Compounds for homeotropic alignment of liquid crystaline media

A compound, fused ring technology, applied in the direction of liquid crystal materials, organic chemistry, chemical instruments and methods, etc., can solve the problem of VA display is not completely satisfactory, achieve low non-uniformity defects, good processability, handling and improved storability

Pending Publication Date: 2019-08-13
MERCK PATENT GMBH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0027] However, existing methods for obtaining VA display applications without polyimide layers are not entirely satisfactory

Method used

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  • Compounds for homeotropic alignment of liquid crystaline media
  • Compounds for homeotropic alignment of liquid crystaline media
  • Compounds for homeotropic alignment of liquid crystaline media

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0462] Step 1: Synthesis of intermediate 5 (boronic acid)

[0463]

[0464] 9.7 g (0.4 mol) magnesium was covered with 40 ml THF and both were heated to 50°C. A solution of about 10% bromo-aromatic compound 2 (69.9 g, 0.4 mol) in 100 ml THF was then added dropwise. After the reaction had started, 2 was metered in at such a rate that the mixture continued to boil. When the addition was complete, the mixture was cooled to 65°C and 100 g (0.4 mol) of ketone 1 dissolved in 100 ml THF were added dropwise. Work-up yielded 128.3 g of alcohol 3, which was dissolved without further purification in 800 ml of toluene, added 3.2 g of p-toluenesulfonic acid hydrate, and boiled at reflux for 2 hours. Workup yielded 98 g of crude olefin, which was converted to 4 by catalytic hydrogenation.

[0465] 71.7 g (217 mmol) of 4 were dissolved in 200 ml of THF and cooled to -70°C. Then 170 ml (0.239 mol) of a 1.4 molar hexane solution of sec-butyllithium were added dropwise at this temperatur...

Embodiment 2

[0480] Example 2. (Self-aligned Additive No.1)

[0481]

[0482] Phase: glass transition temperature (Tg) -9°C, melting point 80°C.

[0483] 1 H NMR (500MHz, chloroform-d) δ 7.57 (d, J = 1.9Hz, 2H), 7.50 (dd, J = 7.8, 1.9Hz, 2H), 7.38–7.20 (m, 6H), 7.07 (s, 2H), 6.13(t, J=1.3Hz, 2H), 5.58(p, J=1.7Hz, 2H), 4.26(t, J=6.5Hz, 4H), 3.99(t, J=6.3Hz, 2H) , 3.71(s, 4H), 2.96–2.63(m, 9H), 2.55(tt, J=12.1, 3.4Hz, 1H), 2.17–1.84(m, 16H), 1.53(qd, J=12.8, 3.2Hz , 3H), 1.41–1.01(m, 23H), 0.93(dt, J=8.7, 7.0Hz, 6H).

Embodiment 3

[0485]

[0486] Phase: glass transition temperature (Tg) -17°C melting point 65°C

[0487] 1 H NMR (500MHz, chloroform-d) δ 7.58 (d, J = 1.8Hz, 2H), 7.51 (dd, J = 7.9, 2.0Hz, 2H), 7.36–7.21 (m, 6H), 7.07 (s, 2H), 6.14(s, 2H), 5.59(q, J=1.7Hz, 2H), 4.28(t, J=6.6Hz, 4H), 3.95(dt, J=10.4, 5.3Hz, 4H), 3.84( dd, J=10.8, 6.7Hz, 2H), 2.86–2.60(m, 10H), 2.56(tt, J=12.1, 3.4Hz, 1H), 2.15(tt, J=6.5, 4.2Hz, 1H), 2.11 –2.04(m, 4H), 2.03–1.85(m, 12H), 1.54(qd, J=12.8, 3.3Hz, 3H), 1.32(dddd, J=26.7, 15.0, 8.8, 6.3Hz, 9H), 1.20 (td, J=7.5, 4.6Hz, 6H), 1.11 (qd, J=13.1, 3.3Hz, 2H), 0.93 (t, J=7.0Hz, 3H).

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Abstract

Liquid-crystalline media (LC media) comprising self-aligning mesogens (self-alignment additives) which effect homeotropic (vertical) alignment of the LC media at a surface or the cell walls of a liquid-crystal display (LC display). The self-alignment additives contain five-ring systems. LC displays having homeotropic alignment of the liquid-crystalline medium (LC medium) without conventional alignment layers are provided.

Description

technical field [0001] The invention relates to liquid crystal media (LC media) comprising novel self-aligning mesogens (self-alignment additives) which enable the vertical alignment of the LC media at the surface or cell wall of a liquid crystal display (LC display) Planar (vertical) alignment. The new self-aligning additive contains a pentacyclic ring system. The invention also includes LC displays with homeotropic alignment of liquid crystal media (LC media) without conventional alignment layers. Background technique [0002] The principle of electrically controlled birefringence, the ECB effect or also the DAP (Alignment Distortion) effect was first described in 1971 (M.F.Schieckel and K.Fahrenschon, "Deformation of nematic liquid crystals with vertical orientation in electrical fields", Appl. Phys. Lett .19(1971), 3912). Then there are papers by J.F. Kahn (Appl. Phys. Lett. 20 (1972), 1193) and G. Labrunie and J. Robert (J. Appl. Phys. 44 (1973), 4869). [0003] Pap...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C69/54C09K19/38G02F1/1337
CPCC07C69/54C09K19/3852G02F1/133711C07C2601/14C09K2019/0425C09K19/02C09K19/04C09K19/12C09K19/3003C09K2019/0448C09K2019/125C07C69/602C09K19/56C09K19/544C09K19/30G02F1/1337C09K19/542C09K2019/548
Inventor M·克拉森-梅默E·普鲁默R·福特H·哈恩赛尔T·尤贝尔T·勒曼
Owner MERCK PATENT GMBH
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