WO2015072243A1 - 液晶組成物および液晶表示素子 - Google Patents
液晶組成物および液晶表示素子 Download PDFInfo
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- WO2015072243A1 WO2015072243A1 PCT/JP2014/076527 JP2014076527W WO2015072243A1 WO 2015072243 A1 WO2015072243 A1 WO 2015072243A1 JP 2014076527 W JP2014076527 W JP 2014076527W WO 2015072243 A1 WO2015072243 A1 WO 2015072243A1
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- carbons
- liquid crystal
- hydrogen
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- 0 CCCC1CCC(*c2ccc(*(C)C3(C)SC3)cc2)CC1 Chemical compound CCCC1CCC(*c2ccc(*(C)C3(C)SC3)cc2)CC1 0.000 description 5
- YEJCHVFCLNKZPU-UHFFFAOYSA-N CC1COC(C)CC1 Chemical compound CC1COC(C)CC1 YEJCHVFCLNKZPU-UHFFFAOYSA-N 0.000 description 3
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Definitions
- the present invention relates to a liquid crystal composition, a liquid crystal display element containing the composition, and the like.
- the present invention relates to a liquid crystal composition having a negative dielectric anisotropy and a liquid crystal display element containing the composition and having a mode such as IPS, VA, FFS, and FPA.
- the present invention also relates to a polymer-supported alignment type liquid crystal display element.
- the classification based on the operation mode of the liquid crystal molecules is as follows: PC (phase change), TN (twisted nematic), STN (super twisted nematic), ECB (electrically controlled birefringence), OCB (optically compensated bend), IPS. (In-plane switching), VA (vertical alignment), FFS (Fringe field Switching), FPA (field-induced photo-reactive alignment), etc.
- the classification based on the element drive system is PM (passive matrix) and AM (active matrix). PM is classified into static, multiplex, etc., and AM is classified into TFT (thin film insulator), MIM (metal film insulator), and the like. TFTs are classified into amorphous silicon and polycrystalline silicon. The latter is classified into a high temperature type and a low temperature type according to the manufacturing process.
- the classification based on the light source includes a reflection type using natural light, a transmission type using backlight, and a semi-transmission type using both natural light and backlight.
- the liquid crystal display element contains a liquid crystal composition having a nematic phase.
- This composition has suitable properties. By improving the characteristics of the composition, an AM device having good characteristics can be obtained. The relationship between the two characteristics is summarized in Table 1 below. The characteristics of the composition will be further described based on a commercially available AM device.
- the temperature range of the nematic phase is related to the temperature range in which the device can be used.
- a preferred upper limit temperature of the nematic phase is about 70 ° C. or more, and a preferred lower limit temperature of the nematic phase is about ⁇ 10 ° C. or less.
- the viscosity of the composition is related to the response time of the device. A short response time is preferred for displaying moving images on the device. A shorter response time is desirable even at 1 millisecond. Therefore, a small viscosity in the composition is preferred. Small viscosities at low temperatures are more preferred.
- the optical anisotropy of the composition is related to the contrast ratio of the device. Depending on the mode of the device, a large optical anisotropy or a small optical anisotropy, ie an appropriate optical anisotropy is required.
- the product ( ⁇ n ⁇ d) of the optical anisotropy ( ⁇ n) of the composition and the cell gap (d) of the device is designed to maximize the contrast ratio.
- the appropriate product value depends on the type of operation mode. This value is in the range of about 0.30 ⁇ m to about 0.40 ⁇ m for the VA mode element and in the range of about 0.20 ⁇ m to about 0.30 ⁇ m for the IPS mode or FFS mode element.
- a composition having a large optical anisotropy is preferable for a device having a small cell gap.
- a large dielectric anisotropy in the composition contributes to a low threshold voltage, a small power consumption and a large contrast ratio in the device. Therefore, a large dielectric anisotropy is preferable.
- a large specific resistance in the composition contributes to a large voltage holding ratio and a large contrast ratio in the device. Therefore, a composition having a large specific resistance not only at room temperature but also at a high temperature in the initial stage is preferable.
- a composition having a large specific resistance not only at room temperature but also at a high temperature after being used for a long time is preferable.
- the stability of the composition to ultraviolet light and heat is related to the lifetime of the device. When this stability is high, the lifetime of the device is long. Such characteristics are preferable for an AM device used in a liquid crystal projector, a liquid crystal television, and the like.
- a liquid crystal composition containing a polymer is used.
- a composition to which a small amount of a polymerizable compound is added is injected into the device.
- the composition is irradiated with ultraviolet rays while applying a voltage between the substrates of the device.
- the polymerizable compound polymerizes to form a polymer network in the composition.
- the response time of the device is shortened, and image burn-in is improved.
- Such an effect of the polymer can be expected for a device having modes such as TN, ECB, OCB, IPS, VA, FFS, and FPA.
- a composition having a positive dielectric anisotropy is used for an AM device having a TN mode.
- a composition having a negative dielectric anisotropy is used in an AM device having a VA mode.
- a composition having a positive or negative dielectric anisotropy is used in an AM device having an IPS mode or an FFS mode.
- a composition having a positive or negative dielectric anisotropy is used in an AM device having an IPS mode or an FFS mode.
- a composition having a positive or negative dielectric anisotropy is used in a polymer-supported alignment (PSA) type AM device.
- PSA polymer-supported alignment
- An example of a liquid crystal composition having negative dielectric anisotropy is disclosed in the following Patent Document 1.
- One object of the present invention is to provide a high maximum temperature of the nematic phase, a low minimum temperature of the nematic phase, a small viscosity, a suitable optical anisotropy, a large negative dielectric anisotropy, a large specific resistance, and a high stability to ultraviolet light.
- the liquid crystal composition satisfies at least one characteristic in characteristics such as high stability to heat.
- Another object is a liquid crystal composition having an appropriate balance between at least two properties.
- Another object is a liquid crystal display device containing such a composition.
- Another object is an AM device having characteristics such as a short response time, a large voltage holding ratio, a low threshold voltage, a large contrast ratio, and a long lifetime.
- the present invention includes a liquid crystal composition containing at least one compound selected from the group of compounds represented by formula (1) and having a negative dielectric anisotropy, and a liquid crystal display containing the composition It is an element.
- R 1 is alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, alkenyl having 2 to 12 carbons, or C 2 to 12 having at least one hydrogen replaced with fluorine.
- A is an integer of 0-12.
- the advantages of the present invention are that the upper limit temperature of the nematic phase, the lower limit temperature of the nematic phase, the small viscosity, the appropriate optical anisotropy, the negative dielectric constant anisotropy, the large specific resistance, the high stability to ultraviolet rays, the heat It is a liquid crystal composition satisfying at least one of the properties such as high stability against the liquid crystal. Another advantage is a liquid crystal composition having an appropriate balance between at least two properties. Another advantage is a liquid crystal display device containing such a composition. Another advantage is an AM device having characteristics such as a short response time, a large voltage holding ratio, a low threshold voltage, a large contrast ratio, and a long lifetime.
- liquid crystal composition and “liquid crystal display element” may be abbreviated as “composition” and “element”, respectively.
- a liquid crystal display element is a general term for a liquid crystal display panel and a liquid crystal display module.
- a liquid crystalline compound is a compound having a liquid crystal phase such as a nematic phase and a smectic phase, and does not have a liquid crystal phase.
- a generic term for compounds to be mixed. This compound has a six-membered ring such as 1,4-cyclohexylene and 1,4-phenylene, and its molecular structure is rod-like.
- the polymerizable compound is a compound added for the purpose of forming a polymer in the composition.
- the liquid crystal composition is prepared by mixing a plurality of liquid crystal compounds.
- the ratio (content) of the liquid crystal compound is expressed as a percentage by weight (% by weight) based on the weight of the liquid crystal composition.
- additives such as an optically active compound, an antioxidant, an ultraviolet absorber, a dye, an antifoaming agent, a polymerizable compound, a polymerization initiator, and a polymerization inhibitor are added to the composition.
- the ratio (addition amount) of the additive is represented by a weight percentage (% by weight) based on the weight of the liquid crystal composition, similarly to the ratio of the liquid crystal compound. Weight parts per million (ppm) may be used.
- the ratio of the polymerization initiator and the polymerization inhibitor is exceptionally expressed based on the weight of the polymerizable compound.
- the upper limit temperature of the nematic phase may be abbreviated as “the upper limit temperature”.
- “Lower limit temperature of nematic phase” may be abbreviated as “lower limit temperature”.
- High specific resistance means that the composition has a large specific resistance not only at room temperature in the initial stage but also at a temperature close to the upper limit temperature of the nematic phase. It means having a large specific resistance even at a close temperature.
- High voltage holding ratio means that the device has a large voltage holding ratio not only at room temperature in the initial stage but also at a temperature close to the upper limit temperature of the nematic phase. It means having a large voltage holding ratio even at a temperature close to.
- increasing dielectric anisotropy means that when the composition has a positive dielectric anisotropy, the value increases positively, and the composition having a negative dielectric anisotropy When it is a thing, it means that the value increases negatively.
- the expression“ at least one ‘A’ may be replaced by ‘B’ ” means that the number of‘ A ’is arbitrary. When the number of ‘A’ is one, the position of ‘A’ is arbitrary, and when the number of ‘A’ is two or more, the positions can be selected without limitation. This rule also applies to the expression “at least one 'A' is replaced by 'B'”.
- the compound represented by Formula (1) may be abbreviated as Compound (1).
- This abbreviation also applies to compounds represented by formula (2) and the like.
- Compound (1) means one compound or two or more compounds represented by formula (1).
- the symbol of the terminal group R 2 is used for a plurality of compounds.
- two groups represented by any two R 2 may be the same or different.
- R 2 of the compound (2-1) is ethyl
- R 2 of compound (2-1) is ethyl
- R 2 of compound (2-1) is ethyl
- R 2 of compound (2-1) is ethyl
- R 2 of compound (2-2) is propyl.
- This rule also applies to symbols such as other end groups.
- when b is 2 there are two rings A.
- the two rings represented by the two rings A may be the same or different.
- This rule also applies to any two rings A when b is greater than 2.
- This rule also applies to symbols such as Z 1 and ring D.
- 2-Fluoro-1,4-phenylene means the following two divalent groups.
- fluorine may be leftward (L) or rightward (R). This rule also applies to asymmetric ring divalent groups such as tetrahydropyran-2,5-diyl.
- the present invention includes the following items.
- Item 1 A liquid crystal composition containing at least one compound selected from the group of compounds represented by formula (1) as a first component and having negative dielectric anisotropy.
- R 1 is alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, alkenyl having 2 to 12 carbons, or C 2 to 12 having at least one hydrogen replaced with fluorine.
- A is an integer of 0-12.
- Item 2. The liquid crystal composition according to item 1, wherein the ratio of the first component is in the range of 3% by weight to 30% by weight based on the weight of the liquid crystal composition.
- Item 3. The liquid crystal composition according to item 1 or 2, containing at least one compound selected from the group of compounds represented by formula (2) as the second component.
- R 2 and R 3 are independently alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, alkenyl having 2 to 12 carbons, alkenyloxy having 2 to 12 carbons, 1 to 12 alkyls in which one hydrogen is replaced by fluorine, or alkenyls having 2 to 12 carbons in which at least one hydrogen is replaced by fluorine;
- ring A and ring C are independently 1, 4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, 1,4-phenylene in which at least one hydrogen is replaced by fluorine or chlorine, or tetrahydropyran-2,5-diyl;
- Ring B is 2,3-difluoro-1,4-phenylene, 2-chloro-3-fluoro-1,4-phenylene, 2,3-difluoro-5 Me
- Item 4. The liquid crystal composition according to any one of items 1 to 3, comprising at least one compound selected from the group of compounds represented by formulas (2-1) to (2-11) as a second component: object.
- R 2 and R 3 are independently alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, alkenyl having 2 to 12 carbons, carbon The alkenyloxy having 2 to 12 carbon atoms, alkyl having 1 to 12 carbon atoms in which at least one hydrogen is replaced with fluorine, or alkenyl having 2 to 12 carbon atoms in which at least one hydrogen is replaced with fluorine.
- Item 5 The liquid crystal composition according to item 3 or 4, wherein the ratio of the second component is in the range of 5% by weight to 70% by weight based on the weight of the liquid crystal composition.
- Item 6. The liquid crystal composition according to any one of items 1 to 5, further containing at least one compound selected from the group of compounds represented by formula (3) as a third component.
- R 4 and R 5 are independently alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, alkenyl having 2 to 12 carbons, and at least one hydrogen is replaced by fluorine.
- ring D, ring E, and ring F are each independently 1,4-cyclohexylene , 1,4-phenylene, 2-fluoro-1,4-phenylene, or 2,5-difluoro-1,4-phenylene;
- Z 1 and Z 2 are independently a single bond, —CH 2 CH 2 —, —CH 2 O—, —OCH 2 —, —COO—, or —OCO—;
- d is 0, 1, or 2; where d is 1, ring E is 1,4-Cyclohexyl , 2-fluoro-1,4-phenylene or 2,5-difluoro-1,4-phenylene.
- Item 7. The liquid crystal composition according to any one of items 1 to 6, comprising at least one compound selected from the group of compounds represented by formulas (3-1) to (3-12) as a third component: object.
- R 4 and R 5 are independently alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, alkenyl having 2 to 12 carbons, It is alkyl having 1 to 12 carbons in which one hydrogen is replaced with fluorine, or alkenyl having 2 to 12 carbons in which at least one hydrogen is replaced with fluorine.
- Item 8 The liquid crystal composition according to item 6 or 7, wherein the ratio of the third component is in the range of 10% by weight to 90% by weight based on the weight of the liquid crystal composition.
- Item 9 The liquid crystal composition according to any one of items 1 to 8, comprising at least one compound selected from the group of compounds represented by formula (4) as a fourth component.
- R 6 and R 7 are independently alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, alkenyl having 2 to 12 carbons, alkenyloxy having 2 to 12 carbons, An alkyl having 1 to 12 carbons in which one hydrogen is replaced by fluorine, or an alkenyl having 2 to 12 carbons in which at least one hydrogen is replaced by fluorine;
- ring G and ring J are independently 1, 4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, 1,4-phenylene in which at least one hydrogen is replaced by fluorine or chlorine, or tetrahydropyran-2,5-diyl; Ring I is 2,3-difluoro-1,4-phenylene, 2-chloro-3-fluoro-1,4-phenylene, 2,
- Item 10 The liquid crystal composition according to any one of items 1 to 9, comprising at least one compound selected from the group of compounds represented by formulas (4-1) to (4-8) as a fourth component: object.
- R 6 and R 7 are independently alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, alkenyl having 2 to 12 carbons, carbon The alkenyloxy having 2 to 12 carbon atoms, alkyl having 1 to 12 carbon atoms in which at least one hydrogen is replaced with fluorine, or alkenyl having 2 to 12 carbon atoms in which at least one hydrogen is replaced with fluorine.
- Item 11 The liquid crystal composition according to item 9 or 10, wherein the ratio of the fourth component is in the range of 5% by weight to 60% by weight based on the weight of the liquid crystal composition.
- Item 12. The liquid crystal composition according to any one of items 1 to 11, comprising at least one polymerizable compound selected from the group of compounds represented by formula (5) as an additive component.
- ring K and ring M are independently cyclohexyl, cyclohexenyl, phenyl, 1-naphthyl, 2-naphthyl, tetrahydropyran-2-yl, 1,3-dioxane-2-yl, pyrimidine- 2-yl or pyridin-2-yl, in which at least one hydrogen is halogen, alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, or at least one hydrogen being halogen.
- ring L is 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, naphthalene-1,2-diyl Naphthalene-1,3-diyl, naphthalene-1,4-diyl, naphthalene-1,5-diyl, naphthalene-1,6-diyl, Phthalene-1,7-diyl, naphthalene-1,8-diyl, naphthalene-2,3-diyl, naphthalene-2,6-diyl, naphthalene-2,7-diyl, tetrahydropyran-2,5-diyl, , 3-dioxane-2,5-diyl, pyrimidine-2,5-diyl, or pyridine-2,5-diyl, in
- At least one hydrogen may be replaced with fluorine or chlorine; g is 0, 1, or 2; h, j, and k are independently 0, 1, 2, 3, or 4; And the sum of h, j, and k is 1 or greater.
- P 1 , P 2 and P 3 are each independently selected from the group of groups represented by formula (P-1) to formula (P-6) Item 13.
- M 1 , M 2 , and M 3 are independently hydrogen, fluorine, alkyl having 1 to 5 carbons, or at least one hydrogen is replaced by halogen
- at least one of Sp 1 and Sp 3 Is alkylene in which at least one —CH 2 — is replaced by —O—, —COO—, —OCO—, or —OCOO—.
- Item 14 The item according to any one of Items 1 to 13, comprising at least one polymerizable compound selected from the group of compounds represented by formula (5-1) to formula (5-27) as an additive component: Liquid crystal composition.
- P 4 , P 5 , and P 6 are independently from the group of groups represented by formula (P-1) to formula (P-3).
- M 1 , M 2 , and M 3 are independently hydrogen, fluorine, alkyl having 1 to 5 carbons, or at least one hydrogen is replaced by halogen
- Sp 1 , Sp 2 , and Sp 3 are independently a single bond or a carbon number of 1 to 10 In which at least one —CH 2 — may be replaced by —O—, —COO—, —OCO—, or —OCOO—, and at least one —CH 2 —CH 2 — May be replaced with —CH ⁇ CH— or —C ⁇ C—, in which at least one hydrogen may be replaced with fluorine or chlorine.
- Item 15 The liquid crystal composition according to any one of items 12 to 14, wherein the addition ratio of the additive component is in the range of 0.03% to 10% by weight based on the weight of the liquid crystal composition.
- Item 16 A liquid crystal display device comprising the liquid crystal composition according to any one of items 1 to 15.
- Item 17. The liquid crystal display element according to item 16, wherein the operation mode of the liquid crystal display element is an IPS mode, a VA mode, an FFS mode, or an FPA mode, and the driving method of the liquid crystal display element is an active matrix method.
- Item 18 A polymer-supported alignment type liquid crystal display device comprising the liquid crystal composition according to any one of items 12 to 15, wherein a polymerizable compound in the liquid crystal composition is polymerized.
- Item 19 Use of the liquid crystal composition according to any one of items 1 to 15 in a liquid crystal display device.
- Item 20 Use of the liquid crystal composition according to any one of items 12 to 15 in a polymer-supported alignment type liquid crystal display element.
- the present invention includes the following items.
- the above composition further containing at least one of additives such as an optically active compound, an antioxidant, an ultraviolet absorber, a dye, an antifoaming agent, a polymerizable compound, a polymerization initiator, and a polymerization inhibitor.
- additives such as an optically active compound, an antioxidant, an ultraviolet absorber, a dye, an antifoaming agent, a polymerizable compound, a polymerization initiator, and a polymerization inhibitor.
- B An AM device containing the above composition.
- PSA polymer-supported orientation type AM device comprising the above-described composition, wherein the polymerizable compound in the composition is polymerized.
- (E) A device containing the above composition and having a mode of PC, TN, STN, ECB, OCB, IPS, VA, FFS, or FPA.
- (F) A transmissive device containing the above composition.
- (G) Use of the above composition as a composition having a nematic phase.
- (H) Use as an optically active composition by adding an optically active compound to the above composition.
- composition of the present invention will be described in the following order. First, the constitution of component compounds in the composition will be described. Second, the main characteristics of the component compounds and the main effects of the compounds on the composition will be explained. Third, the combination of components in the composition, the preferred ratio of the components, and the basis thereof will be described. Fourth, a preferred form of the component compound will be described. Fifth, preferred component compounds are shown. Sixth, additives that may be added to the composition will be described. Seventh, a method for synthesizing the component compounds will be described. Finally, the use of the composition will be described.
- composition A further includes other liquid crystal compounds, additives, and the like. You may contain.
- the “other liquid crystal compound” is a liquid crystal compound different from the compound (1), the compound (2), the compound (3), and the compound (4). Such compounds are mixed into the composition for the purpose of further adjusting the properties.
- Additives include optically active compounds, antioxidants, ultraviolet absorbers, dyes, antifoaming agents, polymerizable compounds, polymerization initiators, polymerization inhibitors, and the like.
- Composition B consists essentially of a compound selected from compound (1), compound (2), compound (3), compound (4), and compound (5). “Substantially” means that the composition may contain an additive but no other liquid crystal compound. Composition B has fewer components than composition A. From the viewpoint of reducing the cost, the composition B is preferable to the composition A. The composition A is preferable to the composition B from the viewpoint that the characteristics can be further adjusted by mixing other liquid crystal compounds.
- the main characteristics of the component compounds and the main effects of the compounds on the characteristics of the composition will be explained.
- the main characteristics of the component compounds are summarized in Table 2 based on the effects of the present invention.
- L means large or high
- M means moderate
- S means small or low.
- L, M, and S are classifications based on a qualitative comparison among the component compounds, and 0 (zero) means that the value is zero or close to zero.
- Compound (1) increases the maximum temperature and decreases the minimum temperature.
- Compound (2) increases the dielectric anisotropy and decreases the minimum temperature.
- Compound (3) decreases the viscosity or increases the maximum temperature.
- Compound (4) increases the dielectric anisotropy and decreases the minimum temperature.
- Compound (5) gives a polymer by polymerization, and this polymer shortens the response time of the device and improves image burn-in.
- first component + second component first component + third component, first component + fourth component, first component + additive component, first component + second component + first component
- first component + second component + additive component first component + third component + fourth component
- first component + third component + additive component first component + additive component
- First component + fourth component + additive component first component + second component + third component + fourth component
- first component + second component + third component + additive component first component + second component + third component + additive component
- second component + third component + additive component first component + first component + first component
- Two components + fourth component + additive component first component + third component + fourth component + additive component, or first component + second component + third component + fourth component + additive component.
- Further preferred combinations are first component + second component + third component, first component + second component + third component + fourth component, first component + second component + third component + additive component, or First component + second component + third component + fourth component + additive component.
- a desirable ratio of the first component is approximately 3% by weight or more for increasing the maximum temperature, and approximately 30% by weight or less for decreasing the minimum temperature.
- a more desirable ratio is in the range of approximately 5% by weight to approximately 25% by weight.
- a particularly preferred ratio is in the range of approximately 5% by weight to approximately 20% by weight.
- a desirable ratio of the second component is approximately 5% by weight or more for increasing the dielectric anisotropy, and approximately 70% by weight or less for decreasing the minimum temperature.
- a more desirable ratio is in the range of approximately 10% by weight to approximately 65% by weight.
- a particularly preferred ratio is in the range of approximately 15% by weight to approximately 60% by weight.
- a desirable ratio of the third component is approximately 10% by weight or more for increasing the maximum temperature or decreasing the viscosity, and approximately 90% by weight or less for increasing the dielectric anisotropy.
- a more desirable ratio is in the range of approximately 20% by weight to approximately 80% by weight.
- a particularly desirable ratio is in the range of approximately 30% by weight to approximately 70% by weight.
- a desirable ratio of the fourth component is approximately 5% by weight or more for increasing the dielectric anisotropy, and approximately 60% by weight or less for decreasing the minimum temperature.
- a more desirable ratio is in the range of approximately 10% by weight to approximately 50% by weight.
- a particularly preferred ratio is in the range of approximately 10% by weight to approximately 40% by weight.
- Compound (5) is added to the composition for the purpose of adapting to a polymer-supported orientation type device.
- a preferable addition ratio of this additive is about 0.03% by weight or more for aligning liquid crystal molecules based on the weight of the liquid crystal composition, and about 10% by weight or less for preventing display defects of the device.
- a more preferred addition ratio is in the range of approximately 0.1% by weight to approximately 2% by weight.
- a particularly preferred addition ratio is in the range of about 0.2% by weight to about 1.0% by weight.
- R 1 is alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, alkenyl having 2 to 12 carbons, Or alkenyl having 2 to 12 carbon atoms in which at least one hydrogen is replaced by fluorine. Desirable R 1 is alkyl having 1 to 12 carbons for increasing the stability.
- R 2 , R 3 , R 6 , and R 7 are independently alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, alkenyl having 2 to 12 carbons, alkenyloxy having 2 to 12 carbons, It is alkyl having 1 to 12 carbons in which at least one hydrogen is replaced with fluorine, or alkenyl having 2 to 12 carbons in which at least one hydrogen is replaced with fluorine.
- Desirable R 2 , R 3 , R 6 , or R 7 is alkyl having 1 to 12 carbons for increasing the stability, and alkoxy having 1 to 12 carbons for increasing the dielectric anisotropy.
- R 4 and R 5 are independently alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, alkenyl having 2 to 12 carbons, or 1 to 12 carbons in which at least one hydrogen is replaced by fluorine. Alkyl or alkenyl having 2 to 12 carbons in which at least one hydrogen is replaced by fluorine. Desirable R 4 or R 5 is alkenyl having 2 to 12 carbons for decreasing the viscosity, and alkyl having 1 to 12 carbons for increasing the stability.
- Preferred alkyl is methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl or octyl. More desirable alkyl is ethyl, propyl, butyl, pentyl, or heptyl for decreasing the viscosity.
- alkyl in which at least one hydrogen is replaced by fluorine are fluoromethyl, 2-fluoroethyl, 3-fluoropropyl, 4-fluorobutyl, 5-fluoropentyl, 6-fluorohexyl, 7-fluoroheptyl, or 8-Fluorooctyl. Further preferred examples are 2-fluoroethyl, 3-fluoropropyl, 4-fluorobutyl or 5-fluoropentyl for increasing the dielectric anisotropy.
- Preferred alkoxy is methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy, or heptyloxy. More desirable alkoxy is methoxy or ethoxy for decreasing the viscosity.
- Preferred alkenyl is vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, or 5-hexenyl. More desirable alkenyl is vinyl, 1-propenyl, 3-butenyl, or 3-pentenyl for decreasing the viscosity.
- the preferred configuration of —CH ⁇ CH— in these alkenyls depends on the position of the double bond.
- Trans is preferable in alkenyl such as 1-propenyl, 1-butenyl, 1-pentenyl, 1-hexenyl, 3-pentenyl and 3-hexenyl for decreasing the viscosity.
- Cis is preferred for alkenyl such as 2-butenyl, 2-pentenyl, and 2-hexenyl.
- linear alkenyl is preferable to branching.
- Preferred alkenyloxy is vinyloxy, allyloxy, 3-butenyloxy, 3-pentenyloxy, or 4-pentenyloxy. More preferable alkenyloxy is allyloxy or 3-butenyloxy for decreasing the viscosity.
- alkenyl in which at least one hydrogen is replaced by fluorine are 2,2-difluorovinyl, 3,3-difluoro-2-propenyl, 4,4-difluoro-3-butenyl, 5,5-difluoro-4 -Pentenyl, or 6,6-difluoro-5-hexenyl. Further preferred examples are 2,2-difluorovinyl or 4,4-difluoro-3-butenyl for decreasing the viscosity.
- Ring A, Ring C, Ring G, and Ring J are independently 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, at least one hydrogen is replaced by fluorine or chlorine 1,4-phenylene or tetrahydropyran-2,5-diyl.
- Preferred examples of “1,4-phenylene in which at least one hydrogen is replaced by fluorine or chlorine” are 2-fluoro-1,4-phenylene, 2,3-difluoro-1,4-phenylene or 2-chloro- 3-fluoro-1,4-phenylene.
- Preferred ring A, ring C, ring G or ring J is 1,4-cyclohexylene for decreasing the viscosity, tetrahydropyran-2,5-diyl for increasing the dielectric anisotropy, and optical 1,4-phenylene for increasing anisotropy.
- trans is preferable to cis for increasing the maximum temperature.
- Tetrahydropyran-2,5-diyl is
- Ring B and Ring I are independently 2,3-difluoro-1,4-phenylene, 2-chloro-3-fluoro-1,4-phenylene, 2,3-difluoro-5-methyl-1,4- Phenylene, 3,4,5-trifluoronaphthalene-2,6-diyl, or 7,8-difluorochroman-2,6-diyl.
- Preferred ring B or ring I is 2,3-difluoro-1,4-phenylene for decreasing the viscosity, and 2-chloro-3-fluoro-1,4-phenylene for decreasing the optical anisotropy. In order to increase the dielectric anisotropy, it is 7,8-difluorochroman-2,6-diyl.
- Ring D, Ring E, and Ring F are independently 1,4-cyclohexylene, 1,4-phenylene, 2-fluoro-1,4-phenylene, or 2,5-difluoro-1,4-phenylene. It is. Desirable ring D, ring E, or ring F is 1,4-cyclohexylene for decreasing the viscosity or increasing the maximum temperature, and 1,4-phenylene for decreasing the minimum temperature.
- Z 1 and Z 2 are each independently a single bond, —CH 2 CH 2 —, —CH 2 O—, —OCH 2 —, —COO—, or —OCO—. Desirable Z 1 or Z 2 is a single bond for increasing the stability.
- Z 3 and Z 4 are each independently a single bond, —CH 2 CH 2 —, —CH 2 O—, —OCH 2 —, —COO—, or —OCO—, and at least one of Z 3 and Z 4 One is —CH 2 CH 2 —, —CH 2 O—, —OCH 2 —, —COO—, or —OCO—. Desirable Z 3 or Z 4 is a single bond for decreasing the viscosity, —CH 2 CH 2 — for decreasing the minimum temperature, and —CH 2 O— for increasing the dielectric anisotropy.
- A is an integer from 0 to 12.
- Preferred a is 0 or 1 for decreasing the viscosity.
- b is 1, 2 or 3
- c is 0 or 1, and the sum of b and c is 3 or less.
- Preferred b is 1 for decreasing the viscosity, and 2 or 3 for increasing the maximum temperature.
- Desirable c is 0 for decreasing the viscosity, and is 1 for decreasing the minimum temperature.
- d is 0, 1, or 2, and when d is 1, ring E is 1,4-cyclohexylene, 2-fluoro-1,4-phenylene, or 2,5-difluoro-1, 4-phenylene.
- Preferred d is 0 for decreasing the viscosity, and 1 or 2 for increasing the maximum temperature.
- e is 1, 2 or 3, f is 0 or 1, and the sum of e and f is 3 or less.
- Preferred e is 1 for decreasing the viscosity, and 2 or 3 for increasing the maximum temperature.
- Preferred f is 0 for decreasing the viscosity, and 1 for decreasing the minimum temperature.
- P 1 , P 2 and P 3 are polymerizable groups.
- Preferred P 1 , P 2 , or P 3 is a polymerizable group selected from the group of groups represented by formula (P-1) to formula (P-6).
- Further preferred P 1 , P 2 or P 3 is a group (P-1) and a group (P-2).
- Particularly preferred groups (P-1) are —OCO—CH ⁇ CH 2 and —OCO—C (CH 3 ) ⁇ CH 2 .
- the wavy line from the group (P-1) to the group (P-6) indicates a binding site.
- M 1 , M 2 and M 3 are independently hydrogen, fluorine, alkyl having 1 to 5 carbons, or at least one hydrogen is replaced by halogen. And alkyl having 1 to 5 carbon atoms.
- Preferred M 1 , M 2 or M 3 is hydrogen or methyl for increasing the reactivity. More preferred M 1 is methyl, and more preferred M 2 or M 3 is hydrogen.
- both P 1 and P 3 are groups (P-4), at least one of Sp 1 and Sp 3 is at least one —CH 2 — is —O—, —COO—, —OCO—, Or alkylene substituted with —OCOO—. That is, both P 1 and P 3 are not alkenyl such as 1-propenyl.
- P 4 , P 5 , and P 6 are each independently a group represented by formula (P-1) to formula (P-3).
- Preferred P 4 , P 5 or P 6 are group (P-1) and group (P-2).
- Further preferred groups (P-1) are —OCO—CH ⁇ CH 2 and —OCO—C (CH 3 ) ⁇ CH 2 .
- the wavy line from the group (P-1) to the group (P-3) indicates a bonding site.
- P 4 P 5, and when all of the P 6 is a group (P-1), M 1 ( or M 2 or M 3) of P 4, the same M 1 of M 1 or P 6, the P 5 May be different or different.
- Preferred Sp 1 , Sp 2 or Sp 3 is a single bond.
- Ring K and Ring M are independently cyclohexyl, cyclohexenyl, phenyl, 1-naphthyl, 2-naphthyl, tetrahydropyran-2-yl, 1,3-dioxane-2-yl, pyrimidin-2-yl, or pyridine -2-yl, and in these rings, at least one hydrogen is halogen, alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, or 1 carbon in which at least one hydrogen is replaced by halogen. To 12 alkyls. Preferred ring K or ring M is phenyl.
- Ring L is 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, naphthalene-1,2-diyl, naphthalene-1,3-diyl, naphthalene-1,4-diyl, Naphthalene-1,5-diyl, naphthalene-1,6-diyl, naphthalene-1,7-diyl, naphthalene-1,8-diyl, naphthalene-2,3-diyl, naphthalene-2,6-diyl, naphthalene- 2,7-diyl, tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, pyrimidine-2,5-diyl, or pyridine-2,5-diyl, in these rings , At least one hydrogen is halogen, al
- Z 5 and Z 6 are each independently a single bond or alkylene having 1 to 10 carbon atoms, in which at least one —CH 2 — is —O—, —CO—, —COO—, or — OCO— may be substituted, and at least one —CH 2 —CH 2 — may be —CH ⁇ CH—, —C (CH 3 ) ⁇ CH—, —CH ⁇ C (CH 3 ) —, or —C (CH 3 ) ⁇ C (CH 3 ) — may be replaced, and in these groups at least one hydrogen may be replaced with fluorine or chlorine.
- Preferred Z 5 or Z 6 is a single bond, —CH 2 CH 2 —, —CH 2 O—, —OCH 2 —, —COO—, or —OCO—. Further preferred Z 5 or Z 6 is a single bond.
- G is 0, 1, or 2.
- Preferred g is 0 or 1.
- h, j, and k are independently 0, 1, 2, 3, or 4, and the sum of h, j, and k is 1 or greater.
- Preferred h, j, or k is 1 or 2.
- Desirable compounds (2) are the compounds (2-1) to (2-11) according to item 4.
- at least one of the second components is the compound (2-1), the compound (2-2), the compound (2-4), or the compound (2-8). It is preferable that at least two of the second components are the compound (2-1) and the compound (2-4), or the combination of the compound (2-1) and the compound (2-8).
- Desirable compound (3) is the compound (3-1) to the compound (3-12) according to item 7.
- at least one of the third components is the compound (3-1), the compound (3-3), the compound (3-5), the compound (3-6), or the compound (3-7). It is preferable. It is preferable that at least two of the third components are a combination of the compound (3-1), the compound (3-3), the compound (3-1), and the compound (3-5).
- Desirable compound (4) is the compound (4-1) to the compound (4-8) according to item 10.
- at least one of the fourth components is the compound (4-1), the compound (4-2), the compound (4-4), or the compound (4-8). It is preferable that at least two of the fourth components are a combination of the compound (4-2) and the compound (4-4).
- Desirable compound (5) is the compound (5-1) to the compound (5-27) according to item 14.
- at least one of the additive components is compound (5-1), compound (5-2), compound (5-24), compound (5-25), compound (5-26), or compound (5-27) is preferred.
- At least two of the additive components are compound (5-1) and compound (5-2), compound (5-1) and compound (5-18), compound (5-2) and compound (5-24), Compound (5-2) and Compound (5-25), Compound (5-2) and Compound (5-26), Compound (5-25) and Compound (5-26), or Compound (5-18) and A combination of compounds (5-24) is preferred.
- preferred M 1 , M 2 , or M 3 is hydrogen or methyl.
- additives that may be added to the composition will be described.
- Such additives are optically active compounds, antioxidants, ultraviolet absorbers, dyes, antifoaming agents, polymerizable compounds, polymerization initiators, polymerization inhibitors, and the like.
- An optically active compound is added to the composition for the purpose of inducing a helical structure of liquid crystal to give a twist angle. Examples of such a compound are the compound (6-1) to the compound (6-5).
- a desirable ratio of the optically active compound is approximately 5% by weight or less. A more desirable ratio is in the range of approximately 0.01% by weight to approximately 2% by weight.
- an antioxidant is composed. Added to the product.
- a preferred example of the antioxidant is a compound (7) wherein n is an integer of 1 to 9.
- n 1, 3, 5, 7, or 9. Further preferred n is 7. Since the compound (7) in which n is 7 has low volatility, it is effective for maintaining a large voltage holding ratio not only at room temperature but also at a temperature close to the upper limit temperature after the device has been used for a long time.
- a desirable ratio of the antioxidant is approximately 50 ppm or more for achieving its effect, and is approximately 600 ppm or less for avoiding a decrease in the maximum temperature or avoiding an increase in the minimum temperature.
- a more desirable ratio is in the range of approximately 100 ppm to approximately 300 ppm.
- the ultraviolet absorber examples include benzophenone derivatives, benzoate derivatives, triazole derivatives and the like. Also preferred are light stabilizers such as sterically hindered amines.
- a desirable ratio of these absorbers and stabilizers is approximately 50 ppm or more for achieving the effect thereof, and approximately 10,000 ppm or less for avoiding a decrease in the maximum temperature or avoiding an increase in the minimum temperature. A more desirable ratio is in the range of approximately 100 ppm to approximately 10,000 ppm.
- a dichroic dye such as an azo dye or an anthraquinone dye is added to the composition in order to adapt it to a GH (guest host) mode element.
- a preferred ratio of the dye is in the range of approximately 0.01% by weight to approximately 10% by weight.
- an antifoaming agent such as dimethyl silicone oil or methylphenyl silicone oil is added to the composition.
- a desirable ratio of the antifoaming agent is approximately 1 ppm or more for obtaining the effect thereof, and approximately 1000 ppm or less for preventing a display defect.
- a more desirable ratio is in the range of approximately 1 ppm to approximately 500 ppm.
- a polymerizable compound is used to adapt to a polymer support alignment (PSA) type device.
- Compound (5) is suitable for this purpose.
- a polymerizable compound different from the compound (5) may be added to the composition together with the compound (5).
- Preferable examples of such a polymerizable compound are compounds such as acrylate, methacrylate, vinyl compound, vinyloxy compound, propenyl ether, epoxy compound (oxirane, oxetane), vinyl ketone and the like. Further preferred examples are acrylate or methacrylate derivatives.
- a desirable ratio of compound (5) is 10% by weight or more based on the total weight of the polymerizable compound. A more desirable ratio is 50% by weight or more. A particularly desirable ratio is 80% by weight or more. The most preferred ratio is 100% by weight.
- a polymerizable compound such as compound (5) is polymerized by ultraviolet irradiation.
- the polymerization may be performed in the presence of a suitable initiator such as a photopolymerization initiator.
- a suitable initiator such as a photopolymerization initiator.
- Appropriate conditions for polymerization, the appropriate type of initiator, and the appropriate amount are known to those skilled in the art and are described in the literature.
- Irgacure 651 registered trademark; BASF
- Irgacure 184 registered trademark; BASF
- Darocur 1173 registered trademark; BASF
- a desirable ratio of the photopolymerization initiator is in the range of approximately 0.1% by weight to approximately 5% by weight based on the total weight of the polymerizable compound.
- a more desirable ratio is in the range of approximately 1% by weight to approximately 3% by weight.
- a polymerization inhibitor When storing a polymerizable compound such as compound (5), a polymerization inhibitor may be added to prevent polymerization.
- the polymerizable compound is usually added to the composition without removing the polymerization inhibitor.
- the polymerization inhibitor include hydroquinone derivatives such as hydroquinone and methylhydroquinone, 4-tert-butylcatechol, 4-methoxyphenol, phenothiazine and the like.
- Compound (1) is synthesized by the method described in JP-A-59-176221.
- Compound (2-1) is synthesized by the method described in Japanese Patent Application Laid-Open No. 2000-053602.
- Compound (3-1) is synthesized by the method described in JP-A-59-176221.
- Compound (3-12) is synthesized by the method described in JP-A-2-237949.
- Compound (4-1) is synthesized by the method described in JP-T-2-503441.
- a compound of formula (7) where n is 1 is available from Sigma-Aldrich Corporation.
- Compound (7) etc. in which n is 7 is synthesized by the method described in US Pat. No. 3,660,505.
- the composition mainly has a minimum temperature of about ⁇ 10 ° C. or lower, a maximum temperature of about 70 ° C. or higher, and an optical anisotropy in the range of about 0.07 to about 0.20.
- a device containing this composition has a large voltage holding ratio.
- This composition is suitable for an AM device.
- This composition is particularly suitable for a transmissive AM device.
- a composition having an optical anisotropy in the range of about 0.08 to about 0.25 by controlling the proportion of the component compounds or by mixing other liquid crystal compounds, and further from about 0.10 Compositions having optical anisotropy in the range of about 0.30 may be prepared.
- This composition can be used as a composition having a nematic phase, or can be used as an optically active composition by adding an optically active compound.
- This composition can be used for an AM device. Further, it can be used for PM elements.
- This composition can be used for an AM device and a PM device having modes such as PC, TN, STN, ECB, OCB, IPS, FFS, VA, and FPA.
- Use for an AM device having a TN, OCB, IPS mode or FFS mode is particularly preferable.
- the alignment of liquid crystal molecules may be parallel to or perpendicular to the glass substrate.
- These elements may be reflective, transmissive, or transflective. Use in a transmissive element is preferred. It can also be used for an amorphous silicon-TFT device or a polycrystalline silicon-TFT device.
- NCAP non-curvilinear-aligned-phase
- PD polymer-dispersed
- the present invention will be described in more detail with reference to examples. The invention is not limited by these examples.
- the present invention includes a mixture of the composition of Example 1 and the composition of Example 2.
- the invention also includes a mixture of at least two of the example compositions.
- the synthesized compound was identified by a method such as NMR analysis. The properties of the compounds and compositions were measured by the methods described below.
- NMR analysis DRX-500 manufactured by Bruker BioSpin Corporation was used for measurement.
- the sample was dissolved in a deuterated solvent such as CDCl 3, and the measurement was performed at room temperature, 500 MHz, and 16 times of integration.
- Tetramethylsilane was used as an internal standard.
- CFCl 3 was used as an internal standard and the number of integrations was 24.
- s is a singlet
- d is a doublet
- t is a triplet
- q is a quartet
- quint is a quintet
- sex is a sextet
- m is a multiplet
- br is broad.
- GC-14B gas chromatograph manufactured by Shimadzu Corporation was used for measurement.
- the carrier gas is helium (2 mL / min).
- the sample vaporization chamber was set at 280 ° C, and the detector (FID) was set at 300 ° C.
- capillary column DB-1 (length 30 m, inner diameter 0.32 mm, film thickness 0.25 ⁇ m; stationary liquid phase is dimethylpolysiloxane; nonpolar) manufactured by Agilent Technologies Inc. was used.
- the column was held at 200 ° C. for 2 minutes and then heated to 280 ° C. at a rate of 5 ° C./min.
- a sample was prepared in an acetone solution (0.1% by weight), and 1 ⁇ L thereof was injected into the sample vaporization chamber.
- the recorder is a C-R5A Chromatopac manufactured by Shimadzu Corporation, or an equivalent product.
- the obtained gas chromatogram showed the peak retention time and peak area corresponding to the component compounds.
- capillary column As a solvent for diluting the sample, chloroform, hexane or the like may be used.
- the following capillary column may be used.
- HP-1 from Agilent Technologies Inc. (length 30 m, inner diameter 0.32 mm, film thickness 0.25 ⁇ m), Rtx-1 from Restek Corporation (length 30 m, inner diameter 0.32 mm, film thickness 0.25 ⁇ m), BP-1 (length 30 m, inner diameter 0.32 mm, film thickness 0.25 ⁇ m) manufactured by SGE International Pty.
- a capillary column CBP1-M50-025 length 50 m, inner diameter 0.25 mm, film thickness 0.25 ⁇ m
- Shimadzu Corporation may be used.
- the ratio of the liquid crystal compound contained in the composition may be calculated by the following method.
- a mixture of liquid crystal compounds is detected by a gas chromatograph (FID).
- the area ratio of peaks in the gas chromatogram corresponds to the ratio (weight ratio) of liquid crystal compounds.
- the correction coefficient of each liquid crystal compound may be regarded as 1. Therefore, the ratio (% by weight) of the liquid crystal compound can be calculated from the peak area ratio.
- Measurement sample When measuring the properties of the composition, the composition was used as it was as a sample.
- a sample for measurement was prepared by mixing this compound (15% by weight) with mother liquid crystals (85% by weight). The characteristic value of the compound was calculated from the value obtained by the measurement by extrapolation.
- (Extrapolated value) ⁇ (Measured value of sample) ⁇ 0.85 ⁇ (Measured value of mother liquid crystal) ⁇ / 0.15.
- the ratio of the compound and the mother liquid crystal is 10% by weight: 90% by weight, 5% by weight: 95% by weight, 1% by weight: 99% by weight in this order. changed.
- the maximum temperature, optical anisotropy, viscosity, and dielectric anisotropy values for the compound were determined.
- the following mother liquid crystals were used.
- the ratio of the component compounds is shown by weight%.
- Measurement method The characteristics were measured by the following method. Many of these methods have been modified by the methods described in the JEITA standard (JEITA ED-2521B) established by the Japan Electronics and Information Technology Industries Association (hereinafter referred to as JEITA). Was the way. No thin film transistor (TFT) was attached to the TN device used for the measurement.
- JEITA Japan Electronics and Information Technology Industries Association
- nematic phase (NI; ° C.): A sample was placed on a hot plate of a melting point measuring apparatus equipped with a polarizing microscope and heated at a rate of 1 ° C./min. The temperature was measured when a part of the sample changed from a nematic phase to an isotropic liquid.
- the upper limit temperature of the nematic phase may be abbreviated as “upper limit temperature”.
- T C Minimum temperature of nematic phase
- a sample having a nematic phase is placed in a glass bottle and placed in a freezer at 0 ° C., ⁇ 10 ° C., ⁇ 20 ° C., ⁇ 30 ° C., and ⁇ 40 ° C. for 10 days. After storage, the liquid crystal phase was observed. For example, when the sample remained in a nematic phase at ⁇ 20 ° C. and changed to a crystalline or smectic phase at ⁇ 30 ° C., the TC was described as ⁇ 20 ° C.
- the lower limit temperature of the nematic phase may be abbreviated as “lower limit temperature”.
- Viscosity Bulk viscosity; ⁇ ; measured at 20 ° C .; mPa ⁇ s: An E-type viscometer manufactured by Tokyo Keiki Co., Ltd. was used for the measurement.
- Viscosity (rotational viscosity; ⁇ 1; measured at 25 ° C .; mPa ⁇ s): The measurement was performed according to the method described in M. ⁇ Imai et al., Molecular Crystals and Liquid Crystals, Vol. I followed. A sample was put in a VA device having a distance (cell gap) between two glass substrates of 20 ⁇ m. This element was applied stepwise in increments of 1 volt within a range of 39 to 50 volts. After no application for 0.2 seconds, the application was repeated under the condition of only one rectangular wave (rectangular pulse; 0.2 seconds) and no application (2 seconds).
- the peak current (peak current) and peak time (peak time) of the transient current (transient current) generated by this application were measured. These measurements and M.I.
- the value of rotational viscosity was obtained from the paper by Tsuji Imai et al. The dielectric anisotropy necessary for this calculation was measured in the item (6).
- the dielectric constants ( ⁇ and ⁇ ) were measured as follows. 1) Measurement of dielectric constant ( ⁇ ): An ethanol (20 mL) solution of octadecyltriethoxysilane (0.16 mL) was applied to a well-cleaned glass substrate. The glass substrate was rotated with a spinner and then heated at 150 ° C. for 1 hour. A sample was put in a VA element in which the distance between two glass substrates (cell gap) was 4 ⁇ m, and the element was sealed with an adhesive that was cured with ultraviolet rays.
- Sine waves (0.5 V, 1 kHz) were applied to the device, and after 2 seconds, the dielectric constant ( ⁇ ) in the major axis direction of the liquid crystal molecules was measured.
- 2) Measurement of dielectric constant ( ⁇ ) A polyimide solution was applied to a well-cleaned glass substrate. After baking this glass substrate, the obtained alignment film was rubbed. A sample was put in a TN device in which the distance between two glass substrates (cell gap) was 9 ⁇ m and the twist angle was 80 degrees. Sine waves (0.5 V, 1 kHz) were applied to the device, and after 2 seconds, the dielectric constant ( ⁇ ) in the minor axis direction of the liquid crystal molecules was measured.
- Threshold voltage (Vth; measured at 25 ° C .; V): An LCD5100 luminance meter manufactured by Otsuka Electronics Co., Ltd. was used for the measurement.
- the light source was a halogen lamp.
- a sample is placed in a normally black mode VA element in which the distance between two glass substrates (cell gap) is 4 ⁇ m and the rubbing direction is anti-parallel, and an adhesive that cures the element with ultraviolet rays is used. And sealed.
- the voltage (60 Hz, rectangular wave) applied to this element was increased stepwise from 0V to 20V by 0.02V.
- the device was irradiated with light from the vertical direction, and the amount of light transmitted through the device was measured.
- a voltage-transmittance curve was created in which the transmittance was 100% when the light amount reached the maximum and the transmittance was 0% when the light amount was the minimum.
- the threshold voltage was expressed as a voltage when the transmittance reached 10%.
- VHR-1 Voltage holding ratio
- the TN device used for the measurement had a polyimide alignment film, and the distance between two glass substrates (cell gap) was 5 ⁇ m. . This element was sealed with an adhesive that was cured with ultraviolet rays after the sample was placed.
- the TN device was charged by applying a pulse voltage (60 microseconds at 5 V).
- the decaying voltage was measured for 16.7 milliseconds with a high-speed voltmeter, and the area A between the voltage curve and the horizontal axis in a unit cycle was determined.
- Area B was the area when it was not attenuated.
- the voltage holding ratio was expressed as a percentage of area A with respect to area B.
- VHR-2 Voltage holding ratio (VHR-2; measured at 80 ° C .;%): The voltage holding ratio was measured in the same procedure as above except that it was measured at 80 ° C. instead of 25 ° C. The obtained value was expressed as VHR-2.
- VHR-3 Voltage holding ratio
- the TN device used for the measurement had a polyimide alignment film, and the cell gap was 5 ⁇ m.
- a sample was injected into this element and irradiated with light for 20 minutes.
- the light source was an ultra high pressure mercury lamp USH-500D (manufactured by USHIO), and the distance between the element and the light source was 20 cm.
- a decaying voltage was measured for 16.7 milliseconds.
- a composition having a large VHR-3 has a large stability to ultraviolet light.
- VHR-3 is preferably 90% or more, and more preferably 95% or more.
- VHR-4 Voltage holding ratio
- the TN device injected with the sample was heated in a constant temperature bath at 80 ° C. for 500 hours, and then the voltage holding ratio was measured to determine the stability against heat. Evaluated. In the measurement of VHR-4, a voltage decaying for 16.7 milliseconds was measured. A composition having a large VHR-4 has a large stability to heat.
- the response time was expressed as the time required for the change from 90% transmittance to 10% transmittance (fall time; millisecond).
- the compounds in Examples were represented by symbols based on the definitions in Table 3 below.
- Table 3 the configuration regarding 1,4-cyclohexylene is trans.
- the number in parentheses after the symbol corresponds to the compound number.
- the symbol ( ⁇ ) means other liquid crystal compounds.
- the ratio (percentage) of the liquid crystal compound is a weight percentage (% by weight) based on the weight of the liquid crystal composition.
- Example 6 was selected from the compositions disclosed in WO2012-053323. The reason is that this composition contains a compound similar to compound (1).
- the components and properties of this composition are as follows. 3-HBB-2 (1) Similarity 5% 5-BB (2F, 3F) -O2 (2-2) 5% V2-BB (2F, 3F) -O2 (2-2) 5% 1V2-BB (2F, 3F) -O2 (2-2) 3% 2-BB (2F, 3F) B-4 (2-5) 3% 5-HBB (2F, 3F) -O2 (2-8) 5% 3-HHB (2F, 3CL) -O2 (2-10) 3% 5-DhBB (2F, 3F) -O2 (2) 3% 5-DhB (2F, 3F) -O2 (2) 3% 3-HH-V (3-1) 6% 3-HH-V1 (3-1) 5% 3-HH-VFF (3-1) 5% 1-BB-1 (3-3) 5% 1-BB-5 (3-3) 5% 2-BB-3 (3-3) 5% 3-BB-5
- Example 1 to Example 10 had a smaller viscosity than that of Comparative Example 1. Therefore, it is concluded that the liquid crystal composition of the present invention has excellent characteristics.
- the liquid crystal composition of the present invention has a high maximum temperature, a low minimum temperature, a small viscosity, a suitable optical anisotropy, a large negative dielectric anisotropy, a large specific resistance, a high stability against ultraviolet rays, and a high stability against heat. Or the like, satisfying at least one characteristic or having an appropriate balance with respect to at least two characteristics.
- a liquid crystal display element containing this composition has characteristics such as a short response time, a large voltage holding ratio, a low threshold voltage, a large contrast ratio, and a long lifetime, and thus can be used for a liquid crystal projector, a liquid crystal television, and the like. .
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Abstract
Description
式(1)において、R1は、炭素数1から12のアルキル、炭素数1から12のアルコキシ、炭素数2から12のアルケニル、または少なくとも1つの水素がフッ素で置き換えられた炭素数2から12のアルケニルであり;aは0から12の整数である。
式(2)において、R2およびR3は独立して、炭素数1から12のアルキル、炭素数1から12のアルコキシ、炭素数2から12のアルケニル、炭素数2から12のアルケニルオキシ、少なくとも1つの水素がフッ素で置き換えられた炭素数1から12のアルキル、または少なくとも1つの水素がフッ素で置き換えられた炭素数2から12のアルケニルであり;環Aおよび環Cは独立して、1,4-シクロへキシレン、1,4-シクロへキセニレン、1,4-フェニレン、少なくとも1つの水素がフッ素または塩素で置き換えられた1,4-フェニレン、またはテトラヒドロピラン-2,5-ジイルであり;環Bは、2,3-ジフルオロ-1,4-フェニレン、2-クロロ-3-フルオロ-1,4-フェニレン、2,3-ジフルオロ-5-メチル-1,4-フェニレン、3,4,5-トリフルオロナフタレン-2,6-ジイル、または7,8-ジフルオロクロマン-2,6-ジイルであり;bは、1、2、または3であり;cは0または1であり;そして、bとcとの和は3以下である。
式(2-1)から式(2-11)において、R2およびR3は独立して、炭素数1から12のアルキル、炭素数1から12のアルコキシ、炭素数2から12のアルケニル、炭素数2から12のアルケニルオキシ、少なくとも1つの水素がフッ素で置き換えられた炭素数1から12のアルキル、または少なくとも1つの水素がフッ素で置き換えられた炭素数2から12のアルケニルである。
式(3)において、R4およびR5は独立して、炭素数1から12のアルキル、炭素数1から12のアルコキシ、炭素数2から12のアルケニル、少なくとも1つの水素がフッ素で置き換えられた炭素数1から12のアルキル、または少なくとも1つの水素がフッ素で置き換えられた炭素数2から12のアルケニルであり;環D、環E、および環Fは独立して、1,4-シクロへキシレン、1,4-フェニレン、2-フルオロ-1,4-フェニレン、または2,5-ジフルオロ-1,4-フェニレンであり;Z1およびZ2は独立して、単結合、-CH2CH2-、-CH2O-、-OCH2-、-COO-、または-OCO-であり;dは、0、1、または2であり;ここで、dが1であるときの環Eは、1,4-シクロへキシレン、2-フルオロ-1,4-フェニレン、または2,5-ジフルオロ-1,4-フェニレンである。
式(3-1)から式(3-12)において、R4およびR5は独立して、炭素数1から12のアルキル、炭素数1から12のアルコキシ、炭素数2から12のアルケニル、少なくとも1つの水素がフッ素で置き換えられた炭素数1から12のアルキル、または少なくとも1つの水素がフッ素で置き換えられた炭素数2から12のアルケニルである。
式(2)において、R6およびR7は独立して、炭素数1から12のアルキル、炭素数1から12のアルコキシ、炭素数2から12のアルケニル、炭素数2から12のアルケニルオキシ、少なくとも1つの水素がフッ素で置き換えられた炭素数1から12のアルキル、または少なくとも1つの水素がフッ素で置き換えられた炭素数2から12のアルケニルであり;環Gおよび環Jは独立して、1,4-シクロへキシレン、1,4-シクロへキセニレン、1,4-フェニレン、少なくとも1つの水素がフッ素または塩素で置き換えられた1,4-フェニレン、またはテトラヒドロピラン-2,5-ジイルであり;環Iは、2,3-ジフルオロ-1,4-フェニレン、2-クロロ-3-フルオロ-1,4-フェニレン、2,3-ジフルオロ-5-メチル-1,4-フェニレン、3,4,5-トリフルオロナフタレン-2,6-ジイル、または7,8-ジフルオロクロマン-2,6-ジイルであり;Z3およびZ4は独立して、単結合、-CH2CH2-、-CH2O-、-OCH2-、-COO-、または-OCO-であり;Z3およびZ4の少なくとも1つが、-CH2CH2-、-CH2O-、-OCH2-、-COO-、または-OCO-であり;eは、1、2、または3であり;fは0または1であり;そして、eとfとの和は3以下である。
式(4-1)から式(4-8)において、R6およびR7は独立して、炭素数1から12のアルキル、炭素数1から12のアルコキシ、炭素数2から12のアルケニル、炭素数2から12のアルケニルオキシ、少なくとも1つの水素がフッ素で置き換えられた炭素数1から12のアルキル、または少なくとも1つの水素がフッ素で置き換えられた炭素数2から12のアルケニルである。
式(5)において、環Kおよび環Mは独立して、シクロヘキシル、シクロヘキセニル、フェニル、1-ナフチル、2-ナフチル、テトラヒドロピラン-2-イル、1,3-ジオキサン-2-イル、ピリミジン-2-イル、またはピリジン-2-イルであり、これらの環において、少なくとも1つの水素は、ハロゲン、炭素数1から12のアルキル、炭素数1から12のアルコキシ、または少なくとも1つの水素がハロゲンで置き換えられた炭素数1から12のアルキルで置き換えられてもよく;環Lは、1,4-シクロへキシレン、1,4-シクロヘキセニレン、1,4-フェニレン、ナフタレン-1,2-ジイル、ナフタレン-1,3-ジイル、ナフタレン-1,4-ジイル、ナフタレン-1,5-ジイル、ナフタレン-1,6-ジイル、ナフタレン-1,7-ジイル、ナフタレン-1,8-ジイル、ナフタレン-2,3-ジイル、ナフタレン-2,6-ジイル、ナフタレン-2,7-ジイル、テトラヒドロピラン-2,5-ジイル、1,3-ジオキサン-2,5-ジイル、ピリミジン-2,5-ジイル、またはピリジン-2,5-ジイルであり、これらの環において、少なくとも1つの水素は、ハロゲン、炭素数1から12のアルキル、炭素数1から12のアルコキシ、または少なくとも1つの水素がハロゲンで置き換えられた炭素数1から12のアルキルで置き換えられてもよく;Z5およびZ6は独立して、単結合または炭素数1から10のアルキレンであり、このアルキレンにおいて、少なくとも1つの-CH2-は、-O-、-CO-、-COO-、または-OCO-で置き換えられてもよく、少なくとも1つの-CH2-CH2-は、-CH=CH-、-C(CH3)=CH-、-CH=C(CH3)-、または-C(CH3)=C(CH3)-で置き換えられてもよく、これらの基において、少なくとも1つの水素は、フッ素または塩素で置き換えられてもよく;P1、P2、およびP3は独立して、重合性基であり;Sp1、Sp2、およびSp3は独立して、単結合、または炭素数1から10のアルキレンであり、このアルキレンにおいて、少なくとも1つの-CH2-は、-O-、-COO-、-OCO-、または-OCOO-で置き換えられてもよく、少なくとも1つの-CH2-CH2-は、-CH=CH-または-C≡C-で置き換えられてもよく、これらの基において、少なくとも1つの水素は、フッ素または塩素で置き換えられてもよく;gは、0、1、または2であり;h、j、およびkは独立して、0、1、2、3、または4であり;そして、h、j、およびkの和は、1以上である。
式(P-1)から式(P-6)において、M1、M2、およびM3は独立して、水素、フッ素、炭素数1から5のアルキル、または少なくとも1つの水素がハロゲンで置き換えられた炭素数1から5のアルキルであり;P1およびP3の両方が式(P-4)で表される基であるとき、式(5)において、Sp1およびSp3の少なくとも1つは、少なくとも1つの-CH2-が、-O-、-COO-、-OCO-、または-OCOO-で置き換えられたアルキレンである。
式(5-1)から式(5-27)において、P4、P5、およびP6は独立して、式(P-1)から式(P-3)で表される基の群から選択された重合性基であり;
式(P-1)から式(P-3)において、M1、M2、およびM3は独立して、水素、フッ素、炭素数1から5のアルキル、または少なくとも1つの水素がハロゲンで置き換えられた炭素数1から5のアルキルであり;式(5-1)から式(5-27)において、Sp1、Sp2、およびSp3は独立して、単結合、または炭素数1から10のアルキレンであり、このアルキレンにおいて、少なくとも1つの-CH2-は、-O-、-COO-、-OCO-、または-OCOO-で置き換えられてもよく、少なくとも1つの-CH2-CH2-は、-CH=CH-または-C≡C-で置き換えられてもよく、これらの基において、少なくとも1つの水素は、フッ素または塩素で置き換えられてもよい。
1)誘電率(ε∥)の測定:よく洗浄したガラス基板にオクタデシルトリエトキシシラン(0.16mL)のエタノール(20mL)溶液を塗布した。ガラス基板をスピンナーで回転させたあと、150℃で1時間加熱した。2枚のガラス基板の間隔(セルギャップ)が4μmであるVA素子に試料を入れ、この素子を紫外線で硬化する接着剤で密閉した。この素子にサイン波(0.5V、1kHz)を印加し、2秒後に液晶分子の長軸方向における誘電率(ε∥)を測定した。
2)誘電率(ε⊥)の測定:よく洗浄したガラス基板にポリイミド溶液を塗布した。このガラス基板を焼成した後、得られた配向膜にラビング処理をした。2枚のガラス基板の間隔(セルギャップ)が9μmであり、ツイスト角が80度であるTN素子に試料を入れた。この素子にサイン波(0.5V、1kHz)を印加し、2秒後に液晶分子の短軸方向における誘電率(ε⊥)を測定した。
国際公開2012-053323号に開示された組成物の中から実施例6を選んだ。根拠は、この組成物が化合物(1)と類似の化合物を含有しているからである。この組成物の成分および特性は下記のとおりである。
3-HBB-2 (1)類似 5%
5-BB(2F,3F)-O2 (2-2) 5%
V2-BB(2F,3F)-O2 (2-2) 5%
1V2-BB(2F,3F)-O2 (2-2) 3%
2-BB(2F,3F)B-4 (2-5) 3%
5-HBB(2F,3F)-O2 (2-8) 5%
3-HHB(2F,3CL)-O2 (2-10) 3%
5-DhBB(2F,3F)-O2 (2) 3%
5-DhB(2F,3F)-O2 (2) 3%
3-HH-V (3-1) 6%
3-HH-V1 (3-1) 5%
3-HH-VFF (3-1) 5%
1-BB-1 (3-3) 5%
1-BB-5 (3-3) 5%
2-BB-3 (3-3) 5%
3-BB-5 (3-3) 5%
3-HHB-O1 (3-5) 3%
5-B(F)BB-3 (3-6) 3%
5-HBB(F)B-3 (3-12) 3%
5-HH2B(2F,3F)-O2 (4-3) 5%
3-HH1OB(2F,3F)-O2 (4-4) 7%
5-HH1OB(2F,3F)-O2 (4-4) 8%
NI=83.9℃;Tc≦-20℃;Δn=0.135;η=18.7mPa・s;Δε=-3.5;VHR-1=99.1%;VHR-2=98.1%;VHR-3=98.2%.
V-HBB-2 (1) 5%
V-HBB-4 (1) 3%
3-BB(2F,3F)-O4 (2-2) 3%
V2-BB(2F,3F)-O2 (2-2) 11%
1V2-BB(2F,3F)-O2 (2-2) 6%
2O-B(2F,3F)B(2F,3F)-O6
(2-3) 3%
V-HHB(2F,3F)-O1 (2-4) 4%
V-HHB(2F,3F)-O2 (2-4) 11%
2-BB(2F,3F)B-3 (2-5) 6%
3-HH-V (3-1) 29%
3-HH-V1 (3-1) 9%
3-HH1OB(2F,3F)-O2 (4-4) 10%
NI=75.6℃;Tc<-20℃;Δn=0.114;Δε=-3.1;Vth=2.36V;η=16.7mPa・s;VHR-1=99.1%;VHR-2=98.2%.
V-HBB-2 (1) 10%
3-HB(2F,3F)-O4 (2-1) 5%
3-BB(2F,3F)-O2 (2-2) 10%
2O-BB(2F,3F)-O2 (2-2) 3%
3-dhBB(2F,3F)-O2 (2-9) 3%
2-HH-3 (3-1) 23%
3-HH-O1 (3-1) 6%
4-HH-V1 (3-1) 9%
1-BB-3 (3-3) 3%
2-HH1OB(2F,3F)-O2 (4-4) 7%
3-HH1OB(2F,3F)-O2 (4-4) 21%
NI=72.6℃;Tc<-20℃;Δn=0.095;Δε=-3.3;Vth=2.17V;η=16.4mPa・s.
V-HBB-2 (1) 8%
3-BB(2F,3F)-O2 (2-2) 10%
5-BB(2F,3F)-O2 (2-2) 4%
V2-BB(2F,3F)-O2 (2-2) 8%
V-HHB(2F,3F)-O1 (2-4) 6%
V-HHB(2F,3F)-O2 (2-4) 12%
V2-HHB(2F,3F)-O2 (2-4) 8%
3-HDhB(2F,3F)-O2 (2-7) 7%
2-HH-3 (3-1) 14%
3-HH-V1 (3-1) 9%
3-HB-O2 (3-2) 8%
V-HHB-1 (3-5) 3%
3-HHEBH-3 (3-8) 3%
NI=83.2℃;Tc<-20℃;Δn=0.109;Δε=-3.3;Vth=2.22V;η=13.2mPa・s.
V-HBB-1 (1) 6%
V2-HBB-1 (1) 3%
V2-HBB(2F,3F)-O2 (2-8) 5%
3-HHB(2F,3CL)-O2 (2-10) 4%
3-HBB(2F,3CL)-O2 (2-11) 6%
5-HBB(2F,3CL)-O2 (2-11) 6%
3-HH-V (3-1) 24%
V-HHB-1 (3-5) 5%
2-BB(F)B-3 (3-7) 3%
3-H2B(2F,3F)-O2 (4-1) 18%
5-H2B(2F,3F)-O2 (4-1) 17%
3-HH2B(2F,3F)-O2 (4-3) 3%
NI=73.8℃;Tc<-20℃;Δn=0.103;Δε=-2.8;Vth=2.31V;η=15.9mPa・s.
V-HBB-2 (1) 11%
V2-HBB-3 (1) 3%
1V2-BB(2F,3F)-O4 (2-2) 4%
3-HHB(2F,3F)-O2 (2-4) 7%
V-HHB(2F,3F)-O1 (2-4) 5%
V-HHB(2F,3F)-O2 (2-4) 8%
2-HBB(2F,3F)-O2 (2-8) 4%
5-HBB(2F,3F)-O2 (2-8) 7%
V-HBB(2F,3F)-O2 (2-8) 3%
2-HH-3 (3-1) 21%
2-HH-5 (3-1) 3%
3-HB-O2 (3-2) 4%
1-BB-3 (3-3) 6%
2-H1OB(2F,3F)-O2 (4-2) 3%
3-H1OB(2F,3F)-O2 (4-2) 11%
NI=77.0℃;Tc<-20℃;Δn=0.108;Δε=-2.8;Vth=2.21V;η=16.7mPa・s.
V-HBB-3 (1) 5%
3-HB(2F,3F)-O2 (2-1) 7%
V-HB(2F,3F)-O2 (2-1) 12%
V-HB(2F,3F)-O4 (2-1) 4%
3-HBB(2F,3F)-O2 (2-8) 10%
5-HBB(2F,3F)-O2 (2-8) 7%
1V2-HBB(2F,3F)-O2 (2-8) 3%
3-HHB(2F,3CL)-O2 (2-10) 5%
2-HH-3 (3-1) 22%
3-HH-4 (3-1) 4%
4-HH-V1 (3-1) 3%
3-HB-O2 (3-2) 6%
5-HB-O2 (3-2) 5%
3-HHB-1 (3-5) 4%
5-HBB(F)B-2 (3-12) 3%
NI=71.5℃;Tc<-20℃;Δn=0.098;Δε=-2.4;Vth=2.36V;η=15.1mPa・s.
V-HBB-2 (1) 6%
1V2-BB(2F,3F)-O2 (2-2) 10%
V-HHB(2F,3F)-O1 (2-4) 8%
V-HHB(2F,3F)-O2 (2-4) 7%
3-HH-V (3-1) 27%
5-HH-V (3-1) 3%
3-HH-V1 (3-1) 8%
3-HH-VFF (3-1) 4%
V2-HHB-1 (3-5) 4%
5-B(F)BB-2 (3-6) 3%
3-H1OB(2F,3F)-O2 (4-2) 12%
3-HH1OB(2F,3F)-O2 (4-4) 5%
3-H1OCro(7F,8F)-5 (4-7) 3%
NI=72.9℃;Tc<-20℃;Δn=0.097;Δε=-3.2;Vth=2.16V;η=16.9mPa・s.
V-HBB-2 (1) 3%
V2-HBB-2 (1) 3%
3-BB(2F,3F)-O2 (2-2) 8%
2O-BB(2F,3F)-O2 (2-2) 3%
3-HDhB(2F,3F)-O2 (2-7) 5%
3-HH-V (3-1) 31%
3-HH-V1 (3-1) 4%
V2-BB-1 (3-3) 6%
V2-HHB-1 (3-5) 8%
5-HBBH-3 (3-10) 3%
3-H1OB(2F,3F)-O2 (4-2) 13%
3-HH1OB(2F,3F)-O2 (4-4) 7%
3-HEB(2F,3F)B(2F,3F)-O2
(4-6) 3%
3-HH1OCro(7F,8F)-5 (4-8) 3%
NI=74.4℃;Tc<-20℃;Δn=0.100;Δε=-3.4;Vth=2.22V;η=16.6mPa・s.
V-HBB-2 (1) 5%
3-HB(2F,3F)-O2 (2-1) 8%
3-HB(2F,3F)-O4 (2-1) 9%
5-HB(2F,3F)-O4 (2-1) 5%
V2-BB(2F,3F)-O2 (2-2) 6%
3-DhHB(2F,3F)-O2 (2-6) 3%
3-HBB(2F,3F)-O2 (2-8) 9%
5-HBB(2F,3F)-O2 (2-8) 8%
2-HH-3 (3-1) 22%
3-HH-4 (3-1) 7%
F3-HH-V (3-1) 3%
7-HB-1 (3-2) 4%
3-HHB-3 (3-5) 3%
5-HB(F)BH-3 (3-11) 5%
1O1-HBBH-5 (-) 3%
NI=73.6℃;Tc<-20℃;Δn=0.094;Δε=-2.3;Vth=2.40V;η=16.0mPa・s.
V-HBB-2 (1) 7%
3-BB(2F,3F)-O2 (2-2) 10%
5-BB(2F,3F)-O2 (2-2) 6%
V2-BB(2F,3F)-O2 (2-2) 5%
V-HHB(2F,3F)-O1 (2-4) 6%
V-HHB(2F,3F)-O2 (2-4) 12%
V2-HHB(2F,3F)-O2 (2-4) 5%
2-HH-3 (3-1) 14%
3-HH-V1 (3-1) 7%
3-HB-O2 (3-2) 4%
3-HHEH-3 (3-4) 3%
V-HHB-1 (3-5) 11%
3-HB(F)HH-2 (3-9) 3%
2-H1OB(2F,3F)-O2 (4-2) 4%
3-DhH1OB(2F,3F)-O2 (4-5) 3%
NI=82.1℃;Tc<-20℃;Δn=0.106;Δε=-2.9;Vth=2.36V;η=13.9mPa・s.
Claims (20)
- 液晶組成物の重量に基づいて、第一成分の割合が3重量%から30重量%の範囲である、請求項1に記載の液晶組成物。
- 第二成分として式(2)で表される化合物の群から選択された少なくとも1つの化合物を含有する、請求項1または2に記載の液晶組成物。
式(2)において、R2およびR3は独立して、炭素数1から12のアルキル、炭素数1から12のアルコキシ、炭素数2から12のアルケニル、炭素数2から12のアルケニルオキシ、少なくとも1つの水素がフッ素で置き換えられた炭素数1から12のアルキル、または少なくとも1つの水素がフッ素で置き換えられた炭素数2から12のアルケニルであり;環Aおよび環Cは独立して、1,4-シクロへキシレン、1,4-シクロへキセニレン、1,4-フェニレン、少なくとも1つの水素がフッ素または塩素で置き換えられた1,4-フェニレン、またはテトラヒドロピラン-2,5-ジイルであり;環Bは、2,3-ジフルオロ-1,4-フェニレン、2-クロロ-3-フルオロ-1,4-フェニレン、2,3-ジフルオロ-5-メチル-1,4-フェニレン、3,4,5-トリフルオロナフタレン-2,6-ジイル、または7,8-ジフルオロクロマン-2,6-ジイルであり;bは、1、2、または3であり;cは0または1であり;そしてbとcとの和は3以下である。 - 液晶組成物の重量に基づいて、第二成分の割合が5重量%から70重量%の範囲である、請求項3または4に記載の液晶組成物。
- 第三成分として式(3)で表される化合物の群から選択された少なくとも1つの化合物をさらに含有する、請求項1から5のいずれか1項に記載の液晶組成
式(3)において、R4およびR5は独立して、炭素数1から12のアルキル、炭素数1から12のアルコキシ、炭素数2から12のアルケニル、少なくとも1つの水素がフッ素で置き換えられた炭素数1から12のアルキル、または少なくとも1つの水素がフッ素で置き換えられた炭素数2から12のアルケニルであり;環D、環E、および環Fは独立して、1,4-シクロへキシレン、1,4-フェニレン、2-フルオロ-1,4-フェニレン、または2,5-ジフルオロ-1,4-フェニレンであり;Z1およびZ2は独立して、単結合、-CH2CH2-、-CH2O-、-OCH2-、-COO-、または-OCO-であり;dは、0、1、または2であり;ここで、dが1であるときの環Eは、1,4-シクロへキシレン、2-フルオロ-1,4-フェニレン、または2,5-ジフルオロ-1,4-フェニレンである。 - 液晶組成物の重量に基づいて、第三成分の割合が10重量%から90重量%の範囲である、請求項6または7に記載の液晶組成物。
- 第四成分として式(4)で表される化合物の群から選択された少なくとも1つの化合物を含有する、請求項1から8のいずれか1項に記載の液晶組成物。
式(2)において、R6およびR7は独立して、炭素数1から12のアルキル、炭素数1から12のアルコキシ、炭素数2から12のアルケニル、炭素数2から12のアルケニルオキシ、少なくとも1つの水素がフッ素で置き換えられた炭素数1から12のアルキル、または少なくとも1つの水素がフッ素で置き換えられた炭素数2から12のアルケニルであり;環Gおよび環Jは独立して、1,4-シクロへキシレン、1,4-シクロへキセニレン、1,4-フェニレン、少なくとも1つの水素がフッ素または塩素で置き換えられた1,4-フェニレン、またはテトラヒドロピラン-2,5-ジイルであり;環Iは、2,3-ジフルオロ-1,4-フェニレン、2-クロロ-3-フルオロ-1,4-フェニレン、2,3-ジフルオロ-5-メチル-1,4-フェニレン、3,4,5-トリフルオロナフタレン-2,6-ジイル、または7,8-ジフルオロクロマン-2,6-ジイルであり;Z3およびZ4は独立して、単結合、-CH2CH2-、-CH2O-、-OCH2-、-COO-、または-OCO-であり;Z3およびZ4の少なくとも1つが、-CH2CH2-、-CH2O-、-OCH2-、-COO-、または-OCO-であり;eは、1、2、または3であり;fは0または1であり;そしてeとfとの和は3以下である。 - 液晶組成物の重量に基づいて、第四成分の割合が5重量%から60重量%の範囲である、請求項9または10に記載の液晶組成物。
- 添加物成分として式(5)で表される化合物の群から選択された少なくとも1つの重合性化合物を含有する、請求項1から11のいずれか1項に記載の液晶組成物。
式(5)において、環Kおよび環Mは独立して、シクロヘキシル、シクロヘキセニル、フェニル、1-ナフチル、2-ナフチル、テトラヒドロピラン-2-イル、1,3-ジオキサン-2-イル、ピリミジン-2-イル、またはピリジン-2-イルであり、これらの環において、少なくとも1つの水素は、ハロゲン、炭素数1から12のアルキル、炭素数1から12のアルコキシ、または少なくとも1つの水素がハロゲンで置き換えられた炭素数1から12のアルキルで置き換えられてもよく;環Lは、1,4-シクロへキシレン、1,4-シクロヘキセニレン、1,4-フェニレン、ナフタレン-1,2-ジイル、ナフタレン-1,3-ジイル、ナフタレン-1,4-ジイル、ナフタレン-1,5-ジイル、ナフタレン-1,6-ジイル、ナフタレン-1,7-ジイル、ナフタレン-1,8-ジイル、ナフタレン-2,3-ジイル、ナフタレン-2,6-ジイル、ナフタレン-2,7-ジイル、テトラヒドロピラン-2,5-ジイル、1,3-ジオキサン-2,5-ジイル、ピリミジン-2,5-ジイル、またはピリジン-2,5-ジイルであり、これらの環において、少なくとも1つの水素は、ハロゲン、炭素数1から12のアルキル、炭素数1から12のアルコキシ、または少なくとも1つの水素がハロゲンで置き換えられた炭素数1から12のアルキルで置き換えられてもよく;Z5およびZ6は独立して、単結合または炭素数1から10のアルキレンであり、このアルキレンにおいて、少なくとも1つの-CH2-は、-O-、-CO-、-COO-、または-OCO-で置き換えられてもよく、少なくとも1つの-CH2-CH2-は、-CH=CH-、-C(CH3)=CH-、-CH=C(CH3)-、または-C(CH3)=C(CH3)-で置き換えられてもよく、これらの基において、少なくとも1つの水素は、フッ素または塩素で置き換えられてもよく;P1、P2、およびP3は独立して、重合性基であり;Sp1、Sp2、およびSp3は独立して、単結合、または炭素数1から10のアルキレンであり、このアルキレンにおいて、少なくとも1つの-CH2-は、-O-、-COO-、-OCO-、または-OCOO-で置き換えられてもよく、少なくとも1つの-CH2-CH2-は、-CH=CH-または-C≡C-で置き換えられてもよく、これらの基において、少なくとも1つの水素は、フッ素または塩素で置き換えられてもよく;gは、0、1、または2であり;h、j、およびkは独立して、0、1、2、3、または4であり;そして、h、j、およびkの和は、1以上である。 - 添加物成分として式(5-1)から式(5-27)で表される化合物の群から選択された少なくとも1つの重合性化合物を含有する、請求項1から13のいずれか1項に記載の液晶組成物。
式(5-1)から式(5-27)において、P4、P5、およびP6は独立して、式(P-1)から式(P-3)で表される基の群から選択された重合性基であり;
式(P-1)から式(P-3)において、M1、M2、およびM3は独立して、水素、フッ素、炭素数1から5のアルキル、または少なくとも1つの水素がハロゲンで置き換えられた炭素数1から5のアルキルであり;式(5-1)から式(5-27)において、Sp1、Sp2、およびSp3は独立して、単結合、または炭素数1から10のアルキレンであり、このアルキレンにおいて、少なくとも1つの-CH2-は、-O-、-COO-、-OCO-、または-OCOO-で置き換えられてもよく、少なくとも1つの-CH2-CH2-は、-CH=CH-または-C≡C-で置き換えられてもよく、これらの基において、少なくとも1つの水素は、フッ素または塩素で置き換えられてもよい。 - 液晶組成物の重量に基づいて、添加物成分の添加割合が0.03重量%から10重量%の範囲である、請求項12から14のいずれか1項に記載の液晶組成物。
- 請求項1から15のいずれか1項に記載の液晶組成物を含有する液晶表示素子。
- 液晶表示素子の動作モードが、IPSモード、VAモード、FFSモード、またはFPAモードであり、液晶表示素子の駆動方式がアクティブマトリックス方式である、請求項16に記載の液晶表示素子。
- 請求項12から15のいずれか1項に記載の液晶組成物を含有し、この液晶組成物中の重合性化合物が重合されている、高分子支持配向型の液晶表示素子。
- 請求項1から15のいずれか1項に記載の液晶組成物の、液晶表示素子における使用。
- 請求項12から15のいずれか1項に記載の液晶組成物の、高分子支持配向型の液晶表示素子における使用。
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JP2020097678A (ja) * | 2018-12-18 | 2020-06-25 | Dic株式会社 | 液晶組成物及び液晶表示素子 |
JP7409047B2 (ja) | 2019-11-27 | 2024-01-09 | Dic株式会社 | 組成物及びそれを使用した液晶表示素子 |
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US11008515B2 (en) * | 2017-11-24 | 2021-05-18 | Merck Patent Gmbh | Liquid-crystalline medium |
CN109880639B (zh) * | 2019-03-29 | 2020-12-01 | 石家庄诚志永华显示材料有限公司 | 液晶组合物、液晶显示元件、液晶显示器 |
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JP2017075095A (ja) * | 2015-10-13 | 2017-04-20 | Jnc株式会社 | テトラヒドロピラン環を有する化合物、液晶組成物および液晶表示素子 |
WO2017195585A1 (ja) * | 2016-05-10 | 2017-11-16 | Dic株式会社 | 液晶表示素子 |
JP2020097678A (ja) * | 2018-12-18 | 2020-06-25 | Dic株式会社 | 液晶組成物及び液晶表示素子 |
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KR20150100859A (ko) | 2015-09-02 |
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