TW201819601A - Compound, liquid crystal medium containing the compound, and display unit effectively reducing startup voltage and increasing the degree of penetration of the display unit - Google Patents

Compound, liquid crystal medium containing the compound, and display unit effectively reducing startup voltage and increasing the degree of penetration of the display unit Download PDF

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TW201819601A
TW201819601A TW105138564A TW105138564A TW201819601A TW 201819601 A TW201819601 A TW 201819601A TW 105138564 A TW105138564 A TW 105138564A TW 105138564 A TW105138564 A TW 105138564A TW 201819601 A TW201819601 A TW 201819601A
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phenylene
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TWI599640B (en
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李清田
林怡君
王俊智
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達興材料股份有限公司
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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
    • C09K19/3402—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D319/04—1,3-Dioxanes; Hydrogenated 1,3-dioxanes
    • C07D319/08—1,3-Dioxanes; Hydrogenated 1,3-dioxanes condensed with carbocyclic rings or ring systems
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
    • C09K19/3402—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom
    • C09K2019/3422—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom the heterocyclic ring being a six-membered ring
    • C09K2019/3425—Six-membered ring with oxygen(s) in fused, bridged or spiro ring systems

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Abstract

A liquid crystal medium which comprises at least one compound I represented by chemical formula 1. The definitions of R1, R2, X1, X2, A1, A2, A3, A4, n, m, and o in the chemical formula 1 are as described in the specification and the claims of the patent application. The present invention also refers to a compound represented by the chemical formula 1, and a display unit containing the liquid crystal medium. Since the liquid crystal medium of the present invention contains the compound I represented by the chemical formula 1 having higher [DELTA][epsilon] and [epsilon]&bottom, when it is subsequently applied to a liquid crystal display unit, it can effectively reduce the startup voltage and increase the degree of penetration.

Description

化合物、含有此化合物的液晶介質及顯示單元Compound, liquid crystal medium and display unit containing the same

本發明是有關於一種化合物、含有此化合物的液晶介質及顯示單元，特別是指一種由化學式1所示的化合物、含有此化合物的液晶介質及顯示單元。The present invention relates to a compound, a liquid crystal medium and a display unit containing the compound, and particularly to a compound represented by Chemical Formula 1, a liquid crystal medium and a display unit containing the compound.

因應液晶顯示單元的廣泛使用，液晶化合物的各項性質，如介電各異向性(Δε)、折射各異向性(Δn)、旋轉黏度(γ1)等，仍被要求不斷地改善，所以，目前業界還需就新穎的液晶化合物或液晶介質(matrix)進行研發。In response to the wide use of liquid crystal display units, various properties of liquid crystal compounds, such as dielectric anisotropy (Δε), refractive anisotropy (Δn), and rotational viscosity (γ1), are still required to be continuously improved, so Currently, the industry still needs to research and develop novel liquid crystal compounds or liquid crystal media.

美國專利公開案US 2009/0066905 A1揭示一種含有苯并二噁烷(dioxatetralin)基團的化合物，其具有以下結構(A)： (A)， 於以上結構(A)中，G1 和G2 表示氰基、鹵基、選擇性取代的烴基(hydrocarbyl)、選擇性取代的烷氧基、選擇性取代的雜環基(heterocyclyl)、RC(O)O-或ROC(O)-，其中，R表示選擇性取代的烴基；G3 、G4 及G5 分別表示氫、鹵素、CF3 或SF5 ；Y1 、Y2 、Y3 及Y4 分別表示單鍵、-CH2 CH2 -、-(CH2 )4 -、-CH2 O-、-CH=CH-、-C≡C-、-COO-、-OCO-或-OCH2 -；E1 、E2 、E3 和E4 分別表示1,4-伸苯基、1,4-伸環己基或伸雜環基，前述基團可選擇地被取代；及t1、t2、t3和t4分別為0或1，其條件是t1+t2+t3+t4大於0；當t1為0時，t2為0；及當t3為0時，t4為0。於此美國專利公開案的多數實施例中，結構(A)之t3=t4=0，或者t3及t4其中一者為1，另一者為0。實施例中的多數化合物的Δε＜0，顯示此美國專利案中的化合物是以負型液晶為主。United States Patent Publication US 2009/0066905 A1 discloses a compound containing a benzodioxane (dioxatetralin) group, which has the following structure (A): (A) In the above structure (A), G 1 and G 2 represent cyano, halo, optionally substituted hydrocarbyl, selectively substituted alkoxy, selectively substituted heterocyclyl, RC (O) O- or ROC (O)-, wherein R represents a selectively substituted hydrocarbon group; G 3 , G 4 and G 5 represent hydrogen, halogen, CF 3 or SF 5 respectively ; Y 1 , Y 2 , Y 3 And Y 4 represent a single bond, -CH 2 CH 2 -,-(CH 2 ) 4- , -CH 2 O-, -CH = CH-, -C≡C-, -COO-, -OCO-, or- OCH 2- ; E 1 , E 2 , E 3 and E 4 respectively represent 1,4-phenylene, 1,4-cyclohexyl or heterocyclo, the aforementioned groups are optionally substituted; and t1 t2, t3, and t4 are 0 or 1, respectively, provided that t1 + t2 + t3 + t4 is greater than 0; when t1 is 0, t2 is 0; and when t3 is 0, t4 is 0. In most embodiments of this U.S. Patent Publication, t3 = t4 = 0 of the structure (A), or one of t3 and t4 is 1 and the other is 0. Most of the compounds in the examples have Δε <0, which shows that the compounds in this US patent are mainly negative liquid crystals.

因此，本發明之目的，即在提供一種液晶介質，其能夠達成以下至少一種功效：降低顯示器的啟動電壓、縮短反應時間和提升穿透度。Therefore, the object of the present invention is to provide a liquid crystal medium that can achieve at least one of the following effects: reducing the startup voltage of the display, shortening the response time, and increasing the penetration.

於是，本發明液晶介質，包含：至少一種由化學式1所示的化合物I： [化學式1]， 於化學式1中，R1 表示碳數範圍為1~10的烷基、碳數範圍為1~10的烷氧基、碳數範圍為2~10的烯基或碳數範圍為2~10的烯氧基，該烷基、烷氧基、烯基或烯氧基中的一或多個氫可選擇地被氟取代； X1 及X2 各自表示氫或氟； A1 、A2 、A3 及A4 各自表示1,4-伸環己基、1,4-伸苯基、3,5-二氟-1,4-伸苯基、2,3-二氟-1,4-伸苯基或3-氟-1,4-伸苯基； n表示0、1或2，當n為2時，兩個A2 可為相同或不同； m及o表示0或1，且m+o≥1；及 R2 表示鹵素、OCF3 、CF3 或CN。Therefore, the liquid crystal medium of the present invention includes: at least one compound I represented by Chemical Formula 1: [Chemical Formula 1] In Chemical Formula 1, R 1 represents an alkyl group having a carbon number range of 1 to 10, an alkoxy group having a carbon number range of 1 to 10, an alkenyl group having a carbon number range of 2 to 10 or a carbon number range of 2 to 10 One or more hydrogens in the alkyl, alkoxy, alkenyl, or alkenyl group may be optionally substituted with fluorine; X 1 and X 2 each represent hydrogen or fluorine; A 1 , A 2 , A 3 and A 4 each represent 1,4-cyclohexyl, 1,4-phenylene, 3,5-difluoro-1,4-phenylene, 2,3-difluoro-1,4-phenylene Phenyl or 3-fluoro-1,4-phenylene; n represents 0, 1, or 2, when n is 2, two A 2 may be the same or different; m and o represent 0 or 1, and m + o≥1; and R 2 represents halogen, OCF 3 , CF 3 or CN.

本發明的另一目的，即在提供一種由該化學式1所示的化合物，其為正型液晶化合物，同時具備較高Δε、較高ε⊥ 、及合適的γ1，且對酸、熱及紫外光的性質穩定。Another object of the present invention is to provide a compound represented by the chemical formula 1, which is a positive-type liquid crystal compound, and has a higher Δε, a higher ε ⊥ , and a suitable γ1, and is resistant to acids, heat, and ultraviolet rays. The nature of light is stable.

本發明的又另一目的，即在提供一種包含前述液晶介質的顯示單元。Yet another object of the present invention is to provide a display unit including the aforementioned liquid crystal medium.

本發明之功效在於：本發明液晶介質因為含有特殊結構設計且具備較高Δε及ε⊥ 的化學式1所示化合物I，於後續應用於液晶顯示單元時，可至少有效降低啟動電壓及提升穿透度。The effect of the present invention is that the liquid crystal medium of the present invention has a special structure design and has a high compound Δε and ε 化合物 of compound I shown in Chemical Formula 1. When it is subsequently applied to a liquid crystal display unit, it can effectively reduce at least the startup voltage and increase the penetration. degree.

以下就本發明內容進行詳細說明：The following describes the content of the present invention in detail:

較佳地，該化合物I是選自於化學式1-1所示化合物、化學式1-2所示化合物或化學式1-3所示化合物： [化學式1-1]， [化學式1-2]， [化學式1-3]。Preferably, the compound I is selected from a compound represented by Chemical Formula 1-1, a compound represented by Chemical Formula 1-2, or a compound represented by Chemical Formula 1-3: [Chemical Formula 1-1] , [Chemical Formula 1-2] [Chemical Formula 1-3] .

較佳地，於該化學式1-1、1-2及1-3中，A1 、A2 、A3 及A4 各自表示1,4-伸環己基、1,4-伸苯基、3,5-二氟-1,4-伸苯基或3-氟-1,4-伸苯基；R1 表示碳數範圍為1~10的烷基或碳數範圍為1~10的烷氧基；及R2 表示鹵素、OCF3 、CF3 或CN。Preferably, in the chemical formulae 1-1, 1-2 and 1-3, A 1 , A 2 , A 3 and A 4 each represent 1,4-cyclohexyl, 1,4-phenylene, 3 1,5-difluoro-1,4-phenylene or 3-fluoro-1,4-phenylene; R 1 represents an alkyl group having a carbon number of 1 to 10 or an alkoxy group having a carbon number of 1 to 10 And R 2 represents halogen, OCF 3 , CF 3 or CN.

於本發明的具體例中，該化合物I是由化學式1-2所示且該化學式1-2所示化合物是選自於由下列所構成之群組： [化學式1-2A]， [化學式1-2B]及 [化學式1-2C]。In a specific example of the present invention, the compound I is represented by Chemical Formula 1-2 and the compound represented by Chemical Formula 1-2 is selected from the group consisting of: [Chemical Formula 1-2A] , [Chemical Formula 1-2B] And [chemical formula 1-2C] .

較佳地，於化學式1-2A、1-2B及1-2C中，R1 表示碳數範圍為1~10的烷基以及R2 表示鹵素、OCF3 、CF3 或CN。Preferably, in the chemical formulae 1-2A, 1-2B and 1-2C, R 1 represents an alkyl group having a carbon number ranging from 1 to 10 and R 2 represents halogen, OCF 3 , CF 3 or CN.

該化學式1所示的化合物I的製法可依據已知方法進行製備，例如但不限於利用以下步驟1至步驟4的反應式進行製備： [步驟1][步驟2][步驟3][步驟4]。The method for preparing the compound I represented by Chemical Formula 1 can be prepared according to a known method, such as, but not limited to, using the following reaction formulas of Step 1 to Step 4: [Step 1] [Step 2] [Step 3] [Step 4] .

本發明液晶介質可以依據實際需要進一步選用其他液晶化合物。較佳地，該液晶介質還包含至少一種化合物II，是由化學式2所示： [化學式2]， 於化學式2中，R3 表示碳數範圍為1~10的烷基、碳數範圍為1~10的烷氧基、碳數範圍為2~10的烯基或碳數範圍為2~10的烯氧基，該烷基、烷氧基、烯基或烯氧基中的一或多個氫可選擇地被氟取代； B1 表示1,4-伸環己基、1,4-伸苯基、或； B2 及B3 各自表示1,4-伸環己基、1,4-伸苯基、3,5-二氟-1,4-伸苯基、2,3-二氟-1,4-伸苯基或3-氟-1,4-伸苯基； p表示0或1； Z1 表示單鍵、−(CH2 )2 −、−COO−、−CH2 O−、−OCO−、−CF2 O−、−OCF2 −、−C≡C−或−CH=CH−；及 R4 表示鹵素、OCF3 、OCHCF2 、OCF2 H、CF3 或CN。The liquid crystal medium of the present invention can further select other liquid crystal compounds according to actual needs. Preferably, the liquid crystal medium further comprises at least one compound II, which is represented by Chemical Formula 2: [Chemical Formula 2] In Chemical Formula 2, R 3 represents an alkyl group having a carbon number range of 1 to 10, an alkoxy group having a carbon number range of 1 to 10, an alkenyl group having a carbon number range of 2 to 10 or a carbon number range of 2 to 10 Alkenyloxy, one or more hydrogens of the alkyl, alkoxy, alkenyl or alkenyloxy may be optionally substituted by fluorine; B 1 represents 1,4-cyclohexyl, 1,4-benzene base, or B 2 and B 3 each represent 1,4-cyclohexyl, 1,4-phenylene, 3,5-difluoro-1,4-phenylene, 2,3-difluoro-1,4- Phenylene or 3-fluoro-1,4-phenylene; p represents 0 or 1; Z 1 represents a single bond, − (CH 2 ) 2 −, −COO−, −CH 2 O−, −OCO−, −CF 2 O−, −OCF 2 −, −C≡C−, or −CH = CH−; and R 4 represents halogen, OCF 3 , OCHCF 2 , OCF 2 H, CF 3, or CN.

較佳地，該化合物II是選自於化學式2-1所示化合物或化學式2-2所示化合物： [化學式2-1][化學式2-2]。Preferably, the compound II is selected from a compound represented by Chemical Formula 2-1 or a compound represented by Chemical Formula 2-2: [Chemical Formula 2-1] [Chemical Formula 2-2] .

較佳地，該化學式2-1及2-2中，R3 表示碳數範圍為1~10的烷基；B2 及B3 各自表示1,4-伸環己基、1,4-伸苯基、3,5-二氟-1,4-伸苯基或3-氟-1,4-伸苯基；Z1 表示單鍵或−CF2 O−；R4 表示氟、OCHCF2 或OCF2 H。Preferably, in the chemical formulae 2-1 and 2-2, R 3 represents an alkyl group having a carbon number ranging from 1 to 10; B 2 and B 3 each represent 1,4-cyclohexyl, 1,4-benzene Group, 3,5-difluoro-1,4-phenylene or 3-fluoro-1,4-phenylene; Z 1 represents a single bond or −CF 2 O−; R 4 represents fluorine, OCHCF 2 or OCF 2 H.

較佳地，該液晶介質還包含至少一種化合物III，是由化學式3所示： [化學式3]， 於化學式3中，R5 表示碳數範圍為1~10的烷基、碳數範圍為1~10的烷氧基、碳數範圍為2~10的烯基或碳數範圍為2~10的烯氧基，該烷基、烷氧基、烯基或烯氧基中的一或多個氫可選擇地被氟取代； C1 、C2 、C3 及C4 各自表示1,4-伸環己基、1,4-伸苯基、2,3-二氟-1,4-伸苯基、3-氟-1,4-伸苯基、2,5-伸苯并呋喃基或2,6-伸7,8-二氟-1,3-苯并二噁烷基； q、r及s各自表示0或1； Z2 、Z3 及Z4 各自表示單鍵、−(CH2 )2 −、−COO−、−CH2 O−、−OCO−、−CF2 O−、−OCF2 −、−C≡C−或−CH=CH−；及 R6 表示鹵素、OCF3 、CF3 、CN、碳數範圍為1~10的烷基、碳數範圍為1~10的烷氧基、碳數範圍為2~10的烯基或碳數範圍為2~10的烯氧基，該烷基、烷氧基、烯基或烯氧基中的一或多個氫可選擇地被氟取代。Preferably, the liquid crystal medium further comprises at least one compound III, which is represented by Chemical Formula 3: [Chemical Formula 3] In Chemical Formula 3, R 5 represents an alkyl group having a carbon number range of 1 to 10, an alkoxy group having a carbon number range of 1 to 10, an alkenyl group having a carbon number range of 2 to 10 or a carbon number range of 2 to 10 Alkenyloxy, one or more hydrogens of the alkyl, alkoxy, alkenyl or alkenyloxy may be optionally substituted by fluorine; C 1 , C 2 , C 3 and C 4 each represent 1,4- Cyclohexyl, 1,4-phenylene, 2,3-difluoro-1,4-phenylene, 3-fluoro-1,4-phenylene, 2,5-phenylbenzofuranyl, or 2 , 6-Extended 7,8-difluoro-1,3-benzodioxane; q, r and s each represent 0 or 1; Z 2 , Z 3 and Z 4 each represent a single bond, − (CH 2 ) 2 −, −COO−, −CH 2 O−, −OCO−, −CF 2 O−, −OCF 2 −, −C≡C−, or −CH = CH−; and R 6 represents halogen, OCF 3 , CF 3 , CN, alkyl with 1 to 10 carbons, alkoxy with 1 to 10 carbons, alkenyl with 2 to 10 carbons or alkenyl with 2 to 10 carbons One or more hydrogens in the alkyl, alkoxy, alkenyl, or alkenyloxy group may be optionally substituted with fluorine.

較佳地，該化合物III是選自於化學式3-1所示化合物、化學式3-2所示化合物、化學式3-3所示化合物、化學式3-4所示化合物或化學式3-5所示化合物： [化學式3-1][化學式3-2][化學式3-3][化學式3-4][化學式3-5]。Preferably, the compound III is selected from a compound represented by Chemical Formula 3-1, a compound represented by Chemical Formula 3-2, a compound represented by Chemical Formula 3-3, a compound represented by Chemical Formula 3-4, or a compound represented by Chemical Formula 3-5 : [Chemical Formula 3-1] [Chemical Formula 3-2] [Chemical Formula 3-3] [Chemical Formula 3-4] [Chemical Formula 3-5] .

較佳地，於化學式3-1至3-5中，R5 表示碳數範圍為1~10的烷基或碳數範圍為2~10的烯基；Z2 、Z3 及Z4 各自表示單鍵或−C≡C−；R6 表示氟、OCF3 、碳數範圍為1~10的烷基、碳數範圍為1~10的烷氧基或碳數範圍為2~10的烯基。Preferably, in the chemical formulae 3-1 to 3-5, R 5 represents an alkyl group having a carbon number ranging from 1 to 10 or an alkenyl group having a carbon number ranging from 2 to 10; Z 2 , Z 3 and Z 4 each represent Single bond or −C≡C−; R 6 represents fluorine, OCF 3 , alkyl group having 1 to 10 carbon atoms, alkoxy group having 1 to 10 carbon atoms or alkenyl group having 2 to 10 carbon atoms .

較佳地，該液晶介質還包含至少一種化合物IV，是由化學式4所示： [化學式4]， 於化學式4中，R7 表示碳數範圍為1~10的烷基、碳數範圍為1~10的烷氧基、碳數範圍為2~10的烯基或碳數範圍為2~10的烯氧基，該烷基、烷氧基、烯基或烯氧基中的一或多個氫可選擇地被氟取代； X3 、X4 、X5 及X6 各自表示氫或氟； D1 表示1,4-伸環己基、1,4-伸苯基、3,5-二氟-1,4-伸苯基、2,3-二氟-1,4-伸苯基或3-氟-1,4-伸苯基；及 R8 表示鹵素、碳數範圍為1~10的烷氧基、碳數範圍為2~10的烯氧基、OCHCF2 、OCF3 、CF3 或CN，該烷氧基或烯氧基的一或多個氫可選擇地被氟取代。Preferably, the liquid crystal medium further comprises at least one compound IV, which is represented by Chemical Formula 4: [Chemical Formula 4] In Chemical Formula 4, R 7 represents an alkyl group having a carbon number range of 1 to 10, an alkoxy group having a carbon number range of 1 to 10, an alkenyl group having a carbon number range of 2 to 10 or a carbon number range of 2 to 10 Alkenyloxy, one or more hydrogens of the alkyl, alkoxy, alkenyl or alkenyloxy are optionally substituted by fluorine; X 3 , X 4 , X 5 and X 6 each represent hydrogen or fluorine; D 1 represents 1,4-cyclohexyl, 1,4-phenylene, 3,5-difluoro-1,4-phenylene, 2,3-difluoro-1,4-phenylene, or 3 -Fluoro-1,4-phenylene; and R 8 represents halogen, alkoxy having 1 to 10 carbons, alkenoxy having 2 to 10 carbons, OCHCF 2 , OCF 3 , CF 3 or CN, one or more hydrogens of the alkoxy or alkenyloxy group are optionally substituted with fluorine.

較佳地，該化學式4所示的化合物IV中，R7 表示碳數範圍為1~10的烷基；X3 、X4 、X5 及X6 各自表示氫；D1 表示1,4-伸苯基；R8 表示OCHCF2 。Preferably, in the compound IV represented by Chemical Formula 4, R 7 represents an alkyl group having a carbon number ranging from 1 to 10; X 3 , X 4 , X 5 and X 6 each represent hydrogen; D 1 represents 1,4- Phenylene; R 8 represents OCHCF 2 .

當該液晶介質包含至少一種化合物I、至少一種化合物II、至少一種化合物III及至少一種化合物IV時，較佳地，以該液晶介質的總重為100 wt%計算，該化合物I的總含量範圍為1~30 wt%，該化合物II的總含量範圍為1~30 wt%，該化合物III的總含量範圍為40~90 wt%及該化合物IV的總含量範圍為0~10 wt%。更佳地，以該液晶介質的總重為100 wt%計算，該化合物I的總含量範圍為1~25 wt%，該化合物II的總含量範圍為5~20 wt%，該化合物III的總含量範圍為50~90 wt%及該化合物IV的總含量範圍為0~5 wt%。When the liquid crystal medium includes at least one compound I, at least one compound II, at least one compound III, and at least one compound IV, preferably, the total content range of the compound I is calculated based on the total weight of the liquid crystal medium being 100 wt%. It is 1 to 30 wt%, the total content of the compound II ranges from 1 to 30 wt%, the total content of the compound III ranges from 40 to 90 wt%, and the total content of the compound IV ranges from 0 to 10 wt%. More preferably, based on the total weight of the liquid crystal medium being 100 wt%, the total content of the compound I ranges from 1 to 25 wt%, and the total content of the compound II ranges from 5 to 20 wt%. The content ranges from 50 to 90 wt% and the total content of the compound IV ranges from 0 to 5 wt%.

本發明顯示單元包含上述的液晶介質。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 includes the above-mentioned liquid crystal medium. 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 present invention will be further described with reference to the following examples, but it should be understood that this example is for illustrative purposes only and should not be construed as a limitation on the implementation of the present invention.

以下實施例與比較例中的液晶化合物結構分別運用下表1的代號來表示： [表1] The structures of the liquid crystal compounds in the following examples and comparative examples are represented by the codes in Table 1 below: [Table 1]

[ 測試 ] 下述實施例及比較例分別選擇地依據以下方法進行測試： 1. 澄清點溫度(Tni ，°C)：使用差示掃描量熱儀(DSC)系統，將待測液或液晶介質置於鋁盤上精秤0.5至10 mg，藉由待測液或液晶介質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(Tni )。 2. 介電各向異性(Δε)：將待測液或液晶介質裝入液晶盒中，於溫度25°C下，對該液晶盒施加0 V至20 V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⊥ ，介電各向異性(Δε)＝ε‖ －ε⊥ 。依據Japanese Journal of Applied Physics , 53, p.010304, 2014可以得知當ε⊥ 越大，光穿透度越大。 3. 旋轉黏度(γ1，mPa•S)：將待測液或液晶介質裝入液晶盒中，於溫度25°C下，對該液晶盒施加20 V的電壓，經儀器加入介電各向異性(Δε)因數換算，即可得到旋轉黏度γ1。 4. K11彈性常數(「斜展」，在20°C下的pN)：將待測液或液晶介質裝入液晶盒中，於溫度25°C下，對該液晶盒施加20 V的電壓，經儀器加入介電各向異性(Δε)因數換算，即可得到K11。 5. K33彈性常數(「彎曲」，在20°C下的pN)：將待測液或液晶介質裝入液晶盒中，於溫度25°C下，對該液晶盒施加20 V的電壓，經儀器加入介電異方性(Δε)因數換算，即可得到K33。 6. 折射率各向異性(Δn)：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)，對待測液或液晶介質進行量測。首先，以單方向擦拭阿貝折射儀的主稜鏡表面，接著在主稜鏡上滴加少量的待測液，接著在測試溫度25°C，使用波長為589 nm的濾光光片進行折射率各向異性的測量。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⊥ ；折射率各向異性(Δn)＝n‖ －n⊥ 。 7. 低溫儲存天數(low temperature storage，簡稱LTS，單位：天)：將0.3 g的待測液或液晶介質裝入7 mL玻璃瓶中，再將玻璃瓶置入-30°C的定溫冷凍櫃中，記錄液晶析出的時間，即為低溫儲存天數。低溫儲存天數越長越佳。 [ Test ] The following examples and comparative examples were selected for testing according to the following methods: 1. Clearing point temperature ( Tni , ° C): Using a differential scanning calorimeter (DSC) system, the test liquid or liquid crystal The medium is placed on an aluminum pan and finely weighed from 0.5 to 10 mg. The phase change temperature is determined by the starting point of the endothermic peak and the exothermic peak of the liquid or liquid crystal medium due to the phase change. The phase change is expressed as follows: 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. Dielectric anisotropy (Δε): Put the test liquid or liquid crystal medium into the liquid crystal cell, and apply a voltage of 0 V to 20 V to the liquid crystal cell at a temperature of 25 ° C. The average dielectric constant measured in the axial direction is ε ‖ , the average dielectric constant measured perpendicular to the long axis of the liquid crystal molecules is ε ⊥ , and the dielectric anisotropy (Δε) = ε ‖- ε ⊥ . According to the Japanese Journal of Applied Physics , 53, p.010304, 2014, it can be known that the larger the ε ⊥, the greater the light transmission. 3. Rotary viscosity (γ1, mPa • S): Put the liquid to be measured or the liquid crystal medium into the liquid crystal cell, apply a voltage of 20 V to the liquid crystal cell at a temperature of 25 ° C, and add the dielectric anisotropy through the instrument (Δε) factor conversion, the rotational viscosity γ1 can be obtained. 4. K11 elastic constant ("slope spread", pN at 20 ° C): Put the liquid to be measured or the liquid crystal medium into the liquid crystal cell, and apply a voltage of 20 V to the liquid crystal cell at a temperature of 25 ° C. After adding the dielectric anisotropy (Δε) factor conversion to the instrument, K11 can be obtained. 5. K33 elastic constant ("bend", pN at 20 ° C): Put the liquid to be measured or the liquid crystal medium into the liquid crystal cell, and apply a voltage of 20 V to the liquid crystal cell at a temperature of 25 ° C. K33 can be obtained by adding dielectric anisotropy (Δε) factor to the instrument. 6. Refractive index anisotropy (Δn): An Abbe refractometer (manufacturer: ATAGO; model: DR-M2) with a polarizing plate mounted on an eyepiece is used to measure the liquid to be measured or the liquid crystal medium. First, wipe the surface of the main ridge of the Abbe refractometer in one direction, then drop a small amount of liquid to be measured on the main ridge, and then refract with a filter with a wavelength of 589 nm at a test temperature of 25 ° C. Measurement of rate anisotropy. When the polarization direction is parallel to the wiping direction, the measured refractive index is n ‖ ; when the polarization direction is perpendicular to the wiping direction, the measured refractive index is n ⊥ ; the refractive index anisotropy (Δn) = n ‖ -n ⊥ . 7. Low temperature storage (LTS, unit: day): Put 0.3 g of the test solution or liquid crystal medium into a 7 mL glass bottle, and place the glass bottle in a fixed temperature of -30 ° C to freeze In the cabinet, record the liquid crystal precipitation time, which is the number of days of low temperature storage. The longer the cold storage days, the better.

[ 製備例 1 及 2] 化學式 1-2B 所示化合物 I 下面以製備例1為例進行說明： 1. 將4-丙基苯酚(3.3g，24mmol)、氯化鎂(3.9g，36mmol)，多聚甲醛(paraformaldehyde，5g，165mmol)、三乙胺(13.5mL，9.3mmol)及乙腈(60mL)放置於250mL雙頸瓶中並進行混合，獲得一反應液。使該反應液於氮氣下進行加熱迴流，反應期間以薄膜色層分析片(TLC)確認反應是否完全。待反應4小時後，確認反應完全，將鹽酸水溶液(1N，50mL)加入反應液中，得到一混合液。接著，利用乙酸乙酯對該混合液反覆進行三次萃取並收集有機層，並於該有機層中加入無水硫酸鎂，再進行過濾及減壓濃縮，得到粗產物。利用管柱層析法(沖提液為乙酸乙酯及正己烷混合液，乙酸乙酯與正己烷的體積比例為1：9)來純化該粗產物，最後獲得2-羥基-5-丙基-苯甲醛(3.2g，黃色液體)。前述反應過程如下反應式：(R1 =C3 H7 ) 2. 將硼氫化鈉(0.9g，24mmol)及甲醇(30mL)放置於250mL雙頸瓶中並冷卻至0°C。然後將2-羥基-5-丙基-苯甲醛(2.0g，12mmol)慢慢滴入雙頸瓶中，待攪拌1小時後，以TLC確認反應是否完全。待確認反應完全後，將鹽酸水溶液(1N，25mL)加入雙頸瓶中，得到一混合液。利用乙酸乙酯對該混合液反覆進行三次萃取並收集有機層，並於該有機層中加入無水硫酸鎂，再進行過濾及減壓濃縮，得到粗產物。利用管柱層析法(沖提液為乙酸乙酯及正己烷混合液，乙酸乙酯與正己烷的體積比例為2：8)來純化該粗產物，最後獲得2-羥甲基-4-丙基苯酚(1.7g，白色固體，SL1)。前述反應過程如下反應式：3. 將四(三苯基膦)鈀(0.34g，3mol%)、4-溴-3-氟-苯甲醛(3.0g，14.8mmol)、4-[(3’,4’,5’-三氟苯基)-二氟甲氧基]-3,5-二氟苯基硼酸(8.6g，60mmol，此化合物的合成可以參考EP 1341742A1)、碳酸鉀(6.1g，44.4mmol)、水(20mL)及四氫呋喃(180mL)加入雙頸圓底瓶中進行攪拌並獲得一反應液。使該反應液進行加熱及迴流，反應期間以TLC確認反應是否完全。待反應24小時後，確認反應完全，將水(100mL)加入反應液中，得到一混合液。接著，利用乙酸乙酯對該混合液反覆進行三次萃取並收集有機層，並於該有機層中加入無水硫酸鎂，再進行過濾及減壓濃縮，得到粗產物。利用管柱層析法(沖提液為正己烷)來純化該粗產物，最後獲得化合物SR2 (5.8g，白色固體)。前述反應過程如下反應式：(R2 =F) 4. 將化合物SR2(1.0g，2.4mmol)、二氯甲烷(30mL)及三甲基氯矽烷(0.5g，4.8mmol)加入250mL雙頸瓶中並於室溫下進行攪拌混合；接著，將2-羥甲基-4-丙基苯酚溶液[透過將1.2g的2-羥甲基-4-丙基苯酚(如SL1，R1 為C3 H7 )溶於10mL二氯甲烷而獲得]慢慢滴入雙頸瓶中，待攪拌0.5小時後，以TLC確認反應是否完全。待確認反應完全後，將水(25mL)加入雙頸瓶中，得到一混合液。利用二氯甲烷對該混合液反覆進行三次萃取並收集有機層，並於該有機層中加入無水硫酸鎂，再進行過濾及減壓濃縮，得到粗產物。利用管柱層析法(沖提液為乙酸乙酯及正己烷混合液，乙酸乙酯與正己烷的體積比例為1：9)來純化該粗產物，最後獲得製備例1之化學式1-2B所示化合物I(0.9g，白色固體，R1 為C3 H7 ，R2 為F)。前述反應過程如下反應式：(R1 為C3 H7 ，R2 為F，於以下標示為「3SGUQUF」) 利用氣相層析儀串聯質譜儀(GC-MS)進行製備例1化合物的分子量測量，結果為：m/z=580.1362[M]+ 。 再利用核磁共振儀進行製備例1化合物的光譜量測，結果為：1 H-NMR(CDCl3 , 400MHz),d (ppm): 0.968(3H, t,J =7.2Hz), 1.637(2H, m), 2.563(2H, t,J =7.6Hz), 5.025(1H, d,J =14.8Hz), 5.226(1H, d,J =14.8Hz), 6.871(1H, s), 6.913(2H, d,J =8.4Hz), 7.039(3H, m), 7.250(2H, d,J =10.4), 7.531(3H,m)。 製備例2之化學式1-2B所示化合物(R1 為C2 H5 ，R2 為F)的製法與製備例1相同，也同樣依據以上各個反應式進行製備；製備例2與製備例1的不同之處在於：反應式中的R1 為C2 H5 ，於以下標示為「2SGUQUF」。利用氣相層析儀串聯質譜儀(GC-MS)進行製備例2化合物的分子量測量，結果為：m/z=580.1362[M]+ 。再利用核磁共振儀進行製備例2化合物的光譜量測，結果為：1 H-NMR(CDCl3 , 400MHz),d (ppm): 1.205(3H, t,J =7.2Hz), 2.580(2H, q,J =7.6Hz), 4.983(1H, d,J =14.8Hz), 5.188(1H, d,J =14.8Hz), 5.979(1H, s), 6.849(1H, s), 6.878(1H, d,J =8.4Hz), 6.994(3H, m), 7.208(2H,J =10.4Hz), 7.472(3H, m)。 [ Preparation Examples 1 and 2] Compound I represented by Chemical Formula 1-2B The following description uses Preparation Example 1 as an example: 1. 4-propylphenol (3.3 g, 24 mmol), magnesium chloride (3.9 g, 36 mmol), paraformaldehyde (5 g, 165 mmol), and triethylamine (13.5 mL (9.3 mmol) and acetonitrile (60 mL) were placed in a 250 mL double-necked flask and mixed to obtain a reaction solution. This reaction solution was heated under reflux under nitrogen, and during the reaction, it was confirmed whether the reaction was complete with a thin film chromatograph (TLC). After 4 hours of reaction, the reaction was confirmed to be complete, and an aqueous hydrochloric acid solution (1N, 50 mL) was added to the reaction solution to obtain a mixed solution. Next, the mixed solution was repeatedly extracted three times with ethyl acetate, and the organic layer was collected. Anhydrous magnesium sulfate was added to the organic layer, followed by filtration and concentration under reduced pressure to obtain a crude product. The crude product was purified by column chromatography (eluent was a mixed solution of ethyl acetate and n-hexane, and the volume ratio of ethyl acetate to n-hexane was 1: 9), and finally 2-hydroxy-5-propyl was obtained -Benzaldehyde (3.2 g, yellow liquid). The aforementioned reaction process is as follows: (R 1 = C 3 H 7 ) 2. Place sodium borohydride (0.9 g, 24 mmol) and methanol (30 mL) in a 250 mL double-necked flask and cool to 0 ° C. Then 2-hydroxy-5-propyl-benzaldehyde (2.0 g, 12 mmol) was slowly dropped into the double-necked flask, and after stirring for 1 hour, it was confirmed by TLC whether the reaction was complete. After confirming the completion of the reaction, an aqueous hydrochloric acid solution (1N, 25 mL) was added to the double-necked flask to obtain a mixed solution. The mixture was repeatedly extracted three times with ethyl acetate, and the organic layer was collected. Anhydrous magnesium sulfate was added to the organic layer, followed by filtration and concentration under reduced pressure to obtain a crude product. The crude product was purified by column chromatography (the extract was a mixed solution of ethyl acetate and n-hexane, and the volume ratio of ethyl acetate to n-hexane was 2: 8), and finally 2-hydroxymethyl-4- Propylphenol (1.7 g, white solid, SL1). The aforementioned reaction process is as follows: 3. Tetrakis (triphenylphosphine) palladium (0.34g, 3mol%), 4-bromo-3-fluoro-benzaldehyde (3.0g, 14.8mmol), 4-[(3 ', 4', 5'- Trifluorophenyl) -difluoromethoxy] -3,5-difluorophenylboronic acid (8.6g, 60mmol, the synthesis of this compound can refer to EP 1341742A1), potassium carbonate (6.1g, 44.4mmol), water ( 20 mL) and tetrahydrofuran (180 mL) were added to a double-necked round bottom flask and stirred to obtain a reaction solution. This reaction liquid was heated and refluxed, and it was confirmed by TLC that the reaction was complete during the reaction. After 24 hours of reaction, the reaction was confirmed to be complete, and water (100 mL) was added to the reaction solution to obtain a mixed solution. Next, the mixed solution was repeatedly extracted three times with ethyl acetate, and the organic layer was collected. Anhydrous magnesium sulfate was added to the organic layer, followed by filtration and concentration under reduced pressure to obtain a crude product. The crude product was purified by column chromatography (eluent: n-hexane) to obtain compound SR2 (5.8 g, white solid). The aforementioned reaction process is as follows: (R 2 = F) 4. Add compound SR2 (1.0 g, 2.4 mmol), dichloromethane (30 mL), and trimethylchlorosilane (0.5 g, 4.8 mmol) to a 250 mL double-necked flask and perform at room temperature. stirring and mixing; Subsequently, the 2-hydroxymethyl-4-propyl phenol solution [via the 2-hydroxymethyl-4-propylphenol 1.2g (e.g. SL1, R 1 is C 3 H 7) was dissolved in 10mL Obtained by dichloromethane] Slowly dripped into a double-necked flask, and after stirring for 0.5 hours, it was confirmed by TLC whether the reaction was complete. After confirming that the reaction is complete, water (25 mL) was added to the double-necked flask to obtain a mixed solution. The mixture was repeatedly extracted three times with dichloromethane, and the organic layer was collected. Anhydrous magnesium sulfate was added to the organic layer, followed by filtration and concentration under reduced pressure to obtain a crude product. The crude product was purified by column chromatography (the extract was a mixed solution of ethyl acetate and n-hexane, and the volume ratio of ethyl acetate to n-hexane was 1: 9), and finally the chemical formula 1-2B of Preparation Example 1 was obtained. Compound I shown (0.9 g, white solid, R 1 is C 3 H 7 , R 2 is F). The aforementioned reaction process is as follows: (R 1 is C 3 H 7 , R 2 is F, and is designated as “3SGUQUF” below) The molecular weight measurement of the compound of Preparation 1 was performed using a gas chromatograph tandem mass spectrometer (GC-MS), and the result was: m / z = 580.1362 [M] + . The spectrum measurement of the compound of Preparation 1 was performed by a nuclear magnetic resonance apparatus, and the results were: 1 H-NMR (CDCl 3 , 400MHz), d (ppm): 0.968 (3H, t, J = 7.2Hz), 1.637 (2H, m), 2.563 (2H, t, J = 7.6Hz), 5.025 (1H, d, J = 14.8Hz), 5.226 (1H, d, J = 14.8Hz), 6.871 (1H, s), 6.913 (2H, d, J = 8.4 Hz), 7.039 (3H, m), 7.250 (2H, d, J = 10.4), 7.531 (3H, m). The compound (R 1 is C 2 H 5 and R 2 is F) shown in Chemical Formula 1-2B in Preparation Example 2 is prepared in the same manner as in Preparation Example 1, and is also prepared according to the above reaction formulas; Preparation Example 2 and Preparation Example 1 The difference is that R 1 in the reaction formula is C 2 H 5 , and it is marked as "2SGUQUF" below. A gas chromatograph tandem mass spectrometer (GC-MS) was used to measure the molecular weight of the compound of Preparation Example 2, and the result was: m / z = 580.1362 [M] + . The spectrum measurement of the compound of Preparation 2 was performed with a nuclear magnetic resonance instrument, and the results were: 1 H-NMR (CDCl 3 , 400MHz), d (ppm): 1.205 (3H, t, J = 7.2Hz), 2.580 (2H, q, J = 7.6Hz), 4.983 (1H, d, J = 14.8Hz), 5.188 (1H, d, J = 14.8Hz), 5.979 (1H, s), 6.849 (1H, s), 6.878 (1H, d, J = 8.4 Hz), 6.994 (3H, m), 7.208 (2H, J = 10.4 Hz), 7.472 (3H, m).

[ 製備例 3 及 4] 化學式 1-2A 所示化合物 I 製備例3之化學式1-2A所示化合物(R1 為C3 H7 ，R2 為F)的製法與製備例1相同，也同樣依據以上各個反應式進行製備；製備例3與製備例1的不同之處在於：反應式中的SR2化合物是以下述SR1取代，SR1的製法如下(將SR2製法中的4-溴-3-氟-苯甲醛置換為4-溴-苯甲醛)。製備例3於以下標示為「3SPUQUF」。利用氣相層析儀串聯質譜儀(GC-MS)進行製備例3化合物的分子量測量，結果為：m/z=562.1467[M]+ 。再利用核磁共振儀進行製備例3化合物的光譜量測，結果為：1 H-NMR(CDCl3 , 400MHz),d (ppm): 1.105(3H, t,J =7.2Hz), 1.645(2H, m), 2.263(2H,t,J =7.6Hz), 5.103(1H, d,J =14.8Hz), 5.221(1H, d,J =14.8Hz), 6.156(1H, s), 6.871(1H, s), 6.892(1H, d,J =8.4Hz), 7.036(3H, m), 7.178(2H,J =10Hz), 7.633(2H, d,J =10.4Hz), 7.724(2H, d,J =10.4Hz)。 製備例4之化學式1-2A所示化合物(R1 為C2 H5 ，R2 為F)的製法與製備例3相同；製備例4與製備例3的不同之處在於：反應式中的R1 為C2 H5 ，於以下標示為「2SPUQUF」。利用氣相層析儀串聯質譜儀(GC-MS)進行製備例4化合物的分子量測量，結果為：m/z=548.1196[M]+ 。再利用核磁共振儀進行製備例4化合物的光譜量測，結果為：1 H-NMR(CDCl3 , 400MHz),d (ppm): 1.207(3H, t,J =7.2Hz), 2.285(2H, q,J =7.6Hz), 4.985(1H, d,J =14.8Hz), 5.193(1H, d,J =14.8Hz), 6.006(1H, s), 6.849(1H, s), 6.860(1H, d,J =8.4Hz ), 7.015(3H, m), 7.145(2H,J =10Hz), 7.612(2H, d,J =10.4Hz), 7.713(2H, d,J =10.4Hz)。 [ Preparation Examples 3 and 4] Compound I represented by Chemical Formula 1-2A The compound of Formula 1-2A (R 1 is C 3 H 7 , R 2 is F) in Preparation Example 3 is prepared in the same manner as in Preparation Example 1, and is also prepared according to the above reaction formulas; Preparation Example 3 and Preparation Example 1 The difference is that the SR2 compound in the reaction formula is substituted with the following SR1, and the preparation method of SR1 is as follows (the 4-bromo-3-fluoro-benzaldehyde in the SR2 production method is replaced with 4-bromo-benzaldehyde). Preparation Example 3 is designated as "3SPUQUF" below. A gas chromatograph tandem mass spectrometer (GC-MS) was used to measure the molecular weight of the compound of Preparation Example 3, and the result was: m / z = 562.1467 [M] + . The spectrum measurement of the compound of Preparation Example 3 was performed by a nuclear magnetic resonance apparatus, and the results were: 1 H-NMR (CDCl 3 , 400 MHz), d (ppm): 1.105 (3H, t, J = 7.2Hz), 1.645 (2H, m), 2.263 (2H, t, J = 7.6Hz), 5.103 (1H, d, J = 14.8Hz), 5.221 (1H, d, J = 14.8Hz), 6.156 (1H, s), 6.871 (1H, s), 6.892 (1H, d, J = 8.4Hz), 7.036 (3H, m), 7.178 (2H, J = 10Hz), 7.633 (2H, d, J = 10.4Hz), 7.724 (2H, d, J = 10.4Hz). The preparation method of the compound represented by Chemical Formula 1-2A in Preparation Example 4 (R 1 is C 2 H 5 and R 2 is F) is the same as that in Preparation Example 3; The difference between Preparation Example 4 and Preparation Example 3 is that: R 1 is C 2 H 5 and is designated as "2SPUQUF" below. A gas chromatograph-tandem mass spectrometer (GC-MS) was used to measure the molecular weight of the compound of Preparation Example 4, and the result was: m / z = 548.1196 [M] + . The spectrum measurement of the compound of Preparation 4 was performed with a nuclear magnetic resonance instrument, and the results were: 1 H-NMR (CDCl 3 , 400 MHz), d (ppm): 1.207 (3H, t, J = 7.2 Hz), 2.285 (2H, q, J = 7.6Hz), 4.985 (1H, d, J = 14.8Hz), 5.193 (1H, d, J = 14.8Hz), 6.006 (1H, s), 6.849 (1H, s), 6.860 (1H, d, J = 8.4Hz), 7.015 (3H, m), 7.145 (2H, J = 10Hz), 7.612 (2H, d, J = 10.4Hz), 7.713 (2H, d, J = 10.4Hz).

[ 製備例 5] 化學式 1-2C 所示化合物 I 製備例5之化學式1-2C所示化合物(R1 為OC4 H9 ，R2 為F)的製法與製備例1相同，也同樣依據以上各個反應式進行製備；製備例5與製備例1的不同之處在於：反應式中的SL1化合物是以下述SL2取代，SL2的製法如下(將SL1製法中的4-丙基苯酚置換為2,3-二氟-4-丁氧基苯酚)。 最終是將SL2化合物與SR1化合物進行反應製得製備例5化合物，反應過程如下：製備例5於以下標示為「4OSyPUQUF」。利用氣相層析儀串聯質譜儀(GC-MS)進行製備例5化合物的分子量測量，結果為：m/z=628.1195[M]+ 。再利用核磁共振儀進行製備例5化合物的光譜量測，結果為：1 H-NMR(CDCl3 , 400MHz),d (ppm): 1.104(3H, t,J =7.2Hz), 1.514(2H, m), 1.819(2H, m), 4.003 (2H, t,J =6.4Hz), 4.978(1H, d,J =14.4Hz), 5.170(1H, d,J =14.8Hz), 6.052(1H, s), 6.427(1H, d,J =8.0Hz), 7.012(2H, m), 7.257(2H,J =10Hz), 7.655(2H, d,J =10.4Hz), 7.751(2H, d,J =10.4Hz) [ Production Example 5] Compound I represented by Chemical Formula 1-2C The compound of Formula 1-2C (R 1 is OC 4 H 9 and R 2 is F) in Preparation Example 5 is prepared in the same manner as in Preparation Example 1, and is also prepared according to the above reaction formulas; Preparation Example 5 and Preparation Example 1 The difference is that the SL1 compound in the reaction formula is substituted with the following SL2, and the production method of SL2 is as follows (the 4-propylphenol in the SL1 production method is replaced with 2,3-difluoro-4-butoxyphenol). Finally, the compound of Preparation Example 5 is prepared by reacting the SL2 compound with the SR1 compound. The reaction process is as follows: Preparation Example 5 is designated as "4OSyPUQUF" below. A gas chromatograph tandem mass spectrometer (GC-MS) was used to measure the molecular weight of the compound of Preparation Example 5, and the result was: m / z = 628.1195 [M] + . The spectrum measurement of the compound of Preparation 5 was performed by a nuclear magnetic resonance instrument, and the results were: 1 H-NMR (CDCl 3 , 400 MHz), d (ppm): 1.104 (3H, t, J = 7.2 Hz), 1.514 (2H, m), 1.819 (2H, m), 4.003 (2H, t, J = 6.4Hz), 4.978 (1H, d, J = 14.4Hz), 5.170 (1H, d, J = 14.8Hz), 6.052 (1H, s), 6.427 (1H, d, J = 8.0Hz), 7.012 (2H, m), 7.257 (2H, J = 10Hz), 7.655 (2H, d, J = 10.4Hz), 7.751 (2H, d, J = 10.4Hz)

[ 實施例 1 至 16] 液晶介質的製備 依據下表2的組成及含量，分別選用化合物I、化合物II、化合物III及化合物IV進行混合，以製得實施例1至16的液晶介質。接著，依據[0027]段的測試方法進行實施例1至16之液晶介質的性質測試，結果整理於表3中。 [ Examples 1 to 16] Preparation of liquid crystal media According to the composition and content of Table 2 below, compounds I, II, III and IV were selected and mixed to prepare the liquid crystal media of Examples 1 to 16. Next, the properties of the liquid crystal media of Examples 1 to 16 were tested according to the test method of paragraph [0027], and the results are summarized in Table 3.

[表2] [續表2] [續表2] [Table 2] [Continued Table 2] [Continued Table 2]

[表3] [table 3]

由表2的組成含量及表3的性質測試，證明實施例1至16的液晶介質具備較高的Δε及ε⊥ 、較低的γ1，且Tni 、K11、K33及Δn皆能符合業界需求。A composition content of Table 2 and Table 3 Properties of the test, the liquid-crystalline medium demonstrated in Example 1 to 16 have a high Δε and ε ⊥, lower [gamma] l, and T ni, K11, K33, and meet the requirements of the industry have encountered Δn .

[ 比較例 1 及 2] 依據下表4的組成及含量，分別選用化合物II及化合物III進行混合，以製得比較例1及2的液晶介質。接著，依據[0027]段的測試方法進行比較例1及2之液晶介質的性質測試，結果分別整理於表5及表6中。另外，於表5中，將實施例16及比較例2的液晶介質進行比較；於表6中，將實施例1與比較例1進行比較。 [ Comparative Examples 1 and 2] According to the composition and content of Table 4 below, Compound II and Compound III were respectively selected and mixed to prepare the liquid crystal media of Comparative Examples 1 and 2. Next, the properties of the liquid crystal media of Comparative Examples 1 and 2 were tested according to the test method of paragraph [0027]. The results are summarized in Tables 5 and 6, respectively. In Table 5, the liquid crystal media of Example 16 and Comparative Example 2 are compared; in Table 6, Example 1 and Comparative Example 1 are compared.

[表4] [Table 4]

[表5] [table 5]

由表5結果，可以發現實施例16因含有13wt%的化合物I，故能展現較高的Δε及ε⊥ ，以及較長的低溫儲存天數，顯示含有化合物I的液晶介質於後續應用於液晶顯示單元時，更能有效降低啟動電壓及提升穿透度。From the results in Table 5, it can be found that Example 16 can exhibit higher Δε and ε ⊥ as it contains 13% by weight of compound I, as well as a longer period of low-temperature storage, indicating that the liquid crystal medium containing compound I will be used in subsequent liquid crystal displays. When it is a unit, it can effectively reduce the starting voltage and increase the penetration.

[表6] [TABLE 6]

於表6中，比較例1是由化合物II及化合物III所組成，實施例1是由化合物I及化合物III所組成；由性質測試結果可知，實施例1的Tni 溫度、Δε、ε⊥ 、K11及K33皆高於比較例1，顯示含有化合物I的液晶介質於後續應用於液晶顯示單元時，更能有效降低啟動電壓及提升穿透度。In Table 6, Comparative Example 1 is composed of Compound II and Compound III, and Example 1 is composed of Compound I and Compound III. From the results of the property test, it can be known that the Tni temperature, Δε, ε 、, K11 and K33 are both higher than Comparative Example 1, showing that the liquid crystal medium containing Compound I can more effectively reduce the start-up voltage and increase the penetration when it is subsequently applied to a liquid crystal display unit.

綜上所述，本發明液晶介質因為含有特殊結構設計且具有較高Δε及ε⊥ 的化學式1所示之化合物I，於後續應用於液晶顯示單元時，可有效降低啟動電壓及提升穿透度。，故確實能達成本發明之目的。In summary, since the liquid crystal medium of the present invention contains the compound I shown in Chemical Formula 1 with a special structure design and high Δε and ε ⊥ , it can effectively reduce the startup voltage and increase the penetration when it is subsequently applied to a liquid crystal display unit. . , So it can indeed achieve the purpose of cost invention.

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 are only examples of the present invention. When the scope of implementation of the present invention cannot be limited in this way, any simple equivalent changes and modifications made in accordance with the scope of the patent application and the content of the patent specification of the present invention are still Within the scope of the invention patent.

Claims (10)

一種液晶介質，包含： 至少一種化合物I，是由化學式1所示： [化學式1]， 於化學式1中，R1 表示碳數範圍為1~10的烷基、碳數範圍為1~10的烷氧基、碳數範圍為2~10的烯基或碳數範圍為2~10的烯氧基，該烷基、烷氧基、烯基或烯氧基中的一或多個氫可選擇地被氟取代； X1 及X2 各自表示氫或氟； A1 、A2 、A3 及A4 各自表示1,4-伸環己基、1,4-伸苯基、3,5-二氟-1,4-伸苯基、2,3-二氟-1,4-伸苯基或3-氟-1,4-伸苯基； n表示0、1或2，當n為2時，兩個A2 可為相同或不同； m及o表示0或1，且m+o≥1；及 R2 表示鹵素、OCF3 、CF3 或CN。A liquid crystal medium including: at least one compound I is represented by Chemical Formula 1: [Chemical Formula 1] In Chemical Formula 1, R 1 represents an alkyl group having a carbon number range of 1 to 10, an alkoxy group having a carbon number range of 1 to 10, an alkenyl group having a carbon number range of 2 to 10 or a carbon number range of 2 to 10 One or more hydrogens in the alkyl, alkoxy, alkenyl, or alkenyl group may be optionally substituted with fluorine; X 1 and X 2 each represent hydrogen or fluorine; A 1 , A 2 , A 3 and A 4 each represent 1,4-cyclohexyl, 1,4-phenylene, 3,5-difluoro-1,4-phenylene, 2,3-difluoro-1,4-phenylene Phenyl or 3-fluoro-1,4-phenylene; n represents 0, 1, or 2, when n is 2, two A 2 may be the same or different; m and o represent 0 or 1, and m + o≥1; and R 2 represents halogen, OCF 3 , CF 3 or CN. 如請求項1所述的液晶介質，其中，該化合物I是選自於化學式1-1所示化合物、化學式1-2所示化合物或化學式1-3所示化合物： [化學式1-1]， [化學式1-2]， [化學式1-3]。The liquid crystal medium according to claim 1, wherein the compound I is selected from a compound represented by Chemical Formula 1-1, a compound represented by Chemical Formula 1-2, or a compound represented by Chemical Formula 1-3: [Chemical Formula 1-1] , [Chemical Formula 1-2] [Chemical Formula 1-3] . 如請求項2所述的液晶介質，其中，該化學式1-2是選自於由下列所構成之群組：，及。The liquid crystal medium according to claim 2, wherein the chemical formula 1-2 is selected from the group consisting of: , and . 如請求項1所述的液晶介質，還包含至少一種化合物II，是由化學式2所示： [化學式2]， 於化學式2中，R3 表示碳數範圍為1~10的烷基、碳數範圍為1~10的烷氧基、碳數範圍為2~10的烯基或碳數範圍為2~10的烯氧基，該烷基、烷氧基、烯基或烯氧基中的一或多個氫可選擇地被氟取代； B1 表示1,4-伸環己基、1,4-伸苯基、或； B2 及B3 各自表示1,4-伸環己基、1,4-伸苯基、3,5-二氟-1,4-伸苯基、2,3-二氟-1,4-伸苯基或3-氟-1,4-伸苯基； p表示0或1； Z1 表示單鍵、−(CH2 )2 −、−COO−、−CH2 O−、−OCO−、−CF2 O−、−OCF2 −、−C≡C−或−CH=CH−；及 R4 表示鹵素、OCF3 、OCF2 H、CF3 或CN。The liquid crystal medium according to claim 1, further comprising at least one compound II, which is represented by Chemical Formula 2: [Chemical Formula 2] In Chemical Formula 2, R 3 represents an alkyl group having a carbon number range of 1 to 10, an alkoxy group having a carbon number range of 1 to 10, an alkenyl group having a carbon number range of 2 to 10 or a carbon number range of 2 to 10 Alkenyloxy, one or more hydrogens of the alkyl, alkoxy, alkenyl or alkenyloxy may be optionally substituted by fluorine; B 1 represents 1,4-cyclohexyl, 1,4-benzene base, or B 2 and B 3 each represent 1,4-cyclohexyl, 1,4-phenylene, 3,5-difluoro-1,4-phenylene, 2,3-difluoro-1,4- Phenylene or 3-fluoro-1,4-phenylene; p represents 0 or 1; Z 1 represents a single bond, − (CH 2 ) 2 −, −COO−, −CH 2 O−, −OCO−, −CF 2 O−, −OCF 2 −, −C≡C−, or −CH = CH−; and R 4 represents halogen, OCF 3 , OCF 2 H, CF 3, or CN. 如請求項4所述的液晶介質，其中，該化合物II是選自於化學式2-1所示化合物或化學式2-2所示化合物： [化學式2-1][化學式2-2]。The liquid crystal medium according to claim 4, wherein the compound II is selected from a compound represented by Chemical Formula 2-1 or a compound represented by Chemical Formula 2-2: [Chemical Formula 2-1] [Chemical Formula 2-2] . 如請求項1或4所述的液晶介質，還包含至少一種化合物III，是由化學式3所示： [化學式3]， 於化學式3中，R5 表示碳數範圍為1~10的烷基、碳數範圍為1~10的烷氧基、碳數範圍為2~10的烯基或碳數範圍為2~10的烯氧基，該烷基、烷氧基、烯基或烯氧基中的一或多個氫可選擇地被氟取代； C1 、C2 、C3 及C4 各自表示1,4-伸環己基、1,4-伸苯基、2,3-二氟-1,4-伸苯基、3-氟-1,4-伸苯基、2,5-伸苯并呋喃基或2,6-伸7,8-二氟-1,3-苯并二噁烷基； q、r及s各自表示0或1； Z2 、Z3 及Z4 各自表示單鍵、−(CH2 )2 −、−COO−、−CH2 O−、−OCO−、−CF2 O−、−OCF2 −、−C≡C−或−CH=CH−；及 R6 表示鹵素、OCF3 、CF3 、CN、碳數範圍為1~10的烷基、碳數範圍為1~10的烷氧基、碳數範圍為2~10的烯基或碳數範圍為2~10的烯氧基，該烷基、烷氧基、烯基或烯氧基中的一或多個氫可選擇地被氟取代。The liquid crystal medium according to claim 1 or 4, further comprising at least one compound III, which is represented by Chemical Formula 3: [Chemical Formula 3] In Chemical Formula 3, R 5 represents an alkyl group having a carbon number range of 1 to 10, an alkoxy group having a carbon number range of 1 to 10, an alkenyl group having a carbon number range of 2 to 10 or a carbon number range of 2 to 10 Alkenyloxy, one or more hydrogens of the alkyl, alkoxy, alkenyl or alkenyloxy may be optionally substituted by fluorine; C 1 , C 2 , C 3 and C 4 each represent 1,4- Cyclohexyl, 1,4-phenylene, 2,3-difluoro-1,4-phenylene, 3-fluoro-1,4-phenylene, 2,5-phenylbenzofuranyl, or 2 , 6-Extended 7,8-difluoro-1,3-benzodioxane; q, r and s each represent 0 or 1; Z 2 , Z 3 and Z 4 each represent a single bond, − (CH 2 ) 2 −, −COO−, −CH 2 O−, −OCO−, −CF 2 O−, −OCF 2 −, −C≡C−, or −CH = CH−; and R 6 represents halogen, OCF 3 , CF 3 , CN, alkyl with 1 to 10 carbons, alkoxy with 1 to 10 carbons, alkenyl with 2 to 10 carbons or alkenyl with 2 to 10 carbons One or more hydrogens in the alkyl, alkoxy, alkenyl, or alkenyloxy group may be optionally substituted with fluorine. 如請求項6所述的液晶介質，其中，該化合物III是選自於化學式3-1所示化合物、化學式3-2所示化合物、化學式3-3所示化合物、化學式3-4所示化合物或化學式3-5所示化合物： [化學式3-1][化學式3-2][化學式3-3][化學式3-4][化學式3-5]。The liquid crystal medium according to claim 6, wherein the compound III is selected from the group consisting of a compound represented by Chemical Formula 3-1, a compound represented by Chemical Formula 3-2, a compound represented by Chemical Formula 3-3, and a compound represented by Chemical Formula 3-4. Or a compound represented by Chemical Formula 3-5: [Chemical Formula 3-1] [Chemical Formula 3-2] [Chemical Formula 3-3] [Chemical Formula 3-4] [Chemical Formula 3-5] . 如請求項1所述的液晶介質，還包含至少一種化合物IV，是由化學式4所示： [化學式4]， 於化學式4中，R7 表示碳數範圍為1~10的烷基、碳數範圍為1~10的烷氧基、碳數範圍為2~10的烯基或碳數範圍為2~10的烯氧基，該烷基、烷氧基、烯基或烯氧基中的一或多個氫可選擇地被氟取代； X3 、X4 、X5 及X6 各自表示氫或氟； D1 表示1,4-伸環己基、1,4-伸苯基、3,5-二氟-1,4-伸苯基、2,3-二氟-1,4-伸苯基或3-氟-1,4-伸苯基；及 R8 表示鹵素、碳數範圍為1~10的烷氧基、碳數範圍為2~10的烯氧基、OCHCF2 、OCF3 、CF3 或CN，該烷氧基或烯氧基的一或多個氫可選擇地被氟取代。The liquid crystal medium according to claim 1, further comprising at least one compound IV, which is represented by Chemical Formula 4: [Chemical Formula 4] In Chemical Formula 4, R 7 represents an alkyl group having a carbon number range of 1 to 10, an alkoxy group having a carbon number range of 1 to 10, an alkenyl group having a carbon number range of 2 to 10 or a carbon number range of 2 to 10 Alkenyloxy, one or more hydrogens of the alkyl, alkoxy, alkenyl or alkenyloxy are optionally substituted by fluorine; X 3 , X 4 , X 5 and X 6 each represent hydrogen or fluorine; D 1 represents 1,4-cyclohexyl, 1,4-phenylene, 3,5-difluoro-1,4-phenylene, 2,3-difluoro-1,4-phenylene, or 3 -Fluoro-1,4-phenylene; and R 8 represents halogen, alkoxy having 1 to 10 carbons, alkenoxy having 2 to 10 carbons, OCHCF 2 , OCF 3 , CF 3 or CN, one or more hydrogens of the alkoxy or alkenyloxy group are optionally substituted with fluorine. 一種化合物，是由化學式1所示： [化學式1]， 於化學式1中，R1 表示碳數範圍為1~10的烷基、碳數範圍為1~10的烷氧基、碳數範圍為2~10的烯基或碳數範圍為2~10的烯氧基，該烷基、烷氧基、烯基或烯氧基中的一或多個氫可選擇地被氟取代； X1 及X2 各自表示氫或氟； A1 、A2 、A3 及A4 各自表示1,4-伸環己基、1,4-伸苯基、3,5-二氟-1,4-伸苯基、2,3-二氟-1,4-伸苯基或3-氟-1,4-伸苯基； n表示0、1或2，當n為2時，兩個A2 可為相同或不同； m及o表示0或1，且m+o≥1；及 R2 表示鹵素、OCF3 、CF3 或CN。A compound is shown by Chemical Formula 1: [Chemical Formula 1] In Chemical Formula 1, R 1 represents an alkyl group having a carbon number range of 1 to 10, an alkoxy group having a carbon number range of 1 to 10, an alkenyl group having a carbon number range of 2 to 10 or a carbon number range of 2 to 10 One or more hydrogens in the alkyl, alkoxy, alkenyl, or alkenyl group may be optionally substituted with fluorine; X 1 and X 2 each represent hydrogen or fluorine; A 1 , A 2 , A 3 and A 4 each represent 1,4-cyclohexyl, 1,4-phenylene, 3,5-difluoro-1,4-phenylene, 2,3-difluoro-1,4-phenylene Phenyl or 3-fluoro-1,4-phenylene; n represents 0, 1, or 2, when n is 2, two A 2 may be the same or different; m and o represent 0 or 1, and m + o≥1; and R 2 represents halogen, OCF 3 , CF 3 or CN. 一種顯示單元，包含一種如請求項1至8中任一項所述的液晶介質。A display unit includes a liquid crystal medium according to any one of claims 1 to 8.
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