TW202214826A - Thiophene-containing liquid crystal compound, preparation method therefor and use thereof - Google Patents

Thiophene-containing liquid crystal compound, preparation method therefor and use thereof Download PDF

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TW202214826A
TW202214826A TW110136096A TW110136096A TW202214826A TW 202214826 A TW202214826 A TW 202214826A TW 110136096 A TW110136096 A TW 110136096A TW 110136096 A TW110136096 A TW 110136096A TW 202214826 A TW202214826 A TW 202214826A
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thiophene
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朱波
戴雄
邊坤
程友文
呂永清
王靜
王學濤
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大陸商北京八億時空液晶科技股份有限公司
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Abstract

The present invention belongs to the technical field of liquid crystal materials, and specifically relates to a thiophene-containing liquid crystal compound, a preparation method therefor and the use thereof. The thiophene-containing liquid crystal compound has a structure as shown in general formula (I), and has high optical anisotropy and low rotational viscosity, such that the response time is improved.

Description

一種含噻吩的液晶化合物及其製備方法和應用 A kind of liquid crystal compound containing thiophene and its preparation method and application

本發明屬於液晶材料技術領域，具體涉及一種含噻吩的液晶化合物及其製備方法和應用。 The invention belongs to the technical field of liquid crystal materials, and particularly relates to a thiophene-containing liquid crystal compound and a preparation method and application thereof.

目前，液晶在資訊顯示領域得到廣泛應用，同時在光通訊中的應用也取得了一定的進展(S.T.Wu，D.K.Yang.Reflective Liquid Crystal Displays.Wiley，2001)。近幾年，液晶化合物的應用領域已經顯著拓寬到各類顯示器件、電光器件、電子元件、感測器等。為此，已經提出許多不同的結構，特別是在向列型液晶領域，向列型液晶化合物迄今已經在平板顯示器中得到最為廣泛的應用。特別是用於TFT有源矩陣的系統中。 At present, liquid crystals are widely used in the field of information display, and some progress has also been made in the application of optical communication (S.T.Wu, D.K.Yang.Reflective Liquid Crystal Displays.Wiley, 2001). In recent years, the application fields of liquid crystal compounds have been significantly expanded to various display devices, electro-optical devices, electronic components, sensors, and the like. To this end, many different structures have been proposed, especially in the field of nematic liquid crystals, which have so far been the most widely used in flat panel displays. Especially used in TFT active matrix systems.

彩色顯示大多採用有源矩陣顯示方式。TFT-LCD已經廣泛用於直視型電視、大螢幕投影電視、電腦終端顯示和某些軍用儀錶顯示，相信TFT-LCD技術具有更為廣闊的應用前景。 Most of the color display adopts the active matrix display method. TFT-LCD has been widely used in direct-view TV, large-screen projection TV, computer terminal display and some military instrument display. It is believed that TFT-LCD technology has a broader application prospect.

目前，TFT-LCD產品技術已經成熟，成功地解決了視角、解析度、色飽和度和亮度等技術難題，其顯示性能已經接近或超過CRT顯示器。大尺寸和中小尺寸TFT-LCD顯示器在各自的領域已逐漸佔據平板顯示器的主流地 位。但是因受液晶材料本身的限制，TFT-LCD仍然存在著回應不夠快，電壓不夠低，電荷保持率不夠高等諸多缺陷。 At present, TFT-LCD product technology has matured, successfully solved technical problems such as viewing angle, resolution, color saturation and brightness, and its display performance has approached or exceeded CRT displays. Large size and small and medium size TFT-LCD displays have gradually occupied the mainstream of flat panel displays in their respective fields. bit. However, due to the limitation of the liquid crystal material itself, TFT-LCD still has many defects such as insufficient response, low voltage, and insufficient charge retention.

對於液晶介質來說，需要快速的回應時間，減少液晶的厚度可以縮短反應時間，這就需要高的光學介電常數△n以保證足夠的光延遲值d*△n，然而有高的光學介電常數△n的液晶一般具有高的旋轉粘度，又導致回應時間變長。 For the liquid crystal medium, a fast response time is required. Reducing the thickness of the liquid crystal can shorten the response time, which requires a high optical dielectric constant Δn to ensure sufficient optical retardation value d*Δn. However, there is a high optical dielectric constant. The liquid crystal with the electric constant Δn generally has a high rotational viscosity, which in turn leads to a longer response time.

因此尋找低粘度、高光學各向異性的單晶化合物尤為重要。 Therefore, it is particularly important to find single crystal compounds with low viscosity and high optical anisotropy.

本發明的第一目的是提供一種新型的含噻吩的液晶化合物，該化合物具有較高的光學各向異性和低的旋轉粘度，改善回應時間。 The first object of the present invention is to provide a novel thiophene-containing liquid crystal compound, which has high optical anisotropy and low rotational viscosity, and improves response time.

所述含噻吩的液晶化合物具有如通式(I)所示的結構： The thiophene-containing liquid crystal compound has a structure represented by the general formula (I):

Figure 110136096-A0101-12-0002-2
Figure 110136096-A0101-12-0002-2

式中， In the formula,

R1表示-H、-Cl、-F、-CN、-OCN、-OCF3、-CF3、-CHF2、-CH2F、-OCHF2、-OCF=CF2，-OCF2CF3，-SCN、-NCS、-SF5、C1-C15的烷基、C1-C15的烷氧基、C2-C15的烯基或C2-C15的烯氧基，其中所述C1-C15的烷基、C1-C15的烷氧基、C2-C15的烯基或C2-C15的烯氧基中的一個或多個氫可任選地被氟或氯取代，且一個或多個不相鄰的-CH2-可彼此獨立地被-CH=CH-、-C≡C-、-COO-、-OOC-、-O-或-S-取代； R 1 represents -H, -Cl, -F, -CN, -OCN, -OCF 3 , -CF 3 , -CHF 2 , -CH 2 F, -OCHF 2 , -OCF=CF 2 , -OCF 2 CF 3 , -SCN, -NCS, -SF 5 , C 1 -C 15 alkyl, C 1 -C 15 alkoxy, C 2 -C 15 alkenyl or C 2 -C 15 alkenyloxy, wherein One or more hydrogens in the C 1 -C 15 alkyl, C 1 -C 15 alkoxy, C 2 -C 15 alkenyl or C 2 -C 15 alkenyloxy may optionally be substituted by fluorine or chlorine, and one or more non-adjacent -CH 2 - may be independently of each other by -CH=CH-, -C≡C-, -COO-, -OOC-, -O- or -S -replace;

R2表示-H、C1-C15的烷基、C1-C15的烷氧基、C2-C15的烯基或C2-C15的烯氧基，其中所述C1-C15的烷基、C1-C15的烷氧基、C2-C15的烯基或C2-C15的烯氧基中的一個或多個氫可任選地被氟或氯取代，且一個或多個不相鄰的-CH2-可彼此獨立地被-CH=CH-、-C≡C-、-COO-、-OOC-、-O-或-S-取代； R2 represents -H, C1-C15 alkyl, C1-C15 alkoxy, C2-C15 alkenyl or C2-C15 alkenyl, wherein the C1-C15 alkyl, C1-C15 alkane One or more hydrogens in oxy, C2-C15 alkenyl or C2-C15 alkenyloxy may be optionally substituted by fluorine or chlorine, and one or more non-adjacent -CH2- may be independent of each other replaced by -CH=CH-, -C≡C-, -COO-, -OOC-, -O- or -S-;

A1代表單鍵或下列基團中的一種： A1 represents a single bond or one of the following groups:

Figure 110136096-A0101-12-0003-3
Figure 110136096-A0101-12-0003-3

A2代表單鍵或下列基團中的一種： A2 represents a single bond or one of the following groups:

Figure 110136096-A0101-12-0003-4
Figure 110136096-A0101-12-0003-4

Z1、Z2各自獨立地表示單鍵、-CH2-、-CH2-CH2-、-(CH2)3-、-(CH2)4-、-CH=CH-、-C≡C-、-COO-、-OOC-、-OCH2-、-CH2O-、-CF2O-、-OCF2-、-CF2CH2-、-CH2CF2-、-C2F4-或-CF=CF-。 Z1 and Z2 each independently represent a single bond, -CH2-, -CH2-CH2-, -(CH2)3-, -(CH2)4-, -CH=CH-, -C≡C-, -COO-, -OOC-, -OCH2-, -CH2O-, -CF2O-, -OCF2-, -CF2CH2-, -CH2CF2-, -C2F4-, or -CF=CF-.

n=0、1、2、3或4。 n=0, 1, 2, 3 or 4.

優選的，上述含噻吩的液晶化合物中，R1，R2各自獨立地表示H、C1-C7的烷基或C1-C7的烷氧基，且所述C1-C7的烷基或C1-C7的烷氧基中的一個或多個氫可任選地被氟或氯取代，優選被氟取代。 Preferably, in the above-mentioned thiophene-containing liquid crystal compound, R1 and R2 each independently represent H, a C1-C7 alkyl group or a C1-C7 alkoxy group, and the C1-C7 alkyl group or a C1-C7 alkoxy group One or more hydrogens in the oxy group may be optionally substituted by fluorine or chlorine, preferably by fluorine.

優選的，上述含噻吩的液晶化合物中，A1代表單鍵或下列基團中的一種： Preferably, in the above-mentioned thiophene-containing liquid crystal compound, A 1 represents a single bond or one of the following groups:

Figure 110136096-A0101-12-0004-5
Figure 110136096-A0101-12-0004-5

優選的，上述含噻吩的液晶化合物中，Z1、Z2各自獨立地表示單鍵、-CH2-、-CH2-CH2-、-(CH2)3-、-(CH2)4-、-COO-、-OOC-、-OCH2-、-CH2O-、-CF2O-或-OCF2-。 Preferably, in the above-mentioned thiophene-containing liquid crystal compound, Z1 and Z2 each independently represent a single bond, -CH2-, -CH2-CH2-, -(CH2)3-, -(CH2)4-, -COO-, - OOC-, -OCH2-, -CH2O-, -CF2O- or -OCF2-.

作為進一步優選的技術方案，所述含噻吩的液晶化合物選自以下結構中的一種或多種： As a further preferred technical solution, the thiophene-containing liquid crystal compound is selected from one or more of the following structures:

Figure 110136096-A0101-12-0005-6
Figure 110136096-A0101-12-0005-6

Figure 110136096-A0101-12-0006-7
Figure 110136096-A0101-12-0006-7

Figure 110136096-A0101-12-0007-8
Figure 110136096-A0101-12-0007-8

Figure 110136096-A0101-12-0008-9
Figure 110136096-A0101-12-0008-9

Figure 110136096-A0101-12-0009-10
Figure 110136096-A0101-12-0009-10

Figure 110136096-A0101-12-0010-11
Figure 110136096-A0101-12-0010-11

Figure 110136096-A0101-12-0011-12
Figure 110136096-A0101-12-0011-12

Figure 110136096-A0101-12-0012-13
Figure 110136096-A0101-12-0012-13

Figure 110136096-A0101-12-0013-14
Figure 110136096-A0101-12-0013-14

Figure 110136096-A0101-12-0014-15
Figure 110136096-A0101-12-0014-15

Figure 110136096-A0101-12-0015-16
Figure 110136096-A0101-12-0015-16

Figure 110136096-A0101-12-0016-17
Figure 110136096-A0101-12-0016-17

Figure 110136096-A0101-12-0017-18
Figure 110136096-A0101-12-0017-18

Figure 110136096-A0101-12-0018-19
Figure 110136096-A0101-12-0018-19

Figure 110136096-A0101-12-0019-20
Figure 110136096-A0101-12-0019-20

Figure 110136096-A0101-12-0020-21
Figure 110136096-A0101-12-0020-21

Figure 110136096-A0101-12-0021-22
Figure 110136096-A0101-12-0021-22

Figure 110136096-A0101-12-0022-23
Figure 110136096-A0101-12-0022-23

Figure 110136096-A0101-12-0023-24
Figure 110136096-A0101-12-0023-24

Figure 110136096-A0101-12-0024-25
Figure 110136096-A0101-12-0024-25

Figure 110136096-A0101-12-0025-26
Figure 110136096-A0101-12-0025-26

Figure 110136096-A0101-12-0026-27
Figure 110136096-A0101-12-0026-27

Figure 110136096-A0101-12-0027-28
Figure 110136096-A0101-12-0027-28

Figure 110136096-A0101-12-0028-29
Figure 110136096-A0101-12-0028-29

Figure 110136096-A0101-12-0029-30
Figure 110136096-A0101-12-0029-30

Figure 110136096-A0101-12-0030-31
。
Figure 110136096-A0101-12-0030-31
 .

本發明的另一目的是提供上述含噻吩的液晶化合物的製備方法，其合成路線如下： Another object of the present invention is to provide the preparation method of the above-mentioned liquid crystal compound containing thiophene, and its synthetic route is as follows:

Figure 110136096-A0101-12-0031-32
Figure 110136096-A0101-12-0031-32

具體包括如下步驟： Specifically include the following steps:

化合物I-1-01與化合物I-1-02，在碳酸鈉以及催化劑作用下反應得到目標化合物I； Compound I-1-01 and compound I-1-02 are reacted under the action of sodium carbonate and a catalyst to obtain the target compound I;

其中，上述步驟所涉及化合物中的R1、R2、A1、A2、Z1、Z2的定義同上。 Wherein, the definitions of R 1 , R 2 , A 1 , A 2 , Z 1 and Z 2 in the compounds involved in the above steps are the same as above.

本發明的第三目的是保護含有上述含噻吩的液晶化合物的液晶組合物。其中，上述含噻吩的液晶化合物的加入量以1-80%為宜，更優選3-50%。本領域技術人員可以預見，基於上述含噻吩的液晶化合物的加入，能夠進一步提高已有慣用液晶組合物的光學各向異性，具有縮短器件的回應時間的技術效果。 The third object of the present invention is to protect a liquid crystal composition containing the above-mentioned thiophene-containing liquid crystal compound. Wherein, the addition amount of the above-mentioned thiophene-containing liquid crystal compound is preferably 1-80%, more preferably 3-50%. Those skilled in the art can predict that the addition of the above-mentioned thiophene-containing liquid crystal compound can further improve the optical anisotropy of the conventional liquid crystal composition, and has the technical effect of shortening the response time of the device.

本發明的第四目的是保護上述含噻吩的液晶化合物以及含有上述含噻吩的液晶化合物的組合物在液晶顯示領域的應用。優選為在液晶顯示裝置中的應用。所述的液晶顯示裝置包括但並不限於TN、ADS、VA、PSVA、FFS或IPS液晶顯示器。將上述含噻吩的液晶組合物應用至液晶顯示裝置後，具有縮短器件的回應時間的技術效果。 The fourth object of the present invention is to protect the application of the above-mentioned thiophene-containing liquid crystal compound and the composition containing the above-mentioned thiophene-containing liquid crystal compound in the field of liquid crystal display. Preferred is the application in liquid crystal display devices. Said liquid crystal display device includes but is not limited to TN, ADS, VA, PSVA, FFS or IPS liquid crystal display. After the above-mentioned thiophene-containing liquid crystal composition is applied to a liquid crystal display device, it has the technical effect of shortening the response time of the device.

以下實施例用於說明本發明，但不用來限制本發明的範圍。 The following examples are intended to illustrate the present invention, but not to limit the scope of the present invention.

除非另有說明，本發明中百分比為重量百分比；溫度單位為攝氏度。 Unless otherwise specified, the percentages in the present invention are by weight; the temperature is in degrees Celsius.

實施例1 Example 1

Figure 110136096-A0101-12-0032-36
Figure 110136096-A0101-12-0032-36

合成路線如下： The synthetic route is as follows:

Figure 110136096-A0101-12-0032-35
Figure 110136096-A0101-12-0032-35

在反應瓶中加入27.6g(0.1mol)化合物BYLC-01-1(反應物)，24gBYLC-01-2(反應物)100ml甲苯(溶劑)，100ml乙醇，100ml水，通氮氣保護，加入1g四三苯基膦鈀，12g碳酸鈉，加熱回流反應6小時，分液，100ml甲苯(溶劑)提取水相，水洗有機相至中性，蒸幹溶劑得淡黃色固體，200ml乙醇200ml正庚烷重結晶兩次得34.3gBYLC-01，收率90%，氣相色譜純度99.8%。 Add 27.6g (0.1mol) of compound BYLC-01-1 (reactant), 24g BYLC-01-2 (reactant), 100ml toluene (solvent), 100ml ethanol, 100ml water to the reaction flask, nitrogen protection, add 1g tetrafluoroethylene Triphenylphosphine palladium, 12g of sodium carbonate, heated under reflux for 6 hours, separated into layers, extracted the aqueous phase with 100ml of toluene (solvent), washed the organic phase with water until neutral, evaporated the solvent to dryness to obtain a pale yellow solid, weighed in 200ml of ethanol and 200ml of n-heptane 34.3 g of BYLC-01 were obtained by crystallization twice, the yield was 90%, and the gas chromatography purity was 99.8%.

質譜分析碎片：382.1(分子離子峰)。 Mass spectrometry fragment: 382.1 (molecular ion peak).

實施例2 Example 2

Figure 110136096-A0101-12-0032-33
Figure 110136096-A0101-12-0032-33

合成路線如下： The synthetic route is as follows:

Figure 110136096-A0101-12-0032-34
Figure 110136096-A0101-12-0032-34

在反應瓶中加入35.2g(0.1mol)化合物BYLC-02-1(反應物)，24gBYLC-01-2,100ml甲苯(溶劑)，100ml乙醇，100ml水，通氮氣保護，加入1g四三苯基膦鈀，12g碳酸鈉，加熱回流反應6小時，分液，100ml甲苯(溶劑)提取水相，水洗有機相至中性，蒸幹溶劑得淡黃色固體，200ml乙醇200ml正庚烷重結晶兩次得38.9gBYLC-02，收率85%，氣相色譜純度99.8%。 Add 35.2g (0.1mol) compound BYLC-02-1 (reactant), 24g BYLC-01-2, 100ml toluene (solvent), 100ml ethanol, 100ml water to the reaction flask, nitrogen protection, add 1g tetrakistriphenylphosphine Palladium, 12g of sodium carbonate, heated to reflux for 6 hours, liquid separation, 100ml of toluene (solvent) to extract the aqueous phase, washed the organic phase to neutrality, evaporated to dryness to obtain a pale yellow solid, recrystallized twice from 200ml of ethanol and 200ml of n-heptane to obtain 38.9g BYLC-02, the yield is 85%, and the gas chromatography purity is 99.8%.

質譜分析碎片：458.2(分子離子峰)。 Mass spectrometry fragment: 458.2 (molecular ion peak).

實施例3 Example 3

Figure 110136096-A0101-12-0033-37
Figure 110136096-A0101-12-0033-37

合成路線如下： The synthetic route is as follows:

Figure 110136096-A0101-12-0033-38
Figure 110136096-A0101-12-0033-38

在反應瓶中加入36g(0.1mol)化合物BYLC-03-1(反應物)，24gBYLC-01-2,100ml甲苯(溶劑)，100ml乙醇，100ml水，通氮氣保護，加入1g四三苯基膦鈀，12g碳酸鈉，加熱回流反應6小時，分液，100ml甲苯(溶劑)提取水相，水洗有機相至中性，蒸幹溶劑得淡黃色固體，200ml乙醇200ml正庚烷重結晶兩次得40gBYLC-03，收率86%，氣相色譜純度99.8%。 Add 36g (0.1mol) compound BYLC-03-1 (reactant), 24g BYLC-01-2, 100ml toluene (solvent), 100ml ethanol, 100ml water, nitrogen protection, 1g tetrakistriphenylphosphine palladium into the reaction flask , 12g of sodium carbonate, heated to reflux for 6 hours, liquid separation, 100ml of toluene (solvent) to extract the aqueous phase, washed the organic phase to neutrality, evaporated to dryness to obtain a light yellow solid, 200ml of ethanol and 200ml of n-heptane were recrystallized twice to obtain 40g BYLC -03, yield 86%, gas chromatography purity 99.8%.

質譜分析碎片：466.2(分子離子峰)。 Mass spectrometry fragment: 466.2 (molecular ion peak).

實施例4 Example 4

Figure 110136096-A0101-12-0034-42
Figure 110136096-A0101-12-0034-42

採用GC-MS對所得白色固體BYLC-04進行分析，產物的m/z為368.1(M+)。 The resulting white solid BYLC-04 was analyzed by GC-MS and the product had m/z of 368.1 (M+).

實施例5 Example 5

Figure 110136096-A0101-12-0034-41
Figure 110136096-A0101-12-0034-41

採用GC-MS對所得白色固體BYLC-05進行分析，產物的m/z為354.1(M+)。 The resulting white solid BYLC-05 was analyzed by GC-MS and the product had m/z of 354.1 (M+).

實施例6 Example 6

Figure 110136096-A0101-12-0034-40
Figure 110136096-A0101-12-0034-40

採用GC-MS對所得白色固體BYLC-06進行分析，產物的m/z為408.1(M+)。 The resulting white solid BYLC-06 was analyzed by GC-MS and the product had m/z of 408.1 (M+).

實施例7 Example 7

Figure 110136096-A0101-12-0034-39
Figure 110136096-A0101-12-0034-39

採用GC-MS對所得白色固體BYLC-07進行分析，產物的m/z為380.1(M+)。 The resulting white solid, BYLC-07, was analyzed by GC-MS, and the m/z of the product was 380.1 (M+).

實施例8 Example 8

Figure 110136096-A0101-12-0035-43
Figure 110136096-A0101-12-0035-43

採用GC-MS對所得白色固體BYLC-08進行分析，產物的m/z為412.1(M+)。 The resulting white solid BYLC-08 was analyzed by GC-MS and the product had m/z of 412.1 (M+).

實施例9 Example 9

Figure 110136096-A0101-12-0035-44
Figure 110136096-A0101-12-0035-44

採用GC-MS對所得白色固體BYLC-09進行分析，產物的m/z為396.1(M+)。 The resulting white solid, BYLC-09, was analyzed by GC-MS, and the m/z of the product was 396.1 (M+).

實驗例 Experimental example

本實驗例涉及對實施例1~9所述化合物的相關性能測定。 This experimental example involves the determination of the relevant properties of the compounds described in Examples 1 to 9.

按照本領域的常規檢測方法，γ 1的檢測採用粘度計測試，△n的檢測採用阿貝折射儀測試，△ε的檢測採用惠普公司型號為HP-4284A的電容電抗測試儀進行測定。 According to the conventional detection methods in the art, the detection of γ 1 adopts the viscometer test, the detection of Δn adopts the Abbe refractometer test, and the detection of Δε adopts the capacitive reactance tester of Hewlett-Packard Company model HP-4284A to measure.

通過線性擬合得到液晶化合物的各項性能參數，其中，各性能參數的具體含義如下： Various performance parameters of the liquid crystal compound are obtained by linear fitting, wherein the specific meanings of each performance parameter are as follows:

△n代表光學各向異性(25℃)；γ 1代表旋轉粘度(mPa.s，25℃)；△ε代表介電各向異性(25℃，1000Hz)。 Δn represents optical anisotropy (25°C); γ 1 represents rotational viscosity (mPa·s, 25°C); Δε represents dielectric anisotropy (25°C, 1000Hz).

將實施例1~9所制得的液晶化合物和對比例1~2液晶化合物的性能參數資料進行對比整理，檢測結果如表1所示： The performance parameter data of the liquid crystal compounds prepared in Examples 1 to 9 and the liquid crystal compounds of Comparative Examples 1 to 2 are compared and sorted, and the test results are shown in Table 1:

Figure 110136096-A0101-12-0036-45
Figure 110136096-A0101-12-0036-45

Figure 110136096-A0101-12-0037-46
Figure 110136096-A0101-12-0037-46

由表1的檢測結果可以明顯看出，本發明提供的含噻吩的液晶化合物與傳統的相似化學結構化合物相比，具有較高的光學各向異性△n，低的旋轉粘度γ 1，從而很好的改善回應時間。 It can be clearly seen from the test results in Table 1 that the thiophene-containing liquid crystal compounds provided by the present invention have higher optical anisotropy Δn and lower rotational viscosity γ 1 compared with traditional compounds with similar chemical structures, so that Good to improve response time.

雖然，上文中已經用一般性說明、具體實施方式及試驗，對本發明作了詳盡的描述，但在本發明基礎上，可以對之作一些修改或改進，這對本領域技術人員而言是顯而易見的。因此，在不偏離本發明精神的基礎上所做的這些修改或改進，均屬於本發明要求保護的範圍。 Although the present invention has been described in detail above with general description, specific embodiments and tests, some modifications or improvements can be made on the basis of the present invention, which is obvious to those skilled in the art . Therefore, these modifications or improvements made without departing from the spirit of the present invention fall within the scope of the claimed protection of the present invention.

Claims (10)

一種含噻吩的液晶化合物，其特徵在於，具有如通式(I)所示的結構： A thiophene-containing liquid crystal compound, characterized in that it has the structure shown in general formula (I):
Figure 110136096-A0101-13-0001-47
Figure 110136096-A0101-13-0001-47
 式中， In the formula, R1表示-H、-Cl、-F、-CN、-OCN、-OCF3、-CF3、-CHF2、-CH2F、-OCHF2、-OCF=CF2，-OCF2CF3，-SCN、-NCS、-SF5、C1-C15的烷基、C1-C15的烷氧基、C2-C15的烯基或C2-C15的烯氧基，其中所述C1-C15的烷基、C1-C15的烷氧基、C2-C15的烯基或C2-C15的烯氧基中的一個或多個氫可任選地被氟或氯取代，且一個或多個不相鄰的-CH2-可彼此獨立地被-CH=CH-、-C≡C-、-COO-、-OOC-、-O-或-S-取代； R 1 represents -H, -Cl, -F, -CN, -OCN, -OCF 3 , -CF 3 , -CHF 2 , -CH 2 F, -OCHF 2 , -OCF=CF 2 , -OCF 2 CF 3 , -SCN, -NCS, -SF 5 , C 1 -C 15 alkyl, C 1 -C 15 alkoxy, C 2 -C 15 alkenyl or C 2 -C 15 alkenyloxy, wherein One or more hydrogens in the C 1 -C 15 alkyl, C 1 -C 15 alkoxy, C 2 -C 15 alkenyl or C 2 -C 15 alkenyloxy may optionally be substituted by fluorine or chlorine, and one or more non-adjacent -CH 2 - may be independently of each other by -CH=CH-, -C≡C-, -COO-, -OOC-, -O- or -S -replace; R2表示-H、C1-C15的烷基、C1-C15的烷氧基、C2-C15的烯基或C2-C15的烯氧基，其中所述C1-C15的烷基、C1-C15的烷氧基、C2-C15的烯基或C2-C15的烯氧基中的一個或多個氫可任選地被氟或氯取代，且一個或多個不相鄰的-CH2-可彼此獨立地被-CH=CH-、-C≡C-、-COO-、-OOC-、-O-或-S-取代； R 2 represents -H, a C 1 -C 15 alkyl group, a C 1 -C 15 alkoxy group, a C 2 -C 15 alkenyl group or a C 2 -C 15 alkenyloxy group, wherein the C 1 -C 15 alkenyl group One or more hydrogens in a C 15 alkyl, C 1 -C 15 alkoxy, C 2 -C 15 alkenyl or C 2 -C 15 alkenyloxy may be optionally substituted with fluorine or chlorine , and one or more non-adjacent -CH 2 - can be independently replaced by -CH=CH-, -C≡C-, -COO-, -OOC-, -O- or -S-; A1代表單鍵或下列基團中的一種： A 1 represents a single bond or one of the following groups:
Figure 110136096-A0101-13-0002-48
Figure 110136096-A0101-13-0002-48
 A2代表單鍵或下列基團中的一種： A 2 represents a single bond or one of the following groups:
Figure 110136096-A0101-13-0002-49
Figure 110136096-A0101-13-0002-49
 Z1、Z2各自獨立地表示單鍵、-CH2-、-CH2-CH2-、-(CH2)3-、-(CH2)4-、-CH=CH-、-C≡C-、-COO-、-OOC-、-OCH2-、-CH2O-、-CF2O-、-OCF2-、-CF2CH2-、-CH2CF2-、-C2F4-或-CF=CF-； Z 1 and Z 2 each independently represent a single bond, -CH 2 -, -CH 2 -CH 2 -, -(CH 2 ) 3 -, -(CH 2 ) 4 -, -CH=CH-, -C≡ C-, -COO-, -OOC-, -OCH 2 -, -CH 2 O-, -CF 2 O-, -OCF 2 -, -CF 2 CH 2 -, -CH 2 CF 2 -, -C 2 F 4 -or -CF=CF-; n=0、1、2、3或4。 n=0, 1, 2, 3 or 4. 如請求項1所述的含噻吩的液晶化合物，其特徵在於，R1，R2各自獨立地表示H、C1-C7的烷基或C1-C7的烷氧基，且所述C1-C7的烷基或C1-C7的烷氧基中的一個或多個氫可任選地被氟或氯取代，優選被氟取代。 The thiophene-containing liquid crystal compound according to claim 1, wherein R 1 and R 2 each independently represent H, a C 1 -C 7 alkyl group or a C 1 -C 7 alkoxy group, and the One or more hydrogens in a C 1 -C 7 alkyl group or a C 1 -C 7 alkoxy group may be optionally substituted by fluorine or chlorine, preferably by fluorine. 如請求項1或2所述的含噻吩的液晶化合物，其特徵在於，A1代表單鍵或下列基團中的一種： The thiophene-containing liquid crystal compound according to claim 1 or 2, wherein A 1 represents a single bond or one of the following groups:
Figure 110136096-A0101-13-0003-50
Figure 110136096-A0101-13-0003-50
 如請求項1~3任一項所述的含噻吩的液晶化合物，其特徵在於，Z1、Z2各自獨立地表示單鍵、-CH2-、-CH2-CH2-、-(CH2)3-、-(CH2)4-、-COO-、-OOC-、-OCH2-、-CH2O-、-CF2O-或-OCF2-。 The thiophene-containing liquid crystal compound according to any one of claims 1 to 3, wherein Z 1 and Z 2 each independently represent a single bond, -CH 2 -, -CH 2 -CH 2 -, -(CH 2 ) 3- , -( CH2 ) 4- , -COO-, -OOC- , -OCH2- , -CH2O- , -CF2O- or -OCF2- . 如請求項1所述的含噻吩的液晶化合物，其特徵在於，所述通式(I)代表的化合物選自以下結構中的一種或多種： The thiophene-containing liquid crystal compound according to claim 1, wherein the compound represented by the general formula (I) is selected from one or more of the following structures:
Figure 110136096-A0101-13-0004-51
Figure 110136096-A0101-13-0004-51
Figure 110136096-A0101-13-0005-52
Figure 110136096-A0101-13-0005-52
Figure 110136096-A0101-13-0006-53
Figure 110136096-A0101-13-0006-53
Figure 110136096-A0101-13-0007-54
Figure 110136096-A0101-13-0007-54
Figure 110136096-A0101-13-0008-55
Figure 110136096-A0101-13-0008-55
Figure 110136096-A0101-13-0009-56
Figure 110136096-A0101-13-0009-56
Figure 110136096-A0101-13-0010-57
Figure 110136096-A0101-13-0010-57
Figure 110136096-A0101-13-0011-58
Figure 110136096-A0101-13-0011-58
Figure 110136096-A0101-13-0012-59
Figure 110136096-A0101-13-0012-59
Figure 110136096-A0101-13-0013-60
Figure 110136096-A0101-13-0013-60
Figure 110136096-A0101-13-0014-61
Figure 110136096-A0101-13-0014-61
Figure 110136096-A0101-13-0015-62
Figure 110136096-A0101-13-0015-62
Figure 110136096-A0101-13-0016-63
Figure 110136096-A0101-13-0016-63
Figure 110136096-A0101-13-0017-64
Figure 110136096-A0101-13-0017-64
Figure 110136096-A0101-13-0018-65
Figure 110136096-A0101-13-0018-65
Figure 110136096-A0101-13-0019-66
Figure 110136096-A0101-13-0019-66
Figure 110136096-A0101-13-0020-68
Figure 110136096-A0101-13-0020-68
Figure 110136096-A0101-13-0021-69
Figure 110136096-A0101-13-0021-69
Figure 110136096-A0101-13-0022-70
Figure 110136096-A0101-13-0022-70
Figure 110136096-A0101-13-0023-71
Figure 110136096-A0101-13-0023-71
Figure 110136096-A0101-13-0024-72
Figure 110136096-A0101-13-0024-72
Figure 110136096-A0101-13-0025-73
Figure 110136096-A0101-13-0025-73
Figure 110136096-A0101-13-0026-74
Figure 110136096-A0101-13-0026-74
Figure 110136096-A0101-13-0027-75
Figure 110136096-A0101-13-0027-75
Figure 110136096-A0101-13-0028-76
Figure 110136096-A0101-13-0028-76
Figure 110136096-A0101-13-0029-77
 。
Figure 110136096-A0101-13-0029-77
 . 請求項1~5任一項所述的含噻吩的液晶化合物的製備方法，其特徵在於，其合成路線如下： The method for preparing a thiophene-containing liquid crystal compound according to any one of claims 1 to 5, characterized in that the synthesis route is as follows:
Figure 110136096-A0101-13-0030-78
Figure 110136096-A0101-13-0030-78
 具體包括如下步驟： Specifically include the following steps: 化合物I-1-01與化合物I-1-02，在碳酸鈉以及催化劑作用下反應得到目標化合物I； Compound I-1-01 and compound I-1-02 are reacted under the action of sodium carbonate and a catalyst to obtain the target compound I; 其中，R1、R2、A1、A2、Z1、Z2的指代同權利要求1-4任一項所述。 Wherein, the designations of R 1 , R 2 , A 1 , A 2 , Z 1 , and Z 2 are the same as those described in any one of claims 1-4. 一種液晶組合物，其特徵在於，包括請求項1~5任一項所述的含噻吩的液晶化合物。 A liquid crystal composition, characterized by comprising the thiophene-containing liquid crystal compound according to any one of claims 1 to 5. 如請求項7所述的液晶組合物，其特徵在於，所述含噻吩的液晶化合物在所述液晶組合物中的品質百分比為1~60%，優選為3~50%，進一步優選為5~25%。 The liquid crystal composition according to claim 7, wherein the mass percentage of the thiophene-containing liquid crystal compound in the liquid crystal composition is 1 to 60%, preferably 3 to 50%, and more preferably 5 to 50%. 25%. 一種液晶組合物在液晶顯示裝置中的應用，其含有請求項1~5任一項所述的含噻吩的液晶化合物或請求項7或8所述的液晶組合物。 An application of a liquid crystal composition in a liquid crystal display device, comprising the thiophene-containing liquid crystal compound according to any one of claims 1 to 5 or the liquid crystal composition according to claim 7 or 8. 一種液晶顯示領域的液晶顯示裝置，其含有請求項9所述在液晶顯示領域中的應用，包含TN、ADS、VA、PSVA、FFS或IPS液晶顯示器。 A liquid crystal display device in the field of liquid crystal display, comprising the application in the field of liquid crystal display according to claim 9, including a TN, ADS, VA, PSVA, FFS or IPS liquid crystal display.
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