# US 7,195,719 B1 · High polarization ferroelectric liquid crystal compositions

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- Number: US 7,195,719 B1
- Document ID: US7195719B1
- Status: Granted
- Kind: B1
- Application number: 10/038,054
- Filed: 2002-01-03
- Granted: 2007-03-27
- Earliest claimed: 2001-01-03
- Assignees: Displaytech, Inc.
- Inventors: Michael Wand; Xin Hua Chen; William N. Thurmes
- Web page: https://patentgrep.com/patent/US7195719B1

## CPC

- C09K 19/586: {Optically active dopants; chiral dopants}
- C07D 239/26: with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D 405/12: linked by a chain containing hetero atoms as chain links
- C09K 19/0225: {Ferroelectric}
- C09K 19/3458: {Uncondensed pyrimidines}
- C09K 19/3469: {Pyrimidine with a specific end-group other than alkyl, alkoxy or -C*-}
- C09K 19/588: {Heterocyclic compounds}
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

The invention relates to chiral nonracemic liquid crystal compounds having achiral tails comprising a perfluoroalkyl terminal portion which are useful as components in liquid crystal to impart high polarization to the mixture. The materials of this invention can be combined with known liquid crystal host materials to impart improved properties. Chiral nonracemic compounds of this invention can function as additives or dopants in host materials to impart chirality into an LC material.

## Claims

### Claim 1

A chiral, non-racemic liquid crystal composition comprising a chiral compound of the formula:
CnF2n+1CmH2m—Y—RT-[A]a-[RA]p-[B]b—[RB]q—XCR
wherein
n is an integer from 1 to 20;
m is an integer from 2 to 20;
a, b, p and q are either 0 or 1, when p is 0, a is 0 and when q is 0, b is 0;
Y is a single bond or oxygen;
X is selected from the group consisting of a single bond, oxygen, —CO—, —O—CO—, —CO—O— and a lower alkylene group where one or more carbon atoms is optionally substituted with one or more of oxygen or —CO—;
CR is selected from the group consisting of:
wherein
each of R1 and R3 is independently hydrogen, lower alkyl, lower alkenyl, lower haloalkyl, or lower haloalkenyl;
R2 is an alkyl, alkenyl, ether, thioether, or silyl group having from 1 to about 20 carbon atoms wherein one or more CH2 groups are optionally replaced with —S—, —O—, —CO—, —CO—O—, —O—CO—, or —Si(R′)2, and where R′ is lower alkyl or lower haloalkyl,
provided at least one carbon center indicated by * is an asymmetric carbon center;
A and B, independently, are linker groups selected from the group consisting of —CO—, —O—CO—, —CO—O—, —CH2—CH2—, —CH2—CH2—O—, —O—CH2—CH2—, —C≡C—, —CH═CH—, and —CH═CH—CH═CH—, and
RT, RA, and RB together represent a mesogenic core, wherein each of the RT, RA, and RB is independently selected from the group consisting of cycloalkylene, and heterocycloalkylene, cycloalkylene, heterocycloalkenylene, arylene, and heteroarylene each of which is independently optionally substituted with one or more substituents selected from the group consisting of halide, alkyl, haloalkyl, alkenyl, haloalkenyl, nitro, and nitrile.

### Claim 2 (depends on 1)

The composition of claim 1 wherein CR is selected from the group consisting:
each RT, RA, and RB is independently selected from the group consisting of naphthylene, cyclohexylene, 6-membered heterocycloalkylene comprising one or two ring nitrogen atoms, cyclohexenylene, 6-membered heterocycloalkenylene comprising one or two ring nitrogen atoms, phenylene, and heteroarylene comprising one or two ring nitrogen atoms each of which is independently optionally substituted with one or more substituents selected from the group consisting of halide, alkyl, haloalkyl, alkenyl, haloalkenyl, nitro, and nitrile.

### Claim 3 (depends on 1)

The composition of claim 1 wherein each of RT, RA, and RB is independently selected from the group consisting of naphthylene, phenylene, cyclohexylene, cyclohexenylene, pyrimidinylene, pyridinylene, 1,2,34-tetrahydronaphthylene, and 1,4-dihydronaphthylene.

### Claim 4 (depends on 1)

The composition of claim 1, wherein said mesogenic core is a biaryl moiety.

### Claim 5 (depends on 1)

The composition of claim 1 wherein said mesogenic core selected from the group consisting of:
where R″ is lower alkyl.

### Claim 6 (depends on 1)

The composition of claim 1, wherein said chiral, non-racemic liquid crystal composition further comprises an achiral liquid crystal host.

### Claim 7 (depends on 6)

The composition of claim 6, wherein the said achiral liquid crystal host comprises an achiral compound selected from the group consisting of:
and a mixture of two or more thereof.

### Claim 8 (depends on 1)

The composition of claim 1 wherein n=m.

### Claim 9 (depends on 1)

The composition of claim 1 wherein Y is O.

### Claim 10 (depends on 1)

The composition of claim 1 wherein the total amount of chiral compound in said chiral, non-racemic liquid crystal composition is 10% or less.

### Claim 11 (depends on 1)

The composition of claim 1 which has Ps of 10 nC/cm2 or more at room temperature.

### Claim 12 (depends on 11)

The composition of claim 11 wherein the total amount of chiral compound in said chiral, non-racemic liquid crystal composition is 5% by weight or less.

### Claim 13

A compound having the formula:
wherein
n and m are integers ranging from 1 to about 20;
X is selected from the group consisting of a single bond, oxygen, —CO—, —OCO—, —CO—O—2 and a lower alkyl group, wherein one or more carbon atoms of said lower alkyl group is optionally replaced with oxygen or —CO—; and
CR is selected from the group consisting of:
wherein
R1 and R3, independently of each other, are hydrogen, lower alkyl, lower alkenyl, lower haloalkyl, or lower haloalkenyl; and
R2 is hydrogen, alkyl, alkenyl, ether, thioether, or silyl group having from 1 to about 20 carbon atoms wherein one or more CH2 groups are optionally replaced with —S—, —O—, —CO—, —CO—O—, —O—CO—, or —Si(R′)2—, wherein R′ is a lower alkyl optionally substituted with one or more halogens;
provided at least one carbon center indicated by * is an asymmetric carbon center.

### Claim 14

A chiral, non-racemic liquid crystal composition comprising a chiral compound of the formula:
CnF2n+1CmH2m—Y—RT—[A]a—[RA]p—[B]b—[RB]q—XCR
wherein
n is an integer from 1 to 20;
m is an integer from 2 to 20;
a, b, p and q are either 0 or 1, when p is 0, a is 0 and when q is 0, b is 0;
Y is a singe bond or an oxygen;
X is selected from the group consisting of a single bond, oxygen, —CO—, —O—CO—, —CO—O— and a lower alkyl group where one or more carbon atoms is optionally substituted with one or more of oxygen or —CO—;
CR is selected from the group consisting of:
wherein
each of R1 and R3 is independently hydrogen, lower alkyl, lower alkenyl, lower haloalkyl, or lower haloalkenyl;
R2 is an alkyl, alkenyl, ether, thioether, or silyl group having from 1 to about 20 carbon atoms wherein one or more CH2 groups are optionally replaced with —S—, —O—, —CO—, —CO—O—, —O—CO—, or —Si(R′)2, and where R′ is lower alkyl lower haloalkyl,
provided at least one carbon center indicated by * is an asymmetric carbon center;
A and B, independently, are linker groups selected from the group consisting of —CO—, —O—CO—, —CO—O—, —CH2—CH2—, —CH2—CH2—O—, —O—CH2—CH2—, —C≡C—, —CH═CH—, and —CH═CH—CH═CH—; and
RT, RA, and RB together represent a mesogenic core, wherein each of RT, RA, and RB is independently selected from the group consisting of:
(a) cyclohexylene,
(b) 6-membered heterocycloalkylene comprising one or two heteroatoms each of which is independently selected from the group consisting of nitrogen and oxygen,
(c) cycloalkenylene,
(d) 6-membered heterocycloalkenylene comprising one or two heteroatoms each of which is independently selected from the group consisting of nitrogen and oxygen,
(e) phenylene,
(f) naphthylene, and
(g) heteroarylene comprising one or two heteroatoms each of which is independently selected from the group consisting of nitrogen and oxygen,
wherein each of RT, RA, and RB is independently optionally substituted with one or more substituents selected from the group consisting of halide, alkyl, haloalkyl, alkenyl, haloalkenyl, nitro, and nitrile.

### Claim 15 (depends on 13)

A chiral, non-racemic liquid crystal composition which comprises one or more chiral compounds of claim 13.

### Claim 16

A compound of the formula:

### Claim 17 (depends on 14)

The chiral, non-racemic liquid crystal composition of claim 14, wherein the chiral compound is the formula:

### Claim 18

A non-racemic liquid crystal composition comprising a rod-like chiral liquid crystal compound and optionally an achiral liquid crystal host, wherein said rod-like chiral liquid crystal compound comprises a mesogenic core moiety having an achiral fluorinated alkyl tail on one end of the long axis of said mesogenic core moiety and a chiral tail on the other end of the long axis of said mesogenic core moiety, wherein:
said mesogenic core comprises a cyclic ring system, wherein said cyclic ring system is selected from the group consisting of cycloalkylene, cycloalkenylene, heterocycloalkylene, heterocycloalkenylene, arylene, heteroarylene, and a combination of two or more thereof; and
said chiral tail comprises a chiral moiety selected from the group consisting of:
wherein
each of R1 and R3 is independently hydrogen, lower alkyl, lower alkenyl, lower haloalkyl, or lower haloalkenyl; and
R2 is an alkyl, alkenyl, ether, thioether, or silyl group having from 1 to about 20 carbon atoms wherein one or more CH2 groups are optionally replaced with —S—, —O—, —CO—, —CO—O—, —O—CO—, or —Si(R′)2, and where R′ is lower alkyl or lower haloalkyl;
provided at least one carbon center indicated by * is an asymmetric carbon center.

### Claim 19 (depends on 18)

The non-racemic liquid crystal composition of claim 18, wherein said mesogenic core moiety comprises three cyclic ring systems or less.

### Claim 20 (depends on 19)

The non-racemic liquid crystal composition of claim 19, wherein each of said cyclic ring system is selected from the group consisting of cyclohexylene, cyclohexenylene, heterocycloalkylene comprising one or two ring nitrogen atoms, heterocycloalkenylene comprising one or two ring nitrogen atoms, phenylene, naphthylene, an heteroarylene comprising one or two ring nitrogen atoms.

### Claim 21 (depends on 18)

The non-racemic liquid crystal composition of claim 18, wherein each of said cyclic ring system is independently a six-membered monocyclic ring system or a ten-membered bicyclic ring system.

### Claim 22

A rod-like liquid crystal compound comprising mesogenic core moiety, wherein said mesogenic core moiety is substituted with an achiral fluorinated alkyl substituent on one end of the long axis of said mesogenic core moiety and a chiral substituent on the other end of the long axis of said mesogenic core moiety, wherein:
said mesogenic core comprises a cyclic ring system, wherein said cyclic ring system is selected from the group consisting of cycloalkylene, cycloalkenylene, heterocycloalkylene, heterocycloalkenylene, arylene, heteroarylene, and a combination of two or more thereof, and
said chiral substituent comprises a chiral moiety selected from the group consisting of:
wherein
each of R1 and R3 is independently hydrogen, lower alkyl, lower alkenyl, lower haloalkyl, or lower haloalkenyl; and
R2 is an alkyl, alkenyl, ether, thioether, or silyl group having from 1 to about 20 carbon atoms wherein one or more CH2 groups are optionally replaced with —S—, —O—, —CO—, —CO—O—, O—CO—, or —Si(R′)2, and where R′ is lower alkyl or lower haloalkyl;
provided at least one carbon center indicated by * is an asymmetric carbon center.