TW201722924A

TW201722924A - A compound containing a 2,5-benzofuran group, a liquid crystal composition containing same, and a display unit having specific characteristics like light and heat stability and UV stability after curing by a light

Info

Publication number: TW201722924A
Application number: TW104143847A
Authority: TW
Inventors: Ching-Tien Lee; Hsin-Cheng Liu; Chun-Chih Wang
Original assignee: Daxin Mat Corp
Priority date: 2015-12-25
Filing date: 2015-12-25
Publication date: 2017-07-01
Also published as: TWI608000B

Abstract

A kind of 2,5 compound containing a 2,5-benzofuran group has the structure represented by the following chemical formula 1, wherein R1, R2, L1 to L7 Z1, Z2, and n in the chemical formula are as defined in the specification and the scope of the patent, respectively. The present invention further provides a liquid crystal composition comprising at least one compound containing a 2,5-benzofuran group, and a display unit containing the liquid crystal composition. The compound containing the 2,5-benzofuran group of the present invention has good liquid crystal properties such as a wide liquid crystal state temperature range, good low temperature miscibility, higher birefringence, lower viscosity, larger K value, and light and heat stability, and can enhance the performance of liquid crystal composition like Tni, [Delta]n and UV stability.

Description

含有2,5-苯并呋喃基團的化合物、含有此化合物的液晶組成物及顯示單元 Compound containing 2,5-benzofuran group, liquid crystal composition containing the same, and display unit

本發明是有關於一種液晶化合物、含有此液晶化合物的液晶組成物及顯示單元，特別是指一種含有2,5-苯并呋喃基團的化合物、含有此化合物的液晶組成物及顯示單元。 The present invention relates to a liquid crystal compound, a liquid crystal composition containing the liquid crystal compound, and a display unit, and more particularly to a compound containing a 2,5-benzofuran group, a liquid crystal composition containing the compound, and a display unit.

為了因應液晶顯示裝置的迅速發展，各種新穎的液晶化合物或液晶組成物也有大量的研發需求，其中，雜環類液晶化合物即為倍受注目的研發目標之一。雜環類液晶化合物由於在環結構中含有雜原子，可藉由化合物極性及分子間作用力的改變，而進一步改變液晶化合物的液晶性質和光物理性質。雜環類液晶化合物，例如苯并呋喃(benzofuran)、苯并噻唑(benzothiazole)、苯并噻二唑(benzothiadiazole)、苯并噁唑(benzoxazole)等。 In order to cope with the rapid development of liquid crystal display devices, various novel liquid crystal compounds or liquid crystal compositions have also been in great demand for research and development. Among them, heterocyclic liquid crystal compounds are one of the most research and development targets. Since the heterocyclic liquid crystal compound contains a hetero atom in the ring structure, the liquid crystal properties and photophysical properties of the liquid crystal compound can be further changed by the change in the polarity of the compound and the intermolecular force. Heterocyclic liquid crystal compounds, such as benzofuran, benzothiazole, benzothiadiazole, benzoxazole, and the like.

CN 100415730C公開一種具有下述結構式的苯并呋喃衍生物： R¹⁰為C₁~C₁₅烷基或烯基、C₁~C₁₅烷氧基或烯氧基、C₁~C₁₅氟烷基或氟烯基；r、s及t為0~2但不同時為0；R¹¹為H、F、Cl、Br、I、OCF₃、CN、CF₃、C₁~C₁₅烷基或烯基、C₁~C₁₅烷氧基或烯氧基、C₁~C₁₅氟烷基或氟烯基；X¹~X⁵為H、F、Cl、CH₃、OCF₃、CF₃或OCHF₂；Z⁰為單鍵、-CH₂CH₂-、-CH=CH-、-C≡C-、-COO-、-OOC-、-CH₂O-、-OCH₂-、或。上述的苯并呋喃衍生物具有較寬的液晶態溫度範圍、良好的低溫互溶性、較小的雙折射率、較低的黏度等性質。 CN 100415730C discloses a benzofuran derivative having the formula: R ¹⁰ is C ₁ -C ₁₅ alkyl or alkenyl, C ₁ -C ₁₅ alkoxy or alkenyloxy, C ₁ -C ₁₅ fluoroalkyl or fluoroalkenyl; r, s and t are 0-2 Not necessarily 0; R ¹¹ is H, F, Cl, Br, I, OCF ₃ , CN, CF ₃ , C ₁ -C ₁₅ alkyl or alkenyl, C ₁ -C ₁₅ alkoxy or alkenyloxy, C ₁ to C ₁₅ fluoroalkyl or fluoroalkenyl; X ¹ to X ⁵ are H, F, Cl, CH ₃ , OCF ₃ , CF ₃ or OCHF ₂ ; Z ⁰ is a single bond, -CH ₂ CH ₂ -, -CH=CH-, -C≡C-, -COO-, -OOC-, -CH ₂ O-, -OCH ₂ -, or . The above benzofuran derivatives have a wide liquid crystal temperature range, good low temperature miscibility, a small birefringence, and a low viscosity.

目前針對液晶化合物的研發多著重於物理或光學性質的改善，並未注意到由液晶化合物所配製而得的液晶組成物於後續填入液晶盒後，必須於液晶盒外塗上封裝膠，再經過紫外線照射，使封裝膠進行固化；在此封裝過程中，液晶盒內的液晶組成物可能會受到紫外線照射而產生性質的改變，因此，液晶組成物之紫外線穩定性的提升也成為目前液晶化合物的主要研發方向。 At present, the research and development of liquid crystal compounds pay more attention to the improvement of physical or optical properties. It is not noticed that the liquid crystal composition prepared by the liquid crystal compound must be coated with the encapsulant outside the liquid crystal cell after being filled into the liquid crystal cell. After the ultraviolet irradiation, the encapsulant is cured; in the encapsulation process, the liquid crystal composition in the liquid crystal cell may be subjected to ultraviolet light to change the properties, and therefore, the ultraviolet stability of the liquid crystal composition is also a liquid crystal compound. The main research and development direction.

因此，本發明之目的，即在提供一種可提升液晶組成物的T_ni、△n等性質及紫外線穩定性的含有2,5-苯并呋喃基團的化合物。 Accordingly, it is an object of the present invention to provide a compound containing a 2,5-benzofuran group which can enhance properties such as T _ni and Δn of a liquid crystal composition and ultraviolet stability.

於是，本發明含有2,5-苯并呋喃基團的化合物具有以下化學式1所示的結構：於化學式1中， R¹表示鹵素原子、-CN、C₁~C₁₀的烷基、C₁~C₁₀的烷氧基或C₂~C₁₀烯基，該烷基、該烷氧基或該烯基中的至少一個氫可選擇地被鹵素原子所取代，或者至少一個-CH₂-可選擇地被-O-取代，且各個-O-彼此不直接相連接；環A表示1,4-伸苯基或1,4-伸環己烷基；Z¹及Z²各自獨立地表示單鍵、-(CH₂)₂-、-COO-、-OCO-、-OOC-、-C≡C-或-CH=CH-；L¹~L⁷各自獨立地表示H、-CN或鹵素原子；R²表示C₁~C₁₀的烷基或C₂~C₁₀烯基，該烷基或該烯基中的至少一個氫可選擇地被鹵素原子所取代，或者至少一個-CH₂-可選擇地被-O-取代，且各個-O-彼此不直接相連接；及n表示0或1。 Thus, the compound containing a 2,5-benzofuran group of the present invention has a structure represented by the following Chemical Formula 1: In Chemical Formula 1, R ¹ represents a halogen atom, -CN, a C ₁ -C ₁₀ alkyl group, a C ₁ -C ₁₀ alkoxy group or a C ₂ -C ₁₀ alkenyl group, the alkyl group, the alkoxy group or At least one hydrogen in the alkenyl group may be optionally substituted by a halogen atom, or at least one -CH ₂ - may be optionally substituted by -O-, and each -O- is not directly bonded to each other; ring A represents 1,4 - a phenyl or 1,4-cyclohexane group; Z ¹ and Z ² each independently represent a single bond, -(CH ₂ ) ₂ -, -COO-, -OCO-, -OOC-, -C≡ C- or -CH=CH-; L ¹ to L ⁷ each independently represent H, -CN or a halogen atom; R ² represents a C ₁ -C ₁₀ alkyl group or a C ₂ -C ₁₀ alkenyl group, the alkyl group or At least one hydrogen in the alkenyl group may be optionally substituted by a halogen atom, or at least one -CH ₂ - may be optionally substituted by -O-, and each -O- is not directly connected to each other; and n represents 0 or 1 .

本發明之另一目的在於提供一種具有良好紫外線穩定性的液晶組成物。 Another object of the present invention is to provide a liquid crystal composition having good ultraviolet stability.

本發明液晶組成物包含至少一種前述含有2,5-苯并呋喃基團的化合物。 The liquid crystal composition of the present invention contains at least one of the aforementioned compounds containing a 2,5-benzofuran group.

本發明之又另一目的在於提供一種顯示單元。 Still another object of the present invention is to provide a display unit.

本發明顯示單元包含前述的液晶組成物。 The display unit of the present invention comprises the aforementioned liquid crystal composition.

本發明之功效在於：本發明含有2,5-苯并呋喃基團的化合物具備新穎的結構設計及良好的液晶特性，例如較寬的液晶態溫度範圍、良好的低溫互溶性、較高的雙折射率、較低的黏度、較大的K值、及光、熱穩定等特性。於後續應用於液晶組成物時，能有效提升液晶組成物的T_ni、△n等性質，更能讓液晶組成物具備良好的紫外線穩定性。 The invention has the advantages that the compound containing the 2,5-benzofuran group of the invention has novel structural design and good liquid crystal characteristics, such as a wide liquid crystal temperature range, good low temperature miscibility, and a high double Refractive index, low viscosity, large K value, and light and heat stability. When applied to the liquid crystal composition in the subsequent application, the properties of T _ni and Δn of the liquid crystal composition can be effectively improved, and the liquid crystal composition can have good ultraviolet stability.

以下將就本發明內容進行詳細說明：較佳地，該化學式1中的R²表示C₁~C₁₀烷基或C₂~C₁₀烯基。更佳地，該R²表示C₁~C₁₀烷基。 Hereinafter, the present invention will be described in detail. Preferably, R ² in the chemical formula 1 represents a C ₁ -C ₁₀ alkyl group or a C ₂ -C ₁₀ alkenyl group. More preferably, R ² represents a C ₁ -C ₁₀ alkyl group.

較佳地，該化學式1中的R¹表示C₁~C₁₀烷基或C₂~C₁₀烯基。更佳地，該R¹表示C₁~C₁₀烷基。於本發明的一具體例中，該R¹及R²各自表示C₁~C₁₀烷基。 Preferably, in the chemical formula 1 R ¹ represents a C ₁ ~ C ₁₀ alkyl or C ₂ ~ C ₁₀ alkenyl group. More preferably, R ¹ represents a C ₁ -C ₁₀ alkyl group. In a specific example of the present invention, each of R ¹ and R ² represents a C ₁ -C ₁₀ alkyl group.

較佳地，該化學式1中的n表示0。 Preferably, n in the chemical formula 1 represents 0.

較佳地，該化學式1中的Z¹及Z²為單鍵。 Preferably, Z ¹ and Z ² in the chemical formula 1 are a single bond.

較佳地，該化學式1中的L¹~L⁷皆表示氫。 Preferably, L ¹ to L ⁷ in the chemical formula 1 all represent hydrogen.

於本發明的另一具體例中，該n表示0，該Z¹及Z²為單鍵，該L¹~L⁷皆表示氫，及該R¹及R²各自表示C₁~C₁₀烷基，如下述化學式2所示： In another embodiment of the present invention, the n represents 0, the Z ¹ and Z ² are single bonds, the L ¹ to L ⁷ represent hydrogen, and the R ¹ and R ² each represent a C ₁ to C ₁₀ alkane. Base, as shown in the following Chemical Formula 2:

更具體地，該化學式2所示的化合物的例子如下表：於上表中，P代表1,4-伸苯基，G代表2-氟-1,4-伸苯基，及B代表2,5-苯并呋喃基團。 More specifically, examples of the compound represented by Chemical Formula 2 are as follows: In the above table, P represents 1,4-phenylene, G represents 2-fluoro-1,4-phenylene, and B represents a 2,5-benzofuran group.

於本發明的另一具體例中，該n表示1，環A表示伸環己基，該Z¹及Z²為單鍵，該L¹~L⁷皆表示氫，及該R¹及R²各自表示C₁~C₁₀烷基，如下述化學式3所示： In another embodiment of the present invention, the n represents 1, the ring A represents a cyclohexylene group, the Z ¹ and Z ² are a single bond, and the L ¹ to L ⁷ represent hydrogen, and the respective R ¹ and R ² Represents a C ₁ -C ₁₀ alkyl group as shown in the following Chemical Formula 3:

更具體地，該化學式3所示的化合物的例子如下表： More specifically, examples of the compound represented by Chemical Formula 3 are as follows:

於本發明的另一具體例中，該n表示0，該Z¹表示伸炔基，Z²為單鍵，該L¹~L⁷皆表示氫，及該R¹及R²各自表示C₁~C₁₀烷基，如下述化學式4所示： In another embodiment of the present invention, the n represents 0, the Z ¹ represents an alkynyl group, the Z ² is a single bond, the L ¹ to L ⁷ represent a hydrogen, and the R ¹ and R ² each represent a C ₁ ~C ₁₀ alkyl group, as shown in the following Chemical Formula 4:

更具體地，該化學式4所示的化合物的例子如下表：於上表中，T代表伸炔基(-C≡C-)。 More specifically, examples of the compound represented by Chemical Formula 4 are as follows: In the above table, T represents an alkynyl group (-C≡C-).

本發明含有2,5-苯并呋喃基團的化合物可以依據已知合成方法進行製備，以具有化學式2結構的化合物為例，可透過如下述合成路徑進行製備：在上述合成路徑中，經對位R²取代的苯酚先與多聚甲醛反應而生成經R²取代水楊醛，接著，該經R²取代水楊醛與四溴化碳於三苯基膦存在下在二氯甲烷溶劑中進行反應並獲得式(i)化合物。再以磷酸鉀作為鹼，碘化銅作為催化劑，使該式(i)化合物於四氫呋喃中加熱迴流並進行合環反應，以獲得式(ii)化合物。利用該式(ii)化合物作為前驅物，再依據所欲獲得液晶化合物的結構選用與該前驅物反應的起始物，然後使該前驅物與起始物進行Suzuki cross-coupling反應，即可製備本發明的液晶化合物。於上述合成路徑中，該起始物為式(iii)化合物。此外，具有化學式3及4結構的化合物的製法有可以經由上述製法進行製備，同樣可利用該式(ii)化合物作為前驅物，再依據所欲獲得液晶化合物的結構選用與該前驅物反應的起始物，然後使該前驅物與起始物進行Suzuki cross-coupling反應，即可製得具有化學式3及4結構的液晶化合物。 The compound containing a 2,5-benzofuran group of the present invention can be produced according to a known synthesis method, and a compound having a structure of the chemical formula 2 can be exemplified by a synthetic route as follows: In the above synthetic route, the phenol substituted by the para-R ² is first reacted with paraformaldehyde to form an R ² -substituted salicylaldehyde, and then the R ² -substituted salicylaldehyde and the carbon tetrabromide are in the triphenylphosphine. The reaction is carried out in a dichloromethane solvent in the presence of a compound of formula (i). Further, using potassium phosphate as a base and copper iodide as a catalyst, the compound of the formula (i) is heated under reflux in tetrahydrofuran and subjected to a ring-closing reaction to obtain a compound of the formula (ii). The compound of the formula (ii) is used as a precursor, and the starting material reacted with the precursor is selected according to the structure of the liquid crystal compound to be obtained, and then the precursor is subjected to a Suzuki cross-coupling reaction with the starting material to prepare a precursor. The liquid crystal compound of the present invention. In the above synthetic route, the starting material is a compound of formula (iii). In addition, the preparation of the compound having the chemical formulas 3 and 4 can be carried out by the above-mentioned production method, and the compound of the formula (ii) can also be used as a precursor, and the reaction with the precursor can be selected depending on the structure of the liquid crystal compound to be obtained. The starting material is then subjected to a Suzuki cross-coupling reaction with the starting material to obtain a liquid crystal compound having a chemical formula of 3 and 4.

本發明含有2,5-苯并呋喃基團的化合物適用於作為液晶組成物的組成成分，有助於提升液晶組成物之由向列相至液體的相變溫度(T_ni)、介電異向性(△ε)、折射率異向性(△n)、彈性常數(K₁₁及K₃₃)及紫外線穩定性等性質。 The compound containing a 2,5-benzofuran group of the present invention is suitable as a constituent component of a liquid crystal composition, and contributes to a phase transition temperature (T _ni ) and dielectric difference from a nematic phase to a liquid of a liquid crystal composition. Properties such as tropism (Δε), refractive index anisotropy (Δn), elastic constant (K ₁₁ and K ₃₃ ), and ultraviolet stability.

本發明液晶組成物包含至少一種含有2,5-苯并呋喃基團的化合物。較佳地，該液晶組成物包含至少一種由前述化學式2所示的化合物。該液晶組成物也可依據後續應用需求，包含各種市售常用的液晶化合物。 The liquid crystal composition of the present invention contains at least one compound containing a 2,5-benzofuran group. Preferably, the liquid crystal composition contains at least one compound represented by the aforementioned Chemical Formula 2. The liquid crystal composition can also contain various commercially available liquid crystal compounds according to the needs of subsequent applications.

本發明顯示單元包含上述的液晶組成物。本發明顯示單元可應用於各種顯示器中，例如但不限於TN、STN、FFS、IPS、VA、PSA等。 The display unit of the present invention comprises the above liquid crystal composition. The display unit of the present invention can be applied to various displays such as, but not limited to, TN, STN, FFS, IPS, VA, PSA, and the like.

本發明將就以下實施例作進一步說明，但應瞭解的是，該實施例僅為例示說明之用，而不應被解釋為本發明實施之限制。 The invention is further illustrated by the following examples, but it should be understood that this embodiment is intended to be illustrative only and not to be construed as limiting.

<實施例><Example> [實施例1]由式(2-1)所示化合物(2PGB3)的製備[Example 1] Preparation of Compound (2PGB3) represented by Formula (2-1)

依據上述的合成路徑進行製備，首先取4-丙基苯酚(3.3g，24mmol)、氯化鎂(3.9g，36mmol)、多聚甲醛(polyoxymethylene，5g，165mmol)、三乙胺(13.5mL，9.3mmol)溶於乙腈(60mL)中獲得一反應液，使該反應液進行加熱迴流並反應4小時，以TLC確認反應完全後，於該反應液中加入稀鹽酸(1N，50mL)中止反應並形成一混合液。以乙酸乙酯反覆對混合液進行3次萃取並收集有機層，於有機層中加入無水硫酸鎂去除水份，再進行過濾及減壓濃縮得到一粗產物。利用管柱層析法(沖提液為乙酸乙酯與正己烷混合液，其中乙酸乙酯與正己烷的體積比例為1：9)進行該粗產物的純化，獲得2-羥基-5-丙基-苯甲醛(3.2g，黃色液體)。 Prepared according to the above synthetic route, first taking 4-propylphenol (3.3g, 24mmol), magnesium chloride (3.9g, 36mmol), polyoxymethylene (5g, 165mmol), triethylamine (13.5mL, 9.3mmol) Dissolved in acetonitrile (60 mL) to obtain a reaction mixture, and the reaction mixture was heated and refluxed for 4 hours. After confirming the completion of the reaction by TLC, dilute hydrochloric acid (1N, 50 mL) was added to the reaction mixture to terminate the reaction and form a Mixture. The mixture was extracted three times with ethyl acetate and the organic layer was collected. The organic layer was evaporated to dryness with anhydrous magnesium sulfate, and then filtered and concentrated to give a crude product. The crude product was purified by column chromatography (the extract was a mixture of ethyl acetate and n-hexane, wherein the volume ratio of ethyl acetate to n-hexane was 1:9) to obtain 2-hydroxy-5-propyl. Base-benzaldehyde (3.2 g, yellow liquid).

在双頸圓底瓶中，加入三苯基膦(15.8g，60mmol)、四溴化碳(13g，40mmol)及二氯甲烷(80mL)並開始攪拌，以冰水浴降溫到0℃後，慢慢加入由2-羥基-5-丙基-苯甲醛(3.2g，20mmol)、三乙胺(8.4mL，60mmol)及二氯甲烷(10mL)組成的混合液而得到一反應液。使該反應液攪拌1小時，並以TLC確認反應完全後，於該反應液中加入水(50mL)中止反應，以二氯甲烷反覆進行三次萃取並收集有機層，再以無水硫酸鎂去除水份，最後進行過濾及減壓濃縮，得到由式(i-1)所示的中間體。再將此中間體溶於四氫呋喃(150mL)中，加入磷酸鉀(8g，40mmol)及碘化銅(0.19g，1mmol)得到中間反應液。使該中間反應液加熱廻流6小時，以TLC確認反應完全後，於中間反應液中加入水(100mL)中止反應，以乙酸乙酯反覆對中間反應液進行三次萃取並收集有機層，再於有機層中加入無水硫酸鎂去除水份，再進行過濾及減壓濃縮獲得粗產物。最後利用管柱層析法(沖提液為乙酸乙酯及正己烷混合液，其中乙酸乙酯與正己烷的體積比例為1：9)進行粗產物的純化，獲得3.5g由式(ii-1)所示的2-溴-5-丙基苯并呋喃(黃色液體)。 In a double necked round bottom flask, triphenylphosphine (15.8 g, 60 mmol), carbon tetrabromide (13 g, 40 mmol) and dichloromethane (80 mL) were added and stirring was started, and the temperature was lowered to 0 ° C in an ice water bath. A mixture of 2-hydroxy-5-propyl-benzaldehyde (3.2 g, 20 mmol), triethylamine (8.4 mL, 60 mmol) and dichloromethane (10 mL) was slowly added to give a mixture. The reaction solution. The reaction solution was stirred for 1 hour, and after completion of the reaction was confirmed by TLC, water (50 mL) was added to the reaction mixture to terminate the reaction, and the mixture was extracted three times with dichloromethane and the organic layer was collected. Finally, filtration and concentration under reduced pressure gave an intermediate represented by the formula (i-1). This intermediate was dissolved in tetrahydrofuran (150 mL), and potassium phosphate (8 g, 40 mmol) and copper iodide (0.19 g, 1 mmol) were added to obtain an intermediate reaction mixture. The intermediate reaction solution was heated and turbulent for 6 hours. After confirming the completion of the reaction by TLC, water (100 mL) was added to the intermediate reaction mixture to terminate the reaction. The intermediate reaction solution was extracted three times with ethyl acetate and the organic layer was collected. Anhydrous magnesium sulfate was added to the organic layer to remove water, followed by filtration and concentration under reduced pressure to give a crude product. Finally, the crude product was purified by column chromatography (the extract was a mixture of ethyl acetate and n-hexane, wherein the volume ratio of ethyl acetate to n-hexane was 1:9) to obtain 3.5 g of the formula (ii- 1) 2-Bromo-5-propylbenzofuran (yellow liquid) as shown.

在双頸圓底瓶中，加入四(三苯基膦)鈀(0.56g，5mol%)、2-溴-5-丙基苯并呋喃(2.3g，9.6mmol)、2-氟，4’-乙基聯苯硼酸(3.6g，14.8mmol)、碳酸鉀(6.1g，44.4mmol)、水(15mL)及四氫呋喃(100ml)得到混合液。使該混合液進行加熱廻流6小時，以TLC確認反應完全後，於混合液中加入水(100mL)中止反應，以乙酸乙酯反覆進行三次萃取並收集有機層，於有機層中加入無水硫酸鎂去除水份，再進行過濾及減壓濃縮獲得粗產物。最後利用管柱層析法(沖提液為正己烷)進行粗產物的純化，獲得2.8g的由式(2-1)所示化合物2PGB3(白色固體)。 In a double neck round bottom bottle, tetrakis(triphenylphosphine)palladium (0.56 g, 5 mol%), 2-bromo-5-propylbenzofuran (2.3 g, 9.6 mmol), 2-fluoro, 4' were added. -ethylbiphenylboronic acid (3.6 g, 14.8 mmol), potassium carbonate (6.1 g, 44.4 mmol), water (15 mL) and tetrahydrofuran (100 ml) gave a mixture. The mixture was heated and turbulent for 6 hours. After confirming the completion of the reaction by TLC, water (100 mL) was added to the mixture to terminate the reaction. The mixture was extracted three times with ethyl acetate and the organic layer was collected. The magnesium was removed from the water, filtered and concentrated under reduced pressure to give a crude material. Finally, purification of the crude product was carried out by column chromatography (purified solvent: n-hexane) to obtain 2.8 g of compound 2PGB3 (white solid) of formula (2-1).

以400MHz的核磁共振儀(¹H-NMR)進行該化合物2PGB3的測試，結果為：¹H-NMR(CDCl₃,400MHz),δ(ppm)：1.20-1.27 (m,6H),1.63-1.72(m,2H),2.65-2.72(m,4H),7.115(dd,1H,J=8.8、2.4Hz),7.180(d,1H,J=4Hz),7.287(d,2H,J=8.4Hz),7.36-7.55(m,6H),8.040(t,1H,J=8Hz)。 The compound 2PGB3 was tested by a 400 MHz nuclear magnetic resonance apparatus ( ¹ H-NMR), and the results were as follows: ¹ H-NMR (CDCl ₃ , 400 MHz), δ (ppm): 1.20-1.27 (m, 6H), 1.63-1.72 (m, 2H), 2.65-2.72 (m, 4H), 7.115 (dd, 1H, J = 8.8, 2.4 Hz), 7.180 (d, 1H, J = 4 Hz), 7.287 (d, 2H, J = 8.4 Hz) ), 7.36-7.55 (m, 6H), 8.040 (t, 1H, J = 8 Hz).

再以氣相層析-質譜儀(GC-MS)進行該化合物2PGB3的測試，結果為：GC-MS：m/z=358.4241[M]⁺。 The compound 2PGB3 was tested by gas chromatography-mass spectrometry (GC-MS) and found to be: GC-MS: m/z = 358.4241 [M] ⁺ .

[實施例2]由式(2-2)所示化合物(3PGB2)的製備[Example 2] Preparation of Compound (3PGB2) represented by Formula (2-2)

除了將4-丙基苯酚(24mmol)置換為4-乙基苯酚(24mmol)、將2-溴-5-丙基苯并呋喃(2.3g，9.6mmol)置換成2-溴-5-乙基苯并呋喃(2.2g，9.6mmol)，及將2-氟，4’-乙基聯苯硼酸(3.6g，14.8mmol)置換成2-氟，4’-丙基聯苯硼酸(3.8g，14.8mmol)外，其餘製程及條件與實施例1相同，最後製得2.9g的由式(2-2)所示化合物3PGB2。 Substituting 4-propylphenol (24 mmol) with 4-ethylphenol (24 mmol) and 2-bromo-5-propylbenzofuran (2.3 g, 9.6 mmol) with 2-bromo-5-ethyl Benzofuran (2.2 g, 9.6 mmol), and 2-fluoro, 4'-ethylbiphenylboronic acid (3.6 g, 14.8 mmol) was replaced with 2-fluoro, 4'-propylbiphenylboronic acid (3.8 g, The other processes and conditions were the same as in Example 1 except that 14.8 mmol), and finally 2.9 g of the compound 3PGB2 represented by the formula (2-2) was obtained.

以400MHz的核磁共振儀(¹H-NMR)進行該化合物3PGB2的測試，結果為：¹H-NMR(CDCl₃,400MHz),δ(ppm)：1.140(t,3H,J=8Hz),1.272(t,3H,J=8Hz),1.64-1.69(m,2H),2.64-2.76(m,4H),7.115(dd,1H,J=8.8、2.4Hz),7.140(d,1H,J=4Hz),7.245(d,2H,J=8.4Hz),7.36-7.54(m,6H),8.036(t,1H,J=8Hz)。 Carried out in a 400MHz NMR spectrometer ⁽¹ H-NMR) of this compound 3PGB2 test, the ^{_{results: 1 H-NMR (CDCl 3}} , 400MHz), δ (ppm): 1.140 (t, 3H, J = 8Hz), 1.272 (t, 3H, J = 8 Hz), 1.64-1.69 (m, 2H), 2.64 - 2.76 (m, 4H), 7.115 (dd, 1H, J = 8.8, 2.4 Hz), 7.140 (d, 1H, J = 4 Hz), 7.245 (d, 2H, J = 8.4 Hz), 7.36-7.54 (m, 6H), 8.036 (t, 1H, J = 8 Hz).

再以氣相層析-質譜儀(GC-MS)進行該化合物3PGB2的測試，結果為：GC-MS：m/z=358.2833[M]⁺。 The test of the compound 3PGB2 was carried out by gas chromatography-mass spectrometry (GC-MS). The result was: GC-MS: m/z = 358.2833 [M] ⁺ .

[實施例3]由式(2-3)所示化合物(2PGB2)的製備[Example 3] Preparation of Compound (2PGB2) represented by Formula (2-3)

除了將4-丙基苯酚(24mmol)置換為4-乙基苯酚(24mmol)，及將2-溴-5-丙基苯并呋喃(2.3g，9.6mmol)置換成2-溴-5-乙基苯并呋喃(2.2克，9.6mmol)外，其餘製程及條件與實施例1相同，最後製得2.7g的由式(2-3)所示化合物2PGB2。 In addition to replacing 4-propylphenol (24 mmol) with 4-ethylphenol (24 mmol) and 2-bromo-5-propylbenzofuran (2.3 g, 9.6 mmol) with 2-bromo-5-B Benzo The other processes and conditions were the same as in Example 1 except for furan (2.2 g, 9.6 mmol), and finally 2.7 g of the compound 2PGB2 of the formula (2-3) was obtained.

[實施例4]由式(2-4)所示化合物(3PGB1)的製備[Example 4] Preparation of Compound (3PGB1) represented by Formula (2-4)

除了將4-丙基苯酚(24mmol)置換為4-甲基苯酚(24mmol)、將2-溴-5-丙基苯并呋喃(2.3g，9.6mmol)置換成2-溴-5-甲基苯并呋喃(2.0g，9.6mmol)，及將2-氟，4’-乙基聯苯硼酸(3.6g，14.8mmol)置換成2-氟，4’-丙基聯苯硼酸(3.8g，14.8mmol)外，其餘製程及條件與實施例1相同，最後製得3.1g的由式(2-4)所示化合物3PGB1。 Substituting 4-propylphenol (24 mmol) for 4-methylphenol (24 mmol) and 2-bromo-5-propylbenzofuran (2.3 g, 9.6 mmol) for 2-bromo-5-methyl Benzofuran (2.0 g, 9.6 mmol), and 2-fluoro, 4'-ethylbiphenylboronic acid (3.6 g, 14.8 mmol) was replaced with 2-fluoro, 4'-propylbiphenylboronic acid (3.8 g, The other processes and conditions were the same as in Example 1 except that 14.8 mmol), and finally 3.1 g of the compound 3PGB1 represented by the formula (2-4) was obtained.

利用氣相層析-質譜儀(GC-MS)進行該式(2-4)所示化合物3PGB1的測試，結果為：GC-MS：m/z=344.3957[M]⁺。 The test of the compound 3PGB1 of the formula (2-4) was carried out by gas chromatography-mass spectrometry (GC-MS), and the result was: GC-MS: m/z = 344.3957 [M] ⁺ .

[實施例5]由式(3-1)所示化合物(3CPGB2)的製備[Example 5] Preparation of Compound (3CPGB2) represented by Formula (3-1)

除了將4-丙基苯酚(24mmol)置換為4-乙基苯酚(24mmol)、將2-溴-5-丙基苯并呋喃(2.3g，9.6mmol)置換成2-溴-5-乙基苯并呋喃(2.2g，9.6mmol)，及將2-氟，4’-乙基聯苯硼酸(3.6，14.8mmol)置換成3-氟-4’-(4-丙基環己基)-聯苯硼酸(5g，14.8mmol)外，其餘製程及條件與實施例1相同，最後製得3.2g的由式(3-1)所示化合物3CPGB2。 Substituting 4-propylphenol (24 mmol) with 4-ethylphenol (24 mmol) and 2-bromo-5-propylbenzofuran (2.3 g, 9.6 mmol) with 2-bromo-5-ethyl Benzofuran (2.2 g, 9.6 mmol), and 2-fluoro, 4'-ethylbiphenylboronic acid (3.6,14.8 mmol) was replaced by 3-fluoro-4'-(4-propylcyclohexyl)-linked Except for phenylboronic acid (5 g, 14.8 mmol), the other processes and conditions were the same as in Example 1, and finally 3.2 g of the compound of the formula (3-1), 3CPGB2, was obtained.

以400MHz的核磁共振儀(¹H-NMR)進行該由式(3-1)所示化合物3CPGB2的測試，結果為：¹H-NMR(CDCl₃,400MHz),δ(ppm)：0.901(t,3H,J=8Hz),1.10-1.49(m,11H),1.85-1.93(m,4H),2.47-2.53(m,2H),2.745(q,2H,J=8Hz),7.125(dd, 1H,J=8.8、2.4Hz),7.177(d,1H,J=4Hz),7.292(d,2H,J=8.4Hz),7.36-7.54(m,6H),8.055(t,1H,J=8Hz)。 In a 400MHz NMR spectrometer ⁽¹ H-NMR) for the formula (3-1), a compound 3CPGB2 test ^{_{results: 1 H-NMR (CDCl 3}} , 400MHz), δ (ppm): 0.901 (t , 3H, J = 8 Hz), 1.10- 1.49 (m, 11H), 1.85-1.93 (m, 4H), 2.47-2.53 (m, 2H), 2.745 (q, 2H, J = 8 Hz), 7.125 (dd, 1H, J = 8.8, 2.4 Hz), 7.177 (d, 1H, J = 4 Hz), 7.292 (d, 2H, J = 8.4 Hz), 7.36-7.54 (m, 6H), 8.055 (t, 1H, J = 8Hz).

再以氣相層析-質譜儀(GC-MS)進行該由式(3-1)所示化合物3CPGB2的測試，結果為：GC-MS：m/z=440.2963[M]⁺。 The test of the compound 3CPGB2 of the formula (3-1) was carried out by gas chromatography-mass spectrometry (GC-MS). The result was: GC-MS: m/z = 440.2963 [M] ⁺ .

[實施例6]由式(4-1)所示化合物(3PTGB2)的製備[Example 6] Preparation of Compound (3PTGB2) represented by Formula (4-1)

除了將4-丙基苯酚(24mmol)置換為4-乙基苯酚(24mmol)、將2-溴-5-丙基苯并呋喃(2.3g，9.6mmol)置換成2-溴-5-乙基苯并呋喃(2.2g，9.6mmol)，及將2-氟，4’-乙基聯苯硼酸(3.6g，14.8mmol)置換成3-氟-4’-苯基乙炔基-4-丙基-苯硼酸(4.17g，14.8mmol)外，其餘製程及條件與實施例1相同，最後製得2.6g的由式(4-1)所示化合物3PTGB2。 Substituting 4-propylphenol (24 mmol) with 4-ethylphenol (24 mmol) and 2-bromo-5-propylbenzofuran (2.3 g, 9.6 mmol) with 2-bromo-5-ethyl Benzofuran (2.2 g, 9.6 mmol), and 2-fluoro, 4'-ethylbiphenylboronic acid (3.6 g, 14.8 mmol) was replaced by 3-fluoro-4'-phenylethynyl-4-propyl Except for phenylboronic acid (4.17 g, 14.8 mmol), the other processes and conditions were the same as in Example 1, and finally 2.6 g of compound 3PTGB2 represented by formula (4-1) was obtained.

以400MHz的核磁共振儀(¹H-NMR)進行該由式(4-1)所示化合物3PTGB2的測試，結果為：¹H-NMR(CDCl₃,400MHz),δ(ppm)：0.922(t,3H,J=8Hz),1.129(t,3H,J=8Hz),1.58-1.67(m,2H),2.55-2.78(m,4H),7.10-7.47(m,11H)。 In a 400MHz NMR spectrometer ⁽¹ H-NMR) for the formula (4-1), a compound 3PTGB2 test ^{_{results: 1 H-NMR (CDCl 3}} , 400MHz), δ (ppm): 0.922 (t , 3H, J = 8 Hz), 1.129 (t, 3H, J = 8 Hz), 1.58-1.67 (m, 2H), 2.55-2.78 (m, 4H), 7.10-7.47 (m, 11H).

再以氣相層析-質譜儀(GC-MS)進行該由式(4-1)所示化合物3PTGB2的測試，結果為：GC-MS：m/z=382.2563[M]⁺。 The test of the compound 3PTGB2 of the formula (4-1) was carried out by gas chromatography-mass spectrometry (GC-MS). The result was: GC-MS: m/z = 382.2563 [M] ⁺ .

[比較例1]如以下化學式的化合物CE1[Comparative Example 1] Compound CE1 of the following chemical formula

(為CN 100415730C所保護的具體例) (Specific example protected by CN 100415730C)

除了將4-丙基苯酚(24mmol)置換為4-乙基苯酚(24mmol)、將2-溴-5-丙基苯并呋喃(2.3g，9.6mmol)置換成2-溴-5-乙基苯并呋喃(2.2g，9.6mmol)，及將2-氟，4’-乙基聯苯硼酸(3.6g，14.8mmol)置換成1-氟-3-(4-丙基環己基)-苯基硼酸(3.9g，14.8mmol)外，其餘製程及條件與實施例1相同，最後製得2.5g的由上式所示化合物CE1。 Substituting 4-propylphenol (24 mmol) with 4-ethylphenol (24 mmol) and 2-bromo-5-propylbenzofuran (2.3 g, 9.6 mmol) with 2-bromo-5-ethyl Benzofuran (2.2 g, 9.6 mmol), and 2-fluoro, 4'-ethylbiphenylboronic acid (3.6 g, 14.8 mmol) was replaced by 1-fluoro-3-(4-propylcyclohexyl)-benzene Except for the boronic acid (3.9 g, 14.8 mmol), the other processes and conditions were the same as in Example 1, and finally 2.5 g of the compound CE1 represented by the above formula was obtained.

以400MHz的核磁共振儀(¹H-NMR)進行該化合物CE1的測試，結果為：¹H-NMR(CDCl₃,400MHz),δ(ppm)：0.98-1.48(m,15H),1.84-1.91(m,4H),2.44-2.51(m,1H),2.715(q,2H,J=8Hz),7.005(d,1H,J=12Hz)7.05-7.12(m,3H),7.38-7.40(m,2H),7.884(t,1H,J=8Hz)。 The test of the compound CE1 was carried out by a 400 MHz nuclear magnetic resonance apparatus ( ¹ H-NMR), and the results were as follows: ¹ H-NMR (CDCl ₃ , 400 MHz), δ (ppm): 0.98-1.48 (m, 15H), 1.84-1.91 (m, 4H), 2.44-2.51 (m, 1H), 2.715 (q, 2H, J = 8 Hz), 7.005 (d, 1H, J = 12 Hz) 7.05-7.12 (m, 3H), 7.38-7.40 (m , 2H), 7.848 (t, 1H, J = 8 Hz).

再以氣相層析-質譜儀(GC-MS)進行該化合物CE1的測試，結果為：GC-MS：m/z=364.2108[M]⁺。 The test of the compound CE1 was carried out by gas chromatography-mass spectrometry (GC-MS). The result was: GC-MS: m/z = 364.2108 [M] ⁺ .

[比較例2]如以下化學式的化合物CE2[Comparative Example 2] Compound CE2 of the following chemical formula

除了將2-氟，4’-乙基聯苯硼酸(3.6g，14.8mmol)置換成1-丁氧基-2,3-二氟-苯基硼酸(3.4g，14.8mmol)外，其餘製程及條件與實施例1相同，最後製得2.1g的由上式所示化合物CE2。 Except for 2-fluoro, 4'-ethylbiphenylboronic acid (3.6 g, 14.8 mmol) was replaced by 1-butoxy-2,3-difluoro-phenylboronic acid (3.4 g, 14.8 mmol), the rest of the process The conditions were the same as in Example 1, and finally 2.1 g of the compound CE2 represented by the above formula was obtained.

以400MHz的核磁共振儀(¹H-NMR)進行該化合物CE2的測試，結果為：¹H-NMR(CDCl₃,400MHz),δ(ppm)：0.92-0.99(m,6H),1.41-1.84(m,6H),2.657(t,2H,J=7.8Hz),4.034(t,2H, J=8.0Hz),6.78-6.83(m,1H),7.04-7.10(m,2H),7.36-7.41(m,2H),7.61-7.65(m,1H)。 The test compound is performed to CE2 400MHz nuclear magnetic resonance apparatus ⁽¹ H-NMR), the result ^{_{is: 1 H-NMR (CDCl 3}} , 400MHz), δ (ppm): 0.92-0.99 (m, 6H), 1.41-1.84 (m,6H), 2.657 (t, 2H, J = 7.8 Hz), 4.034 (t, 2H, J = 8.0 Hz), 6.78-6.83 (m, 1H), 7.04-7.10 (m, 2H), 7.36- 7.41 (m, 2H), 7.61-7.65 (m, 1H).

再以氣相層析-質譜儀(GC-MS)進行該化合物CE2的測試，結果為：GC-MS：m/z=344.2975[M]⁺。 The compound CE2 was tested by gas chromatography-mass spectrometry (GC-MS) and found to be: GC-MS: m/z = 344.2975 [M] ⁺ .

[比較例3]如以下化學式的化合物CE3[Comparative Example 3] Compound CE3 of the following chemical formula

除了將4-丙基苯酚(24mmol)置換為4-乙基苯酚(24mmol)、將2-溴-5-丙基苯并呋喃(2.3g，9.6mmol)置換成2-溴-5-乙基苯并呋喃(2.2g，9.6mmol)，及將2-氟，4’-乙基聯苯硼酸(3.6g，14.8mmol)置換成4-丙基-苯硼酸(2.4g，14.8mmol)外，其餘製程及條件與實施例1相同，最後製得1.8g的由上式所示化合物CE3。 Substituting 4-propylphenol (24 mmol) with 4-ethylphenol (24 mmol) and 2-bromo-5-propylbenzofuran (2.3 g, 9.6 mmol) with 2-bromo-5-ethyl Benzofuran (2.2 g, 9.6 mmol), and 2-fluoro, 4'-ethylbiphenylboronic acid (3.6 g, 14.8 mmol) were replaced with 4-propyl-benzeneboronic acid (2.4 g, 14.8 mmol). The rest of the processes and conditions were the same as in Example 1, and finally 1.8 g of the compound CE3 represented by the above formula was obtained.

以400MHz的核磁共振儀(¹H-NMR)進行該化合物CE3的測試，結果為：¹H-NMR(CDCl₃,400MHz),δ(ppm)：0.893(t,3H,J=8Hz),1.242(t,3H,J=8Hz),1.63-1.72(m,2H),2.66-2.70(m,4H),5.899(s,1H),7.072(d,1H,J=8Hz)7.24-7.40(m,4H),7.760(d,2H,J=8Hz)。 The compound CE3 was tested by a 400 MHz nuclear magnetic resonance apparatus ( ¹ H-NMR). The results were as follows: ¹ H-NMR (CDCl ₃ , 400 MHz), δ (ppm): 0.893 (t, 3H, J = 8 Hz), 1.242 (t,3H, J =8Hz),1.63-1.72(m,2H),2.66-2.70(m,4H),5.899(s,1H),7.072(d,1H, J =8Hz)7.24-7.40(m , 4H), 7.760 (d, 2H, J = 8 Hz).

再以氣相層析-質譜儀(GC-MS)進行該化合物CE3的測試，結果為：GC-MS：m/z=264.1614[M]⁺。 The test of the compound CE3 was carried out by gas chromatography-mass spectrometry (GC-MS). The result was: GC-MS: m/z = 264.1614 [M] ⁺ .

[比較例4]如以下化學式的化合物CE4[Comparative Example 4] Compound CE4 of the following chemical formula

除了將4-丙基苯酚(24mmol)置換為4-(4’-乙基苯基)苯酚(24mmol)、將2-溴-5-丙基苯并呋喃(2.3g，9.6mmol)置換成2-溴-5-(4’-乙基苯基)苯并呋喃(2.9g，9.6mmol)，及將2-氟，4’-乙基聯苯硼酸(3.6g，14.8mmol)置換成4-乙基-苯硼酸(2.2g，14.8mmol)外，其餘製程及條件與實施例1相同，最後製得1.9g的由上式所示化合物CE4。 Substituting 4-propylphenol (24 mmol) with 4-(4'-ethylphenyl)phenol (24 mmol) and 2-bromo-5-propylbenzofuran (2.3 g, 9.6 mmol) with 2 -Bromo-5-(4'-ethylphenyl)benzofuran (2.9 g, 9.6 mmol), and 2-fluoro, 4'-ethylbiphenylboronic acid (3.6 g, 14.8 mmol) was replaced with 4- Except for ethyl-benzeneboronic acid (2.2 g, 14.8 mmol), the other processes and conditions were the same as in Example 1, and finally 1.9 g of the compound CE4 of the above formula was obtained.

以400MHz的核磁共振儀(¹H-NMR)進行該化合物的測試，結果為：¹H-NMR(CDCl₃,400MHz),δ(ppm)：1.23-1.29(m,6H),2.65-2.71(m,4H),6.989(s,1H),7.26-7.28(m,4H,)7.44-7.54(m,4H),7.71-7.79(m,3H)。 The compound was tested by a 400 MHz nuclear magnetic resonance apparatus ( ¹ H-NMR) and found to be: ¹ H-NMR (CDCl ₃ , 400 MHz), δ (ppm): 1.23-1.29 (m, 6H), 2.65-2.71 ( m, 4H), 6.899 (s, 1H), 7.26-7.28 (m, 4H,) 7.44 - 7.54 (m, 4H), 7.71 - 7.79 (m, 3H).

再以氣相層析-質譜儀(GC-MS)進行該上式所示化合物CE4的測試，結果為：GC-MS：m/z=326.1583[M]⁺。 The test of the compound CE4 of the above formula was carried out by gas chromatography-mass spectrometry (GC-MS). The result was: GC-MS: m/z = 326.1583 [M] ⁺ .

[性質測試][Property test]

母液配製：依據重量比例1：1：1，將以下三種液晶化合物A、B及C進行混合，再加熱至澄清，然後冷卻至室溫而得到母液。 Preparation of mother liquor: The following three liquid crystal compounds A, B and C were mixed according to a weight ratio of 1:1:1, heated to clarification, and then cooled to room temperature to obtain a mother liquor.

然後分別將10重量份的上述實施例1至6及比較例1至4所製得的液晶化合物與90重量份的母液進行混合而各自形成一待測液。接著，分別運用以下方法進行實施例1至6及比較例1至4之待測液的性質測試，再由已知的母液性質並利用外插方式得出實施例1至6及比較例1至4的液晶化合物的測試結果。所有測試結果整理於表1中。 Then, 10 parts by weight of the liquid crystal compound obtained in the above Examples 1 to 6 and Comparative Examples 1 to 4 and 90 parts by weight of the mother liquid were respectively mixed to form a test liquid. Next, the properties of the liquid to be tested of Examples 1 to 6 and Comparative Examples 1 to 4 were respectively tested by the following methods, and Examples 1 to 6 and Comparative Example 1 were obtained by the known mother liquor properties and by extrapolation. Test results of 4 liquid crystal compounds. All test results are summarized in Table 1.

1.澄清點溫度(T_ni，℃)：使用差示掃描量熱儀(DSC)系統，將液晶化合物置於鋁盤上精秤0.5至10mg，藉由液晶化合物因相變化而出現的吸熱峰及放熱峰的起始點來確定相變化溫度。相變化的表示方式為：結晶相標示為C，近晶相標示為S，向列相標示為N，液體標示為I。其中，由向列相至液體的相變溫度為澄清點溫度(T_ni)。 1. Clarification point temperature (T _ni , ° C): using a differential scanning calorimeter (DSC) system, the liquid crystal compound is placed on an aluminum plate with a scale of 0.5 to 10 mg, and the endothermic peak due to the phase change of the liquid crystal compound And the starting point of the exothermic peak to determine the phase change temperature. The phase change is expressed as: the crystalline phase is labeled C, the smectic phase is labeled S, the nematic phase is labeled N, and the liquid is labeled I. Among them, the phase transition temperature from the nematic phase to the liquid is the clearing point temperature (T _ni ).

2.介電異方性(△ε)：將待測液裝入液晶盒中，於溫度25℃下，對該液晶盒施加0V至20V的電壓，在平行於液晶分子長軸方向所測得的平均介電常數為ε_∥，垂直於液晶分子長軸所測得的平均介電常數為ε_⊥，介電異方性(△ε)=ε_∥-ε_⊥。 2. Dielectric anisotropy (Δε): The liquid to be tested is placed in a liquid crystal cell, and a voltage of 0 V to 20 V is applied to the liquid crystal cell at a temperature of 25 ° C, which is measured parallel to the long axis direction of the liquid crystal molecules. The average dielectric constant is ε _∥ , and the average dielectric constant measured perpendicular to the long axis of the liquid crystal molecule is ε _⊥ , and dielectric anisotropy ( Δ ε ) = ε _∥ - ε _⊥ .

3.旋轉黏度(γ₁，mPa‧S)：將待測液裝入液晶盒中，於溫度25℃下，對該液晶盒施加20V的電壓，經儀器加入介電異方性(△ε)因數換算，即可得到旋轉黏度γ₁。 3. Rotational viscosity (γ ₁ , mPa‧S): The liquid to be tested is placed in a liquid crystal cell, and a voltage of 20 V is applied to the liquid crystal cell at a temperature of 25 ° C, and dielectric anisotropy (Δ ε) is added by the instrument. By factor conversion, the rotational viscosity γ ₁ can be obtained.

4. K₁₁彈性常數(「斜展」，在20℃下的pN)：將待測液裝入液晶盒中，於溫度25℃下，對該液晶盒施加20V的電壓，經儀器加入介電異方性(△ε)因數換算，即可得到K₁₁。 4. K ₁₁ elastic constant ("slanting", pN at 20 ° C): The liquid to be tested is placed in a liquid crystal cell, and a voltage of 20 V is applied to the liquid crystal cell at a temperature of 25 ° C, and a dielectric is added by the instrument. The anisotropy (Δε) factor is converted to obtain K ₁₁ .

5. K₃₃彈性常數(「彎曲」，在20℃下的pN)：將待測液裝入液晶盒中，於溫度25℃下，對該液晶盒施加20V的電壓，經儀器加入介電異方性(△ε)因數換算，即可得到K₃₃。 5. K ₃₃ elastic constant ("bending", pN at 20 ° C): The liquid to be tested is placed in a liquid crystal cell, and a voltage of 20 V is applied to the liquid crystal cell at a temperature of 25 ° C, and a dielectric difference is added by the instrument. The squareness (Δε) factor is converted to obtain K ₃₃ .

折射率異方性(△n)：利用一目鏡上安裝有偏光板的阿貝(Abbe)折射儀(廠商：ATAGO；型號：DR-M2)，對待測液進行量測。首先，以單方向擦拭阿貝折射儀的主稜鏡的表面，接著在主稜鏡上滴加少量的待測液，接著在測試溫度25℃，使用波長為589nm的濾光光片進行折射率異方性的測量。當偏光方向與擦拭方向平行時，測得的折射率為n_∥；當偏光方向與擦拭方向垂直時，測得的折射率為n_⊥；折射率異方性(△n)=n_∥-n_⊥。 Refractive index anisotropy (Δn): The liquid to be measured was measured using an Abbe refractometer (manufacturer: ATAGO; model: DR-M2) on which a polarizing plate was attached. First, wipe the surface of the main surface of the Abbe refractometer in a single direction, then add a small amount of the liquid to be tested on the main crucible, and then perform the refractive index at a test temperature of 25 ° C using a filter of 589 nm. Measurement of anisotropy. When the polarizing direction is parallel to the wiping direction, the measured refractive index is n _∥ ; when the polarizing direction is perpendicular to the wiping direction, the measured refractive index is n _⊥ ; the refractive index anisotropy (Δn)=n _∥ -n _Oh .

[結果][result]

由表1的結果可知，相較於比較例2至4的液晶化合物CE2至4，實施例1至6的液晶化合物具有較高的T_ni、△ε及△n，且液晶化合物的添加量為10重量份，也顯示實施例1至6之液晶化合物具備不錯的相溶性。 As is clear from the results of Table 1, the liquid crystal compounds of Examples 1 to 6 had higher T _ni , Δ ε and Δ n than the liquid crystal compounds CE 2 to 4 of Comparative Examples 2 to 4, and the amount of the liquid crystal compound added was 10 parts by weight also showed that the liquid crystal compounds of Examples 1 to 6 had good compatibility.

相較於比較例1的液晶化合物CE1，實施例1至6的化合物具有較高的△ε。 The compounds of Examples 1 to 6 have a higher Δε than the liquid crystal compound CE1 of Comparative Example 1.

[紫外線穩定性測試][UV stability test]

依據【0040】段的性質測試步驟分別進行實施例1至5及比較例1至4的待測液配製，同時運用以下方法進行待測液經紫外線照射前後性質差異的比較。所有測試結果整理於表2中。 The test liquids of Examples 1 to 5 and Comparative Examples 1 to 4 were separately prepared according to the nature test steps of [0040], and the following methods were used to compare the difference in properties of the test liquid before and after ultraviolet irradiation. All test results are summarized in Table 2.

1.閾值電壓(V_th，V)：將液晶盒放置於紫外線(20mW/cm²)下照射90分鐘，再依據上述閾值電壓的測試步驟進行測試，得到UV照射後的閾值電壓。 1. Threshold voltage (V _th , V): The liquid crystal cell was placed under ultraviolet light (20 mW/cm ² ) for 90 minutes, and then tested according to the above-described threshold voltage test procedure to obtain a threshold voltage after UV irradiation.

2.介電異方性(△ε)：將液晶盒放置於紫外線(20mW/cm²)下照射90分鐘，再依據上述介電異方性的測試步驟進行測試，得到UV照射後的介電異方性。 2. Dielectric anisotropy (Δε): The liquid crystal cell is placed under ultraviolet light (20 mW/cm ² ) for 90 minutes, and then tested according to the above test procedure of dielectric anisotropy to obtain a dielectric after UV irradiation. Anisotropy.

3. K₁₁彈性常數(「斜展」，在20℃下的pN)：將液晶盒放置於紫外線(20mW/cm²)下照射90分鐘，再依據上述K₁₁彈性常數的測試步驟進行測試，得到UV照射後的K₁₁彈性常數。 3. K ₁₁ elastic constant ("oblique", pN at 20 ° C): The liquid crystal cell was placed under ultraviolet light (20 mW/cm ² ) for 90 minutes, and then tested according to the above K ₁₁ elastic constant test procedure. The K ₁₁ elastic constant after UV irradiation was obtained.

4. K₃₃彈性常數(「彎曲」，在20℃下的pN)：將液晶盒放置於紫外線(20mW/cm²)下照射90分鐘，再依據上述K₃₃彈性常數的測試步驟進行測試，得到UV照射後的K₃₃彈性常數。 4. K ₃₃ elastic constant ("bending", pN at 20 ° C): The liquid crystal cell was placed under ultraviolet light (20 mW/cm ² ) for 90 minutes, and then tested according to the above K ₃₃ elastic constant test procedure, K ₃₃ elastic constant after UV irradiation.

表2 Table 2

[結果][result]

由表2結果可知，相較於比較例1至4的化合物CE1至CE4，實施例1至5的化合物2-1至2-5於UV照射前後的性質數值差異是於±8.8%以內，顯示實施例1至5的化合物2-1至2-5具備較優異的紫外線穩定性，更證明本發明含有2,5-苯并呋喃基團的化合物可以讓液晶組成物具備較佳的紫外線穩定性。 As is clear from the results of Table 2, the difference in the property values of the compounds 2-1 to 2-5 of Examples 1 to 5 before and after UV irradiation was within ±8.8% as compared with the compounds CE1 to CE4 of Comparative Examples 1 to 4, showing The compounds 2-1 to 2-5 of Examples 1 to 5 have excellent ultraviolet stability, and it is further confirmed that the compound containing a 2,5-benzofuran group of the present invention can provide a liquid crystal composition with better ultraviolet stability. .

綜上所述，本發明含有2,5-苯并呋喃基團的化合物具備新穎的結構設計及良好的液晶特性，例如較寬的液晶態溫度範圍、良好的低溫互溶性、較高的雙折射率、較低的黏度、較大的K值、及光、熱穩定等特性。而於後續應用於液晶組成物時，能有效提升液晶組成物的T_ni、△n等性質，更能讓液晶組成物具備良好的紫外線穩定性，故確實能達成本發明之目的。 In summary, the compound containing a 2,5-benzofuran group of the present invention has novel structural design and good liquid crystal characteristics, such as a wide liquid crystal temperature range, good low temperature miscibility, and high birefringence. Rate, low viscosity, large K value, and light and heat stability. When it is applied to the liquid crystal composition in the subsequent application, the properties of T _ni and Δn of the liquid crystal composition can be effectively improved, and the liquid crystal composition can be made to have good ultraviolet stability, so that the object of the present invention can be achieved.

惟以上所述者，僅為本發明之實施例而已，當不能以此限定本發明實施之範圍，凡是依本發明申請專利範圍及專利說明書內容所作之簡單的等效變化與修飾，皆仍屬本發明專利涵蓋之範圍內。 However, the above is only the embodiment of the present invention, and the scope of the invention is not limited thereto, and all the equivalent equivalent changes and modifications according to the scope of the patent application and the patent specification of the present invention are still The scope of the invention is covered.

Claims

一種含有2,5-苯并呋喃基團的化合物，具有以下化學式1所示的結構：於化學式1中，R¹表示鹵素原子、-CN、C₁~C₁₀烷基、C₁~C₁₀烷氧基或C₂~C₁₀烯基，該烷基、該烷氧基或該烯基中的至少一個氫可以被鹵素原子所取代，或者至少一個-CH₂-可被-O-取代，且各個-O-彼此不直接相連接；環A表示1,4-伸苯基或1,4-伸環己烷基；Z¹及Z²各自獨立地表示單鍵、-(CH₂)₂-、-COO-、-OCO-、-OOC-、-C≡C-或-CH=CH-；L¹~L⁷各自獨立地表示H、-CN或鹵素原子；R²表示C₁~C₁₀烷基或C₂~C₁₀烯基，該烷基或該烯基中的至少一個氫可以被鹵素原子所取代，或者至少一個-CH₂-可被-O-取代，且各個-O-彼此不直接相連接；及n表示0或1。 A compound containing a 2,5-benzofuran group having the structure shown in the following Chemical Formula 1: In Chemical Formula 1, R ¹ represents a halogen atom, -CN, C ₁ -C ₁₀ alkyl group, C ₁ -C ₁₀ alkoxy group or C ₂ -C ₁₀ alkenyl group, the alkyl group, the alkoxy group or the alkene At least one hydrogen in the group may be substituted by a halogen atom, or at least one -CH ₂ - may be substituted by -O-, and each -O- is not directly bonded to each other; ring A represents 1,4-phenylene or 1 , 4-cyclohexyl group; Z ¹ and Z ² each independently represent a single bond, -(CH ₂ ) ₂ -, -COO-, -OCO-, -OOC-, -C≡C- or -CH= CH-; L ¹ to L ⁷ each independently represent H, -CN or a halogen atom; R ² represents a C ₁ -C ₁₀ alkyl group or a C ₂ -C ₁₀ alkenyl group, at least one of the alkyl group or the alkenyl group Hydrogen may be substituted by a halogen atom, or at least one -CH ₂ - may be substituted by -O-, and each -O- is not directly bonded to each other; and n represents 0 or 1.

如請求項1所述的含有2,5-苯并呋喃基團的化合物，其中，R²表示C₁~C₁₀烷基或C₂~C₁₀烯基。 The compound containing a 2,5-benzofuran group according to claim 1, wherein R ² represents a C ₁ -C ₁₀ alkyl group or a C ₂ -C ₁₀ alkenyl group.

如請求項1所述的含有2,5-苯并呋喃基團的化合物，其中，該n表示0。 The compound containing a 2,5-benzofuran group according to claim 1, wherein the n represents 0.

如請求項1所述的含有2,5-苯并呋喃基團的化合物，其中，該Z¹及Z²為單鍵。 The compound containing a 2,5-benzofuran group according to claim 1, wherein the Z ¹ and Z ² are a single bond.

如請求項1所述的含有2,5-苯并呋喃基團的化合物，其中，該L¹~L⁷皆表示氫。 The compound containing a 2,5-benzofuran group according to claim 1, wherein the L ¹ to L ⁷ represent hydrogen.

如請求項1所述的含有2,5-苯并呋喃基團的化合物，其中，該R¹及R²各自表示C₁~C₁₀烷基。 The compound containing a 2,5-benzofuran group according to claim 1, wherein each of R ¹ and R ² represents a C ₁ -C ₁₀ alkyl group.

如請求項1所述的含有2,5-苯并呋喃基團的化合物，其中，該n表示0，該Z¹及Z²為單鍵，該L¹~L⁷皆表示氫，及該R¹及R²各自表示C₁~C₁₀烷基。 The compound containing a 2,5-benzofuran group according to claim 1, wherein the n represents 0, the Z ¹ and Z ² are single bonds, and the L ¹ to L ⁷ represent hydrogen, and the R ¹ and R ² each represent a C ₁ to C ₁₀ alkyl group.

一種液晶組成物，包含至少一種如請求項1至7中任一項所述的含有2,5-苯并呋喃基團的化合物。 A liquid crystal composition comprising at least one compound containing a 2,5-benzofuran group according to any one of claims 1 to 7.

一種顯示單元，包含一種如請求項8所述的液晶組成物。 A display unit comprising the liquid crystal composition as claimed in claim 8.