KR20120122045A - Liquid crystal orientation agent, liquid crystal orientation layer, and liquid crystal display - Google Patents

Liquid crystal orientation agent, liquid crystal orientation layer, and liquid crystal display Download PDF

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KR20120122045A
KR20120122045A KR1020110040008A KR20110040008A KR20120122045A KR 20120122045 A KR20120122045 A KR 20120122045A KR 1020110040008 A KR1020110040008 A KR 1020110040008A KR 20110040008 A KR20110040008 A KR 20110040008A KR 20120122045 A KR20120122045 A KR 20120122045A
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South Korea
Prior art keywords
liquid crystal
crystal aligning
aligning agent
formula
dianhydride
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KR1020110040008A
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Korean (ko)
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김경찬
지문배
채기성
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엘지디스플레이 주식회사
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Publication of KR20120122045A publication Critical patent/KR20120122045A/en

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
    • C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
    • C08G73/12—Unsaturated polyimide precursors
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L79/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen or carbon only, not provided for in groups C08L61/00 - C08L77/00
    • C08L79/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
    • C08L79/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/52—Liquid crystal materials characterised by components which are not liquid crystals, e.g. additives with special physical aspect: solvents, solid particles
    • C09K19/54—Additives having no specific mesophase characterised by their chemical composition
    • C09K19/56—Aligning agents
    • G—PHYSICS
    • G02—OPTICS
    • G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
    • G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
    • G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour 
    • G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on liquid crystals, e.g. single liquid crystal display cells
    • G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
    • G02F1/1333—Constructional arrangements; Manufacturing methods
    • G02F1/1337—Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers

Abstract

Liquid crystal aligning agent according to an embodiment of the present invention is one selected from one carboxylic dianhydride selected from the carboxylic dianhydride group represented by the formula (1) and one formula selected from the diamine group represented by the formula (2) to formula (4) The diamine may be reacted to produce a polyamic acid, which may be prepared by imidization thereof.

Description

Liquid crystal aligning agent, liquid crystal aligning film, and liquid crystal display device {LIQUID CRYSTAL ORIENTATION AGENT, LIQUID CRYSTAL ORIENTATION LAYER, AND LIQUID CRYSTAL DISPLAY}

The present invention relates to a liquid crystal aligning agent, a liquid crystal aligning film and a liquid crystal display device, and more particularly, to a liquid crystal aligning agent, a liquid crystal aligning film and a liquid crystal display device which can prevent the afterimage caused by the liquid crystal aligning film.

In general, a liquid crystal display device includes a thin film transistor array substrate on which pixel electrodes are formed and a color filter substrate facing each other, and a liquid crystal alignment layer is formed on a surface of the liquid crystal display panel facing each other. The liquid crystal layer is interposed between the thin film transistor array substrate and the color filter substrate.

Many rubbing alignment films are used as the liquid crystal alignment film. The rubbing alignment layer is easy to adjust the pretilt angle, various chemical and thermal stability is very high, and also has excellent reliability. However, due to the uncontrollable factor of the rubbing cloth, undesired tearing of the alignment layer and disorientation of the alignment layer and uneven alignment at the stepped portion of the liquid crystal display device cause light leakage. In addition, there is a problem that the aperture ratio is lowered by forming a wide black matrix to prevent such light leakage.

Recently, in order to solve such a problem, a photo alignment layer (UV alignment layer) has been used. The photoalignment film is an alignment film which is exposed to light to solve the problem of the above-described rubbing alignment film. Such a photo-alignment film is comprised with the cyclobutane tetracarboxylic dianhydride (CBDA) which contributes to the anisotropy of liquid-crystal orientation as a photoreactor, and phenylenediamine (PDA) which contributes to liquid-crystal orientation. After dissolving this CBDA and PDA in a solvent (NMP or DMAC), a polyamic acid (PAA) was produced and calcined in an oven at 230 ° C./1 Hr to prepare a photo alignment layer of polyimide (PI).

Figure pat00001

However, in the case of the photo alignment layer, only about 70 to 80% of the polyamic acid is deformed into polyimide, and maleic anhydride, which has been photodegraded upon prolonged exposure to the atmosphere, is reduced to CBDA, so that the anisotropic characteristic disappears, and the afterimage of the photo alignment layer disappears. There is a problem that is not greatly improved.

This invention provides the liquid crystal aligning agent, the liquid crystal aligning film, and the liquid crystal display device which can prevent the afterimage by a liquid crystal aligning film from appearing.

In order to achieve the above object, the liquid crystal aligning agent according to an embodiment of the present invention is one carboxylic dianhydride selected from the group of carboxylic dianhydride represented by the following formula (1) and diamine represented by the following formulas (2) to (4) It can be prepared by reacting one diamine selected from one formula selected from the group to prepare a polyamic acid and imidize it.

[Formula 1]

Figure pat00002

[Formula 2]

Figure pat00003

(3)

Figure pat00004

[Formula 4]

Figure pat00005

The diamine represented by Formulas 2 to 4 may include a polar group.

The polar group may be any one or more selected from the group consisting of -CF, -CN, -COOH, -CO, -OH and -NH 2 .

In addition, the liquid crystal aligning agent according to an embodiment of the present invention, in the liquid crystal aligning agent in which cyclobutane tetracarboxylic dianhydride (CBDA) and pyromellitic dianhydride (PMDA) are mixed, the cyclobutane tetracarboxylic dianhydride Silver may be mixed at 60 to 99.9% with respect to 100% of the total liquid crystal aligning agent, and the pyromellitic dianhydride may be mixed at 0.1 to 40% with respect to 100% of the total liquid crystal aligning agent.

In addition, the liquid crystal aligning agent may further include one selected from the diamine group represented by the following Chemical Formulas 2 to 4.

[Formula 2]

Figure pat00006

(3)

Figure pat00007

[Formula 4]

Figure pat00008

In addition, the liquid crystal alignment layer according to the exemplary embodiment of the present invention may be formed by baking the liquid crystal alignment agent in a state of a film.

In addition, a liquid crystal display according to an exemplary embodiment of the present invention includes a thin film transistor array substrate on which pixel electrodes are formed, a color filter substrate, a liquid crystal layer interposed therebetween, and a surface on which the thin film transistor array substrate and the color filter substrate face each other. In the liquid crystal display device comprising a liquid crystal alignment film formed on each of the, the liquid crystal alignment film may be the above-mentioned liquid crystal alignment film.

The liquid crystal aligning agent, the liquid crystal alignment layer, and the liquid crystal display according to the exemplary embodiment of the present invention have an advantage of preventing the afterimage caused by the liquid crystal alignment layer from appearing.

1 is a view showing a liquid crystal display according to an exemplary embodiment of the present invention.

Hereinafter, embodiments of the present invention will be described in detail with reference to the accompanying drawings.

1 is a diagram illustrating a liquid crystal display according to an exemplary embodiment of the present invention.

Referring to FIG. 1, the liquid crystal display device 100 of the present invention faces the thin film transistor array substrate 110, the thin film transistor array substrate 110, and is bonded to the color filter substrate 150 and the thin film transistor array substrate 110. ) And the color filter substrate 150 may be included.

The thin film transistor array substrate 110 includes a thin film transistor TFT formed on the thin film transistor array substrate 110, a pixel electrode 145 electrically connected to the thin film transistor TFT, a thin film transistor TFT and a pixel electrode 145. ) May include an organic insulating layer 140 formed therebetween.

The thin film transistor TFT is formed to face the gate electrode 115 connected to the gate line, the source electrode 135a connected to the data line, and the source electrode 135a, and the drain electrode 135b electrically connected to the pixel electrode 145. ), A gate insulating layer 120 that insulates the gate electrode 115, an active layer 125 and an ohmic contact layer 130 formed in a region corresponding to the gate electrode 115 with the gate insulating layer 120 interposed therebetween. Can be.

Accordingly, the thin film transistor TFT supplies the data voltage from the data line to the pixel electrode 145 in response to the gate on / off voltage from the gate line.

The pixel electrode 145 is formed of a transparent metal such as indium tin oxide (ITO), indium zinc oxide (IZO), or the like, and applies a data voltage to the liquid crystal layer 180 from the drain electrode 135b. Therefore, the pixel electrode 145 is electrically connected to the drain electrode 135b through the contact hole 141 penetrating the organic insulating layer 140.

The organic insulating layer 140 is formed to cover the thin film transistor TFT and is formed on the entire surface of the thin film transistor array substrate 110. The organic insulating layer 140 protects the thin film transistor TFT and serves to form the pixel electrode 145 flat. An inorganic insulating film 147 is formed on the pixel electrode 145, and a liquid crystal alignment film 149 is formed on the inorganic insulating film 147 to align the liquid crystal.

Meanwhile, the color filter substrate 150 may include a black matrix 155 formed to prevent light leakage on the color filter substrate 150, a color filter 160 formed to implement color, a black matrix 155 and a color filter 160. The overcoat layer 165 and the common electrode 170 formed on the overcoat layer 165 may be included.

The black matrix 155 is formed of an opaque organic material or an opaque metal to prevent light from being transmitted through an area beyond the control of the liquid crystal layer 180. The color filter 160 may be formed of a red, green, and blue color filter 160 to implement color. In addition, the overcoat layer 165 may be formed of a transparent organic material to protect the color filter 160 and to provide good step coverage of the common electrode 170. The common electrode 170 is formed of a transparent metal such as indium tin oxide (ITO) or indium zinc oxide (IZO), and serves to apply a common voltage to the liquid crystal layer 180. And the liquid crystal aligning film 149 which orientates a liquid crystal on the overcoat layer 165 is formed.

As described above, the liquid crystal display device 200 includes a thin film transistor array substrate 110, a color filter substrate 150, and a liquid crystal layer 180 interposed between the thin film transistor array substrate 110 and the color filter substrate 150. It may include.

Hereinafter, it demonstrates in detail about the liquid crystal aligning agent of the above-mentioned liquid crystal aligning film.

The liquid crystal aligning agent of the present invention reacts one diamine selected from one carboxylic dianhydride selected from the group of carboxylic dianhydrides represented by the following general formula (1) and one diamine selected from the diamine group represented by the following general formulas (2) to (4). To prepare a polyamic acid and imidize it.

[Formula 1]

Figure pat00009

[Formula 2]

Figure pat00010

(3)

Figure pat00011

[Formula 4]

Figure pat00012

Among these, when one carboxylic dianhydride selected from the carboxylic dianhydride group represented by the formula (1) and the diamine selected from the diamine group represented by the formula (2) to react to produce a liquid crystal aligning agent, the number of benzene rings is By using a large number of diamines, the benzene ring of the liquid crystal and the benzene ring of the alignment agent interact with each other by π-π, thereby increasing the anchoring energy, thereby improving the afterimage occurrence.

In addition, in the case of preparing a liquid crystal aligning agent by reacting one carboxylic dianhydride selected from the carboxylic dianhydride group represented by the formula (1) with a diamine selected from the diamine group represented by the formula (3), an aliphatic bond between the benzene rings By using aliphatic linkaged diamines, there is an advantage that thermal / chemical stabilization can be achieved by increasing binding energy than hetero atom linkages other than carbon.

In addition, in the case of preparing a liquid crystal aligning agent by reacting one carboxylic dianhydride selected from the carboxylic dianhydride group represented by the general formula (1) with a diamine selected from the diamine group represented by the general formula (4), a straight chain between benzene rings By using diamines of straight chains, the bonds are more rigid than the band chains, resulting in an increased chain orientation. Accordingly, there is an advantage that the afterimage property can be improved by increasing the property of returning the liquid crystal in the original direction.

Meanwhile, the diamine represented by Formulas 2 to 4 may include a polar group, and the polar group may be any one or more selected from the group consisting of -CF, -CN, -COOH, -CO, -OH, and -NH 2 . . Accordingly, there is an advantage that the alignment characteristics can be improved by increasing the interaction between the liquid crystal and the side chain of the alignment agent.

Meanwhile, in another embodiment of the present invention, the liquid crystal aligning agent may be prepared by mixing cyclobutanetetracarboxylic dianhydride (CBDA) and pyromellitic dianhydride (PMDA) in a predetermined ratio. In this case, the cyclobutane tetracarboxylic dianhydride is mixed in 60 to 99.9% with respect to 100% of the total liquid crystal aligning agent, the pyromellitic dianhydride is mixed in 0.1 to 40% with respect to 100% of the total liquid crystal aligning agent Can be. Here, when the content of cyclobutanetetracarboxylic dianhydride is 60% or more, the afterimage of AC can be reduced, and when the content of pyromellitic dianhydride is 0.1% or more, the DC afterimage can be reduced.

Such a liquid crystal aligning agent may further include one selected from the diamine groups represented by the following Chemical Formulas 2 to 4.

[Formula 2]

Figure pat00013

(3)

Figure pat00014

[Formula 4]

Figure pat00015

The liquid crystal aligning agent prepared according to the embodiments of the present invention as described above may be used as the liquid crystal alignment layer of the liquid crystal display device described above.

As mentioned above, this invention has the advantage that the liquid crystal aligning agent, a liquid crystal aligning film, and a liquid crystal display device can prevent the afterimage by a liquid crystal aligning film from appearing.

While the present invention has been described in connection with what is presently considered to be practical exemplary embodiments thereof, it is to be understood that the invention is not limited to the disclosed embodiments, but, on the contrary, It will be understood that the invention may be practiced. Therefore, the embodiments described above are to be understood as illustrative and not restrictive in all aspects. In addition, the scope of the present invention is shown by the claims below, rather than the above detailed description. Also, all changes or modifications derived from the meaning and scope of the claims and their equivalents should be construed as being included within the scope of the present invention.

Claims (7)

To prepare a polyamic acid by reacting one carboxylic dianhydride selected from the carboxylic dianhydride group represented by the formula (1) and one diamine selected from one formula selected from the diamine group represented by the following formulas (2) to (4) Liquid crystal aligning agent manufactured by imidation.
[Formula 1]
Figure pat00016


(2)
Figure pat00017

(3)
Figure pat00018

[Chemical Formula 4]
Figure pat00019

 The method of claim 1,
The diamine represented by Formulas 2 to 4 includes a polar group.
The method of claim 2,
The polar group is any one or more selected from the group consisting of -CF, -CN, -COOH, -CO, -OH and -NH 2 .
In the liquid crystal aligning agent in which cyclobutane tetracarboxylic dianhydride (CBDA) and pyromellitic dianhydride (PMDA) are mixed,
The cyclobutanetetracarboxylic dianhydride is mixed at 60 to 99.9% with respect to 100% of the total liquid crystal aligning agent, and the pyromellitic dianhydride is mixed at 0.1 to 40% with respect to 100% of the total liquid crystal aligning agent. Alignment agent.
The liquid crystal aligning agent further comprises one selected from the group of diamines represented by the following formulas (2) to (4).
(2)
Figure pat00020

(3)
Figure pat00021

[Chemical Formula 4]
Figure pat00022

 The liquid crystal aligning film formed by baking the liquid crystal aligning agent in any one of Claims 1-5 in the state of a film | membrane.
A liquid crystal display device comprising a thin film transistor array substrate having a pixel electrode, a color filter substrate, a liquid crystal layer interposed therebetween, and a liquid crystal alignment layer formed on surfaces of the thin film transistor array substrate and the color filter substrate facing each other.
The liquid crystal aligning film is a liquid crystal display device according to claim 6.
KR1020110040008A 2011-04-28 2011-04-28 Liquid crystal orientation agent, liquid crystal orientation layer, and liquid crystal display KR20120122045A (en)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20170051852A (en) * 2015-11-02 2017-05-12 삼성디스플레이 주식회사 Liquid crystal photo alinement agent and method of manufacturing liquid crystal display device using the same

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20170051852A (en) * 2015-11-02 2017-05-12 삼성디스플레이 주식회사 Liquid crystal photo alinement agent and method of manufacturing liquid crystal display device using the same

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