WO2022190896A1 - 液晶配向剤、液晶配向膜及び液晶表示素子 - Google Patents
液晶配向剤、液晶配向膜及び液晶表示素子 Download PDFInfo
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- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 1
- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-UHFFFAOYSA-N 0.000 description 1
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Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/52—Liquid crystal materials characterised by components which are not liquid crystals, e.g. additives with special physical aspect: solvents, solid particles
- C09K19/54—Additives having no specific mesophase characterised by their chemical composition
- C09K19/56—Aligning agents
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
-
- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
- G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
- G02F1/1333—Constructional arrangements; Manufacturing methods
- G02F1/1337—Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers
Definitions
- the present invention relates to a liquid crystal aligning agent, a liquid crystal aligning film, and a liquid crystal display element.
- a liquid crystal display device includes, for example, a liquid crystal layer sandwiched between an element substrate and a color filter substrate, a pixel electrode and a common electrode for applying an electric field to the liquid crystal layer, an alignment film for controlling the orientation of liquid crystal molecules in the liquid crystal layer, A thin film transistor (TFT) or the like is provided for switching an electric signal supplied to the pixel electrode.
- TFT thin film transistor
- Vertical electric field methods such as TN method and VA method
- horizontal electric field methods such as IPS (In Plane Switching) method and FFS (fringe field switching) method are known as methods for driving liquid crystal molecules.
- the liquid crystal alignment film that is most widely used industrially is formed on an electrode substrate, and the surface of a film made of polyamic acid and/or polyimide imidized thereof is covered with a cloth such as cotton, nylon, polyester, or the like. It is produced by rubbing in one direction, that is, by performing a so-called rubbing process.
- the rubbing treatment is a simple, highly productive and industrially useful method.
- Non-Patent Document 1, Patent Document 1, Patent Document 2 reference a method using a photoisomerization reaction, a method using a photocrosslinking reaction, a method using a photodecomposition reaction, etc.
- Liquid crystal alignment films used in liquid crystal display elements of the IPS driving method and the FFS driving method require a high alignment regulating force for suppressing afterimages (hereinafter also referred to as AC afterimages) generated by long-term AC driving.
- AC afterimages afterimages generated by long-term AC driving.
- the alignment treatment is performed by a photo-alignment method, the amount of light irradiation is a factor that affects the energy cost and the production speed, so it is preferable that the alignment treatment can be performed with a small amount of light irradiation.
- a liquid crystal alignment film that can realize liquid crystal alignment with a small amount of light irradiation is a liquid crystal alignment film with small variation (non-uniformity) in the twist angle of the liquid crystal in the plane of the liquid crystal alignment film. It became clear that the range of the light irradiation amount obtained is narrow. Therefore, the liquid crystal alignment becomes incomplete in a part of the liquid crystal alignment film obtained when the screen of the liquid crystal display element is enlarged, and when an image is displayed for a long time, the brightness in the plane becomes uneven. There is a concern that the display quality will be degraded.
- the object of the present invention is to expand the range of light irradiation amount to obtain a liquid crystal alignment film with small variation (non-uniformity) in the twist angle of the liquid crystal in the plane of the liquid crystal alignment film, and to improve the quality of the liquid crystal alignment film. It aims at providing the liquid crystal aligning agent which can obtain this efficiently, this liquid crystal aligning film obtained from this liquid crystal aligning agent, and the liquid crystal display element using this liquid crystal aligning film.
- a liquid crystal aligning agent capable of efficiently obtaining a high-quality liquid crystal alignment film by expanding the range of light irradiation amount for obtaining a liquid crystal alignment film capable of suppressing AC afterimage, and the liquid crystal alignment obtained from the liquid crystal alignment agent
- An object of the present invention is to provide a film and a liquid crystal display device using the liquid crystal alignment film.
- the present inventors have found that the above problems can be solved by using a liquid crystal aligning agent containing a specific component, and have completed the present invention.
- the gist is as follows.
- a liquid crystal aligning agent characterized by:
- X 1 represents a tetravalent organic group.
- Y 1 is a divalent organic group represented by the following formula (H) and having three or more benzene rings.
- R and Z each independently represents a hydrogen atom or a monovalent organic group.
- A represents an alkylene group having 4 to 10 carbon atoms.
- Ar 1 and Ar 1' each independently represent a benzene ring, a biphenyl structure, or a naphthalene ring. Any hydrogen atom on the ring of Ar 1 and Ar 1′ may be substituted with a monovalent group. ) Throughout the present specification, halogen atoms include fluorine, chlorine, bromine, and iodine atoms, and * represents a bond.
- a liquid crystal alignment film having a small variation (non-uniformity) in the twist angle of the liquid crystal within the plane of the liquid crystal alignment film can be obtained by expanding the range of the light irradiation amount, thereby efficiently producing a liquid crystal alignment film of good quality.
- the liquid crystal aligning agent which can be obtained well, this liquid crystal aligning film obtained from this liquid crystal aligning agent, and the liquid crystal display element using this liquid crystal aligning film are obtained.
- liquid crystal aligning agent capable of efficiently obtaining a high-quality liquid crystal alignment film by expanding the range of light irradiation amount for obtaining a liquid crystal alignment film capable of suppressing AC afterimage, and the liquid crystal alignment obtained from the liquid crystal alignment agent A film and a liquid crystal display device using the liquid crystal alignment film are obtained.
- FIG. 1 is a schematic cross-sectional view showing an example of a lateral electric field liquid crystal display device of the present invention
- FIG. 4 is a schematic cross-sectional view showing another example of the horizontal electric field liquid crystal display device of the present invention
- the liquid crystal aligning agent of the present invention is at least one polymer selected from the group consisting of a polyimide precursor having a repeating unit (a1) represented by the following formula (1) and a polyimide which is an imidized product of the polyimide precursor. Contains (A).
- the polymer (A) may be composed of one type or two or more types.
- X 1 represents a tetravalent organic group.
- Y 1 is a divalent organic group represented by the following formula (H) and having three or more benzene rings.
- R and Z each independently represents a hydrogen atom or a monovalent organic group.
- the polymer (A) more preferably has a divalent organic group represented by the above formula (H) in the main chain direction of the polymer (A). Moreover, the polymer (A) more preferably has the benzene ring of Y 1 in the main chain direction of the polymer (A).
- the main chain of a polymer refers to the portion of the polymer that consists of the longest chain of atoms.
- the polymer (A) has a divalent organic group represented by the formula (H) in the main chain direction of the polymer (A) means 2 represented by the formula (H) It means that the longest chain of atoms in the valent organic group constitutes the main chain of the polymer (A).
- the polymer (A) has a divalent organic group represented by the above formula (H) in the main chain direction of the polymer (A)
- the formula (H) It means that both ends of the longest chain of atoms in the divalent organic group are respectively bonded to two nitrogen atoms bonded to Y 1 in formula (1). It also means that at least two carbon atoms of each benzene ring of all the benzene rings of Y 1 constitute the main chain of the polymer (A).
- the benzene ring in the "divalent organic group having 3 or more benzene rings” includes a benzene ring constituting a condensed ring. And when counting the number of benzene rings in the formula (H), it is counted as follows.
- a naphthalene ring shall have two benzene rings.
- the biphenyl structure shall have two benzene rings.
- the number of benzene rings in Y 1 is not particularly limited as long as it is 3 or more, and may be, for example, 3 or more and 8 or less, or 3 or more and 6 or less. From the viewpoint of suitably obtaining the effects of the present invention, the number may be 4 or more and 6 or less.
- A represents an alkylene group having 4 to 10 carbon atoms, more preferably an alkylene group having 4, 6, 8 or 10 carbon atoms, and still more preferably an alkylene group having 4 or 6 carbon atoms.
- Ar 1 and Ar 1' each independently represent a benzene ring, a biphenyl structure, or a naphthalene ring. Any hydrogen atom on the ring of Ar 1 and Ar 1′ may be substituted with a monovalent group.
- Monovalent organic groups in which a part of atoms are substituted with at least one of halogen atoms and hydroxy groups are included.
- the monovalent group which is a substituent of any hydrogen atom on the ring of Ar 1 and Ar 1′ in the above formula (H) includes at least a halogen atom, an alkyl group having 1 to 3 carbon atoms, and a hydrogen atom.
- the group “*-L 1 -AL 1' -*” is the group “*-(CH 2 ) n -*", the group “*- O—(CH 2 ) n —O—*” and the group “*—O—(CH 2 ) n —*” are preferred.
- n is an integer of 4 to 10, preferably an integer of 4, 6, 8 or 10, more preferably an integer of 4 or 6.
- Y 1 in the above formula (1) is preferably a divalent organic group represented by any one of the following formulas (h-1) to (h-4) from the viewpoint of favorably obtaining the effects of the present invention.
- R a1 to R a4 represent monovalent organic groups. Specific examples thereof include Ar 1 and Ar 1′ in formula (H) above. and L is the group "*-L 1 -AL 1' -*" (* represents a bond) in the above formula (H). represents Each m is independently an integer of 0 to 6, and each n is independently an integer of 0 to 4. When a plurality of R a1 to R a4 are present, they may be the same or different. )
- a monovalent hydrocarbon group having 1 to 20 carbon atoms the methylene group of the hydrocarbon group is -O-, -S-, -CO -, -COO-, -COS-, -NR 3 -, -CO-NR 3 -, -Si(R 3 ) 2 - (where R 3 is a hydrogen atom or a monovalent carbonized carbon atom having 1 to 10 carbon atoms) is a hydrogen group), a monovalent group A substituted with —SO 2 —, etc., the above monovalent hydrocarbon group, or at least one hydrogen atom bonded to a carbon atom of the above monovalent group A is a halogen Atoms, hydroxy groups, alkoxy groups, nitro groups, amino groups, mercapto groups, nitroso groups, alkylsilyl groups, alkoxysilyl groups, silanol groups, sulphino groups, phosphino groups
- Examples include a substituted monovalent group and a monovalent group having a heterocyclic ring.
- the monovalent organic groups for R and Z in the above formula (1) include, among others, an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkynyl group having 2 to 10 carbon atoms, a tert- A butoxycarbonyl group or a 9-fluorenylmethoxycarbonyl group is preferred, an alkyl group having 1 to 3 carbon atoms is more preferred, and a methyl group is even more preferred.
- R and Z are each independently preferably a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, more preferably a hydrogen atom or a methyl group.
- the polymer (A) is a polyimide precursor having a repeating unit (a2) represented by the following formula (2) and an imidized product of the polyimide precursor At least one polymer selected from the group consisting of may be used.
- the polymer (A) further includes at least one of the repeating unit (a2) represented by the following formula (2) and the imidized structure of the repeating unit (a2) represented by the following formula (2) may have.
- the repeating unit (a2) may be composed of one type or two or more types.
- X 2 represents a tetravalent organic group.
- Y 2 represents a divalent organic group represented by the following formulas (o-1) to (o-14).
- R, and Z has the same meaning as R and Z in formula (1) above.
- the monovalent group which is a substituent of any hydrogen atom on the benzene ring, biphenyl structure or naphthalene ring in the formulas (o-1) to (o-14) includes a halogen atom, a C 1-3 Alkyl groups, alkyl groups in which at least part of the hydrogen atoms are substituted with at least one of the above halogen atoms and hydroxy groups; alkoxy groups having 1 to 3 carbon atoms, and at least part of the hydrogen atoms are the above halogen atoms and hydroxy groups an alkoxy group substituted with at least one; an alkenyl group having 2 to 3 carbon atoms; an acyl group having 2 to 3 carbon atoms; an alkylsilyl group having 1 to 3 carbon atoms, an alkoxysilyl group having 1 to 3 carbon atoms, and a hydroxy group , a monovalent group such as a nitrile group.
- the polymer (A) further includes a repeating unit (a2′) represented by the following formula (2′) and a repeating unit (a3) represented by the following formula (3) ), and at least one polymer selected from the group consisting of a polyimide that is an imidized product of the polyimide precursor.
- the polymer (A) further includes a repeating unit (a2′) represented by the following formula (2′), an imidated structure of the repeating unit (a2) represented by the following formula (2), It may have at least one of the repeating unit (a3) represented by (3) and the imidized structure of the repeating unit (a3) represented by the following formula (3).
- X 2′ and X 3 represent a tetravalent organic group
- Y 2′ represents a divalent organic group represented by the following formula (O2).
- Y 3 represents a divalent organic group having 6 to 30 carbon atoms having a group “—N(D)—(D represents a carbamate-based protective group)” in the molecule, and R and Z are respectively It is synonymous with R and Z in the above formula (1).
- m represents an integer of 0 to 2.
- Ar 2' represents a benzene ring or a naphthalene ring
- Ar 2' is each independently represents a benzene ring
- Any hydrogen atom on the ring of Ar 2′ may be replaced with a monovalent group, and the substituents include the above formulas (o-1) to (o- Structures exemplified as a monovalent group which is a substituent of an arbitrary hydrogen atom of a benzene ring, a biphenyl structure or a naphthalene ring in 14),
- Q 2′ represents a single bond or —O—, and Ar 2′ , and Q 2′ are present, the plurality of Ar 2′ and Q 2′ may be the same or different.
- divalent organic group represented by the above formula (O2) p-phenylenediamine, m-phenylenediamine, 2,5-diaminotoluene, 2,5-diamino-p from the viewpoint of less occurrence of AC afterimage.
- D in Y 3 above represents a carbamate-based protecting group
- examples of the carbamate-based protecting group include a tert-butoxycarbonyl group and a 9-fluorenylmethoxycarbonyl group.
- Specific examples of Y 3 include divalent organic groups represented by the following formula (Dx).
- Q 5 is a single bond, —(CH 2 ) n — (n is an integer of 1 to 20), or any —CH 2 — of —(CH 2 ) n — is —O -, -Si(CH 3 ) 2 -, -COO-, -OCO-, -NQ 9 -, -NQ 9 CO-, -CONQ 9 - , -NQ 9 CONQ 10 -, -NQ 9 COO- or -OCOO -, a group substituted with Q 9 and Q 10 each independently represent a hydrogen atom or a monovalent organic group; Q 6 and Q 7 each independently represents a group having —H, —NHD, —N(D) 2 , —NHD, or a group having —N(D) 2 (D represents a carbamate-based protecting group).
- Q 6 has a carbamate-based protecting group
- Q 6 and Q 7 represent a group other than a hydrogen atom
- the number of carbon atoms is preferably 1-8.
- the monovalent organic groups of Q 9 and Q 10 include an alkyl group having 1 to 3 carbon atoms, an alkenyl group having 2 to 3 carbon atoms, an alkynyl group having 2 to 3 carbon atoms, and a fluorine atom-containing 1 carbon atom group. to 3 monovalent organic groups.
- Y 3 examples include divalent organic groups represented by any one of the following formulas (Y3-1) to (Y3-9) from the viewpoint of less AC afterimage.
- "Boc” represents a tert-butoxycarbonyl group.
- X 1 , X 2 , X 2′ and X 3 are an acyclic aliphatic tetracarboxylic dianhydride or its derivative, an alicyclic tetracarboxylic dianhydride or its derivative, or an aromatic tetracarboxylic Examples include tetravalent organic groups derived from acid dianhydrides or derivatives thereof. Examples of tetracarboxylic dianhydride derivatives include tetracarboxylic acid dihalides, tetracarboxylic acid dialkyl esters, and tetracarboxylic acid dialkyl ester dihalides.
- a tetravalent organic group derived from a tetracarboxylic dianhydride or a derivative thereof having at least one partial structure selected from the group consisting of a cyclobutane ring structure, a cyclopentane ring structure and a cyclohexane ring structure is more preferred.
- X 1 , X 2 , X 2′ and X 3 include a tetravalent organic group represented by the following formula (g), and the following formulas (X-1) to (X-25). ), a tetravalent organic group derived from an aromatic tetracarboxylic dianhydride, and the like.
- X 1 , X 2 , X 2′ and X 3 are represented by the following formulas (g), (X-1) to (X-5), (X-11), ( A tetravalent organic group represented by X-21) to (X-23) is more preferable, and a tetravalent organic group represented by the following formula (g) is even more preferable.
- R 1 to R 4 are each independently a hydrogen atom, a halogen atom, an alkyl group having 1 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, an alkynyl group having 2 to 6 carbon atoms, , represents a monovalent organic group having 1 to 6 carbon atoms containing a fluorine atom, or a phenyl group, and at least one of R 1 to R 4 represents a group other than a hydrogen atom as defined above.
- alkyl groups having 1 to 6 carbon atoms in R 1 to R 4 in the above formula (g) include methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, isobutyl group and sec-butyl. groups, tert-butyl groups, n-pentyl groups, and the like.
- alkenyl group having 2 to 6 carbon atoms in R 1 to R 4 include vinyl group, propenyl group, butynyl group and the like, and these may be linear or branched.
- R 1 to R 4 Specific examples of the alkynyl group having 2 to 6 carbon atoms for R 1 to R 4 include ethynyl group, 1-propynyl group and 2-propynyl group.
- fluorine atom-containing monovalent organic group having 1 to 6 carbon atoms for R 1 to R 4 include a fluoromethyl group, a trifluoromethyl group, a pentafluoroethyl group and a pentafluoropropyl group.
- a more preferable combination of R 1 to R 4 is that, from the viewpoint of high photoreactivity, R 1 to R 4 are hydrogen atoms or methyl groups, and at least one of R 1 to R 4 is a methyl group. , R 1 to R 4 are more preferably methyl groups. More preferably, R 1 and R 4 is a methyl group, and R 2 and R 3 are hydrogen atoms.
- an aromatic tetracarboxylic dianhydride is an acid dianhydride obtained by intramolecular dehydration of a carboxy group bonded to an aromatic ring such as a benzene ring or a naphthalene ring.
- an aromatic ring such as a benzene ring or a naphthalene ring.
- Specific examples include a tetravalent organic group represented by any of the following formulas (Xa-1) to (Xa-2), and any of the following formulas (Xr-1) to (Xr-7).
- a tetravalent organic group can be mentioned.
- x and y are each independently a single bond, ether, carbonyl, ester, alkanediyl group having 1 to 10 carbon atoms, 1,4-phenylene, sulfonyl or an amide bond.
- j and k are integers of 0 or 1.
- the tetravalent organic group represented by the above formula (Xa-1) or (Xa-2) may have a structure represented by any one of the following formulas (Xa-3) to (Xa-19).
- the polymer (A) includes, in addition to the repeating unit (a1), the repeating unit (a2), the repeating unit (a2′), and the repeating unit (a3), a repeating unit (a4 ) and at least one polymer selected from the group consisting of a polyimide which is an imidized product of the polyimide precursor.
- X 4 represents a tetravalent organic group
- Y 4 represents a divalent organic group represented by the above formula (H)
- the above formulas (o-1) to (o-14) a divalent organic group represented by the above formula
- a divalent organic group represented by the above formula a divalent organic group having 6 to 30 carbon atoms having the above group "-N(D)-(D represents a carbamate-based protecting group)" in the molecule
- the above formula Re represents a divalent organic group other than the divalent organic group represented by (O2).
- R and Z have the same definitions as R and Z in formula (1) above, respectively.
- X 4 examples include the tetravalent organic groups exemplified in the explanations of X 1 , X 2 , X 2′ and X 3 above. From the viewpoint of suitably obtaining the effects of the present invention, X 4 is a tetravalent organic group represented by the above formula (g), or any one of the above formulas (X-1) to (X-25). is preferably a tetravalent organic group represented by the above formulas (g), (X-1) to (X-5), (X-11), (X-21) to (X-23). and more preferably a tetravalent organic group represented by the above formula (g).
- Y 4 is a divalent organic group represented by the above formula (H), a divalent organic group represented by the above formulas (o-1) to (o-14), the above group "-N(D) —(D represents a carbamate-based protecting group.)” in the molecule and a divalent organic group having 6 to 30 carbon atoms in the molecule, and a divalent organic group other than the divalent organic group represented by the above formula (O2)
- diamines having a photo-alignable group diamines having a photo-alignable group; diamines having a urea bond such as diamines represented by the following formulas (u-1) to (u-3) (provided that the diamines do not have a carbamate-based protective group in the molecule ); diamines having an amide bond such as diamines represented by the following formulas (u-4) to (u-8) (provided that the diamines do not have a carbamate-based protective group in the molecule); nitrogen atom-containing A heterocyclic ring and a group “* 21 -NR-* 22 ” (* 21 and * 22 represent a bond bonding to a carbon atom constituting an aromatic ring, provided that the carbon atom is bonded to R does not form a ring with a nitrogen atom, R represents a hydrogen atom or a monovalent organic group, and the above monovalent organic group is bonded to the nitrogen atom at a carbon atom other than the carbonyl carbon.
- nitrogen atom-containing structure selected from the group; 3,5-diaminobenzyl alcohol, 2,4-diaminobenzyl alcohol; 2,4-diaminobenzoic acid, 2,5-diaminobenzoic acid, 3,5-diaminobenzoic acid, 4,4'-diaminobiphenyl-3-carboxylic acid, 4,4'-diaminodiphenylmethane-3-carboxylic acid, 4,4'-diaminodiphenylethane -3-carboxylic acid, 4,4'-diaminobiphenyl-3,3'-dicarboxylic acid, 4,4'-diaminobiphenyl-2,2'-dicarboxylic acid, 3,3'-diaminobiphenyl-4,4' -dicarboxylic acid, 3,3'-diaminobiphenyl-2,4'-dicarboxylic acid, 3,3'-diaminobiphenyl-2,4
- diamines having a steroid skeleton diamines represented by the following formulas (V-1) to (V-6); diamines having a siloxane bond such as 1,3-bis(3-aminopropyl)-tetramethyldisiloxane; Diamines having an oxazoline ring structure such as formulas (Ox-1) to (Ox-2); 1-(4-(2,4-diaminophenoxy)ethoxy)phenyl)-2-hydroxy-2-methylpropanone, 2 -(4-(2-Hydroxy-2-methylpropanoyl)phenoxy)ethyl-3,5-diaminobenzoate, 4,4'-diaminobenzophenone, 3,3'-diaminobenzophenone, etc. having radical polymerization initiator function
- Examples include a divalent organic group obtained by removing two amino groups from a diamine such as diamine, and a group represented by any one of formulas (Y-1) to
- X v1 to X v4 and X p1 to X p2 are each independently —(CH 2 ) a — (a is an integer of 1 to 15; ), -CONH-, -NHCO-, -CO-N(CH 3 )-, -NH-, -O-, -CH 2 O-, -CH 2 -OCO-, -COO-, or -OCO -, X v5 represents -O-, -CH 2 O-, -CH 2 -OCO-, -COO- or -OCO-, X a is a single bond, -O-, -NH-, —O—(CH 2 ) m —O— (m represents an integer of 1 to 6), —C(CH 3 ) 2 —, —CO—, —(CH 2 ) m — (m is 1 to 6 ), —SO 2
- nitrogen atom-containing heterocyclic ring examples include pyrrole, imidazole, pyrazole, triazole, pyridine, pyrimidine, pyridazine, pyrazine, indole, benzimidazole, purine, quinoline, isoquinoline, naphthyridine, quinoxaline, phthalazine, triazine, carbazole, acridine, piperidine, piperazine, pyrrolidine, hexamethyleneimine and the like.
- pyridine, pyrimidine, pyrazine, piperidine, piperazine, quinoline, carbazole or acridine are preferred.
- R is preferably a hydrogen atom or a methyl group.
- diamines having a nitrogen atom-containing structure include 2,6-diaminopyridine, 3,4-diaminopyridine, 2,4-diaminopyrimidine, 3,6-diaminocarbazole, N-methyl-3,6 -diaminocarbazole, N-ethyl-3,6-diaminocarbazole, N-phenyl-3,6-diaminocarbazole, 1,4-bis-(4-aminophenyl)-piperazine, 3,6-diaminoacridine, the following formula Compounds represented by (Dp-1) to (Dp-8), and compounds represented by the following formulas (z-1) to (z-13) can be mentioned.
- the other divalent organic group is preferably a divalent organic group that does not have a side chain structure having 4 or more carbon atoms, and the side chain having 4 or more carbon atoms.
- the divalent organic group having no structure include the above-mentioned other diamines, 2-(2,4-diaminophenoxy)ethyl methacrylate, 2,4-diamino-N,N-diallylaniline, and the above-mentioned steroid skeleton.
- Diamines diamines represented by the above formulas (V-1) to (V-6), 1-(4-(2-(2,4-diaminophenoxy)ethoxy)phenyl)-2-hydroxy-2-methylpropane non, 2-(4-(2-hydroxy-2-methylpropanoyl)phenoxy)ethyl-3,5-diaminobenzoate, N-phenyl-3,6-diaminocarbazole, (z-4) and (z-6) ), and includes divalent organic groups obtained by removing two amino groups from the diamine.
- the polymer (A) preferably contains 5 to 100 mol% of the total repeating units (a1) and the imidized structure of the repeating units (a1) in the total repeating units. , preferably 10 to 100 mol %.
- the total here includes the case where either the repeating unit (a1) or the imidized structure of the repeating unit (a1) is 0 mol %.
- the term "total” also includes the case where one or more of the constituent elements are 0 mol %.
- the polymer (A) contains the repeating unit (a1) and a repeating unit other than the imidized structure of the repeating unit (a1)
- the polymer (A) is an imide of the repeating unit (a1) and the repeating unit (a1) It preferably contains 95 mol % or less, more preferably 90 mol % or less, and even more preferably 80 mol % or less of the total repeating units.
- the polymer (A) preferably contains 5 mol% or more of the total repeating units (a2) and the imidized structure of the repeating units (a2), More preferably 10 mol% or more, more preferably 20 mol% or more. Moreover, the upper limit thereof is preferably 90 mol %, more preferably 85 mol %.
- the polymer (A) should be such that the sum of the repeating units (a1) and (a2) and their imidized structures is 10 mol% or more of all repeating units. Preferably, it is more preferably 20 mol % or more.
- the polymer (A) contains repeating units other than repeating units (a1) and repeating units (a2) and their imidized structures, repeating units (a1) and repeating units (a2) and their imidized structures
- the upper limit of the total is preferably 95 mol%, more preferably 90 mol%.
- the polymer (A) contains at least one of the repeating unit (a2′) and the imidized structure of the repeating unit (a2′), the polymer (A) contains repeating
- the total of the unit (a2') and the imidized structure of the repeating unit (a2') preferably contains 1 to 50 mol% of the total repeating units, more preferably 1 to 40 mol%, and 1 to 30 mol. % is more preferable.
- the repeating unit (a1) and the repeating unit (a2 ') and the total lower limit of the imidized structure is preferably 5 mol %, more preferably 10 mol %.
- the polymer (A) comprises at least one of the repeating unit (a1) and its imidized structure, at least one of the repeating unit (a2) and its imidized structure, and the repeating unit (a2′) and at least one of its imidized structure, and the total of the repeating unit (a1), the repeating unit (a2) and the repeating unit (a2′) and their imidized structures is 30 mol% of all repeating units It is preferably at least 40 mol %, more preferably at least 40 mol %.
- repeating units (a1), repeating units (a2), repeating units (a2′), and repeating units other than those imidized structures is preferably 95 mol %, more preferably 90 mol %.
- the polymer (A) contains at least one of the repeating unit (a3) and the imidized structure of the repeating unit (a3)
- the polymer (A) contains the repeating unit ( The total of a3) and the imidized structure of the repeating unit (a3) preferably contains 1 to 40 mol%, more preferably 1 to 30 mol%, and 1 to 25 mol% of the total repeating units. More preferred.
- the polymer (A) may contain at least one of repeating units (a2') and repeating units (a3), and imidized structures thereof.
- the liquid crystal aligning agent of the present invention may contain, in addition to the polymer (A), a polymer (B) that does not have the repeating unit (a1) and its imidized structure in the molecule.
- the polymer (B) may be composed of one type or two or more types.
- examples of the polymer (B) include a polymer having a repeating unit represented by the following formula (5) or an imidized structure thereof.
- the repeating units or imidized structures thereof constituting the polymer (B) may be of one kind or may be composed of two or more kinds.
- X 5 is a tetravalent organic group
- Y 5 is a divalent organic group.
- R and Z are the same as R and Z in formula (1) above, respectively. be.
- the tetravalent organic group in X 5 above includes a tetravalent organic group derived from an acyclic aliphatic tetocarboxylic dianhydride or a derivative thereof, and a tetravalent organic group derived from an alicyclic tetracarboxylic dianhydride or a derivative thereof.
- a tetravalent organic group derived from a valent organic group or an aromatic tetracarboxylic dianhydride or a derivative thereof may be mentioned, and specific examples thereof include the tetravalent organic groups exemplified for X1 above.
- the acyclic aliphatic or alicyclic tetracarboxylic dianhydride or derivative thereof has a cyclobutane ring structure and a cyclopentane ring structure from the viewpoint of enhancing the liquid crystal orientation. and a tetracarboxylic dianhydride having at least one partial structure selected from the group consisting of a cyclohexane ring structure or a derivative thereof.
- X 5 is a tetravalent organic group represented by the above formula (g), a tetravalent organic group represented by any one of the above formulas (X-1) to (X-25), the above formula ( Xa-1) to (Xa-2) or tetravalent organic groups represented by the above formulas (Xr-1) to (Xr-7) (these are collectively referred to as specific Also referred to as a tetravalent organic group).
- the polymer ( B) is a polymer ( It preferably contains 5 mol % or more, more preferably 10 mol % or more, of the total repeating units contained in B).
- Examples of the divalent organic group for Y 5 include the divalent organic groups exemplified for Y 4 above. From the standpoint of less residual DC-derived afterimage, the polymer (B) is such that Y 5 is the diamine having the urea bond, the diamine having the amide bond, the diamine having the nitrogen atom-containing structure, 2,4-diaminophenol, 3,5-diaminophenol, 3,5-diaminobenzyl alcohol, 2,4-diaminobenzyl alcohol, 4,6-diaminoresorcinol, diamine having the above carboxy group, 4,4'-diaminodiphenylmethane, 3,4'- diaminodiphenylmethane, 3,3′-dimethyl-4,4′-diaminodiphenylmethane, p-phenylenediamine and m-phenylenediamine, divalent organic groups excluding two amino groups (these are collectively referred to as specific 2 It is preferably a poly
- the polymer (B) has two or more types of repeating units represented by the above formula (5) or imidized structures thereof, the diamine having the urea bond, and the diamine having the amide bond. , or at least one of the repeating unit represented by the formula ( 5 ) having Y5, which is a divalent organic group excluding two amino groups from the diamine having the nitrogen atom-containing structure, and an imidized structure thereof, It is more preferable to include at least one of the repeating unit represented by the formula ( 5 ) having Y5, which is a divalent organic group obtained by removing two amino groups from the other diamine, and the imidized structure thereof.
- the polymer (B) is the sum of the repeating unit represented by the formula (5) in which Y 5 is the above-mentioned specific divalent organic group and the imidized structure thereof, from the viewpoint of less residual DC-derived afterimage. It may be contained in an amount of 1 mol % or more, or 5 mol % or more of all repeating units contained in (B). It is more preferably 10 mol % or more, and still more preferably 20 mol % or more.
- the content ratio of the polymer (A) and the polymer (B) in the liquid crystal aligning agent is 10 in the mass ratio of [polymer (A)] / [polymer (B)]. /90 to 90/10, 20/80 to 90/10, or 20/80 to 80/20.
- the polyamic acid ester which is a polyimide precursor, and polyamic acid, which are polyimide precursors used in the present invention, and polyimide, which is an imidized product thereof, can be synthesized by known methods such as those described in WO2013/157586, for example.
- tetracarboxylic acid derivative component examples include tetracarboxylic dianhydrides and derivatives thereof (tetracarboxylic acid dihalides, tetracarboxylic acid diesters, and tetracarboxylic acid diester dihalides).
- a part of the polymer (A) or (B) contains an amic acid structure
- a polymer having an amic acid structure is obtained by reacting a tetracarboxylic dianhydride component and a diamine component. is obtained.
- the solvent is not particularly limited as long as it dissolves the produced polymer.
- Specific examples of the above solvents include N-methyl-2-pyrrolidone, N-ethyl-2-pyrrolidone, ⁇ -butyrolactone, N,N-dimethylformamide, N,N-dimethylacetamide, dimethylsulfoxide, 1,3-dimethyl -2-imidazolidinones.
- D 1 represents an alkyl group having 1 to 3 carbon atoms
- D 2 represents an alkyl group having 1 to 3 carbon atoms
- D 3 represents an alkyl group having 1 to 4 carbon atoms.
- the reaction can be carried out at any concentration, preferably 1 to 50% by mass, more preferably 5 to 30% by mass.
- the initial stage of the reaction can be carried out at a high concentration, and then the solvent can be added.
- the ratio of the total number of moles of the diamine component to the total number of moles of the tetracarboxylic acid derivative component is preferably 0.8 to 1.2. Similar to a normal polycondensation reaction, the closer the molar ratio is to 1.0, the larger the molecular weights of the polymers (A) and (B) produced.
- Polyamic acid esters are produced by, for example, [I] a method of reacting the polyamic acid obtained by the above method with an esterifying agent, [II] a method of reacting a tetracarboxylic acid diester with a diamine, [III] a tetracarboxylic acid It can be obtained by a known method such as a method of reacting a diester dihalide and a diamine.
- Examples of methods for obtaining polyimide include known methods such as thermal imidization in which the polymer solution obtained by the above reaction is heated as it is, and catalytic imidization in which a catalyst is added to the polymer solution.
- the imidization rate is preferably 20 to 95%, more preferably 30 to 95%, still more preferably 50 to 95%.
- the polyamic acid, polyamic acid ester, and polyimide used in the present invention preferably have a solution viscosity of, for example, 10 to 1000 mPa s when made into a solution having a concentration of 10 to 15% by mass, from the viewpoint of workability. , is not particularly limited.
- the solution viscosity (mPa s) of the polymer is a polymer having a concentration of 10 to 15 mass% prepared using a good solvent for the polymer (eg, ⁇ -butyrolactone, N-methyl-2-pyrrolidone, etc.). It is a value measured at 25° C. for a solution using an E-type rotational viscometer.
- the polystyrene equivalent weight average molecular weight (Mw) measured by gel permeation chromatography (GPC) of the polyamic acid, polyamic acid ester and polyimide is preferably 1,000 to 500,000, more preferably 2,000. ⁇ 300,000.
- the molecular weight distribution (Mw/Mn) represented by the ratio of Mw to the polystyrene equivalent number average molecular weight (Mn) measured by GPC is preferably 15 or less, more preferably 10 or less. With such a molecular weight range, good orientation and stability of the liquid crystal display device can be ensured.
- a terminal-blocked polymer is prepared using an appropriate terminal-blocking agent together with the tetracarboxylic acid derivative component and the diamine component as described above. It is good also as synthesize
- the end-blocking polymer has effects of improving the film hardness of the liquid crystal alignment film obtained by the coating film and improving the adhesion properties between the sealing agent and the liquid crystal alignment film.
- Examples of the terminal of polymer (A) and polymer (B) in the present invention include an amino group, a carboxyl group, an acid anhydride group, or a group derived from a terminal blocking agent to be described later.
- An amino group, a carboxyl group, and an acid anhydride group can be obtained by a normal condensation reaction, or can be obtained by terminal blocking using the following terminal blocking agents.
- Terminal blockers include, for example, acetic anhydride, maleic anhydride, nadic anhydride, phthalic anhydride, itaconic anhydride, cyclohexanedicarboxylic anhydride, 3-hydroxyphthalic anhydride, trimellitic anhydride, 3-( 3-trimethoxysilyl)propyl)-3,4-dihydrofuran-2,5-dione, 4,5,6,7-tetrafluoroisobenzofuran-1,3-dione, 4-ethynylphthalic anhydride, etc.
- the proportion of the end blocking agent used is preferably 0.01 to 20 mol parts, more preferably 0.01 to 10 mol parts, per 100 mol parts in total of the diamine components used.
- the liquid crystal aligning agent of the present invention contains a polymer (A) and, if necessary, a polymer (B).
- the liquid crystal aligning agent of the present invention may contain other polymers in addition to the polymer (A) and polymer (B). Specific examples of other polymers include polysiloxane, polyester, polyamide, polyurea, polyurethane, polyorganosiloxane, cellulose derivative, polyacetal, polystyrene derivative, poly(styrene-maleic anhydride) copolymer, poly(isobutylene).
- poly(styrene-maleic anhydride) copolymers examples include SMA1000, 2000, 3000 (manufactured by Cray Valley), GSM301 (manufactured by Gifu Shellac Manufacturing Co., Ltd.), etc.
- Poly(isobutylene-maleic acid Anhydride) copolymers include Isoban-600 (manufactured by Kuraray Co., Ltd.), and specific examples of poly(vinyl ether-maleic anhydride) copolymers include Gantrez AN-139 (methyl vinyl ether anhydride). maleic acid resin, manufactured by Ashland). Other polymers may be used singly or in combination of two or more.
- the content of the other polymer is preferably 90 parts by mass or less, more preferably 10 to 90 parts by mass, and further 20 to 80 parts by mass with respect to the total 100 parts by mass of the polymer contained in the liquid crystal aligning agent. preferable.
- the liquid crystal alignment agent is used to produce the liquid crystal alignment film, and takes the form of a coating liquid from the viewpoint of forming a uniform thin film.
- the liquid crystal aligning agent of the present invention it is preferable that the liquid crystal aligning agent is a coating liquid containing the above-described polymer component and an organic solvent.
- the concentration of the polymer in the liquid crystal aligning agent can be appropriately changed by setting the thickness of the coating film to be formed.
- the concentration of the polymer in the liquid crystal aligning agent is preferably 1% by mass or more from the viewpoint of forming a uniform and defect-free coating film, and is preferably 10% by mass or less from the viewpoint of the storage stability of the solution.
- a particularly preferred polymer concentration is 2 to 8% by weight.
- the organic solvent contained in the liquid crystal aligning agent is not particularly limited as long as it dissolves the polymer component uniformly.
- Specific examples include N,N-dimethylformamide, N,N-dimethylacetamide, N,N-dimethyllactamide, N,N-dimethylpropionamide, tetramethylurea, N,N-diethylformamide, N-methyl -2-pyrrolidone, N-ethyl-2-pyrrolidone, dimethylsulfoxide, ⁇ -butyrolactone, ⁇ -valerolactone, 1,3-dimethyl-2-imidazolidinone, methyl ethyl ketone, cyclohexanone, cyclopentanone, 3-methoxy-N ,N-dimethylpropanamide, 3-butoxy-N,N-dimethylpropanamide, N-(n-propyl)-2-pyrrolidone, N-isopropyl-2-pyrrolidone, N-(
- N-methyl-2-pyrrolidone, N-ethyl-2-pyrrolidone, 3-methoxy-N,N-dimethylpropanamide, 3-butoxy-N,N-dimethylpropanamide and ⁇ -butyrolactone are preferred.
- the content of the good solvent is preferably 20 to 99% by mass, more preferably 20 to 90% by mass, and particularly preferably 30 to 80% by mass of the total solvent contained in the liquid crystal aligning agent. .
- the organic solvent contained in the liquid crystal aligning agent is a mixture of the above solvents and a solvent (also referred to as a poor solvent) that improves the coatability and the surface smoothness of the coating film when applying the liquid crystal aligning agent.
- a solvent also referred to as a poor solvent
- the use of solvents is preferred.
- the content of the poor solvent is preferably 1 to 80% by mass, more preferably 10 to 80% by mass, particularly preferably 20 to 70% by mass, of the total solvent contained in the liquid crystal aligning agent.
- the type and content of the poor solvent are appropriately selected according to the liquid crystal aligning agent coating device, coating conditions, coating environment, and the like. Specific examples of the poor solvent used in combination are shown below, but are not limited thereto.
- diisobutyl carbinol propylene glycol monobutyl ether, propylene glycol diacetate, diethylene glycol diethyl ether, dipropylene glycol monomethyl ether, dipropylene glycol dimethyl ether, 4-hydroxy-4-methyl-2-pentanone, ethylene glycol monobutyl ether, ethylene Glycol monobutyl ether acetate or diisobutyl ketone are preferred.
- Preferred solvent combinations of a good solvent and a poor solvent include N-methyl-2-pyrrolidone and ethylene glycol monobutyl ether, N-methyl-2-pyrrolidone, ⁇ -butyrolactone and ethylene glycol monobutyl ether, N-methyl-2- Pyrrolidone and ⁇ -butyrolactone and propylene glycol monobutyl ether, N-ethyl-2-pyrrolidone and propylene glycol monobutyl ether, N-ethyl-2-pyrrolidone and 4-hydroxy-4-methyl-2-pentanone, N-ethyl-2- pyrrolidone and propylene glycol diacetate, N,N-dimethyllactamide and diisobutyl ketone, N-methyl-2-pyrrolidone and ethyl 3-ethoxypropionate, N-ethyl-2-pyrrolidone and ethyl 3-ethoxypropionate, N- Methy
- the liquid crystal aligning agent of the present invention may additionally contain components (hereinafter also referred to as additive components) other than the polymer component and the organic solvent.
- additive components include adhesion aids for enhancing the adhesion between the liquid crystal alignment film and the substrate and the adhesion between the liquid crystal alignment film and the sealant, compounds for increasing the strength of the liquid crystal alignment film (hereinafter referred to as Also referred to as a crosslinkable compound.), compounds for promoting imidization, dielectrics and conductive substances for adjusting the dielectric constant and electrical resistance of the liquid crystal alignment film, and the like.
- crosslinkable compound oxiranyl group, oxetanyl group, protected isocyanate group, protected isothiocyanate group, group containing oxazoline ring structure, Meldrum, from the viewpoint of exhibiting good resistance to AC afterimage and highly improving film strength.
- a group containing an acid structure, a compound having at least one group selected from the group consisting of a cyclocarbonate group and a hydroxyalkylamide bond, and a phenolic compound having at least one of an alkoxymethyl group and a methylol group. may be at least one compound.
- compounds having an oxiranyl group include ethylene glycol diglycidyl ether, polyethylene glycol diglycidyl ether, propylene glycol diglycidyl ether, tripropylene glycol diglycidyl ether, polypropylene glycol diglycidyl ether, neopentyl glycol diglycidyl ether, 1 ,6-hexanediol diglycidyl ether, glycerin diglycidyl ether, 2,2-dibromoneopentyl glycol diglycidyl ether, 1,3,5,6-tetraglycidyl-2,4-hexanediol, Epicoat 828 (Mitsubishi Chemical Co., Ltd.) ), bisphenol F type epoxy resins such as Epicoat 807 (manufactured by Mitsubishi Chemical Corporation), hydrogenated bisphenol A type epoxy resins such as YX-8000 (manufactured by Mitsubishi Chemical Corporation), YX6954BH30 (Mitsubishi Chemical
- triglycidyl isocyanurates such as TEPIC (manufactured by Nissan Chemical Industries, Ltd.), alicyclic epoxy resins such as Celoxide 2021P (manufactured by Daicel Chemical Industries, Ltd.), N,N,N',N'-tetraglycidyl-m- xylylenediamine, 1,3-bis(N,N-diglycidylaminomethyl)cyclohexane, N,N,N',N'-tetraglycidyl-4,4'-diaminodiphenylmethane, tetrakis(glycidyloxymethyl)methane mentioned.
- TEPIC manufactured by Nissan Chemical Industries, Ltd.
- alicyclic epoxy resins such as Celoxide 2021P (manufactured by Daicel Chemical Industries, Ltd.)
- N,N,N',N'-tetraglycidyl-m- xylylenediamine 1,3-bis(N,
- compounds having an oxetanyl group include compounds having two or more oxetanyl groups described in paragraphs [0170] to [0175] of WO2011/132751.
- the compound having a protected isocyanate group include compounds having two or more protected isocyanate groups described in paragraphs [0046] to [0047] of JP-A-2014-224978, paragraphs of WO2015/141598.
- Examples include compounds having three or more protected isocyanate groups described in [0119] to [0120], and commercially available products include, for example, Coronate AP Stable M, Coronate 2503, 2515, 2507, 2513, 2555, Millionate MS.
- B-830, B-815N, B-820NSU, B-842N, B-846N, B-870N, B-874N, B-882N (manufactured by Mitsui Chemicals) etc. can be preferably used.
- Specific examples of compounds having protected isothiocyanate groups include compounds having two or more protected isothiocyanate groups described in Japanese Patent Application Laid-Open No. 2016-200798.
- Specific examples of compounds having a group containing an oxazoline ring structure include compounds containing two or more oxazoline ring structures described in paragraph [0115] of JP-A-2007-286597.
- Specific examples of the compound having a group containing a Meldrum's acid structure include compounds having two or more Meldrum's acid structures described in WO2012/091088.
- Specific examples of compounds having a cyclocarbonate group include compounds described in WO2011/155577.
- the compound having a hydroxyalkylamide bond include two groups represented by the following formula (d) described in WO2015/072554 and paragraph [0058] of Japanese Patent Application Laid-Open No. 2016-118753. compounds having one or more, compounds described in Japanese Patent Application Laid-Open No. 2016-200798, and the like.
- R 2 and R 3 are each independently a hydrogen atom, an alkyl group having 1 to 3 carbon atoms, or "*-CH 2 -OH".
- phenol compound having at least one of the alkoxyalkyl group and the methylol group include compounds described in WO2010/074269.
- crosslinkable compounds are examples of crosslinkable compounds, and are not limited to these.
- components other than those described above disclosed on pages 53 [0105] to 55 [0116] of WO2015/060357 may be used.
- the crosslinkable compounds are, among others, N,N,N',N'-tetraglycidyl-m-xylylenediamine, 1,3-bis(N,N-diglycidylaminomethyl)cyclohexane, N,N,N' , N'-tetraglycidyl-4, 4'-diaminodiphenylmethane, Takenate B-830, B-815N, B-820NSU, B-842N, B-846N, B-870N, B-874N, B-882N, 1, 3,5-tris(2-hydroxyethyl)isocyanurate, triglycidyl isocyanurate, n,n,n',n'-tetrakis(2-hydroxyethyl)adipamide, 2,2-bis(4-hydroxy-3 ,5-dihydroxymethylphenyl)propane, 2,2-bis(4-hydroxy-3,5-dimethoxymethylphenyl)propane, 2,2-bis(
- the content of the crosslinkable compound in the liquid crystal aligning agent of the present invention is preferably 0.5 to 20 parts by mass with respect to 100 parts by mass of the polymer component contained in the liquid crystal aligning agent. , and more preferably 1 to 15 parts by mass from the viewpoint of exhibiting good resistance to AC afterimages.
- adhesion aid examples include 3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, 3-aminopropyldiethoxymethylsilane, 2-aminopropyltrimethoxysilane, 2-aminopropyltriethoxysilane, N -(2-aminoethyl)-3-aminopropyltrimethoxysilane, N-(2-aminoethyl)-3-aminopropylmethyldimethoxysilane, 3-ureidopropyltrimethoxysilane, 3-ureidopropyltriethoxysilane, N -ethoxycarbonyl-3-aminopropyltrimethoxysilane, vinyltrimethoxysilane, vinyltriethoxysilane, 2-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, 3-glycidoxypropylmethyldimeth
- silane coupling agent When using a silane coupling agent, from the viewpoint of expressing good resistance to AC afterimage, it is 0.1 to 30 parts by weight with respect to 100 parts by weight of the polymer component contained in the liquid crystal aligning agent. It is preferably from 0.1 to 20 parts by mass.
- Compounds for promoting the imidization include basic sites (e.g., primary amino groups, aliphatic heterocycles (e.g., pyrrolidine skeleton), aromatic heterocycles (e.g., imidazole ring, indole ring), or a guanidino group, etc.) (excluding the crosslinkable compound and the adhesion promoter), or a compound in which the basic site is generated during baking. More preferably, it is a compound in which the above-mentioned basic site is generated during firing, and specific examples thereof include compounds represented by the following formulas (B-1) to (B-17).
- the content of the compound for promoting imidization is preferably 2 mol parts or less, more preferably 1 mol part or less, with respect to 1 mol part of the amic acid or amic acid ester site of the polymer (A), Preferably, it is 0.5 mol part or less.
- D represents an organic group that is eliminated by heating, preferably a tert-butoxycarbonyl group or a 9-fluorenylmethoxycarbonyl group.
- the solid content concentration in the liquid crystal aligning agent (ratio of the total mass of components other than the solvent of the liquid crystal aligning agent to the total mass of the liquid crystal aligning agent) is appropriately selected in consideration of viscosity, volatility, etc., but preferably It is in the range of 1 to 10% by mass.
- a particularly preferable solid content concentration range varies depending on the method used when applying the liquid crystal aligning agent to the substrate.
- the solid content concentration is particularly preferably in the range of 1.5 to 4.5% by mass.
- the printing method it is particularly preferable to set the solid content concentration in the range of 3 to 9% by mass, thereby setting the solution viscosity in the range of 12 to 50 mPa ⁇ s.
- the ink jet method it is particularly preferable to set the solid content concentration in the range of 1 to 5% by mass, thereby setting the solution viscosity in the range of 3 to 15 mPa ⁇ s.
- the temperature in preparing the polymer composition is preferably 10-50°C, more preferably 20-30°C.
- the liquid crystal alignment film of the present invention is obtained from the above liquid crystal alignment agent.
- the liquid crystal alignment film of the present invention can be used for a horizontal alignment type or vertical alignment type (VA type) liquid crystal alignment film. membrane.
- the liquid crystal alignment film of the present invention is preferably used as a liquid crystal alignment film for photo-alignment treatment.
- the liquid crystal alignment film of the present invention can be effectively applied to various technical applications. Alignment film or liquid crystal alignment film for transmission scattering type liquid crystal light control element), or other uses such as protective film (e.g.
- the liquid crystal display element of the present invention comprises the liquid crystal alignment film.
- the liquid crystal display device of the present invention can be manufactured, for example, by a method including the following steps (1) to (3).
- the liquid crystal display device of the present invention can be manufactured, for example, by a method including the following steps (1) to (3) and (5) or steps (1) to (2) and (5). More preferably, it is produced by a method comprising steps (1) to (5).
- a process (1) is a process of apply
- a specific example of step (1) is as follows.
- the liquid crystal aligning agent of the present invention is applied to one surface of the substrate provided with the patterned transparent conductive film by an appropriate coating method such as a roll coater method, a spin coat method, a printing method, an inkjet method, or the like.
- the substrate is not particularly limited as long as it is highly transparent, and in addition to a glass substrate and a silicon nitride substrate, a plastic substrate such as an acrylic substrate or a polycarbonate substrate can also be used.
- a reflective liquid crystal display element if only one substrate is used, an opaque material such as a silicon wafer can be used, and in this case, a light-reflecting material such as aluminum can be used for the electrodes.
- a substrate provided with electrodes made of a transparent conductive film or a metal film patterned in a comb shape and a counter substrate provided with no electrodes are used.
- Screen printing, offset printing, flexographic printing, inkjet method, spray method, etc. can be used as methods for applying the liquid crystal aligning agent to the substrate and forming a film.
- the coating method and the film-forming method by the inkjet method can be preferably used.
- a process (2) is a process of baking the liquid crystal aligning agent apply
- a specific example of step (2) is as follows. After applying the liquid crystal aligning agent on the substrate in step (1), the solvent is evaporated or the polyamic acid or polyamic acid ester is heated by heating means such as a hot plate, a thermal circulation oven, or an IR (infrared) oven. Thermal imidization can be performed.
- the drying and baking steps after applying the liquid crystal aligning agent of the present invention can be performed at any desired temperature and time, and may be performed multiple times.
- the firing temperature can be, for example, 40 to 180°C.
- the firing time at that time is not particularly limited, but may be 1 to 10 minutes or 1 to 5 minutes.
- a step of baking at a temperature range of 150 to 300 ° C. or 150 to 250 ° C. may be added.
- the firing time at that time is not particularly limited, but includes a firing time of 5 to 40 minutes or 5 to 30 minutes.
- the thickness of the film after baking is preferably 5 to 300 nm, more preferably 10 to 200 nm, because if it is too thin, the reliability of the liquid crystal display element may be lowered.
- Step (3) is a step of subjecting the baked film (coating film) obtained in step (2) to an orientation treatment depending on the case. That is, in a horizontally aligned liquid crystal display element such as an IPS system or an FFS system, the coating film is subjected to an alignment ability imparting treatment. On the other hand, in a vertical alignment type liquid crystal display element such as VA mode or PSA mode, the formed coating film can be used as a liquid crystal alignment film as it is, but the coating film may be subjected to an alignment ability imparting treatment.
- the alignment treatment method for the liquid crystal alignment film includes a rubbing treatment method and a photo-alignment treatment method, and the photo-alignment treatment method is more preferable.
- the surface of the film is irradiated with radiation polarized in a certain direction, and in some cases, preferably, heat treatment is performed at a temperature of 150 to 250 ° C. to improve liquid crystal alignment (liquid crystal alignment (also referred to as ability).
- radiation ultraviolet light or visible light having a wavelength of 100 to 800 nm can be used. Among them, ultraviolet rays having a wavelength of 100 to 400 nm, more preferably 200 to 400 nm are preferred.
- the irradiation dose of the radiation is preferably 1 to 10,000 mJ/cm 2 , more preferably 100 to 5,000 mJ/cm 2 , still more preferably 100 to 1,500 mJ/cm 2 , and 100 to 1,000 mJ/cm 2 . is particularly preferred, and 100-400 mJ/cm 2 is even more preferred.
- the light irradiation amount in the alignment treatment is 100 to 5,000 mJ/cm 2 , but in the liquid crystal aligning agent of the present invention, the light irradiation amount in the alignment treatment is reduced. Even so, it is possible to obtain a liquid crystal alignment film in which variation (non-uniformity) in liquid crystal alignment in the plane of the liquid crystal alignment film is suppressed.
- the substrate having the film-like material may be irradiated while being heated at 50 to 250° C. in order to improve liquid crystal orientation.
- the liquid crystal alignment film thus produced can stably orient liquid crystal molecules in a fixed direction.
- the liquid crystal alignment film irradiated with polarized radiation can be subjected to contact treatment using water or a solvent, or the liquid crystal alignment film irradiated with radiation can be heat-treated.
- the solvent used in the contact treatment is not particularly limited as long as it dissolves the decomposed product produced from the film-like material by irradiation with radiation.
- Specific examples include water, methanol, ethanol, 2-propanol, acetone, methyl ethyl ketone, 1-methoxy-2-propanol, 1-methoxy-2-propanol acetate, butyl cellosolve, ethyl lactate, methyl lactate, diacetone alcohol, 3- methyl methoxypropionate, ethyl 3-ethoxypropionate, propyl acetate, butyl acetate, cyclohexyl acetate and the like.
- water, 2-propanol, 1-methoxy-2-propanol and ethyl lactate are preferable from the viewpoint of versatility and solvent safety. More preferred are water, 1-methoxy-2-propanol or ethyl lactate.
- Solvents may be used singly or in combination of two or more.
- Step (4) is a step of heat-treating the liquid crystal alignment film oriented in step (3). You may heat-process with respect to the irradiation film (coating film) which irradiated the said radiation.
- the temperature of the heat treatment for the coating film irradiated with radiation is preferably 50 to 300.degree. C., more preferably 120 to 250.degree.
- the heat treatment time is preferably 1 to 30 minutes.
- Step (5) Step of producing a liquid crystal cell> Two substrates on which liquid crystal alignment films are formed as described above are prepared, and liquid crystal is arranged between the two substrates facing each other. Specifically, the following two methods are mentioned. In the first method, first, two substrates are arranged to face each other with a gap (cell gap) interposed therebetween so that the respective liquid crystal alignment films face each other. Then, the two substrates are bonded together using a sealant on the periphery, and the liquid crystal composition is injected and filled into the cell gap defined by the substrate surfaces and the sealant to contact the film surface, and then the injection hole is sealed. stop.
- the second method is a method called ODF (One Drop Fill) method.
- ODF One Drop Fill
- a predetermined place on one of the two substrates on which the liquid crystal alignment film is formed is coated with, for example, an ultraviolet light-curing sealant, and a liquid crystal composition is applied to several predetermined places on the surface of the liquid crystal alignment film. drip.
- the other substrate is attached so that the liquid crystal alignment films face each other, and the liquid crystal composition is spread over the entire surface of the substrate and brought into contact with the film surface.
- the entire surface of the substrate is irradiated with ultraviolet light to cure the sealant.
- the two substrates are arranged opposite to each other so that the rubbing directions of the respective coating films are at a predetermined angle, for example, orthogonal or antiparallel.
- the sealant for example, an epoxy resin or the like containing a curing agent and aluminum oxide spheres as spacers can be used.
- the liquid crystal composition is not particularly limited, and various liquid crystal compositions containing at least one liquid crystal compound (liquid crystal molecule) and having positive or negative dielectric anisotropy can be used.
- a liquid crystal composition with a positive dielectric anisotropy is also referred to as a positive liquid crystal
- a liquid crystal composition with a negative dielectric anisotropy is also referred to as a negative liquid crystal.
- the liquid crystal composition include a liquid crystal composition exhibiting a nematic phase and a liquid crystal composition exhibiting a smectic phase. Among them, a liquid crystal composition exhibiting a nematic phase is preferable.
- the liquid crystal composition includes a fluoro group, a hydroxy group, an amino group, a fluorine atom-containing group (e.g., trifluoromethyl group), a cyano group, an alkyl group, an alkoxy group, an alkenyl group, an isothiocyanate group, a heterocyclic ring, a cycloalkane,
- a liquid crystal compound having a cycloalkene, a steroid skeleton, a benzene ring, or a naphthalene ring may be included, and a compound having two or more rigid sites (mesogenic skeleton) exhibiting liquid crystallinity in the molecule (for example, two rigid biphenyl structures or terphenyl structures linked by alkyl groups).
- the liquid crystal composition may further contain an additive from the viewpoint of improving liquid crystal orientation.
- additives include photopolymerizable monomers such as compounds having a polymerizable group; optically active compounds (eg, S-811 manufactured by Merck Co., Ltd.); antioxidants; UV absorbers; dyes; antifoaming agents; polymerization initiators; or polymerization inhibitors.
- Positive liquid crystals include ZLI-2293, ZLI-4792, MLC-2003, MLC-2041, MLC-3019, and MLC-7081 manufactured by Merck.
- Negative liquid crystals include, for example, MLC-6608, MLC-6609, MLC-6610, and MLC-7026-100 manufactured by Merck.
- MLC-3023 manufactured by Merck & Co., Ltd. can be mentioned.
- a liquid crystal display element can be obtained by bonding a polarizing plate to the outer surface of the liquid crystal cell as necessary.
- a polarizing plate to be attached to the outer surface of the liquid crystal cell, a polarizing film called "H film” in which polyvinyl alcohol is stretched and oriented while absorbing iodine is sandwiched between cellulose acetate protective films, or the H film itself.
- a polarizing plate consisting of
- the IPS substrate which is a comb-teeth electrode substrate used in IPS (In-Plane Switching) mode, includes a substrate, a plurality of linear electrodes formed on the substrate and arranged in a comb-teeth shape, and and a liquid crystal alignment film formed to cover the linear electrodes.
- the FFS substrate which is a comb-teeth electrode substrate used in the FFS (Fringe Field Switching) mode, includes a base material, a plane electrode formed on the base material, an insulating film formed on the plane electrode, and an insulating film. It has a plurality of linear electrodes formed on the film and arranged in a comb shape, and a liquid crystal alignment film formed on the insulating film so as to cover the linear electrodes.
- FIG. 1 is a schematic cross-sectional view showing an example of the horizontal electric field liquid crystal display device of the present invention, which is an example of an IPS mode liquid crystal display device.
- the liquid crystal 3 is sandwiched between the comb-teeth electrode substrate 2 having the liquid crystal alignment film 2c and the opposing substrate 4 having the liquid crystal alignment film 4a.
- the comb-shaped electrode substrate 2 includes a base material 2a, a plurality of linear electrodes 2b formed on the base material 2a and arranged in a comb-like shape, and a plurality of linear electrodes 2b formed on the base material 2a so as to cover the linear electrodes 2b. and a liquid crystal alignment film 2c.
- the counter substrate 4 has a base material 4b and a liquid crystal alignment film 4a formed on the base material 4b.
- the liquid crystal alignment film 2c is, for example, the liquid crystal alignment film of the present invention.
- the liquid crystal alignment film 4c is also the liquid crystal alignment film of the present invention.
- the horizontal electric field liquid crystal display element 1 when a voltage is applied to the linear electrodes 2b, an electric field is generated between the linear electrodes 2b as indicated by electric lines of force L.
- FIG. 2 is a schematic sectional view showing another example of the horizontal electric field liquid crystal display device of the present invention, which is an example of the FFS mode liquid crystal display device.
- the liquid crystal 3 is sandwiched between the comb-teeth electrode substrate 2 having the liquid crystal alignment film 2h and the counter substrate 4 having the liquid crystal alignment film 4a.
- the comb-shaped electrode substrate 2 includes a substrate 2d, a plane electrode 2e formed on the substrate 2d, an insulating film 2f formed on the plane electrode 2e, and a comb-shaped electrode formed on the insulating film 2f.
- the counter substrate 4 has a base material 4b and a liquid crystal alignment film 4a formed on the base material 4b.
- the liquid crystal alignment film 2h is, for example, the liquid crystal alignment film of the present invention.
- the liquid crystal alignment film 4a is also the liquid crystal alignment film of the present invention.
- WA-1 to WA-2 compounds represented by the following formulas (WA-1) to (WA-2), respectively
- (tetracarboxylic dianhydride) B1 to B2 compounds represented by the following formulas (B1) to (B2), respectively
- AD-1 to AD-2 compounds represented by the following formulas (AD-1) to (AD-2), respectively
- the viscosity of the solution was measured using an E-type viscometer TVE-22H (manufactured by Toki Sangyo Co., Ltd.) with a sample volume of 1.1 mL and a cone rotor TE-1 (1°34', R24) at a temperature of 25°C. did.
- the molecular weight of the polyamic acid was determined using a room temperature gel permeation chromatography (GPC) device (GPC-101) (manufactured by Showa Denko KK) and a column (KD-803, KD-805 in series) (manufactured by Showa Denko KK) as follows.
- GPC room temperature gel permeation chromatography
- WA-1-1 (20.0 g, 40 mmol), benzophenone imine (15.9 g, 88 mmol), tris(dibenzylideneacetone) dipalladium (Pd 2 (dba) 3 ) (0.7 g, 0.8 mmol), 2-dicyclohexylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl (XPhos) (1.52 g, 3.2 mmol), sodium tert-butoxide (10.8 g , 112 mmol) and THF (400 g) were added, heated to 70° C., and stirred for 1 hour.
- Table 1 summarizes the types and amounts of the diamine components and tetracarboxylic acid components used in Synthesis Examples 1-7. Numerical values in parentheses in the table represent the amounts (mol parts) of monomers used per 100 mol parts in total in each component.
- Example 2 The polyamic acid (A-1) solution (5.30 g) obtained in Synthesis Example 1 was added with the polyamic acid (B-1) solution (9.54 g) obtained in Synthesis Example 3, NMP (3.78 g), BCS (9.00 g), NMP10 wt% diluted solution of AD-1 (0.800 g) and NMP1 wt% diluted solution of AD-2 (1.59 g) were added, stirred for 2 hours at room temperature, liquid crystal aligning agent (V-2) was obtained.
- Example 3 A liquid crystal aligning agent (V-3) was obtained in the same manner as in Example 2, except that the polyamic acid solution used was changed from the (A-1) solution to the (A-2) solution.
- Table 2 shows the specifications of the liquid crystal aligning agents obtained in Examples 1 to 3 and Comparative Examples 1 to 6 above.
- the numbers in parentheses for the polymer components represent the ratio (parts by mass) of each polymer component with respect to the total 100 parts by mass of the polymer components.
- an FFS-driven liquid crystal cell was produced according to the procedure shown below, and various evaluations were performed.
- a liquid crystal cell having the structure of an FFS mode liquid crystal display element was produced.
- a substrate with electrodes was prepared.
- a glass plate having a rectangular shape of 30 mm ⁇ 50 mm and a thickness of 0.7 mm was used as the substrate.
- An ITO electrode having a solid pattern is formed as the first layer on the substrate to constitute the counter electrode.
- a SiN (silicon nitride) film was used to form.
- the SiN film of the second layer has a film thickness of 500 nm and functions as an interlayer insulating film.
- a comb-shaped pixel electrode formed by patterning an ITO film is arranged as a third layer, and two pixels of a first pixel and a second pixel are formed.
- the size of each pixel was 10 mm long and 5 mm wide.
- the counter electrode of the first layer and the pixel electrode of the third layer were electrically insulated by the action of the SiN film of the second layer.
- the pixel electrode of the third layer has a comb shape in which a plurality of electrode elements each having a width of 3 ⁇ m and having a central portion bent at an internal angle of 160° are arranged in parallel with an interval of 6 ⁇ m.
- the pixel had a first region and a second region bounded by a line connecting bent portions of a plurality of electrode elements.
- the liquid crystal aligning agents (V-1) to (V-3) and (RV-1) to (RV-6) obtained in Examples 1 to 3 and Comparative Examples 1 to 6 were used with a pore size of 1.0 ⁇ m.
- the prepared substrate with electrodes (first glass substrate) and a glass substrate (second glass substrate) having a columnar spacer with a height of 4 ⁇ m and having an ITO film formed on the back surface (second glass substrate) was applied by a spin coating method. After drying on a hot plate at 80° C.
- the coated film surface was subjected to alignment treatment by irradiating linearly polarized ultraviolet light having a wavelength of 254 nm and an extinction ratio of 26:1 through a polarizing plate for each dose shown in Table 3 to obtain a substrate with a liquid crystal alignment film.
- the liquid crystal alignment film formed on the substrate with the electrode is aligned so that the direction of equally dividing the interior angle of the bent portion of the pixel is orthogonal to the alignment direction of the liquid crystal, and the liquid crystal alignment film is formed on the second glass substrate.
- Liquid crystal MLC-3019 (manufactured by Merck & Co.) was injected into this empty cell by a vacuum injection method, and the injection port was sealed to obtain an FFS-driven liquid crystal cell. After that, the obtained liquid crystal cell was heated at 120° C. for 1 hour and left to stand overnight before being used for evaluation.
- a liquid crystal cell is placed between two polarizing plates whose polarization axes are orthogonal to each other, the backlight is turned on, and the liquid crystal cell is arranged so that the transmitted light intensity in the first region of the pixel is minimized. was adjusted, and then the rotation angle required when the liquid crystal cell was rotated so that the intensity of transmitted light in the second region of the pixel was minimized was obtained. It can be said that the smaller the rotation angle, the better the stability of the liquid crystal alignment. As evaluation criteria, the case of less than 0.05° was evaluated as "excellent", the case of 0.05° or more and 0.10° or less as "good”, and the case of more than 0.10° as "bad".
- Table 3 shows the evaluation results of the liquid crystal display elements using the liquid crystal aligning agents of the above Examples and Comparative Examples.
- the liquid crystal alignment films obtained from the liquid crystal alignment agents using the specific diamines WA-1 and WA-2 are obtained from liquid crystal alignment agents composed of diamine components that do not contain the specific diamines. High in-plane uniformity was obtained with a smaller amount of light irradiation than a film. Furthermore, the stability of the liquid crystal alignment was shown to be as high as or higher than that of the conventional liquid crystal alignment film.
- the liquid crystal alignment film obtained from the liquid crystal alignment agent of the present invention can be suitably used for liquid crystal display elements. These elements are also useful in liquid crystal displays intended for display, as well as light control windows and optical shutters for controlling the transmission and blocking of light.
- the variation (non-uniformity) of the twist angle of the liquid crystal in the plane of the liquid crystal alignment film is small, and the range of the light irradiation amount for obtaining the liquid crystal alignment film is expanded, and the quality It is possible to efficiently obtain a liquid crystal alignment film having a good Therefore, it can be expected to be used in liquid crystal display devices that require high display quality.
- These elements are also useful in liquid crystal displays intended for display, as well as light control windows and optical shutters for controlling the transmission and blocking of light.
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Abstract
Description
しかし、本発明者らが検討したところ、少ない光照射量で液晶配向が実現できる液晶配向膜は、液晶配向膜面内での液晶のツイスト角度のバラツキ(不均一性)が小さい液晶配向膜が得られる光照射量の範囲が狭いことが明らかとなった。そのため、液晶表示素子の大画面化を図った際に得られる液晶配向膜の一部において液晶配向が不完全になり、画像表示を長時間行った際、面内の明るさにバラツキが生じ、表示品位を低下させることが懸念される。
Aは、炭素数4~10のアルキレン基を表す。
Ar1、及びAr1’は、それぞれ独立して、ベンゼン環、ビフェニル構造、又はナフタレン環を表す。Ar1、及びAr1’の環上の任意の水素原子は、1価の基で置換されていてもよい。)
なお、本明細書全体を通して、ハロゲン原子としては、フッ素原子、塩素原子、臭素原子、ヨウ素原子等が挙げられ、*は結合手を表す。
本発明の液晶配向剤は、下記式(1)で表される繰り返し単位(a1)を有するポリイミド前駆体及び該ポリイミド前駆体のイミド化物であるポリイミドからなる群から選ばれる少なくとも1種の重合体(A)を含有する。尚、重合体(A)は1種類又は2種類以上で構成されてもよい。
重合体の主鎖とは、重合体のうち最も長い原子の連鎖からなる部分をいう。
そして、「重合体(A)は、上記式(H)で表される2価の有機基を、重合体(A)の主鎖方向に有する」とは、式(H)で表される2価の有機基における最も長い原子の連鎖が、重合体(A)の主鎖を構成することをいう。言い換えれば、「重合体(A)は、上記式(H)で表される2価の有機基を、重合体(A)の主鎖方向に有する」とは、式(H)で表される2価の有機基における最も長い原子の連鎖の両端が、式(1)中のY1と結合する2つの窒素原子にそれぞれ結合していることをいう。
また、Y1が有する全てのベンゼン環のそれぞれのベンゼン環の少なくとも2つの炭素原子が、重合体(A)の主鎖を構成することをいう。
ナフタレン環は、ベンゼン環を2つ有するものとする。
ビフェニル構造は、ベンゼン環を2つ有するものとする。
Y1におけるベンゼン環の数は、3つ以上であれば、特に制限されないが、例えば、3つ以上8つ以下であってもよいし、3つ以上6つ以下であってもよい。本発明の効果を好適に得る観点から、4つ以上6つ以下であってもよい。
Aは、炭素数4~10のアルキレン基を表し、より好ましくは炭素数4、6、8、又は10のアルキレン基であり、さらに好ましくは炭素数4又は6のアルキレン基である。
Ar1、及びAr1’は、それぞれ独立して、ベンゼン環、ビフェニル構造、又はナフタレン環を表す。Ar1、及びAr1’の環上の任意の水素原子は、1価の基で置換されていてもよい。)
nは4~10の整数であり、好ましくは4、6、8、又は10の整数であり、さらに好ましくは4又は6の整数である。
mは、それぞれ独立して0~6の整数であり、nは、それぞれ独立して0~4の整数である。Ra1~Ra4は、複数存在する場合、それぞれ同一でも異なってもよい。)
上記式(1)におけるR、及びZにおける1価の有機基としては、中でも、炭素数1~10のアルキル基、炭素数2~10のアルケニル基、炭素数2~10のアルキニル基、tert-ブトキシカルボニル基、又は9-フルオレニルメトキシカルボニル基が好ましく、炭素数1~3のアルキル基が更に好ましく、メチル基がより一層好ましい。
R及びZは、本発明の効果を好適に得る観点から、それぞれ独立に、水素原子又は炭素数1~3のアルキル基が好ましく、水素原子またはメチル基がより好ましい。
上記Y3の具体例としては、下記式(Dx)で表される2価の有機基が挙げられる。
Q6及びQ7はそれぞれ独立して-H、-NHD、-N(D)2、-NHDを有する基、又は-N(D)2を有する基(Dはカルバメート系保護基を表す。)を表す。但し、m=0の場合、Q6はカルバメート系保護基を有し、m=1の場合、Q5、Q6及びQ7の少なくとも一つは基中にカルバメート系保護基を有する。また、Q6、及びQ7において、水素原子以外の基を表す場合、好ましい炭素数は1~8である。
上記Q9及びQ10の1価の有機基としては、炭素数1~3のアルキル基、炭素数2~3のアルケニル基、炭素数2~3のアルキニル基、フッ素原子を含有する炭素数1~3の1価の有機基が挙げられる。
ここで、テトラカルボン酸二無水物の誘導体としては、例えば、テトラカルボン酸ジハライド、テトラカルボン酸ジアルキルエステル、及びテトラカルボン酸ジアルキルエステルジハライドが挙げられる。
中でも、シクロブタン環構造、シクロペンタン環構造及びシクロヘキサン環構造よりなる群から選ばれる少なくとも一種の部分構造を有するテトラカルボン酸二無水物又はその誘導体に由来する4価の有機基がより好ましい。X1、X2、X2’、及びX3の好ましい具体例を挙げると、下記式(g)で表される4価の有機基の他、下記式(X-1)~(X-25)のいずれかで表される4価の有機基、芳香族テトラカルボン酸二無水物に由来する4価の有機基等が挙げられる。本発明の効果を好適に得る観点から、X1、X2、X2’及びX3は、下記式(g)、(X-1)~(X-5)、(X-11)、(X-21)~(X-23)で表される4価の有機基であることがより好ましく、下記式(g)で表される4価の有機基であることがさらに好ましい。
及びR4がメチル基であり、R2及びR3が水素原子である場合である。
4,4’-ジアミノジフェニルメタン、3,4’-ジアミノジフェニルメタン、3,3’-ジメチル-4,4’-ジアミノジフェニルメタン;下記式(g-1)~(g-10)で表されるジアミンなどの光配向性基を有するジアミン;下記式(u-1)~(u-3)で表されるジアミンなどのウレア結合を有するジアミン(但し、該ジアミンは分子内にカルバメート系保護基を有しない。);下記式(u-4)~(u-8)で表されるジアミンなどのアミド結合を有するジアミン(但し、該ジアミンは分子内にカルバメート系保護基を有しない。);窒素原子含有複素環、及び、基「*21-NR-*22」(*21、及び*22は、芳香族環を構成する炭素原子と結合する結合手を表す。但し、該炭素原子はRが結合する窒素原子と環を形成しない。Rは水素原子又は1価の有機基を表し、上記1価の有機基はカルボニル炭素以外の炭素原子で窒素原子と結合する。)で表されるアミノ基よりなる群から選ばれる少なくとも一種の窒素原子含有構造(以下、窒素原子含有構造ともいう。)を有するジアミン;3,5-ジアミノベンジルアルコール、2,4-ジアミノベンジルアルコール;2,4-ジアミノ安息香酸、2,5-ジアミノ安息香酸、3,5-ジアミノ安息香酸、4,4’-ジアミノビフェニル-3-カルボン酸、4,4’-ジアミノジフェニルメタン-3-カルボン酸、4,4’-ジアミノジフェニルエタン-3-カルボン酸、4,4’-ジアミノビフェニル-3,3’-ジカルボン酸、4,4’-ジアミノビフェニル-2,2’-ジカルボン酸、3,3’-ジアミノビフェニル-4,4’-ジカルボン酸、3,3’-ジアミノビフェニル-2,4’-ジカルボン酸、4,4’-ジアミノジフェニルメタン-3,3’-ジカルボン酸、4,4’-ジアミノジフェニルエタン-3,3’-ジカルボン酸及び4,4’-ジアミノジフェニルエーテル-3,3’-ジカルボン酸などのカルボキシ基を有するジアミン;4-(2-(メチルアミノ)エチル)アニリン、4-(2-アミノエチル)アニリン、4,4’-ジアミノベンゾフェノン、1-(4-アミノフェニル)-1,3,3-トリメチル-1H-インダン-5-アミン、1-(4-アミノフェニル)-2,3-ジヒドロ-1,3,3-トリメチル-1H-インデン-6-アミン;メタクリル酸2-(2,4-ジアミノフェノキシ)エチル及び2,4-ジアミノ-N,N-ジアリルアニリン等の光重合性基を末端に有するジアミン;コレスタニルオキシ-3,5-ジアミノベンゼン、コレステニルオキシ-3,5-ジアミノベンゼン、コレスタニルオキシ-2,4-ジアミノベンゼン、3,5-ジアミノ安息香酸コレスタニル、3,5-ジアミノ安息香酸コレステニル、3,5-ジアミノ安息香酸ラノスタニル及び3,6-ビス(4-アミノベンゾイルオキシ)コレスタン等のステロイド骨格を有するジアミン;下記式(V-1)~(V-6)で表されるジアミン;1,3-ビス(3-アミノプロピル)-テトラメチルジシロキサン等のシロキサン結合を有するジアミン;下記式(Ox-1)~(Ox-2)等のオキサゾリン環構造を有するジアミン;1-(4-(2,4-ジアミノフェノキシ)エトキシ)フェニル)-2-ヒドロキシ-2-メチルプロパノン、2-(4-(2-ヒドロキシ-2-メチルプロパノイル)フェノキシ)エチル-3,5-ジアミノベンゾエート、4,4’-ジアミノベンゾフェノン、3,3’-ジアミノベンゾフェノン等のラジカル重合開始剤機能を有するジアミン等のジアミンから2つのアミノ基を除いた2価の有機基、WO2018/117239号公報に記載の式(Y-1)~(Y-167)のいずれかで表される基が挙げられる。
重合体(A)が繰り返し単位(a1)及び繰り返し単位(a1)のイミド化構造以外の繰り返し単位を含む場合は、重合体(A)は、繰り返し単位(a1)と繰り返し単位(a1)のイミド化構造との合計を全繰り返し単位の95モル%以下含むことが好ましく、90モル%以下含むことがより好ましく、80モル%以下含むことがさらに好ましい。
重合体(A)は、本発明の効果を好適に得る観点から、繰り返し単位(a1)及びそのイミド化構造の少なくともいずれかと、繰り返し単位(a2)及びそのイミド化構造の少なくともいずれかと、繰り返し単位(a2’)及びそのイミド化構造の少なくともいずれかとを含み、繰り返し単位(a1)、繰り返し単位(a2)及び繰り返し単位(a2’)並びにそれらのイミド化構造の合計が全繰り返し単位の30モル%以上であることが好ましく、40モル%以上であることがより好ましい。重合体(A)が、繰り返し単位(a1)、繰り返し単位(a2)及び繰り返し単位(a2’)並びにそれらのイミド化構造以外の繰り返し単位を含む場合は、繰り返し単位(a1)、繰り返し単位(a2)及び繰り返し単位(a2’)並びにそれらのイミド化構造の合計の上限が95モル%であることが好ましく、90モル%であることが更に好ましい。
本発明の液晶配向剤は、上記重合体(A)以外に、上記繰り返し単位(a1)及びそのイミド化構造を分子内に有しない重合体(B)を含有してもよい。尚、重合体(B)は1種類又は2種類以上で構成されてもよい。本発明の効果を好適に得る観点から、重合体(B)としては、下記式(5)で表される繰り返し単位又はそのイミド化構造を有する重合体が挙げられる。また、重合体(B)を構成する繰り返し単位又はそのイミド化構造は1種類であってもよく、2種類以上で構成されてもよい。
本発明に用いられるポリイミド前駆体であるポリアミック酸エステル、及びポリアミック酸並びにこれらのイミド化物であるポリイミドは、例えば、WO2013/157586号公報に記載されるような公知の方法で合成出来る。
上記溶媒の具体例としては、N-メチル-2-ピロリドン、N-エチル-2-ピロリドン、γ-ブチロラクトン、N,N-ジメチルホルムアミド、N,N-ジメチルアセトアミド、ジメチルスルホキシド、1,3-ジメチル-2-イミダゾリジノンが挙げられる。また、重合体の溶媒溶解性が高い場合は、メチルエチルケトン、シクロヘキサノン、シクロペンタノン、4-ヒドロキシ-4-メチル-2-ペンタノン、又は下記の式[D-1]~式[D-3]で示される溶媒を用いることができる。
ジアミン成分とテトラカルボン酸誘導体成分とを溶媒中で反応させる際には、反応は任意の濃度で行うことができるが、好ましくは1~50質量%、より好ましくは5~30質量%である。反応初期は高濃度で行い、その後、溶媒を追加することもできる。
反応においては、ジアミン成分の合計モル数とテトラカルボン酸誘導体成分の合計モル数の比は0.8~1.2であることが好ましい。通常の縮重合反応同様、このモル比が1.0に近いほど生成する重合体(A)、重合体(B)の分子量は大きくなる。
本発明に用いられるポリアミック酸、ポリアミック酸エステル及びポリイミドは、これを濃度10~15質量%の溶液としたときに、例えば10~1000mPa・sの溶液粘度を持つものが作業性の観点から好ましいが、特に限定されない。なお、上記重合体の溶液粘度(mPa・s)は、当該重合体の良溶媒(例えばγ-ブチロラクトン、N-メチル-2-ピロリドンなど)を用いて調製した濃度10~15質量%の重合体溶液につき、E型回転粘度計を用いて25℃において測定した値である。
上記ポリアミック酸、ポリアミック酸エステル及びポリイミドのゲルパーミエーションクロマトグラフィー(GPC)により測定したポリスチレン換算の重量平均分子量(Mw)は、好ましくは1,000~500,000であり、より好ましくは2,000~300,000である。また、Mwと、GPCにより測定したポリスチレン換算の数平均分子量(Mn)との比で表される分子量分布(Mw/Mn)は、好ましくは15以下であり、より好ましくは10以下である。このような分子量範囲にあることで、液晶表示素子の良好な配向性及び安定性を確保することができる。
本発明における重合体(A)、重合体(B)を合成するに際して、上記の如きテトラカルボン酸誘導体成分、及びジアミン成分とともに、適当な末端封止剤を用いて末端封止型の重合体を合成することとしてもよい。末端封止型の重合体は、塗膜によって得られる液晶配向膜の膜硬度の向上や、シール剤と液晶配向膜の密着特性の向上という効果を有する。
本発明における重合体(A)、重合体(B)の末端の例としては、アミノ基、カルボキシ基、酸無水物基又は後述する末端封止剤に由来する基が挙げられる。アミノ基、カルボキシ基、酸無水物基は通常の縮合反応により得るか、又は以下の末端封止剤を用いて末端を封止することにより得ることができる。
本発明の液晶配向剤は、重合体(A)及び必要に応じて重合体(B)を含有する。本発明の液晶配向剤は、重合体(A)、重合体(B)に加えて、その他の重合体を含有していてもよい。その他の重合体の具体例を挙げると、ポリシロキサン、ポリエステル、ポリアミド、ポリウレア、ポリウレタン、ポリオルガノシロキサン、セルロース誘導体、ポリアセタール、ポリスチレン誘導体、ポリ(スチレン-マレイン酸無水物)共重合体、ポリ(イソブチレン-マレイン酸無水物)共重合体、ポリ(ビニルエーテル-マレイン酸無水物)共重合体、ポリ(スチレン-フェニルマレイミド)誘導体、ポリ(メタ)アクリレートからなる群から選ばれる重合体などが挙げられる。ポリ(スチレン-マレイン酸無水物)共重合体の具体例としては、SMA1000、2000、3000(Cray Valley社製)、GSM301(岐阜セラツク製造所社製)などが挙げられ、ポリ(イソブチレン-マレイン酸無水物)共重合体の具体例としては、イソバン-600(クラレ社製)が挙げられ、ポリ(ビニルエーテル-マレイン酸無水物)共重合体の具体例としては、Gantrez AN-139(メチルビニルエーテル無水マレイン酸樹脂、アシュランド社製)が挙げられる。その他の重合体は、一種を単独で使用してもよく、また二種以上を組み合わせて使用してもよい。
その他の重合体の含有割合は、液晶配向剤中に含まれる重合体の合計100質量部に対して、90質量部以下が好ましく、10~90質量部がより好ましく、20~80質量部が更に好ましい。
例えば、ジイソプロピルエーテル、ジイソブチルエーテル、ジイソブチルカルビノール(2,6-ジメチル-4-ヘプタノール)、エチレングリコールジメチルエーテル、エチレングリコールジエチルエーテル、エチレングリコールジブチルエーテル、1,2-ジブトキシエタン、ジエチレングリコールジメチルエーテル、ジエチレングリコールジエチルエーテル、4-ヒドロキシ-4-メチル-2-ペンタノン、ジエチレングリコールメチルエチルエーテル、ジエチレングリコールジブチルエーテル、3-エトキシブチルアセタート、1-メチルペンチルアセタート、2-エチルブチルアセタート、2-エチルヘキシルアセタート、エチレングリコールモノアセタート、エチレングリコールジアセタート、プロピレンカーボネート、エチレンカーボネート、エチレングリコールモノブチルエーテル、エチレングリコールモノイソアミルエーテル、エチレングリコールモノヘキシルエーテル、プロピレングリコールモノメチルエーテル、プロピレングリコールモノブチルエーテル、1-(2-ブトキシエトキシ)-2-プロパノール、2-(2-ブトキシエトキシ)-1-プロパノール、プロピレングリコールモノメチルエーテルアセタート、プロピレングリコールジアセテート、ジプロピレングリコールモノメチルエーテル、ジプロピレングリコールモノエチルエーテル、ジプロピレングリコールジメチルエーテル、エチレングリコールモノブチルエーテルアセタート、ジエチレングリコールモノプロピルエーテル、ジエチレングリコールモノエチルエーテルアセタート、ジエチレングリコールモノブチルエーテルアセタート、2-(2-エトキシエトキシ)エチルアセタート、ジエチレングリコールアセタート、プロピレングリコールジアセテート、酢酸n-ブチル、酢酸プロピレングリコールモノエチルエーテル、酢酸シクロヘキシル、酢酸4-メチル-2-ペンチル、3-メトキシプロピオン酸メチル、3-エトキシプロピオン酸エチル、3-メトキシプロピオン酸エチル、3-メトキシプロピオン酸プロピル、3-メトキシプロピオン酸ブチル、乳酸n-ブチル、乳酸イソアミル、ジエチレングリコールモノエチルエーテル、ジイソブチルケトン(2,6-ジメチル-4-ヘプタノン)などを挙げることができる。
オキサゾリン環構造を含む基を有する化合物の具体例としては、日本特開2007-286597号公報の段落[0115]に記載の、2個以上のオキサゾリン環構造を含む化合物が挙げられる。
メルドラム酸構造を含む基を有する化合物の具体例としては、WO2012/091088号公報に記載の、メルドラム酸構造を2個以上有する化合物が挙げられる。
シクロカーボネート基を有する化合物の具体例としては、WO2011/155577号公報に記載の化合物が挙げられる。
本発明の液晶配向膜は、上記液晶配向剤から得られる。本発明の液晶配向膜は、水平配向型若しくは垂直配向型(VA型)の液晶配向膜に用いることができるが、中でもIPS方式又はFFS方式等の水平配向型の液晶表示素子に好適な液晶配向膜である。また、本発明の液晶配向膜は、光配向処理法用の液晶配向膜により好ましく用いられる。その他、本発明の液晶配向膜は、種々の技術用途に有効に適用することができ、例えば上記用途以外の液晶配向膜(位相差フィルム用の液晶配向膜、走査アンテナや液晶アレイアンテナ用の液晶配向膜又は透過散乱型の液晶調光素子用の液晶配向膜)、或いは、その他の用途、例えば、保護膜(例:カラーフィルタ用の保護膜)、スペーサー膜、層間絶縁膜、反射防止膜、配線被覆膜、帯電防止フィルム、電動機絶縁膜(フレキシブルディスプレイのゲート絶縁膜)等にも適用できる。本発明の液晶表示素子は、上記液晶配向膜を具備するものである。本発明の液晶表示素子は、例えば、以下の工程(1)~(3)を含む方法により製造することができる。本発明の液晶表示素子は、例えば、以下の工程(1)~(3)及び(5)或いは工程(1)~(2)及び(5)を含む方法により製造することができる。より好ましくは、工程(1)~(5)を含む方法により製造される。
工程(1)は、本発明の液晶配向剤を基板上に塗布する工程である。工程(1)の具体例は以下のとおりである。
パターニングされた透明導電膜が設けられている基板の一面に、本発明の液晶配向剤を、例えばロールコーター法、スピンコート法、印刷法、インクジェット法などの適宜の塗布方法により塗布する。ここで基板としては、透明性の高い基板であれば特に限定されず、ガラス基板、窒化珪素基板とともに、アクリル基板やポリカーボネート基板等のプラスチック基板等を用いることもできる。また、反射型の液晶表示素子では、片側の基板のみにならば、シリコンウエハー等の不透明な物でも使用でき、この場合の電極にはアルミニウム等の光を反射する材料も使用できる。また、IPS型又はFFS型の液晶表示素子を製造する場合には、櫛歯型にパターニングされた透明導電膜又は金属膜からなる電極が設けられている基板と、電極が設けられていない対向基板とを用いる。
工程(2)は、基板上に塗布した液晶配向剤を焼成し、膜を形成する工程である。工程(2)の具体例は以下のとおりである。
工程(1)において液晶配向剤を基板上に塗布した後は、ホットプレート、熱循環型オーブン又はIR(赤外線)型オーブンなどの加熱手段により、溶媒を蒸発させたり、ポリアミック酸又はポリアミック酸エステルの熱イミド化を行ったりすることができる。本発明の液晶配向剤を塗布した後の乾燥、焼成工程は、任意の温度と時間を選択することができ、複数回行ってもよい。焼成温度としては、例えば40~180℃で行うことができる。プロセスを短縮する観点で、40~150℃で行ってもよい。その際の焼成時間としては特に限定されないが、1~10分又は、1~5分が挙げられる。ポリアミック酸又はポリアミック酸エステルの熱イミド化を行う場合には、上記有機溶媒を除去する工程の後、例えば150~300℃、又は150~250℃の温度範囲で焼成する工程を追加してもよい。その際の焼成時間としては特に限定されないが、5~40分、又は、5~30分の焼成時間が挙げられる。
焼成後の膜状物は、薄すぎると液晶表示素子の信頼性が低下する場合があるので、5~300nmが好ましく、10~200nmがより好ましい。
工程(3)は、場合により、工程(2)で得られた焼成膜(塗膜)に配向処理する工程である。即ち、IPS方式又はFFS方式等の水平配向型の液晶表示素子では該塗膜に対し配向能付与処理を行う。一方、VA方式又はPSAモード等の垂直配向型の液晶表示素子では、形成した塗膜をそのまま液晶配向膜として使用することができるが、該塗膜に対し配向能付与処理を施してもよい。液晶配向膜の配向処理方法としては、ラビング処理法、光配向処理法が挙げられ、光配向処理法がより好適である。光配向処理法としては、上記膜状物の表面に、一定方向に偏向された放射線を照射し、場合により、好ましくは、150~250℃の温度で加熱処理を行い、液晶配向性(液晶配向能ともいう)を付与する方法が挙げられる。放射線としては、100~800nmの波長を有する紫外線又は可視光線を用いることができる。なかでも、好ましくは100~400nm、より好ましくは、200~400nmの波長を有する紫外線である。
更に、上記の方法で、偏光された放射線を照射した液晶配向膜に、水や溶媒を用いて、接触処理するか、放射線を照射した液晶配向膜を加熱処理することもできる。
工程(4)は、工程(3)で配向処理された液晶配向膜に対して加熱処理を行う工程である。
上記の放射線を照射した照射膜(塗膜)に対して加熱処理を行ってもよい。
上記の放射線を照射した塗膜に対する加熱処理の温度は、50~300℃が好ましく、120~250℃がより好ましい。加熱処理の時間は、1~30分が好ましい。
上記のようにして液晶配向膜が形成された基板を2枚準備し、対向配置した2枚の基板間に液晶を配置する。具体的には以下の2つの方法が挙げられる。
第一の方法は、先ず、それぞれの液晶配向膜が対向するように間隙(セルギャップ)を介して2枚の基板を対向配置する。次いで、2枚の基板を周辺部にシール剤を用いて貼り合わせ、基板表面及びシール剤により区画されたセルギャップ内に液晶組成物を注入充填して膜面に接触した後、注入孔を封止する。
なお、塗膜に対してラビング処理を行った場合には、2枚の基板は、各塗膜におけるラビング方向が互いに所定の角度、例えば直交又は逆平行となるように対向配置される。
シール剤としては、例えば硬化剤及びスペーサーとしての酸化アルミニウム球を含有するエポキシ樹脂等を用いることができる。上記液晶組成物としては、特に制限はなく、少なくとも一種の液晶化合物(液晶分子)を含む組成物であって、誘電率異方性が正または負の各種の液晶組成物を用いることができる。なお、以下では、誘電率異方性が正の液晶組成物を、ポジ型液晶ともいい、誘電率異方性が負の液晶組成物を、ネガ型液晶ともいう。液晶組成物としては、ネマチック相を呈する液晶組成物及びスメクチック相を呈する液晶組成物を挙げることができ、その中でもネマチック相を呈する液晶組成物が好ましい。
上記液晶組成物は、フルオロ基、ヒドロキシ基、アミノ基、フッ素原子含有基(例えば、トリフルオロメチル基)、シアノ基、アルキル基、アルコキシ基、アルケニル基、イソチオシアネート基、複素環、シクロアルカン、シクロアルケン、ステロイド骨格、ベンゼン環、又はナフタレン環を有する液晶化合物を含んでもよく、分子内に液晶性を発現する剛直な部位(メソゲン骨格)を2つ以上有する化合物(例えば、剛直な二つのビフェニル構造、又はターフェニル構造がアルキル基で連結されたバイメソゲン化合物)を含んでもよい。
上記液晶組成物は、液晶配向性を向上させる観点から、添加物をさらに含有してもよい。このような添加物は、重合性基を有する化合物などの光重合性モノマー;光学活性な化合物(例:メルク(株)社製のS-811など);酸化防止剤;紫外線吸収剤;色素;消泡剤;重合開始剤;又は重合禁止剤などが挙げられる。
ポジ型液晶としては、メルク社製のZLI-2293、ZLI-4792、MLC-2003、MLC-2041、MLC-3019、又はMLC-7081などが挙げられる。
ネガ型液晶としては、例えばメルク社製のMLC-6608、MLC-6609、MLC-6610、又はMLC-7026-100などが挙げられる。
また、重合性基を有する化合物を含有する液晶として、メルク社製のMLC-3023が挙げられる。
なお、FFS(Frindge Field Switching)モードにおいて使用される櫛歯電極基板であるFFS基板は、基材と、基材上に形成された面電極と、面電極上に形成された絶縁膜と、絶縁膜上に形成され、櫛歯状に配置された複数の線状電極と、絶縁膜上に線状電極を覆うように形成された液晶配向膜とを有する。
図1に例示する横電界液晶表示素子1においては、液晶配向膜2cを具備する櫛歯電極基板2と液晶配向膜4aを具備する対向基板4との間に、液晶3が挟持されている。櫛歯電極基板2は、基材2aと、基材2a上に形成され、櫛歯状に配置された複数の線状電極2bと、基材2a上に線状電極2bを覆うように形成された液晶配向膜2cとを有している。対向基板4は、基材4bと、基材4b上に形成された液晶配向膜4aとを有している。液晶配向膜2cは、例えば、本発明の液晶配向膜である。液晶配向膜4cも同様に本発明の液晶配向膜である。
この横電界液晶表示素子1においては、線状電極2bに電圧が印加されると、電気力線Lで示すように線状電極2b間で電界が発生する。
図2に例示する横電界液晶表示素子1においては、液晶配向膜2hを具備する櫛歯電極基板2と液晶配向膜4aを具備する対向基板4との間に、液晶3が挟持されている。櫛歯電極基板2は、基材2dと、基材2d上に形成された面電極2eと、面電極2e上に形成された絶縁膜2fと、絶縁膜2f上に形成され、櫛歯状に配置された複数の線状電極2gと、絶縁膜2f上に線状電極2gを覆うように形成された液晶配向膜2hとを有している。対向基板4は、基材4bと、基材4b上に形成された液晶配向膜4aとを有している。液晶配向膜2hは、例えば、本発明の液晶配向膜である。液晶配向膜4aも同様に本発明の液晶配向膜である。
この横電界液晶表示素子1においては、面電極2eおよび線状電極2gに電圧が印加されると、電気力線Lで示すように面電極2eおよび線状電極2g間で電界が発生する。
NMP:N-メチル-2-ピロリドン
BCS:エチレングリコールモノブチルエーテル
DMF:ジメチルホルムアミド
DMAc:ジメチルアセトアミド
THF:テトラヒドロフラン
溶液の粘度は、E型粘度計TVE-22H(東機産業社製)を用い、サンプル量1.1mL、コーンロータTE-1(1°34’、R24)を用いて、温度25℃で測定した。
ポリアミック酸の分子量は、常温ゲル浸透クロマトグラフィー(GPC)装置(GPC-101)(昭和電工社製)、カラム(KD-803,KD-805の直列)(昭和電工社製)を用いて、以下のようにして測定した。
カラム温度:50℃
溶離液:N,N-ジメチルホルムアミド(添加剤として、臭化リチウム一水和物(LiBr・H2O)が30mmol/L(リットル)、リン酸・無水結晶(o-リン酸)が30mmol/L、テトラヒドロフラン(THF)が10mL/L)
流速:1.0ml/分
検量線作成用標準サンプル:TSK 標準ポリエチレンオキサイド(分子量;約900,000、150,000、100,000及び30,000)(東ソー社製)及びポリエチレングリコール(分子量;約12,000、4,000及び1,000)(ポリマーラボラトリー社製)。
特定ジアミン(WA-1)~(WA-2)の合成法を以下に詳述する。なお、ジアミン(WA-2)は、文献等未公開の新規化合物である。
装置:フーリエ変換型超伝導核磁気共鳴装置(FT-NMR)「AVANCE III」(BRUKER製)500MHz。
溶媒:重水素化ジメチルスルホキシド(DMSO-d6、標準物質:テトラメチルシラン)、
下記に示す経路に従って、ジアミン(WA-1)を合成した。
1H-NMR(500MHz,DMSO-d6);δ(ppm)=8.10(2H,s)、7.83-7.75(4H,m)、7.56-7.54(2H,m)、7.38(2H,s)、7.23-7.22(2H,m)、4.19(4H,t)、1.99-1.95(4H,m)
以下に示す1H-NMRの結果から、この固体がジアミン(WA-1)であることを確認した。
1H-NMR(500MHz,DMSO-d6);δ(ppm)=7.49-7.47(2H,m)、7.44―7.42(2H、m)、7.10(2H,d)、6.99-6.97(2H,m)、6.90-6.88(2H,m)、6.79(2H,d)、5.08-5.06(4H,m)、4.08(4H,t)、1,96-1.92(4H,m)
1H-NMR(500MHz,DMSO-d6);δ(ppm)=7.61-7.58(6H、m)、7.02(2H,d)、4.05(2H,t)、3.72(2H,t)、1.88-1.87(4H,m)
1H-NMR(500MHz,DMSO-d6);δ(ppm)=8.11(1H,m)、7.83-7.75(2H,m)、7.61-7.55(7H,m)、7.37(1H,m)、7.23(1H、m)、7.04-7.03(2H,m)、4.17-4.11(4H,m)、1.04-1.03(4H,m)
以下に示す1H-NMRの結果から、この固体がジアミン(WA-2)であることを確認した。
1H-NMR(500MHz,DMSO-d6);δ(ppm)=7.49-7.42(4H,m)、7.28-7.27(2H,m)、7.09(1H,d)、6.99-6.88(4H,m)、6.79(1H,d)、6.622-6.60(2H,m)、5.11-5.10(4H,m)、4.07-4.05(4H、m)、1.98-1.90(4H,m)
(合成例1)
撹拌装置付き及び窒素導入管付きの100mL四つ口フラスコに、A1(0.973g、9.00mmol)、A2(2.20g、9.00mmol)、WA-1(2.23g、6.00mmol)、A7(2.39g、6.00mmol)、B1(6.39g、28.5mmol)及びNMP(104g)を加えて、40℃で20時間撹拌することで、固形分濃度12質量%のポリアミック酸(A-1)の溶液(粘度:379mPa・s)を得た。このポリアミック酸の数平均分子量(Mn)は13,242、重量平均分子量(Mw)は34,231であった。
撹拌装置付き及び窒素導入管付きの100mL四つ口フラスコに、A1(0.973g、9.00mmol)、A2(2.20g、9.00mmol)、WA-2(2.39g、6.00mmol)、A7(2.39g、6.00mmol)、B1(6.42g、28.7mmol)及びNMP(105g)を加えて、40℃で20時間撹拌することで、固形分濃度12質量%のポリアミック酸(A-2)の溶液(粘度:398mPa・s)を得た。このポリアミック酸のMnは12,019、Mwは33,291であった。
撹拌装置付き及び窒素導入管付きの100mL四つ口フラスコに、A1(0.649g、6.00mmol)、A8(4.78g、24.0mmol)、B2(5.59g、28.5mmol)及びNMP(99.2g)を加えて、室温で5時間撹拌することで、固形分濃度10質量%のポリアミック酸(B-1)の溶液(粘度:338mPa・s)を得た。このポリアミック酸のMnは15,932、Mwは39,013であった。
撹拌装置付き及び窒素導入管付きの100mL四つ口フラスコに、A1(0.973g、9.00mmol)、A2(2.20g、9.00mmol)、A3(1.92g、6.00mmol)、A7(2.39g、6.00mmol)、B1(6.42g、28.7mmol)及びNMP(101g)を加えて、40℃で20時間撹拌することで、固形分濃度12質量%のポリアミック酸(RA-1)の溶液(粘度:382mPa・s)を得た。このポリアミック酸のMnは11,912、Mwは33,413であった。
撹拌装置付き及び窒素導入管付きの100mL四つ口フラスコに、A1(0.973g、9.00mmol)、A2(2.20g、9.00mmol)、A4(2.07g、6.00mmol)、A7(2.39g、6.00mmol)、B1(6.38g、28.4mmol)及びNMP(102g)を加えて、40℃で20時間撹拌することで、固形分濃度12質量%のポリアミック酸(RA-2)の溶液(粘度:411mPa・s)を得た。このポリアミック酸のMnは12,018、Mwは37,021であった。
撹拌装置付き及び窒素導入管付きの100mL四つ口フラスコに、A1(0.973g、9.00mmol)、A2(2.20g、9.00mmol)、A5(2.22g、6.00mmol)、A7(2.39g、6.00mmol)、B1(6.38g、28.4mmol)及びNMP(103g)を加えて、40℃で20時間撹拌することで、固形分濃度12質量%のポリアミック酸(RA-3)の溶液(粘度:404mPa・s)を得た。このポリアミック酸のMnは10,383、Mwは36,113であった。
撹拌装置付き及び窒素導入管付きの100mL四つ口フラスコに、A1(0.973g、9.00mmol)、A2(2.20g、9.00mmol)、A6(2.15g、6.00mmol)、A7(2.39g、6.00mmol)、B1(6.46g、28.8mmol)及びNMP(103g)を加えて、40℃で20時間撹拌することで、固形分濃度12質量%のポリアミック酸(RA-4)の溶液(粘度:401mPa・s)を得た。このポリアミック酸のMnは10,099、Mwは36,030であった。
(実施例1)
合成例1で得られたポリアミック酸(A-1)溶液(6.67g)に、NMP(9.33g)及びBCS(4.00g)を加え、室温で2時間撹拌して、液晶配向剤(V-1)を得た。
合成例1で得られたポリアミック酸(A-1)溶液(5.30g)に、合成例3で得られたポリアミック酸(B-1)溶液(9.54g)、NMP(3.78g)、BCS(9.00g)、AD-1のNMP10質量%希釈溶液(0.800g)及びAD-2のNMP1質量%希釈溶液(1.59g)を加え、室温で2時間撹拌して、液晶配向剤(V-2)を得た。
使用するポリアミック酸の溶液を(A-1)溶液から(A-2)溶液に変更した点以外は、実施例2と同様に操作することで、液晶配向剤(V-3)を得た。
使用するポリアミック酸の溶液を(A-1)溶液から(RA-1)~(RA-4)溶液に変更した以外は、実施例1と同様に操作することで、液晶配向剤(RV-1)~(RV-4)を得た。
使用するポリアミック酸の溶液を(A-1)溶液から(RA-2)~(RA-3)溶液に変更した点以外は、実施例2と同様に操作することで、液晶配向剤(RV-5)~(RV-6)を得た。
FFSモード液晶表示素子の構成を備えた液晶セルを作製した。
始めに、電極付きの基板を準備した。基板は、30mm×50mmの長方形で、厚みが0.7mmのガラス板を用いた。基板上には第1層目として対向電極を構成する、ベタ状のパターンを備えたITO電極が形成されて、第1層目の対向電極の上には第2層目として、CVD(化学蒸着)法により成膜されたSiN(窒化珪素)膜が形成されていた。第2層目のSiN膜の膜厚は500nmであり、層間絶縁膜として機能する。第2層目のSiN膜の上には、第3層目としてITO膜をパターニングして形成された櫛歯状の画素電極が配置され、第1画素及び第2画素の2つの画素が形成されており、各画素のサイズは、縦10mm、横5mmであった。このとき、第1層目の対向電極と第3層目の画素電極とは、第2層目のSiN膜の作用により電気的に絶縁されていた。
第3層目の画素電極は、中央部分が内角160°で屈曲した幅3μmの電極要素が6μmの間隔を開けて平行になるように複数配列された櫛歯形状を有しており、1つの画素は、複数の電極要素の屈曲部を結ぶ線を境に第1領域と第2領域を有していた。
次に、上記実施例1~3及び比較例1~6で得られた液晶配向剤(V-1)~(V-3)、(RV-1)~(RV-6)を孔径1.0μmのフィルターで濾過した後、準備された上記電極付き基板(第1のガラス基板)と裏面にITO膜が成膜されている高さ4μmの柱状スペーサーを有するガラス基板(第2のガラス基板)に、スピンコート法にて塗布した。80℃のホットプレート上で2分間乾燥させた後、230℃の熱風循環式オーブンで30分間焼成を行い、膜厚100nmの塗膜を形成させた。この塗膜面に偏光板を介して消光比26:1の直線偏光した波長254nmの紫外線を表3に示すそれぞれの照射量分を照射して配向処理を施し、液晶配向膜付き基板を得た。なお、上記電極付き基板に形成する液晶配向膜は、画素屈曲部の内角を等分する方向と液晶の配向方向とが直交するように配向処理し、第2のガラス基板に形成する液晶配向膜は、液晶セルを作製した時に第1のガラス基板上の液晶の配向方向と第2のガラス基板上の液晶の配向方向とが一致するように配向処理した。上記2枚の基板を一組とし、基板上にシール剤(三井化学社製 XN-1500T)を印刷し、もう1枚の基板を、液晶配向膜面が向き合う配向方向が0°になるようにして張り合わせた。その後、150℃で60分間の加熱処理を行い、シール剤を硬化させて空セルを作製した。この空セルに減圧注入法によって、液晶MLC-3019(メルク社製)を注入し、注入口を封止して、FFS駆動液晶セルを得た。その後、得られた液晶セルを120℃で1時間加熱し、一晩放置してから評価に使用した。
AXOMETRICS社製AxoStepを用いて液晶セルのツイスト角のばらつきの評価を行った。上記で作製した液晶セルを測定ステージに設置し、電圧無印加の状態で、画素面内のCircular Retardanceの分布を測定して標準偏差σの3倍である3σを算出した。面内均一性は、この3σの値が小さいほど良好であると言える。評価基準として、1.00未満の場合を「優良」、1.00以上で1.10以下の場合を「良」、1.10より大きい場合を「不良」とした。
上記実施例及び比較例の各液晶配向剤を使用する液晶表示素子に関して実施した評価結果を表3に示す。
本評価は、長期交流駆動において液晶配向膜の配向性能が低下することによって生ずる残像(AC残像ともいう。)を評価するものである。
上記で作製したFFS駆動液晶セルに対し、60℃の恒温環境下、周波数60Hzで±4Vの交流電圧を120時間印加した。その後、液晶セルの画素電極と対向電極との間をショートさせた状態にし、そのまま室温に一日放置した。上記の処理を行った液晶セルに関して、電圧無印加状態における、画素の第1領域の液晶の配向方向と第2領域の液晶の配向方向とのずれを角度として算出した。具体的には、偏光軸が直交するように配置された2枚の偏光板の間に液晶セルを設置し、バックライトを点灯させ、画素の第1領域の透過光強度が最も小さくなるように液晶セルの配置角度を調整し、次に画素の第2領域の透過光強度が最も小さくなるように液晶セルを回転させたときに要する回転角度を求めた。液晶配向の安定性は、この回転角度の値が小さいほど良好であると言える。評価基準として、0.05°未満の場合を「優良」、0.05°以上で0.10°以下の場合を「良」、0.10°より大きい場合を「不良」とした。
2 櫛歯電極基板
2a 基材
2b 線状電極
2c 液晶配向膜
2d 基材
2e 面電極
2f 絶縁膜
2g 線状電極
2h 液晶配向膜
3 液晶
4 対向基板
4a 液晶配向膜
4b 基材
L 電気力線
Claims (17)
- 下記式(1)で表される繰り返し単位(a1)を有するポリイミド前駆体及び該ポリイミド前駆体のイミド化物であるポリイミドからなる群から選ばれる少なくとも1種の重合体(A)を含有することを特徴とする液晶配向剤。
Aは、炭素数4~10のアルキレン基を表す。
Ar1、及びAr1’は、それぞれ独立して、ベンゼン環、ビフェニル構造、又はナフタレン環を表す。Ar1、及びAr1’の環上の任意の水素原子は、1価の基で置換されていてもよい。*は結合手を表す。) - 前記式(H)における基「*-L1-A-L1’-*」(*は結合手を表す。)が、基「*-(CH2)n-*」、基「*-O-(CH2)n-O-*」、基「*-C(=O)-(CH2)n-C(=O)-*」、基「*-C(=O)-NR-(CH2)n-O-*」、基「*-O-C(=O)-(CH2)n-O-*」、基「*-O-C(=O)-(CH2)n-O-C(=O)-*」、基「*-O-C(=O)-(CH2)n-C(=O)-O-*」、基「*-S-(CH2)n-S-*」、基「*-C(=O)-NR-(CH2)n-NR-C(=O)-*」、基「*-C(=O)-O-(CH2)n-O-C(=O)-*」、基「*-O-(CH2)n-*」、基「*-S-(CH2)n-*」、又は基「*-NR-C(=O)-(CH2)n-C(=O)-NR-*」(Rは水素原子または1価の有機基を表し、nは4~10の整数である。*は結合手を表す。)で表される基である、請求項1に記載の液晶配向剤。
- 前記重合体(A)が、さらに下記式(2)で表される繰り返し単位(a2)を有するポリイミド前駆体及び該ポリイミド前駆体のイミド化物であるポリイミドからなる群から選ばれる少なくとも1種の重合体である、請求項1~3のいずれか一項に記載の液晶配向剤。
- 前記重合体(A)が、さらに下記式(2’)で表される繰り返し単位(a2’)及び下記式(3)で表される繰り返し単位(a3)よりなる群から選ばれる少なくとも一つを有するポリイミド前駆体及び該ポリイミド前駆体のイミド化物であるポリイミドからなる群から選ばれる少なくとも1種の重合体である、請求項1~4のいずれか一項に記載の液晶配向剤。
- 上記X1が、非環式脂肪族テトラカルボン酸二無水物又はその誘導体、脂環式テトラカルボン酸二無水物又はその誘導体、又は芳香族テトラカルボン酸二無水物又はその誘導体に由来する4価の有機基であって、シクロブタン環構造、シクロペンタン環構造及びシクロヘキサン環構造よりなる群から選ばれる少なくとも一種の部分構造を有するテトラカルボン酸二無水物又はその誘導体に由来する4価の有機基である、請求項1~5のいずれか一項に記載の液晶配向剤。
- 前記重合体(A)が、前記繰り返し単位(a1)と前記繰り返し単位(a1)のイミド化構造との合計を全繰り返し単位の5~100モル%含む、請求項1~6のいずれか一項に記載の液晶配向剤。
- 前記重合体(A)が、前記繰り返し単位(a1)と前記繰り返し単位(a1)のイミド化構造との合計を全繰り返し単位の5モル%以上、且つ、95モル%以下含む、請求項1~7のいずれか一項に記載の液晶配向剤。
- 前記重合体(A)が、前記繰り返し単位(a1)、及び前記繰り返し単位(a2)並びにそれらのイミド化構造の合計を全繰り返し単位の10モル%以上含む、請求項4、及び6~8のいずれか一項に記載の液晶配向剤。
- 光配向処理法用の液晶配向膜の形成に用いられる、請求項1~9のいずれか一項に記載の液晶配向剤。
- 請求項1~10のいずれか一項に記載の液晶配向剤から得られる液晶配向膜。
- 請求項11に記載の液晶配向膜を具備する液晶表示素子。
- 下記の工程(1)~(3)を含む、液晶表示素子の製造方法。
工程(1):請求項1~10のいずれか一項に記載の液晶配向剤を基板上に塗布する工程
工程(2):塗布した液晶配向剤を焼成する工程
工程(3):工程(2)で得られた焼成膜に配向処理する工程 - 前記配向処理が、光配向処理である、請求項13に記載の液晶表示素子の製造方法。
- 前記光配向処理における放射線の照射量が、100~1,500mJ/cm2である、請求項14に記載の液晶表示素子の製造方法。
- 下記の工程(4)を更に含む、請求項13~15のいずれか一項に記載の液晶表示素子の製造方法。
工程(4):工程(3)で配向処理された焼成膜に対して50~300℃の加熱処理を更に行う工程 - 請求項13~16のいずれか一項に記載の液晶表示素子の製造方法により得られる液晶表示素子。
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US7718234B2 (en) | 2002-12-09 | 2010-05-18 | Hitachi Displays, Ltd. | Liquid crystal display and method for manufacturing same |
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JP2005154436A (ja) * | 2003-11-05 | 2005-06-16 | Chisso Corp | 新規ジアミンおよびそれを原料とするポリマー |
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