KR0166886B1 - Photopolymer using polyimide fluoro cinnamate and liquid crystal aligning film using same - Google Patents

Photopolymer using polyimide fluoro cinnamate and liquid crystal aligning film using same Download PDF

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KR0166886B1
KR0166886B1 KR1019940015012A KR19940015012A KR0166886B1 KR 0166886 B1 KR0166886 B1 KR 0166886B1 KR 1019940015012 A KR1019940015012 A KR 1019940015012A KR 19940015012 A KR19940015012 A KR 19940015012A KR 0166886 B1 KR0166886 B1 KR 0166886B1
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polyimide
liquid crystal
same
alignment layer
fluoro
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KR960001086A (en
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신현호
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이헌조
엘지전자주식회사
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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
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D179/00—Coating compositions based on 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 C09D161/00 - C09D177/00
    • C09D179/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
    • C09D179/08—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
    • G02F1/133711—Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers by organic films, e.g. polymeric films
    • G02F1/133723—Polyimide, polyamide-imide

Abstract

본 발명은 액정셀의 배향막 물질인 전폴리머(Prepolymer)를 폴리이미드 플루오로 신나메이트(Polyimide fluoro cinnamate)로 함으로써 열안정성이 뛰어나고 러빙(Rubbing)하지 않으면서 액정을 원하는 방향으로 배향할 수 있는 광고분자 물질과 이를 이용한 배향막에 관한 것으로, 폴리이미드계 폴리머에 플루오로 신남산(fluoro cinnamic acid)이 치환된 폴리이미드 플루오로 신나메이트(Polyimide fluoro cinnamate)에 선평광된 UV 빛을 조사하여서 된 광고분자 물질과 이를 이용한 배향막에 관한 것이다.According to the present invention, the prepolymer, which is an alignment layer material of the liquid crystal cell, is made of polyimide fluoro cinnamate, which is excellent in thermal stability and can adsorb liquid molecules in a desired direction without rubbing. The present invention relates to a material and an alignment layer using the same, wherein the ad-molecule material is obtained by irradiating UV light linearly coated on a polyimide fluoro cinnamate substituted with fluoro cinnamic acid in a polyimide polymer. And an alignment layer using the same.

Description

폴리이미드계 플루오르 신나 메이트로 이루어진 광고분자물질 및 이를 이용한 액정셀의 배향막Advertising molecule made of polyimide fluorine cinnamate and alignment layer of liquid crystal cell using same

제1도는 PIFC에 빛을 조사하여 복굴절률을 측정한 실험 장치도.FIG. 1 is a test apparatus diagram for measuring birefringence by irradiating PIFC with light.

본 발명은 액정을 이요한 디스플레이에서 액정을 규칙적으로 배향하기 위한 광고분자 물질과 이를 이용한 배향막에 관한 것으로, 특히 액정셀의 배향막 물질인 전폴리머(Prepolymer)를 폴리이미드 플루오르 신나 메이트(Polyimide fluoro cinna mate)로 하여 열안정성이 뛰어나고 러빙(rubbing)하지 않으면서 액정을 원하는 방향으로 배향할 수 있는 광고분자 물질과 배향막에 관한 것이다.BACKGROUND OF THE INVENTION 1. Field of the Invention [0001] The present invention relates to an advertisement molecule material for regularly aligning liquid crystals in a display using liquid crystals and an alignment layer using the same. The present invention relates to an advertisement molecule material and an alignment film which are excellent in thermal stability and can align liquid crystals in a desired direction without rubbing.

액정을 이용한 디스플레이에서 액정을 규칙적으로 배향하기 위한 액정셀(cell) 배향막은 액정 분자를 평면구조(planar)로 배향시키는 몇가지 방법들이 알려져 있다.Several methods of orienting liquid crystal molecules in a planar structure are known as liquid crystal cell alignment layers for regularly aligning liquid crystals in displays using liquid crystals.

고분자 물질 표면을 기계적인 마찰(rubbing)에 의해서 규칙적인 미세홈(micro groove)들을 형성시키고 그것을 통해 액정 분자들을 전체 배향막 표면에서 규칙적으로 배향시키는 방법으로서, 여기에 사용되는 고분자로는 폴리이미드(polyimide)계나 폴리아미드(polyamide)계의 물질들이 널리 사용되고 있다.A method of forming regular micro grooves by mechanical rubbing on the surface of a polymer material and regularly aligning liquid crystal molecules on the surface of the entire alignment layer, through which polyimide is used. ) Or polyamide-based materials are widely used.

또한 전폴리머(prepolymer)의 광고분자에 의한 배향막 제작방법도 알려져 있다.In addition, a method for producing an alignment film using an advertising molecule of a prepolymer is also known.

이때 사용되는 전폴리머는 폴리비닐 알콜(polyvinyl alcohol:PVA)과 4-메톡시 신남산(4-methoxy cinnamic acid)의 반응에서 생성되는데, 여기에서 선평관된 자외선(UV)빛을 조사하면 광반응에 의해 크로스링킹(cross-linking)된 배향막이 형성된다.The prepolymer used here is produced by the reaction of polyvinyl alcohol (PVA) and 4-methoxy cinnamic acid, which is irradiated with UV rays. By this, an alignment film cross-linked is formed.

이 배향막은 액정분자들을 원하는 방향으로 평면구조로 배향시킬 수 있다. 그러나 종래의 기계적 마찰(rubbing)에 의한 배향막 형성방법에서는 생성되는 미세홈(miceogroove)들의 위상왜곡(random phase distortion)과 광산란(light scattering)을 야기시켰고 이 때문에 디스플레이의 특성에 나쁜 영향을 미치게 된다.This alignment film can orientate liquid crystal molecules in a planar structure in a desired direction. However, in the conventional method of forming an alignment layer by mechanical rubbing, it causes random phase distortion and light scattering of generated microgrooves, which adversely affects display characteristics.

특히, 기계적 마찰시에 발생되는 정전기는 액티브 매트릭스(Active matrix) 디스플레이에서 결함의 원인이 된다.In particular, static electricity generated during mechanical friction causes defects in active matrix displays.

또한 이 방법으로는 배향막 표면에서 국부적으로 다른 배향을 가진 상태를 만들 수 없게된다.This method also makes it impossible to create states with locally different orientations on the surface of the alignment film.

PVCN-M(polyvinyl-4-methoxycinnamate)인 전폴리머의 광고분자화에 의해 생성되는 배향막은 낮은 열안정성을 가진다.The alignment film produced by the adsorption of the prepolymer of PVCN-M (polyvinyl-4-methoxycinnamate) has low thermal stability.

따라서 상기한 광고분자 물질을 이용한 배향막을 사용한 디스플레이는 전통적인 높은 온도에서의 기술을 사용할 수 없는 문제점이 있다.Therefore, the display using the alignment layer using the above-described advertising molecule material has a problem that cannot use the technology at a high temperature.

본 발명은 상기한 문제점을 해결하기 위해 안출한 것으로, 새로운 유도체인 폴리이미드계 플루오로 신나 메이트(polyimide fluoro cinnamate:PIFC)를 합성한 전폴리머(Prepolymer)로써 이를 광고분자화시켜 열안정성과 배향력이 우수한 광고분자 물질과 그를 이용한 배향막을 제공하고자 하는데 그 목적이 있다.The present invention has been made to solve the above problems, it is a prepolymer synthesized with a new derivative polyimide fluoro cinnamate (PIFC) as a pre-polymer (Prepolymer) by heat-stable stability and orientation An object of the present invention is to provide an excellent advertising molecule and an alignment layer using the same.

이하, 본 발명을 설명한다.Hereinafter, the present invention will be described.

하기의 화학반응식 1 및 화학반응식 2는 본 발명의 폴리이미드 플루오로 신나메이트(PIFC)를 제조하는 합성방법을 나타낸 것이다.Scheme 1 and Scheme 2 below show a synthetic method for preparing the polyimide fluoro cinnamate (PIFC) of the present invention.

우선, 화학반응식 1에 개시된 내용을 설명하면 다음과 같다.First, the contents disclosed in Chemical Scheme 1 will be described.

같은 몰의 상기 (A)의 구조식을 갖는 유기산과 (B)의 구조식을 갖는 디아민을 1γ-부티로락톤(1γ-butyrolactone)중에 약 60℃의 온도에서 반응시킴으로써 상기와 같은 중간산물인 폴리아믹산(C') 용액을 얻게 된다.A polyamic acid, which is an intermediate product as described above, is reacted by reacting an organic acid having a structural formula of (A) with the same mole and a diamine having a structural formula of (B) at a temperature of about 60 ° C. C ') solution.

상기 중간산물인 폴리아믹산 용액(C')에 적정량의 피리딘과 무수초산을 가하고 탈수반응시킴으로써 폴리이미드계 화합물을 얻게 되는 것이다.A polyimide compound is obtained by adding an appropriate amount of pyridine and acetic anhydride to the polyamic acid solution (C ′), which is the intermediate product, and dehydrating the reaction.

이러한 폴리이미드 합성 반응은 당업자에게 일반적인 화학반응이다.Such polyimide synthesis reactions are common chemical reactions to one skilled in the art.

이때, 상기 치환기 R은 본 발명에서 하기의 구조식을 갖는 플루오로 신나메이트(fluoro cinnamate)기로써, 러빙하지 않으면서 액정을 원하는 방향으로 배향할 수 있도록 하는 감광성 치환기이다.In this case, the substituent R is a fluoro cinnamate group having the following structural formula in the present invention, and is a photosensitive substituent that allows the liquid crystal to be oriented in a desired direction without rubbing.

이처럼 치환기 R을 상기의 구조식으로 특정하였을 경우 본 발명의 폴리이미드 플루오르 신나메이트(Polyimide Fouoro Cinnamate; PIFC)가 합성된다.As such, when the substituent R is specified by the above structural formula, the polyimide Fouoro Cinnamate (PIFC) of the present invention is synthesized.

한편, 상기 화학반응식에는 구체적으로 어떤 전자의 이동으로 반응이 일어나게 되는지에 관한 전자의 움직임을 보여주기 위하여 반응 화살표를 기재하였다. 즉, N이 C=O의 탄소를 공격하여 C=O의 더블 본드(double bond)가 끊어지면서 []가 -OH의 본드(bond)를 공격하여 -OH와 NH2의 H가 반응하여 H2O가 빠지는 반응, 즉 탈수반응이 일어나는 것이다.On the other hand, the chemical reaction formula has described the reaction arrows to show the movement of the electrons specifically to the movement of the electrons. In other words, when N attacks C = O carbon and C = O double bond is broken, [ ] Attacks the bond of -OH and -OH reacts with H of NH 2 to release H 2 O, that is, dehydration.

다음으로, 화학반응식 2는 다음과 같은 화학반응을 개시하고 있다.Next, Chemical Scheme 2 discloses the following chemical reaction.

즉, 같은 몰의 폴리이미드(A')와, 벤제고리의 하나의 수소기가 불소기로 치환된 신나모일 클로라이드(B')(cinnamoyl chloride)를, 반응 용액 NMP에서 가열하여 반응시켜 본 발명의 폴리이미드 플루오로 신나메이트(Polyimide Fluoro Cinnamate)를 제조하였다.That is, the polyimide of the present invention is reacted by heating the same moiety of polyimide (A ') and cinnamoyl chloride (B') (cinnamoyl chloride) in which one hydrogen group of the benze ring is substituted with a fluorine group. Polyimide Fluoro Cinnamate was prepared.

이와 같은 반응으로얻어진 전폴리머(Prepolymer)를 이용한 배향막의 형성과정은 다음과 같다.The formation process of the alignment layer using the prepolymer obtained by such a reaction is as follows.

1) 전폴리머(Prepolymer) 배향막형성: 4g/l 농도의 PIFC를 사용하여(용매 NMP) 스핀 코팅(Spin Coating)의 방법으로 유리기판 혹은 1TO가 도포된 기판위에 막을 형성시켰다. 코팅은 20-30초 동안 3000rpm의 속도로 진행시켰고 막의 형성후에 60℃에서 30분간 프리베이킹(Prebaking)시켰다.1) Prepolymer alignment film formation: A film was formed on a glass substrate or 1TO coated substrate by spin coating using 4 g / l of PIFC (solvent NMP). The coating was run at 3000 rpm for 20-30 seconds and prebaked at 60 ° C. for 30 minutes after formation of the film.

2) 전폴리머(Prepolymer)막의 광고분자화 및 광응답속도(Photoresponse)측정: 형성된 전폴리머(Prepolymer)막에 선평광된 UV 빛 (λ ＜ 360㎚)을 조사하면 이방성(anisotropy)의 폴리머가 생성된다.2) Ad molecule formation and photoresponse measurement of prepolymer membrane: Anisotropy polymer is produced by irradiating linearly formed UV light (λ <360 nm) on the formed prepolymer membrane. do.

나타난 이방성은 복굴절률로서 표시된다. (△n = ne - no, ne와 no는 각각 이상광(extraordinary)과 정상광(ordinary) 굴절률을 나타낸다.)The anisotropy shown is expressed as birefringence. (Δn = ne-no, ne and no represent extraordinary and ordinary refractive indices, respectively.)

PIFC에 의해 코팅된 기판에 UV를 조사하기 위한 실험장치를(제1도)에 나타내었고 빛을 조사하는 동안 유도되는 복굴절률 또한 동시에 측정할 수 있다.An experimental apparatus for irradiating UV to a substrate coated by PIFC is shown in FIG. 1 and the birefringence induced during light irradiation can also be measured simultaneously.

UV빛을 조사하는 장치는 250-500W의 평균출력을 갖는 수은램프(1), 렌즈(2), 글랜-톰슨(Glan-Thompson) 프리즘(3) 그리고 스플리팅(Splitting) 거울로 구성되어있고 복굴절률의 측정장치는 헬륨-네온 레이저(8), 편광판(Polarizer)(7), 포토다이오드(photodiode)(9), 그리고 디지털 오실로 그래프(10)으로 구성되어 있다.The UV-irradiation device consists of a mercury lamp (1), a lens (2), a Gran-Thompson prism (3) and a splitting mirror with an average power of 250-500 W. The birefringence measuring device is composed of a helium-neon laser 8, a polarizer 7, a photodiode 9, and a digital oscilloscope graph 10.

편광판(7)들을 서로 직교하게 설치하고 UV빛의 E-벡터는 편광판의 투과축(polarizer axis)과 45도 각도를 이루게 한다.The polarizers 7 are orthogonal to each other and the E-vector of UV light makes a 45 degree angle with the polarizer axis of the polarizer.

유리기판위의 PIFC막(5)은 충분한 광학 이방성이 나타날때까지 빛을 조사한다.The PIFC film 5 on the glass substrate is irradiated with light until sufficient optical anisotropy appears.

빛을 조사하는 시간 t는 UV빛의 강도(power density) I에 의존한다.The time t for irradiating light depends on the power density I of the UV light.

(I=10mW/㎠의 빛에서 t=5-15분 노출시킨다.)(T = 5-15 minutes exposure in light of I = 10mW / cm 2)

광고분자화 된 PIFC막을 사용한 셀(cell)은 일반적으로 사용되는 기술로 조립되고 액정을 모세관 현상에 의해 셀(cell)에 채워진다.A cell using an ad-polymerized PIFC film is assembled by a commonly used technique and the liquid crystal is filled in the cell by capillary action.

이렇게 조립된 셀(cell)에서의 액정 배향은 뛰어난 평면구조(plannar) 혹은 90도 트위스트 배향을 가지며 높은 앵커링 에너지(polar anchoring energy)를 가진다.The liquid crystal alignment in the cell thus assembled has an excellent plannar or 90 degree twist orientation and high polar anchoring energy.

이상에서와 같이 PIFC 물질을 이용한 배향막은 종래의 폴리비닐 4-메톡시 신나메이트(poly viny 4-methoxy cinnamate)를 이용한 것 보다 우수한 열안정성을 갖는 것으로, 종래의 물질을 이용한 배향막에서는 50-55℃로 가열한 후 상온으로 냉각시키면 전경(disclination)이 나타나며 비가열적으로 V10값이 증가하고 g(V10/V90)값이 25-40%정도 감소하게 되나 본 발명인 PIFC를 이용한 배향막은 150℃에서 10시간 두었을 경우에도 배향력이 변하지 않음을 알 수 있었다.As described above, the alignment layer using the PIFC material has better thermal stability than that using the conventional poly vinyl 4-methoxy cinnamate, and is 50-55 ° C. in the alignment layer using the conventional material. When heated to room temperature and then cooled to room temperature, the foreground (disclination) appears and the non-heated V 10 value increases and the g (V 10 / V 90 ) value decreases by about 25-40%. It was found that even if left for 10 hours at the orientation force does not change.

Claims (1)

하기 구조식으로 표시되는 전폴리머(Prepolymer)인 폴리이미드 플루오로 신나 메이트(Polyimide fluoro cinnamate)(PIFC)에 선편광된 자외선(UV)빛을 조사하여서 된, 액정셀의 배향막으로 사용하기 위한 광고분자물질.Ad molecular material for use as an alignment layer of a liquid crystal cell by irradiating linearly polarized ultraviolet (UV) light to a polyimide fluoro cinnamate (PIFC), which is a prepolymer represented by the following structural formula.
KR1019940015012A 1994-06-28 1994-06-28 Photopolymer using polyimide fluoro cinnamate and liquid crystal aligning film using same KR0166886B1 (en)

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR101411830B1 (en) * 2011-02-25 2014-06-25 한국화학연구원 Low temperature processable and photo-crosslinkable organic gate insulator, and organic thin film transistor device using the same
KR101702302B1 (en) 2016-08-11 2017-02-03 황승하 Method for manufacturing synthetic resin clad metal pipe

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KR100762832B1 (en) * 2004-12-03 2007-10-02 주식회사 엘지화학 Photoreactive compounds, liquid crystal alignment layer using the same, method for manufacturing thereof, and liquid crystal display device containing the alignment layer

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR101411830B1 (en) * 2011-02-25 2014-06-25 한국화학연구원 Low temperature processable and photo-crosslinkable organic gate insulator, and organic thin film transistor device using the same
KR101702302B1 (en) 2016-08-11 2017-02-03 황승하 Method for manufacturing synthetic resin clad metal pipe

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