TW202235589A - Liquid crystal composition and liquid crystal display device capable of enabling a liquid crystal display device to have a better contrast ratio - Google Patents

Liquid crystal composition and liquid crystal display device capable of enabling a liquid crystal display device to have a better contrast ratio Download PDF

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TW202235589A
TW202235589A TW110108991A TW110108991A TW202235589A TW 202235589 A TW202235589 A TW 202235589A TW 110108991 A TW110108991 A TW 110108991A TW 110108991 A TW110108991 A TW 110108991A TW 202235589 A TW202235589 A TW 202235589A
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liquid crystal
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林則學
王辰
蔡明潔
李清田
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達興材料股份有限公司
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Priority to CN202210207373.0A priority patent/CN115074138A/en
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    • C—CHEMISTRY; METALLURGY
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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
    • C09K19/42—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40
    • C09K19/44—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40 containing compounds with benzene rings directly linked
    • G—PHYSICS
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    • G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
    • G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
    • G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour 
    • G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on liquid crystals, e.g. single liquid crystal display cells
    • G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
    • G02F1/1333—Constructional arrangements; Manufacturing methods

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Abstract

A liquid crystal composition which comprises a liquid crystal component. The liquid crystal component includes a liquid crystal compound represented by formula I, and a liquid crystal compound represented by one of formula II and formula III. The definitions of ring A to ring E, Z1 , X1 , X2 , R1 to R5 , m, n, o and q in the formula I to the formula III are respectively as described in the specification and the claims of the application. In the present invention, the liquid crystal compound of the formula I and the liquid crystal compound of the formula II or the formula III cooperate with each other, so that the liquid crystal composition has high transmittance, thereby enabling a liquid crystal display device to have a better contrast ratio.

Description

液晶組成物及液晶顯示裝置Liquid crystal composition and liquid crystal display device

本發明是有關於一種液晶組成物及液晶顯示裝置，特別是指一種包含末端基含氟之液晶化合物的液晶組成物，及包含該液晶組成物的液晶顯示裝置。The present invention relates to a liquid crystal composition and a liquid crystal display device, in particular to a liquid crystal composition comprising a liquid crystal compound containing fluorine in an end group, and a liquid crystal display device comprising the liquid crystal composition.

隨著液晶顯示裝置的廣泛使用，消費者對於該液晶顯示裝置所具備的規格的要求也更高，例如解析度、對比度、亮度等。當該液晶顯示裝置使用的液晶組成物具有較高的穿透度時，能有效地增加該液晶顯示裝置的對比度。且若該液晶組成物具有較高的穿透度，該液晶顯示裝置還能以較低的電壓達到一定的亮度，進而達到省電的功效。With the widespread use of liquid crystal display devices, consumers have higher requirements on the specifications of the liquid crystal display devices, such as resolution, contrast, brightness, and the like. When the liquid crystal composition used in the liquid crystal display device has a relatively high transmittance, the contrast of the liquid crystal display device can be effectively increased. Moreover, if the liquid crystal composition has a higher transmittance, the liquid crystal display device can also achieve a certain brightness with a lower voltage, thereby achieving the effect of saving power.

因此，為使液晶顯示裝置具有較佳的對比度且省電，有需要研發出具有高穿透度的液晶組成物。Therefore, in order to make the liquid crystal display device have better contrast and save power, it is necessary to develop a liquid crystal composition with high transparency.

因此，本發明的第一目的，即在提供一種具有高穿透度的液晶組成物。Therefore, the first object of the present invention is to provide a liquid crystal composition with high transparency.

於是，本發明液晶組成物，包含一液晶組分。Therefore, the liquid crystal composition of the present invention includes a liquid crystal component.

該液晶組分包括式I所示的液晶化合物，及式II及式III的其中一者所示的液晶化合物： [式I]

Figure 02_image001
[式II]
Figure 02_image003
[式III]
Figure 02_image005
； 在該式I至該式III中， 環A及環B各自獨立地表示1,4-伸環己基或1,4-伸苯基，上述基團為未經取代或環上任一位置的氫被氟所取代； 環C、環D及環E各自獨立地表示1,4-伸環己基、1,4-伸苯基、萘-2,6-二基、茚滿-1,5-二基或茚滿-2,5-二基，上述基團為未經取代或環上任一位置的氫被氟、直鏈烷基或支鏈烷基所取代，上述烷基為未經取代或至少一個－CH 2－被－O－或－C=C－所取代； Z 1表示－COO－、－OCO－、－OCH 2－、－CH 2O－、－CH 2CH 2－或單鍵； X 1及X 2各自獨立地表示C 1-C 5伸烷基，上述伸烷基為未經取代或至少一個－CH 2－被－O－所取代； R 1表示為氫或氟； R 2及R 3各自獨立地表示氫、C 1-C 12直鏈烷基、C 3-C 12支鏈烷基、C 1-C 12直鏈烷氧基、C 3-C 12支鏈烷氧基、C 2-C 12直鏈烯基、C 3-C 12支鏈烯基、C 2-C 12直鏈氧烯基或C 3-C 12支鏈氧烯基，上述烷基、烷氧基、烯基或氧烯基為未經取代； R 4表示為氫、C 1-C 12直鏈烷基、C 3-C 12支鏈烷基、C 1-C 12直鏈烷氧基、C 3-C 12支鏈烷氧基、C 2-C 12直鏈烯基、C 3-C 12支鏈烯基、C 2-C 12直鏈氧烯基或C 3-C 12支鏈氧烯基，上述烷基、烷氧基、烯基或氧烯基為未經取代或任意碳上的氫被氟所取代； R 5表示為氫、氟、氯、C 1-C 12直鏈烷基、C 3-C 12支鏈烷基、C 1-C 12直鏈烷氧基、C 3-C 12支鏈烷氧基、C 2-C 12直鏈烯基、C 3-C 12支鏈烯基、C 2-C 12直鏈氧烯基或C 3-C 12支鏈氧烯基，上述烷基、烷氧基、烯基或氧烯基為未經取代或任意碳上的氫被氟所取代； m及n分別表示0、1或2，且m與n的和為1或2，當m為2時，每個環A為相同或不同，當n為2時，每個環B為相同或不同； o表示1、2或3，當o為2或3，每個環C為相同或不同，每個Z 1為相同或不同； q表示1、2或3，當 q為2或3，每個環E為相同或不同。 The liquid crystal component includes a liquid crystal compound shown in formula I, and a liquid crystal compound shown in one of formula II and formula III: [Formula I]
Figure 02_image001
[Formula II]
Figure 02_image003
[Formula III]
Figure 02_image005
; In the formula I to the formula III, ring A and ring B each independently represent 1,4-cyclohexyl or 1,4-phenylene, and the above-mentioned groups are unsubstituted or hydrogen at any position on the ring Substituted by fluorine; Ring C, Ring D and Ring E each independently represent 1,4-cyclohexyl, 1,4-phenylene, naphthalene-2,6-diyl, indane-1,5-di group or indan-2,5-diyl, the above-mentioned group is unsubstituted or the hydrogen at any position on the ring is substituted by fluorine, straight-chain alkyl or branched-chain alkyl, and the above-mentioned alkyl is unsubstituted or at least A -CH 2 - is replaced by -O- or -C=C-; Z 1 represents -COO-, -OCO-, -OCH 2 -, -CH 2 O-, -CH 2 CH 2 - or a single bond; X 1 and X 2 each independently represent a C 1 -C 5 alkylene group, the above-mentioned alkylene group is unsubstituted or at least one -CH 2 - is substituted by -O-; R 1 represents hydrogen or fluorine; R 2 and R 3 each independently represent hydrogen, C 1 -C 12 straight chain alkyl, C 3 -C 12 branched chain alkyl, C 1 -C 12 straight chain alkoxy, C 3 -C 12 branched chain alkoxy , C 2 -C 12 straight chain alkenyl, C 3 -C 12 branched alkenyl, C 2 -C 12 straight chain oxyalkenyl or C 3 -C 12 branched oxyalkenyl, the above-mentioned alkyl, alkoxy , alkenyl or oxyalkenyl is unsubstituted; R 4 represents hydrogen, C 1 -C 12 straight chain alkyl, C 3 -C 12 branched chain alkyl, C 1 -C 12 straight chain alkoxy, C 3 -C 12 branched alkoxy, C 2 -C 12 straight chain alkenyl, C 3 -C 12 branched alkenyl, C 2 -C 12 straight chain oxyalkenyl or C 3 -C 12 branched chain oxyalkene The above-mentioned alkyl, alkoxy, alkenyl or oxyalkenyl is unsubstituted or hydrogen on any carbon is replaced by fluorine; R 5 represents hydrogen, fluorine, chlorine, C 1 -C 12 straight chain alkyl , C 3 -C 12 branched chain alkyl, C 1 -C 12 straight chain alkoxy, C 3 -C 12 branched alkoxy, C 2 -C 12 straight chain alkenyl, C 3 -C 12 branched chain Alkenyl, C 2 -C 12 straight chain oxyalkenyl or C 3 -C 12 branched oxyalkenyl, the above-mentioned alkyl, alkoxy, alkenyl or oxyalkenyl is unsubstituted or hydrogen on any carbon is replaced by Substituted by fluorine; m and n represent 0, 1 or 2 respectively, and the sum of m and n is 1 or 2, when m is 2, each ring A is the same or different, when n is 2, each ring B is the same or different; o means 1, 2 or 3, when o is 2 or 3, each ring C is the same or different, each Z 1 is the same or different; q means 1, 2 or 3, when q is 2 or 3, each ring E is the same or different.

本發明的第二目的，即在提供一種具有較佳對比度的液晶顯示裝置。The second object of the present invention is to provide a liquid crystal display device with better contrast.

於是，本發明液晶顯示裝置，包含上述的液晶組成物。Therefore, the liquid crystal display device of the present invention includes the above-mentioned liquid crystal composition.

本發明的功效在於：本發明液晶組成物透過該式I液晶化合物與該式II或式III液晶化合物相互配合，使得該液晶組成物具有高的穿透度，有利於後續將該液晶組成物應用於液晶顯示裝置時，使該液晶顯示裝置具有較佳的對比度，且該液晶顯示裝置能以較低的電壓達到一定的亮度而具有省電的功效。The efficacy of the present invention lies in that the liquid crystal composition of the present invention cooperates with the liquid crystal compound of formula I and the liquid crystal compound of formula II or III, so that the liquid crystal composition has high penetration, which is beneficial to the subsequent application of the liquid crystal composition When used in a liquid crystal display device, the liquid crystal display device has a better contrast ratio, and the liquid crystal display device can achieve a certain brightness with a lower voltage and has the effect of saving power.

本發明液晶組成物包含一液晶組分，該液晶組分包括式I所示的液晶化合物，及式II及式III的其中一者所示的液晶化合物。The liquid crystal composition of the present invention comprises a liquid crystal component, and the liquid crystal component includes a liquid crystal compound represented by formula I, and a liquid crystal compound represented by one of formula II and formula III.

[式I液晶化合物] [式I]

Figure 02_image001
[Formula I liquid crystal compound] [Formula I]
Figure 02_image001

在該式I中，環A及環B各自獨立地表示1,4-伸環己基或1,4-伸苯基，上述基團為未經取代或環上任一位置的氫被氟所取代。In the formula I, ring A and ring B each independently represent 1,4-cyclohexylene or 1,4-phenylene, and the above-mentioned groups are unsubstituted or hydrogen at any position on the ring is replaced by fluorine.

X 1及X 2各自獨立地表示C 1-C 5伸烷基，上述伸烷基為未經取代或至少一個－CH 2－被－O－所取代。較佳地，該X 1及該X 2各自獨立地表示C 1-C 5伸烷基，上述伸烷基為未經取代。 X 1 and X 2 each independently represent a C 1 -C 5 alkylene group, and the above-mentioned alkylene group is unsubstituted or at least one -CH 2 - is substituted by -O-. Preferably, the X 1 and the X 2 each independently represent a C 1 -C 5 alkylene group, and the above-mentioned alkylene group is unsubstituted.

R 1表示為氫或氟。 R 1 represents hydrogen or fluorine.

m及n分別表示0、1或2，且m與n的和為1或2，當m為2時，每個環A為相同或不同，當n為2時，每個環B為相同或不同。m and n represent 0, 1 or 2 respectively, and the sum of m and n is 1 or 2. When m is 2, each ring A is the same or different; when n is 2, each ring B is the same or different.

以該液晶組分的總量為100 wt%計，該式I所示的液晶化合物的含量範圍為0.5 wt%至15 wt%。較佳地，該式I所示的液晶化合物的含量範圍為0.9 wt%至12.5 wt%。更佳地，該式I所示的液晶化合物的含量範圍為1.2 wt%至11 wt%。Based on the total amount of the liquid crystal components being 100 wt%, the content of the liquid crystal compound represented by formula I ranges from 0.5 wt% to 15 wt%. Preferably, the content of the liquid crystal compound represented by formula I ranges from 0.9 wt% to 12.5 wt%. More preferably, the content of the liquid crystal compound represented by formula I ranges from 1.2 wt% to 11 wt%.

較佳地，該式I液晶化合物是選自於由式I-1、式I-2及式I-3所組成的群組中至少一者： [式I-1]

Figure 02_image012
[式I-2]
Figure 02_image014
[式I-3]
Figure 02_image016
。 Preferably, the liquid crystal compound of formula I is at least one selected from the group consisting of formula I-1, formula I-2 and formula I-3: [Formula I-1]
Figure 02_image012
[Formula I-2]
Figure 02_image014
[Formula I-3]
Figure 02_image016
.

式I-1至式I-3中，R 1表示為氫或氟，該X 1及該X 2各自獨立地表示C 1-C 5伸烷基，上述伸烷基為未經取代。 In the formulas I-1 to I-3, R 1 represents hydrogen or fluorine, the X 1 and the X 2 each independently represent a C 1 -C 5 alkylene group, and the above alkylene group is unsubstituted.

較佳地，該式I-1液晶化合物是選自於由式I-1a至式I-1i所組成的群組中至少一者。較佳地，該式I-2液晶化合物是選自於由式I-2a至式I-2c所組成的群組中至少一者。較佳地，該式I-3液晶化合物是選自於式I-3a。 編號 簡稱 結構 式I-1a 3PP1F

Figure 02_image018
式I-1b 5PP1F
Figure 02_image020
 式I-1c 1PP2F
Figure 02_image022
 式I-1d 3PP2F
Figure 02_image024
 式I-1e 1PP3F
Figure 02_image026
 式I-1f 2PP3F
Figure 02_image028
 式I-1g 3PP3F
Figure 02_image030
 式I-1h 1PP4F
Figure 02_image032
 式I-1i F3PP3F
Figure 02_image034
 式I-2a 1PCC2F
Figure 02_image036
 式I-2b 1PCC3F
Figure 02_image038
 式I-2c 1PCC4F
Figure 02_image040
 式I-3a 3PGP1F
Figure 02_image042
 Preferably, the liquid crystal compound of formula I-1 is at least one selected from the group consisting of formulas I-1a to I-1i. Preferably, the liquid crystal compound of formula I-2 is at least one selected from the group consisting of formulas I-2a to I-2c. Preferably, the liquid crystal compound of formula I-3 is selected from formula I-3a. serial number Abbreviation structure Formula I-1a 3PP1F
Figure 02_image018
 Formula I-1b 5PP1F
Figure 02_image020
 Formula I-1c 1PP2F
Figure 02_image022
 Formula I-1d 3PP2F
Figure 02_image024
 Formula I-1e 1PP3F
Figure 02_image026
 Formula I-1f 2PP3F
Figure 02_image028
 Formula I-1g 3PP3F
Figure 02_image030
 Formula I-1h 1PP4F
Figure 02_image032
 Formula I-1i F3PP3F
Figure 02_image034
 Formula I-2a 1PCC2F
Figure 02_image036
 Formula I-2b 1PCC3F
Figure 02_image038
 Formula I-2c 1PCC4F
Figure 02_image040
 Formula I-3a 3PGP1F
Figure 02_image042

[式II液晶化合物] [式II]

Figure 02_image003
[Formula II liquid crystal compound] [Formula II]
Figure 02_image003

在該式II中，環C表示為1,4-伸環己基、1,4-伸苯基、萘-2,6-二基、茚滿-1,5-二基或茚滿-2,5-二基，上述基團為未經取代或環上任一位置的氫被氟、直鏈烷基或支鏈烷基所取代，上述烷基為未經取代或至少一個－CH 2－被－O－或－C=C－所取代。較佳地，該環C表示為1,4-伸環己基、1,4-伸苯基，上述基團為未經取代。 In this formula II, ring C is represented as 1,4-cyclohexylene, 1,4-phenylene, naphthalene-2,6-diyl, indan-1,5-diyl or indan-2, 5-diyl group, the above-mentioned group is unsubstituted or the hydrogen at any position on the ring is substituted by fluorine, straight-chain alkyl or branched-chain alkyl, the above-mentioned alkyl is unsubstituted or at least one -CH 2 - is replaced by- O- or -C=C- replaced. Preferably, the ring C represents 1,4-cyclohexylene or 1,4-phenylene, and the above groups are unsubstituted.

Z 1表示－COO－、－OCO－、－OCH 2－、－CH 2O－、－CH 2CH 2－或單鍵。較佳地，該Z 1表示為－CH 2O－或單鍵。 Z 1 represents -COO-, -OCO-, -OCH 2 -, -CH 2 O-, -CH 2 CH 2 - or a single bond. Preferably, the Z 1 represents -CH 2 O- or a single bond.

R 2及R 3各自獨立地表示氫、C 1-C 12直鏈烷基、C 3-C 12支鏈烷基、C 1-C 12直鏈烷氧基、C 3-C 12支鏈烷氧基、C 2-C 12直鏈烯基、C 3-C 12支鏈烯基、C 2-C 12直鏈氧烯基或C 3-C 12支鏈氧烯基，上述烷基、烷氧基、烯基或氧烯基為未經取代。較佳地，該R 2及該R 3各自獨立地表示C 1-C 12直鏈烷基、C 1-C 12直鏈烷氧基，上述烷基或烷氧基為未經取代。更佳地，該R 2及該R 3各自獨立地表示C 1-C 5直鏈烷基、C 1-C 4直鏈烷氧基，上述烷基或烷氧基為未經取代。 R 2 and R 3 each independently represent hydrogen, C 1 -C 12 straight chain alkyl, C 3 -C 12 branched chain alkyl, C 1 -C 12 straight chain alkoxy, C 3 -C 12 branched chain alkane Oxygen, C 2 -C 12 straight chain alkenyl, C 3 -C 12 branched chain alkenyl, C 2 -C 12 straight chain oxyalkenyl or C 3 -C 12 branched chain oxyalkenyl, the above-mentioned alkyl, alkyl Oxy, alkenyl or oxyalkenyl is unsubstituted. Preferably, the R 2 and the R 3 each independently represent a C 1 -C 12 linear alkyl group, a C 1 -C 12 linear alkoxy group, and the above-mentioned alkyl group or alkoxy group is unsubstituted. More preferably, the R 2 and the R 3 each independently represent a C 1 -C 5 linear alkyl group, a C 1 -C 4 linear alkoxy group, and the above-mentioned alkyl group or alkoxy group is unsubstituted.

o表示1、2或3，當o為2或3，每個環C為相同或不同，每個Z 1為相同或不同。較佳地，該o表示為1或2。 o represents 1, 2 or 3, when o is 2 or 3, each ring C is the same or different, and each Z 1 is the same or different. Preferably, o is represented as 1 or 2.

以該液晶組分的總量為100 wt%計，該式II所示的液晶化合物的含量範圍為35 wt%至65 wt%。較佳地，該式II所示的液晶化合物的含量範圍為39 wt%至60 wt%。更佳地，該式II所示的液晶化合物的含量範圍為40.5 wt%至58 wt%。Based on the total amount of the liquid crystal component as 100 wt%, the content of the liquid crystal compound represented by formula II ranges from 35 wt% to 65 wt%. Preferably, the content of the liquid crystal compound represented by formula II ranges from 39 wt% to 60 wt%. More preferably, the content of the liquid crystal compound represented by formula II ranges from 40.5 wt% to 58 wt%.

較佳地，該式II液晶化合物是選自於由式II-1、式II-2、式II-3、式II-4、式II-5及式II-6所組成的群組中至少一者： [式II-1]

Figure 02_image044
[式II-2]
Figure 02_image046
[式II-3]
Figure 02_image048
[式II-4]
Figure 02_image050
[式II-5]
Figure 02_image052
[式II-6]
Figure 02_image054
。 Preferably, the liquid crystal compound of formula II is selected from the group consisting of formula II-1, formula II-2, formula II-3, formula II-4, formula II-5 and formula II-6. One: [Formula II-1]
Figure 02_image044
[Formula II-2]
Figure 02_image046
[Formula II-3]
Figure 02_image048
[Formula II-4]
Figure 02_image050
[Formula II-5]
Figure 02_image052
[Formula II-6]
Figure 02_image054
.

式II-1至式II-6中，該R 2及該R 3各自獨立地表示C 1-C 12直鏈烷基或C 1-C 12直鏈烷氧基，上述烷基或烷氧基為未經取代。更佳地，該R 2及該R 3各自獨立地表示C 1-C 5直鏈烷基、C 1-C 4直鏈烷氧基，上述烷基或烷氧基為未經取代。 In formula II-1 to formula II-6, the R 2 and the R 3 each independently represent a C 1 -C 12 straight chain alkyl group or a C 1 -C 12 straight chain alkoxy group, the above-mentioned alkyl or alkoxy group is not replaced. More preferably, the R 2 and the R 3 each independently represent a C 1 -C 5 linear alkyl group, a C 1 -C 4 linear alkoxy group, and the above-mentioned alkyl group or alkoxy group is unsubstituted.

較佳地，該式II-1液晶化合物是選自於由式II-1a、式II-1b所組成的群組中至少一者。較佳地，該式II-2液晶化合物是選自於由式II-2a至式II-2d所組成的群組中至少一者。較佳地，該式II-3液晶化合物是選自於由式II-3a至式II-3d所組成的群組中至少一者。較佳地，該式II-4液晶化合物是選自於式II-4a。較佳地，該式II-5液晶化合物是選自於由式II-5a至式II-5c所組成的群組中至少一者。較佳地，該式II-6液晶化合物是選自於由式II-6a及式II-6b所組成的群組中至少一者。 編號 簡稱 結構 式II-1a 3CYO2

Figure 02_image056
式II-1b 5CYO2
Figure 02_image058
 式II-2a 2CCY1
Figure 02_image060
 式II-2b 3CCY1
Figure 02_image062
 式II-2c 3CCYO1
Figure 02_image064
 式II-2d 3CCYO2
Figure 02_image066
 式II-3a 2CPYO2
Figure 02_image068
 式II-3b 3CPYO2
Figure 02_image070
 式II-3c 3CPYO3
Figure 02_image072
 式II-3d 3CPYO4
Figure 02_image074
 式II-4a 3PYO2
Figure 02_image076
 式II-5a 3C1OYO2
Figure 02_image078
 式II-5b 2C1OYO2
Figure 02_image080
 式II-5c 3C1OYO1
Figure 02_image082
 式II-6a 3CC1OYO2
Figure 02_image084
 式II-6b 2CC1OYO2
Figure 02_image086
 Preferably, the liquid crystal compound of formula II-1 is at least one selected from the group consisting of formula II-1a and formula II-1b. Preferably, the liquid crystal compound of formula II-2 is at least one selected from the group consisting of formula II-2a to formula II-2d. Preferably, the liquid crystal compound of formula II-3 is at least one selected from the group consisting of formula II-3a to formula II-3d. Preferably, the liquid crystal compound of formula II-4 is selected from formula II-4a. Preferably, the liquid crystal compound of formula II-5 is at least one selected from the group consisting of formula II-5a to formula II-5c. Preferably, the liquid crystal compound of formula II-6 is at least one selected from the group consisting of formula II-6a and formula II-6b. serial number Abbreviation structure Formula II-1a 3CYO2
Figure 02_image056
 Formula II-1b 5CYO2
Figure 02_image058
 Formula II-2a 2CCY1
Figure 02_image060
 Formula II-2b 3CCY1
Figure 02_image062
 Formula II-2c 3CCYO1
Figure 02_image064
 Formula II-2d 3CCYO2
Figure 02_image066
 Formula II-3a 2CPYO2
Figure 02_image068
 Formula II-3b 3CPYO2
Figure 02_image070
 Formula II-3c 3CPYO3
Figure 02_image072
 Formula II-3d 3CPYO4
Figure 02_image074
 Formula II-4a 3PYO2
Figure 02_image076
 Formula II-5a 3C1OYO2
Figure 02_image078
 Formula II-5b 2C1OYO2
Figure 02_image080
 Formula II-5c 3C1OYO1
Figure 02_image082
 Formula II-6a 3CC1OYO2
Figure 02_image084
 Formula II-6b 2CC1OYO2
Figure 02_image086

[式III液晶化合物] [式III]

Figure 02_image005
[Formula III liquid crystal compound] [Formula III]
Figure 02_image005

在該式III中，環D及環E各自獨立地表示1,4-伸環己基、1,4-伸苯基、萘-2,6-二基、茚滿-1,5-二基或茚滿-2,5-二基，上述基團為未經取代或環上任一位置的氫被氟、直鏈烷基或支鏈烷基所取代，上述烷基為未經取代或至少一個－CH 2－被－O－或－C=C－所取代。較佳地，該環D及該環E各自獨立地表示1,4-伸環己基、1,4-伸苯基、茚滿-1,5-二基或茚滿-2,5-二基，上述基團為未經取代或環上任一位置的氫被氟所取代。 In the formula III, ring D and ring E each independently represent 1,4-cyclohexylene, 1,4-phenylene, naphthalene-2,6-diyl, indan-1,5-diyl or Indan-2,5-diyl, the above-mentioned group is unsubstituted or the hydrogen at any position on the ring is substituted by fluorine, straight-chain alkyl or branched-chain alkyl, the above-mentioned alkyl is unsubstituted or at least one- CH 2 - is replaced by -O- or -C=C-. Preferably, the ring D and the ring E independently represent 1,4-cyclohexylene, 1,4-phenylene, indan-1,5-diyl or indan-2,5-diyl , the above group is unsubstituted or hydrogen at any position on the ring is replaced by fluorine.

R 4表示為氫、C 1-C 12直鏈烷基、C 3-C 12支鏈烷基、C 1-C 12直鏈烷氧基、C 3-C 12支鏈烷氧基、C 2-C 12直鏈烯基、C 3-C 12支鏈烯基、C 2-C 12直鏈氧烯基或C 3-C 12支鏈氧烯基，上述烷基、烷氧基、烯基或氧烯基為未經取代或任意碳上的氫被氟所取代。較佳地，該R 4表示為C 1-C 12直鏈烷基，上述烷基為未經取代。更佳地，該R 4表示為C 2-C 5直鏈烷基，上述烷基為未經取代。 R 4 represents hydrogen, C 1 -C 12 straight chain alkyl, C 3 -C 12 branched chain alkyl, C 1 -C 12 straight chain alkoxy, C 3 -C 12 branched chain alkoxy, C 2 -C 12 straight chain alkenyl, C 3 -C 12 branched alkenyl, C 2 -C 12 straight chain oxyalkenyl or C 3 -C 12 branched oxyalkenyl, the above-mentioned alkyl, alkoxy, alkenyl Or oxyalkenyl is unsubstituted or hydrogen on any carbon is replaced by fluorine. Preferably, the R 4 represents a C 1 -C 12 linear alkyl group, and the above-mentioned alkyl group is unsubstituted. More preferably, the R 4 represents a C 2 -C 5 linear alkyl group, and the above-mentioned alkyl group is unsubstituted.

R 5表示為氫、氟、氯、C 1-C 12直鏈烷基、C 3-C 12支鏈烷基、C 1-C 12直鏈烷氧基、C 3-C 12支鏈烷氧基、C 2-C 12直鏈烯基、C 3-C 12支鏈烯基、C 2-C 12直鏈氧烯基或C 3-C 12支鏈氧烯基，上述烷基、烷氧基、烯基或氧烯基為未經取代或任意碳上的氫被氟所取代。較佳地，該R 5表示為氟。 R 5 represents hydrogen, fluorine, chlorine, C 1 -C 12 straight chain alkyl, C 3 -C 12 branched chain alkyl, C 1 -C 12 straight chain alkoxy, C 3 -C 12 branched chain alkoxy C 2 -C 12 straight chain alkenyl, C 3 -C 12 branched alkenyl, C 2 -C 12 straight chain oxyalkenyl or C 3 -C 12 branched oxyalkenyl, the above-mentioned alkyl, alkoxy The radical, alkenyl or oxyalkenyl is unsubstituted or hydrogen on any carbon is replaced by fluorine. Preferably, the R 5 represents fluorine.

q表示1、2或3，當 q為2或3，每個環E為相同或不同。較佳地，該q表示為2或3。q represents 1, 2 or 3, and when q is 2 or 3, each ring E is the same or different. Preferably, the q represents 2 or 3.

以該液晶組分的總量為100 wt%計，該式III所示的液晶化合物的含量範圍為5 wt%至18 wt%。較佳地，該式III所示的液晶化合物的含量範圍為8 wt%至15 wt%。更佳地，該式III所示的液晶化合物的含量範圍為10 wt%至12 wt%。Based on the total amount of the liquid crystal components being 100 wt%, the content of the liquid crystal compound represented by formula III ranges from 5 wt% to 18 wt%. Preferably, the content of the liquid crystal compound represented by formula III ranges from 8 wt% to 15 wt%. More preferably, the content of the liquid crystal compound represented by formula III ranges from 10 wt% to 12 wt%.

較佳地，該式III液晶化合物是選自於由式III-1、III-2、III-3、III-4及III-5所組成的群組中至少一者： [式III-1]

Figure 02_image088
[式III-2]
Figure 02_image090
[式III-3]
Figure 02_image092
[式III-4]
Figure 02_image094
[式III-5]
Figure 02_image096
。 Preferably, the liquid crystal compound of formula III is at least one selected from the group consisting of formulas III-1, III-2, III-3, III-4 and III-5: [Formula III-1]
Figure 02_image088
[Formula III-2]
Figure 02_image090
[Formula III-3]
Figure 02_image092
[Formula III-4]
Figure 02_image094
[Formula III-5]
Figure 02_image096
.

式III-1至式III-5中，該R 4表示為C 1-C 12直鏈烷基，上述烷基為未經取代。更佳地，該R 4表示為C 2-C 5直鏈烷基，上述烷基為未經取代。該R 5表示為氟。 In formula III-1 to formula III-5, the R 4 represents a C 1 -C 12 linear alkyl group, and the above-mentioned alkyl group is unsubstituted. More preferably, the R 4 represents a C 2 -C 5 linear alkyl group, and the above-mentioned alkyl group is unsubstituted. The R 5 represents fluorine.

較佳地，該式III-1液晶化合物是選自於由式III-1a、式III-1b所組成的群組中至少一者。較佳地，該式III-2液晶化合物是選自於由式III-2a、式III-2b所組成的群組中至少一者。較佳地，該式III-3液晶化合物是選自於由式III-3a至式III-3d所組成的群組中至少一者。較佳地，該式III-4液晶化合物是選自於由式III-4a、式III-4b所組成的群組中至少一者。較佳地，該式III-5液晶化合物是選自於由式III-5a、式III-5b所組成的群組中至少一者。 編號 簡稱 結構 式III-1a 2RIUQUF

Figure 02_image098
式III-1b 3RIUQUF
Figure 02_image100
 式III-2a 2RIGUQUF
Figure 02_image102
 式III-2b 3RIGUQUF
Figure 02_image104
 式III-3a 2PGUQUF
Figure 02_image106
 式III-3b 3PGUQUF
Figure 02_image108
 式III-3c 4PGUQUF
Figure 02_image110
 式III-3d 5PGUQUF
Figure 02_image112
 式III-4a 2PUQUF
Figure 02_image114
 式III-4b 3PUQUF
Figure 02_image116
 式III-5a 2CUQUF
Figure 02_image118
 式III-5b 3CUQUF
Figure 02_image120
 Preferably, the liquid crystal compound of formula III-1 is at least one selected from the group consisting of formula III-1a and formula III-1b. Preferably, the liquid crystal compound of formula III-2 is at least one selected from the group consisting of formula III-2a and formula III-2b. Preferably, the liquid crystal compound of formula III-3 is at least one selected from the group consisting of formula III-3a to formula III-3d. Preferably, the liquid crystal compound of formula III-4 is at least one selected from the group consisting of formula III-4a and formula III-4b. Preferably, the liquid crystal compound of formula III-5 is at least one selected from the group consisting of formula III-5a and formula III-5b. serial number Abbreviation structure Formula III-1a 2RIUQUF
Figure 02_image098
 Formula III-1b 3RIUQUF
Figure 02_image100
 Formula III-2a 2RIGUQUF
Figure 02_image102
 Formula III-2b 3RIGUQUF
Figure 02_image104
 Formula III-3a 2PGUQUF
Figure 02_image106
 Formula III-3b 3PGUQUF
Figure 02_image108
 Formula III-3c 4PGUQUF
Figure 02_image110
 Formula III-3d 5PGUQUF
Figure 02_image112
 Formula III-4a 2PUQUF
Figure 02_image114
 Formula III-4b 3PUQUF
Figure 02_image116
 Formula III-5a 2CUQUF
Figure 02_image118
 Formula III-5b 3CUQUF
Figure 02_image120

較佳地，在本發明液晶組成物中，該液晶組分還包括式IV所示的液晶化合物。 [式IV]

Figure 02_image122
Preferably, in the liquid crystal composition of the present invention, the liquid crystal component further includes a liquid crystal compound represented by formula IV. [Formula IV]
Figure 02_image122

在該式IV中，環F及環G各自獨立地表示1,4-伸環己基或1,4-伸苯基，上述基團為未經取代。In this formula IV, ring F and ring G each independently represent a 1,4-cyclohexylene group or a 1,4-phenylene group, and these groups are unsubstituted.

R 6表示C 1-C 5直鏈烷基、C 1-C 5直鏈烷氧基或C 2-C 5直鏈烯基，上述烷基、烷氧基或烯基為未經取代。 R 6 represents C 1 -C 5 straight chain alkyl, C 1 -C 5 straight chain alkoxy or C 2 -C 5 straight chain alkenyl, and the above alkyl, alkoxy or alkenyl is unsubstituted.

R 7表示氟、C 1-C 5直鏈烷基、C 3-C 5支鏈烷基、C 1-C 5直鏈烷氧基、C 3-C 5支鏈烷氧基或C 2-C 5直鏈烯基，上述烷基、烷氧基或烯基為未經取代。較佳地，該R 7表示氟、C 1-C 5直鏈烷基、C 1-C 5直鏈烷氧基或C 2-C 5直鏈烯基，上述烷基、烷氧基或烯基為未經取代。 R 7 represents fluorine, C 1 -C 5 straight chain alkyl, C 3 -C 5 branched chain alkyl, C 1 -C 5 straight chain alkoxy, C 3 -C 5 branched chain alkoxy or C 2 - C5 straight-chain alkenyl, the above-mentioned alkyl, alkoxy or alkenyl is unsubstituted. Preferably, the R 7 represents fluorine, C 1 -C 5 linear alkyl, C 1 -C 5 linear alkoxy or C 2 -C 5 linear alkenyl, the above-mentioned alkyl, alkoxy or alkenyl The base is unsubstituted.

Z 2表示－COO－、－OCO－、－OCH 2－、－CH 2O－、－CH=CH－、－C≡C－、－CH 2CH 2－或單鍵。較佳地，該Z表示為－C≡C－或單鍵。 Z 2 represents -COO-, -OCO-, -OCH 2 -, -CH 2 O-, -CH=CH-, -C≡C-, -CH 2 CH 2 -, or a single bond. Preferably, the Z represents -C≡C- or a single bond.

r表示1或2。r means 1 or 2.

以該液晶組分的總量為100 wt%計，該式IV所示的液晶化合物的含量範圍為30 wt%至80 wt%。較佳地，該式IV所示的液晶化合物的含量範圍為33 wt%至77 wt%。更佳地，該式IV所示的液晶化合物的含量範圍為35 wt%至75 wt%。Based on the total amount of the liquid crystal component as 100 wt%, the content of the liquid crystal compound represented by the formula IV ranges from 30 wt% to 80 wt%. Preferably, the content of the liquid crystal compound represented by formula IV ranges from 33 wt% to 77 wt%. More preferably, the content of the liquid crystal compound represented by formula IV ranges from 35 wt% to 75 wt%.

較佳地，該式IV液晶化合物是選自於由式IV-1、式IV-2、式IV-3、式IV-4、式IV-5及式IV-6所組成的群組中至少一者： [式IV-1]

Figure 02_image124
[式IV-2]
Figure 02_image126
[式IV-3]
Figure 02_image128
[式IV-4]
Figure 02_image130
[式IV-5]
Figure 02_image132
[式IV-6]
Figure 02_image134
。 Preferably, the liquid crystal compound of formula IV is selected from the group consisting of formula IV-1, formula IV-2, formula IV-3, formula IV-4, formula IV-5 and formula IV-6. One: [Formula IV-1]
Figure 02_image124
[Formula IV-2]
Figure 02_image126
[Formula IV-3]
Figure 02_image128
[Formula IV-4]
Figure 02_image130
[Formula IV-5]
Figure 02_image132
[Formula IV-6]
Figure 02_image134
.

式IV-1至式IV-6中，該R 6表示C 1-C 5直鏈烷基、C 1-C 5直鏈烷氧基或C 2-C 5直鏈烯基，上述烷基、烷氧基或烯基為未經取代。該R 7表示氟、C 1-C 5直鏈烷基、C 1-C 5直鏈烷氧基、C 2-C 5直鏈烯基，上述烷基、烷氧基或烯基為未經取代。 In formula IV-1 to formula IV-6, the R 6 represents C 1 -C 5 straight chain alkyl, C 1 -C 5 straight chain alkoxy or C 2 -C 5 straight chain alkenyl, the above-mentioned alkyl, Alkoxy or alkenyl is unsubstituted. The R 7 represents fluorine, C 1 -C 5 straight chain alkyl, C 1 -C 5 straight chain alkoxy, C 2 -C 5 straight chain alkenyl, the above-mentioned alkyl, alkoxy or alkenyl is not replace.

較佳地，該式IV-1化合物是選自於由式IV-1a至式IV-1h所組成的群組中至少一者。較佳地，該式IV-2化合物是選自於由式IV-2a、式IV-2b所組成的群組中至少一者。較佳地，該式IV-3化合物是選自於由式IV-3a、式IV-3b所組成的群組中至少一者。較佳地，該式IV-4化合物是選自於由式IV-4a至式IV-4c所組成的群組中至少一者。較佳地，該式IV-5化合物是選自於由式IV-5a至式IV-5d所組成的群組中至少一者。較佳地，該式IV-6化合物是選自於式IV-6a。 編號 簡稱 結構 式IV-1a 3CC2

Figure 02_image136
式IV-1b 3CC3
Figure 02_image138
 式IV-1c 3CC4
Figure 02_image140
 式IV-1d 3CC5
Figure 02_image142
 式IV-1e 5CC2
Figure 02_image144
 式IV-1f 3CCO1
Figure 02_image146
 式IV-1g 3CCV1
Figure 02_image148
 式IV-1h 3CCV
Figure 02_image150
 式IV-2a 3CPO1
Figure 02_image152
 式IV-2b 3CPO2
Figure 02_image154
 式IV-3a 3PPO2
Figure 02_image156
 式IV-3b 1V2PPO1
Figure 02_image158
 式IV-4a 3CCP1
Figure 02_image160
 式IV-4b 3CCPO1
Figure 02_image162
 式IV-4c VCCP1
Figure 02_image164
 式IV-5a 3CPP1
Figure 02_image166
 式IV-5b 3CPP2
Figure 02_image168
 式IV-5c 3CPPF
Figure 02_image170
 式IV-5d 2CPPF
Figure 02_image172
 式IV-6a 3CPTP2
Figure 02_image174
 Preferably, the compound of formula IV-1 is at least one selected from the group consisting of formula IV-1a to formula IV-1h. Preferably, the compound of formula IV-2 is at least one selected from the group consisting of formula IV-2a and formula IV-2b. Preferably, the compound of formula IV-3 is at least one selected from the group consisting of formula IV-3a and formula IV-3b. Preferably, the compound of formula IV-4 is at least one selected from the group consisting of formula IV-4a to formula IV-4c. Preferably, the compound of formula IV-5 is at least one selected from the group consisting of formula IV-5a to formula IV-5d. Preferably, the compound of formula IV-6 is selected from formula IV-6a. serial number Abbreviation structure Formula IV-1a 3CC2
Figure 02_image136
 Formula IV-1b 3CC3
Figure 02_image138
 Formula IV-1c 3CC4
Figure 02_image140
 Formula IV-1d 3CC5
Figure 02_image142
 Formula IV-1e 5CC2
Figure 02_image144
 Formula IV-1f 3CCO1
Figure 02_image146
 Formula IV-1g 3CCV1
Figure 02_image148
 Formula IV-1h 3CCV
Figure 02_image150
 Formula IV-2a 3CPO1
Figure 02_image152
 Formula IV-2b 3CPO2
Figure 02_image154
 Formula IV-3a 3PPO2
Figure 02_image156
 Formula IV-3b 1V2PPO1
Figure 02_image158
 Formula IV-4a 3CCP1
Figure 02_image160
 Formula IV-4b 3CCPO1
Figure 02_image162
 Formula IV-4c VCCP1
Figure 02_image164
 Formula IV-5a 3CPP1
Figure 02_image166
 Formula IV-5b 3CPP2
Figure 02_image168
 Formula IV-5c 3CPPF
Figure 02_image170
 Formula IV-5d 2CPPF
Figure 02_image172
 Formula IV-6a 3CPTP2
Figure 02_image174

較佳地，在本發明液晶組成物中，該液晶組分還包括式V所示的液晶化合物。 [式V]

Figure 02_image176
Preferably, in the liquid crystal composition of the present invention, the liquid crystal component further includes a liquid crystal compound represented by formula V. [Formula V]
Figure 02_image176

在該式V中，環J及環I各自獨立地表示1,4-伸環己基、1,4-伸苯基、萘-2,6-二基、茚滿-1,5-二基或茚滿-2,5-二基，上述基團為未經取代或環上任一位置的氫被氟所取代。In the formula V, ring J and ring I each independently represent 1,4-cyclohexylene, 1,4-phenylene, naphthalene-2,6-diyl, indan-1,5-diyl or Indan-2,5-diyl, the above group is unsubstituted or hydrogen at any position on the ring is replaced by fluorine.

R 8表示為氫、C 1-C 12直鏈烷基、C 3-C 12支鏈烷基、C 1-C 12直鏈烷氧基、C 3-C 12支鏈烷氧基、C 2-C 12直鏈烯基、C 3-C 12支鏈烯基、C 2-C 12直鏈氧烯基或C 3-C 12支鏈氧烯基，上述烷基、烷氧基、烯基或氧烯基為未經取代或任意碳上的氫被氟所取代。 R 8 represents hydrogen, C 1 -C 12 straight chain alkyl, C 3 -C 12 branched chain alkyl, C 1 -C 12 straight chain alkoxy, C 3 -C 12 branched chain alkoxy, C 2 -C 12 straight chain alkenyl, C 3 -C 12 branched alkenyl, C 2 -C 12 straight chain oxyalkenyl or C 3 -C 12 branched oxyalkenyl, the above-mentioned alkyl, alkoxy, alkenyl Or oxyalkenyl is unsubstituted or hydrogen on any carbon is replaced by fluorine.

s表示1或2，當s為2，每個環I為相同或不同。s represents 1 or 2, when s is 2, each ring I is the same or different.

以該液晶組分的總量為100 wt%計，該式V所示的液晶化合物的含量範圍為2 wt%至15 wt%。較佳地，該式V所示的液晶化合物的含量範圍為3 wt%至10 wt%。更佳地，該式V所示的液晶化合物的含量範圍為5 wt%至8 wt%。Based on the total amount of the liquid crystal components being 100 wt%, the content of the liquid crystal compound represented by the formula V ranges from 2 wt% to 15 wt%. Preferably, the content of the liquid crystal compound represented by the formula V ranges from 3 wt% to 10 wt%. More preferably, the content of the liquid crystal compound represented by the formula V ranges from 5 wt% to 8 wt%.

較佳地，該式V液晶化合物是選自於式V-1： [式V-1]

Figure 02_image178
Preferably, the liquid crystal compound of formula V is selected from formula V-1: [Formula V-1]
Figure 02_image178

式V-1中，該R 8表示為氫、C 1-C 12直鏈烷基、C 3-C 12支鏈烷基、C 1-C 12直鏈烷氧基、C 3-C 12支鏈烷氧基、C 2-C 12直鏈烯基、C 3-C 12支鏈烯基、C 2-C 12直鏈氧烯基或C 3-C 12支鏈氧烯基，上述烷基、烷氧基、烯基或氧烯基為未經取代或任意碳上的氫被氟所取代。 In formula V-1, the R 8 represents hydrogen, C 1 -C 12 straight chain alkyl, C 3 -C 12 branched chain alkyl, C 1 -C 12 straight chain alkoxy, C 3 -C 12 branched Alkoxy, C 2 -C 12 straight chain alkenyl, C 3 -C 12 branched alkenyl, C 2 -C 12 straight chain oxyalkenyl or C 3 -C 12 branched oxyalkenyl, the above-mentioned alkyl , alkoxy, alkenyl or oxyalkenyl is unsubstituted or hydrogen on any carbon is replaced by fluorine.

較佳地，該式V-1液晶化合物是選自於由式V-1a至式V-1c所組成的群組中至少一者。 編號 簡稱 結構 式V-1a 1RIGUO2F

Figure 02_image180
式V-1b 2RIGUO2F
Figure 02_image182
 式V-1c 3RIGUO2F
Figure 02_image184
 Preferably, the liquid crystal compound of formula V-1 is at least one selected from the group consisting of formula V-1a to formula V-1c. serial number Abbreviation structure Formula V-1a 1RIGUO2F
Figure 02_image180
 Formula V-1b 2RIGUO2F
Figure 02_image182
 Formula V-1c 3RIGUO2F
Figure 02_image184

較佳地，本發明液晶組成物還包含一添加劑，該添加劑包括式VI所示的化合物。 [式VI]

Figure 02_image186
Preferably, the liquid crystal composition of the present invention further includes an additive, and the additive includes a compound represented by formula VI. [Formula VI]
Figure 02_image186

在該式VI中，環K表示1,4-伸苯基或茚滿-2,5-二基，上述基團為未經取代或環上任一位置的氫被氟所取代。In the formula VI, the ring K represents a 1,4-phenylene group or an indan-2,5-diyl group, and the above group is unsubstituted or hydrogen at any position on the ring is replaced by fluorine.

Z 3表示－OCH 2－、－CH 2O－、－CH 2CH 2－或單鍵。 Z 3 represents -OCH 2 -, -CH 2 O-, -CH 2 CH 2 - or a single bond.

t及u分別表示1或2，且t與u的總和為2、3或4，當u為2時，每個環K為相同或不同。t and u represent 1 or 2 respectively, and the sum of t and u is 2, 3 or 4. When u is 2, each ring K is the same or different.

以該液晶組成物的總量為100 wt%計，該式VI所示的化合物的含量範圍為0.1 wt%至1 wt%。較佳地，該式VI所示的化合物的含量範圍為0.2 wt%至0.7 wt%。Based on the total amount of the liquid crystal composition being 100 wt%, the content of the compound represented by the formula VI ranges from 0.1 wt% to 1 wt%. Preferably, the content of the compound represented by formula VI ranges from 0.2 wt% to 0.7 wt%.

較佳地，該式VI化合物是選自於由式VI-1、式VI-2及式VI-3所組成的群組中至少一者： [式VI-1]

Figure 02_image188
[式VI-2]
Figure 02_image190
[式VI-3]
Figure 02_image192
Preferably, the compound of formula VI is at least one selected from the group consisting of formula VI-1, formula VI-2 and formula VI-3: [Formula VI-1]
Figure 02_image188
[Formula VI-2]
Figure 02_image190
[Formula VI-3]
Figure 02_image192

式VI-1至式VI-3中，該Z 3表示－OCH 2－、－CH 2O－、－CH 2CH 2－或單鍵。 In the formulas VI-1 to VI-3, the Z 3 represents -OCH 2 -, -CH 2 O-, -CH 2 CH 2 - or a single bond.

較佳地，該式VI-1化合物是選自於式VI-1a。較佳地，該式VI-2化合物是選自於式VI-2a。較佳地，該式VI-3化合物是選自於式VI-3a。 編號 簡稱 結構 式VI-1a BMA

Figure 02_image194
式VI-2a PG1OGPMA
Figure 02_image196
 式VI-3a PGRIMA
Figure 02_image198
 Preferably, the compound of formula VI-1 is selected from formula VI-1a. Preferably, the compound of formula VI-2 is selected from formula VI-2a. Preferably, the compound of formula VI-3 is selected from formula VI-3a. serial number Abbreviation structure Formula VI-1a BMA
Figure 02_image194
 Formula VI-2a PG1OGPMA
Figure 02_image196
 Formula VI-3a PGRIMA
Figure 02_image198

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 these examples are for illustrative purposes only and should not be construed as limitations on the implementation of the present invention.

[合成例1]式I-1e所示液晶化合物

Figure 02_image200
[Synthesis Example 1] Liquid crystal compound shown in formula I-1e
Figure 02_image200

(1).化合物A1的合成：將4-溴苯丙醇(15 g，69.8 mmol)、對甲苯磺醯氯(12.6 g，66.3 mmol，簡稱TsCl)、三乙胺(9.6 mL，69.8 mmol，簡稱TEA)及二氯甲烷(280 mL，簡稱DCM)混合得到一混合物，將該混合物加熱至30°C進行反應，並以矽膠薄層層析(沖提液：乙酸乙酯/正己烷的體積比＝3/7)追蹤該反應至TsCl反應完畢，接著，加入少許濃度為1N的鹽酸中止反應，得到一粗產物。將該粗產物以蒸餾水及乙酸乙酯進行萃取並收集有機層，之後，將該有機層先以硫酸鎂除水，再過濾後進行減壓濃縮移除殘留有機溶劑，即得到化合物A1。(1). Synthesis of compound A1: 4-bromophenylpropanol (15 g, 69.8 mmol), p-toluenesulfonyl chloride (12.6 g, 66.3 mmol, referred to as TsCl), triethylamine (9.6 mL, 69.8 mmol, TEA for short) and dichloromethane (280 mL, DCM for short) were mixed to obtain a mixture, and the mixture was heated to 30°C for reaction, and thin-layer chromatography on silica gel (eluent: the volume of ethyl acetate/n-hexane Ratio=3/7) Follow the reaction until the reaction of TsCl is completed, then, add a little concentration of 1N hydrochloric acid to stop the reaction to obtain a crude product. The crude product was extracted with distilled water and ethyl acetate, and the organic layer was collected. After that, the organic layer was dehydrated with magnesium sulfate, filtered, and then concentrated under reduced pressure to remove the residual organic solvent to obtain compound A1.

(2).化合物A2的合成：將該化合物A1、四正丁基氟化銨·1M四氫呋喃溶液(140 mL，139.6 mmol，簡稱TBAF)及四氫呋喃(270mL，簡稱THF)混合後進行反應，並以矽膠薄層層析(沖提液：乙酸乙酯/正己烷的體積比=1/19)追蹤該反應至該化合物A1反應完畢得到一粗產物，接著，以減壓濃縮移除該粗產物中的有機溶劑後，進行矽膠管柱層析純化(沖提液：乙酸乙酯/正己烷的體積比=1/19)，即得到化合物A2。(2). Synthesis of compound A2: Mix the compound A1, tetra-n-butylammonium fluoride 1M tetrahydrofuran solution (140 mL, 139.6 mmol, referred to as TBAF) and tetrahydrofuran (270 mL, referred to as THF) to react, and Silica gel thin-layer chromatography (eluent: volume ratio of ethyl acetate/n-hexane=1/19) traced the reaction to the completion of the reaction of compound A1 to obtain a crude product, and then concentrated under reduced pressure to remove the crude product The organic solvent was purified by silica gel column chromatography (eluent: volume ratio of ethyl acetate/n-hexane = 1/19) to obtain compound A2.

(3).化合物I-1e的合成：將該化合物A2、4-甲基苯硼酸(14.2 g，104.7 mmol)、四(三苯基膦)鈀(2 g，1.73 mmol，簡稱Pd(PPh 3) 4)、碳酸鉀水溶液(3M， 115mL)及四氫呋喃(450mL)進行混合得到一混合物，將該混合物在一充滿乾燥氮氣的回流裝置中加熱至四氫呋喃的回流溫度並進行反應，並以矽膠薄層層析(沖提液為正己烷)追蹤反應至該化合物A2反應完畢而得到一粗產物。待該粗產物的溫度回到室溫後，將該粗產物以蒸餾水及乙酸乙酯進行萃取並收集有機層，之後，將該有機層先以硫酸鎂除水，再過濾後進行減壓濃縮移除殘留有機溶劑，並進行矽膠管柱層析純化(沖提液為正己烷)，得到式I-1e所示液晶化合物。 (3). Synthesis of compound I-1e: the compound A2, 4-methylphenylboronic acid (14.2 g, 104.7 mmol), tetrakis (triphenylphosphine) palladium (2 g, 1.73 mmol, referred to as Pd (PPh 3 ) 4 ), potassium carbonate aqueous solution (3M, 115mL) and tetrahydrofuran (450mL) were mixed to obtain a mixture, which was heated to the reflux temperature of tetrahydrofuran in a reflux device filled with dry nitrogen and reacted, and a thin layer of silica gel Chromatography (the eluent is n-hexane) traced the reaction until the reaction of the compound A2 was completed to obtain a crude product. After the temperature of the crude product returned to room temperature, the crude product was extracted with distilled water and ethyl acetate, and the organic layer was collected. After that, the organic layer was dehydrated with magnesium sulfate, filtered, concentrated under reduced pressure, and removed. Residual organic solvents were removed, and purified by silica gel column chromatography (the eluent was n-hexane) to obtain the liquid crystal compound shown in formula I-1e.

利用核磁共振光譜儀進行式I-1e所示液晶化合物的鑑定，結果為： 1H-NMR(400 MHz，CDCl 3):δ7.51-7.46(m，4H)，δ7.23-7.22(m，4H)，δ4.48(dt，2H)，δ2.77(t，2H)，δ2.38(s，3H)，δ2.03(dtt，2H)。 The identification of the liquid crystal compound shown in formula I-1e was carried out by nuclear magnetic resonance spectrometer, and the result was: 1 H-NMR (400 MHz, CDCl 3 ): δ7.51-7.46 (m, 4H), δ7.23-7.22 (m, 4H), δ 4.48 (dt, 2H), δ 2.77 (t, 2H), δ 2.38 (s, 3H), δ 2.03 (dtt, 2H).

[合成例2] 式I-1h所示液晶化合物

Figure 02_image202
[Synthesis Example 2] Liquid crystal compound shown in formula I-1h
Figure 02_image202

(1).化合物B2的合成：先將化合物B1(2 g，9 mmol)與硼烷二甲硫醚(4.5 mL，9 mmol，簡稱BH 3-SMe 2)在0°C下混合後得到一混合物，並使該混合物於氮氣氣氛下緩慢回到室溫後反應3小時，接著，在冰浴條件下，於該混合物中緩慢地加入蒸餾水(10 mL)、30%氫氧化鈉(簡稱NaOH)水溶液(5 mL)及30%過氧化氫(簡稱H 2O 2)水溶液(5 mL，44 mmol)混合並進行反應30分鐘後，待反應溫度回到室溫後，加入少許飽和碳酸鉀水溶液攪拌至白色懸浮固體消失得到一粗產物，將該粗產物以蒸餾水及乙酸乙酯進行萃取並收集有機層，之後，將該有機層先以硫酸鎂除水，再過濾後進行減壓濃縮移除殘留有機溶劑，即得到化合物B2。 (1). Synthesis of compound B2: firstly mix compound B1 (2 g, 9 mmol) with borane dimethyl sulfide (4.5 mL, 9 mmol, referred to as BH 3 -SMe 2 ) at 0°C to obtain a mixture, and the mixture was slowly returned to room temperature under a nitrogen atmosphere and reacted for 3 hours, then, under ice-bath conditions, slowly added distilled water (10 mL), 30% sodium hydroxide (NaOH for short) to the mixture Aqueous solution (5 mL) and 30% hydrogen peroxide (referred to as H 2 O 2 ) aqueous solution (5 mL, 44 mmol) were mixed and reacted for 30 minutes. After the reaction temperature returned to room temperature, a little saturated potassium carbonate aqueous solution was added and stirred. A crude product was obtained until the white suspended solid disappeared. The crude product was extracted with distilled water and ethyl acetate and the organic layer was collected. After that, the organic layer was dehydrated with magnesium sulfate, filtered, and then concentrated under reduced pressure to remove the residual organic solvent to obtain compound B2.

(2).化合物I-1h的合成：將該化合物B2、三氟化二乙胺基硫(1.9 g，11.7 mmol，簡稱DAST)及二氯甲烷(80 mL，簡稱DCM) 在-60°C下混合後進行反應，並以矽膠薄層層析(沖提液：乙酸乙酯/正己烷的體積比=1/4)追蹤該反應至該化合物B2反應完畢而得到一混合物。待該混合物的溫度回到室溫後，加入飽和碳酸氫鈉水溶液中止反應得到一粗產物，將該粗產物以蒸餾水及乙酸乙酯進行萃取並收集有機層，之後，將該有機層先以硫酸鎂除水，再過濾後進行減壓濃縮移除殘留有機溶劑，並進行矽膠管柱層析純化(沖提液為正己烷)，得到式I-1h所示液晶化合物。(2). Synthesis of compound I-1h: the compound B2, diethylaminosulfur trifluoride (1.9 g, 11.7 mmol, referred to as DAST) and dichloromethane (80 mL, referred to as DCM) at -60 ° C The reaction was carried out after mixing down, and the reaction was followed by silica gel thin layer chromatography (eluent: volume ratio of ethyl acetate/n-hexane=1/4) until the reaction of the compound B2 was completed to obtain a mixture. After the temperature of the mixture returned to room temperature, a saturated aqueous sodium bicarbonate solution was added to terminate the reaction to obtain a crude product, which was extracted with distilled water and ethyl acetate and the organic layer was collected. After that, the organic layer was washed with sulfuric acid Magnesium was used to remove water, and then filtered, concentrated under reduced pressure to remove residual organic solvent, and purified by silica gel column chromatography (the eluent was n-hexane), and the liquid crystal compound shown in formula I-1h was obtained.

利用核磁共振光譜儀進行式I-1h所示液晶化合物的鑑定，結果為： 1H-NMR(400 MHz，CDCl 3):δ7.50-7.46(m，4H)，δ7.26-7.22(m，4H)，δ4.47(dt，2H)，δ2.69(t，2H)，δ2.38(s，3H)，δ1.82-1.70(m，4H)。 The identification of the liquid crystal compound shown in Formula I-1h was carried out using a nuclear magnetic resonance spectrometer, and the results were: 1 H-NMR (400 MHz, CDCl 3 ): δ7.50-7.46 (m, 4H), δ7.26-7.22 (m, 4H), δ4.47 (dt, 2H), δ2.69 (t, 2H), δ2.38 (s, 3H), δ1.82-1.70 (m, 4H).

[合成例3] 式I-2a所示液晶化合物

Figure 02_image204
[Synthesis Example 3] Liquid crystal compound shown in formula I-2a
Figure 02_image204

(1).化合物C2的合成：先將化合物C1(15 g，56.08 mmol)與硼烷二甲硫醚(28.1 mL，56.08 mmol，簡稱BH 3-SMe 2)在0°C下混合後，並於氮氣氣氛下緩慢回到室溫反應3小時後，接著，在冰浴條件下，緩慢地加入蒸餾水(9mL)、30%氫氧化鈉(簡稱NaOH)水溶液(22.5 mL)及30%過氧化氫(簡稱H 2O 2)水溶液(22.5 mL，198 mmol)混合並進行反應30分鐘後，得到一混合物，待該混合物的溫度回到室溫後，加入少許飽和碳酸鉀水溶液攪拌至白色懸浮固體消失得到一粗產物，將該粗產物以蒸餾水及乙酸乙酯進行萃取並收集有機層，之後，將該有機層先以硫酸鎂除水，再過濾後進行減壓濃縮移除殘留有機溶劑，即得到化合物C2。 (1). Synthesis of compound C2: first mix compound C1 (15 g, 56.08 mmol) with borane dimethyl sulfide (28.1 mL, 56.08 mmol, referred to as BH 3 -SMe 2 ) at 0°C, and Slowly return to room temperature under nitrogen atmosphere and react for 3 hours, then, under ice bath conditions, slowly add distilled water (9 mL), 30% sodium hydroxide (NaOH for short) aqueous solution (22.5 mL) and 30% hydrogen peroxide (referred to as H 2 O 2 ) aqueous solution (22.5 mL, 198 mmol) was mixed and reacted for 30 minutes to obtain a mixture. After the temperature of the mixture returned to room temperature, a little saturated potassium carbonate aqueous solution was added and stirred until the white suspended solid disappeared. A crude product was obtained, the crude product was extracted with distilled water and ethyl acetate, and the organic layer was collected. After that, the organic layer was dehydrated with magnesium sulfate, filtered, and then concentrated under reduced pressure to remove the residual organic solvent, to obtain Compound C2.

(2).化合物C3的合成：將該化合物C2、對甲苯磺醯氯(16 g，84.12 mmol，簡稱TsCl)、三乙胺(11.7 mL，84.12 mmol，簡稱TEA)、4-二甲氨基吡啶(1.7 g，14.02 mmol，簡稱DMAP)及二氯甲烷(275 mL，簡稱DCM)進行混合後得到一混合物，將該混合物加熱至30℃進行反應，並以矽膠薄層層析(沖提液：乙酸乙酯/正己烷的體積比=3/17)追蹤該反應至TsCl反應完畢，接著，加入少許濃度為1N的鹽酸中止反應，得到一粗產物，將該粗產物以蒸餾水及乙酸乙酯進行萃取並收集有機層，之後，將該有機層先以硫酸鎂除水，再過濾後進行減壓濃縮移除殘留有機溶劑後，進行矽膠管柱層析純化(沖提液：乙酸乙酯/正己烷的體積比=1/9)，即得到化合物C3。(2). Synthesis of compound C3: the compound C2, p-toluenesulfonyl chloride (16 g, 84.12 mmol, referred to as TsCl), triethylamine (11.7 mL, 84.12 mmol, referred to as TEA), 4-dimethylaminopyridine (1.7 g, 14.02 mmol, referred to as DMAP) and dichloromethane (275 mL, referred to as DCM) were mixed to obtain a mixture, the mixture was heated to 30 ° C for reaction, and silica gel thin layer chromatography (eluent: The volume ratio of ethyl acetate/n-hexane=3/17) track the reaction until the TsCl reaction is complete, then, add a little concentration of 1N hydrochloric acid to stop the reaction to obtain a crude product, which is carried out with distilled water and ethyl acetate Extract and collect the organic layer. Afterwards, the organic layer was dehydrated with magnesium sulfate, filtered, concentrated under reduced pressure to remove residual organic solvent, and purified by silica gel column chromatography (eluant: ethyl acetate/n-hexane The volume ratio of alkane=1/9), promptly obtains compound C3.

(3).化合物I-2a的合成：將該化合物C3、四正丁基氟化銨·1M四氫呋喃溶液(112.16 mL，112.16 mmol，簡稱TBAF)及四氫呋喃(110 mL，簡稱THF)混合並進行反應12小時後得到一混合物，進行減壓濃縮移除該混合物中的有機溶劑得到一粗產物，將該粗產物以蒸餾水及乙酸乙酯進行萃取並收集有機層，之後，將該有機層先以硫酸鎂除水，再過濾後進行減壓濃縮移除殘留有機溶劑後，進行矽膠管柱層析純化(沖提液：乙酸乙酯/正己烷的體積比=1/9)，得到式I-2a所示液晶化合物。(3). Synthesis of compound I-2a: The compound C3, tetra-n-butylammonium fluoride 1M tetrahydrofuran solution (112.16 mL, 112.16 mmol, referred to as TBAF) and tetrahydrofuran (110 mL, referred to as THF) were mixed and reacted After 12 hours, a mixture was obtained, which was concentrated under reduced pressure to remove the organic solvent in the mixture to obtain a crude product. The crude product was extracted with distilled water and ethyl acetate and the organic layer was collected. After that, the organic layer was first washed with sulfuric acid Magnesium to remove water, and then filtered and then concentrated under reduced pressure to remove residual organic solvents, then purified by silica gel column chromatography (eluent: volume ratio of ethyl acetate/n-hexane = 1/9), to obtain formula I-2a The liquid crystal compounds shown.

利用核磁共振光譜儀進行式I-2a所示液晶化合物的鑑定，結果為： 1H-NMR(400 MHz，CDCl 3):δ7.08(s，4H)，δ4.49(dt，2H)，δ2.39(tt，1H)，δ2.30(t，3H)，δ1.90-1.73(m，8H)，δ1.58(dtt，2H)，δ1.45-1.34(m，3H)，δ1.15-0.87(m，8H)。 The identification of the liquid crystal compound shown in formula I-2a was carried out by nuclear magnetic resonance spectrometer, and the result was: 1 H-NMR (400 MHz, CDCl 3 ): δ7.08 (s, 4H), δ4.49 (dt, 2H), δ2 .39(tt, 1H), δ2.30(t, 3H), δ1.90-1.73(m, 8H), δ1.58(dtt, 2H), δ1.45-1.34(m, 3H), δ1. 15-0.87 (m, 8H).

[合成例4] 式I-2b所示液晶化合物

Figure 02_image206
[Synthesis Example 4] Liquid crystal compound shown in formula I-2b
Figure 02_image206

(1).化合物D1的合成：將乙二醯氯(3.6 mL，41.69 mmol，簡稱(COCl) 2)及四氫呋喃(190 mL，簡稱THF)混合並於乾燥氮氣氣氛下降溫至-78°C，接著，緩慢加入二甲基亞碸(3.9 mL，簡稱DMSO)並攪拌30分鐘，再緩慢地加入該化合物C2(8.35 g，27.79 mmol)及四氫呋喃(190 mL，簡稱THF)並攪拌45分鐘後，再加入三乙胺(18 mL，111.16 mmol，簡稱TEA)得到一混合物，並攪拌2小時使該混合物的溫度緩慢回室溫後，加入飽和氯化銨水溶液中止反應得到一粗產物，將該粗產物以蒸餾水及乙酸乙酯進行萃取並收集有機層，之後，將該有機層先以硫酸鎂除水，再過濾後進行減壓濃縮移除殘留有機溶劑後，進行矽膠管柱層析純化(沖提液：乙酸乙酯/正己烷的體積比=1/4)，即得到化合物D1。 (1). Synthesis of compound D1: Mix acetyl chloride (3.6 mL, 41.69 mmol, referred to as (COCl) 2 ) and tetrahydrofuran (190 mL, referred to as THF) and lower the temperature to -78°C in a dry nitrogen atmosphere. Then, slowly add dimethylsulfoxide (3.9 mL, referred to as DMSO) and stir for 30 minutes, then slowly add the compound C2 (8.35 g, 27.79 mmol) and tetrahydrofuran (190 mL, referred to as THF) and stir for 45 minutes, Then add triethylamine (18 mL, 111.16 mmol, referred to as TEA) to obtain a mixture, and stir for 2 hours to slowly return the temperature of the mixture to room temperature, add saturated aqueous ammonium chloride solution to stop the reaction to obtain a crude product, the crude The product was extracted with distilled water and ethyl acetate and the organic layer was collected. After that, the organic layer was dehydrated with magnesium sulfate, filtered, concentrated under reduced pressure to remove the residual organic solvent, and purified by silica gel column chromatography (washing Extraction solution: volume ratio of ethyl acetate/n-hexane=1/4) to obtain compound D1.

(2).化合物D2的合成：將甲基三苯基溴化膦(11.8 g，33.05 mmol，簡稱Ph 3PCH 3Br) 及四氫呋喃(60 mL，簡稱THF)進行混合並降溫至0°C後，緩慢加入正丁基鋰(簡稱n-BuLi)·2.5 M正己烷溶液(9.9 mL，24.75 mmol) 攪拌2小時，再加入該化合物D1及四氫呋喃(40 mL，簡稱THF)進行反應得到一混合物，將該混合物攪拌2小時後，使該混合物的溫度回到室溫後繼續攪拌10小時，接著，加入飽和氯化銨水溶液中止反應得到一粗產物，將該粗產物以蒸餾水及乙酸乙酯進行萃取並收集有機層，之後，將該有機層先以硫酸鎂除水，再過濾後進行減壓濃縮移除殘留有機溶劑後，進行矽膠管柱層析純化(沖提液：乙酸乙酯/正己烷的體積比=1/19)，即得到化合物D2。 (2). Synthesis of compound D2: Mix methyltriphenylphosphine bromide (11.8 g, 33.05 mmol, referred to as Ph 3 PCH 3 Br) and tetrahydrofuran (60 mL, referred to as THF) and cool to 0°C , slowly added n-butyllithium (abbreviated as n-BuLi) · 2.5 M n-hexane solution (9.9 mL, 24.75 mmol) and stirred for 2 hours, then added the compound D1 and tetrahydrofuran (40 mL, referred to as THF) to react to obtain a mixture, After the mixture was stirred for 2 hours, the temperature of the mixture was returned to room temperature and continued to stir for 10 hours. Then, a saturated ammonium chloride aqueous solution was added to terminate the reaction to obtain a crude product, which was extracted with distilled water and ethyl acetate And collect the organic layer, after that, the organic layer is dehydrated with magnesium sulfate first, then filtered, then concentrated under reduced pressure to remove the residual organic solvent, and then purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane The volume ratio=1/19), promptly obtains compound D2.

(3).化合物D3的合成：化合物D3的合成方法是與化合物C2的合成方法類似，差別在於，在化合物D3的合成方法中，是將化合物C1置換成化合物D2以製得化合物D3。(3). Synthesis of compound D3: the synthesis method of compound D3 is similar to the synthesis method of compound C2, the difference is that in the synthesis method of compound D3, compound C1 is replaced by compound D2 to obtain compound D3.

(4).化合物D4的合成：化合物D4的合成方法是與化合物C3的合成方法類似，差別在於，在化合物D4的合成方法中，是將化合物C2置換成化合物D3以製得化合物D4。(4). Synthesis of compound D4: the synthesis method of compound D4 is similar to the synthesis method of compound C3, the difference is that in the synthesis method of compound D4, compound C2 is replaced by compound D3 to obtain compound D4.

(5).化合物I-2b的合成：化合物I-2b的合成方法是與化合物I-2a的合成方法類似，差別在於，在化合物I-2b的合成方法中，是將化合物C3置換成化合物D4以製得式I-2b所示液晶化合物。(5). Synthesis of compound I-2b: the synthesis method of compound I-2b is similar to the synthesis method of compound I-2a, the difference is that in the synthesis method of compound I-2b, compound C3 is replaced by compound D4 To prepare the liquid crystal compound shown in formula I-2b.

利用核磁共振光譜儀進行式I-2b所示液晶化合物的鑑定，結果為： 1H-NMR(400 MHz，CDCl 3):δ7.08(s，4H)，δ4.41(dt，2H)，δ2.39(tt，1H)，δ2.30(t，3H)，δ1.90-0.84(m，23H)。 The identification of the liquid crystal compound shown in Formula I-2b was carried out using a nuclear magnetic resonance spectrometer, and the results were: 1 H-NMR (400 MHz, CDCl 3 ): δ7.08 (s, 4H), δ4.41 (dt, 2H), δ2 .39 (tt, 1H), δ2.30 (t, 3H), δ1.90-0.84 (m, 23H).

[合成例5] 式I-2c所示液晶化合物

Figure 02_image208
[Synthesis Example 5] Liquid crystal compound shown in formula I-2c
Figure 02_image208

(1).化合物E2的合成：化合物E2的合成方法是與化合物B2的合成方法類似，差別在於，在化合物E2的合成中，是將化合物B1置換成化合物E1以製得化合物E2。(1). Synthesis of compound E2: the synthesis method of compound E2 is similar to the synthesis method of compound B2, the difference is that in the synthesis of compound E2, compound B1 is replaced by compound E1 to obtain compound E2.

(2).化合物I-2c的合成：化合物I-2c的合成方法是與化合物I-1h的合成方法類似，差別在於，在化合物I-2c的合成方法中，是將化合物B2置換成化合物E2以製得式I-2c所示液晶化合物。(2). Synthesis of compound I-2c: the synthesis method of compound I-2c is similar to the synthesis method of compound I-1h, the difference is that in the synthesis method of compound I-2c, compound B2 is replaced by compound E2 To prepare the liquid crystal compound shown in formula I-2c.

利用核磁共振光譜儀進行式I-2c所示液晶化合物的鑑定，結果為： 1H-NMR(400 MHz，CDCl 3):δ7.08(s，4H)，δ4.43(dt，2H)，δ2.39(tt，1H)，δ2.30(t，3H)，δ1.90-0.81(m，25H)。 The identification of the liquid crystal compound shown in formula I-2c was carried out by nuclear magnetic resonance spectrometer, and the result was: 1 H-NMR (400 MHz, CDCl 3 ): δ7.08 (s, 4H), δ4.43 (dt, 2H), δ2 .39 (tt, 1H), δ2.30 (t, 3H), δ1.90-0.81 (m, 25H).

實施例1至16及比較例1至2Examples 1 to 16 and Comparative Examples 1 to 2

[液晶組成物的製備][Preparation of Liquid Crystal Composition]

依據下表1至表3中所列的成分的種類及用量配製實施例1至16的液晶組成物及比較例1至2的液晶組成物。The liquid crystal compositions of Examples 1 to 16 and the liquid crystal compositions of Comparative Examples 1 to 2 were prepared according to the types and amounts of the components listed in Tables 1 to 3 below.

其中，比較例1及2與實施例1至16的主要差異在於，比較例1及2未使用式I所示的液晶化合物，而是使用3CC1F的液晶化合物。 簡稱 結構 3CC1F

Figure 02_image210
Among them, the main difference between Comparative Examples 1 and 2 and Examples 1 to 16 is that Comparative Examples 1 and 2 did not use the liquid crystal compound represented by formula I, but used the liquid crystal compound of 3CC1F. Abbreviation structure 3CC1F
Figure 02_image210

[液晶顯示裝置][Liquid crystal display device]

實施例1的液晶顯示裝置是利用實施例1的液晶組成物進行製備。該液晶顯示裝置是透過將兩片含有氧化銦錫層的基板(下稱ITO基板)間隔設置(間隔為3.5 mm)，然後將實施例1的液晶組成物注入兩片ITO基板之間的間隙內，並依據液晶盒製作方式進行封口而形成一液晶盒。對該液晶盒施加12V直流電壓，同時照射紫外光(峰值波長313 nm)進行固化，形成一液晶顯示裝置。實施例2至16及比較例1至2的液晶顯示裝置是以與實施例1相同的製備方法得到液晶顯示裝置，差別在於實施例2至16及比較例1至2分別使用實施例2至16及比較例1至2的液晶組成物。The liquid crystal display device of Example 1 is prepared using the liquid crystal composition of Example 1. This liquid crystal display device is by setting two substrates containing indium tin oxide layers (hereinafter referred to as ITO substrates) at intervals (the interval is 3.5 mm), and then injecting the liquid crystal composition of Example 1 into the gap between the two ITO substrates , and seal according to the manufacturing method of the liquid crystal cell to form a liquid crystal cell. A 12V DC voltage was applied to the liquid crystal cell, and at the same time, ultraviolet light (peak wavelength: 313 nm) was irradiated for curing to form a liquid crystal display device. The liquid crystal display devices of Examples 2 to 16 and Comparative Examples 1 to 2 are obtained by the same preparation method as that of Example 1, the difference is that Examples 2 to 16 and Comparative Examples 1 to 2 use Examples 2 to 16 respectively and the liquid crystal compositions of Comparative Examples 1 to 2.

表1 用量(wt%) 實施例 1 2 3 4 5 6 液晶 組分 式I 1PP3F 4 8 -- -- 9 4.4 3PP3F -- -- 1.5 5 -- -- F2CCP1 -- -- -- -- -- -- F3CCP1 -- -- -- -- -- -- 式II 3CYO2 18.5 19 19 19 -- 18.5 5CYO2 -- -- 6.5 3 -- -- 2CCY1 -- -- -- -- -- 2 3CCY1 -- -- 10 10 -- -- 3CCYO1 5 -- -- -- -- -- 3CCYO2 8 10 8 -- -- 12.5 2CPYO2 -- -- -- -- -- -- 3CPYO2 17 15 13 13 -- 16.5 3CPYO3 -- -- -- -- -- -- 3CPYO4 1 -- -- 8 -- -- 式III 2RIGUQUF -- -- -- -- 7 -- 3RIGUQUF -- -- -- -- 4 -- 式IV 3CC2 9.5 20 20 20 -- 9.9 3CC3 2.5 -- -- -- -- 2 3CC4 13.5 -- 6 6 -- 14.1 3CC5 -- -- -- -- -- 5.8 5CC2 2.5 -- -- -- -- 1.3 3CCO1 -- -- -- -- 5 0.5 3CCV1 -- -- -- -- 5 -- 3CCV -- -- -- -- 35 -- 3CPO1 -- -- -- -- -- 2 3CPO2 8 10 -- -- -- -- 3PPO2 6 -- -- -- -- 6 1V2PPO1 -- -- -- -- -- -- 3CCP1 -- 8 9 8 -- -- VCCP1 -- -- -- -- -- -- 3CPP1 4.5 -- -- -- -- 4.5 3CPP2 -- 10 7 8 9 -- 2CPPF -- -- -- -- 4 -- 3CPPF -- -- -- -- 5 -- 3CPTP2 -- -- -- -- 11 -- 式V 3RIGUO2F -- -- -- -- 6 -- 添加劑 式VI BMA -- -- -- -- -- --   3CC1F -- -- -- -- -- -- Table 1 Dosage (wt%) Example 1 2 3 4 5 6 liquid crystal composition Formula I 1PP3F 4 8 -- -- 9 4.4 3PP3F -- -- 1.5 5 -- -- F2CCP1 -- -- -- -- -- -- F3CCP1 -- -- -- -- -- -- Formula II 3CYO2 18.5 19 19 19 -- 18.5 5CYO2 -- -- 6.5 3 -- -- 2CCY1 -- -- -- -- -- 2 3CCY1 -- -- 10 10 -- -- 3CCYO1 5 -- -- -- -- -- 3CCYO2 8 10 8 -- -- 12.5 2CPYO2 -- -- -- -- -- -- 3CPYO2 17 15 13 13 -- 16.5 3CPYO3 -- -- -- -- -- -- 3CPYO4 1 -- -- 8 -- -- Formula III 2RIGUQUF -- -- -- -- 7 -- 3RIGUQUF -- -- -- -- 4 -- Formula IV 3CC2 9.5 20 20 20 -- 9.9 3CC3 2.5 -- -- -- -- 2 3CC4 13.5 -- 6 6 -- 14.1 3CC5 -- -- -- -- -- 5.8 5CC2 2.5 -- -- -- -- 1.3 3CCO1 -- -- -- -- 5 0.5 3CCV1 -- -- -- -- 5 -- 3CCV -- -- -- -- 35 -- 3CPO1 -- -- -- -- -- 2 3CPO2 8 10 -- -- -- -- 3PPO2 6 -- -- -- -- 6 1V2PPO1 -- -- -- -- -- -- 3CCP1 -- 8 9 8 -- -- VCCP1 -- -- -- -- -- -- 3CPP1 4.5 -- -- -- -- 4.5 3CPP2 -- 10 7 8 9 -- 2CPPF -- -- -- -- 4 -- 3CPPF -- -- -- -- 5 -- 3CPTP2 -- -- -- -- 11 -- Formula V 3RIGUO2F -- -- -- -- 6 -- additive Formula VI BMA -- -- -- -- -- -- 3CC1F -- -- -- -- -- --

表2 用量(wt%) 實施例 7 8 9 10 11 12 液晶 組分 式I 1PP3F 10.5 3.5 4 -- 9.5 8.5 3PP3F -- -- -- 4 -- -- F2CCP1 -- 7 1 -- -- -- F3CCP1 -- -- -- -- -- -- 式II 3CYO2 12 20 19 18 15 15 5CYO2 1 -- 3 -- -- -- 2CCY1 -- -- -- 2 -- -- 3CCY1 5.5 3.9 -- -- 7.5 5 3CCYO1 -- -- -- -- 8 8 3CCYO2 4 4 12 12 4.5 4 2CPYO2 2.5 -- -- -- 3 2.5 3CPYO2 16.5 17 16 17 16 16.5 3CPYO3 -- 4.5 -- -- -- -- 3CPYO4 -- -- -- -- -- -- 式III 2RIGUQUF -- -- -- -- -- -- 3RIGUQUF -- -- -- -- -- -- 式IV 3CC2 15.5 15.5 15.5 10 15.5 15.5 3CC3 2.5 3 2.5 2.5 -- 2 3CC4 12.5 8 10 13.5 12.5 12.5 3CC5 3 4.4 -- 7 -- -- 5CC2 -- -- 4 3.5 -- -- 3CCO1 -- -- -- -- -- -- 3CCV1 -- -- -- -- -- -- 3CCV -- -- -- -- -- -- 3CPO1 8 -- -- -- -- -- 3CPO2 -- -- -- -- 4 4 3PPO2 2.5 5.2 -- 6 2 2 1V2PPO1 -- -- 6.5 -- -- -- 3CCP1 -- -- -- -- -- -- VCCP1 -- -- -- -- -- -- 3CPP1 4 4 6 4.5 2.5 4.5 3CPP2 -- -- 0.5 -- -- -- 2CPPF -- -- -- -- -- -- 3CPPF -- -- -- -- -- -- 3CPTP2 -- -- -- -- -- -- 式V 3RIGUO2F -- -- -- -- -- -- 添加劑 式VI BMA -- -- -- -- -- --   3CC1F -- -- -- -- -- -- Table 2 Dosage (wt%) Example 7 8 9 10 11 12 liquid crystal composition Formula I 1PP3F 10.5 3.5 4 -- 9.5 8.5 3PP3F -- -- -- 4 -- -- F2CCP1 -- 7 1 -- -- -- F3CCP1 -- -- -- -- -- -- Formula II 3CYO2 12 20 19 18 15 15 5CYO2 1 -- 3 -- -- -- 2CCY1 -- -- -- 2 -- -- 3CCY1 5.5 3.9 -- -- 7.5 5 3CCYO1 -- -- -- -- 8 8 3CCYO2 4 4 12 12 4.5 4 2CPYO2 2.5 -- -- -- 3 2.5 3CPYO2 16.5 17 16 17 16 16.5 3CPYO3 -- 4.5 -- -- -- -- 3CPYO4 -- -- -- -- -- -- Formula III 2RIGUQUF -- -- -- -- -- -- 3RIGUQUF -- -- -- -- -- -- Formula IV 3CC2 15.5 15.5 15.5 10 15.5 15.5 3CC3 2.5 3 2.5 2.5 -- 2 3CC4 12.5 8 10 13.5 12.5 12.5 3CC5 3 4.4 -- 7 -- -- 5CC2 -- -- 4 3.5 -- -- 3CCO1 -- -- -- -- -- -- 3CCV1 -- -- -- -- -- -- 3CCV -- -- -- -- -- -- 3CPO1 8 -- -- -- -- -- 3CPO2 -- -- -- -- 4 4 3PPO2 2.5 5.2 -- 6 2 2 1V2PPO1 -- -- 6.5 -- -- -- 3CCP1 -- -- -- -- -- -- VCCP1 -- -- -- -- -- -- 3CPP1 4 4 6 4.5 2.5 4.5 3CPP2 -- -- 0.5 -- -- -- 2CPPF -- -- -- -- -- -- 3CPPF -- -- -- -- -- -- 3CPTP2 -- -- -- -- -- -- Formula V 3RIGUO2F -- -- -- -- -- -- additive Formula VI BMA -- -- -- -- -- -- 3CC1F -- -- -- -- -- --

表3 用量(wt%) 實施例 比較例 13 14 15 16 1 2 液晶 組分 式I 1PP3F -- -- 1.7 2 -- -- 3PP3F -- 9.5 -- -- -- -- F2CCP1 6 -- -- 6 -- -- F3CCP1 -- -- 4 -- -- -- 式II 3CYO2 24.4 15 21 20 19 -- 5CYO2 -- -- 3.4 -- -- -- 2CCY1 -- -- -- -- -- -- 3CCY1 -- 7.5 -- 4.4 -- -- 3CCYO1 -- 8 -- -- -- -- 3CCYO2 4 4.5 9 4 10 -- 2CPYO2 -- 3 -- -- -- -- 3CPYO2 17 16 17 17 15.5 -- 3CPYO3 4.5 -- -- 4.5 -- -- 3CPYO4 -- -- -- -- -- -- 式III 2RIGUQUF -- -- -- -- -- 7 3RIGUQUF -- -- -- -- -- 4 式IV 3CC2 15.5 15.5 15.5 15.5 20 -- 3CC3 3 -- 2.5 3 -- -- 3CC4 8 12.5 8 8 -- -- 3CC5 -- -- -- 6.4 -- -- 5CC2 -- -- -- -- -- -- 3CCO1 -- -- -- -- 1.5 7 3CCV1 -- -- -- -- -- 3 3CCV -- -- -- -- -- 35 3CPO1 -- -- -- -- -- -- 3CPO2 6.4 4 5.4 -- 10 -- 3PPO2 5.2 2 5.5 5.2 -- -- 1V2PPO1 -- -- -- -- -- -- 3CCP1 -- -- -- -- 6 -- VCCP1 -- -- 2 -- -- -- 3CPP1 6 2.5 5 4 -- -- 3CPP2 -- -- -- -- 10 7 2CPPF -- -- -- -- -- 4 3CPPF -- -- -- -- -- 5 3CPTP2 -- -- -- -- -- 11 式V 3RIGUO2F -- -- -- -- -- 6 添加劑 式VI BMA -- -- -- 0.3 -- --   3CC1F -- -- -- -- 8 11 table 3 Dosage (wt%) Example comparative example 13 14 15 16 1 2 liquid crystal composition Formula I 1PP3F -- -- 1.7 2 -- -- 3PP3F -- 9.5 -- -- -- -- F2CCP1 6 -- -- 6 -- -- F3CCP1 -- -- 4 -- -- -- Formula II 3CYO2 24.4 15 twenty one 20 19 -- 5CYO2 -- -- 3.4 -- -- -- 2CCY1 -- -- -- -- -- -- 3CCY1 -- 7.5 -- 4.4 -- -- 3CCYO1 -- 8 -- -- -- -- 3CCYO2 4 4.5 9 4 10 -- 2CPYO2 -- 3 -- -- -- -- 3CPYO2 17 16 17 17 15.5 -- 3CPYO3 4.5 -- -- 4.5 -- -- 3CPYO4 -- -- -- -- -- -- Formula III 2RIGUQUF -- -- -- -- -- 7 3RIGUQUF -- -- -- -- -- 4 Formula IV 3CC2 15.5 15.5 15.5 15.5 20 -- 3CC3 3 -- 2.5 3 -- -- 3CC4 8 12.5 8 8 -- -- 3CC5 -- -- -- 6.4 -- -- 5CC2 -- -- -- -- -- -- 3CCO1 -- -- -- -- 1.5 7 3CCV1 -- -- -- -- -- 3 3CCV -- -- -- -- -- 35 3CPO1 -- -- -- -- -- -- 3CPO2 6.4 4 5.4 -- 10 -- 3PPO2 5.2 2 5.5 5.2 -- -- 1V2PPO1 -- -- -- -- -- -- 3CCP1 -- -- -- -- 6 -- VCCP1 -- -- 2 -- -- -- 3CPP1 6 2.5 5 4 -- -- 3CPP2 -- -- -- -- 10 7 2CPPF -- -- -- -- -- 4 3CPPF -- -- -- -- -- 5 3CPTP2 -- -- -- -- -- 11 Formula V 3RIGUO2F -- -- -- -- -- 6 additive Formula VI BMA -- -- -- 0.3 -- -- 3CC1F -- -- -- -- 8 11

[性質測試][nature test]

使用以下方法進行各實施例及比較例的液晶組成物的性質測試，測試結果整理於下表4至表6：The following methods were used to test the properties of the liquid crystal compositions of the examples and comparative examples, and the test results are summarized in Table 4 to Table 6 below:

澄清點溫度(T ni，°C)：使用差示掃描量熱儀(DSC)系統，將液晶組成物置於鋁盤上精秤0.5至10 mg，藉由液晶組成物因相變化而出現的吸熱峰及放熱峰的起始點來確定相變化溫度。相變化的表示方式為：結晶相標示為C，近晶相標示為S，向列相標示為N，液體標示為I。其中，由向列相至液體的相變溫度為澄清點溫度(T ni)。 Clearing point temperature (T ni , °C): Using a differential scanning calorimeter (DSC) system, place the liquid crystal composition on an aluminum pan and weigh 0.5 to 10 mg accurately, and use the heat absorption of the liquid crystal composition due to phase change The peak and the onset of the exothermic peak were used to determine the phase change temperature. The expression of the phase change is: the crystalline phase is marked as C, the smectic phase is marked as S, the nematic phase is marked as N, and the liquid is marked as I. Wherein, the phase transition temperature from nematic phase to liquid is the clear point temperature (T ni ).

介電各向異性(Δε)：將液晶組成物裝入液晶盒中，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⊥。Dielectric anisotropy (Δε): Put the liquid crystal composition into a liquid crystal cell, apply a voltage of 0 V to 20 V to the liquid crystal cell at a temperature of 25°C, and measure it in the direction parallel to the long axis of the liquid crystal molecules The average dielectric constant of the liquid crystal is ε‖, the average dielectric constant measured perpendicular to the long axis of the liquid crystal molecule is ε⊥, and the dielectric anisotropy (Δε)=ε‖-ε⊥.

旋轉黏度(γ1，mPa•S)：將液晶組成物裝入液晶盒中，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。Rotational viscosity (γ1, mPa•S): Put the liquid crystal composition into a liquid crystal cell, apply a voltage of 20 V to the liquid crystal cell at a temperature of 25°C, and convert it by adding a dielectric anisotropy (Δε) factor into the instrument , the rotational viscosity γ1 can be obtained.

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)，對液晶組成物進行量測。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液晶組成物，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⊥。Refractive index anisotropy (Δn): The liquid crystal composition was measured using an Abbe refractometer (manufacturer: ATAGO; model: DR-M2) with a polarizing plate installed on an eyepiece. First, wipe the main surface of the Abbe refractometer in one direction, then drop a small amount of liquid crystal composition on the main surface, and then use a filter with a wavelength of 589 nm to perform refraction 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⊥; refractive index anisotropy (Δn)=n‖-n⊥ .

穿透度(T@5V)：將液晶組成物裝入液晶盒中，於溫度25°C下，對該液晶盒施加5 V的電壓，並利用一光感測模組(廠商： HAMAMATSU；型號： H10721-20)量測穿透過該液晶盒之透射光強度，並以對該液晶盒施加5 V的電壓前所量測的該液晶盒之透射光強度作爲基準計算得到液晶組成物的穿透度。Transmittance (T@5V): Put the liquid crystal composition into a liquid crystal cell, apply a voltage of 5 V to the liquid crystal cell at a temperature of 25°C, and use a light sensing module (manufacturer: HAMAMATSU; model : H10721-20) Measure the transmitted light intensity through the liquid crystal cell, and use the measured transmitted light intensity of the liquid crystal cell before applying a voltage of 5 V to the liquid crystal cell as a reference to calculate the penetration of the liquid crystal composition Spend.

穿透度差值(ΔT)：將液晶組成物裝入液晶盒中，於溫度25°C下，對該液晶盒施加6 V的電壓，並利用一光感測模組(廠商：HAMAMATSU；型號：H10721-20)量測穿透過該液晶盒之透射光強度。之後，再以不施加電壓的條件對該液晶盒進行透射光強度的量測。最後，再將施加電壓為6V時該液晶組成物的透射光強度與不施加電壓時該液晶組成物的透射光強度相減即得到穿透度差值。Transmittance difference (ΔT): Put the liquid crystal composition into a liquid crystal cell, apply a voltage of 6 V to the liquid crystal cell at a temperature of 25°C, and use a light sensing module (manufacturer: HAMAMATSU; model : H10721-20) Measure the transmitted light intensity through the liquid crystal cell. Afterwards, the transmitted light intensity of the liquid crystal cell was measured under the condition of no voltage applied. Finally, the transmitted light intensity of the liquid crystal composition when the applied voltage is 6V is subtracted from the transmitted light intensity of the liquid crystal composition when no voltage is applied to obtain the transmittance difference.

表4   T ni Δε γ1 Δn T@5V 實施例 2 74.2 -2.45 102 0.1058 4749 3 82.7 -2.85 112 0.0944 4417 4 79.3 -2.57 110 0.1014 4738 比較例 1 74.8 -2.45 102 0.0944 4299 Table 4 T ni Δε gamma 1 Δn T@5V Example 2 74.2 -2.45 102 0.1058 4749 3 82.7 -2.85 112 0.0944 4417 4 79.3 -2.57 110 0.1014 4738 comparative example 1 74.8 -2.45 102 0.0944 4299

表5   T ni Δε γ1 Δn ΔT 實施例 5 77.1 3.34 53.3 0.1098 580 比較例 2 78.1 3.39 54.0 0.1237 493 table 5 T ni Δε gamma 1 Δn ΔT Example 5 77.1 3.34 53.3 0.1098 580 comparative example 2 78.1 3.39 54.0 0.1237 493

表6   T ni Δε γ1 Δn 實施例 1 74.0 -2.76 105.6 0.1043 6 73.0 -2.69 110.4 0.1032 7 75.2 -2.56 100.1 0.1033 8 73.7 -2.65 105.5 0.1038 9 74.6 -2.72 106.1 0.1024 10 74.4 -2.64 100.6 0.1022 11 73.4 -2.83 103.8 0.1015 12 75.3 -2.67 100.8 0.1025 13 72.6 -2.79 98.8 0.1026 14 74.2 -2.77 110.4 0.1012 15 73.8 -2.88 109.3 0.1021 16 74.3 -2.66 99.5 0.1026 Table 6 T ni Δε gamma 1 Δn Example 1 74.0 -2.76 105.6 0.1043 6 73.0 -2.69 110.4 0.1032 7 75.2 -2.56 100.1 0.1033 8 73.7 -2.65 105.5 0.1038 9 74.6 -2.72 106.1 0.1024 10 74.4 -2.64 100.6 0.1022 11 73.4 -2.83 103.8 0.1015 12 75.3 -2.67 100.8 0.1025 13 72.6 -2.79 98.8 0.1026 14 74.2 -2.77 110.4 0.1012 15 73.8 -2.88 109.3 0.1021 16 74.3 -2.66 99.5 0.1026

由表1至表3的液晶組成物的組成及表4的性質測試結果可知，當該液晶組成物具有負的介電各向異性時，相較於沒有使用式I液晶化合物的比較例1，實施例2至4由於含有式I液晶化合物而具有較高的穿透度。From the composition of the liquid crystal composition in Table 1 to Table 3 and the property test results in Table 4, it can be seen that when the liquid crystal composition has negative dielectric anisotropy, compared with Comparative Example 1 that does not use the liquid crystal compound of formula I, Examples 2 to 4 have higher transmittance due to containing the liquid crystal compound of formula I.

由表1至表3的液晶組成物的組成及表5的性質測試結果可知，當該液晶組成物具有正的介電各向異性時，相較於沒有使用式I液晶化合物的比較例2，實施例5由於含有式I液晶化合物而具有較高的穿透度差值，表示實施例5的液晶組成物具有較高的穿透度。From the composition of the liquid crystal composition in Table 1 to Table 3 and the property test results in Table 5, it can be seen that when the liquid crystal composition has positive dielectric anisotropy, compared with Comparative Example 2 that does not use the liquid crystal compound of formula I, Example 5 has a higher transmittance difference due to containing the liquid crystal compound of formula I, which means that the liquid crystal composition of Example 5 has a higher transmittance.

綜上所述，本發明液晶組成物透過具有特定結構設計的式I液晶化合物與式II及式III液晶化合物的其中一者互相配合，使得該液晶組成物具有高的穿透度，有利於後續將該液晶組成物應用於液晶顯示裝置時，使該液晶顯示裝置具有較佳的對比度，且該液晶顯示裝置能以較低的電壓達到一定的亮度而具有省電的功效，故確實能達成本發明的目的。In summary, the liquid crystal composition of the present invention cooperates with one of the liquid crystal compounds of formula II and formula III through the liquid crystal compound of formula I having a specific structural design, so that the liquid crystal composition has high transparency, which is beneficial to subsequent When the liquid crystal composition is applied to a liquid crystal display device, the liquid crystal display device has a better contrast ratio, and the liquid crystal display device can achieve a certain brightness with a lower voltage and has the effect of saving power, so the cost can indeed be achieved. purpose of the invention.

惟以上所述者，僅為本發明的實施例而已，當不能以此限定本發明實施的範圍，凡是依本發明申請專利範圍及專利說明書內容所作的簡單的等效變化與修飾，皆仍屬本發明專利涵蓋的範圍內。But the above-mentioned ones are only embodiments of the present invention, and should not limit the scope of the present invention. All simple equivalent changes and modifications made according to the patent scope of the present invention and the content of the patent specification are still within the scope of the present invention. Within the scope covered by the patent of the present invention.

Figure 110108991-A0101-11-0002-2
Figure 110108991-A0101-11-0002-2

Claims (12)

一種液晶組成物，包含： 一液晶組分，包括 式I所示的液晶化合物，及 式II及式III的其中一者所示的液晶化合物， [式I]
Figure 03_image001
[式II]
Figure 03_image003
[式III]
Figure 03_image005
； 在該式I至該式III中， 環A及環B各自獨立地表示1,4-伸環己基或1,4-伸苯基，上述基團為未經取代或環上任一位置的氫被氟所取代， 環C、環D及環E各自獨立地表示1,4-伸環己基、1,4-伸苯基、萘-2,6-二基、茚滿-1,5-二基或茚滿-2,5-二基，上述基團為未經取代或環上任一位置的氫被氟、直鏈烷基或支鏈烷基所取代，上述烷基為未經取代或至少一個－CH 2－被－O－或－C=C－所取代， Z 1表示－COO－、－OCO－、－OCH 2－、－CH 2O－、－CH 2CH 2－或單鍵， X 1及X 2各自獨立地表示C 1-C 5伸烷基，上述伸烷基為未經取代或至少一個－CH 2－被－O－所取代； R 1表示為氫或氟， R 2及R 3各自獨立地表示氫、C 1-C 12直鏈烷基、C 3-C 12支鏈烷基、C 1-C 12直鏈烷氧基、C 3-C 12支鏈烷氧基、C 2-C 12直鏈烯基、C 3-C 12支鏈烯基、C 2-C 12直鏈氧烯基或C 3-C 12支鏈氧烯基，上述烷基、烷氧基、烯基或氧烯基為未經取代， R 4表示為氫、C 1-C 12直鏈烷基、C 3-C 12支鏈烷基、C 1-C 12直鏈烷氧基、C 3-C 12支鏈烷氧基、C 2-C 12直鏈烯基、C 3-C 12支鏈烯基、C 2-C 12直鏈氧烯基或C 3-C 12支鏈氧烯基，上述烷基、烷氧基、烯基或氧烯基為未經取代或任意碳上的氫被氟所取代， R 5表示為氫、氟、氯、C 1-C 12直鏈烷基、C 3-C 12支鏈烷基、C 1-C 12直鏈烷氧基、C 3-C 12支鏈烷氧基、C 2-C 12直鏈烯基、C 3-C 12支鏈烯基、C 2-C 12直鏈氧烯基或C 3-C 12支鏈氧烯基，上述烷基、烷氧基、烯基或氧烯基為未經取代或任意碳上的氫被氟所取代， m及n分別表示0、1或2，且m與n的和為1或2，當m為2時，每個環A為相同或不同，當n為2時，每個環B為相同或不同， o表示1、2或3，當o為2或3，每個環C為相同或不同，每個Z 1為相同或不同， q表示1、2或3，當 q為2或3，每個環E為相同或不同。 A liquid crystal composition, comprising: a liquid crystal component, including a liquid crystal compound shown in formula I, and a liquid crystal compound shown in one of formula II and formula III, [formula I]
Figure 03_image001
[Formula II]
Figure 03_image003
[Formula III]
Figure 03_image005
; In the formula I to the formula III, ring A and ring B each independently represent 1,4-cyclohexyl or 1,4-phenylene, and the above-mentioned groups are unsubstituted or hydrogen at any position on the ring Substituted by fluorine, ring C, ring D and ring E each independently represent 1,4-cyclohexyl, 1,4-phenylene, naphthalene-2,6-diyl, indane-1,5-di group or indan-2,5-diyl, the above-mentioned group is unsubstituted or the hydrogen at any position on the ring is substituted by fluorine, straight-chain alkyl or branched-chain alkyl, and the above-mentioned alkyl is unsubstituted or at least One -CH 2 - is replaced by -O- or -C=C-, Z 1 represents -COO-, -OCO-, -OCH 2 -, -CH 2 O-, -CH 2 CH 2 - or a single bond, X 1 and X 2 each independently represent a C 1 -C 5 alkylene group, the above-mentioned alkylene group is unsubstituted or at least one -CH 2 - is substituted by -O-; R 1 represents hydrogen or fluorine, R 2 and R 3 each independently represent hydrogen, C 1 -C 12 straight chain alkyl, C 3 -C 12 branched chain alkyl, C 1 -C 12 straight chain alkoxy, C 3 -C 12 branched chain alkoxy , C 2 -C 12 straight chain alkenyl, C 3 -C 12 branched alkenyl, C 2 -C 12 straight chain oxyalkenyl or C 3 -C 12 branched oxyalkenyl, the above-mentioned alkyl, alkoxy , alkenyl or oxyalkenyl is unsubstituted, R 4 represents hydrogen, C 1 -C 12 straight chain alkyl, C 3 -C 12 branched chain alkyl, C 1 -C 12 straight chain alkoxy, C 3 -C 12 branched alkoxy, C 2 -C 12 straight chain alkenyl, C 3 -C 12 branched alkenyl, C 2 -C 12 straight chain oxyalkenyl or C 3 -C 12 branched chain oxyalkene The above-mentioned alkyl, alkoxy, alkenyl or oxyalkenyl is unsubstituted or hydrogen on any carbon is replaced by fluorine, R 5 represents hydrogen, fluorine, chlorine, C 1 -C 12 straight chain alkyl , C 3 -C 12 branched chain alkyl, C 1 -C 12 straight chain alkoxy, C 3 -C 12 branched alkoxy, C 2 -C 12 straight chain alkenyl, C 3 -C 12 branched chain Alkenyl, C 2 -C 12 straight chain oxyalkenyl or C 3 -C 12 branched oxyalkenyl, the above-mentioned alkyl, alkoxy, alkenyl or oxyalkenyl is unsubstituted or hydrogen on any carbon is replaced by substituted by fluorine, m and n represent 0, 1 or 2 respectively, and the sum of m and n is 1 or 2, when m is 2, each ring A is the same or different, when n is 2, each ring B is the same or different, o means 1, 2 or 3, when o is 2 or 3, each ring C is the same or different, each Z 1 is the same or different, q means 1, 2 or 3, when q is 2 or 3, each ring E is the same or different. 如請求項1所述的液晶組成物，其中，該式I液晶化合物是選自於由式I-1、式I-2及式I-3所組成的群組中至少一者： [式I-1]
Figure 03_image012
[式I-2 ]
Figure 03_image014
[式I-3 ]
Figure 03_image016
式I-1至式I-3中，該R 1、X 1及X 2表示的基團分別如請求項1所界定。 The liquid crystal composition as claimed in item 1, wherein the liquid crystal compound of formula I is at least one selected from the group consisting of formula I-1, formula I-2 and formula I-3: [Formula I -1]
Figure 03_image012
[Formula I-2]
Figure 03_image014
[Formula I-3]
Figure 03_image016
In formula I-1 to formula I-3, the groups represented by R 1 , X 1 and X 2 are as defined in Claim 1, respectively. 如請求項1或2所述的液晶組成物，其中，該X 1及X 2各自獨立地表示C 1-C 5伸烷基，上述伸烷基為未經取代。 The liquid crystal composition according to claim 1 or 2, wherein X 1 and X 2 each independently represent a C 1 -C 5 alkylene group, and the above alkylene group is unsubstituted. 如請求項1所述的液晶組成物，其中，該式II液晶化合物是選自於由式II-1、式II-2、式II-3、式II-4、式II-5及式II-6所組成的群組中至少一者： [式II-1]
Figure 03_image044
[式II-2]
Figure 03_image046
[式II-3]
Figure 03_image048
[式II-4]
Figure 03_image050
[式II-5]
Figure 03_image052
[式II-6]
Figure 03_image054
式II-1至式II-6中，R 2及R 3表示的基團分別如請求項1所界定。 The liquid crystal composition as claimed in item 1, wherein the liquid crystal compound of formula II is selected from formula II-1, formula II-2, formula II-3, formula II-4, formula II-5 and formula II - At least one member of the group consisting of 6: [Formula II-1]
Figure 03_image044
[Formula II-2]
Figure 03_image046
[Formula II-3]
Figure 03_image048
[Formula II-4]
Figure 03_image050
[Formula II-5]
Figure 03_image052
[Formula II-6]
Figure 03_image054
In formula II-1 to formula II-6, the groups represented by R 2 and R 3 are as defined in Claim 1, respectively. 如請求項1或4所述的液晶組成物，其中，該R 2及R 3各自獨立地表示C 1-C 12直鏈烷基或C 1-C 12直鏈烷氧基，上述烷基或烷氧基為未經取代。 The liquid crystal composition according to claim 1 or 4, wherein, the R 2 and R 3 each independently represent a C 1 -C 12 straight chain alkyl group or a C 1 -C 12 straight chain alkoxy group, the above-mentioned alkyl group or Alkoxy is unsubstituted. 如請求項1所述的液晶組成物，其中，該式III液晶化合物是選自於由式III-1、式III-2、式III-3、式III-4及式III-5所組成的群組中至少一者： [式III-1]
Figure 03_image088
[式III-2]
Figure 03_image090
[式III-3]
Figure 03_image092
[式III-4]
Figure 03_image094
[式III-5]
Figure 03_image096
式III-1至式III-5中，該R 4及R 5表示的基團分別如請求項1所界定。 The liquid crystal composition as claimed in item 1, wherein the liquid crystal compound of formula III is selected from the group consisting of formula III-1, formula III-2, formula III-3, formula III-4 and formula III-5 At least one of the group: [Formula III-1]
Figure 03_image088
[Formula III-2]
Figure 03_image090
[Formula III-3]
Figure 03_image092
[Formula III-4]
Figure 03_image094
[Formula III-5]
Figure 03_image096
In formula III-1 to formula III-5, the groups represented by R 4 and R 5 are as defined in Claim 1, respectively. 如請求項1或6所述的液晶組成物，其中，該R 4表示C 1-C 12直鏈烷基，上述烷基為未經取代，該R 5表示氟。 The liquid crystal composition according to claim 1 or 6, wherein, the R 4 represents a C 1 -C 12 linear alkyl group, the above-mentioned alkyl group is unsubstituted, and the R 5 represents fluorine. 如請求項1所述的液晶組成物，該液晶組分還包括式IV所示的液晶化合物 [式IV]
Figure 03_image122
式IV中， 環F及環G各自獨立地表示1,4-伸環己基或1,4-伸苯基，上述基團為未經取代， R 6表示C 1-C 5直鏈烷基、C 1-C 5直鏈烷氧基或C 2-C 5直鏈烯基，上述烷基、烷氧基或烯基為未經取代， R 7表示氟、C 1-C 5直鏈烷基、C 3-C 5支鏈烷基、C 1-C 5直鏈烷氧基、C 3-C 5支鏈烷氧基或C 2-C 5直鏈烯基，上述烷基、烷氧基或烯基為未經取代， Z 2表示－COO－、－OCO－、－OCH 2－、－CH 2O－、－CH＝CH－、－C≡C－、－CH 2CH 2－或單鍵； r表示1或2。 The liquid crystal composition as described in claim item 1, the liquid crystal component also includes a liquid crystal compound shown in formula IV [formula IV]
Figure 03_image122
In formula IV, ring F and ring G each independently represent 1,4-cyclohexylene or 1,4-phenylene, and the above groups are unsubstituted, R 6 represents C 1 -C 5 linear alkyl, C 1 -C 5 straight chain alkoxy or C 2 -C 5 straight chain alkenyl, the above-mentioned alkyl, alkoxy or alkenyl is unsubstituted, R 7 represents fluorine, C 1 -C 5 straight chain alkyl , C 3 -C 5 branched chain alkyl, C 1 -C 5 straight chain alkoxy, C 3 -C 5 branched alkoxy or C 2 -C 5 straight chain alkenyl, the above-mentioned alkyl, alkoxy Or alkenyl is unsubstituted, Z 2 represents -COO-, -OCO-, -OCH 2 -, -CH 2 O-, -CH=CH-, -C≡C-, -CH 2 CH 2 - or a single key; r means 1 or 2. 如請求項8所述的液晶組成物，其中，該式IV液晶化合物是選自於由式IV-1、式IV-2、式IV-3、式IV-4、式IV-5及式IV-6所組成的群組中至少一者： [式IV-1]
Figure 03_image124
[式IV-2]
Figure 03_image126
[式IV-3]
Figure 03_image128
[式IV-4]
Figure 03_image130
[式IV-5]
Figure 03_image132
[式IV-6]
Figure 03_image134
式IV-1至式IV-6中，R 6表示C 1-C 5直鏈烷基、C 1-C 5直鏈烷氧基或C 2-C 5直鏈烯基，上述烷基、烷氧基或烯基為未經取代， R 7表示氟、C 1-C 5直鏈烷基、C 1-C 5直鏈烷氧基或C 2-C 5直鏈烯基，上述烷基、烷氧基或烯基為未經取代。 The liquid crystal composition as described in Claim 8, wherein the liquid crystal compound of formula IV is selected from formula IV-1, formula IV-2, formula IV-3, formula IV-4, formula IV-5 and formula IV -At least one member of the group consisting of 6: [Formula IV-1]
Figure 03_image124
[Formula IV-2]
Figure 03_image126
[Formula IV-3]
Figure 03_image128
[Formula IV-4]
Figure 03_image130
[Formula IV-5]
Figure 03_image132
[Formula IV-6]
Figure 03_image134
In formula IV-1 to formula IV-6, R 6 represents C 1 -C 5 straight chain alkyl, C 1 -C 5 straight chain alkoxy or C 2 -C 5 straight chain alkenyl, the above-mentioned alkyl, alkane Oxygen or alkenyl is unsubstituted, R 7 represents fluorine, C 1 -C 5 straight chain alkyl, C 1 -C 5 straight chain alkoxy or C 2 -C 5 straight chain alkenyl, the above-mentioned alkyl, Alkoxy or alkenyl is unsubstituted. 如請求項1所述的液晶組成物，該液晶組分還包括式V所示的液晶化合物 [式V]
Figure 03_image176
式V中， 環J及環I各自獨立地表示1,4-伸環己基、1,4-伸苯基、萘-2,6-二基、茚滿-1,5-二基或茚滿-2,5-二基，上述基團為未經取代或環上任一位置的氫被氟所取代， R 8表示為氫、C 1-C 12直鏈烷基、C 3-C 12支鏈烷基、C 1-C 12直鏈烷氧基、C 3-C 12支鏈烷氧基、C 2-C 12直鏈烯基、C 3-C 12支鏈烯基、C 2-C 12直鏈氧烯基或C 3-C 12支鏈氧烯基，上述烷基、烷氧基、烯基或氧烯基為未經取代或任意碳上的氫被氟所取代， s表示1或2，當s為2，每個環I為相同或不同。 The liquid crystal composition as described in claim item 1, the liquid crystal component also includes a liquid crystal compound shown in formula V [formula V]
Figure 03_image176
In formula V, ring J and ring I each independently represent 1,4-cyclohexylene, 1,4-phenylene, naphthalene-2,6-diyl, indan-1,5-diyl or indane -2,5-diyl, the above group is unsubstituted or the hydrogen at any position on the ring is replaced by fluorine, R 8 represents hydrogen, C 1 -C 12 straight chain alkyl, C 3 -C 12 branched chain Alkyl, C 1 -C 12 straight chain alkoxy, C 3 -C 12 branched alkoxy, C 2 -C 12 straight chain alkenyl, C 3 -C 12 branched alkenyl, C 2 -C 12 Straight-chain oxyalkenyl or C 3 -C 12 branched oxyalkenyl, the above-mentioned alkyl, alkoxy, alkenyl or oxyalkenyl is unsubstituted or hydrogen on any carbon is replaced by fluorine, s represents 1 or 2. When s is 2, each ring I is the same or different. 如請求項1所述的液晶組成物，還包含一添加劑，該添加劑包括式VI所示的化合物 [式VI]
Figure 03_image186
在該式VI中， 環K表示1,4-伸苯基或茚滿-2,5-二基，上述基團為未經取代或環上任一位置的氫被氟所取代， Z 3表示－OCH 2－、－CH 2O－、－CH 2CH 2－或單鍵， t及u分別表示1或2，且t與u的總和為2、3或4，當u為2時，每個環K為相同或不同。 The liquid crystal composition as described in claim item 1, also comprises an additive, and this additive comprises the compound shown in formula VI [formula VI]
Figure 03_image186
In the formula VI, ring K represents 1,4-phenylene or indan-2,5-diyl, and the above-mentioned groups are unsubstituted or hydrogen at any position on the ring is substituted by fluorine, Z 3 represents- OCH 2 -, -CH 2 O-, -CH 2 CH 2 - or single bond, t and u represent 1 or 2 respectively, and the sum of t and u is 2, 3 or 4, when u is 2, each Ring K is the same or different. 一種液晶顯示裝置，包含如請求項1至11中任一項所述的液晶組成物。A liquid crystal display device, comprising the liquid crystal composition according to any one of claims 1 to 11.
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