TWI599640B - Compound, liquid crystal medium containing the compound and display unit - Google Patents

Compound, liquid crystal medium containing the compound and display unit Download PDF

Info

Publication number
TWI599640B
TWI599640B TW105138564A TW105138564A TWI599640B TW I599640 B TWI599640 B TW I599640B TW 105138564 A TW105138564 A TW 105138564A TW 105138564 A TW105138564 A TW 105138564A TW I599640 B TWI599640 B TW I599640B
Authority
TW
Taiwan
Prior art keywords
chemical formula
compound
carbon number
group
liquid crystal
Prior art date
Application number
TW105138564A
Other languages
Chinese (zh)
Other versions
TW201819601A (en
Inventor
Ching Tien Lee
Yi Chun Lin
Chun Chih Wang
Original Assignee
Daxin Mat Corp
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Daxin Mat Corp filed Critical Daxin Mat Corp
Priority to TW105138564A priority Critical patent/TWI599640B/en
Priority to CN201710845722.0A priority patent/CN108102667A/en
Application granted granted Critical
Publication of TWI599640B publication Critical patent/TWI599640B/en
Publication of TW201819601A publication Critical patent/TW201819601A/en

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00Liquid crystal materials
    • C09K19/04Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06Non-steroidal liquid crystal compounds
    • C09K19/34Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
    • C09K19/3402Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D319/00Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D319/041,3-Dioxanes; Hydrogenated 1,3-dioxanes
    • C07D319/081,3-Dioxanes; Hydrogenated 1,3-dioxanes condensed with carbocyclic rings or ring systems
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00Liquid crystal materials
    • C09K19/04Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06Non-steroidal liquid crystal compounds
    • C09K19/34Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
    • C09K19/3402Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom
    • C09K2019/3422Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom the heterocyclic ring being a six-membered ring
    • C09K2019/3425Six-membered ring with oxygen(s) in fused, bridged or spiro ring systems

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Liquid Crystal Substances (AREA)

Description

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

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 containing the same, and a display unit, and more particularly to a compound represented by Chemical Formula 1, a liquid crystal medium containing the same, and a display unit.

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 view of the widespread use of liquid crystal display units, various properties of liquid crystal compounds, such as dielectric anisotropy (Δε), refractive anisotropy (Δn), rotational viscosity (γ1), etc., are still required to be continuously improved, so At present, the industry needs to research and develop novel liquid crystal compounds or liquid crystal media (matrix).

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,G 1和G 2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;G 3、G 4及G 5分別表示氫、鹵素、CF 3或SF 5;Y 1、Y 2、Y 3及Y 4分別表示單鍵、-CH 2CH 2-、-(CH 2) 4-、-CH 2O-、-CH=CH-、-C≡C-、-COO-、-OCO-或-OCH 2-;E 1、E 2、E 3和E 4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。 US Patent Publication No. US 2009/0066905 A1 discloses a compound containing a dioxatetralin group having the following structure (A): (A) In the above structure (A), G 1 and G 2 represent a cyano group, a halogen group, an optionally substituted hydrocarbyl group, a selectively substituted alkoxy group, a selectively substituted heterocyclic group (heterocyclyl), and RC. (O)O- or ROC(O)-, wherein R represents an optionally substituted hydrocarbon group; G 3 , G 4 and G 5 respectively represent hydrogen, halogen, CF 3 or SF 5 ; 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 each represent a 1,4-phenylene group, a 1,4-cyclohexylene group or a heterocyclic group, and the aforementioned groups are optionally substituted; and t1 T2, t3, and t4 are 0 or 1, respectively, with the condition 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 structure (A), or one of t3 and t4 is one and the other is zero. The Δε < 0 of most of the compounds in the examples shows that the compounds in this U.S. patent are predominantly 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。Accordingly, it is an object of the present invention to provide a liquid crystal medium capable of achieving at least one of the following effects: lowering the startup voltage of the display, shortening the reaction 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,R 1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; X 1及X 2各自表示氫或氟; A 1、A 2、A 3及A 4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A 2可為相同或不同; m及o表示0或1,且m+o≥1;及 R 2表示鹵素、OCF 3、CF 3或CN。 Thus, the liquid crystal medium of the present invention comprises: 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 of 1 to 10, an alkoxy group having a carbon number of 1 to 10, an alkenyl group having a carbon number of 2 to 10, or a carbon number ranging from 2 to 10. Alkenyloxy, one or more hydrogens of the alkyl, alkoxy, alkenyl or alkenyloxy group may be optionally substituted by fluorine; X 1 and X 2 each represent hydrogen or fluorine; A 1 , A 2 , A 3 and A 4 each represent 1,4-cyclohexylene, 1,4-phenylene, 3,5-difluoro-1,4-phenylene, 2,3-difluoro-1,4-stretch 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 liquid crystal compound, having a higher Δ ε, a higher ε , and a suitable γ 1 , and to an acid, heat and ultraviolet 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。It is still another object of the present invention to provide a display unit comprising 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 can at least effectively reduce the starting voltage and enhance the penetration when it is subsequently applied to a liquid crystal display unit because it contains a compound I having a special structure and having a higher Δε and ε . degree.

以下就本發明內容進行詳細說明:The details of the present invention are described below:

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 a compound selected from the formula 1-1, a compound represented by the chemical formula 1-2 or a compound represented by the 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,A 1、A 2、A 3及A 4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;R 1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R 2表示鹵素、OCF 3、CF 3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-cyclohexylene, 1,4-phenylene, 3 , 5-difluoro-1,4-phenylene or 3-fluoro-1,4-phenylene; R 1 represents an alkyl group having a carbon number ranging from 1 to 10 or an alkoxy group having a carbon number ranging from 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 the chemical formula 1-2 and the compound represented by the chemical formula 1-2 is selected from the group consisting of the following: [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,R 1表示碳數範圍為1~10的烷基以及R 2表示鹵素、OCF 3、CF 3或CN。 Preferably, in Chemical Formulas 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 a 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 preparation of the compound I represented by the chemical formula 1 can be carried out according to a known method, for example, but not limited to, by the following reaction schemes of the steps 1 to 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,R 3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; B 1表示1,4-伸環己基、1,4-伸苯基、 ; B 2及B 3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; Z 1表示單鍵、−(CH 2) 2−、−COO−、−CH 2O−、−OCO−、−CF 2O−、−OCF 2−、−C≡C−或−CH=CH−;及 R 4表示鹵素、OCF 3、OCHCF 2、OCF 2H、CF 3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 the chemical formula 2: [Chemical Formula 2] In Chemical Formula 2, R 3 represents an alkyl group having a carbon number of 1 to 10, an alkoxy group having a carbon number of 1 to 10, an alkenyl group having a carbon number of 2 to 10, or a carbon number ranging from 2 to 10 Alkenyloxy, one or more hydrogens of the alkyl, alkoxy, alkenyl or alkenyloxy group may be optionally substituted by fluorine; B 1 represents 1,4-cyclohexylene, 1,4-phenylene base, or ; B 2 and B 3 each represent 1,4-cyclohexylene, 1,4-phenylene, 3,5-difluoro-1,4-phenylene, 2,3-difluoro-1,4- Phenyl 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 a compound selected from the chemical formula 2-1 or the compound represented by the 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,R 3表示碳數範圍為1~10的烷基;B 2及B 3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;Z 1表示單鍵或−CF 2O−;R 4表示氟、OCHCF 2或OCF 2H。 Preferably, in the chemical formulas 2-1 and 2-2, R 3 represents an alkyl group having a carbon number ranging from 1 to 10; and B 2 and B 3 each represent a 1,4-cyclohexylene group and a 1,4-phenylene group. a 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,R 5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; C 1、C 2、C 3及C 4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; Z 2、Z 3及Z 4各自表示單鍵、−(CH 2) 2−、−COO−、−CH 2O−、−OCO−、−CF 2O−、−OCF 2−、−C≡C−或−CH=CH−;及 R 6表示鹵素、OCF 3、CF 3、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 the chemical formula 3: [Chemical Formula 3] In Chemical Formula 3, R 5 represents an alkyl group having a carbon number of 1 to 10, an alkoxy group having a carbon number of 1 to 10, an alkenyl group having a carbon number of 2 to 10, or a carbon number ranging from 2 to 10 Alkenyloxy, one or more hydrogens of the alkyl, alkoxy, alkenyl or alkenyloxy group may be optionally substituted by fluorine; C 1 , C 2 , C 3 and C 4 each represent 1,4- Cyclohexylene, 1,4-phenylene, 2,3-difluoro-1,4-phenylene, 3-fluoro-1,4-phenylene, 2,5-benzofuranyl or 2 , 6-extended 7,8-difluoro-1,3-benzodioxanyl; 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, an alkyl group having a carbon number ranging from 1 to 10, an alkoxy group having a carbon number ranging from 1 to 10, an alkenyl group having a carbon number ranging from 2 to 10, or an alkenyl group having a carbon number ranging from 2 to 10. One or more hydrogens of the alkyl, alkoxy, alkenyl or alkenyloxy group are optionally substituted by 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 a compound selected from the group consisting of a compound of the formula 3-1, a compound of the formula 3-2, a compound of the formula 3-3, a compound of the formula 3-4 or a compound of the 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,R 5表示碳數範圍為1~10的烷基或碳數範圍為2~10的烯基;Z 2、Z 3及Z 4各自表示單鍵或−C≡C−;R 6表示氟、OCF 3、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 Chemical Formulas 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; and each of Z 2 , Z 3 and Z 4 represents A single bond or −C≡C−; R 6 represents fluorine, OCF 3 , an alkyl group having a carbon number of 1 to 10, an alkoxy group having a carbon number ranging from 1 to 10, or an alkenyl group having a carbon number ranging from 2 to 10. .

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,R 7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; X 3、X 4、X 5及X 6各自表示氫或氟; D 1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 R 8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、OCHCF 2、OCF 3、CF 3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 of 1 to 10, an alkoxy group having a carbon number of 1 to 10, an alkenyl group having a carbon number of 2 to 10, or a carbon number ranging from 2 to 10 Alkenyloxy, one or more hydrogens of the alkyl, alkoxy, alkenyl or alkenyloxy group are optionally substituted by fluorine; X 3 , X 4 , X 5 and X 6 each represent hydrogen or fluorine; D 1 represents 1,4-cyclohexylene, 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 a halogen, an alkoxy group having a carbon number ranging from 1 to 10, an alkenyloxy group having a carbon number ranging from 2 to 10, OCHCF 2 , OCF 3 , CF 3 or CN, one or more hydrogens of the alkoxy or alkenyloxy group are optionally substituted by fluorine.

較佳地,該化學式4所示的化合物IV中,R 7表示碳數範圍為1~10的烷基;X 3、X 4、X 5及X 6各自表示氫;D 1表示1,4-伸苯基;R 8表示OCHCF 2Preferably, in the compound IV represented by the chemical formula 4, R 7 represents an alkyl group having a carbon number of from 1 to 10; X 3 , X 4 , X 5 and X 6 each represent hydrogen; and D 1 represents 1,4- Phenyl is extended; 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 comprises 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 of the compound I is calculated based on the total weight of the liquid crystal medium being 100 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, the total content of the compound I is in the range of 1 to 25 wt%, and the total content of the compound II is in the range of 5 to 20 wt%, based on the total weight of the liquid crystal medium of 100 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 comprises the liquid crystal medium described above. 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.

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] <TABLE border="1" borderColor="#000000" width="_0011"><TBODY><tr><td> S </td><td><img wi="118" he="64" file="IMG-2/Draw/02_image049.jpg" img-format="jpg"></img></td><td> Sy </td><td><img wi="121" he="88" file="IMG-2/Draw/02_image051.jpg" img-format="jpg"></img></td><td> P </td><td><img wi="85" he="40" file="IMG-2/Draw/02_image053.jpg" img-format="jpg"></img></td></tr><tr><td> C </td><td><img wi="85" he="40" file="IMG-2/Draw/02_image055.jpg" img-format="jpg"></img></td><td> U </td><td><img wi="72" he="73" file="IMG-2/Draw/02_image057.jpg" img-format="jpg"></img></td><td> UF </td><td><img wi="76" he="73" file="IMG-2/Draw/02_image059.jpg" img-format="jpg"></img></td></tr><tr><td> G </td><td><img wi="72" he="53" file="IMG-2/Draw/02_image061.jpg" img-format="jpg"></img></td><td> Y </td><td><img wi="72" he="53" file="IMG-2/Draw/02_image063.jpg" img-format="jpg"></img></td><td> do </td><td><img wi="85" he="50" file="IMG-2/Draw/02_image065.jpg" img-format="jpg"></img></td></tr><tr><td> RI </td><td><img wi="102" he="59" file="IMG-2/Draw/02_image029.jpg" img-format="jpg"></img></td><td> B </td><td><img wi="105" he="44" file="IMG-2/Draw/02_image067.jpg" img-format="jpg"></img></td><td> 數字1至5 </td><td> 烷基 (1~5代表烷基的碳數) </td></tr><tr><td> T </td><td> -C≡C- </td><td> Q </td><td><img wi="90" he="22" file="IMG-2/Draw/02_image069.jpg" img-format="jpg"></img></td><td> O2F </td><td> -OCHCF<sub>2</sub></td></tr><tr><td> V </td><td> -CH=CH<sub>2</sub></td><td> V1 </td><td> -CH=CH-CH<sub>3</sub></td><td> OCF2H </td><td> -OCF<sub>2</sub>H </td></tr><tr><td> V2 </td><td> CH<sub>2</sub>=CH-CH<sub>2</sub>CH<sub>2</sub>- </td><td> 2V </td><td> -CH<sub>2</sub>CH<sub>2</sub>-CH=CH<sub>2</sub></td><td>   </td><td>   </td></tr></TBODY></TABLE>The liquid crystal compound structures in the following examples and comparative examples are respectively represented by the code numbers of Table 1 below: [Table 1]         <TABLE border="1" borderColor="#000000" width="_0011"><TBODY><tr><td> S </td><td><img wi="118" he="64" file= "IMG-2/Draw/02_image049.jpg" img-format="jpg"></img></td><td> Sy </td><td><img wi="121" he="88" File="IMG-2/Draw/02_image051.jpg" img-format="jpg"></img></td><td> P </td><td><img wi="85" he=" 40" file="IMG-2/Draw/02_image053.jpg" img-format="jpg"></img></td></tr><tr><td> C </td><td>< Img wi="85" he="40" file="IMG-2/Draw/02_image055.jpg" img-format="jpg"></img></td><td> U </td><td ><img wi="72" he="73" file="IMG-2/Draw/02_image057.jpg" img-format="jpg"></img></td><td> UF </td> <td><img wi="76" he="73" file="IMG-2/Draw/02_image059.jpg" img-format="jpg"></img></td></tr><tr ><td> G </td><td><img wi="72" he="53" file="IMG-2/Draw/02_image061.jpg" img-format="jpg"></img>< /td><td> Y </td><td><img wi="72" he="53" file="IMG-2/Draw/02_image063.jpg" img-format="jpg"></img ></td><td> do </td><td><img wi="85" he="50" file="IMG-2/Draw/02_image065.jpg" img-format="jpg">< /img></td></tr><tr><td> RI </td ><td><img wi="102" he="59" file="IMG-2/Draw/02_image029.jpg" img-format="jpg"></img></td><td> B < /td><td><img wi="105" he="44" file="IMG-2/Draw/02_image067.jpg" img-format="jpg"></img></td><td> Number 1 to 5 </td><td> Alkyl (1~5 represents the carbon number of the alkyl group) </td></tr><tr><td> T </td><td> -C≡C - </td><td> Q </td><td><img wi="90" he="22" file="IMG-2/Draw/02_image069.jpg" img-format="jpg">< /img></td><td> O2F </td><td> -OCHCF<sub>2</sub></td></tr><tr><td> V </td><td> -CH=CH<sub>2</sub></td><td> V1 </td><td> -CH=CH-CH<sub>3</sub></td><td> OCF2H < /td><td> -OCF<sub>2</sub>H </td></tr><tr><td> V2 </td><td> CH<sub>2</sub>=CH -CH<sub>2</sub>CH<sub>2</sub>- </td><td> 2V </td><td> -CH<sub>2</sub>CH<sub>2 </sub>-CH=CH<sub>2</sub></td><td> </td><td> </td></tr></TBODY></TABLE>

[ 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(T ni,°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(T ni)。 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 selectively tested according to the following methods: 1. Clarification point temperature (T ni , ° C): using a differential scanning calorimeter (DSC) system, the liquid to be tested or liquid crystal The medium is placed on an aluminum pan with a scale of 0.5 to 10 mg, and the phase change temperature is determined by the endothermic peak of the liquid to be measured or the liquid crystal medium due to the phase change and the starting point of the exothermic peak. 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. Dielectric anisotropy (Δε): The liquid to be tested or the liquid crystal medium 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 parallel to the length of the liquid crystal molecules. The average dielectric constant measured in the axial direction is ε , and the average dielectric constant measured perpendicular to the long axis of the liquid crystal molecule is ε and dielectric anisotropy (Δε) = ε - ε . Based on Japanese Journal of Applied Physics, 53, p.010304, 2014 that may be greater when ε ⊥, greater light penetration. 3. Rotational viscosity (γ1, mPa•S): The liquid to be tested or the liquid crystal medium 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 is added by the instrument. The (Δε) factor is converted to obtain the rotational viscosity γ1. 4. K11 elastic constant ("slanting", pN at 20 ° C): The liquid to be tested or the liquid crystal medium 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. K11 can be obtained by adding the dielectric anisotropy (Δε) factor to the instrument. 5. K33 elastic constant ("bending", pN at 20 ° C): The liquid to be tested or the liquid crystal medium 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. The instrument is added with a dielectric anisotropy (Δε) factor conversion to obtain K33. 6. Refractive index anisotropy (Δn): A liquid or liquid crystal medium to be measured was measured using an Abbe refractometer (manufacturer: ATAGO; model: DR-M2) on which a polarizing plate was attached. First, wipe the main surface of the Abbe refractometer in a single direction, then add a small amount of the test solution to the main crucible, and then refract the filter at a temperature of 25 ° C using a filter of 589 nm. Rate anisotropy measurement. 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 ; refractive index anisotropy (Δn) = n -n . 7. Low temperature storage (LTS, unit: day): Put 0.3 g of liquid or liquid crystal medium into a 7 mL glass bottle, and then place the glass bottle at -30 °C. In the cabinet, the time for liquid crystal precipitation is recorded, which is the number of days of low temperature storage. The longer the low temperature storage time, the better.

[ 製備例 1 2] 化學式 1-2B 所示化合物 I<TABLE border="1" borderColor="#000000" width="_0012"><TBODY><tr><td><img wi="488" he="118" file="IMG-2/Draw/02_image013.jpg" img-format="jpg"></img></td></tr><tr><td>   </td><td> R<sup>1</sup></td><td> R<sup>2</sup></td></tr><tr><td> 製備例1 </td><td> C<sub>3</sub>H<sub>7</sub></td><td> F </td></tr><tr><td> 製備例2 </td><td> C<sub>2</sub>H<sub>5</sub></td><td> F </td></tr></TBODY></TABLE>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: (R 1=C 3H 7) 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: (R 2=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,R 1為C 3H 7)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,R 1為C 3H 7,R 2為F)。前述反應過程如下反應式: (R 1為C 3H 7,R 2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: 1H-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=8.4Hz), 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(R 1為C 2H 5,R 2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R 1為C 2H 5,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: 1H-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=8.4Hz), 6.994(3H, m), 7.208(2H, J=10.4Hz), 7.472(3H, m)。 [ Preparation Examples 1 and 2] Compound I shown in Chemical Formula 1-2B <TABLE border="1"borderColor="#000000"width="_0012"><TBODY><tr><td><imgwi="488"He="118"file="IMG-2/Draw/02_image013.jpg"img-format="jpg"></img></td></tr><tr><td></td><td>R<sup>1</sup></td><td>R<sup>2</sup></td></tr><tr><td> Preparation 1 </td><td>C<sub>3</sub>H<sub>7</sub></td><td>F</td></tr><tr><td> Preparation Example 2 </td><td>C<sub>2</sub>H<sub>5</sub></td><td>F</td></tr></TBODY></TABLE> Description: 1. 4-propylphenol (3.3 g, 24 mmol), magnesium chloride (3.9 g, 36 mmol), paraformaldehyde (5 g, 165 mmol), triethylamine (13.5 mL, 9.3 mmol) and acetonitrile (60 mL) Place in a 250 mL two-necked flask and mix to obtain a reaction solution. The reaction solution was heated under reflux under nitrogen, and the reaction was confirmed to be complete by a thin-film chromatography layer (TLC). After reacting for 4 hours, it was confirmed that the reaction was completed, and an aqueous hydrochloric acid solution (1N, 50 mL) was added to the reaction mixture to obtain a mixture. Then, the mixture was subjected to extraction three times with ethyl acetate, and the organic layer was collected, and anhydrous magnesium sulfate was added to the organic layer, and the mixture was filtered and concentrated under reduced pressure to give a crude product. The crude product was purified by column chromatography (the extract was a mixture 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 foregoing reaction process is as follows: (R 1 = C 3 H 7 ) 2. Sodium borohydride (0.9 g, 24 mmol) and methanol (30 mL) were placed in a 250 mL double flask and cooled to 0 °C. Then, 2-hydroxy-5-propyl-benzaldehyde (2.0 g, 12 mmol) was slowly dropped into a 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 (1 N, 25 mL) was placed in a double-necked flask to obtain a mixture. The mixture was subjected to three extractions with ethyl acetate, and the organic layer was collected, and then anhydrous magnesium sulfate was added to the organic layer, followed by filtration and concentration under reduced pressure to give a crude product. The crude product was purified by column chromatography (the extract was a mixture of ethyl acetate and n-hexane, and the volume ratio of ethyl acetate to n-hexane was 2:8) to obtain 2-hydroxymethyl-4- Propylphenol (1.7 g, white solid, SL1). The foregoing reaction process is as follows: 3. Tetrakis(triphenylphosphine)palladium (0.34 g, 3 mol%), 4-bromo-3-fluoro-benzaldehyde (3.0 g, 14.8 mmol), 4-[(3', 4', 5'- Trifluorophenyl)-difluoromethoxy]-3,5-difluorophenylboronic acid (8.6 g, 60 mmol, the synthesis of this compound can be referred to EP 1341742 A1), potassium carbonate (6.1 g, 44.4 mmol), water ( 20 mL) and tetrahydrofuran (180 mL) were added to a double neck round bottom bottle for stirring and a reaction liquid was obtained. The reaction solution was heated and refluxed, and it was confirmed by TLC whether the reaction was complete during the reaction. After reacting for 24 hours, it was confirmed that the reaction was completed, and water (100 mL) was added to the reaction mixture to obtain a mixture. Then, the mixture was subjected to extraction three times with ethyl acetate, and the organic layer was collected, and anhydrous magnesium sulfate was added to the organic layer, and the mixture was filtered and concentrated under reduced pressure to give a crude product. The crude product was purified by column chromatography (purified to n-hexane) to afford compound SR2 (5.8 g, white solid). The foregoing reaction process is as follows: (R 2 =F) 4. Compound SR2 (1.0 g, 2.4 mmol), dichloromethane (30 mL) and trimethylchloromethane (0.5 g, 4.8 mmol) were placed in a 250 mL flask and allowed to stand at room temperature Stirring and mixing; then, 2-hydroxymethyl-4-propylphenol solution [passing 1.2 g of 2-hydroxymethyl-4-propylphenol (such as SL1, R 1 is C 3 H 7 ) dissolved in 10 mL Obtained from methylene chloride] 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 the completion of the reaction, water (25 mL) was added to a double-necked flask to obtain a mixed liquid. The mixture was subjected to three extractions with dichloromethane and the organic layer was collected, and anhydrous magnesium sulfate was added to the organic layer, followed by filtration and concentration under reduced pressure to give a crude product. The crude product was purified by column chromatography (the extract was a mixture 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. a compound I (0.9g, white solid, R 1 is C 3 H 7, R 2 is F). The foregoing reaction process is as follows: (R 1 is C 3 H 7 and R 2 is F, and is designated as "3SGUQUF" hereinafter). The molecular weight of the compound of Preparation Example 1 was measured by gas chromatography tandem mass spectrometry (GC-MS), and the result was: m/ z=580.1362[M] + . The spectral measurements of the compound of Preparation Example 1 were carried out using a nuclear magnetic resonance apparatus. The results were as follows: 1 H-NMR (CDCl 3 , 400 MHz), d (ppm): 0.968 (3H, t, J = 7.2 Hz), 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 preparation method of the compound of Chemical Formula 1-2B (R 1 is C 2 H 5 and R 2 is F) of Preparation Example 2 is the same as that of Preparation Example 1, and is also prepared in accordance with the above respective 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 is labeled as "2SGUQUF" below. The molecular weight of the compound of Preparation Example 2 was measured by gas chromatography tandem mass spectrometry (GC-MS) and found to be m/z = 580.1362 [M] + . The spectral measurement of the compound of Preparation Example 2 was carried out by using a nuclear magnetic resonance apparatus. The results were as follows: 1 H-NMR (CDCl 3 , 400 MHz), d (ppm): 1.205 (3H, t, J = 7.2 Hz), 2.580 (2H, q, J = 7.6 Hz), 4.983 (1H, d, J = 14.8 Hz), 5.188 (1H, d, J = 14.8 Hz), 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 4] 化學式 1-2A 所示化合物 I<TABLE border="1" borderColor="#000000" width="_0013"><TBODY><tr><td><img wi="488" he="118" file="IMG-2/Draw/02_image011.jpg" img-format="jpg"></img></td></tr><tr><td>   </td><td> R<sup>1</sup></td><td> R<sup>2</sup></td></tr><tr><td> 製備例3 </td><td> C<sub>3</sub>H<sub>7</sub></td><td> F </td></tr><tr><td> 製備例4 </td><td> C<sub>2</sub>H<sub>5</sub></td><td> F </td></tr></TBODY></TABLE>製備例3之化學式1-2A所示化合物(R 1為C 3H 7,R 2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: 1H-NMR(CDCl 3, 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(R 1為C 2H 5,R 2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R 1為C 2H 5,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: 1H-NMR(CDCl 3, 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 shown in Chemical Formula 1-2A <TABLE border="1"borderColor="#000000"width="_0013"><TBODY><tr><td><imgwi="488"He="118"file="IMG-2/Draw/02_image011.jpg"img-format="jpg"></img></td></tr><tr><td></td><td>R<sup>1</sup></td><td>R<sup>2</sup></td></tr><tr><td> Preparation 3 </td><td>C<sub>3</sub>H<sub>7</sub></td><td>F</td></tr><tr><td> Preparation Example 4 </td><td>C<sub>2</sub>H<sub>5</sub></td><td>F</td></tr></TBODY></TABLE> Chemical Formula 1-2A of Preparation Example 3 The compound (R 1 is C 3 H 7 , R 2 is F) was prepared in the same manner as in Preparation Example 1, and was also prepared in accordance with the above respective reaction formulas; Preparation Example 3 differs from Preparation Example 1 in that: The SR2 compound in the above is substituted by the following SR1, and the SR1 is produced as follows (4-bromo-3-fluoro-benzaldehyde in the SR2 process is replaced with 4-bromo-benzaldehyde). Preparation Example 3 is indicated below as "3SPUQUF". The molecular weight of the compound of Preparation Example 3 was measured by gas chromatography tandem mass spectrometry (GC-MS) and found to be m/z = 562.1467 [M] + . The spectral measurement of the compound of Preparation Example 3 was carried out by using a nuclear magnetic resonance apparatus. The results were as follows: 1 H-NMR (CDCl 3 , 400 MHz), d (ppm): 1.105 (3H, t, J = 7.2 Hz), 1.645 (2H, m), 2.263 (2H, t, J = 7.6 Hz), 5.103 (1H, d, J = 14.8 Hz), 5.221 (1H, d, J = 14.8 Hz), 6.156 (1H, s), 6.871 (1H, s), 6.892 (1H, d, J = 8.4 Hz), 7.036 (3H, m), 7.178 (2H, J = 10 Hz), 7.633 (2H, d, J = 10.4 Hz), 7.724 (2H, d, J =10.4Hz). The preparation of the compound of Chemical Formula 1-2A (R 1 is C 2 H 5 , R 2 is F) of Preparation Example 4 is the same as that of Preparation Example 3; Preparation Example 4 is different from Preparation Example 3 in the reaction formula. R 1 is C 2 H 5 and is indicated below as "2SPUQUF". The molecular weight of the compound of Preparation Example 4 was measured by gas chromatography tandem mass spectrometry (GC-MS) and found to be m/z = 548.1196 [M] + . The spectral measurement of the compound of Preparation Example 4 was carried out by using a nuclear magnetic resonance apparatus. The results were as follows: 1 H-NMR (CDCl 3 , 400 MHz), d (ppm): 1.207 (3H, t, J = 7.2 Hz), 2.285 (2H, q, J = 7.6 Hz), 4.985 (1H, d, J = 14.8 Hz), 5.193 (1H, d, J = 14.8 Hz), 6.006 (1H, s), 6.849 (1H, s), 6.860 (1H, d, J = 8.4 Hz), 7.015 (3H, m), 7.145 (2H, J = 10 Hz), 7.612 (2H, d, J = 10.4 Hz), 7.713 (2H, d, J = 10.4 Hz).

[ 製備例 5] 化學式 1-2C 所示化合物 I<TABLE border="1" borderColor="#000000" width="_0014"><TBODY><tr><td><img wi="490" he="142" file="IMG-2/Draw/02_image015.jpg" img-format="jpg"></img></td></tr><tr><td>   </td><td> R<sup>1</sup></td><td> R<sup>2</sup></td></tr><tr><td> 製備例5 </td><td> OC<sub>4</sub>H<sub>9</sub></td><td> F </td></tr></TBODY></TABLE>製備例5之化學式1-2C所示化合物(R 1為OC 4H 9,R 2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: 1H-NMR(CDCl 3, 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) [ Preparation Example 5] Compound I represented by Chemical Formula 1-2C <TABLE border="1"borderColor="#000000"width="_0014"><TBODY><tr><td><imgwi="490" he= "142"file="IMG-2/Draw/02_image015.jpg"img-format="jpg"></img></td></tr><tr><td></td><td> R <sup>1</sup></td><td>R<sup>2</sup></td></tr><tr><td> Preparation Example 5 </td><td>OC<Sub>4</sub>H<sub>9</sub></td><td>F</td></tr></TBODY></TABLE> is shown in Chemical Formula 1-2C of Preparation Example 5 The preparation method of the compound (R 1 is OC 4 H 9 and R 2 is F) is the same as that of Preparation Example 1, and is also prepared according to the above respective reaction formulas; Preparation Example 5 is different from Preparation Example 1 in the reaction formula. The SL1 compound was substituted with the following SL2, and the SL2 was produced as follows (the 4-propylphenol in the SL1 process was replaced with 2,3-difluoro-4-butoxyphenol). Finally, the SL2 compound is reacted with the SR1 compound to prepare the compound of Preparation Example 5, and the reaction process is as follows: Preparation Example 5 is indicated below as "4OSyPUQUF". The molecular weight of the compound of Preparation Example 5 was measured by gas chromatography tandem mass spectrometry (GC-MS) and found to be m/z = 628.1195 [M] + . The spectral measurement of the compound of Preparation Example 5 was carried out by a nuclear magnetic resonance apparatus. The results were as follows: 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 = 8.0 Hz), 7.012 (2H, m), 7.257 (2H, J = 10 Hz), 7.655 (2H, d, J = 10.4 Hz), 7.751 (2H, d, J =10.4Hz)

[ 實施例 1 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 medium According to the compositions and contents of Table 2 below, Compound I, Compound II, Compound III and Compound IV were separately mixed to obtain liquid crystal media of Examples 1 to 16. Next, the properties of the liquid crystal media of Examples 1 to 16 were tested in accordance with the test method of [0027], and the results are summarized in Table 3.

[表2] <TABLE border="1" borderColor="#000000" width="_0015"><TBODY><tr><td>   </td><td> 化合物 (含量wt%) </td></tr><tr><td> I </td><td> II </td><td> III </td><td> IV </td></tr><tr><td> 實施例1 </td><td> 2SGUQUF (7) 3SGUQUF (7) 共14wt% </td><td>   </td><td> 3CCV (45.7) 5PP1 (2) 4CCP3 (4) 3CPP2 (4) 3CPPF (2) 3CPGF (7) </td><td> 2CPGF (9.1) 3CPTP2 (4.2) 3CCPC3 (3) 3CCPGF (5) 共86wt% </td><td>   </td></tr><tr><td> 實施例2 </td><td> 2SGUQUF (7) 3SGUQUF (7) 共14wt% </td><td>   </td><td> 3CCV (47.7) 5PP1 (2) V2PTP2V (2.8) 4CCP3 (4) 3CPP2 (4) 3CPPF (2) </td><td> 3CPGF (7) 2CPGF (7) 3CPTP2 (2) 3CPPC3 (3.5) 3CCPGF (4) 共86wt% </td><td>   </td></tr><tr><td> 實施例3 </td><td> 2SPUQUF(3.5) 共3.5wt% </td><td> 1RIGUQUF (2.5) 2RIGUQUF (3.75) 3RIGUQUF (3.75) 3RIGUO2F (2.5) 共12.5wt% </td><td> 3CCV (45) 5PP1 (7.5) 3CCPOCF3(8.5) 3CPP2 (4) </td><td> 2CPPF (5.5) 3CPPF (7) 3PGB2 (4.5) 3CCPGF (2) 共84wt% </td><td>   </td></tr><tr><td> 實施例4 </td><td> 2SGUQUF (5) 共5wt% </td><td> 2RIGUO2F (8) 3RIGUO2F (8) 共16wt% </td><td> 3CCV (42.9) 5PP1 (2) 4CCP3 (4) 3CPP2 (4) 3CPPF (2) </td><td> 3CPGF (7) 2CPGF (7) 3CPTP2 (3.1) 3CPPC3 (3) 3CCPGF (4) 共79wt% </td><td>   </td></tr><tr><td> 實施例5 </td><td> 2SPUQUF (5) 共5wt% </td><td> 2RIGUO2F (8) 3RIGUO2F (8) 共16wt% </td><td> 3CCV (40) 5PP1 (8) 3CCPOCF3 (9) 3CCGF (7) 5CCGF (3) </td><td> 3CPGF (3) 3PGB2 (2) 3CPPC3 (4) 3CCPGF (3) 共79wt% </td><td>   </td></tr></TBODY></TABLE>[續表2] <TABLE border="1" borderColor="#000000" width="85%"><TBODY><tr><td>   </td><td> 化合物 (含量wt%) </td></tr><tr><td> I </td><td> II </td><td> III </td><td> IV </td></tr><tr><td> 實施例6 </td><td> 2SGUQUF (7) 3SGUQUF (7) 2SPUQUF (5) 共19wt% </td><td>   </td><td> 3CCV (38) 3CCV1 (3) 3CC5 (3) 5PP1 (5) 3PTPO1 (4) VCCP1 (5) </td><td> 3CCPOCF3 (7) 3CCPF (3) VCCGF (3) 3CPGF (7) 3CCPGF (3) 共81wt% </td><td>   </td></tr><tr><td> 實施例7 </td><td> 2SGUQUF (7) 3SGUQUF (7) 2SPUQUF (5) 共19wt% </td><td>   </td><td> 3CCV (45) 3CC5 (3) 5PP1 (3) 3CCPOCF3 (5) 3CCPF (3) 3CCGF (2) </td><td> 5CCGF (2) 3CPGF (7) 3PGP2 (4) V2PGP3 (4) 3CCPGF (3) 共81wt% </td><td>   </td></tr><tr><td> 實施例8 </td><td> 2SGUQUF (6) 3SGUQUF (6) 3SPUQUF (3) 共15wt% </td><td> 3CCQUF (3) 3CUQUF (3) 3CGUQUF (2) 3PGUF (4) 共12wt% </td><td> 3CCV (45) 5PP1 (5) 3CCPOCF3 (9) 3CCGF (3) </td><td> 3CPPF (3) 3CPTP2 (3) 3CGPC3 (2) 共70wt% </td><td> 2SPUO2F (3) 共3wt% </td></tr><tr><td> 實施例9 </td><td> 2SGUQUF (6) 3SGUQUF (6) 3SPUQUF (4) 共16wt% </td><td> 3CCPUF (3) 3CCQUF (4) 2CCUF (4) 3CPUF (4) 共15wt% </td><td> 3CCV (45) 3CCO1 (3) 5CP3 (3) </td><td> 3CCPOCF3 (6) 3CCGOCF3 (3) 3PGB2 (5) 共65wt% </td><td> 2SPUO2F(4) 共4wt% </td></tr><tr><td> 實施例10 </td><td> 2SGUQUF (6) 3SGUQUF (6) 3SPUQUF (3) 共15wt% </td><td> 3CGUQUF (3) 3CCUOCF2H (3) 2CGUF (3) 共9wt% </td><td> 3CCV (43) 1PP2V (2) 3CCPOCF3 (8) 3CCGF (3) </td><td> 3CPPF (4) 3CPTP2 (4) 3PGB2 (2) 3CGPC3 (7) 共73wt% </td><td> 2SPUO2F(3) 共3wt% </td></tr><tr><td> 實施例11 </td><td> 2SGUQUF (7) 3SGUQUF (7) 2SPUQUF(5.2) 共19.2wt% </td><td>   </td><td> 3CCV (46) 5PP1 (3) 3CCPOCF3 (9) 5CCPOCF3 (2) 3CPP2 (5.3) </td><td> 2CPPF (3) 3CPPF (5.5) 3PGB2 (1) 3CCPGF (6) 共80.8wt% </td><td>   </td></tr></TBODY></TABLE>[續表2] <TABLE border="1" borderColor="#000000" width="85%"><TBODY><tr><td>   </td><td> 化合物 (含量wt%) </td></tr><tr><td> I </td><td> II </td><td> III </td><td> IV </td></tr><tr><td> 實施例12 </td><td> 2SGUQUF (7) 3SGUQUF (7) 2SPUQUF(5.2) 共19.2wt% </td><td>   </td><td> 3CCV (50) 3CCPOCF3 (9) 5CCPOCF3 (2) 3CPP2 (5.3) </td><td> 2CPPF (3) 3CPPF (5.5) 3PGB2 (1.5) 3CCPGF (4.5) 共80.8wt% </td><td>   </td></tr><tr><td> 實施例13 </td><td> 2SGUQUF (7) 3SGUQUF (7) 2SPUQUF (4) 共18wt% </td><td>   </td><td> 3CCV (47) 5PP1 (3.5) 3CCPOCF3 (9) 5CCPOCF3 (1.5) 3CPP2 (3.5) </td><td> 2CPPF (2.5) 3CPPF (4) 3PGP2 (1.5) 3CCPGF (6) 共78.5wt% </td><td> 2SPUO2F (3.5) 共3.5wt% </td></tr><tr><td> 實施例14 </td><td> 2SGUQUF (6) 2SPUQUF (4) 共10wt% </td><td> 2doPUO2F (2.5) 3doPUO2F (3) 2doPUQUF (4.5) 5doPUQUF (3) 共13wt% </td><td> 3CCYO2 (8) 2CPYO2 (8.5) 3CYO4 (5) 4OSy2 (6) </td><td> 3CCV (29) 3CCP1 (4) 3CCPOCF3(12.5) 2PGB2 (4) 共77wt% </td><td>   </td></tr><tr><td> 實施例15 </td><td> 2SGUQUF(6.5) 3SGUQUF(6.5) 共13wt% </td><td> 5PGUQUF (3) 4PGUQUF (5) 3PGUQUF (5) 共13wt% </td><td> 3CCYO2 (2.5) 2CPYO2 (10) 3CYO4 (11.5) </td><td> 3CCV (35.5) 3CCPOCF3(11.5) 3PGB2 (3) 共74wt% </td><td>   </td></tr><tr><td> 實施例16 </td><td> 2SGUQUF(6.5) 3SGUQUF(6.5) 共13wt% </td><td> 2doPUO2F (2.5) 3doPUO2F (3) 2doPUQUF (4.5) 5doPUQUF (3) 共13wt% </td><td> 3CCYO2 (2.5) 2CPYO2 (10) 3CYO4 (11.5) </td><td> 3CCV (35.5) 3CCPOCF3(11.5) 3PGB2 (3) 共74wt% </td><td>   </td></tr></TBODY></TABLE>[Table 2]         <TABLE border="1" borderColor="#000000" width="_0015"><TBODY><tr><td> </td><td> compound (content wt%) </td></tr>< Tr><td> I </td><td> II </td><td> III </td><td> IV </td></tr><tr><td> Example 1 </td ><td> 2SGUQUF (7) 3SGUQUF (7) 14wt% </td><td> </td><td> 3CCV (45.7) 5PP1 (2) 4CCP3 (4) 3CPP2 (4) 3CPPF (2) 3CPGF (7) </td><td> 2CPGF (9.1) 3CPTP2 (4.2) 3CCPC3 (3) 3CCPGF (5) Total 86wt% </td><td> </td></tr><tr><td> Example 2 </td><td> 2SGUQUF (7) 3SGUQUF (7) Total 14wt% </td><td> </td><td> 3CCV (47.7) 5PP1 (2) V2PTP2V (2.8) 4CCP3 (4 3CPP2 (4) 3CPPF (2) </td><td> 3CPGF (7) 2CPGF (7) 3CPTP2 (2) 3CPPC3 (3.5) 3CCPGF (4) Total 86wt% </td><td> </td> </tr><tr><td> Example 3 </td><td> 2SPUQUF(3.5) Total 3.5wt% </td><td> 1RIGUQUF (2.5) 2RIGUQUF (3.75) 3RIGUQUF (3.75) 3RIGUO2F (2.5 A total of 12.5wt% </td><td> 3CCV (45) 5PP1 (7.5) 3CCPOCF3(8.5) 3CPP2 (4) </td><td> 2CPPF (5.5) 3CPPF (7) 3PGB2 (4.5) 3CCPGF (2) A total of 84wt% </td><td> </td></tr><tr><td> Example 4 </td><td> 2SGUQUF (5) Total 5wt% </td><td> 2R IGUO2F (8) 3RIGUO2F (8) Total 16wt% </td><td> 3CCV (42.9) 5PP1 (2) 4CCP3 (4) 3CPP2 (4) 3CPPF (2) </td><td> 3CPGF (7) 2CPGF (7) 3CPTP2 (3.1) 3CPPC3 (3) 3CCPGF (4) 79% by weight </td><td> </td></tr><tr><td> Example 5 </td><td> 2SPUQUF (5) Total 5wt% </td><td> 2RIGUO2F (8) 3RIGUO2F (8) Total 16wt% </td><td> 3CCV (40) 5PP1 (8) 3CCPOCF3 (9) 3CCGF (7) 5CCGF (3 ) </td><td> 3CPGF (3) 3PGB2 (2) 3CPPC3 (4) 3CCPGF (3) Total 79wt% </td><td> </td></tr></TBODY></TABLE> [Continued Table 2]         <TABLE border="1" borderColor="#000000" width="85%"><TBODY><tr><td> </td><td> compound (content wt%) </td></tr> <tr><td> I </td><td> II </td><td> III </td><td> IV </td></tr><tr><td> Example 6 </ Td><td> 2SGUQUF (7) 3SGUQUF (7) 2SPUQUF (5) 19% by weight </td><td> </td><td> 3CCV (38) 3CCV1 (3) 3CC5 (3) 5PP1 (5) 3PTPO1 (4) VCCP1 (5) </td><td> 3CCPOCF3 (7) 3CCPF (3) VCCGF (3) 3CPGF (7) 3CCPGF (3) 81% by weight </td><td> </td>< /tr><tr><td> Example 7 </td><td> 2SGUQUF (7) 3SGUQUF (7) 2SPUQUF (5) 19% by weight </td><td> </td><td> 3CCV ( 45) 3CC5 (3) 5PP1 (3) 3CCPOCF3 (5) 3CCPF (3) 3CCGF (2) </td><td> 5CCGF (2) 3CPGF (7) 3PGP2 (4) V2PGP3 (4) 3CCPGF (3) 81wt% </td><td> </td></tr><tr><td> Example 8 </td><td> 2SGUQUF (6) 3SGUQUF (6) 3SPUQUF (3) A total of 15wt% </ Td><td> 3CCQUF (3) 3CUQUF (3) 3CGUQUF (2) 3PGUF (4) Total 12wt% </td><td> 3CCV (45) 5PP1 (5) 3CCPOCF3 (9) 3CCGF (3) </td ><td> 3CPPF (3) 3CPTP2 (3) 3CGPC3 (2) 70% by weight </td><td> 2SPUO2F (3) Total 3wt% </td></tr><tr><td> Example 9 </td><td> 2SGUQUF ( 6) 3SGUQUF (6) 3SPUQUF (4) Total 16wt% </td><td> 3CCPUF (3) 3CCQUF (4) 2CCUF (4) 3CPUF (4) Total 15wt% </td><td> 3CCV (45) 3CCO1 (3) 5CP3 (3) </td><td> 3CCPOCF3 (6) 3CCGOCF3 (3) 3PGB2 (5) 65wt% </td><td> 2SPUO2F(4) Total 4wt% </td></ Tr><tr><td> Example 10 </td><td> 2SGUQUF (6) 3SGUQUF (6) 3SPUQUF (3) Total 15wt% </td><td> 3CGUQUF (3) 3CCUOCF2H (3) 2CGUF ( 3) 9wt% </td><td> 3CCV (43) 1PP2V (2) 3CCPOCF3 (8) 3CCGF (3) </td><td> 3CPPF (4) 3CPTP2 (4) 3PGB2 (2) 3CGPC3 (7 73% by weight </td><td> 2SPUO2F(3) Total 3wt% </td></tr><tr><td> Example 11 </td><td> 2SGUQUF (7) 3SGUQUF (7) 2SPUQUF(5.2) Total 19.2wt% </td><td> </td><td> 3CCV (46) 5PP1 (3) 3CCPOCF3 (9) 5CCPOCF3 (2) 3CPP2 (5.3) </td><td> 2CPPF (3) 3CPPF (5.5) 3PGB2 (1) 3CCPGF (6) Total 80.8wt% </td><td> </td></tr></TBODY></TABLE>[Continued Table 2]         <TABLE border="1" borderColor="#000000" width="85%"><TBODY><tr><td> </td><td> compound (content wt%) </td></tr> <tr><td> I </td><td> II </td><td> III </td><td> IV </td></tr><tr><td> Example 12 </ Td><td> 2SGUQUF (7) 3SGUQUF (7) 2SPUQUF(5.2) Total 19.2wt% </td><td> </td><td> 3CCV (50) 3CCPOCF3 (9) 5CCPOCF3 (2) 3CPP2 (5.3 </td><td> 2CPPF (3) 3CPPF (5.5) 3PGB2 (1.5) 3CCPGF (4.5) Total 80.8wt% </td><td> </td></tr><tr><td> Implementation Example 13 </td><td> 2SGUQUF (7) 3SGUQUF (7) 2SPUQUF (4) Total 18wt% </td><td> </td><td> 3CCV (47) 5PP1 (3.5) 3CCPOCF3 (9) 5CCPOCF3 (1.5) 3CPP2 (3.5) </td><td> 2CPPF (2.5) 3CPPF (4) 3PGP2 (1.5) 3CCPGF (6) Total 78.5wt% </td><td> 2SPUO2F (3.5) Total 3.5wt% </td></tr><tr><td> Example 14 </td><td> 2SGUQUF (6) 2SPUQUF (4) Total 10wt% </td><td> 2doPUO2F (2.5) 3doPUO2F (3) 2doPUQUF (4.5) 5doPUQUF (3) 13wt% </td><td> 3CCYO2 (8) 2CPYO2 (8.5) 3CYO4 (5) 4OSy2 (6) </td><td> 3CCV (29) 3CCP1 (4) 3CCPOCF3 (12.5) 2PGB2 (4) 77% by weight </td><td> </td></tr><tr><td> Example 15 </td><td> 2SGU QUF(6.5) 3SGUQUF(6.5) 13wt% </td><td> 5PGUQUF (3) 4PGUQUF (5) 3PGUQUF (5) 13wt% </td><td> 3CCYO2 (2.5) 2CPYO2 (10) 3CYO4 ( 11.5) </td><td> 3CCV (35.5) 3CCPOCF3(11.5) 3PGB2 (3) Total 74wt% </td><td> </td></tr><tr><td> Example 16 </ Td><td> 2SGUQUF(6.5) 3SGUQUF(6.5) 13wt% </td><td> 2doPUO2F (2.5) 3doPUO2F (3) 2doPUQUF (4.5) 5doPUQUF (3) 13wt% </td><td> 3CCYO2 (2.5) 2CPYO2 (10) 3CYO4 (11.5) </td><td> 3CCV (35.5) 3CCPOCF3(11.5) 3PGB2 (3) Total 74wt% </td><td> </td></tr></ TBODY></TABLE>

[表3] <TABLE border="1" borderColor="#000000" width="_0016"><TBODY><tr><td>   </td><td> T<sub>ni</sub>(°C) </td><td> Δε </td><td> ε<sub>⊥</sub></td><td> K11 </td><td> K33 </td><td> γ1(mPa•S) </td><td> Δn </td></tr><tr><td> 實施例 </td><td> 1 </td><td> 87.5 </td><td> 5.1 </td><td> 3.19 </td><td> 10.7 </td><td> 13.8 </td><td> 67.0 </td><td> 0.1050 </td></tr><tr><td> 2 </td><td> 82.1 </td><td> 4.8 </td><td> 3.14 </td><td> 10.3 </td><td> 12.95 </td><td> 60.3 </td><td> 0.1038 </td></tr><tr><td> 3 </td><td> 78.2 </td><td> 4.51 </td><td> 2.88 </td><td> 10.7 </td><td> 11.7 </td><td> 50.2 </td><td> 0.1140 </td></tr><tr><td> 4 </td><td> 84.9 </td><td> 4.8 </td><td> 3.2 </td><td> 10.7 </td><td> 12.9 </td><td> 65.5 </td><td> 0.1162 </td></tr><tr><td> 5 </td><td> 85.3 </td><td> 4.6 </td><td> 3.16 </td><td> 10.6 </td><td> 12.75 </td><td> 63.2 </td><td> 0.1140 </td></tr><tr><td> 6 </td><td> 76.9 </td><td> 6.4 </td><td> 3.37 </td><td> 10.05 </td><td> 13 </td><td> 59.9 </td><td> 0.1002 </td></tr><tr><td> 7 </td><td> 77.5 </td><td> 6.2 </td><td> 3.37 </td><td> 10 </td><td> 12.55 </td><td> 58.8 </td><td> 0.1000 </td></tr><tr><td> 8 </td><td> 69.0 </td><td> 6.84 </td><td> 3.44 </td><td> 8.6 </td><td> 10.7 </td><td> 53.5 </td><td> 0.0952 </td></tr><tr><td> 9 </td><td> 69.7 </td><td> 6.6 </td><td> 3.41 </td><td> 8.3 </td><td> 10.8 </td><td> 56.9 </td><td> 0.0925 </td></tr><tr><td> 10 </td><td> 90.8 </td><td> 6.36 </td><td> 3.27 </td><td> 10.7 </td><td> 14.5 </td><td> 75.7 </td><td> 0.1056 </td></tr><tr><td> 11 </td><td> 87.7 </td><td> 6.35 </td><td> 3.22 </td><td> 10.5 </td><td> 13.5 </td><td> 63.1 </td><td> 0.0999 </td></tr><tr><td> 12 </td><td> 85.1 </td><td> 6.345 </td><td> 3.195 </td><td> 10.5 </td><td> 13.6 </td><td> 63.515 </td><td> 0.0981 </td></tr><tr><td> 13 </td><td> 81.6 </td><td> 6.43 </td><td> 3.27 </td><td> 10.1 </td><td> 12.6 </td><td> 61.2 </td><td> 0.0997 </td></tr><tr><td> 14 </td><td> 79.9 </td><td> 6.9 </td><td> 5.8 </td><td> 10.1 </td><td> 14.2 </td><td> 89.6 </td><td> 0.1053 </td></tr><tr><td> 15 </td><td> 77.2 </td><td> 7.55 </td><td> 5.29 </td><td> 9.8 </td><td> 13 </td><td> 90.6 </td><td> 0.1104 </td></tr><tr><td> 16 </td><td> 75.6 </td><td> 8 </td><td> 5.4 </td><td> 9.5 </td><td> 13.3 </td><td> 93.6 </td><td> 0.1029 </td></tr></TBODY></TABLE>[table 3]         <TABLE border="1" borderColor="#000000" width="_0016"><TBODY><tr><td> </td><td> T<sub>ni</sub>(°C) </ Td><td> Δε </td><td> ε<sub>⊥</sub></td><td> K11 </td><td> K33 </td><td> γ1(mPa•S </td><td> Δn </td></tr><tr><td> Example </td><td> 1 </td><td> 87.5 </td><td> 5.1 < /td><td> 3.19 </td><td> 10.7 </td><td> 13.8 </td><td> 67.0 </td><td> 0.1050 </td></tr><tr> <td> 2 </td><td> 82.1 </td><td> 4.8 </td><td> 3.14 </td><td> 10.3 </td><td> 12.95 </td><td > 60.3 </td><td> 0.1038 </td></tr><tr><td> 3 </td><td> 78.2 </td><td> 4.51 </td><td> 2.88 < /td><td> 10.7 </td><td> 11.7 </td><td> 50.2 </td><td> 0.1140 </td></tr><tr><td> 4 </td> <td> 84.9 </td><td> 4.8 </td><td> 3.2 </td><td> 10.7 </td><td> 12.9 </td><td> 65.5 </td><td > 0.1162 </td></tr><tr><td> 5 </td><td> 85.3 </td><td> 4.6 </td><td> 3.16 </td><td> 10.6 < /td><td> 12.75 </td><td> 63.2 </td><td> 0.1140 </td></tr><tr><td> 6 </td><td> 76.9 </td> <td> 6.4 </td><td> 3.37 </td><td> 10.05 </td><td> 13 </td><td> 59.9 </td><td> 0.1002 </td></ t r><tr><td> 7 </td><td> 77.5 </td><td> 6.2 </td><td> 3.37 </td><td> 10 </td><td> 12.55 < /td><td> 58.8 </td><td> 0.1000 </td></tr><tr><td> 8 </td><td> 69.0 </td><td> 6.84 </td> <td> 3.44 </td><td> 8.6 </td><td> 10.7 </td><td> 53.5 </td><td> 0.0952 </td></tr><tr><td> 9 </td><td> 69.7 </td><td> 6.6 </td><td> 3.41 </td><td> 8.3 </td><td> 10.8 </td><td> 56.9 < /td><td> 0.0925 </td></tr><tr><td> 10 </td><td> 90.8 </td><td> 6.36 </td><td> 3.27 </td> <td> 10.7 </td><td> 14.5 </td><td> 75.7 </td><td> 0.1056 </td></tr><tr><td> 11 </td><td> 87.7 </td><td> 6.35 </td><td> 3.22 </td><td> 10.5 </td><td> 13.5 </td><td> 63.1 </td><td> 0.0999 < /td></tr><tr><td> 12 </td><td> 85.1 </td><td> 6.345 </td><td> 3.195 </td><td> 10.5 </td> <td> 13.6 </td><td> 63.515 </td><td> 0.0981 </td></tr><tr><td> 13 </td><td> 81.6 </td><td> 6.43 </td><td> 3.27 </td><td> 10.1 </td><td> 12.6 </td><td> 61.2 </td><td> 0.0997 </td></tr>< Tr><td> 14 </td><td> 79.9 </td><td> 6.9 </td><td> 5.8 </td><td> 10.1 </td><td> 14.2 </td> <td> 89.6 </td><td> 0.1053 </td></tr><tr><td> 15 </td><td> 77.2 </td><td> 7.55 </td><td> 5.29 </td ><td> 9.8 </td><td> 13 </td><td> 90.6 </td><td> 0.1104 </td></tr><tr><td> 16 </td><td > 75.6 </td><td> 8 </td><td> 5.4 </td><td> 9.5 </td><td> 13.3 </td><td> 93.6 </td><td> 0.1029 </td></tr></TBODY></TABLE>

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T ni、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 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 compositions and contents of Table 4 below, Compound II and Compound III were separately mixed to obtain 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 in accordance with the test method of [0027], and the results were summarized in Tables 5 and 6, respectively. Further, in Table 5, the liquid crystal media of Example 16 and Comparative Example 2 were compared; in Table 6, Example 1 was compared with Comparative Example 1.

[表4] <TABLE border="1" borderColor="#000000" width="_0017"><TBODY><tr><td>   </td><td> 化合物 (含量wt%) </td></tr><tr><td> II </td><td> III </td></tr><tr><td> 比較例1 </td><td> 2RIGUQUF (7) 3RIGUQUF (7) 共14wt% </td><td> 3CCV (50) 5PP1 (3) 4CCP3 (4) 3CPP2 (4) 3CPPF (2) </td><td> 3CPGF (7) 2CPGF (7) 3CPTP2 (2) 3CCPC3 (3) 3CCPGF (4) 共86wt% </td></tr><tr><td> 比較例2 </td><td> 5PGUQUF (3) 4PGUQUF (5) 3PGUQUF (5)   </td><td> 2doPUO2F (2.5) 3doPUO2F (3) 2doPUQUF (4.5) 5doPUQUF (3) 共26wt% </td><td> 3CCYO2 (2.5) 2CPYO2 (10) 3CYO4 (11.5) </td><td> 3CCV (35.5) 3CCPOCF3(11.5) 3PGB2 (3) 共74wt% </td></tr><tr height="0"><td></td><td></td><td></td><td></td><td></td></tr></TBODY></TABLE>[Table 4]         <TABLE border="1" borderColor="#000000" width="_0017"><TBODY><tr><td> </td><td> compound (content wt%) </td></tr>< Tr><td> II </td><td> III </td></tr><tr><td> Comparative Example 1 </td><td> 2RIGUQUF (7) 3RIGUQUF (7) Total 14wt% < /td><td> 3CCV (50) 5PP1 (3) 4CCP3 (4) 3CPP2 (4) 3CPPF (2) </td><td> 3CPGF (7) 2CPGF (7) 3CPTP2 (2) 3CCPC3 (3) 3CCPGF (4) Total 86wt% </td></tr><tr><td> Comparative Example 2 </td><td> 5PGUQUF (3) 4PGUQUF (5) 3PGUQUF (5) </td><td> 2doPUO2F (2.5) 3doPUO2F (3) 2doPUQUF (4.5) 5doPUQUF (3) Total 26wt% </td><td> 3CCYO2 (2.5) 2CPYO2 (10) 3CYO4 (11.5) </td><td> 3CCV (35.5) 3CCPOCF3( 11.5) 3PGB2 (3) Total 74wt% </td></tr><tr height="0"><td></td><td></td><td></td><td>< /td><td></td></tr></TBODY></TABLE>

[表5] <TABLE border="1" borderColor="#000000" width="_0018"><TBODY><tr><td>   </td><td> 化合物 組成 </td><td> T<sub>ni</sub> (°C) </td><td> Δε </td><td> ε<sub>⊥</sub></td><td> K11 </td><td> K33 </td><td> γ1 (mPa•S) </td><td> Δn </td><td> LTS (天) </td></tr><tr><td> 比較例2 </td><td> II + III </td><td> 79.7 </td><td> 6.99 </td><td> 5.12 </td><td> 10.9 </td><td> 13.6 </td><td> 85.8 </td><td> 0.1105 </td><td> 11 </td></tr><tr><td> 實施例16 </td><td> I + II + III </td><td> 75.6 </td><td> 8 </td><td> 5.4 </td><td> 9.5 </td><td> 13.3 </td><td> 93.6 </td><td> 0.1029 </td><td> 16 </td></tr></TBODY></TABLE>[table 5]         <TABLE border="1" borderColor="#000000" width="_0018"><TBODY><tr><td> </td><td> compound composition</td><td> T<sub>ni< /sub> (°C) </td><td> Δε </td><td> ε<sub>⊥</sub></td><td> K11 </td><td> K33 </td ><td> γ1 (mPa•S) </td><td> Δn </td><td> LTS (days) </td></tr><tr><td> Comparative Example 2 </td> <td> II + III </td><td> 79.7 </td><td> 6.99 </td><td> 5.12 </td><td> 10.9 </td><td> 13.6 </td> <td> 85.8 </td><td> 0.1105 </td><td> 11 </td></tr><tr><td> Example 16 </td><td> I + II + III < /td><td> 75.6 </td><td> 8 </td><td> 5.4 </td><td> 9.5 </td><td> 13.3 </td><td> 93.6 </td ><td> 0.1029 </td><td> 16 </td></tr></TBODY></TABLE>

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 of Table 5, it can be found that Example 16 exhibits higher Δε and ε due to the inclusion of 13% by weight of Compound I, and a longer low temperature storage period, indicating that the liquid crystal medium containing Compound I is subsequently applied to the liquid crystal display. When the unit is used, it can effectively reduce the starting voltage and improve the penetration.

[表6] <TABLE border="1" borderColor="#000000" width="_0019"><TBODY><tr><td>   </td><td> 化合物 組成 </td><td> T<sub>ni</sub> (°C) </td><td> Δε </td><td> ε<sub>⊥</sub></td><td> K11 </td><td> K33 </td><td> γ1 (mPa•S) </td><td> Δn </td></tr><tr><td> 比較例 1 </td><td> II + III </td><td> 84.1 </td><td> 4.4 </td><td> 2.95 </td><td> 10.6 </td><td> 13.2 </td><td> 57.2 </td><td> 0.1054 </td></tr><tr><td> 實施例 1 </td><td> I + III </td><td> 87.5 </td><td> 5.1 </td><td> 3.19 </td><td> 10.7 </td><td> 13.8 </td><td> 67.0 </td><td> 0.1050 </td></tr></TBODY></TABLE>[Table 6]         <TABLE border="1" borderColor="#000000" width="_0019"><TBODY><tr><td> </td><td> compound composition</td><td> T<sub>ni< /sub> (°C) </td><td> Δε </td><td> ε<sub>⊥</sub></td><td> K11 </td><td> K33 </td ><td> γ1 (mPa•S) </td><td> Δn </td></tr><tr><td> Comparative Example 1 </td><td> II + III </td>< Td> 84.1 </td><td> 4.4 </td><td> 2.95 </td><td> 10.6 </td><td> 13.2 </td><td> 57.2 </td><td> 0.1054 </td></tr><tr><td> Example 1 </td><td> I + III </td><td> 87.5 </td><td> 5.1 </td><td > 3.19 </td><td> 10.7 </td><td> 13.8 </td><td> 67.0 </td><td> 0.1050 </td></tr></TBODY></TABLE>

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T ni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, the T ni temperature, Δε, ε ⊥ of Example 1, Both K11 and K33 are higher than Comparative Example 1, and it is shown that the liquid crystal medium containing the compound I can effectively lower the starting voltage and improve the transmittance when applied to the 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, the liquid crystal medium of the present invention can effectively reduce the starting voltage and the transmittance of the liquid crystal display unit when it is applied to the liquid crystal display unit because of the compound I having a special structure design and having a higher Δε and ε . . Therefore, 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 (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,R 1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; X 1及X 2各自表示氫或氟; A 1、A 2、A 3及A 4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A 2可為相同或不同; m及o表示0或1,且m+o≥1;及 R 2表示鹵素、OCF 3、CF 3或CN。 A liquid crystal medium comprising: at least one compound I, which is represented by Chemical Formula 1: [Chemical Formula 1] In Chemical Formula 1, R 1 represents an alkyl group having a carbon number of 1 to 10, an alkoxy group having a carbon number of 1 to 10, an alkenyl group having a carbon number of 2 to 10, or a carbon number ranging from 2 to 10. Alkenyloxy, one or more hydrogens of the alkyl, alkoxy, alkenyl or alkenyloxy group may be optionally substituted by fluorine; X 1 and X 2 each represent hydrogen or fluorine; A 1 , A 2 , A 3 and A 4 each represent 1,4-cyclohexylene, 1,4-phenylene, 3,5-difluoro-1,4-phenylene, 2,3-difluoro-1,4-stretch 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 a compound selected from the formula 1-1, a compound represented by the chemical formula 1-2 or a compound represented by the 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: 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,R 3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; B 1表示1,4-伸環己基、1,4-伸苯基、 ; B 2及B 3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; Z 1表示單鍵、−(CH 2) 2−、−COO−、−CH 2O−、−OCO−、−CF 2O−、−OCF 2−、−C≡C−或−CH=CH−;及 R 4表示鹵素、OCF 3、OCF 2H、CF 3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 of 1 to 10, an alkoxy group having a carbon number of 1 to 10, an alkenyl group having a carbon number of 2 to 10, or a carbon number ranging from 2 to 10 Alkenyloxy, one or more hydrogens of the alkyl, alkoxy, alkenyl or alkenyloxy group may be optionally substituted by fluorine; B 1 represents 1,4-cyclohexylene, 1,4-phenylene base, or ; B 2 and B 3 each represent 1,4-cyclohexylene, 1,4-phenylene, 3,5-difluoro-1,4-phenylene, 2,3-difluoro-1,4- Phenyl 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 a compound selected from the chemical formula 2-1 or the compound represented by the 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,R 5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; C 1、C 2、C 3及C 4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; Z 2、Z 3及Z 4各自表示單鍵、−(CH 2) 2−、−COO−、−CH 2O−、−OCO−、−CF 2O−、−OCF 2−、−C≡C−或−CH=CH−;及 R 6表示鹵素、OCF 3、CF 3、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 of 1 to 10, an alkoxy group having a carbon number of 1 to 10, an alkenyl group having a carbon number of 2 to 10, or a carbon number ranging from 2 to 10 Alkenyloxy, one or more hydrogens of the alkyl, alkoxy, alkenyl or alkenyloxy group may be optionally substituted by fluorine; C 1 , C 2 , C 3 and C 4 each represent 1,4- Cyclohexylene, 1,4-phenylene, 2,3-difluoro-1,4-phenylene, 3-fluoro-1,4-phenylene, 2,5-benzofuranyl or 2 , 6-extended 7,8-difluoro-1,3-benzodioxanyl; 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, an alkyl group having a carbon number ranging from 1 to 10, an alkoxy group having a carbon number ranging from 1 to 10, an alkenyl group having a carbon number ranging from 2 to 10, or an alkenyl group having a carbon number ranging from 2 to 10. One or more hydrogens of the alkyl, alkoxy, alkenyl or alkenyloxy group are optionally substituted by 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 a compound 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,R 7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; X 3、X 4、X 5及X 6各自表示氫或氟; D 1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 R 8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、OCHCF 2、OCF 3、CF 3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 of 1 to 10, an alkoxy group having a carbon number of 1 to 10, an alkenyl group having a carbon number of 2 to 10, or a carbon number ranging from 2 to 10 Alkenyloxy, one or more hydrogens of the alkyl, alkoxy, alkenyl or alkenyloxy group are optionally substituted by fluorine; X 3 , X 4 , X 5 and X 6 each represent hydrogen or fluorine; D 1 represents 1,4-cyclohexylene, 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 a halogen, an alkoxy group having a carbon number ranging from 1 to 10, an alkenyloxy group having a carbon number ranging from 2 to 10, OCHCF 2 , OCF 3 , CF 3 or CN, one or more hydrogens of the alkoxy or alkenyloxy group are optionally substituted by fluorine. 一種化合物,是由化學式1所示: [化學式1] , 於化學式1中,R 1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; X 1及X 2各自表示氫或氟; A 1、A 2、A 3及A 4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A 2可為相同或不同; m及o表示0或1,且m+o≥1;及 R 2表示鹵素、OCF 3、CF 3或CN。 A compound which is represented by Chemical Formula 1: [Chemical Formula 1] In Chemical Formula 1, R 1 represents an alkyl group having a carbon number of 1 to 10, an alkoxy group having a carbon number of 1 to 10, an alkenyl group having a carbon number of 2 to 10, or a carbon number ranging from 2 to 10. Alkenyloxy, one or more hydrogens of the alkyl, alkoxy, alkenyl or alkenyloxy group may be optionally substituted by fluorine; X 1 and X 2 each represent hydrogen or fluorine; A 1 , A 2 , A 3 and A 4 each represent 1,4-cyclohexylene, 1,4-phenylene, 3,5-difluoro-1,4-phenylene, 2,3-difluoro-1,4-stretch 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 comprising a liquid crystal medium according to any one of claims 1 to 8.
TW105138564A 2016-11-24 2016-11-24 Compound, liquid crystal medium containing the compound and display unit TWI599640B (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
TW105138564A TWI599640B (en) 2016-11-24 2016-11-24 Compound, liquid crystal medium containing the compound and display unit
CN201710845722.0A CN108102667A (en) 2016-11-24 2017-09-19 Compound, liquid crystal medium containing the compound and display unit

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
TW105138564A TWI599640B (en) 2016-11-24 2016-11-24 Compound, liquid crystal medium containing the compound and display unit

Publications (2)

Publication Number Publication Date
TWI599640B true TWI599640B (en) 2017-09-21
TW201819601A TW201819601A (en) 2018-06-01

Family

ID=60719693

Family Applications (1)

Application Number Title Priority Date Filing Date
TW105138564A TWI599640B (en) 2016-11-24 2016-11-24 Compound, liquid crystal medium containing the compound and display unit

Country Status (2)

Country Link
CN (1) CN108102667A (en)
TW (1) TWI599640B (en)

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH645102A5 (en) * 1980-10-14 1984-09-14 Hoffmann La Roche DISUBSTITUTED PYRIMIDINE.
GB0424308D0 (en) * 2004-11-03 2004-12-01 Qinetiq Ltd Compounds for use in liquid crystal devices
JP4978017B2 (en) * 2006-02-09 2012-07-18 Jnc株式会社 Benzodioxin derivative, liquid crystal composition containing the same, and liquid crystal display device
JP5736670B2 (en) * 2010-06-01 2015-06-17 Jnc株式会社 Liquid crystal compound comprising fused ring having two oxygens and liquid crystal composition using the same
CN102898414B (en) * 2012-10-13 2015-04-08 江苏和成显示科技股份有限公司 Novel dioxa saturation naphthalene nucleus liquid crystal compound, composition of liquid crystal compound and application of liquid crystal compound

Also Published As

Publication number Publication date
TW201819601A (en) 2018-06-01
CN108102667A (en) 2018-06-01

Similar Documents

Publication Publication Date Title
US9404038B2 (en) Cyclopropyl-bearing liquid crystal compounds and mixtures
TWI567170B (en) A liquid crystal compound and a liquid crystal composition containing the same
JP6137419B2 (en) Nematic liquid crystal composition and liquid crystal display device using the same
TW201139354A (en) Liquid-crystalline compounds and liquid-crystalline media
CN105131971B (en) Liquid crystal compound with 2-fluorophenyl group and difluoro methyleneoxy group and preparing method and application thereof
JP4691893B2 (en) Liquid crystal composition, display element and compound containing trifluoronaphthalene derivative.
TWI542669B (en) A liquid crystal compound and a liquid crystal composition containing the same
JP5493596B2 (en) Difluorobenzene derivatives and liquid crystal compositions containing the same.
JP5526686B2 (en) Difluorobenzene derivatives and liquid crystal compositions containing the same.
CN102070601A (en) Benzodioxoheterocycloheptane liquid crystal compound and liquid crystal mixture thereof
JPH0393741A (en) Optically active compounds for use as chiral doping agent for liquid crystal and method of its preparation and use thereof
TWI599640B (en) Compound, liquid crystal medium containing the compound and display unit
JP2013001683A (en) Liquid crystal compound having 2,6,7-trioxa-bicyclo[2.2.2]octane skeleton and liquid crystal composition
TWI608000B (en) Compound containing a 2,5-benzofuran group, a liquid crystal composition containing the compound, and a display unit
JP6166313B2 (en) Liquid crystal compound, liquid crystal composition, and liquid crystal display device
TWI591162B (en) Liquid crystal composition and display unit containing the liquid crystal composition
TW201414811A (en) Novel saturated dioxanaphthalene-based liquid crystal compound, composition and use thereof
JP2019156840A (en) Liquid crystal compound and liquid crystal composition including the same
JP2004149475A (en) Compound having 1,2-propanediyl group as linkage group and liquid crystal composition containing the same
CN110903832B (en) Negative liquid crystal compound, liquid crystal composition containing negative liquid crystal compound and application of negative liquid crystal compound
JP4940560B2 (en) Liquid crystal composition, display element and compound containing trifluoronaphthalene derivative
TWI640501B (en) Liquid crystal compound, liquid crystal composition and liquid crystal display device having thereof
JP4753064B2 (en) Liquid crystal composition, display element and compound containing trifluoronaphthalene derivative.
TWI545182B (en) Chiral compound for liquid crystal and liquid crystal mixture comprising the same
JP4501388B2 (en) Liquid crystal composition and liquid crystalline compound containing difluorotetrahydronaphthalene derivative