CN112812012A - 化合物、液晶组合物、液晶显示元件、液晶显示器 - Google Patents
化合物、液晶组合物、液晶显示元件、液晶显示器 Download PDFInfo
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- CN112812012A CN112812012A CN201911120072.9A CN201911120072A CN112812012A CN 112812012 A CN112812012 A CN 112812012A CN 201911120072 A CN201911120072 A CN 201911120072A CN 112812012 A CN112812012 A CN 112812012A
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- 125000005843 halogen group Chemical group 0.000 claims description 3
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- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
- C07C69/734—Ethers
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- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C217/04—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C217/06—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted
- C07C217/14—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to a carbon atom of a six-membered aromatic ring
- C07C217/18—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to a carbon atom of a six-membered aromatic ring the six-membered aromatic ring or condensed ring system containing that ring being further substituted
- C07C217/22—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to a carbon atom of a six-membered aromatic ring the six-membered aromatic ring or condensed ring system containing that ring being further substituted by carbon atoms having at least two bonds to oxygen atoms
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- C07C219/26—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
- C07C219/28—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton having amino groups bound to acyclic carbon atoms of the carbon skeleton
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- C07C69/593—Dicarboxylic acid esters having only one carbon-to-carbon double bond
- C07C69/60—Maleic acid esters; Fumaric acid esters
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- C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
- C07C69/732—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids of unsaturated hydroxy carboxylic acids
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- C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
- C07C69/738—Esters of keto-carboxylic acids or aldehydo-carboxylic acids
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
- C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D205/06—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/34—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D211/72—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D211/74—Oxygen atoms
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D335/00—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom
- C07D335/02—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
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- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
- C09K19/12—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings at least two benzene rings directly linked, e.g. biphenyls
- C09K19/126—Compounds containing at least one asymmetric carbon atom
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- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
- C09K19/20—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters or ethers
- C09K19/2007—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters or ethers the chain containing -COO- or -OCO- groups
- C09K19/2021—Compounds containing at least one asymmetric carbon atom
- C09K19/2028—Compounds containing at least one asymmetric carbon atom containing additionally a linking group other than -COO- or -OCO-, e.g. -CH2-CH2-, -CH=CH-, -C=C-; containing at least one additional carbon atom in the chain containing -COO- or -OCO- groups, e.g. -COO-CH*-CH3
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Abstract
Description
技术领域
本发明涉及一种可以实现自组装光配向功能的化合物,以及含有此类化合物的液晶组合物,属于液晶显示领域。
背景技术
可聚合介晶单元(RMs)目前是显示行业非常热门且重要的课题,其可能应用的领域包括聚合物稳定配向(PSA)液晶显示,聚合物稳定蓝相(PS-BP)液晶显示以及图形化位相差膜(Pattern Retarder Film)等。其中聚合物稳定取向型的液晶显示元件中,可利用聚合物来控制液晶分子的取向。PSA原理正被应用在不同典型的LC显示器中,例如PSA-VA,PSA-OCB,PS-IPS/FFS和PS-TN等液晶显示器。
目前,液晶分子的取向可利用特定的聚酰亚胺取向膜达成。作为用于赋予取向控制能力的液晶取向膜的取向处理方法,一直以来大多采用刷磨法。然而,对包含聚酰亚胺等的液晶取向膜的表面进行摩擦的刷磨法存在产尘、产生静电的问题。另外,由于近年来的液晶表示元件的高清晰化、相应基板上的电极或液晶驱动用切换能动元件所导致的凹凸,因此,无法用布均匀地摩擦液晶取向膜的表面、无法实现均匀的液晶取向。
另一方面,现有技术中虽然公开有不具有取向膜的液晶显示元件中使用含有聚合物及极性化合物的液晶组合物来控制液晶分析的取向,PSA-VA,PSA-OCB,PS-IPS/FFS和PS-TN等液晶显示元件可期待利用聚合物与极性化合物的组合达到此种效果的报道,但发现LC混合物和RMs在IPS/FFS显示器中的应用方面仍具有一些缺点。例如面板制程需要涂布配向层,不仅制程复杂,影响到产线的产能,而且会造成有机污染物的排放,另外,N.A.Clark等人,Langmuir2010,26(22),17482-17488已记载可使用以下结构的化合物:
发明内容
本发明的目的在于,提供一种能够自组装光配向的化合物,将含有该化合物的液晶组合物应用于液晶显示元件时不需要使用聚酰亚胺取向膜就能够进行配向,并且克服上述现有技术中的至少一个缺点,液晶配向的方法简化且配向稳定。
为了实现上述目的,本发明一方面提供了一种液晶化合物,所述液晶化合物的结构式如下式I所示,
其中,P11、P12各自独立地表示P1、P1-Sp-、-Z3-H、-Z3-L1、H原子、F原子或具有1~12个C原子的直链或支链烷基,其中一个或多个不相邻的-CH2-任选被-C(L0)=C(L00)-、-C≡C-、-N(L00)-、-O-、-S-、-CO-、-CO-O-、-O-CO-或-O-CO-O-替代,一个或多个H原子任选被卤素原子、CN、P1或P1-Sp-替代,且P11及P12中至少之一表示基团P1或P1-Sp-;
K1、K2、K3各自独立地表示4~25个碳原子的芳环、4~25个碳原子的杂芳环、4~25个碳原子的脂肪族环或4~25个碳原子的稠环,其中K1、K2、K3的环上一个或多个不相邻的-CH2-任选被-O-或者-S-替代,一个或多个H原子任选被L1或-Sp-P1取代;
L1表示F原子、碳原子数为1~10的烷基、氟取代的碳原子数为1~10的烷基、碳原子数为1~10的烷氧基、氟取代的碳原子数为1~10的烷氧基、碳原子数为2~10的链烯基、氟取代的碳原子数为2~10的链烯基、碳原子数为3~8的链烯氧基或氟取代的碳原子数为3~8的链烯氧基,且任一个-CH2-任选被亚环戊基、亚环丁基或亚环丙基替代;
Z1、Z2、Z3各自独立地表示单键、-O-、-S-、-CO-、-COO-、-OCO-、-OCOO-、-OCH2-、-CH2O-、-SCH2-、-CH2S-、-CF2O-、-OCF2-、-CF2S-、-SCF2-、-(CH2)n1-、-CF2CH2-、-CH2CF2-、-(CF2)n1-、-(CL0L00)n1-、-CH=CH-、-C≡C-、-CF=CF-、-CH=CH-COO-、-OCO-CH=CH-、-OCO-CH=CH-COO-、-N=N-、
n1表示1、2、3或4;
m、n、o、q各自独立地表示0、1、2、3或4,且m+o+n*q=1;
L0、L00各自独立地表示H原子或具有1~12个C原子的烷基;
G1、G2、G3各自独立地表示-Sp1-R1、-Sp2-R2、-Sp3-R3或R;
X表示三价基团或四价基团;Y表示C原子、N原子、S原子或P原子;
Sp、Sp1、Sp2、Sp3、Sp4、Sp5彼此独立的表示间隔基或单键;P1表示可聚合基团。
本发明另一方面,提供一种液晶组合物,其含有一种或多种式I所示化合物。
本发明的又一方面,提供一种液晶显示元件或液晶显示器,其包含本发明的化合物,或者本发明的液晶组合物,所述显示元件或显示器为有源矩阵显示元件或显示器或无源矩阵显示元件或显示器。
本发明的化合物能够作为自组装光配向剂(SAPA),利用该化合物的极性侧基与基板表面相互作用,由此使得SAPA能够在填充LC盒之后与LC混合物相分离,在基板上形成可利用线性偏振UV光光配向的层。然后,通过将式I所示化合物经偏振紫外光照射原位逐步聚合,得到稳定性好的光控取向膜,能够起到配向层的绝缘与对液晶分子水平配向的作用,液晶遵循经配向的SAPA的定向,以横跨整个显示器给出均匀平面配向。由此,能够避免配向层制程,使液晶显示元件或液晶显示器的制程得到简化,提高生产效率。
进一步,本发明的液晶组合物具有较低的粘度,可以实现快速响应,同时具有适中的介电各向异性Δε、适中的光学各向异性Δn。
附图说明
图1:本发明的式I-1-6所示化合物的核磁共振图谱。
具体实施方式
[化合物]
本发明的上述式I所示化合物优选选自下述式I-1至式I-9所示的化合物组成的组:
其中基团及参数具有与上述式I所示化合物结构式所指示的含义。
更优选地,所述式I所示化合物选自下述式I-1-1至式I-9-2所示的化合物组成的组:
作为本发明的式I所示化合物的制备方法,没有特别的限定。作为其中的一个实施方式,可以列举出例如按照下述的合成路线进行合成的方法,但不限于此:
方案1:
方案2:
其中,P1、L0具有上述式I所示化合物相同含义。
合成通式中原材料及试剂均可通过商业途径购买而得,此类方法原理、操作过程、常规后处理、过硅胶柱、重结晶提纯等手段是本领域合成人员所熟知的,完全可以实现合成过程,得到目标产物。
上述方法的反应均在溶剂中进行,前述溶剂选自四氢呋喃、N,N-二甲基甲酰胺、乙醇、甲醇、二氯甲烷、丙酮、甲苯和去离子水中的至少一种。
[液晶组合物]
本发明的液晶组合物中,包含一种或多种上述式I所示化合物。优选地,所述式I所示化合物在液晶组合物中的含量为0.01~10%。更优选地,所述式I所示化合物在液晶组合物中的含量为0.01~1%。
本发明的液晶组合物的一个实施方式中,还可以包含一种或多种式P所示的聚合性化合物,
Pa-(Spa)s1-A2-(Z-A1)n2-(Spb)s2-Pb P
其中,Pa、Pb各自独立地表示可聚合基团;
Spa、Spb各自独立地表示间隔基团;s1、s2各自独立地为0或1;
A1、A2各自独立地选自以下的组:
a)由反式-1,4-亚环己基、1,4-亚环己烯基及4,4′-亚双环己基组成的组,其中一个或多个不相邻的-CH2-基团任选被-O-或-S-替代,一个或多个H原子任选被F原子替代,
b)由1,4-亚苯基及1,3-亚苯基组成的组,其中一个或两个CH基团任选被N替代,一个或多个H原子任选被L替代,
c)由四氢吡喃-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-2,5-二基组成的组,其中一个或多个H原子任选被L取代;
d)下述基团组成的组:
其中这些基团中的一个或多个H原子任选被L替代,和/或一个或多个双键任选被单键替代,和/或一个或多个CH任选被N替代;n2为0、1、2或3;
Z表示-CO-O-、-O-CO-、-CH2O-、-OCH2-、-CF2O-、-OCF2-、具有2~4个碳原子的直链亚烷基、-O-、-CO-、-C(R0R00)-、-CH2CF2-、-CF2CF2-或单键;
L在每次出现时,相同或不同地表示F原子、Cl原子、CN、SCN、SF5或任选经氟化的具有1~12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、烷氧基羰氧基;
R0、R00各自彼此独立地表示H原子、F原子或具有1~12个C原子的直链或支链烷基,其中一个或多个H原子任选被F原子替代;
M表示-O-、-S-、-CH2-、-CHY1-或-CY1Y2-;Y1、Y2各自彼此独立地表示H原子、F原子、Cl原子、CN或具有1~12个C原子的直链或支链烷基,其中一个或多个H原子任选被F原子替代。
本发明的液晶组合物在含有前述的式P所示化合物的情况下,优选地,所述式P所示化合物在液晶组合物中的含量为0.01~10%。优选地,所述式P所示化合物在液晶组合物中的含量为0.01~1%。
优选地,前述式P的聚合性化合物选自下列式P1所示聚合性化合物,
其中,Pa、Pb各自独立地表示可聚合基团;Spa、Spb各自独立地表示间隔基团;
L1表示F原子、Cl原子、具有1~12个C原子的烷基、具有1~12个C原子的烷氧基;
r表示0、1或2。
优选地,所述式P1所示聚合性化合物选自下列式P1-1~P1-3所示化合物组成的组,
本发明的液晶组合物在含有式P所示化合物的情况下,优选地,所述式P所示化合物在液晶组合物中的含量为0.01~10%。更优选地,所述式P所示化合物在液晶组合物中的含量为0.01~1%。
本发明的液晶组合物的一个实施方式中,还包含一种或多种式II所示化合物和/或一种或多种式III所示化合物,
R5、R6各自独立地表示碳原子数为1~12的烷基,其中一个或多个不相邻的-CH2-基团任选地被-O-、-CH=CH-、-CO-、-O-CO-或-CO-O-替代;
Z4表示-CH2CH2-、-CH=CH-、-CF2O-、-OCF2-、-CH2O-、-OCH2-、-COO-、-OCO-、-C2F4-、-CF=CF-或单键;
R7、R8各自独立地表示碳原子数为1~10的烷基、氟取代的碳原子数为1~10的烷基、碳原子数为1~10的烷氧基、氟取代的碳原子数为1~10的烷氧基、碳原子数为2~10的链烯基、氟取代的碳原子数为2~10的链烯基、碳原子数为3~8的链烯氧基或氟取代的碳原子数为3~8的链烯氧基。
优选地,上述一种或多种式II所示化合物选自下列式II-1~II-17所示化合物组成的组:
优选地,上述一种或多种式III所示的化合物选自式III-1至式III-4所示化合物组成的组,
其中,R71、R81各自独立的表示碳原子数为2~6的烷基或碳原子数为2~6的烯基;其中,前述的碳原子数为2~6的烯基可以列举出例如乙烯基、2-丙烯基或者3-戊烯基。R82表示碳原子数为1~5的烷氧基。
本发明的液晶组合物中含有前述式Ⅱ所示化合物的情况下,式Ⅱ所示化合物在液晶组合物中的添加量(质量比)没有特别的限定,优选地,相对于液晶组合物中不包含式I所示化合物在内的其他成分的总量,可以为例如15~70%,优选为30~70%。
本发明的液晶组合物中含有前述式III所示化合物的情况下,式III所示化合物在液晶组合物中的添加量(质量比)没有特别的限定,优选地,相对于液晶组合物中不包含式I所示化合物在内的其他成分的总量,可以为例如1~30%,优选为5~20%。
通过将前述的式Ⅱ所示化合物与本发明的式I所示化合物在液晶组合物中组合使用,获得了液晶组合物的互溶性提高、响应速度提高的有益效果。通过在本发明的液晶组合物中组合使用式III所示的化合物,从而获得具有较大的光学各向异性Δn和较低的旋转粘度。
所述液晶组合物中还包含一种或多种式IV所示化合物,
其中,
①反式1,4-亚环己基、1,4-环己烯基基团,其中一个或多个不相邻的-CH2-基团任选被-O-或-S-取代;
②1,4-亚苯基基团,其中一个或两个CH基任选被N取代,一个或两个H原子任选被F原子取代;
X1、X2各自独立地表示H原子或F原子;
Y3表示F原子、碳原子数为1~6的直链烷基、碳原子数为1~6的直链烷氧基或碳原子数为2~6的直链烯基,其中一个或多个氢原子任选被F原子替代;
Z5表示单键、-CH2-、-CH2CH2-、-(CH2)3-、-(CH2)4-、-CH=CH-、-C≡C-、-COO-、-OOC-、-OCH2-、-CH2O-、-CF2CH2-、-CH2CF2-、-C2F4-或-CF=CF-;
r表示0、1或2。
优选地,前述一种或多种式Ⅳ所示化合物选自式Ⅳ1~Ⅳ15所示化合物组成的组:
其中,R9与前述的式Ⅳ所示化合物中的R9的含义相同,各自独立地表示碳原子数为1-10的烷基、碳原子数为1-10的烷氧基、碳原子数为2-10的链烯基或碳原子数为3-8的链烯氧基,且R9所示基团中任意一个或多个-CH2-任选被亚环戊基、亚环丁基或亚环丙基替代;式Ⅳ1~式Ⅳ6中的(F)各自独立地表示H或F;式Ⅳ7中的-(O)CF3表示-CF3或-OCF3。
作为前述的式Ⅳ所示化合物中的R9所示的碳原子数为1~10的烷基中一个或多个不相邻的-CH2-被亚环丙基、亚环丁基或亚环戊基取代后得到的基团,可以列举出例如环丙基、环丁基、环戊基、甲基亚环丙基、乙基亚环丙基、丙基亚环丙基、异丙基亚环丙基、正丁基亚环丙基、异丁基亚环丙基、叔丁基亚环丙基、甲基亚环丁基、乙基亚环丁基、丙基亚环丁基、异丙基亚环丁基、正丁基亚环丁基、异丁基亚环丁基、叔丁基亚环丁基、甲基亚环戊基、乙基亚环戊基、丙基亚环戊基、异丙基亚环戊基、正丁基亚环戊基、异丁基亚环戊基等。R9所示的基团中,从液晶化合物旋转粘度、溶解度和清亮点考虑优选的是环丙基或环戊基。
本发明的液晶组合物在含有式Ⅳ所示化合物的情况下,式Ⅳ所示化合物在液晶组合物中的添加量(质量比)没有特别的限定,优选地,相对于液晶组合物中不包含式I所示化合物在内的其他成分的总量,可以为例如1~55%,优选为30~50%。
式Ⅳ所示化合物为正介电各项异性,通过在液晶组合物在含有式Ⅳ所示化合物,能够进一步调节液晶组合物的阈值电压。
本发明的液晶组合物的一个实施方式中,还包含一种或多种式V所示化合物,
其中,R10、R11各自独立地表示碳原子数为1~10的烷基、氟取代的碳原子数为1~10的烷基、碳原子数为1~10的烷氧基、氟取代的碳原子数为1~10的烷氧基、碳原子数为2~10的链烯基、氟取代的碳原子数为2~10的链烯基、碳原子数为3~8的链烯氧基或氟取代的碳原子数为3~8的链烯氧基,且R10、R11中任意一个或多个不相邻的-CH2-任选被亚环戊基、亚环丁基或亚环丙基取代;Z6、Z7各自独立地表示单键、-CH2CH2-或-CH2O-;
s表示1或2;t表示0、1或2。
优选地,前述式V所示化合物选自式V-1至式V-15所示化合物组成的组,
其中,式V-1至式V-15所示化合物中的R10、R11与前述式V所示化合物中的R10、R11的含义相同,各自独立地表示碳原子数为1~10的烷基、氟取代的碳原子数为1~10的烷基、碳原子数为1~10的烷氧基、氟取代的碳原子数为1~10的烷氧基、碳原子数为2~10的链烯基、氟取代的碳原子数为2~10的链烯基、碳原子数为3~8的链烯氧基或氟取代的碳原子数为3~8的链烯氧基,并且R10、R11所示基团中任意一个或多个不相邻的-CH2-任选被亚环戊基、亚环丁基或亚环丙基取代。
本发明的液晶组合物中,通过将式V所示化合物与式I所示化合物组合使用,获得了液晶组合物的负介电各项异性增大的有益效果。
作为前述的式V中的R10、R11所示的碳原子数为1~10的烷基中一个或多个不相邻的-CH2-被亚环丙基、亚环丁基或亚环戊基取代后得到的基团,可以列举出环丙基、环丁基、环戊基、甲基亚环丙基、乙基亚环丙基、丙基亚环丙基、异丙基亚环丙基、正丁基亚环丙基、异丁基亚环丙基、叔丁基亚环丙基、甲基亚环丁基、乙基亚环丁基、丙基亚环丁基、异丙基亚环丁基、正丁基亚环丁基、异丁基亚环丁基、叔丁基亚环丁基、甲基亚环戊基、乙基亚环戊基、丙基亚环戊基、异丙基亚环戊基、正丁基亚环戊基、异丁基亚环戊基等。R10、R11所示的基团中,从液晶化合物旋转粘度、溶解度和清亮点的角度考虑优选的是环丙基、环丁基或环戊基。
本发明的液晶组合物在含有式V所示化合物的情况下,在液晶组合物中的添加量(质量比)没有特别的限定,优选地,相对于液晶组合物中不包含式I所示化合物在内的其他成分的总量,可以为例如10~65%,优选为20~50%。
本发明的液晶组合物的一个实施方式中,还包含一种或多种式VI所示化合物,
其中,R12、R13各自独立地表示碳原子数为1~10的烷基、氟取代的碳原子数为1~10的烷基、碳原子数为1~10的烷氧基、氟取代的碳原子数为1~10的烷氧基、碳原子数为2~10的链烯基、氟取代的碳原子数为2~10的链烯基、碳原子数为3~8的链烯氧基或氟取代的碳原子数为3~8的链烯氧基,并且R5、R6中任意一个或多个不相邻的-CH2-任选被亚环戊基、亚环丁基或亚环丙基替代;W表示-O-、-S-或-CH2O-。
优选地,式VI所示的化合物选自式VI-1至式VI-6所示化合物组成的组:
其中,R131表示碳原子数为2~6的烷基。
本发明的液晶组合物中,含有前述的式VI所示化合物的情况下,式VI所示化合物在液晶组合物中的添加量(质量比)没有特别的限定,相对于液晶组合物中不包含式I所示化合物在内的其他成分的总量,可以为例如1~15%,优选为2~10%。
通过在本申请的液晶组合物中含有前述的式VI所示的化合物,从而能够使得液晶组合物具有较大的负的介电各向异性,有利于降低器件的驱动电压。
另外地,本发明的液晶组合物中,还可以加入各种功能的掺杂剂,在含有掺杂剂的情况下,掺杂剂的含量优选在液晶组合物中所占的质量百分比为0.01~1%,这些掺杂剂可以列举出例如抗氧化剂、光稳定剂、手性剂。
抗氧化剂、光稳定剂可以列举出,
u表示1~10的整数。
通过将本发明的液晶组合物进行光辐照,优选利用线性偏振光对该液晶组合物进行辐照,能够引起液晶组合物的光配向。在优选实施方式中,线性偏振光是紫外光,通过用紫外光辐照使可聚合化合物固化以引起配向的固定,由此,能够同时使自组装光配向剂光配向及可聚合化合物光固化。
本发明的液晶显示器包含本发明的液晶组合物,前述液晶显示器为有源矩阵显示器或无源矩阵显示器。
可选的,前述液晶显示器可以为例如IPS或FFS显示器。
对于前述的本发明的液晶显示器,只要在其使用的液晶组合物中含有本发明的式I所示化合物,则对其结构没有任何限定,本领域技术人员能够根据所需的性能选择合适的液晶显示器的结构。
作为本发明的液晶显示器的一个实施方式,可以列举,例如下述的结构:包括第一基板、第二基板,以及设置在第一基板和第二基板之间的式I所示化合物、式P所示化合物以及其他液晶分子所组成的液晶组合物,第一基板与第二基板平行相对设置,第一基板设有公共电极、第二基板设有像素电极,第一基板与第二基板之间散布有间隔物。
实施例
为了更清楚地说明本发明,下面结合优选实施例和附图对本发明做进一步的说明。附图中相似的部件以相同的附图标记进行表示。本领域技术人员应当理解,下面所具体描述的内容是说明性的而非限制性的,不应以此限制本发明的保护范围。
本发明中,制备方法如无特殊说明则均为常规方法,所用的原料如无特别说明均可从公开的商业途径获得,百分比均是指质量百分比,温度为摄氏度(℃),液晶化合物也成为液晶单体,其他符号的具体意义及测试条件如下:
Cp表示液晶清亮点(℃),DSC定量法测试;
Δn表示光学各向异性,Δn=ne-no,其中,no为寻常光的折射率,ne为非寻常光的折射率,测试条件为25±2℃,589nm,阿贝折射仪测试;
Δε表示介电各向异性,Δε=ε∥-ε⊥,其中,ε∥为平行于分子轴的介电常数,ε⊥为垂直于分子轴的介电常数,测试条件为25±0.5℃,20微米平行盒,INSTEC:ALCT-IR1测试;
VHR表示电压保持率(%),测试条件为20±2℃、电压为±5V、脉冲宽度为10ms、电压保持时间16.7ms。测试设备为TOYO Model6254液晶性能综合测试仪;
γ1表示旋转粘度(mPa·s),测试条件为25±0.5℃,20微米平行盒,INSTEC:ALCT-IR1测试。
本发明实施例中使用的液晶单体结构用代码表示,液晶环结构、端基、连接基团的代码表示方法见下表1、表2。
表1:环结构的对应代码
表2:端基与链接基团的对应代码
举例:
实施例1
化合物结构式如下式I-1-6所示:
制备的具体操作流程:
步骤1
在反应瓶中加入22.8g(0.10mol)化合物1-1,27.9g(0.01mol)化合物1-2、碳酸钾16.6g(0.12mol)、Pd(dppf)2Cl2 0.5g、甲苯300mL和水100mL。氮气保护下加热至回流,反应2小时后,点板检测原料消失。加水和甲苯搅拌萃取分液,水层用甲苯萃取两次后合并甲苯层,用水洗涤后过硅胶柱层析,旋干溶剂,用甲苯和乙醇重结晶3次,得化合物1-3,白色固体32.5g,GC:98.1%。获得的式I-1-6所示化合物的核磁共振图谱如附图1所示。
步骤2
在反应瓶中加入33.8g(0.085mol)化合物1-3,19.0g(0.085mol)化合物1-4、碳酸钾13.8g(0.1mol)和DMF 500mL。氮气保护下加热至80℃,反应2小时后,点板检测原料消失。加水和甲苯搅拌萃取分液,水层用甲苯萃取两次后合并甲苯层,用水洗涤后过硅胶柱层析,旋干溶剂,用甲苯和乙醇重结晶3次,得化合物1-5,白色固体27.7g,GC:97.8%。
步骤3
在反应瓶中加入19.6g(0.036mol)化合物1-5和200mL四氢呋喃,之后,分批加入4.6g(0.040mol)四丁基氟化铵。室温反应2小时,点板检测化合物1-5消失。加水和乙酸乙酯搅拌萃取分液,水层用乙酸乙酯萃取两次后合并有机层,用水洗涤后干燥,旋干溶剂,用甲苯石油醚重结晶2次,得到化合物1-6,类白色固体13.3g,GC:96.8%。
步骤4
在反应瓶中加入15.3g(0.044mol)化合物1-6,4.0g(0.046mol)甲基丙烯酸,200ml二氯甲烷搅拌全溶,室温下加入9.6g(0.046mol)DCC,之后室温搅拌4小时,点板检测化合物1-6消失;加水搅拌分液,水层用二氯甲烷萃取两次后合并二氯甲烷层,用水洗涤后经无水硫酸钠干燥,旋干溶剂,用甲苯溶解后硅胶柱层析,用甲苯和乙醇重结晶3次,得到化合物1-7,白色固体18.5g,HPLC:99.2%。
步骤5
在反应瓶中加入18.5g(0.038mol)化合物1-7和250mL四氢呋喃。室温加入50mL 2N盐酸水溶液,室温反应4小时,点板检测原料消失。加水和甲苯搅拌萃取分液,水层用甲苯萃取两次后合并甲苯层,用水洗涤后过硅胶柱层析,旋干溶剂,用甲苯和石油醚重结晶3次,得到化合物I-1-6,白色固体10.9g,GC:99.0%。
实施例2
化合物结构式如下式I-4-2所示:
制备的具体操作流程:
步骤1
在反应瓶中加入55.6g(0.2mol)化合物2-1,26.7g(0.1mol)化合物2-2,500ml二氯甲烷搅拌全溶,室温下加入51.7g(0.25mol)DCC,之后室温搅拌4小时,点板检测原料消失;加水搅拌分液,水层用二氯甲烷萃取两次后合并二氯甲烷层,用水洗涤后经无水硫酸钠干燥,旋干溶剂,用甲苯溶解后硅胶柱层析,用甲苯和乙醇重结晶2次,得化合物2-3,白色固体60.3g,HPLC:98.3%。
步骤2
在反应瓶中加入28.3g(0.036mol)化合物2-3和200mL四氢呋喃,之后,分批加入4.6g(0.040mol)四丁基氟化铵。室温反应2小时,点板检测化合物2-3消失。加水和乙酸乙酯搅拌萃取分液,水层用乙酸乙酯萃取两次后合并有机层,用水洗涤后干燥,旋干溶剂,用甲苯石油醚重结晶2次,得到化合物2-4,类白色固体13.3g,GC:96.8%。
步骤3
在反应瓶中加入24.6g(0.044mol)化合物2-4,8.0g(0.093mol)甲基丙烯酸,200ml二氯甲烷搅拌全溶,室温下加入19.2g(0.093mol)DCC,之后室温搅拌4小时,点板检测化合物2-4消失;加水搅拌分液,水层用二氯甲烷萃取两次后合并二氯甲烷层,用水洗涤后经无水硫酸钠干燥,旋干溶剂,用甲苯溶解后硅胶柱层析,用甲苯和乙醇重结晶3次,得到化合物2-5,白色固体18.5g,HPLC:99.2%。
步骤4
在反应瓶中加入43.8g(0.063mol)化合物2-5和500mL四氢呋喃。室温加入100mL4N盐酸水溶液,室温反应4小时,点板检测原料消失。加水和甲苯搅拌萃取分液,水层用甲苯萃取两次后合并甲苯层,用水洗涤后过硅胶柱层析,旋干溶剂,用甲苯和石油醚重结晶3次,得到化合物I-4-2,白色固体28.7g,GC:98.5%。
制造显示器盒
通过原始未处理的无碱玻璃使用5μm间隔珠以Norland 65粘合剂制得显示器盒。用手组装该盒且接着使用具有50mW/cm2及3000mJ/cm2的高压水银灯固化。
盒填充及固化
在室温下使用毛细管作用对LC混合物进行毛细管填充,在100℃下退火1小时且接着在相同温度下通过线性偏振UV光(50mW/cm2)照射60秒。接着使该盒冷却至室温。
母体液晶组合物
如表3~8中所指示制备母体液晶组合物A-1~A-6
表3母体液晶组合物A-1
表4母体液晶组合物A-2
表5母体液晶组合物A-3
表6母体液晶组合物A-4
表7母体液晶组合物A-5
表8母体液晶组合物A-6
液晶组合物实施例
由上文所列的液晶组合物A-1至A-6及式I的化合物,根据下表中给出的组合物制备根据本发明的液晶组合物B-1至B-6。
配向实验
使用原始未处理的玻璃或ITO玻璃制造测试显示器,随后分别用根据混合物实施例B-1~B-6的向列型混合物填充且接着如上文所描述来固化。
然后,在光匣(light box)上的交叉偏振器之间研究配向质量。当该盒放置于交叉偏振器之间时观测到良好的暗态。在该盒旋转45°时观测到良好的透射状态。这展示通过来自实施例B-1~B-6的混合物实现的优异的均匀平面配向。液晶盒在78-80℃温度环境下,持续施加电压并切换暗态与亮态,500小时,配向稳定存在。在比较实验中,测试显示器在无式I的化合物的情况下用向列型主体混合物A-1~A-6填充,且以如针对根据本发明的混合物实施例B-1~B-6所描述的相同方式固化。在比较实验中,在所有偏振器配置下观测到非均匀的透射状态。
显然,本发明的上述实施例仅仅是为清楚地说明本发明所作的举例,而并非是对本发明的实施方式的限定,对于所属领域的普通技术人员来说,在上述说明的基础上还可以做出其它不同形式的变化或变动,这里无法对所有的实施方式予以穷举,凡是属于本发明的技术方案所引伸出的显而易见的变化或变动仍处于本发明的保护范围之列。
Claims (10)
1.一种化合物,其为式I所示,
其中,P11、P12各自独立地表示P1、P1-Sp-、-Z3-H、-Z3-L1、H原子、F原子或具有1~12个C原子的直链或支链烷基,其中一个或多个不相邻的-CH2-任选被-C(L0)=C(L00)-、-C≡C-、-N(L00)-、-O-、-S-、-CO-、-CO-O-、-O-CO-或-O-CO-O-替代,一个或多个H原子任选被卤素原子、CN、P1或P1-Sp-替代,且P11及P12中至少之一表示基团P1或P1-Sp-;
K1、K2、K3各自独立地表示4~25个碳原子的芳环、4~25个碳原子的杂芳环、4~25个碳原子的脂肪族环或4~25个碳原子的稠环,其中K1、K2、K3的环上一个或多个不相邻的-CH2-任选被-O-、-S-替代,一个或多个H原子任选被L1或-Sp-P1取代;
L1表示F原子、碳原子数为1~10的烷基、氟取代的碳原子数为1~10的烷基、碳原子数为1~10的烷氧基、氟取代的碳原子数为1~10的烷氧基、碳原子数为2~10的链烯基、氟取代的碳原子数为2~10的链烯基、碳原子数为3~8的链烯氧基或氟取代的碳原子数为3~8的链烯氧基,且任一个-CH2-任选被亚环戊基、亚环丁基或亚环丙基替代;
Z1、Z2、Z3各自独立地表示单键、-O-、-S-、-CO-、-COO-、-OCO-、-OCOO-、-OCH2-、-CH2O-、-SCH2-、-CH2S-、-CF2O-、-OCF2-、-CF2S-、-SCF2-、-(CH2)n1-、-CF2CH2-、-CH2CF2-、-(CF2)n1-、-(CL0L00)n1-、-CH=CH-、-C≡C-、-CF=CF-、-CH=CH-COO-、-OCO-CH=CH-、-OCO-CH=CH-COO-、-N=N-、
n1表示1、2、3或4;
m、n、o、q各自独立地表示0、1、2、3或4,且m+o+n*q=1;
L0、L00各自独立地表示H原子或具有1~12个C原子的烷基;
G1、G2、G3各自独立地表示-Sp1-R1、-Sp2-R2、-Sp3-R3或R;
p表示2或3;
X表示三价基团或四价基团;
Y表示C原子、N原子、S原子或P原子;
L11、L22各自独立地表示H原子或1~12个C原子的烷基;
Sp、Sp1、Sp2、Sp3、Sp4、Sp5彼此独立的表示间隔基或单键;
P1表示可聚合基团。
2.根据权利要求1所述的化合物,其特征在于,所述式I所示化合物选自下述式I-1至式I-9所示的化合物组成的组:
其中,P11、P12相同或不同地表示P1、P1-Sp-、-Z3-H、-Z3-L1、H原子、F原子或具有1~12个C原子的直链或支链烷基,其中一个或多个不相邻的-CH2-任选被-C(L0)=C(L00)-、-C≡C-、-N(L00)-、-O-、-S-、-CO-、-CO-O-、-O-CO-或-O-CO-O-替代,一个或多个H原子任选被卤素原子、CN、P1或P1-Sp-替代,且P11及P12中至少之一表示基团P1或P1-Sp-;
L1表示F原子、碳原子数为1~10的烷基、氟取代的碳原子数为1~10的烷基、碳原子数为1~10的烷氧基、氟取代的碳原子数为1~10的烷氧基、碳原子数为2~10的链烯基、氟取代的碳原子数为2~10的链烯基、碳原子数为3~8的链烯氧基或氟取代的碳原子数为3~8的链烯氧基,且任一个-CH2-任选被亚环戊基、亚环丁基或亚环丙基替代;
Z1、Z2、Z3各自独立地表示单键、-O-、-S-、-CO-、-COO-、-OCO-、-OCOO-、-OCH2-、-CH2O-、-SCH2-、-CH2S-、-CF2O-、-OCF2-、-CF2S-、-SCF2-、-(CH2)n1-、-CF2CH2-、-CH2CF2-、-(CF2)n1-、-(CL0L00)n1-、-CH=CH-、-C≡C-、-CF=CF-、-CH=CH-COO-、-OCO-CH=CH-、-OCO-CH=CH-COO-、-N=N-、
n1表示1、2、3或4;
L0、L00各自独立地表示H原子或具有1~12个C原子的烷基;
L11表示H原子或1~12个C原子的烷基;
Sp、Sp1各自独立地表示间隔基或单键;
P1表示可聚合基团。
4.一种液晶组合物,其特征在于,包含权利要求1~3中任一项所述的一种或多种式I所示化合物。
5.根据权利要求4所述的液晶组合物,其特征在于,还包含一种或多种式P所示的聚合性化合物,
Pa-(Spa)s1-A2-(Z-A1)n2-(Spb)s2-Pb P
其中,Pa、Pb各自独立地表示可聚合基团;
Spa、Spb各自独立地表示间隔基团;
s1、s2各自独立地为0或1;
A1、A2各自独立地表示选自以下组:
a)由反式-1,4-亚环己基、1,4-亚环己烯基及4,4′-亚双环己基组成的组,其中一个或多个不相邻的-CH2-基团任选被-O-或-S-替代,一个或多个H原子任选被F原子替代;
b)由1,4-亚苯基及1,3-亚苯基组成的组,其中一个或两个CH基团任选被N替代,一个或多个H原子任选被L替代;
c)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-2,5-二基组成的组,其中一个或多个H原子任选被L取代;
d)下述基团组成的组,
其中这些基团中的一个或多个H原子任选被L替代,和/或一个或多个双键任选被单键替代,和/或一个或多个CH任选被N原子替代;
n2为0、1、2或3;
Z表示-CO-O-、-O-CO-、-CH2O-、-OCH2-、-CF2O-、-OCF2-、具有2~4个碳原子的直链亚烷基、-O-、-CO-、-C(R0R00)-、-CH2CF2-、-CF2CF2-或单键;
L在每次出现时,相同或不同地表示F原子、Cl原子、CN、SCN、SF5或任选经氟化的具有1~12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、烷氧基羰氧基;
R0、R00各自彼此独立地表示H原子、F原子或具有1~12个C原子的直链或支链烷基,其中一个或多个H原子任选被F原子替代;
M表示-O-、-S-、-CH2-、-CHY1-或-CY1Y2-;
Y1、Y2各自彼此独立地表示H原子、F原子、Cl原子、CN或具有1~12个C原子的直链或支链烷基,其中一个或多个H原子任选被F原子替代。
6.根据权利要求4所述的液晶组合物,其特征在于,所述液晶组合物中还包含一种或多种式II所示化合物和/或一种或多种式III所示化合物,
其中,
R5、R6各自独立地表示碳原子数为1~12的烷基,其中一个或多个不相邻的-CH2-基团任选地被-O-、-CH=CH-、-CO-、-O-CO-或-CO-O-替代;
Z4表示-CH2CH2-、-CH=CH-、-CF2O-、-OCF2-、-CH2O-、-OCH2-、-COO-、-OCO-、-C2F4-、-CF=CF-或单键;
R7、R8各自独立地表示碳原子数为1~10的烷基、氟取代的碳原子数为1~10的烷基、碳原子数为1~10的烷氧基、氟取代的碳原子数为1~10的烷氧基、碳原子数为2~10的链烯基、氟取代的碳原子数为2~10的链烯基、碳原子数为3~8的链烯氧基或氟取代的碳原子数为3~8的链烯氧基。
7.根据权利要求6所述的液晶组合物,其特征在于,所述液晶组合物中还包含一种或多种式IV所示化合物,
其中,
①反式1,4-亚环己基、1,4-环己烯基,其中一个或多个不相邻的-CH2-基团任选被-O-或-S-取代;
②1,4-亚苯基,其中一个或两个CH基任选被N取代,一个或两个H原子任选被F原子取代;
X1、X2各自独立地表示H原子或F原子;
Y3表示F原子、碳原子数为1~6的直链烷基或碳原子数为2~6的直链烯基,其中一个或多个氢原子任选被F原子替代;
Z5表示单键、-CH2-、-CH2CH2-、-(CH2)3-、-(CH2)4-、-CH=CH-、-C≡C-、-COO-、-OOC-、-OCH2-、-CH2O-、-CF2CH2-、-CH2CF2-、-C2F4-或-CF=CF-;
r表示0、1或2。
8.根据权利要求6或权利要求7任一项所述的液晶组合物,其特征在于,所述液晶组合物中还包含一种或多种式V所示化合物,
其中,R10、R11各自独立地表示碳原子数为1~10的烷基、氟取代的碳原子数为1~10的烷基、碳原子数为1~10的烷氧基、氟取代的碳原子数为1~10的烷氧基、碳原子数为2~10的链烯基、氟取代的碳原子数为2~10的链烯基、碳原子数为3~8的链烯氧基或氟取代的碳原子数为3~8的链烯氧基,且R10、R11中任意一个或多个不相邻的-CH2-任选被亚环戊基、亚环丁基或亚环丙基取代;
Z6、Z7各自独立地表示单键、-CH2CH2-或-CH2O-;
s表示1或2;t表示0、1或2。
9.一种液晶显示元件或液晶显示器,其包含权利要求1~3任一项所述的化合物,或者权利要求4~8中任一项所述的液晶组合物,所述显示元件或显示器为有源矩阵显示元件或显示器或无源矩阵显示元件或显示器。
10.根据权利要求9所述的液晶显示元件或液晶显示器,其显示模式为IPS或FFS。
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