WO2007011911A2 - Poly(aryletherimides) destines a des films birefringents negatifs pour lcd - Google Patents

Poly(aryletherimides) destines a des films birefringents negatifs pour lcd Download PDF

Info

Publication number
WO2007011911A2
WO2007011911A2 PCT/US2006/027782 US2006027782W WO2007011911A2 WO 2007011911 A2 WO2007011911 A2 WO 2007011911A2 US 2006027782 W US2006027782 W US 2006027782W WO 2007011911 A2 WO2007011911 A2 WO 2007011911A2
Authority
WO
WIPO (PCT)
Prior art keywords
dianhydride
bis
film
poly
aryletherimide
Prior art date
Application number
PCT/US2006/027782
Other languages
English (en)
Other versions
WO2007011911A3 (fr
Inventor
Frank Harris
Limin Sun
Dong Zhang
Stephen Z. D. Cheng
Original Assignee
Akron Polymer Systems
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Akron Polymer Systems filed Critical Akron Polymer Systems
Priority to JP2008522884A priority Critical patent/JP2009506349A/ja
Priority to EP06800097A priority patent/EP1904603A2/fr
Publication of WO2007011911A2 publication Critical patent/WO2007011911A2/fr
Publication of WO2007011911A3 publication Critical patent/WO2007011911A3/fr

Links

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
    • C08G73/1042—Copolyimides derived from at least two different tetracarboxylic compounds or two different diamino compounds
    • 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
    • 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
    • C08G73/1039—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors comprising halogen-containing substituents
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
    • C08J5/18—Manufacture of films or sheets
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
    • C08J7/04—Coating
    • C08J7/0427—Coating with only one layer of a composition containing a polymer binder
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L79/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen or carbon only, not provided for in groups C08L61/00 - C08L77/00
    • C08L79/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
    • C08L79/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
    • 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
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
    • G02B1/08—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of polarising materials
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2379/00—Characterised by the use of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen, or carbon only, not provided for in groups C08J2361/00 - C08J2377/00
    • C08J2379/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
    • C08J2379/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2479/00—Characterised by the use of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen, or carbon only, not provided for in groups C08J2461/00 - C08J2477/00
    • 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
    • G02F1/1335—Structural association of cells with optical devices, e.g. polarisers or reflectors
    • G02F1/13363—Birefringent elements, e.g. for optical compensation
    • G02F1/133634—Birefringent elements, e.g. for optical compensation the refractive index Nz perpendicular to the element surface being different from in-plane refractive indices Nx and Ny, e.g. biaxial or with normal optical axis

Definitions

  • the invention relates to the manufacture of negative birefringent polymer films for use in compensation layers in liquid crystal displays (LCDs). More particularly, the invention relates to the manufacture and use of poly(aryletherimides) (PAEIs), which can be dissolved in variety of organic solvents and coated on a variety of polymer substrates. More particularly, the invention relates to the manufacture of PAEIs, which are prepared from dianhydrides containing flexible ether or perfluoroisopropylidene linkages and aromatic diamines containing flexible ether linkages.
  • PAEIs poly(aryletherimides)
  • the invention relates to the manufacture of PAEIs based on 2,2-bis(3,4-dicarboxyphenyl)-l,l,l,3,3,3-hexafluoropropane dianhydride (6FD A) and low-cost, fluorine-containing, aromatic ether diamines, which can be dissolved in selected solvents, such as ketone solvents and/or ketone solvent mixtures, and coated on preferred polymeric substrates, resulting in multi-layer polymeric optical films.
  • 6FD A 2,2-bis(3,4-dicarboxyphenyl)-l,l,l,3,3,3-hexafluoropropane dianhydride
  • 6FD A 2,2-bis(3,4-dicarboxyphenyl)-l,l,l,3,3,3-hexafluoropropane dianhydride
  • selected solvents such as ketone solvents and/or ketone solvent mixtures
  • Liquid crystals are useful for electronic displays because light traveling through a thin film of liquid crystal is affected by the birefringence of the film, which can be controlled by the application of a voltage across the film.
  • Liquid crystal displays are desirable because the transmission or reflection of light from an external source, including ambient light, can be controlled with much less power than is required for luminescent materials used in other displays.
  • Optical axis herein refers to the direction in which propagating light does not see birefringence.
  • Negative C-plate herein refers to the plate in which the optical axis is perpendicular to the plate.
  • Out of-plane birefringence is defined by ⁇ n ⁇ - n z -(n x +n y )/2, where n z refractive index is in z direction.
  • LCDs now are commonly used in such applications as digital watches, calculators, cell phones, portable computers, televisions, and many other types of electronic equipment where the need exists for long life and small room operation with low power consumption.
  • portable computer and large screen television LCDs benefit from their lightweight, small room occupation, low power consumption, and long life operation. It is expected that LCDs will replace cathode ray tubes (CRT) as monitors and television screens in the near future.
  • CTR cathode ray tubes
  • LCDs there is intrinsic viewing angle dependence in LCDs, which affects the quality of the display performance, such as contrast, coloration, and/or brightness.
  • the primary factor limiting the quality of an LCDs' performance is the propensity of the light to leak through liquid crystal elements or cell, and this leakage's dependence on the direction from which the display is viewed.
  • the best quality LCD picture is observed only within a narrow viewing angle range centered perpendicular to the display screen.
  • One of common methods to widen LCDs' viewing angles is to apply compensation films.
  • Several LCD modes including Twisted Nematic (TN), Super Twisted Nematic (STN), Vertical Alignment (VA), and Optically Compensated Bend (OCB), with or without an applied field, show positive C-plate symmetry, which can be compensated for by a compensation film with negative C-plate symmetry.
  • TN Twisted Nematic
  • STN Super Twisted Nematic
  • VA Vertical Alignment
  • OCB Optically Compensated Bend
  • Negative birefringent films have been prepared by several different methods, such as, but not limited to precision stretching of polymer films, precisely controlled vapor deposition of thin ceramic layers, mixing of a swellable inorganic clay layer in a crosslinked polymer matrix, and solution casting or coating of thin polymer films.
  • the solution casting or coating method is preferred due to ease of processing and enhanced performance.
  • a currently used technology involves stretching the film. The drawback to utilizing a stretching of these films involves the resultant stress relaxation which can distort the film, namely at a film/screen's corners. Using a poly(aryletherimide) would eliminate the need for stretching as not only is it nearly impossible to stretch, it is simply not necessary to achieve the results desired.
  • the negative birefringent film prepared with the casting or coating method onto an LCD component which is an integral part of the LCD device, such as a polarizer.
  • the negative birefringent film is solution cast on a solvent-passive carrier substrate, adhesive is then applied to the negative birefringent film surface. The combination is laminated on the LCD component and then the carrier substrate is removed (peeled off).
  • the negative birefringent film is made by coating the polymer solution directly on an LCD unit component such as a polarizer or a polarizer substrate. This procedure is preferred due to its simplicity and cost saving. However, this procedure requires that the polymer be soluble in select solvents.
  • the solvent must dissolve the polymer which forms the negative birefringent film, but not dissolve or significantly swell the LCD component.
  • the solvent must also be able to be used in large-scale, commercial coating operations.
  • MIBK methylisobutyl ketone
  • MIBK also does not dissolve triacetylcellulose (TAC), a commonly used substrate.
  • TAC triacetylcellulose
  • pendent fluorene groups are incorporated in aromatic polyimide backbones through the polymerization of 9,9-bis(4-aminophenyl)fluorenes in order to attain solubility in useful solvents.
  • very rigid dianhydrides such as 3,3',4,4'-benzophenonetetracarboxylic acid dianhydride (BTDA), 3,3',4,4'-tetracarboxylicbiphenyl dianhydride (BPDA) or pyromellitic dianhydride (PMDA) must be used to prepare the polyimide.
  • solubilizing monomer is 4,4'-(hexahydro- 4,7-methanoindan-5-ylidene)bisphenol, which provides pendent bulky norbornene groups along the polymer backbone that hinder chain packing and enhance solubility, while still maintaining chain rigidity. Solubility can also be enhanced by copolymerization with monomers containing more flexible units such as 1,3 -dioxophenylene groups or hexafluoroisopropylidene linkages.
  • films of poly(terephthalates) prepared with this monomer have negative birefringences of ⁇ 0.01.
  • more rigid comonomers such as 4,4'-(hexahydro- 4,7-melhanoindan-5-ylidene) bisphenol must also be used to attain a polyester chain rigid enough to form films with negative birefringences > 0.01.
  • more rigid than other polyesters they are not as rigid as polyimides.
  • a negative birefringence film prepared from a poly(aryletherimide), the film having a negative birefringence greater than 0.01, at a thickness of less than 15 ⁇ m, in which the poly(aryletherimide) is solution cast or coated onto a substrate.
  • the film has one or more layers in which at least one layer is made from a poly(aryletherimide) soluble in ketone solvents, at least one layer is a polymer substrate film and the poly(aryletherimide) layer is cast or coated onto the substrate.
  • a possible material for the substrate layer may be triacetylcellulose.
  • Another embodiment of this invention is to provide homopoly(aryletherimides) and copoly(aryletherimdes), that are soluble in ketone solvents and ketone solvent mixtures, which are capable of forming thin films by casting or coating procedures, which exhibit negative birefringence.
  • Another embodiment of this invention is to be able to coat or cast the soluble poly(aryletherimides) in ketone solvents and ketone solvent mixtures on another polymeric substrate film to form multi-layers polymeric films.
  • Another embodiment of this invention is to provide a negative birefringence film prepared from a poly(aryletherimide), the film having a negative birefringence greater than 0.01 and a thickness less than 15 ⁇ m, the poly(aryletherimide) combining a dianhydride and a diamine, and the poly(aryletherimide) is solution cast or coated onto the film.
  • Another embodiment of this invention is to prepare a negative birefringence film prepared from a poly(aryletherimide), the film having a negative birefringence greater than 0.01 and a thickness less than 15 ⁇ m, the poly(aryletherimide) combining a dianhydride chosen from the group consisting of: 2,2-bis(3,4-dicarboxyphenyl)-l, 1,1,3, 3,3- hexafluoropropane dianhydride (6FD A), bis(3,4-dicarboxyphenyi)ether dianhydride (ODPA), 4,4'-[4,4'-(p-phenyleneoxy)isopropylidene]-bis(phthalic anhydride) (Bis- A-D A), 4,4 ' - [4,4 ' -(p-phenyleneoxy)hexafluoroisopropylidene] -bis(phthalic anhydride) (Bis- AF-D A), l,4-bis(3,4-dicarbox
  • Another embodiment of this invention is to provide a liquid crystal display using a negative birefringence film prepared from a poly(aryletherimide) having a negative birefringence greater than 0.01, at a thickness of less than 15 ⁇ m, in which the poly(aryletherimide) is solution cast or coated onto the film.
  • Another embodiment of this invention is to provide a liquid crystal display using a polymeric film comprising one or more layers in which at least one layer is made from a poly(aryletherimide) soluble in ketone solvents, at least one layer is a polymer substrate film and the poly(aryletherimide) layer is cast or coated onto the film.
  • Another embodiment of this invention is to provide a liquid crystal display using a negative birefringence film prepared from a poly(aryletherimide), the film having a negative birefringence greater than 0.01 and a thickness less than 15 ⁇ m, the poly(aryletherimide) combining a dianhydride and a diamine, and the poly(aryletherimide) is solution cast or coated onto the film.
  • Colorless poly(aryletherirnide) films less than 15 ⁇ m thick with negative birefringences greater than 0.01 can be prepared by solution coating or casting procedures using the preferred solvents, ketones and ketone solvent mixtures. These films achieve their birefringence values as cast and need not be subjected to further stretching. These results are unexpected in that the poly(aryletherimides) are prepared from dianhydrides containing flexible perfluoroisopropylidene or ether linkages and diamines containing flexible ether linkages. Neither component need be rigid if this combination of monomers is used.
  • Especially preferred dianhydrides would include:
  • the diamines that are especially useful for the invention include:
  • diamines 2,2-bis[4-(4-amino-2-trifluoromethylphenoxy)-phenyl]propane, 2,2-bis[4-(4-ammo-2-trifluoromethylphenoxy)-phenyl]l,l,l,3,3,3-hexafluoropropane.
  • diamines would include:
  • One embodiment includes the combination which utilize at least one ether linkage and one perfluoromethyl in the diamine and at least two perfluoromethyl groups in the dianhydride.
  • the films of the present invention are soluble in cyclopentanone and MIBK. Solubility of the films in cyclopentanone is appropriate for many applications, a significant number of applications use MIBK solubility as well. As stated before, solubility in MIBK is the preferred solvent for solution coating on cellulosic substrates such as TAC.
  • the PAEI film will include the trifluoromethyl (or perfluoromethyl) groups (CF 3 ) on both the diamine and dianhydirde.
  • the presence of the trifluormethyl group(s) enhances the solubility of the film in MEBK.
  • the solvent mixture can be a mixture of solvents such as 95% MIBK and 5% ethyl acetate. Although, the percentages are not critical as long as it is predominantly 50% MD3K.
  • Mixtures of dianhydrides and diamines can be employed in the present invention. Mixtures of dianhydrides can be employed, preferably one of the dianhydrides has perfluoromethyl groups, while the other suitable dianhydrides that can be used include pyromellitic anhydride (I):
  • Mixtures of aromatic diamines can be used in combination preferably with the diamines of the invention including
  • G and F are independently selected from the representative and illustrative group consisting of a covalent bond, a CH 2 group, a C(CH 3 ) 2 group, a C(CF 3 ) 2 group, a C(CX 3 ) 2 group wherein X is a halogen, a CO group, a O atom, a S atom, a SO2 group, a Si(CH 2 CH 3 ) 2 group or a N(CH 3 ) group; and m is an integer from 1 to 3.
  • One embodiment involving a mixture includes a dianhydride mixture of 2,2-bis(3,4- dicarboxyphenyl)-l,l,l,3,3,3-hexafiuoropropane dianhydride (6FDA) and 4, 4' biphenyl dianhyride and the diamine is 4, 4'-bis(4-amino-trifluoromethylphenoxy) biphenyl (6FOBDA).
  • the mixture of 2,2-bis(3,4-dicarboxyphenyl)-l,l,l,3,3,3-hexafluoropropane dianhydride (6FD A) and 4, 4' biphenyl dianhydride is a molar ration between 99 to 1 (99:1) and 40 to 60 (40:60).
  • Another embodiment involves the molar ratio of the mixture of 2,2- bis(3,4-dicarboxyphenyl)-l,l,l,3,3,3-hexafluoropropane dianhydride (6FD A) and 4, 4' biphenyl dianhyride being 80 to 20 (80:20).
  • Another embodiment involving a mixture includes a dianhydride mixture of 2,2- bis(3,4-dicarboxyphenyl)-l,l,l,3,3,3-hexafluoropropane dianhydride (6FDA) and 4, 4' biphenyl dianhyride and the diamine is 2,2'-bis(trifluoromethyl)-4,4'-diaminophenyl ether (6FODA).
  • 6FDA 2,2- bis(3,4-dicarboxyphenyl)-l,l,l,3,3,3-hexafluoropropane dianhydride
  • 6FODA 2,2'-bis(trifluoromethyl)-4,4'-diaminophenyl ether
  • the mixture of 2,2-bis(3,4-dicarboxyphenyl)-l,l,l,3,3,3-hexafluoropropane dianhydride (6FD A) and 4, 4' biphenyl dianhyride is a molar ratio between 99 to 1 (99:1) and 40 to 60 (40:60).
  • Another embodiment involves the molar ratio of the mixture of 2,2-bis(3,4- dicarboxyphenyl)-l,l,l,3,3,3-hexafluoropropane dianhydride (6FDA) and 4, 4' biphenyl dianhyride being 80 to 20 (80:20).
  • This example illustrates the preparation of 2,2'-bis(trifluoromethyl)-4,4'- diaminophenyl ether (6FOD A).
  • 2-chloro-5-nitrobenzotrifluoride 480.7g, 2.132 mol
  • sodium carbonate 112.96g, 0.122 mol
  • m-nitrobenzoic acid 1.77g, 0.01 mol
  • DMAc 700 ml
  • EXAMPLE 2 This example illustrates the preparation of 2-trifluoromethyl- 4, 4'-diaminophenyl ether (3FOD A).
  • This example illustrates the preparation of 2-trifluoromethyl-2'-methyl-4, 4'- diaminophenyl ether (3FHODA)
  • 2-chloro-5-nitrobenzotrifluoride 33.83g, 0.15 mol
  • 2-methyl-4-nitrophenol 23g, 0.15 mol
  • potassium carbonate 2 Ig, 0.15 mol
  • DMF 100 ml
  • the mixture was heated to 100 0 C overnight. After being cooled to room temperature, the mixture was filtered to remove any solid. Most of the solvent, DMF, was removed by distillation under reduced pressure. The residue was poured into water.
  • This example illustrates the preparation of 4, 4'-bis(4-amino-trifluoromethylphenoxy) biphenyl (6FOQDA).
  • This example illustrates the preparation of 4, 4'-bis(4-amino-trifluoromethylphenoxy) biphenyl (6FOBDA).
  • This example illustrates the preparation of 2, 2-bis[4-(4-amino-2- trifluoromethylphenoxy)-phenyl] 1, 1, 1, 3, 3, 3-hexafluoropropane (12FOBDA).
  • This example illustrates the general procedure to prepare a homopolyimide of a dianhydride and a diamine.
  • This example illustrates the general procedure to prepare a copolyimide from a mixture of dianhydrides and one diamine.
  • This example illustrates the general procedure to prepare a copolyimide of one dianhydride and multi-components diamines.
  • Polyimide films displaying negative birefringence were prepared by the following procedure: the polyimide was dissolved in cyclopentanone or MBBK to a solids content between 4 ⁇ 5%. After filtration, the solution was poured on a glass substrate. The solvent was allowed to evaporate at ambient temperature. The glass substrate containing the film was dried at 100°C under reduced pressure. The polyimide film was removed from the glass by dipping the substrate glass in water. The birefringence of the polyimide film was determined on a Metricon Prism Coupler 2010/M. The birefringences of typical examples are given in
  • a MIBK solution of the poly(aryletherimide) was rod-coated on a glass plate or on a triacetylcellulose (TAC) film.
  • TAC triacetylcellulose
  • a solution containing 3 to 5 wt% of the poly(aryletherimide) was used, while in the case of a TAC film, a solution containing 8 to 20 wt% of the poly(aryletherimide) was used.
  • a Cyclopentanone.
  • b Methylisobutyl ketone.
  • c Negative birefringence of 15-20 ⁇ m thick film on a glass substrate.
  • d Negative birefringence of 1-5 ⁇ m thick film on a triacetylcellulose (TAC) film.
  • TAC triacetylcellulose

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Engineering & Computer Science (AREA)
  • Manufacturing & Machinery (AREA)
  • Materials Engineering (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
  • Polarising Elements (AREA)
  • Coating Of Shaped Articles Made Of Macromolecular Substances (AREA)
  • Laminated Bodies (AREA)

Abstract

L'invention concerne une classe de poly(arylétherimides) solubles (PAEI) possédant des squelettes souples et utiles dans la fabrication de films optiques polymères. Les poly(arylétherimides) sont dissous dans des solvants organiques, tels que des cétones et des mélanges de solvants de cétones et revêtus sur une palette de substrats, tels que la triacétyl-cellulose (TAC), de manière à former des films à couche mince clairs affichant une biréfringence négative. Les films minces peuvent servir de couches de compensation dans des affichages à cristaux liquides (LCD) et peuvent être combinés avec d'autres types de films optiques, tels que des polariseurs, des films d'amélioration de la brillance ou d'autres films de compensation, aux fins de formation de films multicouches spécialement utiles dans la fabrication de LCD.
PCT/US2006/027782 2005-07-18 2006-07-18 Poly(aryletherimides) destines a des films birefringents negatifs pour lcd WO2007011911A2 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
JP2008522884A JP2009506349A (ja) 2005-07-18 2006-07-18 Ｌｃｄの負複屈折フィルムのためのポリ（アリールエーテルイミド）
EP06800097A EP1904603A2 (fr) 2005-07-18 2006-07-18 Poly(aryletherimides) destines a des films birefringents negatifs pour lcd

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US70016905P 2005-07-18 2005-07-18
US60/700,169 2005-07-18

Publications (2)

Publication Number Publication Date
WO2007011911A2 true WO2007011911A2 (fr) 2007-01-25
WO2007011911A3 WO2007011911A3 (fr) 2007-08-09

Family

ID=37669492

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2006/027782 WO2007011911A2 (fr) 2005-07-18 2006-07-18 Poly(aryletherimides) destines a des films birefringents negatifs pour lcd

Country Status (5)

Country Link
EP (1) EP1904603A2 (fr)
JP (1) JP2009506349A (fr)
KR (1) KR20080030671A (fr)
CN (1) CN101258223A (fr)
WO (1) WO2007011911A2 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2020187751A1 (fr) * 2019-03-15 2020-09-24 Technische Universität Wien Procédé de production de polyimides

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101492377B (zh) * 2009-02-25 2012-11-07 东华大学 一种2,2-双[4-(2-三氟甲基-4-硝基苯氧基)苯基]六氟丙烷的制备方法
KR101543478B1 (ko) * 2010-12-31 2015-08-10 코오롱인더스트리 주식회사 투명 폴리이미드 필름 및 그 제조방법
JP6192172B2 (ja) * 2012-05-31 2017-09-06 山本化成株式会社 エーテル化合物および該化合物の製造方法
CN104230717B (zh) * 2014-08-26 2016-06-15 天津市众泰化工科技有限公司 一种制备2,2′-二(三氟甲基)-4,4′-二硝基二苯醚的方法
KR101943516B1 (ko) * 2017-04-06 2019-01-30 한국과학기술연구원 디아민 화합물, 이로부터 형성된 폴리아믹산과 폴리이미드 및 폴리이미드를 포함한 폴리이미드 필름
WO2018190179A1 (fr) * 2017-04-10 2018-10-18 大日本印刷株式会社 Film de polyimide, produit stratifié et matériau de surface pour unité d'affichage
CN108587164B (zh) * 2018-05-09 2020-07-07 哈尔滨工业大学 一种色彩可调节的形状记忆聚酰亚胺及其制备方法
WO2024070802A1 (fr) * 2022-09-27 2024-04-04 東レ株式会社 Composition de résine, produit durci et dispositif d'affichage électroluminescent organique

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5089593A (en) * 1988-06-28 1992-02-18 Amoco Corporation Polyimide containing 4,4'-bis(4-amino-2-trifluoromethylphenoxy)-biphenyl moieties
US5344916A (en) * 1993-04-21 1994-09-06 The University Of Akron Negative birefringent polyimide films
US6074709A (en) * 1996-05-23 2000-06-13 3M Innovative Properties Company Polyimide angularity enhancement layer

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5089593A (en) * 1988-06-28 1992-02-18 Amoco Corporation Polyimide containing 4,4'-bis(4-amino-2-trifluoromethylphenoxy)-biphenyl moieties
US5344916A (en) * 1993-04-21 1994-09-06 The University Of Akron Negative birefringent polyimide films
US6074709A (en) * 1996-05-23 2000-06-13 3M Innovative Properties Company Polyimide angularity enhancement layer

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2020187751A1 (fr) * 2019-03-15 2020-09-24 Technische Universität Wien Procédé de production de polyimides

Also Published As

Publication number Publication date
EP1904603A2 (fr) 2008-04-02
JP2009506349A (ja) 2009-02-12
WO2007011911A3 (fr) 2007-08-09
CN101258223A (zh) 2008-09-03
KR20080030671A (ko) 2008-04-04

Similar Documents

Publication Publication Date Title
US7438957B2 (en) Poly(aryletherimides) for negative birefringent films for LCDs
JP4237251B2 (ja) 負複屈折のポリイミド膜
WO2007011911A2 (fr) Poly(aryletherimides) destines a des films birefringents negatifs pour lcd
JP3817604B2 (ja) ポリイミド広角化層
CN110684195B (zh) 聚酰亚胺膜、聚酰亚胺前体和聚酰亚胺
EP2847250B1 (fr) Substrats flexibles thermiquement stables pour dispositifs électroniques
EP0698052B1 (fr) Films de polyimide birefringents negatifs
TWI437328B (zh) An optical film, an image display device, a diethynyl group and a polymer thereof
WO2006129771A1 (fr) Acide tétracarboxylique ou polyesterimide dudit acide, et procédé de synthèse dudit acide
KR20190095556A (ko) 폴리이미드 및 그의 성형체
JP2010180349A (ja) 新規なジアミン、ポリイミド前駆体およびポリイミドとこれよりなる塗布型光学補償フィルムおよびその製造方法
KR102441126B1 (ko) 역 파장 분산을 갖는 광학 보상 필름
TW201410738A (zh) 聚醯胺酸、聚醯亞胺、聚醯胺酸溶液及聚醯亞胺之用途
JP2008074769A (ja) テトラカルボン酸類及びそのポリイミド、ならびにその製造方法
KR20230066490A (ko) 테트라카르복실산 이무수물로부터 유도되는 폴리이미드, 및 그 폴리이미드로 이루어지는 성형체
JP5325491B2 (ja) 新規な塗布型光学補償フィルムおよびその製造方法
JP7054064B2 (ja) フレキシブルデバイス基板形成用組成物
US20090137770A1 (en) Polymide optical compensation films
JP5015070B2 (ja) 新規な塗布型光学補償フィルムおよびその製造方法
KR20150137700A (ko) 폴리이미드 공중합체를 포함하는 위상차 필름 및 이를 포함하는 디스플레이 장치
KR101622831B1 (ko) 폴리이미드 수지 조성물 및 이를 포함하는 광학 필름
KR20150137701A (ko) 폴리이미드 수지 조성물 및 이를 포함하는 광학 필름

Legal Events

Date Code Title Description
WWE Wipo information: entry into national phase

Ref document number: 200680031234.6

Country of ref document: CN

121 Ep: the epo has been informed by wipo that ep was designated in this application
WWE Wipo information: entry into national phase

Ref document number: 2008522884

Country of ref document: JP

NENP Non-entry into the national phase

Ref country code: DE

WWE Wipo information: entry into national phase

Ref document number: 2006800097

Country of ref document: EP

WWE Wipo information: entry into national phase

Ref document number: 1020087003882

Country of ref document: KR