POLYMERIZABLE POLAR COMPOUND, LIQUID CRYSTAL COMPOSITION AND LIQUID CRYSTAL DISPLAY DEVICE

TECHNICAL FIELD

The invention relates to a polymerizable polar compound, a liquid crystal composition, and a liquid crystal display device. More specifically, the invention relates to a polymerizable polar compound having an acryloyloxy group that is replaced by a polar group such as a hydroxyalkyl group, a liquid crystal composition that contains the compound and has positive or negative dielectric anisotropy, and a liquid crystal display device including the composition.

BACKGROUND ART

In a liquid crystal display device, a classification based on an operating mode for liquid crystal molecules includes a phase change (PC) mode, a twisted nematic (TN) mode, a super twisted nematic (STN) mode, an electrically controlled birefringence (ECB) mode, an optically compensated bend (OCB) mode, an in-plane switching (IPS) mode, a vertical alignment (VA) mode, a fringe field switching (FFS) mode and a field-induced photo-reactive alignment (FPA) mode. A classification based on a driving mode in the device includes a passive matrix (PM) and an active matrix (AM). The PM is classified into static, multiplex and so forth, and the AM is classified into a thin film transistor (TFT), a metal insulator metal (MIM) and so forth. The TFT is further classified into amorphous silicon and polycrystal silicon. The latter is classified into a high temperature type and a low temperature type based on a production process. A classification based on a light source includes a reflective type utilizing natural light, a transmissive type utilizing backlight and a transflective type utilizing both the natural light and the backlight.

The liquid crystal display device includes a liquid crystal composition having a nematic phase. The composition has suitable characteristics. An AM device having good characteristics can be obtained by improving characteristics of the composition. Table 1 below summarizes a relationship of the characteristics between two aspects. The characteristics of the composition will be further described based on a commercially available AM device. A temperature range of the nematic phase relates to a temperature range in which the device can be used. A preferred maximum temperature of the nematic phase is about 70° C. or higher, and a preferred minimum temperature of the nematic phase is about −10° C. or lower. Viscosity of the composition relates to a response time in the device. A short response time is preferred for displaying moving images on the device. A shorter response time even by one millisecond is desirable. Accordingly, small viscosity of the composition is preferred. The small viscosity at a low temperature is further preferred.

TABLE 1

Characteristics of composition and AM device

No.
Characteristics of composition
Characteristics of AM device

1
Wide temperature range of a
Wide usable temperature range

nematic phase

2
Small viscosity¹⁾
Short response time

3
Suitable optical anisotropy
Large contrast ratio

4
Large positive or negative
Low threshold voltage and

dielectric anisotropy
small electric power consumption

Large contrast ratio

5
Large specific resistance
Large voltage holding ratio and

large contrast ratio

6
High stability to ultraviolet
Long service life

light and heat

7
Large elastic constant
Large contrast ratio and

short response time

¹⁾A liquid crystal composition can be injected into a liquid crystal display device in a short time.

Optical anisotropy of the composition relates to a contrast ratio in the device. According to a mode of the device, large optical anisotropy or small optical anisotropy, more specifically, suitable optical anisotropy is required. A product (Δn×d) of the optical anisotropy (Δn) of the composition and a cell gap (d) in the device is designed so as to maximize the contrast ratio. A suitable value of the product depends on a type of the operating mode. In a device having a mode such as TN, the value is about 0.45 micrometer. The suitable value is in the range of about 0.30 micrometer to about 0.40 micrometer in a device having the VA mode, and is in the range of about 0.20 micrometer to about 0.30 micrometer in a device having the IPS mode or the FFS mode. In the above case, a composition having large optical anisotropy is preferred for a device having a small cell gap. Large dielectric anisotropy in the composition contributes to a low threshold voltage, small electric power consumption and a large contrast ratio in the device. Accordingly, large positive or negative dielectric anisotropy is preferred. Large specific resistance in the composition contributes to a large voltage holding ratio and the large contrast ratio in the device. Accordingly, a composition having large specific resistance at room temperature and also at a temperature close to the maximum temperature of the nematic phase in an initial stage is preferred. The composition having large specific resistance at room temperature and also at a temperature close to the maximum temperature of the nematic phase even after the device has been used for a long period of time is preferred. Stability of the composition to ultraviolet light and heat relates to a service life of the device. In the case where the stability is high, the device has a long service life. Such characteristics are preferred for an AM device used in a liquid crystal projector, a liquid crystal television and so forth.

A composition having positive dielectric anisotropy is used in an AM device having the TN mode. A composition having negative dielectric anisotropy is used in an AM device having the VA mode. In an AM device having the IPS mode or the FFS mode, a composition having positive or negative dielectric anisotropy is used. In an AM device having a polymer sustained alignment (PSA) mode, a composition having positive or negative dielectric anisotropy is used. In a liquid crystal display device having a polymer sustained alignment (PSA) mode, a liquid crystal composition containing a polymer is used. First, a composition to which a small amount of a polymerizable compound is added is injected into the device. Next, the composition is irradiated with ultraviolet light while voltage is applied between substrates of the device. The polymerizable compound is polymerized to form a network structure of the polymer in the composition. In the composition, alignment of liquid crystal molecules can be controlled by the polymer, and therefore the response time of the device is shortened and also image persistence is improved. Such an effect of the polymer can be expected for a device having the mode such as the TN mode, the ECB mode, the OCB mode, the IPS mode, the VA mode, the FFS mode and the FPA mode.

A report has been made on a method of controlling alignment of liquid crystals by using a low molecular weight compound having a cinnamate group, polyvinyl cinnamate, a low molecular weight compound having a chalcone structure, a low molecular weight compound having an azobenzene structure and dendrimers in place of an alignment film such as polyimide (Patent literature No. 1 or No. 2). In the method of Patent literature No. 1 or No. 2, first, the low molecular compound or polymer is dissolved in a liquid crystal composition as an additive. Next, the additive is subjected to phase-separation to form a thin film composed of the low molecular weight compound or polymer on the substrate. Finally, the substrate is irradiated with linearly polarized light at a temperature higher than the maximum temperature of the liquid crystal composition. When the low molecular weight compound or polymer is dimerized or isomerized by this linearly polarized light, the molecules are aligned in a fixed direction. In this method, a horizontal alignment mode device such as IPS and FFS and a vertical alignment mode device such as VA can be produced by selecting a kind of low molecular compounds or polymers. In this method, easily caused phase-separation of the compound from the liquid crystal composition is important when the low molecular weight compound or polymer is easily dissolved at a temperature higher than the maximum temperature of the liquid crystal composition, and then the temperature of the resulting material is returned to room temperature. However, allowance to ensure a compatibility between the low molecular weight compound or polymer and the liquid crystal composition is difficult.

In the liquid crystal display device having no alignment film, a compound (Formula 2) having a methacrylate group at a terminal has been so far described in Patent literature No. 2 as a compound in which liquid crystal molecules can be horizontally aligned. However, in the compound, capability of horizontally aligning liquid crystal molecules is not sufficient.

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CITATION LIST
Patent Literature

Patent literature No. 1: WO 2015/146369 A.

Patent literature No. 2: WO 2017/057162 A.

SUMMARY OF INVENTION
Technical Problem

A first object of the invention is to provide a polar compound having high chemical stability, high capability of horizontally aligning liquid crystal molecules, high solubility in a liquid crystal composition, and a large voltage holding ratio when the compound is used in a liquid crystal display device. A second object is to provide a liquid crystal composition that contains the compound, and satisfies at least one of characteristics such as high maximum temperature of a nematic phase, low minimum temperature of the nematic phase, small viscosity, suitable optical anisotropy, large positive or negative dielectric anisotropy, large specific resistance, high stability to ultraviolet light, high stability to heat and a large elastic constant. A third object is to provide a liquid crystal display device that includes the composition, and has characteristics such as a wide temperature range in which the device can be used, a short response time, a high voltage holding ratio, low threshold voltage, a large contrast ratio and a long service life.

Solution to Problem

The invention concerns a compound represented by formula (1), a liquid crystal composition using the compound, and a liquid crystal display device:

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wherein in formula (1),

a and b are 0, 1 or 2, and expressions: 0≤a+b≤3 hold;

ring A¹, ring A², ring A³and ring A⁴are independently 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, naphthalene-2,6-diyl, decahydronaphthalene-2,6-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl, tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, pyrimidine-2,5-diyl, pyridine-2,5-diyl, fluorene-2,7-diyl, phenanthrene-2,7-diyl, anthracene-2,6-diyl, perhydrocyclopenta[a]phenanthrene-3,17-diyl or 2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydrocyclopenta[a]phenanthrene-3,17-diyl, and in the rings, at least one hydrogen may be replaced by fluorine, chlorine, alkyl having 1 to 12 carbons, alkenyl having 2 to 12 carbons, alkoxy having 1 to 11 carbons or alkenyloxy having 2 to 11 carbons, and in the groups, at least one hydrogen may be replaced by fluorine or chlorine, and when a or b is 2, two of arbitrary ring A¹or ring A⁴may be different;

Z¹, Z², Z³, Z⁴and Z⁵are independently a single bond or alkylene having 1 to 10 carbons, and in the alkylene, at least one piece of —CH₂— may be replaced by —O—, —CO—, —COO—, —OCO— or —OCOO—, and at least one piece of —(CH₂)₂— may be replaced by —CH═CH— or —C≡C—, and in the groups, at least one hydrogen may be replaced by halogen, in which at least one in Z², Z³or Z⁴is any one of —COO—, —OCO—, —CH═CHCOO—, —OCOCH═CH—, —CH═CH—, —CH═CHCO— or —COCH═CH—, and when a or b is 2, two of arbitrary Z¹or Z⁵may be different;

Sp¹and Sp²are independently a single bond or alkylene having 1 to 10 carbons, and in the alkylene, at least one piece of —CH₂— may be replaced by —O—, —CO—, —COO—, —OCO— or —OCOO—, and at least one piece of —(CH₂)₂— may be replaced by —CH═CH— or —C≡C—, and in the groups, at least one hydrogen may be replaced by halogen;

P¹is a group represented by any one of formulas (1a) to (1i);

P²is a group represented by formula (1a),

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wherein in formulas (1a) to (1i), M¹and M²are independently halogen, alkyl having 1 to 5 carbons, or alkyl having 1 to 5 carbons in which at least one hydrogen is replaced by halogen;

R¹is a group represented by any one of formula (2a), (2b) or (2c),

R²is any one of hydrogen, halogen, alkyl having 1 to 5 carbons, alkyl having 1 to 5 carbons in which at least one hydrogen is replaced by halogen, formula (2a), formula (2b) or formula (2c),

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wherein, R³, R⁴and R⁵are independently hydrogen or alkyl having 1 to 15 carbons, and in the alkyl, at least one piece of —CH₂— may be replaced by —O— or —S—, at least one piece of —(CH₂)₂— may be replaced by —CH═CH— or —C≡C—, and in the groups, at least one hydrogen may be replaced by halogen:

wherein, in formulas (2a), (2b) and (2c), Sp³and Sp⁴are independently a single bond or alkylene having 1 to 10 carbons, and in the alkylene, at least one piece of —CH₂— may be replaced by —O—, —NH—, —CO—, —COO—, —OCO— or —OCOO—, and at least one piece of —(CH₂)₂— may be replaced by —CH═CH— or —C≡C—, and in the groups, at least one hydrogen may be replaced by halogen;

S¹is >CH—, >SiH— or >N—;

S²is >C< or >Si<; and

X¹is independently a group represented by —OH, —NH₂, —OR³, —N(R³)₂, —COOH, —SH, —B(OH)₂or a group represented by —Si(R⁶) 3, in which R⁶is hydrogen or alkyl having 1 to 10 carbons, and in the alkyl, at least one piece of —CH₂— may be replaced by —O—, and at least one piece of —(CH₂)₂— may be replaced by —CH═CH—, and in the groups, at least one hydrogen may be replaced by halogen.

Advantageous Effects of Invention

A first advantage of the invention is to provide a polar compound having high chemical stability, high capability of horizontally aligning liquid crystal molecules, high solubility in a liquid crystal composition, and a large voltage holding ratio when the compound is used in a liquid crystal display device. A second advantage is to provide a liquid crystal composition that contains the compound, and satisfies at least one of characteristics such as high maximum temperature of a nematic phase, low minimum temperature of the nematic phase, small viscosity, suitable optical anisotropy, large positive or negative dielectric anisotropy, large specific resistance, high stability to ultraviolet light, high stability to heat and a large elastic constant. A third advantage is to provide a liquid crystal display device that includes the composition, and has characteristics such as a wide temperature range in which the device can be used, a short response time, a high voltage holding ratio, low threshold voltage, a large contrast ratio and a long service life. A formation step of an alignment film becomes unnecessary by utilizing the liquid crystal composition containing the compound of the invention, and therefore a liquid crystal display device in which manufacturing cost is reduced can be obtained.

DESCRIPTION OF EMBODIMENTS

Usage of terms herein is as described below. Terms “liquid crystal composition” and “liquid crystal display device” may be occasionally abbreviated as “composition” and “device,” respectively. “Liquid crystal display device” is a generic term for a liquid crystal display panel and a liquid crystal display module. “Liquid crystal compound” is a generic term for a compound having a liquid crystal phase such as a nematic phase and a smectic phase, and a compound having no liquid crystal phase but to be mixed with the composition for the purpose of adjusting characteristics such as a temperature range of a nematic phase, viscosity and dielectric anisotropy. The compound has a six-membered ring such as 1,4-cyclohexylene and 1,4-phenylene, and rod like molecular structure. “Polymerizable compound” is a compound to be added for the purpose of forming a polymer in the composition. “Polar compound” assists alignment of liquid crystal molecules by interaction of a polar group with a substrate surface.

The liquid crystal composition is prepared by mixing a plurality of liquid crystal compounds. A proportion (content) of the liquid crystal compounds is expressed in terms of weight percent (% by weight) based on the weight of the liquid crystal composition. An additive such as an optically active compound, an antioxidant, an ultraviolet light absorber, a dye, an antifoaming agent, the polymerizable compound, a polymerization initiator, a polymerization inhibitor and a polar compound is added to the liquid crystal composition when necessary. A proportion (amount of addition) of the additive is expressed in terms of weight percent (% by weight) based on the weight of the liquid crystal composition in a manner similar to the proportion of the liquid crystal compound. Weight parts per million (ppm) may be occasionally used. A proportion of the polymerization initiator and the polymerization inhibitor is exceptionally expressed based on the weight of the polymerizable compound.

A compound represented by formula (1) may be occasionally abbreviated as “compound (1).” Compound (1) means one compound, a mixture of two compounds or a mixture of three or more compounds represented by formula (1). A same rule applies also to at least one compound selected from the group of compounds represented by formula (2), or the like. Symbol B¹, C¹, F or the like surrounded by a hexagonal shape corresponds to ring B¹, ring C¹and ring F, respectively. The hexagonal shape represents a six-membered ring such as a cyclohexane ring and a benzene ring, or a condensed ring such as a naphthalene ring. An oblique line crossing the hexagonal shape represents that arbitrary hydrogen on the ring may be replaced by a group such as —Sp¹-P¹. A subscript such as e represents the number of groups subjected to replacement. When the subscript is 0, no such replacement exists.

A symbol of terminal group R¹¹is used in a plurality of component compounds. In the compounds, two groups represented by two pieces of arbitrary R¹¹may be identical or different. For example, in one case, R¹¹of compound (2) is ethyl and R¹¹of compound (3) is ethyl. In another case, R¹¹of compound (2) is ethyl and R¹¹of compound (3) is propyl. A same rule applies also to a symbol of any other terminal group, ring, bonding group or the like. In formula (8), when i is 2, two of rings D¹exist. In the compound, two groups represented by two of rings D¹may be identical or different. A same rule applies also to two of arbitrary rings D¹when i is larger than 2. A same rule applies also to a symbol of any other ring, bonding group or the like.

An expression “at least one piece of ‘A’” means that the number of ‘A’ is arbitrary. An expression “at least one piece of ‘A’ may be replaced by ‘B’” means that, when the number of ‘A’ is 1, a position of ‘A’ is arbitrary, and also when the number of ‘A’ is 2 or more, positions thereof can be selected without restriction. A same rule applies also to an expression “at least one piece of ‘A’ is replaced by ‘B’.” An expression “at least one piece of ‘A’ may be replaced by ‘B’, ‘C’ or ‘D’” includes a case where at least one piece of ‘A’ is replaced by ‘B’, a case where at least one piece of ‘A’ is replaced by ‘C’, and a case where at least one piece of ‘A’ is replaced by ‘D’, and also a case where a plurality of pieces of ‘A’ are replaced by at least two pieces of ‘B’, ‘C’ and ‘D’. For example, “alkyl in which at least one piece of —CH₂— (or —CH₂CH₂—) may be replaced by —O— (or —CH═CH—)” includes alkyl, alkenyl, alkoxy, alkoxyalkyl, alkoxyalkenyl and alkenyloxyalkyl. In addition, a case where two pieces of consecutive —CH₂— are replaced by —O— to form —O—O— is not preferred. In alkyl or the like, a case where —CH₂— of a methyl part (—CH₂—H) is replaced by —O— to form —O—H is not preferred, either.

Halogen means fluorine, chlorine, bromine or iodine. Preferred halogen is fluorine or chlorine. Further preferred halogen is fluorine. Alkyl is straight-chain alkyl or branched-chain alkyl, but includes no cyclic alkyl. In general, straight-chain alkyl is preferred to branched-chain alkyl. A same rule applies also to a terminal group such as alkoxy and alkenyl. With regard to a configuration of 1,4-cyclohexylene, trans is preferred to cis for increasing the maximum temperature of the nematic phase. Then, 2-fluoro-1,4-phenylene means two divalent groups described below. In a chemical formula, fluorine may be leftward (L) or rightward (R). A same rule applies also to an asymmetrical divalent group formed by eliminating two hydrogens from a ring, such as tetrahydropyran-2,5-diyl.

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The invention includes items described below.

Item 1. A compound, represented by formula (1):

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wherein, in formula (1),

a and b are 0, 1 or 2, and expressions: 0≤a+b≤3 hold,

P¹is a group represented by any one of formulas (1b) to (1i); and

P²is a group represented by formula (1a);

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wherein, in formulas (1a) to (1i), M¹and M²are independently hydrogen, halogen, alkyl having 1 to 5 carbons, or alkyl having 1 to 5 carbons in which at least one hydrogen is replaced by halogen; and

R¹is a group represented by any one of formula (2a), (2b) or (2c):

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wherein, R²is hydrogen, halogen or alkyl having 1 to 5 carbons, and in the alkyl, at least one hydrogen may be replaced by halogen, and at least one piece of —CH₂— may be replaced by —O—;

R³, R⁴and R⁵are independently hydrogen or alkyl having 1 to 15 carbons, and in the alkyl, at least one piece of —CH₂— may be replaced by —O— or —S—, and at least one piece of —(CH₂)₂— may be replaced by —CH═CH— or —C≡C—, and in the groups, at least one hydrogen may be replaced by halogen:

in formulas (2a), (2b) and (2c), Sp³and Sp4 are independently a single bond or alkylene having 1 to 10 carbons, and in the alkylene, at least one piece of —CH₂— may be replaced by —O—, —NH—, —CO—, —COO—, —OCO— or —OCOO—, and at least one piece of —(CH₂)₂— may be replaced by —CH═CH— or —C≡C—, and in the groups, at least one hydrogen may be replaced by halogen;

S¹is >CH—, >SiH— or >N—;

S²is >C< or >Si<;

X¹is independently a group represented by —OH, —NH₂, —OR⁶, —N(R⁶)₂, —COOH, —SH, —B(OH)₂or —Si(R⁶)₃, in which R⁶is hydrogen or alkyl having 1 to 10 carbons, and in the alkyl, at least one piece of —CH₂— may be replaced by —O—, and at least one piece of —(CH₂)₂— may be replaced by —CH═CH—, and in the groups, at least one hydrogen may be replaced by halogen; and

a and b are 0, 1 or 2, and expressions: 0≤a+b≤3 hold.

Item 2. The compound according to item 1, represented by formula (1):

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wherein, in formula (1),

a and b are 0, 1 or 2, and expressions: 0≤a+b≤2 hold;

Z¹, Z², Z³, Z⁴and Z⁵are independently a single bond, —(CH₂)₂—, —CH═CH—, —C≡C—, —COO—, —OCO—, —CF₂O—, —OCF₂—, —CH₂O—, —OCH₂—, —CF═CF—, —CH═CHCOO—, —OCOCH═CH—, —CH═CHCO— or —COCH═CH—, in which at least one in Z², Z³or Z⁴is any one of —COO—, —OCO—, —CH═CHCOO—, —OCOCH═CH—, —CH═CH—, —CH═CHCO— or —COCH═CH—, and when a or b is 2, two of arbitrary Z¹or Z⁵may be different;

Sp¹and Sp²are independently a single bond or alkylene having 1 to 10 carbons, and in the alkylene, at least one piece of —CH₂— may be replaced by —O—, —COO— or —OCO—, and at least one piece of —(CH₂)₂— may be replaced by —CH═CH—, and in the groups, at least one hydrogen may be replaced by fluorine or chlorine; and

P¹is a group represented by any one of formulas (1b) to (1i), and P²is a group represented by formula (1a):

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wherein, in the formulas,

M¹and M²are independently hydrogen, halogen, alkyl having 1 to 5 carbons, or alkyl having 1 to 5 carbons in which at least one hydrogen is replaced by halogen; and

R¹is a group represented by formula (2a):

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wherein, R²is hydrogen, halogen and alkyl having 1 to 5 carbons, and in the alkyl, at least one hydrogen may be replaced by halogen, and at least one piece of —CH₂— may be replaced by —O—;

R³, R⁴and R⁸are independently hydrogen or alkyl having 1 to 15 carbons, and in the alkyl, at least one piece of —CH₂— may be replaced by —O— or —S—, and at least one piece of —(CH₂)₂— may be replaced by —CH═CH— or —C≡C—, and in the groups, at least one hydrogen may be replaced by halogen:

wherein, in formula (2a),

Sp³is independently a single bond or alkylene having 1 to 10 carbons, and in the alkylene, at least one piece of —CH₂— may be replaced by —O—, —NH—, —CO—, —COO—, —OCO— or —OCOO—, and at least one piece of —(CH₂)₂— may be replaced by —CH═CH— or —C≡C—, and in the groups, at least one hydrogen may be replaced by halogen; and

X¹is a group represented by —OH, —NH₂, —OR³, —N(R³)₂, —COOH, —SH, —B(OH)₂or —Si(R³)₃, in which R³is hydrogen or alkyl having 1 to 10 carbons, and in the alkyl, at least one piece of —CH₂— may be replaced by —O—, and at least one piece of —(CH₂)₂— may be replaced by —CH═CH—, and in the groups, at least one hydrogen may be replaced by halogen.

Item 3. The compound according to any one of item 1 or 2, represented by any one of formulas (1-1) to (1-3):

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wherein, in formulas (1-1) to (1-3),

ring A¹, ring A², ring A³and ring A⁴are independently 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, naphthalene-2,6-diyl, tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, pyrimidine-2,5-diyl, pyridine-2,5-diyl, fluorene-2,7-diyl, phenanthrene-2,7-diyl or anthracene-2,6-diyl, and in the rings, at least one hydrogen may be replaced by fluorine, chlorine, alkyl having 1 to 12 carbons, alkenyl having 2 to 12 carbons, alkoxy having 1 to 11 carbons or alkenyloxy having 2 to 11 carbons, and in the groups, at least one hydrogen may be replaced by fluorine or chlorine;

Z¹, Z², Z³, Z⁴and Z⁵are independently a single bond, —(CH₂)₂—, —CH═CH—, —C≡C—, —COO—, —OCO—, —CF₂O—, —OCF₂—, —CH₂O—, —OCH₂—, —CF═CF—, —CH═CHCOO—, —OCOCH═CH—, —CH═CHCO— or —COCH═CH—, in which at least any one of Z², Z³and Z⁴is any one of —COO—, —OCO—, —CH═CHCOO—, —OCOCH═CH—, —CH═CH—, —CH═CHCO— or —COCH═CH—;

Sp¹, Sp²and Spa are independently a single bond or alkylene having 1 to 10 carbons, and in the alkylene, at least one piece of —CH₂— may be replaced by —O—, —COO—, —OCOO— or —OCO—, and at least one piece of —(CH₂)₂— may be replaced by —CH═CH—, and in the groups, at least one hydrogen may be replaced by fluorine or chlorine; and

P¹is independently a group represented by any one of formulas (1b) to (1i):

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wherein, in the formulas,

M¹and M²are independently hydrogen, halogen, alkyl having 1 to 5 carbons, or alkyl having 1 to 5 carbons in which at least one hydrogen is replaced by halogen; and

R¹is a group represented by formula (2a):

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wherein, R²is hydrogen, halogen or alkyl having 1 to 5 carbons, and in the alkyl, at least one hydrogen may be replaced by halogen, and at least one piece of —CH₂— may be replaced by —O—; and

R³, R⁴and R⁸are independently hydrogen or a straight-chain, branched-chain or cyclic alkyl having 1 to 15 carbons, and in the alkyl, at least one piece of —CH₂— may be replaced by —O— or —S—, and at least one piece of —(CH₂)₂— may be replaced by —CH═CH— or —C≡C—, and in the groups, at least one hydrogen may be replaced by halogen.

Item 4. The compound according to any one of items 1 to 3, represented by any one of formulas (1-1A) to (1-3A):

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wherein, in formulas (1-1A) to (1-3A),

ring A¹, ring A², ring A³and ring A⁴are independently 1,4-cyclohexylene, 1,4-phenylene, naphthalene-2,6-diyl, pyrimidine-2,5-diyl, pyridine-2,5-diyl, fluorene-2,7-diyl, phenanthrene-2,7-diyl and anthracene-2,6-diyl, and in the rings, at least one hydrogen may be replaced by fluorine, chlorine, alkyl having 1 to 12 carbons, alkenyl having 2 to 12 carbons, alkoxy having 1 to 11 carbons or alkenyloxy having 2 to 11 carbons, and in the groups, at least one hydrogen may be replaced by fluorine or chlorine;

Z², Z³and Z⁴are independently a single bond, —(CH₂)₂—, —CH═CH—, —C≡C—, —COO—, —OCO—, —CF₂O—, —OCF₂—, —CH₂O—, —OCH₂—, —CF═CF—, —CH═CHCOO—, —OCOCH═CH—, —CH═CHCO— or —COCH═CH—, in which at least any one of Z², Z³and Z⁴is any one of —COO—, —OCO—, —CH═CHCOO—, —OCOCH═CH—, —CH═CH—, —CH═CHCO— or —COCH═CH—;

Sp¹and Sp²are independently a single bond or alkylene having 1 to 10 carbons, and in the alkylene, at least one piece of —CH₂— may be replaced by —O—, —COO—, —OCOO— or —OCO—, and at least one piece of —(CH₂)₂— may be replaced by —CH═CH—, and in the groups, at least one hydrogen may be replaced by fluorine or chlorine; and

P¹is independently a group represented by any one of formulas (1b) to (1i);

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wherein, in the formulas,

M¹and M²are independently hydrogen, halogen, alkyl having 1 to 5 carbons, or alkyl having 1 to 5 carbons in which at least one hydrogen is replaced by halogen; and

R¹is a group represented by formula (2a);

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R³, R⁴and R⁵are independently hydrogen or a straight-chain, branched-chain or cyclic alkyl having 1 to 15 carbons, and in the alkyl, at least one piece of —CH₂— may be replaced by —O— or —S—, and at least one piece of —(CH₂)₂— may be replaced by —CH═CH— or —C≡C—, and in the groups, at least one hydrogen may be replaced by halogen.

Item 5. The compound according to any one of items 1 to 4, represented by any one of formulas (1-1-1) to (1-3-1):

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wherein, in formulas (1-1-1), (1-2-1) and (1-3-1),

ring A¹, ring A², ring A³and ring A⁴are independently 1,4-cyclohexylene, 1,4-phenylene or fluorene-2,7-diyl, and in the rings, at least one hydrogen may be replaced by fluorine, chlorine, alkyl having 1 to 12 carbons, alkenyl having 2 to 12 carbons, alkoxy having 1 to 11 carbons or alkenyloxy having 2 to 11 carbons;

Z², Z³and Z⁴are independently a single bond, —COO—, —OCO—, —CH═CHCOO—, —OCOCH═CH—, —CH═CH—, —CH═CHCO— or —COCH═CH—, in which at least any one of Z², Z³or Z⁴is any one of —COO—, —OCO—, —CH═CHCOO—, —OCOCH═CH—, —CH═CH—, —CH═CHCO— or —COCH═CH—;

Sp¹and Sp²are independently a single bond or alkylene having 1 to 10 carbons, and in the alkylene, at least one piece of —CH₂— may be replaced by —O—, —OCO—, —OCOO— or —OCO—, and at least one piece of —(CH₂)₂— may be replaced by —CH═CH—; and

P¹is independently a group represented by any one of formula (1b), (1c) or (1d);

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R⁵is independently hydrogen or alkyl having 1 to 15 carbons, and in the alkyl, at least one piece of —CH₂— may be replaced by —O— or —S—, and at least one piece of —(CH₂)₂— may be replaced by —CH═CH— or —C≡C—, and in the groups, at least one hydrogen may be replaced by halogen.

Item 6. The compound according to item 5, wherein, in formulas (1-1-1), (1-2-1) and (1-3-1), any one of Z², Z³or Z⁴is —COO— or —OCO—.

Item 7. The compound according to item 5, wherein, in formulas (1-1-1), (1-2-1) and (1-3-1), any one of Z², Z³or Z⁴is —CH═CHCOO—, —OCOCH═CH—, —CH═CH—, —CH═CHCO— or —COCH═CH—.

Item 8. The compound according to any one of items 1 to 5, represented by formula (1-A):

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wherein, P¹is independently a group represented by formula (1b), (1c) or (1d);

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wherein, R²is hydrogen, halogen or alkyl having 1 to 5 carbons, and in the alkyl, at least one hydrogen may be replaced by halogen, and at least one piece of —CH₂— may be replaced by —O—;

wherein, in the formulas,

Y is a group represented by any one of formulas (MES-1-01) to (MES-1-10);

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wherein, in the formulas,

R^ais independently fluorine, chlorine, methyl or ethyl;

R^bis independently hydrogen, fluorine, methyl or ethyl; and

in the formulas, the following notation in which 1,4-phenylene and (R^a) are connected by a straight line represents 1,4-phenylene in which one or two hydrogens may be replaced by Ra:

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Item 9. The compound according to any one of items 1 to 5, represented by formula (1-A):

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wherein, P¹is independently a group represented by formula (1b), (1c) or (1d);

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wherein, in the formulas

R²is hydrogen, halogen or alkyl having 1 to 5 carbons, and in the alkyl, at least one hydrogen may be replaced by halogen, and at least one piece of —CH₂— may be replaced by —O—;

Y is a group represented by any one of (MES-2-01) to (MES-2-16);

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wherein, R^ais independently fluorine, chlorine, methyl or ethyl; and

in the formulas, the following notation in which 1,4-phenylene and (R^a) are connected by a straight line represents 1,4-phenylene in which one or two hydrogens may be replaced by Ra:

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Item 10. A liquid crystal composition, containing at least one of compounds according to any one of items 1 to 9.

Item 11. The liquid crystal composition according to item 10, further containing at least one compound selected from the group of compounds represented by formulas (2) to (4):

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wherein, in formulas (2) to (4),

R¹¹and R¹²are independently alkyl having 1 to 10 carbons or alkenyl having 2 to 10 carbons, and in the alkyl and the alkenyl, at least one piece of —CH₂— may be replaced by —O—, and at least one hydrogen may be replaced by fluorine;

ring B¹, ring B², ring B³and ring B⁴are independently 1,4-cyclohexylene, 1,4-phenylene, 2-fluoro-1,4-phenylene, 2,5-difluoro-1,4-phenylene or pyrimidine-2,5-diyl; and

Z¹¹, Z¹²and Z¹³are independently a single bond, —CH₂CH₂—, —CH═CH—, —C≡C— or —COO—.

Item 12. The liquid crystal composition according to item 10 or 11, further containing at least one compound selected from the group of compounds represented by formulas (5) to (7):

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wherein, in formulas (5) to (7),

R¹³is alkyl having 1 to 10 carbons or alkenyl having 2 to 10 carbons, and in the alkyl and the alkenyl, at least one piece of —CH₂— may be replaced by —O—, and at least one hydrogen may be replaced by fluorine;

X¹¹is fluorine, chlorine, —OCF₃, —OCHF₂, —CF₃, —CHF₂, —CH₂F, —OCF₂CHF₂or —OCF₂CHFCF₃;

ring C¹, ring C²and ring C³are independently 1,4-cyclohexylene, 1,4-phenylene in which at least one hydrogen may be replaced by fluorine, tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl or pyrimidine-2,5-diyl;

Z¹⁴, Z¹⁵and Z¹⁶are independently a single bond, —CH₂CH₂—, —CH═CH—, —C≡C—, —COO—, —CF₂O—, —OCF₂—, —CH₂O—, —CF═CF—, —CH═CF— or —(CH₂)₄—; and

L¹¹and L¹²are independently hydrogen or fluorine.

Item 13. The liquid crystal composition according to item 10 or 11, further containing at least one compound selected from the group of compounds represented by formula (8):

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wherein, in formula (8),

R¹⁴is alkyl having 1 to 10 carbons or alkenyl having 2 to 10 carbons, and at least one piece of —CH₂— may be replaced by —O—, and at least one hydrogen may be replaced by fluorine;

X¹²is —C≡N or —C≡C—C≡N;

ring D¹is 1,4-cyclohexylene, 1,4-phenylene in which at least one hydrogen may be replaced by fluorine, tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl or pyrimidine-2,5-diyl;

Z¹⁷is a single bond, —CH₂CH₂—, —C≡C—, —COO—, —CF₂O—, —OCF₂— or —CH₂O—;

L¹³and L¹⁴are independently hydrogen or fluorine; and

i is 1, 2, 3 or 4.

Item 14. The liquid crystal composition according to item 10 or 11, further containing at least one compound selected from the group of compounds represented by formulas (9) to (15):

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wherein, in formulas (9) to (15),

R¹⁵and R¹⁶are independently alkyl having 1 to 10 carbons or alkenyl having 2 to 10 carbons, and in the alkyl and the alkenyl, at least one piece of —CH₂— may be replaced by —O—, and at least one hydrogen may be replaced by fluorine;

R¹⁷is hydrogen, fluorine, alkyl having 1 to 10 carbons or alkenyl having 2 to 10 carbons, and in the alkyl and the alkenyl, at least one piece of —CH₂— may be replaced by —O—, and at least one hydrogen may be replaced by fluorine;

ring E¹, ring E², ring E³and ring E⁴are independently 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene in which at least one hydrogen may be replaced by fluorine, tetrahydropyran-2,5-diyl or decahydronaphthalene-2,6-diyl;

ring E⁵and ring E⁶are independently, 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, tetrahydropyran-2,5-diyl or decahydronaphthalene-2,6-diyl;

Z¹⁸, Z¹⁹, Z²⁰and Z²¹are independently a single bond, —CH₂CH₂—, —COO—, —CH₂O—, —OCF₂— or —OCF₂CH₂CH₂—;

L¹⁵and L¹⁶are independently fluorine or chlorine;

S¹¹is hydrogen or methyl;

X is —CHF— or —CF₂—; and

j, k, m, n, p, q, r and s are independently 0 or 1, a sum of k, m, n and p is 1 or 2, a sum of q, r and s is 0, 1, 2 or 3, and t is 1, 2 or 3.

Item 15. The liquid crystal composition according to any one of items 10 to 14, containing at least one polymerizable compound selected from the group of compounds represented by formula (16):

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wherein, in formula (16),

ring F and ring I are independently cyclohexyl, cyclohexenyl, phenyl, 1-naphthyl, 2-naphthyl, tetrahydropyran-2-yl, 1,3-dioxane-2-yl, pyrimidine-2-yl or pyridine-2-yl, and in the rings, at least one hydrogen may be replaced by halogen, alkyl having 1 to 12 carbons, or alkyl having 1 to 12 carbons in which at least one hydrogen is replaced by halogen;

ring G 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, and in the rings, at least one hydrogen may be replaced by halogen, alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, or alkyl having 1 to 12 carbons in which at least one hydrogen is replaced by halogen;

Z²²and Z²³are independently a single bond or alkylene having 1 to 10 carbons, and in the alkylene, at least one piece of —CH₂— may be replaced by —O—, —CO—, —COO— or —OCO—, and at least one piece of —CH₂CH₂— may be replaced by —CH═CH—, —C(CH₃)═CH—, —CH═C(CH₃)— or —C(CH₃)═C(CH₃)—, and in the groups, at least one hydrogen may be replaced by fluorine or chlorine; and

P¹¹, P¹²and P¹³are independently a polymerizable group selected from the group of groups represented by formulas (P-1) to (P-5);

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wherein, M¹¹, M¹²and M¹³are independently hydrogen, fluorine, alkyl having 1 to 5 carbons, or alkyl having 1 to 5 carbons in which at least one hydrogen is replaced by fluorine or chlorine;

Sp¹¹, Sp¹²and Sp¹³are independently a single bond or alkylene having 1 to 10 carbons, and in the alkylene, at least one piece of —CH₂— may be replaced by —O—, —COO—, —OCO— or —OCOO—, and at least one piece of —CH₂CH₂— may be replaced by —CH═CH— or —C≡C—, and in the groups, at least one hydrogen may be replaced by fluorine or chlorine;

u is 0, 1 or 2; and

f, g and h are independently 0, 1, 2, 3 or 4, and a sum of f, g and h is 2 or more.

Item 16. The liquid crystal composition according to any one of items 10 to 15, containing at least one polymerizable compound selected from the group of compounds represented by formulas (16-1) to (16-27):

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wherein, in formulas (16-1) to (16-27), P¹¹, P¹²and P¹³are independently a polymerizable group selected from the group of groups represented by formulas (P-1) to (P-3), in which M¹¹, M¹²and M¹³are independently hydrogen, fluorine, alkyl having 1 to 5 carbons, or alkyl having 1 to 5 carbons in which at least one hydrogen is replaced by halogen:

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wherein, Sp¹¹, Sp¹²and Sp¹³are independently a single bond or alkylene having 1 to 10 carbons, and in the alkylene, at least one piece of —CH₂— may be replaced by —O—, —COO—, —OCO— or —OCOO—, and at least one piece of —CH₂CH₂— may be replaced by —CH═CH— or —C≡C—, and in the groups, at least one hydrogen may be replaced by fluorine or chlorine.

Item 17. The liquid crystal composition according to any one of items 10 to 16, further containing at least one of a polymerizable compound other than formulas (1) and (16), a polymerization initiator, a polymerization inhibitor, an optically active compound, an antioxidant, an ultraviolet light absorber, a light stabilizer, a heat stabilizer and an antifoaming agent.

Item 18. A liquid crystal display device, including at least one liquid crystal composition according to any one of items 10 to 19.

The invention further includes the following items: (a) the liquid crystal composition, further containing at least two of additives such as a polymerizable compound, a polymerization initiator, a polymerization inhibitor, an optically active compound, an antioxidant, an ultraviolet light absorber, a light stabilizer, a heat stabilizer and an antifoaming agent; (b) a polymerizable composition, prepared by adding a polymerizable compound different from compound (1) or compound (16) to the liquid crystal composition; (c) the polymerizable composition prepared by adding compound (1) and compound (16) to the liquid crystal composition; (d) a liquid crystal composite prepared by polymerizing the polymerizable composition; (e) a device that has a polymer sustained alignment mode, and contains the liquid crystal composite; and (f) a polymer sustained alignment mode device, prepared by using a polymerizable composition prepared by adding compound (1), compound (16), and a polymerizable compound different from compound (1) or compound (16) to the liquid crystal composition.

An aspect of compound (1), synthesis of compound (1), the liquid crystal composition and the liquid crystal display device will be described in the following order.

1. Aspect of Compound (1)

Compound (1) of the invention has features of having a mesogen moiety formed of at least one ring and an acryloyloxy group replaced by a polar group such as a hydroxyalkyl group. The polar group noncovalently interacts with a substrate surface of glass (or metal oxide), and therefore compound (1) tends to be unevenly distributed in a vicinity of the substrate surface in comparison with a compound having no polar group, and is useful. Thereby, an addition amount thereof becomes small. One of applications is as an additive for the liquid crystal composition used in the liquid crystal display device. Compound (1) is added for the purpose of horizontally controlling the alignment of liquid crystal molecules. Such an additive preferably has chemical stability under conditions in which the additive is sealed in the device, high solubility in the liquid crystal composition, and a large voltage holding ratio when the compound is used in the liquid crystal display device. Compound (1) satisfies such characteristics to a significant extent.

Preferred examples of compound (1) will be described.

Preferred examples of R¹, Z¹to Z⁵, A¹to A⁵, Sp¹, Sp², P²and a in compound (1) apply also to a subordinate formula of formula (1) for compound (1). In compound (1), characteristics can be arbitrarily adjusted by suitably combining kinds of the groups. Compound (1) may contain a larger amount of isotope such as ²H (deuterium) and ¹³C than an amount of natural abundance because no significant difference exists in the characteristics of the compound.

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Rings A¹, A², A³and A⁴are independently 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, naphthalene-2,6-diyl, decahydronaphthalene-2,6-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl, tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, pyrimidine-2,5-diyl, pyridine-2,5-diyl, fluorene-2,7-diyl, phenanthrene-2,7-diyl, anthracene-2,6-diyl, perhydrocyclopenta[a]phenanthrene-3,17-diyl or 2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydrocyclopenta[a]phenanthrene-3,17-diyl, and in the rings, at least one hydrogen may be replaced by fluorine, chlorine, alkyl having 1 to 12 carbons, alkenyl having 2 to 12 carbons, alkoxy having 1 to 11 carbons or alkenyloxy having 2 to 11 carbons, and in the groups, at least one hydrogen may be replaced by fluorine or chlorine, and when a is 2, two rings A¹may be different, and when b is 2, two rings A⁴may be different.

Preferred ring A¹, A², A³and A⁴are 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, naphthalene-2,6-diyl, decahydronaphthalene-2,6-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl, tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, pyrimidine-2,5-diyl, pyridine-2,5-diyl, perhydrocyclopenta[a]phenanthrene-3,17-diyl or 2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydrocyclopenta[a]phenanthrene-3,17-diyl, and in the rings, at least one hydrogen may be replaced by fluorine, chlorine, alkyl having 1 to 12 carbons, alkenyl having 2 to 12 carbons, alkoxy having 1 to 11 carbons or alkenyloxy having 2 to 11 carbons, and in the groups, at least one hydrogen may be replaced by fluorine or chlorine. Further preferred rings A¹, A², A³and A⁴are 1,4-cyclohexylene, 1,4-phenylene, perhydrocyclopenta[a]phenanthrene-3,17-diyl or 2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydrocyclopenta[a]phenanthrene-3,17-diyl, and in the rings, at least one hydrogen may be replaced by fluorine or alkyl having 1 to 5 carbons. Particularly preferred rings A¹, A², A³and A⁴are 1,4-cyclohexylene, 1,4-phenylene or perhydrocyclopenta[a]phenanthrene-3,17-diyl, and in the rings, at least one hydrogen may be replaced by fluorine, methyl or ethyl.

Z¹, Z², Z³, Z⁴and Z⁵are independently a single bond or alkylene having 1 to 10 carbons, and in the alkylene, at least one piece of —CH₂— may be replaced by —O—, —CO—, —COO—, —OCO— or —OCOO—, and at least one piece of —(CH₂)₂— may be replaced by —CH═CH— or —C≡C—, and in the groups, at least one hydrogen may be replaced by halogen, in which at least one in Z², Z³or Z⁴is —COO— and —OCO—, —CH═CHCOO—, —OCOCH═CH—, —CH═CH—, —CH═CHCO— or —COCH═CH—, and when a or b is 2, two of arbitrary Z¹or Z⁵may be different.

Preferred Z¹, Z², Z³, Z⁴and Z⁵are a single bond, —(CH₂)₂—, —CH═CH—, —C≡C—, —COO—, —OCO—, —CF₂O—, —OCF₂—, —CH₂O—, —OCH₂— or —CF═CF—. Further preferred Z¹, Z², Z³, Z⁴and Z⁵are a single bond, —(CH₂)₂— or —CH═CH—. Particularly preferred Z¹, Z², Z³, Z⁴and Z⁵are a single bond.

Preferred Sp¹and Sp²are a single bond, alkylene having 1 to 6 carbons, alkylene having 1 to 6 carbons in which one piece of —CH₂— is replaced by —O—, or —OCOO—. Further preferred Sp¹and Sp²are alkylene having 1 to 6 carbons or —OCOO—.

P¹is a group represented by any one of formulas (1b) to (1i).

Preferred P¹is represented by formulas (1b), (1c) and (1d).

P²is represented by formula (1a).

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In the formulas (1a) to (1i), M¹and M²are independently hydrogen, halogen, alkyl having 1 to 5 carbons, or alkyl having 1 to 5 carbons in which at least one hydrogen is replaced by halogen.

Preferred M¹or M²is hydrogen, fluorine, methyl, ethyl or trifluoromethyl. Further preferred M¹or M²is hydrogen.

R¹is represented by any one of formula (2a), (2b) or (2c).

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Preferred R¹is a group represented by formula (2a) or (2b). Further preferred R¹is a group represented by formula (2a).

R²is hydrogen, halogen or alkyl having 1 to 5 carbons, and in the alkyl, at least one hydrogen may be replaced by halogen, and at least one piece of —CH₂— may be replaced by —O—.

Preferred R²is hydrogen, fluorine, methyl, ethyl, methoxymethyl or trifluoromethyl. Further preferred R²is hydrogen.

R³, R⁴and R⁵are independently hydrogen or straight-chain alkyl having 1 to 15 carbons, branched-chain alkyl having 1 to 15 carbons or cyclic alkyl having 1 to 15 carbons, and in the alkyl, at least one piece of —CH₂— may be replaced by —O— or —S—, and at least one piece of —(CH₂)₂— may be replaced by —CH═CH— or —C≡C—, and in the groups, at least one hydrogen may be replaced by halogen.

Preferred R³, R⁴and R⁵are hydrogen, straight-chain alkyl having 1 to 10 carbons, straight-chain alkenyl having 2 to 10 carbons, straight-chain alkoxy having 1 to 10 carbons or cyclic alkyl having 3 to 6 carbons. Further preferred R³, R⁴and R⁵are hydrogen, straight-chain alkyl having 2 to 6 carbons, straight-chain alkenyl having 2 to 6 carbons, straight-chain alkoxy having 1 to 5 carbons or cyclic alkyl having 4 to 6 carbons.

In formulas (2a), (2b) and (2c), Sp³and Sp⁴are independently a single bond or alkylene having 1 to 10 carbons, and in the alkylene, at least one piece of —CH₂— may be replaced by —O—, —NH—, —CO—, —COO—, —OCO— or —OCOO—, and at least one piece of —(CH₂)₂— may be replaced by —CH═CH— or —C≡C—, and in the groups, at least one hydrogen may be replaced by halogen.

Preferred Sp³and Sp⁴are a single bond, alkylene having 1 to 6 carbons, or alkylene having 1 to 6 carbons in which one piece of —CH₂— is replaced by —O—. Further preferred Sp³and Sp⁴are alkylene having 1 to 4 carbons. Particularly preferred Sp³and Sp⁴are —CH₂—.

S¹is >CH—, >SiH— or >N—.

S²is >C< or >Si<.

Preferred S¹is >CH— or >N—, and preferred S²is >C<.

X¹is a group represented by —OH, —NH₂, —OR³, —N(R³)₂, —COOH, —SH, —B(OH)₂or —Si(R⁶)₃, in which R⁶is hydrogen or alkyl having 1 to 10 carbons, and in the alkyl, at least one piece of —CH₂— may be replaced by —O—, and at least one piece of —(CH₂)₂— may be replaced by —CH═CH—, and in the groups, at least one hydrogen may be replaced by halogen.

Preferred X¹is a group represented by —OH, —NH₂, —OR⁶, —N(R⁶)₂or —Si(R⁶)₃, in which R⁶is hydrogen or alkyl having 1 to 5 carbons, and in the alkyl, at least one piece of —CH₂— may be replaced by —O—, and at least one piece of —(CH₂)₂— may be replaced by —CH═CH—, and in the groups, at least one hydrogen may be replaced by fluorine. Further preferred X¹is —OH or —NH₂. Particularly preferred X¹is —OH.

Then, a and b are 0, 1 or 2, and expressions: 0≤a+b≤3 hold.

Then, expressions: 0≤a+b≤2 preferably hold.

Preferred examples of compound (1) include formulas (1-1) to (1-3).

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Definition of a symbol in formulas (1-1) to (1-3) and preferred examples are identical with compound (1). Moreover, specific examples of compound (1) will be described in Examples described later.

In formulas (2) to (15), component compounds of the liquid crystal composition are shown. Compounds (2) to (4) have small dielectric anisotropy. Compounds (5) to (7) have large positive dielectric anisotropy. Compound (8) has a cyano group, and therefore has large positive dielectric anisotropy. Compounds (9) to (15) have large negative dielectric anisotropy. Specific examples of the compounds will be described later.

In compound (16), P¹¹, P¹²and P¹³are independently a polymerizable group.

Preferred P¹¹, P¹²or P¹³is a polymerizable group selected from the group of groups represented by formulas (P-1) to (P-5). Further preferred P¹, P²or P³is group (P-1), group (P-2) or group (P-3). Particularly preferred group (P-1) is —OCO—CH═CH₂or —OCO—C(CH₃)═CH₂. A wavy line in group (P-1) to group (P-5) represents a site to form a bonding.

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In the groups (P-1) to (P-5), M¹¹, M¹²and M¹³are independently hydrogen, fluorine, alkyl having 1 to 5 carbons, or alkyl having 1 to 5 carbons in which at least one hydrogen is replaced by halogen.

Preferred M¹¹, M¹²or M¹³is hydrogen or methyl for increasing reactivity. Further preferred M¹¹is methyl, and further preferred M¹²or M¹³is hydrogen.

Preferred Sp¹¹, SP¹²or Sp¹³is a single bond.

Ring F and ring I are independently cyclohexyl, cyclohexenyl, phenyl, 1-naphthyl, 2-naphthyl, tetrahydropyran-2-yl, 1,3-dioxane-2-yl, pyrimidine-2-yl or pyridine-2-yl, and in the rings, at least one hydrogen may be replaced by halogen, alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, or alkyl having 1 to 12 carbons in which at least one hydrogen is replaced by halogen.

Preferred ring F or ring I is phenyl. Ring G 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, and in the rings, at least one hydrogen may be replaced by halogen, alkyl having 1 to 12 carbons, alkoxy having 1 to 12 carbons, or alkyl having 1 to 12 carbons in which at least one hydrogen is replaced by halogen. Particularly preferred ring G is 1,4-phenylene or 2-fluoro-1,4-phenylene.

Preferred Z⁷or Z⁸is a single bond, —CH₂CH₂—, —CH₂O—, —OCH₂—, —COO— or —OCO—. Further preferred Z²²or Z²³is a single bond.

Then, u is 0, 1 or 2.

Preferred u is 0 or 1. Then, f, g and h are independently 0, 1, 2, 3 or 4, and a sum of f, g and h is 1 or more. Preferred f, g or h is 1 or 2.

2. Synthesis of Compound (1)

A synthesis method of compound (1) will be described. Compound (1) can be prepared by suitably combining methods in synthetic organic chemistry. Any compounds whose synthetic methods are not described above are prepared according to methods described in books such as “Organic Syntheses” (John Wiley & Sons, Inc.), “Organic Reactions” (John Wiley & Sons, Inc.), “Comprehensive Organic Synthesis” (Pergamon Press) and “New Experimental Chemistry Course (Shin Jikken Kagaku Koza in Japanese)” (Maruzen Co., Ltd.).

2-1. Formation of Bonding Groups Z¹, Z², Z³, Z⁴and Z⁵

An example of a method of forming a bonding group in compound (1) is as described in a scheme described below. In the scheme, MSG¹(or MSG²) is a monovalent organic group having at least one ring. Monovalent organic groups represented by a plurality of MSG¹(or MSG²) may be identical or different. Compounds (1A) to (1G) correspond to compound (1) or an intermediate of compound (1).

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(I) Formation of a Single Bond

Compound (1A) is prepared by allowing aryl boronic acid (21) to react with compound (22) in the presence of carbonate and a tetrakis(triphenylphosphine)palladium catalyst. Compound (1A) is also prepared by allowing compound (23) to react with n-butyllithium and subsequently with zinc chloride, and further with compound (22) in the presence of a dichlorobis(triphenylphosphine)palladium catalyst.

(II) Formation of —COO— and —OCO—

Carboxylic acid (24) is obtained by allowing compound (23) to react with n-butyllithium and subsequently with carbon dioxide. Compound (1B) having —COO— is prepared by dehydration of carboxylic acid (24) and phenol (25) derived from compound (21) in the presence of 1,3-dicyclohexylcarbodiimide (DCC) and 4-dimethylaminopyridine (DMAP). A compound having —OCO— is also prepared according to the method.

(III) Formation of —CF₂O— and —OCF₂—

Compound (26) is obtained by sulfurizing compound (1B) with Lawesson's reagent. Compound (1C) having —CF₂O— is prepared by fluorinating compound (26) with a hydrogen fluoride-pyridine complex and N-bromosuccinimide (NBS). Refer to M. Kuroboshi et al., Chem. Lett., 1992, 827. Compound (1C) is also prepared by fluorinating compound (26) with (diethylamino)sulfur trifluoride (DAST). Refer to W. H. Bunnelle et al., J. Org. Chem. 1990, 55, 768. A compound having —OCF₂— is also prepared according to the method.

(IV) Formation of —CH═CH—

Aldehyde (27) is obtained by allowing compound (22) to react with n-butyllithium and subsequently with N,N-dimethylformamide (DMF). Compound (1D) is prepared by allowing phosphorus ylide generated by allowing phosphonium salt (28) to react with potassium t-butoxide to react with aldehyde (27). A cis isomer may be formed depending on reaction conditions, and therefore the cis isomer is isomerized into a trans isomer according to a publicly-known method when necessary.

(V) Formation of —CH₂CH₂—

Compound (1E) is prepared by hydrogenating compound (10) in the presence of a palladium on carbon catalyst.

(VI) Formation of —C≡C—

Compound (29) is obtained by allowing compound (23) to react with 2-methyl-3-butyn-2-ol in the presence of a catalyst of dichloropalladium and copper iodide, and then performing deprotection under basic conditions. Compound (1F) is prepared by allowing compound (29) to react with compound (22) in the presence of a catalyst of dichlorobis(triphenylphosphine)palladium and copper halide.

(VII) Formation of —CH₂O— and —OCH₂—

Compound (30) is obtained by reducing compound (27) with sodium borohydride. Compound (31) is obtained by brominating the obtained compound with hydrobromic acid. Compound (1G) is prepared by allowing compound (25) to react with compound (31) in the presence of potassium carbonate. A compound having —OCH₂— is also prepared according to the method.

(VIII) Formation of —CF═CF—

Compound (32) is obtained by treating compound (23) with n-butyllithium, and then allowing the treated material to react with tetrafluoroethylene. Compound (1H) is prepared by treating compound (22) with n-butyllithium, and then allowing the treated material to react with compound (32).

(VIV) Formation of —CH═CHCO— and —COCH═CH—

Compound (1J) is prepared by allowing compound (40) to be subjected to aldol condensation reaction with compound (27) in the presence of NaCH.

(X) Formation of —CH═CHCOO— and —OCOCH═CH—

Compound (1J) is prepared by dehydration of cinnamic acid (41) and compound (25) in the presence of 1,3-dicyclohexylcarbodiimide (DCC) and 4-dimethylaminopyridine (DMAP).

2-2. Formation of Rings A¹, A², A³and A⁴

A starting material is commercially available or a synthetic method is well known with regard to a ring such as 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, 2-fluoro-1,4-phenylene, 2-methyl-1,4-phenylene, 2-ethyl-1,4-phenylene, naphthalene-2,6-diyl, decahydronaphthalene-2,6-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl, tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, pyrimidine-2,5-diyl, pyridine-2,5-diyl, perhydrocyclopenta[a]phenanthrene-3,17-diyl and 2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydrocyclopenta[a]phenanthrene-3,17-diyl.

2-3. Formation of Linking Group Sp¹or Sp²and Polymerizable Group P¹or P²

Preferred examples of polymerizable group P¹or P²include acryloyloxy (1b), maleimide (1c), itaconate (1d), oxiranyl (1h) or vinyloxy (1i).

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An example of a method for preparing a compound in which the polymerizable group is bonded to a ring through linking group Sp¹or Sp²is as described below. First, an example in which linking group Sp¹or Sp²is a single bond will be described.

(1) Formation of a Single Bond

An example of a method for forming a single bond is as described in a scheme below. In the scheme, MSG¹is a monovalent organic group having at least one ring. Compounds (1S) to (1Z) correspond to compound (1).

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A synthesis method of the compound in which linking group Sp¹or Sp²is a single bond is described above. As for a method for producing other linking groups, other linking groups can be prepared according to the synthesis method of bonding groups Z¹, Z², Z³, Z⁴and Z⁵.

2-4. Synthesis Example

An example of a method for preparing compound (1) is as described below. In the compounds, MES is a mesogen group having at least one ring. Definitions of P¹, M¹, M², Sp¹and Sp²are identical to the definitions described above.

Compound (51A) or compound (51B) is commercially available, or can be prepared according to a common organic synthesis method by using a mesogen (MES) having a suitable ring structure as a starting material. When a compound in which MES and Sp¹is connected through an ether bond is prepared, compound (53) can be obtained by allowing compound (51A) as a starting material to perform etherification by using compound (52) and a base such as potassium hydroxide. Moreover, when a compound in which MES and Sp¹is connected by a single bond is prepared, compound (53) can be obtained by allowing compound (51B) as a starting material to perform cross-coupling reaction by using compound (52), a metal catalyst such as palladium and a base. Compound (53) may be derived to compound (54) in which a protective group such as TMS and THP is allowed to act therewith, when necessary.

Then, compound (56) can be obtained by allowing compound (53) or compound (54) to perform etherification again in the presence of a base such as compound (55) and potassium hydroxide. On this occasion, when the protective group is allowed to act in a previous stage, the protective group is removed by a deprotection reaction.

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Compound (1A) in which P²is a group represented by formula (1a), R²is represented by formula (2a), Sp³is —CH₂— and X¹is —OH can be prepared from compound (56) according to a method described below. Compound (59) is obtained by allowing compound (57) to perform an esterification reaction in the presence of compound (58), DCC and DMAP. Compound (59) can be derived to compound (1A) by performing reaction in the presence of formaldehyde and 1,4-diazabicyclo[2.2.2]octane (DABCO). In addition, compound (59) can be prepared by allowing compound (57) and compound (60) to perform an esterification reaction in the presence of a base such as triethylamine.

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Compound (1A) can also be prepared by the method described below. Compound (62) is obtained by allowing compound (61) to react in the presence of formaldehyde and DABCO. Next, for example, compound (63) in which a hydroxyl group is protected by using t-butyldimethylsilyl chloride and a base is obtained, and then compound (64) is obtained by hydrolyzing compound (63) with a base such as lithium hydroxide. Compound (57) and compound (64) obtained are derived to compound (65) by allowing to react in the presence of DCC and DMAP, and then compound (1A) can be obtained by performing deprotection of compound (65) using tetrabutylammonium fluoride (TBAF).

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Compound (1B) in which P²is a group represented by formula (1a), R²is represented by formula (2a), Sp⁴is —(CH₂)₂— and X¹is —OH can be prepared according to a method described below. Compound (66) is obtained by acting phosphorus tribromide on compound (1A). Then, compound (1B) can be obtained therefrom by acting indium on compound (66), and then allowing the resulting compound to react with formaldehyde.

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3. Liquid Crystal Composition

A liquid crystal composition of the invention contains compound (1) as component A. Compound (1) can control the alignment of liquid crystal molecules by non-covalent interaction with a substrate of the device. The composition contains compound (1) as component A, and preferably further contains a liquid crystal compound selected from components B, C, D and E described below. Component B includes compounds (2) to (4). Component C includes compounds (5) to (7). Component D includes compound (8). Component E includes compounds (9) to (15). The composition may contain any other liquid crystal compound different from compounds (2) to (15). When the composition is prepared, components B, C, D and E are preferably selected by taking into account magnitude of positive or negative dielectric anisotropy or the like. The composition in which the components are appropriately selected has a high maximum temperature, a low minimum temperature, small viscosity, suitable optical anisotropy (more specifically, large optical anisotropy or small optical anisotropy), large positive or negative dielectric anisotropy, large specific resistance, high stability to heat and ultraviolet light and a suitable elastic constant (more specifically, a large elastic constant or a small elastic constant).

A preferred proportion of compound (1) is about 0.01% by weight or more for maintaining high stability to ultraviolet light, and about 5% by weight or less for dissolution in the liquid crystal composition. A further preferred proportion is in the range of about 0.05% by weight to about 2% by weight. A most preferred proportion is in the range of about 0.05% by weight to about 1% by weight.

Component B includes a compound in which two terminal groups are alkyl or the like. Preferred examples of component B include compounds (2-1) to (2-11), compounds (3-1) to (3-19) and compounds (4-1) to (4-7). In the compound of component B, R¹¹and R¹²are independently alkyl having 1 to 10 carbons or alkenyl having 2 to 10 carbons, and in the alkyl or the alkenyl, at least one piece of —CH₂— may be replaced by —O—, and at least one hydrogen may be replaced by fluorine.

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Component B has a small absolute value of dielectric anisotropy, and therefore is a compound close to neutrality. Compound (2) is mainly effective in decreasing the viscosity or adjusting the optical anisotropy. Compounds (3) and (4) are effective in extending a temperature range of a nematic phase by increasing the maximum temperature, or in adjusting the optical anisotropy.

As a content of component B increases, the dielectric anisotropy of the composition decreases, but the viscosity decreases. Thus, as long as a desired value of threshold voltage of a device is met, the content is preferably as large as possible. When a composition for the IPS mode, the VA mode or the like is prepared, the content of component B is preferably 30% by weight or more, and further preferably 40% by weight or more, based on the weight of the liquid crystal composition.

Component C is a compound having a halogen-containing group or a fluorine-containing group at a right terminal. Preferred examples of component C include compounds (5-1) to (5-16), compounds (6-1) to (6-120) and compounds (7-1) to (7-62). In the compound of component C, R¹³is alkyl having 1 to 10 carbons or alkenyl having 2 to 10 carbons, and in the alkyl and the alkenyl, at least one piece of —CH₂— may be replaced by —O—, and at least one hydrogen may be replaced by fluorine; and X¹¹is fluorine, chlorine, —OCF₃, —OCHF₂, —CF₃, —CHF₂, —CH₂F, —OCF₂CHF₂or —OCF₂CHFCF₃.

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Component C has positive dielectric anisotropy, and superb stability to heat, light and so forth, and therefore is used when a composition for the IPS mode, the FFS mode, the OCB mode or the like is prepared. A content of component C is suitably in the range of 1% by weight to 99% by weight, preferably in the range of 10% by weight to 97% by weight, and further preferably in the range of 40% by weight to 95% by weight, based on the weight of the liquid crystal composition. When component C is added to a composition having negative dielectric anisotropy, the content of component C is preferably 30% by weight or less based on the weight of the liquid crystal composition. Addition of component C allows adjustment of the elastic constant of the composition and adjustment of a voltage-transmittance curve of the device.

Component D is compound (8) in which a right-terminal group is —C≡N or —C≡C—C≡N. Preferred examples of component D include compounds (8-1) to (8-64). In the compounds of component D, R¹⁴is alkyl having 1 to 10 carbons or alkenyl having 2 to 10 carbons, and in the alkyl and the alkenyl, at least one piece of —CH₂— may be replaced by —O—, and at least one hydrogen may be replaced by fluorine; and —X¹²is —C≡N or —C≡C—C≡N.

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Component D has positive dielectric anisotropy and a value thereof is large, and therefore is mainly used when a composition for the TN mode or the like is prepared. Addition of component D can increase the dielectric anisotropy of the composition. Component D is effective in extending a temperature range of a liquid crystal phase, adjusting the viscosity or adjusting the optical anisotropy. Component D is also useful for adjustment of the voltage-transmittance curve of the device.

When the composition for the TN mode or the like is prepared, a content of component D is suitably in the range of 1% by weight to 99% by weight, preferably in the range of 10% by weight to 97% by weight, and further preferably in the range of 40% by weight to 95% by weight, based on the weight of the liquid crystal composition. When component D is added to a composition having negative dielectric anisotropy, the content of component D is preferably 30% by weight or less based on the weight of the liquid crystal composition. Addition of component D allows adjustment of the elastic constant of the composition and adjustment of the voltage-transmittance curve of the device.

Component E includes compounds (9) to (15). The compounds have phenylene in which hydrogen in lateral positions are replaced by two halogens, such as 2,3-difluoro-1,4-phenylene.

Preferred examples of component E include compounds (9-1) to (9-8), compounds (10-1) to (10-17), compound (11-1), compounds (12-1) to (12-3), compounds (13-1) to (13-11), compounds (14-1) to (14-3), compounds (15-1) to (15-3) and compound (16-1). In the compounds of component E, R¹⁵and R¹⁶are independently alkyl having 1 to 10 carbons or alkenyl having 2 to 10 carbons, and in the alkyl and the alkenyl, at least one piece of —CH₂— may be replaced by —O—, and at least one hydrogen may be replaced by fluorine; and R¹⁷is hydrogen, fluorine, alkyl having 1 to 10 carbons or alkenyl having 2 to 10 carbons, and in the alkyl and the alkenyl, at least one piece of —CH₂— may be replaced by —O—, and at least one hydrogen may be replaced by fluorine.

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Component E has large negative dielectric anisotropy. Component E is used when a composition for the IPS mode, the VA mode, the PSA mode or the like is prepared. As a content of component E increases, the dielectric anisotropy of the composition negatively increases, but the viscosity increases. Thus, as long as a desired value of threshold voltage of the device is met, the content is preferably as small as possible. When the dielectric anisotropy at a degree of −5 is taken into account, the content is preferably 40% by weight or more in order to allow a sufficient voltage driving.

Among types of component E, compound (9) is a bicyclic compound, and therefore is mainly effective in decreasing the viscosity, adjusting the optical anisotropy or increasing the dielectric anisotropy. Compounds (10) and (11) are a tricyclic compound, and therefore are effective in increasing the maximum temperature, the optical anisotropy or the dielectric anisotropy. Compounds (12) to (15) are effective in increasing the dielectric anisotropy.

When a composition for the IPS mode, the VA mode, the PSA mode or the like is prepared, the content of component E is preferably 40% by weight or more, and further preferably in the range of 50% by weight to 95% by weight, based on the weight of the liquid crystal composition. When component E is added to a composition having positive dielectric anisotropy, the content of component E is preferably 30% by weight or less based on the weight of the liquid crystal composition. Addition of component E allows adjustment of the elastic constant of the composition and adjustment of the voltage-transmittance curve of the device.

The liquid crystal composition satisfying at least one of characteristics such as the high maximum temperature, the low minimum temperature, the small viscosity, the suitable optical anisotropy, the large positive or negative dielectric anisotropy, the large specific resistance, the high stability to ultraviolet light, the high stability to heat and the large elastic constant can be prepared by suitably combining component B, C, D and E described above. A liquid crystal compound different from components B, C, D and E may be added when necessary.

A liquid crystal composition is prepared according to a publicly-known method. For example, the component compounds are mixed and dissolved in each other by heating. According to an application, an additive may be added to the composition. Specific examples of the additives include a polymerizable compound other than formula (1) and formula (16), a polymerization initiator, a polymerization inhibitor, an optically active compound, an antioxidant, an ultraviolet light absorber, a light stabilizer, a heat stabilizer and an antifoaming agent. Such additives are well known to those skilled in the art, and described in literature.

The polymerizable compound is added for the purpose of forming a polymer in the liquid crystal composition. The polymerizable compound and compound (1) are copolymerized by irradiation with ultraviolet light while voltage is applied between electrodes, whereby the polymer is formed in the liquid crystal composition. On the occasion, compound (1) is immobilized in a state in which the polar group non-covalently interacts with the substrate surface of glass (or metal oxide). Thus, capability of controlling the alignment of liquid crystal molecules is further improved, and simultaneously the polar compound no longer leaks into the liquid crystal composition. Moreover, suitable pretilt can be obtained even in the substrate surface of glass (or metal oxide), and therefore a liquid crystal display device in which a response time is shortened and the voltage holding ratio is large can be obtained.

Preferred examples of the polymerizable compound include acrylate, methacrylate, a vinyl compound, a vinyloxy compound, propenyl ether, an epoxy compound (oxirane, oxetane) and vinyl ketone. Further preferred examples include a compound having at least one acryloyloxy, and a compound having at least one methacryloyloxy. Still further preferred examples also include a compound having both acryloyloxy and methacryloyloxy.

Still further preferred examples include compounds (M-1) to (M-17). In compounds (M-1) to (M-17), R²⁵to R³¹are independently hydrogen or methyl; s, v and x are independently 0 or 1; t and u are independently an integer from 1 to 10; and L²¹to L²⁶are independently hydrogen or fluorine, and L²⁷and L²⁸are independently hydrogen, fluorine or methyl.

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The polymerizable compound can be rapidly polymerized by adding the polymerization initiator. An amount of a remaining polymerizable compound can be decreased by optimizing a reaction temperature. Examples of a photoradical polymerization initiator include TPO, 1173 and 4265 from Darocur series of BASF SE, and 184, 369, 500, 651, 784, 819, 907, 1300, 1700, 1800, 1850 and 2959 from Irgacure series thereof.

Additional examples of the photoradical polymerization initiator include 4-methoxyphenyl-2,4-bis(trichloromethyl)triazine, 2-(4-butoxystyryl)-5-trichloromethyl-1,3,4-oxadiazole, 9-phenylacridine, 9,10-benzphenazine, a benzophenone-Michler's ketone mixture, a hexaarylbiimidazole-mercaptobenzimidazole mixture, 1-(4-isopropylphenyl)-2-hydroxy-2-methylpropane-1-one, benzyl dimethyl ketal, 2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropane-1-one, a mixture of 2,4-diethylxanthone and methyl p-dimethylaminobenzoate, and a mixture of benzophenone and methyltriethanolamine.

After the photoradical polymerization initiator is added to the liquid crystal composition, polymerization can be performed by irradiation with ultraviolet light in a state in which an electric field is applied thereto. However, an unreacted polymerization initiator or a decomposition product of the polymerization initiator may cause poor display such as image persistence in the device. In order to prevent such an event, photopolymerization may be performed with no addition of the polymerization initiator. A preferred wavelength of light to be irradiated is in the range of 150 nanometers to 500 nanometers. A further preferred wavelength is in the range of 250 nanometers to 450 nanometers, and a most preferred wavelength is in the range of 300 nanometers to 400 nanometers.

Upon mixing compound (1) having an ester bonding group, a cinnamic acid ester bond, a chalcone skeleton or a stilbene skeleton in the composition, a main effect of the component compound on the characteristics of the composition is as described below. When Fries rearrangement, photodimerization or cis-trans isomerization of a double bond is caused by polarized light, the compound (1) is aligned in a fixed direction at a molecular level. Accordingly, a thin film prepared from the polar compound aligns the liquid crystal molecules in the same manner as an alignment film of polyimide or the like.

In a compound having an aromatic ester and a polymerizable group, photolysis in an aromatic ester moiety is caused by irradiation with ultraviolet light to form a radical, and photo-Fries rearrangement is caused. In the photo-Fries rearrangement, the photolysis of the aromatic ester moiety is caused when a polarization direction of polarized ultraviolet light and a major axis direction of the aromatic ester moiety are identical. Recombination of the compound is caused after photolysis to generate a hydroxyl group in the molecule by tautomerization. Interaction in a substrate interface is caused by the hydroxyl group, and the polar compound is considered to be easily adsorbed with anisotropy on a side of the substrate interface. Moreover, the compound has the polymerizable group, and therefore is immobilized by polymerization. The property is utilized, whereby the thin film capable of aligning the liquid crystal molecule can be prepared. Linearly polarized light is suitable as ultraviolet light to be irradiated in order to prepare the thin film. First, the polar compound is added to the liquid crystal composition in the range of 0.1% by weight to 10% by weight, and the resulting composition is warmed in order to dissolve the polar compound thereinto. The composition is injected into the device having no alignment film. Next, the devise is irradiated with the linearly polarized light while warming the device to cause the photo-Fries rearrangement of the polar compound to polymerize the compound. The polar compound in which the photo-Fries rearrangement is caused is aligned in a fixed direction, and the thin film formed after polymerization has a function as a liquid crystal alignment film.

Upon storing the polymerizable compound, the polymerization inhibitor may be added thereto for preventing polymerization. The polymerizable compound is ordinarily added to the composition without removing the polymerization inhibitor. Specific examples of the polymerization inhibitor include hydroquinone, a hydroquinone derivative such as methylhydroquinone, 4-t-butylcatechol, 4-methoxyphenol and phenothiazine.

The optically active compound is effective in inducing helical structure in the liquid crystal molecules to give a required twist angle, thereby preventing a reverse twist. A helical pitch can be adjusted by adding the optically active compound thereto. Two or more optically active compounds may be added for the purpose of adjusting temperature dependence of the helical pitch. Specific examples of a preferred optically active compound include compounds (Op-1) to (Op-18) described below. In compound (Op-18), ring J is 1,4-cyclohexylene or 1,4-phenylene, and R²⁸is alkyl having 1 to 10 carbons.

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The antioxidant is effective for maintaining the large voltage holding ratio. Preferred examples of the antioxidant include compounds (AO-1) and (AO-2) described below; and Irganox 415, Irganox 565, Irganox 1010, Irganox 1035, Irganox 3114 and Irganox 1098 (trade names; BASF SE). The ultraviolet light absorber is effective for preventing a decrease of the maximum temperature. Preferred examples of the ultraviolet light absorber include a benzophenone derivative, a benzoate derivative, and a triazole derivative. Specific examples thereof include compounds (AO-3) and (AO-4) described below; Tinuvin 329, Tinuvin P, Tinuvin 326, Tinuvin 234, Tinuvin 213, Tinuvin 400, Tinuvin 328 and Tinuvin 99-2 (trade names; BASF SE); and 1,4-diazabicyclo[2.2.2]octane (DABCO).

The light stabilizer such as an amine having steric hindrance is preferred for maintaining the large voltage holding ratio. Specific examples of a preferred light stabilizer include compounds (AO-5) and (AO-6) described below; and Tinuvin 144, Tinuvin 765 and Tinuvin 770DF (trade names: BASF SE). The heat stabilizer is also effective for maintaining the large voltage holding ratio, and specific preferred examples include Irgafos 168 (trade name; BASF SE). The antifoaming agent is effective for preventing foam formation. Preferred examples of the antifoaming agent include dimethyl silicone oil and methylphenyl silicone oil.

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In compound (AO-1), R⁴⁰is alkyl having 1 to 20 carbons, alkoxy having 1 to 20 carbons, —COOR⁴¹or —CH₂CH₂COOR⁴¹, in which R⁴¹is alkyl having 1 to 20 carbons. In compounds (AO-2) and (AO-5), R⁴²is alkyl having 1 to 20 carbons. In compound (AO-5), R⁴³is hydrogen, methyl or O. (oxygen radical), ring G is 1,4-cyclohexylene or 1,4-phenylene, and z is 1, 2 or 3.

4. Liquid Crystal Display Device

The liquid crystal composition can be used in a liquid crystal display device having an operating mode such as the PC mode, the TN mode, the STN mode, the OCB mode and the PSA mode, and driven by an active matrix mode. The composition can also be used in a liquid crystal display device having the operating mode such as the PC mode, the TN mode, the STN mode, the OCB mode, the VA mode and the IPS mode, and driven by a passive matrix mode. The device can be applied to any of a reflective type, a transmissive type and a transflective type.

The composition can also be used in a nematic curvilinear aligned phase (NCAP) device prepared by microencapsulating a nematic liquid crystal, and a polymer dispersed liquid crystal display device (PDLCD) and a polymer network liquid crystal display device (PNLCD), in which a three-dimensional network-polymer is formed in the liquid crystal. When an amount of addition of the polymerizable compound is about 10% by weight or less based on the weight of the liquid crystal composition, a liquid crystal display device having the PSA mode is prepared. A preferred proportion thereof is in the range of about 0.1% by weight to about 2% by weight. A further preferred proportion is in the range of about 0.2% by weight to about 1.0% by weight. The device having the PSA mode can be driven by the driving mode such as the active matrix mode and the passive matrix mode. Such a device can be applied to any of the reflective type, the transmissive type and the transflective type. A polymer dispersed mode device can also be prepared by increasing the amount of addition of the polymerizable compound.

In the polymer sustained alignment mode device, the polymer contained in the composition aligns the liquid crystal molecules. The polar compound assists alignment of the liquid crystal molecules. More specifically, the polar compound can be used in place of the alignment film. One example of a method for manufacturing such a device is as described below.

A device having two substrates called an array substrate and a color filter substrate is arranged. The substrate has no the alignment film. At least one of the substrates has an electrode layer. A liquid crystal composition is prepared by mixing liquid crystal compounds. A polymerizable compound and a polar compound are added to the composition. An additive may be further added thereto when necessary. The composition is injected into the device. The device is irradiated with light. Ultraviolet light is preferred. The polymerizable compound is polymerized by irradiation with light. The composition containing a polymer is formed by the polymerization to prepare a device having a PSA mode.

A method of producing a device will be described. First, the method includes a step of adding a polar compound to a liquid crystal composition, and then warming the resulting composition to a temperature higher than the maximum temperature thereof to dissolve the polar compound. Second, the method includes a step of injecting the composition into a liquid crystal display device. Third, the method includes a step of irradiating the composition with polarized ultraviolet light while warming the liquid crystal composition to a temperature higher than the maximum temperature thereof. The polar compound causes the photo-Fries rearrangement by linearly polarized light, and simultaneously polymerization thereof also progresses. A polymer formed of the polar compound is formed as the thin film on the substrate and immobilized thereon. The compound is aligned in a fixed direction at a molecular level, and therefore the thin film has the function as the liquid crystal alignment film. A liquid crystal display device having no alignment film such as polyimide can be produced by the method described above.

In the procedure, the polar compound is unevenly distributed on the substrate because the polar group interacts with the surface of the substrate. If the polar compound is unevenly distributed, an amount of addition of the compound can be suppressed in comparison with the compound having no polar group. The polar compound aligns the liquid crystal molecules by irradiation with polarized ultraviolet light, and simultaneously the polymerizable compound is polymerized by ultraviolet light, and therefore a polymer maintaining the alignment is formed. The alignment of the liquid crystal molecules is additionally stabilized by an effect of the polymer, and therefore the response time in the device is shortened. The image persistence is caused due to poor operation of the liquid crystal molecules, and therefore the persistence is also simultaneously improved by the effect of the polymer. In particular, compound (1) of the invention is a polymerizable polar compound, and therefore aligns liquid crystal molecules, and also is copolymerized with any other polymerizable compound. Thus, the polar compound is no longer leaked into the liquid crystal composition, and therefore the liquid crystal display device having a large voltage holding ratio can be obtained.

EXAMPLES

Hereinafter, the invention will be described in greater detail by way of Examples (including Synthesis Examples and Use Examples of devices). However, the invention is not limited by the Examples. The invention includes a mixture of a composition in Use Example 1 and a composition in Use Example 2. The invention also includes a mixture prepared by mixing at least two compositions in each Use Example.

1. Example of Compound (1)

Compound (1) was prepared according to procedures shown in Example. Unless otherwise specified, a reaction was performed under a nitrogen atmosphere. Compound (1) was prepared according to procedures shown in Example 1 or the like. The thus prepared compound was identified by methods such as an NMR analysis. Characteristics of compound (1), the liquid crystal compound, the composition and the device were measured by methods described below.

NMR analysis: For measurement, DRX-500 made by Bruker BioSpin Corporation was used. In ¹H-NMR measurement, a sample was dissolved in a deuterated solvent such as CDCl₃, and measurement was carried out under conditions of room temperature, 500 MHz and 16 times of accumulation. Tetramethylsilane was used as an internal standard. In ¹⁹F-NMR measurement, CFCl₃was used as an internal standard, and measurement was carried out under conditions of 24 times of accumulation. In explaining nuclear magnetic resonance spectra obtained, s, d, t, q, quin, sex and m stand for a singlet, a doublet, a triplet, a quartet, a quintet, a sextet and a multiplet, and br being broad, respectively.

Gas chromatographic analysis: For measurement, GC-2010 Gas Chromatograph made by Shimadzu Corporation was used. As a column, a capillary column DB-1 (length 60 m, bore 0.25 mm, film thickness 0.25 μm) made by Agilent Technologies, Inc. was used. As a carrier gas, helium (1 mL/minute) was used. A temperature of a sample vaporizing chamber and a temperature of a detector (FID) part were set to 300° C. and 300° C., respectively. A sample was dissolved in acetone and prepared to be a 1 weight % solution, and then 1 microliter of the solution obtained was injected into the sample vaporizing chamber. As a recorder, GC Solution System made by Shimadzu Corporation or the like was used.

HPLC analysis: For measurement, Prominence (LC-20AD; SPD-20A) made by Shimadzu Corporation was used. As a column, YMC-Pack ODS-A (length 150 mm, bore 4.6 mm, particle diameter 5 μm) made by YMC Co., Ltd. was used. As an eluate, acetonitrile and water were appropriately mixed and used. As a detector, a UV detector, an RI detector, a CORONA detector or the like was appropriately used. When the UV detector was used, a detection wavelength was set to 254 nanometers. A sample was dissolved in acetonitrile and prepared to be a 0.1 weight % solution, and then 1 microliter of the solution was introduced into a sample chamber. As a recorder, C-R7Aplus made by Shimadzu Corporation was used.

Ultraviolet-visible spectrophotometry: For measurement, PharmaSpec UV-1700 made by Shimadzu Corporation was used. A detection wavelength was adjusted in the range of 190 nanometers to 700 nanometers. A sample was dissolved in acetonitrile and prepared to be a 0.01 mmol/L solution, and measurement was carried out by putting the solution in a quartz cell (optical path length: 1 cm).

Sample for measurement: Upon measuring phase structure and a transition temperature (a clearing point, a melting point, a polymerization starting temperature or the like), the compound itself was used as a sample.

Measuring method: Measurement of characteristics was carried out by the methods described below. Most of the measuring methods are applied as described in the Standard of the Japan Electronics and Information Technology Industries Association (JEITA) (JEITA EIAJ ED-2521B) discussed and established by JEITA, or modified thereon. No thin film transistor (TFT) was attached to a TN device used for measurement.

(1) Phase Structure

A sample was placed on a hot plate in a melting point apparatus (FP-52 Hot Stage made by Mettler-Toledo International Inc.) equipped with a polarizing microscope. A state of phase and a change thereof were observed with the polarizing microscope while the sample was heated at a rate of 3° C. per minute, and a kind of the phase was specified.

(2) Transition Temperature (° C.)

For measurement, a differential scanning calorimeter, Diamond DSC System, made by PerkinElmer, Inc., or a high sensitivity differential scanning calorimeter, X-DSC7000, made by SSI NanoTechnology Inc. was used. A sample was heated and then cooled at a rate of 3° C. per minute, and a starting point of an endothermic peak or an exothermic peak caused by a phase change of the sample was determined by extrapolation, whereby a transition temperature was determined. A melting point and a polymerization starting temperature of a compound were also measured using the apparatus. Temperature at which a compound undergoes transition from a solid to a liquid crystal phase such as the smectic phase and the nematic phase may be occasionally abbreviated as “minimum temperature of the liquid crystal phase.” Temperature at which the compound undergoes transition from the liquid crystal phase to liquid may be occasionally abbreviated as “clearing point.”

A crystal was expressed as C. When the kind of crystals were distinguishable, each of the crystals was expressed as C₁or C₂. The smectic phase or the nematic phase was expressed as S or N. In the smectic phase, when smectic A phase, smectic B phase, smectic C phase or smectic F phase was distinguishable, the phases were expressed as S_A, S_B, S_Cor S_F, respectively. A liquid (isotropic) was expressed as I. A transition temperature was expressed as “C 50.0 N 100.0 I,” for example. The expression indicates that a transition temperature from the crystals to the nematic phase is 50.0° C., and a transition temperature from the nematic phase to the liquid is 100.0° C.

(3) Maximum Temperature of Nematic Phase (T_NIor NI; ° C.)

A sample was placed on a hot plate in a melting point apparatus equipped with a polarizing microscope, and heated at a rate of 1° C. per minute. Temperature when part of the sample began to change from a nematic phase to an isotropic liquid was measured. A maximum temperature of the nematic phase may be occasionally abbreviated as “maximum temperature.” When the sample was a mixture of compound (1) and the base liquid crystal, the maximum temperature was expressed in terms of a symbol T_NI. When the sample was a mixture of compound (1) and a compound such as components B, C and D, the maximum temperature was expressed in terms of a symbol NI.

(4) Minimum Temperature of Nematic Phase (T_C; ° C.)

Samples each having a nematic phase were kept in freezers at temperatures of 0° C., −10° C., −20° C., −30° C. and −40° C. for 10 days, and then liquid crystal phases were observed. For example, when the sample maintained the nematic phase at −20° C. and changed to crystals or a smectic phase at −30° C., T_Cwas expressed as T_C≤−20° C. A minimum temperature of the nematic phase may be occasionally abbreviated as “minimum temperature.”

(5) Viscosity (Bulk Viscosity; η; Measured at 20° C.; mPa·s)

For measurement, a cone-plate (E type) rotational viscometer made by Tokyo Keiki Inc. was used.

(6) Optical Anisotropy (Refractive Index Anisotropy; Measured at 25° C.; Δn)

Measurement was carried out by an Abbe refractometer with a polarizing plate mounted on an ocular, using light at a wavelength of 589 nanometers. A surface of a main prism was rubbed in one direction, and then a sample was added dropwise onto the main prism. A refractive index (n∥) was measured when a direction of polarized light was parallel to a direction of rubbing. A refractive index (n⊥) was measured when the direction of polarized light was perpendicular to the direction of rubbing. A value of optical anisotropy (Δn) was calculated from an equation: Δn=n∥−n⊥.

(7) Specific Resistance (ρ; Measured at 25° C.; ΩCm)

Into a vessel equipped with electrodes, 1.0 milliliter of sample was injected. A direct current voltage (10 V) was applied to the vessel, and a direct current after 10 seconds was measured. Specific resistance was calculated from the following equation: (specific resistance)={(voltage)×(electric capacity of a vessel)}/{(direct current)×(dielectric constant of vacuum)}.

The measuring method of the characteristics may be different between a sample having positive dielectric anisotropy and a sample having negative dielectric anisotropy. When the dielectric anisotropy was positive, the measuring methods were described in sections (8a) to (12a). When the dielectric anisotropy was negative, the measuring methods were described in sections (8b) to (12b).

(8a) Viscosity (Rotational Viscosity; γ1; Measured at 25° C.; mPa·s)

Positive dielectric anisotropy: Measurement was carried out according to a method described in M. Imai et al., Molecular Crystals and Liquid Crystals, Vol. 259, p. 37 (1995). A sample was put in a TN device in which a twist angle was 0 degrees and a distance (cell gap) between two glass substrates was 5 micrometers. Voltage was applied stepwise to the device in the range of 16 V to 19.5 V at an increment of 0.5 V. After a period of 0.2 second with no voltage application, voltage was repeatedly applied under conditions of only one rectangular wave (rectangular pulse; 0.2 second) and no voltage application (2 seconds). A peak current and a peak time of transient current generated by the applied voltage were measured. A value of rotational viscosity was obtained from the measured values and calculation equation (8) described on page 40 of the paper presented by M. Imai et al. A value of dielectric anisotropy required for the calculation was determined using the device by which the rotational viscosity was measured and by a method described below.

(8b) Viscosity (Rotational Viscosity; γ1; Measured at 25° C.; mPa·s)

Negative dielectric anisotropy: Measurement was carried out according to a method described in M. Imai et al., Molecular Crystals and Liquid Crystals, Vol. 259, p. 37 (1995). A sample was put in a VA device in which a distance (cell gap) between two glass substrates was 20 micrometers. Voltage was applied stepwise to the device in the range of 39 V to 50 V at an increment of 1 V. After a period of 0.2 second with no voltage application, voltage was repeatedly applied under conditions of only one rectangular wave (rectangular pulse; 0.2 second) and no voltage application (2 seconds). A peak current and a peak time of transient current generated by the applied voltage were measured. A value of rotational viscosity was obtained from the measured values and calculation equation (8) described on page 40 of the paper presented by M. Imai et al. In dielectric anisotropy required for the calculation, a value measured according to items of dielectric anisotropy described below was used.

(9a) Dielectric Anisotropy (Δε; Measured at 25° C.)

Positive dielectric anisotropy: A sample was put in a TN device in which a distance (cell gap) between two glass substrates was 9 micrometers and a twist angle was 80 degrees. Sine waves (10 V, 1 kHz) were applied to the device, and after 2 seconds, a dielectric constant (ε∥) of liquid crystal molecules in a major axis direction was measured. Sine waves (0.5 V, 1 kHz) were applied to the device, and after 2 seconds, a dielectric constant (ε⊥) of liquid crystal molecules in a minor axis direction was measured. A value of dielectric anisotropy was calculated from an equation: Δε=ε∥−ε⊥.

(9b) Dielectric Anisotropy (Δε; Measured at 25° C.)

Negative dielectric anisotropy: A value of dielectric anisotropy was calculated from an equation: Δε=ε∥−ε⊥. A dielectric constant (ε∥ and ε⊥) was measured as described below.

(1) Measurement of dielectric constant (ε∥): an ethanol (20 mL) solution of octadecyltriethoxysilane (0.16 mL) was applied to a well-cleaned glass substrate. After rotating the glass substrate with a spinner, the glass substrate was heated at 150° C. for 1 hour. A sample was put in a VA device in which a distance (cell gap) between two glass substrates was 4 micrometers, and the device was sealed with an ultraviolet-curable adhesive. Sine waves (0.5 V, 1 kHz) were applied to the device, and after 2 seconds, a dielectric constant (ε∥) of liquid crystal molecules in a major axis direction was measured.

(2) Measurement of dielectric constant (ε⊥): a polyimide solution was applied to a well-cleaned glass substrate. After calcining the glass substrate, rubbing treatment was applied to the alignment film obtained. A sample was put in a TN device in which a distance (cell gap) between two glass substrates was 9 micrometers and a twist angle was 80 degrees. Sine waves (0.5 V, 1 kHz) were applied to the device, and after 2 seconds, a dielectric constant (ε⊥) of liquid crystal molecules in a minor axis direction was measured.

(10a) Elastic constant (K; measured at 25° C.; pN)

Positive dielectric anisotropy: For measurement, HP4284A LCR Meter made by Yokogawa-Hewlett-Packard Co. was used. A sample was put in a horizontal alignment device in which a distance (cell gap) between two glass substrates was 20 micrometers. An electric charge of 0 V to 20 V was applied to the device, and electrostatic capacity and applied voltage were measured. The measured values of electrostatic capacity (C) and applied voltage (V) were fitted to equation (2.98) and equation (2.101) on page 75 of “Liquid Crystal Device Handbook” (Ekisho Debaisu Handobukku in Japanese; Nikkan Kogyo Shimbun, Ltd.), and values of K₁₁and K₃₃were obtained from equation (2.99). Next, K₂₂was calculated using the previously determined values of K₁₁and K₃₃in equation (3.18) on page 171. Elastic constant K was expressed in terms of a mean value of the thus determined K₁₁, K₂₂and K₃₃.

(10b) Elastic Constant (K₁₁and K₃₃; Measured at 25° C.; pN)

Negative dielectric anisotropy: For measurement, Elastic Constant Measurement System Model EC-1 made by TOYO Corporation was used. A sample was put in a vertical alignment device in which a distance (cell gap) between two glass substrates was 20 micrometers. An electric charge of 20 V to 0 V was applied to the device, and electrostatic capacity and applied voltage were measured. Values of electrostatic capacity (C) and applied voltage (V) were fitted to equation (2.98) and equation (2.101) on page 75 of “Liquid Crystal Device Handbook” (Ekisho Debaisu Handobukku in Japanese; Nikkan Kogyo Shimbun, Ltd.), and a value of elastic constant was obtained from equation (2.100).

(11a) Threshold Voltage (Vth; Measured at 25° C.; V)

Positive dielectric anisotropy: For measurement, an LCD-5100 luminance meter made by Otsuka Electronics Co., Ltd. was used. A light source was a halogen lamp. A sample was put in a normally white mode TN device in which a distance (cell gap) between two glass substrates was 0.45/Δn (μm) and a twist angle was 80 degrees. A voltage (32 Hz, rectangular waves) to be applied to the device was stepwise increased from 0 V to 10 V at an increment of 0.02 V. On the occasion, the device was irradiated with light from a direction perpendicular to the device, and an amount of light transmitted through the device was measured. A voltage-transmittance curve was prepared, in which the maximum amount of light corresponds to 100% transmittance and the minimum amount of light corresponds to 0% transmittance. A threshold voltage is expressed in terms of voltage at 90% transmittance.

(11b) Threshold Voltage (Vth; Measured at 25° C.; V)

Negative dielectric anisotropy: For measurement, an LCD-5100 luminance meter made by Otsuka Electronics Co., Ltd. was used.

A light source was a halogen lamp. A sample was put in a normally black mode VA device in which a distance (cell gap) between two glass substrates was 4 micrometers and a rubbing direction was anti-parallel, and the device was sealed with an ultraviolet-curable adhesive. A voltage (60 Hz, rectangular waves) to be applied to the device was stepwise increased from 0 V to 20 V at an increment of 0.02 V. On the occasion, the device was irradiated with light from a direction perpendicular to the device, and an amount of light transmitted through the device was measured. A voltage-transmittance curve was prepared, in which the maximum amount of light corresponds to 100% transmittance and the minimum amount of light corresponds to 0% transmittance. A threshold voltage is expressed in terms of voltage at 10% transmittance.

(12a) Response Time (τ; Measured at 25° C.; Ms)

Positive dielectric anisotropy: For measurement, an LCD-5100 luminance meter made by Otsuka Electronics Co., Ltd. was used. A light source was a halogen lamp. A low-pass filter was set to 5 kHz. A sample was put in a normally white mode TN device in which a distance (cell gap) between two glass substrates was 5.0 micrometers and a twist angle was 80 degrees. A voltage (rectangular waves; 60 Hz, 5 V, 0.5 second) was applied to the device. On the occasion, the device was irradiated with light from a direction perpendicular to the device, and an amount of light transmitted through the device was measured. The maximum amount of light corresponds to 100% transmittance, and the minimum amount of light corresponds to 0% transmittance. A rise time (τr; millisecond) was expressed in terms of time required for a change from 90% transmittance to 10% transmittance. A fall time (τf; millisecond) was expressed in terms of time required for a change from 10% transmittance to 90% transmittance. A response time was expressed by a sum of the rise time and the fall time thus determined.

(12b) Response Time (τ; Measured at 25° C.; Ms)

Negative dielectric anisotropy: For measurement, an LCD-5100 luminance meter made by Otsuka Electronics Co., Ltd. was used. A light source was a halogen lamp. A low-pass filter was set to 5 kHz. A sample was put in a normally black mode PVA device in which a distance (cell gap) between two glass substrates was 3.2 micrometers, and a rubbing direction was anti-parallel. The device was sealed with an ultraviolet-curable adhesive. The device was applied with a voltage of a little exceeding a threshold voltage for 1 minute, and then was irradiated with ultraviolet light of 23.5 mW/cm²for 8 minutes, while applying a voltage of 5.6 V. A voltage (rectangular waves; 60 Hz, 10 V, 0.5 second) was applied to the device. On the occasion, the device was irradiated with light from a direction perpendicular to the device, and an amount of light transmitted through the device was measured. The maximum amount of light corresponds to 100% transmittance, and the minimum amount of light corresponds to 0% transmittance. A response time was expressed in terms of time required for a change from 90% transmittance to 10% transmittance (fall time; millisecond).

Raw Material

Solmix (registered trademark) A-11 is a mixture of ethanol (85.5%), methanol (13.4%) and isopropanol (1.1%), and was purchased from Japan Alcohol Trading Co., Ltd.

Synthesis Example 1
Synthesis of Compound (No. 164)

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First Step

Compound (T-1) (30 g), 3,4-dihydro-2H-pyran (23.3 g), pyridinium p-toluenesulfonate (PPTS) (5.80 g) and dichloromethane (300 mL) were put in a reaction vessel, and the resulting mixture was stirred at 50° C. for 10 hours. After an insoluble matter was filtered off, the reaction mixture was poured into water, and an aqueous layer was subjected to extraction with dichloromethane. An organic layer was washed with water, and dried over anhydrous magnesium sulfate. The resulting solution was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (heptane:ethyl acetate=2:1 in a volume ratio) to obtain compound (T-2) (39.5 g; 80%).

Second Step

Compound (T-2) (39.5 g), THF (400 mL), methanol (100 mL) and water (400 mL) were put in a reaction vessel, and the resulting mixture was cooled to 0° C. Thereto, lithium hydroxide monohydrate (15.4 g) was added, and the resulting mixture was stirred for 12 hours while returning to room temperature. The reaction mixture was poured into water, and 6 N hydrochloric acid (60 mL) was slowly added to be acidified, and an aqueous layer was subjected to extraction with ethyl acetate. An organic layer was washed with water, and dried over anhydrous magnesium sulfate. The resulting solution was concentrated under reduced pressure to obtain compound (T-3) (32.6 g; 95%).

Third Step

Compound (T-4) (10 g), compound (T-3) (12.2 g), DMAP (0.80 g) and dichloromethane (100 mL) were put in a reaction vessel, and the resulting mixture was cooled to 0° C. Thereto, DCC (13.48 g) was added, and the resulting mixture was stirred for 12 hours while returning to room temperature. After an insoluble matter was filtered off, the reaction mixture was poured into water, and an aqueous layer was subjected to extraction with dichloromethane. An organic layer was washed with water, and dried over anhydrous magnesium sulfate. The resulting solution was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (ethyl acetate:toluene=1:9 in a volume ratio) to obtain compound (T-5) (8 g; 38%).

Fourth Step

Compound (T-5) (4 g), potassium carbonate (5.16 g), 4,4′-biphenyldiol (4.63 g) and DMF (100 mL) were put in a reaction vessel, and the resulting mixture was stirred at 60° C. for 2 hours. The reaction mixture was poured into water, and an aqueous layer was subjected to extraction with ethyl acetate. An organic layer was washed with water, and dried over anhydrous magnesium sulfate. The resulting solution was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (ethyl acetate:toluene=1:3 in a volume ratio) to obtain compound (T-6) (6.00 g; 100%).

Fifth Step

Compound (T-6) (6 g), compound (T-7) (9.04 g), DMAP (0.34 g) and dichloromethane (100 mL) were put in a reaction vessel, and the resulting mixture was cooled to 0° C. Thereto, DCC (6.39 g) was added, and the resulting mixture was stirred for 12 hours while returning to room temperature. After an insoluble matter was filtered off, the reaction mixture was poured into water, and an aqueous layer was subjected to extraction with dichloromethane. An organic layer was washed with water, and dried over anhydrous magnesium sulfate. The resulting solution was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (ethyl acetate:toluene=1:5 in a volume ratio) to obtain compound (T-8) (10 g; 100%).

Sixth Step

Compound (T-8) (3 g), pyridinium p-toluenesulfonate (PPTS) (2.15 g), THF (50 mL) and methanol (50 mL) were put in a reaction vessel, and the resulting mixture was stirred at 50° C. for 5 hours. After an insoluble matter was filtered off, the reaction mixture was poured into water, and an aqueous layer was subjected to extraction with ethyl acetate. An organic layer was washed with water, and dried over anhydrous magnesium sulfate. The resulting solution was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (toluene:ethyl acetate=2:1 in a volume ratio) to obtain compound (No. 164) (2 g; 75%).

An NMR analysis value of the resulting compound (No. 164) was as described below.

¹H-NMR: chemical shift δ (ppm; CDCl₃): 8.15 (d, 2H), 7.58 (d, 2H), 7.50 (d, 2H), 7.25 (d, 2H), 6.97 (d, 2H), 6.96 (d, 2H), 6.41 (d, 1H), 6.26 (s, 1H), 6.13 (dd, 1H), 5.84 (s, 1H), 5.83 (d, 1H), 4.34 (d, 2H), 4.28 (t, 2H), 4.18 (t, 2H), 4.05 (t, 2H), 4.05 (t, 2H), 2.30 (t, 1H), 1.95-1.87 (m, 4H), 1.84 (quint, 2H), 1.73 (quint, 2H), 1.58-1.48 (m, 4H).

Physical properties of compound (No. 164) were as described below.

Transition temperature (° C.): C 88.95 N, Polymerization starting temperature (° C.): 123.02.

Synthesis Example 2
Synthesis of Compound (No. 165)

Compound (No. 165) (4.9 g) was obtained by using compound (T-9) in place of 4,4′-biphenyldiol in Example 1.

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An NMR analysis value of the resulting compound (No. 165) was as described below.

¹H-NMR: chemical shift δ (ppm; CDCl₃): 8.17 (d, 2H), 7.50 (d, 2H), 7.43 (s, 1H), 7.40 (d, 1H), 7.17 (d, 1H), 6.98 (d, 2H), 6.95 (d, 2H), 6.41 (d, 1H), 6.26 (s, 1H), 6.13 (dd, 1H), 5.84 (s, 1H), 5.82 (d, 1H), 4.34 (d, 2H), 4.29 (t, 2H), 4.18 (t, 2H), 4.05 (t, 2H), 4.04 (t, 2H), 2.27 (s, 3H), 2.24 (t, 1H), 1.95-1.87 (m, 4H), 1.85 (quint, 2H), 1.73 (quint, 2H), 1.58-1.48 (m, 4H).

Physical properties of compound (No. 165) were as described below.

Transition temperature (° C.): C 66.1 N 106.3 I, Polymerization starting temperature (° C.): 134.

Synthesis Example 3
Synthesis of Compound (No. 216)

Compound (No. 216) (6.1 g) was obtained by using compound (T-10) in place of 4,4′-biphenyldiol, and (T-11) in place of (T-4) in Example 1.

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An NMR analysis value of the resulting compound (No. 216) was as described below.

¹H-NMR: chemical shift δ (ppm; CDCl₃): 8.17 (d, 2H), 7.64 (dd, 2H), 7.30 (s, 1H), 7.16 (d, 1H), 7.04 (s, 1H), 6.98 (d, 2H), 6.90 (d, 1H), 6.41 (d, 1H), 6.26 (s, 1H), 6.13 (dd, 1H), 5.84 (s, 1H), 5.82 (d, 1H), 4.43 (t, 2H), 4.34 (d, 2H), 4.18 (t, 2H), 4.14 (t, 2H), 4.05 (t, 2H), 3.92 (q, 1H), 2.26 (t, 1H), 2.23 (quint, 2H), 1.85 (quint, 2H), 1.73 (quint, 2H), 1.58-1.45 (m, 4H), 1.51 (d, 3H).

Physical properties of compound (No. 216) were as described below.

Transition temperature (° C.): C 84.6 N 95.3 I, Polymerization starting temperature (° C.): 176.6.

Synthesis Example 4
Synthesis of Compound (No. 303)

(No. 303) (1.7 g) was prepared according to the following scheme. The compound can be easily synthesized according to the Synthesis Examples with reference to the Synthesis Examples described above for details.

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An NMR analysis value of the resulting compound (No. 303) was as described below.

¹H-NMR: chemical shift δ (ppm; CDCl₃): 8.17 (d, 2H), 8.17 (d, 2H), 7.64 (dd, 2H), 7.30 (s, 1H), 7.16 (d, 1H), 7.04 (s, 1H), 6.98 (d, 2H), 6.90 (d, 1H), 6.41 (d, 1H), 6.26 (s, 1H), 6.13 (dd, 1H), 5.84 (s, 1H), 5.82 (d, 1H), 4.43 (t, 2H), 4.34 (d, 2H), 4.18 (t, 2H), 4.14 (t, 2H), 4.05 (t, 2H), 3.92 (q, 1H), 2.26 (t, 1H), 2.23 (quint, 2H), 1.85 (quint, 2H), 1.73 (quint, 2H), 1.58-1.45 (m, 4H), 1.51 (d, 3H).

Physical properties of compound (No. 303) were as described below.

Transition temperature (° C.): C 84.6 N 95.3 I, Polymerization starting temperature (° C.): 176.6.

Compounds (No. 1) to (No. 588) described below were prepared according to the synthesis methods described in Synthesis Examples.

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577

578

579

580

581

582

583

584

585

586

587

588

2. Use Examples of Devices

The compounds in Use Examples were represented using symbols according to definitions in Table 3 described below. In Table 3, the configuration of 1,4-cyclohexylene is trans. A parenthesized number next to a symbolized compound corresponds to the number of the compound. A symbol (-) means any other liquid crystal compound. A proportion (percentage) of the liquid crystal compound is expressed in terms of weight percent (% by weight) based on the weight of the liquid crystal composition. Values of the characteristics of the composition were summarized in a last part.

TABLE 3

Method for description of compounds using symbols

R—(A₁)—Z₁— . . . —Z_n—(A_n)—R′

1) Left-terminal group R—
Symbol

FC_nH_2n—
Fn-

C_nH_2n+1—
n-

C_nH_2n-+1O—
nO—

C_mH_2m+1OC_nH_2n—
mOn-

CH₂═CH—
V—

C_nH2_n+1—CH═CH—
nV—

CH₂═CH—C_nH_2n—
Vn-

C_mH_2m+1—CH═CH—C_nH_2n—
mVn-

CF₂═CH—
VFF—

CF₂═CH—C_nH_2n—
VFFn-

C_mH_2m+1CF₂C_nH_2n—
m(CF2)n-

CH₂═CHCOO—
AC—

CH₂═C(CH₃)COO—
MAC—

2) Right-terminal group —R′
Symbol

—C_nH_2n+1
-n

—OC_nH_2n+1
—On

—COOCH₃
—EMe

—CH═CH₂
—V

—CH═CH—C_nH_2n+1
—Vn

—C_nH_2n—CH═CH₂
-nV

—C_mH_2m—CH═CH—C_nH_2n+1
-mVn

—CH═CF₂
—VFF

—F
—F

—Cl
—CL

—OCF₃
—OCF3

—OCF₂H
—OCF2H

—CF₃
—CF3

—CF═CH—CF₃
—FVCF3

—OCH═CH—CF₃
—OVCF3

—C≡N
—C

—OCOCH═CH₂
—AC

—OCOC(CH₃)═CH₂
—MAC

3) Bonding group —Z_n—
Symbol

—C_nH_2n—
n

—COO—
E

—CH═CH—
V

—CH₂O—
1O

—CH═CHO—
VO

—OCH═CH—
OV

—CF═CF—
VFF

—CH═CF—
VF

—OCH₂—
O1

—OCF₂—
x

—CF₂O—
X

—C≡C—
T

4) Ring structure —A_n—
Symbol

embedded image

B(F)

B(2F)

B(F,F)

B(2F,5F)

B(2F,3F)

Bm(n)

B(2F,3Cl)

Cro(7F,8F)

5) Examples of description

Example 1 3-HBB(2F,3F)—O2

embedded image

Example 2 5-HHBB(F,F)—F

embedded image

Example 3 3-HB—O2

embedded image

Example 4 3-HBB(F,F)—F

embedded image

1. Raw Material

A composition to which an alignment control monomer was added was injected into a device having no alignment film. After the device was irradiated with linearly polarized light, alignment of liquid crystal molecules in the device was confirmed. First, a raw material will be described. The raw material was appropriately selected from a composition such as compositions (M1) to (M41), and an alignment control monomer such as compounds (No. 1) to (No. 588). The compositions are as described below.

Composition (M1)

3-hb(2f,3f)-o2
(9-1)
10%

5-hb(2f,3f)-o2
(9-1)
7%

2-bb(2f,3f)-o2
(9-3)
7%

3-bb(2f,3f)-o2
(9-3)
7%

3-b(2f,3f)b(2f,3f)-o2
(9-7)
3%

2-hhb(2f,3f)-o2
(10-1)
5%

3-hhb(2f,3f)-o2
(10-1)
10%

2-hbb(2f,3f)-o2
(10-7)
8%

3-hbb(2f,3f)-o2
(10-7)
10%

2-hh-3
(2-1)
14%

3-hb-o1
(2-5)
5%

3-hhb-1
(3-1)
3%

3-hhb-o1
(3-1)
3%

3-hhb-3
(3-1)
4%

2-bb(f)b-3
(3-6)
4%

NI=73.2° C.; Tc<−20° C.; Δn=0.133; Δε=4.0; Vth=2.18 V; η=22.6 mPa·s.

Composition (M2)

3-HB(2F,3F)-O4
(9-1)
6%

3-H2B(2F,3F)-O2
(9-4)
8%

3-H1OB(2F,3F)-O2
(9-5)
4%

3-BB(2F,3F)-O2
(9-3)
7%

2-HHB(2F,3F)-O2
(10-1)
7%

3-HHB(2F,3F)-O2
(10-1)
7%

3-HH2B(2F,3F)-O2
(10-4)
7%

5-HH2B(2F,3F)-O2
(10-4)
4%

2-HBB(2F,3F)-O2
(10-7)
5%

3-HBB(2F,3F)-O2
(10-7)
5%

4-HBB(2F,3F)-O2
(10-7)
6%

2-HH-3
(2-1)
12%

1-BB-5
(2-8)
12%

3-HHB-1
(3-1)
4%

3-HHB-O1
(3-1)
3%

3-HBB-2
(3-4)
3%

NI=82.8° C.; Tc<−30° C.; Δn=0.118; Δε=−4.4; Vth=2.13 V; η=22.5 mPa·s.

Composition (M3)

3-HB(2F,3F)-O2
(9-1)
7%

5-HB(2F,3F)-O2
(9-1)
7%

3-BB(2F,3F)-O2
(9-3)
8%

3-HHB(2F,3F)-O2
(10-1)
5%

5-HHB(2F,3F)-O2
(10-1)
4%

3-HH1OB(2F,3F)-O2
(10-5)
4%

2-BB(2F,3F)B-3
(11-1)
5%

2-HBB(2F,3F)-O2
(10-7)
3%

3-HBB(2F,3F)-O2
(10-7)
8%

4-HBB(2F,3F)-O2
(10-7)
5%

5-HBB(2F,3F)-O2
(10-7)
8%

3-HH-V
(2-1)
27%

3-HH-V1
(2-1)
6%

V-HHB-1
(3-1)
3%

NI=78.1° C.; Tc<−30° C.; Δn=0.107; Δε=−3.2; Vth=2.02 V; η=15.9 mPa·s.

Composition (M4)

3-HB(2F,3F)-O2
(9-1)
10%

5-HB(2F,3F)-O2
(9-1)
10%

3-H2B(2F,3F)-O2
(9-4)
8%

5-H2B(2F,3F)-O2
(9-4)
8%

2-HBB(2F,3F)-O2
(10-7)
6%

3-HBB(2F,3F)-O2
(10-7)
8%

4-HBB(2F,3F)-O2
(10-7)
7%

5-HBB(2F,3F)-O2
(10-7)
7%

3-HDhB(2F,3F)-O2
(10-3)
5%

3-HH-4
(2-1)
14%

V-HHB-1
(3-1)
10%

3-HBB-2
(3-4)
7%

NI=88.5° C.; Tc<−30° C.; Δn=0.108; 6, Δε=−3.8; Vth=2.25 V; η=24.6 mPa·s; VHR-1=99.1%; VHR-2=98.2%; VHR-3=97.8%.

Composition (M5)

3-HB(2F,3F)-O2
(9-1)
7%

3-HB(2F,3F)-O4
(9-1)
8%

3-H2B(2F,3F)-O2
(9-4)
8%

3-BB(2F,3F)-O2
(9-3)
10%

2-HHB(2F,3F)-O2
(10-1)
4%

3-HHB(2F,3F)-O2
(10-1)
7%

3-HHB(2F,3F)-1
(10-1)
6%

2-HBB(2F,3F)-O2
(10-7)
6%

3-HBB(2F,3F)-O2
(10-7)
6%

4-HBB(2F,3F)-O2
(10-7)
5%

5-HBB(2F,3F)-O2
(10-7)
4%

3-HEB(2F,3F)B(2F,3F)-O2
(16-1)
3%

3-H1OCro(7F,8F)-5
(13-2)
3%

3-HDhB(2F,3F)-O2
(10-3)
5%

3-HH-O1
(2-1)
5%

1-BB-5
(2-8)
4%

V-HHB-1
(3-1)
4%

5-HB(F)BH-3
(4-2)
5%

NI=81.1° C.; Tc<−30° C.; Δn=0.119; Δε=−4.5; Vth=1.69 V; η=31.4 mPa·s.

Composition (M6)

3-HB(2F,3F)-O4
(9-1)
15%

3-HBB(2F,3F)-O2
(10-7)
8%

4-HBB(2F,3F)-O2
(10-7)
5%

5-HBB(2F,3F)-O2
(10-7)
7%

3-dhBB(2F,3F)-O2
(10-9)
5%

3-chB(2F,3F)-O2
(16-2)
7%

2-HchB(2F,3F)-O2
(16-3)
8%

5-HH-V
(2-1)
18%

7-HB-1
(2-5)
5%

V-HHB-1
(3-1)
7%

V2-HHB-1
(3-1)
7%

3-HBB(F)B-3
(4-5)
8%

NI=98.8° C.; Tc<−30° C.; Δn=0.111; Δε=−3.2; Vth=2.47 V; η=23.9 mPa·s.

Composition (M7)

3-H2B(2F,3F)-O2
(9-4)
18%

5-H2B(2F,3F)-O2
(9-4)
17%

3-HHB(2F,3Cl)-O2
(10-12)
5%

3-HBB(2F,3Cl)-O2
(10-13)
8%

5-HBB(2F,3Cl)-O2
(10-13)
7%

3-HDhB(2F,3F)-O2
(10-3)
5%

3-HH-V
(2-1)
11%

3-HH-VFF
(2-1)
7%

F3-HH-V
(2-1)
10%

3-HHEH-3
(3-13)
4%

3-HB(F)HH-2
(4-7)
4%

3-HHEBH-3
(4-6)
4%

NI=77.5° C.; Tc<−30° C.; Δn=0.084; Δε=−2.6; Vth=2.43 V; η=22.8 mPa·s.

Composition (M8)

3-HB(2F,3F)-O2
(9-1)
8%

3-H2B(2F,3F)-O2
(9-4)
10%

3-BB(2F,3F)-O2
(9-3)
10%

2O-BB(2F,3F)-O2
(9-3)
3%

2-HHB(2F,3F)-O2
(10-1)
4%

3-HHB(2F,3F)-O2
(10-1)
7%

2-HHB(2F,3F)-1
(10-1)
5%

2-BB(2F,3F)B-3
(11-1)
6%

2-BB(2F,3F)B-4
(11-1)
6%

2-HBB(2F,3F)-O2
(10-7)
4%

3-HBB(2F,3F)-O2
(10-7)
7%

3-HH1OCro(7F,8F)-5
(13-6)
4%

3-HDhB(2F,3F)-O2
(10-3)
6%

3-dhBB(2F,3F)-O2
(10-9)
4%

3-HH-V
(2-1)
11%

1-BB-5
(2-8)
5%

NI=70.6° C.; Tc<−20° C.; Δn=0.129; Δε=−4.3; Vth=1.69 V; η=27.0 mPa·s.

Composition (M9)

3-HB(2F,3F)-O4
(9-1)
14%

3-H1OB(2F,3F)-O2
(9-5)
3%

3-BB(2F,3F)-O2
(9-3)
10%

2-HHB(2F,3F)-O2
(10-1)
7%

3-HHB(2F,3F)-O2
(10-1)
7%

3-HH1OB(2F,3F)-O2
(10-5)
6%

2-HBB(2F,3F)-O2
(10-7)
4%

3-HBB(2F,3F)-O2
(10-7)
6%

4-HBB(2F,3F)-O2
(10-7)
4%

3-HH-V
(2-1)
14%

1-BB-3
(2-8)
3%

3-HHB-1
(3-1)
4%

3-HHB-O1
(3-1)
4%

V-HBB-2
(3-4)
4%

1-BB(F)B-2V
(3-6)
6%

5-HBBH-1O1
(4-1)
4%

NI=93.0° C.; Tc<−30° C.; Δn=0.123; Δε=−4.0; Vth=2.27 V; η=29.6 mPa·s.

Composition (M10)

3-HB(2F,3F)-O4
(9-1)
6%

3-H2B(2F,3F)-O2
(9-4)
8%

3-H1OB(2F,3F)-O2
(9-5)
5%

3-BB(2F,3F)-O2
(9-3)
10%

2-HHB(2F,3F)-O2
(10-1)
7%

3-HHB(2F,3F)-O2
(10-1)
7%

5-HHB(2F,3F)-O2
(10-1)
7%

2-HBB(2F,3F)-O2
(10-7)
4%

3-HBB(2F,3F)-O2
(10-7)
7%

5-HBB(2F,3F)-O2
(10-7)
6%

3-HH-V
(2-1)
11%

1-BB-3
(2-8)
6%

3-HHB-1
(3-1)
4%

3-HHB-O1
(3-1)
4%

3-HBB-2
(3-4)
4%

3-B(F)BB-2
(3-8)
4%

NI=87.6° C.; Tc<−30° C.; Δn=0.126; Δε=−4.5; Vth=2.21 V; η=25.3 mPa·s.

Composition (M11)

3-HB(2F,3F)-O4
(9-1)
6%

3-H2B(2F,3F)-O2
(9-4)
8%

3-H1OB(2F,3F)-O2
(9-5)
4%

3-BB(2F,3F)-O2
(9-3)
7%

2-HHB(2F,3F)-O2
(10-1)
6%

3-HHB(2F,3F)-O2
(10-1)
10%

5-HHB(2F,3F)-O2
(10-1)
8%

2-HBB(2F,3F)-O2
(10-7)
5%

3-HBB(2F,3F)-O2
(10-7)
7%

5-HBB(2F,3F)-O2
(10-7)
5%

2-HH-3
(2-1)
12%

1-BB-3
(2-8)
6%

3-HHB-1
(3-1)
3%

3-HHB-O1
(3-1)
4%

3-HBB-2
(3-4)
6%

3-B(F)BB-2
(3-8)
3%

NI=93.0° C.; Tc<−20° C.; Δn=0.124; Δε=−4.5; Vth=2.22 V; η=25.0 mPa·s.

Composition (M12)

3-HB(2F,3F)-O2
(9-1)
7%

5-HB(2F,3F)-O2
(9-1)
7%

3-BB(2F,3F)-O2
(9-3)
8%

3-HHB(2F,3F)-O2
(10-1)
4%

5-HHB(2F,3F)-O2
(10-1)
5%

3-HH1OB(2F,3F)-O2
(10-5)
5%

2-BB(2F,3F)B-3
(11-1)
4%

2-HBB(2F,3F)-O2
(10-7)
3%

3-HBB(2F,3F)-O2
(10-7)
8%

4-HBB(2F,3F)-O2
(10-7)
5%

5-HBB(2F,3F)-O2
(10-7)
8%

3-HH-V
(2-1)
33%

V-HHB-1
(3-1)
3%

NI=76.4° C.; Tc<−30° C.; Δn=0.104; Δε=−3.2; Vth=2.06 V; η=15.6 mPa·s.

Composition (M13)

2-H1OB(2F,3F)-O2
(9-5)
6%

3-H1OB(2F,3F)-O2
(9-5)
4%

3-BB(2F,3F)-O2
(9-3)
3%

2-HH1OB(2F,3F)-O2
(10-5)
14%

2-HBB(2F,3F)-O2
(10-7)
7%

3-HBB(2F,3F)-O2
(10-7)
11%

5-HBB(2F,3F)-O2
(10-7)
9%

2-HH-3
(2-1)
5%

3-HH-VFF
(2-1)
30%

1-BB-3
(2-8)
5%

3-HHB-1
(3-1)
3%

3-HBB-2
(3-4)
3%

NI=78.3° C.; Tc<−20° C.; Δn=0.103; Δε=−3.2; Vth=2.17 V; η=17.7 mPa·s.

Composition (M14)

3-HB(2F,3F)-O2
(9-1)
5%

5-HB(2F,3F)-O2
(9-1)
7%

3-BB(2F,3F)-O2
(9-3)
8%

3-HHB(2F,3F)-O2
(10-1)
5%

5-HHB(2F,3F)-O2
(10-1)
4%

3-HH1OB(2F,3F)-O2
(10-5)
5%

2-BB(2F,3F)B-3
(11-1)
4%

2-HBB(2F,3F)-O2
(10-7)
3%

3-HBB(2F,3F)-O2
(10-7)
9%

4-HBB(2F,3F)-O2
(10-7)
4%

5-HBB(2F,3F)-O2
(10-7)
8%

3-HH-V
(2-1)
27%

3-HH-V1
(2-1)
6%

V-HHB-1
(3-1)
5%

NI=81.2° C.; Tc<−20° C.; Δn=0.107; Δε=−3.2; Vth=2.11 V; η=15.5 mPa·s.

Composition (M15)

3-H2B(2F,3F)-O2
(9-4)
7%

3-HHB(2F,3F)-O2
(10-1)
8%

3-HH1OB(2F,3F)-O2
(10-5)
5%

2-BB(2F,3F)B-3
(11-1)
7%

2-BB(2F,3F)B-4
(11-1)
7%

3-HDhB(2F,3F)-O2
(10-3)
3%

5-HDhB(2F,3F)-O2
(10-3)
4%

2-HchB(2F,3F)-O2
(16-3)
8%

4-HH-V
(2-1)
15%

3-HH-V1
(2-1)
6%

1-HH-2V1
(2-1)
6%

3-HH-2V1
(2-1)
4%

V2-BB-1
(2-8)
5%

1V2-BB-1
(2-8)
5%

3-HHB-1
(3-1)
6%

3-HB(F)BH-3
(4-2)
4%

NI=88.7° C.; Tc<−30° C.; Δn=0.115; Δε=−1.9; Vth=2.82 V; η=17.3 mPa·s.

Composition (M16)

V2-H2B(2F,3F)-O2
(9-4)
8%

V2-H1OB(2F,3F)-O4
(9-5)
4%

3-BB(2F,3F)-O2
(9-3)
7%

2-HHB(2F,3F)-O2
(10-1)
7%

3-HHB(2F,3F)-O2
(10-1)
7%

3-HH2B(2F,3F)-O2
(10-4)
7%

5-HH2B(2F,3F)-O2
(10-4)
4%

V-HH2B(2F,3F)-O2
(10-4)
6%

V2-HBB(2F,3F)-O2
(10-7)
5%

V-HBB(2F,3F)-O2
(10-7)
5%

V-HBB(2F,3F)-O4
(10-7)
6%

2-HH-3
(2-1)
12%

1-BB-5
(2-8)
12%

3-HHB-1
(3-1)
4%

3-HHB-O1
(3-1)
3%

3-HBB-2
(3-4)
3%

NI=89.9° C.; Tc<−20° C.; Δn=0.122; Δε=−4.2; Vth=2.16 V; η=23.4 mPa·s.

Composition (M17)

3-HB(2F,3F)-O2
(9-1)
3%

V-HB(2F,3F)-O2
(9-1)
3%

V2-HB(2F,3F)-O2
(9-1)
5%

5-H2B(2F,3F)-O2
(9-4)
5%

V2-BB(2F,3F)-O2
(9-3)
3%

1V2-BB(2F,3F)-O2
(9-3)
3%

3-HHB(2F,3F)-O2
(10-1)
6%

V-HHB(2F,3F)-O2
(10-1)
6%

V-HHB(2F,3F)-O4
(10-1)
5%

V2-HHB(2F,3F)-O2
(10-1)
4%

V2-BB(2F,3F)B-1
(11-1)
4%

V2-HBB(2F,3F)-O2
(10-7)
5%

V-HBB(2F,3F)-O2
(10-7)
4%

V-HBB(2F,3F)-O4
(10-7)
5%

V-HHB(2F,3Cl)-O2
(10-12)
3%

3-HH-V
(2-1)
27%

3-HH-V1
(2-1)
6%

V-HHB-1
(3-1)
3%

NI=77.1° C.; Tc<−20° C.; Δn=0.101; Δε=−3.0; Vth=2.04 V; η=13.9 mPa·s.

Composition (M18)

V-HB(2F,3F)-O2
(9-1)
10%

V2-HB(2F,3F)-O2
(9-1)
10%

2-H1OB(2F,3F)-O2
(9-5)
3%

3-H1OB(2F,3F)-O2
(9-5)
3%

2O-BB(2F,3F)-O2
(9-3)
3%

V2-BB(2F,3F)-O2
(9-3)
8%

V2-HHB(2F,3F)-O2
(10-1)
5%

2-HBB(2F,3F)-O2
(10-7)
3%

3-HBB(2F,3F)-O2
(10-7)
3%

V-HBB(2F,3F)-O2
(10-7)
6%

V-HBB(2F,3F)-O4
(10-7)
8%

V-HHB(2F,3Cl)-O2
(10-12)
7%

3-HH-4
(2-1)
14%

V-HHB-1
(3-1)
10%

3-HBB-2
(3-4)
7%

NI=75.9° C.; Tc<−20° C.; Δn=0.114; Δε=−3.9; Vth=2.20 V; η=24.7 mPa·s.

Composition (M19)

2-H1OB(2F,3F)-O2
(9-5)
7%

3-H1OB(2F,3F)-O2
(9-5)
11%

3-HH1OB(2F,3F)-O2
(10-5)
8%

2-HBB(2F,3F)-O2
(10-7)
3%

3-HBB(2F,3F)-O2
(10-7)
9%

5-HBB(2F,3F)-O2
(10-7)
7%

V-HBB(2F,3F)-O2
(10-7)
8%

3-HDhB(2F,3F)-O2
(10-3)
3.5%

2-HH-3
(2-1)
21%

3-HH-4
(2-1)
5%

3-HB-O2
(2-5)
2.5%

1-BB-3
(2-8)
4%

3-HHB-1
(3-1)
1.5%

3-HBB-2
(3-4)
9.5%

NI=80.8° C.; Tc<−20° C.; Δn=0.108; Δε=−3.8; Vth=2.02 V; η=19.8 mPa·s.

Composition (M20)

2-H1OB(2F,3F)-O2
(9-5)
5.5%

2-BB(2F,3F)-O2
(9-3)
11%

2-HH1OB(2F,3F)-O2
(10-5)
13%

3-HH1OB(2F,3F)-O2
(10-5)
15.5%

3-HBB(2F,3F)-O2
(10-7)
9%

2-HH-3
(2-1)
25%

3-HH-4
(2-1)
3%

3-HBB-2
(3-4)
14%

5-B(F)BB-2
(3-8)
4%

NI=85.3° C.; Tc<−20° C.; Δn=0.109; Δε=−3.6; Vth=2.06 V; η=20.9 mPa·s.

Composition (M21)

V-HB(2F,3F)-O2
(9-1)
7%

V-2BB(2F,3F)-O2
(9-3)
10%

V-HHB(2F,3F)-O1
(10-1)
7%

V-HHB(2F,3F)-O2
(10-1)
9%

V-2HHB(2F,3F)-O2
(10-1)
8%

3-HH2B(2F,3F)-O2
(10-4)
9%

V-HBB(2F,3F)-O2
(10-7)
7%

V-HBB(2F,3F)-O4
(10-7)
7%

2-HH-3
(2-1)
9%

3-HH-4
(2-1)
3%

3-HH-V
(2-1)
15%

3-HH-V1
(2-1)
6%

1V2-HH-3
(2-1)
3%

NI=87.5° C.; Tc<−20° C.; Δn=0.100; Δε=−3.4; Vth=2.25 V; η=16.6 mPa·s.

Composition (M22)

3-HHXB(F,F)-F
(6-100)
6%

3-BB(F,F)XB(F,F)-F
(6-97)
13%

3-HHBB(F,F)-F
(7-6)
4%

4-HHBB(F,F)-F
(7-6)
5%

3-HBBXB(F,F)-F
(7-32)
3%

3-BB(F)B(F,F)XB(F)-F
(7-46)
2%

4-BB(F)B(F,F)XB(F,F)-F
(7-47)
8%

5-BB(F)B(F,F)XB(F,F)-F
(7-47)
7%

3-HH-V
(2-1)
44%

V-HHB-1
(3-1)
6%

2-BB(F)B-3
(3-6)
2%

NI=79.8° C.; Tc<−30° C.; Δn=0.106; Δε=8.5; Vth=1.45 V; η=11.6 mPa·s; γ1=60.0 mPa·s.

Composition (M23)

5-HXB(F,F)-F
(5-13)
3%

3-HHXB(F,F)-F
(6-100)
3%

3-HHXB(F,F)-CF3
(6-100)
3%

3-HGB(F,F)-F
(6-103)
3%

3-HB(F)B(F,F)-F
(6-50)
5%

3-BB(F,F)XB(F,F)-F
(6-97)
6%

3-HHBB(F,F)-F
(7-6)
6%

5-BB(F)B(F,F)XB(F)B(F,F)-F
(—)
2%

3-BB(2F,3F)XB(F,F)-F
(6-114)
4%

3-B(2F,3F)BXB(F,F)-F
(6-115)
5%

3-HHB(F,F)XB(F,F)-F
(7-29)
4%

3-HB-CL
(5-2)
3%

3-HHB-OCF3
(6-1)
3%

3-HH-V
(2-1)
22%

3-HH-V1
(2-1)
10%

5-HB-O2
(2-5)
5%

3-HHEH-3
(3-13)
3%

3-HBB-2
(3-4)
7%

5-B(F)BB-3
(3-8)
3%

NI=71.2° C.; Tc<−20° C.; Δn=0.099; Δε=6.1; Vth=1.74 V; η=13.2 mPa·s; γ1=59.3 mPa·s.

Composition (M24)

5-HXB(F,F)-F
(5-13)
6%

3-HHXB(F,F)-F
(6-100)
6%

V-HB(F)B(F,F)-F
(6-50)
5%

3-HHB(F)B(F,F)-F
(7-9)
7%

2-BB(F)B(F,F)XB(F)-F
(7-47)
3%

3-BB(F)B(F,F)XB(F)-F
(7-47)
3%

4-BB(F)B(F,F)XB(F)-F
(5-2)
5%

2-HH-5
(2-1)
8%

3-HH-V
(2-1)
10%

3-HH-V1
(2-1)
7%

4-HH-V
(2-1)
10%

4-HH-V1
(2-1)
8%

5-HB-O2
(2-5)
7%

4-HHEH-3
(3-13)
3%

1-BB(F)B-2V
(3-6)
3%

1O1-HBBH-3
(4-1)
5%

NI=78.5° C.; Tc<−20° C.; Δn=0.095; Δε=3.4; Vth=1.50 V; η=8.4 mPa·s; γ1=54.2 mPa·s.

Composition (M25)

3-HHEB(F,F)-F
(6-12)
5%

3-HHXB(F,F)-F
(6-100)
7%

5-HBEB(F,F)-F
(6-39)
5%

3-BB(F,F)XB(F,F)-F
(6-97)
10%

2-HHB(F)B(F,F)-F
(7-9)
3%

3-HB(2F,3F)BXB(F,F)-F
(7-58)
3%

3-BB(2F,3F)BXB(F,F)-F
(7-59)
2%

5-HHB(F,F)XB(F,F)-F
(7-28)
6%

2-HH-3
(2-1)
8%

3-HH-V
(2-1)
20%

3-HH-V1
(2-1)
7%

4-HH-V
(2-1)
6%

5-HB-O2
(2-5)
5%

V2-B2BB-1
(3)
3%

3-HHEBH-3
(4-6)
5%

3-HHEBH-5
(4-6)
5%

NI=90.3° C.; Tc<−20° C.; Δn=0.089; Δε=5.5; Vth=1.65 V; η=13.6 mPa·s; γl=60.1 mPa·s.

Composition (M26)

3-BB(F,F)XB(F,F)-F
(6-97)
12%

3-HHBB(F,F)-F
(7-6)
5%

4-HHBB(F,F)-F
(7-6)
4%

3-HBBXB(F,F)-F
(7-32)
3%

3-BB(F)B(F,F)XB(F)-F
(7-46)
3%

3-BB(F)B(F,F)XB(F,F)-F
(7-47)
3%

4-BB(F)B(F,F)XB(F,F)-F
(7-47)
5%

5-BB(F)B(F,F)XB(F,F)-F
(7-47)
4%

2-HH-3
(2-1)
6%

3-HH-5
(2-1)
6%

3-HH-V
(2-1)
25%

3-HH-VFF
(2-1)
6%

5-HB-O2
(2-5)
7%

V-HHB-1
(3-1)
6%

V-HBB-2
(3-4)
5%

NI=78.3° C.; Tc<−20° C.; Δn=0.107; Δε=7.0; Vth=1.55 V; η=11.6 mPa·s; γ1=55.6 mPa·s.

Composition (M27)

3-HHXB(F,F)-F
(6-100)
3%

3-BBXB(F,F)-F
(6-91)
3%

3-BB(F,F)XB(F,F)-F
(6-97)
8%

3-HHBB(F,F)-F
(7-6)
5%

4-HHBB(F,F)-F
(7-6)
4%

3-BB(F)B(F,F)XB(F,F)-F
(7-47)
3%

4-BB(F)B(F,F)XB(F,F)-F
(7-47)
6%

5-BB(F)B(F,F)XB(F,F)-F
(7-47)
5%

3-HH-V
(2-1)
30%

3-HH-V1
(2-1)
5%

3-HHB-O1
(3-1)
2%

V-HHB-1
(3-1)
5%

2-BB(F)B-3
(3-6)
6%

F3-HH-V
(2-1)
15%

NI=80.4° C.; Tc<−20° C.; Δn=0.106; Δε=5.8; Vth=1.40 V; η=11.6 mPa·s; γ1=61.0 mPa·s.

Composition (M28)

3-HGB(F,F)-F
(6-103)
3%

5-GHB(F,F)-F
(6-109)
4%

3-GB(F,F)XB(F,F)-F
(6-113)
5%

3-BB(F)B(F,F)-CF3
(6-69)
2%

3-HHBB(F,F)-F
(7-6)
4%

3-GBB(F)B(F,F)-F
(7-55)
2%

2-dhBB(F,F)XB(F,F)-F
(7-50)
4%

3-GB(F)B(F,F)XB(F,F)-F
(7-57)
3%

3-HGB(F,F)XB(F,F)-F
(—)
5%

7-HB(F,F)-F
(5-4)
3%

2-HH-3
(2-1)
14%

2-HH-5
(2-1)
4%

3-HH-V
(2-1)
26%

1V2-HH-3
(2-1)
5%

1V2-BB-1
(2-8)
3%

2-BB(F)B-3
(3-6)
3%

3-HB(F)HH-2
(4-7)
4%

5-HBB(F)B-2
(4-5)
6%

NI=78.4° C.; Tc<−20° C.; Δn=0.094; Δε=5.6; Vth=1.45 V; η=11.5 mPa·s; γ1=61.7 mPa·s.

Composition (M29)

3-HBB(F,F)-F
(6-24)
5%

5-HBB(F,F)-F
(6-24)
4%

3-BB(F)B(F,F)-F
(6-69)
3%

3-BB(F)B(F,F)XB(F,F)-F
(7-47)
3%

4-BB(F)B(F,F)XB(F,F)-F
(7-47)
5%

3-BB(F,F)XB(F)B(F,F)-F
(7-60)
3%

5-BB(F)B(F,F)XB(F)B(F,F)-F
(—)
4%

3-HH2BB(F,F)-F
(7-15)
3%

4-HH2BB(F,F)-F
(7-15)
3%

2-HH-5
(2-1)
8%

3-HH-V
(2-1)
25%

3-HH-V1
(2-1)
7%

4-HH-V1
(2-1)
6%

5-HB-O2
(2-5)
5%

7-HB-1
(2-5)
5%

VFF-HHB-O1
(3-1)
8%

VFF-HHB-1
(3-1)
3%

NI=80.0° C.; Tc<−20° C.; Δn=0.101; Δε=4.6; Vth=1.71 V; η=11.0 mPa·s; γ1=47.2 mPa·s.

Composition M30

3-HHB(F,F)-F
(6-3)
8%

3-GB(F)B(F)-F
(6-116)
2%

3-GB(F)B(F,F)-F
(6-117)
3%

3-BB(F,F)XB(F,F)-F
(6-97)
8%

3-GB(F)B(F,F)XB(F,F)-F
(7-57)
6%

5-GB(F)B(F,F)XB(F,F)-F
(7-57)
5%

3-HH-V
(2-1)
30%

3-HH-V1
(2-1)
10%

1V2-HH-3
(2-1)
8%

3-HH-VFF
(2-1)
8%

V2-BB-1
(2-8)
2%

5-HB(F)BH-3
(4-2)
5%

5-HBBH-3
(4-1)
5%

NI=78.6° C.; Tc<−20° C.; Δn=0.088; Δε=5.6; Vth=1.85 V; η=13.9 mPa·s; γ1=66.9 mPa·s.

Composition (M31)

3-HHEB(F,F)-F
(6-12)
4%

5-HHEB(F,F)-F
(6-12)
3%

3-HBEB(F,F)-F
(6-39)
3%

5-HBEB(F,F)-F
(6-39)
3%

3-BB(F)B(F,F)-F
(6-69)
3%

3-GB(F)B(F,F)XB(F,F)-F
(7-57)
5%

4-GB(F)B(F,F)XB(F,F)-F
(7-57)
5%

5-HB-CL
(2-5)
5%

3-HHB-OCF3
(3-1)
4%

3-HHB(F,F)XB(F,F)-F
(7-29)
5%

5-HHB(F,F)XB(F,F)-F
(7-29)
3%

3-HGB(F,F)XB(F,F)-F
(—)
5%

2-HH-5
(2-1)
3%

3-HH-5
(2-1)
5%

3-HH-V
(2-1)
24%

4-HH-V
(2-1)
5%

1V2-HH-3
(2-1)
5%

3-HHEH-3
(3-13)
5%

5-B(F)BB-2
(3-8)
3%

5-B(F)BB-3
(3-8)
2%

NI=82.9° C.; Tc<−20° C.; Δn=0.093; Δε=6.9; Vth=1.50 V; η=16.3 mPa·s; γ1=65.2 mPa·s.

Composition (M32)

3-HHXB(F,F)-F
(6-100)
9%

3-HBB(F,F)-F
(6-24)
3%

3-BB(F)B(F,F)-F
(6-69)
4%

3-BB(F)B(F,F)-CF3
(6-69)
4%

3-BB(F,F)XB(F,F)-F
(6-97)
5%

3-GBB(F)B(F,F)-F
(7-55)
3%

4-GBB(F)B(F,F)-F
(7-55)
4%

3-HH-V
(2-1)
25%

3-HH-V1
(2-1)
10%

5-HB-O2
(2-5)
10%

7-HB-1
(2-5)
5%

V2-BB-1
(2-8)
3%

3-HHB-1
(3-1)
4%

1V-HBB-2
(3-4)
5%

5-HBB(F)B-2
(4-5)
6%

NI=79.6° C.; Tc<−20° C.; Δn=0.111; Δε=4.7; Vth=1.86 V; η=9.7 mPa·s; γ1=49.9 mPa·s.

Composition (M33)

3-BB(F,F)XB(F,F)-F
(6-97)
14%

5-BB(F)B(F,F)XB(F,F)-F
(7-47)
7%

7-HB(F,F)-F
(5-4)
6%

2-HH-5
(2-1)
5%

3-HH-V
(2-1)
30%

3-HH-V1
(2-1)
3%

3-HH-VFF
(2-1)
10%

3-HHB-1
(3-1)
4%

3-HHB-3
(3-1)
5%

3-HHB-O1
(3-1)
3%

1-BB(F)B-2V
(3-6)
3%

3-HHEBH-3
(4-6)
3%

3-HHEBH-4
(4-6)
4%

3-HHEBH-5
(4-6)
3%

NI=83.0° C.; Tc<−20° C.; Δn=0.086; Δε=3.8; Vth=1.94 V; η=7.5 mPa·s; γ1=51.5 mPa·s.

Composition (M34)

3-HBB(F,F)-F
(6-24)
5%

5-HBB(F,F)-F
(6-24)
4%

3-BB(F)B(F,F)-F
(6-69)
3%

3-BB(F)B(F,F)XB(F,F)-F
(7-47)
3%

4-BB(F)B(F,F)XB(F,F)-F
(7-47)
5%

3-BB(F,F)XB(F)B(F,F)-F
(7-60)
3%

5-BB(F)B(F,F)XB(F)B(F,F)-F
(—)
4%

3-HH2BB(F,F)-F
(7-15)
3%

4-HH2BB(F,F)-F
(7-15)
3%

2-HH-5
(2-1)
8%

3-HH-V
(2-1)
28%

4-HH-V1
(2-1)
7%

5-HB-O2
(2-5)
2%

7-HB-1
(2-5)
5%

VFF-HHB-O1
(3-1)
8%

VFF-HHB-1
(3-1)
3%

2-BB(2F,3F)B-3
(11-1)
4%

3-HBB(2F,3F)-O2
(10-7)
2%

NI=81.9° C.; Tc<−20° C.; Δn=0.109; Δε=4.8; Vth=1.75 V; η=13.3 mPa·s; γ1=57.4 mPa·s.

Composition (M35)

3-HHEB(F,F)-F
(6-12)
4%

3-HBEB(F,F)-F
(6-39)
3%

5-HBEB(F,F)-F
(6-39)
3%

3-BB(F)B(F,F)-F
(6-69)
3%

3-HBBXB(F,F)-F
(7-32)
6%

4-GBB(F,F)XB(F,F)-F
(7-62)
2%

5-GBB(F,F)XB(F,F)-F
(7-62)
2%

3-GB(F)B(F,F)XB(F,F)-F
(7-57)
5%

4-GB(F)B(F,F)XB(F,F)-F
(7-57)
5%

5-HHB(F,F)XB(F,F)-F
(7-29)
3%

5-HEB(F,F)-F
(5-10)
3%

5-HB-CL
(5-2)
2%

3-HHB-OCF3
(6-1)
4%

3-HH-5
(2-1)
4%

3-HH-V
(2-1)
21%

3-HH-V1
(2-1)
3%

4-HH-V
(2-1)
4%

1V2-HH-3
(2-1)
6%

5-B(F)BB-2
(3-8)
3%

5-B(F)BB-3
(3-8)
2%

3-HB(2F,3F)-O2
(10-7)
3%

3-BB(2F,3F)-O2
(9-3)
2%

3-HHB(2F,3F)-O2
(10-1)
4%

F3-HH-V
(2-1)
3%

NI=78.2° C.; Tc<−20° C.; Δn=0.101; Δε=6.7; Vth=1.45 V; η=17.8 mPa·s; γ1=67.8 mPa·s.

Composition (M36)

3-HHB(F,F)-F
(6-3)
10%

3-HHXB(F,F)-F
(6-100)
2%

3-GHB(F,F)-F
(6-109)
5%

3-BB(F)B(F,F)-F
(6-69)
6%

3-BB(F,F)XB(F,F)-F
(6-97)
14%

4-BB(F)B(F,F)XB(F,F)-F
(7-47)
10%

5-BB(F)B(F,F)XB(F,F)-F
(7-47)
6%

2-HH-3
(2-1)
5%

3-HH-4
(2-1)
11%

3-HH-O1
(2-1)
5%

5-HB-O2
(2-5)
8%

3-HHB-1
(3-1)
6%

3-HHB-3
(3-1)
6%

3-HHB-O1
(3-1)
6%

NI=77.6° C.; Tc<−20° C.; Δn=0.109; Δε=10.6; Vth=1.34 V; η=22.6 mPa·s; γ1=92.4 mPa·s.

Composition (M37)

3-HBB-F
(6-22)
3%

3-BB(F,F)XB(F)-OCF3
(6-96)
3%

3-HHB(F)-F
(6-2)
3%

3-HGB(F,F)-F
(6-103)
3%

5-GHB(F,F)-F
(6-109)
3%

3-HBB(F,F)-F
(6-24)
4%

3-BB(F,F)XB(F,F)-F
(6-97)
5%

3-HHBB(F,F)-F
(7-6)
5%

3-HBBXB(F,F)-F
(7-32)
5%

3-BBVFFXB(F,F)-F
(6-119)
8%

3-HH-V
(2-1)
39%

1-HH-V1
(2-1)
3%

1-HH-2V1
(2-1)
4%

3-HHEH-5
(3-13)
3%

1-BB(F)B-2V
(3-6)
3%

3-HHEBH-3
(4-6)
3%

5-HBB(F)B-2
(4-5)
3%

NI=85.2° C.; Tc<−20° C.; Δn=0.102; Δε=4.1; γ1=43.0 mPa·s.

Composition (M38)

3-HHBB(F)-F
(7-5)
3%

2-HHEB(F,F)-F
(6-12)
3%

5-BB(F)B(F,F)-F
(6-69)
7%

3-HHB(F)B(F,F)-F
(7-9)
3%

3-GB(F)B(F,F)XB(F,F)-F
(7-57)
3%

3-BB(F,F)XB(F)B(F,F)-F
(7-60)
3%

3-HHVFFXB(F,F)-F
(6-120)
5%

3-BBVFFXB(F,F)-F
(6-119)
5%

3-HBBVFFXB(F,F)-F
(7-61)
3%

2-HH-5
(2-1)
5%

3-HH-V
(2-1)
20%

5-HH-V
(2-1)
12%

3-HH-V1
(2-1)
4%

4-HH-V1
(2-1)
5%

2-HH-2V1
(2-1)
3%

1-BB-3
(2-8)
3%

V2-BB(F)B-1
(3-6)
5%

V2-B(F)BB-1
(3-8)
5%

3-HB(F)HH-5
(4-7)
3%

NI=85.8° C.; Tc<−20° C.; Δn=0.115; Δε=4.2; γ1=41.4 mPa·s.

Composition (M39)

3-BB(F)XB(F)B(F,F)-F
(7-60)
5%

3-HGB(F,F)-F
(6-103)
3%

5-GHB(F,F)-F
(6-109)
4%

3-GB(F,F)XB(F,F)-F
(6-113)
5%

3-HHBB(F,F)-F
(7-6)
4%

2-dhBB(F,F)XB(F,F)-F
(7-50)
4%

3-GB(F)B(F,F)XB(F,F)-F
(7-57)
3%

3-HGB(F,F)XB(F,F)-F
(7)
5%

7-HB(F,F)-F
(5-4)
3%

2-HH-3
(2-1)
14%

2-HH-5
(2-1)
4%

3-HH-V
(2-1)
26%

1V2-HH-3
(2-1)
5%

1V2-BB-1
(2-8)
3%

2-BB(F)B-3
(3-6)
3%

3-HB(F)HH-2
(4-7)
4%

5-HBB(F)B-2
(4-5)
5%

NI=78.4° C.; Tc<−20° C.; Δn=0.094; Δε=5.6; Vth=1.45 V; η=11.5 mPa·s; γ1=61.7 mPa·s.

Composition (M40)

3-HBB(F,F)-F
(6-24)
5%

5-HBB(F,F)-F
(6-24)
4%

3-BB(F)B(F,F)XB(F,F)-F
(7-47)
3%

4-BB(F)B(F,F)XB(F,F)-F
(7-47)
5%

3-BB(F,F)XB(F)B(F,F)-F
(7-60)
10%

3-HH2BB(F,F)-F
(7-15)
3%

4-HH2BB(F,F)-F
(7-15)
3%

2-HH-5
(2-1)
4%

3-HH-V
(2-1)
25%

3-HH-V1
(2-1)
10%

4-HH-V1
(2-1)
7%

5-HB-O2
(2-5)
5%

7-HB-1
(2-5)
5%

VFF-HHB-O1
(3-1)
8%

VFF-HHB-1
(3-1)
3%

NI=79.3° C.; Tc<−20° C.; Δn=0.099; Δε=5.0; Vth=1.64 V; η=10.4 mPa·s; γ1=44.7 mPa·s.

Composition (M41)

3-GBXB(F)B(F,F)-F
(7)
5%

3-HHB(F,F)-F
(6-3)
7%

3-GB(F)B(F)-F
(6-116)
2%

3-GB(F)B(F,F)-F
(6-117)
3%

3-BB(F,F)XB(F,F)-F
(6-97)
7%

3-GB(F)B(F,F)XB(F,F)-F
(7-57)
4%

5-GB(F)B(F,F)XB(F,F)-F
(7-57)
5%

3-HH-V
(2-1)
30%

3-HH-V1
(2-1)
10%

1V2-HH-3
(2-1)
8%

3-HH-VFF
(2-1)
8%

V2-BB-1
(2-8)
2%

5-HB(F)BH-3
(4-2)
4%

5-HBBH-3
(4-1)
5%

NI=79.7° C.; Tc<−20° C.; Δn=0.091; Δε=5.7; Vth=1.83 V; η=14.9 mPa·s; γ1=69.3 mPa·s.

2. Alignment of Liquid Crystal Molecules
Use Example 1

To composition (M1), compound (No. 164) was added at a proportion of 0.1% by weight as a first additive, and compound (AO-1) in which R⁴⁰is n-heptyl was added at a proportion of 150 ppm as an antioxidant. The resulting mixture was injected into an IPS device having no alignment film at 90° C. (equal to or higher than a maximum temperature of a nematic phase). The IPS device was irradiated with linearly polarized ultraviolet light (313 nm, 2.0 J/cm²) from a direction normal to the device while heating the device at 90° C. to obtain a device subjected to alignment treatment. The resulting device was set on a polarizing microscope in which a polarizer and an analyzer were arranged perpendicularly to each other to be parallel to a polarization axis of linearly polarized light in the device. The device was irradiated with light from below, and presence or absence of light leakage was observed. A case where no light passed through the device was judged to be “Good” in alignment. A case where light passing through the device was observed was expressed by “Poor.” No light leakage was observed in the present Example 1, and therefore alignment was good.

Use Examples 2 to 589

As shown in Table 4 described below, compositions (M1) to (M41) were used, compound (AO-1) in which R⁴⁰is n-heptyl was added at a proportion of 150 ppm as an antioxidant, and a first additive was mixed thereto at a proportion of 0.1% by weight as described in the following table. Operation was performed in the same manner as in Use Example 1 except for the operation described above. When presence or absence of light leakage was observed in the same manner as in Use Example 1, no light leakage was observed, and therefore alignment was good.

TABLE 4

Liquid crystal

Use Example
composition
First additive
Alignment

2
M2
No. 1
Good

3
M3
No. 2
Good

4
M4
No. 3
Good

5
M5
No. 4
Good

6
M6
No. 5
Good

7
M7
No. 6
Good

8
M8
No. 7
Good

9
M9
No. 8
Good

10
M10
No. 9
Good

11
M11
No. 10
Good

12
M12
No. 11
Good

13
M13
No. 12
Good

14
M14
No. 13
Good

15
M15
No. 14
Good

16
M16
No. 15
Good

17
M17
No. 16
Good

18
M18
No. 17
Good

19
M19
No. 18
Good

20
M20
No. 19
Good

21
M21
No. 20
Good

22
M22
No. 21
Good

23
M23
No. 22
Good

24
M24
No. 23
Good

25
M25
No. 24
Good

26
M26
No. 25
Good

27
M27
No. 26
Good

28
M28
No. 27
Good

29
M29
No. 28
Good

30
M30
No. 29
Good

31
M31
No. 30
Good

32
M32
No. 31
Good

33
M33
No. 32
Good

34
M34
No. 33
Good

35
M35
No. 34
Good

36
M36
No. 35
Good

37
M37
No. 36
Good

38
M38
No. 37
Good

39
M39
No. 38
Good

40
M40
No. 39
Good

41
M41
No. 40
Good

42
M1
No. 41
Good

43
M2
No. 42
Good

44
M3
No. 43
Good

45
M4
No. 44
Good

46
M5
No. 45
Good

47
M6
No. 46
Good

48
M7
No. 47
Good

49
M8
No. 48
Good

50
M9
No. 49
Good

51
M10
No. 50
Good

52
M11
No. 51
Good

53
M12
No. 52
Good

54
M13
No. 53
Good

55
M14
No. 54
Good

56
M15
No. 55
Good

57
M16
No. 56
Good

58
M17
No. 57
Good

59
M18
No. 58
Good

60
M19
No. 59
Good

61
M20
No. 60
Good

62
M21
No. 61
Good

63
M22
No. 62
Good

64
M23
No. 63
Good

65
M24
No. 64
Good

66
M25
No. 65
Good

67
M26
No. 66
Good

68
M27
No. 67
Good

69
M28
No. 68
Good

70
M29
No. 69
Good

71
M30
No. 70
Good

72
M31
No. 71
Good

73
M32
No. 72
Good

74
M33
No. 73
Good

75
M34
No. 74
Good

76
M35
No. 75
Good

77
M36
No. 76
Good

78
M37
No. 77
Good

79
M38
No. 78
Good

80
M39
No. 79
Good

81
M40
No. 80
Good

82
M41
No. 81
Good

83
M1
No. 82
Good

84
M2
No. 83
Good

85
M3
No. 84
Good

86
M4
No. 85
Good

87
M5
No. 86
Good

88
M6
No. 87
Good

89
M7
No. 88
Good

90
M8
No. 89
Good

91
M9
No. 90
Good

92
M10
No. 91
Good

93
M11
No. 92
Good

94
M12
No. 93
Good

95
M13
No. 94
Good

96
M14
No. 95
Good

97
M15
No. 96
Good

98
M16
No. 97
Good

99
M17
No. 98
Good

100
M18
No. 99
Good

101
M19
No. 100
Good

102
M20
No. 101
Good

103
M21
No. 102
Good

104
M22
No. 103
Good

105
M23
No. 104
Good

106
M24
No. 105
Good

107
M25
No. 106
Good

108
M26
No. 107
Good

109
M27
No. 108
Good

110
M28
No. 109
Good

111
M29
No. 110
Good

112
M30
No. 111
Good

113
M31
No. 112
Good

114
M32
No. 113
Good

115
M33
No. 114
Good

116
M34
No. 115
Good

117
M35
No. 116
Good

118
M36
No. 117
Good

119
M37
No. 118
Good

120
M38
No. 119
Good

121
M39
No. 120
Good

122
M40
No. 121
Good

123
M41
No. 122
Good

124
M1
No. 123
Good

125
M2
No. 124
Good

126
M3
No. 125
Good

127
M4
No. 126
Good

128
M5
No. 127
Good

129
M6
No. 128
Good

130
M7
No. 129
Good

131
M8
No. 130
Good

132
M9
No. 131
Good

133
M10
No. 132
Good

134
M11
No. 133
Good

135
M12
No. 134
Good

136
M13
No. 135
Good

137
M14
No. 136
Good

138
M15
No. 137
Good

139
M16
No. 138
Good

140
M17
No. 139
Good

141
M18
No. 140
Good

142
M19
No. 141
Good

143
M20
No. 142
Good

144
M21
No. 143
Good

145
M22
No. 144
Good

146
M23
No. 145
Good

147
M24
No. 146
Good

148
M25
No. 147
Good

149
M26
No. 148
Good

150
M27
No. 149
Good

151
M28
No. 150
Good

152
M29
No. 151
Good

153
M30
No. 152
Good

154
M31
No. 153
Good

155
M32
No. 154
Good

156
M33
No. 155
Good

157
M34
No. 156
Good

158
M35
No. 157
Good

159
M36
No. 158
Good

160
M37
No. 159
Good

161
M38
No. 160
Good

162
M39
No. 161
Good

163
M40
No. 162
Good

164
M41
No. 163
Good

165
M1
No. 164
Good

166
M2
No. 165
Good

167
M3
No. 166
Good

168
M4
No. 167
Good

169
M5
No. 168
Good

170
M6
No. 169
Good

171
M7
No. 170
Good

172
M8
No. 171
Good

173
M9
No. 172
Good

174
M10
No. 173
Good

175
M11
No. 174
Good

176
M12
No. 175
Good

177
M13
No. 176
Good

178
M14
No. 177
Good

179
M15
No. 178
Good

180
M16
No. 179
Good

181
M17
No. 180
Good

182
M18
No. 181
Good

183
M19
No. 182
Good

184
M20
No. 183
Good

185
M21
No. 184
Good

186
M22
No. 185
Good

187
M23
No. 186
Good

188
M24
No. 187
Good

189
M25
No. 188
Good

190
M26
No. 189
Good

191
M27
No. 190
Good

192
M28
No. 191
Good

193
M29
No. 192
Good

194
M30
No. 193
Good

195
M31
No. 194
Good

196
M32
No. 195
Good

197
M33
No. 196
Good

198
M34
No. 197
Good

199
M35
No. 198
Good

200
M36
No. 199
Good

201
M37
No. 200
Good

202
M38
No. 201
Good

203
M39
No. 202
Good

204
M40
No. 203
Good

205
M41
No. 204
Good

206
M1
No. 205
Good

207
M2
No. 206
Good

208
M3
No. 207
Good

209
M4
No. 208
Good

210
M5
No. 209
Good

211
M6
No. 210
Good

212
M7
No. 211
Good

213
M8
No. 212
Good

214
M9
No. 213
Good

215
M10
No. 214
Good

216
M11
No. 215
Good

217
M12
No. 216
Good

218
M13
No. 217
Good

219
M14
No. 218
Good

220
M15
No. 219
Good

221
M16
No. 220
Good

222
M17
No. 221
Good

223
M18
No. 222
Good

224
M19
No. 223
Good

225
M20
No. 224
Good

226
M21
No. 225
Good

227
M22
No. 226
Good

228
M23
No. 227
Good

229
M24
No. 228
Good

230
M25
No. 229
Good

231
M26
No. 230
Good

232
M27
No. 231
Good

233
M28
No. 232
Good

234
M29
No. 233
Good

235
M30
No. 234
Good

236
M31
No. 235
Good

237
M32
No. 236
Good

238
M33
No. 237
Good

239
M34
No. 238
Good

240
M35
No. 239
Good

241
M36
No. 240
Good

242
M37
No. 241
Good

243
M38
No. 242
Good

244
M39
No. 243
Good

245
M40
No. 244
Good

246
M41
No. 245
Good

247
M1
No. 246
Good

248
M2
No. 247
Good

249
M3
No. 248
Good

250
M4
No. 249
Good

251
M5
No. 250
Good

252
M6
No. 251
Good

253
M7
No. 252
Good

254
M8
No. 253
Good

255
M9
No. 254
Good

256
M10
No. 255
Good

257
M11
No. 256
Good

258
M12
No. 257
Good

259
M13
No. 258
Good

260
M14
No. 259
Good

261
M15
No. 260
Good

262
M16
No. 261
Good

263
M17
No. 262
Good

264
M18
No. 263
Good

265
M19
No. 264
Good

266
M20
No. 265
Good

267
M21
No. 266
Good

268
M22
No. 267
Good

269
M23
No. 268
Good

270
M24
No. 269
Good

271
M25
No. 270
Good

272
M26
No. 271
Good

273
M27
No. 272
Good

274
M28
No. 273
Good

275
M29
No. 274
Good

276
M30
No. 275
Good

277
M31
No. 276
Good

278
M32
No. 277
Good

279
M33
No. 278
Good

280
M34
No. 279
Good

281
M35
No. 280
Good

282
M36
No. 281
Good

283
M37
No. 282
Good

284
M38
No. 283
Good

285
M39
No. 284
Good

286
M40
No. 285
Good

287
M41
No. 286
Good

288
M1
No. 287
Good

289
M2
No. 288
Good

290
M3
No. 289
Good

291
M4
No. 290
Good

292
M5
No. 291
Good

293
M6
No. 292
Good

294
M7
No. 293
Good

295
M8
No. 294
Good

296
M9
No. 295
Good

297
M10
No. 296
Good

298
M11
No. 297
Good

299
M12
No. 298
Good

300
M13
No. 299
Good

301
M14
No. 300
Good

302
M15
No. 301
Good

303
M16
No. 302
Good

304
M17
No. 303
Good

305
M18
No. 304
Good

306
M19
No. 305
Good

307
M20
No. 306
Good

308
M21
No. 307
Good

309
M22
No. 308
Good

310
M23
No. 309
Good

311
M24
No. 310
Good

312
M25
No. 311
Good

313
M26
No. 312
Good

314
M27
No. 313
Good

315
M28
No. 314
Good

316
M29
No. 315
Good

317
M30
No. 316
Good

318
M31
No. 317
Good

319
M32
No. 318
Good

320
M33
No. 319
Good

321
M34
No. 320
Good

322
M35
No. 321
Good

323
M36
No. 322
Good

324
M37
No. 323
Good

325
M38
No. 324
Good

326
M39
No. 325
Good

327
M40
No. 326
Good

328
M41
No. 327
Good

329
M1
No. 328
Good

330
M2
No. 329
Good

331
M3
No. 330
Good

332
M4
No. 331
Good

333
M5
No. 332
Good

334
M6
No. 333
Good

335
M7
No. 334
Good

336
M8
No. 335
Good

337
M9
No. 336
Good

338
M10
No. 337
Good

339
M11
No. 338
Good

340
M12
No. 339
Good

341
M13
No. 340
Good

342
M14
No. 341
Good

343
M15
No. 342
Good

344
M16
No. 343
Good

345
M17
No. 344
Good

346
M18
No. 345
Good

347
M19
No. 346
Good

348
M20
No. 347
Good

349
M21
No. 348
Good

350
M22
No. 349
Good

351
M23
No. 350
Good

352
M24
No. 351
Good

353
M25
No. 352
Good

354
M26
No. 353
Good

355
M27
No. 354
Good

356
M28
No. 355
Good

357
M29
No. 356
Good

358
M30
No. 357
Good

359
M31
No. 358
Good

360
M32
No. 359
Good

361
M33
No. 360
Good

362
M34
No. 361
Good

363
M35
No. 362
Good

364
M36
No. 363
Good

365
M37
No. 364
Good

366
M38
No. 365
Good

367
M39
No. 366
Good

368
M40
No. 367
Good

369
M41
No. 368
Good

370
M1
No. 369
Good

371
M2
No. 370
Good

372
M3
No. 371
Good

373
M4
No. 372
Good

374
M5
No. 373
Good

375
M6
No. 374
Good

376
M7
No. 375
Good

377
M8
No. 376
Good

378
M9
No. 377
Good

379
M10
No. 378
Good

380
M11
No. 379
Good

381
M12
No. 380
Good

382
M13
No. 381
Good

383
M14
No. 382
Good

384
M15
No. 383
Good

385
M16
No. 384
Good

386
M17
No. 385
Good

387
M18
No. 386
Good

388
M19
No. 387
Good

389
M20
No. 388
Good

390
M21
No. 389
Good

391
M22
No. 390
Good

392
M23
No. 391
Good

393
M24
No. 392
Good

394
M25
No. 393
Good

395
M26
No. 394
Good

396
M27
No. 395
Good

397
M28
No. 396
Good

398
M29
No. 397
Good

399
M30
No. 398
Good

400
M31
No. 399
Good

401
M32
No. 400
Good

402
M33
No. 401
Good

403
M34
No. 402
Good

404
M35
No. 403
Good

405
M36
No. 404
Good

406
M37
No. 405
Good

407
M38
No. 406
Good

408
M39
No. 407
Good

409
M40
No. 408
Good

410
M41
No. 409
Good

411
M1
No. 410
Good

412
M2
No. 411
Good

413
M3
No. 412
Good

414
M4
No. 413
Good

415
M5
No. 414
Good

416
M6
No. 415
Good

417
M7
No. 416
Good

418
M8
No. 417
Good

419
M9
No. 418
Good

420
M10
No. 419
Good

421
M11
No. 420
Good

422
M12
No. 421
Good

423
M13
No. 422
Good

424
M14
No. 423
Good

425
M15
No. 424
Good

426
M16
No. 425
Good

427
M17
No. 426
Good

428
M18
No. 427
Good

429
M19
No. 428
Good

430
M20
No. 429
Good

431
M21
No. 430
Good

432
M22
No. 431
Good

433
M23
No. 432
Good

434
M24
No. 433
Good

435
M25
No. 434
Good

436
M26
No. 435
Good

437
M27
No. 436
Good

438
M28
No. 437
Good

439
M29
No. 438
Good

440
M30
No. 439
Good

441
M31
No. 440
Good

442
M32
No. 441
Good

443
M33
No. 442
Good

444
M34
No. 443
Good

445
M35
No. 444
Good

446
M36
No. 445
Good

447
M37
No. 446
Good

448
M38
No. 447
Good

449
M39
No. 448
Good

450
M40
No. 449
Good

451
M41
No. 450
Good

452
M1
No. 451
Good

453
M2
No. 452
Good

454
M3
No. 453
Good

455
M4
No. 454
Good

456
M5
No. 455
Good

457
M6
No. 456
Good

458
M7
No. 457
Good

459
M8
No. 458
Good

460
M9
No. 459
Good

461
M10
No. 460
Good

462
M11
No. 461
Good

463
M12
No. 462
Good

464
M13
No. 463
Good

465
M14
No. 464
Good

466
M15
No. 465
Good

467
M16
No. 466
Good

468
M17
No. 467
Good

469
M18
No. 468
Good

470
M19
No. 469
Good

471
M20
No. 470
Good

472
M21
No. 471
Good

473
M22
No. 472
Good

474
M23
No. 473
Good

475
M24
No. 474
Good

476
M25
No. 475
Good

477
M26
No. 476
Good

478
M27
No. 477
Good

479
M28
No. 478
Good

480
M29
No. 479
Good

481
M30
No. 480
Good

482
M31
No. 481
Good

483
M32
No. 482
Good

484
M33
No. 483
Good

485
M34
No. 484
Good

486
M35
No. 485
Good

487
M36
No. 486
Good

488
M37
No. 487
Good

489
M38
No. 488
Good

490
M39
No. 489
Good

491
M40
No. 490
Good

492
M41
No. 491
Good

493
M1
No. 492
Good

494
M2
No. 493
Good

495
M3
No. 494
Good

496
M4
No. 495
Good

497
M5
No. 496
Good

498
M6
No. 497
Good

499
M7
No. 498
Good

500
M8
No. 499
Good

501
M9
No. 500
Good

502
M10
No. 501
Good

503
M11
No. 502
Good

504
M12
No. 503
Good

505
M13
No. 504
Good

506
M14
No. 505
Good

507
M15
No. 506
Good

508
M16
No. 507
Good

509
M17
No. 508
Good

510
M18
No. 509
Good

511
M19
No. 510
Good

512
M20
No. 511
Good

513
M21
No. 512
Good

514
M22
No. 513
Good

515
M23
No. 514
Good

516
M24
No. 515
Good

517
M25
No. 516
Good

518
M26
No. 517
Good

519
M27
No. 518
Good

520
M28
No. 519
Good

521
M29
No. 520
Good

522
M30
No. 521
Good

523
M31
No. 522
Good

524
M32
No. 523
Good

525
M33
No. 524
Good

526
M34
No. 525
Good

527
M35
No. 526
Good

528
M36
No. 527
Good

529
M37
No. 528
Good

530
M38
No. 529
Good

531
M39
No. 530
Good

532
M40
No. 531
Good

533
M41
No. 532
Good

534
M1
No. 533
Good

535
M2
No. 534
Good

536
M3
No. 535
Good

537
M4
No. 536
Good

538
M5
No. 537
Good

539
M6
No. 538
Good

540
M7
No. 539
Good

541
M8
No. 540
Good

542
M9
No. 541
Good

543
M10
No. 542
Good

544
M11
No. 543
Good

545
M12
No. 544
Good

546
M13
No. 545
Good

547
M14
No. 546
Good

548
M15
No. 547
Good

549
M16
No. 548
Good

550
M17
No. 549
Good

551
M18
No. 550
Good

552
M19
No. 551
Good

553
M20
No. 552
Good

554
M21
No. 553
Good

555
M22
No. 554
Good

556
M23
No. 555
Good

557
M24
No. 556
Good

558
M25
No. 557
Good

559
M26
No. 558
Good

560
M27
No. 559
Good

561
M28
No. 560
Good

562
M29
No. 561
Good

563
M30
No. 562
Good

564
M31
No. 563
Good

565
M32
No. 564
Good

566
M33
No. 565
Good

567
M34
No. 566
Good

568
M35
No. 567
Good

569
M36
No. 568
Good

570
M37
No. 569
Good

571
M38
No. 570
Good

572
M39
No. 571
Good

573
M40
No. 572
Good

574
M41
No. 573
Good

575
M1
No. 574
Good

576
M2
No. 575
Good

577
M3
No. 576
Good

578
M4
No. 577
Good

579
M5
No. 578
Good

580
M6
No. 579
Good

581
M7
No. 580
Good

582
M8
No. 581
Good

583
M9
No. 582
Good

584
M10
No. 583
Good

585
M11
No. 584
Good

586
M12
No. 585
Good

587
M13
No. 586
Good

588
M14
No. 587
Good

589
M15
No. 588
Good

Comparative Examples 1 to 123

As shown in Table 5 described below, compound (A-1-1-1) or (A-1-3-1) in which both polymerizable groups are an acrylate group, or compound (Formula 2) in which both polymerizable groups are a methacrylate group, as described in Patent literature No. 2, was added to each of compositions (M1) to (M41) at a proportion of 0.1% by weight. The resulting mixture was injected into an IPS device having no alignment film. When operation was performed in the same manner as in Use Example 1 except for injecting the mixture, and presence or absence of light leakage was observed in the same manner as in Use Example 1, light leakage was observed in all cases, and therefore alignment was poor.

embedded image

TABLE 5

Comparative
Liquid crystal

Example
composition
First additive
Alignment

1
M1
A-1-1-1
Poor

2
M2
A-1-1-1
Poor

3
M3
A-1-1-1
Poor

4
M4
A-1-1-1
Poor

5
M5
A-1-1-1
Poor

6
M6
A-1-1-1
Poor

7
M7
A-1-1-1
Poor

8
M8
A-1-1-1
Poor

9
M9
A-1-1-1
Poor

10
M10
A-1-1-1
Poor

11
M11
A-1-1-1
Poor

12
M12
A-1-1-1
Poor

13
M13
A-1-1-1
Poor

14
M14
A-1-1-1
Poor

15
M15
A-1-1-1
Poor

16
M16
A-1-1-1
Poor

17
M17
A-1-1-1
Poor

18
M18
A-1-1-1
Poor

19
M19
A-1-1-1
Poor

20
M20
A-1-1-1
Poor

21
M21
A-1-1-1
Poor

22
M22
A-1-1-1
Poor

23
M23
A-1-1-1
Poor

24
M24
A-1-1-1
Poor

25
M25
A-1-1-1
Poor

26
M26
A-1-1-1
Poor

27
M27
A-1-1-1
Poor

28
M28
A-1-1-1
Poor

29
M29
A-1-1-1
Poor

30
M30
A-1-1-1
Poor

31
M31
A-1-1-1
Poor

32
M32
A-1-1-1
Poor

33
M33
A-1-1-1
Poor

34
M34
A-1-1-1
Poor

35
M35
A-1-1-1
Poor

36
M36
A-1-1-1
Poor

37
M37
A-1-1-1
Poor

38
M38
A-1-1-1
Poor

39
M39
A-1-1-1
Poor

40
M40
A-1-1-1
Poor

41
M41
A-1-1-1
Poor

42
M1
A-1-3-1
Poor

43
M2
A-1-3-1
Poor

44
M3
A-1-3-1
Poor

45
M4
A-1-3-1
Poor

46
M5
A-1-3-1
Poor

47
M6
A-1-3-1
Poor

48
M7
A-1-3-1
Poor

49
M8
A-1-3-1
Poor

50
M9
A-1-3-1
Poor

51
M10
A-1-3-1
Poor

52
M11
A-1-3-1
Poor

53
M12
A-1-3-1
Poor

54
M13
A-1-3-1
Poor

55
M14
A-1-3-1
Poor

56
M15
A-1-3-1
Poor

57
M16
A-1-3-1
Poor

58
M17
A-1-3-1
Poor

59
M18
A-1-3-1
Poor

60
M19
A-1-3-1
Poor

61
M20
A-1-3-1
Poor

62
M21
A-1-3-1
Poor

63
M22
A-1-3-1
Poor

64
M23
A-1-3-1
Poor

65
M24
A-1-3-1
Poor

66
M25
A-1-3-1
Poor

67
M26
A-1-3-1
Poor

68
M27
A-1-3-1
Poor

69
M28
A-1-3-1
Poor

70
M29
A-1-3-1
Poor

71
M30
A-1-3-1
Poor

72
M31
A-1-3-1
Poor

73
M32
A-1-3-1
Poor

74
M33
A-1-3-1
Poor

75
M34
A-1-3-1
Poor

76
M35
A-1-3-1
Poor

77
M36
A-1-3-1
Poor

78
M37
A-1-3-1
Poor

79
M38
A-1-3-1
Poor

80
M39
A-1-3-1
Poor

81
M40
A-1-3-1
Poor

82
M41
A-1-3-1
Poor

83
M1
Formula 2
Poor

84
M2
Formula 2
Poor

85
M3
Formula 2
Poor

86
M4
Formula 2
Poor

87
M5
Formula 2
Poor

88
M6
Formula 2
Poor

89
M7
Formula 2
Poor

90
M8
Formula 2
Poor

91
M9
Formula 2
Poor

92
M10
Formula 2
Poor

93
M11
Formula 2
Poor

94
M12
Formula 2
Poor

95
M13
Formula 2
Poor

96
M14
Formula 2
Poor

97
M15
Formula 2
Poor

98
M16
Formula 2
Poor

99
M17
Formula 2
Poor

100
M18
Formula 2
Poor

101
M19
Formula 2
Poor

102
M20
Formula 2
Poor

103
M21
Formula 2
Poor

104
M22
Formula 2
Poor

105
M23
Formula 2
Poor

106
M24
Formula 2
Poor

107
M25
Formula 2
Poor

108
M26
Formula 2
Poor

109
M27
Formula 2
Poor

110
M28
Formula 2
Poor

111
M29
Formula 2
Poor

112
M30
Formula 2
Poor

113
M31
Formula 2
Poor

114
M32
Formula 2
Poor

115
M33
Formula 2
Poor

116
M34
Formula 2
Poor

117
M35
Formula 2
Poor

118
M36
Formula 2
Poor

119
M37
Formula 2
Poor

120
M38
Formula 2
Poor

121
M39
Formula 2
Poor

122
M40
Formula 2
Poor

123
M41
Formula 2
Poor

In Use Examples 1 to 589, a kind and an amount of compositions or alignment control monomers and a heating temperature during polarization exposure were changed, and no light leakage was observed. The results indicate that alignment is good even if the device has no alignment film of polyimide or the like, and all liquid crystal molecules are arranged in a fixed direction. On the other hand, in Comparative Examples 1 to 123, light leakage was observed, indicating that the liquid crystal compound was not aligned. From the results described above, the compounds of the present application are known to be able to form a thin film in which the liquid crystal composition can be aligned by addition with a concentration lower than the comparative compounds. Accordingly, if the liquid crystal composition of the invention is used, a liquid crystal display device having characteristics such as a wide temperature range in which the device can be used, a short response time, a high voltage holding ratio, low threshold voltage, a large contrast ratio and a long service life can be obtained. Further, a liquid crystal display device having a liquid crystal composition satisfying at least one of characteristics such as a high maximum temperature of a nematic phase, a low minimum temperature of the nematic phase, small viscosity, suitable optical anisotropy, large negative dielectric anisotropy, large specific resistance, high stability to ultraviolet light and high stability to heat can be obtained.

INDUSTRIAL APPLICABILITY

A liquid crystal composition of the invention can be used in a liquid crystal monitor, a liquid crystal television and so forth.

POLYMERIZABLE POLAR COMPOUND, LIQUID CRYSTAL COMPOSITION AND LIQUID CRYSTAL DISPLAY DEVICE

Information

Publication Number

Date Filed

Date Published

Inventors

Original Assignees

CPC

International Classifications

Abstract

Description

Claims

Priority Claims (1)

PCT Information