CN110016002B - 一种含氟芴类光引发剂及其应用 - Google Patents

一种含氟芴类光引发剂及其应用 Download PDF

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CN110016002B
CN110016002B CN201810020889.8A CN201810020889A CN110016002B CN 110016002 B CN110016002 B CN 110016002B CN 201810020889 A CN201810020889 A CN 201810020889A CN 110016002 B CN110016002 B CN 110016002B
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photoinitiator
fluorine
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butoxide
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钱晓春
胡春青
于培培
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Changzhou Tronly New Electronic Materials Co Ltd
Changzhou Tronly Advanced Electronic Materials Co Ltd
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Changzhou Tronly New Electronic Materials Co Ltd
Changzhou Tronly Advanced Electronic Materials Co Ltd
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Abstract

本发明公开一种含氟芴类光引发剂，具有如通式(I)所示结构。该光引发剂引发效率高，相比于类似结构的现有芴类光引发剂，其可带来更加优异的表干性能和耐候性，并且只需很少的用量就能达到所需效果，具有很好的应用前景。

Description

一种含氟芴类光引发剂及其应用
技术领域
本发明属于有机化学领域，具体涉及一种含氟芴类光引发剂及其在光固化领域中的应用。
背景技术
氟是电负性最强的元素，C-F键短，键角小，氟原子沿碳链呈螺旋分布，键链四周被性质稳定的氟原子包围，这对主链具有极强的保护作用，这种特殊结构使得整个分子十分僵硬，分子转动势垒很大，因此具有很好的耐候性和耐化学品性。虽然C-F建是极性的，但由于分子对称，极性相互抵消，整个分子呈现非极性，表面能和表面张力非常低，具有既憎水又憎油的特性。鉴于氟原子这一优良特性，其被逐步应用于光固化油墨、光固化涂料、光致抗蚀剂等光固化领域，如专利文献CN1119874A、CN1053915A、TW201736532A、CN105026127A等分别公开了将含氟基团引入到不同的树脂或单体中，专利文献CN10338755A、CN10326466A公开了将氟原子引入到二苯甲酮及1173等普通光引发剂中，提高引发剂的抗氧阻聚能力及耐候性。但在实际应用中，这些小分子光引发剂存在光解碎片容易迁移的特点，而若提高分子量，通常又会降低光引发效果。
发明内容
本发明的目的主要在于提供一种含氟芴类光引发剂，其引发效率高，相比于类似结构的现有芴类光引发剂，其可带来更加优异的表干性能和耐候性，并且只需很少的用量就能达到所需效果，具有很好的应用前景。
本发明的含氟芴类光引发剂，具有通式(I)所示结构：
Figure BDA0001543502700000021
其中，
R1和R1’各自独立地表示含氟基团；
R2和R3各自独立地表示C1-C20的直链或支链烷基、C3-C12的环烷基、C4-C18的环烷基烷基、C6-C20的芳基、C7-C24的芳基烷基、取代或未取代的C4-C20的杂芳基，或者R2和R3彼此相连形成C3-C10的环烷基；
R4表示羟基、N-吗啉基、N-哌啶基、N-哌嗪基、N-吡咯基或N-仲胺基；
A表示氢、硝基、-CO-CR2R3R4基团、或-R5-(R6)n，其中，R5表示O、S、N或羰基，R6表示C1-C20的直链或支链烷基、C3-C12的环烷基、C4-C18的环烷基烷基、取代或未取代的C6-C20的芳基、C7-C24的芳基烷基、五元或六元的不饱和杂环基团、取代或未取代的C4-C20的杂芳基，n表示1或2。
作为优选技术方案，上述通式(I)所示的含氟芴类光引发剂中，R1和R1’各自独立地表示C2-C10的直链或支链的含氟烷基，任选地(optionally)，其中的-CH2-可被-O-或亚苯基所取代，且亚苯基上的H可任选地被C1-C4的烷基所取代。进一步优选地，R1和R1’各自独立地表示以-CF3、-CF2CF3、-CF2-CH2F或-CF2-CHF2为端基的、C3-C8的直链或支链的含氟烷基，任选地，其中的-CH2-可被-O-或1,4-亚苯基所取代，且1,4-亚苯基上的H可任选地被C1-C4的烷基所取代。
优选地，R2和R3各自独立地表示C1-C8的直链或支链烷基、C4-C12的环烷基烷基、C7-C14的芳基烷基，或者R2和R3彼此相连形成C3-C8的环烷基。进一步优选地，R2和R3各自独立地表示C1-C4的直链或支链烷基、C4-C10的环烷基烷基、C7-C10的苯基烷基，或者R2和R3彼此相连形成C3-C8的环烷基。
优选地，R4表示羟基、N-吗啉基、N-哌啶基、或两个氢被C1-C4烷基取代的胺基。
优选地，A表示氢、硝基、-CO-CR2R3R4基团、或-R5-(R6)n，其中，R5表示O、S、N或羰基，R6表示C1-C8的直链或支链烷基、C6-C12的芳基、被C1-C5烷基、硝基或氰基取代的C6-C12的芳基、五元不饱和杂环基团，n表示1或2。进一步优选地，R6表示C1-C4的直链或支链烷基、呋喃基、吡咯基、噻吩基、C6-C10的芳基、被C1-C4烷基、硝基或氰基取代的C6-C10的芳基。
非限制性地，所述含氟芴类光引发剂可选自如下结构：
Figure BDA0001543502700000031
Figure BDA0001543502700000041
Figure BDA0001543502700000051
Figure BDA0001543502700000061
Figure BDA0001543502700000071
相应地，本发明还涉及上述通式(I)所示的含氟芴类光引发剂的制备方法，将原料a和b在催化剂作用下反应，反应式如下所示：
Figure BDA0001543502700000072
其中，M表示H或OH，
当M表示H时，R0即为R1、R0’即为R1’，
当M表示OH时，R0、R0’分别对应于R1、R1’，且R1表示OR0、R1’表示OR0’，
X表示Cl或Br。
上述制备方法中使用的原料和试剂均为现有技术中的已知化合物或可通过已知工艺方便地制得，其中原料a可通过如申请号为201510937328.0、201710088234.X、201710530354.0、201710835527.X等的中国发明专利申请中记载的合成方法制备而成。
反应在有机溶剂中进行，对溶剂种类并无特别的限定，只要能够溶解原料且对反应无不良影响即可，优选极性溶剂，特别是DMF。所述的催化剂是碱性催化剂，优选叔丁醇锂、叔丁醇钠和叔丁醇钾中的至少一种。反应温度为10-50℃。反应时间根据原料种类略有差异，通常为1-6h。
本发明还涉及上述通式(I)所示的含氟芴类光引发剂在光固化领域中的应用。非限制性地，该光引发剂可应用在彩色光阻(RGB)、黑色矩阵(BM)、光间隔物(photo-spacer)、肋栅(rib)、干膜、半导体光刻胶及油墨等方面。该光引发剂引发效率高，可带来优异的表干性能和耐候性能。
具体实施方式
以下将结合具体实施例对本发明作进一步详细说明，但不应将其理解为对本发明保护范围的限制。
制备实施例
实施例1
化合物1的合成
Figure BDA0001543502700000081
向250mL的四口烧瓶中加入36.8g原料1a、叔丁醇钠10.6g和DMF50mL，室温(约25℃)搅拌，滴加26.6g原料1b，约1h滴加完，滴加完后继续搅拌3h，液相跟踪反应至完全。将物料缓慢倒入200g水中，二氯甲烷(每次50mL，共2次)萃取，用5％的碳酸氢钠水溶液(每次100mL，共3次)清洗二氯甲烷层，接着水洗二氯甲烷层至pH呈中性，用80g无水硫酸镁干燥二氯甲烷层，过滤后旋蒸二氯甲烷产物溶液，甲醇重结晶，70℃烘箱干燥2h，得41.9g化合物1，收率75％，纯度98％。
化合物1的结构通过核磁共振氢谱和质谱得到确认:
1H-NMR(CDCl3，500MHz)：1.3662-1.3772(6H，s)，1.8068-1.8925(8H,m)，2.3675-2.4704(7H，m)，3.6523-3.6744(4H，t)，7.3027-8.1823(6H，m)。
MS(m/z)：560(M+1)+。
实施例2
化合物2的合成
Figure BDA0001543502700000091
向250mL的四口烧瓶中加入50.5g原料2a、叔丁醇钾10.6g和DMF50mL，室温(约25℃)搅拌，滴加27,3g原料2b，约1h滴加完，滴加完后继续搅拌3h，液相跟踪反应至完全。将物料缓慢倒入200g水中，二氯甲烷(每次50mL，共2次)萃取，用5％的碳酸氢钠水溶液(每次100mL，共3次)清洗二氯甲烷层，接着水洗二氯甲烷层至pH呈中性，用80g无水硫酸镁干燥二氯甲烷层，过滤后旋蒸二氯甲烷产物溶液，甲醇重结晶，70℃烘箱干燥2h，得51.4g化合物2，收率68％，纯度98％。
化合物1的结构通过核磁共振氢谱和质谱得到确认:
1H-NMR(CDCl3，500MHz)：0.9556-0.9918(3H,t)，1.5208-1.5476(2H，m)，2.2675-2.2807(6H,s)，2.7598-2.7604(2H,s)，5.9989-6.0387(2H，d)，7.1225-8.1783(16H，m)。
MS(m/z)：706(M+1)+。
实施例3-20
参照实施例1的方法，由相应原料制备具有表1中所示结构的化合物。
表1
Figure BDA0001543502700000101
Figure BDA0001543502700000111
Figure BDA0001543502700000121
Figure BDA0001543502700000131
性能表征
配置示例性的光固化树脂组合物，对本发明通式(I)所示光引发剂的关键应用性能进行评价。
1.光固化树脂组合物的配制
光固化树脂组合物由下列组分组成：
Figure BDA0001543502700000132
Figure BDA0001543502700000141
将各组分混合均匀，即可得到用于性能评价的光固化树脂组合物。其中，所述的光引发剂是本发明通式(I)所示的含氟芴类光引发剂或作为对比的现有技术中已知的代表性芴类光引发剂。
2.性能评价
对光固化树脂组合物的性能评价包括固化速度、表干性能和耐候性。
(1)固化速度
将光固化树脂组合物在黄光灯下搅拌，取料于PET模板上利用滚涂成膜，在90℃下干燥2min，得到干膜厚为2μm的涂膜，然后冷却至室温，用高压汞灯(曝光机型号：RW-UV70201，单次曝光量50mJ/cm2)照射对涂膜进行曝光，使其固化成膜。
以涂膜固化成固化膜所需经过履式曝光带的次数评价，经过次数越多，表明固化速度越不理想。
(2)耐候性
参照GB/T-1740-2007，采用漆膜耐湿热性测定方法。将充分固化的固化膜放入预先调节好的调温调湿箱中(温度50±1℃，相对湿度96±2％)，放置240h后，评定固化膜表面起泡、开裂、黄变等破坏现象。
如果没有变化，记为A；
如果有气泡、开裂或黄变等破坏现象，记为B。
(3)表干性能
参照GB/T 1728-1979(1989)，采用吹棉球法进行测定。在固化膜表面轻放1个约1cm2的疏松脱脂棉球，用嘴距棉球15cm沿水平方向轻吹棉球。
如能吹走棉球，且膜表面不留棉丝，记为A；
如能吹走棉球，但膜表面留有棉丝，记为B；
如不能吹走棉球，记为C。
若能吹走棉球且膜表面不留棉丝，即为表面干燥，说明膜的表干性能优异。
性能评价结果如表2中所示。
表2
Figure BDA0001543502700000151
Figure BDA0001543502700000161
表2中，比较化合物1和2的结构如下所示：
Figure BDA0001543502700000162
从表2的测试结果可以看出，使用本发明通式(I)所示的含氟芴类光引发剂的光固化树脂组合物，在单次50mJ/cm2曝光剂量下就能充分固化，展现出了明显更高的引发效率，且耐候性和表干性能也明显优于采用现有芴类光引发剂的样品。

Claims (6)

1.一种含氟芴类光引发剂，具有通式(I)所示结构：
Figure FDA0004059827950000011
其中，
R1和R1 ’各自独立地表示以-CF3、-CF2CF3、-CF2-CH2F或-CF2-CHF2为端基的、C3-C8的直链或支链的含氟烷基，任选地，其中的-CH2-可被-O-或1,4-亚苯基所取代，且1,4-亚苯基上的H可任选地被C1-C4的烷基所取代；
R2和R3各自独立地表示C1-C4的直链或支链烷基、C4-C10的环烷基烷基、C7-C10的苯基烷基，或者R2和R3彼此相连形成C3-C8的环烷基；
R4表示羟基、N-吗啉基、N-哌啶基、或两个氢被C1-C4烷基取代的胺基；
A表示氢、硝基、-CO-CR2R3R4基团、或-R5-(R6)n，其中，R5表示S、N或羰基，R6表示C1-C4的直链或支链烷基、呋喃基、吡咯基、噻吩基、C6-C10的芳基、被C1-C4烷基或硝基取代的C6芳基；n表示1或2。
2.权利要求1所述的含氟芴类光引发剂的制备方法，将原料a和b在催化剂作用下反应，反应式如下所示：
Figure FDA0004059827950000012
其中，M表示H或OH，
当M表示H时，R0即为R1、R0’即为R1’，
当M表示OH时，R1表示OR0、R1’表示OR0’，
X表示Cl或Br。
3.根据权利要求2所述的制备方法，其特征在于：所述的催化剂是碱性催化剂。
4.根据权利要求3所述的制备方法，其特征在于：所述的催化剂选自叔丁醇锂、叔丁醇钠和叔丁醇钾中的至少一种。
5.权利要求1所述的含氟芴类光引发剂在光固化领域中的应用。
6.根据权利要求5所述的应用，其特征在于：所述的光引发剂被用于制备彩色光阻、黑色矩阵、光间隔物、肋栅、干膜、半导体光刻胶及油墨。
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