CN113785032A - 反应性介晶 - Google Patents
反应性介晶 Download PDFInfo
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- CN113785032A CN113785032A CN202080031978.8A CN202080031978A CN113785032A CN 113785032 A CN113785032 A CN 113785032A CN 202080031978 A CN202080031978 A CN 202080031978A CN 113785032 A CN113785032 A CN 113785032A
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- 229950009883 tocopheryl nicotinate Drugs 0.000 description 1
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- INNSFNJTGFCSRN-UHFFFAOYSA-N tridecyl 2-[(3,5-ditert-butyl-4-hydroxyphenyl)methylsulfanyl]acetate Chemical compound CCCCCCCCCCCCCOC(=O)CSCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 INNSFNJTGFCSRN-UHFFFAOYSA-N 0.000 description 1
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- WGKLOLBTFWFKOD-UHFFFAOYSA-N tris(2-nonylphenyl) phosphite Chemical compound CCCCCCCCCC1=CC=CC=C1OP(OC=1C(=CC=CC=1)CCCCCCCCC)OC1=CC=CC=C1CCCCCCCCC WGKLOLBTFWFKOD-UHFFFAOYSA-N 0.000 description 1
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- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- QUEDXNHFTDJVIY-UHFFFAOYSA-N γ-tocopherol Chemical class OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1 QUEDXNHFTDJVIY-UHFFFAOYSA-N 0.000 description 1
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- Polarising Elements (AREA)
Abstract
本发明涉及新颖反应性介晶(RM)、包含该介晶的混合物及配制剂、由该RM及RM混合物获得的聚合物以及该RM、RM混合物及聚合物在如用于液晶显示器(LCD)的光学膜的光学或电光学组件或装置中的用途。
Description
发明领域
本发明涉及新颖反应性介晶(RM)、包含该介晶的混合物及配制剂、由该RM及RM混合物获得的聚合物及RM、RM混合物及聚合物在如用于液晶显示器(LCD)的光学膜的光学或电光学组件或装置中的用途。
背景及现有技术
可聚合液晶材料在制备各向异性聚合物膜的现有技术中已知。这些膜常通过以下制备:将可聚合液晶混合物的薄层涂布于基板上,使混合物配向而呈均一定向且最终通过使可聚合液晶材料聚合以固定液晶分子的定向。因此,聚合的膜中的液晶分子的定向可为平面的,即,其中液晶分子经定向而实质上相对于该层平行、垂直(与该层成直角或正交)或倾斜。相应光学膜描述于例如EP 0 940 707 B1、EP 0 888 565 B1及GB 2 329 393 B1中。
如专家通常已知,基于可聚合液晶材料的光学膜通常呈现波长依赖性延迟。就此而言,已知光学特性的三种主要类型:
i)“正常”或“正”光色散,例如描述于EP 0 940 707 B1中
ii)“逆向”或“负”光色散,例如描述于WO 2016/020035 A1中,及
iii)“平面”光色散,例如描述于WO 2009/058396 A1中。
举例而言,平面或负色散可聚合液晶材料可通过将至少一种具有(no)高于非常折射率(ne)的寻常折射率(no)的组分添加至配制剂中而制成。因此,在相对于分子的长轴的正交位置中需要高度共轭的取代基。当固化光学膜时,后述材料吸收部分UV剂量,这导致固化程度差及固化膜的耐热性差。此外,后述分子嵌段可在氧气存在的情况下在高温下易于氧化。上述适用于含有高度共轭的反应性介晶的高双折射配制剂,其降低固化膜的耐热性且其通常易于变黄。
举例而言,WO 2008/119427 A1描述具有负光色散的双折射聚合物膜,其可获自可聚合LC材料,该材料包含具有下文显示的结构作为负色散组分的化合物或其衍生物:
WO 2008/119427 A1中公开的可聚合LC材料中的负色散组分的比率是例如固体(即,不含溶剂)的总量的50-60%。然而,根据现有技术的负色散化合物的庞大体积特性通常难以配向或为配制剂提供用于退火温度的狭窄工艺窗口,其不便于大量生产。
减少上文描述的混合物中的材料的量对混合物的可溶性、耐久性及工艺窗口具有显著正面作用。当前,无法在不损害膜的负色散特性的情况下实现此目标。
WO 2015/115390 A1公开以下通用结构的化合物:
包含这些化合物的可聚合组合物;由此可聚合组合物形成的膜;及用于显示投射的图像的半反射镜,其包含此膜且表示诸如低双折射率延迟膜及对反射波长范围具有高选择性的反射膜的膜可使用此可聚合组合物制造。然而,WO 2015/115390 A1未提及在呈现负光色散的聚合物膜中使用这些化合物。
因此,本发明的目标是提供改良的RM、RM混合物及RM配制剂,其不具有现有技术已知的材料的缺点。特别地,目标是提供优选具有负光色散的RM及RM混合物及RM配制剂,其适用于通过原位UV光聚合制备聚合物,呈现良好溶解度,显示改良的加宽潜能,且其具有有利转化温度。本发明的其他目标根据以下描述而对专家显而易见。
出人意料地,本发明的发明人已发现根据权利要求1的化合物及其用途可显著改良当前已知的光学膜。
发明概述
因此,本发明涉及式I化合物,
P是可聚合基团,
Sp是间隔基团或单键,Sp优选表示-(CH2)n-,其中n表示1至9,诸如亚甲基、亚乙基、亚丙基、亚丁基、亚戊基、亚己基、亚庚基、亚辛基、亚壬基;n优选表示5与7之间的整数,诸如亚甲基、亚乙基、亚丙基、亚丁基、亚戊基、亚己基、亚庚基,
R11是优选具有1至15个C原子的烷基、烷氧基、硫代烷基、烷羰基、烷氧基羰基、烷基羰氧基或烷氧基羰氧基,其任选地经氟化,
A表示芳族或脂环基团,其任选地含有一个或多个选自N、O及S的杂原子,且任选地经L单取代或多取代,
L是F、Cl、Br、I、-CN、-NO2、-NCO、-NCS、-OCN、-SCN、-C(=O)NRxRy、-C(=O)ORx、-C(=O)Rx、-NRxRy、-OH、-SF5或是具有1至12个C原子的直链或支链烷基、烷氧基、烷羰基、烷氧基羰基、烷基羰氧基或烷氧基羰氧基,其中一个或多个H原子任选地经F或Cl替代,优选F、-CN或具有1至6个C原子的直链或支链烷基、烷氧基、烷羰基、烷氧基羰基、烷基羰氧基或烷氧基羰氧基,
R00、R000、Rx及Ry彼此独立地表示H或具有1至12个C原子的烷基,
Z11及Z12若多次出现,则彼此独立地表示-O-、-S-、-CO-、-COO-、-OCO-、-S-CO-、-CO-S-、-O-COO-、-CO-NR00-、-NR00-CO-、-NR00-CO-NR000、-NR00-CO-O-、-O-CO-NR00-、-OCH2-、-CH2O-、-SCH2-、-CH2S-、-CF2O-、-OCF2-、-CF2S-、-SCF2-、-CH2CH2-、-(CH2)n1、-CF2CH2-、-CH2CF2-、-CF2CF2-、-CH=N-、-N=CH-、-N=N-、-CH=CR00-、-CY1=CY2-、-C≡C-、-CH=CH-COO-、-OCO-CH=CH-或单键,优选是-COO-、-OCO-或单键,更优选是-COO-或-OCO-。
Y1及Y2彼此独立地表示H、F、Cl或CN,及
n1是1至10的整数,优选是1、2、3或4。
本发明进一步涉及包含两种或更多种RM的混合物,其在下文称为“RM混合物”,所述两种或更多种RM的至少一种为式I的化合物。
本发明进一步涉及包含一种或多种式I的化合物或如上下文所述RM混合物、并进一步包含一种或多种溶剂和/或添加剂的配制剂,其在下文称为“RM配制剂”。
本发明进一步涉及可通过式I的化合物或如上下文所述的RM混合物聚合获得的聚合物,优选其中RM为配向的,和优选在其中RM或RM混合物展示出液晶相的温度下进行。
本发明进一步涉及式I的化合物、RM混合物或如上下文所述的聚合物在光学、电光学或电子组件或器件中的用途。
本发明进一步涉及包含RM、RM混合物或如上下文所述聚合物的光学、电光学或电子器件或其组件。
所述组件包括但不限于光学延迟膜、偏振器、补偿器、分束器、反射膜、配向层、滤色器、抗静电保护片、电磁干扰保护片、偏振控制型透镜(例如用于自动立体3D显示器)、IR反射膜(例如用于窗应用),及用于光导、聚焦及光学效应(例如3D、全像摄影、电信)的透镜。
所述器件包括,但不限于,电光学显示器(尤其是LC显示器、自动立体3D显示器)、有机发光二极管(OLED)、光学数据储存器件、和窗。
术语的定义
如本文所用的,术语“聚合物”将被理解为是指包含一种或多种不同类型的重复单元(分子的最小构成单元)的主链的分子,并且其包括公知的术语“低聚物”、“共聚物”、“均聚物”等。此外,应当理解术语聚合物除了该聚合物本身之外,还包含来自引发剂、催化剂和伴随这样的聚合物的合成的其他要素的残留物,其中这样的残留物被理解为不是共价掺入其中。此外,这样的残留物和其他要素尽管通常在聚合后纯化过程中被移除,但是它们通常与聚合物混合或掺和,使得当聚合物在容器之间或溶剂或分散介质之间转移时,它们通常保留在聚合物中。
在本发明中所用的术语“(甲基)丙烯酸类聚合物”包括由丙烯酸类单体得到的聚合物,可由甲基丙烯酸类单体得到的聚合物,以及可由这样的单体的混合物得到的相应的共聚物。
术语“聚合”是指通过使多个可聚合基团或包含这样的可聚合基团的聚合物前体(可聚合化合物)键合在一起以形成聚合物的化学方法。
术语“膜”或“层”包括刚性或柔性,自承或自立的具有机械稳定性的膜,以及在支撑基材上或两个基材之间的涂层或层。
术语“液晶化合物或介晶化合物”意谓包含一个或多个棒状(杆状或板/板条状)或盘状(圆盘状)介晶基团的化合物。术语“介晶基团”意谓具有诱导液晶(LC)相特性的能力的基团。包含介晶基团的化合物本身不必呈现LC相。其也可仅在与其他化合物的混合物中,或当介晶化合物或材料或其混合物聚合时显示LC相特性。为简洁起见,术语“液晶”在下文中用于介晶材料及LC材料两者。对于定义的概述,参见C.Tschierske,G.Pelzl及S.Diele,Angew.Chem.2004,116,6340-6368。
棒状介晶基团通常包含由一个或多个芳族或非芳族环状基团彼此直接连接或经由连接基团连接组成的介晶核,任选地包含附接至介晶核的末端的端基,且任选地包含一个或多个附接至介晶核的长侧的侧基,其中这些端基和侧基通常选自例如碳基(carbyl)或烃基、极性基团(如卤素、硝基、羟基等)或可聚合的基团。
术语“反应性介晶”(RM)意谓可聚合介晶化合物或液晶化合物。
具有一个可聚合基团的可聚合化合物也被称为“单反应性”化合物,具有两个可聚合基团的化合物也被称为“双反应性”化合物,和具有多于两个可聚合基团的化合物也被称为“多反应性”化合物。不含有可聚合基团的化合物也被称为“非反应性”化合物。
术语“可聚合LC材料”意谓包含超过90重量%、优选超过95重量%、更优选超过98重量%的如上文及下文描述的可聚合化合物的材料。
术语“非介晶化合物或材料”是指不含有如上文所限定的介晶基团的化合物或材料。
可见光是具有在约400nm至约740nm范围内的波长的电磁辐射。紫外(UV)光是具有在约200nm至约450nm范围内的波长的电磁辐射。
辐照度(Ee)或辐射功率被定义为入射在表面上的每单位面积(dA)的电磁辐射(dθ)的功率:
Ee=dθ/dA。
辐射暴露量或辐射剂量(He)为每时刻(t)的辐照或辐射功率(Ee):
He=Ee·t。
所有温度,例如液晶的熔点T(C,N)或T(C,S),从近晶(S)向向列(N)相的转变T(S,N)和清亮点T(N,I)以摄氏度给出。所有温度差以差别的度数给出。
术语“清亮点”是指具有最高温度范围的中间相和各向同性相出现之间的转变的温度。
术语“指向矢”是现有技术已知的并且是指液晶或RM分子的长分子轴(在棒状化合物的情况下)或者短分子轴(在盘状化合物的情况下)的优选的取向方向。在这样的各向异性分子单轴有序化的情况下,指向矢是各向异性轴。
除非另外明确陈述,否则所有物理特性均已根据或根据的“Merck LiquidCrystals,Physical Properties of Liquid Crystals”Status 1997年11月,Merck KGaA,Germany测定,且针对20℃的温度给出。光学各向异性(Δn)是在589.3nm的波长处测定。
如有疑问,如在C.Tschierske,G.Pelzl和S.Diele,Angew.Chem.2004,116,6340-6368中给出的定义将适用。
除非另外说明,在给出的通式中,以下术语具有以下含义:
“碳基”表示含有至少一个碳原子的单价或多价有机基团,其不含其他原子(诸如-C≡C-)或任选地含有一个或多个其他原子,诸如N、O、S、P、Si、Se、As、Te或Ge(例如羰基等)。“烃基”表示碳基,其另外含有一个或多个H原子和任选的一个或多个杂原子,诸如N、O、S、P、Si、Se、As、Te或Ge。
碳基或烃基可为饱和或不饱和基团。不饱和基团为例如芳基、烯基或炔基。具有大于3个C原子的碳基或烃基可为直链、支链和/或环状且可含有螺连接或稠合环。
优选的碳基和烃基为具有1至40个C原子,优选1至25个C原子,特别优选1至18个C原子的任选地被取代的烷基、烯基、炔基、烷氧基、烷基羰基、烷氧基羰基、烷基羰基氧基和烷氧基羰基氧基,具有6至40个C原子,优选6至25个C原子的任选地被取代的芳基或芳氧基,或具有6至40个C原子,优选6至25个C原子的任选地被取代的烷基芳基、芳基烷基、烷基芳氧基、芳基烷基氧基、芳基羰基、芳氧基羰基、芳基羰基氧基和芳氧基羰基氧基。
其他优选的碳基和烃基为C1-C40烷基、C2-C40烯基、C2-C40炔基、C3-C40烯丙基、C4-C40烷基二烯基、C4-C40多烯基、C6-C40芳基、C6-C40烷基芳基、C6-C40芳基烷基、C6-C40烷基芳氧基、C6-C40芳基烷基氧基、C2-C40杂芳基、C4-C40环烷基、C4-C40环烯基等。特别优选C1-C22烷基、C2-C22烯基、C2-C22炔基、C3-C22烯丙基、C4-C22烷基二烯基、C6-C12芳基、C6-C20芳基烷基和C2-C20杂芳基。
其他优选的碳基和烃基为具有1至40个C原子,优选1至25个C原子,更优选1至12个C原子的直链、支链或环状烷基,其未被取代或由F、Cl、Br、I或CN单取代或多取代,且其中一个或多个不相邻的CH2基团可各自彼此独立地被-C(Rx)=C(Rx)-、-C≡C-、-N(Rx)-、-O-、-S-、-CO-、-CO-O-、-O-CO-、-O-CO-O-以使得O和/或S原子不直接彼此相连的方式替代。
在上文中,Rx优选表示H、卤素、具有1至25个C原子的直链、支链或环状烷基链,其中此外一个或多个不相邻的C原子可经-O-、-S-、-CO-、-CO-O-、-O-CO-、-O-CO-O-替代,且其中一个或多个H原子可经氟、具有6至40个C原子的任选地被取代的芳基或芳氧基或具有2至40个C原子的任选地被取代的杂芳基或杂芳氧基替代。
优选的烷基为例如甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、2-甲基丁基、正戊基、仲戊基、正己基、2-乙基己基、正庚基、正辛基、正壬基、正癸基、正十一烷基、正十二烷基、十二烷基、三氟甲基、全氟正丁基、2,2,2-三氟乙基、全氟辛基、全氟己基等。
优选的烯基为例如乙烯基、丙烯基、丁烯基、戊烯基、环戊烯基、己烯基、环己烯基、庚烯基、环庚烯基、辛烯基、环辛烯基等。
优选的炔基为例如乙炔基、丙炔基、丁炔基、戊炔基、己炔基、辛炔基等。
优选的烷氧基为例如甲氧基、乙氧基、2-甲氧基乙氧基、正丙氧基、异丙氧基、正丁氧基、异丁氧基、仲丁氧基、叔丁氧基、2-甲基丁氧基、正戊氧基、正己氧基、正庚氧基、正辛氧基、正壬氧基、正癸氧基、正十一烷氧基、正十二烷氧基等。
优选的氨基为例如二甲氨基、甲氨基、甲基苯基氨基、苯基氨基等。
芳基和杂芳基可为单环或多环,即它们可具有一个环(诸如苯基)或两个或更多个环,该环也可稠合(诸如萘基)或共价连接(诸如联苯),或含有稠合环与连接环的组合。杂芳基含有一个或多个杂原子,优选选自O、N、S和Se。
特别优选具有6至25个C原子的单环、双环或三环芳基和具有2至25个C原子的单环、双环或三环杂芳基,其任选地含有稠合环并且其任选地被取代。此外,优选的是5元、6元或7元芳基和杂芳基,其中此外一个或多个CH基团可以经N、S或O以使得O原子和/或S原子不直接彼此相连的方式替代。
优选的芳基基团例如为苯基、联苯基、联三苯基、[1,1':3',1”]-联三苯-2'-基、萘、蒽、联萘、菲、芘、二氢芘、二萘嵌苯、并四苯、并五苯、苯并芘、芴、茚、茚并芴、螺双芴(spirobifluorene)等。
优选的杂芳基基团例如为5-元环,例如吡咯、吡唑、咪唑、1,2,3-***、1,2,4-***、四唑、呋喃、噻吩、硒吩、噁唑、异噁唑、1,2-噻唑、1,3-噻唑、1,2,3-噁二唑、1,2,4-噁二唑、1,2,5-噁二唑、1,3,4-噁二唑、1,2,3-噻二唑、1,2,4-噻二唑、1,2,5-噻二唑、1,3,4-噻二唑、6-元环,例如吡啶、哒嗪、嘧啶、吡嗪、1,3,5-三嗪、1,2,4-三嗪、1,2,3-三嗪、1,2,4,5-四嗪、1,2,3,4-四嗪、1,2,3,5-四嗪或稠合基团,例如吲哚、异吲哚、吲嗪、吲唑、苯并咪唑、苯并***、嘌呤、萘并咪唑、菲并咪唑、吡啶并咪唑、吡嗪并咪唑、喹喔啉并咪唑、苯并噁唑、萘并噁唑、蒽并噁唑、菲并噁唑、异噁唑、苯并噻唑、苯并呋喃、异苯并呋喃、二苯并呋喃、喹啉、异喹啉、蝶啶、苯并-5,6-喹啉、苯并-6,7-喹啉、苯并-7,8-喹啉、苯并异喹啉、吖啶、吩噻嗪、吩噁嗪、苯并哒嗪、苯并嘧啶、喹喔啉、吩嗪、萘啶、氮杂咔唑、苯并咔啉、菲啶、菲咯啉、噻吩并[2,3b]噻吩、噻吩并[3,2b]噻吩、二噻吩并噻吩、异苯并噻吩、二苯并噻吩、苯并噻二唑噻吩,或者这些基团的组合。杂芳基也可经烷基、烷氧基、硫代烷基、氟、氟烷基或其他芳基或杂芳基取代。
(非芳族)脂环基团和杂环基既包含饱和的环,即仅含有单键的那些,且包含部分不饱和的环,即也可以包含多重键的那些。杂环含有一个或多个杂原子,优选选自Si、O、N、S和Se。
(非芳族)脂环基团和杂环基团可为单环的,即仅含一个环(例如环己烷),或者是多环的,即含有多个环(例如十氢化萘或者双环辛烷)。特别优选饱和的基团。此外优选具有3-25个原子的单-、双-或三环状基团,其任选含有稠合环且其为任选取代的。进一步优选的是5-、6-、7-或8-元碳环基团,其中此外,一个或多个C原子可被Si替代和/或一个或多个CH基团可被N替代和/或一个或多个不相邻的CH2基团可被-O-和/或-S-替代。
优选的脂环基团和杂环基团例如为5-元基团,例如环戊烷、四氢呋喃、四氢噻吩、吡咯烷;6-元基团,例如环己烷、硅杂环己烷(silinane)、环己烯、四氢吡喃、四氢噻喃、1,3-二噁烷、1,3-二噻烷、哌啶;7-元基团,例如环庚烷;和稠合基团,例如四氢化萘、十氢化萘、茚满、双环[1.1.1]戊烷-1,3-二基、双环[2.2.2]辛烷-1,4-二基、螺[3.3]庚烷-2,6-二基、八氢-4,7-桥亚甲基茚满-2,5-二基。
芳基、杂芳基、(非芳族)脂环和杂环基团任选具有一个或多个取代基,所述取代基优选选自甲硅烷基、磺酸基、磺酰基、甲酰基、胺基、亚胺基、腈基、巯基、硝基、卤素、C1-C12烷基、C6-C12芳基、C1-C12烷氧基、羟基或这些基团的组合。
优选的取代基为例如溶解性促进基团,例如烷基或烷氧基;吸电子基团,例如氟、硝基或腈;或者是用于提高聚合物玻璃化转变温度(Tg)的取代基,特别是大体积基团,例如叔丁基或任选取代的芳基。
优选的取代基(下文也称作“L”)为例如F、Cl、Br、I、OH、-CN、-NO2、-NCO、-NCS、-OCN、-SCN、-C(=O)N(Rx)2、-C(=O)Yx、-C(=O)Rx、-C(=O)ORx、-N(Rx)2,其中Rx具有上文所提及的含义,和上述Yx表示卤素;任选地被取代的甲硅烷基;具有4至40个、优选4至20个环原子的任选地被取代的芳基或杂芳基;和具有1至25个C原子的直链或支链烷基、烯基、炔基、烷氧基、烷基羰基、烷氧基羰基、烷基羰基氧基或烷氧基羰基氧基,其中一个或多个H原子可任选地被F或Cl替代。
“取代的甲硅烷基或芳基”优选是指被卤素、-CN、Ry、-ORy、-CO-Ry、-CO-O-Ry、-O-CO-Ry或-O-CO-O-Ry取代,其中Ry表示H,具有1至12个C原子的直链、支链或环状烷基链。
在上下文显示的式中,取代的亚苯基环
其中L在每次出现时相同或不同地具有上下文给出的含义之一,并且优选是F、Cl、CN、NO2、CH3、C2H5、C(CH3)3、CH(CH3)2、CH2CH(CH3)C2H5、OCH3、OC2H5、COCH3、COC2H5、COOCH3、COOC2H5、CF3、OCF3、OCHF2、OC2F5或P-Sp-,非常优选是F、Cl、CN、CH3、C2H5、OCH3、COCH3、OCF3或P-Sp-,最优选是F、Cl、CH3、OCH3、COCH3或OCF3。
“卤素”表示F、Cl、Br或I,优选F或Cl,更优选F。
“可聚合基团”(P)优选选自包含C=C双键或C≡C三键的基团,和适用于开环聚合的基团,如例如氧杂环丁烷基或环氧基。
优选地,可聚合基团(P)选自CH2=CW1-COO-、CH2=CW1-CO-、CH2=CW2-(O)k3-、CW1=CH-CO-(O)k3-、CW1=CH-CO-NH-、CH2=CW1-CO-NH-、CH3-CH=CH-O-、(CH2=CH)2CH-OCO-、(CH2=CH-CH2)2CH-OCO-、(CH2=CH)2CH-O-、(CH2=CH-CH2)2N-、(CH2=CH-CH2)2N-CO-、CH2=CW1-CO-NH-、CH2=CH-(COO)k1-Phe-(O)k2-、CH2=CH-(CO)k1-Phe-(O)k2-、Phe-CH=CH-,
其中
W1表示H、F、Cl、CN、CF3、苯基或具有1至5个C原子的烷基,特别是H、F、Cl或CH3,
W2表示H或具有1至5个C原子的烷基,特别是H、甲基、乙基或正丙基,
W3和W4各自彼此独立地表示H、Cl或具有1至5个C原子的烷基,Phe表示1,4-亚苯基,其任选被一个或多个如上文所限定但不同于P-Sp的基团L取代,优选地,优选的取代基L是F、Cl、CN、NO2、CH3、C2H5、OCH3、OC2H5、COCH3、COC2H5、COOCH3、COOC2H5、CF3、OCF3、OCHF2、OC2F5,还有苯基,和
k1、k2和k3各自彼此独立地表示0或1,k3优选表示1,和k4是1至10的整数。
特别优选的可聚合基团P是CH2=CH-COO-,CH2=C(CH3)-COO-,CH2=CF-COO-,CH2=CH-,CH2=CH-O-,(CH2=CH)2CH-OCO-,(CH2=CH)2CH-O-,其中W2表示H或具有1至5个C原子的烷基,特别是H、甲基、乙基或正丙基。
进一步优选的可聚合基团(P)是乙烯氧基、丙烯酸酯基、甲基丙烯酸酯基、氟代丙烯酸酯基、氯代丙烯酸酯基、氧杂环丁烷基和环氧基,最优选丙烯酸酯基或甲基丙烯酸酯基,特别是丙烯酸酯基。
所有多反应性可聚合化合物及其子式可任选地包含一个或多个包含两个或更多个可聚合基团P的支链基团(多反应性可聚合基团),而不是一个或多个基团P-Sp-。
合适的该类型的基团和包含它们的可聚合化合物描述于例如US 7,060,200 B1或US 2006/0172090 A1中。
特别优选选自下式的多反应性可聚合基团:
-X-alkyl-CHPx-CH2-CH2Py I*a
-X-alkyl-C(CH2Px)(CH2Py)-CH2Pz I*b
-X-alkyl-CHPxCHPy-CH2Pz I*c
-X-alkyl-C(CH2Px)(CH2Py)-CaaH2aa+1 I*d
-X-alkyl-CHPx-CH2Py I*e
-X-alkyl-CHPxPy I*f
-X-alkyl-CPxPy-CaaH2aa+1 I*g
-X-alkyl-C(CH2Pv)(CH2Pw)-CH2OCH2-C(CH2Px)(CH2Py)CH2Pz I*h
-X-alkyl-CH((CH2)aaPx)((CH2)bbPy) I*i
-X-alkyl-CHPxCHPy-CaaH2aa+1 I*k
其中
alkyl表示单键或具有1至12个C原子的直链或支链亚烷基,其中一个或多个不相邻的CH2基团可以各自彼此独立地被-C(Rx)=C(Rx)-、-C≡C-、-N(Rx)-、-O-、-S-、-CO-、-CO-O-、-O-CO-、-O-CO-O-以O和/或S原子不直接彼此连接的方式替代,和此外其中,一个或多个H原子可以被F、Cl或CN替代,其中Rx具有一种上文提及的含义,
aa和bb各自彼此独立地表示0、1、2、3、4、5或6,
X具有对X'指出的含义之一,和
Pv至Pz各自彼此独立地具有上文对P指出的含义之一。
除非另有明确说明,优选的间隔基团Sp选自式Sp'-X',使得基团“P-Sp-”符合式“P-Sp'-X'-”,其中
Sp'表示具有1至20个,优选1至12个C原子的亚烷基,其任选被F、Cl、Br、I或CN单-或多-取代,和此外其中,一个或多个不相邻的CH2基团可以各自彼此独立地被-O-、-S-、-NH-、-NRxx-、-SiRxxRyy-、-CO-、-COO-、-OCO-、-OCO-O-、-S-CO-、-CO-S-、-NRxx-CO-O-、-O-CO-NR0xx-、-NRxx-CO-NRyy-、-CH=CH-或-C≡C-以O和/或S原子不直接彼此连接的方式替代,
X'表示-O-、-S-、-CO-、-COO-、-OCO-、-O-COO-、-CO-NRxx-、-NRxx-CO-、-NRxx-CO-NRyy-、-OCH2-、-CH2O-、-SCH2-、-CH2S-、-CF2O-、-OCF2-、-CF2S-、-SCF2-、-CF2CH2-、-CH2CF2-、-CF2CF2-、-CH=N-、-N=CH-、-N=N-、-CH=CRxx-、-CYxx=CYxx-、-C≡C-、-CH=CH-COO-、-OCO-CH=CH-或单键,
Rxx和Ryy各自彼此独立地表示H或具有1至12个C原子的烷基,和
Yxx和Yyy各自彼此独立地表示H、F、Cl或CN。
X'优选是-O-、-S--CO-、-COO-、-OCO-、-O-COO-、-CO-NRxx-、-NRxx-CO-、-NRxx-CO-NRyy-或单键。
通常的间隔基团Sp'是例如-(CH2)p1-、-(CH2CH2O)q1-CH2CH2-、-CH2CH2-S-CH2CH2-、-CH2CH2-NH-CH2CH2-或-(SiRxxRyy-O)p1-,其中p1是1至12的整数,q1是1至3的整数,和Rxx和Ryy具有上文提及的含义。
特别优选的基团-X'-Sp'-是-(CH2)p1-、-O-(CH2)p1-、-OCO-(CH2)p1-、-OCOO-(CH2)p1-,其中p1为1至12的整数。
特别优选的基团Sp'在每种情况下是例如直链亚甲基、亚乙基、亚丙基、亚丁基、亚戊基、亚己基、亚庚基、亚辛基、亚壬基、亚癸基、亚十一烷基、亚十二烷基、亚十八烷基、亚乙基氧基亚乙基、亚甲基氧基亚丁基、亚乙基硫代亚乙基、亚乙基-N-甲基亚氨基亚乙基、1-甲基亚烷基、亚乙烯基、亚丙烯基和亚丁烯基。
对于本发明而言,
表示反式-1,4-亚环己基,和
表示1,4-亚苯基。
在分子水平上,液晶的双折射率视极化度(Δα=α||-α┴)的各向异性而定。“极化度”意谓原子或分子中电子分布可发生变形的容易程度。极化度随电子的数目增大及电子云的扩散程度增加而增加。极化度可使用例如Jap.J.Appl.Phys.42,(2003)第3463页中描述的方法计算。
液晶或双折射材料的层在给定波长R(λ)(以nm为单位)处的“光延迟”定义为根据如下等式的那波长处的双折射率Δn(λ)与层厚度d(以nm为单位)的乘积
R(λ)=Δn(λ).d
光延迟R表示在以纳米为单位的光学路径长度中由同时穿过双折射材料的S偏光及P偏光行进的差值。“同轴”延迟意谓与样本表面呈正入射角的延迟。
术语“负(光学)色散”是指显示反向双折射色散的双折射或液晶材料或层,其中双折射率(Δn)的大小随波长(λ)的增加而增大,即|Δn(450)|<|Δn(550)|,或Δn(450)/Δn(550)<1,其中Δn(450)和Δn(550)分别是在450nm和550nm的波长下测量的材料的双折射率。相反,“正(光学)色散”是指具有|Δn(450)|>|Δn(550)|或Δn(450)/Δn(550)>1的材料或层。还参见例如A.Uchiyama,T.Yatabe“Control of Wavelength Dispersion ofBirefringence for Oriented Copolycarbonate Films Containing Positive andNegative Birefringent Units”.J.Appl.Phys.第42卷,第6941-6945页(2003)。“平面(光)色散”意谓|Δn(450)|>|Δn(550)|或Δn(450)/Δn(550)≈1的材料或层。
由于在给定波长下的光学延迟定义为如上文[R(λ)=Δn(λ)·d]所描述的双折射率和层厚度的乘积,因此光色散可以通过比率Δn(450)/Δn(550)表示为“双折射率色散”,或者通过比率R(450)/R(550)表示为“延迟色散”,其中R(450)和R(550)分别是在450nm和550nm的波长下测量的材料的延迟。由于层厚度d不随波长改变,因此R(450)/R(550)等于Δn(450)/Δn(550)。因此,具有负或反向(reverse)色散的材料或层具有R(450)/R(550)<1或|R(450)|<|R(550)|,具有正或正常色散的材料或层具有R(450)/R(550)>1或|R(450)|>|R(550)|,且具有平面色散的材料或层的R(450)/R(550)≈1或|R(450)|≈|R(550)|。
在本发明中,除非另外说明,“光色散”是指延迟色散即比率R(450)/R(550)。
术语“高色散”是指色散的绝对值显示离1大的偏差,而术语“低色散”是指色散的绝对值显示离1小的偏差。因此,例如,“高的负色散”是指色散值显著小于1,和“低的负色散”是指色散值仅略微小于1。
材料的延迟(R(λ))可以使用光谱椭偏仪测量,例如J.A.Woollam公司的M2000光谱椭偏仪。该仪器能够测量通常在370nm至2000nm波长范围内的双折射材料(例如石英)的以纳米为单位的光学延迟。可以由该数据计算材料的色散(R(450)/R(550)或Δn(450)/Δn(550))。
进行这些测量的方法在国家物理实验室(英国伦敦)由N.Singh于2006年10月提出,并且标题为“Spectroscopic Ellipsometry,Part1-Theory and Fundamentals,Part2–Practical Examples and Part 3-measurements”。根据由J.A.Woollam公司(美国内布拉斯加州林肯)出版的延迟测量(RetMeas)手册(Retardation Measurement(RetMeas)Manual)(2002)和WVASE(Woollam可变角光谱椭圆仪)指南(2002)描述的测试程序。除非另外说明,使用该方法以测定在本发明中描述的材料、膜和器件的延迟。
术语“A板”是指利用其非寻常轴平行于层平面取向的单轴双折射材料层的光学延迟器。
术语“C-板”是指利用其非寻常轴垂直于层平面取向的单轴双折射材料层的光学延迟器。
在包含具有均匀取向的光学单轴双折射液晶材料的A/C-板中,膜的光学轴由非寻常轴的方向给出。包含具有正双折射率的光学单轴双折射材料的A(或C)板也被称为“正A(或C)板”或“+A(或+C)板”。
包含具有负双折射率的光学单轴双折射材料的膜的A(或C)板,例如盘状各向异性材料也被称为“负A(或C)板”或“-A(或C)板”,这取决于盘状材料的取向。由在光谱的UV部分中具有反射带的胆甾棒状材料制得的膜也具有负C板的光学。
双折射率Δn如下定义
Δn=ne-no
其中ne是非寻常折射率和no是寻常折射率,且有效平均折射率nav.由以下等式给出:
nav.=((2no 2+ne 2)/3)1/2
平均折射率nav.和寻常折射率no可以使用Abbe折射计测量。然后可以由以上等式计算Δn。
除非上下文另外明确表明,否则如本文所用,本文的术语的复数形式应理解为包括单数形式,且反之亦然。
贯穿本说明书的描述及权利要求,措词“包含”及“含有”及该措词的变化形式(例如“包含(comprising)”及“包含(comprises)”)意指“包括但不限于”,且不意欲(且不)排除其他组分。另一方面,措词“包含”还涵盖但不限于术语“由……组成”。
在整个本说明书的描述和权利要求书中,措辞“可获得的”及“获得的”及该措辞的变化形式意指“包括但不限于”,且并不意欲(且不)排除其他组分。另一方面,措词“可获得的”还涵盖但不限于术语“获得的”。
所有浓度以重量百分比引述且涉及整体各个混合物,所有温度以摄氏度引述且所有温度差异以度数差(differential degree)引述。
详细说明
优选式I化合物是以下化合物,其中
a)由以下组成的组:1,4-亚苯基及1,3-亚苯基,其中此外,一或两个CH基团可经N替代,且其中此外,一个或多个H原子可经L替代,
b)选自由以下组成的组:
其中此外,这些基团中的一个或多个H原子可经L替代,及/或一个或多个双键可经单键替代,及/或一个或多个CH基团可经N替代,
c)由以下组成的组:反式-1,4-亚环己基、1,4-亚环己烯基,其中此外,一个或多个不相邻的CH2基团可经-O-及/或-S-替代,且其中此外,一个或多个H原子可经F替代,或
d)由以下组成的组:四氢吡喃-2,5-二基、1,3-二噁烷-2,5-二基、四氢呋喃-2,5-二基、环丁烷-1,3-二基、哌啶-1,4-二基、噻吩-2,5-二基及硒吩-2,5-二基,其中的每一者也可经L单取代或多取代,且其中
L在每次出现时,相同或不同地表示-OH、-F、-Cl、-Br、-I、-CN、-NO2、SF5、-NCO、-NCS、-OCN、-SCN、-C(=O)N(Rz)2、-C(=O)Rz、-N(Rz)2、任选地经取代的甲硅烷基、具有6至20个C原子的任选地经取代的芳基或具有1至25个C原子、优选1至12个C原子、更优选1至6个C原子的直链或支链或环状烷基、烷氧基、烷羰基、烷氧基羰基、烷基羰氧基或烷氧基羰氧基,其中此外,一个或多个H原子可经F或Cl替代。
进一步优选式I化合物是以下化合物,其中
L在每次出现时,相同或不同地表示-OH、-F、-Cl或具有1至25个C原子、优选1至12个C原子、更优选1至6个C原子的直链、支链或环状烷基、烷氧基、烷羰基、烷氧基羰基、烷基羰氧基或烷氧基羰氧基,其中此外一个或多个H原子可经F或Cl替代。
进一步优选式I化合物是下表的化合物:
其中
P是可聚合基团,
优选是甲基丙烯酸或丙烯酸基团,
s表示0与9之间的整数,优选是1与7之间的整数,诸如亚甲基、亚乙基、亚丙基、亚丁基、亚戊基、亚己基、亚庚基,
R11是优选具有1至15个C原子的烷基、烷氧基、硫代烷基、烷羰基、烷氧基羰基、烷基羰氧基或烷氧基羰氧基,其更优选任选地经氟化,
优选是具有1至12个C原子的烷基,
L在每次出现时,相同或不同地表示-OH、-F、-Cl或具有1至12个C原子、更优选1至6个C原子的直链、支链或环状烷基、烷氧基、烷羰基、烷氧基羰基、烷基羰氧基或烷氧基羰氧基,其中此外一个或多个H原子可经F或Cl替代,
优选是F、Cl、甲基、乙基、丙基、甲氧基、乙氧基、丙氧基或OH。
进一步优选式I化合物是下表的化合物:
其中
X表示H或-CH3,
s表示0、1、2、3、4、5、6或7,
优选是5、6或7,及
t表示0、1、2、3、4或5,
优选是2、3、4或5。
式I化合物及其子式的合成可以类似于下文或实施例中显示的说明性反应进行。根据本发明的其他化合物的制备也可通过文献中本领域技术人员本身已知的其他方法进行。
示例性地,式I化合物可根据如方案1中所说明的方法或以与其类似的方式合成。
方案1
条件:
步骤a.1:二异丙胺,CuI,Pd(OAc)2,[(t-Bu)3PH]BF4,40℃,4小时。
步骤a.2:HCl(aq),冰。
步骤b:H2,Pd(0)/碳(10%),THF,室温,7小时。
步骤c:对甲苯磺酸,甲苯,回流,3小时。
步骤d.1:DMAP,DCC,DCM,室温,12小时。
步骤d.2:Et3N,40℃,8小时。
步骤d.3:HCl,0℃,30分钟。
且其中参数s、t及L具有如式I中所给出的含义之一,且r表示0、1或2。
本发明的另一目标是一种可聚合LC或RM混合物,其包含两种或更多种RM,其中的至少一者是式I化合物。
优选RM混合物包含一种或多种仅具有一个可聚合官能团的RM(单反应性RM),其至少一种为式I的化合物,和一种或多种具有两个或更多个可聚合官能团的RM(二或多反应性RM)。
二反应性或多反应性RM优选地选自式DRM
P1-Sp1-MG-Sp2-P2 DRM
其中
P1及P2彼此独立地表示可聚合基团,
Sp1及Sp2彼此独立地是间隔基团或单键,且
MG是棒形介晶基团,其优选地选自式MG
-(A1-Z1)n-A2- MG
其中A1及A2在多次出现的情形下彼此独立地表示芳香族或脂环族基团,其任选地含有一个或多个选自N、O及S的杂原子,且任选地经L单取代或多取代,
L是P-Sp-、F、Cl、Br、I、-CN、-NO2、-NCO、-NCS、-OCN、-SCN、-C(=O)NRxRy、-C(=O)ORx、-C(=O)Rx、-NRxRy、-OH、-SF5、任选地经取代的甲硅烷基、芳基或杂芳基(具有1至12个、优选地1至6个C原子的),及具有1至12个、优选地1至6个C原子的直链或支链烷基、烷氧基、烷基羰基、烷氧基羰基、烷基羰氧基或烷氧基羰氧基,其中一个或多个H原子任选地经F或Cl替代,
Rx及Ry彼此独立地表示H或具有1至12个C原子的烷基,
Z1在多次出现的情形下彼此独立地表示-O-、-S-、-CO-、-COO-、-OCO-、-S-CO-、-CO-S-、-O-COO-、-CO-NR00-、-NR00-CO-、-NR00-CO-NR000、-NR00-CO-O-、-O-CO-NR00-、-OCH2-、-CH2O-、-SCH2-、-CH2S-、-CF2O-、-OCF2-、-CF2S-、-SCF2-、-CH2CH2-、-(CH2)n1、-CF2CH2-、-CH2CF2-、-CF2CF2-、-CH=N-、-N=CH-、-N=N-、-CH=CR00-、-CY1=CY2-、-C≡C-、-CH=CH-COO-、-OCO-CH=CH-或单键,优选地-COO-、-OCO-或单键,
Y1及Y2彼此独立地表示H、F、Cl或CN,
n是1、2、3或4,优选地1或2,最优选地2,
n1是1至10的整数,优选地1、2、3或4。
优选的基团A1和A2包括,但不限于,呋喃、吡咯、噻吩、噁唑、噻唑、噻二唑、咪唑、亚苯基、亚环己基、双亚环辛基、亚环己烯基、吡啶、嘧啶、吡嗪、甘菊环、茚满、芴、萘、四氢化萘、蒽、菲和二噻吩并噻吩,其全部为未取代的或被1、2、3或4个如上所述的基团L取代。
特别优选的基团A1和A2选自1,4-亚苯基、吡啶-2,5-二基、嘧啶-2,5-二基、噻吩-2,5-二基、萘-2,6-二基、1,2,3,4-四氢化-萘-2,6-二基、茚满-2,5-二基、双亚环辛基或1,4-亚环己基,其中一个或两个不相邻的CH2基团任选被O和/或S替代,其中这些基团为未取代的或被1、2、3或4个如上所述的基团L取代。
式DRM的优选RM选自式DRMa
其中
P0在多次出现的情形下彼此独立地是可聚合基团,优选地是丙烯酰基、甲基丙烯酰基、氧杂环丁烷、环氧基、乙烯基、庚二烯、乙烯基氧基、丙烯基醚或苯乙烯基团,
Z0是-COO-、-OCO-、-CH2CH2-、-CF2O-、-OCF2-、-C≡C-、-CH=CH-,-OCO-CH=CH-、-CH=CH-COO-或单键,
L在每次出现时相同或不同地具有针对式I中的L1所给的含义之一,且优选地在多次出现的情形下彼此独立地选自F、Cl、CN或具有1至5个C原子的任选地卤化的烷基、烷氧基、烷基羰基、烷氧基羰基、烷基羰氧基或烷氧基羰氧基,
r是0、1、2、3或4,
x及y彼此独立地为0或1至12的相同或不同的整数,
z是0或1,且若相邻的x或y是0,则z是0。
非常优选的式DRM的RM选自下式:
其中P0、L、r、x、y及z是如式DRMa中所定义。
尤其优选的是式DRMa1、DRMa2及DRMa3的化合物,特别是具有式DRMa1的那些。
RM混合物中二反应性或多反应性RM(优选地具有式DRM及其子式的那些)的浓度优选地为1%至60%,非常优选地5%至50%。
在另一实施方案中,RM混合物除式I化合物以外包含一种或多种单反应性RM。这些额外的单反应性RM优选地选自式MRM:
P1-Sp1-MG-R MRM
其中P1、Sp1及MG具有式DRM中所给出的含义,
R表示P-Sp-、F、Cl、Br、I、-CN、-NO2、-NCO、-NCS、-OCN、-SCN、-C(=O)NRxRy、-C(=O)X、-C(=O)ORx、-C(=O)Ry、-NRxRy、-OH、-SF5、任选地经取代的甲硅烷基、具有1至12个、优选地1至6个C原子的直链或支链烷基、烷氧基、烷基羰基、烷氧基羰基、烷基羰氧基或烷氧基羰氧基,其中一个或多个H原子任选地经F或Cl替代,
X是卤素,优选地F或Cl,且
Rx及Ry彼此独立地为H或具有1至12个C原子的烷基。
优选地式MRM的RM选自下式。
其中P0、L、r、x、y及z是如式DRMa中所定义,
R0是具有1或多个、优选地1至15个C原子的烷基、烷氧基、硫代烷基、烷基羰基、烷氧基羰基、烷基羰氧基或烷氧基羰氧基或表示Y0或P-(CH2)y-(O)z-,
X0是-O-、-S-、-CO-、-COO-、-OCO-、-O-COO-、-CO-NR01-、-NR01-CO-、-NR01-CO-NR01-、-OCH2-、-CH2O-、-SCH2-、-CH2S-、-CF2O-、-OCF2-、-CF2S-、-SCF2-、-CF2CH2-、-CH2CF2-、-CF2CF2-、-CH=N-、-N=CH-、-N=N-、-CH=CR01-、-CF=CF-、-C≡C-、-CH=CH-COO-、-OCO-CH=CH-或单键
Y0是F、Cl、CN、NO2、OCH3、OCN、SCN、SF5或具有1至4个C原子的单氟化、寡氟化或多氟化烷基或烷氧基,
Z0是-COO-、-OCO-、-CH2CH2-、-CF2O-、-OCF2-、-CH=CH-,-OCO-CH=CH-、-CH=CH-COO-或单键,
A0在多次出现的情形下彼此独立地为未经取代或经1个、2个、3个或4个基团L取代的1,4-亚苯基,或反式-1,4-亚环己基,
R01,02彼此独立地为H、R0或Y0,
u及v彼此独立地为0、1或2,
w是0或1,
且其中苯及萘环可另外经一个或多个相同或不同基团L取代,且式MRM15中的z表示1。
尤其优选的是式MRM1、MRM2、MRM3、MRM4、MRM5、MRM6、MRM7、MRM9及MRM10的化合物,特别是具有式MRM1、MRM4、MRM6及MRM7的那些。
RM混合物中所有单反应性RM(包括具有式I的那些)的浓度优选地均为1%至80%,非常优选地5%至20%。
在式DRM、MRM及其优选子式中,L优选地选自F、Cl、CN、NO2或具有1至12个C原子的直链或支链烷基、烷氧基、烷基羰基、烷氧基羰基、烷基羰氧基或烷氧基羰氧基(其中烷基任选地经全氟化),或P-Sp-。
非常优选地L选自F、Cl、CN、NO2、CH3、C2H5、C(CH3)3、CH(CH3)2、CH2CH(CH3)C2H5、OCH3、OC2H5、COCH3、COC2H5、COOCH3、COOC2H5、CF3、OCF3、OCHF2、OC2F5或P-Sp-,特别是F、Cl、CN、CH3、C2H5、C(CH3)3、CH(CH3)2、OCH3、COCH3或OCF3,最优选地F、Cl、CH3、C(CH3)3、OCH3或COCH3或P-Sp-。
下式的经取代苯环
其中L各自独立地具有上文所给的含义之一。
在式I、DRM、MRM及其优选子式中,烷基或烷氧基,即其中末端CH2基团被-O-替代,可为直链或支链的。其优选为直链,具有2、3、4、5、6、7或8个碳原子和相应地优选例如为乙基、丙基、丁基、戊基、己基、庚基、辛基、乙氧基、丙氧基、丁氧基、戊氧基、己氧基、庚氧基、或辛氧基,以及甲基、壬基、癸基、十一烷基、十二烷基、十三烷基、十四烷基、十五烷基、壬氧基、癸氧基、十一烷氧基、十二烷氧基、十三烷氧基或十四烷氧基。
氧杂烷基,即其中一个CH2基团被-O-替代,优选例如直链2-氧杂丙基(=甲氧基甲基)、2-(=乙氧基甲基)或3-氧杂丁基(=2-甲氧基乙基)、2-、3-、或4-氧杂戊基、2-、3-、4-、或5-氧杂己基、2-、3-、4-、5-、或6-氧杂庚基、2-、3-、4-、5-、6-或7-氧杂辛基、2-、3-、4-、5-、6-、7-或8-氧杂壬基或2-、3-、4-、5-、6-、7-、8-或9-氧杂癸基。
其中一个或多个CH2基团被-CH=CH-替代的烷基可为直链或支链的。其优选为直链,具有2-10个C原子并相应地优选为乙烯基、丙-1-、或丙-2-烯基、丁-1-、2-或丁-3-烯基、戊-1-、2-、3-或戊-4-烯基、己-1-、2-、3-、4-或己-5-烯基、庚-1-、2-、3-、4-、5-或庚-6-烯基、辛-1-、2-、3-、4-、5-、6-或辛-7-烯基、壬-1-、2-、3-、4-、5-、6-、7-或壬-8-烯基、癸-1-、2-、3-、4-、5-、6-、7-、8-或癸-9-烯基。
尤其优选的烯基为C2-C7-1E-烯基、C4-C7-3E-烯基、C5-C7-4-烯基、C6-C7-5-烯基和C7-6-烯基,特别是C2-C7-1E-烯基、C4-C7-3E-烯基和C5-C7-4-烯基。特别优选的烯基实例为乙烯基、1E-丙烯基、1E-丁烯基、1E-戊烯基、1E-己烯基、1E-庚烯基、3-丁烯基、3E-戊烯基、3E-己烯基、3E-庚烯基、4-戊烯基、4Z-己烯基、4E-己烯基、4Z-庚烯基、5-己烯基、6-庚烯基等。通常优选具有最多5个C原子的基团。
在其中一个CH2基团被-O-替代和一个CH2被-CO-替代的烷基中,这些基团优选相邻。相应地,这些基团一起形成羰基氧基-CO-O-或氧基羰基-O-CO-。优选该基团为直链并具有2-6个C原子。相应地优选乙酰氧基、丙酰氧基、丁酰氧基、戊酰氧基、己酰氧基、乙酰氧基甲基、丙酰氧基甲基、丁酰氧基甲基、戊酰氧基甲基、2-乙酰氧基乙基、2-丙酰氧基乙基、2-丁酰氧基乙基、3-乙酰氧基丙基、3-丙酰氧基丙基、4-乙酰氧基丁基、甲氧基羰基、乙氧基羰基、丙氧基羰基、丁氧基羰基、戊氧基羰基、甲氧基羰基甲基、乙氧基羰基甲基、丙氧基羰基甲基、丁氧基羰基甲基、2-(甲氧基羰基)乙基、2-(乙氧基羰基)乙基、2-(丙氧基羰基)乙基、3-(甲氧基羰基)丙基、3-(乙氧基羰基)丙基、4-(甲氧基羰基)-丁基。
其中两个或更多个CH2基团被-O-和/或-COO-替代的烷基可为直链或支链。其优选为直链并具有3-12个C原子。相应地,其优选为双-羧基-甲基、2,2-双-羧基-乙基、3,3-双-羧基-丙基、4,4-双-羧基-丁基、5,5-双-羧基-戊基、6,6-双-羧基-己基、7,7-双-羧基-庚基、8,8-双-羧基-辛基、9,9-双-羧基-壬基、10,10-双-羧基-癸基、双-(甲氧基羰基)-甲基、2,2-双-(甲氧基羰基)-乙基、3,3-双-(甲氧基羰基)-丙基、4,4-双-(甲氧基羰基)-丁基、5,5-双-(甲氧基羰基)-戊基、6,6-双-(甲氧基羰基)-己基、7,7-双-(甲氧基羰基)-庚基、8,8-双-(甲氧基羰基)-辛基、双-(乙氧基羰基)-甲基、2,2-双-(乙氧基羰基)-乙基、3,3-双-(乙氧基羰基)-丙基、4,4-双-(乙氧基羰基)-丁基、5,5-双-(乙氧基羰基)-己基。
被CN或CF3单取代的烷基或烯基优选为直链。被CN或CF3取代可在任意所需位置。
至少被卤素单取代的烷基或烯基优选为直链。卤素优选为F或Cl,在多取代的情况下优选F。所得基团也包括全氟化基团。在单取代的情况下,F或Cl取代可在任意所需位置,但优选在ω-位。尤其优选的末端F取代的直链基团的实例为氟甲基、2-氟乙基、3-氟丙基、4-氟丁基、5-氟戊基、6-氟己基和7-氟庚基。然而,不排除F的其它位置。
Rx和Ry优选选自H、具有1-12个C原子的直链或支链烷基。
-CY1=CY2-优选为-CH=CH-、-CF=CF-或-CH=C(CN)-。
卤素为F、Cl、Br或I,优选F或Cl。
R、R0、R1、R2和R11可为非手性或手性基团。特别优选的手性基团例如为2-丁基(=1-甲基丙基)、2-甲基丁基、2-甲基戊基、3-甲基戊基、2-乙基己基、2-丙基戊基,特别是2-甲基丁基、2-甲基丁氧基、2-甲基戊氧基、3-甲基戊氧基、2-乙基己氧基、1-甲基己氧基、2-辛基氧基、2-氧杂-3-甲基丁基、3-氧杂-4-甲基戊基、4-甲基己基、2-己基、2-辛基、2-壬基、2-癸基、2-十二烷基、6-甲氧基辛氧基、6-甲基辛氧基、6-甲基辛酰基氧基、5-甲基庚基氧基羰基、2-甲基丁酰基氧基、3-甲基戊酰基氧基、4-甲基己酰基氧基、2-氯丙酰基氧基、2-氯-3-甲基丁酰基氧基、2-氯-4-甲基戊酰基氧基、2-氯-3-甲基戊酰基氧基、2-甲基-3-氧杂戊基、2-甲基-3-氧杂己基、1-甲氧基丙基-2-氧基、1-乙氧基丙基-2-氧基、1-丙氧基丙基-2-氧基、1-丁氧基丙基-2-氧基、2-氟辛基氧基、2-氟癸基氧基、1,1,1-三氟-2-辛基氧基、1,1,1-三氟-2-辛基、2-氟甲基辛基氧基。非常优选的是2-己基、2-辛基、2-辛基氧基、1,1,1-三氟-2-己基、1,1,1-三氟-2-辛基和1,1,1-三氟-2-辛基氧基。
优选的手性支链基团为异丙基、异丁基(=甲基丙基)、异戊基(=3-甲基丁基)、异丙氧基、2-甲基-丙氧基和3-甲基丁氧基。
在另一优选实施方案中,尤其对于负光学色散应用,如上文所描述的可聚合的LC材料另外包含一种或多种式ND化合物,
其中
U1,2彼此独立地选自
包括它们的镜像,其中环U1和U2各自通过直立键键合至基团-(B)q-,和在这些环中一个或两个不相邻的CH2基团任选被O和/或S替代,
Q1,2彼此独立地是CH或SiH,
Q3是C或Si,
B在每次出现时彼此独立地是-C≡C-、-CY1=CY2-或任选取代的芳族或杂芳族基团,
Y1,2彼此独立地是H、F、Cl、CN或R0,
q是1至10的整数,优选1、2、3、4、5、6或7,
A1-4彼此独立地选自非芳族、芳族或杂芳族碳环或杂环基团,其任选被一个或多个基团R5取代,和其中-(A1-Z1)m-U1-(Z2-A2)n-和-(A3-Z3)o-U2-(Z4-A4)p-中的每一个不包含比非芳族基团多的芳族基团并优选不包含多于一个芳族基团,
Z1-4彼此独立地是-O-、-S-、-CO-、-COO-、-OCO-、-O-COO-、-CO-NR0-、-NR0-CO-、-NR0-CO-NR00-、-OCH2-、-CH2O-、-SCH2-、-CH2S-、-CF2O-、-OCF2-、-CF2S-、-SCF2-、-CH2CH2-、-(CH2)3-、-(CH2)4-、-CF2CH2-、-CH2CF2-、-CF2CF2-、-CH=CH-、-CY1=CY2-、-CH=N-、-N=CH-、-N=N-、-CH=CR0-、-C≡C-、-CH=CH-COO-、-OCO-CH=CH-、CR0R00或单键,
R0和R00彼此独立地是H或具有1至12个C原子的烷基,
m和n彼此独立地是0、1、2、3或4,
o和p彼此独立地是0、1、2、3或4,
R1-5彼此独立地是相同或不同的选自以下的基团:H、卤素、-CN、-NC、-NCO、-NCS、-OCN、-SCN、-C(=O)NR0R00、-C(=O)X0、-C(=O)R0、-NH2、-NR0R00、-SH、-SR0、-SO3H、-SO2R0、-OH、-NO2、-CF3、-SF5、P-Sp-,任选取代的甲硅烷基,或具有1至40个C原子的碳基或烃基,所述碳基或烃基任选被取代并任选包含一个或多个杂原子,或者表示P或P-Sp-,或者被P或P-Sp-取代,其中所述化合物包含至少一个表示P或P-Sp-或被P或P-Sp-取代的基团R1-5,
P是可聚合基团,
Sp是间隔基团或单键。
优选地,在式ND中形成桥连基团B的子基优选选自具有120°或更大,优选在180°范围内的键角的基团。非常优选-C≡C-基团或在对位连接至其相邻基团的二价芳族基团,如例如1,4-亚苯基,萘-2,6-二基,茚满-2,6-二基或噻吩并[3,2-b]噻吩-2,5-二基。
另外可行的子基包括-CH=CH-、-CY1=CY2-、-CH=N-、-N=CH-、-N=N-和-CH=CR0-,其中Y1、Y2、R0具有上文给出的含义。
优选在式ND中桥连基团或-(B)q-包含一个或多个选自-C≡C-、任选取代的1,4-亚苯基和任选取代的9H-芴-2,7-二基的基团。在式ND中子基或B优选选自-C≡C-、任选取代的1,4-亚苯基和任选取代的9H-芴-2,7-二基,其中在芴基中在9位的H原子任选被碳基或烃基替代。
非常优选在式ND中桥连基团或-(B)q-选自-C≡C-,-C≡C-C≡C-,-C≡C-
其中r是0、1、2、3或4,和L具有如下所述的含义。
优选地,在式ND中芳族基团A1-4可以是单环的,即仅具有一个芳族环(如例如苯基或亚苯基),或者是多环的,即具有两个或更多个稠环(如例如萘基或亚萘基)。特别优选具有至多25个C原子的单-、二-或三环芳族或杂芳族基团,所述芳族或杂芳族基团还可以包含稠环并且任选被取代。
优选地,在式ND的化合物中非芳族碳环和杂环A1-4,包括饱和的(也被称为“完全饱和的”)那些,即它们仅包含通过单键连接的C原子或杂原子,和不饱和的(也被称为“部分饱和的”)那些,即它们还包含通过双键连接的C原子或杂原子。非芳族环还可以包含一个或多个杂原子,所述杂原子优选选自Si、O、N和S。
优选在式ND中非芳族和芳族环或A1-4选自任选被一个或多个基团L取代的反式-1,4-亚环己基和1,4-亚苯基。
非常优选式ND的化合物,其中m和p是1,和n和o是1或2。进一步优选式ND的化合物,其中m和p是1或2,和n和o是0。进一步优选化合物,其中m、n、o和p是2。
在式ND的化合物中,介晶基团中连接芳族和非芳族环状基团的连接基团或Z1-4优选选自-O-、-S-、-CO-、-COO-、-OCO-、-O-COO-、-CO-NR0-、-NR0-CO-、-NR0-CO-NR0-、-OCH2-、-CH2O-、-SCH2-、-CH2S-、-CF2O-、-OCF2-、-CF2S-、-SCF2-、-CH2CH2-、-(CH2)3-、-(CH2)4-、-CF2CH2-、-CH2CF2-、-CF2CF2-、-CH=CH-、-CY1=CY2-、-CH=N-、-N=CH-、-N=N-、-CH=CR0-、-C≡C-、-CH=CH-COO-、-OCO-CH=CH-、CR0R00或单键,非常优选选自-COO-、-OCO-和单键。
优选地,在式ND的化合物中,在环上的取代基如L,优选选自P-Sp-、F、Cl、Br、I、-CN、-NO2、-NCO、-NCS、-OCN、-SCN、-C(=O)NR0R00、-C(=O)X、-C(=O)OR0、-C(=O)R0、-NR0R00、-OH、-SF5,任选取代的甲硅烷基,具有1至12个C原子,优选1至6个C原子的芳基或杂芳基,和具有1至12个C原子,优选1至6个C原子的直链或支链烷基、烷氧基、烷基羰基、烷氧基羰基、烷基羰基氧基或烷氧基羰基氧基,其中一个或多个H原子任选被F或Cl替代,其中R0和R00如在式ND中所限定,和X是卤素。
优选地,式ND的化合物包含一个或多个被两个或更多个可聚合基团P或P-Sp-取代的端基如R1-4或取代基如R5(多官能可聚合基团)。合适的该类型的多官能可聚合基团例如公开于US 7,060,200 B1或US 2006/0172090 A1中。
非常优选的式ND的化合物是以下子式的那些:
其中R1-5、A1-4、Z1-4、B、m、n、o、p和q具有一种上文给出的含义。
特别优选以下子式的化合物:
其中Z具有上文给出的Z1的含义中的一种,R具有如上文给出的不同于P-Sp-的R1的含义中的一种,和P、Sp、L和r如上文所限定,和在介晶基团中苯环任选被一个或多个如上文所限定的基团L取代。
此外,优选可聚合液晶介质,其中式ND的化合物选自式ND 25或ND 26的化合物,特别是其中Z表示-COO-,r在每次出现时是0,和P、Sp如上文所限定。
在这些优选的化合物中P-Sp-优选是P-Sp'-X',其中X'优选是-O-、-COO-或-OCOO-。
式ND、其子式的化合物和其合适的合成方法公开于WO 2008/119427 A1中。
在可聚合LC材料中式ND的化合物的量优选是1至50%,非常优选1至40%。
化合物或式I与式ND化合物的组合相较于不使用该特定组合的可聚合LC材料尤其引起光色散的有利减小,且引起光色散及/或延迟的有利耐热性。
本发明的另一目标是一种RM配制剂,其包含如上文及下文描述的一种或多种式I化合物或包含RM混合物,且进一步包含一种或多种溶剂及/或添加剂。
在优选的实施方案中,RM配制剂任选地包含一种或多种选自聚合引发剂、表面活性剂、稳定剂、催化剂、感光剂、抑制剂、链转移剂、共反应单体、反应性减黏剂、表面活性化合物、润滑剂、润湿剂、分散剂、疏水剂、粘合剂、流动改进剂、脱气剂或消泡剂、除气剂、稀释剂、反应性稀释剂、助剂、着色剂、染料、颜料和纳米颗粒的添加剂。
在另一实施方案中,RM配制剂任选地包含一种或多种选自可聚合非介晶化合物的添加剂(反应性减黏剂)。RM配制剂中这些添加剂的量优选地为0至30%,非常优选地为0至25%。
所使用的反应性减黏剂不仅为在实际意义上称作反应性减黏剂的物质且也为上文已提及的助剂化合物,该化合物含有一个或多个补充性反应性单元(例如羟基、硫醇-或氨基),经由该单元可与液晶化合物的可聚合单元发生反应。
通常能够光聚合的物质包括例如包含至少一个烯属双键的单-、二-或多官能化合物。其实例是羧酸的乙烯基酯,例如月桂酸、肉豆蔻酸、棕榈酸和硬脂酸的乙烯基酯,和二羧酸的乙烯基酯,例如丁二酸、己二酸的乙烯基酯,单官能醇的烯丙基和乙烯基醚和甲基丙烯酸和丙烯酸酯,例如月桂醇、肉豆蔻醇、棕榈醇和硬脂醇的烯丙基醚和乙烯基醚和甲基丙烯酸酯和丙烯酸酯,和双官能醇的二烯丙基醚和二乙烯基醚,例如乙二醇和1,4-丁二醇的二烯丙基醚和二乙烯基醚。
也合适的是例如多官能醇的甲基丙烯酸酯和丙烯酸酯,特别是那些,其除了羟基之外不包含另外的官能团,或至多包含醚基。这样的醇的实例是双官能醇,如乙二醇、丙二醇和它们的更高缩合的代表,例如二乙二醇、三乙二醇、二丙二醇、三丙二醇等,丁二醇、戊二醇、己二醇、新戊二醇,烷氧基化酚类化合物,如乙氧基化和丙氧基化双酚,环己烷二甲醇,三官能和多官能醇,如丙三醇、三羟甲基丙烷、丁三醇、三羟甲基乙烷、季戊四醇、二三羟甲基丙烷、二季戊四醇、山梨醇、甘露醇,以及相应的烷氧基化,特别是乙氧基化和丙氧基化的醇。
其他合适的反应性减黏剂是聚酯(甲基)丙烯酸酯,其是聚酯多元醇的(甲基)丙烯酸酯。
合适的聚酯多元醇的实例是那些,其可以通过使用多元醇,优选二醇,使多元羧酸,优选二羧酸酯化来制备。用于这样的含羟基聚酯的起始材料是本领域技术人员已知的。可以使用的二羧酸是丁二酸、戊二酸、己二酸、癸二酸、邻苯二甲酸和其异构体和加氢产物,和所述酸的可酯化或酯基可转移的衍生物,例如酸酐和二烷基酯。合适的多元醇是上文提及的醇,优选乙二醇、1,2-和1,3-丙二醇、1,4-丁二醇、1,6-己二醇、新戊二醇、环己烷二甲醇和乙二醇和丙二醇类的聚二醇。
此外,合适的反应性减黏剂是1,4-二乙烯基苯、氰尿酸三烯丙酯、下式的三环癸烯基醇的丙烯酸酯
也被称为丙烯酸二氢二环戊二烯基酯,以及丙烯酸、甲基丙烯酸和氰基丙烯酸的烯丙酯。
在通过实例的方式提及的反应性减黏剂中,特别地并且考虑到上文提及的优选的组合物,使用包含可光聚合基团的那些。
该基团包括例如二元醇和多元醇,例如乙二醇、丙二醇及其更高缩合的代表,例如二乙二醇、三乙二醇、二丙二醇、三丙二醇等,丁二醇、戊二醇、己二醇、新戊二醇、环己烷二甲醇、丙三醇、三羟甲基丙烷、丁三醇、三羟甲基乙烷、季戊四醇、二三羟甲基丙烷、二季戊四醇、山梨醇、甘露醇以及相应的烷氧基化,特别是乙氧基化和丙氧基化的醇。
此外,所述基团还包括例如烷氧基化的酚类化合物,如乙氧基化和丙氧基化双酚。
此外,这些反应性减黏剂可以是例如环氧或氨基甲酸酯(甲基)丙烯酸酯。
例如,环氧(甲基)丙烯酸酯是可通过本领域技术人员已知的,环氧化烯烃或多-或二缩水甘油醚如双酚A二缩水甘油醚与(甲基)丙烯酸反应得到的那些。
特别地,氨基甲酸酯(甲基)丙烯酸酯是本领域技术人员同样已知的,(甲基)丙烯酸羟基烷基酯与多-或二异氰酸酯反应的产物。
这样的环氧和氨基甲酸酯(甲基)丙烯酸酯作为“混合的形式”被包括在上文列举的化合物中。
如果使用反应性减黏剂,则它们的量和性能必须与相应的条件相匹配,使得一方面实现满意的期望的效果,例如根据本发明的组合物的期望的颜色,但是另一方面,不过度地损害液晶组合物的相行为。例如,低交联(高交联)液晶组合物可以使用具有相对低(高)的每分子反应性单元的数量的相应的反应性减黏剂制备。
例如,稀释剂的组包括:
C1-C4-醇,例如甲醇、乙醇、正丙醇、异丙醇、丁醇、异丁醇、仲丁醇,和特别地C5-C12-醇,正戊醇、正己醇、正庚醇、正辛醇、正壬醇、正癸醇、正十一烷醇和正十二烷醇及其异构体,二醇,例如1,2-乙二醇、1,2-和1,3-丙二醇、1,2-、2,3-和1,4-丁二醇、二-和三乙二醇及二-和三-丙二醇,醚,例如甲基叔丁基醚、1,2-乙二醇单-和二-甲基醚、1,2-乙二醇单-和二-乙基醚、3-甲氧基丙醇、3-异丙氧基丙醇、四氢呋喃和二氧六环,酮,例如丙酮、甲基乙基酮、甲基异丁基酮和二丙酮醇(4-羟基-4-甲基-2-戊酮),C1-C5-烷基酯,例如乙酸甲酯、乙酸乙酯、乙酸丙酯、乙酸丁酯和乙酸戊酯,脂肪族和芳族烃,例如戊烷、己烷、庚烷、辛烷、异辛烷、石油醚、甲苯、二甲苯、乙苯、四氢萘、十氢萘、二甲基萘,白色溶剂油、和矿物油,例如汽油、煤油、柴油和取暖油,还有天然油,例如橄榄油、大豆油、菜籽油、亚麻籽油和葵花籽油。
当然还可以在根据本发明的组合物中使用这些稀释剂的混合物。
只要存在至少部分的混溶性,这些稀释剂就还可以与水混合。在此合适的稀释剂的实例是C1-C4-醇,例如甲醇、乙醇、正丙醇、异丙醇、丁醇、异丁醇和仲丁醇,二醇,例如1,2-乙二醇、1,2-和1,3-丙二醇、1,2-、2,3-和1,4-丁二醇、二-和三-乙二醇及二-和三-丙二醇,醚,例如四氢呋喃和二氧六环,酮,例如丙酮、甲基乙基酮和二丙酮醇(4-羟基-4-甲基-2-戊酮),和C1-C4-烷基酯,例如乙酸甲酯、乙酸乙酯、乙酸丙酯和乙酸丁酯。
任选以约0至10.0重量%,优选约0至5.0重量%的比例使用稀释剂,基于所述RM配制剂的总重量。
不能将消泡剂和除气剂(c1))、润滑剂和流动助剂(c2))、热固化或辐射固化助剂(c3))、基板润湿助剂(c4))、润湿和分散助剂(c5))、疏水剂(c6))、粘合促进剂(c7))和促进抗划伤性的助剂(c8))严格地以其作用彼此划定界限。
例如,润滑剂和流动助剂还常常用作消泡剂和/或除气剂和/或促进抗划伤性的助剂。辐射固化助剂还可以用作润滑剂和流动助剂和/或除气剂和/或基板润湿助剂。在各种情况下,这些助剂中的一些还可以实现粘合促进剂(c8))的功能。
相应于上文所述的,因此可以将某些添加剂分类为下文描述的若干个c1)至c8)组。
在c1)组中消泡剂包括无硅和含硅聚合物。含硅聚合物是例如未改性或改性的聚二烷基硅氧烷或包含聚二烷基硅氧烷和聚醚单元的支化共聚物、梳形或嵌段共聚物,后者可由环氧乙烷或环氧丙烷得到。
在c1)组中除气剂包括例如有机聚合物,例如聚醚和聚丙烯酸酯、二烷基聚硅氧烷,特别是二甲基聚硅氧烷,有机改性的聚硅氧烷,例如芳基烷基改性的聚硅氧烷,以及氟硅酮。
消泡剂的作用基本上基于防止泡沫形成或破坏已经形成的泡沫。在待脱气的介质中,例如根据本发明的组合物中,消泡剂基本上通过促进细分气体或空气气泡合并以得到更大的气泡来起作用,并由此加速气体(或空气)的逸出。由于消泡剂经常还可以用作除气剂并且反之亦然,因此这些添加剂已经一并被包括在c1)组中。
例如,这样的助剂可以从Tego以Foamex 800、Foamex 805、Foamex 810、Foamex 815、Foamex 825、Foamex835、Foamex 840、Foamex 842、Foamex 1435、Foamex 1488、Foamex 1495、Foamex 3062、Foamex 7447、Foamex 8020、Foamex N、Foamex K 3、Antifoam2-18、Antifoam 2-18、Antifoam 2-57、Antifoam 2-80、Antifoam 2-82、Antifoam 2-89、Antifoam 2-92、Antifoam 14、Antifoam 28、Antifoam 81、Antifoam D 90、Antifoam 93、Antifoam 200、Antifoam201、Antifoam 202、Antifoam 793、ntifoam 1488、Antifoam 3062、5803、5852、5863、7008、Antifoam 1-60、Antifoam 1-62、Antifoam 1-85、Antifoam 2-67、Antifoam WM 20、Antifoam 50、Antifoam 105、Antifoam730、Antifoam MR 1015、Antifoam MR1016、Antifoam1435、Antifoam N、Antifoam KS 6、Antifoam KS 10、Antifoam KS 53、Antifoam KS 95、Antifoam KS 100、Antifoam KE 600、Antifoam KS 911、Antifoam MR 1000、Antifoam KS 1100、Airex 900、Airex 910、Airex931、Airex 935、Airex 936、Airex 960、Airex 970、Airex 980和Airex 985商购得到和从BYK以 和商购得到。
在c1)组中的助剂任选以约0至3.0重量%,优选约0至2.0重量%的比例使用,基于RM配制剂的总重量。
在c2)组中,润滑剂和流动助剂通常包括无硅和含硅的聚合物,例如聚丙烯酸酯或改性剂,低分子量聚二烷基硅氧烷。所述改性在于烷基中的一些已经被宽泛的多种有机基团替代。这些有机基团是例如聚醚、聚酯或甚至长链烷基基团,前者最常使用。
在相应地改性的聚硅氧烷中聚醚基团通常由环氧乙烷和/或环氧丙烷单元构成。通常,在改性的聚硅氧烷中这些环氧烷烃单元的比例越高,所得产物的亲水性越高。
例如,这样的助剂可以从Tego以Glide 100、Glide ZG 400、Glide 406、Glide 410、Glide 411、Glide415、Glide 420、Glide 435、Glide440、Glide450、Glide A115、Glide B 1484(还可以用作消泡剂和除气剂)、Flow ATF、Flow 300、Flow 460、Flow 425和Flow ZFS 460商购得到。合适的可辐射固化的润滑剂和流动助剂,其还可以用于改进抗划伤性,是产品Rad 2100、Rad 2200、Rad 2500、Rad 2600和Rad 2700,其同样可得自TEGO。
在c2)组中的助剂任选以约0至3.0重量%,优选约0至2.0重量%的量使用,基于所述RM配制剂的总重量。
在c3)组中,辐射固化助剂包括特别是具有末端双键的聚硅氧烷,例如该末端双键为丙烯酸酯基的成分。这样的助剂可以通过光化或例如电子辐射交联。这些助剂通常将若干种性能结合在一起。在未交联状态下,它们可以用作消泡剂、除气剂、润滑剂和流动助剂和/或基板润湿助剂,而在交联状态下,它们特别地提高例如可以使用根据本发明的组合物制备的涂层或膜的抗划伤性。精确地例如那些涂层或膜的光泽性能的改进基本上被认为是作为消泡剂、除气剂和/或润滑剂和流动助剂(在未交联状态下)的这些助剂作用的结果。
在c3)组中热固化助剂包含例如伯OH基团,其能够与例如粘合剂的异氰酸酯基反应。
在c3)组中的助剂任选以约0至5.0重量%,优选约0至3.0重量%的比例使用,基于RM配制剂的总重量。
在c4)组中的基板润湿助剂特别地用于提高待例如由印刷油墨或涂料组合物(例如根据本发明的组合物)印刷或涂覆的基板的润湿性。通常伴随的这样的印刷油墨或涂料组合物的润滑和流动行为的改进对制成的(例如交联的)印刷品或涂层的外观有影响。
在c4)组中的助剂任选以约0至3.0重量%,优选约0至1.5重量%的比例使用,基于所述液晶组合物的总重量。
在c5)组中的润湿和分散助剂特别地用于防止颜料的浮色和发花及沉积,并因此(如果必要的话)特别适用于根据本发明的着色的组合物中。
这些助剂基本上通过包含这些添加剂的颜料颗粒的静电排斥和/或空间位阻使颜料分散体稳定化,其中在后一种情况下,助剂与周围介质(例如粘合剂)的相互作用起到重要作用。
由于这样润湿和分散助剂的使用例如在印刷油墨和漆料技术领域中是常用实践,因此合适的该类型的助剂的选择通常不会给本领域技术人员带来任何困难(如果使用它们的话)。
这样的润湿和分散助剂例如可从Tego以Dispers 610、Dispers 610S、Dispers 630、Dispers 700、Dispers705、Dispers 710、Dispers 720W、Dispers 725W、Dispers 730W、Dispers 735W和Dispers 740W和从BYK以 和商购得到。
在c5)组中的助剂的量以助剂的平均分子量使用。因此在任何情况下,预先的实验是可取的,但是这可以由本领域技术人员简单地完成。
在c6)组中的疏水剂可以用于赋予例如使用根据本发明的组合物制造的印刷品或涂层憎水性能。这防止或至少大大地抑制了由于水吸收的溶胀和由此例如这样的印刷品或涂层的光学性能的改变。此外,当例如在胶版印刷中使用所述组合物作为印刷油墨时,由此可以防止或至少大幅度地降低水吸收。
这样的疏水剂例如可从Tego以Phobe WF、Phobe 1000、Phobe 1000S、Phobe 1010、Phobe 1030、Phobe 1010、Phobe 1010、Phobe 1030、Phobe 1040、Phobe 1050、Phobe 1200、Phobe 1300、Phobe 1310和Phobe 1400商购得到。
在c6)组中的助剂任选以约0至5.0重量%,优选约0至3.0重量%的比例使用,基于RM配制剂的总重量。
来自c7)组的粘合促进剂用于改进接触的两个界面的粘附性。由此直接显然的是基本上,有效的粘合促进剂的唯一部分是位于一个或另一个界面或两个界面处的部分。如果例如期望将液体或糊状印刷油墨、涂料组合物或漆料施加到固体基板,这通常意味着必须将粘合促进剂直接加入到后者中,或者必须用粘合促进剂预处理基板(也称为上底漆),即赋予该基板改变的化学和/或物理表面性能。
如果已经用底漆预先对基板上底漆,这意味着接触的界面一方面是底漆的界面和另一方面是印刷油墨或涂料组合物或漆料的界面。在这种情况下,不仅基板和底漆之间的粘附性能,而且基板和印刷油墨或涂料组合物或漆料之间的粘附性能也在基板上的整个多层结构的粘附性中起到作用。
可以被提及的更广泛意义上的粘合促进剂也是已经在c4)组中列举的基板润湿助剂,但是这些通常不具有相同的粘合促进能力。
鉴于基板和旨在用于例如它们的印刷或涂覆的印刷油墨、涂料组合物和漆料的广泛变化的物理和化学特性,粘合促进剂体系的多样性并不是令人惊奇的。
基于硅烷的粘合促进剂是例如3-氨基丙基三甲氧基硅烷,3-氨基丙基三乙氧基硅烷,3-氨基丙基甲基二乙氧基硅烷,N-氨基乙基-3-氨基丙基三甲氧基硅烷,N-氨基乙基-3-氨基丙基甲基二甲氧基硅烷,N-甲基-3-氨基丙基三甲氧基硅烷,3-脲基丙基三乙氧基硅烷,3-甲基丙烯酰氧基丙基三甲氧基硅烷,3-缩水甘油基氧基丙基三甲氧基硅烷,3-巯基丙基三甲氧基硅烷,3-氯丙基三甲氧基硅烷和乙烯基三甲氧基硅烷。这些和其他硅烷可从Hüls例如以商品名商购得到。
通常应当使用来自这样的添加剂的制造商的相应的技术信息,或者本领域技术人员可以以简单的方式通过相应的初步实验得到该信息。
然而,如果要将这些添加剂作为来自c7)组的助剂加入到根据本发明的RM配制剂中,则它们的比例任选对应于约0至5.0重量%,基于所述RM配制剂的总重量。这些浓度数据仅仅作为指导,因为添加剂的量和特性(identity)在每种单独的情况下通过基板和印刷/涂料组合物的性质确定。对于该情况,相应的技术信息通常可得自这样的添加剂的制造商,或者可以由本领域技术人员以简单的方式通过相应的初步实验确定。
对c3)组给出的量的数据同样适用于这些助剂,即这些添加剂任选以约0至5.0重量%,优选约0至3.0重量%的比例使用,基于所述液晶组合物的总重量。
可以提及的光、热和/或氧化稳定剂的实例是以下物质:
烷基化单苯酚,如2,6-二-叔丁基-4-甲基苯酚、2-叔丁基-4,6-二甲基苯酚、2,6-二-叔丁基-4-乙基苯酚、2,6-二-叔丁基-4-正丁基苯酚、2,6-二-叔丁基-4-异丁基苯酚、2,6-二环戊基-4-甲基苯酚、2-(α-甲基环己基)-4,6-二甲基苯酚、2,6-二(十八烷基)-4-甲基苯酚、2,4,6-三环己基苯酚、2,6-二-叔丁基-4-甲氧基甲基苯酚,具有直链或支链侧链的壬基苯酚,例如2,6-二壬基-4-甲基苯酚、2,4-二甲基-6-(1′-甲基十一烷-1′-基)苯酚、2,4-二甲基-6-(1′-甲基十七烷-1′-基)苯酚、2,4-二甲基-6-(1′-甲基十三烷-1′-基)苯酚和这些化合物的混合物,烷基硫代甲基苯酚,如2,4-二辛基硫代甲基-6-叔丁基苯酚、2,4-二辛基硫代甲基-6-甲基苯酚、2,4-二辛基硫代甲基-6-乙基苯酚和2,6-二(十二烷基)硫代甲基-4-壬基苯酚,
氢醌和烷基化氢醌,如2,6-二叔丁基-4-甲氧基苯酚、2,5-二叔丁基氢醌、2,5-二叔戊基氢醌(2,5-di-tert-amylhydrocrainone)、2,6-二苯基-4-十八烷氧基苯酚、2,6-二-叔丁基氢醌、2,5-二-叔丁基-4-羟基苯甲醚、3,5-二-叔丁基-4-羟基苯甲醚、硬脂酸3,5-二-叔丁基-4-羟基苯酯和双(3,5-二-叔丁基-4-羟基苯基)己二酸酯,
生育酚,如α-生育酚、β-生育酚、γ-生育酚、δ-生育酚和这些化合物的混合物,以及生育酚衍生物,如生育酚乙酸酯、生育酚琥珀酸酯、生育酚烟酸酯和生育酚聚氧乙烯琥珀酸酯(“tocofersolate”),
羟基化二苯基硫醚,如2,2′-硫代双(6-叔丁基-4-甲基苯酚)、2,2′-硫代双(4-辛基苯酚)、4,4′-硫代双(6-叔丁基-3-甲基苯酚)、4,4′-硫代双(6-叔丁基-2-甲基苯酚)、4,4′-硫代双(3,6-二-仲戊基苯酚)和4,4′-双(2,6-二甲基-4-羟基苯基)二硫醚,
亚烷基双酚,例如2,2′-亚甲基双(6-叔丁基-4-甲基苯酚)、2,2′-亚甲基双(6-叔丁基-4-乙基苯酚)、2,2′-亚甲基双[4-甲基-6-(α-甲基环己基)苯酚]、2,2′-亚甲基双(4-甲基-6-环己基苯酚)、2,2′-亚甲基双(6-壬基-4-甲基苯酚)、2,2′-亚甲基双(4,6-二-叔丁基苯酚)、2,2-亚乙基双(4,6-二-叔丁基苯酚)、2,2′-亚乙基双(6-叔丁基-4-异丁基苯酚)、2,2′-亚甲基双[6-(α-甲基苄基)-4-壬基苯酚]、2,2′-亚甲基双[6-(α,α-二甲基苄基)-4-壬基苯酚]、4,4′-亚甲基双(2,6-二-叔丁基苯酚)、4,4′-亚甲基双(6-叔丁基-2-甲基苯酚)、1,1-双(5-叔丁基-4-羟基-2-甲基苯基)丁烷、2,6-双(3-叔丁基-5-甲基-2-羟基苄基)-4-甲基苯酚、1,1,3-三(5-叔丁基-4-羟基-2-甲基苯基)丁烷、1,1-双(5-叔丁基-4-羟基-2-甲基苯基)-3-正十二烷基-巯基丁烷、乙二醇双[3,3-双(3′-叔丁基-4′-羟基苯基)丁酸酯]、双(3-叔丁基-4-羟基-5-甲基苯基)二环戊二烯,双[2-(3′-叔丁基-2′-羟基-5′-甲基苄基)-6-叔丁基-4-甲基苯基]对苯二甲酸酯、1,1-双(3,5-二甲基-2-羟基苯基)丁烷、2,2-双(3,5-二-叔丁基-4-羟基苯基)丙烷、2,2-双(5-叔丁基-4-羟基-2-甲基苯基)-4-正十二烷基-巯基丁烷和1,1,5,5-四(5-叔丁基-4-羟基-2-甲基苯基)戊烷,
O-、N-和S-苄基化合物,如3,5,3′,5′-四-叔丁基-4,4′-二羟基二苄基醚、4-羟基-3,5-二甲基苄基巯基乙酸十八烷酯、4-羟基-3,5-二-叔丁基苄基巯基乙酸十三烷酯、三(3,5-二-叔丁基-4-羟基苄基)胺、双(4-叔丁基-3-羟基-2,6-二甲基苄基)二硫代对苯二甲酸酯、双(3,5-二-叔丁基-4-羟基苄基)硫醚和异辛基-3,5-二-叔丁基-4-羟基苄基巯基乙酸酯,
芳族羟基苄基化合物,如1,3,5-三(3,5-二-叔丁基-4-羟基苄基)-2,4,6-三甲基-苯、1,4-双(3,5-二-叔丁基-4-羟基苄基)-2,3,5,6-四甲基-苯和2,4,6-三(3,5-二-叔丁基-4-羟基苄基)苯酚,
三嗪化合物,如2,4-双(辛基巯基)-6-(3,5-二-叔丁基-4-羟基苯胺基)-1,3,5-三嗪、2-辛基巯基-4,6-双(3,5-二-叔丁基-4-羟基苯胺基)-1,3,5-三嗪、2-辛基巯基-4,6-双(3,5-二-叔丁基-4-羟基苯氧基)-1,3,5-三嗪、2,4,6-三(3,5-二-叔丁基-4-羟基苯氧基)-1,2,3-三嗪、1,3,5-三(3,5-二-叔丁基-4-羟基苄基)异氰尿酸酯、1,3,5-三(4-叔丁基-3-羟基-2,6-二甲基苄基)异氰尿酸酯、2,4,6-三(3,5-二-叔丁基-4-羟基苯基乙基)-1,3,5-三嗪、1,3,5-三-(3,5-二-叔丁基-4-羟基苯基丙酰基)六氢-1,3,5-三嗪、1,3,5-三(3,5-二环己基-4-羟基苄基)异氰尿酸酯和1,3,5-三(2-羟基乙基)异氰尿酸酯,
苄基膦酸酯,如2,5-二-叔丁基-4-羟基苄基膦酸二甲酯、3,5-二-叔丁基-4-羟基苄基膦酸二乙酯、3,5-二-叔丁基-4-羟基苄基膦酸二(十八烷)酯和5-叔丁基-4-羟基-3-甲基苄基膦酸二(十八烷)酯,
酰基氨基苯酚,如4-羟基月桂酰苯胺、4-羟基硬脂酰苯胺和N-(3,5-二-叔丁基-4-羟基苯基)氨基甲酸辛酯,
例如单羟基或多羟基醇的丙酸酯和乙酸酯,如甲醇、乙醇、正辛醇、异辛醇、十八烷醇、1,6-己二醇、1,9-壬二醇、乙二醇、1,2-丙二醇、新戊二醇、硫代二乙二醇、二乙二醇、三乙二醇、季戊四醇、三(羟基乙基)异氰尿酸酯、N,N′-双(羟基乙基)草酰胺、3-硫杂十一烷醇、3-硫杂十五烷醇、三甲基己二醇、三羟甲基丙烷和4-羟基甲基-1-膦杂(phospha)-2,6,7-三氧杂双环[2.2.2]-辛烷的丙酸酯和乙酸酯,
基于胺衍生物的丙酰胺,如N,N′-双(3,5-二-叔丁基-4-羟基苯基丙酰基)六亚甲基二胺、N,N′-双(3,5-二-叔丁基-4-羟基苯基丙酰基)三亚甲基二胺和N,N′-双(3,5-二-叔丁基-4-羟基苯基丙酰基)肼,
抗坏血酸(维生素C)和抗坏血酸衍生物,如抗坏血酸棕榈酸酯、抗坏血酸月桂酸酯和抗坏血酸硬脂酸酯,以及抗坏血酸硫酸酯和抗坏血酸磷酸酯,
基于胺化合物的抗氧剂,如N,N′-二异丙基-对苯二胺、N,N′-二-仲丁基-对苯二胺、N,N′-双(1,4-二甲基戊基)-对苯二胺、N,N′-双(1-乙基-3-甲基戊基)-对苯二胺、N,N′-双(1-甲基庚基)-对苯二胺、N,N′-二环己基-对苯二胺、N,N′-二苯基-对苯二胺、N,N′-双(2-萘基)-对苯二胺、N-异丙基-N′-苯基-对苯二胺、N-(1,3-二甲基丁基)-N′-苯基-对苯二胺、N-(1-甲基庚基)-N′-苯基-对苯二胺、N-环己基-N′-苯基-对苯二胺、4-(对甲苯氨磺酰基)二苯胺、N,N′-二甲基-N,N′-二-仲丁基-对苯二胺、二苯胺、N-烯丙基二苯胺、4-异丙氧基二苯胺、N-苯基-1-萘胺、N-(4-叔辛基苯基)-1-萘胺、N-苯基-2-萘胺,辛基-取代的二苯胺,如p,p′-二-叔辛基二苯胺、4-正丁基氨基苯酚、4-丁酰基氨基苯酚、4-壬酰基氨基苯酚、4-十二烷酰基氨基苯酚、4-十八烷酰基氨基苯酚、双(4-甲氧基苯基)胺、2,6-二-叔丁基-4-二甲基氨基甲基苯酚、2,4-二氨基二苯基甲烷、4,4′-二氨基二苯基甲烷、N,N,N′,N′-四甲基-4,4′-二氨基二苯基甲烷、1,2-双[(2-甲基苯基)氨基]乙烷、1,2-双(苯基氨基)丙烷、(邻甲苯基)双胍、双[4-(1′,3′-二甲基丁基)苯基]胺、叔辛基-取代的N-苯基-1-萘胺、单-和二-烷基化叔丁基/叔辛基二苯胺的混合物、单-和二-烷基化壬基二苯胺的混合物,单-和二-烷基化十二烷基二苯胺的混合物、单-和二-烷基化异丙基/异己基二苯胺的混合物、单-和二-烷基化叔丁基二苯胺的混合物、2,3-二氢-3,3-二甲基-4H-1,4-苯并噻嗪、吩噻嗪、单-和二-烷基化叔丁基/叔辛基吩噻嗪的混合物、单-和二-烷基化叔辛基吩噻嗪的混合物、N-烯丙基吩噻嗪、N,N,N′,N′-四苯基-1,4-二氨基丁-2-烯、N,N-双(2,2,6,6-四甲基哌啶-4-基)六亚甲基二胺、双(2,2,6,6-四甲基哌啶-4-基)癸二酸酯、2,2,6,6-四甲基哌啶-4-酮和2,2,6,6-四甲基哌啶-4-醇,
膦、亚磷酸酯和亚膦酸酯,如三苯基膦、三苯基亚磷酸酯、二苯基烷基亚磷酸酯、苯基二烷基亚磷酸酯、三(壬基苯基)亚磷酸酯、亚磷酸三月桂基酯、亚磷酸三(十八烷基)酯、二硬脂基季戊四醇二亚磷酸酯、三(2,4-二-叔丁基苯基)亚磷酸酯、二异癸基季戊四醇二亚磷酸酯、双(2,4-二-叔丁基苯基)季戊四醇二亚磷酸酯、双(2,6-二-叔丁基-4-甲基苯基)季戊四醇二亚磷酸酯、二异癸氧基季戊四醇二亚磷酸酯、双(2,4-二-叔丁基-6-甲基苯基)季戊四醇二亚磷酸酯、双(2,4,6-三(叔丁基苯基))季戊四醇二亚磷酸酯、三硬脂基山梨醇三亚磷酸酯、四(2,4-二-叔丁基苯基)4,4′-二亚苯基二亚膦酸酯、6-异辛氧基-2,4,8,10-四-叔丁基-12H-二苯并[d,g]-1,3,2-二氧杂磷杂环辛烯(dioxaphosphocine)、6-氟-2,4,8,10-四-叔丁基-12-甲基-二苯并[d,g]-1,3,2-二氧杂磷杂环辛烯、双(2,4-二-叔丁基-6-甲基苯基)甲基亚磷酸酯和双(2,4-二-叔丁基-6-甲基苯基)乙基亚磷酸酯,
2-(2′-羟基苯基)苯并***,如2-(2′-羟基-5′-甲基苯基)苯并***、2-(3′,5′-二-叔丁基-2′-羟基苯基)苯并***、2-(5′-叔丁基-2′-羟基苯基)苯并***、2-(2′-羟基-5′-(1,1,3,3-四甲基丁基)苯基)苯并***、2-(3′,5′-二-叔丁基-2′-羟基苯基)-5-氯苯并***、2-(3′-叔丁基-2′-羟基-5′-甲基苯基)-5-氯苯并***、2-(3′-仲丁基-5′-叔丁基-2′-羟基苯基)苯并***、2-(2′-羟基-4′-辛氧基苯基)苯并***、2-(3′,5′-二叔戊基-2′-羟基苯基)苯并***、2-(3,5′-双-(α,α-二甲基苄基)-2′-羟基苯基)苯并***,以下的混合物:2-(3′-叔丁基-2′-羟基-5′-(2-辛氧基羰基乙基)苯基)-5-氯苯并***、2-(3′-叔丁基-5′-[2-(2-乙基己氧基)羰基乙基]-2′-羟基苯基)-5-氯苯并***、2-(3′-叔丁基-2′-羟基-5′-(2-甲氧基羰基乙基)苯基)-5-氯苯并***、2-(3′-叔丁基-2′-羟基-5′-(2-甲氧基羰基乙基)苯基)苯并***、2-(3′-叔丁基-2′-羟基-5′-(2-辛氧基羰基乙基)苯基)苯并***、2-(3′-叔丁基-5′-[2-(2-乙基己氧基)羰基乙基]-2′-羟基苯基)苯并***、2-(3′-十二烷基-2′-羟基-5′-甲基苯基)苯并***和2-(3′-叔丁基-2′-羟基-5′-(2-异辛氧基羰基乙基)苯基苯并***、2,2′-亚甲基双[4-(1,1,3,3-四甲基丁基)-6-苯并***-2-基苯酚];2-[3′-叔丁基-5′-(2-甲氧基羰基乙基)-2′-羟基苯基]-2H-苯并***与聚乙二醇300的完全酯化的产物;
含硫过氧化物清除剂和含硫抗氧剂,如3,3′-硫代二丙酸的酯,例如月桂基、硬脂基、肉豆蔻基和十三烷基酯,巯基苯并咪唑和2-巯基苯并咪唑的锌盐,二硫代氨基甲酸二丁基锌,二(十八烷基)二硫醚和季戊四醇四(β-十二烷基巯基)丙酸酯,
2-羟基二苯甲酮,如4-羟基、4-甲氧基、4-辛氧基、4-癸氧基、4-十二烷氧基、4-苄氧基、4,2′,4′-三羟基和2′-羟基-4,4′-二甲氧基衍生物,
未取代和取代苯甲酸的酯,如水杨酸4-叔丁基苯酯、水杨酸苯酯、水杨酸辛基苯酯、二苯甲酰间苯二酚、双(4-叔丁基苯甲酰)间苯二酚、苯甲酰间苯二酚、3,5-二-叔丁基-4-羟基苯甲酸2,4-二-叔丁基苯基酯、十六烷基-3,5-二-叔丁基-4-羟基苯甲酸酯、十八烷基-3,5-二-叔丁基-4-羟基苯甲酸酯和2-甲基-4,6-二-叔丁基苯基-3,5-二-叔丁基-4-羟基苯甲酸酯,
丙烯酸酯,如α-氰基-β,β-二苯基丙烯酸乙酯、α-氰基-β,β-二苯基丙烯酸异辛酯、α-甲氧基羰基肉桂酸甲酯、α-氰基-β-甲基-对甲氧基肉桂酸甲酯、丁基-α-氰基-β-甲基-对甲氧基肉桂酸酯和甲基-α-甲氧基羰基-对甲氧基肉桂酸酯,空间位阻胺,如双(2,2,6,6-四甲基哌啶-4-基)癸二酸酯、双(2,2,6,6-四甲基哌啶-4-基)琥珀酸酯、双(1,2,2,6,6-五甲基哌啶-4-基)癸二酸酯、双(1-辛氧基-2,2,6,6-四甲基哌啶-4-基)癸二酸酯、双(1,2,2,6,6-五甲基哌啶-4-基)-正丁基-3,5-二-叔丁基-4-羟基苄基丙二酸酯、1-(2-羟基乙基)-2,2,6,6-四甲基-4-羟基哌啶和琥珀酸的缩合产物、N,N′-双(2,2,6,6-四甲基哌啶-4-基)六亚甲基二胺和4-叔辛基氨基-2,6-二氯-1,3,5-三嗪的缩合产物、三(2,2,6,6-四甲基哌啶-4-基)次氮基三乙酸酯、四(2,2,6,6-四甲基哌啶-4-基)1,2,3,4-丁烷四羧酸酯、1,1′-(1,2-亚乙基)双(3,3,5,5-四甲基哌嗪酮)、4-苯甲酰基-2,2,6,6-四甲基哌啶、4-硬脂基氧基-2,2,6,6-四甲基哌啶、双(1,2,2,6,6-五甲基哌啶-4-基)2-正丁基-2-(2-羟基-3,5-二-叔丁基苄基)丙二酸酯、3-正辛基-7,7,9,9-四甲基-1,3,8-三氮杂螺[4.5]癸烷-2,4-二酮、双(1-辛氧基-2,2,6,6-四甲基哌啶-4-基)癸二酸酯、双(1-辛氧基-2,2,6,6-四甲基哌啶-4-基)琥珀酸酯、N,N′-双(2,2,6,6-四甲基哌啶-4-基)六亚甲基二胺和4-吗啉代-2,6-二氯-1,3,5-三嗪的缩合产物、2-氯-4,6-双(4-正丁基氨基-2,2,6,6-四甲基哌啶-4-基)-1,3,5-三嗪和1,2-双(3-氨基丙基氨基)乙烷的缩合产物、2-氯-4,6-二(4-正丁基氨基-1,2,2,6,6-五甲基哌啶-4-基)-1,3,5-三嗪和1,2-双(3-氨基丙基氨基)乙烷的缩合产物、8-乙酰基-3-十二烷基-7,7,9,9-四甲基-1,3,8-三氮杂螺[4.5]-癸烷-2,4-二酮、3-十二烷基-1-(2,2,6,6-四甲基哌啶-4-基)吡咯烷-2,5-二酮、3-十二烷基-1-(1,2,2,6,6-五甲基哌啶-4-基)吡咯烷-2,5-二酮、4-十六烷氧基-和4-硬脂基氧基-2,2,6,6-四甲基哌啶的混合物、N,N′-双(2,2,6,6-四甲基哌啶-4-基)六亚甲基二胺和4-环己基氨基-2,6-二氯-1,3,5-三嗪的缩合产物、1,2-双(3-氨基丙基氨基)乙烷和2,4,6-三氯-1,3,5-三嗪的缩合产物、4-丁基氨基-2,2,6,6-四甲基哌啶、N-(2,2,6,6-四甲基哌啶-4-基)-正十二烷基琥珀酰亚胺、N-(1,2,2,6,6-五甲基哌啶-4-基)-正十二烷基琥珀酰亚胺、2-十一烷基-7,7,9,9-四甲基-1-氧杂-3,8-二氮杂-4-氧代-螺[4.5]-癸烷、7,7,9,9-四甲基-2-环十一烷基-1-氧杂-3,8-二氮杂-4-氧代螺-[4.5]癸烷和环氧氯丙烷的缩合产物、4-氨基-2,2,6,6-四甲基哌啶与四羟甲基乙炔二脲和聚(甲氧基丙基-3-氧基)-[4(2,2,6,6-四甲基)哌啶基]-硅氧烷的缩合产物,
草酰胺,如4,4′-二辛氧基草酰苯胺、2,2′-二乙氧基草酰苯胺、2,2′-二辛氧基-5,5′-二-叔丁草酰苯胺(butoxanilide)、2,2′-二(十二烷氧基)-5,5′-二-叔丁草酰苯胺、2-乙氧基-2′-乙基草酰苯胺、N,N′-双(3-二甲基氨基丙基)草酰胺、2-乙氧基-5-叔丁基-2′-乙草酰苯胺(ethoxanilide)及其与2-乙氧基-2′-乙基-5,4′-二-叔丁草酰苯胺的混合物、和邻-、对-甲氧基-二取代的草酰苯胺的混合物及邻-和对-乙氧基-二取代草酰苯胺的混合物,以及
2-(2-羟基苯基)-1,3,5-三嗪,如2,4,6-三-(2-羟基-4-辛氧基苯基)-1,3,5-三嗪、2-(2-羟基-4-辛氧基苯基)-4,6-双(2,4-二甲基苯基)-1,3,5-三嗪、2-(2,4-二羟基苯基)-4,6-双(2,4-二甲基苯基)-1,3,5-三嗪、2,4-双(2-羟基-4-丙氧基苯基)-6-(2,4-二甲基苯基)-1,3,5-三嗪、2-(2-羟基-4-辛氧基苯基)-4,6-双(4-甲基苯基)-1,3,5-三嗪、2-(2-羟基-4-十二烷氧基苯基)-4,6-双(2,4-二甲基苯基)-1,3,5-三嗪、2-(2-羟基-4-十三烷氧基苯基)-4,6-双(2,4-二甲基苯基)-1,3,5-三嗪、2-[2-羟基-4-(2-羟基-3-丁氧基丙氧基)苯基]-4,6-双(2,4-二甲基)-1,3,5-三嗪、2-[2-羟基-4-(2-羟基-3-辛氧基丙氧基)苯基]-4,6-双(2,4-二甲基)-1,3,5-三嗪、2-[4-(十二烷氧基/十三烷氧基-2-羟基丙氧基)-2-羟基苯基]-4,6-双(2,4-二甲基苯基)-1,3,5-三嗪、2-[2-羟基-4-(2-羟基-3-十二烷氧基丙氧基)苯基]-4,6-双-(2,4-二甲基苯基)-1,3,5-三嗪、2-(2-羟基-4-己氧基苯基)-4,6-二苯基-1,3,5-三嗪、2-(2-羟基-4-甲氧基苯基)-4,6-二苯基-1,3,5-三嗪、2,4,6-三[2-羟基-4-(3-丁氧基-2-羟基丙氧基)苯基]-1,3,5-三嗪和2-(2-羟基苯基)-4-(4-甲氧基苯基)-6-苯基-1,3,5-三嗪。
优选如提及使用的光、热及/或氧化稳定剂的其他实例如下:
其中各个基团具有以下含义:
R1至R5表示各自独立地选自由以下组成的组:H、-烷基、-OH、-烷基芳基、-烷基杂芳基、-环烷基、环杂烷基、烯基、芳基及-SO3H,及
R6及R7各自且彼此独立地表示氢原子、羟基或卤素原子,或R6及R7形成任选地经取代的环烷基或环杂烷基环。
及/或
其中各个基团彼此独立地且在每次出现时相同或不同地具有以下含义:
R1、R2、R5及R6各自且彼此独立地表示H、卤素、-OH、-SH、-NRxxRyy-、-CO-Rxx-、-COORxx、-OCORxx、-OCO-ORxx、-S-CORxx、-CO-SRxx、-NRxx-CO-ORyy、-O-CO-NRxxRyy、-NRxx-CO-NRxxRyy,由此式UVI中的R1或R6之一表示-OH,
R3及R4各自代表氢原子、羟基或卤素原子,
Rxx及Ryy各自彼此独立地表示H、具有1至12个C原子的烷基,其中此外,一个或多个不相邻的CH2基团可以O及/或S原子彼此不直接键联的方式各自彼此独立地经-O-、-S-、-NH-、-NRxx-、-SiRxxRyy-、-CO-、-COO-、-OCO-、-OCO-O-、-S-CO-、-CO-S-、-NRxx-CO-O-、-O-CO-NRxx-、-NRxx-CO-NRyy-、-CH=CH-或-C≡C-替代,
及/或
其中各个基团彼此独立地且在每次出现时相同或不同地具有以下含义:
R1至R9各自代表氢原子、羟基、卤素原子、具有1至20个碳原子的烷基、具有3至20个碳原子的烯基、具有1至20个碳原子的烷氧基或具有6至20个碳原子的芳基;
Ra表示具有1至20个,优选1至12个C原子的直链或支链烷基,其任选地经F、Cl、Br、I或CN单取代或多取代,且其中此外,一个或多个不相邻的CH2基团可以O及/或S原子各自彼此不直接键联的方式彼此独立地经-O-、-S-、-NH-、-NRxx-、-SiRxxRyy-、-CO-、-COO-、-OCO-、-OCO-O-、-S-CO-、-CO-S-、-NRxx-CO-O-、-O-CO-NRxx-、-NRxx-CO-NRyy-、-CH=CH-或-C≡C-替代,
Rxx及Ryy各自彼此独立地表示H或具有1至12个C原子的烷基。
及/或
其中各个基团彼此独立地且在每次出现时相同或不同地具有以下含义:
Pa是可聚合基团,优选是(甲基)丙烯酸酯基,
Sp是具有1至12个C原子的直链或支链亚烷基,其中此外,一或两个不相邻的CH2基团可以O原子彼此不直接键联的方式经-O-、-CH=CH-、-CO-、-OCO-或-COO-替代,
X1及X2各自且独立地表示-O-、-CH=CH-、-CF2O-、-OCF2-、-CH2O-、-OCH2-、-CO-O-、-O-CO-、-C2F4-、-CF=CF-或单键,优选表示-O-、-CO-O-、-O-CO-,
Ra-d各自且独立地表示具有1至20个C原子、优选具有1至15个C原子、非常优选具有1至12个C原子的直链或支链烷基,
R1及R2各自且独立地表示H、CH3、OH、ORa或O●,且
n表示1与8之间的整数。
稳定剂的典型可商购的实例是例如HALS型稳定剂,诸如Tinuvin 770、Uvinul3049及/或Tinuvin 970,其均可获自德国BASF,及/或可获自日本Adeka的LA-F70,其优选以0.1至5重量%,非常优选0.2至3重量%的量存在。
在另一种优选实施方案中,RM配制剂包含一种或多种溶剂,其优选选自有机溶剂。溶剂优选选自酮类例如丙酮、甲基乙基酮、甲基丙基酮、甲基异丁基酮或环己酮;乙酸酯类例如乙酸甲酯、乙酸乙酯或乙酸丁酯或乙酰乙酸甲酯;醇类例如甲醇、乙醇或异丙醇;芳族溶剂例如甲苯或二甲苯;脂环族烃类例如环戊烷或环己烷;卤代烃类例如二或三氯甲烷;二醇类或它们的酯类例如PGMEA(丙二醇单甲基醚乙酸酯)、γ-丁内酯。也可以使用二元、三元或更多元的上述溶剂混合物。
在含有一种或多种溶剂的RM配制剂的情况下,全部固体,包括RM,在溶剂中的总浓度优选为10-60%。
RM的聚合优选在引发剂的存在下进行,所述引发剂在光化辐射波长下吸收。为了该目的,优选RM配制剂含有一种或多种聚合引发剂。在另一优选实施方案中,可聚合LC材料包含一种或多种、更优选一或两种光引发剂的组合,该光引发剂例如选自可商购的或(Ciba AG)系列,尤其是Irgacure 127、Irgacure 184、Irgacure 369、Irgacure 651、Irgacure 817、Irgacure 907、Irgacure 1300、Irgacure、Irgacure 2022、Irgacure 2100、Irgacure 2959或Darcure TPO,其进一步选自可商购的OXE02(Ciba AG)、NCI 930、N1919T(Adeka)、SPI-03或SPI-04(Samyang),或优选其组合,诸如SPI-03与NCI-930。
RM配制剂中总体可聚合引发剂的浓度优选是0.1至10%,非常优选是0.5至8%,更优选是2至6%。
优选地,除一种或多种式I化合物外,可聚合LC材料包含:
a)一种或多种二反应性或多反应性可聚合介晶化合物,
b)任选的一种或多种单反应性可聚合介晶化合物,
c)任选的一种或多种抗氧化添加剂,
d)任选的一种或多种附着力促进剂,
e)任选的一种或多种表面活性剂,
f)任选的一种或多种单反应性、二反应性或多反应性可聚合非介晶化合物,
g)任选的一种或多种在用于引发光聚合的波长下显示最大吸收的染料,
h)任选的一种或多种链转移剂,
i)任选的一种或多种稳定剂,
j)任选的一种或多种润滑剂及流动助剂,及
k)任选的一种或多种稀释剂,
l)任选的非可聚合向列组分。
更优选地,可聚合LC材料包含:
a)一种或多种式I化合物,及
b)一种或多种,优选两种或更多种二反应性可聚合介晶化合物,若存在,则优选以10至90重量%,非常优选15至75重量%的量存在,其优选选自式DRMa-1化合物,及/或
c)一种或多种,优选两种或更多种单反应性可聚合介晶化合物,优选以10至95重量%,非常优选25至85重量%的量存在,其优选选自式MRM-1及/或MRM-7化合物,及/或
d)一种或多种式ND化合物,优选以1至50%,更优选1至40%的量存在,及/或
g)任选的一种或多种光引发剂,其优选选自SPI-03及/或Adeka NCI-930,且若存在,则优选以0.1至5重量%,非常优选0.2至3重量%的量存在,及/或
h)任选的一种或多种稳定剂,其优选选自HALS型稳定剂,诸如Tinuvin 770、Uvinul 3049及/或Tinuvin 970及/或LA-F70,且若存在,则优选以0.1至5重量%,非常优选0.2至3重量%的量存在。
根据本发明的聚合物的制备可通过技术人员已知和描述于文献中的方法进行,例如D.J.Broer;G.Challa;G.N.Mol,Macromol.Chem,1991,192,59。
通常,RM、RM混合物或RM配制剂例如通过涂覆或印刷方法涂覆于或以其它方式施加于基板之上,其中RM以统一取向而配向。优选RM以平面取向而配向,即RM分子的长分子轴平行于基板配向。然而,同样优选地将RM配向为垂面配向或倾斜配向。
然后,经配向的RM原位聚合,优选在其中它们展示出LC相的温度下,例如通过暴露于热或光化辐射。优选RM通过光聚合而聚合,非常优选通过UV-光聚合,以固定统一配向。如果需要,统一配向可通过额外的方式如RM的剪切或退火、基板表面处理、或向RM混合物或RM配制剂添加表面活性剂而促进。
作为基板,例如可使用玻璃或石英片或塑料膜。也可在聚合之前和/或期间和/或之后将第二基板放到经涂覆材料的顶部。基板可在聚合之后移除或不移除。当在通过光化辐射固化的情况下使用两块基板时,至少一块基板对于用于聚合的光化辐射必须是透射的。可使用各向同性或双折射基板。在聚合之后基板不自聚合膜移除的情况下,优选使用各向同性基板。
适合和优选的塑料基板为例如聚酯膜例如聚对苯二甲酸亚乙基酯(PET)或聚萘二甲酸亚乙基酯(PEN)、聚乙烯醇(PVA)、聚碳酸酯(PC)或三乙酰基纤维素(TAC),非常优选PET或TAC膜。作为双折射基板,可使用例如单轴拉伸塑料膜。PET膜可商购自例如DuPontTeijin Films,商标名为
优选将RM和其它固体添加剂溶于溶剂。然后将溶液涂覆或印刷于基板上,例如通过旋涂或印刷或其它已知技术,并于聚合之前将溶剂蒸发掉。在许多情况下,适合加热经涂覆的溶液以促进溶剂的蒸发。
RM配制剂可通过常规的涂覆技术如旋涂或刮涂施用于基板上。也可通过专业人员已知的常规的印刷技术施用于基板上,如例如丝网印刷、胶版印刷、卷对卷印刷、凸版印刷、凹版印刷、轮转凹版印刷、柔性版印刷、雕刻凹版印刷、移印、热封印刷、喷墨印刷或通过打印机(stamp)或印刷板的方式印刷。
在优选的实施方案中,RM配制剂展示出平面配向。这可例如通过基板的摩擦处理、通过涂覆期间或之后剪切材料、通过聚合之前退火材料、通过应用配向层、通过向经涂覆的材料应用磁场或电场、或通过向配制剂添加表面活性化合物来实现。配向技术的综述于例如I.Sage在"Thermotropic Liquid Crystals",由G.W.Gray编辑,John Wiley&Sons,1987,第75-77页;和T.Uchida和H.Seki in"Liquid Crystals–Applications and Uses第3卷",由B.Bahadur编辑,World Scientific Publishing,Singapore 1992,第1-63页中给出。配向材料和技术的综述于J.Cognard,Mol.Cryst.Liq.Cryst.78,Supplement 1(1981),第1-77页中给出。
也可将配向层施用于基板上并将RM混合物或RM配制剂提供于该配向层上。适合的配向层为本领域已知的,如例如经摩擦的聚酰亚胺或通过如US 5,602,661、US 5,389,698或US 6,717,644中所描述的光配向制备的配向层。
也可在聚合之前通过升高温度下退火RM诱导或改善配向,但是所述温度低于它们的清亮点温度。
聚合例如通过将可聚合材料暴露于热或光化辐射来实现。光化辐射意指用光,如UV光、IR光或可见光照射,用X-射线或伽马射线照射或用高能粒子,例如离子或电子照射。优选聚合通过UV照射实现。作为光化辐射源,可使用例如单个UV灯或一组UV灯。当使用高功率灯时,可减少固化时间。另一种可能的光化辐射源为激光,如例如UV、IR或可见激光。
固化时间取决于,特别是,RM反应性、经涂覆层的厚度、聚合引发剂的类型和UV灯的功率。固化时间优选≤5分钟,非常优选≤3分钟,最优选≤1分钟。对于大规模生产,优选≤30秒的短固化时间。
聚合过程不限于一个固化步骤。也可通过两个或更多个步骤进行聚合,其中将膜暴露于两个或更多个相同类型的灯,或依次暴露于两个或更多个不同的灯。不同固化步骤的固化温度可相同或不同。来自不同灯的灯功率和剂量也可相同或不同。除了上述条件外,方法步骤也可在暴露于不同的灯之间包括热步骤,如例如JP 2005-345982 A和JP 2005-265896 A中所描述的。
优选聚合于空气中进行,但也可在惰性气体氛围如氮气或氩气中聚合。
本发明聚合物膜的厚度优选地小于15微米,非常优选地小于12微米,最优选地小于10微米。
本发明的RM、RM混合物、RM配制剂及聚合物可用于光学、光电或电子器件或其组件中。
例如,其可用于光学延迟膜、偏振器、补偿器、分束器、反射膜、配向层、滤色器、抗静电保护片或电磁干扰保护片、用于自动立体3D显示器的偏振控制型透镜、RM透镜及用于窗应用的IR反射膜。
本发明的RM、RM混合物、RM配制剂、聚合物及器件组件可用于例如选自光电显示器、尤其是液晶显示器(LCD)、自动立体3D显示器、有机发光二极管(OLED)、光学数据储存器件及窗应用的器件中。
本发明的RM、RM混合物、RM配制剂、聚合物和器件组件可用于LCD的可转换LC盒的外侧或基板,通常为玻璃基板之间,形成可转换LC盒并含有可转换LC介质(盒内应用)。
本发明的RM、RM混合物、RM配制剂、聚合物和器件组件可用于常规的LC显示器,例如具有垂直配向如DAP(配向相畸变)、ECB(电控双折射)、CSH(颜色超垂面)、VA(垂直配向)、VAN或VAC(垂直配向向列型或胆甾型)、MVA(多畴垂直配向)、PVA(图案垂直配向)或PSVA(聚合物稳定垂直配向)型的显示器;具有弯曲或混合配向如OCB(光学补偿弯曲盒或光学补偿双折射)、R-OCB(反射OCB)、HAN(混合配向向列)或Pi-盒(π-盒)型显示器;具有扭转配向如TN(扭曲向列)、HTN(高度扭曲向列)、STN(超扭曲向列)、AMD-TN(有源矩阵驱动TN)型显示器;IPS(平面内切换)型显示器,或具有在光学各向同性相切换的显示器。
本发明的RM、RM混合物、RM配制剂、和聚合物可用于多种类型的光学膜,诸如用于LCD补偿及/或OLED抗反射/光学补偿的A板、+C板、O板。
除非另有说明,如上下文所述的RM混合物或RM配制剂中固体成分的百分数指混合物或配制剂中固体的总量,即无任何溶剂。
除非另有说明,全部光学、电光学性质和物理参数如双折射、介电常数、电导率、电阻率和薄层电阻指20℃温度下的。
除非本文另有明确说明,如本文所用,术语的复数形式在此被解释为包括单数形式,并且反之亦然。
应理解可作出本发明前述实施方案的变形,同时仍落入本发明的范围之内。本说明书中公开的各特征,除非另有说明,可被起到相同、相等或类似目的的替代特征所替代。因此,除非另有说明,所公开的各特征仅为一个通用系列相等或类似特征的一个实例。
本说明书中所公开的全部特征可以任意组合合并,除了其中至少部分该特征和/或步骤为互斥的组合之外。特别地,本发明的优选特征可应用于本发明的全部方面并可以任意组合使用。同样,非必要组合中所描述的特征可单独使用(不以组合形式)。
以下实施例意欲解释本发明而非对其进行限制。下文所描述的方法、结构和性质也可应用或转移至本发明所要求保护但在前述说明书或实施例中未明确描述的材料。
实施例
化合物实施例
化合物实施例1
如下文描述制备化合物(RM-1):
1.1制备2-氟-4-(6-羟基己-1-炔-1-基)苯酚
使4-溴-2-氟苯酚(9.55g,50mmol)及二异丙胺(75ml,536mmol)混合以提供固体。添加己炔-5-醇(4.5g,46mmol)且对混合物进行超声波处理持续30分钟。添加碘化亚铜(I)(285mg,1.5mmol)、乙酸钯(II)(570mg,2mmol)及三(叔丁基鏻)四氟硼酸盐(645mg,2.2mmol),且在40℃下加热混合物4小时。冷却混合物,且倒入浓盐酸(75ml)与冰(150g)的混合物中。用乙酸乙酯(300及2×200ml)提取混合物。在真空下从合并的有机提取物中移除溶剂。将残余物溶解于DCM(50ml)中,且用一定梯度的DCM:乙酸乙酯:IPA洗脱,在二氧化硅(120g)上通过真空快速色谱法纯化。合并含有产物的级分,且在真空下移除溶剂。将油(5.6g)溶解于DCM(50ml)中,且用一定梯度的DCM:乙酸乙酯:IPA洗脱,在二氧化硅(120g)上通过真空快速色谱法纯化。合并含有产物的级分,且在真空下移除溶剂(5.5g)。将油(5.5g)溶解于DCM(50ml)中,且用一定梯度的DCM:乙酸乙酯:IPA洗脱,在碱性氧化铝(120g)上通过真空快速色谱法纯化。随后用一定梯度的DCM/甲醇洗脱柱。合并含有产物的级分,且在真空下移除溶剂以提供所需产物2-氟-4-(6-羟基己-1-炔-1-基)苯酚(3.87g,37%产率)。
1.2制备2-氟-4-(6-羟基己基)苯酚(APN M1859)
在室温下使2-氟-4-(6-羟基己-1-炔-1-基)苯酚(APN M1825,3.87g,18.6mmol)、碳载钯(10%,1g)及THF(100ml)氢化7小时。经由硅藻土滤除催化剂,且在真空下移除溶剂。将残余物溶解于DCM中,且用一定梯度的DCM:乙酸乙酯:IPA洗脱,在二氧化硅(120g)上通过真空快速色谱法纯化。合并含有产物的级分,且在真空下移除溶剂以提供所需产物2-氟-4-(6-羟基己基)苯酚(1.61g,41%产率)。
1.3制备3-氯丙酸6-(3-氟-4-羟基苯基)己酯
使用迪恩-斯塔克(Dean Stark)设备使2-氟-4-(6-羟基己基)苯酚(1.61g,7.6mmol)、3-氯丙酸(1g,9.2mmol)、对甲苯磺酸(1g)及甲苯(20ml)回流3小时。冷却混合物,用水洗涤(2×20ml),且在真空下移除溶剂。将残余物溶解于DCM中,且用一定梯度的DCM:乙酸乙酯洗脱,在二氧化硅(60g)上通过真空快速色谱法纯化。合并含有产物的级分,且在真空下移除溶剂以提供所需产物3-氯丙酸6-(3-氟-4-羟基苯基)己酯(1.9g,83%产率)。
1.4制备RM-1
在室温下搅拌3-氯丙酸6-(3-氟-4-羟基苯基)己酯(APN M1865,1.9g,6.3mmol)、反式-4-(反式-4’-正丙基环己基)环己烷甲酸(1.7g,6.7mmol)、DMAP(0.8g,6.6mmol)及DCM(10ml)。添加一份DCC(10ml,1M于DCM中,10mmol),且搅拌混合物过夜。添加三乙胺(10ml,72mmol),且在40℃下搅拌混合物8小时。冷却混合物。使浓盐酸(10ml)与水(50ml)混合,且添加至反应混合物中。搅拌混合物30分钟,过滤,用DCM洗涤。分离来自过滤物的两层,且用DCM(2×50ml)提取水层。在无水硫酸钠上干燥有机层,过滤,且在真空下从过滤物移除溶剂。将残余物溶解于DCM:石油1:1中,且用一定梯度的石油/DCM洗脱,在二氧化硅(60g)上通过真空快速色谱法纯化。合并含有产物的级分,且在真空下移除溶剂。从DCM(2ml)与石油(30ml)的混合物中结晶出产物。在冰箱中冷却混合物1小时,过滤,用冷石油洗涤,且干燥以提供所需产物RM-1,其呈白色固体(2.18g,69%产率)。
相特性:K-N(S)50.9℃S-N100.9℃N-I 165.2℃
向列范围64.3℃
LC范围114.3℃
1H NMR(400MHz,氯仿-d)δ7.02-6.87(m,1H),6.39(dd,J=17.3,1.4Hz,0H),6.12(dd,J=17.3,10.4Hz,0H),5.81(dd,J=10.4,1.5Hz,0H),4.14(t,J=6.6Hz,1H),2.58(t,J=7.7Hz,1H),2.49(t t,J=12.2,3.6Hz,0H),2.21-2.11(m,1H),1.88-1.79(m,1H),1.80-1.71(m,1H),1.72-1.47(m,2H),1.46-1.23(m,2H),1.06(dddd,J=48.2,24.4,10.7,3.1Hz,3H),0.87(t,J=7.2Hz,2H)。
13C NMR(101MHz,氯仿-d)δ174.07,166.47,155.16,152.69,142.15,142.08,136.24,136.11,130.65,128.73,124.26,124.23,123.40,123.38,116.56,116.38,64.71,43.55,43.36,42.62,39.93,37.73,35.35,33.67,31.14,30.14,29.43,29.25,28.90,28.67,25.93,20.18,14.57。
化合物实施例2
如下文描述制备化合物(RM-2):
2.1制备丙酸6-(4-羟基苯基)己酯
使用反向迪恩-斯塔克设备使4-(6-羟基己基)苯酚(71.7g,369mmol)、3-氯丙酸(44.06g,406mmol)、对甲苯磺酸(5g)及DCM(500ml)回流8小时。冷却混合物,用水(500ml)洗涤。在无水硫酸钠上干燥有机层,过滤,且在真空下从过滤物中移除溶剂。将油溶解于DCM中,且使其向下通过二氧化硅塞,伴随用DCM洗脱,以提供呈无色油的所需产物:丙酸6-(4-羟基苯基)己酯(89.8g,86%产率)。
制备RM-2
在室温下搅拌4’-丙基-[1,1’-双(环己烷)]-4-甲酸((Merck,2.79653)3.78g,15mmol)、丙酸6-(4-羟基苯基)己酯(4.27g,15mmol)、DMAP(1.83g,15mmol)及DCM(50ml)。添加DCC(20ml,1M于DCM中,20mmol),且搅拌混合物过夜。添加三乙胺(25ml,179mmol)、Irganox 1076(几乎无结晶),且在35℃下搅拌混合物过夜。冷却混合物。使水(75ml)与浓盐酸(25ml)混合,添加且搅拌1小时。过滤混合物,且用DCM洗涤。分离两层,且用DCM(2×50ml)提取水层。在无水硫酸钠上干燥合并的有机层,过滤,且在真空下从过滤物移除溶剂。将残余物溶解于石油:DCM(50ml):(50ml)中,且用一定梯度的石油:DCM洗脱,在二氧化硅(120g)上通过真空快速色谱法纯化。合并含有产物的级分,且在真空下移除溶剂。
由异丙醇(50ml)结晶产物,在冰箱中冷却1小时,过滤出,用冷异丙醇洗涤以提供所需产物RM-2,其呈白色固体(5.56g,77%产率)。
相特性:K-N(S)40.7℃S-N 120.7℃N-I 158.1℃
向列范围37.4℃
LC范围117.4℃
1H NMR(400MHz,氯仿-d)δ7.18-7.11(m,2H),6.99-6.91(m,2H),6.39(dd,J=17.3,1.5Hz,1H),6.11(dd,J=17.3,10.4Hz,1H),5.81(dd,J=10.4,1.5Hz,1H),4.14(t,J=6.7Hz,2H),2.59(t,J=7.7Hz,2H),2.44(tt,J=12.2,3.6Hz,1H),2.20-2.10(m,2H),1.86(s,1H),1.84-1.80(m,1H),1.77(d,J=2.8Hz,1H),1.76-1.58(m,6H),1.55-1.45(m,2H),1.46-1.23(m,5H),1.19-1.07(m,5H),1.07-1.04(m,1H),1.04-0.98(m,2H),0.98-0.91(m,1H),0.87(t,J=7.3Hz,5H)。
13C NMR(101MHz,氯仿-d)δ175.04,166.47,148.95,140.05,130.62,129.32,128.75,121.35,64.76,43.84,43.38,42.66,39.93,37.73,35.36,33.67,31.44,30.15,29.44,29.29,28.97,28.68,25.95,20.18,14.57。
化合物实施例3
如下文描述制备化合物(RM-3):
3.1制备丙酸6-(4-羟基苯基)己酯
使用反向迪恩-斯塔克设备使4-(6-羟基己基)苯酚(71.7g,369mmol)、3-氯丙酸(44.06g,406mmol)、对甲苯磺酸(5g)及DCM(500ml)回流8小时。冷却混合物,用水(500ml)洗涤。在无水硫酸钠上干燥有机层,过滤,且在真空下从过滤物移除溶剂。将油溶解于DCM中,且使其通过二氧化硅塞,伴随用DCM洗脱,以提供呈无色油的所需产物:丙酸6-(4-羟基苯基)己酯(89.8g,86%产率)。
3.2制备RM-3
在室温下搅拌4’-戊基-[1,1’-双(环己烷)]-4-甲酸((Merck,2.79656)4.2g,15mmol)、丙酸6-(4-羟基苯基)己酯(4.27g,15mmol)、DMAP(1.83g,15mmol)及DCM(50ml)。添加DCC(20ml,1M于DCM中,20mmol)且搅拌混合物过夜。添加三乙胺(25ml,179mmol)、Irganox1076(几乎无结晶),且在35℃下搅拌混合物过夜。冷却混合物。使水(75ml)与浓盐酸(25ml)混合,添加且搅拌1小时。过滤混合物,且用DCM洗涤。分离两层,且用DCM(2×50ml)提取水层。在无水硫酸钠上干燥合并的有机层,过滤,且在真空下从过滤物移除溶剂。将残余物溶解于石油:DCM(50ml):(50ml)中,且用一定梯度的石油:DCM洗脱,在二氧化硅(120g)上通过真空快速色谱法纯化。合并含有产物的级分,且在真空下移除溶剂。由异丙醇(50ml)结晶产物,在冰箱中冷却1小时,过滤出,用冷异丙醇洗涤以提供所需产物RM-3,其呈白色固体(6.06g,79%产率)。
相特性:K-N(S)45.8℃S-N 1145℃N-I 158.1℃
向列范围13.6℃
LC范围112.3℃
1H NMR(400MHz,氯仿-d)δ7.15(d,J=8.3Hz,2H),6.99-6.91(m,2H),6.39(dd,J=17.3,1.4Hz,1H),6.11(dd,J=17.3,10.4Hz,1H),5.81(dd,J=10.4,1.5Hz,1H),4.14(t,J=6.7Hz,2H),2.59(t,J=7.7Hz,2H),2.44(t t,J=12.2,3.6Hz,1H),2.20-2.09(m,2H),1.88-1.80(m,2H),1.80-1.57(m,7H),1.52(dd,J=12.5,3.2Hz,2H),1.48-1.18(m,10H),1.19-1.07(m,5H),1.07-0.91(m,4H),0.88(t,J=6.9Hz,5H)。
13C NMR(101MHz,氯仿-d)δ175.37,166.79,149.27,140.37,130.94,129.64,129.07,121.67,65.08,44.16,43.70,42.97,38.34,37.90,35.67,34.02,32.70,31.76,30.47,29.76,29.61,29.29,29.00,27.13,26.27,23.18,14.59。
化合物实施例4
如下文描述制备化合物(RM-4):
4.1制备4-(6-羟基己-1-炔-1-基)苯甲酸
将4-碘苯甲酸(100g,403mmol)溶解于THF(500ml)及三乙胺(50ml,359mmol)中。添加碘化亚铜(I)(1g,190mmol)及二氯化双(三苯基膦)钯(10g,14mmol),在冷却时缓慢添加己-5-炔-1-醇(40g,407mmol),随后加热至50℃过夜。冷却反应物,且过滤。在真空下移除溶剂。添加DCM及稀释酸以洗涤且移除剩余三乙胺。伴随着用THF/石油洗脱,在二氧化硅上层析残余物。在真空下蒸发含有产物的级分。在用石油且随后用醚/石油洗脱,在二氧化硅上层析残余物。在真空下蒸发含有产物的级分以提供呈灰白色固体的产物:4-(6-羟基己-1-炔-1-基)苯甲酸(26g,29.5%产率)。
4.2制备4-(6-羟基己基)苯甲酸
在5%碳载钯(3g)存在下于氢气球下剧烈搅拌4-(6-羟基己-1-炔-1-基)苯甲酸(25g;0.11mol)于THF(250ml)中的溶液持续24小时。添加3g 10%碳载钯,且在30℃下另外搅拌反应物24小时。添加3g 10%碳载钯,且在30℃下再次搅拌混合物24小时。使混合物滤过硅藻土,用THF洗涤,随后在真空下蒸发。在添加1:1DCM:石油醚(150ml)时使残余物结晶,且冷却至-20℃。过滤混合物,用少量1:1DCM:石油醚洗涤,随后用石油醚洗涤以提供呈白色固体的所需产物:4-(6-羟基己基)苯甲酸(17.1g;67%)。
4.3制备4-{6-[(3-氯丙酰基)氧基]己基}苯甲酸
在反向迪恩-斯塔克设备中使4-[6-羟基己基)苯甲酸(30g;0.135mol)、3-氯丙酸(16.22g;0.15mol)及PTSA一水合物(1.70g,0.0089mol)于DCM(300ml)中回流(50℃)18小时,在此时,已收集所需体积的水。冷却后,用水洗涤溶液,在硫酸钠上干燥且在真空下蒸发。伴随着用20%乙酸乙酯于石油醚中洗脱,在二氧化硅(300g)上急骤层析残余物。用石油醚研磨以生成呈灰白色固体的所需产物:4-{6-[(3-氯丙酰基)氧基]己基}苯甲酸(42.28g;100%)。
制备实施例4
将DCC(1M于DCM中;13.4ml;0.0134mol)添加至4-{6-[(3-氯丙酰基)氧基]己基}苯甲酸(3.5g;0.0112mol)、DMAP(1.37g;0.011mol)及4’-丙基-[1,1’-双(环己烷)]-4-甲酸((Merck,2.79653)2.51g;0.0112mol)于DCM(30ml)中的溶液中。搅拌所得混合物1.5小时,随后添加三乙胺(10ml)及催化量的Irganox 1076,且将混合物加热至40℃持续16小时。冷却后,添加石油醚(30ml)。过滤所得浆液,且用1:1DCM:石油醚(2×30ml)洗涤。用2M盐酸、水洗涤过滤物,用硫酸钠干燥,随后在真空下蒸发。伴随着用DCM洗脱,在二氧化硅(150g)上层析残余物。在真空下蒸发含有产物的级分,随后用石油醚(60ml)研磨,且冷却至-20℃。过滤,随后在40℃下于真空下干燥提供呈白色固体的所需产物:RM-4(3.2g;59%)。
相特性:K-N(S)69.5℃S-N 102.0℃N-I 145.6℃
向列范围43.6℃
LC范围76.1℃
1H NMR(400MHz,氯仿-d)δ7.94(d,J=8.0Hz,2H),7.22(d,J=8.1Hz,2H),6.39(dd,J=17.4,1.4Hz,1H),6.11(dd,J=17.3,10.4Hz,1H),5.81(dd,J=10.4,1.4Hz,1H),4.87(t t,J=11.1,4.4Hz,1H),4.14(t,J=6.7Hz,2H),2.65(t,J=7.7Hz,2H),2.15-2.05(m,2H),1.86-1.75(m,3H),1.73(s,2H),1.72-1.60(m,5H),1.51-1.09(m,13H),1.11-0.96(m,2H),0.98-0.90(m,1H),0.87(t,J=7.3Hz,5H)。
13C NMR(101MHz,氯仿-d)δ166.46,166.32,148.01,130.65,129.75,128.72,128.65,128.44,74.22,64.71,42.90,42.44,39.92,37.68,36.00,33.65,32.17,31.17,30.34,28.94,28.66,28.11,25.93,20.18,14.57。
化合物实施例5–27
类似上文所给出的合成实施例制备以下化合物:
编号结构
比较实施例1
类似实施例1中描述的合成制备化合物(C1)及化合物(C2)。
方法
混合物制备
将化合物配制为33.33%固体,于甲苯:环己酮(7:3)中。在50℃下于烘箱中加热60分钟,且静置冷却10分钟。使用0.2μm PTFE针头式过滤器过滤。
膜制备:
针对+A膜,以1500rpm将混合物旋涂于摩擦的PI玻璃上持续30秒。在66℃下退火60秒。在20L min-1氮气下于20℃下冷却60秒。在20L min-1氮气下使用LED DELO灯,365nm,80mW cm-2固化60秒。
针对+C膜,以1000rpm将混合物旋涂于玻璃上持续30秒。在60℃下退火60秒。在氮气下于20℃下冷却60秒。在氮气下使用Fusion Light Hammer灯,800mW cm-2,600mJ cm-2固化。
膜的分析
由各混合物制造2种或3种膜。在椭偏仪上测量延迟,且测量膜厚度。计算色散,且引述平均值。针对ND+C膜,也计算双折射率,且引述平均值。
混合物实施例-ND+A
根据下表制备用于ND+A的以下混合物,聚合且测量诸如所得膜的色散的所得光学特性:
比较混合物CM-1:色散(R450/R550)=0.788
比较混合物CM-2:色散(R450/R550)=0.847
比较混合物CM-3:色散(R450/R550)=0.806
比较混合物CM-2与CM-3之间的不同之处在于,比较材料C1经比较材料C2替代。用环己基替代苯基引起聚合后较低的色散,但色散不低于0.79,因而需要进一步调整添加剂。
混合物M-1:色散(R450/R550)=0.778
参考混合物CM-3与实施例混合物M-1之间的不同之处在于,比较材料C2经根据本发明的RM-4替代。使用RM-4而非C2引起聚合后显著较低的色散。
混合物M-2:色散(R450/R550)=0.778
参考混合物CM-3与实施例混合物M-2之间的不同之处在于,比较材料C2经根据本发明的RM-2替代。使用RM-2而非C2引起聚合后显著较低的色散。
混合物M-3:色散(R450/R550)=0.777
参考混合物CM-3与实施例混合物M-3之间的不同之处在于,比较材料C2主要经根据本发明的RM-2替代。使用RM-2而非C2引起聚合后显著较低的色散。
混合物M-4:色散(R450/R550)=0.762
参考混合物CM-3与实施例混合物M-4之间的不同之处在于,比较材料C2主要经根据本发明的RM-1替代。使用RM-1而非C2引起聚合后显著较低的色散。
混合物M-5:
混合物M-6:
混合物M-7:
混合物M-8:
混合物M-9:
混合物实施例-ND+C
根据下表制备用于ND+C的以下混合物,聚合且测量诸如所得膜的色散的所得光学特性:
比较混合物CM-4:
40℃下的色散(R450/R550)=0.878
Δn(Rth/d)=0.046
比较混合物CM-5:
40℃下的色散(R450/R550)=0.924
Δn(Rth/d)=0.054
通过降低式ND(CM-4相对于CM-5)化合物的量,色散以及双折射率显著提高。
混合物M-10:
40℃下的色散(R450/R550)=0.924
Δn(Rth/d)=0.051
通过使用RM-2且降低式ND化合物的量,色散显著提高(CM-4相对于M5)。
Claims (17)
1.一种式I化合物,
P是可聚合基团,
Sp是间隔基团或单键,
R11是优选具有1至15个C原子的烷基、烷氧基、硫代烷基、烷羰基、烷氧基羰基、烷基羰氧基或烷氧基羰氧基,其更优选任选地经氟化,
A表示芳族或脂环基团,其任选地含有一个或多个选自N、O及S的杂原子,且任选地经L单取代或多取代,
L是F、Cl、Br、I、-CN、-NO2、-NCO、-NCS、-OCN、-SCN、-C(=O)NRxRy、-C(=O)ORx、-C(=O)Rx、-NRxRy、-OH、-SF5或是具有1至12个C原子的直链或支链烷基、烷氧基、烷羰基、烷氧基羰基、烷基羰氧基或烷氧基羰氧基,其中一个或多个H原子任选地经F或Cl替代,优选F、-CN或具有1至6个C原子的直链或支链烷基、烷氧基、烷羰基、烷氧基羰基、烷基羰氧基或烷氧基羰氧基,
R00、R000、Rx及Ry彼此独立地表示H或具有1至12个C原子的烷基,
Z11及Z12若多次出现,则彼此独立地表示-O-、-S-、-CO-、-COO-、-OCO-、-S-CO-、-CO-S-、-O-COO-、-CO-NR00-、-NR00-CO-、-NR00-CO-NR000、-NR00-CO-O-、-O-CO-NR00-、-OCH2-、-CH2O-、-SCH2-、-CH2S-、-CF2O-、-OCF2-、-CF2S-、-SCF2-、-CH2CH2-、-(CH2)n1、-CF2CH2-、-CH2CF2-、-CF2CF2-、-CH=N-、-N=CH-、-N=N-、-CH=CR00-、-CY1=CY2-、-C≡C-、-CH=CH-COO-、-OCO-CH=CH-或单键,
Y1及Y2彼此独立地表示H、F、Cl或CN,及
n1是1至10的整数。
2.根据权利要求1的化合物,其特征在于
a)由以下组成的组:1,4-亚苯基及1,3-亚苯基,其中此外,一或两个CH基团可经N替代,且其中此外,一个或多个H原子可经L替代,
b)选自由以下组成的基团的组:
其中此外,这些基团中的一个或多个H原子可经L替代,及/或一个或多个双键可经单键替代,及/或一个或多个CH基团可经N替代,
c)由以下组成的组:反式-1,4-亚环己基、1,4-亚环己烯基,其中此外,一个或多个不相邻的CH2基团可经-O-及/或-S-替代,且其中此外,一个或多个H原子可经F替代,或
d)由以下组成的组:四氢吡喃-2,5-二基、1,3-二噁烷-2,5-二基、四氢呋喃-2,5-二基、环丁烷-1,3-二基、哌啶-1,4-二基、噻吩-2,5-二基及硒吩-2,5-二基,其中的每一者也可经L单取代或多取代,且其中
L在每次出现时,相同或不同地表示-OH、-F、-Cl、-Br、-I、-CN、-NO2、SF5、-NCO、-NCS、-OCN、-SCN、-C(=O)N(Rz)2、-C(=O)Rz、-N(Rz)2、任选地经取代的甲硅烷基、具有6至20个C原子的任选地经取代的芳基或具有1至25个C原子、优选1至12个C原子、更优选1至6个C原子的直链或支链或环状烷基、烷氧基、烷羰基、烷氧基羰基、烷基羰氧基或烷氧基羰氧基,其中此外,一个或多个H原子可经F或Cl替代。
6.一种反应性介晶混合物,其包含至少一种根据权利要求1至5中任一项的式I化合物。
7.根据权利要求6的混合物,其中一种或多种反应性介晶选自式DRM,
P1-Sp1-MG-Sp2-P2 DRM
其中
P1及P2彼此独立地表示可聚合基团,
Sp1及Sp2彼此独立地是间隔基团或单键,及
MG是棒状介晶基团,其优选选自式MG
-(A1-Z1)n-A2- MG
其中
A1及A2若多次出现,则彼此独立地表示芳族或脂环基团,其任选地含有一个或多个选自N、O及S的杂原子,且任选地经L1单取代或多取代,
L1是P-Sp-、F、Cl、Br、I、-CN、-NO2、-NCO、-NCS、-OCN、-SCN、-C(=O)NR00R000、-C(=O)OR00、-C(=O)R00、-NR00R000、-OH、-SF5、任选地经取代的甲硅烷基、具有1至12个C原子的芳基或杂芳基、具有1至12个C原子的直链或支链烷基、烷氧基、烷羰基、烷氧基羰基、烷基羰氧基或烷氧基羰氧基,其中一个或多个H原子任选地经F或Cl替代,
R00及R000彼此独立地表示H或具有1个至12个C原子的烷基,
Z1若多次出现,则彼此独立地表示-O-、-S-、-CO-、-COO-、-OCO-、-S-CO-、-CO-S-、-O-COO-、-CO-NR00-、-NR00-CO-、-NR00-CO-NR000、-NR00-CO-O-、-O-CO-NR00-、-OCH2-、-CH2O-、-SCH2-、-CH2S-、-CF2O-、-OCF2-、-CF2S-、-SCF2-、-CH2CH2-、-(CH2)n1、-CF2CH2-、-CH2CF2-、-CF2CF2-、-CH=N-、-N=CH-、-N=N-、-CH=CR00-、-CY1=CY2-、-C≡C-、-CH=CH-COO-、-OCO-CH=CH-或单键,
Y1及Y2彼此独立地表示H、F、Cl或CN,
n是1、2、3或4,及
n1是1至10的整数。
9.根据权利要求6至8中一项或多项的混合物,其中一种或多种反应性介晶选自下式,
P1-Sp1-MG-R MRM
其中P1、Sp1及MG具有如式DRM中所给出的含义,
R是F、Cl、Br、I、-CN、-NO2、-NCO、-NCS、-OCN、-SCN、-C(=O)NRxRy、-C(=O)X、-C(=O)ORx、-C(=O)Ry、-NRxRy、-OH、-SF5、任选地经取代的甲硅烷基、具有1至12个C原子的直链或支链烷基、烷氧基、烷羰基、烷氧基羰基、烷基羰氧基或烷氧基羰氧基,其中一个或多个H原子任选地经F或Cl替代,
X是卤素,优选是F或Cl,及
Rx及Ry彼此独立地是H或具有1个至12个C原子的烷基。
10.根据权利要求6至9中一项或多项的混合物,其中一种或多种反应性介晶选自下式,
其中P0、L、r、x、y及z根据权利要求10中所给出的那样进行定义,
R0是具有1或多个,优选1至15个C原子的烷基、烷氧基、硫代烷基、烷羰基、烷氧基羰基、烷基羰氧基或烷氧基羰氧基,或表示Y0,
Y0是F、Cl、CN、NO2、OCH3、OCN、SCN、SF5或具有1个至4个C原子的单氟化、寡氟化或多氟化烷基或烷氧基,
Z0是-COO-、-OCO-、-CH2CH2-、-CF2O-、-OCF2-、-CH=CH-、-OCO-CH=CH-、-CH=CH-COO-或单键,
A0若多次出现,则彼此独立地是未经取代或经1、2、3或4个基团L取代的1,4-亚苯基,或反式-1,4-亚环己基,
u及v彼此独立地是0、1或2,
w是0或1,及
其中苯环及萘环可另外经一个或多个相同或不同基团L取代,且式MRM15中的z表示1。
11.根据权利要求6至10中一项或多项的混合物,其中一种或多种反应性介晶选自式ND化合物,
其中
U1、2彼此独立地选自
包括其镜像,其中该环U1及U2各自经由轴键键结至基团-(B)q-,且这些环中的一或两个不相邻的CH2基团任选地经O及/或S替代,
Q1、2彼此独立地是CH或SiH,
Q3是C或Si,
B在每次出现时,彼此独立地是-C≡C-、-CY1=CY2-或任选地经取代的芳族或杂芳族基团,
Y1、2彼此独立地是H、F、Cl、CN或R0,
q是1至10的整数,优选是1、2、3、4、5、6或7,
A1-4彼此独立地选自任选地经一个或多个基团R5取代的非芳族、芳族或杂芳族碳环或杂环基团,且其中-(A1-Z1)m-U1-(Z2-A2)n-及-(A3-Z3)o-U2-(Z4-A4)p-中的每一者均不含多于非芳族基团的芳族基团,且优选不含多于一个芳族基团,
Z1-4彼此独立地是-O-、-S-、-CO-、-COO-、-OCO-、-O-COO-、-CO-NR0-、-NR0-CO-、-NR0-CO-NR00-、-OCH2-、-CH2O-、-SCH2-、-CH2S-、-CF2O-、-OCF2-、-CF2S-、-SCF2-、-CH2CH2-、-(CH2)3-、-(CH2)4-、-CF2CH2-、-CH2CF2-、-CF2CF2-、-CH=CH-、-CY1=CY2-、-CH=N-、-N=CH-、-N=N-、-CH=CR0-、-C≡C-、-CH=CH-COO-、-OCO-CH=CH-、CR0R00或单键,
R0及R00彼此独立地是H或具有1个至12个C原子的烷基,
m及n彼此独立地是0、1、2、3或4,
o及p彼此独立地是0、1、2、3或4,
R1-5彼此独立地选自以下的相同或不同基团:H、卤素、-CN、-NC、-NCO、-NCS、-OCN、-SCN、-C(=O)NR0R00、-C(=O)X0、-C(=O)R0、-NH2、-NR0R00、-SH、-SR0、-SO3H、-SO2R0、-OH、-NO2、-CF3、-SF5、P-Sp-、任选地经取代的甲硅烷基或具有1至40个C原子的任选地经取代且任选地包含一个或多个杂原子的碳基或烃基;或表示P或P-Sp-,或经P或P-Sp-取代,其中该化合物包含至少一个表示P或P-Sp-或经P或P-Sp-取代的基团R1-5,
P是可聚合基团,
Sp是间隔基团或单键。
12.一种配制剂,其包含一种或多种根据权利要求1至5中一项或多项的式I化合物,或包含根据权利要求6或11的RM混合物,且进一步包含一种或多种光引发剂。
13.根据权利要求12的配制剂,其进一步包含一种或多种稳定剂。
14.根据权利要求12或13的配制剂,其进一步包含一种或多种润滑剂。
15.一种聚合物,其可通过使根据权利要求1至13中一项或多项的式I化合物或RM混合物或配制剂聚合而获得。
16.一种根据权利要求1至15中一项或多项的式I化合物、RM混合物、配制剂或聚合物的用途,其用于光学、电光学或电子组件或装置。
17.光学、电光学或电子装置或其组件,其包含根据权利要求1至15中一项或多项的式I化合物、RM混合物或配制剂或聚合物。
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