Negative birefringent polyimide films
First Claim
Patent Images
1. A non-stretched homopolymer polyimide film, soluble in the imide form, for use in negative birefringence layers in liquid crystal displays, the film having a negative birefringence of 0.001 to 0.2, the film having been prepared from solutions of soluble polyimides of the type having an aromatic dianhydride of general formula (I):
- ##STR88## and an aromatic diamine of formula (III) ##STR89## wherein each R is a substituent selected independently from the group consisting of H, halogen, phenyl, substituted phenyl, alkyl and substituted alkyl of from 1 to 20 carbons;
F is selected from the group consisting of a covalent bond, a CH2 group, a C(CH3)2 group, a C(CX3)2 group wherein X is a halogen, a CO group, an O atom, a S atom, a SO2 group, a Si(R)2 group wherein R is as defined previously, and a N(R) group wherein R is as defined previously;
A is selected from the group consisting of hydrogen, halogen, alkyl, substituted alkyl, nitro, cyano, thioalkyl, alkoxy, substituted alkoxy, aryl and substituted aryl, aliphatic and aromatic ester, and combinations thereof from 1 to 20 carbons;
n is an integer from 0 to 4; and
p and q are integers from 1 to 3 and when p and q are greater than 1, the linking group between benzyl or substituted benzyl groups is F; and
wherein the negative birefringence of the film is determined by control of the degree of in-plane orientation of the polyimide by the selection of R, F and A, and the values of n, p and q, which affects the polyimide backbone chain rigidity and linearity, the higher the rigidity and linearity of the polyimide backbone, the larger the value of the negative birefringence of the polyimide film.
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Abstract
A negative birefringent film, useful in liquid crystal displays, and a method for controlling the negative birefringence of a polyimide film is disclosed which allows the matching of an application to a targeted amount of birefringence by controlling the degree of in-plane orientation of the polyimide by the selection of functional groups within both the diamine and dianhydride segments of the polyimide which affect the polyimide backbone chain rigidity, linearity, and symmetry. The higher the rigidity, linearity and symmetry of the polyimide backbone, the larger the value of the negative birefringence of the polyimide film.
161 Citations
26 Claims
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1. A non-stretched homopolymer polyimide film, soluble in the imide form, for use in negative birefringence layers in liquid crystal displays, the film having a negative birefringence of 0.001 to 0.2, the film having been prepared from solutions of soluble polyimides of the type having an aromatic dianhydride of general formula (I):
- ##STR88## and an aromatic diamine of formula (III) ##STR89## wherein each R is a substituent selected independently from the group consisting of H, halogen, phenyl, substituted phenyl, alkyl and substituted alkyl of from 1 to 20 carbons;
F is selected from the group consisting of a covalent bond, a CH2 group, a C(CH3)2 group, a C(CX3)2 group wherein X is a halogen, a CO group, an O atom, a S atom, a SO2 group, a Si(R)2 group wherein R is as defined previously, and a N(R) group wherein R is as defined previously; A is selected from the group consisting of hydrogen, halogen, alkyl, substituted alkyl, nitro, cyano, thioalkyl, alkoxy, substituted alkoxy, aryl and substituted aryl, aliphatic and aromatic ester, and combinations thereof from 1 to 20 carbons; n is an integer from 0 to 4; and p and q are integers from 1 to 3 and when p and q are greater than 1, the linking group between benzyl or substituted benzyl groups is F; and wherein the negative birefringence of the film is determined by control of the degree of in-plane orientation of the polyimide by the selection of R, F and A, and the values of n, p and q, which affects the polyimide backbone chain rigidity and linearity, the higher the rigidity and linearity of the polyimide backbone, the larger the value of the negative birefringence of the polyimide film. - View Dependent Claims (2, 3)
- ##STR88## and an aromatic diamine of formula (III) ##STR89## wherein each R is a substituent selected independently from the group consisting of H, halogen, phenyl, substituted phenyl, alkyl and substituted alkyl of from 1 to 20 carbons;
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4. A non-stretched homopolymer polyimide film, soluble in the imide form, for use in negative birefringence layers in liquid crystal displays, the film having a negative birefringence of 0.001 to 0.2, the film having been prepared from solutions of soluble polyimides of the type having an aromatic dianhydride of general formula (II):
- ##STR90## and a polyaromatic diamine of formula (III) ##STR91## where F and G are selected independently from the group consisting of a covalent bond, a CH2 group, a C(CH3)2 group, a C(CX3)2 group were X is a halogen, a CO group, an O atom, a S atom, a SO2 group, a Si(R)2 group wherein R is a substituent selected independently from the group consisting of H, phenyl, substituted phenyl, alkyl and substituted alkyl from 1 to 20 carbons, and a N(R) group wherein R is as defined previously;
A is selected from the group consisting of hydrogen, halogen, alkyl, substituted alkyl, nitro, cyano, thioalkyl, alkoxy, substituted alkoxy, aryl and substituted aryl, aliphatic and aromatic esters and combinations thereof from 1 to 20 carbons; n is an integer from 0 to 4; and p and q are integers from 0 to 3 and 1 to 3 respectively, and when p and q are greater than 1, the linking group between benzyl or substituted benzyl groups is F; and wherein the negative birefringence of the film is determined by controlling the degree of in-plane orientation of the polyimide by the selection of G, F, and A, and the values of n, p and q, which affects the polyimide backbone chain rigidity and linearity, the higher the rigidity and linearity of the polyimide backbone, the larger the value of the negative birefringence of the polyimide film. - View Dependent Claims (5, 6)
- ##STR90## and a polyaromatic diamine of formula (III) ##STR91## where F and G are selected independently from the group consisting of a covalent bond, a CH2 group, a C(CH3)2 group, a C(CX3)2 group were X is a halogen, a CO group, an O atom, a S atom, a SO2 group, a Si(R)2 group wherein R is a substituent selected independently from the group consisting of H, phenyl, substituted phenyl, alkyl and substituted alkyl from 1 to 20 carbons, and a N(R) group wherein R is as defined previously;
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7. A non-stretched copolyimide film, soluble in the imide form, for use in negative birefringence layers in liquid crystal displays, the film having a negative birefringence of 0.001 to 0.2, the film having been prepared from solutions of soluble polyimides of the type having at least one aromatic dianhydride of general formula (II):
- ##STR92## and at least one polyaromatic diamine of formula (III) ##STR93## where F and G are substituents selected independently from the group consisting of a covalent bond, a CH2 group, a C(CH3)2 group, a C(CX3)2 group wherein X is a halogen, a CO group, an O atom, a S atom, a SO2 group, a Si(R)2 group wherein R is a substituent selected from the group consisting of H, phenyl, substituted phenyl, alkyl and substituted alkyl of from 1 to 20 carbons, and a N(R) group wherein R is as defined previously;
A is selected from the group consisting of hydrogen, halogen, alkyl, substituted alkyl, nitro, cyano, thioalkyl, alkoxy, substituted alkoxy, aryl and substituted aryl, aliphatic and aromatic esters and combinations thereof from 1 to 20 carbons; n is an integer from 0 to 4; and p and q are integers from 0 to 3 and 1 to 3 respectively, and when p and q are greater than 1, the linking group between benzyl or substituted benzyl groups is F; to form a copolyimide of formula (VII) ##STR94## wherein x varies from 100 to 0 while y varies correspondingly from 0 to 100; and
wherein the negative birefringence of the film is determined by the control of the degree of in-plane orientation of the copolyimide by the selection of G, F, and A, and the values of n, p, q, x and y, which affects the polyimide backbone chain rigidity and linearity, the higher the rigidity and linearity of the polyimide backbone, the larger the value of the negative birefringence of the polyimide film. - View Dependent Claims (8, 9)
- ##STR92## and at least one polyaromatic diamine of formula (III) ##STR93## where F and G are substituents selected independently from the group consisting of a covalent bond, a CH2 group, a C(CH3)2 group, a C(CX3)2 group wherein X is a halogen, a CO group, an O atom, a S atom, a SO2 group, a Si(R)2 group wherein R is a substituent selected from the group consisting of H, phenyl, substituted phenyl, alkyl and substituted alkyl of from 1 to 20 carbons, and a N(R) group wherein R is as defined previously;
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10. A non-stretched copolyimide film, soluble in the imide form, for use in negative birefringence layers in liquid crystal displays, the film having a negative birefringence of 0.001 to 0.2, the film having been prepared from solutions of soluble polyimides of the type having at least one aromatic dianhydride of general formula (I):
- ##STR95## and at least one polyaromatic diamine of formula (III) ##STR96## where each R is a substituent selected independently from the group consisting of H, phenyl, substituted phenyl, alkyl and substituted alkyl of from 1 to 20 carbons;
F is a substituent selected from the group consisting of a covalent bond, a CH2 group, a C(CH3)2 group, a C(CX3)2 group wherein X is a halogen, a CO group, an O atom, a S atom, a SO2 group, a Si(R)2 group wherein R is as defined previously and a N(R) group wherein R is as defined previously; A is selected from the group consisting of hydrogen, halogen, alkyl, substituted alkyl, nitro, cyano, thioalkyl, alkoxy, substituted alkoxy, aryl and substituted aryl, aliphatic and aromatic esters and combinations thereof from 1 to 20 carbons; n is an integer from 0 to 4; and p and q are integers from 1 to 3, and when p and q are greater than 1, the linking group between benzyl or substituted benzyl groups is F; to form a copolyimide of formula (VI) ##STR97## wherein x varies from 100 to 0 while y varies correspondingly from 0 to 100; and
wherein the negative birefringence of the film is determined by the control of the degree of in-plane orientation of the polyimide by the selection of R, F and A, and the values of n, p, q, x and y, which affects the polyimide backbone chain rigidity and linearity, the higher the rigidity and linearity of the polyimide backbone, the larger the value of the negative birefringence of the polyimide film. - View Dependent Claims (11, 12)
- ##STR95## and at least one polyaromatic diamine of formula (III) ##STR96## where each R is a substituent selected independently from the group consisting of H, phenyl, substituted phenyl, alkyl and substituted alkyl of from 1 to 20 carbons;
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13. A non-stretched copolyimide film, soluble in the imide form for use in negative birefringence layers in liquid crystal displays, the film having a negative birefringence of 0.001 to 0.2, the film having been prepared from solutions of soluble polyimides of the type having at least one first aromatic dianhydride of general formula (I) ##STR98## and at least one second aromatic dianhydride of formula (II) ##STR99## and at least one polyaromatic diamine of formula (III) ##STR100## where each R is a substituent selected independently from the group consisting of H, phenyl, substituted phenyl, alkyl and substituted alkyl from 1 to 20 carbons;
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F and G are substituents selected independently from the group consisting of a covalent bond, a CH2 group, a C(CH3)2 group, a C(CX3)2 group wherein X is a halogen, a CO group, an O atom, a S atom, a SO2 group, a Si(R)2 group wherein R is as defined previously and a N(R) group wherein R is as defined previously; A is selected from the group consisting of hydrogen, halogen, alkyl, substituted alkyl, nitro, cyano, thioalkyl, alkoxy, substituted alkoxy, aryl and substituted aryl, aliphatic and aromatic ester and combinations thereof from 1 to 20 carbons; n is an integer from 0 to 4; and p and q are integers from 0 to 3 and 1 to 3 respectively, and when p and q are greater than 1, the linking group between benzyl or substituted benzyl groups is F; to form a copolyimide of formula (VIII) ##STR101## wherein x varies from 100 to 0 while y varies correspondingly from 0 to 100; and
wherein the negative birefringence of the film is determined by the control of the degree of in-plane orientation of the polyimide by the section of R, G, F, and A, and the values of n, p, q, x and y, which affects the polyimide backbone chain rigidity and linearity, the higher the rigidity and linearity of the polyimide backbone, the larger the value of the negative birefringence of the polyimide film. - View Dependent Claims (14, 15)
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16. An improved liquid crystal display of the type having a liquid crystal element, at least two light-transmissive birefringent films, at least one film having a positive birefringence and at least one other film having a negative birefringence, and a polarizing sheet arranged such that the films are held between the liquid crystal elements and the polarizing sheet, wherein the improvement comprises at least one non-stretched negative polyimide thin film, soluble in the imide form, having a negative birefringence, the polyimide film being selected from the group consisting of
(a) an organic solvent soluble homopolyimide film, the homopolyimide being selected from the group consisting of formulas (i) and (ii), and ##STR102## (b) an organic solvent soluble copolyimide film, the copolyimide being selected from the group consisting of formulas (i), (ii) and (iii). ##STR103## where each R is a substituent selected independently from the group consisting of H, halogen, phenyl, substituted phenyl, alkyl and substituted alkyl from 1 to 20 carbons; -
E and F are selected independently from the group consisting of a covalent bond, a CH2 group, a C(CH3)2 group, a C(CX3)2 group wherein X is a halogen, a CO group, an O atom, a S atom, a SO2 group, a Si(R)2 group wherein R is as defined previously and a N(R) group wherein R is as defined previously;
A is selected from the group consisting of hydrogen, halogen, alkyl, substituted alkyl, nitro, cyano, thioalkyl, alkoxy, substituted alkoxy, aryl and substituted aryl, aliphatic and aromatic esters and combinations thereof from 1 to 20 carbons;n is an integer from 0 to 4; p and q are integers from 1 to 3 when the polyimide is a homopolyimide and are integers from 0 to 3 and 1 to 3 respectively when the polyimide is a copolyimide, and when p and q are greater than 1, the linking group between benzyl or substituted benzyl groups is F; and x, if present varies from 100 to 0 while y, if present, varies correspondingly from 0 to 100. - View Dependent Claims (17, 18)
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19. An improved liquid crystal display having a polarizer layer, an analyzer layer, a liquid crystal layer disposed between the polarizer layer and the analyzer layer, a first electrode proximate to a first major surface of the liquid crystal layer, a second electrode proximate to a second major surface of the liquid crystal layer, the first and second electrodes being adapted to apply a voltage across the liquid crystal layer when the electrodes are connected to a source of electrical potential, and a multilayer thin film compensator disposed between the polarizer layer and the analyzer layer, including a first plurality of layers, each having a first refractive index and a first thickness, alternating with a second plurality of layers, each having a second refractive index and a second thickness, the values of the first and second refractive indices and thicknesses being such that the phase retardation of the multilayer is equal in magnitude but opposite in sign to the phase retardation of the liquid crystal layer in its homeotropically aligned state over a predetermined range of viewing angles, wherein the improvement comprises at least one non-stretched negative polyimide thin film, soluble in the imide form, within the compensator having a negative birefringence, the polyimide film being selected from the group consisting of
(a) an organic solvent soluble homopolyimide film, the homopolyimide being selected from the group consisting of formulas (i) and (ii), and ##STR104## (b) an organic solvent soluble copolyimide film, the copolyimide being selected from the group consisting of formulas (i), (ii) and (iii). ##STR105## where each R is a substituent selected independently from the group consisting of H, halogen, phenyl, substituted phenyl, alkyl and substituted alkyl from 1 to 20 carbons; -
F and G are independently selected from the group consisting of a covalent bond, a CH2 group, a C(CH3)2 group, a C(CX3)2 group wherein X is a halogen, a CO group, an O atom, a S atom, a SO2 group, a Si(R)2 group wherein R is as defined previously and a N(R) group wherein R is as defined previously; A is selected from the group consisting of hydrogen, halogen, alkyl, substituted alkyl, nitro, cyano, thioalkyl, alkoxy, substituted alkoxy, aryl and substituted aryl, aliphatic and aromatic esters and combinations thereof from 1 to 20 carbons; n is an integer from 0 to 4; p and q are integers from 1 to 3 when the polyimide is a homopolyimide and are integers from 0 to 3 and 1 to 3 respectively when the polyimide is a copolyimide, and wherein when p and q are greater than 1, the linking group between benzyl or substituted benzyl groups is F; and x, if present, varies from 100 to 0 while y, if present, varies correspondingly from 0 to 100.
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20. An improved compensator for use in a liquid crystal display having at least one negative birefringent film layer and at least one positive birefringent film layer, wherein the improvement comprises the inclusion of at least one non-stretched negative polyimide thin film soluble in the imide form, the polyimide film being selected from the group consisting of
(a) an organic soluble homopolyimide film, the homopolyimide being selected from the group consisting of formulas (i) and (ii), and ##STR106## (b) an organic solvent soluble copolyimide film, the copolyimide being selected from the group consisting of formulas (i), (ii) and (iii). ##STR107## where each R is a substituent selected independently from the group consisting of H, halogen, phenyl, substituted phenyl, alkyl and substituted alkyl from 1 to 20 carbons; -
E and F are selected independently from the group consisting of a covalent bond, a CH2 group, a C(CH3)2 group, a C(CX3)2 group wherein X is a halogen, a CO group, an O atom, a S atom, a SO2 group, a Si(R)2 group wherein R is as defined previously and a N(R) group wherein R is as defined previously; A is selected from the group consisting of hydrogen, halogen, alkyl, substituted alkyl, nitro, cyano, thioalkyl, alkoxy, substituted alkoxy, aryl and substituted aryl, aliphatic and aromatic esters and combinations thereof from 1 to 20 carbons; n is an integer from 0 to 4; p and q are integers from 1 to 3 when the polyimide is a homopolyimide and are integers from 0 to 3 and 1 to 3 respectively when the polyimide is a copolyimide, and when p and q are greater than 1, the linking group between benzyl or substituted benzyl group is F; and x, if present, varies from 100 to 0 while y, if present, varies correspondingly from 0 to 100.
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21. An improved liquid crystal display comprising a liquid crystal element, at least two birefringent films and a polarizing sheet arranged that said films are held between said liquid crystal element and said polarizing sheet, characterized in that said birefringent films are composed of at least one polymer having a positive intrinsic birefringence and light transmission properties and at least one film having negative intrinsic birefringence and light transmission properties, wherein the improvement comprises at least one non-stretched polyimide film, soluble in the imide form, having a negative birefringence, the polyimide film being selected from the group consisting of:
(a) an organic solvent soluble homopolyimide film, the homopolyimide being selected from the group consisting of formulas (i) and (ii), and ##STR108## (b) an organic solvent soluble copolyimide film, the copolyimide being selected from the group consisting of formulas (i), (ii) and (iii). ##STR109## where each R is a substituent selected independently from the group cocsisting of H, halogen, phenyl, substituted phenyl, alkyl and substituted alkyl from 1 to 20 carbons; E and F are selected independently from the group consisting of a covalent bond, a CH2 group, a C(CH3)2 group, a C(CX3)2 group wherein X is a halogen, a CO group, an O atom, a S atom, a SO2 group, a Si(R)2 group wherein R is as defined previously and a N(R) group wherein R is as defined previously; A is selected from the group consisting of hydrogen, halogen, alkyl, substituted alkyl, nitro, cyano, thioalkyl, alkoxy, substituted alkoxy, aryl and substituted aryl, aliphatic and aromatic esters and combinations thereof from 1 to 20 carbons; n is an integer from 0 to 4; p and q are integers from 1 to 3 when the polyimide is a homopolyimide and are integers from 0 to 3 and 1 to 3 respectively when the polyimide is a copolyimide, and when p and q are greater than 1, the linking group between benzyl or substituted benzyl groups is F; and x, if present, varies from 100 to 0 while y, if present, varies correspondingly from 0 to 100. - View Dependent Claims (22, 23)
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24. An improved liquid crystal display of the type having a liquid crystal element, at least two light-transmissive birefringent coatings, at least one coating having a positive birefringence and at least one other coating having a negative birefringence, and a polarizing sheet arranged such that the coatings are held between the liquid crystal elements and the polarizing sheet, wherein the improvement comprises at least one non-stretched negative polyimide coating, soluble in the imide form, having a negative birefringence, the polyimide coating being selected from the group consisting of
(a) an organic solvent soluble homopolyimide coating, the homopolyimide being selected from the group consisting of formulas (i) and (ii), and ##STR110## (b) an organic solvent soluble copolyimide coating, the copolyimide being selected from the group consisting of formulas (i), (ii) and (iii). ##STR111## where each R is a substituent selected independently from the group consisting of H, halogen, phenyl, substituted phenyl, alkyl and substituted alkyl from 1 to 20 carbons; -
E and F are selected independently from the group consisting of a covalent bond, a CH2 group, a C(CH3)2 group, a C(CX3)2 group wherein X is a halogen, a CO group, an O atom, a S atom, a SO2 group, a Si(R)2 group wherein R is as defined previously and a N(R) group wherein R is as defined previously;
A is selected from the group consisting of hydrogen, halogen, alkyl, substituted alkyl, nitro, cyano, thioalkyl, alkoxy, substituted alkoxy, aryl and substituted aryl, aliphatic and aromatic esters and combinations thereof from 1 to 20 carbons;n is an integer from 0 to 4; p and q are integers from 1 to 3 when the polyimide is a homopolyimide and are integers from 0 to 3 and 1 to 3 respectively when the polyimide is a copolyimide, and when p and q are greater than 1, the linking group between benzyl or substituted benzyl groups is F; and x, if present, varies from 100 to 0 while y, if present, varies correspondingly from 0 to 100. - View Dependent Claims (25, 26)
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Specification
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Current AssigneeJingxu He, University of Akron
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Original AssigneeUniversity of Akron
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InventorsHarris, Frank W., Cheng, Stephen Z. D.
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Primary Examiner(s)Kight, III, John
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Assistant Examiner(s)HAMPTON HIGHTOWER, PATRICIA
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Application NumberUS08/072,137Time in Patent Office459 DaysField of Search428/1, 428/473.5, 528/125, 528/128, 528/172, 528/173, 528/170, 528/185, 528/188, 528/220, 528/229, 528/350, 528/353, 359/73, 359/63, 359/93, 350/347 R, 350/339 RUS Class Current528/353CPC Class CodesC08G 69/26 derived from polyamines and...C08G 69/265 from at least two different...C08G 69/32 from aromatic diamines and ...C08G 69/44 Polyester-amidesC08G 73/10 Polyimides; Polyester-imide...C08G 73/1039 comprising halogen-containi...C08G 73/106 containing siliconC08G 73/1064 containing sulfurC08G 73/1067 Wholly aromatic polyimides,...C08G 73/1071 Wholly aromatic polyimides ...C08G 73/14 Polyamide-imidesC08G 73/16 Polyester-imidesC09K 2323/027 PolyimideC09K 2323/0271 PolyimidfluorideG02F 1/13363 Birefringent elements, e.g....G02F 1/133634 the refractive index Nz per...G02F 2413/02 Number of plates being 2G02F 2413/07 All plates on one side of t...Y10T 428/31721 Of polyimide
