Classifications

• • 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
  • C08G73/12—Unsaturated 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 suitable for a photo-alignment method treatment, a liquid crystal aligning film obtained from the liquid crystal aligning agent, and a liquid crystal display element using the liquid crystal aligning film.
• the liquid crystal alignment film obtained by the photo-alignment method is used for an IPS driving type or FFS driving type liquid crystal display element using a negative liquid crystal material, it is expected to have higher display performance than a conventional liquid crystal display element.
• the liquid crystal alignment film obtained by the photo-alignment method has a high incidence of display defects (bright spots) in the case of a liquid crystal display element using a negative liquid crystal material and causes display defects. I found out there was a problem.
• the present invention provides at least one polymer (A) selected from the group consisting of a polyimide precursor having a structural unit represented by the following formula (1) and the following formula (2) and an imidized polymer of the polyimide precursor (A).
• a liquid crystal aligning agent characterized by comprising: (Equation (1), wherein (2), X 1 and X 2 are each independently at least 1 selected from the group consisting of structures represented by the following formula (X1-1) and (Xl-2)
• R 1 , R 2, R 3 , R 4 , and R 6 are each independently a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and R 5 is an alkyl group having 1 to 4 carbon atoms.
• N is an integer of 1 to 6.
• a diamine that gives a structural unit represented by the formula (1) and a diamine that gives a structural unit represented by the formula (2) are each 1 It is preferable to produce a polyimide precursor having a structural unit represented by the formula (1) and a structural unit represented by the formula (2) by using more than one type.
• Examples of the method for imidizing the polyimide precursor include thermal imidization in which the polyimide precursor solution is heated as it is, or catalytic imidization in which a catalyst is added to the polyimide precursor solution.
• the temperature at which the polyimide precursor is thermally imidized in the solution is 100 to 400 ° C., preferably 120 to 250 ° C., and it is preferable to carry out while removing water generated by the imidation reaction from the system.
• the reaction time is preferably 30 minutes to 4 hours.
• the catalytic imidation of the polyimide precursor can be carried out by adding a basic catalyst and an acid anhydride to the polyimide precursor solution and stirring at -20 to 250 ° C, preferably 0 to 180 ° C.
• Nylmethylmorpholinium O- (benzotriazol-1-yl) -N, N, N ′, N′-tetramethyluronium tetrafluoroborate, O- (benzotriazol-1-yl) -N, N , N ′, N′-tetramethyluronium hexafluorophosphate, (2,3-dihydro-2-thioxo-3-benzoxazolyl) phosphonate diphenyl, and the like can be used.
• the amount of the condensing agent to be used is preferably 2 to 3 times, more preferably 2 to 2.5 times, mol of the tetracarboxylic acid diester.
• crosslinkable compound having an epoxy group or an isocyanate group examples include bisphenolacetone glycidyl ether, phenol novolac epoxy resin, cresol novolac epoxy resin, triglycidyl isocyanurate, tetraglycidylaminodiphenylene, tetraglycidyl-m-xylenediamine, tetra Glycidyl-1,3-bis (aminoethyl) cyclohexane, tetraphenyl glycidyl ether ethane, triphenyl glycidyl ether ethane, bisphenol hexafluoroacetodiglycidyl ether, 1,3-bis (1- (2,3-epoxypropoxy)- 1-trifluoromethyl-2,2,2-trifluoromethyl) benzene, 4,4-bis (2,3-epoxypropoxy) octafluorobiphenyl Triglycidyl-p-amin
• crosslinkable compound having a polymerizable unsaturated bond examples include trimethylolpropane tri (meth) acrylate, pentaerythritol tri (meth) acrylate, dipentaerythritol penta (meth) acrylate, and tri (meth) acryloyloxyethoxytrimethylol.
• the content of the crosslinkable compound in the liquid crystal aligning agent of the present invention is preferably 0.1 to 150 parts by mass with respect to 100 parts by mass of all polymer components.
• the amount is preferably 0.1 to 100 parts by mass with respect to 100 parts by mass of all the polymer components. More preferred is 1 to 50 parts by mass.
• F-top EF301, EF303, EF352 (above, manufactured by Tochem Products), MegaFuck F171, F173, R-30 (above, manufactured by Dainippon Ink), Florard FC430, FC431 (or more) And Asahi Guard AG710, Surflon S-382, SC101, SC102, SC103, SC104, SC105, SC106 (above, manufactured by Asahi Glass Co., Ltd.).
• the amount of the surfactant used is preferably 0.01 to 2 parts by mass, more preferably 0.01 to 1 part by mass with respect to 100 parts by mass of all the polymer components contained in the liquid crystal aligning agent.
• the liquid crystal aligning agent is published on pages 69 to 73 of International Publication No. WO2011 / 132751 (published on 10.27.2011) as a compound that promotes charge transfer in the liquid crystal alignment film and promotes charge release of the device. It is also possible to add nitrogen-containing heterocyclic amine compounds represented by the formulas [M1] to [M156].
• the amine compound may be added directly to the liquid crystal aligning agent, but it is preferable to add the amine compound after forming a solution having a concentration of 0.1 to 10% by mass, preferably 1 to 7% by mass.
• the solvent is not particularly limited as long as the specific polymer (A) is dissolved.
• the liquid crystal aligning agent of the present invention includes, in addition to the above-mentioned poor solvent, crosslinkable compound, resin film or compound that improves the film thickness uniformity and surface smoothness of the liquid crystal aligning film, and a compound that promotes charge removal. As long as the effects of the invention are not impaired, a dielectric or conductive material for changing the electrical properties such as the dielectric constant and conductivity of the liquid crystal alignment film may be added.
• the solvent used for the contact treatment is not particularly limited as long as it is a solvent that dissolves a decomposition product generated from the liquid crystal alignment film 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- Examples include methyl methoxypropionate, ethyl 3-ethoxypropionate, propyl acetate, butyl acetate, cyclohexyl acetate and the like.
• Viscosity of polyamic acid ester, polyamic acid solution, etc. was measured using an E-type viscometer TVE-22H (manufactured by Toki Sangyo Co., Ltd.), sample volume 1.1 mL, cone rotor TE-1 (1 ° 34 ′, R24), temperature Measured at 25 ° C.
• Standard samples for use TSK standard polyethylene oxide (weight average molecular weight (Mw) of about 900,000, 150,000, 100,000, 30,000) manufactured by Tosoh Corporation, and polyethylene glycol (peak top molecular weight (Mp) manufactured by Polymer Laboratories) ) About 12,000, 4,000, 1,000).
• Mw weight average molecular weight
• Mp peak top molecular weight
• the measurement was performed by mixing four types of 900,000, 100,000, 12,000, and 1,000, and three types of 150,000, 30,000, and 4,000. Two samples of the mixed sample were measured separately.
• a liquid crystal cell having a configuration of a fringe field switching (FFS) mode liquid crystal display element is manufactured.
• a substrate with electrodes was prepared.
• the substrate is a glass substrate having a size of 30 mm ⁇ 50 mm and a thickness of 0.7 mm.
• an ITO electrode having a solid pattern constituting a counter electrode as a first layer is formed.
• a SiN (silicon nitride) film formed by the CVD method is formed as the second layer.
• the second layer SiN film has a thickness of 500 nm and functions as an interlayer insulating film.
• Example 3> A liquid crystal aligning agent (3) was obtained in the same manner as in Example 1 except that 15.00 g of a 12% by mass polyamic acid solution (C) was used. This liquid crystal aligning agent was confirmed to be a uniform solution without any abnormality such as turbidity and precipitation.
• ⁇ Comparative Example 1> Except having used 15.00 g of 12 mass% polyamic acid solutions (D), it implemented similarly to Example 1 and obtained the liquid crystal aligning agent (4). This liquid crystal aligning agent was confirmed to be a uniform solution without any abnormality such as turbidity and precipitation.
• Example 12 A coating film having a thickness of 100 nm was formed in the same manner as in Example 8 except that the liquid crystal aligning agent (7) was used. The surface of the coating film was irradiated with 0.6 J / cm 2 of linearly polarized ultraviolet light having an extinction ratio of 26: 1 and a wavelength of 254 nm through a polarizing plate. Then, it heated for 14 minutes on a 230 degreeC hotplate, and obtained the board
• An FFS drive liquid crystal cell was produced by the same method as in Example 8 except that this substrate with a liquid crystal alignment film was used, and afterimage evaluation by long-term alternating current drive was performed on the obtained cell. The value of the angle ⁇ of this liquid crystal cell after long-term AC driving was 0.24 degrees. Further, as a result of observation of the bright spots in the cell, the number of bright spots was 10 or more, which was poor.

Landscapes

• Physics & Mathematics (AREA)
• Chemical & Material Sciences (AREA)
• Nonlinear Science (AREA)
• Organic Chemistry (AREA)
• Crystallography & Structural Chemistry (AREA)
• Medicinal Chemistry (AREA)
• General Physics & Mathematics (AREA)
• Optics & Photonics (AREA)
• Health & Medical Sciences (AREA)
• Chemical Kinetics & Catalysis (AREA)
• Mathematical Physics (AREA)
• Polymers & Plastics (AREA)
• Spectroscopy & Molecular Physics (AREA)
• Liquid Crystal (AREA)
• Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
• Engineering & Computer Science (AREA)
• Materials Engineering (AREA)

Priority Applications (4)

Applications Claiming Priority (2)

Publications (1)

Family

ID=55857424

Family Applications (1)

Country Status (5)

Citations (4)

Family Cites Families (8)

• 2015
  • 2015-10-26 KR KR1020177011879A patent/KR102488715B1/ko active IP Right Grant
  • 2015-10-26 WO PCT/JP2015/080131 patent/WO2016068085A1/ja active Application Filing
  • 2015-10-26 CN CN201580059292.9A patent/CN107111190A/zh active Pending
  • 2015-10-26 CN CN202211325804.XA patent/CN115746874A/zh active Pending
  • 2015-10-26 JP JP2016556560A patent/JP6776897B2/ja active Active
  • 2015-10-28 TW TW104135439A patent/TWI780023B/zh active

Patent Citations (4)

Also Published As

Similar Documents

Legal Events