Biaxial-optical polynorbornene-based film and method of manufacturing the same, integrated optical compensation polarizer having the film and method of manufacturing the polarizer, and liquid crystal display panel containing the film and/or polarizer

An integrated optical compensation polarizer comprising:

• a biaxial-optical compensation film composed of an addition-type polynorbornene-based polymer, in which, when nx is a refractive index in a slow axis direction (x-direction) in-plane of film, ny is a refractive index in a y-direction which is perpendicular to the x-direction in-plane of film, and Nz=(nx−nz)/(nx−ny), the film satisfies the two requirements of nx>ny>nz and 1<Nz≦10, and a polarizer composed of polyvinylalcohol (PVA), which is laminated with said biaxial-optical compensation film and comprises iodine and/or a dichroic dye, wherein the polynorbornene-based polymer is a copolymer obtained by addition-polymerizing two or more norbornene-based monomers composed of a monomer represented by formula (1)
• wherein m is an integer of 0-4;
• and each of R1, R2, R3, and R4 can be the same or different and is a hydrogen atom, a halogen atom, a linear or branched alkyl, alkenyl, or vinyl having 1-20 carbon atoms, a hydrocarbon-substituted or unsubstituted cycloalkyl having 5-12 carbon atoms, a hydrocarbon-substituted or unsubstituted aryl having 6-40 carbon atoms, a hydrocarbon-substituted or unsubstituted aralkyl having 7-15 carbon atoms, an alkynyl having 3-20 carbon atoms, a linear or branched haloalkyl, haloalkenyl, or halovinyl having 1-20 carbon atoms, a hydrocarbon-substituted or unsubstituted halocycloalkyl having 5-12 carbon atoms, a hydrocarbon-substituted or unsubstituted haloaryl having 6-40 carbon atoms, a hydrocarbon-substituted or unsubstituted haloaralkyl having 7-15 carbon atoms, a haloalkynyl having 3-20 carbon atoms, or a polar group consisting of —C(═O)OR6, —R5C(═O)OR6, —OR6, —R5OR6, —OC(O)OR6, —R5OC(═O)OR6, —C(═O)R6, —R5C(O)R6, —OC(═O)R6, —R5OC(═O)R6, —(R5O)p-OR6, —(OR5)p-OR6, —C(═O)—O—C(O)R6 and —R5C(═O)—O—C(═O)R6, wherein R5 is a linear or branched alkyl, haloalkyl, alkenyl, haloalkenyl, or halovinyl having 1-20 carbon atoms, a hydrocarbon-substituted or unsubstituted cycloalkyl or halocycloalkyl having 4-12 carbon atoms, a hydrocarbon-substituted or unsubstituted aryl or haloaryl having 6-40 carbon atoms, a hydrocarbon-substituted or unsubstituted aralkyl or haloaralkyl having 7-15 carbon atoms, or an alkynyl or haloalkynyl having 3-20 carbon atoms;
• R6 is a hydrogen atom, a halogen atom, a linear or branched alkyl, haloalkyl, alkenyl, haloalkenyl, halovinyl, alkoxy, haloalkoxy, carbonyloxy, or halocarbonyloxy having 1-20 carbon atoms, a hydrocarbon-substituted or unsubstituted cycloalkyl or halocycloalkyl having 4-12 carbon atoms, a hydrocarbon-substituted or unsubstituted aryl, haloaryl, aryloxy, or haloaryloxy having 6-40 carbon atoms, a hydrocarbon-substituted or unsubstituted aralkyl or haloaralkyl having 7-15 carbon atoms, or an alkynyl or haloalkynyl having 3-20 carbon atoms;
• and p is an integer of 1-10;
• provided at least one of R1, R2, R3 and R4 is a polar group consisting of —C(═O)OR6, —R5C(═O)OR6, —OR6, —R5OR6, —OC(O)OR6, —R5OC(═O)OR6, —C(═O)R6, —R5C(O)R6, —OC(═O)R6, —R5OC(═O)R6, —(R5O)p-OR6, —(OR5)p-OR6, —C(═O)—O—C(O)R6 and —R5C(═O)—O—C(═O)R6.

A liquid crystal display panel comprising:

• a liquid crystal cell;
• a biaxial-optical compensation film formed on a first surface of the liquid crystal cell;
• a first protective film formed on the biaxial-optical compensation film;
• a first polarizer formed on the first protective film;
• a second protective film formed on the first polarizer;
• a third protective film formed on a second surface of the liquid cell;
• a second polarizer formed on the third protective film;
• and a fourth protective film formed on the second polarizer, in which the biaxial-optical compensation film is composed of an addition-type polynorbornene-based polymer;
• and when nx is a refractive index in an x-direction in-plane of film, ny is a refractive index in a y-direction which is perpendicular to the x-direction in-plane of film, and Nz=(nx−nz)/(nx−ny), the biaxial-optical compensation film satisfies the two requirements of nx>ny>nz and 1<Nz≦10, wherein the polynorbornene-based polymer is a copolymer obtained by addition-polymerizing two or more norbornene-based monomers composed of a monomer represented by formula (1)
• wherein m is an integer of 0-4;
• and each of R1, R2, R3, and R4 can be the same or different and is a hydrogen atom, a halogen atom, a linear or branched alkyl, alkenyl, or vinyl having 1-20 carbon atoms, a hydrocarbon-substituted or unsubstituted cycloalkyl having 5-12 carbon atoms, a hydrocarbon-substituted or unsubstituted aryl having 6-40 carbon atoms, a hydrocarbon-substituted or unsubstituted aralkyl having 7-15 carbon atoms, an alkynyl having 3-20 carbon atoms, a linear or branched haloalkyl, haloalkenyl, or halovinyl having 1-20 carbon atoms, a hydrocarbon-substituted or unsubstituted halocycloalkyl having 5-12 carbon atoms, a hydrocarbon-substituted or unsubstituted haloaryl having 6-40 carbon atoms, a hydrocarbon-substituted or unsubstituted haloaralkyl having 7-15 carbon atoms, a haloalkynyl having 3-20 carbon atoms, or a polar group consisting of —C(═O)OR6, —R5C(═O)OR6, —OR6, —R5OR6, —OC(O)OR6, —R5OC(═O)OR6, —C(═O)R6, —R5C(O)R6, —OC(═O)R6, —R5OC(═O)R6, —(R5O)p-OR6, —(OR5)p-OR6, —C(═O)—O—C(O)R6 and —R5C(═O)—O—C(═O)R6, wherein R5 is a linear or branched alkyl, haloalkyl, alkenyl, haloalkenyl, or halovinyl having 1-20 carbon atoms, a hydrocarbon-substituted or unsubstituted cycloalkyl or halocycloalkyl having 4-12 carbon atoms, a hydrocarbon-substituted or unsubstituted aryl or haloaryl having 6-40 carbon atoms, a hydrocarbon-substituted or unsubstituted aralkyl or haloaralkyl having 7-15 carbon atoms, or an alkynyl or haloalkynyl having 3-20 carbon atoms;
• R6 is a hydrogen atom, a halogen atom, a linear or branched alkyl, haloalkyl, alkenyl, haloalkenyl, halovinyl, alkoxy, haloalkoxy, carbonyloxy, or halocarbonyloxy having 1-20 carbon atoms, a hydrocarbon-substituted or unsubstituted cycloalkyl or halocycloalkyl having 4-12 carbon atoms, a hydrocarbon-substituted or unsubstituted aryl, haloaryl, aryloxy, or haloaryloxy having 6-40 carbon atoms, a hydrocarbon-substituted or unsubstituted aralkyl or haloaralkyl having 7-15 carbon atoms, or an alkynyl or haloalkynyl having 3-20 carbon atoms;
• and p is an integer of 1-10;
• provided at least one of R1, R2, R3 and R4 is a polar group consisting of —C(═O)OR6, —R5C(═O)OR6, —OR6, —R5OR6, —OC(O)OR6, —R5OC(═O)OR6, —C(═O)R6, —R5C(O)R6, —OC(═O)R6, —R5OC(═O)R6, —(R5O)p-OR6, —(OR5)p-OR6, —C(═O)—O—C(O)R6 and —R5C(═O)—O—C(═O)R6.

A liquid crystal display panel comprising:

• a liquid crystal cell;
• an integrated optical compensation polarizer formed on a first surface of the liquid crystal cell, which consists of a biaxial-optical compensation film adjacent to the liquid crystal cell, which also acts as a first protective film, and a first polarizer formed on the biaxial-optical compensation film;
• a second protective film formed on the first polarizer;
• a third protective film formed on a second surface of the liquid cell;
• a second polarizer formed on the third protective film;
• and a fourth protective film formed on the second polarizer, in which the biaxial-optical compensation film is composed of an addition-type polynorbornene-based polymer;
• when nx is a refractive index in an x-direction in-plane of film, ny is a refractive index in a y-direction which is perpendicular to the x-direction in-plane of film, and Nz=(nx−nz)/(nx−ny), the biaxial-optical compensation film satisfies the two requirements of nx>ny>nz and 1<Nz≦10, and the first polarizer is composed of polyvinyl alcohol (PVA) comprising iodine or a dichroic dye, wherein the polynorbornene-based polymer is a copolymer obtained by addition-polymerizing two or more norbornene-based monomers composed of a monomer represented by formula (1)
• wherein m is an integer of 0-4;
• and each of R1, R2, R3, and R4 can be the same or different and is a hydrogen atom, a halogen atom, a linear or branched alkyl, alkenyl, or vinyl having 1-20 carbon atoms, a hydrocarbon-substituted or unsubstituted cycloalkyl having 5-12 carbon atoms, a hydrocarbon-substituted or unsubstituted aryl having 6-40 carbon atoms, a hydrocarbon-substituted or unsubstituted aralkyl having 7-15 carbon atoms, an alkynyl having 3-20 carbon atoms, a linear or branched haloalkyl, haloalkenyl, or halovinyl having 1-20 carbon atoms, a hydrocarbon-substituted or unsubstituted halocycloalkyl having 5-12 carbon atoms, a hydrocarbon-substituted or unsubstituted haloaryl having 6-40 carbon atoms, a hydrocarbon-substituted or unsubstituted haloaralkyl having 7-15 carbon atoms, a haloalkynyl having 3-20 carbon atoms, or a polar group consisting of —C(═O)OR6, —R5C(═O)OR6, —OR6, —R5OR6, —OC(O)OR6, —R5OC(═O)OR6, —C(═O)R6, —R5C(O)R6, —OC(═O)R6, —R5OC(═O)R6, —(R5O)p-OR6, —(OR5)p-OR6, —C(═O)—O—C(O)R6 and —R5C(═O)—O—C(═O)R6, wherein R5 is a linear or branched alkyl, haloalkyl, alkenyl, haloalkenyl, or halovinyl having 1-20 carbon atoms, a hydrocarbon-substituted or unsubstituted cycloalkyl or halocycloalkyl having 4-12 carbon atoms, a hydrocarbon-substituted or unsubstituted aryl or haloaryl having 6-40 carbon atoms, a hydrocarbon-substituted or unsubstituted aralkyl or haloaralkyl having 7-15 carbon atoms, or an alkynyl or haloalkynyl having 3-20 carbon atoms;
• R6 is a hydrogen atom, a halogen atom, a linear or branched alkyl, haloalkyl, alkenyl, haloalkenyl, halovinyl, alkoxy, haloalkoxy, carbonyloxy, or halocarbonyloxy having 1-20 carbon atoms, a hydrocarbon-substituted or unsubstituted cycloalkyl or halocycloalkyl having 4-12 carbon atoms, a hydrocarbon-substituted or unsubstituted aryl, haloaryl, aryloxy, or haloaryloxy having 6-40 carbon atoms, a hydrocarbon-substituted or unsubstituted aralkyl or haloaralkyl having 7-15 carbon atoms, or an alkynyl or haloalkynyl having 3-20 carbon atoms;
• and p is an integer of 1-10;
• provided at least one of R1, R2, R3 and R4 is a polar group consisting of —C(═O)OR6, —R5C(═O)OR6, —OR6, —R5OR6, —OC(O)OR6, —R5OC(═O)OR6, —C(═O)R6, —R5C(O)R6, —OC(═O)R6, —R5OC(═O)R6, —(R5O)p-OR6, —(OR5)p-OR6, —C(═O)—O—C(O)R6 and —R5C(═O)—O—C(═O)R6.

A liquid crystal display panel comprising:

• a liquid crystal cell;
• a first biaxial-optical compensation film formed on a first surface of the liquid crystal cell;
• a first protective film formed on the first biaxial-optical compensation film;
• a first polarizer formed on the first protective film;
• a second protective film formed on the first polarizer;
• a second biaxial-optical compensation film formed on a second surface of the liquid crystal cell;
• a third protective film formed on the second biaxial-optical compensation film;
• a second polarizer formed on the third protective film;
• and a fourth protective film formed on the second polarizer, in which the first and second biaxial-optical compensation films are composed of an addition-type polynorbornene-based polymer;
• and when nx is a refractive index in an x-direction in-plane of film, ny is a refractive index in a y-direction which is perpendicular to the x-direction in-plane of film, and Nz=(nx−nz)/(nx−ny), the first and second biaxial-optical compensation films satisfy the two requirements of nx>ny>nz and 1<Nz≦10, wherein the polynorbornene-based polymer is a copolymer obtained by addition-polymerizing two or more norbornene-based based monomers composed of a monomer represented by formula (1)
• wherein m is an integer of 0-4;
• and each of R1, R2, R3, and R4 can be the same or different and is a hydrogen atom, a halogen atom, a linear or branched alkyl, alkenyl, or vinyl having 1-20 carbon atoms, a hydrocarbon-substituted or unsubstituted cycloalkyl having 5-12 carbon atoms, a hydrocarbon-substituted or unsubstituted aryl having 6-40 carbon atoms, a hydrocarbon-substituted or unsubstituted aralkyl having 7-15 carbon atoms, an alkynyl having 3-20 carbon atoms, a linear or branched haloalkyl, haloalkenyl, or halovinyl having 1-20 carbon atoms, a hydrocarbon-substituted or unsubstituted halocycloalkyl having 5-12 carbon atoms, a hydrocarbon-substituted or unsubstituted haloaryl having 6-40 carbon atoms, a hydrocarbon-substituted or unsubstituted haloaralkyl having 7-15 carbon atoms, a haloalkynyl having 3-20 carbon atoms, or a polar group consisting of —C(═O)OR6, —R5C(═O)OR6, —OR6, —R5OR6, —OC(O)OR6, —R5OC(═O)OR6, —C(═O)R6, —R5C(O)R6, —OC(═O)R6, —R5OC(═O)R6, —(R5O)p-OR6, —(OR5)p-OR6, —C(═O)—O—C(O)R6 and —R5C(═O)—O—C(═O)R6, wherein R5 is a linear or branched alkyl, haloalkyl, alkenyl, haloalkenyl, or halovinyl having 1-20 carbon atoms, a hydrocarbon-substituted or unsubstituted cycloalkyl or halocycloalkyl having 4-12 carbon atoms, a hydrocarbon-substituted or unsubstituted aryl or haloaryl having 6-40 carbon atoms, a hydrocarbon-substituted or unsubstituted aralkyl or haloaralkyl having 7-15 carbon atoms, or an alkynyl or haloalkynyl having 3-20 carbon atoms;
• R6 is a hydrogen atom, a halogen atom, a linear or branched alkyl, haloalkyl, alkenyl, haloalkenyl, halovinyl, alkoxy, haloalkoxy, carbonyloxy, or halocarbonyloxy having 1-20 carbon atoms, a hydrocarbon-substituted or unsubstituted cycloalkyl or halocycloalkyl having 4-12 carbon atoms, a hydrocarbon-substituted or unsubstituted aryl, haloaryl, aryloxy, or haloaryloxy having 6-40 carbon atoms, a hydrocarbon-substituted or unsubstituted aralkyl or haloaralkyl having 7-15 carbon atoms, or an alkynyl or haloalkynyl having 3-20 carbon atoms;
• and p is an integer of 1-10;
• provided at least one of R1, R2, R3 and R4 is a polar group consisting of —C(═O)OR6, —R5C(═O)OR6, —OR6, —R5OR6, —OC(O)OR6, —R5OC(═O)OR6, —C(═O)R6, —R5C(O)R6, —OC(═O)R6, —R5OC(═O)R6, —(R5O)p-OR6, —(OR5)p-OR6, —C(═O)—O—C(O)R6 and —R5C(═O)—O—C(═O)R6.

A liquid crystal display panel comprising:

• a liquid crystal cell;
• an integrated optical compensation polarizer formed on a first surface of the liquid crystal cell, which consists of a first biaxial-optical compensation film adjacent to the liquid crystal cell, which also acts as a first protective film, and a first polarizer formed on the first biaxial-optical compensation film;
• a second protective film formed on the first polarizer;
• an integrated optical compensation polarizer formed on a second surface of the liquid crystal cell, which consists of a second biaxial-optical compensation film adjacent to the liquid crystal cell, which also acts as a third protective film, and a second polarizer formed on the second biaxial-optical compensation film;
• and a fourth protective film formed on the second polarizer, in which the first and second biaxial-optical compensation films are composed of an addition-type polynorbornene-based polymer;
• when nx is a refractive index in an x-direction in-plane of film, ny is a refractive index in a y-direction which is perpendicular to the x-direction in-plane of film, and Nz=(nx−nz)/(nx−ny), the first and second biaxial-optical compensation films satisfy the two requirements of nx>ny>nz and 1<Nz≦10, and the first and second polarizers are composed of polyvinyl alcohol (PVA) including iodine or a dichroic dye, wherein the polynorbornene-based polymer is a copolymer obtained by addition-polymerizing two or more norbornene-based monomers composed of a monomer represented by formula (1)
• wherein m is an integer of 0-4;
• and each of R1, R2, R3, and R4 can be the same or different and is a hydrogen atom, a halogen atom, a linear or branched alkyl, alkenyl, or vinyl having 1-20 carbon atoms, a hydrocarbon-substituted or unsubstituted cycloalkyl having 5-12 carbon atoms, a hydrocarbon-substituted or unsubstituted aryl having 6-40 carbon atoms, a hydrocarbon-substituted or unsubstituted aralkyl having 7-15 carbon atoms, an alkynyl having 3-20 carbon atoms, a linear or branched haloalkyl, haloalkenyl, or halovinyl having 1-20 carbon atoms, a hydrocarbon-substituted or unsubstituted halocycloalkyl having 5-12 carbon atoms, a hydrocarbon-substituted or unsubstituted haloaryl having 6-40 carbon atoms, a hydrocarbon-substituted or unsubstituted haloaralkyl having 7-15 carbon atoms, a haloalkynyl having 3-20 carbon atoms, or a polar group consisting of —C(═O)OR6, —R5C(═O)OR6, —OR6, —R5OR6, —OC(O)OR6, —R5OC(═O)OR6, —C(═O)R6, —R5C(O)R6, —OC(═O)R6, —R5OC(═O)R6, —(R5O)p-OR6, —(OR5)p-OR6, —C(═O)—O—C(O)R6 and —R5C(═O)—O—C(═O)R6, wherein R5 is a linear or branched alkyl, haloalkyl, alkenyl, haloalkenyl, or halovinyl having 1-20 carbon atoms, a hydrocarbon-substituted or unsubstituted cycloalkyl or halocycloalkyl having 4-12 carbon atoms, a hydrocarbon-substituted or unsubstituted aryl or haloaryl having 6-40 carbon atoms, a hydrocarbon-substituted or unsubstituted aralkyl or haloaralkyl having 7-15 carbon atoms, or an alkynyl or haloalkynyl having 3-20 carbon atoms;
• R6 is a hydrogen atom, a halogen atom, a linear or branched alkyl, haloalkyl, alkenyl, haloalkenyl, halovinyl, alkoxy, haloalkoxy, carbonyloxy, or halocarbonyloxy having 1-20 carbon atoms, a hydrocarbon-substituted or unsubstituted cycloalkyl or halocycloalkyl having 4-12 carbon atoms, a hydrocarbon-substituted or unsubstituted aryl, haloaryl, aryloxy, or haloaryloxy having 6-40 carbon atoms, a hydrocarbon-substituted or unsubstituted aralkyl or haloaralkyl having 7-15 carbon atoms, or an alkynyl or haloalkynyl having 3-20 carbon atoms;
• and p is an integer of 1-10;
• provided at least one of R1, R2, R3 and R4 is a polar group consisting of —C(═O)OR6, —R5C(═O)OR6, —OR6, —R5OR6, —OC(O)OR6, —R5OC(═O)OR6, —C(═O)R6, —R5C(O)R6, —OC(═O)R6, —R5OC(═O)R6, —(R5O)p-OR6, —(OR5)p-OR6, —C(═O)—O—C(O)R6 and —R5C(═O)—O—C(═O)R6.