Compounds for the homeotropic alignment of liquid-crystalline media

Abstract

Disclosed are liquid-crystalline media (LC media) comprising a low-molecular-weight component and a polymerisable component. The polymerisable component contains self-aligning, polymerisable mesogens(polymerisable 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). Disclosed are also LC displays having homeotropic alignment of the LC medium without alignment layers. Further disclosed are the structures for polymerisable self-alignment additives.

Description

Contents of the invention

[0001] The invention relates to liquid-crystalline media (LC media) comprising low molecular weight components and polymerizable components. The polymerizable component comprises self-aligning, polymerizable mesogens (polymerizable self-aligning additives) that achieve a homeotropic (vertical) alignment of the LC medium at the surface or cell wall of a liquid crystal display (LC display). The invention therefore also includes LC displays with homeotropic alignment of liquid-crystalline media (LC media), which do not have an alignment layer for homeotropic alignment. The present invention discloses novel structures for polymerizable self-aligning additives. 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",...

Examples

Embodiment 1

[0429] Example 1. Synthesis of 3-{2-[4-hydroxyl-3-(hydroxymethyl)butoxy]-3-{3-[(2-methylprop-2-enoyl)oxyl]propyl }-5-[4-(4-pentylcyclohexyl)cyclohexyl]phenyl}-propyl 2-methylprop-2-enoate 1

[0430]

[0431] 1.1. Synthesis of 1-(benzyloxy)-4-[4-(4-pentylcyclohexyl)cyclohex-1-en-1-yl]-benzene (A)

[0432]

[0433] First, 3.40 g (140 mmol) of magnesium chips were added to 10 ml of tetrahydrofuran (THF), the mixture was warmed to the boiling point, and a 10 ml solution of 36.0 g (137 mmol) of 1-(benzyloxy)-4-bromobenzene in 90 ml of THF was added to initiate the Grignard reaction. The heat source was removed, and the remaining solution was slowly added dropwise to the reaction mixture at such a rate that the reaction solution boiled under reflux. During this addition, the color of the reaction mixture turned brown, and when the addition was complete, the mixture was stirred at the boil for an additional 1 hour. A solution of 30.0 g (120 mmol) of 4-(4-pentylcyclohexyl)cycl...

Embodiment 2

[0460]

[0461] Colorless crystals.

[0462] Phase: Tg-28°C, melting point 47°C.

[0463] 1 H NMR (500MHz, CDCl 3 ):δ=0.91ppm(m c ,8H,CH 3 , CH 2 ), 1.03(m c , 3H), 1.10-1.21(m, 6H), 1.22-1.50(m, 14H), 1.67-1.92(m, 8H), 1.97(s (重叠的) ,8H,CH 3 ), 2.02(m c , 4H), 2.37(tt (重叠的，具有2 X OH(superimposed with 2 X OH) ), 2.94, 9.18Hz, 3H, CH(CH 2 ) 2 ), 2.72 (m c 4H), 3.67 (2Xd (重叠的)， J=11.58Hz, 4H), 3.90(t, J=6.26Hz, 2H), 4.23(t, J=6.6Hz, 4H), 5.58(t, J=1.54Hz, 2H, O(CO)C(CH 3 )CH 2 ), 6.13(s (宽) , 2H, O(CO)C(CH 3 )CH 2 ), 6.89(s, 2H).

Embodiment 3

[0465]

[0466] Colorless crystals.

[0467] Phase: Tg-18°C, melting point 73°C.

[0468] 1 H NMR (500MHz, CDCl 3 ):δ=0.82-0.94ppm(s (重叠的)， 14H,t-Bu,CH 3 , CH 2 ), 1.02(m c , 3H), 1.16(m c ,8H), 1.30(m c ,8H), 1.40(m c , 2H), 1.70-1.92(m, 8H), 1.94(t, J=6.28Hz, 2H), 1.97(s (重叠的) ,6H,CH 3 ), 2.02 (quint. (宽) J=7.53Hz, 4H), 2.37(tt, J=2.92, 12.08Hz, 1H, CH(CH 2 ) 2 ), 2.50(s (宽) , 2H, OH), 2.71 (m c , 4H), 3.65(d, J=11.13Hz, 2H, CH 2 OH), 3.68(d, J=11.14Hz, CH 2 -OH), 3.89(t, J=6.23H, 2H), 4.23(t, J=6.61, 4H), 5.59(s (宽) , 2H, O(CO)C(CH 3 )CH 2 ), 6.13(s (宽) , 2H, O(CO)C(CH 3 )CH 2 ), 6.89(s, 2H).

Contents of the invention

[0001] The invention relates to liquid-crystalline media (LC media) comprising low molecular weight components and polymerizable components. The polymerizable component comprises self-aligning, polymerizable mesogens (polymerizable self-aligning additives) that achieve a homeotropic (vertical) alignment of the LC medium at the surface or cell wall of a liquid crystal display (LC display). The invention therefore also includes LC displays with homeotropic alignment of liquid-crystalline media (LC media), which do not have an alignment layer for homeotropic alignment. The present invention discloses novel structures for polymerizable self-aligning additives. 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",...

Examples

Embodiment 1

[0429] Example 1. Synthesis of 3-{2-[4-hydroxyl-3-(hydroxymethyl)butoxy]-3-{3-[(2-methylprop-2-enoyl)oxyl]propyl }-5-[4-(4-pentylcyclohexyl)cyclohexyl]phenyl}-propyl 2-methylprop-2-enoate 1

[0430]

[0431] 1.1. Synthesis of 1-(benzyloxy)-4-[4-(4-pentylcyclohexyl)cyclohex-1-en-1-yl]-benzene (A)

[0432]

[0433] First, 3.40 g (140 mmol) of magnesium chips were added to 10 ml of tetrahydrofuran (THF), the mixture was warmed to the boiling point, and a 10 ml solution of 36.0 g (137 mmol) of 1-(benzyloxy)-4-bromobenzene in 90 ml of THF was added to initiate the Grignard reaction. The heat source was removed, and the remaining solution was slowly added dropwise to the reaction mixture at such a rate that the reaction solution boiled under reflux. During this addition, the color of the reaction mixture turned brown, and when the addition was complete, the mixture was stirred at the boil for an additional 1 hour. A solution of 30.0 g (120 mmol) of 4-(4-pentylcyclohexyl)cycl...

Embodiment 2

[0460]

[0461] Colorless crystals.

[0462] Phase: Tg-28°C, melting point 47°C.

[0463] 1 H NMR (500MHz, CDCl 3 ):δ=0.91ppm(m c ,8H,CH 3 , CH 2 ), 1.03(m c , 3H), 1.10-1.21(m, 6H), 1.22-1.50(m, 14H), 1.67-1.92(m, 8H), 1.97(s (重叠的) ,8H,CH 3 ), 2.02(m c , 4H), 2.37(tt (重叠的，具有2 X OH(superimposed with 2 X OH) ), 2.94, 9.18Hz, 3H, CH(CH 2 ) 2 ), 2.72 (m c 4H), 3.67 (2Xd (重叠的)， J=11.58Hz, 4H), 3.90(t, J=6.26Hz, 2H), 4.23(t, J=6.6Hz, 4H), 5.58(t, J=1.54Hz, 2H, O(CO)C(CH 3 )CH 2 ), 6.13(s (宽) , 2H, O(CO)C(CH 3 )CH 2 ), 6.89(s, 2H).

Embodiment 3

[0465]

[0466] Colorless crystals.

[0467] Phase: Tg-18°C, melting point 73°C.

[0468] 1 H NMR (500MHz, CDCl 3 ):δ=0.82-0.94ppm(s (重叠的)， 14H,t-Bu,CH 3 , CH 2 ), 1.02(m c , 3H), 1.16(m c ,8H), 1.30(m c ,8H), 1.40(m c , 2H), 1.70-1.92(m, 8H), 1.94(t, J=6.28Hz, 2H), 1.97(s (重叠的) ,6H,CH 3 ), 2.02 (quint. (宽) J=7.53Hz, 4H), 2.37(tt, J=2.92, 12.08Hz, 1H, CH(CH 2 ) 2 ), 2.50(s (宽) , 2H, OH), 2.71 (m c , 4H), 3.65(d, J=11.13Hz, 2H, CH 2 OH), 3.68(d, J=11.14Hz, CH 2 -OH), 3.89(t, J=6.23H, 2H), 4.23(t, J=6.61, 4H), 5.59(s (宽) , 2H, O(CO)C(CH 3 )CH 2 ), 6.13(s (宽) , 2H, O(CO)C(CH 3 )CH 2 ), 6.89(s, 2H).

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