TW200844610A - Liquid crystal alignment agent and liquid crystal display element - Google Patents

Abstract

The present invention provides a liquid crystal alignment agent and a liquid crystal display element using the same. The liquid crystal alignment agent maintains the voltage holding ratio while reducing accumulated charges and further has outstanding printability. The liquid crystal alignment agent comprises (a) a polymer and/or its imidized polymer obtained by means of a reaction of a specific tetracarboxylic acid dianhydride and diamine, (b) at least one selected from the group consisting of 2-pyrrolidone, N-methyl succinimide, and solvent, the solid matter concentration is 1 to 10 wt%, the viscosity is 5 to 12 mPa*s and the water content is 0.0 to 0.5wt%. The liquid crystal display element is provided with the liquid crystal alignment film made from the liquid crystal alignment agent.

Description

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a liquid crystal alignment agent used for forming a liquid crystal alignment film of a liquid crystal display element, and a liquid crystal display element. More specifically, it relates to a liquid crystal alignment agent which can form a liquid crystal alignment film having good electrical properties and excellent printability, and a liquid crystal display element having a liquid crystal alignment film obtained from the liquid crystal alignment agent. [Prior Art] As a liquid crystal display element, a TN type liquid crystal display element having a so-called TN (twisted nematic) type liquid crystal cell is known, which is provided on a substrate surface of a transparent conductive film such as ITO (indium oxide-tin oxide). A liquid crystal alignment film formed of polyacrylic acid, polyimine or the like is formed thereon, and as a substrate for a liquid crystal display element, two substrates are opposed to each other, and a nematic type having positive dielectric anisotropy is formed in the gap. The liquid crystal layer constitutes a unit cell of the sandwich structure, and the long axis of the liquid crystal molecules is continuously twisted by 90 degrees from one substrate to the other substrate. Further, an STN (Super Torsional Nematic) type liquid crystal display element having a higher contrast ratio and a smaller viewing angle dependency than a TN type liquid crystal display element has been developed. Such an STN type liquid crystal display device uses a liquid crystal in which a chiral agent as an optically active substance is blended in a nematic liquid crystal as a liquid crystal by using a long axis of liquid crystal molecules to continuously twist more than 180 degrees between substrates. The birefringence effect produced by the state of the amplitude. In addition, a vertical alignment type liquid crystal display element called MVA (Multi-Domain Vertical Alignment) type in which protrusions are formed on a transparent conductive film to control the alignment direction of liquid crystals has been proposed (refer to Patent Document 1 and Non-Patent Document 1). . 200844610 MVA type liquid crystal display element is excellent not only in viewing angle and contrast, but also in the process of forming a liquid crystal alignment film, and it is not necessary to perform polishing treatment, and is excellent in the process. As the liquid crystal alignment film which is applied to the TN, STN and MVA types described above, electrical performance such as short image erasing time of the liquid crystal display element is required. Further, as an alignment agent for forming these liquid crystal alignment films, it is required to have excellent printability in ink jet printing or lithography. [Patent Document 1] Japanese Laid-Open Patent Publication No. Hei 6-222366 (Patent Document 3) Japanese Patent Application Laid-Open No. Hei No. Hei. Japanese Unexamined Patent Publication No. Hei No. Hei. No. Hei. No. Hei. No. Hei. The object is to provide a liquid crystal alignment agent capable of maintaining a high voltage holding ratio of a polyfluorene-based liquid crystal alignment film while reducing accumulated charge (afterimage), and having excellent printability, and a liquid crystal using the same Display component. According to the present invention, the above object of the present invention, first, is achieved by a liquid crystal alignment agent which contains (a) at least one selected from the group consisting of the following formula (1) and a group of tetracarboxylic dianhydrides selected from the group consisting of a polymer obtained by reacting at least one of the diamine groups represented by the following formulas (3) to (6) and/or a quinone imidized polymer thereof, (b) selected from the group consisting of 2-pyrrolidone and N-methyl At least one of the group consisting of amber succinimide and N-methyl pentene 200844610 diimine, and a solvent having a solid concentration of 1 to 10% by weight, a viscosity of 5 to 12 mPa_s, and a moisture content of 0.0 1 to 0.5% by weight,

200844610

(wherein R/ to R4 are each independently a linear, branched or cyclic alkyl group having a carbon number of 1 to 40 or a linear, branched or cyclic group having a carbon number of 4 to 40; The alkenyl group, 1 to 15 of the hydrogen atoms of R1 to R4 may be substituted by a fluorine atom, and each of A1 and A2 is independently a hydrogen atom or a methyl group). According to the present invention, the above object of the present invention, and secondly, is achieved by a liquid crystal display member having a liquid crystal alignment film produced from the above liquid crystal alignment agent. [Embodiment] (a) Component The liquid crystal alignment agent of the present invention contains at least one selected from the group consisting of tetradecanoic acid-Sf selected from the above formulas (1) and (2), and is selected from the above formulas (3) to (6). a polymer obtained by at least one reaction of the indicated diamine groups (hereinafter referred to as "specific poly-proline acid") and/or a quinone imidized polymer thereof (hereinafter collectively referred to as "(a) polymer") As component (a). Hereinafter, the tetracarboxylic anhydride and the diamine which can be used for synthesizing the (a) polymer contained in the liquid crystal alignment agent of the present invention will be described. <tetracarboxylic dianhydride> The tetracarboxylic dianhydride used in the synthesis of the specific polyamic acid contains 2,3,5·tricarboxycyclopentyl acetic acid dianhydride represented by the above formula (1) In the group consisting of 5-(2,5-dioxotetrahydro-3-furanyl)-3-methyl-3-cyclohexene-1,2-dicarboxylic anhydride represented by the above formula (2) It is formed by at least one (hereinafter referred to as "specific tetracarboxylic dianhydride"). In the synthesis of a specific polyamine, it is also possible to use other tetracarboxylic dianhydrides other than the specific tetracarboxylic dianhydride. Examples of the other tetracarboxylic dianhydride include an alicyclic tetracarboxylic dianhydride (excluding a specific tetracarboxylic dianhydride), an aliphatic tetracarboxylic dianhydride, and an aromatic tetracarboxylic dianhydride. Examples of the alicyclic tetracarboxylic dianhydride include 1,2,3,4-cyclobutanetetracarboxylic dianhydride and 1,2-dimethyl-1,2,3,4-cyclobutane. Alkane tetracarboxylic dianhydride, 1,3-dimethyl-1,2,3,4-cyclobutane tetracarboxylic dianhydride, 1,3-dichloro-1,2,3,4-cyclobutane Tetracarboxylic dianhydride, 1,2,3,4-tetramethyl-1,2,3,4-cyclobutyl"tetracarboxylic dianhydride, 1,2,3,4-cyclopentanetetracarboxylic acid Dihydride, 1,2,4,5-cyclohexanin tetracarboxylic dianhydride, 3,3',4,4'-dicyclohexyltetracarboxylic dianhydride, cis-3,7-dibutyl ring Xin·1,5-diene-1,2,5,6-tetracarboxylic dianhydride, 3,5,6-tricarbonyl-2-carboxy 200844610 base norbornane-2:3,5:6-two Anhydride, 2,3,4,5-tetrahydrofuran tetracarboxylic dianhydride, 1,2,4-tricarboxycyclopentyl acetic acid dianhydride, tetracyclo[4.4.0.12,5,r,1Q]dodecane-3 , 4,8,9-tetracarboxylic dianhydride, 1,3,3&,4,5,91)-hexahydro-5-(tetrahydro-2,5-dioxo-3-furanyl)- Naphthalene [l,2-c]-furan-1,3-dione, 1,3,3&,4,5,913-hexahydro-5-methyl-5-(tetrahydro-2,5-dioxo) -3-furanyl)·naphthalene [l,2·c]-furan-l,3·dione, 1,3,3a,4,5,9b-hexahydro-5-ethyl-5-(tetrahydrogen -2,5-dioxo- 3-furyl)-naphthalene [l,2-c]-furan-1,3-dione, 1,3,3&,4,5,91)-hexahydro-7-methyl-5-(four Hydrogen-2,5-dioxo-3-furanyl)-naphthalene[l,2-c]-furan-1,3-dione, ® 1,3,3&,4,5,913-hexahydro-7 -ethyl-5-(tetrahydro-2,5-dioxo-3-furanyl)-. naphthalene [l,2-c]-furan-1,3-dione, l,3,3a,4 ,5,9b-hexahydro-8-methyl-5-(tetra-hydro-2,5-dioxo-3-furanyl)-naphthalene[l,2-c]-furan-1,3-di Ketone, 1,3,3&,4,5,91)-hexahydro-8-ethyl-5-(tetrahydro-2,5-dioxo-3-furanyl)-naphthalene [l,2- c]-purine-1,3-dione, 1,3,3&,4,5,913-hexahydro-5,8-dimethyl-5-(tetrahydro-2,5-dioxo-3 -furyl)-naphthalene [l,2-c]-furan-1,3-dione, bicyclo[2.2.2]-oct-7-ene-2,3,5,6-tetracarboxylic dianhydride, 3-oxabicyclo[3.2.1] φ octane-2,4-dione-6-spiro-3'-(tetrahydrofuran-2',5'-dione), 3,5,6-tricarboxy- 2-carboxynorbornane-2:3,5:6-dianhydride, 4,9-dioxatricyclo[5.3.1.0''5]undecane-3,5,8,10-tetraketone, lower a compound represented by the formula (I) or (II), etc., -10- 200844610

(wherein R5 and R7 represent a divalent organic group having an aromatic ring, R6 and R8 represent a hydrogen atom or an alkyl group, and a plurality of R6 and R8 present may be the same or different). The aliphatic tetracarboxylic dianhydride may, for example, be butane tetracarboxylic acid dianhydride or the like. Examples of the aromatic tetracarboxylic dianhydride include pyromellitic dianhydride, 3,3', 4,4'-benzophenonetetracarboxylic dianhydride, and 3,3',4,4'- Biphenyl sulfonium tetracarboxylic dianhydride, 1,4,5,8-naphthalenetetracarboxylic dianhydride, 2,3,6,7-naphthalenetetracarboxylic dianhydride, 3,3',4,4' - Biphenyl ether tetracarboxylic dianhydride, 3,3',4,4'-dimethyldiphenylnonane tetracarboxylic dianhydride, 3,3',4,4'-tetraphenylnonane tetracarboxylic acid Dihydride, 1,2,3,4·furan tetracarboxylic dianhydride, 4,4′·bis(3,4-dicarboxyphenoxy)diphenyl sulfide dianhydride, 4,4′-di ( 3,4-Dicarboxyphenoxy)diphenylphosphonium dianhydride, 4,4'-bis(3,4-dicarboxyphenoxy)diphenylpropane dianhydride, 3,3',4,4' - perfluoroisopropylidene di phthalic anhydride, 2,2',3,3'-biphenyltetracarboxylic dianhydride, 3,3',4,4'-biphenyltetracarboxylic dianhydride, Di(phthalic acid) phenylphosphine oxide dianhydride, p-phenylene-bis(triphenylphthalic acid) dianhydride, -11- 200844610 phenyl-bis(triphenylphthalic acid) dianhydride , bis(triphenylphthalic acid)-4,4'-diphenyl ether dianhydride, two ( Phenylphthalic acid)-4,4'-diphenylmethane dianhydride, ethylene glycol-di(hydrogen trimellitate), propylene glycol-di(hydrogen trimellitate), 1,4-butyl Glycol-di(hydrogen trimellitate), 1,6-hexanediol-di(hydrogen trimellitate), 1,8-octanediol-di(anhydroelellitic acid ester), 2 , 2-bis(4-hydroxyphenyl)propane-di(hydrogen trimellitate), a compound represented by the following formulas (7) to (10), and the like.

-12- 200844610

These other tetracarboxylic dianhydrides may be used alone or in combination of two or more of the above-mentioned other tetracarboxylic dianhydrides as alicyclic tetracarboxylic dianhydrides 1, 2, 3 from the viewpoint of exhibiting good alignment. 4-cyclobutane tetracarboxylic dianhydride, 1,3-dimethyl-1,2,3,4-cycloacid dianhydride, 1,2,3,4-tetramethyl-1,2,3, 4-cyclobutanetetracarboxylic acid di-S is used in combination. A good liquid crystal, preferably butane tetracarboxy: 1,2,3,4· -13- 200844610 cyclopentane tetracarboxylic dianhydride, 1,2,4-tricarboxycyclopentyl acetic acid dianhydride, cis Formula 3,7-dibutylcyclooctane-1,5-diene-1,2,5,6·tetracarboxylic dianhydride, 3,5,6-tricarbonyl-2-carboxynorbornane-2 :3,5:6-dianhydride, 1,3,3&,4,5,913-hexahydro-5-(tetrahydro-2,5-dioxo-3.furanyl)·naphthalene [l,2- c]-furan-1,3-dione, 1,3,31,4,5,91)-hexahydro-8-methyl-.5-(tetrahydro-2,5-dioxo-3- Furyl)-naphthalene [l,2-c]-furan-1,3-dione, 1,3,3&,4,5,913-hexahydro-5,8-dimethyl-5-(tetrahydro- 2,5-dioxo-3·furanyl)-naphthalene [l,2-c]-furan-1,3-dione, bicyclo[2.2.2]-oct-7-ene-2,3,5 , 6-tetracarboxylic dianhydride, 3-oxabicyclo[3.2.1]octane-2,4-dione-6-spiro-3'-(tetrahydrofuran-2',5'-dione), The compound represented by the following formula (11) to (13) or the compound represented by the following formula (14) in the compound represented by the above formula (II) in the compound represented by the formula (I),

-14- 200844610

Particularly preferred are 1,2,3,4-cyclobutanetetracarboxylic dianhydride, hydrazine, 3-dimethyl-1,2,3,4-cyclobutanetetracarboxylic dianhydride, and ,3,3a,4,5,9b-hexahydro-5-(tetrahydro-2,5-dioxo-3-furanyl)-naphthalene[l,2-c]furan-1,3-dione ,cis-3,7-dibutylcyclooctane-1,5-diene-1,2,5,6-tetracarboxylic dianhydride, 1,2,4-tricarboxycyclopentyl acetic acid dianhydride, 3,5,6-Tricarbonyl-2-carboxynorborner-2:3,5:6-dianhydride, 1,3,3&amp;,4,5,91)-hexahydro-8-methyl-5 -(tetrahydro-2,5-dioxo-3-furanyl)-naphthalene [1,2&lt;]furan-1,3-dione, 3-oxabicyclo[3.2.1]octane-2, 4-dione-6-spiro-3'-(tetrahydrofuran-2,5,-dione) and a compound represented by the above formula (12). Among other tetracarboxylic dianhydrides, preferred examples of the aliphatic tetracarboxylic dianhydride or the aromatic tetracarboxylic dianhydride include butane tetracarboxylic dianhydride, pyromellitic dianhydride, and 3,3'. , 4,4'-benzophenonetetracarboxylic dianhydride, 2,2',3,3'-biphenyl maple tetracarboxylic dianhydride, 3,3',4,4'-biphenyl fluorene Carboxylic dianhydride or 1,4,5,8-naphthalenetetracarboxylic dianhydride. As the other tetracarboxylic dianhydride, an alicyclic tetracarboxylic dianhydride is preferably used. When a specific polycarboxylic acid is synthesized, when a specific tetracarboxylic dianhydride is used together with other tetracarboxylic dianhydride, the use ratio of the specific tetracarboxylic dianhydride is preferably 50 with respect to the entire tetracarboxylic dianhydride. More than Mole. <Diamine> -15- 200844610 The diamine used in the synthesis of the poly-proline is at least one selected from the group consisting of diamines represented by the above formulas (3) to (6) (hereinafter referred to as "Specific diamine"). In the synthesis of a specific polyamine, it is also possible to use other diamines other than the specific diamine. Examples of the other diamine include an aromatic diamine, an aliphatic or alicyclic diamine, a diamine having a two-stage amine group in the molecule, and a nitrogen atom other than the amine group of the first-order amine group. Oxane and the like. Examples of the aromatic diamine include p-phenylenediamine, 2-methyl-1,4-phenylenediamine, 2-ethyl-1,4-phenylenediamine, and 2,5-dimethyl group. 1,4-phenylenediamine, 2,5-monoethyl-indole, 4-phenylenediamine, 2,3,5,6-tetramethyl-1,4-phenylenediamine, m-phenyl-amine, 4 , 4'-diaminodiphenylmethane, 4,4,-diaminodiphenyl phenylene, 4,4 '-diaminodiphenyl sulfide, 4,4,-diaminodiphenyl Base, 2,2 •-methyl-4,4, _diaminobiphenyl, 3,3, dimethyl- 4,4, _diaminobiphenyl, 4,4' _diamine Benzoquinone aniline, 4,4,-diaminodiphenyl ether, 1,5-diaminonaphthalene, 3,3-dimethyl-4,4,-diaminobiphenyl, 5j-anthracene 1-(4'-aminophenyl)-1,3,3-trimethylindan, 6-amino-1-(4,-aminophenyl)-1,3,3-trimethyl Indane, 3,4,-diaminodiphenyl ether, 3,3,-diaminobenzophenone, 3,4'-diaminobenzophenone, 4,4,-diaminodiphenyl Ketone, 2,2·bis[4-(4-aminophenoxy)phenyl]propane, 2,2-bis[4_(4j-ampenylphenoxy)phenyl]hexafluoropropane, 2,2- Bis(4-aminophenyl)hexafluoropropane, 2,2-[4-(4-amine Benzo)phenyl]anthracene, anthracene, 4_bis(4•aminophenoxy)benzene, iota, 3-(4-amine basic oxy)benzene, iota, 3-bis(3-aminobenzene) Oxy)benzene, 9,9•bis(4-aminophenyl)-1 0-hydroquinone, 2,7-diaminopurine, 9,9-dimethyl-2,7-diamino-16 - 200844610 芴,9,9-bis(4-aminophenyl)anthracene, 4,4'-methylene-bis(2-chloroaniline), 2,2',5,5'-tetrachloro-4 ,4,-Diaminobiphenyl, 2,2'-dichloro-4,4'-diamino-5,5'-dimethoxybiphenyl, 3,3'-dimethoxy-4 , 4'-diaminobiphenyl, 1,4,4'-(p-phenylisopropylene)diphenylamine, 4,4'-(meta-phenylisopropylene)diphenylamine, 2, 2'-bis[4-(4-Amino-2-trifluoromethylphenoxy)phenyl]hexafluoropropane, 4,4'-diamino-2,2'-bis(trifluoromethyl) Biphenyl, 4,4'-bis[(4-amino-2-trifluoromethyl)phenoxy]-octafluorobiphenyl, 3,6-diaminocarbazole, oxime-methyl-3 , 6-diaminocarbazole, oxime-ethyl-3,6-diamino group; oxazolium, fluorene-phenyl _3,6-diaminocarbazole, etc.; as the above aliphatic or alicyclic The amine may, for example, be 1,1- Meta-xylylenediamine, 1,3-propanediamine, butanediamine, pentanediamine, hexamethylenediamine, heptanediamine, octanediamine, decanediamine, 4,4-diaminoheptamethylenediamine, hydrazine , 4-diaminocyclohexane, isophoronediamine, tetrahydrodicyclopentadiene diamine, hexahydro-4,7-methylene dimethylene diamine, tricyclo[6.2.1 · 02'7]-undecene dimethyldiamine, 4,4'-methyl bis(cyclohexylamine), etc.; as the above molecule, having two first-order amine groups and the first-order amine group Examples of the diamine of the nitrogen atom include, for example, 2,3-diaminopyridine, 2,6-dijiridylpyridine, 3,4-diaminopyridine, 2,4-diaminopyrimidine, and 5. 6-Diamine oxime-2,3-dicyanopyrazine, 5,6-diamino-2,4-dihydroxypyrimidine, 2,4-diamino-6-dimethylamino-1,3 ,5·Triazine, 1,4-bis(3-aminopropyl)pyridazine, 2,4-di-l--6-isopropoxy-1,3,5-triazine, 2,4_ Diamino-6-methoxy j,3,5-triazine, 2,4-diamino-6-phenyl-1,3,5.triazine, 2,4-diamino-6- Methyl-s-triazine, 2,4-diamino-1,3,5-triazine, 4,6-diamino-2-vinyl-17- 200844610-s·triazine, 2,4 -diamino-5-phenylthiophene' 2,6 Diamine hydrazine, 5,6_February, 1,3 -*, methyl urinary 1! 疋, 3,5--amino-1,24-diindole, 69--amino-2 - Ethyl acridine lactate, 3,8-diaminophenylphenanthridine, = Aminoguanidine, 3,6 - a fe:yl η疋, mono(4-aminophenyl)benzene Examples of the above-mentioned diamine organooxosiloxane include a compound represented by the following formula (15), and H2N-^-CH2^~Si-rO-Sr.

{*CH2]^NH2 (15) (wherein R9 represents a hydrocarbon group having a carbon number of 1 to 12, and a plurality of existing R9 may be the same or different 'p is an integer of 1 to 3, and q is 1 to 2 〇 an integer). These other diamines may be used alone or in combination of two or more. Among these other diamines, preferred are p-phenylenediamine, 2-methyl-1,4-phenylenediamine, 2-ethyl-1,4-phenylenediamine, 2,5-dimethyl-i, 4-phenylenediamine, 2,5-diethyl-1,4-phenylenediamine, 2,3,5,6-tetramethyl-1,4-phenylenediamine, 4,4,-diamino Diphenylmethane, 4,4, diaminodiphenyl sulfide, 2,2'-dimethyl-4,4,-diaminobiphenyl, 1,5-diaminonaphthalene, 2,7- Diamino hydrazine, 9,9-dimethyl-2,7-diamino fluorene, 4,4'-diaminodiphenyl ether, 2,2-bis[4-(4-aminophenoxyl) Phenyl]propane, 9,9-bis(4.aminophenyl)anthracene, 2,2-bis[4-(4-aminophenoxy)phenyl]hexafluoropropane, 2,2 _ Bis(4-aminophenyl)hexafluoropropane, 4,4'-(p-phenylenediisopropylidene)diphenylamine, 4,4'-(inter)phenyldiisopropylidene)diphenylamine 1,4_cyclohexanediamine '4,4,-methylenebis(cyclohexyl-18 - 200844610 amine), 1,4-bis(4-aminophenoxy)benzene, 4,4' - bis(4-aminophenoxy)biphenyl, 2,6-diaminopyridine, 3,4-diaminopyridine, 2,4-diaminopyrimidine, 3,6-diaminoacridine , 3,6-diaminoisoxazole, N-methyl-3,6-diamine Carbazole, N-ethyl-3,6-diaminocarbazole or N-phenyl-3,6-diaminocarbazole, more preferably p-phenylenediamine, 2-methyl-1,4- Phenylenediamine, 2-ethyl-1,4-phenylenediamine, 2,5-dimethyl-1,4-phenylenediamine, 2,5-diethyl-1,4-phenylenediamine or 2 , 3,5,6-tetramethyl-1,4-benzene-*amine. When the pretilt performance of the liquid crystal alignment agent of the present invention is to be improved, in addition to the specific diamine and any of the other diamines used arbitrarily, it may be selected from the following formula (Q-1).

(wherein X1 is a single bond, -〇-, -CO-, -C〇〇·, -〇C〇-, -NHCO-, φ-CONH-, -S- or an aryl group, and Rl° is a carbon number It is an alkyl group of 10 to 20, a monovalent organic group having an alicyclic skeleton of 4 to 40 carbon atoms or a fluorine atom-containing monovalent organic group having a carbon number of 6 to 20, and the following formula (Q) - 2)

-19- 200844610 (where 'X2 is a single bond, -Ο -, · C Ο -, - C 〇〇-, · 0 C Ο -, - nH C 〇., -C〇NH-, -S- or The aryl group, R11 is at least one diamine of the diamine group represented by a divalent organic group having an alicyclic skeleton of 4 to 40 carbon atoms. They may be used alone or in combination of two or more. In the above formula (Q-1), the number of carbon atoms represented by R1Q in the range of 1 〇 to 2 Å may, for example, be n-decyl, n-dodecyl, n-xyl or n-hexadecyl. , n-octadecyl, n-icosyl and the like. The monovalent or divalent organic group having an alicyclic skeleton having 4 to 40 carbon atoms represented by R1{) of the above formula (Q-1) and Rn in the above formula (Q-2) may be mentioned. For example, a group having an alicyclic skeleton derived from a cycloalkane such as cyclobutane, cyclopentane, cyclohexane or cyclodecane; a group having a steroid skeleton such as cholesterol or cholestyl alcohol; and having a norbornene A group having a bridged alicyclic skeleton such as an alkane or adamantane. Among them, a group having a steroid skeleton is particularly preferred. The above-mentioned organic group having an alicyclic skeleton may have a part or all of a hydrogen atom which may be substituted by a halogen atom (preferably a fluorine atom) or a fluoroalkyl group (preferably φ trifluoromethyl group). The fluorine atom-containing group having 6 to 20 carbon atoms represented by R1 ( ) in the above formula (Q-1) may, for example, be a carbon number of 6 to 20 such as an n-hexyl group, an n-octyl group or a n-decyl group. a straight-chain alkyl group; an alicyclic hydrocarbon group having a carbon number of 6 to 20 such as a cyclohexyl group or a cyclooctyl group; a part of a hydrogen atom in an organic group such as an aromatic hydrocarbon group having a carbon number of 6 to 20 such as a phenyl group or a biphenyl group; All groups substituted by a fluorine atom or a fluoroalkyl group such as a trifluoromethyl group. X1 in the above formula (Q-1) and X2 in the above formula (Q-2) are a single bond, -20-200844610 _〇-, -C〇-, -C〇0-, -〇C〇-, -NHC〇-, -CONH-, -S- or an aryl group, and examples of the aryl group include a phenyl group, a tolyl group, a phenyl group, a naphthyl group, and the like. As X1 and X2, a group represented by -0-, -COO-, -OCO- is particularly preferred. Preferred examples of the diamine having a group represented by the above formula (Q-1) include dodecyloxy-2,4-diaminobenzene and pentadecyloxy-2,4-. Diaminobenzene, hexadecyloxy-2,4-diaminobenzene, octadecyloxy-2,4-diaminobenzene or a compound represented by the following formulas (16) to (25). 200844610

H2N

Nh2 (18)

-22- 200844610

Coo iii -C^oocO~cf3 h2n (22)

-23- 200844610

Preferred examples of the diamine having a group represented by the above formula (Q-2) include compounds represented by the following formulas (26) to (28).

(2 6)

Among them, particularly preferred are compounds represented by the above formula (16), (17), (22), and -24-200844610 (23) or (26). When a specific diamine is used in combination with other diamines in the synthesis of a specific polyamine, the use ratio of the specific diamine is preferably 丨 mol% or more, particularly preferably 5 mol% or more, based on the entire diamine. . &lt;Synthesis of Specific Polylysine&gt; Next, a method for synthesizing a specific polyamic acid, which may be contained in the liquid crystal alignment agent of the present invention, will be described. The specific polyamine can be obtained by adding the above specific tetracarboxylic dianhydride and other tetracarboxylic dianhydrides as required, to a specific diamine and, if necessary, other diamines, preferably in an organic solvent, preferably When the temperature is -20 ° C to 150 ° C, more preferably 0 to 100 ° C, it is preferably synthesized by reacting it for ～. The ratio of use of the tetracarboxylic dianhydride to the diamine supplied to the specific polyaminic acid synthesis reaction is preferably a ratio of the acid anhydride group of the tetracarboxylic dianhydride to 0.5 to 2 equivalents per 1 equivalent of the amine group of the diamine. It is better to make it a ratio of 〇.7~^ when the amount of φ. Here, 'as an organic solvent, it is not particularly limited as long as it can dissolve the specific polylysine synthesized, and examples thereof include methyl-2-pyrrolidone, N,N-dimethylacetamide, and n. , N-dimethylformamide, 3-butoxy-N,N-dimethylpropanamide, 3-methoxy-N, Nc methyl propylamine, 3-hexyloxy-N, An aprotic solvent such as a guanamine solvent such as N-dimethylpropionamide; an aprotic polar solvent such as dimethyl hydrazine, r-butyrolactone, tetramethyl urea or hexamethylphosphonium triamine; m-methyl acid, An anthraquinone solvent such as mono-toluic acid, benzoquinone or halogenated benzoquinone. Further, the amount (α) of the organic solvent is preferably a ratio of the total amount (/?) of the tetracarboxylic dianhydride and the diamine compound to the total amount of the reaction solution (α + no) (monomer) The concentration is an amount of 〜·1 to 30% by weight. In the above organic solvent, a poor solvent (P〇〇r solvent) of a specific polyglycolic acid, a ketone, an ester, or an ether may be used in a range in which the specific polyamic acid to be produced is not precipitated. , halogenated hydrocarbons, hydrocarbons, etc. Specific examples of such a poor solvent include methanol, ethanol, isopropanol, cyclohexanol, 4-hydroxy-4-methyl-2-pentanone, ethylene glycol, propylene glycol, and 1,4· ® diol, triethylene glycol, ethylene glycol monomethyl ether, ethyl lactate, butyl lactate, acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, methyl acetate, ethyl acetate , butyl acetate, methyl methoxypropionate, ethyl ethoxy propionate, diethyl oxalate, diethyl malonate, diethyl ether, ethylene glycol methyl ether, ethylene glycol ethyl Ether, ethylene glycol n-propyl ether, ethylene glycol isopropyl ether, ethylene glycol n-butyl ether, ethylene glycol dimethyl ether, ethylene glycol ethyl ether acetate, diethylene glycol dimethyl ether, Diethylene glycol diethyl ether, diethylene glycol monomethyl ether, diethylene alcohol monoethyl ether, diethylene glycol monomethyl ether acetate, diethylene glycol monoethyl ether acetate, tetrahydrofuran, two Methyl chloride, 1,2-dichloroethane, 1,4-dichlorobutane, trichloroethane, chlorobenzene, o-dichlorobenzene, hexane, heptane, octane, benzene, toluene, xylene, Isoamyl propionate, isoamyl isobutyrate, Diisoamyl ether and the like. As described above, a reaction solution in which a specific polyamine is dissolved is obtained. Then, the reaction solution is poured into a large amount of a poor solvent to obtain a precipitate, and the precipitate is dried under reduced pressure or the reaction solution is distilled under reduced pressure with an evaporator to obtain a polyamine. Further, the specific polylysine is further dissolved in an organic solvent, and then subjected to a process of precipitating with a poor solvent once or several times or a process of vacuum distillation using an evaporator, whereby a specific poly can be refined. Proline. &lt;Synthesis method of quinone imidized polymer of specific polyamic acid&gt; Next, a method for synthesizing a quinone imidized polymer of a specific polyamine which can be contained in the liquid crystal alignment agent of the present invention will be described. The quinone imidized polymer of a specific polyamic acid can be synthesized by dehydrating a part or all of the proline structure of the specific polyamic acid described above. The ratio of the repeating unit having a quinone ring in all the repeating units of the quinone imidized polymer which can be used in the present invention (hereinafter, also referred to as "deuteration rate") is 40 mol% or more. Good is 50% or more. By using a polymer having a ruthenium iodide ratio of 40 mol% or more, the afterimage erasing time of the obtained liquid crystal alignment film can be made shorter. The dehydration ring-closure reaction of the specific polyamine can be carried out by (i) heating a specific poly-proline, or (ii) dissolving a specific poly-lysine in the organic solvent φ, adding a dehydrating agent and a dehydration ring to the solution. The catalyst is carried out according to the method of heating as needed. In the above method (i) of heating a specific polyamic acid, the reaction temperature is preferably from 50 to 200 ° C, more preferably from 60 to 170 ° C. When the reaction temperature is less than 50 °C, the dehydration ring-closure reaction cannot proceed sufficiently. If the reaction temperature exceeds 200 °C, the molecular weight of the obtained quinone imidized polymer may decrease. On the other hand, in the above method (ii) in which a dehydrating agent and a dehydration ring-closing catalyst are added to a specific polyaminic acid solution, as a dehydrating agent, -27-200844610 such as acetic anhydride, propionic anhydride, trifluoroacetic anhydride can be used. Anhydride. The amount of the dehydrating agent to be used is preferably 0.01 to 20 moles per 1 unit of the repeating unit of the specific poly-proline. As the dehydration ring-closure catalyst, a tertiary amine such as pyridine, trimethylpyridine, lutidine or triethylamine can be used. However, it is not limited to these. The amount of the dehydration ring-closing catalyst is preferably 〇. 〇 1 〜 1 1 Moule relative to the dehydrating agent used in 1 mol. The higher the amount of the above dehydrating agent and the dehydration ring-closing catalyst, the higher the yield of ruthenium imide. The organic solvent used in the dehydration ring-closure reaction may, for example, be an organic solvent exemplified as a solvent used in the synthesis of a specific polylysine. The reaction temperature of the dehydration ring closure reaction is preferably from 0 to 180 ° C, more preferably from 10 to 150 ° C. The obtained ruthenium iodide polymer can be purified by subjecting the reaction solution thus obtained to the same operation as in the specific polyamic acid preparation method. &lt;End-Modified Polymer&gt; The (a) polymer used in the present invention, that is, the specific poly-proline or its quinone imidized polymer, may also be a terminal-modified poly-compound having a molecular weight adjustment. . By using the terminal-modified polymer, the coating characteristics and the like of the liquid crystal alignment agent can be improved without impairing the effects of the present invention. Such a terminal-modified polymer can be synthesized by adding a monobasic acid anhydride, a monoamine compound, a monoisocyanate compound or the like to a reaction system during the synthesis of a specific polyamine. Among them, examples of the monobasic acid anhydride include maleic anhydride, phthalic anhydride, itaconic anhydride, n-decyl benzoic acid anhydride, n-xyl-based succinic anhydride, n-tetradecyl succinic anhydride, and n-hexadecyl anhydride. Alkyl succinic anhydride and the like. The monoamine compound may, for example, be aniline, cyclohexylamine, n-butylamine, n--28-200844610 pentylamine, n-hexylamine, n-heptylamine, n-octylamine, n-decylamine, n-decylamine, n-undecane. Amine, n-dodecylamine, n-tridecylamine, n-tetradecylamine, n-pentadecylamine, n-hexadecaneamine, n-heptadecaneamine, n-octadecylamine, n-icosylamine, etc. . The monoisocyanate compound may, for example, be phenyl isocyanate or naphthyl isocyanate. &lt;Solid viscosity of polymer&gt; The polymer (a) obtained as above preferably has a viscosity of 20 to 800 mPa_s, more preferably 30 to 500 mPa.s, when formulated into a 10% solution. Viscosity. Further, the solution viscosity (mPa's) of the polymer was determined by using a predetermined solvent, and the solution having a solid content concentration of 10% was measured at 25 ° C using an E-type rotational viscometer. &lt;Other Polymers&gt; In the liquid crystal alignment agent of the present invention, a part of the above (a) polymer may be selected from other poly-proline Φ and its oxime iridization without impairing the effects of the present invention. At least one of the groups consisting of the polymers (hereinafter referred to as "other polymers") is replaced. The above other polymer is not particularly limited as long as it is a polyamic acid other than a specific polyamic acid or a quinone imidized polymer thereof, and is preferably composed of the above other tetracarboxylic dianhydride and other diamines. The resulting polymer or its oxime imidized polymer is reacted. The other tetracarboxylic dianhydride used herein is preferably an alicyclic tetracarboxylic dianhydride or an aromatic tetracarboxylic dianhydride, particularly preferably 1,2,3,4-cyclobutane tetracarboxylic dianhydride. Or pyromellitic dianhydride. As the other diamine used herein, -29-200844610, an aromatic diamine is preferred, and 4,4'-diaminodiphenylmethane is particularly preferred. The synthesis of such other polymers is the same as the synthesis of the specific polyamine and its ruthenium imidized polymer, except that other tetracarboxylic dianhydrides and other diamines are used in place of the specific tetracarboxylic dianhydride and the specific diamine. Conducted. When the liquid crystal alignment agent of the present invention contains other polymers, the ratio of use of the other polymers is preferably 80% by weight or less based on the total amount of the specific polyamine and its ruthenium iodide polymer and other polymers. More preferably, it is 60% by weight or less. (b) Component The liquid crystal alignment agent of the present invention contains at least one selected from the group consisting of 2-pyrrolidone, N-methylsuccinimide and N-methylpentamethyleneimine as the component (b). The component (b) is added in order to impart good printability to the liquid crystal alignment agent of the present invention and to improve the electrical properties of the obtained liquid crystal alignment film. The content of the component (b) in the liquid crystal alignment agent of the present invention is preferably 0.001 to 1% by weight, more preferably 0.001 to 0.1% by weight based on the total amount of the liquid crystal alignment agent. Other additives The liquid crystal alignment agent of the present invention contains the above-mentioned (a) component and (b) component and the following solvent as essential components, but may contain other additives insofar as the effects of the present invention are not impaired. As such other additives, for example, (c) a functional decane-containing compound, (d) an epoxy compound, and the like can be given. Examples of the (c) functional decane-containing compound include, for example, 3- 30-200844610 aminopropyltrimethoxydecane, 3-aminopropyltriethoxydecane, and 2-aminopropyltrimethyl. Oxydecane, 2-aminopropyltriethoxydecane, N-(2-aminoethyl)-3-aminopropyltrimethoxydecane, Ν-(2·aminoethyl)-3 -Aminopropylmethyldimethoxydecane, 3-ureidopropyltrimethoxydecane, 3-ureidopropyltriethoxycutane, N-ethoxycarbonyl-3-aminopropyltrimethyl Oxydecane, N-ethoxycarbonyl_3_aminopropyltriethoxydecane, N-triethoxyindolylpropyltriethylamine, N-trimethoxysilylpropyl Tri-extension ethyltriamine, 10·trimethoxydecyl-1,4,7-triazadecane, 10-triethoxyoxyalkyl-1,4,7-triazadecane, 9 -trimethoxydecyl-3,6-diazaindolyl acetate, 9-triethoxydecyl-3,6-diazaindolyl acetate, N-benzyl-3-amine Propyltrimethoxydecane, N-benzyl-3-aminopropyltriethoxydecane, N-phenyl-3-aminopropyltrimethoxydecane, N-phenyl-3-amine Silane triethoxysilane, N- bis (oxyethylene) -3-aminopropyl trimethoxy Silane, N- bis (oxyethylene) -3-aminopropyl triethoxy silane-like. Examples of the epoxy compound (d) include ethylene glycol dihydrate glycerol ether, polyethylene glycol diglycidyl ether, propylene glycol diglycidyl ether, tripropylene glycol diglycidyl ether, and polypropylene glycol diglycidyl ether. , neopentyl glycol diglycidyl ether, 1,6-hexanediol diglycidyl ether, glycerol diglycidyl ether, 2,2-dibromoneopentyl glycol diglycidyl ether, 1,3,5,6 -tetraglycidyl-2,4-hexanediol, N,N,N',N'-tetraglycidyl-m-xylylenediamine, 1,3-bis(indole, hydrazine-diglycidylamine) Methyl)cyclohexane, hydrazine, hydrazine, Ν', Ν'-tetraglycidyl-4,4'-diaminodiphenylmethane, 3-(Ν-allyl-Ν-glycidyl Aminopropyltrimethoxydecane, -31- 200844610 3-(N,N-diglycidyl)aminopropyltrimethoxydecane, N,N-diglycidyl-benzylamine, N, N-diglycidyl-aminomethylcyclohexane or the like. The mixing ratio of the (c) functional decane-containing compound and (d) the epoxy-containing compound is preferably 40 parts by weight or less per 100 parts by weight of the total polymer, more preferably .0.1 to 3 parts by weight. 0 parts by weight θ &lt;solvent&gt; The solvent contained in the liquid crystal alignment agent of the present invention is preferably an organic solvent, and examples thereof include a solvent exemplified as a solvent used in a specific polyamine acid synthesis reaction. Further, it is also possible to appropriately select a poor solvent which is exemplified as a poor solvent which can be used in a specific polyamic acid synthesis reaction. Preferred examples of the organic solvent to be used in the liquid crystal alignment agent of the present invention include 1-methyl-2-pyrrolidone, r-butyrolactone, r-butyrolactone, and N,N-dimethylformamidine. Amine, N,N-dimethylacetamide, 4·hydroxy-4-methyl-2-pentanone, ethylene glycol monomethyl ether, butyl lactate, butyl acetate, methoxypropyl φ acid Ester, ethyl ethoxypropionate, methyl carbitol, ethyl carbitol, butyl carbitol, ethylene glycol methyl ether, ethylene glycol ethyl ether, ethylene glycol n-propyl ether, B Glycol isopropyl ether, ethylene glycol n-butyl ether (butyl cellosolve), ethylene glycol dimethyl ether, ethylene glycol ethyl ether acetate, dimethyl carbitol, diethyl carbitol , diethylene glycol monomethyl ether acetate, ethyl carbitol acetate, butyl carbitol acetate, butyl cellosolve acetate, triethylene glycol dimethyl ether, 3-butoxy -N,N-dimethylpropanamide, 3-methoxy-N,N-dimethylpropanamide, 3-hexyloxy-N,N-dimethylpropanamide, triethylene glycol Methyl ether, isobutyl-32-200844610 Isoamyl acid ester, diisoamyl ether, and the like. These solvents may be used alone or in combination. The liquid crystal alignment agent of the present invention comprises a solvent selected from the group consisting of methyl carbitol, dimethyl carbitol, ethyl carbitol, ethyl carbitol acetate, butyl carbitol At least one of the group consisting of an acid ester, a butyl cellosolve acetate, a triethylene glycol dimethyl-2-pyrrolidone, an r-butyrolactone, and an ethylene glycol n-butyl ether (hereinafter referred to as "specific rotation" It can show good printability. It is specifically dissolved in methyl carbitol, dimethyl carbitol, ethyl carbitol, ethyl carbitol acetate, butyl carbitol, butyl card. The butyl cellosolve acetate and the triethylene glycol dimethyl ether are at least the above ratio of the solvent contained in the solvent of the liquid crystal alignment agent of the present invention, preferably 1% by weight or more, more preferably % of the total solvent. &gt; The liquid crystal alignment agent of the present invention contains the above-mentioned (a) polymer as an essential component, and optionally contains other additives, and it is preferred that the components other than the solvent in the crystal alignment agent are dissolved and dissolved. The solid content of the liquid crystal alignment agent of the present invention Concentration (total weight of components other than liquid solvent divided by liquid crystal A mixture of two or more kinds of agents is preferably a carbitol, a diol, a butyl carbitol, a methyl (butyl cellosolve) I agent, and an agent, preferably a diethyl carbitol. Acetate, a certain amount of the solvent is 5 to 50 parts by weight (b) of the component and the solvent is prepared to make the total weight of the solution in the solution of the liquid crystal agent in addition to 1) -33- 200844610 Preferably, the liquid crystal alignment agent of the present invention is applied to the surface of the substrate to form a coating film as a liquid crystal. When the solid content concentration is less than 1% by weight, the ratio is preferably 1 to 10% by weight. If the coating thickness is too small, a good liquid crystal alignment film cannot be obtained; when the solid content concentration exceeds 10% by weight, the coating film thickness is too large to obtain a good liquid crystal alignment film, and the viscosity of the liquid crystal agent increases. The large result is that the coating characteristics are deteriorated, and thus it is not preferable. The liquid crystal alignment agent has a viscosity of 5 to 12 mPai. Further, the liquid crystal alignment agent of the present invention has a moisture content of from 0.01 to 0.5%. By setting the moisture content in this range, the liquid crystal alignment agent can be extremely excellent in brushability. When a liquid crystal alignment agent is prepared by a practitioner having ordinary knowledge and technology in accordance with the contents described in the specification other than the content, the moisture content in the crystal alignment agent is usually lower than the above range. Therefore, if the moisture content of the liquid to the agent falls within the above range, an appropriate amount of water may be added to the liquid crystal alignment agent at any stage of the preparation of the liquid crystal agent. Further, the surface tension of the liquid crystal alignment agent of the present invention is preferably 40 dyn. The range of /cm. The temperature at which the liquid crystal alignment agent of the present invention is prepared is preferably 〇 ° C ° C, more preferably 20 ° C to 60 ° C. &lt;Liquid Crystal Display Element&gt; The liquid crystal display element of the present invention is characterized by having a liquid crystal alignment film obtained by obtaining the liquid crystal alignment agent of the invention as described above. The liquid crystal display element of the present invention can be produced, for example, by the following. The surface of the film and the thickness of the film will be aligned with the moisture of the hair and the liquid crystal will be matched. 25~ ~200^ This process (1) -34- 200844610 ~(3) is manufactured. (1) The liquid crystal alignment agent of the present invention is applied onto one surface of a substrate provided with a transparent conductive film by a lithography method, a spin coating method or an inkjet printing method, and then a coating film is formed on the coated surface. . The coating which is suitable as the liquid crystal alignment agent of the present invention is preferably an ink jet printing method. Here, as the substrate, glass such as glass or soda lime glass can be used; and a substrate made of plastic such as polyethylene terephthalate vinegar I dicarboxylate, polyether oxime or polycarbonate can be used. As a transparent conductive film provided on one side of the substrate, a bright conductive film such as an ITO film composed of tin oxide (Sm〇2) and an ITO film composed of indium tin oxide (ImCh-Sn2) registered by PPG Corporation of the United States can be used. The pattern is formed by photolithography or a method of pre-using a mask during transparent conduction, etc. The coating of the liquid crystal alignment agent further improves the surface of the substrate and the transparent conductive film and the coating film to be pre-coated on the surface of the substrate. The compound of the φ functional titanium containing functional decane is applied, and the heating after coating the liquid crystal alignment agent is 80 to 300 ° C, more preferably 120 to 25 ° C. Further, after the application of the present alignment agent The organic solvent is removed to form a liquid crystal coating film. When the liquid crystal alignment agent of the present invention contains a proline acid ester, the proline structure can be further removed by heating to form a further yttrium-imided coating film. The thickness of the coating film is preferably 0.001 to 1 / / m, more preferably ~ 0.5 / zm 〇 such as a suitable heating method for forming a pattern, such as float glass, polyphenylene is transparent to use the oxygen trademark). When these transparent films are formed, for the purpose of the composition, a closed loop of a composition of a liquid crystal alignment film having a relatively good temperature is preferably 0.005 - 35 - 200844610 (2). Next, the coating formed as described above is usually used. The surface of the film is subjected to a rubbing treatment which is rubbed in a certain direction by a roll wrapped with a cloth composed of fibers such as nylon, rayon, cotton or the like. In addition, the liquid crystal alignment film which is formed by the liquid crystal alignment agent of the present invention is shown in, for example, Patent Document 2 (JP-A-H06-222366) or Patent Document 3 (Japanese Laid-Open Patent Publication No. Hei No. Hei No. Hei. A process of partially irradiating ultraviolet rays to change the pretilt angle, or partially forming a protective layer on the surface of the liquid crystal alignment film after performing the polishing process as shown in Patent Document 4 (Japanese Laid-Open Patent Publication No. Hei No. Hei No. Hei No. Hei No. Hei No. Hei. The film is subjected to a treatment in which the film is polished in a direction different from the previous polishing process, and the protective film is removed to change the liquid crystal alignment of the liquid crystal alignment film, thereby improving the viewing property of the liquid crystal display element. (3) Producing two substrates for forming a liquid crystal alignment film as described in (1) or (2) above, and placing the two substrates relatively through a gap (cell gap) so that the polishing directions of the respective liquid crystal alignment films are perpendicular or opposite to each other. In parallel, the peripheral portions of the two substrates are bonded together with a sealant, and the liquid crystal is filled into the gap of the cell φ which is separated from the surface of the substrate and the sealant, and the injection holes are closed to constitute a liquid crystal cell. Then, on the outer surface of the liquid crystal cell, that is, on the other side surface of each of the substrates constituting the liquid crystal cell, the polarizing plate is bonded so that the polarizing direction is the same as or perpendicular to the polishing direction of the liquid crystal alignment film formed on one side of the substrate. A liquid crystal display element is obtained. Here, as the sealant, for example, an alumina ball-containing epoxy resin or the like which is a curing agent and a spacer can be used. Examples of the liquid crystal include a nematic liquid crystal and a smectic liquid crystal. Among them, a nematic liquid crystal is preferable, and for example, a Schiff base liquid crystal, an oxidized azo liquid crystal, a biphenyl liquid crystal, or a phenyl group can be used. 36- 200844610 Cyclohexane liquid crystal, ester liquid crystal, terphenyl liquid crystal, biphenyl cyclohexane liquid crystal, mute liquid crystal, one-time liquid crystal, double ring Xinyuan liquid crystal, cubic courtyard liquid crystal, etc. In addition, cholesteric liquid crystals such as cholesteryl cholesteryl, cholesteryl phthalate, and cholesteryl carbonate may be added to the liquid crystal and may be manufactured under the trade names "C-15" and "CB-15" (Merck). The chiral agent sold, etc. is used. Further, a ferroelectric liquid crystal such as p-methoxybenzylidene-p-amino-2-methylbutylcinnamate may also be used. The polarizing plate to be bonded to the outer surface of the liquid crystal cell is a polarizing plate obtained by sandwiching a polarizing film called a ruthenium film which is obtained by absorbing iodine while absorbing iodine, and sandwiching it on a cellulose acetate protective film, or A polarizing plate made of the enamel film itself. [Examples] Hereinafter, the present invention will be more specifically described by examples, but the present invention is not limited to the examples. In the following examples and comparative examples, the evaluation of the prepared liquid crystal alignment agent φ was carried out by the following method. [Printability Evaluation] The liquid crystal alignment agents prepared in the respective Examples and Comparative Examples were stored in a freezer at -1 ° C for 7 days, and then heated to room temperature, using a JET-CM continuous inkjet printer (Jizhou) The technology (manufacturing by the company) is continuously applied to a transparent conductive film made of an ITO film provided on one surface of a glass substrate having a thickness of imm for 1 minute, and the amount of the coating liquid is a film after the solvent is removed. The thickness is 6Onm. After continuous application for 1 minute, the coating was further continued, and the obtained substrate of the coated film of -37-200844610 was prebaked on a hot plate at 80 ° C for 1 minute, and then in a clean oven in a nitrogen atmosphere. After heating at 200 ° C for 60 minutes, the peripheral portion and the central portion of the liquid crystal alignment film were observed by a microscope at 20 magnification. When the coating unevenness was not applied, it was judged as "excellent", and when a slight pinhole or uneven coating (uneven film thickness, unevenness of streaks, etc.) was observed, it was judged as "good", and pinhole or coating was noticeably observed. The case of unevenness is judged as "bad". [Evaluation of Voltage Retention Rate] A glass substrate having a patterned germanium electrode having a thickness of about 1 mm formed on one surface was used, and the liquid crystal alignment agent was directly used in the liquid crystal alignment agent obtained in each of the examples or the comparative examples. The above [Printability Evaluation] A pair of (two sheets) glass substrates having a coating film having a film thickness of about 0.06 / zm were produced in the same manner. Next, on each of the outer edges of the liquid crystal alignment film of the liquid crystal alignment film coating substrate of the pair of transparent electrodes/transparent substrates, an alumina having a diameter of 5 · 5 // m is applied in addition to the liquid crystal injection port. The epoxy resin binder of the ball is then relatively recombined and pressed against the liquid crystal alignment film surface to cure the adhesive. Next, the liquid crystal injection port is used to fill the liquid crystal between the substrates (negative type, manufactured by Merck & Co., MLC-6608), and then the liquid crystal injection port is sealed with an acrylic photocurable adhesive, and the two sides of the substrate are attached. The polarizing plate is combined to form a liquid crystal display element. Applying a voltage of 5 V to the liquid crystal display element at a time interval of 1 6 · 7 msec at room temperature, the voltage application time was 60 μm, and then the voltage was released from the electric -38-200844610 to 1 6 · 7 msec. After the voltage retention rate. The measuring device was a VHR-1 manufactured by Dongyang Science and Technology Co., Ltd. [Residual image evaluation] A liquid crystal display element was produced in the same manner as in the above [voltage holding rate evaluation] except that a substrate having a Ιτ〇 film having a pattern as shown in Fig. 1 was used. The liquid crystal display element was applied with a DC voltage of 6.0 V for 24 hours to the electrode crucible at room temperature, and a DC voltage of 0.5 V was applied to the electrode B for 24 hours. After the voltage was removed, 0.1 to 5.0 V DC voltage was applied to the electrodes A and B at a gradient of 0.1 V, respectively, and the residual image characteristics were judged by the difference in luminance between the electrodes A and B at the respective voltages. That is, when the luminance difference is large, the afterimage characteristic is judged to be poor. No sign of the afterimage is found as 〇, and the sign of the weaker afterimage is recorded as △. Synthesis Example &lt;Synthesis Example of Specific Diamine&gt; Synthesis Example A-1 (Synthesis of 1-(3,5-diaminophenyloctadecyl amber 醯imine) 300 ml of three ventilated by nitrogen 12.81 g (0.07 mol) of 3,5-dinitroaniline and 70 ml of acetic acid were added to the flask, and the solid matter was dissolved while stirring with nitrogen gas, and 24.64 g (〇.〇7 mol) of octadecyl group was added thereto. The succinic anhydride was refluxed under nitrogen for 20 hours, and the reaction mixture was cooled to room temperature, and then 70 ml of methanol was added thereto, and the mixture was allowed to stand overnight. The precipitated solid component was filtered, washed with methanol and dried to give 30 g (yield 83). %) Dinitrophenyl)-3-octadecyl amber imine. -39- 200844610 Then, into a 500 ml flask ventilated with nitrogen, 30 g (0.05 8 mol) of 1-(3,5-dinitrophenyl)-3-octadecyl aminide synthesized as described above was added. 100 ml of ethanol, 100 ml of tetrahydrofuran (THF) and 25 g of a reduction catalyst palladium carbon (Pd/C) were stirred at 70 ° C for 1 hour. 42.5 ml (4 3.7 5 g) of hydrazine monohydrate was added thereto, and the mixture was heated under reflux for 6 hours to cause a reaction. The Pd/C was filtered off and the filtrate was concentrated in a rotary evaporator. The obtained crude product was dissolved in N-methyl-2-pyrrolidone by heating, and then recrystallized by cooling to obtain 14.6 g (0.032 mol, yield 55%) of the desired product 1-(3,5-diaminophenyl)-3. -β octadecyl amber imine. Synthesis Example Α - 2 (Synthesis of 1-(3,5-diaminophenyl)-3-dodecyl succinimide) except that 18.76 g (0.07 mol) of dodecyl succinic anhydride was used instead of 24.64 § (0.07111〇1) except for octadecyl succinic anhydride, llg (〇.〇30 mol, yield 51%) 1-(3,5-diaminophenyl) was obtained in the same manner as in Synthesis Example-1. -3-dodecyl amber imine. φ Synthesis Example A-3 (Synthesis of 1-(3,5-diaminophenyl)-3·heptadecyl-4·methylmaleimide) to a 2000 ml three-necked flask ventilated with nitrogen 31.5 g (0.25 mol) of dimethyl maleic anhydride, 89.0 g (0.5 mol) of N-bromosuccinimide, 1.0 g (4.15 mmol) of dibenzoguanidine peroxide and 1,500 ml of carbon tetrachloride were added thereto, followed by heating. Reflux for 5 hours. The reaction solution was cooled to room temperature, and after standing at room temperature overnight, it was filtered. After the filtrate was washed with water, the organic layer was concentrated in a rotary evaporator. The obtained crude oily product was distilled under high vacuum (120~125 ° C / 2 mmHg) to give -40·200844610 to 20.0 g (0.1 mol, yield 39%) of intermediate 3-bromomethyl-4-methyl maleic anhydride. Then, to a 2000 ml three-necked flask ventilated with argon, 16.4 g (80 mmol) of 3-bromomethyl-4-methylmaleic anhydride prepared as above, 1.52 g (8.0 mmol) of copper iodide, and 400 ml were added. After diethyl ether and 160 ml of hydrazine PA (hexamethylphosphonium triamine), it was cooled to -5 to 0 ° C under argon gas. While stirring the mixture, a separately prepared solution of 400 mmo of cetylmagnesium bromide dissolved in 400 ml of diethyl ether was added dropwise over about 20 minutes. The mixture was allowed to warm to room temperature and stirred for additional 8 hours. Then, the mixture was diluted with 600 ml of diethyl ether, and then 600 ml of 4N-sulfuric acid was added to make the solution acidic. The separated aqueous layer was further washed with 600 ml of diethyl ether and the organic layer was combined. The organic layer was washed with water and water was evaporated over sodium sulfate. The crude product was purified in a cerium oxide gel column using a petroleum ether/ethyl acetate (1 9 : 1) mixed solution as a developing solvent to obtain 1 4 · 0 g (0. 〇4 m ο 1, Rate 50%) 3 -heptadecyl-4 -φ methyl maleic anhydride. Then, 6.4 g (〇.〇35 mol) of 3,5-dinitroaniline and 35 ml of acetic acid were placed in a 200 ml three-necked flask which was purged with nitrogen. The mixture was stirred while passing nitrogen gas to dissolve the solid matter. 12.3 g (0.035 mol) of the 3-17 yard-base 4-methyl maleic acid liver obtained above was added thereto, and the mixture was refluxed under nitrogen for 20 hours to cause a reaction. After cooling the reaction mixture to room temperature, 3 5 m of methanol was added and the mixture was allowed to stand overnight. The solid component was filtered off, washed with methanol and dried to give 14.6 g (0.029 mol, yield 81%) of 1-(3,5-dinitrophenyl)-3_heptadecyl-41-200844610 -4- Kimadine imine. Then, to a 300 ml flask ventilated with nitrogen, 13.4 g (0.026 m〇l) of 1-(3,5-dinitrophenyl)-3-heptadecyl-4-methylmalayiya was added. Amine, 50 ml of ethanol, 50 ml of THF and 12.5 g of a reduction catalyst Pd/C were stirred at 70 ° C for 1 hour. Then, 19 ml (19.6 g) of hydrazine monohydrate was added, and the mixture was heated under reflux for 6 hours to cause a reaction. The Pd/C was filtered off and the filtrate was concentrated in a rotary evaporator. The obtained crude product was dissolved in N-methyl-2-pyrrolidone by heating, and recrystallized by cooling to obtain 6.6 g (0.015 mol, yield: 56%) of the objective product 1-(3,5-diaminophenyl)- 3-heptadecyl-4-methylmaleimide. Synthesis Example A-4 (Synthesis of 1-(3,5-diaminophenyl)-3-hexadecanyloxymethyl-4-methylmaleimide) to 300 ml of a gas ventilated by nitrogen After adding 12.81 g (0.07 mol) of 3,5-dinitroaniline and 70 ml of acetic acid to the neck flask, the mixture was stirred while passing nitrogen gas to dissolve the solid matter. Φ 1 4.3 5 g (0.07 mol) of 3-(bromomethyl)-4-methylmaleic anhydride synthesized in the same manner as the intermediate of Synthesis Example A-3 was added thereto, and the mixture was refluxed under nitrogen for 20 hours. reaction. After the reaction solution was cooled to room temperature, 70 mmol of methanol was added and the mixture was allowed to stand overnight. The solid component was filtered off, washed with methanol and dried to give 18.9 g (············· Kimadine imine. Next, to a 500 ml three-necked flask ventilated with nitrogen, I8.1 g (0.04 9 mol) of 1-(3,5-dinitrophenyl)-3-bromomethylmethyl-M-42- was added.

200844610 Sodium imine, 12.9 g (0.049 mol) of sodium 1-hexadecanol, after stirring at 100 ° C for 10 hours, was allowed to go to room temperature, and then added with 70 ml of methanol, and allowed to stand overnight. After washing with methanol, the mixture was dried to give 20.8 g (0.039 m,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,, 0.026 mol) 1-(3,5-dinitrophenyl)·3-decamethyl maleimine, 50 ml of ethanol, 50 ml of a THF reagent Pd/C, and stirred at 70 ° C for 1 hour. Then, the monohydrate was heated and refluxed for 6 hours to cause a reaction (the liquid was concentrated in a rotary evaporator. The obtained crude methyl-2-pyrrolidone was cooled and recrystallized to give a yield of 67%). , 5-diaminophenylmethylmaleimide. &lt;Specific poly-proline and its quinone imidized polymer synthesis Example P-1~P-8 to N-methylpyrrolidone in order Diamine and tetracarboxylic dianhydride were added to prepare a monomer concentration of 2 Torr, which was reacted at 60 ° C for 4 hours to obtain a solution containing polyfluorene 8). To each of the obtained polyaminic acid solutions, the total amount of acid units was added to a ratio of 3.0 times mole of the mouth to acetic anhydride, and then heated at 110 ° C for 4 hours to remove the resulting solution in diethyl The ether was again precipitated, back to 100 ml of dimethyl S. The reaction solution was cooled to give a solid component, and the yield was 80%) 1-(3,5- quinone imine. In the flask, 'hexadecyloxymethyl-4- and 12.5 g of reducing hydration were added [19 ml was added] (19.6 g) - Pd/C was filtered off, and the filtrate was heated and dissolved in N-8.2 g (0.018 mol, synthesis formula of hexamethyleneoxymethyl-4-)&gt; % solution to make the amine acid (A-1)~(A-closed to the solution of the amidoxime in solution and 3.0 times the molar: water closed-loop reaction. By collecting and drying under reduced pressure, -43-200844610 Polymers (B-1)~(B-8). The oxime imidization ratio of these quinone imidized polymers is shown in Table 1. Synthesis Examples P-9 and P-1 0 Except for diamines and tetracarboxylic acids Polyacrylic acid (A-9) and (A-10) were produced in the same manner as in Synthesis Examples P-1 to P-8 except that the acid dianhydride was used as shown in Table 1. Further, in Synthesis Example P-9 In the case of P - 1 0, the dehydration ring closure reaction of polylysine is not carried out.

-44- 200844610 Table 1 Synthesis of diamined hetero-ambient ratio) 邝 )) Poly 雠 安 安 化 mm) Surface ambiguity (%) P-1 Specific diamine A (20), diamine chat - 1(20),Τ-2(80) Α4 Bl 88 P-2 Specific diamine A(20), diamine chatter-1(50), Τ-2(50) Α-2 Β-2 82 P- 3 specific diamine B (10), diamine 1 (10) Τ-1 (20), Τ-2 (80) Α-3 Β-3 86 P-4 specific diamine B (10), diamine chatter -1 (50), Τ-2 (50) Α-4 Β4 81 P-5 specific diamine C(10), diamine _) Τ-1(20), Τ-2(80) Α-5 Β-5 87 P-6 specific diamine C(10), diamine Chat T-K50), 1-2(50) Α-6 Β-6 83 P-7 specific diamine DG〇), diamine 1 (80) Τ-1(20), Τ-2(80) Α- 7 Β-7 86 P-8 Specific diamine D(10), diamine Τ-1 (50), Τ-2(50) Α-8 Β·8 80 P-9 Diamine 1 (100) Τ-3 (100 ) Α-9 — — P-10 Diamine 1_ Τ-3(80), Τ·4(20) Α-10 —

In Table 1, for diamines and tetracarboxylic dianhydrides, the numbers in parentheses indicate the content ratio (mol ratio), and the abbreviations in the table have the following meanings.

Specific diamine A: 1-(3,5-diaminophenyl)-3-octadecyl succinimide specific diamine B: diaminophenyl)-3-dodecyl amber Amine specific diamine C: 1-(3,5-diaminophenyl)-3-heptadecyl-4-methylmaleimide specific diamine D: 1-(3,5-diamine Phenyl)-3-hexadecyloxymethyl-4-methylmaleimide-45- 200844610 Diamine 1:4,4 '-diaminodiphenylmethane&lt;tetracarboxylic acid Anhydride &gt; T — 1 : 2,3,5-tricarboxycyclopentyl acetic acid dianhydride T 2 : 5-(2,5-dioxotetrahydro-3-furanyl)-3 -methyl-3 -cyclohexene-1,2-dicarboxylic anhydride T-3: pyromellitic dianhydride di- 4: 1,2,3,4-cyclobutane tetracarboxylic dianhydride &lt; Synthesis of (b) component Example &gt; Φ Synthesis Example b-1 (Synthesis Example of N-Methylpentadienimide) Methylpentayleneimine was synthesized according to the following reaction formula. The specific process is as follows.

K, co, acetone, refluxed to a 200 ml three-necked flask equipped with a cerium oxide drying tube. Add 1.0 g (8.84 mmol) of pentaneimine, 1.51 g (10.6 mmol) of methyl iodide, 1.47 g. (10. 6 mmol) potassium carbonate and 20 ml of dehydrated acetone were heated and refluxed. After 16 hours, it was cooled to room temperature, and 0.6 g (4.42 mmol) of methyl iodide and 0.61 g (4.42 mmol) of potassium carbonate were added, followed by heating under reflux for 7.5 hours. The reaction liquid was cooled to 0 ° C, and potassium carbonate was removed by filtration, and dried under reduced pressure to yield 1.10 g (8.65 mmol, yield 98%) of N-methylpentadiimide. Example 1 The ruthenium imidized polymer B-1 obtained in Synthesis Example P-1 and the polylysine A-9 (weight ratio 5 0: 50) obtained in Synthesis Example P-9 were dissolved. A solution having a solid content concentration of 3.5% by weight was prepared in a mixed solution of γ-butyrolactone/Ν-methyl-2-pyrrolidone/butyl cellosolve (weight ratio -46-200844610 40:30:30). To these solutions, 2-pyrrolidone (commercial product) as the component (b) was added so as to have a weight of 液晶·〇05% by weight based on the total liquid crystal alignment agent, so that the moisture content was relative to the entire liquid crystal. The weight of the alignment agent is 〇. 3 wt%. Next, the liquid crystal alignment agent of the present invention was prepared by filtration through a filter having a pore size of 0.2 μm. The viscosity of the obtained liquid crystal alignment agent is shown in Table 2. Using these liquid crystal alignment agents, the printability, the voltage holding ratio, and the afterimage were evaluated in accordance with the above method. The results are shown in Table 5. 9 Examples 2 to 3 2 The liquid crystals were separately prepared in the same manner as in Example 1 except that the types of the components (polymer) and (b) of the components of the U) and the solid content concentration and the water content of the obtained liquid crystal alignment agent were as shown in Table 2. An aligning agent. The viscosity of each liquid crystal alignment agent is shown in Table 2. Further, the results of evaluation using these liquid crystal alignment agents in accordance with the above methods are shown in Table 5. Further, N-methylpentadienimide in the component (b) was synthesized by the above synthesis example m W b-1. •47- 200844610 Table 2 Sinus application polynomial ratio (b) Component solid separation (% by weight) Moisture (% by volume) Viscosity (mPa.s) 1 Bl/A-9 (50/50 ) pyrrolidone 3.5 0.3 6.2 2 N-methylsuccinimide 3.5 0.3 6.2 3 N-pentyl quinone imine 3.5 0.3 6.2 4 B-2/A-9 (50/50) 2-D ratio Academy ketone 3.5 0.3 6.6 5 N-methylsuccinimide 3.5 0.3 6.6 6 N-methylglutarase imine 3.5 0.3 6.6 7 B-3/A-9 (50/50) 2-port ratio Ketone 3.5 0.3 6.1 8 N-methyl oxime imine 3.5 0.3 6.1 9 N-methylpentadienimide 3.5 0.3 6.1 10 B-4/A-9 (50/50) 2-pyrrolidone 3.5 0.3 6.7 11 N-methyl oxime imine 3.5 0.3 6.7 12 N-methylpentadienimide 3.5 0.3 6.7 13 B-5/A-9 (50/50) 2-pyrrolidone 3.5 0.3 6.2 14 N- Methyl sulfonium imide 3.5 0.3 6.2 15 N-methylpentaneimine 3.5 0.3 6.2 16 B-6/A-9 (50/50) 2-pyrrolidone 3.5 0.3 6.8 17 N-methyl number Persinimide 3.5 0.3 6.8 18 N-methylpentadienimide 3.5 0.3 6.8 19 B-7/A-9 (50/50) 2-_Veteran Ketone 3.5 0.3 6.2 20 N-Methyl Imine 3.5 0.3 6.2 21 N-methylpentadienimide 3.5 0.3 6.2 22 B-8/A-9(50/50) 2-D isololone 3.5 0.3 6.6 23 N-Kana white imine 3.5 0.3 6.6 24 N-methylpentadienimide 3.5 0.3 6.6 25 Bl/A-10(50/50) 2-_Ketney ketone 3.5 0.3 6.2 26 N-Methyl ketone Imine 3.5 0.3 6.2 27 N-methylpentamethyleneimine 3*5 0.3 6.2 28 Bl/A-9(50/50) N-Met Fibrillaryimine 3.0 0.3 6.0 29 N-A Μ 醯 4.0 4.0 0.3 81 30 Ν-甲纤珀安安4.5 0.3 8.9 31 Bl/A-9( 50/50) Ν-Methyl-sodium bromide imide 3.5 0.5 6.2 32 Ν-甲纤拍醯iimide 3.5 0.1 6.2

Example 3 3 to 3 6 In addition to 7-butyrolactone / N-methyl-2-pyrrolidone / butyl cellosolve / -48- 200844610 The mixed solvent of the specific solvent shown in Table 3 (weight ratio 4 0/30 / 15/15) A liquid crystal alignment agent was prepared in the same manner as in Example 2 except that the solvent was used. The viscosity of each liquid crystal alignment agent is shown in Table 3. Further, the results of evaluation using these liquid crystal alignment agents in accordance with the above methods are shown in Table 5. Table 3 Example Residual (weight composition ratio) (b) Component specific solvent 雠 page solid content miscellaneous (% by weight) Moisture content (% by weight) Viscosity (mPa.s) 33 Bl/A-9(50/50) N -Methyl-sodium acetonide diethyl carbitol 3.5 0.3 6.2 34 Bl/A-9(50/50) N-methyl acetonide ethyl carbitol acetate 3.5 0.3 63 35 Bl/A -9(50/50) N-methyl-Pymamine butyl carbitol 3.5 0.3 6.2 36 Bl/A-9(50/50) N-methyl 1 succinate and triethylene glycol dimethyl ether 3.5 0.3 6.2 Comparative Examples 1 to 4 Except that the type of the component (a) (polymer) and the solid content concentration and moisture content of the obtained liquid crystal alignment agent are as shown in Table 4, and the component (b) is not used, and Example 1 The liquid crystal alignment agent was separately prepared in the same manner. The viscosity of each liquid crystal alignment agent is shown in Table 4. Further, the results of evaluation using these liquid crystal alignment agents in accordance with the above methods are shown in Table 5. -49- 200844610 Table 4 Comparative examples of poly (heavy weight ratio) (b) Component solid separation (% of moisture, % moisture content) Viscosity (mPa.s) 1 Bl/A-9 (50/50) 4πτ. ΐ 11II ^\\\ 3.5 0.3 6.2 2 B-2/A-9(50/50) 4rrf Ί111: JXW 3.5 0.3 6.6 3 Bl/A-9(50/50) &gt;fnrr ..· ΠΙΓ 4 \\\ 6.1 0.3 18.0 4 Bl/A-9(50/50) Μ j\\\ 3.5 5.0 6.3

Table 5 Inkjet SJE Retention Rate Penalty Inkjet 6 Brushability WM Retention Rate Afterimage Example 1 Good &gt; 99% 〇 Example 21 Good &gt; 99% 〇mwn Good &gt; 99% 〇 Example 22 Good &gt; 99% 〇 Example 3 Good &gt; 99% 〇 Example 23 Good &gt; 99% 〇 Example 4 Good &gt; 99% 〇 Example 24 Good &gt; 99% 〇 Example 5 Good &gt; 99% 〇 Example 25 good &gt;99% 〇Example 6 Good &gt;99% 〇Example 26 Good &gt;99% 〇Example 7 Good &gt;99% 〇Example 27 Good &gt;99% 〇Example 8 Good &gt;99 % 〇Example 28 Good &gt;99% 〇Example 9 Good &gt;99% 〇Example 29 Good &gt;99% 〇实面10 良&gt;99% 〇Example 30 良&gt;99% 〇Example 11 Good &gt; 99% 〇 Example 31 Good &gt; 99% 丨〇 Example 12 Good &gt; 99% 〇 Example 32 Good &gt; 99% 〇 Example 13 Good &gt; 99% 〇 Example 33 Excellent &gt;99 % 〇 Example 14 Good &gt; 99% 〇 Example 34 Excellent &gt; 99% 〇 Example 15 Good &gt; 99% 〇 Example 35 'Excellent> 99% 〇 Example 16 Good &gt; 99% 〇 Example 36 Excellent &gt;99% 〇Example 17 Good & Gt 99% 〇Comparative Example 1 Good 96% △ Example 18 Good &gt; 99% 〇Comparative Example 2 Good 97% Δ Example 19 Good &gt;99% 〇Comparative adjustment 3 Poor 96% Δ Example 20 Good, &gt 99% 〇Comparative adjustment 4 Poor 96% Δ -50- 200844610 [Simplified description of the drawings] Fig. 1 is a schematic view showing an ITO electrode pattern of a liquid crystal display element produced for the evaluation of the residual image in the examples and the comparative examples. [Main component symbol description] Μ . &gt;\ \\

-51-

Claims (1)

200844610 X. Patent application scope: 1 . A liquid crystal alignment agent comprising: U) at least one selected from the group consisting of tetracarboxylic dianhydrides represented by the following formulas (1) and (2) and selected from the group consisting of a polymer obtained by reacting at least one of the diamine groups represented by the formulas (3) to (6) and/or a quinone imidized polymer thereof, (b) selected from the group consisting of 2-pyrrolidone and N-methyl amber At least one of the group consisting of quinone imine and methyl pentyleneimine, and φ solvent, the liquid crystal alignment agent having a solid concentration of 1 to 1% by weight, a viscosity of 5 to 12 mPa_s, and a moisture content 0.01 to 0.5% by weight, -52- 200844610 ο Wherein 'R1 to R4 are each independently a straight-chain-chain or cyclic alkyl group having a carbon number of 1 to 40 or a linear, cyclic or cyclic alkenyl group having a carbon number of 4 to 40, R1; 〜1 of the hydrogen atom of R4 may be substituted by a fluorine atom, and each of A1 and A2 is independently a hydrogen atom or 2. The liquid crystal alignment agent of claim 1 wherein the solvent contains free methyl carbitol , dimethyl carbitol, ethyl carbitol, carbitol, ethyl carbitol acetate, butyl carbitol, butyl carbamide, butyl cellosolve acetate and triglyceride Alcohol dimethyl ether is composed of 15 methyl groups. There is at least one selected from the group consisting of ethyl hexanol in the group -53- 200844610. A liquid crystal display element characterized by having a liquid crystal alignment film produced by a liquid crystal alignment agent according to claim 1 or 2. -54-