Liquid crystal alignment agent, liquid crystal alignment film, liquid crystal element and method for producing the same, and compound

Abstract

To provide a liquid crystal alignment agent that enables low-voltage driving of liquid crystal elements while maintaining good orientation uniformity of liquid crystal molecules. [Solution] A liquid crystal alignment agent containing a compound (Q) which is a reaction product of a compound (E) having at least one selected from the group consisting of an oxiranil group and an oxetanyl group, and a reactive compound having a functional group that can react with an oxiranil group or an oxetanyl group. Compound (E) has a molecular weight of 1,000 or less and has multiple at least one selected from the group consisting of an oxiranil group and an oxetanyl group in one molecule, or has one oxiranil group or one oxetanyl group and one polymerizable carbon-carbon unsaturated bond group in one molecule. The reactive compound contains a compound (R1) having one functional group that can react with an oxiranil group or an oxetanyl group in one molecule.

Description

Technical Field

[0001] The present invention relates to a liquid crystal aligning agent, a liquid crystal alignment film, a liquid crystal element, a method for manufacturing the same, and a compound.

Background Art

[0002] In a liquid crystal element, the initial alignment of liquid crystal molecules is generally defined by the anchoring of liquid crystal molecules by a liquid crystal alignment film. In recent years, in a liquid crystal element having a horizontal alignment mode such as an IPS type or an FFS type, a liquid crystal alignment film having strong anchoring energy (hereinafter, also referred to as a "strong anchoring liquid crystal alignment film") is formed on one of a pair of substrates, and a liquid crystal alignment film having no anchoring energy or very small anchoring energy (hereinafter, also referred to as a "weak anchoring liquid crystal alignment film") is formed on the other substrate. Various liquid crystal elements have been proposed. In a liquid crystal element utilizing a weak anchoring state, further improvements such as an improvement in luminance and contrast ratio, low voltage driving, and high-speed response (fast rise) are expected as compared with a normal liquid crystal element in which strong anchoring liquid crystal alignment films are formed on both substrates. Note that "weak anchoring" is also referred to as "zero surface anchoring".

[0003] For example, Patent Document 1 discloses a method for forming a zero surface anchoring film on a first substrate by a method including a step of applying energy sufficient to cause a polymerization reaction of a radical-polymerizable compound to a liquid crystal composition containing a liquid crystal and a radical-polymerizable compound while bringing the liquid crystal composition into contact with a radical generating film, and forming a liquid crystal alignment film on a second substrate with a known liquid crystal aligning agent to manufacture a liquid crystal cell.

Prior Art Documents

Patent Documents

[0004]

Patent Document 1

Summary of the Invention

Problems to be Solved by the Invention

[0005] In the technology described in Patent Document 1, when producing a weakly anchored liquid crystal alignment film, it is necessary to bring a liquid crystal composition containing liquid crystal and a radical polymerizable compound into contact with a radical generating film formed on a first substrate, and in that state, provide sufficient energy to cause a polymerization reaction of the radical polymerizable compound. From the viewpoint of productivity, it is desirable to be able to produce a weakly anchored liquid crystal alignment film with simple operations, while maintaining good liquid crystal alignment and achieving low-voltage driving derived from the weakly anchored state.

[0006] In recent years, liquid crystal displays (LCDs) have been used in a wide range of applications, and there is a growing demand for even higher performance. In particular, the characteristic of liquid crystal molecules aligning uniformly within the plane (alignment uniformity) is an important performance characteristic for LCDs, as it not only increases brightness when voltage is applied but also improves brightness reduction when no voltage is applied, leading to further improvements in the contrast ratio.

[0007] This invention has been made in view of the above problems, and one of its objectives is to provide a liquid crystal alignment agent that can achieve low-voltage driving of liquid crystal elements while maintaining good uniformity of liquid crystal molecule orientation. [Means for solving the problem]

[0008] The present invention provides the following liquid crystal alignment agents, liquid crystal alignment films, liquid crystal elements, methods for producing the same, and compounds.

[0009] [1] A compound (Q) is a reaction product of a compound (E) having at least one selected from the group consisting of an oxiranyl group and an oxetanyl group, and a reactive compound having a functional group that can react with an oxiranyl group or an oxetanyl group. The compound (E) has a molecular weight of 1,000 or less and contains multiple groups of at least one selected from the group consisting of oxyranyl groups and oxetanyl groups within one molecule, or contains one oxyranyl group or one oxetanyl group and one polymerizable carbon-carbon unsaturated bond group within one molecule. A liquid crystal aligning agent comprising a compound (R1) having one functional group capable of reacting with an oxiranyl group or an oxetanyl group in one molecule. 〔2〕 The liquid crystal aligning agent according to 〔1〕, wherein the compound (E) has 1 to 10 of at least one selected from the group consisting of an oxiranyl group and an oxetanyl group in one molecule. 〔3〕 The liquid crystal aligning agent according to 〔1〕 or 〔2〕, wherein the compound (R1) is a non-polymer. 〔4〕 The liquid crystal aligning agent according to any one of 〔1〕 to 〔3〕, wherein the compound (R1) further has an alkyl group having 4 to 50 carbon atoms, a monovalent group represented by the following formula (1), or a monovalent alicyclic saturated hydrocarbon group having 4 to 50 carbon atoms and having one aliphatic hydrocarbon ring. *-R 1 -(O-R 2 ) r -OR 3 …(1) (In formula (1), R 1 and R 2 are each independently an alkanediyl group. r is an integer of 0 or more. R 3 is an alkyl group. However, the total number of carbon atoms of R 1 and r R 2 and R 3 is 4 to 50. "*" represents a bond.) 〔5〕 The liquid crystal aligning agent according to any one of 〔1〕 to 〔4〕, wherein the compound (R1) does not have an aromatic ring. 〔6〕 The liquid crystal aligning agent according to any one of 〔1〕 to 〔5〕, wherein the reactive compound includes the compound (R1) and a compound (R2) which is a non-polymer having a plurality of functional groups capable of reacting with an oxiranyl group or an oxetanyl group in one molecule. 〔7〕 The liquid crystal aligning agent according to 〔6〕, wherein the compound (R2) has 2 to 10 functional groups capable of reacting with an oxiranyl group or an oxetanyl group in one molecule. 〔8〕 The liquid crystal aligning agent according to 〔6〕 or 〔7〕, wherein the compound (R2) does not have an aromatic ring. [9] The liquid crystal alignment agent according to any one of [1] to [8], wherein the compound (Q) has at least one selected from the group consisting of an oxiranyl group and an oxetanyl group.

[10] The liquid crystal alignment agent according to any one of [1] to [9], further comprising at least one polymer selected from the group consisting of polyamic acid, polyamic acid ester, and polyimide.

[11] A liquid crystal alignment agent according to any one of [1] to

[10] , further containing a crosslinking agent.

[12] A liquid crystal alignment agent according to any one of [1] to

[11] , for forming a weak anchoring film.

[13] A liquid crystal alignment agent containing the reaction product of compound (E), compound (R1), and compound (R2) shown below. Compound (E): A compound having a molecular weight of 1,000 or less, and containing multiple groups of at least one selected from the group consisting of oxiranyl groups and oxetanyl groups within one molecule, or containing one oxiranyl group or one oxetanyl group and one polymerizable carbon-carbon unsaturated bond group within one molecule. Compound (R1): A compound having one functional group in one molecule that can react with an oxiranyl group or an oxetanyl group. Compound (R2): A nonpolymer having multiple functional groups capable of reacting with oxiranyl or oxetanyl groups within a single molecule.

[14] A liquid crystal alignment film formed using any of the liquid crystal alignment agents described in [1] to

[13] .

[15] A liquid crystal element comprising the liquid crystal alignment film described in

[14] .

[16] A method for manufacturing a liquid crystal element comprising a pair of substrates consisting of a first substrate and a second substrate, and a liquid crystal layer disposed between the pair of substrates, the method comprising the step of applying a liquid crystal alignment agent described in any of [1] to

[13] to the surface of one of the pair of substrates to form a liquid crystal alignment film.

[17] The liquid crystal alignment film formed with any of the liquid crystal alignment agents described in [1] to

[13] is a weak anchoring liquid crystal alignment film, and the method for manufacturing a liquid crystal element according to

[16] further comprises the step of forming a strong anchoring liquid crystal alignment film having a stronger anchoring energy than the weak anchoring liquid crystal alignment film on the surface of a substrate different from the substrate on which the weak anchoring liquid crystal alignment film was formed, among the first substrate and the second substrate.

[18] The method for manufacturing a liquid crystal element according to

[17] , wherein the strongly anchoring liquid crystal alignment film is a rubbing alignment film or a photo-alignment film.

[19] A method for manufacturing a liquid crystal element according to

[17] or

[18] , wherein the first substrate has a pair of electrodes, the second substrate does not have electrodes, the strongly anchored liquid crystal alignment film is formed on the surface of the first substrate, and the weakly anchored liquid crystal alignment film is formed on the surface of the second substrate.

[20] A compound which is the reaction product of compound (E) and compound (R1) shown below. Compound (E): A compound having a molecular weight of 1,000 or less and containing multiple groups of at least one selected from the group consisting of oxyranyl groups and oxetanyl groups within a single molecule. Compound (R1): A nonpolymer having one functional group in each molecule that can react with at least one selected from the group consisting of an oxyranyl group and an oxetanyl group, and having an alkyl group having 4 to 50 carbon atoms, a monovalent group represented by the following formula (1), or a monovalent alicyclic saturated hydrocarbon group having 4 to 50 carbon atoms with one aliphatic hydrocarbon ring. *-R 1 -(OR 2 ) r -OR 3 …(1) (In formula (1), R 1 and R 2 These are alkanediyl groups, independent of each other. r is a non-negative integer. 3 R is an alkyl group. 1 and r R 2 and R 3 The total number of carbon atoms is between 4 and 50. (* represents a bond.)

[21] A compound which is the reaction product of compound (E), compound (R1), and compound (R2) shown below. Compound (E): A compound having a molecular weight of 1,000 or less and containing multiple groups of at least one selected from the group consisting of oxyranyl groups and oxetanyl groups within a single molecule. Compound (R1): A nonpolymer having one functional group in each molecule that can react with at least one selected from the group consisting of an oxyranyl group and an oxetanyl group, and having an alkyl group having 4 to 50 carbon atoms, a monovalent group represented by the following formula (1), or a monovalent alicyclic saturated hydrocarbon group having 4 to 50 carbon atoms with one aliphatic hydrocarbon ring. *-R 1 -(OR 2 ) r -OR 3 …(1) (In formula (1), R 1 and R 2 These are alkanediyl groups, independent of each other. r is a non-negative integer. 3 R is an alkyl group. 1 and r R 2 and R 3 The total number of carbon atoms is between 4 and 50. (* represents a bond.) Compound (R2): A nonpolymer having multiple functional groups capable of reacting with oxiranyl or oxetanyl groups within a single molecule. [Effects of the Invention]

[0010] According to the present invention, it is possible to achieve low-voltage driving of liquid crystal elements while maintaining good orientation uniformity of liquid crystal molecules. [Brief explanation of the drawing]

[0011] [Figure 1] A schematic plan view of the top electrode used in the manufacturing of a liquid crystal display element. (a) is a top view of the top electrode, and (b) is a magnified view of a portion of the top electrode. [Figure 2] A diagram showing four drive electrodes. [Modes for carrying out the invention]

[0012] The following describes in detail matters related to the embodiments. In this specification, numerical ranges indicated using "~" include the values ​​indicated before and after "~" as the lower and upper limits, respectively. A "structural unit" is a unit that mainly constitutes the main chain structure and is included in the main chain structure in pairs or more. A structural unit is typically a repeating unit composed of a single monomer. A structural unit may also be obtained by reacting a repeating unit having a reactive group with a compound having a functional group that can react with the reactive group.

[0013] In this specification, "hydrocarbon group" includes linear hydrocarbon groups, alicyclic hydrocarbon groups, and aromatic hydrocarbon groups. "Linear hydrocarbon group" means a linear hydrocarbon group or a branched hydrocarbon group that does not contain a cyclic structure and consists only of a linear structure. However, linear hydrocarbon groups may be saturated or unsaturated. "Alicyclic hydrocarbon group" means a hydrocarbon group that contains only the structure of an alicyclic hydrocarbon as its ring structure and does not contain any other structure. However, an alicyclic hydrocarbon group does not have to consist only of the structure of an alicyclic hydrocarbon, and may also include a linear structure as part of it. "Aromatic hydrocarbon group" means a hydrocarbon group that contains an aromatic ring structure as its ring structure. However, an aromatic hydrocarbon group does not have to consist only of an aromatic ring structure, and may include a linear structure or an alicyclic hydrocarbon structure as part of it. "Organic group" means an atomic group obtained by removing any hydrogen atom from a carbon-containing compound (i.e., an organic compound).

[0014] The "main chain" of a polymer refers to the "trunk" portion of the polymer, which consists of the longest chain of atoms. This "trunk" portion may contain a ring structure. For example, "having a specific structure in the main chain" means that the specific structure constitutes a part of the main chain. A "side chain" refers to a portion of the polymer that branches off from the "trunk" portion. "(meth)acrylic" is a term that encompasses acrylic and methacrylic, and "(meth)acrylo" is a term that encompasses acrylo and methacrylo. "(meth)acrylate" is a term that encompasses acrylate and methacrylate. "Epoxy group" is a term that encompasses oxyranyl group and oxetanyl group.

[0015] Liquid crystal alignment agent The liquid crystal alignment agent of this disclosure contains compound (Q), which is a reaction product of compound (E) and a reactive compound as shown below. Compound (E): A compound having a molecular weight of 1,000 or less, and containing multiple groups of at least one selected from the group consisting of oxiranyl groups and oxetanyl groups within one molecule, or containing one oxiranyl group or one oxetanyl group and one polymerizable carbon-carbon unsaturated bond group within one molecule. Reactive compounds: Compounds having a functional group that can react with an oxiranyl group or an oxetanyl group. However, reactive compounds include compounds that have one functional group capable of reacting with an oxiranil group or an oxetanil group within a single molecule (hereinafter also referred to as "compound (R1)").

[0016] The liquid crystal alignment agent of this disclosure containing compound (Q) is suitable as a liquid crystal alignment agent used for forming a weakly anchored liquid crystal alignment film (i.e., a liquid crystal alignment agent for forming a weakly anchored film). Here, "weakly anchored liquid crystal alignment films" and "strongly anchored liquid crystal alignment films" will be described in detail. The difference between a "weakly anchored liquid crystal alignment film" and a "strongly anchored liquid crystal alignment film" lies in the difference in the orientation constraint force that constrains the orientation direction of the liquid crystal molecules. That is, in a weakly anchored liquid crystal alignment film, the orientation constraint force of the liquid crystal molecules in the in-plane direction is substantially zero, while in a strongly anchored liquid crystal alignment film, the anchoring energy is stronger than that of a weakly anchored liquid crystal alignment film.

[0017] More specifically, in a liquid crystal cell, when the orientation of liquid crystal molecules near the alignment film is controlled by a strongly anchored liquid crystal alignment film, when an electric field is applied, the liquid crystal molecules at the interface between the liquid crystal layer and the liquid crystal alignment film maintain their orientation direction from before the electric field was applied, while still being subjected to the orientation constraint force by the liquid crystal alignment film. In contrast, with a weakly anchored liquid crystal alignment film, there is either no orientation constraint force on liquid crystal molecules at the interface between the liquid crystal layer and the liquid crystal alignment film, or if there is an orientation constraint force on liquid crystal molecules at the interface between the liquid crystal layer and the liquid crystal alignment film, it is very weak, and the orientation direction of the liquid crystal molecules is easily changed when an electric field is applied. By making the liquid crystal alignment film weakly anchored, the orientation constraint force on liquid crystal molecules in that liquid crystal alignment film decreases not only in the horizontal direction but also in the vertical direction. For this reason, it is thought that a liquid crystal cell equipped with a weakly anchored liquid crystal alignment film can achieve a lower voltage when driving liquid crystal molecules. Specifically, weak anchoring refers to, for example, an azimuthal anchoring strength (A2) of 10 -4 J / m 2 This refers to the case where the azimuth anchoring strength (A2) is less than 10 -5 J / m 2 It is preferable that it be smaller than [value]. In this specification, the azimuthal angle anchoring intensity (A2) of the liquid crystal alignment film is a value calculated from the electric field response threshold.

[0018] In conventional liquid crystal elements, the orientation of liquid crystal molecules is controlled by a pair of liquid crystal alignment films (strong anchoring liquid crystal alignment films). However, the orientation of liquid crystal molecules can also be controlled by combining a weak anchoring liquid crystal alignment film and a strong anchoring liquid crystal alignment film. For example, in an FFS-type liquid crystal cell, if a strong anchoring liquid crystal alignment film is formed on the substrate side where a pair of electrodes are provided (electrode substrate) using a liquid crystal alignment agent for horizontal alignment, and a weak anchoring liquid crystal alignment film is formed on the other substrate side (opposing substrate), then when the liquid crystal element is not driven, a state in which the liquid crystal molecules are horizontally aligned is formed throughout the entire liquid crystal layer.

[0019] The components contained in the liquid crystal alignment agent of this disclosure, and components that may be added as needed, are described in detail below. Unless otherwise specified, each component may be used alone or in combination of two or more.

[0020] <Compound (Q)> (Compound (E)) Compound (E) is a component that makes up the main skeleton of compound (Q), and includes compound (1a) and compound (1b) as shown below. Compound (1a): A compound with a molecular weight of 1,000 or less, having multiple groups of at least one selected from the group consisting of oxiranyl groups and oxetanyl groups within a single molecule. Compound (1b): A compound with a molecular weight of 1,000 or less, having one oxiranyl group or oxetanyl group and one polymerizable carbon-carbon unsaturated bond group in each molecule.

[0021] From the viewpoint of obtaining a liquid crystal element exhibiting uniform orientation of liquid crystal molecules by low-voltage driving, the molecular weight of compound (E) is preferably 900 or less, more preferably 800 or less, and even more preferably 750 or less. Furthermore, from the viewpoint of ensuring the voltage retention rate and reliability of the liquid crystal element, the molecular weight of compound (E) is preferably 150 or more, more preferably 200 or more, and even more preferably 250 or more.

[0022] Of the compounds (E), compound (1a) has two or more epoxy groups in one molecule, and compound (1b) has one epoxy group in one molecule. From the viewpoint of sufficiently enabling low-voltage driving of the liquid crystal element, the number of epoxy groups per molecule of compound (E) is preferably 1 to 10, more preferably 1 to 8, and even more preferably 1 to 6.

[0023] If compound (E) is compound (1a), then compound (1a) may be a compound represented by the following formula (1-a). W 1 -(X 1 ) n …(1-a) (In formula (1-a), X 1 This is a glycidyl group or an epoxycyclohexyl group.1 X is an n-valent organic group, where n is an integer greater than or equal to 2. 1 They are either the same or different.

[0024] In the above equation (1-a), W 1 Examples of n-valent organic groups represented by include substituted or unsubstituted n-valent hydrocarbon groups; n-valent groups in which one or more methylene groups of a substituted or unsubstituted hydrocarbon group are replaced with -O-, -S-, -CO-, -CO-O-, -NR-, -NR-CO-, etc.; n-valent groups having heterocycles; etc. R is a hydrogen atom or a monovalent hydrocarbon group having 1 to 10 carbon atoms (the same applies hereinafter).

[0025] Examples of hydrocarbon groups include chain hydrocarbon groups with 1 to 20 carbon atoms, alicyclic hydrocarbon groups with 3 to 20 carbon atoms, and aromatic hydrocarbon groups with 6 to 20 carbon atoms. Examples of substituents include halogen atoms (fluorine, chlorine, bromine, iodine, etc.), hydroxyl groups, amino groups, nitro groups, and cyano groups. Examples of heterocycles include imide rings, cyclic siloxanes, and isocyanuric rings. n is preferably 2 to 10, more preferably 2 to 8, and even more preferably 3 to 6.

[0026] Specific examples of compound (1a) include, for example, ethylene glycol diglycidyl ether, polyethylene glycol diglycidyl ether, propylene glycol diglycidyl ether, tripropylene glycol diglycidyl ether, triglycidyl isocyanurate, glycerol polyglycidyl ether, pentaerythritol tetraglycidyl ether, 1,4-cyclohexanedimethanol diglycidyl ether, N,N,N',N'-tetraglycidyl glycol uryl, 1,4-butanediol diglycidyl ether, neopentyl glycol diglycidyl ether, 1,6-hexanediol diglycidyl ether, 1,8-octanediol diglycidyl ether, 1,10-decanediol diglycidyl ether, and 1,12-dodecanediol diglycidyl ether. Examples include diglycidyl ethers, 1,6-hexanediol di(3,4-epoxycyclohexylmethyl) ether, trimethylolpropane triglycidyl ether, 2,2-dibromoneopentyl glycol diglycidyl ether, N,N,N',N'-tetraglycidyl-m-xylylenediamine, 1,3-bis(N,N-diglycidylaminomethyl)cyclohexane, N,N,N',N'-tetraglycidyl-4,4'-diaminodiphenylmethane, N,N-diglycidyl-benzylamine, N,N-diglycidyl-aminomethylcyclohexane, N,N-diglycidyl-cyclohexylamine, epoxidation reaction products of 2,2'-diallylbisphenol A diallyl ether with hydrogen peroxide, and compounds represented by formulas (1a-1) to (1a-9) below. Furthermore, commercially available cyclic polysiloxanes having two or more epoxy groups include, for example, CS-697, CS-783 (both manufactured by Sigma-Aldrich Corporation), KR-470, X-40-2670, and X-40-2678 (all manufactured by Shin-Etsu Silicone Co., Ltd.). [ka]

[0027] When compound (E) is compound (1b), examples of polymerizable carbon-carbon unsaturated bond groups include vinyl groups, (meth)acryloyloxy groups, (meth)acryloylamino groups, maleimide groups, vinyl ether groups, vinylphenyl groups, etc. Of these, (meth)acryloyloxy groups or maleimide groups are preferred due to their high reactivity with heat (specifically, heating during film formation), and (meth)acryloyloxy groups are even more preferred.

[0028] Compound (1b) is represented by the following formula (1-b). Y 1 -W 2 -X 1 …(1-b) (In formula (1-b), X 1 This is a glycidyl group or an epoxycyclohexyl group. 1 W is a polymerizable carbon-carbon unsaturated bond group. 2 (It is a divalent organic group.)

[0029] In the above equation (1-b), W 2 Examples of divalent organic groups represented by include substituted or unsubstituted divalent hydrocarbon groups; divalent groups in which one or more methylene groups of a substituted or unsubstituted hydrocarbon group are replaced by heteroatom-containing groups such as -O-, -S-, -CO-, -CO-O-, -NR-, -NR-CO-, etc. Specific examples of hydrocarbon groups and substituents include W 1 Examples of groups similar to those exemplified in the explanation include the following.

[0030] Specific examples of compound (1b) include, for example, (meth)acrylic compounds such as glycidyl (meth)acrylate, 4-hydroxybutyl (meth)acrylate glycidyl ether, 3,4-epoxycyclohexylmethyl (meth)acrylate, and (3-ethyloxetan-3-yl)methyl (meth)acrylate; maleimide compounds such as N-(2-glycidyloxyethyl)maleimide; and styrene compounds such as p-glycidylstyrene.

[0031] Compound (E) is preferably compound (1a) in terms of its ability to further improve the low-voltage driving effect of liquid crystal elements, and among compounds (1a), compounds with 2 to 10 epoxy groups per molecule are more preferable.

[0032] (Reactive compound) Reactive compounds include compounds (i.e., compound (R1)) that have one functional group (hereinafter also referred to as a reactive group) capable of reacting with an epoxy group in one molecule. Examples of reactive groups include carboxyl groups, amino groups (including primary and secondary amino groups), alcoholic hydroxyl groups, phenolic hydroxyl groups, and thiol groups. These functional groups may be protected. Hereinafter, "alcoholic hydroxyl group" refers to a hydroxyl group directly bonded to a carbon atom constituting an aliphatic hydrocarbon. The aliphatic hydrocarbon may be a chain hydrocarbon or an alicyclic hydrocarbon. "Phenolic hydroxyl group" refers to a hydroxyl group directly bonded to a carbon atom constituting an aromatic ring. In terms of high reactivity with epoxy groups, the reactive group of the reactive compound is preferably a carboxyl group or an amino group, with the carboxyl group being more preferred.

[0033] ·Compound (R1) From the viewpoint of sufficiently enabling low-voltage driving of the liquid crystal element, compound (R1) is preferably a nonpolymer. The molecular weight of compound (R1) is preferably 2,000 or less, more preferably 1,000 or less, and even more preferably 700 or less, from the viewpoint of suppressing excessively high pretilt angles of liquid crystal molecules near the weakly anchored liquid crystal alignment film. Furthermore, from the viewpoint of obtaining a liquid crystal element exhibiting good liquid crystal alignment, the molecular weight of compound (R1) is preferably 40 or more, and more preferably 50 or more.

[0034] In order to sufficiently enable low-voltage driving of the liquid crystal element, it is preferable that compound (R1) does not have an aromatic ring (including aromatic hydrocarbon rings and aromatic heterocycles). Furthermore, in order to enable low-voltage driving of the liquid crystal element while exhibiting good orientation uniformity, it is preferable that compound (R1) has a functional group that can react with the epoxy group, along with an alkyl group having 4 to 50 carbon atoms, a monovalent group represented by the following formula (1), or a monovalent alicyclic saturated hydrocarbon group having 4 to 50 carbon atoms with one aliphatic hydrocarbon ring. *-R 1 -(OR 2 ) r -OR 3 …(1) (In formula (1), R 1 and R 2 These are alkanediyl groups, independent of each other. r is a non-negative integer. 3 R is an alkyl group. 1 and r R 2 and R 3 The total number of carbon atoms is between 4 and 50. (* represents a bond.)

[0035] Alkyl groups having 4 to 50 carbon atoms may be linear or branched. Specific examples of alkyl groups having 4 to 50 carbon atoms include n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, isopentyl group, sec-pentyl group, tert-pentyl group, hexyl group, heptyl group, octyl group, nonyl group, decyl group, undecyl group, dodecyl group, tridecyl group, tetradecyl group, pentadecyl group, hexadecyl group, heptadecyl group, octadecyl group, and the like.

[0036] Examples of monovalent groups represented by the above formula (1) include alkoxyalkyl groups having 4 to 50 carbon atoms and polyalkylene oxy groups having 4 to 50 carbon atoms. Specific examples of alkoxyalkyl groups having 4 to 50 carbon atoms include groups obtained by replacing one methylene group in an alkyl group having 5 to 51 carbon atoms with -O-. Furthermore, in the case of a polyalkylene oxy group having 4 to 50 carbon atoms (i.e., when r is 1 or greater), R 2 or R 3It can be linear or branched. 3 The polyalkylene oxy group may be linear or branched, but a linear structure is preferred from the viewpoint of improving liquid crystal orientation. Specific examples of polyalkylene oxy groups include groups having a polyethylene oxide structure, groups having a polypropylene oxide structure, and groups having both a polyethylene oxide structure and a polypropylene oxide structure.

[0037] A monovalent alicyclic hydrocarbon group having 4 to 50 carbon atoms and possessing one aliphatic hydrocarbon ring includes a group having a saturated chain hydrocarbon ring with 3 to 12 carbon atoms as the aliphatic hydrocarbon ring. Examples of aliphatic hydrocarbon rings include cyclopropane rings, cyclobutane rings, cyclopentane rings, cyclohexane rings, cycloheptane rings, cyclooctane rings, cyclononane rings, and cyclodecane rings. To reduce the anchoring force of the liquid crystal, an aliphatic hydrocarbon ring different from the cyclohexane ring is preferred. Specifically, an aliphatic hydrocarbon ring with 7 or more members is more preferred, and an aliphatic hydrocarbon ring with 7 to 12 members is even more preferred. The monovalent alicyclic hydrocarbon group may have substituents on the ring portion. Examples of such substituents include methyl groups, ethyl groups, propyl groups, halogen atoms, cyano groups, and nitro groups.

[0038] In order to exhibit good alignment uniformity while further improving the effect of low-voltage driving of the liquid crystal element, it is preferable that compound (R1) has an alkyl group having 4 to 50 carbon atoms. From the viewpoint of obtaining a liquid crystal element that exhibits good liquid crystal alignment under low-voltage driving, the alkyl group of compound (R1) is preferably 5 or more. Furthermore, from the viewpoint of suppressing the pre-tilt angle of liquid crystal molecules near the weakly anchored liquid crystal alignment film from becoming too high, the alkyl group of compound (R1) is preferably 20 or less carbon atoms, more preferably 15 or less carbon atoms, and even more preferably 10 or less carbon atoms.

[0039] As compound (R1), an aliphatic monocarboxylic acid can be preferably used, and specifically, a compound represented by the following formula (2) can be mentioned. Z 1 -W 3 …(2) (In formula (2), Z 1 W is a functional group that can react with epoxy groups. 3 This refers to an alkyl group having 4 to 50 carbon atoms, a monovalent group represented by formula (1) above, or a monovalent alicyclic saturated hydrocarbon group having 4 to 50 carbon atoms with one aliphatic hydrocarbon ring.

[0040] Specific examples of compound (R1) include, for example, butanoic acid, pentanoic acid, isopentanoic acid, hexanoic acid, isohexanoic acid, heptanoic acid, octanoic acid, 2-ethylhexanoic acid, 1-methylheptanoic acid, nonanoic acid, decanoic acid, dodecanoic acid, tetradecanoic acid, hexadecanoic acid, 2-hexyldecanoic acid, 2-(1,3,3-trimethylbutyl)-5,7,7-trimethyloctanoic acid, octadecanoic acid, 2-(4,4-dimethyl-2-pentyl)-5,7,7-trimethyl-n-octanoic acid, nonadecanoic acid, arachidic acid, and 2-hydro Examples include linear or branched saturated fatty acids such as xyoctanoic acid; alicyclic monocarboxylic acids such as cyclohexanecarboxylic acid, cyclohexaneacetic acid, 3-cyclopentylpropionic acid, 4-butylcyclohexanecarboxylic acid, 4-isobutylcyclohexanecarboxylic acid, 4-propylcyclohexanecarboxylic acid, 4-pentylcyclohexanecarboxylic acid, cyclooctanoacetic acid, norbornane-2-carboxylic acid, and 1-adamantaneacetic acid; and ether group-containing monocarboxylic acids such as glycolic acid ethoxylate trauryl ether.

[0041] When compound (R1) has a polymerizable carbon-carbon unsaturated bond group along with a reactive group, compound (R1) can be preferably used in the production of liquid crystal alignment agents for PSA-type modes. Specific examples of the polymerizable carbon-carbon unsaturated bond group in this case include the same groups as those exemplified as polymerizable carbon-carbon unsaturated bond groups in the description of compound (1b). Specific examples of compound (R1) having a polymerizable carbon-carbon unsaturated bond group include, for example, (meth)acrylic acid, α-ethylacrylic acid, 3-butenoic acid, 4-pentenoic acid, 2-methyl-4-pentenoic acid, vinylbenzoic acid, and the like.

[0042] While compound (R1) alone may be used as the reactive compound to react with compound (E), it is preferable to use compound (R2) together with compound (R1). Compound (R2): A nonpolymer having multiple functional groups capable of reacting with oxiranyl or oxetanyl groups within a single molecule. By using compounds (R1) and (R2) as reactive compounds and reacting them with compound (E), it is possible to suppress unevenness and repulsion caused by polymer aggregation when the liquid crystal alignment agent is applied to a substrate by inkjet printing. This makes it possible to obtain a liquid crystal alignment agent with excellent inkjet coating properties while driving liquid crystal elements at low voltages.

[0043] ·Compound (R2) Compound (R2) has two or more functional groups (i.e., reactive groups) that can react with epoxy groups within one molecule. Examples of reactive groups include carboxyl groups, amino groups, alcoholic hydroxyl groups, and phenolic hydroxyl groups. These functional groups may be protected. Of these, carboxyl groups or amino groups are preferred due to their high reactivity with epoxy groups, and carboxyl groups are more preferred. The number of reactive groups in compound (R2) per molecule is preferably 2 to 10, more preferably 2 to 6, and even more preferably 2 to 4.

[0044] From the viewpoint of sufficiently enabling low-voltage driving of the liquid crystal element, compound (R2) is preferably a nonpolymer. For the same reason, the molecular weight of compound (R2) is preferably 2,000 or less, more preferably 1,000 or less, and even more preferably 700 or less. Furthermore, from the viewpoint of obtaining a liquid crystal alignment film that exhibits good liquid crystal alignment properties, the molecular weight of compound (R2) is preferably 40 or more, and more preferably 100 or more.

[0045] In order to sufficiently enable low-voltage driving of the liquid crystal element and to suppress the deterioration of various performance characteristics such as voltage holding characteristics, it is preferable that compound (R2) does not have an aromatic ring (including aromatic hydrocarbon rings and aromatic heterocycles). As compound (R2), a compound represented by the following formula (3) can be preferably used. W 4 -(Z 2 ) m …(3) (In formula (3), Z 2 W is a functional group that can react with epoxy groups. 4 This is an m-valent organic group that does not have an aromatic ring. m is an integer greater than or equal to 2. Multiple Z in the formula 2 They are either the same or different.

[0046] In the above equation (3), W 4 Examples of m-valent organic groups represented by include: substituted or unsubstituted m-valent saturated chain hydrocarbon groups having 1 to 30 carbon atoms; m groups containing heteroatom-containing groups such as -O-, -S-, -CO-, -CO-O-, -NR-, -NR-CO- between carbon-carbon bonds of substituted or unsubstituted saturated chain hydrocarbon groups having 2 to 30 carbon atoms; substituted or unsubstituted m-valent saturated alicyclic hydrocarbon groups having 3 to 30 carbon atoms; m groups containing heteroatom-containing groups such as -O-, -S-, -CO-, -CO-O-, -NR-, -NR-CO- between carbon-carbon bonds of substituted or unsubstituted saturated alicyclic hydrocarbon groups having 3 to 30 carbon atoms; and so on. From the viewpoint of low-voltage driving, W 4 Of these, the m-valent organic groups represented by are preferably substituted or unsubstituted saturated chain hydrocarbon groups with 1 to 30 carbon atoms.

[0047] Preferred specific examples of compound (R2) include polycarboxylic acids and polyamines. Examples of polycarboxylic acids include linear polycarboxylic acids in which two or more carboxyl groups are bonded to a linear hydrocarbon group having 1 to 20 carbon atoms; alicyclic polycarboxylic acids having an alicyclic structure; and so on. Examples of polyamines include linear polyamines in which two or more amino groups are bonded to a linear hydrocarbon group having 1 to 20 carbon atoms; alicyclic polyamines having an alicyclic structure; and so on.

[0048] Further specific examples of these include chain-like polycarboxylic acids such as saturated carboxylic acids including malonic acid, dimethylmalonic acid, succinic acid, glutaric acid, adipic acid, 2-methyladipic acid, trimethyladipic acid, pimelic acid, 2,2-dimethylglutaric acid, 3,3-diethylsuccinic acid, azelaic acid, sebacic acid, and suberic acid; and unsaturated carboxylic acids such as fumaric acid, maleic acid, itaconic acid, and muconic acid.

[0049] Examples of alicyclic polycarboxylic acids include 1,1-cyclopropanedicarboxylic acid, 1,2-cyclopropanedicarboxylic acid, 1,1-cyclobutanedicarboxylic acid, 1,2-cyclobutanedicarboxylic acid, 1,3-cyclobutanedicarboxylic acid, 1-cyclobutene-1,2-dicarboxylic acid, 1-cyclobutene-3,4-dicarboxylic acid, 1,1-cyclopentanedicarboxylic acid, 1,2-cyclopentanedicarboxylic acid, 1,3-cyclopentanedicarboxylic acid, 1,1-cyclohexanedicarboxylic acid, 1,2-cyclohexanedicarboxylic acid, and 1,3-cyclohexanedicarboxylic acid. Examples include rubonic acid, 1,4-cyclohexanedicarboxylic acid, 1,4-(2-norbornene)dicarboxylic acid, norbornene-2,3-dicarboxylic acid, bicyclo[2.2.2]octane-1,4-dicarboxylic acid, bicyclo[2.2.2]octane-2,3-dicarboxylic acid, 2,5-dioxo-1,4-bicyclo[2.2.2]octanedicarboxylic acid, 1,3-adamantanedicarboxylic acid, 4,8-dioxo-1,3-adamantanedicarboxylic acid, 2,6-spiro[3.3]heptanedicarboxylic acid, 1,3-adamantanediacetic acid, camphoric acid, etc.

[0050] Examples of linear polyhydric amines include ethylenediamine, 1,3-propanediamine, tetramethylenediamine, pentamethylenediamine, hexamethylenediamine, N,N'-dimethylhexamethylenediamine, and octamethylenediamine. Examples of alicyclic polyhydric amines include 1,4-diaminocyclohexane, 4,4'-methylenebis(cyclohexylamine), and 1,3-bis(aminomethyl)cyclohexane. Furthermore, compounds having both a carboxyl group and an amino group can also be used as compound (R2).

[0051] • Synthesis of compound (Q) Compound (Q) can be obtained by reacting compound (E) with a reactive compound. In this reaction, the epoxy group of compound (E) reacts with the reactive group of the reactive compound to obtain a compound (i.e., compound (Q)) in which a substructure derived from compound (R1) is bonded to a main skeleton derived from compound (E). Furthermore, by using compound (R2) as the reactive compound when reacting compound (E) with the reactive compound to obtain compound (Q), a compound (Q) crosslinked by compound (R2) can be obtained.

[0052] In the reaction to obtain compound (Q), the method of charging each raw material (compound (E), compound (R1), and compound (R2)) may be a batch method in which all raw materials are charged at once, a semi-continuous method in which at least some of the raw materials are continuously supplied into the reactor, or a continuous polymerization method in which all raw materials are continuously supplied into the reactor and the product in the reactor is continuously withdrawn at the same time.

[0053] When compound (E), compound (R1), and compound (R2) are reacted to obtain compound (Q) as a reaction product of compound (E), compound (R1), and compound (R2), the order in which each raw material is charged into the reactor is not particularly limited. For example, (i) a method in which compound (E), compound (R1), and compound (R2) are reacted simultaneously; (ii) a method in which compound (E) and compound (R1) are charged into the reactor and reacted to obtain an intermediate, and then compound (R2) is added into the reactor and the intermediate is reacted with compound (R2); (iii) a method in which compound (E) and compound (R2) are charged into the reactor and reacted to obtain an intermediate, and then compound (R1) is added into the reactor and the intermediate is reacted with compound (R1). Of these, methods (i) and (ii) are preferred because they make it easier to obtain a low molecular weight compound (Q) and allow for sufficient low-voltage driving of the liquid crystal element.

[0054] In the synthesis of compound (Q), the amounts of compound (E) and compound (R1) used are preferably such that, for every mole of epoxy groups in compound (E), the amount of reactive groups (functional groups that can react with epoxy groups) in compound (R1) is 0.01 moles or more, more preferably 0.02 moles or more, and even more preferably 0.05 moles or more. Furthermore, the amounts of compound (E) and compound (R1) used are preferably such that, for every mole of epoxy groups in compound (E), the amount of reactive groups in compound (R1) is 0.9 moles or less, more preferably 0.8 moles or less, and even more preferably 0.75 moles or less.

[0055] When compound (R2) is used in the synthesis of compound (Q), the amount of compound (R2) used is preferably such that the amount of reactive groups (functional groups that can react with epoxy groups) of compound (R2) is 0.005 moles or more, more preferably 0.01 moles or more, and even more preferably 0.03 moles or more, per mole of epoxy groups of compound (E). Furthermore, the amount of compound (R2) used is preferably such that the amount of reactive groups of compound (R2) is 0.7 moles or less, more preferably 0.6 moles or less, and even more preferably 0.5 moles or less, per mole of epoxy groups of compound (E).

[0056] Furthermore, the total amount of compound (R1) and compound (R2) used is preferably such that the total amount of reactive groups of compound (R1) and compound (R2) is 0.02 moles or more, more preferably 0.05 moles or more, and even more preferably 0.1 moles or more, per mole of epoxy groups of compound (E). Furthermore, the total amount of compound (R1) and compound (R2) used is preferably such that the total amount of reactive groups of compound (R1) and compound (R2) is 0.9 moles or less, more preferably 0.8 moles or less, and even more preferably 0.75 moles or less, per mole of epoxy groups of compound (E).

[0057] The reaction between compound (E) and the reactive compound can preferably be carried out in the presence of a catalyst and an organic solvent. As the catalyst, for example, an organic base or a compound known as a so-called curing accelerator that promotes the reaction of compound (E) can be used (e.g., tertiary organic amines, quaternary organic amines, quaternary ammonium salts, etc.). The amount of catalyst used is preferably 100 parts by mass or less, and more preferably 0.1 to 20 parts by mass, per 100 parts by mass of compound (E).

[0058] Examples of organic solvents used in the above reaction include hydrocarbons, ethers, esters, ketones, amides, and alcohols. The organic solvent is preferably used in a proportion such that its solid content concentration (the ratio of the total mass of components other than the solvent in the reaction solution to the total weight of the solution) is 0.1% by mass or more, and more preferably 5% to 50% by mass. The reaction solvent may also contain a small amount of water along with the organic solvent. In the above reaction, the reaction temperature is preferably 0 to 200°C, and more preferably 50 to 150°C. The reaction time is preferably 0.1 to 50 hours, and more preferably 0.5 to 20 hours. After the reaction is complete, it is preferable to wash the organic solvent layer separated from the reaction solution with water. After washing with water, the organic solvent layer can be dried with a suitable drying agent as needed, and then the solvent can be removed to obtain compound (Q).

[0059] Compound (Q) preferably has at least one group (epoxy group) selected from the group consisting of oxiranyl groups and oxetanyl groups. The presence of epoxy groups in compound (Q) allows for the formation of a liquid crystal alignment film with excellent mechanical strength, voltage retention characteristics, and reliability, for example, through reactions between compounds (Q) themselves or with a separately added crosslinking agent during heating during film formation. The amount of epoxy groups in compound (Q) can be adjusted by the ratio of the amount of epoxy groups in compound (E) to the total amount of reactive groups in the reactive compound. Specifically, compound (Q) having epoxy groups can be obtained by setting the amounts of compound (E), compound (R1), and compound (R2) used such that the amount of epoxy groups in compound (E) is greater than the total amount of reactive groups in the reactive compound.

[0060] In the liquid crystal alignment agent of this disclosure, the content of compound (Q) is preferably 1 part by mass or more, more preferably 5 parts by mass or more, and even more preferably 10 parts by mass or more, per 100 parts by mass of solids (components other than the solvent of the liquid crystal alignment agent) contained in the liquid crystal alignment agent. By setting the content of compound (Q) within the above range, a liquid crystal element with good alignment uniformity of liquid crystal molecules can be obtained, and the inkjet coating properties of the liquid crystal alignment agent can be improved. When forming a weakly anchored liquid crystal alignment film using the liquid crystal alignment agent of this disclosure, from the viewpoint of sufficiently achieving low-voltage driving, the content of compound (Q) is more preferably 15 parts by mass or more, and particularly preferably 20 parts by mass or more, per 100 parts by mass of solids contained in the liquid crystal alignment agent.

[0061] <Other ingredients> The liquid crystal alignment agent of this disclosure may further contain components other than compound (Q) (hereinafter also referred to as "other components"). Examples of other components include polymers that do not correspond to compound (Q) (hereinafter also referred to as "polymer (P)"), crosslinking agents, adhesion aids, solvents, etc.

[0062] ·Polymer (P) The main skeleton of polymer (P) is not particularly limited. Examples of polymer (P) include polyamic acid, polyamic acid ester, polyimide, polyorganosiloxane, polyester, polyenamine, polyurea, polyamide, polyamideimide, polybenzoxazole precursor, polybenzoxazole, cellulose derivative, polyacetal, and addition polymers. Examples of addition polymers include (meth)acrylic polymers, styrene polymers, maleimide polymers, (meth)acrylic-styrene copolymers, (meth)acrylic-maleimide copolymers, (meth)acrylic-styrene-maleimide copolymers, and styrene-maleimide copolymers.

[0063] From the viewpoint of obtaining a liquid crystal element with excellent performance in various aspects such as liquid crystal alignment, voltage retention characteristics, and reliability, while also enabling low-voltage driving of the liquid crystal element, the polymer (P) is preferably at least one selected from the group consisting of polyamic acid, polyamic acid ester, and polyimide. A liquid crystal alignment agent containing at least one selected from the group consisting of polyamic acid, polyamic acid ester, and polyimide, and compound (Q) is preferable because it makes it easier to concentrate compound (Q) in the upper layer, thereby significantly improving the low-voltage driving effect and making it easier to adjust the electrical characteristics.

[0064] The weight-average molecular weight (Mw) of the polymer (P) is preferably 2,000 or more, more preferably 2,500 or more, and even more preferably 3,000 or more, from the viewpoint of ensuring film-forming properties and ensuring the liquid crystal alignment and reliability of the liquid crystal element. Furthermore, from the viewpoint of sufficiently enabling low-voltage driving of the liquid crystal element, the Mw of the polymer (P) is preferably 100,000 or less, and more preferably 50,000 or less. In this specification, the Mw of the polymer is a polystyrene equivalent value measured by gel permeation chromatography (GPC).

[0065] The solution viscosity of the polymer (P) is preferably 10 to 800 mPa·s when it is a 10% by mass solution, and more preferably 15 to 500 mPa·s. The solution viscosity (mPa·s) is the value measured at 25°C using an E-type rotational viscometer for a 10% by mass polymer solution prepared using a good solvent for the polymer (γ-butyrolactone, N-methyl-2-pyrrolidone, etc.).

[0066] When polymer (P) is included in the liquid crystal alignment agent, the polymer (P) content is preferably 5 parts by mass or more, and more preferably 10 parts by mass or more, per 100 parts by mass of the total amount of compound (Q) and polymer (P), from the viewpoint of fully obtaining the effect of performance improvement by incorporating polymer (P). Furthermore, from the viewpoint of improving the inkjet coating properties of the liquid crystal element, the polymer (P) content is preferably 95 parts by mass or less, and more preferably 90 parts by mass or less, per 100 parts by mass of the total amount of compound (Q) and polymer (P). When polymer (P) is incorporated into the liquid crystal alignment agent, it is preferable to purify the polymer (P) by liquid-liquid extraction before incorporation. In the liquid-liquid extraction of polymer (P), one solvent selected from the group consisting of water and organic solvents may be used, or multiple solvents from this group may be used.

[0067] • Crosslinking agent The liquid crystal alignment agent of this disclosure may further contain a crosslinking agent. By further containing a crosslinking agent, it is possible to achieve low-voltage driving while sufficiently suppressing display defects caused by abrasion of the liquid crystal alignment film due to thinning (slimming) of the glass substrate or vibration during transport of the liquid crystal panel. Examples of crosslinking agents include compounds having two or more of at least one selected from the group consisting of oxyranyl groups, oxetanyl groups, cyclic carbonate groups, hydroxyl groups, protected hydroxyl groups, carboxyl groups, protected carboxyl groups, mercapto groups, protected mercapto groups, amino groups, protected amino groups, protected isocyanate groups, and polymerizable carbon-carbon unsaturated bond groups in one molecule.

[0068] From the viewpoint of obtaining a liquid crystal alignment film that exhibits good weak anchoring characteristics while sufficiently suppressing afterimages, the number of crosslinking groups in one molecule of the crosslinking agent is preferably 2 to 10, and more preferably 2 to 6. Furthermore, the molecular weight of the crosslinking agent is preferably 100 to 1,000, more preferably 100 to 800, and even more preferably 100 to 700.

[0069] Specific examples of crosslinking agents include compounds having an oxiranil group or an oxetanil group, such as the compound exemplified as compound (E). Examples of compounds having a cyclic carbonate group include those represented by the following formulas (d1-1) and (d1-2).

[0070] Compounds having a hydroxyl group or a protected hydroxyl group can preferably include compounds having a methylol group, a protected methylol group, a hydroxyalkylamide group, or a protected hydroxyalkylamide group. Specific examples of these include compounds represented by formulas (d2-1) to (d2-5) and (d3-1) to (d3-5) below.

[0071] Examples of compounds having a carboxyl group or a protected carboxyl group include the compounds exemplified as polycarboxylic acids that may be used in the production of compound (Q) and their protected derivatives. Examples of compounds having a mercapto group or a protected mercapto group include 1,2-ethanedithiol, 1,3-propanedithiol, 1,3,4-thiadiazole-2,5-dithiol, 1,10-decanedithiol, pentaerythritol tetrakis(3-mercaptobutyrate), and 1,3,5-tris(2-(3-sulfanylbutanoyloxy)ethyl)-1,3,5-triazinan-2,4,6-trione.

[0072] Examples of compounds having an amino group or a protected amino group include those represented by formulas (d4-1) to (d4-5) below. Furthermore, the exemplified polyhydric amines and their protected derivatives may also be used in the production of compound (Q).

[0073] Examples of compounds having a protected isocyanate group include compounds in which the isocyanate group in tolylene diisocyanate, xylylene diisocyanate, chlorophenyl diisocyanate, hexamethylene diisocyanate, tetramethylene diisocyanate, isophorone diisocyanate, or diphenylmethane diisocyanate is protected with 3,6-dimethylpyrazole, methyl ethyl ketoxime, diethyl malonate, or ε-caprolactam, and compounds represented by the following formula (d5-1).

[0074] Examples of compounds having polymerizable carbon-carbon unsaturated bond groups include compounds having (meth)acryloyl groups, maleimide groups, alkenyl groups, vinylphenyl groups, vinyl ether groups, or 3-methylenetetrahydrofuran-2(3H)-on-5-yl groups. Specific examples of these include ethylene glycol di(meth)acrylate, 1,6-hexanediol di(meth)acrylate, pentaerythritol tri(meth)acrylate, and compounds represented by the following formulas (d6-1) to (d6-7).

[0075] [ka] [ka] (In formula (d2-4), Ac represents an acetyl group.) [ka] [ka] [ka] [ka]

[0076] In order to obtain a liquid crystal element with sufficiently reduced afterimages while achieving low-voltage driving while maintaining good liquid crystal alignment and voltage holding characteristics, the crosslinking agent is preferably a compound having two or more crosslinkable groups in one molecule, selected from the group consisting of compounds having an oxyranil group, an oxetanil group, a cyclic carbonate group, a methylol group, a hydroxyalkylamide group, a protected hydroxyalkylamide group, an amino group, a protected amino group, a protected isocyanate group, and a polymerizable carbon-carbon unsaturated bond group. More preferably, the crosslinking agent is a compound having two or more crosslinkable groups in one molecule, selected from the group consisting of compounds having an oxyranil group, an oxetanil group, a cyclic carbonate group, a methylol group, and a hydroxyalkylamide group.

[0077] As a crosslinking agent, compounds without aromatic rings (hereinafter also referred to as "aliphatic crosslinking agents") can be preferably used because they allow for sufficient low-voltage driving of the liquid crystal element while obtaining a liquid crystal element with superior liquid crystal alignment properties. Aliphatic crosslinking agents may be compounds with a chain structure or may have a cyclic structure. Specific examples of aliphatic crosslinking agents include compounds without aromatic rings among those exemplified above.

[0078] From the viewpoint of obtaining a liquid crystal alignment film exhibiting weak anchoring characteristics while improving the mechanical properties and adhesion of the liquid crystal alignment film, and from the viewpoint of obtaining a liquid crystal element with sufficiently reduced afterimage, the crosslinking agent content is preferably 0.5 parts by mass or more per 100 parts by mass of the total amount of compound (Q) and polymer (P) contained in the liquid crystal alignment agent. More preferably, the crosslinking agent content is 1 part by mass or more, and even more preferably 2 parts by mass or more, per 100 parts by mass of the total amount of compound (Q) and polymer (P). Furthermore, from the viewpoint of obtaining a liquid crystal element exhibiting good liquid crystal alignment, the crosslinking agent content is preferably 30 parts by mass or less, more preferably 20 parts by mass or less, and even more preferably 15 parts by mass or less, per 100 parts by mass of the total amount of compound (Q) and polymer (P).

[0079] • Adhesion enhancer Adhesion aids are components that improve the adhesion between a liquid crystal alignment film formed using a liquid crystal alignment agent and a substrate or sealing material. Functional silane coupling agents having reactive functional groups are preferably used as adhesion aids. Examples of reactive functional groups in functional silane coupling agents include carboxyl groups, (meth)acryloyl groups, oxyranyl groups, oxetanyl groups, vinyl groups, and isocyanate groups.

[0080] Specific examples of functional coupling agents include, for example, trimethoxysilyl benzoic acid, γ-glycidoxypropyltrimethoxysilane, γ-glycidoxypropyltriethoxysilane, 2-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, 3-(meth)acryloxypropyltrimethoxysilane, 3-(meth)acryloxypropyltriethoxysilane, vinyltriacetoxysilane, vinyltrimethoxysilane, and 3-isocyanatepropyltriethoxysilane.

[0081] When the liquid crystal alignment agent of this disclosure contains an adhesion aid, the amount of the adhesion aid is preferably 0.1 to 20 parts by mass, and more preferably 0.2 to 10 parts by mass, per 100 parts by mass of the polymer component contained in the liquid crystal alignment agent.

[0082] ·solvent The liquid crystal alignment agent of this disclosure is prepared as a liquid composition in which compound (Q) and optionally used components are preferably dispersed or dissolved in a suitable solvent.

[0083] Organic solvents are preferred as solvents. Specific examples include amides such as N,N-dimethylformamide and N,N-dimethylacetamide; lactams such as N-methyl-2-pyrrolidone, N-ethyl-2-pyrrolidone, and γ-butyrolactam; ureas such as 1,2-dimethyl-2-imidazolidinone and 1,3-dimethyl-2-imidazolidinone; lactones such as γ-butyrolactone; and carbonates such as ethylene carbonate and propylene carbonate. (Poly)alkylene glycol monoalkyl ethers such as ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol mono-n-propyl ether, ethylene glycol mono-n-butyl ether (butyl cellosolve), diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol mono-n-propyl ether, diethylene glycol mono-n-butyl ether, triethylene glycol monomethyl ether, triethylene glycol monoethyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol mono-n-propyl ether, propylene glycol mono-n-butyl ether, dipropylene glycol monomethyl ether, dipropylene glycol monoethyl ether, dipropylene glycol mono-n-propyl ether, dipropylene glycol mono-n-butyl ether, tripropylene glycol monomethyl ether, and tripropylene glycol monoethyl ether; Alkyl lactate esters such as methyl lactate, ethyl lactate, and butyl lactate; alkyl alcohols that may have linear, branched, or cyclic structures such as methanol, ethanol, propanol, butanol, isopropanol, isobutanol, t-butanol, octanol, 2-ethylhexanol, and cyclohexanol; alkoxy alcohols such as 3-methoxy-1-butanol; keto alcohols such as diacetone alcohol; ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, diethylene glycol monomethyl ether acetate, diethylene glycol monoethyl ether acetate (Poly)alkylene glycol monoalkyl ether acetates such as acetates, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, dipropylene glycol monomethyl ether acetate, 3-methoxybutyl acetate, and 3-methyl-3-methoxybutyl acetate; ethers such as diethylene glycol dimethyl ether, diethylene glycol methyl ethyl ether, diethylene glycol diethyl ether, and tetrahydrofuran; ketones such as methyl ethyl ketone, diisobutyl ketone, cyclohexanone, cyclopentanone, 2-heptanone, and 3-heptanone; Examples include diacetates such as propylene glycol diacetate, 1,3-butylene glycol diacetate, and 1,6-hexanediol diacetate; alkoxycarboxylic acid esters such as methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, ethyl ethoxyacetate, and 3-methyl-3-methoxybutylpropionate; other esters such as ethyl acetate, n-propyl acetate, i-propyl acetate, n-butyl acetate, i-butyl acetate, n-amyl formate, i-amyl acetate, n-butyl propionate, ethyl butyrate, n-propyl butyrate, i-propyl butyrate, n-butyl butyrate, methyl pyruvate, ethyl pyruvate, n-propyl pyruvate, methyl acetoacetate, ethyl acetoacetate, and ethyl 2-oxobutanoate; aromatic hydrocarbons such as toluene and xylene; and phenols such as phenol and methylphenol.

[0084] Other components to be included in the liquid crystal alignment agent of this disclosure include, in addition to those mentioned above, surfactants, antioxidants, metal chelating compounds, curing accelerators, fillers, dispersants, photosensitizers, and the like. The proportion of these other components can be appropriately selected depending on the compound, as long as it does not impair the effects of this disclosure.

[0085] The solid content concentration of the liquid crystal alignment agent in this disclosure (the ratio of the total mass of components other than the solvent in the liquid crystal alignment agent to the total mass of the liquid crystal alignment agent) is appropriately selected considering viscosity, volatility, etc. The solid content concentration of the liquid crystal alignment agent in this disclosure is preferably in the range of 1 to 10% by mass. If the solid content concentration is 1% by mass or more, a sufficient film thickness of the coating can be secured, and a liquid crystal alignment film exhibiting better liquid crystal alignment properties can be obtained. If the solid content concentration is 10% by mass or less, the coating can be made of an appropriate thickness, and a liquid crystal alignment film exhibiting good liquid crystal alignment properties can be easily obtained. Furthermore, the viscosity of the liquid crystal alignment agent becomes appropriate, and good coatability can be ensured.

[0086] ≪Liquid crystal alignment film and method for manufacturing the same≫ The liquid crystal alignment film of this disclosure is preferably a weakly anchored liquid crystal alignment film manufactured using the liquid crystal alignment agent prepared as described above. The method for manufacturing a weakly anchored liquid crystal alignment film using the liquid crystal alignment agent of this disclosure is not particularly limited and can be carried out in the same manner as when manufacturing a liquid crystal alignment film using a conventionally known liquid crystal alignment agent. A preferred method is to apply the liquid crystal alignment agent of this disclosure onto a substrate and preferably heat the applied surface, as this allows for easy film formation.

[0087] The substrate on which the liquid crystal alignment film is formed is not particularly limited. Examples of substrates include glass such as float glass and soda glass; and transparent substrates made of plastics such as polyethylene terephthalate, polybutylene terephthalate, polyethersulfone, polycarbonate, and poly(alicyclic olefin).

[0088] The method for applying the liquid crystal alignment agent to the substrate is not particularly limited. The liquid crystal alignment agent can be applied by, for example, a spin coating method, a printing method (e.g., offset printing method, flexographic printing method, etc.), an inkjet method, a slit coating method, a bar coater method, an extrusion die method, a direct gravure coater method, a chamber doctor coater method, an offset gravure coater method, an impregnation coater method, an MB coater method, etc.

[0089] After applying the liquid crystal alignment agent, preheating (pre-bake) is preferably performed to prevent dripping of the liquid crystal alignment agent. The pre-bake temperature is preferably 30 to 200°C, and the pre-bake time is preferably 0.25 to 10 minutes. Subsequently, a baking (post-bake) process is performed to further remove the solvent. The baking temperature (post-bake temperature) is preferably 80 to 280°C, more preferably 80 to 250°C. The post-bake time is preferably 5 to 200 minutes. The film thickness of the formed film is preferably 0.001 to 2.5 μm. By the above operation, a weakly anchoring liquid crystal alignment film can be easily manufactured. After post-bake, the coating film may be subjected to an alignment treatment (e.g., rubbing alignment treatment or photo-alignment treatment) as needed to obtain a liquid crystal alignment film.

[0090] ≪Method for manufacturing liquid crystal elements≫ The liquid crystal element of this disclosure is manufactured using a liquid crystal alignment agent containing the compound (Q) described above. The liquid crystal element manufactured by the manufacturing method of this disclosure comprises a pair of substrates consisting of a first substrate and a second substrate, and a liquid crystal layer disposed between the pair of substrates. The operating mode of the liquid crystal in the liquid crystal element is not particularly limited and can be applied to various modes such as TN type, STN type, VA type (including VA-MVA type, VA-PVA type, etc.), IPS (In-Plane Switching) type, FFS (Fringe Field Switching) type, OCB (Optically Compensated Bend) type, and PSA (Polymer Sustained Alignment) type. When a weak anchoring liquid crystal alignment film is provided in the liquid crystal element of this disclosure, the manufacturing method of this disclosure includes a step of applying the liquid crystal alignment agent of this disclosure to the surface of one of the pair of substrates to form a liquid crystal alignment film (this is referred to as step A).

[0091] When forming a weakly anchored liquid crystal alignment film using the liquid crystal alignment agent of the present disclosure, the manufacturing method of the present disclosure preferably further includes the following step B in addition to step A. Step B: A step of forming a strongly anchored liquid crystal alignment film having a stronger anchoring energy than the weakly anchored liquid crystal alignment film on the surface of a substrate other than the substrate on which the weakly anchored liquid crystal alignment film was formed, among the first and second substrates. The order of processes A and B is not particularly limited; process A may be performed before process B, or process B may be performed before process A. Furthermore, processes A and B may be performed simultaneously.

[0092] Step A is preferably performed according to Step 1 shown below, and Step B is preferably performed according to Steps 1 and 2 shown below. Furthermore, a liquid crystal element can be obtained by constructing a liquid crystal cell in Step 3 using a substrate on which a liquid crystal alignment film has been formed, obtained in Steps A and B. Note that the substrate used in Step 1 differs depending on the desired operating mode. Steps 2 and 3 are common to all operating modes.

[0093] <Step 1: Formation of the coating> In step 1, a liquid crystal alignment agent is applied to each substrate surface, and preferably the applied surface is heated to form a coating on the substrate. Conventional known liquid crystal alignment agents can be used as appropriate for forming a strongly anchoring liquid crystal alignment film.

[0094] When manufacturing, for example, an IPS (In-Plane Switching) type or FFS (Fringe Field Switching) type liquid crystal element using a pair of substrates, an electrode substrate with comb-shaped patterned electrodes and a counter substrate without electrodes are used. Transparent conductive films can be used as electrodes. Examples of transparent conductive films include NESA films (registered trademark of PPG, Inc., USA) made of tin oxide (SnO2), and ITO films made of indium oxide-tin oxide (In2O3-SnO2). When forming liquid crystal alignment films on the electrode substrate and the counter substrate, there are two embodiments: a first embodiment in which a strongly anchored liquid crystal alignment film is formed on the electrode substrate and a weakly anchored liquid crystal alignment film is formed on the counter substrate; and a second embodiment in which a weakly anchored liquid crystal alignment film is formed on the electrode substrate and a strongly anchored liquid crystal alignment film is formed on the counter substrate. Of these, the first embodiment is preferred from the viewpoint of driving the liquid crystal element at a low voltage. More specifically, in a pair of substrates consisting of a first substrate and a second substrate, where the first substrate has a pair of electrodes and the second substrate does not have electrodes, it is preferable to form a strongly anchored liquid crystal alignment film on the surface of the first substrate and a weakly anchored liquid crystal alignment film on the surface of the second substrate.

[0095] <Step 2: Orientation Treatment> When manufacturing IPS-type or FFS-type liquid crystal elements, it is preferable to apply a treatment (alignment treatment) to the coating film formed on the substrate in step 1 to impart liquid crystal alignment ability. Preferred alignment treatments include rubbing, where the surface of the coating film formed on the substrate is rubbed with cotton or nylon, or photo-alignment, where the coating film is irradiated with light to impart liquid crystal alignment ability. The alignment treatment may be performed on either a coating film formed with a liquid crystal alignment agent for a strongly anchoring liquid crystal alignment film or a coating film formed with a liquid crystal alignment agent for a weakly anchoring liquid crystal alignment film, or on both. Of these, it is preferable, from the viewpoint of obtaining a liquid crystal element exhibiting good liquid crystal alignment, to apply a liquid crystal alignment agent for forming a strongly anchoring liquid crystal alignment film to one of the electrode substrate and the opposing substrate, and then perform the alignment treatment only on the resulting coating film. The liquid crystal alignment agent used to form the strongly anchoring liquid crystal alignment film preferably contains a crosslinking agent, which can improve the mechanical strength of the liquid crystal alignment film and its adhesion to the substrate or sealing material.

[0096] Furthermore, with the weakly anchored liquid crystal alignment film formed by the liquid crystal alignment agent of this disclosure, a liquid crystal element exhibiting good liquid crystal alignment can be obtained without performing alignment treatments such as rubbing alignment treatment or photo-alignment treatment on the coating film used to obtain the weakly anchored liquid crystal alignment film. Utilizing these characteristics, the weakly anchored liquid crystal alignment film formed by the liquid crystal alignment agent of this disclosure may be arranged as a protective film provided on a color filter in a liquid crystal element, thereby giving the weakly anchored liquid crystal alignment film protective functions (specifically, planarization and protection from impurities or humidity).

[0097] <Step 3: Liquid Crystal Cell Construction> Next, a liquid crystal cell is manufactured in which a liquid crystal layer is placed between two opposing substrates, using a substrate on which a strongly anchoring liquid crystal alignment film is formed and a substrate on which a weakly anchoring liquid crystal alignment film is formed. Methods for manufacturing a liquid crystal cell include, for example, placing two substrates opposite each other with a gap in between so that the liquid crystal alignment films face each other, bonding the periphery of the two substrates with a sealing material, injecting and filling liquid crystal into the cell gap surrounded by the substrate surface and the sealing material, and sealing the injection hole; an ODF method; and so on. As the sealing material, for example, an epoxy resin containing a curing agent and aluminum oxide spheres as spacers can be used. Examples of liquid crystals constituting the liquid crystal layer include nematic liquid crystals and smectic liquid crystals, with nematic liquid crystals being preferred.

[0098] When manufacturing a PSA-type liquid crystal element using the liquid crystal alignment agent of this disclosure, both substrates of the pair may be provided with the liquid crystal alignment film of this disclosure, or one substrate may be provided with the liquid crystal alignment film of this disclosure, and the other substrate may be provided with a liquid crystal alignment film formed from a polymer composition having a different composition from the liquid crystal alignment agent of this disclosure. It is preferable that the liquid crystal alignment films on both substrates of the pair are formed with the liquid crystal alignment agent of this disclosure, from the viewpoint of forming a liquid crystal alignment film with good adhesion to the substrate (particularly adhesion in high temperature and high humidity environments) and from the viewpoint of reducing the number of manufacturing steps.

[0099] PSA-type liquid crystal elements can be manufactured by a method that includes the following steps. A step of forming a coating film by applying the liquid crystal alignment agent of this disclosure onto the conductive film of each of a pair of substrates having a conductive film. A process for constructing a liquid crystal cell by arranging a pair of substrates coated with a liquid crystal alignment agent so that the coating films face each other with a liquid crystal layer in between. • A process of applying a voltage between conductive films and irradiating a liquid crystal cell with light.

[0100] Specifically, a liquid crystal cell is constructed in the same manner as in steps 1 to 3 above, except that a photopolymerizable monomer is injected or dropped together with the liquid crystal between a pair of substrates having a conductive film. Conventionally known compounds can be used as the photopolymerizable monomer injected or dropped together with the liquid crystal. Preferably, it is a polyfunctional (meth)acrylic monomer.

[0101] In the manufacturing of PSA-type liquid crystal elements, after constructing the liquid crystal cell, a voltage is applied between the conductive films of a pair of substrates, and the liquid crystal cell is irradiated with light. The applied voltage can be, for example, 5 to 50 V DC or AC. As the irradiated light, ultraviolet light and visible light including wavelengths of 150 to 800 nm can be used. Of these, ultraviolet light including wavelengths of 300 to 400 nm is preferred. As the light source for the irradiation light, for example, a low-pressure mercury lamp, a high-pressure mercury lamp, a deuterium lamp, a metal halide lamp, an argon resonance lamp, a xenon lamp, an excimer laser, etc. can be used. The amount of light irradiated is preferably 1,000 to 200,000 J / m 2 More preferably, 1,000 to 100,000 J / m 2 That is the case.

[0102] When manufacturing liquid crystal display elements, a polarizing plate is then bonded to the outer surface of the liquid crystal cell. Examples of polarizing plates include a polarizing film called an "H film," which is made by stretching and oriented polyvinyl alcohol while absorbing iodine, sandwiched between cellulose acetate protective films, or a polarizing plate made of the H film itself.

[0103] The liquid crystal elements of this disclosure can be effectively applied to a variety of uses. Specifically, they can be used, for example, in various display devices such as watches, portable game consoles, word processors, notebook computers, car navigation systems, camcorders, PDAs, digital cameras, mobile phones, smartphones, various monitors, liquid crystal televisions, information displays, head-mounted displays, smart glasses, as well as in dimming devices, phase difference films, and the like. [Examples]

[0104] The present invention will be described in detail below with reference to examples, but it is not limited to the following examples.

[0105] In the following example, the imidation rate of the polyimide and the molecular weight (Mw, Mn) of the polymer were measured by the following method. <Imidification rate of polyimides> A polyimide solution was added to pure water, and the resulting precipitate was thoroughly dried under reduced pressure at room temperature. Then it was dissolved in deuterated dimethyl sulfoxide, with tetramethylsilane as the reference material, at room temperature. 1 1H-NMR measurements were performed. 1 The imidization rate [%] was determined from the 1H-NMR spectrum using the following formula (1). Imidization rate [%] = (1 - (β 1 / ( β 2 ×α)))×100 …(1) (In formula (1), β 1 This represents the peak area originating from the proton of the NH group, appearing around a chemical shift of 10 ppm, and β 2 α represents the peak area derived from other protons, and α is the ratio of other protons to one proton of the NH group in the polymer precursor (polyamic acid). <Molecular weight of polymer (Mw, Mn)> The weight-average molecular weight (Mw) and number-average molecular weight (Mn) were measured by gel permeation chromatography (GPC) under the following conditions. Equipment: Showa Denko Corporation's "GPC-101" GPC columns: Combining "GPC-KF-801", "GPC-KF-802", "GPC-KF-803", and "GPC-KF-804" manufactured by Shimadzu GLC Co., Ltd. Mobile phase: Tetrahydrofuran (THF) Column temperature: 40℃ Flow rate: 1.0mL / min Sample concentration: 1.0% by mass Sample injection volume: 100 μL Detector: Differential refractometer Standard material: Monodisperse polystyrene

[0106] The abbreviations for the compounds used in the following examples are shown below. For convenience, the compound represented by formula (X) may be simply referred to as "compound (X)" below. In the examples and comparative examples, "parts" and "%" are based on mass unless otherwise specified.

[0107] ·Compound (E): A-1~A-8, M-1 [ka]

[0108] ·Compound (R1): B-1~B-7 [ka]

[0109] ·Compound (R2): C-1~C-8 [ka]

[0110] • Siloxane monomer, maleimide monomer: S-1, M-1 [ka]

[0111] • Tetracarboxylic acid dianhydrides: T-1 to T-8 [ka]

[0112] • Diamine compounds: D-1 to D-17 [ka]

[0113] • Additives: AD-1 to AD-8 [ka]

[0114] ≪Synthesis of Compounds≫ <Synthesis of compound (Q)> [Synthesis Example 1] In a 200 mL three-necked flask, 100 mole parts of compound (A-1), compound (B-3) as compound (R1) at 45 mol% relative to the amount of epoxy groups in compound (A-1), 1.071 g of tetrabutylammonium bromide, and 85 g of propylene glycol methyl ether acetate were added, and the mixture was stirred at 100 °C for 8 hours. After cooling to room temperature, the mixture was separated and washed 10 times with distilled water. The organic layer was then collected, concentrated and diluted twice using a rotary evaporator and NMP, and then prepared using NMP to obtain an NMP solution of compound (Q-1) with a solid content concentration of 10% by mass.

[0115] [Synthesis Examples 6, 12, 13, 15] The same procedure as in Synthesis Example 1 was followed, except that the types and amounts of compound (E) and compound (R1) were changed as shown in Table 1, to obtain compounds (Q-6), (Q-12), (Q-13), and (Q-15), respectively.

[0116] [Synthesis Example 2] In a 200 mL three-necked flask, 100 mole parts of compound (A-1), compound (B-2) as compound (R1) at 35 mol% relative to the amount of epoxy groups in compound (A-1), compound (C-3) as compound (R2) at 15 mol% relative to the amount of epoxy groups in compound (A-1), 0.956 g of tetrabutylammonium bromide, and 85 g of propylene glycol methyl ether acetate were added, and the mixture was stirred at 100 °C for 8 hours. After cooling to room temperature, the mixture was separated and washed 10 times with distilled water. The organic layer was then collected, concentrated and diluted twice using a rotary evaporator and NMP, and then prepared using NMP to obtain an NMP solution of compound (Q-2) with a solid content concentration of 10% by mass.

[0117] [Synthesis examples 3-5, 7-11, 14] The same procedure as in Synthesis Example 2 was performed, except that the types and amounts of compound (E), compound (R1), and compound (R2) were changed as shown in Table 1, to obtain compounds (Q-3) to (Q-5), (Q-7) to (Q-11), and (Q-14), respectively. [Comparative Synthesis Example 1] Compound (Q-16) was obtained by performing the same procedure as in Synthesis Example 2, except that compound (A-2) was used, compound (C-3) was used as compound (R2) at a concentration of 15 mol% relative to the amount of epoxy groups in compound (A-2), and compound (R1) was not used.

[0118] [Table 1]

[0119] <Synthesis of Addition Polymers> [Comparative Synthesis Example 2] Under nitrogen, 100 moles of compound (M-1) as the polymerization monomer, 2.0 g of 2,2'-azobis(2,4-dimethylvaleronitrile) as a radical polymerization initiator, and 50 mL of N-methyl-2-pyrrolidone (NMP) as a solvent were added to a 100 mL two-necked flask, and polymerization was carried out at 70°C for 6 hours. After reprecipitation in methanol, the precipitate was filtered to obtain the polymer. Next, the polymer obtained by the above polymerization was added to a 200 mL three-necked flask. Compound (B-4) was added at a concentration of 25 mol% relative to the epoxy group amount of the polymer, along with 1.268 g of tetrabutylammonium bromide and 85 g of propylene glycol methyl ether acetate. The mixture was stirred at 100°C for 8 hours. After cooling to room temperature, the solution was washed 10 times with distilled water. The organic layer was then collected and concentrated and diluted twice using a rotary evaporator with NMP. Finally, the solution was prepared using NMP to a solid content concentration of 10% by mass to obtain an NMP solution of the maleimide polymer (referred to as polymer (PM-1)). The weight-average molecular weight Mw, measured in polystyrene equivalent by GPC, was 40,000, and the molecular weight distribution Mw / Mn was 1.9. [Comparative Synthesis Example 3] The same procedure as in Comparative Synthesis Example 2 was performed, except that the type and amount of carboxylic acid used were changed as shown in Table 2, to obtain a maleimide polymer (this polymer (PM-2)).

[0120] <Synthesis of polyorganosiloxanes> [Comparative Synthesis Example 4] In a 1000 mL three-necked flask, 100.0 g of 2-(3,4-epoxycyclohexyl)ethyltrimethoxysilane (compound (S-1)) as a siloxane monomer, 500 g of methyl isobutyl ketone, and 10.0 g of triethylamine were charged and mixed at room temperature. Then, 100 g of deionized water was added dropwise from a dropping funnel over 30 minutes, and the reaction was carried out at 80°C for 6 hours while mixing under reflux. After the reaction was complete, the organic layer was removed and washed with a 0.2% by mass aqueous solution of ammonium nitrate until the water after washing was neutral, and then the solvent and water were removed under reduced pressure. An appropriate amount of methyl isobutyl ketone was added to obtain a 50% by mass solution of the polymer (ESSQ-1), which is a polyorganosiloxane having epoxy groups. In a 500 mL three-necked flask, compound (B-5) was added at a concentration of 25 mol% relative to the amount of epoxy groups in polymer (ESSQ-1), along with 1.00 g of tetrabutylammonium bromide, 20.0 g of polymer (ESSQ-1)-containing solution, and 290.0 g of methyl isobutyl ketone. The mixture was stirred at 90°C for 18 hours. After cooling to room temperature, the solution was separated and washed 10 times with distilled water. The organic layer was then collected and concentrated and diluted twice using a rotary evaporator with NMP. Finally, the solution was prepared using NMP to a solid content concentration of 10% by mass to obtain an NMP solution of polyorganosiloxane (referred to as polymer (PS-1)). The weight-average molecular weight of polymer (PS-1) was 4,500.

[0121] [Table 2]

[0122] <Synthesis of polyamic acids> [Synthesis Example 16] 100 moles of compound (T-3) as a tetracarboxylic dianhydride and 100 moles of compound (D-1) as a diamine compound were dissolved in N-methyl-2-pyrrolidone (NMP), and the reaction was carried out at 60°C for 6 hours to obtain a solution containing 20% ​​by mass of polyamic acid (referred to as polymer (PI-1)).

[0123] [Synthesis Examples 17-23, 25-27] Polyamic acids (polymers (PI-2) to (PI-8), (PI-10) to (PI-12)) were obtained by performing the same procedure as in Synthesis Example 16, except that the types and amounts of tetracarboxylic dianhydrides and diamine compounds used were changed as shown in Table 3. In Table 3, the values ​​for tetracarboxylic dianhydrides (acid dianhydrides 1 to 3) represent the proportion (molar ratio) of each compound relative to 100 moles of the total amount of tetracarboxylic dianhydrides used in the synthesis of the polymer. The values ​​for diamine compounds (diamines 1 to 4) represent the proportion (molar ratio) of each compound relative to 100 moles of the total amount of diamine compounds used in the synthesis of the polymer.

[0124] <Synthesis of polyimides> [Synthesis Example 24] 100 moles of compound (T-5) as a tetracarboxylic dianhydride and 100 moles of compound (D-14) as a diamine compound were dissolved in NMP, and the reaction was carried out at 60°C for 6 hours to obtain a solution containing 20% ​​by mass of polyamic acid. Next, NMP was added to the obtained polyamic acid solution to make a 10% by mass solution of polyamic acid, and pyridine and acetic anhydride were added to carry out a dehydration and cyclization reaction at 80°C for 4 hours. After the dehydration and cyclization reaction, the solvent in the system was replaced with fresh NMP to obtain a solution containing 15% by mass of polyimide with an imidization rate of approximately 30% (this is referred to as polymer (PI-9)).

[0125] [Table 3]

[0126] <<Preparation and Evaluation of Liquid Crystal Alignment Agents (1)>> <Preparation of liquid crystal alignment agent> (1) Preparation of liquid crystal alignment agent for weak anchoring film formation [Example 1] A solution containing 30 parts by mass of compound (Q-1) obtained in Synthesis Example 1 and a solution containing 70 parts by mass of polymer (PI-1) obtained in Synthesis Example 16 were mixed. 5 parts by mass of compound (AD-2) were added to this mixture, and the mixture was further diluted with N-methyl-2-pyrrolidone (NMP), gamma-butyrolactone (GBL), butyl cellosolve (BC), diacetone alcohol (DAA), and diethylene glycol diethyl ether (DEDG) to obtain a solution with a solvent composition of NMP:GBL:BC:DAA:DEDG = 30:30:15:15:10 (by mass ratio) and a solid content concentration of 3.5% by mass. This solution was filtered through a 0.2 μm pore size filter to prepare a liquid crystal alignment agent (AL-1) for weak anchoring film formation.

[0127] [Examples 2-14, Comparative Examples 1-5] Liquid crystal alignment agents for weak anchoring film formation (AL-2) to (AL-14) and (AR-1) to (AR-5) were prepared in the same manner as in Example 1, except that the types and amounts of raw materials used in the preparation of the liquid crystal alignment agents were changed as shown in Table 4.

[0128] [Table 4]

[0129] (2) Preparation of liquid crystal alignment agent for forming strong anchoring film [Preparation Examples 1-3] Liquid crystal alignment agents (AL-15) to (AL-17) for forming strong anchoring films were prepared in the same manner as in Example 1, except that the types and amounts of raw materials used in the preparation of the liquid crystal alignment agents were changed as shown in Table 5.

[0130] [Table 5]

[0131] <Manufacturing and evaluation of liquid crystal elements (FFS type liquid crystal display elements)> FFS-type liquid crystal cells were manufactured and various characteristics were evaluated. In manufacturing the FFS-type liquid crystal cells, first, a substrate (electrode substrate) having an electrode pair formed in the order of a bottom electrode without a pattern, an insulating layer made of silicon nitride film, and a top electrode patterned in a comb-like manner on one side of the glass substrate, and a counter glass substrate (counter substrate) without electrodes were prepared. A schematic plan view of the top electrode used is shown in Figure 1. Figure 1(a) is a top view of the top electrode, and Figure 1(b) is an enlarged view of the portion C1 enclosed by the dashed line in Figure 1(a). In this embodiment, the line width d1 of the electrode was 4 μm, and the distance d2 between electrodes was 6 μm. In addition, four systems of drive electrodes, electrode A, electrode B, electrode C, and electrode D, were used as the top electrode (Figure 2). The bottom electrode acts as a common electrode that acts on all four systems of drive electrodes, and each of the regions of the four systems of drive electrodes becomes a pixel region.

[0132] [Example 15: Rubbing-oriented FFS type liquid crystal display element] 1. Manufacturing of liquid crystal display elements (1) Formation of weakly anchored liquid crystal alignment film A weak anchoring liquid crystal alignment agent (AL-1) was applied to one substrate surface of opposing substrates using a spin coater, heated on an 80°C hot plate for 1 minute, and then heated in a 230°C oven with nitrogen purging for 30 minutes to form a weak anchoring liquid crystal alignment film with an average thickness of 100 nm.

[0133] (2) Formation of strongly anchored liquid crystal alignment film by rubbing orientation method A liquid crystal alignment agent for strong anchoring film formation (AL-17) was applied to the electrode formation surface of an electrode substrate using a spin coater. After heating on an 80°C hot plate for 1 minute, the substrate was heated in a 230°C oven with nitrogen purging for 30 minutes to form a coating with an average thickness of 100 nm. The surface of this coating was then rubbed twice using a rubbing machine with a roll wrapped in rayon cloth, at a roll rotation speed of 1,000 rpm, a stage movement speed of 30 mm / second, and a pile insertion length of 0.3 mm. At this time, the rubbing direction was set so that it was perpendicular to the direction of the double-headed arrow in Figure 2(b). The coating with the rubbing alignment treatment was ultrasonically cleaned in ultrapure water for 1 minute, and then dried in a 100°C oven for 10 minutes to form a strong anchoring liquid crystal alignment film.

[0134] (3) Manufacturing of Rubbing-oriented FFS type liquid crystal cells On the outer periphery of one of the substrates prepared in (1) and (2) above, which had a liquid crystal alignment film, epoxy resin adhesive containing 3.5 μm diameter aluminum oxide spheres was dispensed using a dispenser, leaving a liquid crystal injection port. Then, the surfaces of the pair of substrates with liquid crystal alignment films were pressed together, and the adhesive was heat-cured at 150°C for 1 hour. Next, positive-type liquid crystal (Merck, MLC-7028-100) was filled into the gap between the substrates through the liquid crystal injection port, and the liquid crystal injection port was sealed with epoxy adhesive. Furthermore, to eliminate the flow orientation during liquid crystal injection, it was heated at 120°C and then slowly cooled to room temperature.

[0135] 2. Evaluation (1) Evaluation of low-voltage operation at room temperature (25°C) The FFS-type liquid crystal cell manufactured in 1.(3) above was sandwiched between two polarizing plates to minimize its brightness, and the liquid crystal cell with polarizing plates (liquid crystal display element) was placed between a backlight and a luminance meter, with the optical axes aligned. Then, a voltage was applied to the liquid crystal display element in 0.1V increments up to 10V. The VT curve was obtained by measuring the brightness as a function of the applied voltage, and the voltage value at which the brightness was maximized was estimated. For evaluation, a liquid crystal display element with a liquid crystal alignment film formed on the opposing substrate using a strong anchoring film formation liquid crystal alignment agent (AL-17) by the rubbing alignment method, similar to the electrode substrate, was prepared as a reference cell, and the evaluation was judged by how much the maximum brightness voltage of the liquid crystal display element manufactured in each example was reduced relative to the maximum brightness voltage of the reference cell. A liquid crystal display element whose maximum brightness voltage was reduced by 0.8V or more compared to the maximum brightness voltage of the reference cell was rated as "exceptionally good (◎)", one whose maximum brightness voltage was reduced by 0.4V or more but less than 0.8V compared to the maximum brightness voltage of the reference cell was rated as "good (○)", and one whose maximum brightness voltage reduction compared to the maximum brightness voltage of the liquid crystal display element of the reference cell was less than 0.4V was rated as "poor (×)". As a result, this embodiment received an evaluation of "exceptionally good (◎)".

[0136] (2) Evaluation of orientation uniformity For the FFS-type liquid crystal cells manufactured in 1.(3) above, retardation was measured at 20 points within a single pixel plane using an Axoscan manufactured by OptoScience, Inc., and the standard deviation was calculated. The evaluation was as follows: a standard deviation of retardation of 0.070 or less was rated as "good (◎)", and a standard deviation greater than 0.070 was rated as "bad (×)". As a result, the orientation uniformity of this embodiment was evaluated as "good (◎)".

[0137] (3) Evaluation of inkjet coating properties (IJ coating properties) As the substrate to which the liquid crystal alignment agent was applied, a glass substrate with transparent electrodes made of ITO was heated on a hot plate at 200°C for 1 minute, and then subjected to ultraviolet / ozone cleaning to reduce the water contact angle on the transparent electrode surface to 10° or less. On this substrate, a liquid crystal alignment agent for weak anchoring film formation (AL-1) was applied to the transparent electrode surface of the glass substrate with transparent electrodes using an inkjet coating machine (manufactured by Shibaura Mechatronics Co., Ltd.). The application conditions were 2,500 strokes / (nozzle·minute), with a discharge rate of 250 mg / 10 seconds, and applied in two passes (a total of four passes). After letting it stand for 1 minute after application, the substrate was heated at 50°C to form a coating with an average film thickness of 0.1 μm. The obtained coating was observed with the naked eye under the irradiation of an interference fringe measurement lamp (sodium lamp) to evaluate unevenness and repulsion. Furthermore, the same procedure as above was performed, except that the heating temperature during coating film formation was changed from 50°C to 60°C and 80°C, and the presence or absence of unevenness and repulsion in the coating film was observed. If neither unevenness nor repulsion was observed at any of the heating temperatures of 50°C, 60°C, and 80°C, the inkjet coating performance was rated as "particularly good (◎)". If at least one of unevenness or repulsion was observed at one of the heating temperatures of 50°C, 60°C, and 80°C, it was rated as "good (○)". If at least one of unevenness or repulsion was observed at two of the heating temperatures, it was rated as "acceptable (△)". If at least one of unevenness or repulsion was observed at all heating temperatures, it was rated as "poor (×)". As a result, this example was rated as "good (○)".

[0138] [Examples 16-28, Comparative Examples 6, 7, 9, 10] Except for changing the type of liquid crystal alignment agent used (weak anchoring film formation alignment agent and strong anchoring film formation liquid crystal alignment agent) as shown in Table 6, a rubbing-aligned FFS type liquid crystal display element was manufactured in the same manner as in Example 15 and various evaluations were performed. The evaluation results are shown in Table 6.

[0139] [Comparative Example 8] An FFS-type liquid crystal display element was manufactured and evaluated in the same manner as in Example 15, except that the type of liquid crystal alignment agent used was changed as shown in Table 6, and rubbing treatment was also applied to the coating film formed on the opposing substrate. When the pair of substrates were stacked, the rubbing directions of each substrate were made to be opposite parallel. The evaluation results are shown in Table 6.

[0140] [Example 29: Photo-aligned FFS type liquid crystal display element] 1. Manufacturing of liquid crystal display elements (1) Formation of weakly anchored liquid crystal alignment film A weak anchoring liquid crystal alignment agent (AL-1) was applied to one side of a counter substrate using a spin coater, heated on an 80°C hot plate for 1 minute, and then heated in a 230°C oven with nitrogen purging for 30 minutes to form a weak anchoring liquid crystal alignment film with an average thickness of 100 nm.

[0141] (2) Formation of strongly anchored liquid crystal alignment films by photo-alignment method A liquid crystal alignment agent (AL-16) for strong anchoring film formation was applied to the electrode formation surface of the electrode substrate using a spin coater. Next, it was heated on an 80°C hot plate for 1 minute, and then heated for 30 minutes in a 230°C oven with nitrogen purging to form a coating with an average thickness of 100 nm. The surface of this coating was then exposed to 200 mJ / cm² of linearly polarized ultraviolet light containing a 254 nm emission line using a Hg-Xe lamp. 2 Photo-alignment treatment was performed by irradiating the substrate from the direction normal to the substrate. At this time, the direction of the polarization plane was set so that the direction of the line segment obtained by projecting the polarization plane of polarized ultraviolet light onto the substrate was parallel to the direction of the double-headed arrow in Figure 2(b). The photo-aligned coating was heat-treated by heating it in a 230°C oven with nitrogen purged for 30 minutes to form a strongly anchored liquid crystal alignment film.

[0142] (3) Manufacturing of photo-aligned FFS type liquid crystal cells Using the pair of substrates prepared in (1) and (2) above, an FFS-type liquid crystal display element was manufactured in the same manner as in Example 15.

[0143] 2. Evaluation Various evaluations were performed in the same manner as in Example 15, except that the photo-aligned FFS type liquid crystal cell manufactured in 1.(3) above was used. The evaluation results are shown in Table 6.

[0144] [Examples 30-42, Comparative Examples 11, 13, 14, 15] An optically aligned FFS type liquid crystal display element was manufactured in the same manner as in Example 29, except that the type of liquid crystal alignment agent used (weak anchoring film formation alignment agent and strong anchoring film formation liquid crystal alignment agent) was changed as shown in Table 6, and various evaluations were performed. The evaluation results are shown in Table 6.

[0145] [Comparative Example 12] A photo-aligned FFS type liquid crystal display element was manufactured and evaluated in the same manner as in Example 29, except that the type of liquid crystal alignment agent used was changed as shown in Table 6, and the coating film formed on the opposing substrate was also subjected to photo-alignment treatment. When the pair of substrates were stacked, the projection direction of the polarization axis onto the substrate surface during light irradiation was made opposite parallel to that of each substrate. The evaluation results are shown in Table 6.

[0146] [Table 6]

[0147] As shown in Table 6, the liquid crystal display elements manufactured using the liquid crystal alignment agents of Examples 1 to 14 as liquid crystal alignment agents for weak anchoring film formation received evaluations of "particularly good," "good," or "acceptable" for low-voltage driving, alignment uniformity, and inkjet coating properties, indicating a good balance of various characteristics. In contrast, the liquid crystal display elements manufactured using the liquid crystal alignment agents of Comparative Examples 1 to 5 instead of the liquid crystal alignment agents of Examples 1 to 14 received an evaluation of "poor" for at least one of the following: low-voltage driving and alignment uniformity.

[0148] <<Preparation and Evaluation of Liquid Crystal Alignment Agents (2)>> <Preparation of liquid crystal alignment agent> [Example 43, Comparative Examples 16, 17] Liquid crystal alignment agents (AL-18), (AR-6), and (AR-7) were prepared by performing the same procedure as in Example 1, except that the types and amounts of raw materials used in the preparation of the liquid crystal alignment agents were changed as shown in Table 7.

[0149] [Table 7]

[0150] <Manufacturing and evaluation of liquid crystal display elements (PSA type liquid crystal display elements)> [Example 44] 1. Preparation of liquid crystal composition Liquid crystal composition LC1 was obtained by adding 0.3% by mass of a photopolymerizable compound represented by the following formula (L-1) to 10 g of nematic liquid crystal (negative liquid crystal manufactured by Merck, MLC-6608) and mixing. [ka]

[0151] 2. Manufacturing of liquid crystal display elements A liquid crystal alignment agent (AL-18) was applied to each electrode surface of two glass substrates, each having ITO electrodes patterned in a slit shape and divided into multiple regions, using a liquid crystal alignment film printing machine (manufactured by Nippon Printing Co., Ltd.). Next, the substrates were heated on an 80°C hot plate for 1 minute (pre-bake) to remove the solvent, and then heated on a 150°C hot plate for 10 minutes (post-bake) to form a coating with an average thickness of 0.06 μm. After ultrasonic cleaning of this coating in ultrapure water for 1 minute, the substrates were dried in a 100°C clean oven for 10 minutes to obtain a pair (2 substrates) with a coating that would become a liquid crystal alignment film. Next, epoxy resin adhesive containing aluminum oxide spheres with a diameter of 5.5 μm was applied to the outer edges of each of the pair of substrates having a coating, and then the two substrates were overlapped and pressed together so that the coating surfaces faced each other, and the adhesive was cured. Then, the liquid crystal composition LC1 prepared in step 1 was filled between the pair of substrates through the liquid crystal injection port, and the liquid crystal injection port was sealed with an acrylic photocurable adhesive. After that, with a voltage applied between the conductive films of the obtained liquid crystal cell, 100,000 J / m2 The light was irradiated with the specified dose.

[0152] 3. Evaluation (1) Evaluation of adhesion in high temperature and high humidity environments In the same manner as described in 2. above, a pair (2) of glass substrates with a coated film was prepared. ODF sealing material (Sekisui Chemical Co., Ltd., S-WB42) was applied to the coated film of one glass substrate to a width of 0.5 mm, and the other glass substrate was bonded together so that the coated film and the ODF sealing material were in contact. After that, a metal halide lamp was used to heat 30,000 J / m². 2 After irradiating with light (equivalent to 365nm), test specimens were prepared by heating in a 120°C oven for 1 hour. Subsequently, they were stored in an oven set to 85°C and 85% humidity for 300 hours, and then the adhesion strength was measured at 25°C using an Imada Manufacturing tensile and compression testing machine (model number: SDWS-0201-100SL). The evaluation was based on an adhesion strength of 180 N / cm². 2 If the result is above this, it is classified as "exceptionally good (◎)", 150 N / cm 2 More than 180N / cm 2 If the value is less than 150 N / cm², it is considered "Good (○)". 2 A result below this value was classified as "Poor (×)". As a result, this example received a rating of "Very Good (◎)".

[0153] (2) Evaluation of orientation uniformity and inkjet coating properties (IJ coating properties) Various evaluations were performed in the same manner as in Example 15, except that the liquid crystal cell manufactured in section 2 above was used. The evaluation results are shown in Table 8.

[0154] [Comparative Examples 18, 19] A PSA-type liquid crystal display element was manufactured and evaluated in the same manner as in Example 44, except that the type of liquid crystal alignment agent used was changed as shown in Table 8. The evaluation results are shown in Table 8.

[0155] [Table 8]

[0156] As shown in Table 8, the PSA-type liquid crystal display element manufactured using the liquid crystal alignment agent of Example 43 received an evaluation of "particularly good" for adhesion to the substrate and alignment uniformity, and an evaluation of "good" for inkjet coating properties, indicating a good balance of various characteristics. In contrast, the liquid crystal display elements manufactured using the liquid crystal alignment agents of Comparative Examples 16 and 17 received an evaluation of "poor" for adhesion to the substrate. These results demonstrate that liquid crystal alignment agents containing compound (Q) can also be used for forming liquid crystal alignment films in PSA-type liquid crystal elements.

Claims

1. The compound (Q) is a reaction product of a compound (E) having at least one selected from the group consisting of an oxiranyl group and an oxetanyl group, and a reactive compound having a functional group that can react with an oxiranyl group or an oxetanyl group. The compound (E) has a molecular weight of 1,000 or less and contains multiple groups of at least one selected from the group consisting of an oxyranyl group and an oxetanyl group within one molecule, or contains one oxyranyl group or one oxetanyl group and one polymerizable carbon-carbon unsaturated bond group within one molecule. A liquid crystal alignment agent comprising a compound (R1) in which the reactive compound has one functional group (R1) in one molecule that can react with an oxiranyl group or an oxetanyl group.

2. The liquid crystal alignment agent according to claim 1, wherein the compound (E) has 1 to 10 groups in one molecule selected from the group consisting of oxiranyl groups and oxetanyl groups.

3. The liquid crystal alignment agent according to claim 1, wherein the compound (R1) is a nonpolymer.

4. The liquid crystal alignment agent according to claim 1, wherein the compound (R1) further comprises an alkyl group having 4 to 50 carbon atoms, a monovalent group represented by the following formula (1), or a monovalent alicyclic saturated hydrocarbon group having 4 to 50 carbon atoms with one aliphatic hydrocarbon ring. *-R １ -(O-R ２ ) ｒ -OR ３ …(1) (In formula (1), R １ and R ２ are each independently an alkanediyl group. r is an integer of 0 or more. R ３ is an alkyl group. However, the total number of carbon atoms of R １ and r R ２ and R ３ is 4 to 50. "*" represents a bond.)

5. The liquid crystal alignment agent according to claim 1, wherein the compound (R1) does not have an aromatic ring.

6. The liquid crystal alignment agent according to claim 1, wherein the reactive compound comprises the compound (R1) and a compound (R2) which is a nonpolymer having multiple functional groups capable of reacting with an oxiranil group or an oxetanil group within one molecule.

7. The liquid crystal alignment agent according to claim 6, wherein the compound (R2) has 2 to 10 functional groups in one molecule that can react with an oxiranil group or an oxetanil group.

8. The liquid crystal alignment agent according to claim 6, wherein the compound (R2) does not have an aromatic ring.

9. The liquid crystal alignment agent according to claim 1, wherein the compound (Q) has at least one selected from the group consisting of an oxiranyl group and an oxetanyl group.

10. Furthermore, the liquid crystal alignment agent according to claim 1 further contains at least one polymer selected from the group consisting of polyamic acid, polyamic acid ester, and polyimide.

11. The liquid crystal alignment agent according to claim 1, further comprising a crosslinking agent.

12. A liquid crystal alignment agent according to claim 1, for forming a weak anchoring film.

13. A liquid crystal alignment agent containing the reaction product of compound (E), compound (R1), and compound (R2) shown below. Compound (E): A compound having a molecular weight of 1,000 or less, and containing multiple groups of at least one selected from the group consisting of oxiranyl groups and oxetanyl groups within one molecule, or containing one oxiranyl group or one oxetanyl group and one polymerizable carbon-carbon unsaturated bond group within one molecule. Compound (R1): A compound having one functional group in one molecule that can react with an oxiranyl group or an oxetanyl group. Compound (R2): A nonpolymer having multiple functional groups capable of reacting with oxiranyl or oxetanyl groups within a single molecule.

14. A liquid crystal alignment film formed using the liquid crystal alignment agent described in any one of claims 1 to 13.

15. A liquid crystal element comprising the liquid crystal alignment film described in claim 14.

16. A method for manufacturing a liquid crystal element comprising a pair of substrates consisting of a first substrate and a second substrate, and a liquid crystal layer disposed between the pair of substrates, A method for manufacturing a liquid crystal element, comprising the step of applying a liquid crystal alignment agent according to any one of claims 1 to 13 to the surface of one of the pair of substrates to form a liquid crystal alignment film.

17. A liquid crystal alignment film formed with the liquid crystal alignment agent according to any one of claims 1 to 13 is a weakly anchored liquid crystal alignment film. The method for manufacturing a liquid crystal element according to claim 16, further comprising the step of forming a strongly anchoring liquid crystal alignment film having a stronger anchoring energy than the weakly anchoring liquid crystal alignment film on the surface of a substrate other than the substrate on which the weakly anchoring liquid crystal alignment film is formed, among the first substrate and the second substrate.

18. The method for manufacturing a liquid crystal element according to claim 17, wherein the strongly anchoring liquid crystal alignment film is a rubbing alignment film or a photoalignment film.

19. The first substrate has a pair of electrodes, and the second substrate does not have electrodes. The strongly anchoring liquid crystal alignment film is formed on the surface of the first substrate. A method for manufacturing a liquid crystal element according to claim 17, wherein the weakly anchoring liquid crystal alignment film is formed on the surface of the second substrate.

20. A compound that is the reaction product of compound (E) and compound (R1) shown below. Compound (E): A compound having a molecular weight of 1,000 or less, and containing multiple groups of at least one selected from the group consisting of oxiranyl groups and oxetanyl groups within a single molecule. Compound (R1): A nonpolymer having one functional group in each molecule that can react with at least one selected from the group consisting of an oxyranyl group and an oxetanyl group, and having an alkyl group having 4 to 50 carbon atoms, a monovalent group represented by the following formula (1), or a monovalent alicyclic saturated hydrocarbon group having 4 to 50 carbon atoms with one aliphatic hydrocarbon ring. *-R １ -(O-R ２ ) ｒ -OR ３ …(1) (In formula (1), R １ and R ２ These are alkanediyl groups, independent of each other. r is a non-negative integer. ３ is an alkyl group. However, R １ and r R ２ and R ３ The total number of carbon atoms is between 4 and 50. (* indicates a bond.)

21. A compound that is the reaction product of compound (E), compound (R1), and compound (R2) shown below. Compound (E): A compound having a molecular weight of 1,000 or less, and containing multiple groups of at least one selected from the group consisting of oxiranyl groups and oxetanyl groups within a single molecule. Compound (R1): A nonpolymer having one functional group in each molecule that can react with at least one selected from the group consisting of an oxyranyl group and an oxetanyl group, and having an alkyl group having 4 to 50 carbon atoms, a monovalent group represented by the following formula (1), or a monovalent alicyclic saturated hydrocarbon group having 4 to 50 carbon atoms with one aliphatic hydrocarbon ring. *-R １ -(O-R ２ ) ｒ -OR ３ …(1) (In formula (1), R １ and R ２ These are alkanediyl groups, independent of each other. r is a non-negative integer. ３ is an alkyl group. However, R １ and r R ２ and R ３ The total number of carbon atoms is between 4 and 50. (* indicates a bond.) Compound (R2): A nonpolymer having multiple functional groups capable of reacting with oxiranyl or oxetanyl groups within a single molecule.

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