GB2583649A - Liquid crystal compound and liquid crystal medium - Google Patents

Liquid crystal compound and liquid crystal medium Download PDF

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GB2583649A
GB2583649A GB2010827.0A GB202010827A GB2583649A GB 2583649 A GB2583649 A GB 2583649A GB 202010827 A GB202010827 A GB 202010827A GB 2583649 A GB2583649 A GB 2583649A
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chex
phe
phel
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Siemianowski Simon
Bremer Matthias
Jehn Jana
Schneider Konstantin
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Merck Patent GmbH
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Merck Patent GmbH
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    • C09K2019/0448—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit characterized by a linking chain between rings or ring systems, a bridging chain between extensive mesogenic moieties or an end chain group the end chain group being a polymerizable end group, e.g. -Sp-P or acrylate
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    • C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
    • C09K19/12—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings at least two benzene rings directly linked, e.g. biphenyls
    • C09K2019/121—Compounds containing phenylene-1,4-diyl (-Ph-)
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    • C09K19/3001—Cyclohexane rings
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    • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
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    • C09K19/3001—Cyclohexane rings
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    • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
    • C09K19/3001—Cyclohexane rings
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    • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
    • C09K19/3001—Cyclohexane rings
    • C09K19/3003—Compounds containing at least two rings in which the different rings are directly linked (covalent bond)
    • C09K2019/3027—Compounds comprising 1,4-cyclohexylene and 2,3-difluoro-1,4-phenylene

Abstract

The invention relates to compounds of formula (I) : R11-A11-(Z11-A12)p-X11-Sp11-X12-(A13-Z13)q-A14-R12, wherein R11, R12, A11 to A14, Z11, Z13, X11, X12, Sp11, p and q have one of the meanings as given herein below. The invention further relates to method of production of compounds of formula (I), to the use of said compounds in LC media and to LC media comprising one or more compounds of formula (I). Further, the invention relates to a method of production of such LC media, to the use of such media in electro optical device, in particular, in flexoelectric electro optical device and to a flexoelectric electro optical device, as such.

Claims (19)

P17310 SL
1. WO 2019/121438 PCT/EP2018/085101 - 85 - Patent Claims
1 . Compounds of formula I, R1 1_A1 1(-Z1 1-A12-)P -X1 1-Sp1 1-Xi2 -(A13-Z12-)q A14-R12 wherein R 1 1 denotes P-Sp 10 P denotes a polymerisable group, Sp denotes a spacer group or a single bond, R12 denotes F, Cl, CN, NO2, NCO, NCS or a straight-chain 15 or branched alkyl group, which may be unsubstituted, mono- or polysubstituted by halogen or CN and in which one or more non-adjacent and non-terminal CH2 groups may be replaced, in each occurrence independently from one another, by -0-, -S-, -NH-, 20 -N(CH3)-, -CO-, -COO-, -OCO-, -O-CO-O-, -S-CO-, -CO-S-, -CH=CH-, -CH=CF-, -CF=CF- or -CºC- in such a manner that oxygen atoms are not linked directly to one another, or R1 1 ,
25 A1 1 to A14 each independently in each occurrence denote, 1 ,4- phenylene, wherein in addition one or more CFI groups may be replaced by N, trans-1 ,4-cyclo- hexylene in which, in addition, one or two non- adjacent CFI2 groups may be replaced by O and/or S,
30 1 ,4-cyclohexylene, naphthalene-2, 6-diyl, decahydro- naphthalene-2,6-diyl, 1 ,2,3,4-tetrahydro-naphthalene- 2, 6-diyl, it being possible for all these groups to be unsubstituted, mono-, di-, tri- or tetrasubstituted with F, Cl, CN or alkyl, alkoxy, alkylcarbonyl or 35 alkoxycarbonyl groups, wherein one or more FI atoms may be substituted by F or Cl, P17310 SL WO 2019/121438 PCT/EP2018/085101 86 Z1 1 and Z12 are, independently of each other in each occurrence, a single bond, -COO-, -OCO-, -O-CO-O-, -OCFI2-, -CH2O-, -OCF2-, -CF2O-, -CH2CH2-, -(CH2)4-, -CF2CF2-, 5 -CH=CH-, -CF=CF-, -CH=CH-COO-, -OCO-CH=CH- or -CºC-, optionally substituted with one or more of F, S and/or Si, p and q is each and independently 0, 1 , 2, 3 or 4, 10 Sp1 1 is a spacer group comprising 1 , 3 or 5 to 40 C atoms, wherein one or more non-adjacent and non-terminal Chte groups may also be replaced by -0-, -S-, -NH-, -N(CH3)-, -CO-, -O-CO-, -S-CO-, -O-COO-, -CO-S-, 15 -CO-0-, -CF2-, -CF2O-, -OCF2- -C(OH)-, -CH(alkyl)-, -CH(alkenyl)-,-CH(alkoxyl)-, -CH(oxaalkyl)-, -CH=CH- or -CºC-, however in such a way that no two O-atoms are adjacent to one another and no two groups selected from -O-CO-, -S-CO-, -O-COO-, -CO-S-, 20 -CO-O- and -CFI=CFI- are adjacent to each other, X1 1 and X12 are independently from one another selected from a single bond, -CO-O-, -O-CO-, -O-COO-, -0-, -CH=CH-, -CºC-, -CF2-O-, -O-CF2-, -CF2-CF2-, 25 -CH2-O-, -O-CH2-, -CO-S-, -S-CO-, -CS-S-, -S-CS-, - S-CSS- and -S-, wherein in -X1 1-Sp1 1-X12- respectively two O atoms, two -CFI=CFI- groups and two groups selected from -O-CO-, -S-CO-, -O-COO-, -CO-S- and -CO-O- are not linked directly to one another. 30
2. Compounds according to claim 1 , characterized in that the group -A1 1(-Z1 1-A12-)p - or -(A13-Z12-)q A14- is selected from the following formulae, 35 -CHex- MG-12-1 -Phe- MG-12-2 P17310 SL WO 2019/121438 PCT/EP2018/085101 - 87 - -PheL- MG-12-3 -CHex-CHex- MG-12-4 -CHex-Phe- MG-12-5 5 -CHex-PheL- MG-12-6 -Phe-CHex- MG-12-7 -PheL-CHex- MG-12-8 -Phe-Phe- MG-12-9 -PheL-PheL- MG-12-10 10 -PheL-Phe- MG-12-11 -Phe-PheL- MG-12-12 -CHex-Phe-Phe- MG-12-13 -CHex-Phe-PheL- MG-12-14 15 -CHex-PheL-Phe- MG-12-15 -CHex-PheL-PheL- MG-12-16 -Phe-CHex-Phe- MG-12-17 -PheL-CHex-Phe- MG-12-18 -Phe-CHex-PheL- MG-12-19 20 -PheL-CHex-PheL- MG-12-20 -Phe-Phe-CHex- MG-12-21 -Phe-PheL-CHex- MG-12-22 -PheL-Phe-CHex- MG-12-23 -PheL-PheL-CHex- MG-12-24 25 -CHex-Phe-CHex- MG-12-25 -CHex-PheL-CHex- MG-12-26 -CHex-CHex-PheL- MG-12-27 -CHex-CHex-Phe- MG-12-28 -PheL-CHex-CHex- MG-12-29 30 -Phe-CHex-CHex- MG-12-30 -C H ex-C H ex-C H ex- MG-12-31 -Phe-Phe-Phe- MG-12-32 -Phe-Phe-PheL- MG-12-33 -Phe-PheL-Phe- MG-12-34 35 -PheL-Phe-Phe- MG-12-35 -PheL-PheL-Phe- MG-12-36 P17310 SL WO 2019/121438 PCT/EP2018/085101 88 -Phe-PheL-PheL- MG-12-37 -PheL-PheL-PheL- MG-12-38 -CHex-Z-CHex- MG-12-39 5 -CHex-Z-Phe- MG-12-40 -CHex-Z-PheL- MG-12-41 -Phe-Z-CHex- MG-12-42 -PheL-Z-CHex- MG-12-43 -Phe-Z-Phe- MG-12-44 10 -PheL-Z-PheL- MG-12-45 -PheL-Z-Phe- MG-12-46 -Phe-Z-PheL- MG-12-47 -CHex-Z-Phe-Phe- MG-12-48 15 -CHex-Z-Phe-PheL- MG-12-49 -CHex-Z-PheL-Phe- MG-12-50 -CHex-Z-PheL-PheL- MG-12-51 -Phe-Z-CHex-Phe- MG-12-52 -PheL-Z-CHex-Phe- MG-12-53 20 -Phe-Z-CHex-PheL- MG-12-54 -PheL-Z-CHex-PheL- MG-12-55 -Phe-Z-Phe-CHex- MG-12-56 -Phe-Z-PheL-CHex- MG-12-57 -PheL-Z-Phe-CHex- MG-12-58 25 -PheL-Z-PheL-CHex- MG-12-59 -CHex-Z-Phe-CHex- MG-12-60 -CHex-Z-PheL-CHex- MG-12-61 -CHex-Z-CHex-PheL- MG-12-62 -CHex-Z-CHex-Phe- MG-12-63 30 -PheL-Z-CHex-CHex- MG-12-64 -Phe-Z-CHex-CHex- MG-12-65 -CHex-Z-CHex-CHex- MG-12-66 -Phe-Z-Phe-Phe- MG-12-67 -Phe-Z-Phe-PheL- MG-12-68 35 -Phe-Z-PheL-Phe- MG-12-69 -PheL-Z-Phe-Phe- MG-12-70 P17310 SL WO 2019/121438 PCT/EP2018/085101 89 -PheL-Z-PheL-Phe- MG-12-71 -Phe-Z-PheL-PheL- MG-12-72 -PheL-Z-PheL-PheL- MG-12-73 5 -CHex-Phe-Z-Phe- MG-12-74 -CHex-Phe-Z-PheL- MG-12-75 -CHex-PheL-Z-Phe- MG-12-76 -CHex-PheL-Z-PheL- MG-12-77 -Phe-CHex-Z-Phe- MG-12-78 10 -PheL-CHex-Z-Phe- MG-12-79 -Phe-CHex-Z-PheL- MG-12-80 -PheL-CHex-Z-PheL- MG-12-81 -Phe-Phe-Z-CHex- MG-12-82 -Phe-PheL-Z-CHex- MG-12-83 15 -PheL-Phe-Z-CHex- MG-12-84 -PheL-PheL-Z-CHex- MG-12-85 -CHex-Phe-Z-CHex- MG-12-86 -CHex-PheL-Z-CHex- MG-12-87 -CHex-CHex-Z-PheL- MG-12-88 20 -CHex-CHex-Z-Phe- MG-12-89 -PheL-CHex-Z-CHex- MG-12-90 -Phe-CHex-Z-CHex- MG-12-91 -CHex-CHex-Z-CHex- MG-12-92 -Phe-Phe-Z-Phe- MG-12-93 25 -Phe-Phe-Z-PheL- MG-12-94 -Phe-PheL-Z-Phe- MG-12-95 -PheL-Phe-Z-Phe- MG-12-96 -PheL-PheL-Z-Phe- MG-12-97 -Phe-PheL-Z-PheL- MG-12-98 30 -PheL-PheL-Z-PheL- MG-12-99 -CHex-Z-Phe-Z-Phe- MG-12-100 -CHex-Z-Phe-Z-PheL- MG-12-101 -CHex-Z-PheL-Z-Phe- MG-12-102 35 -CHex-Z-PheL-Z-PheL- MG-12-103 -Phe-Z-CHex-Z-Phe- MG-12-104 P17310 SL WO 2019/121438 PCT/EP2018/085101 - 90 - -PheL-Z-CHex-Z-Phe- MG-12-105 -Phe-Z-CHex-Z-PheL- MG-12-106 -PheL-Z-CHex-Z-PheL- MG-12-107 -Phe-Z-Phe-Z-CHex- MG-12-108 5 -Phe-Z-PheL-Z-CHex- MG-12-109 -PheL-Z-Phe-Z-CHex- MG-12-110 -PheL-Z-PheL-Z-CHex- MG-12-111 -CHex-Z-Phe-Z-CHex- MG-12-112 -CHex-Z-PheL-Z-CHex- MG-12-113 10 -CHex-Z-CHex-Z-PheL- MG-12-114 -CHex-Z-CHex-Z-Phe- MG-12-115 -Phe-Z-CHex-Z-CHex- MG-12-116 -Phe-Z-CHex-Z-CHex- MG-12-117 -CHex-Z-CHex-Z-CHex- MG-12-118 15 -Phe-Z-Phe-Z-Phe- MG-12-119 -Phe-Z-Phe-Z-PheL- MG-12-120 -Phe-Z-PheL-Z-Phe- MG-12-121 -PheL-Z-Phe-Z-Phe- MG-12-122 -PheL-PheL-Z-Phe- MG-12-123 20 -Phe-PheL-Z-PheL- MG-12-124 -PheL-PheL-Z-PheL- MG-12-125 wherein
25 CHex is 1 ,4-cyclohexylene, Phe is 1 ,4-phenylene, PheL is 1 ,4-phenylene, which is substituted by one, two or three fluorine atoms, by one or two Cl atoms or by one Cl atom and one F atom and Z has one of the meanings of Z11 as given under partial 30 formula II and if present twice, at least one is selected from -CºC-, -C=C-, -COO-, -OCO-, -0-C0-0-, -OCH2-, -CH2O-, -OCF2- or -CF2O-.
3. Compounds according to claim 1 or 2, characterized in that Sp11 35 denotes -(CFh with n being an integer from 1 to 15, wherein one or more -CFI2- groups may be replaced by -CO-. P17310 SL WO 2019/121438 PCT/EP2018/085101 - 91 -
4. Compounds according to one or more of claims 1 to 3, characterized in that -X1 1-Sp1 1-Xi2. denotes -Sp1 1-, -Sp1 1-0-, -Sp1 1-C0-0-, -Sp1 1-0- CO-, -CO-O-Sp1 1 , -O-CO-Sp1 1 , -O-Sp1 1-, -O-Sp1 1- C0-0-, -0-Sp1 1-0-C0-, -O-CO-Sp1 1-0-, -O-CO- Sp1 1-0-C0-, -CO-O-Sp1 1-0- or -CO-O-Sp1 1-CO- 0-, however under the condition that in 10 -X1 1-Sp1 1-X12- no two O-atoms are adjacent to one another, no two -CH=CH- groups are adjacent to each other and no two groups selected from -0-C0-, -S-CO-, -0-C00-, -CO-S-, -CO-O- and -CH=CH- are adjacent to each other, and
15 Sp 1 1 denotes -(CFtejn- with n being an integer from 1 to 15, wherein one or more -CFte- groups may be replaced by -CO-. Use of the compounds of formula I according to one or more of 20 claims 1 to 4 in a liquid crystalline medium.
6. LC medium comprising one or more compounds of formula I according to one or more of claims 1 to 4.
25 LC medium according to claim 6, comprising one or more compounds of formula II, R21-A21-A22-(CH2)a-A23-A24-R22 30 wherein R21 and R22 denote each and independently H, F, Cl, CN, or a straight-chain or branched alkyl group, which may be unsubstituted, mono- or polysubstituted by halogen or CN, it being also possible for one or more non- 35 adjacent CFte groups to be replaced, in each occurrence independently from one another, by -0-, P17310 SL WO 2019/121438 PCT/EP2018/085101 - 92 - -S-, -NH-, -N(CH3)-, -CO-, -COO-, -OCO-, -0-C0-0-, -S-CO-, -CO-S-, -CH=CH-, -CH=CF-, -CF=CF- or -CºC- in such a manner that oxygen atoms are not linked directly to one another, 5 A21 to A24 denote each and independently in each occurrence a aryl-, heteroaryl-, alicyclic and heterocyclic group and a denotes an integer from 1 to 15. 10
8. LC medium according to claim 6 or 7, comprising one or more compounds of formula III, R31 -A31 -A32-(A33)b-Z31 -(CH2)C-Z32-A34-A35-A36- R32 15 wherein R31 and R32 have each and independently from another one of the meanings as given for R21 under formula II,
20 A31 to A36 have each and independently from another one of the meanings as given for A21 under formula II, Z31 and Z32 denote each and independently in each occurrence, -COO-, -OCO-, -0-C0-0-, -OCH2-, -CH2O-, 25 -CH2CH2-, -(CH2)4-, -, -CF2-O-, -O-CF2-, -CF2CF2-, -CH=CH-, -CF=CF-, -CH=CH-COO-, -OCO-CFI=CFI- or -CºC-, optionally substituted with one or more of F, S and/or Si 30 c denotes an integer from 1 to 15 and a denotes 0 or 1.
9. LC medium according to one or more of claims 6 to 8, comprising 35 one or more compounds of formula IV, P17310 SL WO 2019/121438 PCT/EP2018/085101 93 R41 -A41 -A42-Z41 -(C H2)d-Z42-A43-A44- R42 IV wherein R41 and R42 have each and independently from another one of 5 the meanings as given for R21 under formula II, A41 to A44 have each and independently from another one of the meanings as given for A21 under formula II, 10 Z41 and Z42 are each independently in each occurrence, -COO-, -OCO-, -0-C0-0-, -OCH2-, -CH2O-, -CH2CH2-, -(CH2)4-, -, -CF2-O-, -O-CF2-, -CF2CF2-, -CH=CH-, -CF=CF-, -CH=CH-COO-, 15 -OCO-CFI=CFI- or -CºC-, optionally substituted with one or more of F, S and/or Si, d denotes an integer from 1 to 1 5
20 1 0. LC medium according to one or more of claims 6 to 9, comprising one or more compounds of formula V, R51.A51.Z51.(C|_|2)e.Z52.A52.(A53)f. R52 V 25 wherein R51 and R52 have each and independently from another one of the meanings as given for R21 under formula II, A51 to A53 have each and independently from another one of 30 the meanings as given for A21 under formula II, Z51 and Z52 are each independently in each occurrence, -COO-, -OCO-, -O-CO-O-, -OCH2-, -CH2O-, -CH2CH2-, -(CH2)4-, -, -CF2-O-, -O-CF2-, -CF2CF2-, 35 -CH=CH-, -CF=CF-, -CH=CH-COO-, P17310 SL WO 2019/121438 PCT/EP2018/085101 - 94 - -OCO-CFI=CFI- or -CºC-, optionally substituted with one or more of F, S and/or Si, f denotes 0 or 1 5 e denotes an integer from 1 to 15
1 1 . LC medium according to one or more of claims 6 to 10, comprising one or more compounds of formula VI, 10 R61 -A61 -A62-(CH2)g-Z61 -A63-A64-(A65)h-R62 VI wherein R61 and R62 have each and independently from another one of 15 the meanings as given for R21 and R22 under formula II, A61 to A64 have each and independently one of the meanings as given above for A21 under formula II, 20 Z61 denotes -0-, -COO-, -OCO-, -0-C0-0-, -OCH2-, -CH20, -CH2CH2-, -(CH2)4-, -, -CF2-0-, -O-CF2-, -CF2CF2-, -CH=CH-, -CF=CF-, -CH=CH-COO-, -OCO-CFI=CFI- or -CºC-, optionally substituted with 25 one or more of F, S and/or Si, h denotes 0 or 1 and g denotes an integer from 1 to 15. 30
12. LC medium according to one or more of claims 6 to 1 1 , comprising one or more compounds of formula VII, R71-A71-Z71-A72-(Z72-A73)j-(CH2)k-(A74-Z73-)i-A75-Z74-A76-R72 VII 35 wherein P17310 SL WO 2019/121438 PCT/EP2018/085101 95 R71 and R72 have each and independently one of the meanings as given above for R21 under formula II, A71 to A76 have each and independently one of the meanings 5 as given above for A21 under formula II, Z71 to Z74 each and independently denotes -COO-, -OCO-, -0-C0-0-, -OCH2-, -CH2O-, -OCF2-, -CF2O-, -CH2CH2-, -(CH2)4-,-CF2CF2-, -CH=CH-, -CF=CF-, 10 -CH=CH-COO-, -OCO-CH=CH- or -CºC-, optionally substituted with one or more of F, S and/or Si or a single bond, with the proviso that at least one of Z71 to Z74 is not a single bond, 15 j denotes an integer from 1 to 15 and i and k denotes 0 or 1.
13. LC medium according to one or more of claims 6 to 12, comprising one or more chiral dopants. 20
14. LC medium according to one or more of claims 6 to 13, comprising one or more nematic LC compounds selected from compounds of formula X-1 to X-4, 25 P17310 SL WO 2019/121438 PCT/EP2018/085101 5 in which R2A denotes H, an alkyl, alkenyl or alkoxy radical having 1 to 15 C atoms, where, in addition, one or more CFh groups in these radicals may each be replaced, independently of one another, by -CºC-, 10 -CF2O-, -CH=CH-, - , -OO- , -0-, -CO-O- or -O-CO- in such a way that O atoms are not linked directly to one another and in which, in addition, one or more H atoms may be replaced 15 by halogen, L1 and L2 each, independently of one another, denote F, Cl, CFs or CHF2,
20 Z2 and Z2' each, independently of one another, denote a sin- gle bond, -CH2CH2-, -CH=CH-, -CºC-, -CF2O-, -OCF2-, -CH2O-, -OCH2-, -COO-, -OCO-, -C2F4-, -CF=CF- or -CH=CHCH20-, 25 p denotes 0, 1 or 2, q denotes 0 or 1 , (0)CVH2V+1 denotes OCvFhv+1 or CvFhv+1 and 30 v denotes 1 to 6.
15. Method for the production of an LC medium according to one or more of claims 6 to 14, comprising the step of mixing one or more compounds of formula I according to one or more of claims 1 to 4, P17310 SL WO 2019/121438 PCT/EP2018/085101 - 97 - with at least one compound selected from compounds of formulae II to X.
16. Use of a LC medium according to one or more of claims 6 to 14, in 5 electro optical devices.
17. Process of preparing an electro optical device comprising the steps of 10 a) providing a layer LC medium according to one or more of claims 6 to 14, between two substrates, wherein at least one substrate is transparent to light and electrodes are provided on both sides of the opposing substrates, 15 b) heating the liquid crystal medium to its isotropic phase, c) cooling the liquid crystal medium below the clearing point while applying voltage between the electrodes, which is sufficient to switch the liquid crystal medium between switched states, 20 d) exposing said layer of a liquid crystal medium to photoradiation that induces photopolymerisation of the polymerisable compounds while applying voltage between the electrodes.
25
18. Electro optical device obtainable from the process according to claim
17.
19. Electro optical device according to claim 18, characterized in that it is a flexoelectric device. 30 35
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