液在上述吡咯化合物及上述醌化合物的挥发温度以上进行加热并干燥,残量固体成分成为作为投入原材料的单体的添加量的70重量%以上。未反应的吡咯化合物、醌化合物在进行上述干燥时挥发,不作为固体成分残留。
例如,吡咯的沸点为129℃,对苯醌的升华温度为115℃,因此通过在130℃30分钟的条件下进行干燥,吡咯及对苯醌挥发。另一方面,反应后的聚合物在上述条件下不挥发,作为固体成分残留。因此,通过在上述条件下进行干燥,能够确认单体聚合了何种程度。
另外,根据上述吡咯化合物、上述醌化合物的种类,能够在更高的温度下进行干燥来确认残留固体成分的比例。
另外,将反应液利用气相色谱法进行定量分析,也能够确认残留的单体的比例,从而确认反应的结束。
在制作上述黑色粒子的方法中,可以还进行干燥工序。
上述干燥工序中的干燥温度优选为100℃以上,且优选为220℃以下。上述反应结束后,优选为还将粒子分散液加热至60℃以上且100℃以下。反应结束时的粒子为柔软的树脂状,因此如果直接进行干燥处理等,则有粘合从而损害粒子形状的担心。
另外,干燥时间优选为3小时以上,且优选为48小时以下。
本发明的黑色粒子能够用于涂膜、黑色涂料、滤色器用黑色矩阵等用途。
上述涂膜、黑色涂料、滤色器用黑色矩阵也是本发明之一。
以下对形成本发明的黑色矩阵的方法的一例进行说明。
首先,使用搅拌机将本发明的黑色粒子、固化性化合物、以及根据需要添加的固化剂、溶剂等进行混合,制作包含黑色粒子的组合物。
接下来,使用辊涂机、反向涂布机、凹版涂布机、逗号涂布机、棒涂机等接触型涂布装置、或旋涂机、狭缝涂布机、帘式流动涂敷机等非接触型涂布装置将上述组合物涂布于由玻璃、聚对苯二甲酸乙二醇酯、丙烯酸类树脂、聚碳酸酯等形成的基板上。
进一步地,通过例如使用真空干燥装置将所涂布的组合物在室温下进行减压干燥,然后利用加热板、烘箱在80℃以上且120℃以下、优选为90℃以上且100℃以下的温度下干燥60秒钟以上且180秒钟以下的方法等进行干燥,从而形成涂膜。
借助负型掩膜对所得的涂膜照射紫外线、准分子激光等活性能量射线,从而部分地曝光。需要说明的是,照射活性能量射线前,优选对所得的涂膜和负型掩膜照射近红外线,通过近红外线对准进行两者的位置匹配。
所照射的能量射线量根据所用的本发明的树脂组合物的组成而不同,优选为100~2000mJ/cm2。
通过利用碱性水溶液对曝光后的涂膜进行显影,从而图案化为期望的形状。作为上述利用碱性水溶液的显影方法,例如能够使用浸渍法、喷雾法、浆法等。作为用作显影液的碱性水溶液,可举出氢氧化钠、氢氧化钾、碳酸钠、氨、四甲基氢氧化铵、季铵盐等的水溶液。
通常而言,在使用包含这样的碱性水溶液的显影液的情况下,显影后用纯水清洗(冲洗)除去剩余的显影液。
针对显影后的图案,根据需要,在220℃~250℃左右、优选为230℃~240℃左右进行后烘烤。此时,在后烘烤之前,优选将所形成的图案全面曝光。
通过以上操作,能够形成具有规定的图案形状的黑色矩阵。
作为上述固化性化合物,例如可举出:苯乙烯化合物、苯氧基化合物、氧杂环丁烷化合物、环氧化合物、环硫化合物、(甲基)丙烯酸类化合物、不饱和聚酯化合物、聚氨酯化合物、硅酮化合物、聚酰亚胺化合物、烯丙醇衍生物等。上述固化性化合物可以仅使用1种,也可以组合使用两种以上。
另外,上述固化性化合物可以为分子量小于10000的化合物,也可以为分子量为10000以上的化合物,还可以组合使用两者。
作为上述苯乙烯化合物,例如可举出苯乙烯系单体的均聚物、苯乙烯系单体与丙烯酸系单体的共聚物等。
作为上述苯乙烯系单体,例如可举出:苯乙烯、邻苯乙烯、间苯乙烯、对苯乙烯、对甲氧基苯乙烯、对苯基苯乙烯、对氯苯乙烯、对乙基苯乙烯、对正丁基苯乙烯、对叔丁基苯乙烯、对正己基苯乙烯、对正辛基苯乙烯、对正壬基苯乙烯、对正癸基苯乙烯、对正十二烷基苯乙烯、2,4-二甲基苯乙烯、3,4-二氯苯乙烯等。
作为上述苯氧基化合物,例如可举出使表卤代醇与2元酚化合物反应得到的树脂、或使2价的环氧化合物与2元酚化合物反应得到的树脂。
具体而言,可举出具有双酚A型骨架、双酚F型骨架、双酚A/F混合型骨架、萘骨架、芴骨架、联苯基骨架、蒽骨架、芘骨架、呫吨骨架、金刚烷骨架或二环戊二烯骨架的化合物。
作为上述氧杂环丁烷化合物,例如可举出:烯丙基氧基氧杂环丁烷、苯氧基甲基氧杂环丁烷、3-乙基-3-羟基甲基氧杂环丁烷、3-乙基-3-(苯氧基甲基)氧杂环丁烷、3-乙基-3-((2-乙基己氧基)甲基)氧杂环丁烷、3-乙基-3-((3-(三乙氧基甲硅烷基)丙氧基)甲基)氧杂环丁烷、3-乙基-3-(((3-乙基氧杂环丁烷-3-基)甲氧基)甲基)氧杂环丁烷、氧杂环丁基倍半硅氧烷、苯酚酚醛氧杂环丁烷、1,4-双(((3-乙基-3-氧杂环丁基)甲氧基)甲基)苯等。
作为上述环氧化合物,例如可举出:双酚A型环氧树脂、双酚E型环氧树脂、双酚F型环氧树脂、双酚S型环氧树脂、双酚O型环氧树脂、2,2’-二烯丙基双酚A型环氧树脂、脂环式环氧树脂、氢化双酚型环氧树脂、环氧丙烷加成双酚A型环氧树脂、间苯二酚型环氧树脂、联苯型环氧树脂、硫醚型环氧树脂、二苯基醚型环氧树脂、二环戊二烯型环氧树脂、萘型环氧树脂、苯酚酚醛型环氧树脂、邻甲酚酚醛型环氧树脂、二环戊二烯酚醛型环氧树脂、联苯酚醛型环氧树脂、萘酚酚醛型环氧树脂、缩水甘油胺型环氧树脂、烷基多元醇型环氧树脂、橡胶改性型环氧树脂、缩水甘油基酯化合物等。
作为上述环硫化合物,可举出通过将环氧化合物的环氧基变换为环硫基而得到的环硫化合物等。
作为上述(甲基)丙烯酸类化合物,例如可举出:通过使具有羟基的化合物与(甲基)丙烯酸反应而得到的酯化合物、通过使(甲基)丙烯酸与环氧化合物反应而得到的环氧(甲基)丙烯酸酯、通过使具有羟基的(甲基)丙烯酸衍生物与异氰酸酯化合物反应而得到的氨基甲酸酯(甲基)丙烯酸酯等。
作为上述酯化合物中的单官能的化合物,例如可举出:N-丙烯酰氧基乙基六氢邻苯二甲酰亚胺等邻苯二甲酰亚胺丙烯酸酯类、各种酰亚胺丙烯酸酯、(甲基)丙烯酸甲酯、(甲基)丙烯酸乙酯、(甲基)丙烯酸丙酯、(甲基)丙烯酸正丁酯、(甲基)丙烯酸异丁酯、(甲基)丙烯酸叔丁酯、(甲基)丙烯酸正辛酯、(甲基)丙烯酸异辛酯、(甲基)丙烯酸2-乙基己酯、(甲基)丙烯酸异壬酯、(甲基)丙烯酸异癸酯、(甲基)丙烯酸月桂酯、(甲基)丙烯酸异肉豆蔻酯、(甲基)丙烯酸硬脂酯、(甲基)丙烯酸环己酯、(甲基)丙烯酸异冰片酯、(甲基)丙烯酸二环戊烯酯、(甲基)丙烯酸苄基酯、(甲基)丙烯酸2-羟基乙酯、(甲基)丙烯酸2-羟基丙酯、(甲基)丙烯酸2-羟基丁酯、(甲基)丙烯酸4-羟基丁酯、(甲基)丙烯酸2-甲氧基乙酯、(甲基)丙烯酸2-乙氧基乙酯、(甲基)丙烯酸2-丁氧基乙酯、甲氧基乙二醇(甲基)丙烯酸酯、甲氧基聚乙二醇(甲基)丙烯酸酯、乙基卡必醇(甲基)丙烯酸酯、(甲基)丙烯酸四氢糠基酯、(甲基)丙烯酸2-苯氧基乙酯、苯氧基二乙二醇(甲基)丙烯酸酯、苯氧基聚乙二醇(甲基)丙烯酸酯、(甲基)丙烯酸2,2,2-三氟乙酯、(甲基)丙烯酸2,2,3,3-四氟丙酯、(甲基)丙烯酸1H,1H,5H-八氟戊酯、(甲基)丙烯酸二甲基氨基乙酯、(甲基)丙烯酸二乙基氨基乙酯、琥珀酸2-(甲基)丙烯酰氧基乙酯、六氢邻苯二甲酸2-(甲基)丙烯酰氧基乙酯、邻苯二甲酸2-(甲基)丙烯酰氧基乙基2-羟基丙酯、(甲基)丙烯酸缩水甘油基酯、磷酸2-(甲基)丙烯酰氧基乙酯等。
另外,作为上述酯化合物中的2官能的化合物,例如可举出1,3-丁二醇二(甲基)丙烯酸酯、1,4-丁二醇二(甲基)丙烯酸酯、1,6-己二醇二(甲基)丙烯酸酯、1,9-壬二醇二(甲基)丙烯酸酯、1,10-癸二醇二(甲基)丙烯酸酯、2-正丁基-2-乙基-1,3-丙二醇二(甲基)丙烯酸酯、乙二醇二(甲基)丙烯酸酯、二乙二醇二(甲基)丙烯酸酯、四乙二醇二(甲基)丙烯酸酯、聚乙二醇二(甲基)丙烯酸酯、二丙二醇二(甲基)丙烯酸酯、三丙二醇二(甲基)丙烯酸酯、聚丙二醇(甲基)丙烯酸酯、环氧乙烷加成双酚A二(甲基)丙烯酸酯、环氧丙烷加成双酚A二(甲基)丙烯酸酯、环氧乙烷加成双酚F二(甲基)丙烯酸酯、二羟甲基二环戊二烯基二(甲基)丙烯酸酯、新戊二醇二(甲基)丙烯酸酯、环氧乙烷改性异氰脲酸二(甲基)丙烯酸酯、2-羟基-3-(甲基)丙烯酰氧基丙基(甲基)丙烯酸酯、碳酸酯二醇二(甲基)丙烯酸酯、聚醚二醇二(甲基)丙烯酸酯、聚酯二醇二(甲基)丙烯酸酯、聚己内酯二醇二(甲基)丙烯酸酯、聚丁二烯二醇二(甲基)丙烯酸酯等。
另外,作为上述酯化合物中的3官能以上的化合物,例如可举出三羟甲基丙烷三(甲基)丙烯酸酯、环氧乙烷加成三羟甲基丙烷三(甲基)丙烯酸酯、环氧丙烷加成三羟甲基丙烷三(甲基)丙烯酸酯、己内酯改性三羟甲基丙烷三(甲基)丙烯酸酯、季戊四醇三(甲基)丙烯酸酯、环氧乙烷加成异氰脲酸三(甲基)丙烯酸酯、甘油三(甲基)丙烯酸酯、环氧丙烷加成甘油三(甲基)丙烯酸酯、三(甲基)丙烯酰氧基乙基磷酸酯、二(三羟甲基丙烷)四(甲基)丙烯酸酯、季戊四醇四(甲基)丙烯酸酯、二季戊四醇五(甲基)丙烯酸酯、二季戊四醇六(甲基)丙烯酸酯等。
作为上述环氧(甲基)丙烯酸酯,例如可举出利用常规方法使环氧化合物和(甲基)丙烯酸在碱性催化剂的存在下进行反应而得到的化合物等。
上述烯丙醇衍生物,例如可举出:马来酸二烯丙酯、己二酸二烯丙酯、邻苯二甲酸二烯丙酯、甘油1,3-二烯丙基醚三羟甲基丙烷二烯丙基醚等二烯丙基化合物、氰脲酸三烯丙酯、异氰尿酸三烯丙酯、偏苯三酸三烯丙酯、季戊四醇三烯丙基醚等。
另外,针对分散有红色颜料的感光性树脂组合物、分散有绿色颜料的感光性树脂组合物、及分散有蓝色颜料的感光性树脂组合物,也进行上述的形成本发明的黑色矩阵的方法的操作,形成各色的像素图案,由此能够形成滤色器。
上述分散有红色颜料的感光性树脂组合物、上述分散有绿色颜料的感光性树脂组合物、及上述分散有蓝色颜料的感光性树脂组合物能够使用现有公知的物质。
需要说明的是,上述滤色器也能够通过以下方法制造:从喷墨喷嘴向由本发明的黑色矩阵划分的各区域中喷出红色、绿色、及蓝色的各色墨液,利用热或光使积存的墨液固化。
上述滤色器能够合适地用作液晶显示装置、有机电致发光显示装置等显示装置的构件。
发明效果
根据本发明,能够提供电绝缘性高、且在可见光区域中能够实现高的黑色度的黑色粒子、包含该黑色粒子的黑色涂料、涂膜及滤色器用黑色矩阵。
附图说明
图1为示出将在实施例1中得到的黑色粒子的干燥粉体通过固体13C-NMR进行测定的结果的图。
图2为将在实施例1中得到的黑色粒子的干燥粉体以成为0.1重量%的浓度的方式添加并再分散的水溶液的FE-SEM图像。
图3为将在实施例2中得到的黑色粒子的干燥粉体以成为0.1重量%的浓度的方式添加并再分散的水溶液的FE-SEM图像。
图4为将在实施例3中得到的黑色粒子的干燥粉体以成为0.1重量%的浓度的方式添加并再分散的水溶液的FE-SEM图像。
图5为将在实施例4中得到的黑色粒子的干燥粉体以成为0.1重量%的浓度的方式添加并再分散的水溶液的FE-SEM图像。
图6为将在实施例5中得到的黑色粒子的干燥粉体以成为0.1重量%的浓度的方式添加并再分散的水溶液的FE-SEM图像。
图7为将在比较例1中得到的干燥体以成为0.1重量%的浓度的方式添加并再分散的水溶液的FE-SEM图像。
具体实施方式
以下列举实施例来更加详细地说明本发明的方式,本发明不仅限定于这些实施例。
(实施例1)
将吡咯(东京化成工业公司制)6.7g(0.1mol)溶解于水1.4L,进一步添加甲酸(东京化成工业公司制)1.75g进行搅拌,由此得到吡咯水溶液。
另外,将对苯醌(东京化成工业公司制)10.8g(0.1mol)在水0.35L与乙醇0.35L的混合溶液中溶解而得到对苯醌溶液。
向得到的吡咯水溶液中滴加对苯醌溶液进行混合,得到混合液。
将得到的混合液在室温(25℃)下搅拌48小时后,加热至60℃进一步搅拌48小时,然后,蒸馏去除水等溶剂,在100℃下干燥16小时,进一步在220℃进行3小时加热处理,得到黑色粒子的干燥粉体,所述黑色粒子包含具有来自于吡咯的结构单元和来自于对苯醌的结构单元的共聚物。
需要说明的是,与上述同样地准备混合液,在室温(25℃)下搅拌48小时后,在130℃的条件下干燥30分钟,结果得到吡咯及对苯醌的添加量的70重量%以上的残留固体成分。若考虑到吡咯的沸点及对苯醌的熔点(升华),在130℃以上挥发,不会作为固体成分残留,但干燥后的残留固体成分比吡咯的投料量多,可认为得到了吡咯与对苯醌的共聚物。
另外,针对在实施例1中得到的黑色粒子的干燥粉体,通过固体13C-NMR测定的结果如图1所示。如图1所示,峰非常宽,暗示不是单一结构的树脂,可知形成黑色粒子的树脂的碳原子几乎都是芳香族碳,几乎没有单独的脂肪族碳、双键碳。因此,可认为原料的吡咯环及苯醌环成为稠环结构,例如得到了具有下述式(3)这样的部分结构的共聚物。
[化3]
针对得到的黑色粒子的干燥粉体,制作以成为0.1重量%的浓度的方式添加至水进行再分散的水溶液。使用FE-SEM拍摄所得到的水溶液的显微镜照片示于图2。如图2所示,可知在实施例1中得到的黑色粒子即使在再分散时也具有高的分散性。
(实施例2)
使用次膦酸代替甲酸,除此以外,与实施例1同样地操作,得到黑色粒子的干燥粉体。
针对与实施例1同样地进行再分散的水溶液,使用FE-SEM拍摄的显微镜照片示于图3。如图3所示,可知在实施例2中得到的黑色粒子即使在再分散时也具有高的分散性。
(实施例3)
使用0.01M盐酸水溶液代替甲酸,除此以外,与实施例1同样地操作,得到黑色粒子的干燥粉体。
针对与实施例1同样地进行再分散的水溶液,使用FE-SEM拍摄的显微镜照片示于图4。如图4所示,可知在实施例3中得到的黑色粒子即使在再分散时也具有高的分散性。
(实施例4)
使用柠檬酸代替甲酸,除此以外,与实施例1同样地操作,得到黑色粒子的干燥粉体。
针对与实施例1同样地进行再分散的水溶液,使用FE-SEM拍摄的显微镜照片示于图5。如图5所示,可知在实施例4中得到的黑色粒子即使在再分散时也具有高的分散性。
(实施例5)
将得到的混合液在45℃搅拌2小时后,加热至80℃进一步搅拌48小时,除此以外,与实施例1同样地操作,得到黑色粒子的干燥粉体。
针对与实施例1同样地进行再分散的水溶液,使用FE-SEM拍摄的显微镜照片示于图6。如图6所示,可知在实施例5中得到的黑色粒子即使在再分散时也具有高的分散性。
(比较例1)
将吡咯(东京化成工业公司制)6.7g(0.1mol)溶解于水1.75L,进一步添加过硫酸铵(富士胶片和光纯药公司制)17.5g进行搅拌,由此得到吡咯水溶液。
将得到的吡咯水溶液在室温(25℃)下搅拌48小时后,加热至60℃进一步搅拌48小时,然后,蒸馏去除水等溶剂,在100℃干燥16小时,进一步在220℃进行3小时加热处理,得到干燥体。需要说明的是,在吡咯水溶液的搅拌中途生成沉降物,干燥体成为块状物,无法得到粒子状的干燥物。
针对与实施例1同样地进行再分散的水溶液,使用FE-SEM拍摄的显微镜照片示于图7。如图7所示,可知在比较例1中得到的干燥体为块状物,即使再次分散于水中也无法充分分散。
(比较例2)
作为黑色粒子的干燥粉体,使用了科琴黑(Lion Specialty Chemicals Co.,Ltd.制“EC600JD”)。
(比较例3)
将1,5-二羟基萘(1,5-DHN,东京化成公司制)1.20g和1,3,5-三嗪(东京化成公司制)0.98g依次溶解于乙醇50ml中,制作乙醇混合溶液。
接下来,将得到的混合溶液在80℃下加热搅拌1小时(转速:300rpm)。将溶液用玻璃过滤器过滤,用乙醇清洗3次后,在50℃下真空干燥3小时。然后,在110℃下加热2小时,由此得到黑色粒子的干燥粉体。
针对实施例及比较例的黑色粒子及干燥体,进行以下的评价。结果示于表1。
(比较例4)
使用硼酸代替甲酸,除此以外,与实施例1同样地操作,得到黑色粒子的干燥粉体。
(比较例5)
除了不添加甲酸以外,与实施例1同样地操作,得到黑色粒子的干燥粉体。
(1)水分散体个数平均粒径
将实施例、比较例的干燥粉体添加至水中制作0.1重量%浓度的水分散体10ml,进一步地,照射45kHz的超声波30分钟,得到水分散液。针对得到的分散液,使用动态光散射式(DLS)粒径分布测定装置(Microtrack bell公司制“Nanotrac Wave II”),在近似真球形状、照射光吸收、个数分布的条件下测定平均粒径。
需要说明的是,在比较例1中未得到干燥粉体,因此未进行评价。
(2)Zeta电位
针对实施例、比较例的黑色粒子,使用显微镜电泳方式Zeta电子测定装置(NihonRufuto Co.,Ltd.制“MODEL 502”),测定Zeta电位。具体而言,使用浓度0.01M的KCl水溶液作为支持电解质,将分散了少量的黑色粒子的KCl溶液注入测定用容器中。然后,一边利用显微镜观察一边施加电压,调整至粒子不动(静止)为止,将此时的电位作为Zeta电位。
需要说明的是,在比较例1中未得到干燥粉体,因此未进行评价。
(3)重均分子量
针对在实施例1~5、比较例3~5中得到的黑色粒子,使用动态光散射式(DLS)重均分子量测定装置(Microtrack bell公司制“Nanotrac Wave II”),分析在“(1)水分散体个数平均粒径”中得到的分散液,由此测定共聚物的重均分子量。
(4)体积电阻率
针对实施例、比较例的黑色粒子及干燥体的体积电阻率,使用粉体电阻测定系统(三菱化学Analytech公司制),测定在负载20kN下的体积电阻值。
(5)总透光率
作为固化性化合物,使用将甲基丙烯酸2-羟基乙酯(富士胶片和光纯药公司制)、邻苯二甲酸二烯丙酯(富士胶片和光纯药公司制)、二(三羟甲基丙烷)四丙烯酸酯(新中村化学工业公司制)、氨基甲酸酯丙烯酸酯(U-4HA、新中村化学工业公司制)以重量比3:1:1:1进行混合而得的物质。另外,作为固化剂,使用Irgacure 907(BASF公司制)。
将在实施例、比较例中得到的干燥粉体或干燥体45重量份、上述固化性化合物52.4重量份、上述固化剂2.6重量份在室温下进行混合,得到树脂组合物。
将得到的树脂组合物涂敷于载玻片后,使用高压汞灯照射3500mJ/cm2的紫外线,制作厚度1μm的涂膜。针对得到的涂膜,使用带积分球的分光光度计(日立制作所公司制“U-4100型”),针对10点测定400~800nm的整个可见光区域的透光率,求出该透光率的平均值及10点测量的标准偏差。使用在比较例中得到的干燥粉体或干燥体的情况下,无法得到均匀的树脂组合物,其结果,无法得到均匀的涂膜,透光率的偏差变大。
需要说明的是,总光线反射率受到测定夹具的反射率的影响大,因此通过测定总透光率,能够更高精度地判定涂膜的黑色度。
(6)元素含量(原子%)
利用X射线光电子分光法(XPS)测定实施例、比较例的黑色粒子及干燥体,测定元素含量(原子%)。
[表1]
产业上的可利用性
根据本发明,能够提供电绝缘性高、且在可见光区域中能够实现高的黑色度的黑色粒子、包含该黑色粒子的黑色涂料、涂膜及滤色器用黑色矩阵。
Claims (5)
1.一种黑色粒子,其包含共聚物,所述共聚物具有来自于吡咯化合物的结构单元和来自于醌化合物的结构单元,
所述黑色粒子的水分散体个数平均粒径为100nm以下,
所述黑色粒子的Zeta电位为-5mV以下。
2.根据权利要求1所述的黑色粒子,其包含共聚物,所述共聚物具有来自于吡咯的结构单元和来自于苯醌的结构单元。
3.一种黑色涂料,其包含权利要求1~2中任一项所述的黑色粒子。
4.一种涂膜,其包含权利要求1~2中任一项所述的黑色粒子。
5.一种滤色器用黑色矩阵,其包含权利要求1~2中任一项所述的黑色粒子。
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