KR20130125325A - Composition for polarizing film, polarizing film and display device including the polarizing film - Google Patents

Composition for polarizing film, polarizing film and display device including the polarizing film Download PDF

Info

Publication number
KR20130125325A
KR20130125325A KR1020130051318A KR20130051318A KR20130125325A KR 20130125325 A KR20130125325 A KR 20130125325A KR 1020130051318 A KR1020130051318 A KR 1020130051318A KR 20130051318 A KR20130051318 A KR 20130051318A KR 20130125325 A KR20130125325 A KR 20130125325A
Authority
KR
South Korea
Prior art keywords
substituted
unsubstituted
group
formula
independently
Prior art date
Application number
KR1020130051318A
Other languages
Korean (ko)
Inventor
김명만
원종훈
정명섭
이용주
문득규
Original Assignee
삼성전자주식회사
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 삼성전자주식회사 filed Critical 삼성전자주식회사
Priority to US13/889,653 priority Critical patent/US20130303677A1/en
Publication of KR20130125325A publication Critical patent/KR20130125325A/en

Links

Images

Classifications

    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08LCOMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L101/00Compositions of unspecified macromolecular compounds
    • C08L101/02Compositions of unspecified macromolecular compounds characterised by the presence of specified groups, e.g. terminal or pendant functional groups
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08LCOMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L65/00Compositions of macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain; Compositions of derivatives of such polymers
    • GPHYSICS
    • G02OPTICS
    • G02BOPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B1/00Optical elements characterised by the material of which they are made; Optical coatings for optical elements
    • G02B1/04Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
    • GPHYSICS
    • G02OPTICS
    • G02BOPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00Optical elements other than lenses
    • G02B5/30Polarising elements

Landscapes

  • Physics & Mathematics (AREA)
  • Chemical & Material Sciences (AREA)
  • General Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Polarising Elements (AREA)

Abstract

The present invention relates to a composition for a polarizing film, including a polymer resin, a dichromatic dye, and a liquid crystal oligomer which has a mesogen part and a kink-structured arylene part; a polarizing film including the composition for a polarizing film; and a display device.

Description

A display device comprising the composition for a polarizing film, a polarizing film, and the said polarizing film TECHNICAL FIELD [DEVICE INCLUDING THE POLARIZING FILM}

It relates to a display device comprising the composition for polarizing film, the polarizing film, and the polarizing film.

A display device such as a liquid crystal display (LCD) and an organic light emitting diode (OLED) device has a polarizing plate attached to the outside of the display panel. The polarizing plate can control the direction of light entering the display panel or light exiting the display panel by passing only light that vibrates in a specific direction and absorbing or reflecting the other light.

The polarizing plate generally includes a polarizer and a protective layer for protecting the polarizer. For example, polyvinyl alcohol (PVA) may be used as the polarizer, and triacetyl cellulose (TAC) may be used as the protective layer.

However, the polarizing plate including the polarizer and the protective layer is not only complicated in the process and has a high production cost, but also the thickness of the polarizing plate may be increased, thereby affecting the thickness of the display.

Accordingly, a polarizing film which does not require a protective layer has been studied.

One embodiment provides a composition for a polarizing film that can improve the polarization characteristics.

Another embodiment provides a polarizing film including the composition for the polarizing film and stretched.

Another embodiment provides a display device including the polarizing film.

According to one embodiment, a polymer resin, a dichroic dye, and a liquid crystal oligomer, the liquid crystal oligomer provides a composition for a polarizing film having a mesogenic moiety, and arylene part of the kink structure.

The liquid crystal oligomer may be represented by the following Chemical Formula 1.

[Formula 1]

T 1 -L 1- (Ar 1 ) n -L 2- (Ar 2 ) m -L 3 -T 2

In Formula 1,

Ar 1 is an arylene portion of a folding structure,

Ar 2 is a mesogenic moiety,

L 1 , L 2 and L 3 are each a linking group,

T 1 and T 2 are each a C1 to C20 aromatic or aliphatic group that does not contain a hydrophilic functional group,

The molar ratios n and m satisfy 0.05 ≦ n ≦ 0.6 and 0.4 ≦ m ≦ 0.95.

Ar 1 of Formula 1 may be represented by the following Formula 2.

(2)

-[X 1 -A 1 -Y 1 ]-

In Formula 2,

A 1 is an arylene group having a folding structure,

X 1 and Y 1 are each independently —C (═O) O—, —OC (═O) —, —C (═O) —, —O—, —C (═N) (R a ) —, -C (= 0) N (R b )-, -N (R c )-, -N (R d ) C (= 0)-, -C (= 0) N (R e )-or a combination thereof Wherein R a to R e are each independently a hydrogen atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a combination thereof.

A 1 of Formula 2 may include at least one selected from the groups listed in Groups 1-1 to 1-6.

[Group 1-1]

Figure pat00001

[Group 1-2]

Figure pat00002

[Group 1-3]

Figure pat00003

[Group 1-4]

Figure pat00004

[Group 1-5]

Figure pat00005

[Group 1-6]

Figure pat00006

In the groups 1-1 to 1-6,

R 20 to R 119 each independently represent a hydrogen atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 To C30 cycloalkenyl group, substituted or unsubstituted C7 to C20 arylalkyl group, substituted or unsubstituted C1 to C20 heteroalkyl group, substituted or unsubstituted C2 to C30 heterocycloalkyl group, substituted or unsubstituted C2 to C30 heteroaryl Groups, substituted or unsubstituted C2 to C30 alkenyl groups, substituted or unsubstituted C2 to C30 alkynyl groups, substituted or unsubstituted C1 to C20 acyl groups, substituted or unsubstituted amino groups, halogen groups, halogen-containing groups or these Is a combination of

W is a single bond, -O-, -C (= 0)-, -S-, -SO 2- , -N 2- , substituted or unsubstituted C1 to C30 alkylene group, substituted or unsubstituted C3 to C30 Cycloalkylene group, substituted or unsubstituted C1 to C30 oxyalkylene group, substituted or unsubstituted C6 to C30 arylene group, substituted or unsubstituted C6 to C30 oxyarylene group, substituted or unsubstituted C6 to C30 heteroarylene group , A substituted or unsubstituted C6 to C30 oxyheteroarylene group or a combination thereof.

Ar 2 of Formula 1 may be represented by the following Formula 3.

(3)

-[X 2 -A 2 -Y 2 ]-

In Formula 3,

A 2 is a substituted or unsubstituted C3 to C30 cycloalkylene group, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C3 to C30 heterocycloalkylene group, a substituted or unsubstituted C3 to C30 heteroarylene group Or a group comprising a combination thereof

X 2 and Y 2 are each independently —O—, —C (═O) —, a substituted or unsubstituted C1 to C30 alkylene group, a substituted or unsubstituted C1 to C30 oxyalkylene group, or a combination thereof.

A 2 of Formula 3 may include at least one selected from the groups listed in Group 2 below.

[Group 2]

Figure pat00007

In group 2 above,

Z 1 to Z 6 are each independently a single bond or -O-, -C (= 0)-, -S-, -SO 2- , -N 2- , a substituted or unsubstituted C1 to C20 alkylene group, Substituted or unsubstituted C1 to C20 oxyalkylene group, substituted or unsubstituted C6 to C30 arylene group, substituted or unsubstituted C6 to C30 oxyarylene group, substituted or unsubstituted C6 to C30 heteroarylene group , A substituted or unsubstituted C6 to C30 oxyheteroarylene group or a combination thereof,

R 150 to R 164 each independently represent hydrogen, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 cycloalkenyl group, substituted or unsubstituted C7 to C20 arylalkyl group, substituted or unsubstituted C1 to C20 heteroalkyl group, substituted or unsubstituted C2 to C30 heterocycloalkyl group, substituted or unsubstituted C2 to C30 heteroaryl group , Substituted or unsubstituted C2 to C30 alkenyl group, substituted or unsubstituted C2 to C30 alkynyl group, substituted or unsubstituted C1 to C20 acyl group, substituted or unsubstituted amino group, halogen group, halogen-containing group or It is a combination.

Ar 2 of Chemical Formula 1 may be represented by Chemical Formula 3a.

[Chemical Formula 3]

-[X 21 -A 21 -Y 21 ] k1- [X 22 -A 22 -Y 22 ] k2- [X 23 -A 23 -Y 23 ] k3- [X 24 -A 24 -Y 24 ] k4-

In the above formula (3a)

A 21 , A 22 , A 23 and A 24 are each independently a substituted or unsubstituted C3 to C30 cycloalkylene group, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C3 to C30 heterocycloalkylene group , A substituted or unsubstituted C3 to C30 hetero arylene group or a combination thereof,

X 21 , X 22 , X 23 , X 24 , Y 21 , Y 22 , Y 23 and Y 24 are each independently —O—, —C (═O) —, a substituted or unsubstituted C1 to C20 alkylene group, A substituted or unsubstituted C1 to C20 oxyalkylene group or a combination thereof,

k 1 to k 4 are each independently 0 to 50,

At least one of k 1 to k 4 is not zero.

T 1 and T 2 of Formula 1 may each independently include at least one selected from functional groups represented by Formulas 4-1 to 4-12.

[Formula 4-1]

Figure pat00008

In Chemical Formula 4-1,

n 1 is an integer of 0 to 6,

R 1 is a hydrogen atom, a halogen atom, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C6 to C30 is an aryloxy group which is a substituent, when n 1 is 2 or more, the substituents may be the same or different from each other,

[Formula 4-2]

Figure pat00009

In Chemical Formula 4-2,

n 2 is 1, n 3 is an integer of 0 to 3,

R 2 and R 3 are each independently a hydrogen atom, a halogen atom, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C6 to C30 aryl group, Or a substituent which is a substituted or unsubstituted C6 to C30 aryloxy group, when n 3 is 2 or more, the substituents may be the same or different from each other,

[Formula 4-3]

Figure pat00010

In Chemical Formula 4-3,

n 4 is an integer of 0 to 2,

R 4 is a hydrogen atom, a halogen atom, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted A substituent which is an aryloxy group of C6 to C30, and when n 4 is 2, the substituents may be the same or different from each other,

[Formula 4-4]

Figure pat00011

In Chemical Formula 4-4,

n 5 is an integer of 0 to 8,

R 5 is a hydrogen atom, a halogen atom, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C6 to C30 is an aryloxy group which is a substituent, when n 5 is 2 or more, the substituents may be the same or different from each other,

[Formula 4-5]

Figure pat00012

In Chemical Formula 4-5,

n 6 is an integer of 0 to 7,

R 6 is a hydrogen atom, a halogen atom, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C6 to C30 is an aryloxy group which is a substituent, when n 6 is 2 or more, the substituents may be the same or different from each other,

[Formula 4-6]

Figure pat00013

In Chemical Formula 4-6,

n 7 is an integer of 0 to 9,

R 7 is a hydrogen atom, a halogen atom, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C6 to C30 is an aryloxy group which is a substituent, when n 7 is 2 or more, the substituents may be the same or different from each other,

[Formula 4-7]

Figure pat00014

In Chemical Formula 4-7,

n 8 and n 9 are each independently an integer of 0 to 6,

R 8 and R 9 are each independently a hydrogen atom, a halogen atom, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C6 to C30 aryl group, Or a substituted or unsubstituted C6 to C30 aryloxy group, and when n 8 and n 9 are each 2 or more, the substituents may be different from each other,

Q 1 and Q 2 are each independently a methylene group, -O- or -S-,

m 1 is an integer of 1 to 3,

[Formula 4-8]

Figure pat00015

In Chemical Formula 4-8,

n 10 is an integer from 0 to 7, n 11 is an integer from 0 to 6,

R 10 and R 11 are each independently a hydrogen atom, a halogen atom, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C6 to C30 aryl group, Or a substituent which is a substituted or unsubstituted C6 to C30 aryloxy group, when n 10 and n 11 are each 2 or more, the substituents may be different from each other,

Q 3 and Q 4 are each independently a methylene group, O or S,

m 2 is an integer of 1 to 3,

[Chemical Formula 4-9]

Figure pat00016

In Chemical Formula 4-9,

n 12 is an integer from 0 to 7, n 13 is an integer from 0 to 6, n 14 is an integer from 0 to 8,

R 12 to R 14 are each independently a hydrogen atom, a halogen atom, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C6 to C30 aryl group, Or a substituted or unsubstituted C6 to C30 aryloxy group, and when n 12 to n 14 are each 2 or more, the substituents may be different from each other,

Q 5 and Q 6 are each independently a methylene group, O or S,

m 3 and m 4 are each independently an integer of 1 to 3,

[Formula 4-10]

Figure pat00017

In Chemical Formula 4-10,

n 15 is an integer of 0 to 2,

R 15 is a hydrogen atom, a halogen atom, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted It is a substituent which is an aryloxy group of C6-C30.

[Formula 4-11]

Figure pat00018

[Formula 4-12]

Figure pat00019

The liquid crystal oligomer may have a melting point of about 250 ° C. or less.

The solubility parameter of the liquid crystal oligomer may be about 15 to 30.

The polymer resin may include polyolefin resin, polyethylene terephthalate (PET), glycol modified polyethylene terephthalate (PETG), polyester, nylon, copolymers thereof, or a combination thereof.

The solubility parameter difference between the polymer resin and the dichroic dye may be less than 7.4.

The polymer resin may be a polyolefin resin, the dichroic dye may be represented by the following formula (1).

[Formula 1]

Figure pat00020

In Formula 1,

Ar a To Ar c are each independently a substituted or unsubstituted C6 to C15 aryl group,

R a and R b are each independently a substituted or unsubstituted C1 to C30 aliphatic organic group, a substituted or unsubstituted C1 to C30 aromatic organic group, a substituted or unsubstituted C1 to C30 heteroaliphatic organic group, a substituted or unsubstituted C1 to C30 heteroaromatic organic group or a combination thereof,

o and p are each independently 0 or 1.

In Formula 1, R a is a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C1 to C20 thioalkyl group, a substituted or unsubstituted C1 to C30 ketone group , Substituted or unsubstituted C1 to C30 oxycarbonyl group, substituted or unsubstituted C2 to C20 alkenyl group, substituted or unsubstituted C2 to C30 alkynyl group, or a combination thereof, R b is substituted or unsubstituted C1 To C30 alkyl group, substituted or unsubstituted C6 to C20 aryl group, C1 to C20 alkoxy group, substituted or unsubstituted C1 to C20 thioalkyl group, -NR c R d Or a combination thereof, wherein R c and R d are each independently hydrogen, a substituted or unsubstituted C1 to C10 alkyl group, or may be connected to each other to form a ring.

In Formula 1, o and p may each be 1, R a is a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C1 to C20 thioalkyl group, Substituted or unsubstituted C1 to C30 ketone group, substituted or unsubstituted C1 to C30 oxycarbonyl group, substituted or unsubstituted C2 to C20 alkenyl group, substituted or unsubstituted C2 to C30 alkynyl group, or a combination thereof , R b is a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, -NR c R d or a combination thereof, wherein R c and R d are each independently hydrogen, substituted or It may be an unsubstituted C1 to C10 alkyl group or connected to each other to form a ring.

In Formula 1, o and p may each be 0, R a is a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C1 to C20 thioalkyl group, Substituted or unsubstituted C1 to C30 ketone group, substituted or unsubstituted C1 to C30 oxycarbonyl group, substituted or unsubstituted C2 to C20 alkenyl group, substituted or unsubstituted C2 to C30 alkynyl group, or a combination thereof , R b is a substituted or unsubstituted C1 to C30 alkyl group, -NR c R d Or a combination thereof, wherein R c and R d are each independently hydrogen, a substituted or unsubstituted C1 to C10 alkyl group, or may be connected to each other to form a ring.

In Formula 1, o may be 1 and p may be 0, R a is a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C1 to C20 thioalkyl group , Substituted or unsubstituted C1 to C30 ketone group, substituted or unsubstituted C1 to C30 oxycarbonyl group, substituted or unsubstituted C2 to C20 alkenyl group, substituted or unsubstituted C2 to C30 alkynyl group, or a combination thereof R b is a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, -NR c R d or a combination thereof, wherein R c and R d are each independently hydrogen, substituted Or an unsubstituted C1 to C10 alkyl group or may be linked to each other to form a ring.

The liquid crystal oligomer and the dichroic dye may be included in an amount of about 0.01 to 10 parts by weight and about 0.05 to 5 parts by weight based on 100 parts by weight of the polymer resin.

According to another embodiment, the polarizing film including the composition for polarizing film described above and uniaxially stretched is provided.

According to another embodiment, a display device including the polarizing film is provided.

The polarization characteristic can be improved by extending the stretching orientation of the dichroic dye without affecting the light transmittance.

1 is a schematic view showing a polarizing film according to one embodiment,
2 is a cross-sectional view illustrating a liquid crystal display device according to one embodiment,
3 is a graph showing the polarization efficiency of the polarizing film according to Examples 1-1, 1-2 and Comparative Example 1,
4 is a graph showing absorbance at a wavelength region of 380 to 780 nm of the polarizing film according to Example 2 and Comparative Example 2,
5 is a graph showing dichroic ratios of polarizing films according to Example 2 and Comparative Example 2. FIG.

Hereinafter, exemplary embodiments of the present invention will be described in detail so that those skilled in the art can easily carry out the present invention. The present invention may, however, be embodied in many different forms and should not be construed as limited to the embodiments set forth herein.

Unless otherwise defined herein, 'substituted' means that a hydrogen atom in the compound is a halogen atom (F, Br, Cl or I), a hydroxy group, an alkoxy group, a nitro group, a cyano group, an amino group, A carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid or a salt thereof, a C1 to C20 alkyl group, a C2 to C20 alkenyl group, a C2 to C20 alkenyl group, a C2 to C20 alkenyl group, C6 to C30 arylalkyl groups, C7 to C30 arylalkyl groups, C1 to C4 alkoxy groups, C1 to C20 heteroalkyl groups, C3 to C20 heteroarylalkyl groups, C3 to C30 cycloalkyl groups, C3 to C15 cycloalkenyl groups, C6 to C30 heteroaryl groups, C15 cycloalkynyl group, a C2 to C20 heterocycloalkyl group, and combinations thereof.

In addition, unless otherwise defined herein, "hetero" means containing 1 to 3 heteroatoms selected from N, O, S and P.

Hereinafter, a composition for a polarizing film according to one embodiment is described.

The composition for a polarizing film according to one embodiment includes a polymer resin, a dichroic dye, and a liquid crystal oligomer.

The polymer resin is not particularly limited as long as it is a transparent resin capable of transmitting light, and examples thereof include polyester resins such as polyethylene terephthalate (PET), glycol modified polyethylene terephthalate (PETG), and polyethylene naphthalate; Acrylic resins such as polymethyl (meth) acrylate; Styrene-based resins such as polystyrene (PS) and acrylonitrile-styrene copolymers; Polycarbonate resin; Polyolefin resins such as polyethylene (PE), polypropylene (PP) and copolymers thereof; Vinyl chloride resin; Amide resins such as nylon and aromatic polyamides; Imide resin; Sulfonic resin; Polyether sulfone resin; Polyether-ether ketone resin; Polyphenylene sulfide resin; Vinyl alcohol-based resins; Vinylidene chloride-based resins; Vinyl butyral resin; Allylate series resin; Polyoxymethylene type resin; Epoxy resin; Copolymers thereof or combinations thereof.

Among these, the polymer resin is, for example, a polyolefin resin; Polyesters such as polyethylene terephthalate (PET), polyethylenetaphthalate (PEN) and glycol modified polyethylene terephthalate (PETG); Nylon, copolymers thereof, or a combination thereof, and may be, for example, a polyolefin resin.

The polyolefin resin can be, for example, a mixture of polypropylene (PP) and polyethylene-polypropylene copolymer (PE-PP).

The polypropylene (PP) may have a melt flow index (MFI) of, for example, from about 0.1 g / 10 min to about 5 g / 10 min. Here, the melt flow index (MFI) represents the amount of polymer flowing in a molten state per 10 minutes, which is related to the viscosity of the polymer in a molten state. That is, the smaller the melt flow index (MFI), the higher the viscosity of the polymer and the higher the melt flow index (MFI), the smaller the viscosity of the polymer. When the melt flow index (MFI) of the polypropylene is within the above range, the workability can be effectively improved and the physical properties of the final product can be effectively improved. Specifically, the polypropylene may have a melt flow index (MFI) of from about 0.5 g / 10 min to about 5 g / 10 min.

The polyethylene-polypropylene copolymer (PE-PP) may comprise about 1% to about 50% by weight of ethylene groups relative to the total content of the copolymer. When the content of the ethylene group in the polyethylene-polypropylene copolymer (PE-PP) is within the above range, the phase separation of the polypropylene and the polyethylene-polypropylene copolymer (PE-PP) can be effectively prevented or alleviated. In addition, it is possible to increase elongation at the time of stretching while having excellent light transmittance and orientation, and to realize improved polarization characteristics. Specifically, the polyethylene-polypropylene copolymer (PE-PP) may comprise about 1 wt% to about 25 wt% ethylene groups relative to the total amount of the copolymer.

The polyethylene-polypropylene copolymer (PE-PP) may have a melt flow index (MFI) of from about 5 g / 10 min to about 15 g / 10 min. When the melt flow index (MFI) of the polyethylene-polypropylene copolymer (PE-PP) is within the above range, the workability can be effectively improved and the physical properties of the final product can be effectively improved. Specifically, the polyethylene-polypropylene copolymer (PE-PP) may have a melt flow index (MFI) of about 10 g / 10 min to about 15 g / 10 min.

The polyolefin resin may include the polypropylene (PP) and the polyethylene-polypropylene copolymer (PE-PP) in a weight ratio of about 1: 9 to about 9: 1. When the polypropylene (PP) and the polyethylene-polypropylene copolymer (PE-PP) are contained within the above ranges, crystallization of the polypropylene can be prevented and the haze characteristics can be effectively improved while having excellent mechanical strength. Specifically, the polyolefin resin 71 is prepared by mixing the polypropylene (PP) and the polyethylene-polypropylene copolymer (PE-PP) in a weight ratio of about 4: 6 to about 6: 4, more specifically about 5: 5 .

The polyolefin resin may have a melt flow index (MFI) of about 1 g / 10 min to about 15 g / 10 min. When the melt flow index (MFI) of the polyolefin resin is within the above range, excessive crystals may not be formed in the resin to ensure excellent light transmittance and have a viscosity suitable for manufacturing into a film, thereby improving workability. . Specifically, the polyolefin resin may have a melt flow index (MFI) of about 5g / 10min to about 15g / 10min.

The polyolefin resin may have a haze of about 5% or less. Since the polyolefin resin has a haze in the above range, transmittance may be increased to have excellent optical properties. Specifically, the polyolefin resin may have a haze of about 2% or less, and more specifically, may have a haze of about 0.5% to about 2%.

The polyolefin resin may have a crystallinity of about 50% or less. By the said polyolefin resin having the crystallinity of the said range, haze can be lowered and the outstanding optical characteristic can be achieved. Specifically, the polyolefin resin may have a crystallinity of about 30% to about 50%.

The dichroic dye is a material having a property of transmitting one polarization orthogonal component of two polarization orthogonal components to a predetermined wavelength region.

The dichroic dye may be dispersed in the polymer resin and stretched in one direction to be arranged in one direction.

Such dichroic dyes include, for example, azo compounds, anthraquinone compounds, phthalocyanine compounds, azomethine compounds, indigoid or thioindigoid compounds, and merocyanine compounds. Compound, 1,3-bis dicyano methylene indan (1,3-bis (dicyanomethylene) indan) compound, azulene compound, quinophthalonic compound, triphenodioxazine (triphenodioxazine ) -Based compound, indolo [2,3, b] quinoxaline-based compound, imidazo [1,2-b] -1,2,4 triazine (imidazo [1] , 2-b] -1,2,4 triazines) compound, tetrazine (tetrazines) compound, benzo (benzo) compound, naphtoquinones compound or a compound having a molecular skeleton of a combination thereof Can be mentioned.

The dichroic dye may be selected from compounds having a difference in solubility parameters from the polymer resin of less than about 7.4. The solubility parameter indicates a degree of interaction between two or more kinds of compounds. The smaller the solubility parameter difference between the compounds, the greater the interaction. The larger the solubility parameter between the compounds, the less the interaction. Means that.

The solubility parameter is related to the structure of the compound, and by having a difference in the solubility parameter in the above range can increase the interaction between the polymer resin and the dichroic dye during processing of the polarizing film to increase the melt mixing, and thus The dichroic dyes may be prevented from agglomerating in the polymer resin and the dichroic dye may be uniformly dispersed in the polymer resin.

Hildebrand solubility parameters are used to calculate the compatibility of the polymer resin with the dichroic dye.

Intermolecular cohesion is caused by the combination of van der Waals and dipole moments between molecules. Cohesive energy (Ecoh) is defined as the energy responsible for such cohesion. This cohesive energy can be expressed by the following equation 1 as a change in internal energy per mole.

[Relationship 1]

E coh = ΔU = ΔH-R · ΔT

In Equation 1, E coh is the cohesive energy, ΔU is the amount of change of internal energy per mole, ΔH is the enthalpy change, R is a gas constant, ΔT is the temperature change.

In addition, the cohesive energy per unit volume may be defined as a cohesive energy density (CED), and the cohesive energy density (CED) may be represented by the following Equation 2.

[Relation 2]

CED = (ΔH-R · ΔT) / Vm

In Equation 2, CED is a cohesive energy density, ΔH is an enthalpy change, R is a gas constant, ΔT is a temperature change, and Vm is a molar volume.

The cohesive energy density is used by Hildebrand to define a solubility parameter that can numerically express the solubility, and the solubility parameter can be calculated according to the following equation (3) using the density or molar volume at a specific temperature.

[Relation 3]

δ = (CED) 0.5 = (ΣEcoh i /? Vm i ) 0.5

In Equation 3, δ is solubility parameter, CED is cohesive energy density and Ecoh i is cohesive energy for intramolecular functional group i Vm i is the molar volume.

The Hildebrand solubility parameter values used in the design of dichroic dyes can be calculated through the group contribution of molecules.

The group contribution of cohesive energy (Ecoh) and molar volume (Vm) used to calculate the solubility parameter of the dichroic dye is Polym . Eng . Sci . 1974 , 14 , 147; J. Appl . Polym. Sci . 2005 , 96 , 416.

For example, when the polymer resin is a polyolefin resin, specifically a mixture of the aforementioned polypropylene (PP) and polyethylene-polypropylene copolymer (PE-PP), the polyolefin resin may have a solubility parameter of about 15 to 18.

In this case, the dichroic dye may be selected from compounds having a solubility parameter of less than 24, for example, the dichroic dye may include a compound represented by the following Chemical Formula 1.

[Formula 1]

Figure pat00021

In Formula 1,

Ar a To Ar c are each independently a substituted or unsubstituted C6 to C15 aryl group,

R a and R b are each independently a substituted or unsubstituted C1 to C30 aliphatic organic group, a substituted or unsubstituted C1 to C30 aromatic organic group, a substituted or unsubstituted C1 to C30 heteroaliphatic organic group, a substituted or unsubstituted C1 to C30 heteroaromatic organic group or a combination thereof,

o and p are each independently 0 or 1.

In Formula 1, Ar a to Ar c may include, for example, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthalene group, and a substituted or unsubstituted biphenyl group. In this case, the substituted phenylene group, the substituted naphthalene group and the substituted biphenyl group may be substituted with, for example, a C1 to C10 alkyl group, a halogen group or a combination thereof.

In Formula 1, R a is a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C1 to C20 thioalkyl group, a substituted or unsubstituted C1 to C30 ketone group , Substituted or unsubstituted C1 to C30 oxycarbonyl group, substituted or unsubstituted C2 to C20 alkenyl group, substituted or unsubstituted C2 to C30 alkynyl group, or a combination thereof, R b is substituted or unsubstituted C1 To C30 alkyl group, substituted or unsubstituted C6 to C20 aryl group, C1 to C20 alkoxy group, substituted or unsubstituted C1 to C20 thioalkyl group, -NR c R d Or a combination thereof, wherein R c and R d are each independently hydrogen, a substituted or unsubstituted C1 to C10 alkyl group, or may be connected to each other to form a ring.

For example, in Formula 1, when o and p are each 1,

R a is a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C1 to C20 thioalkyl group, a substituted or unsubstituted C1 to C30 ketone group, a substituted or unsubstituted C1 to C30 oxycarbonyl group, substituted or unsubstituted C2 to C20 alkenyl group, substituted or unsubstituted C2 to C30 alkynyl group, or a combination thereof,

R b is a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, a C1 to C20 alkoxy group, a substituted or unsubstituted C1 to C20 thioalkyl group, -NR c R d or a combination thereof Wherein R c and R d are each independently hydrogen, a substituted or unsubstituted C1 to C10 alkyl group, or may be connected to each other to form a ring.

Table 1 below shows examples of dichroic dyes in which o and p are each 1.

number rescue Solubility parameter 1-1-1

Figure pat00022
22.6 1-1-2
Figure pat00023
23.3
1-1-3
Figure pat00024
23.1
1-1-4
Figure pat00025
21.9
1-1-5
Figure pat00026
22.5
1-1-6
Figure pat00027
22.3
1-1-7
Figure pat00028
22.5
1-1-8
Figure pat00029
21.9
1-1-9
Figure pat00030
22.0
1-1-10
Figure pat00031
22.5
1-1-11
Figure pat00032
23.6
1-1-12
Figure pat00033
22.3

For example, in Formula 1, when o and p are each 0,

R a is a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C1 to C20 thioalkyl group, a substituted or unsubstituted C1 to C30 ketone group, a substituted or unsubstituted A C1 to C30 oxycarbonyl group, a substituted or unsubstituted C2 to C20 alkenyl group, a substituted or unsubstituted C2 to C30 alkynyl group, or a combination thereof,

R b is a substituted or unsubstituted C1 to C30 alkyl group, -NR c R d Or a combination thereof, wherein R c and R d are each independently hydrogen, a substituted or unsubstituted C1 to C10 alkyl group, or may be connected to each other to form a ring.

Table 2 below shows examples of dichroic dyes in which o and p are each zero.

number rescue Solubility parameter 1-2-1

Figure pat00034
21.9 1-2-2
Figure pat00035
23.4
1-2-3
Figure pat00036
21.4
1-2-4
Figure pat00037
21.7
1-2-5
Figure pat00038
21.7
1-2-6
Figure pat00039
21.4

For example, in Formula 1, when o is 1 and p is 0,

R a is a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C1 to C20 thioalkyl group, a substituted or unsubstituted C1 to C30 ketone group, a substituted or unsubstituted C1 to C30 oxycarbonyl group, substituted or unsubstituted C2 to C20 alkenyl group, substituted or unsubstituted C2 to C30 alkynyl group, or a combination thereof,

R b is a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, -NR c R d Or a combination thereof, wherein R c and R d are each independently hydrogen, a substituted or unsubstituted C1 to C10 alkyl group, or may be connected to each other to form a ring.

Table 3 below shows examples of dichroic dyes where o is 1 and p is 0.

number rescue Solubility parameter 1-3-1

Figure pat00040
21.7 1-3-2
Figure pat00041
22.1
1-3-3
Figure pat00042
23.1
1-3-4
Figure pat00043
23.0
1-3-5
Figure pat00044
23.3
1-3-6
Figure pat00045
22.6

The dichroic dye may have a dichroic ratio of about 1.5 to about 14. It may be about 3 to 12 within the above range, and may be about 5 to 10 within the above range. Here, the dichroic ratio is a value obtained by dividing the planar polarization absorption in the direction parallel to the axis of the polymer by the polarization absorption in the vertical direction, and may represent the degree of dichroic dyes arranged side by side in one direction. By having a dichroic ratio in the above range, the dichroic dye may have sufficient compatibility with the polymer resin, thereby enabling melt mixing and inducing the orientation of the dichroic dye according to the orientation of the polymer chain. Can be improved.

The decomposition temperature of the dichroic dye may be at least about 245 ° C. Here, the decomposition temperature refers to the temperature at which the weight of the dichroic dye is reduced by 5% relative to the initial weight.

The dichroic dye may be included in an amount of about 0.05 to 5 parts by weight based on 100 parts by weight of the polymer resin. It is possible to exhibit sufficient polarization characteristics by being included in the above range. It may be included in the range of about 0.05 to 1.5 parts by weight, more specifically about 0.05 to 1 part by weight based on 100 parts by weight of the polymer resin.

The liquid crystal oligomer may have a rigid-rod shape extending in one direction and may be melted and mixed with the dichroic dye in the polymer resin to induce a stretch orientation of the dichroic dye in one direction. Accordingly, it is possible to increase the stretching orientation of the dichroic dye in the polymer resin and consequently to improve the polarization characteristics.

The liquid crystal oligomer has a mesogenic unit and a kine-forming arylene unit having a kink structure.

The mesogen portion is a portion that maintains a rigid-rod shape of the liquid crystal oligomer and may exhibit liquid crystal such as thermotropic.

The arylene portion of the bent structure refers to a portion including an arylene group of the bent structure, and the arylene group of the bent structure refers to a structure in which two connecting portions of the arylene group do not form a straight structure. For example, in the case of phenylene, para-phenyl having o-phenylene and m-phenylene in which the connecting portions do not form a straight structure is included in the arylene group of the above-described folding structure, and the connecting portions form a linear structure. Phenyl (p-phenylene) is not included in the arylene group of the folding structure. The arylene group includes both a substituted or unsubstituted arylene group, and may be, for example, a C6 to C30 arylene group.

The liquid crystal oligomer may have a low melting point by having the arylene portion having the bent structure. Therefore, the liquid crystal oligomer may be melt mixed with the polymer resin at the melting temperature of the polymer resin to be uniformly dispersed in the polymer resin, thereby preventing the transmittance of the polarizing film from being lowered by the liquid crystal oligomer. Can be.

The liquid crystal oligomer may have a melting point that can be melt mixed with the polymer resin at the processing temperature of the polarizing film, for example, the melting point of the liquid crystal oligomer may be about 250 ℃ or less. It may be about 100 to 250 ℃ within the above range.

The liquid crystal oligomer may have a molecular weight of about 500 to 5,000. By having the molecular weight in the above range can be uniformly dispersed in the polymer resin to induce the orientation of the dichroic dye in one direction.

The liquid crystal oligomer may be represented by the following Chemical Formula 1.

[Formula 1]

T 1 -L 1- (Ar 1 ) n -L 2- (Ar 2 ) m -L 3 -T 2

In Formula 1,

Ar 1 is a substituted arylene moiety of a folding structure,

Ar 2 is a mesogenic moiety,

L 1 , L 2 and L 3 are each a linking group,

T 1 and T 2 are each a C1 to C20 aromatic or aliphatic group that does not include hydrophilic functional groups such as, for example, -OH, -COOH, NH2,

The molar ratios n and m satisfy 0.05 ≦ n ≦ 0.6 and 0.4 ≦ m ≦ 0.95.

Ar 1 of Formula 1 may be represented by, for example, the following Formula 2.

(2)

-[X 1 -A 1 -Y 1 ]-

In Formula 2,

A 1 is an arylene group having a folding structure,

X 1 and Y 1 are each independently —C (═O) O—, —OC (═O) —, —C (═O) —, —O—, —C (═N) (R a ) —, -C (= 0) N (R b )-, -N (R c )-, -N (R d ) C (= 0)-, -C (= 0) N (R e )-or a combination thereof Wherein R a to R e are each independently a hydrogen atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a combination thereof.

A 1 , that is, the arylene group of the folding structure of Formula 2 may include at least one selected from the groups listed in the following groups 1-1 to 1-6.

[Group 1-1]

Figure pat00046

[Group 1-2]

Figure pat00047

[Group 1-3]

Figure pat00048

[Group 1-4]

Figure pat00049

[Group 1-5]

Figure pat00050

[Group 1-6]

Figure pat00051

In the groups 1-1 to 1-6,

R 20 to R 119 each independently represent a hydrogen atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 To C30 cycloalkenyl group, substituted or unsubstituted C7 to C20 arylalkyl group, substituted or unsubstituted C1 to C20 heteroalkyl group, substituted or unsubstituted C2 to C30 heterocycloalkyl group, substituted or unsubstituted C2 to C30 heteroaryl Groups, substituted or unsubstituted C2 to C30 alkenyl groups, substituted or unsubstituted C2 to C30 alkynyl groups, substituted or unsubstituted C1 to C20 acyl groups, substituted or unsubstituted amino groups, halogen groups, halogen-containing groups or these Is a combination of

W is a single bond, -O-, -C (= 0)-, -S-, -SO 2- , -N 2- , substituted or unsubstituted C1 to C30 alkylene group, substituted or unsubstituted C3 to C30 Cycloalkylene group, substituted or unsubstituted C1 to C30 oxyalkylene group, substituted or unsubstituted C6 to C30 arylene group, substituted or unsubstituted C6 to C30 oxyarylene group, substituted or unsubstituted C6 to C30 heteroarylene group , A substituted or unsubstituted C6 to C30 oxyheteroarylene group or a combination thereof.

In Groups 1-1 to 1-6, only one substituent (R 20 to R 119 ) is represented in one ring, but is not limited thereto, and may have two or more substituents in one ring, and each of these may be independently listed above. May be selected from substituents.

Ar 2 , that is, the mesogenic group of Formula 1 may have at least one ring, and for example, may be represented by the following Formula 3.

(3)

-[X 2 -A 2 -Y 2 ]-

In Formula 3,

A 2 is a substituted or unsubstituted C3 to C30 cycloalkylene group, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C3 to C30 heterocycloalkylene group, a substituted or unsubstituted C3 to C30 hetero arylene group Or a group comprising a combination thereof,

X 2 and Y 2 are each independently —O—, —C (═O) —, a substituted or unsubstituted C1 to C30 alkylene group, a substituted or unsubstituted C1 to C30 oxyalkylene group, or a combination thereof.

A 2 of Formula 3 may include at least one selected from the groups listed in Group 2, for example.

[Group 2]

Figure pat00052

In group 2 above,

Z 1 to Z 6 are each independently a single bond or -O-, -C (= 0)-, -S-, -SO 2- , -N 2- , a substituted or unsubstituted C1 to C20 alkylene group, Substituted or unsubstituted C1 to C20 oxyalkylene group, substituted or unsubstituted C6 to C30 arylene group, substituted or unsubstituted C6 to C30 oxyarylene group, substituted or unsubstituted C6 to C30 heteroarylene group , A substituted or unsubstituted C6 to C30 oxyheteroarylene group or a combination thereof,

R 150 to R 164 each independently represent hydrogen, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 cycloalkenyl group, substituted or unsubstituted C7 to C20 arylalkyl group, substituted or unsubstituted C1 to C20 heteroalkyl group, substituted or unsubstituted C2 to C30 heterocycloalkyl group, substituted or unsubstituted C2 to C30 heteroaryl group , Substituted or unsubstituted C2 to C30 alkenyl group, substituted or unsubstituted C2 to C30 alkynyl group, substituted or unsubstituted C1 to C20 acyl group, substituted or unsubstituted amino group, halogen group, halogen-containing group or It is a combination.

Ar 2 of Formula 1 may be a structure in which one or more of the same or different structures are connected to each other, for example, may be represented by the following Formula 3a.

[Chemical Formula 3]

-[X 21 -A 21 -Y 21 ] k1- [X 22 -A 22 -Y 22 ] k2- [X 23 -A 23 -Y 23 ] k3- [X 24 -A 24 -Y 24 ] k4-

In the above formula (3a)

A 21 , A 22 , A 23 and A 24 are each independently a substituted or unsubstituted C3 to C30 cycloalkylene group, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C3 to C30 heterocycloalkylene group , A substituted or unsubstituted C3 to C30 hetero arylene group or a combination thereof

X 21 , X 22 , X 23 , X 24 , Y 21 , Y 22 , Y 23 and Y 24 are each independently —O—, —C (═O) —, a substituted or unsubstituted C1 to C20 alkylene group, A substituted or unsubstituted C1 to C20 oxyalkylene group or a combination thereof,

k 1 to k 4 are each independently 0 to 50,

At least one of k 1 to k 4 is not zero.

A 21 , A 22 , A 23, and A 24 of Formula 3a may each independently include at least one selected from, for example, a group listed in Group 2.

L 1 , L 2 and L 3 of Formula 1 are each a linking group, such as a single bond, a substituted or unsubstituted C1 to C30 alkylene group, a substituted or unsubstituted C3 to C30 cycloalkylene group, a substituted or unsubstituted C6 To C30 arylene group, substituted or unsubstituted C3 to C30 cycloalkenylene group, substituted or unsubstituted C7 to C20 arylalkylene group, substituted or unsubstituted C1 to C20 heteroalkylene group, substituted or unsubstituted C2 to C30 Heterocycloalkylene group, substituted or unsubstituted C2 to C30 heteroarylene group, substituted or unsubstituted C2 to C30 alkenylene group, substituted or unsubstituted C2 to C30 alkynylene group, substituted or unsubstituted C2 to C30 alkoxy A silylene group, a substituted or unsubstituted C1 to C30 ester group, a substituted or unsubstituted C1 to C30 ether group, a substituted or unsubstituted amino group, or a combination thereof, but is not limited thereto. The.

T 1 and T 2 in Chemical Formula 1 are end capping groups, respectively, and are C1 to C20 aromatic or aliphatic groups that do not include hydrophilic functional groups such as -OH, -COOH, and NH2.

The T 1 and T 2 may be a hydrophobic functional group having no hydroxyl group and / or carboxyl group in consideration of compatibility with the polymer resin.

The T 1 and T 2 may each independently include at least one selected from functional groups represented by the following Formulas 4-1 to 4-12.

 [Formula 4-1]

Figure pat00053

In Chemical Formula 4-1,

n 1 is an integer of 0 to 6,

R 1 is a hydrogen atom, a halogen atom, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C6 to C30 is an aryloxy group which is a substituent, when n 1 is 2 or more, the substituents may be the same or different from each other,

[Formula 4-2]

Figure pat00054

In Chemical Formula 4-2,

n 2 is 1, n 3 is an integer of 0 to 3,

R 2 and R 3 are each independently a hydrogen atom, a halogen atom, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C6 to C30 aryl group, Or a substituent which is a substituted or unsubstituted C6 to C30 aryloxy group, when n 3 is 2 or more, the substituents may be the same or different from each other,

[Formula 4-3]

Figure pat00055

In Chemical Formula 4-3,

n 4 is an integer of 0 to 2,

R 4 is a hydrogen atom, a halogen atom, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C6 to C30 is an aryloxy group which is a substituent, when n 4 is 2 The substituents may be the same or different from each other,

[Formula 4-4]

Figure pat00056

In Chemical Formula 4-4,

n 5 is an integer of 0 to 8,

R 5 is a hydrogen atom, a halogen atom, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C6 to C30 is an aryloxy group which is a substituent, when n 5 is 2 or more, the substituents may be the same or different from each other,

[Formula 4-5]

Figure pat00057

In Chemical Formula 4-5,

n 6 is an integer of 0 to 7,

R 6 is a hydrogen atom, a halogen atom, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C6 to C30 is an aryloxy group which is a substituent, when n 6 is 2 or more, the substituents may be the same or different from each other,

[Formula 4-6]

Figure pat00058

In Chemical Formula 4-6,

n 7 is an integer of 0 to 9,

R 7 is a hydrogen atom, a halogen atom, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C6 to C30 is an aryloxy group which is a substituent, when n 7 is 2 or more, the substituents may be the same or different from each other,

[Formula 4-7]

Figure pat00059

In Chemical Formula 4-7,

n 8 and n 9 are each independently an integer of 0 to 6,

R 8 and R 9 are each independently a hydrogen atom, a halogen atom, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C6 to C30 aryl group, Or a substituted or unsubstituted C6 to C30 aryloxy group, and when n 8 and n 9 are each 2 or more, the substituents may be different from each other,

Q 1 and Q 2 are each independently a methylene group, -O- or -S-,

m 1 is an integer of 1 to 3,

[Formula 4-8]

Figure pat00060

In Chemical Formula 4-8,

n 10 is an integer from 0 to 7, n 11 is an integer from 0 to 6,

R 10 and R 11 are each independently a hydrogen atom, a halogen atom, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C6 to C30 aryl group, Or a substituent which is a substituted or unsubstituted C6 to C30 aryloxy group, when n 10 and n 11 are each 2 or more, the substituents may be different from each other,

Q 3 and Q 4 are each independently a methylene group, O or S,

m 2 is an integer of 1 to 3,

[Chemical Formula 4-9]

Figure pat00061

In Chemical Formula 4-9,

n 12 is an integer from 0 to 7, n 13 is an integer from 0 to 6, n 14 is an integer from 0 to 8,

R 12 to R 14 are each independently a hydrogen atom, a halogen atom, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C6 to C30 aryl group, Or a substituted or unsubstituted C6 to C30 aryloxy group, and when n 12 to n 14 are each 2 or more, the substituents may be different from each other,

Q 5 and Q 6 are each independently a methylene group, O or S,

m 3 and m 4 are each independently an integer of 1 to 3,

[Formula 4-10]

Figure pat00062

In Chemical Formula 4-10,

n 15 is an integer of 0 to 2,

R 15 is a hydrogen atom, a halogen atom, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted It is a substituent which is an aryloxy group of C6 to C30.

[Formula 4-11]

Figure pat00063

[Formula 4-12]

Figure pat00064
.

As the dissolution parameter of the liquid crystal oligomer is smaller than the dissolution parameter of the polymer resin, melt mixing is easier during processing of the polarizing film. For example, the dissolution parameter may have a difference of about 10 or less.

The dissolution parameter of the liquid crystal oligomer may be between about 15 and 30, and may be about 18 to 25 within the above range. By having the dissolution parameter of the above range can have excellent melt mixing properties with the above-described polymer resin.

The liquid crystal oligomer may be included in an amount of about 0.01 to 10 parts by weight based on 100 parts by weight of the polymer resin. By being included in the above range, it is possible to have an orientation inducing effect of the dichroic dye without lowering the transmittance of the polarizing film.

The polymer resin, the dichroic dye, and the liquid crystal oligomer may each be in solid form such as powder. The composition for a polarizing film may have a solids content of about 90% by weight or more, for example, may not contain a solvent.

The above-mentioned composition for polarizing film can be manufactured into a polarizing film by melt mixing and an extending process.

Polarizing film according to one embodiment comprises the steps of melt-mixing the composition for a polarizing film including the above-mentioned polymer resin, dichroic dye and liquid crystal oligomer at a processing temperature, the step of preparing a sheet by putting the molten mixture into a mold and pressurized, and It can be produced by the step of uniaxial stretching by a roll (roll) or the like.

In the melt mixing step, the processing temperature may be higher than the melting point (Tm) of the polymer resin, for example, higher than the melting point of the polymer resin and may be about 250 ° C. or less, and specifically about 100 to May be 250 ° C.

The step of preparing the sheet may be performed by putting the molten mixture in the mold and pressing it with a high-pressure press, or discharging the mixture through a chill roll through a T-die.

The uniaxial stretching may be performed at an elongation of about 300% to about 1000%, specifically, at an elongation of about 300% to about 800%. The elongation percentage refers to the ratio of the length of the sheet before stretching to the length after stretching, which means the degree to which the sheet is stretched after uniaxially stretching.

1 is a schematic view showing a polarizing film according to one embodiment.

Referring to FIG. 1, a polarizing film 20 according to an embodiment includes a polymer resin 21, a dichroic dye 22, and a liquid crystal oligomer 23, and a dichroic dye 22 and a liquid crystal oligomer 23. ) Is uniaxially stretched in one direction in the polymer resin 21.

The polarizing film 20 may have a dichroic ratio of about 3 to about 10 in a visible wavelength range between about 380 nm and 780 nm. Here, the dichroic ratio is a value obtained by dividing the absorption of the plane polarized light in the direction perpendicular to the axis of the polymer by the polarization absorption in the horizontal direction thereof, and can be obtained by the following equation (1).

[Equation 1]

DR = Abs / Abs

In the above equation (1)

DR is a dichroic ratio,

Abs is the light absorbance of the polarizing film to light incident in parallel to the transmission axis of the polarizing film,

Abs is the light absorption of the polarizing film to the light incident perpendicular to the transmission axis of the polarizing film.

For reference, absorbance Abs and transmittance T have the following correlation by Lambert-Beer's law.

T = 10 - Abs

Polarization degree is calculated | required by following formula (2).

&Quot; (2) "

PE (%) = [(T -T ) / (T + T )] 1/2 ⅹ 100

In Equation (2)

PE is the degree of polarization,

T is the light transmittance of the polarizing film to light incident parallel to the transmission axis of the polarizing film,

T is the light transmittance of the polarizing film to the light incident perpendicular to the transmission axis of the polarizing film.

The dichroic ratio may represent a degree in which the dichroic dye 22 and the liquid crystal oligomer 23 are arranged side by side in one direction in the polarizing film 20, and have a dichroic ratio in the above range in the visible wavelength range. The orientation of the dichroic dye 72 and the liquid crystal oligomer 23 can be induced according to the orientation of the polymer chain, thereby improving the polarization characteristics.

The polarizing film 20 may have a light transmittance of about 30% or more, and may have a light transmittance of about 30% to 95% within the above range. By having the light transmittance in the above range, it is possible to prevent the light emitted from the display device from being disturbed when applied to one surface of the display device.

The polarizing film 20 may be a melt blend of the polymer resin 21, the dichroic dye 22, and the liquid crystal oligomer 23. The polarizing film may be applied to various display devices.

The display device may be a liquid crystal display device.

2 is a cross-sectional view illustrating a liquid crystal display device according to one embodiment.

Referring to FIG. 2, the liquid crystal display includes a liquid crystal display panel 10 and a polarizing film 20 positioned below and above the liquid crystal display panel 10.

The liquid crystal display panel 10 may be in twisted nematic (TN) mode, patterned vertical alignment (PVA) mode, in plane switching (IPS) mode, optically compensated bend (OCB) mode, or the like. have.

The liquid crystal display panel 10 includes a first display panel 100, a second display panel 200 and a liquid crystal layer 300 interposed between the first display panel 100 and the second display panel 200.

The first display panel 100 may include a thin film transistor (not shown) formed on a substrate (not shown) and a first electric field generating electrode (not shown) connected thereto, and a second display panel 200 may include a color filter (not shown) and a second electric field generating electrode (not shown) formed on a substrate (not shown), for example. However, the present invention is not limited to this, and the color filter may be included in the first display panel 100, and the first electric field generating electrode and the second electric field generating electrode may be located together in the first display panel 100.

The liquid crystal layer 300 may include a plurality of liquid crystal molecules. The liquid crystal molecules may have a positive or negative dielectric constant anisotropy. When the liquid crystal molecules have a positive dielectric anisotropy, the long axis of the liquid crystal molecules is oriented so as to be substantially parallel to the surfaces of the first and second display panels 100 and 200 in the absence of an electric field, And may be oriented so as to be substantially perpendicular to the surfaces of the first display panel 100 and the second display panel 200. On the contrary, when the liquid crystal molecules have a negative dielectric anisotropy, the long axis is oriented almost perpendicular to the surfaces of the first and second display panels 100 and 200 in the absence of an electric field, The long axis can be oriented substantially parallel to the surfaces of the first display panel 100 and the second display panel 200.

The polarizing film 20 is positioned on the outer side of the liquid crystal display panel 10 and is formed on the lower and upper sides of the liquid crystal display panel 10 in the figure, It may be formed only on one of the two sides.

As described above, the polarizing film 20 includes a polymer resin, a dichroic dye, and a liquid crystal oligomer, and details are as described above.

In the above, only the example in which the polarizing film according to the embodiment is applied to the liquid crystal display is described. However, the present invention is not limited thereto, and the same may be applied to any display device including the polarizing plate or the polarizing film, for example, an organic light emitting device (OLED).

Hereinafter, embodiments of the present invention will be described in detail with reference to examples. The following examples are for illustrative purposes only and are not intended to limit the scope of the invention.

Liquid crystal Oligomeric  synthesis

In a 1000 ml flask, 32.83 g (0.2 mol) of 5-norbornene-2,3-dicarboxylic anhydride (nadic anhydride) was added to 400 ml of acetic acid (glacial) at 110 ° C. After dissolving by heating, 41.1 g (0.3 mol) of excess 4-aminobenzoic acid is added thereto. After the addition, the reaction was stirred for 2 hours and then precipitated at room temperature. The precipitate was washed with acetic acid and water and dried in a vacuum oven at 60 ° C. to obtain 4-nadimidobenzoic acid with a yield of 95%.

500 ml flask equipped with condenser and mechanical stirrer 10.798 g (0.065 mol) isophthalic acid, 23.974 g (0.127 mol) 6-hydroxy-2-naphthoic acid, 17.60 g (4-hydroxy-benzoic acid) 0.127 mol), 14.187 g (0.130 mol) of 4-aminophenol and 58.396 g (9.5 mol) of acetic anhydride are added slowly, and the temperature is gradually increased to 140 ° C. under a nitrogen atmosphere, followed by reaction for 3 hours while maintaining the temperature to acetylation. Complete the reaction. Subsequently, after adding 36.79 g (0.130 mol) of 4-namidimide benzoic acid prepared above, the reaction product was heated to 215 ° C. at a rate of 1 to 2 ° C. per minute while removing acetic acid and unreacted acetic anhydride. By reacting for 4 hours, a liquid crystal oligomer represented by Chemical Formula A (mp: 150 ° C.) is prepared.

(A)

Figure pat00065

The number average molecular weight (Mn) of the said liquid crystal oligomer is 3300.

Production of polarizing film

Example  1-1

98.5% by weight of polypropylene, 0.5% by weight of dichroic dye (Ciba Black, BASF, Germany) and 1% by weight of the liquid crystal oligomer were mixed to prepare a composition for a polarizing film.

The composition for polarizing film is melted at a temperature of about 230 ° C. The molten mixture is then placed in a sheet-like mold and pressed with a roller to produce a film. Subsequently, the film is uniaxially stretched at 115 ° C. at 300%, 400%, 500%, 600%, 700%, and 800% magnification, respectively, to prepare a polarizing film.

Example  1-2

96.5% by weight of polypropylene, 0.5% by weight of dichroic dye (Ciba Black , BASF, Germany) and 3% by weight of the liquid crystal oligomer were mixed to prepare a composition for a polarizing film.

The composition for polarizing film is melted at a temperature of about 230 ° C. The molten mixture is then placed in a sheet-like mold and pressed with a roller to produce a film. Subsequently, the film is uniaxially stretched at 115 ° C. at 300%, 400%, 500%, 600%, 700%, and 800% magnification, respectively, to prepare a polarizing film.

Example  2

Glycol-modified polyethylene terephthalate (PETG) 98.6% by weight, dichroic dye 1 (Nazo, manufactured by Nematel) 0.2% by weight, dichroic dye 2 (G241, Hayashibara) 0.1% by weight, dichroic dye 3 (AC1, Nematel Co., Ltd.) 0.1% by weight and the liquid crystal oligomer 1% by weight to prepare a composition for a polarizing film.

The composition for polarizing film is melted at a temperature of about 230 ° C. The molten mixture is then placed in a sheet-like mold and pressed with a roller to produce a film. Then, the film is uniaxially stretched at a rate of 500% at 80 ° C. to produce a polarizing film.

Comparative Example  One

99.5% by weight of polypropylene and 0.5% by weight of dichroic dye (Ciba Black, BASF, Germany) were mixed to prepare a composition for a polarizing film.

The composition for polarizing film is melted at a temperature of about 230 ° C. The molten mixture is then placed in a sheet-like mold and pressed with a roller to produce a film. Subsequently, the film is uniaxially stretched at 115 ° C. at 300%, 400%, 500%, 600%, 700%, and 800% magnification, respectively, to prepare a polarizing film.

Comparative Example  2

Glycol denaturation Polyethylene terephthalate (PETG) 99.6% by weight, dichroic dye 1 (Nazo, Nematel) 0.2% by weight, dichroic dye 2 (G241, Hayashibara) 0.1% by weight and dichroic dye 3 (AC1, Nematel) ) 0.1 wt% is mixed to prepare a composition for polarizing film.

The composition for polarizing film is melted at a temperature of about 230 ° C. The molten mixture is then placed in a sheet-like mold and pressed with a roller to produce a film. Subsequently, the film is uniaxially stretched at a rate of 500% at 80 ° C. to produce a polarizing film.

Comparative Example  3

96.8% by weight of mixed polymer resin of polypropylene and polypropyl-polyethylene copolymer (mixing ratio: 50:50 wt / wt), 0.2% by weight of dichroic dye (G241, manufactured by Hayashibara), and nematic liquid crystal (TL203, Merck) Manufacture) 3 weight% is mixed, and the composition for polarizing films is manufactured.

(Note: TL203 is a nematic liquid crystal with pentyl cyanobiphenyl (5CB) / fluoro and chloro substituted mesogens, which does not have a kink structure in its structure)

The composition for polarizing film is melted at a temperature of about 230 ° C. The molten mixture is then placed in a sheet-like mold and pressed with a roller to produce a film. Subsequently, the film is uniaxially stretched at a rate of 1000% at 115 ° C. to produce a polarizing film.

Comparative Example  4

99.8 wt% of a mixed polymer resin (mixing ratio: 50:50 wt / wt) of polypropylene and a polypropyl-polyethylene copolymer and 0.2 wt% of a dichroic dye (G241, manufactured by Hayashibara) were mixed to prepare a composition for a polarizing film do.

The composition for polarizing film is melted at a temperature of about 230 ° C. The molten mixture is then placed in a sheet-like mold and pressed with a roller to produce a film. Subsequently, the film is uniaxially stretched at a rate of 1000% at 115 ° C. to produce a polarizing film.

Rating 1

The polarizing efficiency (PE) of the polarizing film which concerns on Examples 1-1 and 1-2 and Comparative Example 1 is evaluated.

Polarization efficiency based on 40% transmittance at 550 nm Measure

The results are shown in Table 4 and FIG.

3 is a graph showing polarization efficiency of polarizing films according to Examples 1-1 and 1-2 and Comparative Example 1. FIG.

Stretch ratio (%) Polarization efficiency (%) Example 1-1 Examples 1-2 Comparative Example 1 300 36.0 47.7 29.4 400 39.2 54.0 32.0 500 47. 8 70.0 33.2 600 55.9 78.4 39.0 700 63.5 80.0 48.2 800 70.0 82.0 66.5

Referring to Table 4 and Figure 3, it can be seen that the polarizing film according to Examples 1-1, 1-2 is improved compared to the polarizing film according to Comparative Example 1.

Rating 2

The light transmittance, dichroic ratio and polarizing efficiency (PE) of the polarizing films according to Example 2 and Comparative Example 2 were evaluated.

Light transmittance (Ts) refers to the light transmittance of a single film in the visible region (350 to 780nm), and parallel to the transmission axis of the polarizing film using a UV-VIS Spectrophotometer (JASCO, V-7100, Konica-Minolta) The light transmittance of the polarizing film with respect to the light incident to the light beam and the light transmittance of the polarizing film with respect to the light incident perpendicularly to the transmission axis of the polarizing film are respectively measured.

The dichroic ratio is obtained by the above equation (1) using the measured light absorbance.

Polarization degree is calculated | required by the said Formula (2).

The results are shown in Table 5 and FIGS. 4 and 5.

4 is a graph showing absorbance in the wavelength region of 380 to 780 nm of the polarizing film according to Example 2 and Comparative Example 2, Figure 5 is a graph showing the dichroic ratio of the polarizing film according to Example 2 and Comparative Example 2.

Example 2 Comparative Example 2 Light transmittance (Ts,%) 32.6 31.9 Polarization Efficiency (PE,%) 86.8 85.1 Dichroic ratio 400 nm 1.6 1.6 450 nm 2.5 2.3 500 nm 3.1 2.7 550 nm 2.5 2.3 600 nm 1.9 1.8 650nm 1.4 1.2 700 nm 1.1 1.1 Average 2.2 1.9

Referring to Table 5 and FIGS. 4 and 5, it can be seen that the polarizing film and the dichroic ratio are improved while the polarizing film according to Example 2 exhibits the same degree of light transmittance as compared to the polarizing film according to Comparative Example 2. From this, it can confirm that a polarizing characteristic can be improved, without affecting the light transmittance of a polarizing film by a liquid crystal oligomer.

Rating 3

The polarization characteristics of the polarizing films according to Comparative Examples 3 and 4 are compared. This evaluation is to determine whether the polarization characteristics are improved even when the commercially available nematic liquid crystal instead of the liquid crystal oligomer of the structure according to the present embodiment.

The results are shown in Table 6.

Comparative Example 3 Comparative Example 4 Ts (%) 32.38 41.23 T (%) 18.17 29.18 T (%) 2.80 4.83 Polarization Efficiency (PE,%) 85.61 84.62 Dichroic ratio (DR) 2.09 2.46 Film thickness (D, μm), 45 32

Referring to Table 6, it can be seen that when the polarized film includes a commercially available nematic liquid crystal, not only does not improve the polarization characteristics but also the light transmittance is significantly lower than that when the commercialized nematic liquid crystal is not included. have. Accordingly, it can be seen that the liquid crystal oligomers according to the present embodiments described in Evaluations 1 and 2 do not exhibit an effect of improving polarization characteristics without affecting light transmittance.

While the present invention has been particularly shown and described with reference to exemplary embodiments thereof, it is to be understood that the invention is not limited to the disclosed exemplary embodiments, And falls within the scope of the invention.

10: liquid crystal display panel, 20: polarizing film,
100: first display panel, 200: second display panel,
300: liquid crystal layer

Claims (20)

Polymer resins, dichroic dyes and liquid crystal oligomers,
The liquid crystal oligomer
Mesogens, and
Arylene Part of Kink Structure
Composition for a polarizing film having a.
In claim 1,
The liquid crystal oligomer is a composition for a polarizing film represented by the following formula (1):
[Formula 1]
T 1 -L 1- (Ar 1 ) n -L 2- (Ar 2 ) m -L 3 -T 2
In Chemical Formula 1,
Ar 1 is an arylene portion of a folding structure,
Ar 2 is a mesogenic moiety,
L 1 , L 2 and L 3 are each a linking group,
T 1 and T 2 are each a C1 to C20 aromatic or aliphatic group that does not contain a hydrophilic functional group,
The molar ratios n and m satisfy 0.05 ≦ n ≦ 0.6 and 0.4 ≦ m ≦ 0.95.
3. The method of claim 2,
Ar 1 of Formula 1 is a composition for a polarizing film represented by the following formula (2):
(2)
-[X 1 -A 1 -Y 1 ]-
In Formula 2,
A 1 is an arylene group having a folding structure,
X 1 and Y 1 are each independently —C (═O) O—, —OC (═O) —, —C (═O) —, —O—, —C (═N) (R a ) —, -C (= 0) N (R b )-, -N (R c )-, -N (R d ) C (= 0)-, -C (= 0) N (R e )-or a combination thereof Wherein R a to R e are each independently a hydrogen atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a combination thereof.
4. The method of claim 3,
A 1 of Formula 2 is a composition for a polarizing film comprising at least one selected from the groups listed in the following groups 1-1 to 1-6.
[Group 1-1]
Figure pat00066

[Group 1-2]
Figure pat00067

[Group 1-3]
Figure pat00068

[Group 1-4]
Figure pat00069

[Group 1-5]
Figure pat00070

[Group 1-6]
Figure pat00071

In the groups 1-1 to 1-6,
R 20 to R 119 each independently represent a hydrogen atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 To C30 cycloalkenyl group, substituted or unsubstituted C7 to C20 arylalkyl group, substituted or unsubstituted C1 to C20 heteroalkyl group, substituted or unsubstituted C2 to C30 heterocycloalkyl group, substituted or unsubstituted C2 to C30 heteroaryl Groups, substituted or unsubstituted C2 to C30 alkenyl groups, substituted or unsubstituted C2 to C30 alkynyl groups, substituted or unsubstituted C1 to C20 acyl groups, substituted or unsubstituted amino groups, halogen groups, halogen-containing groups or these Is a combination of
W is a single bond, -O-, -C (= 0)-, -S-, -SO 2- , -N 2- , substituted or unsubstituted C1 to C30 alkylene group, substituted or unsubstituted C3 to C30 Cycloalkylene group, substituted or unsubstituted C1 to C30 oxyalkylene group, substituted or unsubstituted C6 to C30 arylene group, substituted or unsubstituted C6 to C30 oxyarylene group, substituted or unsubstituted C6 to C30 heteroarylene group , A substituted or unsubstituted C6 to C30 oxyheteroarylene group or a combination thereof.
3. The method of claim 2,
Ar 2 of Formula 1 is a composition for a polarizing film represented by the following formula (3).
(3)
-[X 2 -A 2 -Y 2 ]-
In Formula 3,
A 2 is a substituted or unsubstituted C3 to C30 cycloalkylene group, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C3 to C30 heterocycloalkylene group, a substituted or unsubstituted C3 to C30 hetero arylene group Or a group comprising a combination thereof
X 2 and Y 2 are each independently —O—, —C (═O) —, a substituted or unsubstituted C1 to C30 alkylene group, a substituted or unsubstituted C1 to C30 oxyalkylene group, or a combination thereof.
The method of claim 5,
A 2 of Formula 3 is a composition for a polarizing film comprising at least one selected from the groups listed in Group 2.
[Group 2]
Figure pat00072

In group 2 above,
Z 1 to Z 6 are each independently a single bond or -O-, -C (= 0)-, -S-, -SO 2- , -N 2- , a substituted or unsubstituted C1 to C20 alkylene group, Substituted or unsubstituted C1 to C20 oxyalkylene group, substituted or unsubstituted C6 to C30 arylene group, substituted or unsubstituted C6 to C30 oxyarylene group, substituted or unsubstituted C6 to C30 heteroarylene group , A substituted or unsubstituted C6 to C30 oxyheteroarylene group or a combination thereof,
R 150 to R 164 each independently represent hydrogen, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 cycloalkenyl group, substituted or unsubstituted C7 to C20 arylalkyl group, substituted or unsubstituted C1 to C20 heteroalkyl group, substituted or unsubstituted C2 to C30 heterocycloalkyl group, substituted or unsubstituted C2 to C30 heteroaryl group , Substituted or unsubstituted C2 to C30 alkenyl group, substituted or unsubstituted C2 to C30 alkynyl group, substituted or unsubstituted C1 to C20 acyl group, substituted or unsubstituted amino group, halogen group, halogen-containing group or It is a combination.
The method of claim 5,
Ar 2 of Chemical Formula 1 is a composition for a polarizing film represented by the following Chemical Formula 3a.
[Chemical Formula 3]
-[X 21 -A 21 -Y 21 ] k1- [X 22 -A 22 -Y 22 ] k2- [X 23 -A 23 -Y 23 ] k3- [X 24 -A 24 -Y 24 ] k4-
In the above formula (3a)
A 21 , A 22 , A 23 and A 24 are each independently a substituted or unsubstituted C3 to C30 cycloalkylene group, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C3 to C30 heterocycloalkylene group , A substituted or unsubstituted C3 to C30 hetero arylene group or a combination thereof,
X 21 , X 22 , X 23 , X 24 , Y 21 , Y 22 , Y 23 and Y 24 are each independently —O—, —C (═O) —, a substituted or unsubstituted C1 to C20 alkylene group, A substituted or unsubstituted C1 to C20 oxyalkylene group or a combination thereof,
k 1 to k 4 are each independently 0 to 50,
At least one of k 1 to k 4 is not zero.
3. The method of claim 2,
T 1 and T 2 of the formula (1) are each independently a composition for a polarizing film comprising at least one selected from the functional groups represented by the formula (4-1 to 4-12).
[Formula 4-1]
Figure pat00073

In Chemical Formula 4-1,
n 1 is an integer of 0 to 6,
R 1 is a hydrogen atom, a halogen atom, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C6 to C30 is an aryloxy group which is a substituent, when n 1 is 2 or more, the substituents may be the same or different from each other,
[Formula 4-2]
Figure pat00074

In Chemical Formula 4-2,
n 2 is 1, n 3 is an integer of 0 to 3,
R 2 and R 3 are each independently a hydrogen atom, a halogen atom, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C6 to C30 aryl group, Or a substituent which is a substituted or unsubstituted C6 to C30 aryloxy group, when n 3 is 2 or more, the substituents may be the same or different from each other,
[Formula 4-3]
Figure pat00075

In Chemical Formula 4-3,
n 4 is an integer of 0 to 2,
R 4 is a hydrogen atom, a halogen atom, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C6 to C30 is an aryloxy group which is a substituent, when n 4 is 2 The substituents may be the same or different from each other,
[Formula 4-4]
Figure pat00076

In Chemical Formula 4-4,
n 5 is an integer of 0 to 8,
R 5 is a hydrogen atom, a halogen atom, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C6 to C30 is an aryloxy group which is a substituent, when n 5 is 2 or more, the substituents may be the same or different from each other,
[Formula 4-5]
Figure pat00077

In Chemical Formula 4-5,
n 6 is an integer of 0 to 7,
R 6 is a hydrogen atom, a halogen atom, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C6 to C30 is an aryloxy group which is a substituent, when n 6 is 2 or more, the substituents may be the same or different from each other,
[Formula 4-6]
Figure pat00078

In Chemical Formula 4-6,
n 7 is an integer of 0 to 9,
R 7 is a hydrogen atom, a halogen atom, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C6 to C30 is an aryloxy group which is a substituent, when n 7 is 2 or more, the substituents may be the same or different from each other,
[Formula 4-7]
Figure pat00079

In Chemical Formula 4-7,
n 8 and n 9 are each independently an integer of 0 to 6,
R 8 and R 9 are each independently a hydrogen atom, a halogen atom, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C6 to C30 aryl group, Or a substituted or unsubstituted C6 to C30 aryloxy group, and when n 8 and n 9 are each 2 or more, the substituents may be different from each other,
Q 1 and Q 2 are each independently a methylene group, -O- or -S-,
m 1 is an integer of 1 to 3,
[Formula 4-8]
Figure pat00080

In Chemical Formula 4-8,
n 10 is an integer from 0 to 7, n 11 is an integer from 0 to 6,
R 10 and R 11 are each independently a hydrogen atom, a halogen atom, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C6 to C30 aryl group, Or a substituent which is a substituted or unsubstituted C6 to C30 aryloxy group, when n 10 and n 11 are each 2 or more, the substituents may be different from each other,
Q 3 and Q 4 are each independently a methylene group, O or S,
m 2 is an integer of 1 to 3,
[Chemical Formula 4-9]
Figure pat00081

In Chemical Formula 4-9,
n 12 is an integer from 0 to 7, n 13 is an integer from 0 to 6, n 14 is an integer from 0 to 8,
R 12 to R 14 are each independently a hydrogen atom, a halogen atom, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C6 to C30 aryl group, Or a substituted or unsubstituted C6 to C30 aryloxy group, and when n 12 to n 14 are each 2 or more, the substituents may be different from each other,
Q 5 and Q 6 are each independently a methylene group, O or S,
m 3 and m 4 are each independently an integer of 1 to 3,
[Formula 4-10]
Figure pat00082

In Chemical Formula 4-10,
n 15 is an integer of 0 to 2,
R 15 is a hydrogen atom, a halogen atom, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted It is a substituent which is an aryloxy group of C6 to C30
[Formula 4-11]
Figure pat00083

[Formula 4-12]
Figure pat00084
.
In claim 1,
The said liquid crystal oligomer is a composition for polarizing films whose melting point is 250 degrees C or less.
In claim 1,
The solubility parameter of the liquid crystal oligomer is 15 to 30 composition for polarizing film.
In claim 1,
The polymer resin is a composition for a polarizing film comprising a polyolefin, polyethylene terephthalate (PET), modified glycol polyethylene terephthalate (PETG), polyester, nylon, copolymers thereof or a combination thereof.
In claim 1,
The solubility parameter difference between the polymer resin and the dichroic dye is less than 7.4 composition for polarizing films.
In claim 1,
The polymer resin is a polyolefin resin,
The dichroic dye is a composition for a polarizing film represented by the following formula (1):
[Formula 1]
Figure pat00085

In Chemical Formula 1,
Ar a To Ar c are each independently a substituted or unsubstituted C6 to C15 aryl group,
R a and R b are each independently a substituted or unsubstituted C1 to C30 aliphatic organic group, a substituted or unsubstituted C1 to C30 aromatic organic group, a substituted or unsubstituted C1 to C30 heteroaliphatic organic group, a substituted or unsubstituted C1 to C30 heteroaromatic organic group or a combination thereof,
o and p are each independently 0 or 1.
The method of claim 13,
R a is a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C1 to C20 thioalkyl group, a substituted or unsubstituted C1 to C30 ketone group, a substituted or unsubstituted A C1 to C30 oxycarbonyl group, a substituted or unsubstituted C2 to C20 alkenyl group, a substituted or unsubstituted C2 to C30 alkynyl group, or a combination thereof,
R b is a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, a C1 to C20 alkoxy group, a substituted or unsubstituted C1 to C20 thioalkyl group, -NR c R d or a combination thereof And wherein R c and R d are each independently hydrogen, a substituted or unsubstituted C1 to C10 alkyl group, or are connected to each other to form a ring.
The method of claim 13,
o and p are each 1,
R a is a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C1 to C20 thioalkyl group, a substituted or unsubstituted C1 to C30 ketone group, a substituted or unsubstituted A C1 to C30 oxycarbonyl group, a substituted or unsubstituted C2 to C20 alkenyl group, a substituted or unsubstituted C2 to C30 alkynyl group, or a combination thereof,
R b is a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, -NR c R d Or a combination thereof, wherein R c and R d are each independently hydrogen, a substituted or unsubstituted C1 to C10 alkyl group, or are connected to each other to form a ring.
The method of claim 13,
o and p are each 0,
R a is a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C1 to C20 thioalkyl group, a substituted or unsubstituted C1 to C30 ketone group, a substituted or unsubstituted A C1 to C30 oxycarbonyl group, a substituted or unsubstituted C2 to C20 alkenyl group, a substituted or unsubstituted C2 to C30 alkynyl group, or a combination thereof,
R b is a substituted or unsubstituted C1 to C30 alkyl group, -NR c R d Or a combination thereof, wherein R c and R d are each independently hydrogen, a substituted or unsubstituted C1 to C10 alkyl group, or are connected to each other to form a ring.
The method of claim 13,
o is 1 and p is 0,
R a is a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C1 to C20 thioalkyl group, a substituted or unsubstituted C1 to C30 ketone group, a substituted or unsubstituted A C1 to C30 oxycarbonyl group, a substituted or unsubstituted C2 to C20 alkenyl group, a substituted or unsubstituted C2 to C30 alkynyl group, or a combination thereof,
R b is a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, -NR c R d Or a combination thereof, wherein R c and R d are each independently hydrogen, a substituted or unsubstituted C1 to C10 alkyl group, or are connected to each other to form a ring.
In claim 1,
The liquid crystal oligomer and the dichroic dye are contained in an amount of 0.01 to 10 parts by weight and 0.05 to 5 parts by weight based on 100 parts by weight of the polymer resin, respectively.
A composition for polarizing film according to any one of claims 1 to 18,
The polarizing film uniaxially stretched.
A display device comprising the polarizing film of claim 19.


KR1020130051318A 2012-05-08 2013-05-07 Composition for polarizing film, polarizing film and display device including the polarizing film KR20130125325A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
US13/889,653 US20130303677A1 (en) 2012-05-08 2013-05-08 Composition for polarizing film, polarizing film, and display device including the polarizing film

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR1020120048618 2012-05-08
KR20120048618 2012-05-08

Publications (1)

Publication Number Publication Date
KR20130125325A true KR20130125325A (en) 2013-11-18

Family

ID=49853790

Family Applications (1)

Application Number Title Priority Date Filing Date
KR1020130051318A KR20130125325A (en) 2012-05-08 2013-05-07 Composition for polarizing film, polarizing film and display device including the polarizing film

Country Status (1)

Country Link
KR (1) KR20130125325A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9268065B1 (en) 2014-10-27 2016-02-23 Samsung Electronics Co., Ltd. Composition for polarizing film, polarizing film, and display device including the polarizing film
KR20160079447A (en) * 2014-12-26 2016-07-06 삼성전자주식회사 Composition for polarizing film and polarizing film and display device
US10156670B2 (en) 2014-12-17 2018-12-18 Samsung Electronics Co., Ltd. Polarizing film having specified zero shear viscosity and yield stress and display device including the same

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9268065B1 (en) 2014-10-27 2016-02-23 Samsung Electronics Co., Ltd. Composition for polarizing film, polarizing film, and display device including the polarizing film
KR20160049373A (en) * 2014-10-27 2016-05-09 삼성전자주식회사 Composition for polarizing film, polarizing film and display device including the polarizing film
US10156670B2 (en) 2014-12-17 2018-12-18 Samsung Electronics Co., Ltd. Polarizing film having specified zero shear viscosity and yield stress and display device including the same
KR20160079447A (en) * 2014-12-26 2016-07-06 삼성전자주식회사 Composition for polarizing film and polarizing film and display device

Similar Documents

Publication Publication Date Title
KR101363479B1 (en) Polymerizable liquid crystal compounds, polymerizable liquid crystal composition, and optically anisotropic body
JP6636077B2 (en) Polarizing film and display device
JP6913152B2 (en) Liquid crystal composition
KR102337607B1 (en) Liquid crystal composition and method for producing the same, and retardation film constituted from the liquid crystal composition
JP2710630B2 (en) Polarizing film and method for producing the same
TW200523646A (en) Method for producing a birefringent film, optical film and imagine display device
KR101999830B1 (en) Polarizing film and display device
TW200815875A (en) Optical compensation film, polarizing plate and liquid crystal display device
JP2017058659A (en) Optical film, manufacturing method thereof and display device
KR102442596B1 (en) Polymerizable compound, mixture, polymerizable liquid crystal composition, polymer, optical film, optically anisotropic body, polarizing plate, display device and anti-reflection film
KR20130125325A (en) Composition for polarizing film, polarizing film and display device including the polarizing film
KR102162291B1 (en) Monomer and polymer and compensation film and optical film and display device
CN115524776A (en) Optical laminate, viewing angle control system, and image display device
KR102118036B1 (en) Composition for polarizing film and polarizing film and display device
JP2017210601A (en) Liquid crystal composition
JP7171886B2 (en) Laminates, circularly polarizing plates, display devices
JP7192085B2 (en) optically anisotropic film, laminate, circularly polarizing plate, display device
JP2004231946A (en) Polyimide film and method for producing the same
KR102057722B1 (en) Composition for polarizing film and polarizing film and display device
KR102422667B1 (en) Composition for optical film and films and display device
CN111886538B (en) Liquid crystal display device having a light shielding layer
WO2021251433A1 (en) Composition and compound
KR20160081656A (en) Polarizing film and display device including the polarizing film
JP7457794B2 (en) Composition, optically anisotropic film, circularly polarizing plate, display device
EP3783406B1 (en) Retardation film, polarizing plate comprising same, and liquid crystal display apparatus comprising same

Legal Events

Date Code Title Description
WITN Withdrawal due to no request for examination