# US 5,346,646 A · Tetralin compound, liquid crystal material, liquid crystal composition and liquid crystal element

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- Number: US 5,346,646 A
- Document ID: US5346646A
- Status: Granted
- Kind: A
- Application number: 08/045,682
- Filed: 1993-04-14
- Granted: 1994-09-13
- Earliest claimed: 1992-04-14
- Assignees: Mitsui Petrochemical Industries, Ltd.
- Inventors: Junichi Kawabata; Hideo Yamaoka; Yuuichirou Tatsuki; Shinichi Nishiyama
- Web page: https://patentgrep.com/patent/US5346646A

## CPC

- C07D 239/28: with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07C 69/757: having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, [IMAGE cpc-sch-C07C-0958.gif] groups,[IMAGE cpc-sch-C07C-0959.gif] groups, or[IMAGE cpc-sch-C07C-0960.gif] in the acid moiety
- C07C 69/88: with esterified carboxyl groups
- C07D 239/34: One oxygen atom
- C09K 19/322: {Compounds containing a naphthalene ring or a completely or partially hydrogenated naphthalene ring}
- C09K 19/3463: {Pyrimidine with a carbon chain containing at least one asymmetric carbon atom, i.e. optically active pyrimidines}
- C09K 2019/325: {containing a tetrahydronaphthalene, e.g. -2,6-diyl (tetralin)}
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE

## Abstract

The present invention provides a tetralin compound represented by the following formula: R--X--A.sup.1 --Y.sup.1 --A.sup.2 --(Y.sup.2 --A.sup.3).sub.n --Z--R* wherein R is an alkyl group of 3-20 carbon atoms; X is --O-- CO--, --O-- or a single bond; n is 0 or 1; each of A.sup.1, A.sup.2 and A.sup.3 is a divalent aromatic group; each of Y.sup.1 and Y.sup.2 is --COO--, --O--CO--, --CH.sub.2 CH.sub.2 --, --CH.sub.2 O-- or --OCH.sub.2 --; Z is --O--, --O--CO-- or a single bond; and R* is a specific optically active group. The invention also provides a liquid crystal material comprising the above-mentioned tetralin compound, a liquid crystal composition comprising the tetralin compound and a liquid crystal compound other than the tetralin compound, and a liquid crystal element using the tetralin compound. The tetralin compound of the invention is favorably used as a liquid crystal material because it has a large tilt angle and shows excellent liquid crystal properties.

## Claims

### Claim 1

A tetralin compound represented by the following formula [I ]:
R--X--A.sup.1 --Y.sup.1 --A.sup.2 (Y.sup.2 --A.sup.3).sub.n --Z--R* [I]
wherein
R is an alkyl group of 3-20 carbon atoms,
X is --O--CO--, --O-- or a single bond,
n is 0 or 1, and
when n is 0, one of A.sup.1 and A.sup.2 is ##STR134## and the residual A.sup.1 or A.sup.2 is a group selected from the group consisting of ##STR135## and when n is 1, one of A.sup.1 A.sup.2 and A.sup.3 is ##STR136## and the residual two of A.sup.1, A.sup.2 and A.sup.3 are 1,4-phenylene group,
Y.sup.1 and Y.sup.2 are each independently a group selected from the group consisting of --COO--, --O--CO--, --CH.sub.2 CH.sub.2 --, --CH.sub.2 O-- and --OCH.sub.2 --,
Z is --O--, --O--CO-- or a single bond, and
R* is a group selected from the group consisting of --C*H (CF.sub.3) --C.sub.6 H.sub.13, --C*H (CH.sub.3) --C.sub.5 H.sub.11, --C*H(CH.sub.2 H.sub.5)--C.sub.5 H.sub.11, --C*H (C.sub.2 H.sub.5)--C.sub.6 H.sub.13, --CH.sub.2 --C*H(CH.sub.3)--C.sub.2 H.sub.5, --(CH.sub.2).sub.3 --C*H(CH.sub.3)--C.sub.2 H.sub.5 and --C*H(CF.sub.3)--CH.sub.2 --COO--C.sub.2 H.sub.5.

### Claim 2 (depends on 1)

The tetralin compound as claimed in claim 1, wherein Y.sup.1 and Y.sup.2 in the formula [I] are each independently --O--CO-- or --COO--.

### Claim 3 (depends on 1)

The tetralin compound as claimed in claim 1, wherein Z in the formula [I ] is --O--.

### Claim 4

A liquid crystal material comprising a tetralin compound represented by the following formula [I]:
R'X'A.sup.1 --Y.sup.1 --A.sup.2 --(Y.sup.2 --A.sup.3).sub.n --Z--R* [I]
wherein
R is an alkyl group of 3-20 carbon atoms,
X is --O--CO--, --O-- or a single bond,
n is 0 or 1, and
when n is 0, one of A.sup.1 and A.sup.2 is ##STR137## and the residual A.sup.1 or A.sup.2 is a group selected from the group consisting of ##STR138## and when n is 1, one of A.sup.1 A.sup.2 and A.sup.3 is ##STR139## and the residual two of A.sup.1 A.sup.2 and A.sup.3 are 1,4-phenylene group,
Y.sup.1 and Y.sup.2 are each independently a group selected from the group consisting of --COO--, --O--CO--, --CH.sub.2 CH.sub.2 --, --CH.sub.2 O-- and --OCH.sub.2 --,
Z is --O--, --O--CO-- or a single bond, and
R* is a group selected from the group consisting of --C*H (CF.sub.3)--C.sub.6 H.sub.13, --C*H(CH.sub.3)--C.sub.6 H.sub.13, --C*H(CH.sub.3)--CsH.sub.11, --C*H(C.sub.2 H.sub.5)CsH.sub.11, --C*H(C.sub.2 H.sub.5)--C.sub.6 H.sub.13, --CH.sub.2 --C*H(CH.sub.3)--C.sub.2 H.sub.5, --(CH.sub.2).sub.3 --C*H(CH.sub.3)--C.sub.2 H.sub.5 and --C*H (CF.sub.3) --CH.sub.2 --COO--C.sub.2 H.sub.5.

### Claim 5 (depends on 4)

The liquid crystal material as claimed in claim 4, wherein Y.sup.1 and Y.sup.2 in the formula [I] are each independently --O--CO--or --COO--.

### Claim 6 (depends on 4)

The liquid crystal material as claimed in claim 4, wherein Z in the formula [I] is --O--.

### Claim 7

A liquid crystal composition comprising a tetralin compound represented by the following formula [I]:
R--X--A.sup.1 --Y.sup.1 --A.sup.2 --(Y.sup.2 --A.sup.3).sub.n --Z--R* [I]
wherein
R is an alkyl group of 3-20 carbon atoms,
X is --O--CO--, --O-- or a single bond,
n is 0 or 1, and
when n is 0, one of A.sup.1 and A.sup.2 is ##STR140## and the residual A.sup.1 or A.sup.2 is a group selected from the group consisting of ##STR141## and when n is 1, one of A.sup.1 A.sup.2 and A.sup.3 is ##STR142## and the residual two of A.sup.1 A.sup.2 and A.sup.3 are 1,4-phenylene group,
Y.sup.1 and Y.sup.2 are each independently a group selected from the group consisting of --COO--, --O--CO--, --CH.sub.2 CH.sub.2 --, --CH.sub.2 O-- and --OCH.sub.2 --,
Z is --O--, --O--CO-- or a single bond, and
R* is a group selected from the group consisting of --C*H (CF.sub.3)--C.sub.6 H.sub.13, --C*H(CH.sub.3)--C.sub.6 H.sub.13, --C*H(CH.sub.3)--C.sub.5 H.sub.11, --C*H(C.sub.2 H.sub.5)--C.sub.5 H.sub.11, --C*H(C.sub.2 H.sub.5)--C.sub.6 H.sub.13, --CH.sub.2 --C*H(CH.sub.3)--C.sub.2 H.sub.5, --(CH.sub.2).sub.3 --C*H(CH.sub.3)--C.sub.2 H.sub.5 and C*H(CF.sub.3) CH.sub.2 --COO'C.sub.2 H.sub.5, and
a liquid crystal compound other than the tetralin compound.

### Claim 8 (depends on 7)

The liquid crystal composition as claimed in claim 7, wherein Y.sup.1 and Y.sup.2 in the formula [I] are each independently --O--CO-- or --COO--.

### Claim 9 (depends on 7)

The liquid crystal composition as claimed in claim 7, wherein Z in the formula [I] is --O--.

### Claim 10

A liquid crystal element comprising a cell and a liquid crystal material, said cell comprising two substrates facing to each other and a gap formed by the substrates, said liquid crystal material being filled in the gap of the cell, in which
the liquid crystal material comprises a tetralin compound represented by the following formula [I]:
R--X--A.sup.1 --Y.sup.1 --A.sup.2 --(Y.sup.2 --A.sup.3).sub.n --Z--R* [I]
wherein
R is an alkyl group of 3-20 carbon atoms,
X is --O--CO--, --O-- or a single bond,
n is 0 or 1, and
when n is 0, one of A.sup.1 and A.sup.2 is ##STR143## and the residual A.sup.1 or A.sup.2 is a group selected from the group consisting of ##STR144## and when n is 1, one of A.sup.1 A.sup.2, and is A.sup.3 is ##STR145## and the residual two of A.sup.1, A.sup.2 and A.sup.3 are 1,4-phenylene group,
Y.sup.1 and Y.sup.2 are each independently a group selected from the group consisting of --COO--, --O--CO--, --CH.sub.2 CH.sub.2 --, --CH.sub.2 O-- and --OCH.sub.2 --,
Z is --O--, --O--CO-- or a single bond, and
R* is a group selected from the group consisting of --C*H(CF.sub.3)--C.sub.6 H.sub.13, --C*H(CH.sub.3)--C.sub.6 H.sub.13, --C*H(CH.sub.3)--C.sub.5 H.sub.11, --C*H(C.sub.2 H.sub.5) C.sub.5 H.sub.11, --C*H (C.sub.2 H.sub.5)--C.sub.6 H.sub.13, --CH.sub.2 -- C*H (CH.sub.3)--C.sub.2 H.sub.5, --(CH.sub.2).sub.3 --C*H(CH.sub.3)--C.sub.2 H.sub.5 and --C*H(CF.sub.3)--CH.sub.2 --COO--C.sub.2 H.sub.5.

### Claim 11 (depends on 10)

The liquid crystal element as claimed in claim 10, wherein Y.sup.1 and Y.sup.2 in the formula [I] are each independently --O--CO-- or --COO--.

### Claim 12 (depends on 10)

The liquid crystal element as claimed in claim 10, wherein Z in the formula [I] is --O--.

### Claim 13

A liquid crystal element comprising a cell and a liquid crystal composition, said cell comprising two substrates facing to each other and a gap formed by the substrates, said liquid crystal material being filled in the gap of the cell, in which
the liquid crystal material comprises a tetralin compound represented by the following formula [I]:
R--X--A.sup.1 --Y.sup.1 --A.sup.2 --(Y.sup.2 --A.sup.3).sub.n --Z--R* [I]
wherein
R is an alkyl group of 3-20 carbon atoms,
X is --O--CO--, --O-- or a single bond,
n is 0 or 1, and
when n is 0, one of A.sup.1 and A.sup.2 is ##STR146## and the residual A.sup.1 or A.sup.2 is a group selected from the group consisting of ##STR147## and when n is 1, one of A.sup.1 , A.sup.2 and A.sup.3 is ##STR148## and the residual two of A.sup.1 A.sup.2 and A.sup.3 are 1,4-phenylene group,
Y.sup.1 and Y.sup.2 are each independently a group selected from the group consisting of --COO--, --O--CO--, --CH.sub.2 CH.sub.2 --, --CH.sub.2 O-- and --OCH.sub.2 --,
Z is --O--, --O--CO-- or a single bond, and
R* is a group selected from the group consisting of --C*H(CF.sub.3)--C.sub.6 H.sub.13, --C*H(CH.sub.3)--C.sub.6 H.sub.13, --C*H(CH)--C.sub.5 H.sub.11, --C*H(C.sub.2 H.sub.5)--C.sub.5 H.sub.11, --C*H(C.sub.2 H.sub.5)--C.sub.6 H.sub.13, --CH.sub.2 --C*H(CH.sub.3)--C.sub.2 H.sub.5, --(CH.sub.2).sub.3 --C*H(CH.sub.3)--C.sub.2 H.sub.5 and --C*H(CF.sub.3) --CH.sub.2 --COO--C.sub.2 H.sub.5, and
a liquid crystal compound other than the tetralin compound.

### Claim 14 (depends on 13)

The liquid crystal element as claimed in claim 13, wherein Y.sup.1 and Y.sup.2 in the formula [I] are each independently --O--CO-- or --COO--.

### Claim 15 (depends on 14)

The liquid crystal element as claimed in claim 14, wherein Z in the formula [I] is --O--.

### Claim 16

A tetralin compound represented by the following formula (I):
R--X--A.sup.1 --Y.sup.1 --A.sup.2 --Z--R* (I)
wherein
R is an alkyl group of 3-20 carbon atoms,
X is --O--CO--, --O-- or a single bond,
one of A.sup.1 and A.sup.2 is ##STR149## and the residual A.sup.1 or A.sup.2 is a group selected from the group consisting of ##STR150## Y.sup.1 is a group selected from the group consisting of --COO--, --O--CO--, --CH.sub.2 CH.sub.2 --, --CH.sub.2 O-- and --OCH.sub.2,
Z is --O--, --O--CO-- or a single bond, and
R* is a group selected from the group consisting of --C*H(CF.sub.3)--C.sub.6 H.sub.13, --C*H(CH.sub.3)--C.sub.6 H.sub.13, --C*H(CH.sub.3)--C.sub.5 H.sub.11, --C*H(C.sub.2 H.sub.5)--C.sub.5 H.sub.11, --C*H(C.sub.2 H.sub.5)--C.sub.6 H.sub.13, --CH.sub.2 --C*H(CH.sub.3)--C.sub.2 H.sub.5, --(CH.sub.2).sub.3 --C*H(CH.sub.3)--C.sub.2 H.sub.5 and --C*H(CF.sub.3)--CH.sub.2 --COO--C.sub.2 H.sub.5.

### Claim 17 (depends on 16)

The tetralin compound as claimed in claim 16, wherein Y.sup.1 in the formula (I) is --O--CO or --COO--.

### Claim 18 (depends on 16)

The tetralin compound is claimed in claim 16, wherein Z in the formula (I) is --O-- or --O--CO--.

### Claim 19 (depends on 16)

The tetralin compound as claimed in claim 16 wherein Z in the formula (I) is --O--.

### Claim 20 (depends on 16)

The tetralin compound as claimed in claim 16 wherein the compound has the formula ##STR151##

### Claim 21

A tetralin compound represented by the following formula (I):
R--X--A.sup.1 --Y.sup.1 --A.sup.2 --(Y.sup.2 --A.sup.3).sub.n --Z--R* (I)
wherein
R is an alkyl group of 3-20 carbon atoms,
X is --O--CO--, --O-- or a single bond,
n is 1, one of A.sup.1, A.sup.2 and A.sup.3 is ##STR152## and the residual two of A.sup.1, A.sup.2, and A.sup.3 are 1,4-phenylene group,
Y.sup.1 and Y.sup.2 are each independently a group selected from the group consisting of --COO--, --O--CO--, --CH.sub.2 CH.sub.2 --, --CH.sub.2 O-- and --OCH.sub.2,
Z is --O--, --O--CO-- or a single bond, and
R is a group selected from the group consisting of --C*H(CF.sub.3)--C.sub.6 H.sub.13, --C*H(CH.sub.3)--C.sub.6 H.sub.13, --C*H(CH.sub.3)--C.sub.5 H.sub.11, --C*H(C.sub.2 H.sub.5)--C.sub.5 H.sub.11, --C*H(C.sub.2 H.sub.5)--C.sub.6 H.sub.13, --CH.sub.2 --C*H(CH.sub.3)--C.sub.2 H.sub.5, --(CH.sub.2).sub.3)--C.sub.2 H.sub.5 and --C*H(CF.sub.3)--CH.sub.2 --COO--C.sub.2 H.sub.5.

### Claim 22 (depends on 21)

The tetralin compound as claimed in claims 21, wherein Y.sup.1 and Y.sup.2 in the formula (I) are each independently --O--CO-- or --COO--.

### Claim 23 (depends on 21)

The tetralin compound as claimed in claim 21, wherein Z in the formula (I) is --O-- or --O--CO--.

### Claim 24 (depends on 21)

The tetralin compound as claimed in claim 21 wherein Z in the formula (I) is --O--.

### Claim 25 (depends on 21)

The tetralin compound as claimed in claim 21 wherein the compound has the formula ##STR153##

### Claim 26 (depends on 21)

The tetralin compound as claimed in claim 21 wherein the compound has the formula ##STR154##

### Claim 27 (depends on 21)

The tetralin compound as claimed in claim 21 wherein the compound has the formula ##STR155##