TWI804688B - Compound, liquid crystal composition and liquid crystal display element - Google Patents

Compound, liquid crystal composition and liquid crystal display element Download PDF

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TWI804688B
TWI804688B TW108136306A TW108136306A TWI804688B TW I804688 B TWI804688 B TW I804688B TW 108136306 A TW108136306 A TW 108136306A TW 108136306 A TW108136306 A TW 108136306A TW I804688 B TWI804688 B TW I804688B
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carbons
substituted
hydrogen
diyl
independently
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森絢子
矢野智広
矢野匡一
高田章
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日商捷恩智股份有限公司
日商捷恩智石油化學股份有限公司
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Abstract

本發明提供一種具有化學穩定性高、使液晶分子配向的能力高、於液晶組成物中的溶解度高，且液晶顯示元件的電壓保持率大的極性化合物。一種化合物，由式（1）表示。R1 為氫或可經取代的烷基；環A1 及環A2 為可經取代的伸苯基等；a為0～4；Z1 為單鍵或可經取代的伸烷基等；R2 為可經取代的烷基；環A2 、或Sp0 中，至少一個氫可經式（1-a）取代；Sp0 、Sp2 ～Sp5 為單鍵或可經取代的伸烷基；M1 ～M4 為氫、氟等；R3 為碳數1至10的烷基；X1 為-OH等。The invention provides a polar compound with high chemical stability, high ability to align liquid crystal molecules, high solubility in liquid crystal composition, and high voltage retention rate of liquid crystal display elements. A compound represented by formula (1). R 1 is hydrogen or an alkyl group that may be substituted; Ring A 1 and Ring A 2 are phenylene that may be substituted; a is 0 to 4; Z 1 is a single bond or alkylene that may be substituted; R 2 is an alkyl group that can be substituted; in ring A 2 or Sp 0 , at least one hydrogen can be replaced by formula (1-a); Sp 0 , Sp 2 ~ Sp 5 are single bonds or alkane that can be substituted group; M 1 to M 4 are hydrogen, fluorine, etc.; R 3 is an alkyl group with 1 to 10 carbons; X 1 is -OH, etc.

Description

化合物、液晶組成物及液晶顯示元件Compound, liquid crystal composition and liquid crystal display element

本發明是有關於一種化合物、液晶組成物及液晶顯示元件。更詳細而言，本發明是有關於一種兼具甲基丙烯醯氧基等聚合性基與兩個經-OH基等極性基取代的丙烯醯氧基等聚合性基的化合物、包含該化合物且介電常數各向異性為正或負的液晶組成物及包含該組成物或其一部分硬化物的液晶顯示元件。The invention relates to a compound, a liquid crystal composition and a liquid crystal display element. More specifically, the present invention relates to a compound having a polymerizable group such as methacryloxy group and two polymerizable groups such as acryloxy group substituted by polar groups such as -OH group, including the compound and A liquid crystal composition having a positive or negative dielectric anisotropy and a liquid crystal display device comprising the composition or a part of its cured product.

若基於液晶分子的運作模式而對液晶顯示元件進行分類，則可分類為相變（phase change，PC）、扭轉向列（twisted nematic，TN）、超扭轉向列（super twisted nematic，STN）、電控雙折射（electrically controlled birefringence，ECB）、光學補償彎曲（optically compensated bend，OCB）、共面切換（in-plane switching，IPS）、垂直配向（vertical alignment，VA）、邊緣場切換（fringe field switching，FFS）、電場感應光反應配向（field-induced photo-reactive alignment，FPA）等模式。另外，若基於元件的驅動方式，則可分類為被動矩陣（passive matrix，PM）與主動矩陣（active matrix，AM）。PM被分類為靜態式（static）、多工式（multiplex）等，AM被分類為薄膜電晶體（thin film transistor，TFT）、金屬-絕緣體-金屬（metal insulator metal，MIM）等。進而，TFT可分類為非晶矽（amorphous silicon）及多晶矽（polycrystal silicon）。後者根據製造步驟而分類為高溫型與低溫型。若進行基於光源的分類，則可分類為利用自然光的反射型、利用背光的透過型、以及利用自然光與背光這兩者的半透過型。If liquid crystal display elements are classified based on the operation mode of liquid crystal molecules, they can be classified into phase change (phase change, PC), twisted nematic (twisted nematic, TN), super twisted nematic (super twisted nematic, STN), Electrically controlled birefringence (ECB), optically compensated bend (OCB), in-plane switching (IPS), vertical alignment (vertical alignment, VA), fringe field switching (fringe field switching (FFS), field-induced photo-reactive alignment (FPA) and other modes. In addition, if the drive method is based on components, it can be classified into passive matrix (passive matrix, PM) and active matrix (active matrix, AM). PM is classified into static type (static), multiplex type (multiplex), etc., AM is classified into thin film transistor (thin film transistor, TFT), metal-insulator-metal (metal insulator metal, MIM), etc. Furthermore, TFT can be classified into amorphous silicon (amorphous silicon) and polycrystalline silicon (polycrystalline silicon). The latter are classified into high temperature type and low temperature type according to the manufacturing steps. When classified based on the light source, it can be classified into reflective type utilizing natural light, transmissive type utilizing backlight, and transflective type utilizing both natural light and backlight.

具有向列相的液晶組成物具有適當的特性。藉由提高該組成物的特性，可獲得具有良好特性的AM元件。將所述組成物的特性與AM元件的特性的關聯歸納於下述表1中。A liquid crystal composition having a nematic phase has suitable characteristics. By improving the properties of this composition, an AM device with good properties can be obtained. The correlation between the properties of the composition and the properties of the AM device is summarized in Table 1 below.

Figure 108136306-A0304-0001
1）可縮短於液晶顯示元件中注入組成物的時間
Figure 108136306-A0304-0001
 1) It can shorten the time to inject the composition into the liquid crystal display element

基於市售的AM元件來對所述組成物的特性進一步進行說明。向列相的溫度範圍（呈現向列相的溫度範圍）與元件可使用的溫度範圍相關聯。向列相的較佳的上限溫度為約70℃以上，而且向列相的較佳的下限溫度為約-10℃以下。 所述組成物的黏度與元件的響應時間相關聯。為了以元件顯示動態圖像，較佳為響應時間短。理想為短於1毫秒的響應時間。因此，較佳為所述組成物的黏度低，進而，更佳為即便於低溫下，所述組成物的黏度亦低。The characteristics of the composition will be further described based on a commercially available AM device. The temperature range of the nematic phase (the temperature range in which the nematic phase appears) is associated with the usable temperature range of the element. A preferable upper limit temperature of the nematic phase is about 70°C or higher, and a preferable lower limit temperature of the nematic phase is about -10°C or lower. The viscosity of the composition correlates with the response time of the element. In order to display a moving image with a device, it is preferable that the response time is short. A response time of less than 1 millisecond is ideal. Therefore, it is preferable that the viscosity of the composition is low, and it is more preferable that the viscosity of the composition is low even at low temperature.

所述組成物的光學各向異性與元件的對比度相關聯。根據元件的模式，需要光學各向異性大或光學各向異性小，即光學各向異性適當。組成物的光學各向異性（Δn）與元件的單元間隙（d）的積（Δn×d）被設計成使對比度成為最大。積的適當值依存於運作模式的種類。於TN等模式的元件中，該值為約0.45 μm。於VA模式的元件中，該值為約0.30 μm至約0.40 μm的範圍，於IPS模式或FFS模式的元件中，該值為約0.20 μm至約0.30 μm的範圍。該些情況下，對單元間隙小的元件而言較佳為具有大的光學各向異性的組成物。 所述組成物的介電常數各向異性大有助於元件的臨限電壓低、消耗電力小與對比度大。因此，較佳為正或負的介電常數各向異性大。組成物的比電阻大有助於元件的電壓保持率大與對比度大。因此，較佳為於初始階段中不僅於室溫下，而且於接近於向列相的上限溫度的溫度下亦具有大的比電阻的組成物。較佳為於長時間使用後，不僅於室溫下而且於接近向列相的上限溫度的溫度下亦具有大的比電阻的組成物。 組成物對紫外線及熱的穩定性與元件的壽命相關聯。於該穩定性高時，元件的壽命長。此種特性對於液晶投影儀、液晶電視等中所使用的AM元件而言較佳。The optical anisotropy of the composition correlates with the contrast of the element. Depending on the mode of the element, it is necessary to have large optical anisotropy or small optical anisotropy, that is, to have appropriate optical anisotropy. The product (Δn×d) of the optical anisotropy (Δn) of the composition and the cell gap (d) of the device is designed so as to maximize the contrast. The appropriate value of the product depends on the type of operation mode. In devices of TN and other modes, this value is about 0.45 μm. In the device of VA mode, the value is in the range of about 0.30 μm to about 0.40 μm, and in the device of IPS mode or FFS mode, the value is in the range of about 0.20 μm to about 0.30 μm. In these cases, a composition having a large optical anisotropy is preferable for a device having a small cell gap. The large dielectric anisotropy of the composition contributes to the low threshold voltage, low power consumption and high contrast of the device. Therefore, it is preferable that the positive or negative dielectric constant anisotropy is large. The high specific resistance of the composition contributes to high voltage retention and high contrast of the device. Therefore, a composition having a large specific resistance not only at room temperature but also at a temperature close to the upper limit temperature of the nematic phase in the initial stage is preferable. It is preferably a composition having a large specific resistance not only at room temperature but also at a temperature close to the upper limit temperature of the nematic phase after long-term use. The stability of the composition to ultraviolet light and heat is related to the lifetime of the device. When the stability is high, the life of the device is long. Such characteristics are preferable for AM elements used in liquid crystal projectors, liquid crystal televisions, and the like.

於聚合物穩定配向（polymer sustained alignment，PSA）型的液晶顯示元件中，使用含有聚合體的液晶組成物。首先，將添加有少量聚合性化合物的組成物注入至元件中。此處，一般使用具有多個聚合性基的聚合性化合物。其次，一面對夾持該元件的基板之間施加電壓，一面對組成物照射紫外線。聚合性化合物進行聚合而於組成物中生成聚合體的網狀結構。若使用該組成物，則可藉由聚合體來控制液晶分子的配向，因此元件的響應時間縮短，圖像的殘像得以改善。具有TN、ECB、OCB、IPS、VA、FFS、FPA等模式的元件可期待聚合體的此種效果。A liquid crystal composition containing a polymer is used in a polymer sustained alignment (PSA) type liquid crystal display device. First, a composition added with a small amount of a polymerizable compound is injected into the device. Here, generally, a polymerizable compound having a plurality of polymerizable groups is used. Next, while applying a voltage between the substrates sandwiching the device, ultraviolet rays are irradiated to the composition. The polymerizable compound polymerizes to form a polymer network structure in the composition. If this composition is used, the alignment of the liquid crystal molecules can be controlled by the polymer, so the response time of the device is shortened and the afterimage of the image is improved. Such an effect of polymers can be expected for devices having modes such as TN, ECB, OCB, IPS, VA, FFS, and FPA.

於通用的液晶顯示元件中，液晶分子的垂直配向是藉由聚醯亞胺配向膜來達成。另一方面，作為不具有配向膜的液晶顯示元件，提出有將極性化合物添加至液晶組成物中，而使液晶分子配向的模式。首先，將添加有少量極性化合物及少量聚合性化合物的組成物注入至元件中。作為該聚合性化合物，一般使用具有多個聚合性基的聚合性化合物。此處，藉由極性化合物的作用而液晶分子進行配向。其次，一面對夾持該元件的基板之間施加電壓，一面對組成物照射紫外線。此處，聚合性化合物進行聚合，並使液晶分子的配向穩定化。若使用該組成物，則可藉由極性化合物及聚合體來控制液晶分子的配向，因此元件的響應時間縮短，圖像的殘像得以改善。進而，於不具有配向膜的元件中，不需要形成配向膜的步驟。由於不存在配向膜，故不存在元件的電阻因配向膜與組成物的相互作用而降低的情況。具有TN、ECB、OCB、IPS、VA、FFS、FPA等模式的元件可期待利用極性化合物與聚合體的組合的此種效果。In common liquid crystal display elements, the vertical alignment of liquid crystal molecules is achieved by polyimide alignment films. On the other hand, as a liquid crystal display element without an alignment film, a mode in which a polar compound is added to a liquid crystal composition to align liquid crystal molecules has been proposed. First, a composition added with a small amount of polar compound and a small amount of polymerizable compound is injected into the device. As the polymerizable compound, a polymerizable compound having a plurality of polymerizable groups is generally used. Here, the liquid crystal molecules are aligned by the action of the polar compound. Next, while applying a voltage between the substrates sandwiching the device, ultraviolet rays are irradiated to the composition. Here, the polymerizable compound polymerizes and stabilizes the alignment of liquid crystal molecules. If this composition is used, the alignment of the liquid crystal molecules can be controlled by the polar compound and the polymer, so the response time of the device is shortened and the afterimage of the image is improved. Furthermore, in an element without an alignment film, the step of forming an alignment film is unnecessary. Since there is no alignment film, the resistance of the device does not decrease due to the interaction between the alignment film and the composition. Devices having modes such as TN, ECB, OCB, IPS, VA, FFS, and FPA can be expected to have such an effect utilizing a combination of a polar compound and a polymer.

迄今為止，於不具有配向膜的液晶顯示元件中，作為兼具極性化合物的作用與聚合性化合物的作用的化合物，合成了具有聚合性的極性化合物（例如，專利文獻1及專利文獻2）。於專利文獻2中，記載了具有多個極性基與多個聚合性基的聚合性化合物（S-1）。So far, polymerizable polar compounds have been synthesized as compounds having both the functions of polar compounds and polymerizable compounds in liquid crystal display elements without an alignment film (for example, Patent Document 1 and Patent Document 2). Patent Document 2 describes a polymerizable compound (S-1) having a plurality of polar groups and a plurality of polymerizable groups.

Figure 02_image005
[現有技術文獻] [專利文獻]
Figure 02_image005
[Prior Art Documents] [Patent Documents]

[專利文獻1]國際公開第2016/129490號 [專利文獻2]國際公開第2017/209161號[Patent Document 1] International Publication No. 2016/129490 [Patent Document 2] International Publication No. 2017/209161

[發明所欲解決之課題] 本發明的第一課題為提供一種化合物，其具有化學穩定性高、使液晶分子配向的能力高、由紫外線照射所引起的聚合反應性高、用於液晶顯示元件的情況下的電壓保持率大的至少一種，而且具有於液晶組成物中的溶解度高。第二課題為提供一種液晶組成物，其包含該化合物，而且滿足向列相的上限溫度高、向列相的下限溫度低、黏度低、光學各向異性適當、正或負的介電常數各向異性大、比電阻大、對紫外線的穩定性高、對熱的穩定性高、彈性常數大等特性的至少一種。第三課題為提供一種液晶顯示元件，其具有可使用元件的溫度範圍廣、響應時間短、透過率高、電壓保持率大、臨限電壓低、對比度大、壽命長、垂直配向性良好等特性的至少一種。 [解決課題之手段][Problem to be Solved by the Invention] The first object of the present invention is to provide a compound having high chemical stability, high ability to align liquid crystal molecules, high polymerization reactivity by ultraviolet irradiation, and high voltage retention when used in a liquid crystal display element At least one of them, and has high solubility in liquid crystal composition. The second problem is to provide a liquid crystal composition, which contains the compound, and satisfies the high upper limit temperature of the nematic phase, low lower limit temperature of the nematic phase, low viscosity, appropriate optical anisotropy, and positive or negative dielectric constants. At least one of characteristics such as large anisotropy, high specific resistance, high stability to ultraviolet rays, high stability to heat, and large elastic constant. The third subject is to provide a liquid crystal display element, which has the characteristics of wide temperature range, short response time, high transmittance, high voltage retention rate, low threshold voltage, high contrast ratio, long life, and good vertical alignment. at least one of . [Means to solve the problem]

本發明是有關於一種式（1）所表示的化合物、包含該化合物的液晶組成物、及包含該組成物及/或該組成物的至少一部分進行聚合而成的聚合物的液晶顯示元件。

Figure 02_image007
式（1）中， R1 為氫或碳數1至15的烷基，該R1 中，至少一個-CH2 -可經-O-或-S-取代，至少一個-(CH2 )2 -可經-CH=CH-或-C≡C-取代，至少一個氫可經氟或氯取代； 環A1 及環A2 獨立地為1,2-伸環丙基、1,3-伸環丁基、1,3-伸環戊基、1,4-伸環己基、1,4-伸環庚基、1,4-伸環己烯基、1,4-伸苯基、萘-2,6-二基、十氫萘-2,6-二基、1,2,3,4-四氫萘-2,6-二基、四氫吡喃-2,5-二基、1,3-二噁烷-2,5-二基、嘧啶-2,5-二基、或吡啶-2,5-二基，該環A1 及環A2 中，至少一個氫可經氟、氯、碳數1至10的烷基、碳數2至10的烯基、碳數1至9的烷氧基、或碳數2至9的烯氧基取代，至少一個氫可經氟或氯取代； a為0、1、2、3、或4； Z1 獨立地為單鍵或碳數1至6的伸烷基，該Z1 中，至少一個-CH2 -可經-O-、-CO-、-COO-、-OCO-、或-OCOO-取代，至少一個-(CH2 )2 -可經-CH=CH-或-C≡C-取代，至少一個氫可經氟或氯取代； Sp0 、Sp2 、Sp3 、及Sp4 獨立地為單鍵或碳數1至15的伸烷基，該Sp0 、Sp2 、Sp3 、及Sp4 中，至少一個-CH2 -可經-O-、-CO-、-COO-、-OCO-、或-OCOO-取代，至少一個-(CH2 )2 -可經-CH=CH-或-C≡C-取代，至少一個氫可經氟或氯取代； M1 、及M2 獨立地為氫、氟、氯、碳數1至5的烷基、或者至少一個氫經氟或氯取代的碳數1至5的烷基； R2 為碳數1至10的烷基，該R2 中，至少一個-CH2 -可經-O-或-S-取代，至少一個-(CH2 )2 -可經-CH=CH-或-C≡C-取代，至少一個氫可經氟或氯取代； X1 獨立地為-OH、-NH2 、-OR4 、-N(R4 )2 、-COOH、-SH、或-Si(R4 )3 ； -OR4 、-N(R4 )2 、及-Si(R4 )3 中， R4 為氫或碳數1至10的烷基，該R4 中，至少一個-CH2 -可經-O-取代，至少一個-(CH2 )2 -可經-CH=CH-取代，該些基中，至少一個氫可經氟或氯取代； 環A2 或Sp0 中，至少一個氫經式（1-a）所表示的基取代；
Figure 02_image009
式（1-a）中， Sp5 為單鍵或碳數1至10的伸烷基，該Sp5 中，至少一個-CH2 -可經-O-、-CO-、-COO-、-OCO-、或-OCOO-取代，至少一個-(CH2 )2 -可經-CH=CH-或-C≡C-取代，至少一個氫可經氟或氯取代； M3 、及M4 獨立地為氫、氟、氯、碳數1至5的烷基、或者至少一個氫經氟或氯取代的碳數1至5的烷基； R3 為碳數1至10的烷基，該R3 中，至少一個-CH2 -可經-O-或-S-取代，至少一個-(CH2 )2 -可經-CH=CH-或-C≡C-取代，至少一個氫可經氟或氯取代。 [發明的效果]The present invention relates to a compound represented by formula (1), a liquid crystal composition containing the compound, and a liquid crystal display device containing the composition and/or a polymer obtained by polymerizing at least a part of the composition.
Figure 02_image007
In formula (1), R 1 is hydrogen or an alkyl group with 1 to 15 carbons, in which at least one -CH 2 - may be substituted by -O- or -S-, and at least one -(CH 2 ) 2 -Can be substituted by -CH=CH- or -C≡C-, at least one hydrogen can be substituted by fluorine or chlorine; Ring A 1 and ring A 2 are independently 1,2-cyclopropyl, 1,3- Cyclobutyl, 1,3-cyclopentyl, 1,4-cyclohexyl, 1,4-cyclohexyl, 1,4-cyclohexenyl, 1,4-phenylene, naphthalene- 2,6-diyl, decalin-2,6-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl, tetrahydropyran-2,5-diyl, 1 , 3-dioxane-2,5-diyl, pyrimidine-2,5-diyl, or pyridine-2,5-diyl, in the ring A 1 and ring A 2 , at least one hydrogen can be fluorine, Chlorine, alkyl with 1 to 10 carbons, alkenyl with 2 to 10 carbons, alkoxy with 1 to 9 carbons, or alkenyloxy with 2 to 9 carbons is substituted, at least one hydrogen can be replaced by fluorine or chlorine Substitution; a is 0, 1, 2, 3, or 4; Z 1 is independently a single bond or an alkylene group with 1 to 6 carbons, and in this Z 1 , at least one -CH 2 - can be passed through -O-, -CO-, -COO-, -OCO-, or -OCOO-, at least one -(CH 2 ) 2 - can be substituted by -CH=CH- or -C≡C-, at least one hydrogen can be fluorine or chlorine Substitution; Sp 0 , Sp 2 , Sp 3 , and Sp 4 are independently a single bond or an alkylene group with 1 to 15 carbons, and among the Sp 0 , Sp 2 , Sp 3 , and Sp 4 , at least one -CH 2 - can be substituted by -O-, -CO-, -COO-, -OCO-, or -OCOO-, at least one -(CH 2 ) 2 - can be substituted by -CH=CH- or -C≡C-, at least One hydrogen can be substituted by fluorine or chlorine; M 1 and M 2 are independently hydrogen, fluorine, chlorine, an alkyl group with 1 to 5 carbons, or an alkane with 1 to 5 carbons in which at least one hydrogen is substituted by fluorine or chlorine group; R 2 is an alkyl group with 1 to 10 carbon atoms, in which at least one -CH 2 - can be substituted by -O- or -S- in this R 2 , and at least one -(CH 2 ) 2 - can be substituted by -CH= CH- or -C≡C-substituted, at least one hydrogen can be replaced by fluorine or chlorine; X 1 is independently -OH, -NH 2 , -OR 4 , -N(R 4 ) 2 , -COOH, -SH, Or -Si(R 4 ) 3 ; in -OR 4 , -N(R 4 ) 2 , and -Si(R 4 ) 3 , R 4 is hydrogen or an alkyl group with 1 to 10 carbons, and in the R 4 , At least one -CH 2 - may be substituted by -O-, at least one -(CH 2 ) 2 - may be substituted by -CH=CH-, and in these groups, at least one hydrogen may be substituted by fluorine or chlorine; Ring A 2 or In Sp 0 , at least one hydrogen is replaced by a group represented by formula (1-a);
Figure 02_image009
In formula (1-a), Sp 5 is a single bond or an alkylene group with 1 to 10 carbons, and in this Sp 5 , at least one -CH 2 - can be passed through -O-, -CO-, -COO-, - OCO-, or -OCOO-substituted, at least one -(CH 2 ) 2 - can be substituted by -CH=CH- or -C≡C-, at least one hydrogen can be substituted by fluorine or chlorine; M 3 , and M 4 are independent is hydrogen, fluorine, chlorine, an alkyl group with 1 to 5 carbons, or an alkyl group with 1 to 5 carbons in which at least one hydrogen is replaced by fluorine or chlorine; R 3 is an alkyl group with 1 to 10 carbons, the R In 3 , at least one -CH 2 - may be substituted by -O- or -S-, at least one -(CH 2 ) 2 - may be substituted by -CH=CH- or -C≡C-, at least one hydrogen may be substituted by fluorine or chlorine substitution. [Effect of the invention]

本發明的第一優點為提供一種化合物，其具有化學穩定性高、使液晶分子配向的能力高、由紫外線照射所引起的聚合反應性高、用於液晶顯示元件的情況下的電壓保持率大的至少一種，而且具有於液晶組成物中的溶解度高。第二優點為提供一種液晶組成物，其包含該化合物，而且滿足向列相的上限溫度高、向列相的下限溫度低、黏度低、光學各向異性適當、正或負的介電常數各向異性大、比電阻大、對紫外線的穩定性高、對熱的穩定性高、彈性常數大等特性的至少一種。第三優點為提供一種液晶顯示元件，其具有可使用元件的溫度範圍廣、響應時間短、透過率高、電壓保持率大、臨限電壓低、對比度大、壽命長、垂直配向性良好等特性的至少一種。The first advantage of the present invention is to provide a compound having high chemical stability, high ability to align liquid crystal molecules, high polymerization reactivity caused by ultraviolet irradiation, and high voltage retention when used in a liquid crystal display element At least one of them, and has high solubility in liquid crystal composition. The second advantage is to provide a liquid crystal composition, which contains the compound, and satisfies the high upper limit temperature of the nematic phase, low lower limit temperature of the nematic phase, low viscosity, appropriate optical anisotropy, and positive or negative dielectric constants. At least one of characteristics such as large anisotropy, high specific resistance, high stability to ultraviolet rays, high stability to heat, and large elastic constant. The third advantage is to provide a liquid crystal display element, which has the characteristics of wide temperature range, short response time, high transmittance, high voltage retention rate, low threshold voltage, high contrast ratio, long life, and good vertical alignment. at least one of .

該說明書中的用語的使用方法如下所述。有時將用語「液晶性化合物」、「液晶組成物」、及「液晶顯示元件」分別簡稱為「化合物」、「組成物」、及「元件」。 「液晶性化合物」是具有向列相、層列相等液晶相的化合物，及雖不具有液晶相，但出於調節上限溫度、下限溫度、黏度、介電常數各向異性等組成物的物性的目的而添加的化合物的總稱。該化合物通常具有1,4-伸環己基或1,4-伸苯基等六員環，且其分子結構為棒狀（rod like）。 「聚合性化合物」是出於在組成物中生成聚合體的目的而添加的化合物。具有烯基的液晶性化合物於其意義方面並非為聚合性化合物。 「極性化合物」是藉由極性基與基板表面等相互作用而幫助液晶分子排列。 「液晶顯示元件」為液晶顯示面板及液晶顯示模組等的總稱。The usage of the terms in this specification is as follows. The terms "liquid crystal compound", "liquid crystal composition", and "liquid crystal display device" are sometimes abbreviated as "compound", "composition", and "device", respectively. "Liquid crystal compound" is a compound that has a nematic phase or a smectic liquid crystal phase, and does not have a liquid crystal phase, but is used to adjust the physical properties of the composition such as upper limit temperature, lower limit temperature, viscosity, and dielectric constant anisotropy. A general term for compounds added for purpose. This compound usually has a six-membered ring such as 1,4-cyclohexylene or 1,4-phenylene, and its molecular structure is rod-like. A "polymerizable compound" is a compound added for the purpose of forming a polymer in the composition. A liquid crystal compound having an alkenyl group is not a polymerizable compound in its meaning. "Polar compounds" help liquid crystal molecules to align by interacting with polar groups and substrate surfaces. "Liquid crystal display device" is a general term for liquid crystal display panels, liquid crystal display modules, and the like.

液晶組成物通常藉由將多種液晶性化合物混合來製備。於該組成物中，出於進一步調整物性的目的而視需要來添加聚合性化合物、聚合起始劑、聚合抑制劑、光學活性化合物、抗氧化劑、紫外線吸收劑、光穩定劑、熱穩定劑、色素、及消泡劑等添加物。關於液晶組成物中的液晶性化合物的比例（含量），即便於添加有添加物的情況下，亦是由基於不包含添加物的液晶組成物的重量的重量百分率（重量%）來表示。液晶組成物中的添加物的比例（添加量）是由基於不包含添加物的液晶組成物的重量的重量百分率（重量%）來表示。即，液晶性化合物或添加物的比例是基於液晶性化合物的總重量而算出。有時亦使用重量百萬分率（ppm）。液晶組成物中的聚合起始劑及聚合抑制劑的比例是例外地基於聚合性化合物的重量來表示。A liquid crystal composition is usually prepared by mixing various liquid crystal compounds. To this composition, polymerizable compounds, polymerization initiators, polymerization inhibitors, optically active compounds, antioxidants, ultraviolet absorbers, light stabilizers, heat stabilizers, Additives such as pigments and defoamers. The ratio (content) of the liquid crystal compound in the liquid crystal composition is represented by weight percentage (wt%) based on the weight of the liquid crystal composition not including the additive even when additives are added. The ratio (addition amount) of the additive in the liquid crystal composition is represented by weight percentage (wt%) based on the weight of the liquid crystal composition not containing the additive. That is, the ratio of the liquid crystal compound or the additive is calculated based on the total weight of the liquid crystal compound. Parts per million (ppm) by weight are also sometimes used. The ratio of the polymerization initiator and the polymerization inhibitor in the liquid crystal composition is exceptionally expressed based on the weight of the polymerizable compound.

「透明點」為液晶性化合物中的液晶相-各向同性相的轉變溫度。「液晶相的下限溫度」為液晶性化合物中的固體-液晶相（層列相、向列相等）的轉變溫度。「向列相的上限溫度」為液晶性化合物與母液晶的混合物或液晶組成物中的向列相-各向同性相的轉變溫度，有時簡稱為「上限溫度」。有時將「向列相的下限溫度」簡稱為「下限溫度」。「提高介電常數各向異性」或「大的介電常數各向異性」的表述是指其值的絕對值增加或大。所謂「電壓保持率大」是指元件於初始階段中不僅於室溫下，而且於接近上限溫度的溫度下亦具有大的電壓保持率，而且於將元件長時間使用後，不僅於室溫下而且於接近上限溫度的溫度下亦具有大的電壓保持率。於組成物或元件中，有時於經時變化試驗（包含加速劣化試驗）的前後研究特性。「於液晶組成物中的溶解度高」的表述是指相對於常溫下的包含液晶性化合物的組成物的任一者，溶解度均高，但作為該組成物，可將用以在下述實施例中對溶解性進行評價的組成物設為基準。The "clearing point" is the transition temperature between a liquid crystal phase and an isotropic phase in a liquid crystal compound. The "lower limit temperature of a liquid crystal phase" is the transition temperature of a solid-liquid crystal phase (smectic phase, nematic phase) in a liquid crystal compound. The "upper limit temperature of the nematic phase" is the transition temperature from the nematic phase to the isotropic phase in the mixture of the liquid crystal compound and the mother liquid crystal or the liquid crystal composition, and is sometimes simply referred to as the "upper limit temperature". The "lower limit temperature of the nematic phase" is sometimes simply referred to as the "lower limit temperature". The expression "increased dielectric constant anisotropy" or "large dielectric constant anisotropy" means that the absolute value of the value is increased or large. The so-called "large voltage retention rate" means that the device has a large voltage retention rate not only at room temperature in the initial stage, but also at a temperature close to the upper limit temperature, and after using the device for a long time, not only at room temperature Moreover, it also has a large voltage retention rate at a temperature close to the upper limit temperature. In a composition or device, characteristics may be studied before and after a time-dependent change test (including accelerated deterioration test). The expression "high solubility in the liquid crystal composition" means that the solubility is high with respect to any composition containing liquid crystal compounds at room temperature, but as this composition, it can be used in the following examples The composition evaluated for solubility was used as a reference.

有時將式（1）所表示的化合物簡稱為「化合物（1）」。化合物（1）是指式（1）所表示的一種化合物、兩種化合物的混合物、或三種以上化合物的混合物。該規則亦適用於選自式（2）所表示的化合物的群組中的至少一種化合物等。 由六邊形包圍的A1 、B1 、C1 等記號分別與環A1 、環B1 、環C1 等相對應。六邊形表示環己烷環或苯環等六員環或者萘環等縮合環。橫切該六邊形的一邊的直線表示環上的任意的氫可經-Sp1 -P1 等基取代。 f、g、h等下標表示經取代的基的個數。於下標為0時，不存在此種取代。 於「環A及環C獨立地為X、Y、或Z」的表述中，由於主語為多個，故使用「獨立地」。於主語為「環A為」時，由於主語為單個，故不使用「獨立地」。The compound represented by formula (1) may be simply referred to as "compound (1)". Compound (1) refers to one compound represented by formula (1), a mixture of two compounds, or a mixture of three or more compounds. This rule also applies to at least one compound selected from the group of compounds represented by formula (2), and the like. Symbols such as A 1 , B 1 , and C 1 surrounded by a hexagon correspond to ring A 1 , ring B 1 , ring C 1 , etc., respectively. The hexagon represents a six-membered ring such as a cyclohexane ring or a benzene ring, or a condensed ring such as a naphthalene ring. A straight line crossing one side of the hexagon indicates that any hydrogen on the ring may be substituted by groups such as -Sp 1 -P 1 . Subscripts such as f, g, and h indicate the number of substituted groups. When the subscript is 0, there is no such substitution. In the expression "ring A and ring C are independently X, Y, or Z", since there are plural subjects, "independently" is used. When the subject is "ring A is", since the subject is singular, "independently" is not used.

於化合物的化學式中，將末端基R11 的記號用於多種化合物中，但該些化合物中的R11 所表示的基分別可相同，或亦可不同。例如，於化合物（2）的R11 為乙基的情況下，化合物（3）的R11 可為乙基，亦可為丙基等其他基。該規則亦適用於其他記號。化合物（8）中，於i為2時，存在兩個環D1 。該化合物中，兩個環D1 所表示的兩個基可相同，或亦可不同。於i大於2時，亦適用於任意的兩個環D1 。該規則亦適用於其他記號。In the chemical formula of the compound, the symbol of the terminal group R 11 is used in various compounds, but the groups represented by R 11 in these compounds may be the same or different. For example, when R 11 of compound (2) is ethyl, R 11 of compound (3) may be ethyl or other groups such as propyl. This rule also applies to other tokens. In compound (8), when i is 2, two rings D 1 exist. In this compound, the two groups represented by the two rings D 1 may be the same or different. When i is greater than 2, it is also applicable to any two rings D 1 . This rule also applies to other tokens.

「至少一個‘A’」的表述是指‘A’的個數為任意。「至少一個‘A’可經‘B’取代」的表述包含未經‘B’取代的‘A’本身的情況、一個‘A’經‘B’取代的情況、兩個以上的‘A’經‘B’取代的情況，該些情況中，經‘B’取代的‘A’位置為任意。取代位置為任意的規則亦適用於「至少一個‘A’經‘B’取代」的表述。「至少一個A可經B、C、或D取代」的表述是指包含A未經取代的情況、至少一個A經B取代的情況、至少一個A經C取代的情況、及至少一個A經D取代的情況、以及多個A經B、C、D的至少兩個取代的情況。例如，至少一個-CH2 -（或-CH2 CH2 -）可經-O-（或-CH=CH-）取代的烷基中，包含烷基、烯基、烷氧基、烷氧基烷基、烷氧基烯基、烯氧基烷基。再者，連續的兩個-CH2 -經-O-取代而成為-O-O-的情況欠佳。於烷基等中，甲基部分（-CH2 -H）的-CH2 -經-O-取代而成為-O-H的情況亦欠佳。The expression "at least one 'A'" means that the number of 'A' is arbitrary. The expression "at least one 'A' may be substituted by 'B'" includes the case where 'A' itself is not substituted by 'B', the case where one 'A' is substituted by 'B', the case where two or more 'A's are In the case of 'B' substitution, in these cases, the position of 'A' substituted with 'B' is arbitrary. The rule that substitution positions are arbitrary also applies to the expression "at least one 'A' is substituted with 'B'". The expression "at least one A may be substituted by B, C, or D" refers to the case where A is unsubstituted, the case where at least one A is substituted by B, the case where at least one A is substituted by C, and the case where at least one A is substituted by D The case of substitution, and the case of a plurality of A being substituted by at least two of B, C, and D. For example, at least one -CH 2 - (or -CH 2 CH 2 -) can be substituted by -O- (or -CH=CH-) in the alkyl group, including alkyl, alkenyl, alkoxy, alkoxy Alkyl, alkoxyalkenyl, alkenyloxyalkyl. Furthermore, the case where two consecutive -CH 2 -s are substituted with -O- to become -OO- is unfavorable. In an alkyl group or the like, it is also unfavorable that -CH 2 - in the methyl moiety (-CH 2 -H) is substituted with -O- to become -OH.

有時使用「R11 及R12 獨立地為碳數1至10的烷基或碳數2至10的烯基，該烷基及烯基中，至少一個-CH2 -可經-O-取代，該些基中，至少一個氫可經氟取代」的表述。該表述中，「該些基中」可按照語句進行解釋。於該表述中，「該些基」是指烷基、烯基、烷氧基、烯氧基等。即，「該些基」表示用語「該些基中」之前所記載的所有基。該常識性解釋亦適用於其他用語。Sometimes "R 11 and R 12 are independently an alkyl group with 1 to 10 carbons or an alkenyl group with 2 to 10 carbons, in which at least one -CH 2 - may be substituted by -O- , in these groups, at least one hydrogen may be substituted by fluorine". In this expression, "these bases" can be interpreted according to the sentence. In this expression, "the groups" refer to alkyl, alkenyl, alkoxy, alkenyloxy and the like. That is, "the groups" means all the groups described before the term "in the groups". This commonsense interpretation applies to other terms as well.

鹵素是指氟、氯、溴、或碘。較佳的鹵素為氟或氯。進而佳的鹵素為氟。液晶性化合物中，烷基為直鏈狀或分支狀，且不包含環狀烷基。一般而言，直鏈狀烷基優於分支狀烷基。該些情況對於烷氧基、烯基等末端基而言亦相同。關於與1,4-伸環己基相關的立體構型，為了提高向列相的上限溫度，反式構型優於順式構型。2-氟-1,4-伸苯基是指下述兩個二價基。化學式中，氟可向左（L），亦可向右（R）。該規則亦適用於四氫吡喃-2,5-二基等藉由自環中去除兩個氫而生成的左右非對稱的二價基。Halogen means fluorine, chlorine, bromine, or iodine. Preferred halogens are fluorine or chlorine. A further preferred halogen is fluorine. In the liquid crystal compound, the alkyl group is linear or branched, and does not contain a cyclic alkyl group. In general, straight-chain alkyl groups are preferred over branched ones. The same applies to terminal groups such as alkoxy and alkenyl. Regarding the configuration related to 1,4-cyclohexylene, the trans configuration is preferable to the cis configuration in order to increase the upper limit temperature of the nematic phase. 2-Fluoro-1,4-phenylene refers to the following two divalent groups. In the chemical formula, fluorine can be left (L) or right (R). This rule also applies to left-right asymmetric divalent radicals such as tetrahydropyran-2,5-diyl formed by removing two hydrogens from the ring.

Figure 02_image011
Figure 02_image011

本發明包括下述項等。The present invention includes the following items and the like.

項1.一種化合物，由式（1）表示。

Figure 02_image013
式（1）中， R1 為氫或碳數1至15的烷基，該R1 中，至少一個-CH2 -可經-O-或-S-取代，至少一個-(CH2 )2 -可經-CH=CH-或-C≡C-取代，至少一個氫可經氟或氯取代； 環A1 及環A2 獨立地為1,2-伸環丙基、1,3-伸環丁基、1,3-伸環戊基、1,4-伸環己基、1,4-伸環庚基、1,4-伸環己烯基、1,4-伸苯基、萘-2,6-二基、十氫萘-2,6-二基、1,2,3,4-四氫萘-2,6-二基、四氫吡喃-2,5-二基、1,3-二噁烷-2,5-二基、嘧啶-2,5-二基、或吡啶-2,5-二基，該環A1 及環A2 中，至少一個氫可經氟、氯、碳數1至10的烷基、碳數2至10的烯基、碳數1至9的烷氧基、或碳數2至9的烯氧基取代，至少一個氫可經氟或氯取代； a為0、1、2、3、或4； Z1 獨立地為單鍵或碳數1至6的伸烷基，該Z1 中，至少一個-CH2 -可經-O-、-CO-、-COO-、-OCO-、或-OCOO-取代，至少一個-(CH2 )2 -可經-CH=CH-或-C≡C-取代，至少一個氫可經氟或氯取代； Sp0 、Sp2 、Sp3 、及Sp4 獨立地為單鍵或碳數1至15的伸烷基，該Sp0 、Sp2 、Sp3 、及Sp4 中，至少一個-CH2 -可經-O-、-CO-、-COO-、-OCO-、或-OCOO-取代，至少一個-(CH2 )2 -可經-CH=CH-或-C≡C-取代，至少一個氫可經氟或氯取代； M1 、及M2 獨立地為氫、氟、氯、碳數1至5的烷基、或者至少一個氫經氟或氯取代的碳數1至5的烷基； R2 為碳數1至10的烷基，該R2 中，至少一個-CH2 -可經-O-或-S-取代，至少一個-(CH2 )2 -可經-CH=CH-或-C≡C-取代，至少一個氫可經氟或氯取代； X1 獨立地為-OH、-NH2 、-OR4 、-N(R4 )2 、-COOH、-SH、或-Si(R4 )3 ； -OR4 、-N(R4 )2 、及-Si(R4 )3 中， R4 為氫或碳數1至10的烷基，該R4 中，至少一個-CH2 -可經-O-取代，至少一個-(CH2 )2 -可經-CH=CH-取代，該些基中，至少一個氫可經氟或氯取代； 環A2 或Sp0 中，至少一個氫經式（1-a）所表示的基取代；
Figure 02_image015
式（1-a）中， Sp5 為單鍵或碳數1至10的伸烷基，該Sp5 中，至少一個-CH2 -可經-O-、-CO-、-COO-、-OCO-、或-OCOO-取代，至少一個-(CH2 )2 -可經-CH=CH-或-C≡C-取代，至少一個氫可經氟或氯取代； M3 、及M4 獨立地為氫、氟、氯、碳數1至5的烷基、或者至少一個氫經氟或氯取代的碳數1至5的烷基； R3 為碳數1至10的烷基，該R3 中，至少一個-CH2 -可經-O-或-S-取代，至少一個-(CH2 )2 -可經-CH=CH-或-C≡C-取代，至少一個氫可經氟或氯取代。Item 1. A compound represented by formula (1).
Figure 02_image013
In formula (1), R 1 is hydrogen or an alkyl group with 1 to 15 carbons, in which at least one -CH 2 - may be substituted by -O- or -S-, and at least one -(CH 2 ) 2 -Can be substituted by -CH=CH- or -C≡C-, at least one hydrogen can be substituted by fluorine or chlorine; Ring A 1 and ring A 2 are independently 1,2-cyclopropyl, 1,3- Cyclobutyl, 1,3-cyclopentyl, 1,4-cyclohexyl, 1,4-cyclohexyl, 1,4-cyclohexenyl, 1,4-phenylene, naphthalene- 2,6-diyl, decalin-2,6-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl, tetrahydropyran-2,5-diyl, 1 , 3-dioxane-2,5-diyl, pyrimidine-2,5-diyl, or pyridine-2,5-diyl, in the ring A 1 and ring A 2 , at least one hydrogen can be fluorine, Chlorine, alkyl with 1 to 10 carbons, alkenyl with 2 to 10 carbons, alkoxy with 1 to 9 carbons, or alkenyloxy with 2 to 9 carbons is substituted, at least one hydrogen can be replaced by fluorine or chlorine Substitution; a is 0, 1, 2, 3, or 4; Z 1 is independently a single bond or an alkylene group with 1 to 6 carbons, and in this Z 1 , at least one -CH 2 - can be passed through -O-, -CO-, -COO-, -OCO-, or -OCOO-, at least one -(CH 2 ) 2 - can be substituted by -CH=CH- or -C≡C-, at least one hydrogen can be fluorine or chlorine Substitution; Sp 0 , Sp 2 , Sp 3 , and Sp 4 are independently a single bond or an alkylene group with 1 to 15 carbons, and among the Sp 0 , Sp 2 , Sp 3 , and Sp 4 , at least one -CH 2 - can be substituted by -O-, -CO-, -COO-, -OCO-, or -OCOO-, at least one -(CH 2 ) 2 - can be substituted by -CH=CH- or -C≡C-, at least One hydrogen can be substituted by fluorine or chlorine; M 1 and M 2 are independently hydrogen, fluorine, chlorine, an alkyl group with 1 to 5 carbons, or an alkane with 1 to 5 carbons in which at least one hydrogen is substituted by fluorine or chlorine group; R 2 is an alkyl group with 1 to 10 carbon atoms, in which at least one -CH 2 - can be substituted by -O- or -S- in this R 2 , and at least one -(CH 2 ) 2 - can be substituted by -CH= CH- or -C≡C-substituted, at least one hydrogen can be replaced by fluorine or chlorine; X 1 is independently -OH, -NH 2 , -OR 4 , -N(R 4 ) 2 , -COOH, -SH, Or -Si(R 4 ) 3 ; in -OR 4 , -N(R 4 ) 2 , and -Si(R 4 ) 3 , R 4 is hydrogen or an alkyl group with 1 to 10 carbons, and in the R 4 , At least one -CH 2 - may be substituted by -O-, at least one -(CH 2 ) 2 - may be substituted by -CH=CH-, and in these groups, at least one hydrogen may be substituted by fluorine or chlorine; Ring A 2 or In Sp 0 , at least one hydrogen is replaced by a group represented by formula (1-a);
Figure 02_image015
In formula (1-a), Sp 5 is a single bond or an alkylene group with 1 to 10 carbons, and in this Sp 5 , at least one -CH 2 - can be passed through -O-, -CO-, -COO-, - OCO-, or -OCOO-substituted, at least one -(CH 2 ) 2 - can be substituted by -CH=CH- or -C≡C-, at least one hydrogen can be substituted by fluorine or chlorine; M 3 , and M 4 are independent is hydrogen, fluorine, chlorine, an alkyl group with 1 to 5 carbons, or an alkyl group with 1 to 5 carbons in which at least one hydrogen is replaced by fluorine or chlorine; R 3 is an alkyl group with 1 to 10 carbons, the R In 3 , at least one -CH 2 - may be substituted by -O- or -S-, at least one -(CH 2 ) 2 - may be substituted by -CH=CH- or -C≡C-, at least one hydrogen may be substituted by fluorine or chlorine substitution.

項2.如項1所述的化合物，其中式（1）中， Z1 獨立地為單鍵、-(CH2 )2 -、-(CH2 )4 -、-CH=CH-、-C≡C-、-COO-、-OCO-、-CF2 O-、-OCF2 -、-CH2 O-、-OCH2 -、或-CF=CF-； 環A1 及環A2 獨立地為1,4-伸環己基、1,4-伸環己烯基、1,4-伸苯基、萘-2,6-二基、四氫吡喃-2,5-二基、1,3-二噁烷-2,5-二基、嘧啶-2,5-二基、或吡啶-2,5-二基，該環A1 及環A2 中，至少一個氫可經氟、氯、碳數1至10的烷基、碳數2至10的烯基、碳數1至9的烷氧基、或碳數2至9的烯氧基取代，至少一個氫可經氟或氯取代；環A2 或Sp0 中，至少一個氫經式（1-a）取代。Item 2. The compound according to Item 1, wherein in formula (1), Z 1 is independently a single bond, -(CH 2 ) 2 -, -(CH 2 ) 4 -, -CH=CH-, -C ≡C-, -COO-, -OCO-, -CF 2 O-, -OCF 2 -, -CH 2 O-, -OCH 2 -, or -CF=CF-; Ring A 1 and Ring A 2 are independently 1,4-cyclohexylene, 1,4-cyclohexenyl, 1,4-phenylene, naphthalene-2,6-diyl, tetrahydropyran-2,5-diyl, 1, 3-dioxane-2,5-diyl, pyrimidine-2,5-diyl, or pyridine-2,5-diyl, in the ring A 1 and ring A 2 , at least one hydrogen can be fluorine, chlorine , alkyl with 1 to 10 carbons, alkenyl with 2 to 10 carbons, alkoxy with 1 to 9 carbons, or alkenyloxy with 2 to 9 carbons, at least one hydrogen may be replaced by fluorine or chlorine ; In ring A 2 or Sp 0 , at least one hydrogen is replaced by formula (1-a).

項3.如項1或項2所述的化合物，由式（1-1）至式（1-8）的任一者表示。

Figure 02_image017
Figure 02_image019
式（1-1）至式（1-8）中， R1 為碳數1至15的烷基、碳數2至15的烯基、碳數1至14的烷氧基、或碳數2～14的烯氧基，該R1 中，至少一個氫可經氟取代； 環A1 至環A5 獨立地為1,4-伸環己基、1,4-伸環己烯基、1,4-伸苯基、萘-2,6-二基、四氫吡喃-2,5-二基、或1,3-二噁烷-2,5-二基，該環A1 至環A5 中，至少一個氫可經氟、碳數1至10的烷基、碳數2至10的烯基、碳數1至9的烷氧基、或碳數2至9的烯氧基取代，至少一個氫可經氟取代； b至e獨立地為0、1、2、3、或4，該些的合計為1、2、3、或4； Z1 至Z4 獨立地為單鍵、-(CH2 )2 -、-CH=CH-、-C≡C-、-COO-、-OCO-、-CF2 O-、-OCF2 -、-CH2 O-、-OCH2 -、或-CF=CF-； Sp0 至Sp8 獨立地為單鍵或碳數1至7的伸烷基，該Sp0 至Sp8 中，至少一個-CH2 -可經-O-、-COO-、或-OCO-取代，至少一個-(CH2 )2 -可經-CH=CH-取代，至少一個氫可經氟取代； M1 至M10 獨立地為氫、氟、碳數1至5的烷基、或者至少一個氫經氟取代的碳數1至5的烷基； R2 至R6 獨立地為碳數1至10的烷基，該R2 至R6 中，至少一個-CH2 -可經-O-取代； X1 獨立地為-OH、-NH2 、或-SH。Item 3. The compound according to Item 1 or Item 2, represented by any one of formula (1-1) to formula (1-8).
Figure 02_image017
Figure 02_image019
In formula (1-1) to formula (1-8), R 1 is alkyl with 1 to 15 carbons, alkenyl with 2 to 15 carbons, alkoxy with 1 to 14 carbons, or 2 carbons ～14 alkenyloxy groups, in the R 1 , at least one hydrogen can be replaced by fluorine; Ring A 1 to Ring A 5 are independently 1,4-cyclohexyl, 1,4-cyclohexenyl, 1, 4-phenylene, naphthalene-2,6-diyl, tetrahydropyran-2,5-diyl, or 1,3-dioxane-2,5-diyl, the ring A 1 to ring A In 5 , at least one hydrogen may be substituted by fluorine, an alkyl group having 1 to 10 carbons, an alkenyl group having 2 to 10 carbons, an alkoxy group having 1 to 9 carbons, or an alkenyloxy group having 2 to 9 carbons, At least one hydrogen can be substituted by fluorine; b to e are independently 0, 1, 2, 3, or 4, and the total of these is 1, 2, 3, or 4; Z 1 to Z 4 are independently single bonds, -(CH 2 ) 2 -, -CH=CH-, -C≡C-, -COO-, -OCO-, -CF 2 O-, -OCF 2 -, -CH 2 O-, -OCH 2 -, Or -CF=CF-; Sp 0 to Sp 8 are independently a single bond or an alkylene group with a carbon number of 1 to 7, and among the Sp 0 to Sp 8 , at least one -CH 2 - can be passed through -O-, -COO -, or -OCO-substituted, at least one -(CH 2 ) 2 - can be substituted by -CH=CH-, at least one hydrogen can be substituted by fluorine; M 1 to M 10 are independently hydrogen, fluorine, carbon number 1 to 5 alkyl, or at least one hydrogen is replaced by fluorine 1 to 5 alkyl; R 2 to R 6 are independently an alkyl group with 1 to 10 carbons, and among the R 2 to R 6 , at least one of - CH 2 - may be substituted by -O-; X 1 is independently -OH, -NH 2 , or -SH.

項4.如項1至項3中任一項所述的化合物，由式（1-9）至式（1-16）的任一者表示。

Figure 02_image021
Figure 02_image023
式（1-9）至式（1-16）中， R1 為碳數1至10的烷基、碳數2至10的烯基、或碳數1至9的烷氧基； 環A1 至環A5 獨立地為1,4-伸環己基、1,4-伸環己烯基、1,4-伸苯基、萘-2,6-二基、四氫吡喃-2,5-二基、或1,3-二噁烷-2,5-二基，該環A1 至環A5 中，至少一個氫可經氟、碳數1至5的烷基、碳數2至5的烯基、或碳數1至4的烷氧基取代； b至e獨立地為0、1、2、3、或4，該些的合計為1、2、3、或4； Z1 至Z4 獨立地為單鍵、-(CH2 )2 -、-CH=CH-、-C≡C-、-CH2 O-、或-OCH2 -； Sp0 至Sp8 獨立地為單鍵或碳數1至5的伸烷基，該Sp0 至Sp8 中，至少一個-CH2 -可經-O-取代，至少一個-(CH2 )2 -可經-CH=CH-取代； M1 至M10 獨立地為氫、氟、碳數1至5的烷基、或至少一個氫經氟取代的碳數1至5的烷基； R2 為碳數1至3的烷基； R3 至R6 獨立地為碳數1至10的烷基、或碳數1至9的烷氧基。Item 4. The compound according to any one of Items 1 to 3, represented by any one of Formula (1-9) to Formula (1-16).
Figure 02_image021
Figure 02_image023
In formula (1-9) to formula (1-16), R 1 is an alkyl group with 1 to 10 carbons, an alkenyl group with 2 to 10 carbons, or an alkoxy group with 1 to 9 carbons; Ring A 1 To ring A 5 is independently 1,4-cyclohexylene, 1,4-cyclohexene, 1,4-phenylene, naphthalene-2,6-diyl, tetrahydropyran-2,5 -diyl, or 1,3-dioxane-2,5-diyl, in the ring A 1 to ring A 5 , at least one hydrogen can be fluorine, an alkyl group with 1 to 5 carbons, and an alkyl group with 2 to 5 carbons 5 alkenyl, or an alkoxy group with 1 to 4 carbons; b to e are independently 0, 1, 2, 3, or 4, and the total of these is 1, 2, 3, or 4; Z 1 to Z 4 are independently a single bond, -(CH 2 ) 2 -, -CH=CH-, -C≡C-, -CH 2 O-, or -OCH 2 -; Sp 0 to Sp 8 are independently a single bond or an alkylene group with 1 to 5 carbons, in the Sp 0 to Sp 8 , at least one -CH 2 - may be substituted by -O-, and at least one -(CH 2 ) 2 - may be substituted by -CH=CH- ; M 1 to M 10 are independently hydrogen, fluorine, an alkyl group with 1 to 5 carbons, or an alkyl group with 1 to 5 carbons in which at least one hydrogen is replaced by fluorine; R 2 is an alkyl group with 1 to 3 carbons R 3 to R 6 are independently an alkyl group with 1 to 10 carbons, or an alkoxy group with 1 to 9 carbons.

項5.如項1至項4中任一項所述的化合物，由式（1-17）至式（1-53）的任一者表示。

Figure 02_image025
Figure 02_image027
Figure 02_image029
Figure 02_image031
Figure 02_image033
Figure 02_image035
式（1-17）至式（1-53）中， R1 為碳數1～10的烷基、碳數2～10的烯基、或碳數1～9的烷氧基； Z1 至Z3 獨立地為單鍵或-(CH2 )2 -； Sp0 、Sp1 、Sp2 、Sp5 、Sp6 、及Sp7 獨立地為單鍵或碳數1至5的伸烷基，該Sp0 、Sp1 、Sp2 、Sp5 、Sp6 、及Sp7 中，至少一個-CH2 -可經-O-取代； Y1 至Y11 獨立地為氫、氟、碳數1至5的烷基、碳數2至5的烯基、或碳數1至4的烷氧基； R2 為碳數1至10的烷基、或碳數1至9的烷氧基； R3 、R4 、及R5 獨立地為碳數1至3的烷基； M1 及M2 獨立地為氫、氟、碳數1至5的烷基、或至少一個氫經氟取代的碳數1至5的烷基。Item 5. The compound according to any one of Items 1 to 4, represented by any one of Formula (1-17) to Formula (1-53).
Figure 02_image025
Figure 02_image027
Figure 02_image029
Figure 02_image031
Figure 02_image033
Figure 02_image035
In formula (1-17) to formula (1-53), R 1 is an alkyl group with 1 to 10 carbons, an alkenyl group with 2 to 10 carbons, or an alkoxy group with 1 to 9 carbons; Z 1 to Z 3 is independently a single bond or -(CH 2 ) 2 -; Sp 0 , Sp 1 , Sp 2 , Sp 5 , Sp 6 , and Sp 7 are independently a single bond or an alkylene group with 1 to 5 carbons, Among the Sp 0 , Sp 1 , Sp 2 , Sp 5 , Sp 6 , and Sp 7 , at least one -CH 2 - may be substituted by -O-; Y 1 to Y 11 are independently hydrogen, fluorine, and carbon number 1 to 5 alkyl, alkenyl with 2 to 5 carbons, or alkoxy with 1 to 4 carbons; R 2 is alkyl with 1 to 10 carbons, or alkoxy with 1 to 9 carbons; R 3 , R 4 , and R 5 are independently an alkyl group with 1 to 3 carbons; M 1 and M 2 are independently hydrogen, fluorine, an alkyl group with 1 to 5 carbons, or a carbon number in which at least one hydrogen is replaced by fluorine 1 to 5 alkyl.

項6.如項1至項5中任一項所述的化合物，由式（1-54）至式（1-88）的任一者表示。

Figure 02_image037
Figure 02_image039
Figure 02_image041
Figure 02_image043
Figure 02_image045
Figure 02_image047
式（1-54）至式（1-88）中， R1 為碳數1～10的烷基； Z1 及Z2 獨立地為單鍵或-(CH2 )2 -； Y1 至Y11 獨立地為氫、氟、甲基、或乙基； Sp0 、Sp1 、Sp2 、Sp5 、Sp6 、及Sp7 獨立地為單鍵或碳數1至5的伸烷基，該Sp0 、Sp1 、Sp2 、Sp5 、Sp6 、及Sp7 中，至少一個-CH2 -可經-O-取代； R2 為碳數1～10的烷基； M1 及M2 獨立地為氫、氟、碳數1至5的烷基、或至少一個氫經氟取代的碳數1至5的烷基。Item 6. The compound according to any one of Items 1 to 5, represented by any one of Formula (1-54) to Formula (1-88).
Figure 02_image037
Figure 02_image039
Figure 02_image041
Figure 02_image043
Figure 02_image045
Figure 02_image047
In formula (1-54) to formula (1-88), R 1 is an alkyl group with 1 to 10 carbons; Z 1 and Z 2 are independently a single bond or -(CH 2 ) 2 -; Y 1 to Y 11 is independently hydrogen, fluorine, methyl, or ethyl; Sp 0 , Sp 1 , Sp 2 , Sp 5 , Sp 6 , and Sp 7 are independently single bonds or alkylene groups with 1 to 5 carbons, which In Sp 0 , Sp 1 , Sp 2 , Sp 5 , Sp 6 , and Sp 7 , at least one -CH 2 - may be substituted by -O-; R 2 is an alkyl group with 1 to 10 carbons; M 1 and M 2 are independently hydrogen, fluorine, an alkyl group having 1 to 5 carbons, or an alkyl group having 1 to 5 carbons in which at least one hydrogen is replaced by fluorine.

項7.一種液晶組成物，含有如項1至項6中任一項所述的化合物的至少一種。Item 7. A liquid crystal composition containing at least one compound according to any one of Items 1 to 6.

項8.如項7所述的液晶組成物，含有選自式（2）至式（4）所表示的化合物的群組中的至少一種化合物。

Figure 02_image049
式（2）至式（4）中， R11 及R12 獨立地為碳數1至10的烷基或碳數2至10的烯基，該R11 及R12 中，至少一個-CH2 -可經-O-取代，至少一個氫可經氟取代； 環B1 、環B2 、環B3 、及環B4 獨立地為1,4-伸環己基、1,4-伸苯基、2-氟-1,4-伸苯基、2,5-二氟-1,4-伸苯基、或嘧啶-2,5-二基； Z11 、Z12 、及Z13 獨立地為單鍵、-COO-、-CH2 CH2 -、-CH=CH-、或-C≡C-。Item 8. The liquid crystal composition according to Item 7, containing at least one compound selected from the group of compounds represented by formula (2) to formula (4).
Figure 02_image049
In formula (2) to formula (4), R 11 and R 12 are independently an alkyl group with 1 to 10 carbons or an alkenyl group with 2 to 10 carbons, and among the R 11 and R 12 , at least one -CH 2 -Can be substituted by -O-, at least one hydrogen can be substituted by fluorine; Ring B 1 , Ring B 2 , Ring B 3 , and Ring B 4 are independently 1,4-cyclohexyl, 1,4-phenylene , 2-fluoro-1,4-phenylene, 2,5-difluoro-1,4-phenylene, or pyrimidine-2,5-diyl; Z 11 , Z 12 , and Z 13 are independently single bond , -COO-, -CH2CH2- , -CH=CH-, or -C≡C-.

項9.如項7或項8所述的液晶組成物，含有選自式（5）至式（7）所表示的化合物的群組中的至少一種化合物。

Figure 02_image051
式（5）至式（7）中， R13 為碳數1至10的烷基或碳數2至10的烯基，該R13 中，至少一個-CH2 -可經-O-取代，至少一個氫可經氟取代； X11 為氟、氯、-OCF3 、-OCHF2 、-CF3 、-CHF2 、-CH2 F、-OCF2 CHF2 、或-OCF2 CHFCF3 ； 環C1 、環C2 、及環C3 獨立地為1,4-伸環己基、1,4-伸苯基、四氫吡喃-2,5-二基、1,3-二噁烷-2,5-二基、嘧啶-2,5-二基、或至少一個氫經氟取代的1,4-伸苯基； Z14 、Z15 、及Z16 獨立地為單鍵、-COO-、-OCO-、-CH2 O-、-OCH2 -、-CF2 O-、-OCF2 -、-CH2 CH2 -、-CH=CH-、-C≡C-、或-(CH2 )4 -； L11 及L12 獨立地為氫或氟。Item 9. The liquid crystal composition according to Item 7 or 8, containing at least one compound selected from the group of compounds represented by formula (5) to formula (7).
Figure 02_image051
In formula (5) to formula (7), R 13 is an alkyl group with 1 to 10 carbons or an alkenyl group with 2 to 10 carbons, and in this R 13 , at least one -CH 2 - may be substituted by -O-, At least one hydrogen may be substituted by fluorine; X 11 is fluorine, chlorine, -OCF 3 , -OCHF 2 , -CF 3 , -CHF 2 , -CH 2 F, -OCF 2 CHF 2 , or -OCF 2 CHFCF 3 ; Ring C 1 , ring C 2 , and ring C 3 are independently 1,4-cyclohexylene, 1,4-phenylene, tetrahydropyran-2,5-diyl, 1,3-dioxane- 2,5-diyl, pyrimidine-2,5-diyl, or 1,4-phenylene with at least one hydrogen substituted by fluorine; Z 14 , Z 15 , and Z 16 are independently single bonds, -COO- , -OCO-, -CH 2 O-, -OCH 2 -, -CF 2 O-, -OCF 2 -, -CH 2 CH 2 -, -CH=CH-, -C≡C-, or -(CH 2 ) 4- ; L 11 and L 12 are independently hydrogen or fluorine.

項10.如項7至項9中任一項所述的液晶組成物，含有選自式（8）所表示的化合物的群組中的至少一種化合物。

Figure 02_image053
式（8）中， R14 為碳數1至10的烷基或碳數2至10的烯基，該R14 中，至少一個-CH2 -可經-O-取代，至少一個氫可經氟取代； X12 為-C≡N或-C≡C-C≡N； 環D1 為1,4-伸環己基、1,4-伸苯基、四氫吡喃-2,5-二基、1,3-二噁烷-2,5-二基、嘧啶-2,5-二基、或至少一個氫經氟取代的1,4-伸苯基； Z17 為單鍵、-COO-、-OCO-、-CH2 O-、-OCH2 -、-CF2 O-、-OCF2 -、-CH2 CH2 -、或-C≡C-； L13 及L14 獨立地為氫或氟； i為1、2、3、或4。Item 10. The liquid crystal composition according to any one of Items 7 to 9, containing at least one compound selected from the group of compounds represented by formula (8).
Figure 02_image053
In formula (8), R 14 is an alkyl group with 1 to 10 carbons or an alkenyl group with 2 to 10 carbons. In this R 14 , at least one -CH 2 - may be replaced by -O-, and at least one hydrogen may be replaced by Fluorine substitution; X 12 is -C≡N or -C≡CC≡N; Ring D 1 is 1,4-cyclohexyl, 1,4-phenylene, tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, pyrimidine-2,5-diyl, or 1,4-phenylene with at least one hydrogen replaced by fluorine; Z 17 is a single bond, -COO-, -OCO-, -CH 2 O-, -OCH 2 -, -CF 2 O-, -OCF 2 -, -CH 2 CH 2 -, or -C≡C-; L 13 and L 14 are independently hydrogen or Fluorine; i is 1, 2, 3, or 4.

項11.如項7至項10中任一項所述的液晶組成物，含有選自式（11）至式（19）所表示的化合物的群組中的至少一種化合物。

Figure 02_image055
式（11）至式（19）中， R15 、R16 、及R17 獨立地為碳數1至10的烷基或碳數2至10的烯基，該R15 、R16 、及R17 中，至少一個-CH2 -可經-O-取代，該些基中，至少一個氫可經氟取代，而且R17 亦可為氫或氟； 環E1 、環E2 、環E3 、及環E4 獨立地為1,4-伸環己基、1,4-伸環己烯基、1,4-伸苯基、四氫吡喃-2,5-二基、十氫萘-2,6-二基、或至少一個氫經氟取代的1,4-伸苯基； 環E5 及環E6 獨立地為1,4-伸環己基、1,4-伸環己烯基、1,4-伸苯基、四氫吡喃-2,5-二基、或十氫萘-2,6-二基； Z18 、Z19 、Z20 、及Z21 獨立地為單鍵、-COO-、-OCO-、-CH2 O-、-OCH2 -、-CF2 O-、-OCF2 -、-CH2 CH2 -、-CF2 OCH2 CH2 -、或-OCF2 CH2 CH2 -； L15 及L16 獨立地為氟或氯； S11 為氫或甲基； X為-CHF-或-CF2 -； j、k、m、n、p、q、r、及s獨立地為0或1，k、m、n、及p的和為1或2，q、r、及s的和為0、1、2、或3， t為1、2、或3。Item 11. The liquid crystal composition according to any one of Items 7 to 10, containing at least one compound selected from the group of compounds represented by formula (11) to formula (19).
Figure 02_image055
In formula (11) to formula (19), R 15 , R 16 , and R 17 are independently an alkyl group with 1 to 10 carbons or an alkenyl group with 2 to 10 carbons, and the R 15 , R 16 , and R In 17 , at least one -CH 2 - can be substituted by -O-, and in these groups, at least one hydrogen can be substituted by fluorine, and R 17 can also be hydrogen or fluorine; Ring E 1 , Ring E 2 , Ring E 3 , and Ring E 4 are independently 1,4-cyclohexyl, 1,4-cyclohexenyl, 1,4-phenylene, tetrahydropyran-2,5-diyl, decahydronaphthalene- 2,6-diyl, or 1,4-phenylene with at least one hydrogen substituted by fluorine; ring E 5 and ring E 6 are independently 1,4-cyclohexyl, 1,4-cyclohexenyl , 1,4-phenylene, tetrahydropyran-2,5-diyl, or decalin-2,6-diyl; Z 18 , Z 19 , Z 20 , and Z 21 are independently single bonds , -COO-, -OCO-, -CH 2 O-, -OCH 2 -, -CF 2 O-, -OCF 2 -, -CH 2 CH 2 -, -CF 2 OCH 2 CH 2 -, or -OCF 2 CH 2 CH 2 -; L 15 and L 16 are independently fluorine or chlorine; S 11 is hydrogen or methyl; X is -CHF- or -CF 2 -; j, k, m, n, p, q, r, and s are independently 0 or 1, the sum of k, m, n, and p is 1 or 2, the sum of q, r, and s is 0, 1, 2, or 3, and t is 1, 2, or 3.

項12.如項7至項11中任一項所述的液晶組成物，含有式（1）所表示的化合物以外的式（20）所表示的至少一種聚合性化合物。

Figure 02_image057
式（20）中， 環F及環I獨立地為環己基、環己烯基、苯基、1-萘基、2-萘基、四氫吡喃-2-基、1,3-二噁烷-2-基、嘧啶-2-基、或吡啶-2-基，該環F及環I中，至少一個氫可經鹵素、碳數1至12的烷基、碳數1至12的烷氧基、或至少一個氫經鹵素取代的碳數1至12的烷基取代； 環G為1,4-伸環己基、1,4-伸環己烯基、1,4-伸苯基、萘-1,2-二基、萘-1,3-二基、萘-1,4-二基、萘-1,5-二基、萘-1,6-二基、萘-1,7-二基、萘-1,8-二基、萘-2,3-二基、萘-2,6-二基、萘-2,7-二基、菲-2,7-二基、四氫吡喃-2,5-二基、1,3-二噁烷-2,5-二基、嘧啶-2,5-二基、或吡啶-2,5-二基，該環G中，至少一個氫可經鹵素、碳數1至12的烷基、碳數1至12的烷氧基、或至少一個氫經鹵素取代的碳數1至12的烷基取代； Z22 及Z23 獨立地為單鍵或碳數1至10的伸烷基，該Z22 及Z23 中，至少一個-CH2 -可經-O-、-CO-、-COO-、或-OCO-取代，至少一個-CH2 CH2 -可經-CH=CH-、-C(CH3 )=CH-、-CH=C(CH3 )-、或-C(CH3 )=C(CH3 )-取代，至少一個氫可經氟或氯取代； P11 、P12 、及P13 獨立地為聚合性基； Sp11 、Sp12 、及Sp13 獨立地為單鍵或碳數1至10的伸烷基，該Sp11 、Sp12 、及Sp13 中，至少一個-CH2 -可經-O-、-COO-、-OCO-、或-OCOO-取代，至少一個-CH2 CH2 -可經-CH=CH-或-C≡C-取代，至少一個氫可經氟或氯取代； u為0、1、或2； f、g、及h獨立地為0、1、2、3、或4，而且f、g、及h的和為1以上。Item 12. The liquid crystal composition according to any one of Items 7 to 11, comprising at least one polymerizable compound represented by formula (20) other than the compound represented by formula (1).
Figure 02_image057
In formula (20), ring F and ring I are independently cyclohexyl, cyclohexenyl, phenyl, 1-naphthyl, 2-naphthyl, tetrahydropyran-2-yl, 1,3-diox Alkyl-2-yl, pyrimidin-2-yl, or pyridin-2-yl, in ring F and ring I, at least one hydrogen can be replaced by halogen, alkyl with 1 to 12 carbons, or alkane with 1 to 12 carbons Oxygen, or at least one hydrogen is substituted by a halogen-substituted alkyl group with 1 to 12 carbons; Ring G is 1,4-cyclohexyl, 1,4-cyclohexenyl, 1,4-phenylene, Naphthalene-1,2-diyl, naphthalene-1,3-diyl, naphthalene-1,4-diyl, naphthalene-1,5-diyl, naphthalene-1,6-diyl, naphthalene-1,7 -Diyl, naphthalene-1,8-diyl, naphthalene-2,3-diyl, naphthalene-2,6-diyl, naphthalene-2,7-diyl, phenanthrene-2,7-diyl, tetra Hydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, pyrimidine-2,5-diyl, or pyridine-2,5-diyl, in the ring G, At least one hydrogen may be substituted by halogen, an alkyl group with 1 to 12 carbons, an alkoxy group with 1 to 12 carbons, or an alkyl group with 1 to 12 carbons substituted by halogen; Z 22 and Z 23 are independently is a single bond or an alkylene group with 1 to 10 carbons, in Z 22 and Z 23 , at least one -CH 2 - may be substituted by -O-, -CO-, -COO-, or -OCO-, at least A -CH 2 CH 2 - may be substituted by -CH=CH-, -C(CH 3 )=CH-, -CH=C(CH 3 )-, or -C(CH 3 )=C(CH 3 )- , at least one hydrogen may be substituted by fluorine or chlorine; P 11 , P 12 , and P 13 are independently polymerizable groups; Sp 11 , Sp 12 , and Sp 13 are independently single bonds or alkanes with 1 to 10 carbons In the Sp 11 , Sp 12 , and Sp 13 , at least one -CH 2 - can be substituted by -O-, -COO-, -OCO-, or -OCOO-, and at least one -CH 2 CH 2 - can be substituted by -CH=CH- or -C≡C-substituted, at least one hydrogen can be substituted by fluorine or chlorine; u is 0, 1, or 2; f, g, and h are independently 0, 1, 2, 3, or 4, and the sum of f, g, and h is 1 or more.

項13.如項12所述的液晶組成物，其中式（20）中， P11 、P12 、及P13 獨立地為選自式（P-1）至式（P-5）所表示的聚合性基的群組中的基。

Figure 02_image059
式（P-1）至式（P-5）中， M11 、M12 、及M13 獨立地為氫、氟、碳數1至5的烷基、或至少一個氫經鹵素取代的碳數1至5的烷基。Item 13. The liquid crystal composition according to Item 12, wherein in formula (20), P 11 , P 12 , and P 13 are independently selected from the group represented by formula (P-1) to formula (P-5). A group in a group of polymerizable groups.
Figure 02_image059
In formula (P-1) to formula (P-5), M 11 , M 12 , and M 13 are independently hydrogen, fluorine, an alkyl group with 1 to 5 carbons, or a carbon number in which at least one hydrogen is replaced by a halogen 1 to 5 alkyl.

項14.如項12或項13所述的液晶組成物，其中式（20）所表示的聚合性化合物為選自式（20-1）至式（20-7）所表示的聚合性化合物的群組中的至少一種化合物。

Figure 02_image061
式（20-1）至式（20-7）中， L31 、L32 、L33 、L34 、L35 、L36 、L37 、及L38 獨立地為氫、氟、或甲基； Sp11 、Sp12 、及Sp13 獨立地為單鍵或碳數1至10的伸烷基，該Sp11 、Sp12 、及Sp13 中，至少一個-CH2 -可經-O-、-COO-、-OCO-、或-OCOO-取代，至少一個-CH2 CH2 -可經-CH=CH-或-C≡C-取代，至少一個氫可經氟或氯取代； P11 、P12 、及P13 獨立地為選自式（P-1）至式（P-3）所表示的聚合性基的群組中的基；
Figure 02_image063
式（P-1）至式（P-3）中， M11 、M12 、及M13 獨立地為氫、氟、碳數1至5的烷基、或至少一個氫經鹵素取代的碳數1至5的烷基。Item 14. The liquid crystal composition according to Item 12 or Item 13, wherein the polymerizable compound represented by formula (20) is selected from the polymerizable compounds represented by formula (20-1) to formula (20-7) At least one compound in the group.
Figure 02_image061
In formula (20-1) to formula (20-7), L 31 , L 32 , L 33 , L 34 , L 35 , L 36 , L 37 , and L 38 are independently hydrogen, fluorine, or methyl; Sp 11 , Sp 12 , and Sp 13 are independently a single bond or an alkylene group with a carbon number of 1 to 10. In the Sp 11 , Sp 12 , and Sp 13 , at least one -CH 2 - can be passed through -O-, - COO-, -OCO-, or -OCOO-substituted, at least one -CH 2 CH 2 - can be substituted by -CH=CH- or -C≡C-, at least one hydrogen can be substituted by fluorine or chlorine; P 11 , P 12 , and P13 are independently selected from the group of polymeric groups represented by formula (P-1) to formula (P-3);
Figure 02_image063
In formula (P-1) to formula (P-3), M 11 , M 12 , and M 13 are independently hydrogen, fluorine, an alkyl group with 1 to 5 carbons, or a carbon number in which at least one hydrogen is replaced by a halogen 1 to 5 alkyl.

項15.如項7至項14中任一項所述的液晶組成物，含有選自與式（1）或式（20）所表示的化合物不同的聚合性化合物、聚合起始劑、聚合抑制劑、光學活性化合物、抗氧化劑、紫外線吸收劑、光穩定劑、熱穩定劑、色素、及消泡劑的群組中的至少一種。Item 15. The liquid crystal composition according to any one of Items 7 to 14, comprising a polymerizable compound, a polymerization initiator, and a polymerization inhibitor selected from the compound represented by formula (1) or formula (20). At least one of the group of agents, optically active compounds, antioxidants, ultraviolet absorbers, light stabilizers, heat stabilizers, pigments, and defoamers.

項16.一種液晶顯示元件，含有選自由如項7至項15中任一項所述的液晶組成物、及如項7至項15中任一項所述的液晶組成物的至少一部分進行聚合而成者所組成的群組中的至少一種。Item 16. A liquid crystal display element comprising the liquid crystal composition as described in any one of Items 7 to 15, and at least a part of the liquid crystal composition as described in any one of Items 7 to 15 is polymerized At least one of the group of winners.

本發明亦包括以下項。 （a）所述液晶組成物，進而含有聚合性化合物、聚合起始劑、聚合抑制劑、光學活性化合物、抗氧化劑、紫外線吸收劑、光穩定劑、熱穩定劑、色素、消泡劑等添加物的至少兩種。 （b）一種聚合性組成物，是藉由在所述液晶組成物中添加與化合物（1）或化合物（20）不同的聚合性化合物而製備。 （c）一種聚合性組成物，是藉由在所述液晶組成物中添加化合物（1）與化合物（20）而製備。 （d）一種液晶複合體，是藉由使所述聚合性組成物聚合而製備。 （e）一種聚合物穩定配向型的元件，含有該液晶複合體。 （f）一種聚合物穩定配向型的元件，是藉由使用聚合性組成物而製成，所述聚合性組成物是藉由在所述液晶組成物中添加化合物（1）與化合物（20）、以及與化合物（1）或化合物（20）不同的聚合性化合物而製備。The present invention also includes the following items. (a) The liquid crystal composition further contains polymerizable compounds, polymerization initiators, polymerization inhibitors, optically active compounds, antioxidants, ultraviolet absorbers, light stabilizers, heat stabilizers, pigments, defoamers, etc. at least two kinds of things. (b) A polymerizable composition prepared by adding a polymerizable compound different from compound (1) or compound (20) to the liquid crystal composition. (c) A polymerizable composition prepared by adding compound (1) and compound (20) to the liquid crystal composition. (d) A liquid crystal composite prepared by polymerizing the polymerizable composition. (e) A polymer stabilized alignment type device comprising the liquid crystal composite. (f) A polymer-stabilized alignment-type device made by using a polymeric composition by adding compound (1) and compound (20) to the liquid crystal composition , and a polymerizable compound different from compound (1) or compound (20).

以下依序對化合物（1）的態樣、化合物（1）的合成、液晶組成物、及液晶顯示元件進行說明。The aspect of the compound (1), the synthesis of the compound (1), the liquid crystal composition, and the liquid crystal display element will be described in order below.

1.化合物（1）的態樣 本發明的化合物（1）的特徵在於：具有由至少一個環構成的液晶原部位、兩個極性基、及兩個以上的聚合性基。化合物（1）因極性基與玻璃（或金屬氧化物）等的基板表面以非共價鍵結的方式相互作用而有用。用途之一為液晶顯示元件中所使用的液晶組成物用的添加物，該用途中，化合物（1）是出於控制液晶分子的配向的目的而添加。此種添加物較佳為於密封於元件中的條件下化學性穩定，使液晶分子配向的能力高，用於液晶顯示元件的情況下的電壓保持率大，而且於液晶組成物中的溶解度大。化合物（1）以相當大的程度滿足此種特性，若為先前的化合物，則無法達成，且於液晶組成物中的溶解度極大，藉由使用該化合物（1），與使用先前的化合物的情況相比，可於將配向性或電壓保持率維持為相同程度或以上的情況下容易獲得長期穩定性優異的元件。1. Form of compound (1) The compound (1) of the present invention is characterized by having a mesogen moiety composed of at least one ring, two polar groups, and two or more polymerizable groups. The compound (1) is useful because the polar group interacts with the surface of a substrate such as glass (or metal oxide) in a non-covalent bonding manner. One of the uses is an additive for a liquid crystal composition used in a liquid crystal display element, and in this use, the compound (1) is added for the purpose of controlling the alignment of liquid crystal molecules. This kind of additive is preferably chemically stable under the condition of being sealed in the element, has a high ability to align liquid crystal molecules, has a high voltage retention rate when used in a liquid crystal display element, and has a high solubility in a liquid crystal composition. . The compound (1) satisfies this characteristic to a considerable extent, which cannot be achieved by the previous compound, and has a very high solubility in the liquid crystal composition. By using the compound (1), it is different from the case of the previous compound In contrast, a device excellent in long-term stability can be easily obtained while maintaining the alignment property or the voltage retention rate at the same level or higher.

對化合物（1）的較佳例進行說明。化合物（1）中的R1 、A1 、Sp0 等記號的較佳例亦適用於化合物（1）的下位式、例如式（1-1）等。化合物（1）中，藉由將該些基的種類適當組合，可任意調整特性。由於化合物的特性不存在大的差異，因此化合物（1）可包含較天然豐度的量更多的2 H（氘）、13 C等同位素。

Figure 02_image065
Preferred examples of the compound (1) will be described. Preferred examples of symbols such as R 1 , A 1 , and Sp 0 in compound (1) are also applicable to sub-formulas of compound (1), such as formula (1-1). In the compound (1), the characteristics can be adjusted arbitrarily by appropriately combining the types of these groups. Compound (1) may contain isotopes such as 2 H (deuterium) and 13 C in a larger amount than the natural abundance, since there is no great difference in the properties of the compounds.
Figure 02_image065

R1 為氫或碳數1至15的烷基，該R1 中，至少一個-CH2 -可經-O-或-S-取代，至少一個-(CH2 )2 -可經-CH=CH-或-C≡C-取代，至少一個氫可經氟或氯取代。R 1 is hydrogen or an alkyl group with 1 to 15 carbons. In this R 1 , at least one -CH 2 - may be substituted by -O- or -S-, and at least one -(CH 2 ) 2 - may be substituted by -CH= CH- or -C≡C-substitution, at least one hydrogen can be replaced by fluorine or chlorine.

較佳的R1 為碳數1至15的烷基、碳數2至15的烯基、碳數1至14的烷氧基、或碳數2至14的烯氧基，該些基中，至少一個氫可經氟取代。 進而佳的R1 為碳數1至10的烷基、碳數2至10的烯基或碳數1至9的烷氧基。 特佳的R1 為碳數1至10的烷基。Preferred R is an alkyl group with 1 to 15 carbons, an alkenyl group with 2 to 15 carbons, an alkoxy group with 1 to 14 carbons, or an alkenyloxy group with 2 to 14 carbons. Among these groups, At least one hydrogen may be replaced by fluorine. More preferably, R 1 is an alkyl group having 1 to 10 carbons, an alkenyl group having 2 to 10 carbons, or an alkoxy group having 1 to 9 carbons. A particularly preferred R 1 is an alkyl group having 1 to 10 carbon atoms.

R1 為碳數1至15的烷基或碳數1至14的烷氧基的化合物的化學穩定性高。R1 為碳數1至15的烷基、碳數2至15的烯基、或碳數2至14的烯氧基的化合物於液晶組成物中的溶解度大。R1 為碳數1～15的烷基的化合物使液晶分子配向的能力高。A compound in which R 1 is an alkyl group having 1 to 15 carbons or an alkoxy group having 1 to 14 carbons has high chemical stability. A compound in which R 1 is an alkyl group having 1 to 15 carbons, an alkenyl group having 2 to 15 carbons, or an alkenyloxy group having 2 to 14 carbons has high solubility in the liquid crystal composition. A compound in which R 1 is an alkyl group having 1 to 15 carbon atoms has a high ability to align liquid crystal molecules.

環A1 及環A2 獨立地為1,2-伸環丙基、1,3-伸環丁基、1,3-伸環戊基、1,4-伸環己基、1,4-伸環庚基、1,4-伸環己烯基、1,4-伸苯基、萘-2,6-二基、十氫萘-2,6-二基、1,2,3,4-四氫萘-2,6-二基、四氫吡喃-2,5-二基、1,3-二噁烷-2,5-二基、嘧啶-2,5-二基、或吡啶-2,5-二基，該環A1 及環A2 中，至少一個氫可經氟、氯、碳數1至10的烷基、碳數2至10的烯基、碳數1至9的烷氧基、或碳數2至9的烯氧基取代，至少一個氫可經氟或氯取代。Ring A 1 and Ring A 2 are independently 1,2-cyclopropyl, 1,3-cyclobutyl, 1,3-cyclopentyl, 1,4-cyclohexyl, 1,4-cyclopropyl Cycloheptyl, 1,4-cyclohexenyl, 1,4-phenylene, naphthalene-2,6-diyl, decalin-2,6-diyl, 1,2,3,4- Tetrahydronaphthalene-2,6-diyl, tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, pyrimidine-2,5-diyl, or pyridine- 2,5-diyl, in ring A 1 and ring A 2 , at least one hydrogen can be replaced by fluorine, chlorine, alkyl with 1 to 10 carbons, alkenyl with 2 to 10 carbons, alkenyl with 1 to 9 carbons Substituted by alkoxy or alkenyloxy with 2 to 9 carbons, at least one hydrogen may be substituted by fluorine or chlorine.

較佳的環A1 及環A2 為1,4-伸環己基、1,4-伸環己烯基、1,4-伸苯基、萘-2,6-二基、四氫吡喃-2,5-二基、1,3-二噁烷-2,5-二基、嘧啶-2,5-二基、或吡啶-2,5-二基，該些環中，至少一個氫可經氟、氯、碳數1至10的烷基、碳數2至10的烯基、碳數1至9的烷氧基、或碳數2至9的烯氧基取代，該些基中，至少一個氫可經氟或氯取代。Preferred ring A 1 and ring A 2 are 1,4-cyclohexylene, 1,4-cyclohexenyl, 1,4-phenylene, naphthalene-2,6-diyl, tetrahydropyran -2,5-diyl, 1,3-dioxane-2,5-diyl, pyrimidine-2,5-diyl, or pyridine-2,5-diyl, in these rings, at least one hydrogen It may be substituted by fluorine, chlorine, alkyl having 1 to 10 carbons, alkenyl having 2 to 10 carbons, alkoxy having 1 to 9 carbons, or alkenyloxy having 2 to 9 carbons, in which , at least one hydrogen may be replaced by fluorine or chlorine.

更佳的環A1 及環A2 為1,4-伸環己基、1,4-伸環己烯基、1,4-伸苯基、萘-2,6-二基、四氫吡喃-2,5-二基、或1,3-二噁烷-2,5-二基，該些環中，至少一個氫可經氟、碳數1至10的烷基、碳數2至10的烯基、碳數1至9的烷氧基、或碳數2至9的烯氧基取代，該些基中，至少一個氫可經氟取代。More preferable ring A 1 and ring A 2 are 1,4-cyclohexylene, 1,4-cyclohexenyl, 1,4-phenylene, naphthalene-2,6-diyl, tetrahydropyran -2,5-diyl, or 1,3-dioxane-2,5-diyl, in these rings, at least one hydrogen can be fluorine, an alkyl group with 1 to 10 carbons, or an alkyl group with 2 to 10 carbons alkenyl, alkoxy having 1 to 9 carbons, or alkenyloxy having 2 to 9 carbons, in which at least one hydrogen may be substituted by fluorine.

進而佳的環A1 及環A2 為1,4-伸環己基、1,4-伸環己烯基、1,4-伸苯基、萘-2,6-二基、四氫吡喃-2,5-二基、或1,3-二噁烷-2,5-二基，該些環中，至少一個氫可經氟、碳數1至5的烷基、碳數2至5的烯基、或碳數1至4的烷氧基取代。Further preferable ring A 1 and ring A 2 are 1,4-cyclohexylene, 1,4-cyclohexenyl, 1,4-phenylene, naphthalene-2,6-diyl, tetrahydropyran -2,5-diyl, or 1,3-dioxane-2,5-diyl, in these rings, at least one hydrogen can be fluorine, an alkyl group with 1 to 5 carbons, or an alkyl group with 2 to 5 carbons Alkenyl, or an alkoxy group with 1 to 4 carbons.

特佳的環A1 及環A2 為1,4-伸環己基、1,4-伸苯基、2位取代1,4-伸苯基、3位取代1,4-伸苯基、或2位及3位取代1,4-伸苯基，作為該取代基，較佳為氫、氟、碳數1至5的烷基、碳數2至5的烯基、或碳數1至4的烷氧基，更佳為氫、氟、甲基、或乙基。Particularly preferred ring A 1 and ring A 2 are 1,4-cyclohexylene, 1,4-phenylene, 2-substituted 1,4-phenylene, 3-substituted 1,4-phenylene, or The 2- and 3-position substituted 1,4-phenylene groups, and the substituents are preferably hydrogen, fluorine, alkyl having 1 to 5 carbons, alkenyl having 2 to 5 carbons, or alkenyl having 1 to 4 carbons The alkoxy group, more preferably hydrogen, fluorine, methyl, or ethyl.

環A1 及環A2 獨立地為1,3-伸環戊基、1,4-伸環己基、1,4-伸環庚基、1,4-伸苯基、至少一個氫經氟取代的1,4-伸苯基、至少一個氫經碳數1至5的烷基取代的1,4-伸苯基、十氫萘-2,6-二基、或四氫吡喃-2,5-二基的化合物的化學穩定性高。環A1 及環A2 獨立地為1,4-伸環己基、1,4-伸環己烯基、1,4-伸苯基、至少一個氫經氟取代的1,4-伸苯基、至少一個氫經碳數1至5的烷基取代的1,4-伸苯基、或至少一個氫經碳數2至5的烯基取代的1,4-伸苯基的化合物於液晶組成物中的溶解度大。環A1 及環A2 獨立地為1,4-伸環己基、1,4-伸苯基、至少一個氫經碳數1至2的烷基取代的1,4-伸苯基的化合物使液晶分子配向的能力高。環A1 及環A2 獨立地為1,4-伸苯基、至少一個氫經碳數1至5的烷基取代的1,4-伸苯基、至少一個氫經碳數1至4的烷氧基取代的1,4-伸苯基、萘-2,6-二基、嘧啶-2,5-二基、或吡啶-2,5-二基的化合物的由紫外線照射所引起的聚合反應性高。Ring A 1 and Ring A 2 are independently 1,3-cyclopentyl, 1,4-cyclohexyl, 1,4-cyclohexyl, 1,4-phenylene, at least one hydrogen is replaced by fluorine 1,4-phenylene, at least one hydrogen substituted by an alkyl group having 1 to 5 carbons, 1,4-phenylene, decahydronaphthalene-2,6-diyl, or tetrahydropyran-2, The chemical stability of the 5-diyl compound is high. Ring A 1 and Ring A 2 are independently 1,4-cyclohexylene, 1,4-cyclohexenyl, 1,4-phenylene, 1,4-phenylene with at least one hydrogen replaced by fluorine , a 1,4-phenylene compound in which at least one hydrogen is substituted by an alkyl group having 1 to 5 carbons, or a 1,4-phenylene compound in which at least one hydrogen is substituted by an alkenyl group having 2 to 5 carbons in a liquid crystal composition High solubility in substances. Ring A 1 and Ring A 2 are independently 1,4-cyclohexylene, 1,4-phenylene, or 1,4-phenylene in which at least one hydrogen is substituted by an alkyl group with 1 to 2 carbons. The ability to align liquid crystal molecules is high. Ring A 1 and Ring A 2 are independently 1,4-phenylene, 1,4-phenylene with at least one hydrogen replaced by an alkyl group with 1 to 5 carbons, at least one hydrogen replaced by an alkyl group with 1 to 4 carbons Polymerization of alkoxy-substituted 1,4-phenylene, naphthalene-2,6-diyl, pyrimidine-2,5-diyl, or pyridine-2,5-diyl compounds induced by ultraviolet irradiation High reactivity.

a為0、1、2、3、或4，較佳為0、1、2、或3，更佳為1、2、或3，特佳為1或2。a is 0, 1, 2, 3, or 4, preferably 0, 1, 2, or 3, more preferably 1, 2, or 3, particularly preferably 1 or 2.

a為0的化合物於液晶組成物中的溶解度大。a為3或4的化合物使液晶分子配向的能力高。a為1或2的化合物於液晶組成物中的溶解度大、使液晶分子配向的能力高、由紫外線照射所引起的聚合反應性高。Compounds where a is 0 have high solubility in liquid crystal compositions. The compound where a is 3 or 4 has a high ability to align liquid crystal molecules. The compound where a is 1 or 2 has high solubility in the liquid crystal composition, high ability to align liquid crystal molecules, and high polymerization reactivity by ultraviolet irradiation.

Z1 為單鍵或碳數1至6的伸烷基，該Z1 中，至少一個-CH2 -可經-O-、-CO-、-COO-、-OCO-、或-OCOO-取代。其中，不存在相鄰的-CH2 -經該些基連續地取代的情況。 至少一個-(CH2 )2 -可經-CH=CH-或-C≡C-取代，該些基中，至少一個氫可經氟或氯取代。Z 1 is a single bond or an alkylene group with 1 to 6 carbons, and in this Z 1 , at least one -CH 2 - may be substituted by -O-, -CO-, -COO-, -OCO-, or -OCOO- . Wherein, there is no case where adjacent -CH 2 - is continuously substituted by these groups. At least one -(CH 2 ) 2 - may be substituted by -CH═CH- or -C≡C-, and in these groups, at least one hydrogen may be substituted by fluorine or chlorine.

較佳的Z1 為單鍵、-(CH2 )2 -、-(CH2 )4 -、-CH=CH-、-C≡C-、-COO-、-OCO-、-CF2 O-、-OCF2 -、-CH2 O-、-OCH2 -、或-CF=CF-。 更佳的Z1 為單鍵、-(CH2 )2 -、-CH=CH-、-C≡C-、-COO-、-OCO-、-CF2 O-、-OCF2 -、-CH2 O-、-OCH2 -、或-CF=CF-。 進而佳的Z1 為單鍵、-(CH2 )2 -、-CH=CH-、-C≡C-、-CH2 O-、或-OCH2 -，進而更佳的Z1 為單鍵或-(CH2 )2 -，特佳的Z1 為單鍵。Preferred Z 1 is a single bond, -(CH 2 ) 2 -, -(CH 2 ) 4 -, -CH=CH-, -C≡C-, -COO-, -OCO-, -CF 2 O- , -OCF 2 -, -CH 2 O-, -OCH 2 -, or -CF=CF-. More preferable Z 1 is a single bond, -(CH 2 ) 2 -, -CH=CH-, -C≡C-, -COO-, -OCO-, -CF 2 O-, -OCF 2 -, -CH 2 O-, -OCH 2 -, or -CF=CF-. More preferably Z 1 is a single bond, -(CH 2 ) 2 -, -CH=CH-, -C≡C-, -CH 2 O-, or -OCH 2 -, and more preferably Z 1 is a single bond or -(CH 2 ) 2 -, particularly preferred Z 1 is a single bond.

Z1 為單鍵的化合物的化學穩定性高。Z1 為單鍵、-(CH2 )2 -、-CF2 O-、或-OCF2 -的化合物於液晶組成物中的溶解度大。Z1 為單鍵或-(CH2 )2 -的化合物使液晶分子配向的能力高。Z1 為單鍵、-CH=CH-、-C≡C-、-COO-、-OCO-、-CH2 O-、-OCH2 -的化合物的由紫外線照射所引起的聚合反應性高。Compounds in which Z 1 is a single bond have high chemical stability. Compounds in which Z 1 is a single bond, -(CH 2 ) 2 -, -CF 2 O-, or -OCF 2 - have high solubility in liquid crystal compositions. A compound in which Z 1 is a single bond or -(CH 2 ) 2 - has a high ability to align liquid crystal molecules. Compounds in which Z 1 is a single bond, -CH=CH-, -C≡C-, -COO-, -OCO-, -CH 2 O-, -OCH 2 - have high polymerization reactivity by ultraviolet irradiation.

Sp0 、Sp2 、Sp3 、及Sp4 獨立地為單鍵或碳數1至15的伸烷基，該Sp0 、Sp2 、Sp3 、及Sp4 中，至少一個-CH2 -可經-O-、-CO-、-COO-、-OCO-、或-OCOO-取代，至少一個-(CH2 )2 -可經-CH=CH-或-C≡C-取代，至少一個氫可經氟或氯取代。Sp 0 , Sp 2 , Sp 3 , and Sp 4 are independently a single bond or an alkylene group with 1 to 15 carbons, and among the Sp 0 , Sp 2 , Sp 3 , and Sp 4 , at least one -CH 2 - can be Substituted by -O-, -CO-, -COO-, -OCO-, or -OCOO-, at least one -(CH 2 ) 2 - may be substituted by -CH=CH- or -C≡C-, at least one hydrogen Can be substituted by fluorine or chlorine.

較佳的Sp0 、Sp2 、Sp3 、及Sp4 獨立地為單鍵或碳數1至7的伸烷基，該Sp0 、Sp2 、Sp3 、及Sp4 中，至少一個-CH2 -可經-O-、-COO-、或-OCO-取代，至少一個-(CH2 )2 -可經-CH=CH-取代，至少一個氫可經氟取代。Preferred Sp 0 , Sp 2 , Sp 3 , and Sp 4 are independently a single bond or an alkylene group with 1 to 7 carbons, and among the Sp 0 , Sp 2 , Sp 3 , and Sp 4 , at least one -CH 2- may be substituted by -O-, -COO-, or -OCO-, at least one -(CH 2 ) 2 - may be substituted by -CH=CH-, and at least one hydrogen may be substituted by fluorine.

Sp0 、Sp2 、Sp3 、及Sp4 獨立地為單鍵或碳數1至7的伸烷基的化合物的化學穩定性高。Sp0 、Sp2 、Sp3 及Sp4 獨立地為碳數1至7的伸烷基、或碳數1至7的伸烷基的至少一個-CH2 -經-O-取代的基的化合物於液晶組成物中的溶解度大。Compounds in which Sp 0 , Sp 2 , Sp 3 , and Sp 4 are independently a single bond or an alkylene group having 1 to 7 carbon atoms have high chemical stability. Compounds in which Sp 0 , Sp 2 , Sp 3 and Sp 4 are independently an alkylene group having 1 to 7 carbons, or at least one -CH 2 -substituted by -O- of an alkylene group having 1 to 7 carbons High solubility in liquid crystal composition.

更佳的Sp0 、Sp2 、Sp3 、及Sp4 獨立地為單鍵或碳數1至5的伸烷基，該Sp0 、Sp2 、Sp3 、及Sp4 中，至少一個-CH2 -可經-O-取代，至少一個-(CH2 )2 -可經-CH=CH-取代。More preferred Sp 0 , Sp 2 , Sp 3 , and Sp 4 are independently a single bond or an alkylene group with 1 to 5 carbons, and among the Sp 0 , Sp 2 , Sp 3 , and Sp 4 , at least one -CH 2 - may be substituted by -O-, at least one -(CH 2 ) 2 - may be substituted by -CH=CH-.

就成為於液晶組成物中的溶解性更優異的化合物等方面而言，特佳的Sp0 為單鍵或碳數1至5的伸烷基，該Sp0 中，至少一個-CH2 -可經-O-取代； 特佳的Sp2 為單鍵或碳數1至5的伸烷基，該Sp2 中，至少一個-CH2 -可經-O-取代，進而佳為-CH2 -； 特佳的Sp4 及Sp3 為-CH2 -。Particularly preferred Sp 0 is a single bond or an alkylene group having 1 to 5 carbons in terms of being a compound having better solubility in a liquid crystal composition, and in this Sp 0 , at least one -CH 2 - may be Substituted by -O-; particularly preferred Sp 2 is a single bond or an alkylene group with a carbon number of 1 to 5, in which Sp 2 at least one -CH 2 - can be substituted by -O-, and is preferably -CH 2 - ; Particularly preferred Sp 4 and Sp 3 are -CH 2 -.

M1 、及M2 獨立地為氫、氟、氯、碳數1至5的烷基、或者至少一個氫經氟或氯取代的碳數1至5的烷基，較佳為氫、氟、碳數1至5的烷基、或至少一個氫經氟取代的碳數1至5的烷基，就成為由紫外線照射所引起的聚合反應性特別高的化合物等方面而言，更佳為氫。M 1 and M 2 are independently hydrogen, fluorine, chlorine, an alkyl group with 1 to 5 carbons, or an alkyl group with 1 to 5 carbons in which at least one hydrogen is replaced by fluorine or chlorine, preferably hydrogen, fluorine, An alkyl group having 1 to 5 carbons, or an alkyl group having 1 to 5 carbons in which at least one hydrogen is substituted by fluorine, is more preferably hydrogen in terms of being a compound having particularly high polymerization reactivity by ultraviolet irradiation. .

R2 為碳數1至10的烷基，該R2 中，至少一個-CH2 -可經-O-或-S-取代，至少一個-(CH2 )2 -可經-CH=CH-或-C≡C-取代，至少一個氫可經氟或氯取代。 較佳的R2 為碳數1至5的烷基，該R2 中，至少一個-CH2 -可經-O-取代。就成為於液晶組成物中的溶解性更優異、化學穩定性高、使液晶分子配向的能力高的化合物等方面而言，更佳的R2 為碳數1至4的烷基，特佳的R2 為乙基、丙基、或丁基。R 2 is an alkyl group with 1 to 10 carbons. In this R 2 , at least one -CH 2 - may be substituted by -O- or -S-, and at least one -(CH 2 ) 2 - may be substituted by -CH=CH- Or -C≡C-substitution, at least one hydrogen may be replaced by fluorine or chlorine. A preferred R 2 is an alkyl group having 1 to 5 carbons, and at least one -CH 2 - in this R 2 may be substituted by -O-. In terms of being a compound having better solubility in liquid crystal compositions, high chemical stability, and a high ability to align liquid crystal molecules, more preferable R is an alkyl group having 1 to 4 carbon atoms, and particularly preferable R 2 is ethyl, propyl, or butyl.

X1 獨立地為-OH、-NH2 、-OR3 、-N(R3 )2 、-COOH、-SH、或-Si(R3 )3 。 就成為於液晶組成物中的溶解性更優異的化合物等方面而言，較佳的X1 為-OH、-NH2 、或-SH，特佳的X1 為-OH。 此處，R3 為氫或碳數1至10的烷基，該R3 中，至少一個-CH2 -可經-O-取代，至少一個-(CH2 )2 -可經-CH=CH-取代，至少一個氫可經氟或氯取代。X 1 is independently -OH, -NH 2 , -OR 3 , -N(R 3 ) 2 , -COOH, -SH, or -Si(R 3 ) 3 . Desirable X 1 is -OH, -NH 2 , or -SH, and particularly preferred X 1 is -OH in terms of being a compound with better solubility in liquid crystal compositions. Here, R 3 is hydrogen or an alkyl group with 1 to 10 carbons. In this R 3 , at least one -CH 2 - may be replaced by -O-, and at least one -(CH 2 ) 2 - may be replaced by -CH=CH - Substitution, at least one hydrogen may be substituted by fluorine or chlorine.

X1 為-OH、-NH2 、或-SH的化合物使液晶分子配向的能力高。X1 為-OH的化合物的化學穩定性高、使液晶分子配向的能力高、用於液晶顯示元件的情況下的電壓保持率大，而且於液晶組成物中的溶解度大。Compounds in which X 1 is -OH, -NH 2 , or -SH have a high ability to align liquid crystal molecules. Compounds in which X 1 is -OH have high chemical stability, high ability to align liquid crystal molecules, high voltage retention when used in liquid crystal display elements, and high solubility in liquid crystal compositions.

其中，環A2 或Sp0 中，至少一個氫經式（1-a）取代。

Figure 02_image067
Wherein, in ring A 2 or Sp 0 , at least one hydrogen is replaced by formula (1-a).
Figure 02_image067

Sp5 為單鍵或碳數1至10的伸烷基，該Sp5 中，至少一個-CH2 -可經-O-、-CO-、-COO-、-OCO-、或-OCOO-取代，至少一個-(CH2 )2 -可經-CH=CH-或-C≡C-取代，至少一個氫可經氟或氯取代。Sp 5 is a single bond or an alkylene group with 1 to 10 carbons, and in this Sp 5 , at least one -CH 2 - may be substituted by -O-, -CO-, -COO-, -OCO-, or -OCOO- , at least one -(CH 2 ) 2 - may be substituted by -CH═CH- or -C≡C-, and at least one hydrogen may be substituted by fluorine or chlorine.

Sp5 為單鍵或碳數1至7的伸烷基的化合物的化學穩定性高。Sp5 為碳數1至7的伸烷基、或碳數1至7的伸烷基的至少一個-CH2 -經-O-取代的基的化合物於液晶組成物中的溶解度大。Compounds in which Sp 5 is a single bond or an alkylene group having 1 to 7 carbon atoms have high chemical stability. A compound in which Sp 5 is an alkylene group having 1 to 7 carbons or at least one -CH 2 -substituted by -O- of an alkylene group having 1 to 7 carbons has high solubility in a liquid crystal composition.

更佳的Sp5 為單鍵或碳數1至5的伸烷基，該Sp5 中，至少一個-CH2 -可經-O-取代，至少一個-(CH2 )2 -可經-CH=CH-取代。More preferred Sp 5 is a single bond or an alkylene group with 1 to 5 carbons. In this Sp 5 , at least one -CH 2 - may be replaced by -O-, and at least one -(CH 2 ) 2 - may be replaced by -CH =CH-substitution.

就成為於液晶組成物中的溶解性更優異的化合物等方面而言，特佳為Sp5 為單鍵或碳數1至5的伸烷基，該Sp5 中，至少一個-CH2 -可經-O-取代。In terms of being a compound having better solubility in liquid crystal compositions, etc., Sp 5 is particularly preferably a single bond or an alkylene group having 1 to 5 carbon atoms, and in Sp 5 , at least one -CH 2 - may be Substituted by -O-.

M3 、及M4 獨立地為氫、氟、氯、碳數1至5的烷基、或者至少一個氫經氟或氯取代的碳數1至5的烷基，較佳為氫、氟、碳數1至5的烷基、或至少一個氫經氟取代的碳數1至5的烷基，就成為由紫外線照射所引起的聚合反應性特高的化合物等方面而言，更佳為氫。M 3 and M 4 are independently hydrogen, fluorine, chlorine, an alkyl group with 1 to 5 carbons, or an alkyl group with 1 to 5 carbons in which at least one hydrogen is replaced by fluorine or chlorine, preferably hydrogen, fluorine, An alkyl group having 1 to 5 carbons, or an alkyl group having 1 to 5 carbons in which at least one hydrogen is substituted by fluorine, is more preferably hydrogen in terms of being a compound having a particularly high polymerization reactivity by ultraviolet irradiation. .

R3 為碳數1至10的烷基，該R3 中，至少一個-CH2 -可經-O-或-S-取代，至少一個-(CH2 )2 -可經-CH=CH-或-C≡C-取代，至少一個氫可經氟或氯取代，更佳為氫、氟、碳數1至5的烷基、或至少一個氫經氟取代的碳數1至5的烷基，就成為由紫外線照射所引起的聚合反應性特高的化合物等方面而言，更佳為氫、甲基或乙基。R 3 is an alkyl group with 1 to 10 carbons. In this R 3 , at least one -CH 2 - may be substituted by -O- or -S-, and at least one -(CH 2 ) 2 - may be substituted by -CH=CH- Or -C≡C-substituted, at least one hydrogen can be replaced by fluorine or chlorine, more preferably hydrogen, fluorine, an alkyl group with 1 to 5 carbons, or an alkyl group with 1 to 5 carbons with at least one hydrogen replaced by fluorine , is more preferably hydrogen, methyl or ethyl in terms of being a compound having particularly high polymerization reactivity by ultraviolet irradiation.

較佳的化合物（1）的例子為項3所述的化合物（1-1）至化合物（1-8）。更佳的化合物（1）的例子為項4所述的化合物（1-9）至化合物（1-16）。進而佳的化合物（1）的例子為項5所述的化合物（1-17）至化合物（1-53）。最佳的化合物（1）的例子為項6所述的化合物（1-54）至化合物（1-88）。Examples of preferable compound (1) are compound (1-1) to compound (1-8) described in Item 3. More preferable examples of compound (1) are compound (1-9) to compound (1-16) described in Item 4. Further preferable examples of the compound (1) include the compound (1-17) to the compound (1-53) described in Item 5. Preferred examples of compound (1) are compound (1-54) to compound (1-88) described in Item 6.

2.化合物（1）的合成 對化合物（1）的合成法進行說明。化合物（1）可藉由將有機合成化學的方法適當組合而合成。未記載合成法的化合物可藉由「有機合成（Organic Syntheses）」（約翰·威利父子出版公司（John Wiley ＆ Sons, Inc））、「有機反應（Organic Reactions）」（約翰·威利父子出版公司（John Wiley ＆ Sons, Inc））、「綜合有機合成（Comprehensive Organic Synthesis）」（培格曼出版社（Pergamon Press））、「新實驗化學講座」（丸善）等書籍中所記載的方法來合成。2. Synthesis of compound (1) The synthesis method of compound (1) will be described. Compound (1) can be synthesized by appropriately combining methods of organic synthetic chemistry. Compounds whose synthesis methods are not described can be obtained by "Organic Syntheses" (John Wiley & Sons, Inc.), "Organic Reactions" (John Wiley & Sons, Inc.) Company (John Wiley & Sons, Inc)), "Comprehensive Organic Synthesis" (Pergamon Press), "New Experimental Chemistry Lecture" (Maruzen) and other books. synthesis.

2-1.鍵結基的生成 生成化合物（1）中的鍵結基的方法的例子如下述的流程所述。於該流程中，MSG1 （或MSG2 ）為具有至少一個環的一價有機基。多個MSG1 （或MSG2 ）所表示的一價有機基可相同，或亦可不同。化合物（1A）至化合物（1G）相當於化合物（1）或化合物（1）的中間體。2-1. Formation of Bonding Group An example of a method for forming a bonding group in compound (1) is as described in the following scheme. In this scheme, MSG 1 (or MSG 2 ) is a monovalent organic group having at least one ring. The monovalent organic groups represented by a plurality of MSG 1 (or MSG 2 ) may be the same or different. Compound (1A) to compound (1G) correspond to compound (1) or an intermediate of compound (1).

Figure 02_image069
Figure 02_image069

Figure 02_image071
Figure 02_image071

Figure 02_image073
Figure 02_image073

Figure 02_image075
Figure 02_image075

Figure 02_image077
Figure 02_image077

Figure 02_image079
Figure 02_image079

（I）單鍵的生成 於碳酸鹽、四(三苯基膦)鈀觸媒的存在下，使硼酸化合物（21）與化合物（22）進行反應來合成化合物（1A）。該化合物（1A）亦可以如下方式來合成：使化合物（23）與正丁基鋰進行反應，繼而與氯化鋅進行反應，並於二氯雙(三苯基膦)鈀觸媒的存在下使化合物（22）進行反應。(I) Generation of a single bond Compound (1A) was synthesized by reacting boronic acid compound (21) with compound (22) in the presence of carbonate and tetrakis(triphenylphosphine)palladium catalyst. The compound (1A) can also be synthesized in the following manner: compound (23) is reacted with n-butyllithium, then reacted with zinc chloride, and in the presence of dichlorobis(triphenylphosphine) palladium catalyst Compound (22) is reacted.

（II）-COO-與-OCO-的生成 使化合物（23）與正丁基鋰進行反應，繼而與二氧化碳進行反應而獲得羧酸（24）。使該羧酸（24）與自化合物（21）衍生出的醇（25）於1,3-二環己基碳二醯亞胺（1,3-dicyclohexyl carbodiimide，DCC）與4-二甲基胺基吡啶（4-dimethylaminopyridine，DMAP）的存在下進行脫水來合成具有-COO-的化合物（1B）。具有-OCO-的化合物亦藉由該方法來合成。(II) Formation of -COO- and -OCO- Carboxylic acid (24) is obtained by reacting compound (23) with n-butyllithium followed by carbon dioxide. Make the carboxylic acid (24) and the alcohol (25) derived from the compound (21) in 1,3-dicyclohexyl carbodiimide (1,3-dicyclohexyl carbodiimide, DCC) and 4-dimethylamine Compound (1B) with -COO- was synthesized by dehydration in the presence of 4-dimethylaminopyridine (DMAP). Compounds with -OCO- are also synthesized by this method.

（III）-CF2 O-與-OCF2 -的生成 利用勞森試劑（Lawesson’s reagent）對化合物（1B）進行硫化而獲得化合物（26）。利用氟化氫吡啶錯合物與N-溴琥珀醯亞胺（N-bromosuccinimide，NBS）對化合物（26）進行氟化而合成具有-CF2 O-的化合物（1C）。參照M.黑星（M. Kuroboshi）等人的「化學快報（Chem. Lett.）」1992年第827期。化合物（1C）亦可利用(二乙基胺基)三氟化硫（(diethylamino)sulphur trifluoride，DAST）對化合物（26）進行氟化來合成。參照W.H.班尼爾（W. H. Bunnelle）等人的「有機化學期刊（J. Org. Chem.）」1990年第55期第768頁。具有-OCF2 -的化合物亦可藉由該方法來合成。(III) Formation of -CF 2 O- and -OCF 2 - Compound (26) was obtained by sulfiding compound (1B) with Lawesson's reagent. Compound (1C) with -CF 2 O- was synthesized by fluorinating compound (26) with hydrogen fluoride pyridine complex and N-bromosuccinimide (NBS). Refer to "Chem. Lett.", No. 827, 1992, by M. Kuroboshi et al. Compound (1C) can also be synthesized by fluorinating compound (26) with (diethylamino)sulfur trifluoride (DAST). See "J. Org. Chem.", 1990, No. 55, p. 768 by WH Bunnelle et al. Compounds having -OCF 2 - can also be synthesized by this method.

（IV）-CH=CH-的生成 使化合物（22）與正丁基鋰進行反應，繼而與N,N-二甲基甲醯胺（N,N-dimethyl formamide，DMF）進行反應而獲得醛（27）。使鏻鹽（28）與第三丁醇鉀進行反應而產生磷偶極體（phosphorus ylide），並使該磷偶極體與醛（27）進行反應來合成化合物（1D）。因反應條件而生成順式體，故視需要藉由公知的方法而將順式體異構化成反式體。(IV) Generation of -CH=CH- Aldehyde (27) is obtained by reacting compound (22) with n-butyllithium and then reacting with N,N-dimethylformamide (N,N-dimethyl formamide, DMF). A compound (1D) is synthesized by reacting a phosphonium salt (28) with potassium tert-butoxide to generate a phosphorus dipole (phosphorus ylide), and reacting this phosphorus dipole with an aldehyde (27). Since the cis-isomer is generated depending on the reaction conditions, the cis-isomer is isomerized to the trans-isomer by a known method if necessary.

（V）-CH2 CH2 -的生成 於鈀碳觸媒的存在下對化合物（1D）進行氫化而合成化合物（1E）。(V) Formation of -CH 2 CH 2 - The compound (1E) was synthesized by hydrogenating the compound (1D) in the presence of a palladium carbon catalyst.

（VI）-C≡C-的生成 於二氯鈀與碘化銅的觸媒存在下，使化合物（23）與2-甲基-3-丁炔-2-醇進行反應後，於鹼性條件下進行脫保護而獲得化合物（29）。於二氯雙(三苯基膦)鈀與鹵化銅的觸媒存在下，使化合物（29）與化合物（22）進行反應而合成化合物（1F）。(VI) Formation of -C≡C- In the presence of a catalyst of dichloropalladium and copper iodide, compound (23) is reacted with 2-methyl-3-butyn-2-ol, and then deprotected under alkaline conditions to obtain compound (29 ). Compound (1F) is synthesized by reacting compound (29) with compound (22) in the presence of a catalyst of dichlorobis(triphenylphosphine)palladium and copper halide.

（VII）-CH2 O-與-OCH2 -的生成 利用硼氫化鈉將化合物（27）還原而獲得化合物（30）。利用氫溴酸對其進行溴化而獲得化合物（31）。於碳酸鉀的存在下，使化合物（25）與化合物（31）進行反應而合成化合物（1G）。具有-OCH2 -的化合物亦可藉由該方法來合成。(VII) Formation of -CH 2 O- and -OCH 2 - Compound (30) was obtained by reducing compound (27) with sodium borohydride. It is brominated with hydrobromic acid to obtain compound (31). Compound (1G) is synthesized by reacting compound (25) and compound (31) in the presence of potassium carbonate. Compounds with -OCH 2 - can also be synthesized by this method.

（VIII）-CF=CF-的生成 利用正丁基鋰對化合物（23）進行處理後，使四氟乙烯進行反應而獲得化合物（32）。利用正丁基鋰對化合物（22）進行處理後，與化合物（32）進行反應而合成化合物（1H）。(VIII) Generation of -CF=CF- Compound (32) is obtained by treating compound (23) with n-butyllithium and then reacting tetrafluoroethylene. Compound (1H) is synthesized by treating compound (22) with n-butyllithium and reacting with compound (32).

2-2.環A1 及環A2 的生成 關於1,2-伸環丙基、1,3-伸環丁基、1,3-伸環戊基、1,4-伸環己基、1,4-伸環庚基、1,4-伸環己烯基、1,4-伸苯基、萘-2,6-二基、十氫萘-2,6-二基、1,2,3,4-四氫萘-2,6-二基、四氫吡喃-2,5-二基、1,3-二噁烷-2,5-二基、嘧啶-2,5-二基、吡啶-2,5-二基等環，起始物質有市售，或合成法為人所熟知。2-2. Formation of Ring A 1 and Ring A 2 Regarding 1,2-cyclopropylidene, 1,3-cyclobutylene, 1,3-cyclopentyl, 1,4-cyclohexylene, 1 ,4-Cycloheptyl, 1,4-cyclohexenyl, 1,4-phenylene, naphthalene-2,6-diyl, decalin-2,6-diyl, 1,2, 3,4-tetrahydronaphthalene-2,6-diyl, tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, pyrimidine-2,5-diyl , pyridine-2,5-diyl and other rings, the starting materials are commercially available, or the synthesis method is well known.

2-3.合成例 合成化合物（1）的方法的例子如下所述。該些化合物中，R1 、R2 、A1 、A2 、Z1 、Sp1 、Sp2 、Sp3 、及a的定義與項1中的記載相同。2-3. Synthesis Example Examples of methods for synthesizing compound (1) are as follows. In these compounds, the definitions of R 1 , R 2 , A 1 , A 2 , Z 1 , Sp 1 , Sp 2 , Sp 3 , and a are the same as those described in Item 1.

式（1）中，M1 、及M2 為氫，X1 為-OH的化合物（1-51）可利用以下的方法來合成。 於對應的丙酮溶媒中使化合物（51）與對甲苯磺酸一水合物及三乙基胺反應而獲得化合物（52）。於二氯甲烷溶媒中使化合物（52）與甲苯磺醯氯及吡啶反應而獲得化合物（53）。於2-丁酮溶媒中使化合物（53）與碘化鈉反應而獲得化合物（54）。 於DMF溶媒中、氫化鈉的存在下，使化合物（54）與化合物（55）進行反應，進而於水的存在下與碳酸鉀及聚甲醛進行反應，藉此獲得化合物（56）。 於四丁基溴化銨（tetrabutyl ammonium bromide，TBAB）、THF及水的存在下，使化合物（56）與氫氧化鋰一水合物反應，利用檸檬酸將pH值調整為4而獲得化合物（57）。 使利用公知的方法而合成的化合物（58）與化合物（57）於二氯甲烷溶媒中、DCC及DMAP的存在下進行反應而獲得化合物（59）。 於獲得化合物（59）後，於THF與甲醇的混合溶媒中使用PPTS進行脫保護，藉此可導出化合物（1-51）。In formula (1), M 1 and M 2 are hydrogen, and the compound (1-51) in which X 1 is -OH can be synthesized by the following method. Compound (52) is obtained by reacting compound (51) with p-toluenesulfonic acid monohydrate and triethylamine in the corresponding acetone solvent. Compound (53) is obtained by reacting compound (52) with tosyl chloride and pyridine in dichloromethane solvent. Compound (54) is obtained by reacting compound (53) with sodium iodide in 2-butanone solvent. Compound (56) is obtained by reacting compound (54) with compound (55) in the presence of sodium hydride in a DMF solvent, and further reacting with potassium carbonate and polyoxymethylene in the presence of water. In the presence of tetrabutyl ammonium bromide (tetrabutyl ammonium bromide, TBAB), THF and water, the compound (56) was reacted with lithium hydroxide monohydrate, and the pH value was adjusted to 4 with citric acid to obtain the compound (57 ). Compound (59) was obtained by reacting compound (58) synthesized by a known method with compound (57) in a dichloromethane solvent in the presence of DCC and DMAP. Compound (1-51) can be derived by deprotecting compound (59) using PPTS in a mixed solvent of THF and methanol after obtaining compound (59).

Figure 02_image081
Figure 02_image081

3.液晶組成物 3-1.成分化合物 本發明的液晶組成物包含化合物（1）作為成分A。化合物（1）藉由與元件的基板以非共價鍵結的方式進行相互作用，可控制液晶分子的配向。該組成物較佳為包含化合物（1）作為成分A，進而包含選自下述成分B、成分C、成分D、及成分E中的至少一種液晶性化合物。成分B為化合物（2）至化合物（4）。成分C為化合物（2）至化合物（4）以外的化合物（5）至化合物（7）。成分D為化合物（8）。成分E為化合物（11）至化合物（19）。該組成物亦可包含與化合物（2）至化合物（8）及化合物（11）至化合物（19）不同的其他液晶性化合物。於製備該組成物時，較佳為考慮到正或負的介電常數各向異性的大小等而選擇成分B、成分C、成分D、及成分E。適當選擇成分的組成物具有高的上限溫度、低的下限溫度、低黏度、適當的光學各向異性（即，大的光學各向異性或小的光學各向異性）、大的正或負的介電常數各向異性、大的比電阻、對熱或紫外線為穩定性、及適當的彈性常數（即，大的彈性常數或小的彈性常數）。3. Liquid crystal composition 3-1. Component compounds The liquid crystal composition of the present invention contains compound (1) as component A. Compound (1) can control the alignment of liquid crystal molecules by interacting with the substrate of the device in a non-covalent manner. The composition preferably contains compound (1) as component A, and further contains at least one liquid crystal compound selected from component B, component C, component D, and component E described below. Component B is compound (2) to compound (4). Component C is compound (5) to compound (7) other than compound (2) to compound (4). Component D is compound (8). Component E is compound (11) to compound (19). The composition may also contain other liquid crystal compounds different from compound (2) to compound (8) and compound (11) to compound (19). When preparing this composition, it is preferable to select component B, component C, component D, and component E in consideration of the size of positive or negative dielectric constant anisotropy and the like. Compositions with properly selected components have high upper limit temperature, low lower limit temperature, low viscosity, appropriate optical anisotropy (ie, large optical anisotropy or small optical anisotropy), large positive or negative Dielectric constant anisotropy, large specific resistance, stability to heat or ultraviolet rays, and appropriate elastic constant (ie, large elastic constant or small elastic constant).

化合物（1）是出於控制液晶分子的配向的目的而添加至組成物中。關於化合物（1）相對於液晶組成物100重量%的較佳的比例，就可容易使液晶分子配向等方面而言為0.05重量%以上，就可進一步防止元件的顯示不良等方面而言，較佳為10重量%以下。進而佳的比例為0.1重量%至7重量%的範圍，特佳的比例為0.4重量%至5重量%的範圍。該些比例亦適用於包含化合物（20）的組成物。Compound (1) is added to the composition for the purpose of controlling the alignment of liquid crystal molecules. Regarding the preferred ratio of the compound (1) to 100% by weight of the liquid crystal composition, it is 0.05% by weight or more in terms of easily aligning the liquid crystal molecules, and in terms of further preventing display defects of the device. Preferably, it is at most 10% by weight. A more preferable ratio is in the range of 0.1% by weight to 7% by weight, and an especially preferable ratio is in the range of 0.4% by weight to 5% by weight. These ratios are also applicable to compositions containing compound (20).

成分B為兩個末端基為烷基等的化合物。成分B具有小的介電常數各向異性。作為成分B的較佳例，可列舉化合物（2-1）至化合物（2-11）、化合物（3-1）至化合物（3-19）、及化合物（4-1）至化合物（4-7）。該些化合物中，R11 及R12 獨立地為碳數1至10的烷基或碳數2至10的烯基，該R11 及R12 中，至少一個-CH2 -可經-O-取代，至少一個氫可經氟取代。Component B is a compound whose two terminal groups are alkyl groups or the like. Component B has small dielectric constant anisotropy. Preferred examples of component B include compound (2-1) to compound (2-11), compound (3-1) to compound (3-19), and compound (4-1) to compound (4- 7). In these compounds, R 11 and R 12 are independently an alkyl group with 1 to 10 carbons or an alkenyl group with 2 to 10 carbons, and among the R 11 and R 12 , at least one -CH 2 - can Substitution, at least one hydrogen may be replaced by fluorine.

Figure 02_image083
Figure 02_image083

成分B由於介電常數各向異性的絕對值小，故為接近中性的化合物。化合物（2）主要於減少黏度或調整光學各向異性的方面有效果。化合物（3）及化合物（4）有藉由提高上限溫度而擴大向列相的溫度範圍的效果，或於調整光學各向異性的方面有效果。Component B is a nearly neutral compound because the absolute value of the dielectric constant anisotropy is small. Compound (2) is mainly effective in reducing viscosity or adjusting optical anisotropy. Compound (3) and compound (4) have the effect of expanding the temperature range of the nematic phase by raising the upper limit temperature, or have the effect of adjusting the optical anisotropy.

隨著使成分B的含量增加，組成物的介電常數各向異性變小，但黏度變小。因此，只要滿足元件的臨限電壓的要求值，則成分B的含量以多為佳。相對於液晶組成物100重量%，成分B的含量較佳為30重量%以上，進而佳為40重量%以上，其上限並無特別限制，例如為99.95重量%。As the content of component B increases, the dielectric anisotropy of the composition decreases, but the viscosity decreases. Therefore, as long as the required value of the threshold voltage of the element is met, the content of the component B is better. With respect to 100% by weight of the liquid crystal composition, the content of component B is preferably at least 30% by weight, more preferably at least 40% by weight, and the upper limit is not particularly limited, for example, 99.95% by weight.

成分C為於至少一末端具有氟、氯或含氟基的化合物。成分C具有大的正的介電常數各向異性。作為成分C的較佳例，可列舉化合物（5-1）至化合物（5-16）、化合物（6-1）至化合物（6-116）、化合物（7-1）至化合物（7-59）。成分C的化合物中，R13 為碳數1至10的烷基或碳數2至10的烯基，該R13 中，至少一個-CH2 -可經-O-取代，至少一個氫可經氟取代；X11 為氟、氯、-OCF3 、-OCHF2 、-CF3 、-CHF2 、-CH2 F、-OCF2 CHF2 、或-OCF2 CHFCF3 。Component C is a compound having fluorine, chlorine or a fluorine-containing group at at least one terminal. Component C has a large positive dielectric constant anisotropy. Preferred examples of component C include compound (5-1) to compound (5-16), compound (6-1) to compound (6-116), compound (7-1) to compound (7-59) ). In the compound of component C, R 13 is an alkyl group with 1 to 10 carbons or an alkenyl group with 2 to 10 carbons, and in this R 13 , at least one -CH 2 - may be replaced by -O-, and at least one hydrogen may be replaced by Fluorine substitution; X 11 is fluorine, chlorine, -OCF 3 , -OCHF 2 , -CF 3 , -CHF 2 , -CH 2 F, -OCF 2 CHF 2 , or -OCF 2 CHFCF 3 .

Figure 02_image085
Figure 02_image085

Figure 02_image087
Figure 02_image087

Figure 02_image089
Figure 02_image089

Figure 02_image091
Figure 02_image091

Figure 02_image093
Figure 02_image093

Figure 02_image095
Figure 02_image095

Figure 02_image097
Figure 02_image097

成分C的介電常數各向異性為正，且對熱、光等的穩定性非常良好，因此可較佳地用於製備IPS、FFS、OCB等模式用的組成物的情況。成分C相對於液晶組成物100重量%的含量合適的是1重量%至99重量%的範圍，較佳為10重量%至97重量%的範圍，進而佳為40重量%至95重量%的範圍。於將成分C添加至介電常數各向異性為負的組成物中的情況下，相對於液晶組成物100重量%，成分C的含量較佳為30重量%以下。藉由添加成分C，可調整組成物的彈性常數，且可調整元件的電壓-透過率曲線。Component C has a positive dielectric anisotropy and is very stable against heat, light, etc., so it can be preferably used in the preparation of compositions for modes such as IPS, FFS, and OCB. The content of component C relative to 100% by weight of the liquid crystal composition is suitably in the range of 1% by weight to 99% by weight, preferably in the range of 10% by weight to 97% by weight, and more preferably in the range of 40% by weight to 95% by weight . When Component C is added to a composition having a negative dielectric anisotropy, the content of Component C is preferably 30% by weight or less relative to 100% by weight of the liquid crystal composition. By adding component C, the elastic constant of the composition can be adjusted, and the voltage-transmittance curve of the device can be adjusted.

成分D是單末端基為-C≡N或-C≡C-C≡N的化合物（8）。成分D由於具有氰基，故具有更大的正的介電常數各向異性。作為成分D的較佳例，可列舉化合物（8-1）至化合物（8-64）。成分D的化合物中，R14 為碳數1至10的烷基或碳數2至10的烯基，該R14 中，至少一個-CH2 -可經-O-取代，至少一個氫可經氟取代；-X12 為-C≡N或-C≡C-C≡N。Component D is a compound (8) whose single terminal group is -C≡N or -C≡CC≡N. Component D has a larger positive dielectric constant anisotropy because it has a cyano group. Preferable examples of component D include compound (8-1) to compound (8-64). In the compound of component D, R 14 is an alkyl group with 1 to 10 carbons or an alkenyl group with 2 to 10 carbons, and in this R 14 , at least one -CH 2 - may be replaced by -O-, and at least one hydrogen may be replaced by Fluorine substitution; -X 12 is -C≡N or -C≡CC≡N.

Figure 02_image099
Figure 02_image099

Figure 02_image101
Figure 02_image101

成分D的介電常數各向異性為正，且其值大，因此主要用於製備TN等模式用的組成物的情況。藉由添加該成分D，可增大組成物的介電常數各向異性。成分D具有擴大液晶相的溫度範圍、調整黏度、或調整光學各向異性的效果。成分D對於調整元件的電壓-透過率曲線而言亦有用。The dielectric constant anisotropy of component D is positive and its value is large, so it is mainly used in the case of preparing compositions for modes such as TN. By adding the component D, the dielectric constant anisotropy of the composition can be increased. Component D has the effect of expanding the temperature range of the liquid crystal phase, adjusting the viscosity, or adjusting the optical anisotropy. Component D is also useful for adjusting the voltage-transmittance curve of the device.

成分D相對於液晶組成物100重量%的含量合適的是1重量%至99重量%的範圍，較佳為10重量%至97重量%的範圍，進而佳為40重量%至95重量%的範圍。於將成分D添加至介電常數各向異性為負的組成物中的情況下，相對於液晶組成物100重量%，成分D的含量較佳為30重量%以下。藉由添加成分D，可調整組成物的彈性常數，且可調整元件的電壓-透過率曲線。The content of component D with respect to 100% by weight of the liquid crystal composition is suitably in the range of 1% by weight to 99% by weight, preferably in the range of 10% by weight to 97% by weight, and more preferably in the range of 40% by weight to 95% by weight . When the component D is added to the composition having a negative dielectric anisotropy, the content of the component D is preferably 30% by weight or less relative to 100% by weight of the liquid crystal composition. By adding component D, the elastic constant of the composition can be adjusted, and the voltage-transmittance curve of the device can be adjusted.

成分E為化合物（11）至化合物（19）。成分E具有大的負的介電常數各向異性。該些化合物具有2,3-二氟-1,4-伸苯基般側位經兩個鹵素（氟或氯）取代的伸苯基。作為成分E的較佳例，可列舉化合物（11-1）至化合物（11-9）、化合物（12-1）至化合物（12-19）、化合物（13-1）及化合物（13-2）、化合物（14-1）至化合物（14-3）、化合物（15-1）至化合物（15-3）、化合物（16-1）至化合物（16-11）、化合物（17-1）至化合物（17-3）、化合物（18-1）至化合物（18-3）、及化合物（19-1）。該些化合物中，R15 、R16 、及R17 獨立地為碳數1至10的烷基或碳數2至10的烯基，該R15 、R16 、及R17 中，至少一個-CH2 -可經-O-取代，至少一個氫可經氟取代，而且R17 亦可為氫或氟。Component E is compound (11) to compound (19). Component E has a large negative dielectric constant anisotropy. These compounds have 2,3-difluoro-1,4-phenylene-like phenylene substituted by two halogens (fluorine or chlorine) at the side positions. Preferred examples of component E include compound (11-1) to compound (11-9), compound (12-1) to compound (12-19), compound (13-1) and compound (13-2 ), compound (14-1) to compound (14-3), compound (15-1) to compound (15-3), compound (16-1) to compound (16-11), compound (17-1) to compound (17-3), compound (18-1) to compound (18-3), and compound (19-1). In these compounds, R 15 , R 16 , and R 17 are independently an alkyl group with 1 to 10 carbons or an alkenyl group with 2 to 10 carbons, and among the R 15 , R 16 , and R 17 , at least one of - CH2- may be substituted by -O-, at least one hydrogen may be substituted by fluorine, and R17 may also be hydrogen or fluorine.

Figure 02_image103
Figure 02_image103

Figure 02_image105
Figure 02_image105

成分E的介電常數各向異性為負且大。成分E可較佳地用於製備IPS、VA、PSA等模式用的組成物的情況。隨著使成分E的含量增加，組成物的介電常數各向異性為負且變大，但黏度變大。因此，只要滿足元件的臨限電壓的要求值，則含量以少為佳。若考慮到介電常數各向異性為-5左右，則為了進行充分的電壓驅動，成分E相對於液晶組成物100重量%的含量較佳為40重量%以上。The dielectric constant anisotropy of component E is negative and large. Component E can be preferably used in the case of preparing compositions for patterns such as IPS, VA, and PSA. As the content of component E increases, the dielectric anisotropy of the composition becomes negative and increases, but the viscosity increases. Therefore, as long as the required value of the threshold voltage of the device is satisfied, the content is preferably less. Considering that the dielectric anisotropy is about −5, the content of component E is preferably 40% by weight or more based on 100% by weight of the liquid crystal composition for sufficient voltage driving.

成分E中，化合物（11）為二環化合物，因此具有降低黏度、調整光學各向異性、或提高介電常數各向異性的效果。化合物（12）及化合物（13）為三環化合物，化合物（14）為四環化合物，因此具有提高上限溫度、提高光學各向異性、或提高介電常數各向異性的效果。化合物（15）至化合物（19）具有提高介電常數各向異性的效果。In component E, the compound (11) is a bicyclic compound, so it has the effect of lowering the viscosity, adjusting the optical anisotropy, or increasing the dielectric constant anisotropy. Compound (12) and compound (13) are tricyclic compounds, and compound (14) is a tetracyclic compound, so they have the effects of increasing the upper limit temperature, increasing optical anisotropy, or increasing dielectric constant anisotropy. Compound (15) to Compound (19) have the effect of increasing the dielectric constant anisotropy.

相對於液晶組成物100重量%，成分E的含量較佳為40重量%以上，進而佳為50重量%至95重量%的範圍。於將成分E添加至介電常數各向異性為正的組成物中的情況下，相對於液晶組成物100重量%，成分E的含量較佳為30重量%以下。藉由添加成分E，可調整組成物的彈性常數，且可調整元件的電壓-透過率曲線。The content of component E is preferably at least 40% by weight relative to 100% by weight of the liquid crystal composition, and more preferably in the range of 50% by weight to 95% by weight. When Component E is added to a composition having a positive dielectric anisotropy, the content of Component E is preferably 30% by weight or less based on 100% by weight of the liquid crystal composition. By adding component E, the elastic constant of the composition can be adjusted, and the voltage-transmittance curve of the device can be adjusted.

藉由將以上所述的成分B、成分C、成分D、及成分E適當組合，可製備滿足如下特性的至少一種的液晶組成物：上限溫度高、下限溫度低、黏度小、光學各向異性適當、正或負的介電常數各向異性大、比電阻大、對紫外線的穩定性高、對熱的穩定性高、彈性常數大等。By appropriately combining the above-mentioned component B, component C, component D, and component E, a liquid crystal composition satisfying at least one of the following characteristics can be prepared: high upper limit temperature, low lower limit temperature, low viscosity, optical anisotropy Appropriate, positive or negative dielectric constant has large anisotropy, large specific resistance, high stability to ultraviolet rays, high stability to heat, and large elastic constant.

3-2.添加物 液晶組成物是藉由公知的方法而製備。例如可列舉將所述成分混合，然後藉由加熱而使其相互溶解的方法。亦可根據用途而於該組成物中添加添加物。添加物的例子為化合物（1）以外的聚合性化合物、聚合起始劑、聚合抑制劑、光學活性化合物、抗氧化劑、紫外線吸收劑、光穩定劑、熱穩定劑、色素、消泡劑等。此種添加物已為本技術領域具通常知識者所熟知，且記載於文獻中。3-2. Additives The liquid crystal composition is prepared by a known method. For example, the method of mixing the said component and making it mutually dissolve by heating is mentioned. Additives may also be added to this composition according to usage. Examples of additives include polymerizable compounds other than compound (1), polymerization initiators, polymerization inhibitors, optically active compounds, antioxidants, ultraviolet absorbers, light stabilizers, heat stabilizers, pigments, antifoamers, and the like. Such additives are well known to those skilled in the art and are described in the literature.

聚合性化合物是出於使液晶組成物中生成聚合體的目的而添加。於將液晶組成物注入元件中，對電極間施加電壓的狀態下照射紫外線，使化合物（1）聚合，藉此可生成聚合體。此時，化合物（1）於其極性基與玻璃（或金屬氧化物）的基板表面以非共價鍵結的方式相互作用的狀態下經固定化。藉此，控制液晶分子的配向的能力進一步提高，且可獲得適當的預傾角，因此可縮短響應時間。The polymerizable compound is added for the purpose of forming a polymer in the liquid crystal composition. A polymer can be produced by injecting a liquid crystal composition into the device and irradiating ultraviolet light with a voltage applied between the electrodes to polymerize the compound (1). At this time, the compound (1) is immobilized in a state where its polar group interacts with the surface of the glass (or metal oxide) substrate in a non-covalent manner. Thereby, the ability to control the alignment of the liquid crystal molecules is further improved, and an appropriate pretilt angle can be obtained, so the response time can be shortened.

聚合性化合物的較佳例為丙烯酸酯、甲基丙烯酸酯、乙烯基化合物、乙烯氧基化合物、丙烯基醚、環氧化合物（氧雜環丙烷、氧雜環丁烷）、及乙烯基酮。進而佳的例子為具有至少一個丙烯醯氧基的化合物及具有至少一個甲基丙烯醯氧基的化合物。進而佳的例子中亦包含具有丙烯醯氧基與甲基丙烯醯氧基這兩者的化合物。 聚合性化合物的特佳的例子可列舉化合物（20）。化合物（20）為與化合物（1）不同的化合物。化合物（1）具有極性基。另一方面，化合物（20）較佳為不具有極性基。Preferred examples of the polymerizable compound are acrylate, methacrylate, vinyl compound, vinyloxy compound, propenyl ether, epoxy compound (oxirane, oxetane), and vinyl ketone. Still more preferable examples are compounds having at least one acryloxy group and compounds having at least one methacryloxy group. Further preferred examples include compounds having both an acryloxy group and a methacryloxy group. Compound (20) is mentioned as a particularly preferable example of a polymeric compound. Compound (20) is a compound different from compound (1). Compound (1) has a polar group. On the other hand, compound (20) preferably does not have a polar group.

Figure 02_image107
Figure 02_image107

式（20）中，環F及環I獨立地為環己基、環己烯基、苯基、1-萘基、2-萘基、四氫吡喃-2-基、1,3-二噁烷-2-基、嘧啶-2-基、或吡啶-2-基，該環F及環I中，至少一個氫可經鹵素、碳數1至12的烷基、碳數1至12的烷氧基、或至少一個氫經鹵素取代的碳數1至12的烷基取代。In formula (20), Ring F and Ring I are independently cyclohexyl, cyclohexenyl, phenyl, 1-naphthyl, 2-naphthyl, tetrahydropyran-2-yl, 1,3-dioxin Alkyl-2-yl, pyrimidin-2-yl, or pyridin-2-yl, in ring F and ring I, at least one hydrogen can be replaced by halogen, alkyl with 1 to 12 carbons, or alkane with 1 to 12 carbons Oxy group, or at least one hydrogen is substituted by a halogen-substituted alkyl group having 1 to 12 carbons.

較佳的環F或環I為環己基、環己烯基、苯基、氟苯基、二氟苯基、1-萘基、或2-萘基。進而佳的環F或環I為環己基、環己烯基、或苯基。特佳的環F或環I為苯基。Preferred ring F or ring I is cyclohexyl, cyclohexenyl, phenyl, fluorophenyl, difluorophenyl, 1-naphthyl, or 2-naphthyl. Further preferable ring F or ring I is cyclohexyl, cyclohexenyl, or phenyl. A particularly preferred ring F or ring I is phenyl.

式（20）中，環G為1,4-伸環己基、1,4-伸環己烯基、1,4-伸苯基、萘-1,2-二基、萘-1,3-二基、萘-1,4-二基、萘-1,5-二基、萘-1,6-二基、萘-1,7-二基、萘-1,8-二基、萘-2,3-二基、萘-2,6-二基、萘-2,7-二基、菲-2,7-二基、四氫吡喃-2,5-二基、1,3-二噁烷-2,5-二基、嘧啶-2,5-二基、或吡啶-2,5-二基，該環G中，至少一個氫可經鹵素、碳數1至12的烷基、碳數1至12的烷氧基、或至少一個氫經鹵素取代的碳數1至12的烷基取代。In formula (20), ring G is 1,4-cyclohexylene, 1,4-cyclohexenyl, 1,4-phenylene, naphthalene-1,2-diyl, naphthalene-1,3- Diyl, naphthalene-1,4-diyl, naphthalene-1,5-diyl, naphthalene-1,6-diyl, naphthalene-1,7-diyl, naphthalene-1,8-diyl, naphthalene- 2,3-diyl, naphthalene-2,6-diyl, naphthalene-2,7-diyl, phenanthrene-2,7-diyl, tetrahydropyran-2,5-diyl, 1,3- Dioxane-2,5-diyl, pyrimidine-2,5-diyl, or pyridine-2,5-diyl, in the ring G, at least one hydrogen can be replaced by a halogen, an alkyl group with 1 to 12 carbons , an alkoxy group having 1 to 12 carbons, or an alkyl group having 1 to 12 carbons in which at least one hydrogen is substituted with a halogen.

較佳的環G為1,4-伸環己基、1,4-伸環己烯基、1,4-伸苯基、2-氟-1,4-伸苯基、萘-1,2-二基、萘-1,3-二基、萘-1,4-二基、萘-1,5-二基、萘-1,6-二基、萘-1,7-二基、萘-1,8-二基、萘-2,3-二基、萘-2,6-二基、萘-2,7-二基。進而佳的環G為1,4-伸環己基、1,4-伸環己烯基、1,4-伸苯基、或2-氟-1,4-伸苯基。特佳的環G為1,4-伸苯基或2-氟-1,4-伸苯基。最佳的環G為1,4-伸苯基。Preferred ring G is 1,4-cyclohexylene, 1,4-cyclohexene, 1,4-phenylene, 2-fluoro-1,4-phenylene, naphthalene-1,2- Diyl, naphthalene-1,3-diyl, naphthalene-1,4-diyl, naphthalene-1,5-diyl, naphthalene-1,6-diyl, naphthalene-1,7-diyl, naphthalene- 1,8-diyl, naphthalene-2,3-diyl, naphthalene-2,6-diyl, naphthalene-2,7-diyl. Further preferable ring G is 1,4-cyclohexylene, 1,4-cyclohexenyl, 1,4-phenylene, or 2-fluoro-1,4-phenylene. Particularly preferred ring G is 1,4-phenylene or 2-fluoro-1,4-phenylene. The most preferred ring G is 1,4-phenylene.

式（20）中，Z22 及Z23 獨立地為單鍵或碳數1至10的伸烷基，該Z22 及Z23 中，至少一個-CH2 -可經-O-、-CO-、-COO-、或-OCO-取代，至少一個-CH2 CH2 -可經-CH=CH-、-C(CH3 )=CH-、-CH=C(CH3 )-、或-C(CH3 )=C(CH3 )-取代，至少一個氫可經氟或氯取代。較佳的Z22 或Z23 為單鍵、-CH2 CH2 -、-CH2 O-、-OCH2 -、-COO-、或-OCO-。進而佳的Z22 或Z23 為單鍵。In formula (20), Z 22 and Z 23 are independently a single bond or an alkylene group with 1 to 10 carbons, and in Z 22 and Z 23 , at least one -CH 2 - can be passed through -O-, -CO- , -COO-, or -OCO-, at least one -CH 2 CH 2 - can be replaced by -CH=CH-, -C(CH 3 )=CH-, -CH=C(CH 3 )-, or -C (CH 3 )=C(CH 3 )-substitution, at least one hydrogen may be replaced by fluorine or chlorine. Desirable Z 22 or Z 23 is a single bond, -CH 2 CH 2 -, -CH 2 O-, -OCH 2 -, -COO-, or -OCO-. More preferably, Z 22 or Z 23 is a single bond.

化合物（20）中，P11 、P12 、及P13 獨立地為聚合性基。較佳的P11 至P13 為選自式（P-1）至式（P-5）所表示的聚合性基的群組中的基。進而佳的P11 至P13 為式（P-1）、式（P-2）、或式（P-3）所表示的基。特佳的P11 至P13 為式（P-1）所表示的基。式（P-1）所表示的較佳的基為丙烯醯氧基（-OCO-CH=CH2 ）或甲基丙烯醯氧基（-OCO-C(CH3 )=CH2 ）。式（P-1）至式（P-5）的波浪線表示進行鍵結的部位。In compound (20), P 11 , P 12 , and P 13 are independently polymerizable groups. Desirable P 11 to P 13 are groups selected from the group of polymerizable groups represented by formula (P-1) to formula (P-5). Further preferable P 11 to P 13 are groups represented by formula (P-1), formula (P-2), or formula (P-3). Particularly preferable P 11 to P 13 are groups represented by formula (P-1). A preferred group represented by formula (P-1) is acryloxy (-OCO-CH=CH 2 ) or methacryloxy (-OCO-C(CH 3 )=CH 2 ). The wavy lines in the formulas (P-1) to (P-5) indicate the sites where bonding takes place.

Figure 02_image109
Figure 02_image109

式（P-1）至式（P-5）中，M11 、M12 、及M13 獨立地為氫、氟、碳數1至5的烷基、或至少一個氫經鹵素取代的碳數1至5的烷基。為了提高反應性，較佳的M11 、M12 、或M13 為氫或甲基。進而佳的M11 為氫或甲基，進而佳的M12 或M13 為氫。In formula (P-1) to formula (P-5), M 11 , M 12 , and M 13 are independently hydrogen, fluorine, an alkyl group with 1 to 5 carbons, or a carbon number in which at least one hydrogen is replaced by a halogen 1 to 5 alkyl. In order to improve reactivity, preferred M 11 , M 12 , or M 13 is hydrogen or methyl. Further preferred M 11 is hydrogen or methyl, further preferred M 12 or M 13 is hydrogen.

式（20）中，Sp11 、Sp12 、及Sp13 獨立地為單鍵或碳數1至10的伸烷基，該Sp11 、Sp12 、及Sp13 中，至少一個-CH2 -可經-O-、-COO-、-OCO-、或-OCOO-取代，至少一個-CH2 CH2 -可經-CH=CH-或-C≡C-取代，至少一個氫可經氟或氯取代。較佳的Sp11 、Sp12 、及Sp13 為單鍵。In formula (20), Sp 11 , Sp 12 , and Sp 13 are independently a single bond or an alkylene group with 1 to 10 carbons, and among the Sp 11 , Sp 12 , and Sp 13 , at least one -CH 2 - can be Substituted by -O-, -COO-, -OCO-, or -OCOO-, at least one -CH 2 CH 2 - may be substituted by -CH=CH- or -C≡C-, at least one hydrogen may be fluorine or chlorine replace. Preferred Sp 11 , Sp 12 , and Sp 13 are single bonds.

式（20）中，u為0、1、或2。較佳的u為0或1。In formula (20), u is 0, 1, or 2. Preferable u is 0 or 1.

式（20）中，f、g、及h獨立地為0、1、2、3、或4，而且，f、g、及h的和為1以上。較佳的f、g、或h為1或2。較佳的和為2、3或4。進而佳的和為2或3。In formula (20), f, g, and h are independently 0, 1, 2, 3, or 4, and the sum of f, g, and h is 1 or more. Preferred f, g, or h is 1 or 2. Preferred sums are 2, 3 or 4. Further preferable sum is 2 or 3.

化合物（20）的較佳例為項15所述的化合物（20-1）至化合物（20-7）及後述的化合物（20-8）至化合物（20-11）。進而佳的例子為化合物（20-1-1）至化合物（20-1-5）、化合物（20-2-1）至化合物（20-2-5）、化合物（20-4-1）、化合物（20-5-1）、化合物（20-6-1）、及化合物（20-7-1）。該些化合物中，R25 至R31 獨立地為氫或甲基；R32 、R33 、及R34 獨立地為氫或碳數1至5的烷基，且R32 、R33 、及R34 的至少一個為碳數1至5的烷基；v、及x獨立地為0或1；t及u獨立地為1至10的整數，t+v及x+u分別最大為10；L31 至L36 獨立地為氫或氟，L37 及L38 獨立地為氫、氟、或甲基。Preferable examples of compound (20) include compound (20-1) to compound (20-7) described in item 15 and compound (20-8) to compound (20-11) described later. Further preferable examples are compound (20-1-1) to compound (20-1-5), compound (20-2-1) to compound (20-2-5), compound (20-4-1), Compound (20-5-1), Compound (20-6-1), and Compound (20-7-1). In these compounds, R 25 to R 31 are independently hydrogen or methyl; R 32 , R 33 , and R 34 are independently hydrogen or an alkyl group with 1 to 5 carbons, and R 32 , R 33 , and R At least one of 34 is an alkyl group with a carbon number of 1 to 5; v and x are independently 0 or 1; t and u are independently integers from 1 to 10, and t+v and x+u are respectively at most 10; L 31 to L36 are independently hydrogen or fluorine, and L37 and L38 are independently hydrogen, fluorine, or methyl.

Figure 02_image111
Figure 02_image111

Figure 02_image113
Figure 02_image113

組成物中的聚合性化合物可藉由使用光自由基聚合起始劑等聚合起始劑而迅速聚合。另外，藉由使聚合時的反應條件最佳化，可減少殘存的聚合性化合物的量。光自由基聚合起始劑的例子可列舉巴斯夫（BASF）公司的達羅固（Darocure）系列中的TPO、1173、及4265，並可列舉豔佳固（Irgacure）系列中的184、369、500、651、784、819、907、1300、1700、1800、1850、及2959。The polymerizable compound in the composition can be rapidly polymerized by using a polymerization initiator such as a photoradical polymerization initiator. In addition, by optimizing the reaction conditions during polymerization, the amount of remaining polymerizable compounds can be reduced. Examples of photoradical polymerization initiators include TPO, 1173, and 4265 in the Darocure series of BASF (BASF), and 184, 369, and 500 in the Irgacure series. , 651, 784, 819, 907, 1300, 1700, 1800, 1850, and 2959.

光自由基聚合起始劑的追加例為4-甲氧基苯基-2,4-雙(三氯甲基)三嗪、2-(4-丁氧基苯乙烯基)-5-三氯甲基-1,3,4-噁二唑、9-苯基吖啶、9,10-苯並啡嗪、二苯甲酮/米其勒酮混合物、六芳基聯咪唑/巰基苯並咪唑混合物、1-(4-異丙基苯基)-2-羥基-2-甲基丙烷-1-酮、苄基二甲基縮酮、2-甲基-1-[4-(甲硫基)苯基]-2-嗎啉基丙烷-1-酮、2,4-二乙基氧雜蒽酮/對二甲基胺基苯甲酸甲酯混合物、二苯甲酮/甲基三乙醇胺混合物。Additional examples of photoradical polymerization initiators are 4-methoxyphenyl-2,4-bis(trichloromethyl)triazine, 2-(4-butoxystyryl)-5-trichloro Methyl-1,3,4-oxadiazole, 9-phenylacridine, 9,10-benzophenazine, benzophenone/michelerone mixture, hexaarylbiimidazole/mercaptobenzimidazole Mixture, 1-(4-isopropylphenyl)-2-hydroxy-2-methylpropan-1-one, benzyl dimethyl ketal, 2-methyl-1-[4-(methylthio )phenyl]-2-morpholinopropan-1-one, 2,4-diethylxanthone/methyl p-dimethylaminobenzoate mixture, benzophenone/methyltriethanolamine mixture .

於液晶組成物中添加光自由基聚合起始劑後，於施加電場的狀態下照射紫外線，藉此可進行聚合。但是，未反應的聚合起始劑或聚合起始劑的分解產物有可能對元件引起圖像的殘像等顯示不良。為了防止該情況，亦可於不添加聚合起始劑的狀態下進行光聚合。所照射的光的較佳波長為150 nm至500 nm的範圍。進而佳的波長為250 nm至450 nm的範圍，最佳的波長為300 nm至400 nm的範圍。After adding a photoradical polymerization initiator to the liquid crystal composition, it can be polymerized by irradiating ultraviolet rays with an electric field applied. However, an unreacted polymerization initiator or a decomposition product of the polymerization initiator may cause display defects such as an afterimage of an image on the device. In order to prevent this, photopolymerization may be performed without adding a polymerization initiator. The preferred wavelength of the irradiated light is in the range of 150 nm to 500 nm. Further preferable wavelength is in the range of 250 nm to 450 nm, and the most preferable wavelength is in the range of 300 nm to 400 nm.

於保管聚合性化合物時，亦可為了防止聚合而添加聚合抑制劑。聚合性化合物通常是以不去除聚合抑制劑的狀態而添加至組成物中。聚合抑制劑的例子為對苯二酚、甲基對苯二酚等對苯二酚衍生物、4-第三丁基鄰苯二酚、4-甲氧基苯酚、啡噻嗪。When storing a polymerizable compound, a polymerization inhibitor may be added to prevent polymerization. A polymerizable compound is usually added to the composition without removing the polymerization inhibitor. Examples of polymerization inhibitors include hydroquinone derivatives such as hydroquinone and methylhydroquinone, 4-tert-butylcatechol, 4-methoxyphenol, and phenanthiazine.

光學活性化合物具有藉由在液晶分子中誘發螺旋結構而賦予所需的扭轉角來防止逆扭轉的效果。藉由添加光學活性化合物，可調整螺旋節距。出於調整螺旋節距的溫度依存性的目的而亦可添加兩種以上的光學活性化合物。作為光學活性化合物的較佳例，可列舉下述化合物（Op-1）至化合物（Op-18）。化合物（Op-18）中，環J為1,4-伸環己基或1,4-伸苯基，R28 為碳數1至10的烷基。*符號表示不對稱碳。The optically active compound has an effect of preventing reverse twist by inducing a helical structure in liquid crystal molecules to impart a desired twist angle. By adding optically active compounds, the helical pitch can be tuned. Two or more optically active compounds may also be added for the purpose of adjusting the temperature dependence of the helical pitch. Preferable examples of the optically active compound include the following compound (Op-1) to compound (Op-18). In compound (Op-18), ring J is 1,4-cyclohexylene or 1,4-phenylene, and R 28 is an alkyl group with 1 to 10 carbons. The * symbol indicates an asymmetric carbon.

Figure 02_image115
Figure 02_image115

抗氧化劑有效用於維持大的電壓保持率。作為抗氧化劑的較佳例，可列舉：下述化合物（AO-1）及化合物（AO-2）；豔佳諾（Irganox）415、豔佳諾（Irganox）565、豔佳諾（Irganox）1010、豔佳諾（Irganox）1035、豔佳諾（Irganox）3114、及豔佳諾（Irganox）1098（商品名；巴斯夫（BASF）公司）。 紫外線吸收劑有效用於防止上限溫度的降低。紫外線吸收劑的較佳例為二苯甲酮衍生物、苯甲酸酯衍生物、***衍生物等，作為具體例，可列舉：下述化合物（AO-3）及化合物（AO-4）；帝奴彬（Tinuvin）329、帝奴彬（Tinuvin）P、帝奴彬（Tinuvin）326、帝奴彬（Tinuvin）234、帝奴彬（Tinuvin）213、帝奴彬（Tinuvin）400、帝奴彬（Tinuvin）328、及帝奴彬（Tinuvin）99-2（商品名；巴斯夫（BASF）公司）；及1,4-二氮雜雙環[2.2.2]辛烷（DABCO）。Antioxidants are effective for maintaining a large voltage retention. Preferred examples of antioxidants include the following compounds (AO-1) and (AO-2); Irganox 415, Irganox 565, and Irganox 1010 , Irganox 1035, Irganox 3114, and Irganox 1098 (trade names; BASF Corporation). The ultraviolet absorber is effectively used to prevent the lowering of the upper limit temperature. Preferable examples of ultraviolet absorbers are benzophenone derivatives, benzoate derivatives, triazole derivatives, etc., and specific examples include the following compound (AO-3) and compound (AO-4) ; Tinuvin 329, Tinuvin P, Tinuvin 326, Tinuvin 234, Tinuvin 213, Tinuvin 400, Tinuvin Tinuvin 328, and Tinuvin 99-2 (trade name; BASF Corporation); and 1,4-diazabicyclo[2.2.2]octane (DABCO).

具有立體阻礙的胺等光穩定劑維持大的電壓保持率，故較佳。作為光穩定劑的較佳例，可列舉：下述化合物（AO-5）、化合物（AO-6）、及化合物（AO-7）；帝奴彬（Tinuvin）144、帝奴彬（Tinuvin）765、及帝奴彬（Tinuvin）770DF（商品名；巴斯夫（BASF）公司）；LA-77Y及LA-77G（商品名；艾迪科（ADEKA）公司）。 熱穩定劑亦有效用於維持大的電壓保持率，作為較佳例，可列舉豔佳富（Irgafos）168（商品名；巴斯夫（BASF）公司）。 為了適合於賓主（guest host，GH）模式的元件，而視需要將偶氮系色素、蒽醌系色素等二色性色素（dichroic dye）添加至組成物中。 消泡劑有效用於防止起泡。消泡劑的較佳例為二甲基矽油、甲基苯基矽油等。Light stabilizers such as amines having steric hindrance are preferable because they maintain a large voltage retention ratio. Preferable examples of light stabilizers include: the following compounds (AO-5), compounds (AO-6), and compounds (AO-7); Tinuvin 144, Tinuvin 765, and Tinuvin 770DF (trade name; BASF); LA-77Y and LA-77G (trade name; ADEKA). A thermal stabilizer is also effective for maintaining a large voltage retention rate, and a preferable example includes Irgafos 168 (trade name; BASF). In order to be suitable for a device in a guest host (GH) mode, dichroic dyes such as azo dyes and anthraquinone dyes are optionally added to the composition. Antifoaming agents are effective in preventing foaming. Preferable examples of the antifoaming agent are dimethyl silicone oil, methyl phenyl silicone oil, and the like.

Figure 02_image117
Figure 02_image117

化合物（AO-1）中，R40 為碳數1至20的烷基、碳數1至20的烷氧基、-COOR41 、或-CH2 CH2 COOR41 ，此處，R41 為碳數1至20的烷基。化合物（AO-2）及化合物（AO-5）中，R42 為碳數1至20的烷基。化合物（AO-5）中，R43 為氫、甲基或O· （氧自由基）；環G1 為1,4-伸環己基或1,4-伸苯基；化合物（AO-7）中，環G2 為1,4-伸環己基、1,4-伸苯基、或1,4-伸苯基的至少一個氫經氟取代的基；化合物（AO-5）及化合物（AO-7）中，z為1、2、或3。In compound (AO-1), R 40 is an alkyl group with 1 to 20 carbons, an alkoxy group with 1 to 20 carbons, -COOR 41 , or -CH 2 CH 2 COOR 41 , where R 41 is carbon Alkyl groups numbered from 1 to 20. In compound (AO-2) and compound (AO-5), R 42 is an alkyl group having 1 to 20 carbon atoms. In compound (AO-5), R 43 is hydrogen, methyl or O (oxygen radical); ring G 1 is 1,4-cyclohexyl or 1,4-phenylene; compound (AO-7) Among them, ring G 2 is 1,4-cyclohexyl, 1,4-phenylene, or a group in which at least one hydrogen of 1,4-phenylene is replaced by fluorine; compound (AO-5) and compound (AO -7), z is 1, 2, or 3.

4.液晶顯示元件 液晶組成物可較佳地用於具有PC、TN、STN、OCB、PSA等運作模式且以主動矩陣方式驅動的液晶顯示元件。該組成物亦可較佳地用於具有PC、TN、STN、OCB、VA、IPS等運作模式且以被動矩陣方式驅動的液晶顯示元件。該些元件亦可適用於反射型、透過型、半透過型的任一類型。4. Liquid crystal display components The liquid crystal composition can be preferably used in liquid crystal display elements with operating modes such as PC, TN, STN, OCB, and PSA and driven by active matrix. The composition can also be preferably used in liquid crystal display elements with operating modes such as PC, TN, STN, OCB, VA, and IPS and driven in a passive matrix manner. These elements can also be applied to any type of reflective type, transmissive type, or semi-transmissive type.

該組成物亦適合於向列曲線排列相（nematic curvilinear aligned phase，NCAP）元件，此處，組成物經微膠囊化。該組成物亦可用於聚合物分散型液晶顯示元件（polymer dispersed liquid crystal display，PDLCD）或聚合物網路液晶顯示元件（polymer network liquid crystal display，PNLCD）中。該些組成物中，大量地添加聚合性化合物。另一方面，關於用於PSA模式的液晶顯示元件的組成物，相對於液晶組成物100重量%，聚合性化合物的比例較佳為10重量%以下，更佳的比例為0.1重量%至2重量%的範圍，進而佳的比例為0.2重量%至1.0重量%的範圍。PSA模式的元件可以主動矩陣方式、被動矩陣方式等驅動方式來驅動。此種元件亦可適用於反射型、透過型、半透過型的任一類型。The composition is also suitable for nematic curvilinear aligned phase (NCAP) devices, where the composition is microencapsulated. The composition can also be used in a polymer dispersed liquid crystal display (PDLCD) or a polymer network liquid crystal display (PNLCD). A large amount of polymerizable compound is added to these compositions. On the other hand, with regard to the composition of the liquid crystal display element used in the PSA mode, the proportion of the polymerizable compound is preferably 10% by weight or less, more preferably 0.1% by weight to 2% by weight, based on 100% by weight of the liquid crystal composition. % range, and a better ratio is in the range of 0.2% by weight to 1.0% by weight. The elements in the PSA mode can be driven by a driving method such as an active matrix method or a passive matrix method. This kind of element can also be applied to any type of reflective type, transmissive type, and semi-transmissive type.

於聚合物穩定配向型的元件中，組成物所含的聚合體使液晶分子配向。極性化合物幫助液晶分子排列。即，極性化合物可代替配向膜而使用。製造此種元件的方法的一例如下所述。準備具有被稱為陣列基板與彩色濾光片基板的兩片基板的元件。該基板不具有配向膜。該基板的至少一片具有電極層。將液晶性化合物混合而製備液晶組成物。於該組成物中添加化合物（1）、以及視需要的其他聚合性化合物及極性化合物。視需要亦可進一步添加添加物。將該組成物注入至元件中。於對該元件施加電壓的狀態下進行光照射。較佳為紫外線。藉由光照射而使聚合性化合物聚合。藉由該聚合而生成包含聚合體的組成物，從而製作具有PSA模式的元件。In polymer-stabilized alignment-type devices, the polymer contained in the composition aligns the liquid crystal molecules. Polar compounds help the liquid crystal molecules to align. That is, a polar compound may be used instead of the alignment film. An example of a method of manufacturing such an element is as follows. A device having two substrates called an array substrate and a color filter substrate is prepared. This substrate does not have an alignment film. At least one of the substrates has an electrode layer. Liquid crystal compounds are mixed to prepare a liquid crystal composition. Compound (1), and optionally other polymerizable compounds and polar compounds are added to this composition. Additives can also be further added as needed. The composition is injected into the device. Light irradiation was performed with a voltage applied to the element. Ultraviolet rays are preferred. The polymerizable compound is polymerized by light irradiation. By this polymerization, a composition containing a polymer is produced, and a device having a PSA mode is produced.

該程序中，極性化合物由於極性基與基板表面相互作用，故於基板上排列。該極性化合物使液晶分子配向。於存在多個極性基的情況下，與基板表面的相互作用變得更強，可以低濃度進行配向。於施加電壓時，藉由電場的作用來進一步促進液晶分子的配向。依據該配向，聚合性化合物亦進行配向。於該狀態下聚合性化合物藉由紫外線而聚合，因此生成維持所述配向的聚合體。藉由該聚合體的效果，液晶分子的配向追加地穩定化，因此元件的響應時間縮短。由於圖像的殘像為液晶分子的運作不良，故藉由該聚合體的效果而亦同時改善殘像。化合物（1）為聚合性，因此藉由聚合而被消耗。化合物（1）亦藉由與其他聚合性化合物進行共聚而被消耗。因此，化合物（1）雖具有極性基，但被消耗，因此可獲得電壓保持率大的液晶顯示元件。再者，若使用具有聚合性的極性化合物，則可以一種化合物達成極性化合物與聚合性化合物這兩者的效果，因此亦有時不需要不具有極性基的聚合性化合物。 [實施例]In this procedure, polar compounds are aligned on the substrate due to the interaction of the polar groups with the substrate surface. The polar compound aligns the liquid crystal molecules. In the presence of a plurality of polar groups, the interaction with the substrate surface becomes stronger, and alignment can be performed at a low concentration. When the voltage is applied, the alignment of the liquid crystal molecules is further promoted by the action of the electric field. According to this alignment, the polymerizable compound also aligns. In this state, the polymerizable compound is polymerized by ultraviolet light, thereby producing a polymer that maintains the above-mentioned alignment. Due to the effect of the polymer, the alignment of the liquid crystal molecules is additionally stabilized, so the response time of the device is shortened. Since the afterimage of the image is due to the poor operation of the liquid crystal molecules, the effect of the polymer also improves the afterimage at the same time. Compound (1) is polymerizable, so it is consumed by polymerization. Compound (1) is also consumed by copolymerization with other polymerizable compounds. Therefore, although compound (1) has a polar group, since it is consumed, the liquid crystal display element with a high voltage retention ratio can be obtained. Furthermore, if a polymerizable polar compound is used, the effects of both the polar compound and the polymerizable compound can be achieved with one compound, and therefore a polymerizable compound not having a polar group may not be necessary. [Example]

藉由實施例（包含合成例、使用例）來對本發明進一步進行詳細說明。本發明並不受該些實施例的限制。本發明亦包含藉由將使用例的組成物的至少兩種混合而製備的混合物。The present invention will be further described in detail with examples (including synthesis examples and use examples). The present invention is not limited by these examples. The present invention also includes mixtures prepared by mixing at least two of the components of the use examples.

1.化合物（1）的實施例 只要無特別記載，則反應是於氮氣環境下進行。化合物（1）是藉由實施例1等所示的程序而合成。所合成的化合物是藉由核磁共振（Nuclear Magnetic Resonance，NMR）分析等方法而鑑定。化合物（1）、液晶性化合物、組成物、元件的特性是藉由下述方法來測定。1. Examples of compound (1) Unless otherwise specified, the reaction was carried out under a nitrogen atmosphere. Compound (1) was synthesized by the procedures shown in Example 1 and the like. The synthesized compounds were identified by nuclear magnetic resonance (Nuclear Magnetic Resonance, NMR) analysis and other methods. The properties of compound (1), liquid crystal compound, composition, and device were measured by the following methods.

NMR分析：於測定時，使用布魯克拜厄斯賓（Bruker BioSpin）公司製造的DRX-500。於1 H-NMR的測定中，使試樣溶解於CDCl3 等氘化溶媒中，於室溫下以500 MHz、累計次數16次的條件進行測定。使用四甲基矽烷作為內部標準。於19 F-NMR的測定中，使用CFCl3 作為內部標準，以累計次數24次進行測定。核磁共振光譜的說明中，s是指單峰（singlet），d是指雙重峰（doublet），t是指三重峰（triplet），q是指四重峰（quartet），quin是指五重峰（quintet），sext是指六重峰（sextet），m是指多重峰（multiplet），br是指寬峰（broad）。NMR analysis: DRX-500 manufactured by Bruker BioSpin was used for measurement. In the measurement of 1 H-NMR, a sample is dissolved in a deuterated solvent such as CDCl 3 , and the measurement is performed at room temperature at 500 MHz and 16 accumulation times. Tetramethylsilane was used as an internal standard. In the measurement of 19 F-NMR, CFCl 3 was used as an internal standard, and the measurement was performed at an accumulated frequency of 24 times. In the explanation of NMR spectrum, s means singlet (singlet), d means doublet (doublet), t means triplet (triplet), q means quartet (quartet), quin means quintet (quintet), sext refers to sextet (sextet), m refers to multiplet (multiplet), br refers to broad (broad).

氣相層析分析：於測定時，使用島津製作所（股）製造的GC-2010型氣相層析儀。管柱是使用安捷倫科技公司（Agilent Technologies Inc.）製造的毛細管柱DB-1（長度60 m、內徑0.25 mm、膜厚0.25 μm）。作為載體氣體，使用氦氣（1 ml/min）。將試樣氣化室的溫度設定為300℃，將檢測器（火焰離子化檢測器（flame ionization detector，FID））部分的溫度設定為300℃。試樣是溶解於丙酮中並以成為1重量%的溶液的方式製備，將1 μl的所獲得的溶液注入至試樣氣化室中。記錄計是使用島津製作所（股）製造的GC溶解（GC Solution）系統等。Gas chromatographic analysis: A GC-2010 gas chromatograph manufactured by Shimadzu Corporation was used for the measurement. The column is a capillary column DB-1 (length 60 m, inner diameter 0.25 mm, film thickness 0.25 μm) manufactured by Agilent Technologies Inc. As carrier gas, helium (1 ml/min) was used. The temperature of the sample vaporization chamber was set to 300°C, and the temperature of the detector (flame ionization detector (FID)) was set to 300°C. The sample was dissolved in acetone to prepare a 1% by weight solution, and 1 μl of the obtained solution was injected into the sample vaporization chamber. As the recorder, a GC solution (GC Solution) system manufactured by Shimadzu Corporation, etc. was used.

高效液相層析（High Performance Liquid Chromatography，HPLC）分析：於測定時，使用島津製作所（股）製造的普羅米納斯（Prominence）（LC-20AD；SPD-20A）。管柱是使用維美希（YMC）（股）製造的YMC-填充（YMC-Pack）ODS-A（長度150 mm、內徑4.6 mm、粒徑5 μm）。溶出液是將乙腈與水適宜混合而使用。作為檢測器，適宜使用紫外線（Ultraviolet，UV）檢測器、折射率（Reflective Index，RI）檢測器、科羅娜（CORONA）檢測器等。於使用UV檢測器的情況下，將檢測波長設為254 nm。試樣是溶解於乙腈中並以成為0.1重量%的溶液的方式製備，將1 μL的該溶液導入至試樣室中。作為記錄計，使用島津製作所（股）製造的C-R7A plus。High Performance Liquid Chromatography (HPLC) analysis: For measurement, Prominence (LC-20AD; SPD-20A) manufactured by Shimadzu Corporation was used. The column is YMC-packed (YMC-Pack) ODS-A (length 150 mm, inner diameter 4.6 mm, particle size 5 μm) manufactured by Vimex (YMC). The eluate was used by appropriately mixing acetonitrile and water. As the detector, an ultraviolet (UV) detector, a reflective index (RI) detector, a Corona (CORONA) detector, etc. are suitably used. In the case of using a UV detector, the detection wavelength was set to 254 nm. The sample was dissolved in acetonitrile to prepare a 0.1% by weight solution, and 1 μL of this solution was introduced into the sample chamber. As the recorder, C-R7A plus manufactured by Shimadzu Corporation was used.

紫外可見分光分析：於測定時，使用島津製作所（股）製造的法碼思拜（PharmaSpec）UV-1700。將檢測波長設為190 nm至700 nm。試樣是溶解於乙腈中並以成為0.01 mmol/L的溶液的方式製備，並放入至石英單元（光程長度1 cm）中進行測定。Ultraviolet-visible spectroscopic analysis: For measurement, PharmaSpec UV-1700 manufactured by Shimadzu Corporation was used. Set the detection wavelength to 190 nm to 700 nm. The sample was prepared by dissolving in acetonitrile so as to be a 0.01 mmol/L solution, and it was placed in a quartz cell (optical path length 1 cm) for measurement.

測定試樣：於測定相結構及轉變溫度（透明點、熔點、聚合起始溫度等）時，將化合物本身用作試樣。Measurement sample: The compound itself is used as a sample when measuring the phase structure and transition temperature (clearing point, melting point, polymerization initiation temperature, etc.).

測定方法：特性的測定是利用下述方法來進行。該些方法大多為社團法人電子資訊技術產業協會（Japan Electronics and Information Technology Industries Association，JEITA）所審議製定的JEITA標準（JEITA·ED-2521B）中所記載的方法或將其加以修飾的方法。用於測定的TN元件中，未安裝薄膜電晶體（TFT）。Measuring method: The characteristic was measured by the following method. Most of these methods are the methods described in the JEITA standard (JEITA·ED-2521B) deliberated and established by the Japan Electronics and Information Technology Industries Association (JEITA) or modified methods. The TN element used for measurement does not have a thin film transistor (TFT).

（1）相結構 將試樣放置於具備偏光顯微鏡的熔點測定裝置的加熱板（梅特勒（Mettler）公司製造，FP-52型熱平台（hot stage））上。對該試樣一面以3℃/min的速度加熱一面利用偏光顯微鏡觀察相狀態及其變化，確定相的種類。(1) Phase structure The sample was placed on a heating plate (manufactured by Mettler, FP-52 hot stage) of a melting point measuring device equipped with a polarizing microscope. While heating the sample at a rate of 3° C./min, the phase state and its change were observed with a polarizing microscope to identify the type of phase.

（2）轉變溫度（℃） 於測定時，使用珀金埃爾默（Perkin Elmer）公司製造的掃描熱量計Diamond DSC系統或日立高科技科學（Hitachi High-Tech Science）（股）製造的高感度示差掃描熱量計X-DSC7000。對試樣以3℃/min的速度進行昇降溫，藉由外推而求出伴隨著試樣的相變化的吸熱峰值或發熱峰值的起始點，決定轉變溫度。化合物的熔點、聚合起始溫度亦是使用該裝置來測定。有時將化合物自固體轉變為層列相、向列相等液晶相的溫度簡稱為「液晶相的下限溫度」。有時將化合物自液晶相轉變為液體的溫度簡稱為「透明點」。(2) Transition temperature (°C) For measurement, a scanning calorimeter Diamond DSC system manufactured by Perkin Elmer Co., Ltd. or a high-sensitivity differential scanning calorimeter X-DSC7000 manufactured by Hitachi High-Tech Science Co., Ltd. was used. The temperature of the sample was raised and lowered at a rate of 3°C/min, and the start point of the endothermic peak or exothermic peak accompanying the phase change of the sample was obtained by extrapolation to determine the transition temperature. The melting point of the compound and the polymerization initiation temperature were also measured using this device. The temperature at which the compound changes from a solid to a smectic phase and a nematic liquid crystal phase is sometimes simply referred to as the "lower limit temperature of the liquid crystal phase". The temperature at which a compound transitions from a liquid crystalline phase to a liquid is sometimes referred to simply as the "clearing point."

將結晶表示為C。於區分結晶的種類的情況下，分別如C1 、C2 般表示。將層列相表示為S，將向列相表示為N。層列相中，於區分層列A相、層列B相、層列C相、或層列F相的情況下，分別表示為SA 、SB 、SC 、或SF 。將液體（各向同性）表示為I。轉變溫度例如是如「C 50.0 N 100.0 I」般表述。其表示自結晶轉變為向列相的溫度為50.0℃，自向列相轉變為液體的溫度為100.0℃。Crystallization is denoted as C. In the case of distinguishing the types of crystals, they are represented as C 1 and C 2 , respectively. The smectic phase is denoted as S, and the nematic phase is denoted as N. Among the smectic phases, when distinguishing the smectic A phase, the smectic B phase, the smectic C phase, or the smectic F phase, they are represented as S A , S B , S C , or S F , respectively. Denote liquid (isotropic) as I. The transition temperature is expressed as "C 50.0 N 100.0 I", for example. It indicates that the temperature of transition from crystal to nematic phase is 50.0°C, and the temperature of transition from nematic phase to liquid is 100.0°C.

（3）向列相的上限溫度（TNI 或NI；℃） 將試樣放置於具備偏光顯微鏡的熔點測定裝置的加熱板上，以1℃/min的速度進行加熱。對試樣的一部分自向列相變化為各向同性液體時的溫度進行測定。有時將向列相的上限溫度簡稱為「上限溫度」。於試樣為化合物（1）與母液晶的混合物時，以TNI 的記號來表示。於試樣為化合物（1）與成分B、成分C、成分D之類的化合物的混合物時，以NI的記號來表示。(3) Upper Limit Temperature of Nematic Phase (T NI or NI; °C) The sample was placed on a heating plate of a melting point measuring device equipped with a polarizing microscope, and heated at a rate of 1 °C/min. The temperature at which a part of the sample changes from a nematic phase to an isotropic liquid is measured. The upper limit temperature of the nematic phase is sometimes simply referred to as "upper limit temperature". When the sample is a mixture of compound (1) and mother liquid crystal, it is indicated by the symbol of T NI . When the sample is a mixture of compound (1) and compounds such as component B, component C, and component D, it is indicated by the symbol of NI.

（4）向列相的下限溫度（TC ；℃） 將具有向列相的試樣於0℃、-10℃、-20℃、-30℃、及-40℃的冷凍器中保管10天後，觀察液晶相。例如當試樣於-20℃下保持向列相、且於-30℃下變化為結晶或層列相時，將TC 記載為≦-20℃。有時將向列相的下限溫度簡稱為「下限溫度」。(4) The lower limit temperature of the nematic phase (T C ; °C) Store the samples with the nematic phase in freezers at 0 °C, -10 °C, -20 °C, -30 °C, and -40 °C for 10 days After that, the liquid crystal phase was observed. For example, when a sample maintains a nematic phase at -20°C and changes to a crystalline or smectic phase at -30°C, T C is described as ≤ -20°C. The lower limit temperature of the nematic phase is sometimes simply referred to as "lower limit temperature".

（5）黏度（體積黏度（bulk viscosity）；η；於20℃下測定；mPa·s） 於測定時，使用東京計器（股）製造的E型旋轉黏度計。(5) Viscosity (bulk viscosity; η; measured at 20°C; mPa s) For the measurement, an E-type rotational viscometer manufactured by Tokyo Keiki Co., Ltd. was used.

（6）光學各向異性（折射率各向異性；於25℃下測定；Δn） 使用波長589 nm的光，藉由在接目鏡上安裝有偏光板的阿貝折射計來進行測定。對主稜鏡的表面朝一個方向摩擦後，將試樣滴加至主稜鏡上。折射率（n∥）是於偏光的方向與摩擦的方向平行時測定。折射率（n⊥）是於偏光的方向與摩擦的方向垂直時測定。光學各向異性（Δn）的值是根據Δn=n∥-n⊥的式子來計算。(6) Optical anisotropy (refractive index anisotropy; measured at 25°C; Δn) Measurement was performed with an Abbe refractometer with a polarizing plate attached to the eyepiece using light with a wavelength of 589 nm. After rubbing the surface of the main ash in one direction, the sample is dropped on the main ash. Refractive index (n∥) is measured when the direction of polarized light is parallel to the direction of rubbing. Refractive index (n⊥) is measured when the direction of polarized light is perpendicular to the direction of rubbing. The value of optical anisotropy (Δn) is calculated according to the formula Δn=n∥-n⊥.

（7）比電阻（ρ；於25℃下測定；Ωcm） 於具備電極的容器中注入1.0 mL試樣。對該容器施加直流電壓（10 V），測定10秒後的直流電流。比電阻是根據下式來算出。（比電阻）=｛（電壓）×（容器的電容）｝/｛（直流電流）×（真空的介電常數）｝。(7) Specific resistance (ρ; measured at 25°C; Ωcm) Inject 1.0 mL of sample into the container with electrodes. A DC voltage (10 V) was applied to the container, and the DC current after 10 seconds was measured. The specific resistance was calculated by the following formula. (Specific resistance)={(voltage)×(capacitance of container)}/{(DC current)×(dielectric constant of vacuum)}.

對於介電常數各向異性為正的試樣與介電常數各向異性為負的試樣，有時特性的測定法不同。於介電常數各向異性為正時的測定法是記載於項（8a）至項（12a）中。於介電常數各向異性為負的情況下，測定法是記載於項（8b）至項（12b）中。The measurement method of the characteristics may be different between a sample having a positive dielectric anisotropy and a sample having a negative dielectric anisotropy. The measurement method when the dielectric constant anisotropy is positive is described in item (8a) to item (12a). In the case where the dielectric constant anisotropy is negative, the measurement method is described in item (8b) to item (12b).

（8a）黏度（旋轉黏度；γ1；於25℃下測定；mPa·s） 正的介電常數各向異性：測定是依據M.今井（M. Imai）等人的「分子晶體及液晶（Molecular Crystals and Liquid Crystals）」（Vol. 259，37（1995））中所記載的方法。於扭轉角為0度、而且兩片玻璃基板的間隔（單元間隙）為5 μm的TN元件中放入試樣。對該元件於16 V至19.5 V的範圍內以0.5 V為單位階段性地施加電壓。不施加電壓0.2秒後，以僅一個矩形波（矩形脈衝；0.2秒）與不施加（2秒）的條件反覆施加電壓。對因該施加而產生的暫態電流（transient current）的峰值電流（peak current）及峰值時間（peak time）進行測定。根據該些測定值及M.今井（M. Imai）等人的論文40頁的計算式（8）而獲得旋轉黏度的值。該計算所必需的介電常數各向異性的值是使用測定了該旋轉黏度的元件並利用以下記載的方法而求出。(8a) Viscosity (rotational viscosity; γ1; measured at 25°C; mPa s) Positive dielectric constant anisotropy: The measurement is based on the records in "Molecular Crystals and Liquid Crystals" (Vol. 259, 37 (1995)) by M. Imai et al. method. The sample was placed in a TN device with a twist angle of 0 degrees and a gap (cell gap) between two glass substrates of 5 μm. A voltage was applied to the element in steps of 0.5 V in the range of 16 V to 19.5 V. After no voltage was applied for 0.2 seconds, the voltage was repeatedly applied under the conditions of only one rectangular wave (rectangular pulse; 0.2 seconds) and no application (2 seconds). The peak current (peak current) and peak time (peak time) of the transient current (transient current) generated by this application were measured. The value of the rotational viscosity was obtained from these measured values and the calculation formula (8) on page 40 of the paper by M. Imai et al. The value of dielectric constant anisotropy necessary for this calculation was obtained by the method described below using the element whose rotational viscosity was measured.

（8b）黏度（旋轉黏度；γ1；於25℃下測定；mPa·s） 負的介電常數各向異性：測定是依據M.今井（M. Imai）等人的「分子晶體及液晶（Molecular Crystals and Liquid Crystals）」（Vol. 259，37（1995））中所記載的方法。於兩片玻璃基板的間隔（單元間隙）為20 μm的VA元件中放入試樣。對該元件於39伏特至50伏特的範圍內以1伏特為單位階段性地施加電壓。不施加電壓0.2秒後，以僅一個矩形波（矩形脈衝；0.2秒）與不施加（2秒）的條件反覆施加電壓。對因該施加而產生的暫態電流（transient current）的峰值電流（peak current）及峰值時間（peak time）進行測定。根據該些測定值及M.今井（M. Imai）等人的論文40頁的計算式（8）而獲得旋轉黏度的值。該計算所必需的介電常數各向異性是使用下述介電常數各向異性的項中測定的值。(8b) Viscosity (rotational viscosity; γ1; measured at 25°C; mPa s) Negative dielectric constant anisotropy: The measurement is based on the records in "Molecular Crystals and Liquid Crystals" (Vol. 259, 37 (1995)) by M. Imai et al. method. The sample is placed in a VA element with a distance (cell gap) between two glass substrates of 20 μm. A voltage was applied to the element in steps of 1 volt in the range of 39 volts to 50 volts. After no voltage was applied for 0.2 seconds, the voltage was repeatedly applied under the conditions of only one rectangular wave (rectangular pulse; 0.2 seconds) and no application (2 seconds). The peak current (peak current) and peak time (peak time) of the transient current (transient current) generated by this application were measured. The value of the rotational viscosity was obtained from these measured values and the calculation formula (8) on page 40 of the paper by M. Imai et al. The dielectric constant anisotropy necessary for this calculation is a value measured using the item of dielectric constant anisotropy described below.

（9a）介電常數各向異性（Δε；於25℃下測定） 正的介電常數各向異性：於兩片玻璃基板的間隔（單元間隙）為9 μm、而且扭轉角為80度的TN元件中放入試樣。對該元件施加正弦波（10 V、1 kHz），2秒後測定液晶分子的長軸方向上的介電常數（ε∥）。對該元件施加正弦波（0.5 V、1 kHz），2秒後測定液晶分子的短軸方向上的介電常數（ε⊥）。介電常數各向異性的值是根據Δε=ε∥-ε⊥的式子來計算。(9a) Dielectric constant anisotropy (Δε; measured at 25°C) Positive dielectric constant anisotropy: Put the sample in a TN element with a distance (cell gap) between two glass substrates of 9 μm and a twist angle of 80 degrees. A sine wave (10 V, 1 kHz) was applied to the device, and the dielectric constant (ε∥) in the long-axis direction of the liquid crystal molecules was measured after 2 seconds. A sine wave (0.5 V, 1 kHz) was applied to the device, and the dielectric constant (ε⊥) in the minor axis direction of the liquid crystal molecules was measured after 2 seconds. The value of dielectric constant anisotropy is calculated according to the formula Δε=ε∥-ε⊥.

（9b）介電常數各向異性（Δε；於25℃下測定） 負的介電常數各向異性：介電常數各向異性的值是根據Δε=ε∥-ε⊥的式子來計算。介電常數（ε∥及ε⊥）是如下般測定。 1）介電常數（ε∥）的測定：於經充分清洗的玻璃基板上塗佈十八烷基三乙氧基矽烷（0.16 mL）的乙醇（20 mL）溶液。利用旋轉器使玻璃基板旋轉後，於150℃下加熱1小時。於兩片玻璃基板的間隔（單元間隙）為4 μm的VA元件中放入試樣，藉由利用紫外線進行硬化的接著劑將該元件密閉。對該元件施加正弦波（0.5 V、1 kHz），2秒後測定液晶分子的長軸方向上的介電常數（ε∥）。 2）介電常數（ε⊥）的測定：於經充分清洗的玻璃基板上塗佈聚醯亞胺溶液。將該玻璃基板煆燒後，對所得的配向膜進行摩擦處理。於兩片玻璃基板的間隔（單元間隙）為9 μm、扭轉角為80度的TN元件中放入試樣。對該元件施加正弦波（0.5 V、1 kHz），2秒後測定液晶分子的短軸方向上的介電常數（ε⊥）。(9b) Dielectric constant anisotropy (Δε; measured at 25°C) Negative permittivity anisotropy: The value of permittivity anisotropy is calculated according to the formula Δε=ε∥-ε⊥. The dielectric constants (ε∥ and ε⊥) were measured as follows. 1) Measurement of dielectric constant (ε∥): Coat octadecyltriethoxysilane (0.16 mL) in ethanol (20 mL) on a fully cleaned glass substrate. After rotating the glass substrate with a rotator, it heated at 150 degreeC for 1 hour. A sample is placed in a VA element with a distance (cell gap) of 4 μm between two glass substrates, and the element is sealed with an adhesive that hardens with ultraviolet rays. A sine wave (0.5 V, 1 kHz) was applied to the device, and after 2 seconds, the dielectric constant (ε∥) in the long-axis direction of the liquid crystal molecules was measured. 2) Measurement of dielectric constant (ε⊥): Coating polyimide solution on a fully cleaned glass substrate. After the glass substrate is fired, rubbing treatment is performed on the obtained alignment film. The sample was placed in a TN device with a gap (cell gap) between two glass substrates of 9 μm and a twist angle of 80 degrees. A sine wave (0.5 V, 1 kHz) was applied to the device, and the dielectric constant (ε⊥) in the minor axis direction of the liquid crystal molecules was measured after 2 seconds.

（10a）彈性常數（K；於25℃下測定；pN） 正的介電常數各向異性：於測定時，使用安捷倫科技（Agilent Technologies）公司製造的HP4284A型LCR計。於兩片玻璃基板的間隔（單元間隙）為20 μm的水平配向元件中放入試樣。對該元件施加0伏特至20伏特的電荷，測定靜電電容及施加電壓。使用「液晶器件手冊」（日刊工業報社）75頁中的式（2.98）、式（2.101）對所測定的靜電電容（C）及施加電壓（V）的值進行擬合，根據式（2.99）而獲得K11 及K33 的值。其次，於171頁中的式（3.18）中，使用之前求出的K11 及K33 的值算出K22 。彈性常數K是以如此般求出的K11 、K22 及K33 的平均值來表示。(10a) Elastic constant (K; measured at 25° C.; pN) Positive dielectric constant anisotropy: During measurement, an HP4284A LCR meter manufactured by Agilent Technologies was used. The sample was placed in a horizontal alignment device with a distance (cell gap) of 20 μm between two glass substrates. A charge of 0 volts to 20 volts was applied to the element, and the capacitance and applied voltage were measured. Using the formula (2.98) and formula (2.101) on page 75 of the "Liquid Crystal Device Handbook" (Nikkan Kogyo Shimbun) to fit the measured capacitance (C) and applied voltage (V), according to the formula (2.99) And obtain the value of K 11 and K 33 . Next, in the formula (3.18) on page 171, K 22 is calculated using the previously obtained values of K 11 and K 33 . The elastic constant K is represented by the average value of K 11 , K 22 and K 33 obtained in this way.

（10b）彈性常數（K11 及K33 ；於25℃下測定；pN） 負的介電常數各向異性：於測定時，使用東陽技術（TOYO Technica）（股）製造的EC-1型彈性常數測定器。於兩片玻璃基板的間隔（單元間隙）為20 μm的垂直配向元件中放入試樣。對該元件施加20伏特至0伏特的電荷，測定靜電電容及施加電壓。使用「液晶器件手冊」（日刊工業報社）75頁中的式（2.98）、式（2.101）對靜電電容（C）及施加電壓（V）的值進行擬合，根據式（2.100）而獲得彈性常數的值。(10b) Elastic constant (K 11 and K 33 ; measured at 25°C; pN) Negative dielectric constant anisotropy: EC-1 type elastic material manufactured by TOYO Technica Co., Ltd. was used for measurement. constant tester. The sample was placed in a vertical alignment element with a distance (cell gap) of 20 μm between two glass substrates. A charge of 20 volts to 0 volts was applied to the element, and the capacitance and applied voltage were measured. Use formula (2.98) and formula (2.101) on page 75 of "Liquid Crystal Device Handbook" (Nikkan Kogyo Shimbun) to fit the values of electrostatic capacitance (C) and applied voltage (V), and obtain elasticity according to formula (2.100) The value of the constant.

（11a）臨限電壓（Vth；於25℃下測定；V） 正的介電常數各向異性：於測定時，使用大塚電子（股）製造的LCD5100型亮度計。光源設為鹵素燈。於兩片玻璃基板的間隔（單元間隙）為0.45/Δn（μm）、扭轉角為80度的常白模式（normally white mode）的TN元件中放入試樣。對該元件施加的電壓（32 Hz、矩形波）是自0 V起以0.02 V為單位階段性地增加至10 V為止。此時，對元件自垂直方向照射光，測定透過元件的光量。製成該光量達到最大時為透過率100%、該光量最小時為透過率0%的電壓-透過率曲線。臨限電壓是以透過率成為90%時的電壓來表示。(11a) Threshold voltage (Vth; measured at 25°C; V) Positive dielectric constant anisotropy: for measurement, an LCD5100 luminance meter manufactured by Otsuka Electronics Co., Ltd. was used. The light source was set as a halogen lamp. The sample was placed in a normally white mode (normally white mode) TN element with an interval (cell gap) between two glass substrates of 0.45/Δn (μm) and a twist angle of 80 degrees. The voltage (32 Hz, rectangular wave) applied to the element was increased stepwise from 0 V to 10 V in units of 0.02 V. At this time, the device was irradiated with light from a vertical direction, and the amount of light transmitted through the device was measured. A voltage-transmittance curve was prepared in which the transmittance was 100% when the amount of light was at its maximum and the transmittance was 0% when the amount of light was at its minimum. The threshold voltage is represented by the voltage at which the transmittance becomes 90%.

（11b）臨限電壓（Vth；於25℃下測定；V） 負的介電常數各向異性：於測定時，使用大塚電子（股）製造的LCD5100型亮度計。光源設為鹵素燈。於兩片玻璃基板的間隔（單元間隙）為4 μm、摩擦方向為反平行的常黑模式（normally black mode）的VA元件中放入試樣，使用利用紫外線進行硬化的接著劑將該元件密閉。對該元件施加的電壓（60 Hz、矩形波）是自0 V起以0.02 V為單位階段性地增加至20 V為止。此時，對元件自垂直方向照射光，測定透過元件的光量。製成該光量達到最大時為透過率100%、該光量最小時為透過率0%的電壓-透過率曲線。臨限電壓是以透過率成為10%時的電壓來表示。(11b) Threshold voltage (Vth; measured at 25°C; V) Negative dielectric constant anisotropy: for measurement, an LCD5100 luminance meter manufactured by Otsuka Electronics Co., Ltd. was used. The light source was set as a halogen lamp. A sample is placed in a normally black mode (normally black mode) VA element with a distance (cell gap) between two glass substrates of 4 μm and an antiparallel rubbing direction, and the element is sealed with an adhesive that hardens with ultraviolet light . The voltage (60 Hz, rectangular wave) applied to the element was increased stepwise from 0 V to 20 V in units of 0.02 V. At this time, the device was irradiated with light from a vertical direction, and the amount of light transmitted through the device was measured. A voltage-transmittance curve was prepared in which the transmittance was 100% when the amount of light was at its maximum and the transmittance was 0% when the amount of light was at its minimum. The threshold voltage is represented by the voltage at which the transmittance becomes 10%.

（12a）響應時間（τ；於25℃下測定；ms） 正的介電常數各向異性：於測定時，使用大塚電子（股）製造的LCD5100型亮度計。光源設為鹵素燈。低通濾波器（Low-pass filter）是設定為5 kHz。於兩片玻璃基板的間隔（單元間隙）為5.0 μm、扭轉角為80度的常白模式（normally white mode）的TN元件中放入試樣。對該元件施加矩形波（60 Hz、5 V、0.5秒）。此時，對元件自垂直方向照射光，測定透過元件的光量。將該光量達到最大時視為透過率100%，該光量最小時視為透過率0%。上昇時間（τr：rise time；毫秒）為透過率自90%變化為10%所需要的時間。下降時間（τf：fall time；毫秒）為透過率自10%變化為90%所需要的時間。響應時間是以如此般求出的上昇時間與下降時間的和來表示。(12a) Response time (τ; determined at 25°C; ms) Positive dielectric constant anisotropy: for measurement, an LCD5100 luminance meter manufactured by Otsuka Electronics Co., Ltd. was used. The light source was set as a halogen lamp. Low-pass filter (Low-pass filter) is set to 5 kHz. The sample was placed in a normally white mode TN device with a distance (cell gap) between two glass substrates of 5.0 μm and a twist angle of 80 degrees. Apply a rectangular wave (60 Hz, 5 V, 0.5 sec) to the element. At this time, the device was irradiated with light from a vertical direction, and the amount of light transmitted through the device was measured. When the amount of light reaches the maximum, the transmittance is regarded as 100%, and when the amount of light is minimized, the transmittance is regarded as 0%. Rise time (τr: rise time; milliseconds) is the time required for the transmittance to change from 90% to 10%. Fall time (τf: fall time; milliseconds) is the time required for the transmittance to change from 10% to 90%. The response time is represented by the sum of the rise time and fall time obtained in this way.

（12b）響應時間（τ；於25℃下測定；ms） 負的介電常數各向異性：於測定時，使用大塚電子（股）製造的LCD5100型亮度計。光源設為鹵素燈。低通濾波器（Low-pass filter）是設定為5 kHz。於兩片玻璃基板的間隔（單元間隙）為3.2 μm、摩擦方向為反平行的常黑模式（normally black mode）的PVA元件中放入試樣。使用利用紫外線進行硬化的接著劑將該元件密閉。對該元件施加稍許超過臨限電壓的程度的電壓1分鐘，其次，一面施加5.6 V的電壓，一面照射23.5 mW/cm2 的紫外線8分鐘。對該元件施加矩形波（60 Hz、10 V、0.5秒）。此時，對元件自垂直方向照射光，測定透過元件的光量。將該光量達到最大時視為透過率100%，該光量最小時視為透過率0%。響應時間是以透過率自90%變化為10%所需要的時間（下降時間；fall time；毫秒）來表示。(12b) Response time (τ; measured at 25° C.; ms) Negative dielectric constant anisotropy: for measurement, an LCD5100 luminance meter manufactured by Otsuka Electronics Co., Ltd. was used. The light source was set as a halogen lamp. Low-pass filter (Low-pass filter) is set to 5 kHz. The sample was placed in a normally black mode (normally black mode) PVA element in which the distance (cell gap) between two glass substrates was 3.2 μm and the rubbing direction was antiparallel. The element is sealed with an adhesive that hardens with ultraviolet rays. A voltage slightly exceeding the threshold voltage was applied to the element for 1 minute, and then 23.5 mW/cm 2 of ultraviolet rays was irradiated for 8 minutes while applying a voltage of 5.6 V. Apply a rectangular wave (60 Hz, 10 V, 0.5 sec) to the element. At this time, the device was irradiated with light from a vertical direction, and the amount of light transmitted through the device was measured. When the amount of light reaches the maximum, the transmittance is regarded as 100%, and when the amount of light is minimized, the transmittance is regarded as 0%. The response time is represented by the time required for the transmittance to change from 90% to 10% (fall time; fall time; milliseconds).

（13）電壓保持率 使用岩琦（Eye Graphics）（股）製造的不可見光（black light）、F40T10/BL（峰值波長369 nm）照射紫外線，藉此使聚合性化合物聚合。對該元件於60℃下施加脈衝電壓（1 V且60微秒）而進行充電。利用高速電壓計於1.67秒的期間中測定衰減的電壓，求出單位週期的電壓曲線與橫軸之間的面積A。面積B為未衰減時的面積。電壓保持率是以面積A相對於面積B的百分率來表示。(13) Voltage retention rate The polymerizable compound was polymerized by irradiating ultraviolet rays with black light F40T10/BL (peak wavelength: 369 nm) manufactured by Eye Graphics Co., Ltd. The element was charged by applying a pulse voltage (1 V, 60 microseconds) at 60°C. The decaying voltage was measured with a high-speed voltmeter in a period of 1.67 seconds, and the area A between the voltage curve per unit cycle and the horizontal axis was obtained. Area B is the area when not attenuated. The voltage retention rate is expressed as a percentage of area A relative to area B.

原料 索爾米克斯（solmix）（註冊商標）A-11為乙醇（85.5%）、甲醇（13.4%）與異丙醇（Isopropanol，IPA）（1.1%）的混合物，是自日本醇銷售（股）獲取。raw material Solmix (registered trademark) A-11 is a mixture of ethanol (85.5%), methanol (13.4%) and isopropanol (Isopropanol, IPA) (1.1%), sold from Japan Alcohol (stock )Obtain.

[合成例1] 化合物（1-2-6）的合成

Figure 02_image119
[Synthesis Example 1] Synthesis of compound (1-2-6)
Figure 02_image119

第1步驟 將化合物（T-1）（100.0 g）、對甲苯磺酸一水合物（PTSA（p-toluene sulfonic acid）·H2 O）（4.25 g）、及丙酮（300 ml）放入至反應器中，於室溫下攪拌5小時後，滴加三乙基胺（3.12 ml）。於減壓下對反應混合物進行濃縮，利用矽膠層析法（容積比，庚烷：乙酸乙酯=1：2）對殘渣進行純化而獲得化合物（T-2）（130.4 g；100%）。Step 1 Put compound (T-1) (100.0 g), p-toluenesulfonic acid monohydrate (PTSA (p-toluene sulfonic acid)·H 2 O) (4.25 g), and acetone (300 ml) into In the reactor, after stirring at room temperature for 5 hours, triethylamine (3.12 ml) was added dropwise. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (volume ratio, heptane:ethyl acetate=1:2) to obtain compound (T-2) (130.4 g; 100%).

第2步驟 將化合物（T-2）（10.0 g）、二氯甲烷（20 ml）放入至反應器中，冷卻至0℃。向其中加入甲苯磺醯氯（10.1 g）、吡啶（5.5 ml），加熱至40℃並攪拌2天。將反應混合物注入至水中，利用二氯甲烷來萃取水層。利用水對所獲得的有機層進行清洗，利用無水硫酸鎂進行乾燥。於減壓下對該溶液進行濃縮，利用矽膠層析法（容積比，庚烷：乙酸乙酯=3：1）對殘渣進行純化而獲得化合物（T-3）（14.3 g；76%）。Step 2 Compound (T-2) (10.0 g) and dichloromethane (20 ml) were put into the reactor, and cooled to 0°C. Tosyl chloride (10.1 g) and pyridine (5.5 ml) were added thereto, heated to 40°C and stirred for 2 days. The reaction mixture was poured into water, and the aqueous layer was extracted with dichloromethane. The obtained organic layer was washed with water, and dried with anhydrous magnesium sulfate. The solution was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (volume ratio, heptane:ethyl acetate=3:1) to obtain compound (T-3) (14.3 g; 76%).

第3步驟 將化合物（T-3）（48.1 g）、碘化鈉（54.9 g）、及2-丁酮（300 ml）放入至反應器中，於70℃下進行4小時加熱攪拌。將反應混合物注入至水中，利用己酸乙酯來萃取水層。利用食鹽水對所獲得的有機層進行清洗，利用無水硫酸鎂進行乾燥。於減壓下對該溶液進行濃縮，利用矽膠層析法（容積比，庚烷：乙酸乙酯=3：1）對殘渣進行純化而獲得化合物（T-4）（38.9 g；93%）。Step 3 Compound (T-3) (48.1 g), sodium iodide (54.9 g), and 2-butanone (300 ml) were put into a reactor, and heated and stirred at 70° C. for 4 hours. The reaction mixture was poured into water, and the aqueous layer was extracted with ethyl hexanoate. The obtained organic layer was washed with brine, and dried with anhydrous magnesium sulfate. The solution was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (volume ratio, heptane:ethyl acetate=3:1) to obtain compound (T-4) (38.9 g; 93%).

第4步驟 將氫化鈉（32.6 g）、DMF（1000 ml）放入至反應器中，冷卻至0℃。滴加化合物（T-5）（159.3 g）的DMF溶液並攪拌1小時。之後，滴加化合物（T-4）（101.0 g），加熱至110℃並攪拌4天。將反應混合物注入至水中，利用甲苯來萃取水層。利用食鹽水對所獲得的有機層進行清洗，利用無水硫酸鎂進行乾燥。於減壓下對該溶液進行濃縮。向其中加入水（500 ml）、碳酸鉀（98.2 g）、聚甲醛（42.7 g），於80℃下進行6小時加熱攪拌。將反應混合物注入至水中，利用己酸乙酯來萃取水層。利用水、食鹽水對所獲得的有機層進行清洗，利用無水硫酸鎂進行乾燥。於減壓下對該溶液進行濃縮，利用矽膠層析法（容積比，庚烷：乙酸乙酯=8：1）對殘渣進行純化而獲得化合物（T-6）（11.4 g；12%）。Step 4 Sodium hydride (32.6 g) and DMF (1000 ml) were put into the reactor and cooled to 0°C. A DMF solution of compound (T-5) (159.3 g) was added dropwise and stirred for 1 hour. Thereafter, compound (T-4) (101.0 g) was added dropwise, heated to 110° C., and stirred for 4 days. The reaction mixture was poured into water, and the aqueous layer was extracted with toluene. The obtained organic layer was washed with brine, and dried with anhydrous magnesium sulfate. The solution was concentrated under reduced pressure. Water (500 ml), potassium carbonate (98.2 g), and polyoxymethylene (42.7 g) were added thereto, and heated and stirred at 80° C. for 6 hours. The reaction mixture was poured into water, and the aqueous layer was extracted with ethyl hexanoate. The obtained organic layer was washed with water and brine, and dried with anhydrous magnesium sulfate. The solution was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (volume ratio, heptane:ethyl acetate=8:1) to obtain Compound (T-6) (11.4 g; 12%).

第5步驟 將化合物（T-6）（12.1 g）、四丁基溴化銨（TBAB）（1.5 g）、水（114.7 ml）、THF（3.82 ml）放入至反應器中，冷卻至0℃。向其中加入氫氧化鋰一水合物（3.95 g），於50℃下加熱攪拌7小時。將反應混合物注入至水中，利用甲苯對水層進行清洗，進而利用檸檬酸水溶液進行清洗而將pH值調整為4。利用己酸乙酯來萃取所獲得的水層。利用食鹽水對所獲得的有機層進行清洗，利用無水硫酸鎂進行乾燥。於減壓下對該溶液進行濃縮，而獲得化合物（T-7）（10.5 g；98%）。Step 5 Compound (T-6) (12.1 g), tetrabutylammonium bromide (TBAB) (1.5 g), water (114.7 ml), and THF (3.82 ml) were put into the reactor, and cooled to 0°C. Lithium hydroxide monohydrate (3.95 g) was added thereto, followed by heating and stirring at 50°C for 7 hours. The reaction mixture was poured into water, and the aqueous layer was washed with toluene, and further washed with a citric acid aqueous solution to adjust the pH to 4. The obtained aqueous layer was extracted with ethyl hexanoate. The obtained organic layer was washed with brine, and dried with anhydrous magnesium sulfate. The solution was concentrated under reduced pressure to obtain Compound (T-7) (10.5 g; 98%).

第6步驟 將化合物（T-7）（3.9 g）、利用公知的方法而合成的化合物（T-8）（5.0 g）、N,N-二環己基碳二醯亞胺（DCC）（3.8 g）、二氯甲烷（50 ml）放入至反應器中，冷卻至0℃。向其中加入N,N-二甲基胺基吡啶（DMAP）（0.75 g），於室溫下攪拌12小時。對反應混合物進行抽吸過濾後將濾液注入至水中，利用二氯甲烷來萃取水層。利用食鹽水對所獲得的有機層進行清洗，利用無水硫酸鎂進行乾燥。於減壓下對該溶液進行濃縮，利用矽膠層析法（容積比，庚烷：乙酸乙酯=7：1）對殘渣進行純化而獲得化合物（T-9）（6.1 g；81%）。Step 6 Compound (T-7) (3.9 g), compound (T-8) (5.0 g) synthesized by a known method, N,N-dicyclohexylcarbodiimide (DCC) (3.8 g), Dichloromethane (50 ml) was put into the reactor and cooled to 0°C. N,N-Dimethylaminopyridine (DMAP) (0.75 g) was added thereto, followed by stirring at room temperature for 12 hours. After suction filtering the reaction mixture, the filtrate was poured into water, and the aqueous layer was extracted with dichloromethane. The obtained organic layer was washed with brine, and dried with anhydrous magnesium sulfate. The solution was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (volume ratio, heptane:ethyl acetate=7:1) to obtain Compound (T-9) (6.1 g; 81%).

第7步驟 將化合物（T-9）（0.5 g）、THF（7.5 ml）、甲醇（7.5 ml）、及對甲苯磺酸吡啶鎓（pyridinium p-toluene sulfonate，PPTS）（0.04 g）放入至反應器中，於室溫下攪拌12小時。將反應混合物注入至水中，利用乙酸乙酯來萃取水層。利用食鹽水對所獲得的有機層進行清洗，利用無水硫酸鎂進行乾燥。於減壓下對該溶液進行濃縮，利用矽膠層析法（容積比，庚烷：乙酸乙酯=2：1）對殘渣進行純化而獲得化合物（1-2-6）（0.3 g；71%）。Step 7 Put compound (T-9) (0.5 g), THF (7.5 ml), methanol (7.5 ml), and pyridinium p-toluene sulfonate (PPTS) (0.04 g) into the reactor , stirred at room temperature for 12 hours. The reaction mixture was poured into water, and the aqueous layer was extracted with ethyl acetate. The obtained organic layer was washed with brine, and dried with anhydrous magnesium sulfate. The solution was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (volume ratio, heptane:ethyl acetate=2:1) to obtain compound (1-2-6) (0.3 g; 71% ).

所獲得的化合物（1-2-6）的NMR分析值如下所述。1 H-NMR：化學位移δ (ppm；CDCl3 )：6.48 (s, 1H), 6.12 (s, 1H), 5.75 (s, 1H), 5.60 (s, 1H), 4.26-4.14 (m, 4H), 3.55-3.51 (m, 2H), 3.41-3.37 (m, 2H), 3.33-3.31 (m, 2H), 2.49 (s, 1H), 2.13-2.08 (m, 1H), 1.97 (s, 3H), 1.77-1.71 (m, 8H), 1.47-1.12 (m, 17H), 1.04-0.84 (m, 16H).The NMR analysis values of the obtained compound (1-2-6) are as follows. 1 H-NMR: Chemical shift δ (ppm; CDCl 3 ): 6.48 (s, 1H), 6.12 (s, 1H), 5.75 (s, 1H), 5.60 (s, 1H), 4.26-4.14 (m, 4H ), 3.55-3.51 (m, 2H), 3.41-3.37 (m, 2H), 3.33-3.31 (m, 2H), 2.49 (s, 1H), 2.13-2.08 (m, 1H), 1.97 (s, 3H ), 1.77-1.71 (m, 8H), 1.47-1.12 (m, 17H), 1.04-0.84 (m, 16H).

轉變溫度：C 50.7 C 52.16 I, 聚合起始溫度：206.8℃Transition temperature: C 50.7 C 52.16 I, Polymerization initiation temperature: 206.8°C

[比較例1] 相容性的比較 作為比較化合物，選擇下述化合物（S-1）。該化合物是依據公知的方法來合成。

Figure 02_image121
[Comparative Example 1] Compatibility Comparison As a comparative compound, the following compound (S-1) was selected. This compound is synthesized according to a known method.
Figure 02_image121

1 H-NMR (ppm；CDCl3 )：6.25 (S, 1H), 6.10 (s, 1H), 5.66 (S, 1H), 5.58-5.57 (m, 1H), 4.22-4.10 (m, 4H), 3.80-3.75 (m, 2H), 3.67-3.62 (m, 2H), 2.55-2.52 (m, 2H), 2.37 (d, J=7.4 Hz, 2H), 2.10-2.05 (m, 1H), 1.94 (s, 3H), 1.90-1.86 (m, 1H), 1.75-1.67 (m, 8H), 1.48-1.37 (m, 2H), 1.32-0.79 (m, 25H). 1 H-NMR (ppm; CDCl 3 ): 6.25 (S, 1H), 6.10 (s, 1H), 5.66 (S, 1H), 5.58-5.57 (m, 1H), 4.22-4.10 (m, 4H), 3.80-3.75 (m, 2H), 3.67-3.62 (m, 2H), 2.55-2.52 (m, 2H), 2.37 (d, J=7.4 Hz, 2H), 2.10-2.05 (m, 1H), 1.94 ( s, 3H), 1.90-1.86 (m, 1H), 1.75-1.67 (m, 8H), 1.48-1.37 (m, 2H), 1.32-0.79 (m, 25H).

對化合物（1-2-6）與比較化合物（S-1）於液晶組成物中的相容性進行比較。評價中使用包含下述化合物（i-1）～化合物（i-9）的母液晶（i）。The compatibility of the compound (1-2-6) and the comparative compound (S-1) in the liquid crystal composition was compared. Mother liquid crystals (i) containing the following compound (i-1) to compound (i-9) were used for the evaluation.

以重量%來表示母液晶（i）的各成分的比例。

Figure 02_image123
The ratio of each component of the mother liquid crystal (i) is expressed in % by weight.
Figure 02_image123

製成於母液晶（i）中以3重量%至0.5重量%的比例添加有化合物（1-2-6）或比較化合物（S-1）的試樣。將該試樣於25℃及-20℃下靜置7天後，藉由目視進行觀察，將維持向列相的情況表示為○，將析出有結晶或層列相的情況表示為×。A sample in which the compound (1-2-6) or the comparative compound (S-1) was added to the mother liquid crystal (i) in a ratio of 3% by weight to 0.5% by weight was prepared. After leaving this sample at 25° C. and −20° C. for 7 days, it was observed visually. The case where the nematic phase was maintained was indicated as ◯, and the case where crystals or smectic phases were precipitated was indicated as ×.

表2.相容性

Figure 108136306-A0304-0002
Table 2. Compatibility
Figure 108136306-A0304-0002

將溶解度加以比較，結果化合物（1-2-6）即便於母液晶（i）中添加3重量%，於25℃及-20℃兩者下亦維持向列相，相對於此，比較化合物（S-1）添加3重量%時於-20℃下析出結晶。該些化合物為於具有相同的環結構並鍵結有多個聚合性基的方面類似的化合物，但兩者的相容性大不同。可考察其原因在於：化合物（1-2-6）藉由導入乙基，與比較化合物（S-1）相比，對液晶組成物的親和性得到改善。因此，本申請案化合物可謂是具有大的相容性的優異的化合物。Comparing the solubility, the compound (1-2-6) was found to maintain a nematic phase at both 25°C and -20°C even when 3% by weight was added to the mother liquid crystal (i). In contrast, the comparative compound ( S-1) When 3% by weight is added, crystals are precipitated at -20°C. These compounds are similar in that they have the same ring structure and bonded with a plurality of polymerizable groups, but the compatibility of the two is greatly different. The reason for this is considered to be that the compound (1-2-6) has improved affinity for the liquid crystal composition compared with the comparative compound (S-1) by introducing an ethyl group. Therefore, the compound of the present application can be said to be an excellent compound having a large compatibility.

可參考合成例中所記載的方法或「2.化合物（1）的合成」的項，來合成以下所示的化合物。The compounds shown below can be synthesized by referring to the methods described in the synthesis examples or the item "2. Synthesis of compound (1)".

Figure 02_image129
Figure 02_image129

Figure 02_image131
Figure 02_image131

Figure 02_image133
Figure 02_image133

Figure 02_image135
Figure 02_image135

Figure 02_image137
Figure 02_image137

Figure 02_image139
Figure 02_image139

Figure 02_image141
Figure 02_image141

Figure 02_image143
Figure 02_image143

Figure 02_image145
Figure 02_image145

Figure 02_image147
Figure 02_image147

Figure 02_image149
Figure 02_image149

Figure 02_image151
Figure 02_image151

Figure 02_image153
Figure 02_image153

Figure 02_image155
Figure 02_image155

Figure 02_image157
Figure 02_image157

Figure 02_image159
Figure 02_image159

Figure 02_image161
Figure 02_image161

Figure 02_image163
Figure 02_image163

Figure 02_image165
Figure 02_image165

Figure 02_image167
Figure 02_image167

Figure 02_image169
Figure 02_image169

Figure 02_image171
Figure 02_image171

Figure 02_image173
Figure 02_image173

2.組成物的實施例 實施例中的化合物基於下述表3的定義而以記號來表示。表3中，與1,4-伸環己基相關的立體構型為反式構型。位於記號後的括弧內的編號與化合物的編號相對應。（-）的記號是指其他液晶性化合物。液晶性化合物的比例（百分率）為基於液晶組成物的重量的重量百分率（重量%）。最後歸納液晶組成物的特性值。特性是依據上文記載的方法來測定，（不進行外推而）直接記載測定值。2. Examples of compositions The compounds in Examples are represented by symbols based on the definitions in Table 3 below. In Table 3, the configuration related to 1,4-cyclohexylene is trans configuration. The numbers placed in parentheses after the symbols correspond to the numbers of the compounds. The mark of (-) means another liquid crystal compound. The ratio (percentage) of the liquid crystal compound is the percentage by weight (% by weight) based on the weight of the liquid crystal composition. Finally, the characteristic values of the liquid crystal composition are summarized. The characteristics are measured according to the methods described above, and the measured values are directly described (without extrapolation).

Figure 02_image175
Figure 02_image175

[使用例1] 1-BB-3                                   （2-8）                    6% 1-BB-5                                   （2-8）                    7% 2-BTB-1                                 （2-10）                  3% 3-HHB-1                                     （3-1）                    7% 3-HHB-3                                     （3-1）                    12% 3-HHB-O1                              （3-1）                    6% 3-HHB-F                                （6-1）                    4% 2-HHB(F)-F                            （6-2）                    8% 3-HHB(F)-F                            （6-2）                    8% 5-HHB(F)-F                            （6-2）                    7% 3-HHB(F,F)-F                         （6-3）                    5% 3-HHEB-F                              （6-10）                  4% 5-HHEB-F                              （6-10）                  4% 2-HB-C                                  （8-1）                    6% 3-HB-C                                  （8-1）                    13% 以1重量%的比例於所述組成物中添加下述化合物（1-2-6）。

Figure 02_image177
NI=95.6℃；η=17.9 mPa·s；Δn=0.107；Δε=5.1.[Example 1] 1-BB-3 (2-8) 6% 1-BB-5 (2-8) 7% 2-BTB-1 (2-10) 3% 3-HHB-1 (3-1 ) 7% 3-HHB-3 (3-1) 12% 3-HHB-O1 (3-1) 6% 3-HHB-F (6-1) 4% 2-HHB(F)-F (6- 2) 8% 3-HHB(F)-F (6-2) 8% 5-HHB(F)-F (6-2) 7% 3-HHB(F,F)-F (6-3) 5 % 3-HHEB-F (6-10) 4% 5-HHEB-F (6-10) 4% 2-HB-C (8-1) 6% 3-HB-C (8-1) 13% or more The following compound (1-2-6) was added to the composition at a rate of 1% by weight.
Figure 02_image177
NI=95.6℃; η=17.9 mPa s; Δn=0.107; Δε=5.1.

[使用例2] 3-HH-4                                  （2-1）                    11% 5-HB-O2                                     （2-5）                    4% 7-HB-1                                   （2-5）                    2% 5-HBB(F)B-2                          （4-5）                    5% 5-HBB(F)B-3                          （4-5）                    5% 3-HB-CL                                （5-2）                    13% 3-HHB(F,F)-F                         （6-3）                    3% 3-HBB(F,F)-F                         （6-24）                  24% 4-HBB(F,F)-F                         （6-24）                  16% 5-HBB(F,F)-F                         （6-24）                  17% 以3重量%的比例於所述組成物中添加下述化合物（1-2-8）。

Figure 02_image179
NI=70.6℃；η=20.8 mPa·s；Δn=0.115；Δε=6.0.[Use example 2] 3-HH-4 (2-1) 11% 5-HB-O2 (2-5) 4% 7-HB-1 (2-5) 2% 5-HBB(F)B-2 (4-5) 5% 5-HBB(F)B-3 (4-5) 5% 3-HB-CL (5-2) 13% 3-HHB(F,F)-F (6-3) 3% 3-HBB(F,F)-F (6-24) 24% 4-HBB(F,F)-F (6-24) 16% 5-HBB(F,F)-F (6-24 ) 17% The following compound (1-2-8) was added to the composition at a ratio of 3% by weight.
Figure 02_image179
NI=70.6℃; η=20.8 mPa s; Δn=0.115; Δε=6.0.

[使用例3] 1V2-HH-1                              （2-1）                    3% 1V2-HH-3                              （2-1）                    4% 7-HB(F,F)-F                           （5-4）                    3% 2-HHB(F)-F                            （6-2）                    8% 3-HHB(F)-F                            （6-2）                    12% 5-HHB(F)-F                            （6-2）                    10% 2-HBB-F                                     （6-22）                  4% 3-HBB-F                                     （6-22）                  2% 5-HBB-F                                     （6-22）                  4% 2-HBB(F)-F                            （6-23）                  9% 3-HBB(F)-F                            （6-23）                  10% 5-HBB(F)-F                            （6-23）                  16% 3-HBB(F,F)-F                         （6-24）                  5% 5-HBB(F,F)-F                         （6-24）                  10% 以5重量%的比例於所述組成物中添加下述化合物（1-2-2）。

Figure 02_image181
NI=85.1℃；η=25.3 mPa·s；Δn=0.111；Δε=5.7.[Example 3] 1V2-HH-1 (2-1) 3% 1V2-HH-3 (2-1) 4% 7-HB(F,F)-F (5-4) 3% 2-HHB( F)-F (6-2) 8% 3-HHB(F)-F (6-2) 12% 5-HHB(F)-F (6-2) 10% 2-HBB-F (6-22 ) 4% 3-HBB-F (6-22) 2% 5-HBB-F (6-22) 4% 2-HBB(F)-F (6-23) 9% 3-HBB(F)-F (6-23) 10% 5-HBB(F)-F (6-23) 16% 3-HBB(F,F)-F (6-24) 5% 5-HBB(F,F)-F ( 6-24) 10% The following compound (1-2-2) was added to the composition at a rate of 5% by weight.
Figure 02_image181
NI=85.1℃; η=25.3 mPa s; Δn=0.111; Δε=5.7.

[使用例4] 2-HH-3                                  （2-1）                    8% 3-HH-4                                  （2-1）                    8% 1O1-HBBH-5                         （4-1）                    4% 5-HB-CL                                （5-2）                    15% 3-HHB-F                                （6-1）                    4% 3-HHB-CL                              （6-1）                    3% 4-HHB-CL                              （6-1）                    4% 3-HHB(F)-F                            （6-2）                    10% 4-HHB(F)-F                            （6-2）                    9% 5-HHB(F)-F                            （6-2）                    9% 7-HHB(F)-F                            （6-2）                    8% 5-HBB(F)-F                            （6-23）                  4% 3-HHBB(F,F)-F                       （7-6）                    2% 4-HHBB(F,F)-F                       （7-6）                    3% 5-HHBB(F,F)-F                       （7-6）                    3% 3-HH2BB(F,F)-F                     （7-15）                  3% 4-HH2BB(F,F)-F                     （7-15）                  3% 以3.5重量%的比例於所述組成物中添加下述化合物（1-3-12）。

Figure 02_image183
NI=114.4℃；η=18.7 mPa·s；Δn=0.091；Δε=3.7.[Example 4] 2-HH-3 (2-1) 8% 3-HH-4 (2-1) 8% 1O1-HBBH-5 (4-1) 4% 5-HB-CL (5-2 ) 15% 3-HHB-F (6-1) 4% 3-HHB-CL (6-1) 3% 4-HHB-CL (6-1) 4% 3-HHB(F)-F (6- 2) 10% 4-HHB(F)-F (6-2) 9% 5-HHB(F)-F (6-2) 9% 7-HHB(F)-F (6-2) 8% 5 -HBB(F)-F (6-23) 4% 3-HHBB(F,F)-F (7-6) 2% 4-HHBB(F,F)-F (7-6) 3% 5- HHBB(F,F)-F (7-6) 3% 3-HH2BB(F,F)-F (7-15) 3% 4-HH2BB(F,F)-F (7-15) 3% or more The following compound (1-3-12) was added to the composition at a rate of 3.5% by weight.
Figure 02_image183
NI=114.4℃; η=18.7 mPa s; Δn=0.091; Δε=3.7.

[使用例5] V-HBB-2                                （3-4）                    10% 1O1-HBBH-4                         （4-1）                    3% 1O1-HBBH-5                         （4-1）                    5% 3-HHB(F,F)-F                         （6-3）                    9% 3-H2HB(F,F)-F                       （6-15）                  10% 4-H2HB(F,F)-F                       （6-15）                  6% 5-H2HB(F,F)-F                       （6-15）                   8% 3-HBB(F,F)-F                         （6-24）                  10% 5-HBB(F,F)-F                         （6-24）                  21% 3-H2BB(F,F)-F                       （6-27）                  10% 5-HHBB(F,F)-F                       （7-6）                    4% 3-HH2BB(F,F)-F                     （7-15）                  2% 5-HHEBB-F                           （7-17）                  2% 以5重量%的比例於所述組成物中添加下述化合物（1-5-13）。

Figure 02_image185
NI=106.7℃；η=32.6 mPa·s；Δn=0.123；Δε=8.3.[Example 5] V-HBB-2 (3-4) 10% 1O1-HBBH-4 (4-1) 3% 1O1-HBBH-5 (4-1) 5% 3-HHB(F,F)- F (6-3) 9% 3-H2HB(F,F)-F (6-15) 10% 4-H2HB(F,F)-F (6-15) 6% 5-H2HB(F,F) -F (6-15) 8% 3-HBB(F,F)-F (6-24) 10% 5-HBB(F,F)-F (6-24) 21% 3-H2BB(F,F )-F (6-27) 10% 5-HHBB(F,F)-F (7-6) 4% 3-HH2BB(F,F)-F (7-15) 2% 5-HHEBB-F ( 7-17) 2% The following compound (1-5-13) was added to the composition at a rate of 5% by weight.
Figure 02_image185
NI=106.7℃; η=32.6 mPa s; Δn=0.123; Δε=8.3.

[使用例6] 5-HBBH-3                              （4-1）                    3% 3-HB(F)BH-3                         （4-2）                    3% 5-HB-F                                  （5-2）                    12% 6-HB-F                                  （5-2）                    9% 7-HB-F                                  （5-2）                    7% 2-HHB-OCF3                         （6-1）                    7% 3-HHB-OCF3                         （6-1）                    4% 4-HHB-OCF3                         （6-1）                    7% 5-HHB-OCF3                         （6-1）                    8% 3-HHB(F,F)-OCF2H                （6-3）                    6% 3-HHB(F,F)-OCF3                  （6-3）                    3% 3-HH2B-OCF3                       （6-4）                    4% 5-HH2B-OCF3                       （6-4）                    4% 3-HH2B(F)-F                          （6-5）                    3% 3-HBB(F)-F                            （6-23）                  5% 5-HBB(F)-F                            （6-23）                  15% 以4重量%的比例於所述組成物中添加下述化合物（1-5-17）。

Figure 02_image187
NI=86.0℃；η=14.6 mPa·s；Δn=0.092；Δε=4.3.[Example 6] 5-HBBH-3 (4-1) 3% 3-HB(F)BH-3 (4-2) 3% 5-HB-F (5-2) 12% 6-HB-F (5-2) 9% 7-HB-F (5-2) 7% 2-HHB-OCF3 (6-1) 7% 3-HHB-OCF3 (6-1) 4% 4-HHB-OCF3 (6 -1) 7% 5-HHB-OCF3 (6-1) 8% 3-HHB(F,F)-OCF2H (6-3) 6% 3-HHB(F,F)-OCF3 (6-3) 3 % 3-HH2B-OCF3 (6-4) 4% 5-HH2B-OCF3 (6-4) 4% 3-HH2B(F)-F (6-5) 3% 3-HBB(F)-F (6 -23) 5% 5-HBB(F)-F (6-23) 15% The following compound (1-5-17) was added to the composition at a rate of 4% by weight.
Figure 02_image187
NI=86.0℃; η=14.6 mPa s; Δn=0.092; Δε=4.3.

[使用例7] 2-HH-5                                  （2-1）                    2% 3-HH-4                                  （2-1）                    7% 5-B(F)BB-2                            （3-8）                    4% 5-HB-CL                                （5-2）                    11% 3-HHB(F,F)-F                         （6-3）                    8% 3-HHEB(F,F)-F                       （6-12）                  5% 4-HHEB(F,F)-F                       （6-12）                  8% 5-HHEB(F,F)-F                       （6-12）                  3% 3-HBB(F,F)-F                         （6-24）                  20% 5-HBB(F,F)-F                         （6-24）                  15% 2-HBEB(F,F)-F                       （6-39）                  3% 3-HBEB(F,F)-F                       （6-39）                  3% 5-HBEB(F,F)-F                       （6-39）                  5% 3-HHBB(F,F)-F                       （7-6）                    6% 以2重量%的比例於所述組成物中添加下述化合物（1-5-25）。

Figure 02_image189
NI=77.1℃；η=22.4 mPa·s；Δn=0.108；Δε=8.5.[Example 7] 2-HH-5 (2-1) 2% 3-HH-4 (2-1) 7% 5-B(F)BB-2 (3-8) 4% 5-HB-CL (5-2) 11% 3-HHB(F,F)-F (6-3) 8% 3-HHEB(F,F)-F (6-12) 5% 4-HHEB(F,F)- F (6-12) 8% 5-HHEB(F,F)-F (6-12) 3% 3-HBB(F,F)-F (6-24) 20% 5-HBB(F,F) -F (6-24) 15% 2-HBEB(F,F)-F (6-39) 3% 3-HBEB(F,F)-F (6-39) 3% 5-HBEB(F,F )-F (6-39) 5% 3-HHBB(F,F)-F (7-6) 6% Add the following compound (1-5-25) to the composition at a rate of 2% by weight .
Figure 02_image189
NI=77.1℃; η=22.4 mPa s; Δn=0.108; Δε=8.5.

[使用例8] V2-HHB-1                              （3-1）                    4% 3-HB-CL                                （5-2）                    3% 5-HB-CL                                （5-2）                    7% 3-HHB-OCF3                         （6-1）                    5% 5-HHB(F)-F                            （6-2）                    7% V-HHB(F)-F                           （6-2）                    4% 3-H2HB-OCF3                       （6-13）                  5% 5-H2HB(F,F)-F                       （6-15）                  5% 5-H4HB-OCF3                       （6-19）                  15% 5-H4HB(F,F)-F                       （6-21）                  7% 3-H4HB(F,F)-CF3                   （6-21）                  8% 5-H4HB(F,F)-CF3                   （6-21）                  10% 2-H2BB(F)-F                          （6-26）                  5% 3-H2BB(F)-F                          （6-26）                  10% 3-HBEB(F,F)-F                       （6-39）                  5% 以0.5重量%的比例於所述組成物中添加下述化合物（1-2-6）。

Figure 02_image191
NI=72.8℃；η=25.0 mPa·s；Δn=0.098；Δε=8.2.[Example 8] V2-HHB-1 (3-1) 4% 3-HB-CL (5-2) 3% 5-HB-CL (5-2) 7% 3-HHB-OCF3 (6-1 ) 5% 5-HHB(F)-F (6-2) 7% V-HHB(F)-F (6-2) 4% 3-H2HB-OCF3 (6-13) 5% 5-H2HB(F ,F)-F (6-15) 5% 5-H4HB-OCF3 (6-19) 15% 5-H4HB(F,F)-F (6-21) 7% 3-H4HB(F,F)- CF3 (6-21) 8% 5-H4HB(F,F)-CF3 (6-21) 10% 2-H2BB(F)-F (6-26) 5% 3-H2BB(F)-F (6 -26) 10% 3-HBEB(F,F)-F (6-39) 5% The following compound (1-2-6) was added to the composition at a rate of 0.5% by weight.
Figure 02_image191
NI=72.8℃; η=25.0 mPa s; Δn=0.098; Δε=8.2.

[使用例9] 3-HH-4                                  （2-1）                    5% 3-HH-5                                  （2-1）                    10% 3-HB-O2                                     （2-5）                    15% 3-HHB-1                                     （3-1）                    5% 3-HHB-O1                              （3-1）                    8% 5-HB-CL                                （5-2）                    17% 7-HB(F,F)-F                           （5-4）                    3% 2-HHB(F)-F                            （6-2）                    8% 3-HHB(F)-F                            （6-2）                    8% 5-HHB(F)-F                            （6-2）                    5% 3-HHB(F,F)-F                         （6-3）                    6% 3-H2HB(F,F)-F                       （6-15）                  5% 4-H2HB(F,F)-F                       （6-15）                  5% 以0.7重量%的比例於所述組成物中添加下述化合物（1-2-8）。

Figure 02_image193
NI=71.9℃；η=14.1 mPa·s；Δn=0.075；Δε=2.9.[Example 9] 3-HH-4 (2-1) 5% 3-HH-5 (2-1) 10% 3-HB-O2 (2-5) 15% 3-HHB-1 (3-1 ) 5% 3-HHB-O1 (3-1) 8% 5-HB-CL (5-2) 17% 7-HB(F,F)-F (5-4) 3% 2-HHB(F) -F (6-2) 8% 3-HHB(F)-F (6-2) 8% 5-HHB(F)-F (6-2) 5% 3-HHB(F,F)-F ( 6-3) 6% 3-H2HB(F,F)-F (6-15) 5% 4-H2HB(F,F)-F (6-15) 5% 0.7% by weight in the composition The following compound (1-2-8) was added to the mixture.
Figure 02_image193
NI=71.9℃; η=14.1 mPa s; Δn=0.075; Δε=2.9.

[使用例10] 3-HH-4                                  （2-1）                    12% 3-HH-5                                  （2-1）                    7% 3-HHB-1                                      （3-1）                    13% 5-HB-CL                                （5-2）                    3% 7-HB(F)-F                              （5-3）                    7% 2-HHB(F,F)-F                         （6-3）                    2% 3-HHB(F,F)-F                         （6-3）                    7% 3-HHEB-F                              （6-10）                  8% 5-HHEB-F                              （6-10）                  8% 3-HHEB(F,F)-F                       （6-12）                  5% 4-HHEB(F,F)-F                       （6-12）                  10% 3-GHB(F,F)-F                         （6-109）                 6% 4-GHB(F,F)-F                         （6-109）                 5% 5-GHB(F,F)-F                         （6-109）                 7% 以0.3重量%的比例於所述組成物中添加下述化合物（1-2-2）。

Figure 02_image195
NI=87.1℃；η=21.7 mPa·s；Δn=0.071；Δε=5.9.[Example 10] 3-HH-4 (2-1) 12% 3-HH-5 (2-1) 7% 3-HHB-1 (3-1) 13% 5-HB-CL (5-2 ) 3% 7-HB(F)-F (5-3) 7% 2-HHB(F,F)-F (6-3) 2% 3-HHB(F,F)-F (6-3) 7% 3-HHEB-F (6-10) 8% 5-HHEB-F (6-10) 8% 3-HHEB(F,F)-F (6-12) 5% 4-HHEB(F,F )-F (6-12) 10% 3-GHB(F,F)-F (6-109) 6% 4-GHB(F,F)-F (6-109) 5% 5-GHB(F, F)-F (6-109) 7% The following compound (1-2-2) was added to the composition at a rate of 0.3% by weight.
Figure 02_image195
NI=87.1℃; η=21.7 mPa s; Δn=0.071; Δε=5.9.

[使用例11] 3-HH-VFF                              （2-1）                    8% 5-HH-VFF                              （2-1）                    22% 2-BTB-1                                 （2-10）                  10% 3-HHB-1                                     （3-1）                    4% VFF-HHB-1                           （3-1）                    10% VFF2-HHB-1                          （3-1）                    9% 3-H2BTB-2                            （3-17）                  5% 3-H2BTB-3                            （3-17）                  5% 3-H2BTB-4                            （3-17）                  3% 3-HB-C                                  （8-1）                    18% 1V2-BEB(F,F)-C                     （8-15）                  6% 以0.2重量%的比例於所述組成物中添加下述化合物（1-3-12）。

Figure 02_image197
NI=80.8℃；η=10.8 mPa·s；Δn=0.130；Δε=6.6.[Example 11] 3-HH-VFF (2-1) 8% 5-HH-VFF (2-1) 22% 2-BTB-1 (2-10) 10% 3-HHB-1 (3-1 ) 4% VFF-HHB-1 (3-1) 10% VFF2-HHB-1 (3-1) 9% 3-H2BTB-2 (3-17) 5% 3-H2BTB-3 (3-17) 5 % 3-H2BTB-4 (3-17) 3% 3-HB-C (8-1) 18% 1V2-BEB(F,F)-C (8-15) 6% 0.2% by weight in all The following compound (1-3-12) was added to the above composition.
Figure 02_image197
NI=80.8℃; η=10.8 mPa s; Δn=0.130; Δε=6.6.

[使用例12] 3-HH-V                                  （2-1）                    30% 3-HH-V1                                （2-1）                    5% 5-HH-V                                  （2-1）                    10% 3-HHB-1                                     （3-1）                    5% V-HHB-1                                （3-1）                    4% 2-BB(F)B-3                            （3-6）                    5% 3-HHEH-5                              （3-13）                  3% 1V2-BB-F                              （5-1）                    3% 3-BB(F,F)XB(F,F)-F                （6-97）                  8% 3-BB(2F,3F)XB(F,F)-F            （6-114）                 5% 3-HHBB(F,F)-F                       （7-6）                    2% 3-HBBXB(F,F)-F                    （7-32）                  4% 5-HB(F)B(F,F)XB(F,F)-F         （7-41）                  5% 3-BB(F)B(F,F)XB(F,F)-F         （7-47）                  4% 4-BB(F)B(F,F)XB(F,F)-F         （7-47）                  4% 5-BB(F)B(F,F)XB(F,F)-F         （7-47）                  3% 以1.5重量%的比例於所述組成物中添加下述化合物（1-5-13）。

Figure 02_image199
NI=78.0℃；η=12.1 mPa·s；Δn=0.097；Δε=5.5.[Example 12] 3-HH-V (2-1) 30% 3-HH-V1 (2-1) 5% 5-HH-V (2-1) 10% 3-HHB-1 (3-1 ) 5% V-HHB-1 (3-1) 4% 2-BB(F)B-3 (3-6) 5% 3-HHEH-5 (3-13) 3% 1V2-BB-F (5 -1) 3% 3-BB(F,F)XB(F,F)-F (6-97) 8% 3-BB(2F,3F)XB(F,F)-F (6-114) 5 % 3-HHBB(F,F)-F (7-6) 2% 3-HBBXB(F,F)-F (7-32) 4% 5-HB(F)B(F,F)XB(F ,F)-F (7-41) 5% 3-BB(F)B(F,F)XB(F,F)-F (7-47) 4% 4-BB(F)B(F,F )XB(F,F)-F (7-47) 4% 5-BB(F)B(F,F)XB(F,F)-F (7-47) 3% 1.5% by weight in The following compound (1-5-13) was added to the composition.
Figure 02_image199
NI=78.0℃; η=12.1 mPa s; Δn=0.097; Δε=5.5.

[使用例13] 3-HH-V                                  （2-1）                    25% 3-HH-V1                                （2-1）                    10% V-HH-V1                                （2-1）                    9% 3-HHB-1                                     （3-1）                    4% V-HHB-1                                （3-1）                    5% 1-BB(F)B-2V                          （3-6）                    4% 3-HHEH-5                              （3-13）                  3% 1V2-BB-F                              （5-1）                    3% 3-BB(F,F)XB(F,F)-F                （6-97）                  6% 3-HHXB(F,F)-CF3                  （6-100）                 2% 3-GB(F,F)XB(F,F)-F                （6-113）                 4% 3-GB(F)B(F,F)-F                     （6-116）                 4% 3-HHBB(F,F)-F                       （7-6）                    3% 3-BB(F)B(F,F)XB(F,F)-F         （7-47）                  5% 4-BB(F)B(F,F)XB(F,F)-F         （7-47）                  5% 5-BB(F)B(F,F)XB(F,F)-F         （7-47）                  3% 3-GB(F)B(F,F)XB(F,F)-F         （7-57）                  5% 以0.5重量%的比例於所述組成物中添加下述化合物（1-5-17）。

Figure 02_image201
NI=81.5℃；η=13.3 mPa·s；Δn=0.106；Δε=7.3.[Example 13] 3-HH-V (2-1) 25% 3-HH-V1 (2-1) 10% V-HH-V1 (2-1) 9% 3-HHB-1 (3-1 ) 4% V-HHB-1 (3-1) 5% 1-BB(F)B-2V (3-6) 4% 3-HHEH-5 (3-13) 3% 1V2-BB-F (5 -1) 3% 3-BB(F,F)XB(F,F)-F (6-97) 6% 3-HHXB(F,F)-CF3 (6-100) 2% 3-GB(F ,F)XB(F,F)-F (6-113) 4% 3-GB(F)B(F,F)-F (6-116) 4% 3-HHBB(F,F)-F ( 7-6) 3% 3-BB(F)B(F,F)XB(F,F)-F (7-47) 5% 4-BB(F)B(F,F)XB(F,F )-F (7-47) 5% 5-BB(F)B(F,F)XB(F,F)-F (7-47) 3% 3-GB(F)B(F,F)XB (F,F)-F (7-57) 5% The following compound (1-5-17) was added to the composition at a rate of 0.5% by weight.
Figure 02_image201
NI=81.5℃; η=13.3 mPa s; Δn=0.106; Δε=7.3.

[使用例14] 3-HH-V                                  （2-1）                    30% 3-HH-V1                                （2-1）                    10% 3-HHB-1                                     （3-1）                    5% V-HHB-1                                （3-1）                    3% 3-HBB-2                                （3-4）                    6% V2-BB(F)B-1                          （3-6）                    5% 3-HHEH-3                              （3-13）                  3% 3-HHEH-5                              （3-13）                  3% 1V2-BB-F                              （5-1）                    3% 3-BB(F,F)XB(F,F)-F                （6-97）                  4% 3-GB(F,F)XB(F,F)-F                （6-113）                 3% 3-HHBB(F,F)-F                       （7-6）                    3% 3-HBB(F,F)XB(F,F)-F             （7-38）                  3% 3-BB(F)B(F,F)XB(F)-F            （7-46）                  4% 4-BB(F)B(F,F)XB(F,F)-F         （7-47）                  2% 5-BB(F)B(F,F)XB(F,F)-F         （7-47）                  3% 3-GB(F)B(F,F)XB(F,F)-F         （7-57）                  3% 4-GB(F)B(F,F)XB(F,F)-F         （7-57）                  5% 5-GB(F)B(F,F)XB(F,F)-F         （7-57）                  2% 以4重量%的比例於所述組成物中添加下述化合物（1-5-25）。

Figure 02_image203
NI=81.9℃；η=13.5 mPa·s；Δn=0.092；Δε=5.8.[Example 14] 3-HH-V (2-1) 30% 3-HH-V1 (2-1) 10% 3-HHB-1 (3-1) 5% V-HHB-1 (3-1 ) 3% 3-HBB-2 (3-4) 6% V2-BB(F)B-1 (3-6) 5% 3-HHEH-3 (3-13) 3% 3-HHEH-5 (3 -13) 3% 1V2-BB-F (5-1) 3% 3-BB(F,F)XB(F,F)-F (6-97) 4% 3-GB(F,F)XB( F,F)-F (6-113) 3% 3-HHBB(F,F)-F (7-6) 3% 3-HBB(F,F)XB(F,F)-F (7-38 ) 3% 3-BB(F)B(F,F)XB(F)-F (7-46) 4% 4-BB(F)B(F,F)XB(F,F)-F (7 -47) 2% 5-BB(F)B(F,F)XB(F,F)-F (7-47) 3% 3-GB(F)B(F,F)XB(F,F) -F (7-57) 3% 4-GB(F)B(F,F)XB(F,F)-F (7-57) 5% 5-GB(F)B(F,F)XB( F,F)-F (7-57) 2% The following compound (1-5-25) was added to the composition at a ratio of 4% by weight.
Figure 02_image203
NI=81.9℃; η=13.5 mPa s; Δn=0.092; Δε=5.8.

[使用例15] 3-HH-V                                  （2-1）                    30% 3-HH-V1                                （2-1）                    8% 3-HHB-1                                     （3-1）                    4% V-HHB-1                                （3-1）                    5% V2-BB(F)B-1                          （3-6）                    4% 3-HHEH-5                              （3-13）                  4% 3-HHEBH-3                           （4-6）                    3% 1V2-BB-F                              （5-1）                    4% 3-BB(F)B(F,F)-F                     （6-69）                  5% 3-BB(F,F)XB(F,F)-F                （6-97）                  3% 3-HHBB(F,F)-F                       （7-6）                    3% 5-HB(F)B(F,F)XB(F,F)-F         （7-41）                  4% 3-BB(F,F)XB(F)B(F,F)-F         （7-56）                  5% 4-BB(F)B(F,F)XB(F,F)-F         （7-47）                  3% 5-BB(F)B(F,F)XB(F,F)-F         （7-47）                  4% 2-dhBB(F,F)XB(F,F)-F            （7-50）                  3% 3-dhBB(F,F)XB(F,F)-F            （7-50）                  2% 3-GBB(F)B(F,F)-F                  （7-55）                  2% 4-GBB(F)B(F,F)-F                  （7-55）                  4% 以3重量%的比例於所述組成物中添加下述化合物（1-2-6）。

Figure 02_image205
NI=84.6℃；η=19.3 mPa·s；Δn=0.102；Δε=5.6.[Example 15] 3-HH-V (2-1) 30% 3-HH-V1 (2-1) 8% 3-HHB-1 (3-1) 4% V-HHB-1 (3-1) ) 5% V2-BB(F)B-1 (3-6) 4% 3-HHEH-5 (3-13) 4% 3-HHEBH-3 (4-6) 3% 1V2-BB-F (5 -1) 4% 3-BB(F)B(F,F)-F (6-69) 5% 3-BB(F,F)XB(F,F)-F (6-97) 3% 3 -HHBB(F,F)-F (7-6) 3% 5-HB(F)B(F,F)XB(F,F)-F (7-41) 4% 3-BB(F,F )XB(F)B(F,F)-F (7-56) 5% 4-BB(F)B(F,F)XB(F,F)-F (7-47) 3% 5-BB (F)B(F,F)XB(F,F)-F (7-47) 4% 2-dhBB(F,F)XB(F,F)-F (7-50) 3% 3-dhBB (F,F)XB(F,F)-F (7-50) 2% 3-GBB(F)B(F,F)-F (7-55) 2% 4-GBB(F)B(F ,F)-F (7-55) 4% The following compound (1-2-6) was added to the composition at a rate of 3% by weight.
Figure 02_image205
NI=84.6℃; η=19.3 mPa s; Δn=0.102; Δε=5.6.

[使用例16] 3-HH-V                                  （2-1）                    25% 3-HH-V1                                （2-1）                    10% 3-HHB-1                                     （3-1）                    5% V-HHB-1                                （3-1）                    7% V2-BB(F)B-1                          （3-6）                    5% 3-HHEH-5                              （3-13）                  3% 1V2-BB-F                              （5-1）                    5% 3-BB(F)B(F,F)-CF3                 （6-69）                  3% 3-BB(F,F)XB(F,F)-F                （6-97）                  5% 3-HHXB(F,F)-F                      （6-100）                 5% 3-GB(F,F)XB(F,F)-F                （6-113）                 3% 3-GB(F)B(F)-F                       （6-115）                 3% 3-HHBB(F,F)-F                       （7-6）                    2% 5-HB(F)B(F,F)XB(F,F)-F         （7-41）                  5% 3-GB(F)B(F,F)XB(F,F)-F         （7-57）                  3% 3-GBB(F,F)XB(F,F)-F             （7-58）                  4% 4-GBB(F,F)XB(F,F)-F             （7-58）                  2% 5-GBB(F,F)XB(F,F)-F             （7-58）                  2% 3-GB(F)B(F)B(F)-F                 （7-59）                  3% 以1重量%的比例於所述組成物中添加下述化合物（1-2-8）。

Figure 02_image207
NI=83.5℃；η=16.6 mPa·s；Δn=0.098；Δε=6.2. [產業上之可利用性][Example 16] 3-HH-V (2-1) 25% 3-HH-V1 (2-1) 10% 3-HHB-1 (3-1) 5% V-HHB-1 (3-1 ) 7% V2-BB(F)B-1 (3-6) 5% 3-HHEH-5 (3-13) 3% 1V2-BB-F (5-1) 5% 3-BB(F)B (F,F)-CF3 (6-69) 3% 3-BB(F,F)XB(F,F)-F (6-97) 5% 3-HHXB(F,F)-F (6- 100) 5% 3-GB(F,F)XB(F,F)-F (6-113) 3% 3-GB(F)B(F)-F (6-115) 3% 3-HHBB( F,F)-F (7-6) 2% 5-HB(F)B(F,F)XB(F,F)-F (7-41) 5% 3-GB(F)B(F, F)XB(F,F)-F (7-57) 3% 3-GBB(F,F)XB(F,F)-F (7-58) 4% 4-GBB(F,F)XB( F,F)-F (7-58) 2% 5-GBB(F,F)XB(F,F)-F (7-58) 2% 3-GB(F)B(F)B(F) -F (7-59) 3% The following compound (1-2-8) was added to the composition at a rate of 1% by weight.
Figure 02_image207
NI=83.5℃; η=16.6 mPa·s; Δn=0.098; Δε=6.2. [Industrial availability]

包含化合物（1）的液晶組成物可用於液晶投影儀、液晶電視等的顯示元件。The liquid crystal composition containing the compound (1) can be used in display elements such as liquid crystal projectors and liquid crystal televisions.

無none

無none

Figure 108136306-A0101-11-0001-1
Figure 108136306-A0101-11-0002-2
Figure 108136306-A0101-11-0001-1
Figure 108136306-A0101-11-0002-2

Claims (16)

一種化合物，由式(1)表示，
Figure 108136306-A0305-02-0146-1
 式(1)中，R1為氫或碳數1至15的烷基，所述R1中，至少一個-CH2-可經-O-或-S-取代，至少一個-(CH2)2-可經-CH=CH-或-C≡C-取代，至少一個氫可經氟或氯取代；環A1及環A2獨立地為1,2-伸環丙基、1,3-伸環丁基、1,3-伸環戊基、1,4-伸環己基、1,4-伸環庚基、1,4-伸環己烯基、1,4-伸苯基、萘-2,6-二基、十氫萘-2,6-二基、1,2,3,4-四氫萘-2,6-二基、四氫吡喃-2,5-二基、1,3-二噁烷-2,5-二基、嘧啶-2,5-二基、或吡啶-2,5-二基，所述環A1及環A2中，至少一個氫可經氟、氯、碳數1至10的烷基、碳數2至10的烯基、碳數1至9的烷氧基、或碳數2至9的烯氧基取代；a為0、1、2、3、或4；Z1獨立地為單鍵或碳數1至6的伸烷基，所述Z1中，至少一個-CH2-可經-O-、-CO-、-COO-、-OCO-、或-OCOO-取代，至少一個-(CH2)2-可經-CH=CH-或-C≡C-取代，至少一個氫可經氟或氯取代； Sp0、Sp2、Sp3、及Sp4獨立地為單鍵或碳數1至15的伸烷基，所述Sp0、Sp2、Sp3、及Sp4中，至少一個-CH2-可經-O-、-CO-、-COO-、-OCO-、或-OCOO-取代，至少一個-(CH2)2-可經-CH=CH-或-C≡C-取代，至少一個氫可經氟或氯取代；M1、及M2獨立地為氫、氟、氯、碳數1至5的烷基、或者至少一個氫經氟或氯取代的碳數1至5的烷基；R2為碳數1至10的烷基，所述R2中，至少一個-CH2-可經-O-或-S-取代，至少一個-(CH2)2-可經-CH=CH-或-C≡C-取代，至少一個氫可經氟或氯取代；X1獨立地為-OH、-NH2、-OR4、-N(R4)2、-COOH、-SH、或-Si(R4)3；-OR4、-N(R4)2、及-Si(R4)3中，R4為氫或碳數1至10的烷基，所述R4中，至少一個-CH2-可經-O-取代，至少一個-(CH2)2-可經-CH=CH-取代，該些基中，至少一個氫可經氟或氯取代；環A2或Sp0中，至少一個氫經式(1-a)所表示的基取代；
Figure 108136306-A0305-02-0147-2
 式(1-a)中，Sp5為單鍵或碳數1至10的伸烷基，所述Sp5中，至少一個-CH2-可經-O-、-CO-、-COO-、-OCO-、或-OCOO-取代，至少一個 -(CH2)2-可經-CH=CH-或-C≡C-取代，至少一個氫可經氟或氯取代；M3、及M4獨立地為氫、氟、氯、碳數1至5的烷基、或者至少一個氫經氟或氯取代的碳數1至5的烷基；R3為碳數1至10的烷基，所述R3中，至少一個-CH2-可經-O-或-S-取代，至少一個-(CH2)2-可經-CH=CH-或-C≡C-取代，至少一個氫可經氟或氯取代。 A compound represented by formula (1),
Figure 108136306-A0305-02-0146-1
 In formula (1), R 1 is hydrogen or an alkyl group with 1 to 15 carbons, and in said R 1 , at least one -CH 2 - may be substituted by -O- or -S-, and at least one -(CH 2 ) 2 - can be substituted by -CH=CH- or -C≡C-, at least one hydrogen can be substituted by fluorine or chlorine; ring A 1 and ring A 2 are independently 1,2-cyclopropyl, 1,3- Cyclobutylene, 1,3-cyclopentyl, 1,4-cyclohexyl, 1,4-cyclohexyl, 1,4-cyclohexenyl, 1,4-phenylene, naphthalene -2,6-diyl, decalin-2,6-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl, tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, pyrimidine-2,5-diyl, or pyridine-2,5-diyl, in the ring A 1 and ring A 2 , at least one hydrogen can be Fluorine, chlorine, alkyl with 1 to 10 carbons, alkenyl with 2 to 10 carbons, alkoxy with 1 to 9 carbons, or alkenyloxy with 2 to 9 carbons; a is 0, 1, 2, 3, or 4; Z 1 is independently a single bond or an alkylene group with 1 to 6 carbons, and in said Z 1 , at least one -CH 2 - can be passed through -O-, -CO-, -COO- , -OCO-, or -OCOO-, at least one -(CH 2 ) 2 - can be substituted by -CH=CH- or -C≡C-, at least one hydrogen can be substituted by fluorine or chlorine; Sp 0 , Sp 2 , Sp 3 , and Sp 4 are independently a single bond or an alkylene group with 1 to 15 carbons, and in the Sp 0 , Sp 2 , Sp 3 , and Sp 4 , at least one -CH 2 - can be passed through -O- , -CO-, -COO-, -OCO-, or -OCOO-, at least one -(CH 2 ) 2 - can be substituted by -CH=CH- or -C≡C-, at least one hydrogen can be substituted by fluorine or Chlorine substitution; M 1 and M 2 are independently hydrogen, fluorine, chlorine, an alkyl group with 1 to 5 carbons, or an alkyl group with 1 to 5 carbons in which at least one hydrogen is substituted by fluorine or chlorine; R 2 is carbon An alkyl group with the number 1 to 10, in the R2 , at least one -CH 2 - may be substituted by -O- or -S-, and at least one -(CH 2 ) 2 - may be substituted by -CH=CH- or -C ≡C-substituted, at least one hydrogen can be replaced by fluorine or chlorine; X 1 is independently -OH, -NH 2 , -OR 4 , -N(R 4 ) 2 , -COOH, -SH, or -Si(R 4 ) 3 ; in -OR 4 , -N(R 4 ) 2 , and -Si(R 4 ) 3 , R 4 is hydrogen or an alkyl group with 1 to 10 carbons, and in said R 4 , at least one -CH 2 - can be substituted by -O-, at least one -(CH 2 ) 2 - can be substituted by -CH=CH-, in these groups, at least one hydrogen can be substituted by fluorine or chlorine; in ring A 2 or Sp 0 , At least one hydrogen is replaced by a group represented by formula (1-a);
Figure 108136306-A0305-02-0147-2
 In formula (1-a), Sp 5 is a single bond or an alkylene group with 1 to 10 carbons, and in said Sp 5 , at least one -CH 2 - can be passed through -O-, -CO-, -COO-, -OCO-, or -OCOO-substituted, at least one -(CH 2 ) 2 - can be substituted by -CH=CH- or -C≡C-, at least one hydrogen can be substituted by fluorine or chlorine; M 3 , and M 4 independently hydrogen, fluorine, chlorine, an alkyl group with 1 to 5 carbons, or an alkyl group with 1 to 5 carbons in which at least one hydrogen is substituted by fluorine or chlorine; R3 is an alkyl group with 1 to 10 carbons, so In the above R 3 , at least one -CH 2 - may be substituted by -O- or -S-, at least one -(CH 2 ) 2 - may be substituted by -CH=CH- or -C≡C-, and at least one hydrogen may be Substituted by fluorine or chlorine. 如申請專利範圍第1項所述的化合物，其中式(1)中，Z1獨立地為單鍵、-(CH2)2-、-(CH2)4-、-CH=CH-、-C≡C-、-COO-、-OCO-、-CF2O-、-OCF2-、-CH2O-、-OCH2-、或-CF=CF-；環A1及環A2獨立地為1,4-伸環己基、1,4-伸環己烯基、1,4-伸苯基、萘-2,6-二基、四氫吡喃-2,5-二基、1,3-二噁烷-2,5-二基、嘧啶-2,5-二基、或吡啶-2,5-二基，所述環A1及環A2中，至少一個氫可經氟、氯、碳數1至10的烷基、碳數2至10的烯基、碳數1至9的烷氧基、或碳數2至9的烯氧基取代；環A2或Sp0中，至少一個氫經式(1-a)取代。 The compound described in item 1 of the scope of the patent application, wherein in formula (1), Z 1 is independently a single bond, -(CH 2 ) 2 -, -(CH 2 ) 4 -, -CH=CH-, - C≡C-, -COO-, -OCO-, -CF 2 O-, -OCF 2 -, -CH 2 O-, -OCH 2 -, or -CF=CF-; ring A 1 and ring A 2 are independent 1,4-cyclohexylene, 1,4-cyclohexenyl, 1,4-phenylene, naphthalene-2,6-diyl, tetrahydropyran-2,5-diyl, 1 , 3-dioxane-2,5-diyl, pyrimidine-2,5-diyl, or pyridine-2,5-diyl, in the ring A 1 and ring A 2 , at least one hydrogen can be fluorine , chlorine, alkyl with 1 to 10 carbons, alkenyl with 2 to 10 carbons, alkoxy with 1 to 9 carbons, or alkenyloxy with 2 to 9 carbons; Ring A 2 or Sp 0 , at least one hydrogen is replaced by formula (1-a). 如申請專利範圍第1項所述的化合物，由式(1-1)至式(1-8)的任一者表示，
Figure 108136306-A0305-02-0149-3
Figure 108136306-A0305-02-0149-4
Figure 108136306-A0305-02-0149-5
Figure 108136306-A0305-02-0149-6
Figure 108136306-A0305-02-0150-7
 式(1-1)至式(1-8)中，R1為碳數1至15的烷基、碳數2至15的烯基、碳數1至14的烷氧基、或碳數2~14的烯氧基，所述R1中，至少一個氫可經氟取代；環A1至環A5獨立地為1,4-伸環己基、1,4-伸環己烯基、1,4-伸苯基、萘-2,6-二基、四氫吡喃-2,5-二基、或1,3-二噁烷-2,5-二基，所述環A1至環A5中，至少一個氫可經氟、碳數1至10的烷基、碳數2至10的烯基、碳數1至9的烷氧基、或碳數2至9的 烯氧基取代；b至e獨立地為0、1、2、3、或4，該些的合計為1、2、3、或4；Z1至Z4獨立地為單鍵、-(CH2)2-、-CH=CH-、-C≡C-、-COO-、-OCO-、-CF2O-、-OCF2-、-CH2O-、-OCH2-、或-CF=CF-；Sp0至Sp8獨立地為單鍵或碳數1至7的伸烷基，所述Sp0至Sp8中，至少一個-CH2-可經-O-、-COO-、或-OCO-取代，至少一個-(CH2)2-可經-CH=CH-取代，至少一個氫可經氟取代；M1至M10獨立地為氫、氟、碳數1至5的烷基、或至少一個氫經氟取代的碳數1至5的烷基；R2至R6獨立地為碳數1至10的烷基，所述R2至R6中，至少一個-CH2-可經-O-取代；X1獨立地為-OH、-NH2、或-SH。 The compound as described in item 1 of the scope of the patent application, represented by any one of formula (1-1) to formula (1-8),
Figure 108136306-A0305-02-0149-3
Figure 108136306-A0305-02-0149-4
Figure 108136306-A0305-02-0149-5
Figure 108136306-A0305-02-0149-6
Figure 108136306-A0305-02-0150-7
 In formula (1-1) to formula (1-8), R 1 is an alkyl group with a carbon number of 1 to 15, an alkenyl group with a carbon number of 2 to 15, an alkoxy group with a carbon number of 1 to 14, or a carbon number of 2 ~14 alkenyloxy groups, in the R 1 , at least one hydrogen can be substituted by fluorine; ring A 1 to ring A 5 are independently 1,4-cyclohexyl, 1,4-cyclohexenyl, 1 , 4-phenylene, naphthalene-2,6-diyl, tetrahydropyran-2,5-diyl, or 1,3-dioxane-2,5-diyl, the ring A 1 to In ring A5 , at least one hydrogen can be fluorine, alkyl having 1 to 10 carbons, alkenyl having 2 to 10 carbons, alkoxy having 1 to 9 carbons, or alkenyloxy having 2 to 9 carbons Substitution; b to e are independently 0, 1, 2, 3, or 4, and the total of these is 1, 2, 3, or 4; Z 1 to Z 4 are independently single bonds, -(CH 2 ) 2 -, -CH=CH-, -C≡C-, -COO-, -OCO-, -CF 2 O-, -OCF 2 -, -CH 2 O-, -OCH 2 -, or -CF=CF- ; Sp 0 to Sp 8 are independently a single bond or an alkylene group with a carbon number of 1 to 7, and in the Sp 0 to Sp 8 , at least one -CH 2 - can be passed through -O-, -COO-, or -OCO - Substitution, at least one -(CH 2 ) 2 - can be substituted by -CH=CH-, at least one hydrogen can be substituted by fluorine; M 1 to M 10 are independently hydrogen, fluorine, alkyl with 1 to 5 carbons, or an alkyl group with 1 to 5 carbons in which at least one hydrogen is replaced by fluorine; R 2 to R 6 are independently alkyl groups with 1 to 10 carbons, and among the R 2 to R 6 , at least one -CH 2 - can be Substituted by -O-; X 1 is independently -OH, -NH 2 , or -SH. 如申請專利範圍第1項所述的化合物，由式(1-9)至式(1-16)的任一者表示，
Figure 108136306-A0305-02-0152-8
Figure 108136306-A0305-02-0152-9
Figure 108136306-A0305-02-0152-10
Figure 108136306-A0305-02-0152-11
Figure 108136306-A0305-02-0153-12
 式(1-9)至式(1-16)中，R1為碳數1至10的烷基、碳數2至10的烯基、或碳數1至9的烷氧基；環A1至環A5獨立地為1,4-伸環己基、1,4-伸環己烯基、1,4-伸苯基、萘-2,6-二基、四氫吡喃-2,5-二基、或1,3-二噁烷-2,5-二基，所述環A1至環A5中，至少一個氫可經氟、碳數1至5的烷基、碳數2至5的烯基、或碳數1至4的烷氧基取代；b至e獨立地為0、1、2、3、或4，該些的合計為1、2、3、 或4；Z1至Z4獨立地為單鍵、-(CH2)2-、-CH=CH-、-C≡C-、-CH2O-、或-OCH2-；Sp0至Sp8獨立地為單鍵或碳數1至5的伸烷基，所述Sp0至Sp8中，至少一個-CH2-可經-O-取代，至少一個-(CH2)2-可經-CH=CH-取代；M1至M10獨立地為氫、氟、碳數1至5的烷基、或至少一個氫經氟取代的碳數1至5的烷基；R2為碳數1至3的烷基；R3至R6獨立地為碳數1至10的烷基、或碳數1至9的烷氧基。 The compound as described in item 1 of the scope of the patent application, represented by any one of formula (1-9) to formula (1-16),
Figure 108136306-A0305-02-0152-8
Figure 108136306-A0305-02-0152-9
Figure 108136306-A0305-02-0152-10
Figure 108136306-A0305-02-0152-11
Figure 108136306-A0305-02-0153-12
 In formula (1-9) to formula (1-16), R 1 is an alkyl group with 1 to 10 carbons, an alkenyl group with 2 to 10 carbons, or an alkoxy group with 1 to 9 carbons; Ring A 1 To ring A 5 is independently 1,4-cyclohexylene, 1,4-cyclohexene, 1,4-phenylene, naphthalene-2,6-diyl, tetrahydropyran-2,5 -diyl, or 1,3-dioxane-2,5-diyl, in the ring A 1 to ring A 5 , at least one hydrogen can be fluorine, an alkyl group with 1 to 5 carbons, or an alkyl group with 2 carbons Alkenyl to 5, or an alkoxy group with 1 to 4 carbons; b to e are independently 0, 1, 2, 3, or 4, and the total of these is 1, 2, 3, or 4; Z 1 to Z 4 are independently a single bond, -(CH 2 ) 2 -, -CH=CH-, -C≡C-, -CH 2 O-, or -OCH 2 -; Sp 0 to Sp 8 are independently A single bond or an alkylene group with 1 to 5 carbons, in the Sp 0 to Sp 8 , at least one -CH 2 - may be replaced by -O-, and at least one -(CH 2 ) 2 - may be replaced by -CH=CH - Substitution; M 1 to M 10 are independently hydrogen, fluorine, an alkyl group with 1 to 5 carbons, or an alkyl group with 1 to 5 carbons in which at least one hydrogen is substituted by fluorine; R 2 is an alkyl group with 1 to 3 carbons Alkyl; R 3 to R 6 are independently alkyl with 1 to 10 carbons, or alkoxy with 1 to 9 carbons. 如申請專利範圍第1項所述的化合物，由式(1-17)至式(1-53)的任一者表示，
Figure 108136306-A0305-02-0155-13
Figure 108136306-A0305-02-0155-14
Figure 108136306-A0305-02-0155-15
Figure 108136306-A0305-02-0155-16
Figure 108136306-A0305-02-0155-17
Figure 108136306-A0305-02-0155-18
Figure 108136306-A0305-02-0155-19
Figure 108136306-A0305-02-0155-20
Figure 108136306-A0305-02-0155-21
Figure 108136306-A0305-02-0156-22
Figure 108136306-A0305-02-0156-23
Figure 108136306-A0305-02-0156-24
Figure 108136306-A0305-02-0156-25
Figure 108136306-A0305-02-0157-26
Figure 108136306-A0305-02-0157-27
Figure 108136306-A0305-02-0157-28
Figure 108136306-A0305-02-0157-29
Figure 108136306-A0305-02-0157-30
Figure 108136306-A0305-02-0157-31
Figure 108136306-A0305-02-0158-32
Figure 108136306-A0305-02-0158-33
Figure 108136306-A0305-02-0158-34
Figure 108136306-A0305-02-0158-35
Figure 108136306-A0305-02-0158-36
Figure 108136306-A0305-02-0158-37
Figure 108136306-A0305-02-0159-38
Figure 108136306-A0305-02-0159-39
Figure 108136306-A0305-02-0159-40
Figure 108136306-A0305-02-0159-41
Figure 108136306-A0305-02-0159-42
Figure 108136306-A0305-02-0159-43
Figure 108136306-A0305-02-0160-44
Figure 108136306-A0305-02-0160-45
Figure 108136306-A0305-02-0160-46
Figure 108136306-A0305-02-0160-47
Figure 108136306-A0305-02-0160-48
Figure 108136306-A0305-02-0160-49
 式(1-17)至式(1-53)中， R1為碳數1~10的烷基、碳數2~10的烯基、或碳數1~9的烷氧基；Z1至Z3獨立地為單鍵或-(CH2)2-；Sp0、Sp1、Sp2、Sp5、Sp6、及Sp7獨立地為單鍵或碳數1至5的伸烷基，所述Sp0、Sp1、Sp2、Sp5、Sp6、及Sp7中，至少一個-CH2-可經-O-取代；Y1至Y11獨立地為氫、氟、碳數1至5的烷基、碳數2至5的烯基、或碳數1至4的烷氧基；R2為碳數1至10的烷基、或碳數1至9的烷氧基；R3、R4、及R5獨立地為碳數1至3的烷基；M1及M2獨立地為氫、氟、碳數1至5的烷基、或至少一個氫經氟取代的碳數1至5的烷基。 The compound as described in item 1 of the patent claims, represented by any one of formula (1-17) to formula (1-53),
Figure 108136306-A0305-02-0155-13
Figure 108136306-A0305-02-0155-14
Figure 108136306-A0305-02-0155-15
Figure 108136306-A0305-02-0155-16
Figure 108136306-A0305-02-0155-17
Figure 108136306-A0305-02-0155-18
Figure 108136306-A0305-02-0155-19
Figure 108136306-A0305-02-0155-20
Figure 108136306-A0305-02-0155-21
Figure 108136306-A0305-02-0156-22
Figure 108136306-A0305-02-0156-23
Figure 108136306-A0305-02-0156-24
Figure 108136306-A0305-02-0156-25
Figure 108136306-A0305-02-0157-26
Figure 108136306-A0305-02-0157-27
Figure 108136306-A0305-02-0157-28
Figure 108136306-A0305-02-0157-29
Figure 108136306-A0305-02-0157-30
Figure 108136306-A0305-02-0157-31
Figure 108136306-A0305-02-0158-32
Figure 108136306-A0305-02-0158-33
Figure 108136306-A0305-02-0158-34
Figure 108136306-A0305-02-0158-35
Figure 108136306-A0305-02-0158-36
Figure 108136306-A0305-02-0158-37
Figure 108136306-A0305-02-0159-38
Figure 108136306-A0305-02-0159-39
Figure 108136306-A0305-02-0159-40
Figure 108136306-A0305-02-0159-41
Figure 108136306-A0305-02-0159-42
Figure 108136306-A0305-02-0159-43
Figure 108136306-A0305-02-0160-44
Figure 108136306-A0305-02-0160-45
Figure 108136306-A0305-02-0160-46
Figure 108136306-A0305-02-0160-47
Figure 108136306-A0305-02-0160-48
Figure 108136306-A0305-02-0160-49
 In formula (1-17) to formula (1-53), R 1 is an alkyl group with 1 to 10 carbons, an alkenyl group with 2 to 10 carbons, or an alkoxy group with 1 to 9 carbons; Z 1 to Z 3 is independently a single bond or -(CH 2 ) 2 -; Sp 0 , Sp 1 , Sp 2 , Sp 5 , Sp 6 , and Sp 7 are independently a single bond or an alkylene group with 1 to 5 carbons, Among the Sp 0 , Sp 1 , Sp 2 , Sp 5 , Sp 6 , and Sp 7 , at least one -CH 2 - may be substituted by -O-; Y 1 to Y 11 are independently hydrogen, fluorine, and carbon number 1 Alkyl to 5, alkenyl with 2 to 5 carbons, or alkoxy with 1 to 4 carbons; R is an alkyl with 1 to 10 carbons, or alkoxy with 1 to 9 carbons; R 3 , R 4 , and R 5 are independently an alkyl group with 1 to 3 carbons; M 1 and M 2 are independently hydrogen, fluorine, an alkyl group with 1 to 5 carbons, or a carbon with at least one hydrogen replaced by fluorine Alkyl groups numbered 1 to 5. 如申請專利範圍第1項所述的化合物，由式(1-54)至式(1-88)的任一者表示，
Figure 108136306-A0305-02-0162-50
Figure 108136306-A0305-02-0162-51
Figure 108136306-A0305-02-0162-52
Figure 108136306-A0305-02-0162-53
Figure 108136306-A0305-02-0162-54
Figure 108136306-A0305-02-0162-55
Figure 108136306-A0305-02-0162-56
Figure 108136306-A0305-02-0163-57
Figure 108136306-A0305-02-0163-58
Figure 108136306-A0305-02-0163-59
Figure 108136306-A0305-02-0163-60
Figure 108136306-A0305-02-0164-61
Figure 108136306-A0305-02-0164-62
Figure 108136306-A0305-02-0164-63
Figure 108136306-A0305-02-0164-64
Figure 108136306-A0305-02-0164-65
Figure 108136306-A0305-02-0164-66
Figure 108136306-A0305-02-0165-67
Figure 108136306-A0305-02-0165-68
Figure 108136306-A0305-02-0165-69
Figure 108136306-A0305-02-0165-70
Figure 108136306-A0305-02-0165-71
Figure 108136306-A0305-02-0165-72
Figure 108136306-A0305-02-0166-73
Figure 108136306-A0305-02-0166-74
Figure 108136306-A0305-02-0166-75
Figure 108136306-A0305-02-0166-76
Figure 108136306-A0305-02-0166-77
Figure 108136306-A0305-02-0166-78
Figure 108136306-A0305-02-0167-79
Figure 108136306-A0305-02-0167-80
Figure 108136306-A0305-02-0167-81
Figure 108136306-A0305-02-0167-82
Figure 108136306-A0305-02-0167-83
Figure 108136306-A0305-02-0167-84
 式(1-54)至式(1-88)中， R1為碳數1~10的烷基；Z1及Z2獨立地為單鍵或-(CH2)2-；Y1至Y11獨立地為氫、氟、甲基、或乙基；Sp0、Sp1、Sp2、Sp5、Sp6、及Sp7獨立地為單鍵或碳數1至5的伸烷基，所述Sp0、Sp1、Sp2、Sp5、Sp6、及Sp7中，至少一個-CH2-可經-O-取代；R2為碳數1~10的烷基；M1及M2獨立地為氫、氟、碳數1至5的烷基、或至少一個氫經氟取代的碳數1至5的烷基。 The compound as described in item 1 of the patent claims, represented by any one of formula (1-54) to formula (1-88),
Figure 108136306-A0305-02-0162-50
Figure 108136306-A0305-02-0162-51
Figure 108136306-A0305-02-0162-52
Figure 108136306-A0305-02-0162-53
Figure 108136306-A0305-02-0162-54
Figure 108136306-A0305-02-0162-55
Figure 108136306-A0305-02-0162-56
Figure 108136306-A0305-02-0163-57
Figure 108136306-A0305-02-0163-58
Figure 108136306-A0305-02-0163-59
Figure 108136306-A0305-02-0163-60
Figure 108136306-A0305-02-0164-61
Figure 108136306-A0305-02-0164-62
Figure 108136306-A0305-02-0164-63
Figure 108136306-A0305-02-0164-64
Figure 108136306-A0305-02-0164-65
Figure 108136306-A0305-02-0164-66
Figure 108136306-A0305-02-0165-67
Figure 108136306-A0305-02-0165-68
Figure 108136306-A0305-02-0165-69
Figure 108136306-A0305-02-0165-70
Figure 108136306-A0305-02-0165-71
Figure 108136306-A0305-02-0165-72
Figure 108136306-A0305-02-0166-73
Figure 108136306-A0305-02-0166-74
Figure 108136306-A0305-02-0166-75
Figure 108136306-A0305-02-0166-76
Figure 108136306-A0305-02-0166-77
Figure 108136306-A0305-02-0166-78
Figure 108136306-A0305-02-0167-79
Figure 108136306-A0305-02-0167-80
Figure 108136306-A0305-02-0167-81
Figure 108136306-A0305-02-0167-82
Figure 108136306-A0305-02-0167-83
Figure 108136306-A0305-02-0167-84
 In formula (1-54) to formula (1-88), R 1 is an alkyl group with 1 to 10 carbons; Z 1 and Z 2 are independently a single bond or -(CH 2 ) 2 -; Y 1 to Y 11 is independently hydrogen, fluorine, methyl, or ethyl; Sp 0 , Sp 1 , Sp 2 , Sp 5 , Sp 6 , and Sp 7 are independently single bonds or alkylene groups with 1 to 5 carbons, so Among Sp 0 , Sp 1 , Sp 2 , Sp 5 , Sp 6 , and Sp 7 , at least one -CH 2 - can be substituted by -O-; R 2 is an alkyl group with 1 to 10 carbons; M 1 and M 2 is independently hydrogen, fluorine, an alkyl group having 1 to 5 carbons, or an alkyl group having 1 to 5 carbons in which at least one hydrogen is replaced by fluorine. 一種液晶組成物，含有如申請專利範圍第1項所述的化合物的至少一種。 A liquid crystal composition containing at least one compound as described in item 1 of the patent application. 如申請專利範圍第7項所述的液晶組成物，含有選自式(2)至式(4)所表示的化合物的群組中的至少一種化合物，
Figure 108136306-A0305-02-0168-85
Figure 108136306-A0305-02-0168-86
Figure 108136306-A0305-02-0168-87
 式(2)至式(4)中，R11及R12獨立地為碳數1至10的烷基或碳數2至10的烯基，所述R11及R12中，至少一個-CH2-可經-O-取代，至少一個氫可經氟取代； 環B1、環B2、環B3、及環B4獨立地為1,4-伸環己基、1,4-伸苯基、2-氟-1,4-伸苯基、2,5-二氟-1,4-伸苯基、或嘧啶-2,5-二基；Z11、Z12、及Z13獨立地為單鍵、-COO-、-CH2CH2-、-CH=CH-、或-C≡C-。 The liquid crystal composition as described in item 7 of the scope of the patent application, comprising at least one compound selected from the group of compounds represented by formula (2) to formula (4),
Figure 108136306-A0305-02-0168-85
Figure 108136306-A0305-02-0168-86
Figure 108136306-A0305-02-0168-87
 In formula (2) to formula (4), R 11 and R 12 are independently an alkyl group with 1 to 10 carbons or an alkenyl group with 2 to 10 carbons, and among the R 11 and R 12 , at least one -CH 2 -can be substituted by -O-, at least one hydrogen can be substituted by fluorine; ring B 1 , ring B 2 , ring B 3 , and ring B 4 are independently 1,4-cyclohexyl, 1,4-phenylene Base, 2-fluoro-1,4-phenylene, 2,5-difluoro-1,4-phenylene, or pyrimidine-2,5-diyl; Z 11 , Z 12 , and Z 13 independently is a single bond, -COO-, -CH 2 CH 2 -, -CH=CH-, or -C≡C-. 如申請專利範圍第7項所述的液晶組成物，含有選自式(5)至式(7)所表示的化合物的群組中的至少一種化合物，
Figure 108136306-A0305-02-0169-88
 式(5)至式(7)中，R13為碳數1至10的烷基或碳數2至10的烯基，所述R13中，至少一個-CH2-可經-O-取代，至少一個氫可經氟取代；X11為氟、氯、-OCF3、-OCHF2、-CF3、-CHF2、-CH2F、-OCF2CHF2、或-OCF2CHFCF3；環C1、環C2、及環C3獨立地為1,4-伸環己基、1,4-伸苯基、四氫吡喃-2,5-二基、1,3-二噁烷-2,5-二基、嘧啶-2,5-二基、或至少一個氫經氟取代的1,4-伸苯基；Z14、Z15、及Z16獨立地為單鍵、-COO-、-OCO-、-CH2O-、 -OCH2-、-CF2O-、-OCF2-、-CH2CH2-、-CH=CH-、-C≡C-、或-(CH2)4-；L11及L12獨立地為氫或氟。 The liquid crystal composition as described in claim 7 of the patent application, comprising at least one compound selected from the group of compounds represented by formula (5) to formula (7),
Figure 108136306-A0305-02-0169-88
 In formulas (5) to (7), R 13 is an alkyl group with 1 to 10 carbons or an alkenyl group with 2 to 10 carbons, and in said R 13 , at least one -CH 2 - may be substituted by -O- , at least one hydrogen may be substituted by fluorine; X 11 is fluorine, chlorine, -OCF 3 , -OCHF 2 , -CF 3 , -CHF 2 , -CH 2 F, -OCF 2 CHF 2 , or -OCF 2 CHFCF 3 ; Ring C 1 , Ring C 2 , and Ring C 3 are independently 1,4-cyclohexylene, 1,4-phenylene, tetrahydropyran-2,5-diyl, 1,3-dioxane -2,5-diyl, pyrimidine-2,5-diyl, or 1,4-phenylene with at least one hydrogen substituted by fluorine; Z 14 , Z 15 , and Z 16 are independently single bonds, -COO -, -OCO-, -CH 2 O-, -OCH 2 -, -CF 2 O-, -OCF 2 -, -CH 2 CH 2 -, -CH=CH-, -C≡C-, or -( CH 2 ) 4 -; L 11 and L 12 are independently hydrogen or fluorine. 如申請專利範圍第7項所述的液晶組成物，含有選自式(8)所表示的化合物的群組中的至少一種化合物，
Figure 108136306-A0305-02-0170-89
 式(8)中，R14為碳數1至10的烷基或碳數2至10的烯基，所述R14中，至少一個-CH2-可經-O-取代，至少一個氫可經氟取代；X12為-C≡N或-C≡C-C≡N；環D1為1,4-伸環己基、1,4-伸苯基、四氫吡喃-2,5-二基、1,3-二噁烷-2,5-二基、嘧啶-2,5-二基、或至少一個氫經氟取代的1,4-伸苯基；Z17為單鍵、-COO-、-OCO-、-CH2O-、-OCH2-、-CF2O-、-OCF2-、-CH2CH2-、或-C≡C-；L13及L14獨立地為氫或氟；i為1、2、3、或4。 The liquid crystal composition as described in claim 7 of the patent application, containing at least one compound selected from the group of compounds represented by formula (8),
Figure 108136306-A0305-02-0170-89
 In formula (8), R 14 is an alkyl group with 1 to 10 carbons or an alkenyl group with 2 to 10 carbons, and in said R 14 , at least one -CH 2 - may be substituted by -O-, and at least one hydrogen may be Substituted by fluorine; X 12 is -C≡N or -C≡CC≡N; Ring D 1 is 1,4-cyclohexyl, 1,4-phenylene, tetrahydropyran-2,5-diyl , 1,3-dioxane-2,5-diyl, pyrimidine-2,5-diyl, or 1,4-phenylene with at least one hydrogen substituted by fluorine; Z 17 is a single bond, -COO- , -OCO-, -CH 2 O-, -OCH 2 -, -CF 2 O-, -OCF 2 -, -CH 2 CH 2 -, or -C≡C-; L 13 and L 14 are independently hydrogen or fluorine; i is 1, 2, 3, or 4. 如申請專利範圍第7項所述的液晶組成物，含有選自式(11)至式(19)所表示的化合物的群組中的至少一種化合物，
Figure 108136306-A0305-02-0171-90
 式(11)至式(19)中，R15、R16、及R17獨立地為碳數1至10的烷基或碳數2至10的烯基，所述R15、R16、及R17中，至少一個-CH2-可經-O-取代，該些基中，至少一個氫可經氟取代，而且R17亦可為氫或氟；環E1、環E2、環E3、及環E4獨立地為1,4-伸環己基、1,4- 伸環己烯基、1,4-伸苯基、四氫吡喃-2,5-二基、十氫萘-2,6-二基、或至少一個氫經氟取代的1,4-伸苯基；環E5及環E6獨立地為1,4-伸環己基、1,4-伸環己烯基、1,4-伸苯基、四氫吡喃-2,5-二基、或十氫萘-2,6-二基；Z18、Z19、Z20、及Z21獨立地為單鍵、-COO-、-OCO-、-CH2O-、-OCH2-、-CF2O-、-OCF2-、-CH2CH2-、-CF2OCH2CH2-、或-OCF2CH2CH2-；L15及L16獨立地為氟或氯；S11為氫或甲基；X為-CHF-或-CF2-；j、k、m、n、p、q、r、及s獨立地為0或1，k、m、n、及p的和為1或2，q、r、及s的和為0、1、2、或3，t為1、2、或3。 The liquid crystal composition as described in claim 7 of the patent application, comprising at least one compound selected from the group of compounds represented by formula (11) to formula (19),
Figure 108136306-A0305-02-0171-90
 In formula (11) to formula (19), R 15 , R 16 , and R 17 are independently an alkyl group with 1 to 10 carbons or an alkenyl group with 2 to 10 carbons, and the R 15 , R 16 , and In R 17 , at least one -CH 2 - may be substituted by -O-, in these groups, at least one hydrogen may be substituted by fluorine, and R 17 may also be hydrogen or fluorine; ring E 1 , ring E 2 , ring E 3 , and Ring E4 are independently 1,4-cyclohexylene, 1,4-cyclohexenyl, 1,4-phenylene, tetrahydropyran-2,5-diyl, decahydronaphthalene -2,6-diyl, or 1,4-phenylene with at least one hydrogen replaced by fluorine; ring E 5 and ring E 6 are independently 1,4-cyclohexylene, 1,4-cyclohexene 1,4-phenylene, tetrahydropyran-2,5-diyl, or decalin-2,6-diyl; Z 18 , Z 19 , Z 20 , and Z 21 are independently a single bond, -COO-, -OCO-, -CH 2 O-, -OCH 2 -, -CF 2 O-, -OCF 2 - , -CH 2 CH 2 -, -CF 2 OCH 2 CH 2 -, or - OCF 2 CH 2 CH 2 -; L 15 and L 16 are independently fluorine or chlorine; S 11 is hydrogen or methyl; X is -CHF- or -CF 2 -; j, k, m, n, p, q , r, and s are independently 0 or 1, the sum of k, m, n, and p is 1 or 2, the sum of q, r, and s is 0, 1, 2, or 3, and t is 1, 2 , or 3. 如申請專利範圍第7項所述的液晶組成物，含有式(1)所表示的化合物以外的式(20)所表示的至少一種聚合性化合物，
Figure 108136306-A0305-02-0172-91
 式(20)中，環F及環I獨立地為環己基、環己烯基、苯基、1-萘基、2-萘基、四氫吡喃-2-基、1,3-二噁烷-2-基、嘧啶-2-基、或吡啶-2-基， 所述環F及環I中，至少一個氫可經鹵素、碳數1至12的烷基、碳數1至12的烷氧基、或至少一個氫經鹵素取代的碳數1至12的烷基取代；環G為1,4-伸環己基、1,4-伸環己烯基、1,4-伸苯基、萘-1,2-二基、萘-1,3-二基、萘-1,4-二基、萘-1,5-二基、萘-1,6-二基、萘-1,7-二基、萘、1,8-二基、萘-2,3-二基、萘-2,6-二基、萘-2,7-二基、菲-2,7-二基、四氫吡喃-2,5-二基、1,3-二噁烷-2,5-二基、嘧啶-2,5-二基、或吡啶-2,5-二基，所述環G中，至少一個氫可經鹵素、碳數1至12的烷基、碳數1至12的烷氧基、或至少一個氫經鹵素取代的碳數1至12的烷基取代；Z22及Z23獨立地為單鍵或碳數1至10的伸烷基，所述Z22及Z23中，至少一個-CH2-可經-O-、-CO-、-COO-、或-OCO-取代，至少一個-CH2CH2-可經-CH=CH-、-C(CH3)=CH-、-CH=C(CH3)-、或-C(CH3)=C(CH3)-取代，至少一個氫可經氟或氯取代；P11、P12、及P13獨立地為聚合性基；Sp11、Sp12、及Sp13獨立地為單鍵或碳數1至10的伸烷基，所述Sp11、Sp12、及Sp13中，至少一個-CH3-可經-O-、-COO-、-OCO-、或-OCOO-取代，至少一個-CH2CH2-可經-CH=CH-或-C≡C-取代，至少一個氫可經氟或氯取代；u為0、1、或2；f、g、及h獨立地為0、1、2、3、或4，而且f、g、及h的和為1以上。 The liquid crystal composition as described in claim 7, comprising at least one polymerizable compound represented by formula (20) other than the compound represented by formula (1),
Figure 108136306-A0305-02-0172-91
 In formula (20), Ring F and Ring I are independently cyclohexyl, cyclohexenyl, phenyl, 1-naphthyl, 2-naphthyl, tetrahydropyran-2-yl, 1,3-dioxin Alkyl-2-yl, pyrimidin-2-yl, or pyridin-2-yl, in the ring F and ring I, at least one hydrogen can be replaced by halogen, alkyl with 1 to 12 carbons, or alkyl with 1 to 12 carbons Alkoxy, or at least one hydrogen substituted by a halogen-substituted alkyl group with 1 to 12 carbons; ring G is 1,4-cyclohexylene, 1,4-cyclohexenyl, 1,4-phenylene , Naphthalene-1,2-diyl, naphthalene-1,3-diyl, naphthalene-1,4-diyl, naphthalene-1,5-diyl, naphthalene-1,6-diyl, naphthalene-1, 7-diyl, naphthalene, 1,8-diyl, naphthalene-2,3-diyl, naphthalene-2,6-diyl, naphthalene-2,7-diyl, phenanthrene-2,7-diyl, Tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, pyrimidine-2,5-diyl, or pyridine-2,5-diyl, the ring G In, at least one hydrogen may be substituted by halogen, alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, or alkyl having 1 to 12 carbons substituted by halogen at least one hydrogen; Z 22 and Z 23 is independently a single bond or an alkylene group with 1 to 10 carbons, and among Z 22 and Z 23 , at least one -CH 2 - can be passed through -O-, -CO-, -COO-, or -OCO- Substitution, at least one -CH 2 CH 2 - can be via -CH=CH-, -C(CH 3 )=CH-, -CH=C(CH 3 )-, or -C(CH 3 )=C(CH 3 )-substituted, at least one hydrogen can be replaced by fluorine or chlorine; P 11 , P 12 , and P 13 are independently polymerizable groups; Sp 11 , Sp 12 , and Sp 13 are independently single bonds or carbon numbers 1 to 10 In the Sp 11 , Sp 12 , and Sp 13 , at least one -CH 3 - may be substituted by -O-, -COO-, -OCO-, or -OCOO-, and at least one -CH 2 CH 2 - can be substituted by -CH=CH- or -C≡C-, at least one hydrogen can be substituted by fluorine or chlorine; u is 0, 1, or 2; f, g, and h are independently 0, 1, 2 , 3, or 4, and the sum of f, g, and h is 1 or more. 如申請專利範圍第12項所述的液晶組成物，其中式(20)中，P11、P12、及P13獨立地為選自式(P-1)至式(P-5)所表示的聚合性基的群組中的基，
Figure 108136306-A0305-02-0174-92
 式(P-1)至式(P-5)中，M11、M12、及M13獨立地為氫、氟、碳數1至5的烷基、或至少一個氫經鹵素取代的碳數1至5的烷基。 The liquid crystal composition as described in item 12 of the scope of the patent application, wherein in formula (20), P 11 , P 12 , and P 13 are independently represented by formula (P-1) to formula (P-5) A group in the group of polymeric groups of ,
Figure 108136306-A0305-02-0174-92
 In formula (P-1) to formula (P-5), M 11 , M 12 , and M 13 are independently hydrogen, fluorine, an alkyl group with 1 to 5 carbons, or a carbon number in which at least one hydrogen is replaced by a halogen 1 to 5 alkyl. 如申請專利範圍第12項所述的液晶組成物，其中式(20)所表示的聚合性化合物為選自式(20-1)至式(20-7)所表示的聚合性化合物的群組中的至少一種化合物，
Figure 108136306-A0305-02-0175-93
Figure 108136306-A0305-02-0175-94
Figure 108136306-A0305-02-0175-95
Figure 108136306-A0305-02-0175-96
Figure 108136306-A0305-02-0175-97
Figure 108136306-A0305-02-0175-98
Figure 108136306-A0305-02-0175-99
 式(20-1)至式(20-7)中， L31、L32、L33、L34、L35、L36、L37、及L38獨立地為氫、氟、或甲基；Sp11、Sp12、及Sp13獨立地為單鍵或碳數1至10的伸烷基，所述Sp11、Sp12、及Sp13中，至少一個-CH2-可經-O-、-COO-、-OCO-、或-OCOO-取代，至少一個-CH2CH2-可經-CH=CH-或-C≡C-取代，至少一個氫可經氟或氯取代；P11、P12、及P13獨立地為選自式(P-1)至式(P-3)所表示的聚合性基的群組中的基；
Figure 108136306-A0305-02-0176-100
 式(P-1)至式(P-3)中，M11、M12、及M13獨立地為氫、氟、碳數1至5的烷基、或至少一個氫經鹵素取代的碳數1至5的烷基。 The liquid crystal composition as described in claim 12, wherein the polymerizable compound represented by formula (20) is selected from the group of polymerizable compounds represented by formula (20-1) to formula (20-7) at least one compound in
Figure 108136306-A0305-02-0175-93
Figure 108136306-A0305-02-0175-94
Figure 108136306-A0305-02-0175-95
Figure 108136306-A0305-02-0175-96
Figure 108136306-A0305-02-0175-97
Figure 108136306-A0305-02-0175-98
Figure 108136306-A0305-02-0175-99
 In formula (20-1) to formula (20-7), L 31 , L 32 , L 33 , L 34 , L 35 , L 36 , L 37 , and L 38 are independently hydrogen, fluorine, or methyl; Sp 11 , Sp 12 , and Sp 13 are independently a single bond or an alkylene group with 1 to 10 carbons, and in the Sp 11 , Sp 12 , and Sp 13 , at least one -CH 2 - can be passed through -O-, -COO-, -OCO-, or -OCOO-substituted, at least one -CH 2 CH 2 - can be substituted by -CH=CH- or -C≡C-, at least one hydrogen can be substituted by fluorine or chlorine; P 11 , P 12 and P 13 are independently selected from the group of polymerizable groups represented by formula (P-1) to formula (P-3);
Figure 108136306-A0305-02-0176-100
 In formula (P-1) to formula (P-3), M 11 , M 12 , and M 13 are independently hydrogen, fluorine, an alkyl group with 1 to 5 carbons, or a carbon number in which at least one hydrogen is replaced by a halogen 1 to 5 alkyl. 如申請專利範圍第7項所述的液晶組成物，含有選自與式(1)或式(20)所表示的化合物不同的聚合性化合物、聚合起始劑、聚合抑制劑、光學活性化合物、抗氧化劑、紫外線吸收劑、光穩定劑、熱穩定劑、色素、及消泡劑的群組中的至少一種，
Figure 108136306-A0305-02-0177-101
 式(20)中，環F及環I獨立地為環己基、環己烯基、苯基、1-萘基、2-萘基、四氫吡喃-2-基、1,3-二噁烷-2-基、嘧啶-2-基、或吡啶-2-基，所述環F及環I中，至少一個氫可經鹵素、碳數1至12的烷基、碳數1至12的烷氧基、或至少一個氫經鹵素取代的碳數1至12的烷基取代；環G為1,4-伸環己基、1,4-伸環己烯基、1,4-伸苯基、萘-1,2-二基、萘、1,3-二基、萘-1,4-二基、萘-1,5-二基、萘-1,6-二基、萘-1,7-二基、萘、1,8-二基、萘-2,3-二基、萘-2,6-二基、萘-2,7-二基、菲-2,7-二基、四氫吡喃-2,5-二基、1,3-二噁烷-2,5-二基、嘧啶-2,5-二基、或吡啶-2,5-二基，所述環G中，至少一個氫可經鹵素、碳數1至12的烷基、碳數1至12的烷氧基、或至少一個氫經鹵素取代的碳數1至12的烷基取代；Z22及Z23獨立地為單鍵或碳數1至10的伸烷基，所述Z22及Z23中，至少一個-CH2-可經-O-、-CO-、-COO-、或-OCO-取代，至少一個-CH2CH2-可經-CH=CH-、-C(CH3)=CH-、-CH=C(CH3)-、或-C(CH3)=C(CH3)-取代，至少一個氫可經氟或氯取代；P11、P12、及P13獨立地為聚合性基； Sp11、Sp12、及Sp13獨立地為單鍵或碳數1至10的伸烷基，所述Sp11、Sp12、及Sp13中，至少一個-CH2-可經-O-、-COO-、-OCO-、或-OCOO-取代，至少一個-CH2CH2-可經-CH=CH-或-C≡C-取代，至少一個氫可經氟或氯取代；u為0、1、或2；f、g、及h獨立地為0、1、2、3、或4，而且f、g、及h的和為1以上。 The liquid crystal composition according to Claim 7 of the patent application, which contains a polymerizable compound different from the compound represented by formula (1) or formula (20), a polymerization initiator, a polymerization inhibitor, an optically active compound, At least one of the group of antioxidants, ultraviolet absorbers, light stabilizers, heat stabilizers, pigments, and defoamers,
Figure 108136306-A0305-02-0177-101
 In formula (20), Ring F and Ring I are independently cyclohexyl, cyclohexenyl, phenyl, 1-naphthyl, 2-naphthyl, tetrahydropyran-2-yl, 1,3-dioxin Alkyl-2-yl, pyrimidin-2-yl, or pyridin-2-yl, in the ring F and ring I, at least one hydrogen can be replaced by halogen, alkyl with 1 to 12 carbons, or alkyl with 1 to 12 carbons Alkoxy, or at least one hydrogen substituted by a halogen-substituted alkyl group with 1 to 12 carbons; ring G is 1,4-cyclohexylene, 1,4-cyclohexenyl, 1,4-phenylene , Naphthalene-1,2-diyl, naphthalene, 1,3-diyl, naphthalene-1,4-diyl, naphthalene-1,5-diyl, naphthalene-1,6-diyl, naphthalene-1, 7-diyl, naphthalene, 1,8-diyl, naphthalene-2,3-diyl, naphthalene-2,6-diyl, naphthalene-2,7-diyl, phenanthrene-2,7-diyl, Tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, pyrimidine-2,5-diyl, or pyridine-2,5-diyl, the ring G In, at least one hydrogen may be substituted by halogen, alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, or alkyl having 1 to 12 carbons substituted by halogen at least one hydrogen; Z 22 and Z 23 is independently a single bond or an alkylene group with 1 to 10 carbons, and among Z 22 and Z 23 , at least one -CH 2 - can be passed through -O-, -CO-, -COO-, or -OCO- Substitution, at least one -CH 2 CH 2 - can be via -CH=CH-, -C(CH 3 )=CH-, -CH=C(CH 3 )-, or -C(CH 3 )=C(CH 3 )-substituted, at least one hydrogen can be substituted by fluorine or chlorine; P 11 , P 12 , and P 13 are independently polymerizable groups; Sp 11 , Sp 12 , and Sp 13 are independently single bonds or carbon numbers 1 to 10 In the Sp 11 , Sp 12 , and Sp 13 , at least one -CH 2 - may be substituted by -O-, -COO-, -OCO-, or -OCOO-, and at least one -CH 2 CH 2 - can be substituted by -CH=CH- or -C≡C-, at least one hydrogen can be substituted by fluorine or chlorine; u is 0, 1, or 2; f, g, and h are independently 0, 1, 2 , 3, or 4, and the sum of f, g, and h is 1 or more. 一種液晶顯示元件，含有選自由如申請專利範圍第7項所述的液晶組成物、及如申請專利範圍第7項所述的液晶組成物的至少一部分進行聚合而成者所組成的群組中的至少一種。A liquid crystal display element, comprising a liquid crystal composition as described in item 7 of the patent application, and a group formed by polymerizing at least a part of the liquid crystal composition as described in item 7 of the patent application at least one of .
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