Photoactive polymers

A photoactive polymer, photodimerization technology, applied in optics, optomechanical equipment, nonlinear optics, etc., can solve the problem of high surface tension

Inactive Publication Date: 2004-07-14
ROLIC AG
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

A disadvantage of known alignment materials that induce very high pretilt angles is that they have high surface tension, which causes wetting problems
It is therefore not possible to apply a uniform layer of LCP prepolymer on top of such an alignment layer

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0212] Poly[1-[11-[5-[4-[(E)-2-methoxycarbonylvinyl]benzoyloxy]-2-(4-propylbenzoyloxy)benzoyl Oxy]undecyloxycarbonyl]-1-methylethylene]

[0213]

[0214] In a sealed tube, 0.89 g (1.22 mmol) of (E)-5-[4-(2-methoxycarbonylvinyl)benzoyloxy]- 11-(2-methacryloyloxy)undecyl 2-(4-propylbenzoyloxy)benzoate and 2.0 mg (0.012 mmol) α,α′-azobisisobutyronitrile (AIBN) mixture was degassed. The tube was then sealed under argon and stirred at 60°C for 17 hours. The polymer was diluted with 2.5 ml THF, precipitated in 500 ml diethyl ether and collected. Dissolution in THF (7.0 ml) and reprecipitation of the polymer in 750 ml of methanol afforded 0.71 g (80%) of poly[1-[11-[5-[4-[(E)-2 -Methoxycarbonylvinyl]benzoyloxy]-2-(4-propylbenzoyloxy)benzoyloxy]undecyloxycarbonyl]-1-methylethylene]; Mn =7.4×10 4 , pdi=6.95, Tg=49.5°C, cl.p.(N / I) 127.3°C.

[0215] (E)-5-[4-(2-Methoxycarbonylvinyl)benzoyloxy]-2-(4-propylbenzoyloxy)benzoic acid was prepared as a starting material as follows 11...

Embodiment 2

[0239] Poly[1-[11-[2-[4-pentylbenzoyloxy]-5-[6-[2-methoxy-4-(methoxycarbonylvinyl)phenoxy]oxy Hexyl]benzoyloxy]deca-alkoxycarbonyl]-1-methylethylene]

[0240]

[0241] With 1.0g (1.17mmol) (E)-2-[4-phenylbenzoyloxy]-5-[6-[2-methoxy-4-(methoxycarbonylvinyl)phenoxy ] Oxyhexyl] 11-(2-methacryloyloxy) undecyl benzoate, prepared in a similar manner to Example 1, to obtain 0.84 g (84%) of hard solid poly[1-[ 11-[2-[4-Pentylbenzoyloxy]-5-[6-[2-methoxy-4-(methoxycarbonylvinyl)phenoxy]oxyhexyl]benzoyl Oxygen]undecyloxycarbonyl]-1-methylethylene]; Mn=7.3×10 4 , pdi=4.40, Tg=34.0°C, cl.p(N / I) 54.2°C.

[0242] (E)-2-[4-phenylbenzoyloxy]-2-[5-[2-methoxy-4-(methoxycarbonylvinyl)benzene used as starting material was prepared as follows Oxy]oxyhexyl]benzoic acid 11-(2-methacryloyloxy)undecyl ester:

[0243] (E)-4-Hydroxy-3-methoxycinnamic acid methyl ester

[0244]

[0245] 25 g (0.13 mmol) of (E)-4-hydroxy-3-methoxycinnamic acid were dissolved in 180 ml of methanol, and 5 ml of c...

Embodiment 3

[0256] Polyimide

[0257] To 0.434g (0.547mmol) 3,5-diaminobenzoic acid 11-[2-[4-pentylbenzoyloxy]-5-[4-(2-methoxycarbonylvinyl)benzoyl To a solution of oxy]benzoyloxy]undecyl ester in 3 ml of tetrahydrofuran was added 96.6 mg (0.493 mmol) of 1,2,3,4-cyclobutanetetracarboxylic dianhydride. It was then stirred at 0°C for 2 hours. 10.7 mg (0.055 mmol) of 1,2,3,4-cyclobutanetetracarboxylic dianhydride were added. The mixture was then allowed to react at room temperature for 69 hours. The polymer mixture was diluted with 3.0 ml THF, precipitated in 150 ml diethyl ether and collected. The polymer was added from THF (10ml) into 500ml of water for reprecipitation, and after vacuum drying at room temperature, 0.51g of light brown powdery polyamic acid A was obtained; [η]=0.51dL / g.

[0258] 3,5-diaminobenzoic acid 11-[2-[4-pentylbenzoyloxy]-5-[4-(2-methoxycarbonylvinyl)benzene as starting material was prepared as follows Formyloxy]benzoyloxy]undecyl ester:

[0259] 11-Bromoundecy...

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Abstract

A photoactive polymer of the general formula I:in which:P is a photoactive group which can photoisomerise and/or photodimerise;B represents an aromatic or alicyclic group, or B further represents a nitrogen atom or -CR<2>-;A, C, D each independently of the other represents an aromatic or alicyclic group;M represents a repeating monomer unit in a homo- or copolymer;S<1>, S<2>, S<3>, S<4>, S<5 >represent a single covalent bond or a spacer unit;n<1>, n<2 >are each independently a positive integer up to 2 with the proviso that n<1>+n<2><=2;R<1 >is a hydrogen atom, or a straight-chain or branched alkyl residue wherein R<2 >represents a hydrogen atom or lower alkyl.The photoactive polymers may be used as orientation layers for liquid crystals and in the construction of unstructured and structured optical elements and multi-layer systems.

Description

technical field [0001] The present invention relates to new photoactive polymers and their use in the construction of alignment layers for liquid crystals and structured and unstructured optical elements and multilayer systems. Background technique [0002] The different optoelectronic effects used in liquid crystal displays (LCDs) require alignment layers with very high pretilt angles. For example, a vertically oriented nematic (VAN) LCD requires a pretilt angle of 85-90° measured from the surface plane. In the case of a mixed-positioned nematic (HAN)-LCD, the pretilt angle must be within the above range on one substrate, while the tilt angle on the other substrate is lower (typically 0-10°) . Brush-coated polyimides, which induce high pretilt angles, suffer from the well-known disadvantages associated with the brush-coating process. For VAN-LCDs, especially scratches caused by brushing and insufficient uniformity of the pretilt angle are well-known problems of the brush...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): G03F7/027C08F12/00C08F20/30C08F246/00C08G73/10C08G85/00G02F1/1337
CPCG02F1/133711C08F246/00G02F1/133723G02F1/133788C09K2323/0271C09K2323/023C09K2323/025C09K2323/027C09K2323/02
Inventor H·希伯勒G·马克O·穆勒
Owner ROLIC AG
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