TWI699429B - 可聚合液晶化合物、液晶組合物及液晶顯示元件 - Google Patents
可聚合液晶化合物、液晶組合物及液晶顯示元件 Download PDFInfo
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- TWI699429B TWI699429B TW107113493A TW107113493A TWI699429B TW I699429 B TWI699429 B TW I699429B TW 107113493 A TW107113493 A TW 107113493A TW 107113493 A TW107113493 A TW 107113493A TW I699429 B TWI699429 B TW I699429B
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- QAXYLRJBHGDTQN-UHFFFAOYSA-N COC1C(OC)=CC(c2ccc(-c(cc3)c(CCC4O)c4c3OC)c(F)c2)=CC1 Chemical compound COC1C(OC)=CC(c2ccc(-c(cc3)c(CCC4O)c4c3OC)c(F)c2)=CC1 QAXYLRJBHGDTQN-UHFFFAOYSA-N 0.000 description 1
- CQYMDXSCUQZYGA-UHFFFAOYSA-N COc(c(OC)c1)ccc1-c(cc1)cc(F)c1-c1c(CCC2)c2c(CCCO)cc1 Chemical compound COc(c(OC)c1)ccc1-c(cc1)cc(F)c1-c1c(CCC2)c2c(CCCO)cc1 CQYMDXSCUQZYGA-UHFFFAOYSA-N 0.000 description 1
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- GGXNNOHLLTXTTD-UHFFFAOYSA-N COc(ccc(-c(c(F)c1)ccc1-c(cc1OC)ccc1OC)c1CC2)c1C2=O Chemical compound COc(ccc(-c(c(F)c1)ccc1-c(cc1OC)ccc1OC)c1CC2)c1C2=O GGXNNOHLLTXTTD-UHFFFAOYSA-N 0.000 description 1
- GJJRBPCAMDJPTF-UHFFFAOYSA-N COc(ccc(C(CC=C1c2cc(CCC3O)c3cc2)C=C1F)c1)c1OC Chemical compound COc(ccc(C(CC=C1c2cc(CCC3O)c3cc2)C=C1F)c1)c1OC GJJRBPCAMDJPTF-UHFFFAOYSA-N 0.000 description 1
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- HNMAWFAOROTHNA-UHFFFAOYSA-N OCC(CC1)c(cc2)c1cc2-c(ccc(-c(cc1)cc(O)c1O)c1)c1F Chemical compound OCC(CC1)c(cc2)c1cc2-c(ccc(-c(cc1)cc(O)c1O)c1)c1F HNMAWFAOROTHNA-UHFFFAOYSA-N 0.000 description 1
- JAQBZEZMWXUMPW-UHFFFAOYSA-N OCCCc(cc1)c(CCC2)c2c1-c(c(F)c1)ccc1-c(cc1O)ccc1O Chemical compound OCCCc(cc1)c(CCC2)c2c1-c(c(F)c1)ccc1-c(cc1O)ccc1O JAQBZEZMWXUMPW-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/52—Esters of acyclic unsaturated carboxylic acids having the esterified carboxyl group bound to an acyclic carbon atom
- C07C69/533—Monocarboxylic acid esters having only one carbon-to-carbon double bond
- C07C69/54—Acrylic acid esters; Methacrylic acid esters
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- 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
- C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
- C09K19/3402—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/017—Esters of hydroxy compounds having the esterified hydroxy group bound to a carbon atom of a six-membered aromatic ring
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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
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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
- C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
- C09K19/3001—Cyclohexane rings
- C09K19/3003—Compounds containing at least two rings in which the different rings are directly linked (covalent bond)
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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
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- C09K19/3001—Cyclohexane rings
- C09K19/3028—Cyclohexane rings in which at least two rings are linked by a carbon chain containing carbon to carbon single bonds
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- C09K19/06—Non-steroidal liquid crystal compounds
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- C09K19/3001—Cyclohexane rings
- C09K19/3066—Cyclohexane rings in which the rings are linked by a chain containing carbon and oxygen atoms, e.g. esters or ethers
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- C09K19/06—Non-steroidal liquid crystal compounds
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- C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
- C09K19/3098—Unsaturated non-aromatic rings, e.g. cyclohexene rings
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- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/32—Non-steroidal liquid crystal compounds containing condensed ring systems, i.e. fused, bridged or spiro ring systems
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- C09K19/38—Polymers
- C09K19/3833—Polymers with mesogenic groups in the side chain
- C09K19/3842—Polyvinyl derivatives
- C09K19/3852—Poly(meth)acrylate derivatives
- C09K19/3861—Poly(meth)acrylate derivatives containing condensed ring systems
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- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/42—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40
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- C09K19/42—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40
- C09K19/44—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40 containing compounds with benzene rings directly linked
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- C09K19/42—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40
- C09K19/46—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40 containing esters
-
- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
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- C09K2019/0444—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit characterized by a linking chain between rings or ring systems, a bridging chain between extensive mesogenic moieties or an end chain group
- C09K2019/0448—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit characterized by a linking chain between rings or ring systems, a bridging chain between extensive mesogenic moieties or an end chain group the end chain group being a polymerizable end group, e.g. -Sp-P or acrylate
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- 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
- C09K2019/121—Compounds containing phenylene-1,4-diyl (-Ph-)
- C09K2019/122—Ph-Ph
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- C09K2019/121—Compounds containing phenylene-1,4-diyl (-Ph-)
- C09K2019/123—Ph-Ph-Ph
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- C09K19/06—Non-steroidal liquid crystal compounds
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- C09K19/3001—Cyclohexane rings
- C09K19/3003—Compounds containing at least two rings in which the different rings are directly linked (covalent bond)
- C09K2019/3004—Cy-Cy
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- C09K19/3003—Compounds containing at least two rings in which the different rings are directly linked (covalent bond)
- C09K2019/3009—Cy-Ph
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- C09K19/06—Non-steroidal liquid crystal compounds
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- C09K2019/301—Cy-Cy-Ph
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- C09K19/54—Additives having no specific mesophase characterised by their chemical composition
- C09K19/542—Macromolecular compounds
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Abstract
本發明提供一種式I所示可聚合液晶化合物以及這種可聚合化合物與特定液晶組分搭配形成的液晶組合物,尤其適用於顯示器或TV應用的PSVA液晶組合物,以及IPS模式的PSA-IPS液晶組合物,尤其是可聚合化合物具有較快的聚合速度並且所選擇的可聚合組分與液晶組分形成的“材料體系”具有低的旋轉黏度、良好的光電性能,且採用(UV)光輻照後具有高的VHR,避免了最終顯示器出現殘像等問題。
Description
本發明涉及液晶顯示領域,具體涉及特定可聚合化合物與特定液晶組分搭配形成的液晶組合物,以及包含有該液晶組合物的顯示元件。
薄膜晶體管液晶顯示器(TFT-LCD)經歷了漫長的基礎研究階段,在實現大生產、商業化之後,以其輕薄、環保、高性能等優點已經成為LCD應用中的主流產品:無論是小尺寸的手機屏、還是大尺寸的筆記本電腦(Notebook PC)或監視器(Monitor),以及大型化的液晶電視(LCD-TV),到處可見TFT-LCD的應用。
早期商用的TFT-LCD產品基本採用了TN顯示模式,其最大問題是視角窄。隨著產品尺寸的增加,特別是在TV領域的應用,具有廣視野角特點的IPS顯示模式、VA顯示模式依次被開發出來並加以應用,尤其是基於VA顯示模式的改進,分別先後在各大公司得到了突破性的發展,這主要取決於VA模式本身所具有的寬視野角、高對比度和無需摩擦配向等優勢,再有就是,VA模式顯示的對比度對液晶的光學各向異性(△n)、液晶盒的厚度(d)和入射光的波長(λ)依賴度較小,必將使得VA這種模式成為極具前景的顯示技術。
但是,VA模式等的主動矩陣尋址方式的顯示元件所用的液晶介質,本身並不完美,例如殘像水平要明顯差於正介電各向異性的顯示元件,響應時間比較慢,驅動電壓比較高等缺點。此時,一些新型的VA顯示技術悄然而
生:像PSVA技術即實現了MVA/PVA類似的廣視野角顯示模式,也簡化了CF製程,從而降低CF成本的同時,提高了開口率,還可以獲得更高的亮度,進而獲得更高的對比度。此外,由於整面的液晶都有預傾角,沒有多米諾延遲現象,在保持同樣的驅動電壓下還可以獲得更快的響應時間,殘像水平也不會受到影響,但是由於像素中Fine Slit密集分佈電極,故如果電極寬度不能均勻分佈,很容易出現顯示不均的問題。像UVVA技術,在保持PSVA技術優勢的基礎上,由於在TFT側沒有Slit結構,出現像素電極寬度不均引起的顯示不均問題還得到了改進。雖然顯示器件在不斷的發展,但是人們還要一直致力於研究新的液晶化合物,得以使液晶介質及其應用於顯示器件的性能不斷的向前發展。
可聚合介晶單元(RMs)目前是顯示行業非常熱門且重要的課題,其可能應用的領域包括聚合物穩定配向(PSA)液晶顯示,聚合物穩定藍相(PS-BP)液晶顯示以及圖形化位相差膜(Pattern Retarder Film)等。
PSA原理正被應用在不同典型的LC顯示器中,例如PSA-VA、PSA-OCB、PS-IPS/FFS和PS-TN等液晶顯示器。以目前最為廣泛應用的PSA-VA顯示器為例,通過PSA方法可以獲得液晶盒的預傾角,該預傾角對響應時間具有積極的影響。對於PSA-VA顯示器,可以使用標準的MVA或PVA像素和電極設計,但是如果在一側的電極設計採用特殊圖形化的而在另一端不採用突起的設計,可以顯著的簡化生產,同時使顯示器得到非常好的對比度、及很高的光透過率。
現有技術已經發現LC混合物和RMs在PSA顯示器中的應用方面仍具有一些缺點。首先,到目前為止並不是每個希望的可溶RM都適合用於PSA顯示器;同時,如果希望借助於UV光而不添加光引發劑進行聚合(這可能對某些
應用而言是有利的),則選擇變得更小;另外,LC混合物(下面也稱為“LC主體混合物”)與所選擇的可聚合組分組合形成的“材料體系”應具有最低的旋轉黏度和最好的光電性能,用於加大“電壓保持率”(VHR)以達到效果。在PSA-VA方面,採用(UV)光輻照後的高VHR是非常重要的,否則會導致最終顯示器出現殘像等問題。到目前為止,並不是所有的LC混合物與可聚合組分組成的組合都適合於PSA顯示器。這主要是由於可聚合單元對於UV敏感性波長過短,或光照後沒有傾角出現或出現不足的傾角,或可聚合組分在光照後的均一性較差,或因為UV後VHR對於TFT顯示器應用而言是較低等方面的影響。
本發明提供一種可聚合化合物以及這種可聚合化合物與特定液晶組分搭配形成的液晶組合物以及包含該液晶組合物的液晶顯示元件,尤其適用於顯示器或TV應用的PSVA液晶組合物,以及IPS模式的PSA-IPS液晶組合物,尤其是可聚合化合物具有較快的聚合速度並且所選擇的可聚合組分與液晶組分形成的“材料體系”具有低的旋轉黏度、良好的光電性能,且採用(UV)光輻照後具有高的VHR,避免了最終顯示器出現殘像等問題。
其中、、各自獨立地表示、、、、、
、、或,並且所述、、不同時為;
並且,、、所示基團中一個或複數個H可以各自獨立地被
S基團取代;所述S基團表示C1-C5的烷基、C1-C5的烷氧基、C2-C5的烯基,氟取代的C1-C5的烷基、氟取代的C1-C5的烷氧基、氟取代的C2-C5的烯基、鹵素、P-Sp,其中,任意不相鄰的亞甲基可各自獨立地被-O-、-S-、-CH2O-、-COO-、-OCH2-、-OOC-、丙烯酸酯基或甲基丙烯酸酯基代替。
當所述、、被所述S基團單取代時,所述S基團表示P-Sp,
當所述、、被所述S基團多取代時,所述S基團中至少一個表
示P-Sp;
P獨立的代表可聚合基團:、或;
Sp各自獨立地表示單鍵、C1-C5的烷基、C1-C5的烯基,其中任意一個或複數個不相連的CH2可以被-O-、-S-、-CO-、-CH2O-、-OCH2-、-COO-、-OOC-或丙烯酸酯基代替。
其中,R1、R2、R3、R4各自獨立地表示碳原子數為1-10的烷基、氟取代的碳原子數為1-10的烷基、碳原子數為1-10的烷氧基、氟取代的碳原子數為1-10的烷氧基、碳原子數為2-10的鏈烯基、氟取代的碳原子數為2-10的鏈烯基、碳原子數為3-8的鏈烯氧基或氟取代的碳原子數為3-8的鏈烯氧基,並且R3、R4所示基團中任意一個或複數個不相連的CH2可以被環戊基、環丁基或環丙基取代;Z1、Z2各自獨立地表示單鍵、-CH2CH2-或-CH2O-;
、各自獨立地表示或;
、各自獨立地表示、、、、、、
和/或中的一種或多種;
m表示1或2;n表示0、1或2。
進一步較佳地,本發明所提供的液晶組合物中,式I化合物的總質量含量為0.01-1%,所述式Ⅱ化合物的總質量含量為15-60%,所述一種或多種通式Ⅲ所示化合物總質量含量為20-60%。
其中,S各自獨立地表示H、C1-C5的烷基、C1-C5的烷氧基、氟取代的C1-C5的烷基、氟取代的C1-C5的烷氧基、F或Cl,其中任意一個或複數個不相連的CH2可以各自獨立地被-O-、-S-、-CO-、-CH2O-、-OCH2-、-COO-、-OOC-或丙烯酸酯基或甲基丙烯酸酯基代替;
P各自獨立地表示、或;
Sp各自獨立地表示單鍵、C1-C5的烷基、C1-C5的烯基,其中任意一個或複數個不相連的CH2可以被-O-、-S-、-CO-、-CH2O-、-OCH2-、-COO-、-OOC-或丙烯酸酯基代替;o各自獨立地表示0、1、2或3。
其中,R3、R4各自獨立地表示碳原子數為1-10的烷基、氟取代的碳原子數為1-10
的烷基、碳原子數為1-10的烷氧基、氟取代的碳原子數為1-10的烷氧基、碳原子數為2-10的鏈烯基、氟取代的碳原子數為2-10的鏈烯基、碳原子數為3-8的鏈烯氧基或氟取代的碳原子數為3-8的鏈烯氧基,並且R3、R4所示基團中任意一個或複數個不相連的CH2可以被環戊基、環丁基或環丙基取代。
應用這些液晶組合物的這些顯示器中,將式I所示化合物加入到LC介質中,且在引入到LC盒中之後,在電極間施加電壓下通過UV光致聚合或交聯,可以形成液晶分子的預傾斜。這對於簡化LCD製作流程、提高響應速度、降低閾值電壓是有利的。
本發明提供的式I所示化合物具有與其他單體互溶性好、紫外線耐受能力好等優點。作為反應性介晶(RM)具有互溶性良好、電荷保持率(VHR)高、聚合活性高(單體殘留少)等優點,非常適合於作為RM用於PSA(聚合物支持的配向)、PS(聚合物穩定的)型模式的液晶混合物,尤其是在PSA-VA、PSA-IPS情況下。
式I可聚合化合物在液晶組合物中的添加量(質量比)較佳在0.01-1%之間,更佳0.03-0.2%之間。
所述式Ⅱ所示化合物在液晶組合物中的添加量(質量比)較佳在15-60%之間,更佳20-40%。
所述式Ⅲ所示化合物在液晶組合物中的添加量(質量比)較佳在20-60%之間,更佳30-50%。
其中,R5、R6各自獨立地表示碳原子數為1-10的烷基、氟取代的碳原子數為1-10的烷基、碳原子數為1-10的烷氧基、氟取代的碳原子數為1-10的烷氧基、碳原子數為2-10的鏈烯基、氟取代的碳原子數為2-10的鏈烯基、碳原子數為3-8的鏈烯氧基或氟取代的碳原子數為3-8的鏈烯氧基,並且R5、R6所示基團中任意一個或複數個CH2可以被環戊基、環丁基或環丙基替代;W表示O、S或-CH2O-。
其中,R61各自獨立地表示碳原子數為2-6烷基。
其中,R7、R8各自獨立地表示碳原子數為1-10的烷基、氟取代的碳原子數為1-10的烷基、碳原子數為1-10的烷氧基、氟取代的碳原子數為1-10的烷氧基、碳原子數為2-10的鏈烯基、氟取代的碳原子數為2-10的鏈烯基、碳原子數為3-8的鏈烯氧基或氟取代的碳原子數為3-8的鏈烯氧基;
、各自獨立地表示1,4-亞苯基、1,4-亞環己基或1,4-亞環己烯基。
其中,R71、R81各自獨立地表示碳原子數為2-6的烷基或原子數為2-6的烯基;R82表示碳原子數為1-5的烷氧基;R71、R81更佳為乙烯基、2-丙烯基、3-戊烯基。
其中,R9、R10各自獨立地表示碳原子數為1-10的烷基、氟取代的碳原子數為1-10的烷基、碳原子數為1-10的烷氧基、氟取代的碳原子數為1-10的烷氧基、碳原子數為2-10的鏈烯基、氟取代的碳原子數為2-10的鏈烯基、碳原子數為3-8的鏈烯氧基或氟取代的碳原子數為3-8的鏈烯氧基;
表示1,4-亞苯基、1,4-亞環己基、1,4-亞環己烯基;
(F)各自獨立地表示H或F。
其中,R9、R10各自獨立地較佳表示碳原子數為2-6的烷基或原子數為2-6的烯基;本發明所提供的液晶化合物中還可以加入各種功能的摻雜劑,摻雜劑含量較佳0.01-1%之間,這些摻雜劑主要是抗氧化劑、紫外線吸收劑、對掌性劑。
本發明還涉及包含上述任意一種液晶組合物的液晶顯示元件;所述顯示元件為主動矩陣顯示元件或顯示器或被動矩陣顯示元件或顯示器。
所述液晶顯示元件較佳主動矩陣尋址液晶顯示元件或液晶顯示器。
所述主動矩陣顯示元件具體為PSVA-TFT或IPS-TFT液晶顯示元件或顯示器。其中,本文所指的液晶顯示元件可包含液晶顯示器、液晶顯示裝置等。
下面結合具體實施例對本發明作進一步闡述,但本發明並不限於以下實施例。所述方法如無特別說明均為習知方法。所述原材料如無特別說明均能從公開商業途徑而得。
反應過程一般通過TLC監控反應的進程,反應結束的後處理一般是水洗、提取、合併有機相後乾燥、減壓下蒸除溶劑,以及重結晶、柱層析,所屬技術領域中具有通常知識者都能夠按照下面的描述來實現本發明。
本說明書中的百分比為質量百分比,溫度為攝氏度(℃),其他符號的具體意義及測試條件如下:Cp表示液晶清晰點(℃),DSC定量法測試;S-N表示液晶的晶態到向列相的熔點(℃);△n表示光學各向異性,no為尋常光的折射率,ne為非尋常光的折射率,測試條件為25±2℃,589nm,阿貝折射儀測試;△ε表示介電各向異性,△ε=ε∥-ε⊥,其中,ε∥為平行於分子軸的介電常數,ε⊥為垂直於分子軸的介電常數,測試條件為25±0.5℃,20微米平行盒,INSTEC:ALCT-IR1測試;
γ1表示旋轉黏度(mPa.s),測試條件為25±0.5℃,20微米平行盒,INSTEC:ALCT-IR1測試;ρ表示電阻率(Ω.cm),測試條件為25±2℃,測試儀器為TOYO SR6517高阻儀和LE-21液體電極。
VHR表示電壓保持率(%),測試條件為20±2℃、電壓為±5V、脈衝寬度為10ms、電壓保持時間16.7ms。測試設備為TOYO Model6254液晶性能綜合測試儀。
τ表示響應時間(ms),的測試儀器為DMS-501,測試條件為25±0.5℃,測試盒為3.3微米IPS測試盒,電極間距和電極寬度均為10微米,摩擦方向與電極夾角為10°。
T(%)表示透過率,T(%)=100%*亮態(Vop)亮度/光源亮度,測試設備DMS501,測試條件為25±0.5℃,測試盒為3.3微米IPS測試盒,電極間距和電極寬度均為10微米,摩擦方向與電極夾角為10°。
可聚合化合物紫外光聚合條件為使用313nm波長且照射光強為0.5Mw/cm2的紫外光
以下採用以下具體實施例來對本發明進行說明:
可聚合化合物的製備:
實施例1
製備的具體操作流程:
中間體2
在2L三口瓶中投入0.1mol的原料1,0.5L四氫呋喃,0.02L水,降溫到0℃,分批加入0.15mol硼氫化鉀,控溫0℃反應3h,自然升至室溫(約25℃)
室溫下反應8小時。向體系加100L水,然後用稀酸調節PH到6-7,分液,水相用乙酸乙酯萃取,無水硫酸鈉乾燥,旋乾,得中間體2。
中間體3
在1L三口瓶中加入上步中間體2,5g對甲苯磺酸,0.5L甲苯,攪拌升溫回流分水2小時。將體系倒入裝有20g矽膠的柱子中,用0.5L甲苯沖洗,洗脫液用水洗三次到中性,旋乾,得中間體3。
中間體4
在2L三口瓶中投入上步中間體3,0.5L甲苯,0.1L無水乙醇,10g鈀碳(5%),氮氣排空5次,氫氣排空3次,攪拌加氫3h,將體系倒入裝有20g矽膠的柱子中,用0.5L甲苯沖洗,洗脫液用水洗三次到中性,旋乾,得中間體4
中間體5
在2L三口瓶中投入上步中間體4,0.5L二氯甲烷,攪拌降溫到0℃,滴加4.5倍mol量的三溴化硼,控溫0℃以下,1h滴完,控溫0℃反應12h,將反應液倒入1kg水中,攪拌15分鐘,分液,分出大部分二氯甲烷(約0.5L),向水相中加入乙酸乙酯0.5L,攪拌至固體全部溶解,分液,水相用0.2L×2乙酸乙酯提取,合併有機相,有機相水洗,分淨水,加入0.5kg無水硫酸鈉乾燥4小時,旋乾溶劑,用5倍石油醚重結晶,得中間體5
產品I-1-1
在1L三口瓶中投入0.02mol的中間體5,0.07mol甲基丙烯酸,0.5L甲苯,氮氣保護下降溫至0℃,控溫0-5℃,加入0.09molDCC,加畢,自然升至室溫(約25℃)室溫下反應8小時。加入500ml水,分液,水相用100ml×2甲苯萃取,合併有機相,用500ml×2食鹽水洗,洗畢,無水硫酸鈉乾燥,蒸乾,取30g
矽膠、3倍石油醚(90-120℃)過柱,2倍石油醚(90-120℃)沖柱,蒸乾2倍乙醇重結晶,得產品I-1-1。
實施例2
中間體7
在2L三口瓶中投入0.1mol原料6,0.8L二氯甲烷,攪拌降溫到0℃,滴加3倍mol量的三溴化硼,控溫0℃以下,1h滴完,控溫0℃反應12h,將反應倒入1kg水中,攪拌15分鐘,分液,分出大部分二氯甲烷(約0.8L),向水相中加入乙酸乙酯0.5L,攪拌至固體全部溶解,分液,水相用0.2L×2乙酸乙酯提取,合併有機相,有機相水洗,分淨水,加入0.5kg無水硫酸鈉乾燥4小時,旋乾溶劑,用5倍石油醚重結晶,得中間體7
產品I-1-8
在1L三口瓶中投入0.05mol的中間體7,0.2mol甲基丙烯酸,0.5L甲苯,氮氣保護下降溫至0℃,控溫0-5℃,加入0.25molDCC,加畢,自然升至室溫(約25℃)室溫下反應12小時。加入500ml水,分液,水相用100ml×2甲苯萃取,合併有機相,用500ml×2食鹽水洗,洗畢,無水硫酸鈉乾燥,蒸乾,取30g矽膠、3倍石油醚(90-120℃)過柱,2倍石油醚(90-120℃)沖柱,蒸乾,2倍乙醇重結晶,得產品I-1-8。
實施例3
中間體9
在2L三口瓶中投入0.1mol原料8,0.8L二氯甲烷,攪拌降溫到0℃,滴加3倍mol量的三溴化硼,控溫0℃以下,1h滴完,控溫0℃反應12h,將反應倒入1kg水中,攪拌15分鐘,分液,分出大部分二氯甲烷(約0.8L),向水相中加入乙酸乙酯0.5L,攪拌至固體全部溶解,分液,水相用0.2L×2乙酸乙酯提取,合併有機相,有機相水洗,分淨水,加入0.5kg無水硫酸鈉乾燥4小時,旋乾溶劑,用5倍石油醚重結晶,得中間體9
產品I-3-10
在1L三口瓶中投入0.05mol的中間體9,0.2mol甲基丙烯酸,0.5L甲苯,氮氣保護下降溫至0℃,控溫0-5℃,加入0.25molDCC,加畢,自然升至室溫(約25℃)室溫下反應12小時。加入500ml水,分液,水相用100ml×2甲苯萃取,合併有機相,用500ml×2食鹽水洗,洗畢,無水硫酸鈉乾燥,蒸乾,取30g矽膠、3倍石油醚(90-120℃)過柱,2倍石油醚(90-120℃)沖柱,蒸乾,2倍乙醇重結晶,得產品I-3-10。
實施例4
製備的具體操作流程:
中間體11
在2L三口瓶中投入0.1mol的原料10,0.5L四氫呋喃,0.02L水,降溫到0℃,分批加入0.15mol硼氫化鉀,控溫0℃反應3h,自然升至室溫(約25℃)室溫下反應8小時。向體系加100L水,然後用稀酸調節PH到6-7,分液,水相用乙酸乙酯萃取,無水硫酸鈉乾燥,旋乾,得中間體11。
中間體12
在2L三口瓶中投入上步中間體11,0.5L二氯甲烷,攪拌降溫到0℃,滴加4.5倍mol量的三溴化硼,控溫0℃以下,1h滴完,控溫0℃反應12h,將反應液倒入1kg水中,攪拌15分鐘,分液,分出大部分二氯甲烷(約0.5L),向水相中加入乙酸乙酯0.5L,攪拌至固體全部溶解,分液,水相用0.2L×2乙酸乙酯提取,合併有機相,有機相水洗,分淨水,加入0.5kg無水硫酸鈉乾燥4小時,旋乾溶劑,用5倍石油醚重結晶,得中間體12
產品I-9-1
在1L三口瓶中投入0.02mol的中間體12,0.07mol甲基丙烯酸,0.5L甲苯,氮氣保護下降溫至0℃,控溫0-5℃,加入0.09molDCC,加畢,自然升至室溫(約25℃)室溫下反應8小時。加入500ml水,分液,水相用100ml×2甲苯萃取,合併有機相,用500ml×2食鹽水洗,洗畢,無水硫酸鈉乾燥,蒸乾,取30g矽膠、3倍石油醚(90-120℃)過柱,2倍石油醚(90-120℃)沖柱,蒸乾2倍乙醇重結晶,得產品I-9-1
實施例5
製備的具體操作流程:
中間體13
在5L三口瓶中投入0.1mol的氯甲醚三苯基膦鹽,0.8L四氫呋喃,攪拌降溫到0℃,分批加入0.11mol叔丁醇鉀,加完控溫0-5℃反應2h。原料10溶於10倍四氫呋喃中,滴加到反應瓶中,控溫0-5℃,滴完反應3h,自然升至室溫(約25℃)室溫下反應8小時。向體系加1L水,分液,水相用乙酸乙酯萃取,乙醇水洗三次,無水硫酸鈉乾燥,旋乾,無水乙醇重結晶,得中間體13。
中間體14
在2L三口瓶中投入上步中間體13,0.5L二氯甲烷,0.5L丙酮,攪拌降溫到0℃,滴加鹽酸水溶液,控溫0-10℃以下,1h滴完,控溫0℃反應12h,將反應液倒入1kg水中,攪拌15分鐘,分液,分出大部分二氯甲烷(約0.5L),向水相中加入二氯甲烷0.5L,攪拌至固體全部溶解,分液,水相用0.2L×2二氯甲烷提取,合併有機相,有機相水洗,分淨水,加入0.5kg無水硫酸鈉乾燥4小時,旋乾溶劑,用5倍石油醚重結晶,得中間體14
中間體15
在2L三口瓶中投入0.05mol的中間體14,0.5L四氫呋喃,0.02L水,降溫到0℃,分批加入0.1mol硼氫化鉀,控溫0℃反應3h,自然升至室溫(約25℃)室溫下反應8小時。向體系加100L水,然後用稀酸調節PH到6-7,分液,水相用乙酸乙酯萃取,無水硫酸鈉乾燥,旋乾,得中間體15。
中間體16
在2L三口瓶中投入上步中間體15,0.5L二氯甲烷,攪拌降溫到0℃,滴加4.5倍mol量的三溴化硼,控溫0℃以下,1h滴完,控溫0℃反應12h,將反應液倒入1kg水中,攪拌15分鐘,分液,分出大部分二氯甲烷(約0.5L),向水相中加入乙酸乙酯0.5L,攪拌至固體全部溶解,分液,水相用0.2L×2乙酸乙酯提取,合併有機相,有機相水洗,分淨水,加入0.5kg無水硫酸鈉乾燥4小時,旋乾溶劑,用5倍石油醚重結晶,得中間體16
產品I-9-14
在1L三口瓶中投入0.02mol的中間體16,0.07mol甲基丙烯酸,0.5L甲苯,氮氣保護下降溫至0℃,控溫0-5℃,加入0.09molDCC,加畢,自然升至室溫(約25℃)室溫下反應8小時。加入500ml水,分液,水相用100ml×2甲苯萃取,合併有機相,用500ml×2食鹽水洗,洗畢,無水硫酸鈉乾燥,蒸乾,取30g矽膠、3倍石油醚(90-120℃)過柱,2倍石油醚(90-120℃)沖柱,蒸乾2倍乙醇重結晶,得產品I-9-14
實施例6
中間體18
在2L三口瓶中投入0.1mol原料17,0.8L二氯甲烷,攪拌降溫到0℃,滴加3倍mol量的三溴化硼,控溫0℃以下,1h滴完,控溫0℃反應12h,將反應倒入1kg水中,攪拌15分鐘,分液,分出大部分二氯甲烷(約0.8L),向水相中加入乙酸乙酯0.5L,攪拌至固體全部溶解,分液,水相用0.2L×2乙酸乙酯提取,合併有機相,有機相水洗,分淨水,加入0.5kg無水硫酸鈉乾燥4小時,旋乾溶劑,用5倍石油醚重結晶,得中間體18
產品I-3-1
在1L三口瓶中投入0.05mol的中間體18,0.2mol甲基丙烯酸,0.5L甲苯,氮氣保護下降溫至0℃,控溫0-5℃,加入0.25molDCC,加畢,自然升至室溫(約25℃)室溫下反應12小時。加入500ml水,分液,水相用100ml×2甲苯萃取,合併有機相,用500ml×2食鹽水洗,洗畢,無水硫酸鈉乾燥,蒸乾,取30g矽膠、3倍石油醚(90-120℃)過柱,2倍石油醚(90-120℃)沖柱,蒸乾,2倍乙醇重結晶,得產品I-3-1。
實施例7
製備的具體操作流程:
中間體19
在1L三口瓶中投入0.1mol的中間體16,0.22mol甲基丙烯醯氯,0.15L三乙胺,0.5L甲苯,室溫(約25℃)室溫下反應12小時。加入500ml水,分液,水相用100ml×2甲苯萃取,合併有機相,用500ml×2食鹽水洗,洗畢,無水硫酸鈉乾燥,蒸乾,取30g矽膠、3倍石油醚(90-120℃)過柱,2倍石油醚(90-120℃)沖柱,蒸乾,2倍乙醇重結晶,得中間體19
產品I-9-8
在1L三口瓶中投入0.05mol的中間體19,0.06mol丙烯酸,0.5L甲苯,氮氣保護下降溫至0℃,控溫0-5℃,加入0.25molDCC,加畢,自然升至室溫(約25℃)室溫下反應12小時。加入500ml水,分液,水相用100ml×2甲苯萃取,合併有機相,用500ml×2食鹽水洗,洗畢,無水硫酸鈉乾燥,蒸乾,取30g矽膠、3倍石油醚(90-120℃)過柱,2倍石油醚(90-120℃)沖柱,蒸乾,2倍乙醇重結晶,得產品I-9-8。
對比例7:
實施例1:
實施例2
實施例3
實施例4
實施例5
實施例6:
實施例7
實施例8
實施例9
實施例10
1.聚合性化合物的轉化率
測定可聚合化合物製備得到的液晶介質在用於液晶顯示器件中的聚合速率:
以對比例6中去掉RM-1的混合物為母體MUTY,分別向其中添加2500ppm的實施例1~7的可聚合化合物RM;作為對比,分別向MUTY中添加等量對比例1-6的RM,以上述提到的液晶介質製備方法製備成液晶介質,灌注液晶盒後,模擬PSA面板製程,測定其聚合速率,具體條件:UV1:80mW/cm2@ 365nm,200s;UV2:5mW/cm2@ 365nm,120min,再剖開液晶盒進行HPLC分析,結果如下表所示。
從上表可以看出,相對於對比例1、2、4,本發明提供的可聚合化合物,具備快速反應速度,實現了相同時間內較高的轉化率。
而對比例3、5、6由於反應時間過快,導致形成的顆粒物偏大,不均勻,形成的預傾角太大,造成了漏光現象。本發明提供的可聚合化合物在保持了較快的反應時間的情況下,形成的顆粒均一,預傾角適當,技術優勢明顯。
2.響應時間
將各種可聚合性化合物和液晶化合物而製備的混合物注入至器件中。通過照射紫外線來使聚合物性化合物聚合後,測定器件的響應時間。未添加聚合性化合物與液晶化合物的混合物時,響應時間慢。因此,可得出結論:
有本發明涉及的聚合性化合物和液晶化合物的組合在縮短響應時間方面效果明顯。
3.信賴性
將各種可聚合性化合物和液晶化合物而製備的混合物注入至測試盒中。通過照射紫外線來使聚合物性化合物聚合後,再在紫外、高溫等條件下測試其電壓保持率(VHR),較佳高信賴性液晶,即高VHR(16.7ms)。實施例數據明顯較優。
Claims (10)
- 一種式I所示可聚合液晶化合物:
- 如申請專利範圍第1項所述之可聚合液晶化合物,其中,該式I所示可聚合液晶化合物為式I-1至I-18所示化合物:
- 一種液晶組合物,其包含一種或多種申請專利範圍第1項至第3項中任一項所述之式I所示可聚合液晶化合物作為第一組分、一種或多種式Ⅱ所示化合物作為第二組分以及一種或多種式Ⅲ所示化合物作為第三組分,
- 如申請專利範圍第4項所述之液晶組合物,其中,該液晶組合物中式I所示可聚合液晶化合物的總質量含量為0.01-1%,該一種或多種式Ⅱ所示化合物的總質量含量為15-60%,該一種或多種式Ⅲ所示化合物總質量含量為20-60%。
- 一種包含如申請專利範圍第4項至第9項中任一項所述之液晶組合物的液晶顯示元件,其中該液晶顯示元件為主動矩陣顯示元件或被動矩陣顯示元件。
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