TWI568839B - Polymerizable liquid crystal composition - Google Patents
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Description
本發明係有關於一種聚合性液晶組成物,更具體地指一種使用於光學薄膜時,能具有熱穩定性以及液晶相區域的溫度範圍寬的特性,並具有成本效益的聚合性液晶組成物。 The present invention relates to a polymerizable liquid crystal composition, and more particularly to a polymerizable liquid crystal composition which is characterized in that it has thermal stability and a wide temperature range of a liquid crystal phase region when used in an optical film, and is cost-effective.
近來隨著資訊通信領域的急速發展,用於顯示各種資訊的顯示器的重要性日益增高。現有的顯示裝置之一的陰極綫管(Cathode Ray Tube)有一定的限制,無法對應最近輕薄化趨勢。於是為符合要求,已經開發出平面液晶顯示器(Liquid Crystal Display)、等離子顯示器(PDP:Plasma Display Panel)、ELD(Electro Luminescence Display)等,而針對此,正在進行積極研究和活動。 Recently, with the rapid development of the information communication field, the importance of displays for displaying various information is increasing. The cathode ray tube of one of the existing display devices has certain limitations and cannot correspond to the recent trend of thinning. Therefore, in order to meet the requirements, a liquid crystal display, a plasma display panel (PDP), an ELD (Electro Luminescence Display), and the like have been developed, and active research and activities are being conducted.
在上述顯示裝置中,液晶顯示裝置係一種具有輕量化、薄型化、低功率等優點的顯示裝置。借助該些優點,液晶顯示器不但能用於移動終端、筆記本電腦等的顯示器,還能廣泛適用於桌上型電腦及大型電視等,於是人們對此的需求亦日益增加。 In the above display device, the liquid crystal display device is a display device which is advantageous in terms of weight reduction, thinning, and low power. With these advantages, the liquid crystal display can be used not only for displays of mobile terminals, notebook computers, etc., but also for desktop computers and large televisions, and the demand for this is increasing.
液晶顯示裝置的驅動原理利用液晶的光學各向異性及偏光性質。由於液晶具有長而細的結構,因此分子排列具有取向性,對液晶施加電場可人為 控制分子排列的取向性。此種特性成為一個改變穿過液晶的光的偏光性的因素。 The driving principle of the liquid crystal display device utilizes the optical anisotropy and polarization properties of the liquid crystal. Since the liquid crystal has a long and thin structure, the molecular arrangement has an orientation, and an electric field applied to the liquid crystal can be artificially Control the orientation of the molecular arrangement. This characteristic becomes a factor that changes the polarization of light passing through the liquid crystal.
因此,若任意調整該液晶的分子排列方向,即可改變液晶的分子排列,由於光學各向異性,光線會向該液晶的分子排列方向折射,由此能顯示畫像資訊。 Therefore, if the molecular alignment direction of the liquid crystal is arbitrarily adjusted, the molecular arrangement of the liquid crystal can be changed, and due to the optical anisotropy, the light is refracted toward the molecular arrangement direction of the liquid crystal, whereby the image information can be displayed.
而且,該液晶顯示裝置由形成有公共電極的彩色濾光膜基板、形成有畫素電極的陣列基板,以及填充於兩基板之間的液晶構成,該液晶顯示裝置通過施加於公共電極和畫素電極之間的垂直電場驅動液晶,具有良好的透光率和開口率的特性,但還存在視角特性差的缺點。 Further, the liquid crystal display device is composed of a color filter film substrate on which a common electrode is formed, an array substrate on which a pixel electrode is formed, and a liquid crystal filled between the two substrates, which is applied to the common electrode and the pixel. The vertical electric field between the electrodes drives the liquid crystal, which has good light transmittance and aperture ratio characteristics, but also has the disadvantage of poor viewing angle characteristics.
另一方面,液晶顯示裝置的液晶盒根據液晶性分子的取向狀態,提出有能表示ON、OFF,而且可適用於任何透過式或反射式的TN(Twist Nematic)、IPS(In-Plane Switching)、OCB(Optically Compensatory Bend)、VA(Vertically Aligned)和ECB(Electrically Controlled Birefingence)等顯示裝置。 On the other hand, the liquid crystal cell of the liquid crystal display device has been proposed to be able to indicate ON or OFF depending on the alignment state of the liquid crystal molecules, and is applicable to any transmissive or reflective TN (Twist Nematic) or IPS (In-Plane Switching). Display devices such as OCB (Optically Compensatory Bend), VA (Vertically Aligned), and ECB (Electrically Controlled Birefingence).
由於液晶係一種各向異性物質,其具有上述驅動形態的雙折射率,即尋常折射率(Ordinary refractive index)和非尋常折射率(Extraordinary refractive index),根據入射光的入射角度會產生對比率(Contrast Ratio:CR)變化和灰階反轉(Gray scale inversion)現象。尤其扭曲向列型(TN)液晶由於隨著光線的進行方向會產生較大的相位延遲變化,因此有窄視角和明暗對比率(CR)特性。為了改善該缺點,使用補償膜進行相位差補償以便提升視角性能。 Since the liquid crystal is an anisotropic substance having a birefringence of the above-described driving form, that is, an ordinary refractive index and an extraordinary refractive index, a contrast ratio is generated according to an incident angle of incident light ( Contrast Ratio: CR) changes and gray scale inversion. In particular, twisted nematic (TN) liquid crystals have a narrow viewing angle and a contrast ratio (CR) characteristic due to a large phase delay variation with respect to the direction in which light is conducted. In order to improve this disadvantage, a compensation film is used for phase difference compensation in order to improve viewing angle performance.
此種液晶光學薄膜要求具有較寬的動作溫度範圍、聚合性基團反應性、塗佈性、良好的取向性及化學穩定性等諸多性能。液晶元件使用能表現出液晶相的材料,而目前無法用單一化合物能滿足此種特性,於是將一種或二種 以上的具有優秀特性的多數個反應性液晶化合物或反應性非液晶性化合物混合使用,以滿足作為液晶組成物所要求的性能。 Such a liquid crystal optical film is required to have a wide range of operating temperature ranges, polymerizable group reactivity, coating properties, good orientation, and chemical stability. The liquid crystal element uses a material which can exhibit a liquid crystal phase, and it is currently impossible to satisfy such a characteristic with a single compound, so one or two kinds will be used. Many of the above reactive liquid crystal compounds or reactive non-liquid crystalline compounds having excellent characteristics are used in combination to satisfy the performance required as a liquid crystal composition.
在液晶光學薄膜領域中,如何在用於液晶組成物的化合物所要求的諸多特性中,提供具有良好的與不同反應性液晶材料或反應性非液晶材料的相容性,化學穩定性,並在較寬的溫度範圍能夠保持液晶相,而且當其用於液晶光學薄膜時具有良好的取向性、化學穩定性的化合物或聚合性液晶組成物,乃成為重要課題。 In the field of liquid crystal optical films, how to provide good compatibility with different reactive liquid crystal materials or reactive non-liquid crystal materials among chemical properties required for compounds for liquid crystal compositions, and A liquid crystal phase can be maintained in a wide temperature range, and a compound having a good orientation and chemical stability or a polymerizable liquid crystal composition when used in a liquid crystal optical film is an important subject.
本發明人等為瞭解決如上問題,不斷努力研究,其結果發現了將液晶性化合物,其中核心結構具有一個以上的或不含連接基團而以單鍵相連或以多環構造相連的環結構,與聚合性介晶化合物混合而構成聚合性液晶組成物時,能具有良好的相容性,化學穩定性,並在較寬的溫度範圍內保持液晶相的特性,於是完成了本發明。 The present inventors have continually diligently studied in order to solve the above problems, and as a result, have found a ring-like structure in which a liquid crystalline compound having a core structure having one or more or no linking groups and having a single bond or a polycyclic structure is attached. When the polymerizable liquid crystal composition is mixed with a polymerizable mesogenic compound, the compatibility can be improved, the chemical stability is maintained, and the characteristics of the liquid crystal phase are maintained over a wide temperature range, and thus the present invention has been completed.
本發明的目的在於提供一種聚合性液晶組成物以及包括其的光學薄膜,其具有良好的二種以上的液晶材料之間的相容性,化學穩定性,在較寬的溫度範圍內能保持液晶相,而且當使用於液晶光學薄膜時具有良好的取向性和化學穩定性。 An object of the present invention is to provide a polymerizable liquid crystal composition and an optical film comprising the same, which have good compatibility between two or more liquid crystal materials, chemical stability, and can maintain liquid crystal over a wide temperature range. Phase, and has good orientation and chemical stability when used in liquid crystal optical films.
為了達到上述目的,本發明提供包括至少一種聚合性介晶化合物和如下化學式1中之一種以上的液晶性化合物之聚合性液晶組成物:【化學式1】P1-AL-P2, 式中,P1和P2為可聚合的基團,AL為核心結構,其具有一個以上的或不具有連接基團而以單鍵相連,或以多環結構相連的環結構。 In order to achieve the above object, the present invention provides a polymerizable liquid crystal composition comprising at least one polymerizable mesogen compound and one or more liquid crystal compounds of the following Chemical Formula 1: [Chemical Formula 1] P1-AL-P2, In the formula, P1 and P2 are a polymerizable group, and AL is a core structure having one or more ring groups which are connected by a single bond or have a polycyclic structure.
本發明還提供包括該聚合性液晶組成物的光學薄膜、液晶面板以及液晶顯示裝置。 The present invention also provides an optical film, a liquid crystal panel, and a liquid crystal display device including the polymerizable liquid crystal composition.
本發明將液晶性化合物,其核心結構具有一個以上的或不含連接基團而以單鍵相連或以多環結構相連的環結構,與聚合性介晶化合物混合而構成聚合性液晶組成物,由此能製造出具有良好的液晶材料之間的相容性,化學穩定性,在較寬的溫度範圍內能保持液晶相,而且當使用於液晶光學薄膜時能具有良好的取向性,化學穩定性的光學薄膜,其製造方法較為簡單,因此具有經濟效益。 In the present invention, a liquid crystalline compound having a core structure having one or more or no linking groups and having a single bond or a polycyclic structure is bonded to the polymerizable mesogenic compound to form a polymerizable liquid crystal composition. Thereby, it is possible to produce a good compatibility between the liquid crystal materials, chemical stability, to maintain the liquid crystal phase over a wide temperature range, and to have good orientation and chemical stability when used in a liquid crystal optical film. The optical film is simple in its manufacturing method and therefore economical.
若非另行界定其含義,在此使用到的所有技術性或科學性詞語,均具有與本發明所屬的技術領域中熟知該技術的人士一般所能理解到的相同含義。一般,本說明書所使用的命名法以及下述實驗方法均在本技術領域公知的,亦是通常使用的。 All technical or scientific terms used herein have the same meaning as commonly understood by those skilled in the art to which the invention pertains, unless otherwise defined. In general, the nomenclature used in the present specification and the experimental methods described below are well known in the art and are also commonly used.
本發明在一方面有關於一種聚合性液晶組成物,其包括至少一種聚合性介晶化合物和如下化學式1中至少一種液晶性化合物。 The present invention relates, in one aspect, to a polymerizable liquid crystal composition comprising at least one polymerizable mesogen compound and at least one liquid crystal compound of the following Chemical Formula 1.
【化學式1】P1-AL-P2, 式中,P1和P2為可聚合的基團,AL為核心結構,該核心結構具有一個以上的或不含連接基團而以單鍵相連,或以多環結構相連的環結構。本發明中,該可聚合的基團係指能透過光照射進行交聯結合的基團,如丙烯醯(acryloyl)、甲基丙烯醯基(methacryloyl)等,其能起到形成三維高分子網絡的作用。至於一個以上的不含連接基團而以單鍵相連的環結構係指以單鍵結合的結構如聯苯基(byphenyl)、三聯苯(terphenyl)等,而具有一個以上的以多環結構相連的環結構係指在環結構中共有一個以上的碳-碳鍵的結構,如萘(napthalene)、蒽(anthracene)和芴(fluorene)等。本發明中發現,當核心結構由一個以上的不含連接基團而以單鍵相連或以多環結構相連的環結構構成時,可減少發生在羧基連接基團結構如酯基連接基團的熱、化學不穩定性,在此若將在核心結構兩端具有可聚合基團的液晶性化合物包括在聚合性液晶組成物中時,可擴大液晶相的溫度範圍。 [Chemical Formula 1] P 1 -A L -P 2 , wherein P 1 and P 2 are polymerizable groups, and A L is a core structure having more than one or no linking group Bonds are connected, or ring structures connected by a multi-ring structure. In the present invention, the polymerizable group refers to a group capable of cross-linking by light irradiation, such as acryloyl, methacryloyl, etc., which can form a three-dimensional polymer network. The role. As for one or more ring structures which are linked by a single bond without a linking group, a structure in which a single bond is bonded, such as a biphenyl group, a terphenyl group or the like, and one or more are connected by a polycyclic structure. The ring structure refers to a structure in which more than one carbon-carbon bond is shared in the ring structure, such as napthalene, anthracene, and fluorene. In the present invention, it has been found that when the core structure is composed of more than one ring structure which does not contain a linking group and is linked by a single bond or a polycyclic structure, the occurrence of a carboxyl linking group structure such as an ester group linking group can be reduced. Thermal and chemical instability. When a liquid crystalline compound having a polymerizable group at both ends of the core structure is included in the polymerizable liquid crystal composition, the temperature range of the liquid crystal phase can be enlarged.
具體地說,根據本發明,其特徵在於:該AL選自如下群:
在較佳實施方式中,其特徵在於:該液晶性化合物為一種化合物,其以如下化學式3所示:【化學式3】
式中,L1及L2分別獨立地為選自H、F、Cl、Br、CH3、OCH3和OCF3群中之取代基。本發明的一實施例中發現,將如上述化學式3所示的液晶性化合物與聚合性介晶化合物混合,制得聚合性液晶組成物時,可擴大液晶相的溫度範圍。更佳地,其特徵在於:該液晶性化合物為4,4’-二(丙烯醯氧基)聯苯4,4'-bis(acryloyloxy)biphenyl)。上述化學式3所示的化合物通過:於丙烯酸(acrylic acid)加入二氯甲烷(dichloromethane)、DMF和草醯氯(oxalic chloride)形成氯化丙烯酸(acrylic chloride),在形成的氯化丙烯酸中添加4,4’聯苯 (4,4’-biphenyl)和三乙胺(triethyl amine)進行反應後,蒸發掉溶劑,可分離獲得。 In the formula, L1 and L2 are each independently a substituent selected from the group consisting of H, F, Cl, Br, CH 3 , OCH 3 and OCF 3 . In one embodiment of the present invention, when a liquid crystalline compound represented by the above Chemical Formula 3 and a polymerizable mesogen compound are mixed to obtain a polymerizable liquid crystal composition, the temperature range of the liquid crystal phase can be enlarged. More preferably, the liquid crystalline compound is 4,4'-bis(acryloyloxy)biphenyl. The compound represented by the above Chemical Formula 3 is obtained by adding acrylic acid to dichloromethane, DMF and oxalic chloride to form acrylic chloride, and adding 4 to the formed chlorinated acrylic acid. After 4' biphenyl (4,4'-biphenyl) and triethylamine are reacted, the solvent is evaporated to obtain a separation.
在本發明中,該聚合性介晶化合物可以用一般通用的公知的RM(reactive mesogen),其與本發明中的液晶性化合物混合用以聚合性液晶組成物時,可提高其特性。具體地說,其特徵在於:該聚合性介晶化合物為如下化學式2所示的至少一種化合物:【化學式2】或P1-A1-Sp-A2-介晶基團-P2 In the present invention, the polymerizable mesogen compound can be obtained by using a generally known RM (reactive mesogen) which is generally used in combination with the liquid crystalline compound of the present invention to improve the properties of the polymerizable liquid crystal composition. Specifically, the polymerizable mesogen compound is at least one compound represented by the following Chemical Formula 2: [Chemical Formula 2] Or P 1 -A 1 -Sp-A 2 - mesogenic group-P 2
式中,P1為可聚合的基團,係指可透過光折射進行交聯結合的基團如丙烯醯(acryloyl)、甲基丙烯醯基(methacryloyl)等;Sp表示具有1至20個碳原子的聯接基團;A1和A2分別獨立地為選自-O-,-S-,-CO-,-COO-,-OCO-,-OCOO-或選自單鍵的基團;P2為選自H,F,CH3,OCH3,OCF3,鹵基、氰基及可聚合的基團中之一種,或具有以-A2-Sp-A1-P1表示的含義。介晶基團以-(X1-A3)n-X2-A4-X3-表示;A3和A4分別獨立地選自-O-,-S-,-CO-,-COO-,-OCO-,-OCOO-或單鍵;X1,X2和X3分別獨立地表示1,4-亞苯基,其中,一個以上的CH基團還可以被N取代、1,4-環己基、1,4-亞環己基或萘-2,6-二基,其中,一個或兩個不相鄰的CH2基團還可以被O和/或S取代,這些基團均可以不被取代,或被鹵素、氰基、硝基、或烷基、烷氧基或烷醯基一取代或多取代,其中,烷基、烷氧基或烷醯基具有1至7個碳原子,其中,一個以上的氫原子被F或Cl取代,n表示0,1或2。 Wherein P1 is a polymerizable group, and means a group which is crosslinkable by light refraction, such as acryloyl, methacryloyl, etc.; and Sp represents 1 to 20 carbon atoms. The linking group; A1 and A2 are each independently selected from the group consisting of -O-, -S-, -CO-, -COO-, -OCO-, -OCOO- or a group selected from a single bond; H, F, CH 3 , OCH 3 , OCF 3 , one of a halogen group, a cyano group and a polymerizable group, or have the meaning represented by -A 2 -Sp-A 1 -P 1 . The mesogenic group is represented by -(X 1 -A 3 ) n -X 2 -A 4 -X 3 -; A3 and A4 are each independently selected from -O-, -S-, -CO-, -COO-, -OCO-, -OCOO- or a single bond; X1, X2 and X3 each independently represent a 1,4-phenylene group, wherein one or more CH groups may also be substituted by N, 1,4-cyclohexyl, 1 a 4-cyclohexylene group or a naphthalene-2,6-diyl group, wherein one or two non-adjacent CH 2 groups may also be substituted by O and/or S, and these groups may not be substituted, or Monosubstituted or polysubstituted by halogen, cyano, nitro, or alkyl, alkoxy or alkanoyl, wherein the alkyl, alkoxy or alkano group has from 1 to 7 carbon atoms, of which more than one The hydrogen atom is replaced by F or Cl, and n represents 0, 1 or 2.
該聚合性介晶化合物根據上述化學式2中的該P2具有哪一種結構可以分為單反應性化合物或雙反應性化合物。一般,該P2若表示為-A2-Sp-A1-P1,或具有可聚合的基團時,由於聚合性介晶化合物的兩個末端具有可聚合的基團,因此這種化合物可稱為雙反應性聚合性介晶化合物。該雙反應性聚合性介晶化合物包含在聚合性液晶組成物中時,對高分子光交聯網絡的形成能起到最主要的作用。另外,該聚合性介晶化合物,P2若不包括可聚合的基團時,可稱為單反應性聚合性介晶化合物。由於單反應性聚合性介晶化合物僅在一個末端具有可聚合的基團,另一個末端可包括H,F,CH3,OCH3,OCF3、鹵基、氰基等基團。這種單反應性聚合性介晶化合物包括在聚合性液晶組成物中時,能起到調節黏度、結晶化溫度、雙折射等作用。該單反應性聚合性介晶化合物在非聚合性末端可以導入具有不同電負性的功能基團,其若是F、OCF3、鹵基、氰基時呈現極性,若是H、烷基、烷氧基時呈現非極性。極性化合物包含在聚合性液晶組成物即可起到降低黏度,提升雙折射率的作用,非極性化合物包含在聚合性液晶組成物可以起到調節結晶化溫度的作用。 The polymerizable mesogenic compounds in which the structure of the chemical formula 2 P 2 can be divided in accordance with a single or a double reactive compound reactive compound. In general, when P 2 is represented by -A 2 -Sp-A 1 -P 1 or has a polymerizable group, since the both ends of the polymerizable mesogen compound have a polymerizable group, the compound It may be referred to as a bireactive polymeric mesogenic compound. When the double-reactive polymerizable mesogen compound is contained in a polymerizable liquid crystal composition, it plays a major role in the formation of a polymer photocrosslinking network. Further, the polymerizable mesogen compound, if P 2 does not include a polymerizable group, may be referred to as a monoreactive polymerizable mesogen compound. Since the monoreactive polymeric mesogen compound has a polymerizable group only at one end, the other end may include a group such as H, F, CH 3 , OCH 3 , OCF 3 , a halogen group, a cyano group or the like. Such a monoreactive polymerizable mesogen compound, when included in a polymerizable liquid crystal composition, can function to adjust viscosity, crystallization temperature, birefringence, and the like. The monoreactive polymerizable mesogenic compound may introduce a functional group having a different electronegativity at the non-polymerizable terminal, and if it is F, OCF 3 , a halogen group or a cyano group, it exhibits a polarity, and if it is H, an alkyl group or an alkoxy group The base time is non-polar. The polar compound is contained in the polymerizable liquid crystal composition to lower the viscosity and enhance the birefringence. The non-polar compound contained in the polymerizable liquid crystal composition can function to adjust the crystallization temperature.
在本發明中,該聚合性液晶組成物的特徵在於包括至少一種55至50重量%的雙反應性化合物、至少一種20至35重量%的單反應性化合物以及1至20重量%的化學式1之化合物,但這僅是一種具體實施例,對於所屬技術人士而言,根據不同光學裝置可以調整該組成比是顯而易見的。 In the present invention, the polymerizable liquid crystal composition is characterized by comprising at least one 55 to 50% by weight of a bireactive compound, at least one 20 to 35% by weight of a monoreactive compound, and 1 to 20% by weight of Chemical Formula 1 Compounds, but this is only one specific embodiment, and it will be apparent to those skilled in the art that the composition ratio can be adjusted for different optical devices.
本發明的特徵還在於包括至少一種45至70重量%的雙反應性化合物、至少一種10至25重量%的負介電性單反應性化合物、至少一種5至20重量%的正介電性單反應性化合物以及1至20重量%的化學式1之化合物,但這 僅是一種具體實施例,對於所屬技術人士而言,根據不同光學裝置可以調整該組成比是顯而易見的。 The invention is also characterized by comprising at least one 45 to 70% by weight of a bireactive compound, at least one 10 to 25% by weight of a negative dielectric monoreactive compound, at least one 5 to 20% by weight of a positive dielectric single a reactive compound and 1 to 20% by weight of a compound of Chemical Formula 1, but It is merely a specific embodiment, and it will be apparent to those skilled in the art that the composition ratio can be adjusted according to different optical devices.
本發明的較佳實施例中發現,本發明中的一個實施例包括:
式中,n為0至10的整數,當使用該聚合性液晶組成物時,可擴大液晶相的溫度範圍。 In the formula, n is an integer of 0 to 10, and when the polymerizable liquid crystal composition is used, the temperature range of the liquid crystal phase can be enlarged.
本發明中,聚合性液晶組成物還可以包括光起始劑。本發明中,光起始劑起到引發光交聯的作用。光聚合較佳地通過UV照射進行,當通過UV進行聚合時,可以使用一種在UV照射下被分解,並能生成引發聚合反應的自由基或離子(Ion)的光起始劑。較佳地使用UV光起始劑,尤其是自由基型(radical)UV光起始劑。自由基型UV光起始劑係用於進行自由基聚合的一種標準型光起始劑,例如包括:a-羰基化合物(美國專利公告第2367661號、美國專利公告第2367670號)、偶姻乙醚(acyloin ethers)(美國專利公告第248828號)、a-碳氫取代芳香族偶姻化合物(美國專利公告第27722512號)、多核醌類化合物(美國專利公報第2951758號)、三芳基咪唑二聚物和p-胺基丙苯酮的組合(美國專利公告第4239850號)、吖啶(acridine)和吩嗪(phenazine)的化合物(日本公開專利公報昭60-105667號、美國專利公告第4239850號)以及惡二唑 (oxadiazole)化合物(美國專利公告第4212970號)。例如,可以使用商用製劑如IrgacureR或DarocureR(均由Ciba Geigy AG製造)等,可以使用公知的能包括在液晶組成物中的光起始劑。 In the present invention, the polymerizable liquid crystal composition may further include a photoinitiator. In the present invention, the photoinitiator acts to initiate photocrosslinking. Photopolymerization is preferably carried out by UV irradiation, and when polymerization is carried out by UV, a photoinitiator which is decomposed under UV irradiation and which generates a radical or ion (Ion) which initiates polymerization can be used. UV photoinitiators, especially radical UV photoinitiators, are preferably used. A radical type UV photoinitiator is a standard type photoinitiator for performing radical polymerization, and includes, for example, a-carbonyl compound (U.S. Patent No. 2,276,661, U.S. Patent No. 2,367,670), (acyloin ethers) (US Patent Publication No. 248828), a-hydrogen-substituted aromatic auxin compounds (US Patent Publication No. 27722212), polynuclear hydrazine compounds (US Patent Publication No. 2951758), triaryl imidazole dimerization a combination of a substance and p-aminopropionone (U.S. Patent No. 4,239,850), acridine and phenazine (Japanese Patent Publication No. Sho 60-105667, U.S. Patent No. 4,239,850 And oxadiazole (oxadiazole) compound (US Patent Publication No. 4212970). For example, a commercial preparation such as IrgacureR or Darocure R (all manufactured by Ciba Geigy AG) or the like can be used, and a known photoinitiator which can be included in the liquid crystal composition can be used.
本發明的聚合性液晶組成物適合用於如TN、STN、AMD-TN或其他類型的顯示器等液晶顯示裝置上的光學薄膜。更具體地說,可以使用於視角補償膜,如利用液晶高分子化的偏光膜、應用液晶分子螺距(pitch)的彩色濾光膜、用於補償LCD面板的視角所造成的亮度變化的光學薄膜等;還用於三維立體畫像的光學薄膜,如為適用雙眼視差的圖形化的相位差膜、用於產生光軸變化的光學薄膜、將綫偏振光轉換為圓偏振光的光學薄膜等,以及光學薄膜,其用於BLU部分以提高LCD的光效率或利用薄膜折射率以調整光線的進行方向。 The polymerizable liquid crystal composition of the present invention is suitably used for an optical film on a liquid crystal display device such as a TN, STN, AMD-TN or other type of display. More specifically, it can be used for a viewing angle compensation film such as a polarizing film which is polymerized by a liquid crystal, a color filter film which uses a pitch of a liquid crystal molecule, and an optical film for compensating for a change in luminance caused by a viewing angle of the LCD panel. An optical film which is also used for a three-dimensional portrait, such as a patterned retardation film for binocular parallax, an optical film for generating optical axis change, an optical film for converting linearly polarized light into circularly polarized light, and the like, And an optical film for the BLU portion to increase the light efficiency of the LCD or to utilize the refractive index of the film to adjust the direction of light travel.
下麵,通過實施例對本發明進行更詳細的說明。任何熟習發明所屬技術領域的通常知識之人士應顯而易見上述實施例僅例示性說明本發明,而非用於限制本發明之範圍。 Hereinafter, the present invention will be described in more detail by way of examples. It will be apparent to those skilled in the art that the present invention is not limited to the scope of the invention.
4,4’-二(丙烯醯氧基)聯苯(4,4'-bis(acryloyloxy)biphenyl)之製備Preparation of 4,4'-bis(acryloyloxy)biphenyl
於裝有冰浴器的500mL圓底燒瓶中加入丙烯酸(23.2g,0.321mol)、二氯甲烷(200ml),滴加兩滴DMF。然後慢慢添加草醯氯(oxalic chloride)(40.8g,0.321mol)後,在室溫攪拌6小時。再加入三乙胺(40g,0.327mol)、4,4’-聯苯(10g,0.053mol)後,在室溫反應24小時。使反應混合物的溶劑蒸發掉,用柱層析(n-hexene:ethyl acetate=10:1)分離,獲得白色固體化合物。 Acrylic acid (23.2 g, 0.321 mol), dichloromethane (200 ml) was added to a 500 mL round bottom flask equipped with an ice bath, and two drops of DMF were added dropwise. Then, oxalic chloride (40.8 g, 0.321 mol) was slowly added, followed by stirring at room temperature for 6 hours. Further, triethylamine (40 g, 0.327 mol) and 4,4'-biphenyl (10 g, 0.053 mol) were added, and the mixture was reacted at room temperature for 24 hours. The solvent of the reaction mixture was evaporated and purified by column chromatography (n-hexene: ethyl acetate = 10:1) to afford white solid.
本實施例將要瞭解根據本發明的聚合性液晶組成物用於光學薄膜時的特性。 This embodiment will understand the characteristics of the polymerizable liquid crystal composition according to the present invention when it is used for an optical film.
本實施例中,混合了聚合性液晶組成物,包括如下組成: In this embodiment, a polymerizable liquid crystal composition is mixed, including the following composition:
如下聚合性介晶化合物(1)60.0wt%;
如下聚合性介晶化合物(2)30.0wt%;
實施例1所製備的如下液晶性化合物(3)5.0wt%;以及
光起始劑(Irgacure 907,由Ciba Geigy AG購得)5.0wt%。 A photoinitiator (Irgacure 907, available from Ciba Geigy AG) 5.0 wt%.
該化合物(1)按WO93/22397所記載的方法製得;該化合物(2)按歐洲專利申請號EP 0331233 B1所記載的方法製得;該光起始劑Irgacure 907具有如下化學式:
為利用該聚合性液晶組成物製備光學薄膜,將含有在甲苯中的該聚合性液晶組成物之30重量%溶液塗佈於TAC膜上,其中該TAC膜用絨塗杆在500mm長度單向擦拭好。然後使甲苯蒸發掉,並收得1μm厚的該引發好的聚合性混合物層。接著,使用10mW/cm2的照度及365nm的UV光照射使該層聚合。 In order to prepare an optical film using the polymerizable liquid crystal composition, a 30% by weight solution containing the polymerizable liquid crystal composition in toluene was applied onto a TAC film, wherein the TAC film was unidirectionally wiped with a velvet coated rod at a length of 500 mm. it is good. The toluene was then evaporated off and a 1 μm thick layer of the initiated polymerizable mixture was obtained. Next, the layer was polymerized by irradiation with an illuminance of 10 mW/cm 2 and UV light of 365 nm.
為確認該實施例2所製成的聚合性液晶組成物在薄膜上的塗層和取向性,利用偏光顯微鏡觀察了區域變化,其結果如下表1所示:
如該表1所示,根據光線的偏光方向不同,偏光顯微鏡所表現出的亮度有顯著差異,因此可以確認其取向狀態良好。 As shown in Table 1, the brightness exhibited by the polarizing microscope was significantly different depending on the polarization direction of the light, and therefore it was confirmed that the orientation state was good.
為與根據本發明的反應性液晶組成物進行比較,將未含有本發明之液晶性化合物的反應性液晶組成物按如下組成進行混合: In order to compare with the reactive liquid crystal composition according to the present invention, a reactive liquid crystal composition not containing the liquid crystalline compound of the present invention is mixed as follows:
如下聚合性介晶化合物(1)65.0wt%;
如下聚合性介晶化合物(2)30.0wt%;以及
光起始劑(Irgacure 907,由Ciba Geigy AG購得)5.0wt%。 A photoinitiator (Irgacure 907, available from Ciba Geigy AG) 5.0 wt%.
該化合物(1)按WO93/22397所記載的方法製得;該化合物(2)按歐洲專利申請號EP 0331233 B1所記載的方法製得;該光起始劑Irgacure 907具有如下化學式:
為利用該聚合性液晶組成物製備光學薄膜,將含有在甲苯中的該聚合性液晶組成物之30重量%溶液塗佈於TAC膜上,其中該TAC膜用絨塗杆在500mm長度單向擦拭好。然後使甲苯蒸發掉,並收得1μm厚的該引發好的聚合性混合物層。接著,使用10mW/cm2的照度及365nm的UV光照射使該層聚合。 In order to prepare an optical film using the polymerizable liquid crystal composition, a 30% by weight solution containing the polymerizable liquid crystal composition in toluene was applied onto a TAC film, wherein the TAC film was unidirectionally wiped with a velvet coated rod at a length of 500 mm. it is good. The toluene was then evaporated off and a 1 μm thick layer of the initiated polymerizable mixture was obtained. Next, the layer was polymerized by irradiation with an illuminance of 10 mW/cm 2 and UV light of 365 nm.
為調查實施例與比較例之聚合性液晶組成物的向列型液晶相的溫度範圍,在70至100℃範圍內調查了向列相。將根據本發明的實施例之聚合性液晶組成物在93℃下表現出的相位與比較例在80℃下表現出的相位進行比較,其照片如下表2所示:
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JP5162985B2 (en) * | 2006-09-21 | 2013-03-13 | Jnc株式会社 | Trifunctional compound, composition and polymer thereof |
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- 2011-08-12 KR KR1020110080683A patent/KR20130017938A/en not_active Application Discontinuation
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- 2012-08-10 TW TW101129004A patent/TWI568839B/en not_active IP Right Cessation
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TW201307539A (en) | 2013-02-16 |
CN103906823B (en) | 2016-11-02 |
CN103906823A (en) | 2014-07-02 |
WO2013025006A2 (en) | 2013-02-21 |
KR20130017938A (en) | 2013-02-20 |
WO2013025006A3 (en) | 2013-05-30 |
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