# US 7,425,281 B2 · Liquid crystal compositions comprising an organogermanium compound and methods for using the same

> Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt

- Number: US 7,425,281 B2
- Document ID: US7425281B2
- Status: Granted
- Kind: B2
- Application number: 11/292,510
- Filed: 2005-12-02
- Published: 2006-07-20
- Granted: 2008-09-16
- Earliest claimed: 2004-12-02
- Assignees: Displaytech, Inc.
- Inventors: Michael D. Wand; Kundalika M. More; William N. Thurmes
- Web page: https://patentgrep.com/patent/US7425281B2

## CPC

- C09K 19/40: containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen or sulfur, e.g. silicon, metals
- C09K 19/0225: {Ferroelectric}
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE

## Abstract

The present invention provides organogermanium compounds and liquid crystal compositions comprising such a compound.

## Claims

### Claim 1

A liquid crystal composition comprising at least two different compounds, wherein at least one of the compounds is an organogermanium compound of the formula:
D-E-F;
wherein
D is a chain having from about 5 to about 20 chain atoms, wherein each of the chain atoms is independently selected from the group consisting of C, O, N, S, and Si;
E is a core moiety having two, three, or four ring moieties, wherein each ring moiety is connected to the other ring moiety by a linker, and wherein each linker is independently comprised of from 0 to about 5 chain atoms;
F is a moiety of the formula:
—[Y]b-R3—[Si(R4)2]c—R5—GeR6R7R8
wherein
each of b and c is independently 0 or 1;
Y is O, S, C(═W),-Z-C(═W)—; —C(═W)-Z-, —C≡C—, or NR2;
W is O or S;
Z is O, S or NR9;
each of R2 and R9 is independently hydrogen, alkyl, or a nitrogen protecting group;
each of R3 and R5 is independently selected from the group consisting of alkylene, haloalkylene, heteroalkylene, alkenylene, alkynylene, heteroalkenylene, and heteroalkynylene;
each R4 is independently selected from the group consisting of hydrogen or C1-4 alkyl; and
each of R6, R7, and R8 is independently C1-4 alkyl.

### Claim 2 (depends on 1)

The liquid crystal composition of claim 1, wherein said Organogermanium compound is a liquid crystal compound.

### Claim 3 (depends on 1)

The liquid crystal composition of claim 1, wherein said liquid Crystal composition is a ferroelectric liquid crystal composition.

### Claim 4 (depends on 1)

The liquid crystal composition of claim 1, wherein at least one of the other compounds in said liquid crystal composition is a non-organogermanium compound.

### Claim 5 (depends on 1)

The liquid crystal composition of claim 1, wherein the total amount of organogermanium compound in said liquid crystal composition is at least 20%.

### Claim 6 (depends on 1)

The liquid crystal composition of claim 1, wherein said liquid Crystal composition further comprises a second organogermanium compound.

### Claim 7 (depends on 1)

The liquid crystal composition of claim 1, wherein the temperature range of smectic C phase exhibited by said liquid crystal composition is at least about 10° C. wide.

### Claim 8

A liquid crystal composition which is in a liquid crystal phase at room temperature, said liquid crystal composition comprising an organogermanium compound.

### Claim 9 (depends on 8)

The liquid crystal composition of claim 8, wherein said liquid crystal composition further comprises a non-organogermanium compound.

### Claim 10 (depends on 8)

The liquid crystal composition of claim 8, wherein said liquid crystal composition is enantiotropic.

### Claim 11 (depends on 8)

The liquid crystal composition of claim 8, wherein said liquid crystal composition further comprises a second organogermanium compound.

### Claim 12 (depends on 11)

The liquid crystal composition of claim 11, wherein the total amount of organogermanium compounds in said liquid crystal composition is at least about 20%.

### Claim 13 (depends on 8)

The liquid crystal composition of claim 8, wherein said organogermanium compound is a chiral compound.

### Claim 14

An enantiotropic liquid crystal composition comprising an organogermanium compound.

### Claim 15 (depends on 14)

The enantiotropic liquid crystal composition of claim 14, wherein said liquid crystal composition is in a liquid crystal phase at room temperature.

### Claim 16 (depends on 14)

The enantiotropic liquid crystal composition of claim 14, wherein said liquid crystal composition further comprises at least one non-organogermanium compound, and wherein the amount of total non-organogermanium compounds in said liquid crystal composition is about 80% or less.

### Claim 17

A liquid crystal organogermanium compound of the formula:
D-E-F;
wherein
D is a chain having from about 5 to about 20 chain atoms, wherein each of the chain atoms is independently selected from the group consisting of C, O, N, S, and Si;
E is a core moiety having two, three, or four ring moieties, wherein each ring moiety is connected to the other ring moiety by a linker, and wherein each linker is independently comprised of from 0 to about 5 chain atoms;
F is a moiety of the formula:
—[Y]b—R3—[Si(R4)2]c—R5—GeR6R7R8
wherein each of b and c is independently 0 or 1;
Y is O, S, C(═W), -Z-C(═W)—;—C(═W)-Z-,—C≡C—, or NR2;
W is O or S;
Z is O, S or NR9;
each of R2 and R9 is independently hydrogen, alkyl, or a nitrogen protecting group;
each of R3 and R5 is independently selected from the group consisting of alkylene, haloalkylene, heteroalkylene, alkenylene, alkynylene, heteroalkenylene, and heteroalkynylene;
each R4 is independently selected from the group consisting of hydrogen or C1-4 alkyl; and
each of R6, R7, and R8 is independently C1-4 alkyl.

### Claim 18 (depends on 17)

The liquid crystal organogermanium compound of claim 17, wherein each ring moiety of E is independently selected from the group consisting of cycloalkylene, heterocycloalkylene, cycloalkenylene, heterocycloalkenylene, arylene, and heteroarylene, each of which is independently optionally substituted.

### Claim 19 (depends on 18)

The liquid crystal organogermanium compound of claim 18, wherein each arylene is independently selected from the group consisting of phenylene, naphthylene, dihydronaphthylene and tetrahydronaphthylene, each of which is independently optionally substituted.

### Claim 20 (depends on 18)

The liquid crystal organogermanium compound of claim 18, wherein each heteroarylene contains one or two nitrogen ring atoms.

### Claim 21 (depends on 20)

The liquid crystal organogermanium compound of claim 20, wherein each heteroarylene is independently selected from the group consisting of optionally substituted pyridinylene and optionally substituted pyrimindinylene.

### Claim 22 (depends on 18)

The liquid crystal organogermanium compound of claim 18, wherein each ring moiety of E is independently arylene or heteroarylene, each of which is independently optionally substituted with one or two substituents, wherein each substituent is independently selected from the group consisting of halide, alkyl, haloalkyl, alkoxide, haloalkoxide, alkenyl, haloalkenyl, nitro, cyano, amino, monoalkylamino, and dialkylamino.

### Claim 23 (depends on 17)

The liquid crystal organogermanium compound of claim 17, wherein each linker chain is independently comprised of from about 0 to about 4 carbon atoms within the linker chain and 0 to 1 heteroatom within the linker chain, wherein each of the heteroatom is independently selected from the group consisting of O, N and S.

### Claim 24 (depends on 17)

The liquid crystal organogermanium compound of claim 17, wherein D is a moiety of the formula:
R1—[X]a—
wherein
a is 0 or 1;
X is O, S, C(═W), -Z-C(═W); —C(═W)-Z-, —C≡C—, or NR2;
W is O or S;
Z is O, S or NR9;
R1 is selected from the group consisting of alkyl, haloalkyl, heteroalkyl, alkenyl, alkynyl, heteroalkenyl, and heteroalkynyl; and
each of R2 and R9 is independently hydrogen, alkyl, or a nitrogen protecting group.

### Claim 25 (depends on 24)

The liquid crystal organogermanium compound of claim 24, wherein R1 is alkyl, haloalkyl, or heteroalkyl.

### Claim 26 (depends on 17)

The liquid crystal organogermanium compound of claim 17, wherein each of R6,R7, and R8 is independently methyl, ethyl, or butyl.

### Claim 27 (depends on 17)

A liquid crystal composition comprising a compound of claim 17.

### Claim 28

A compound of the Formula:
D-E-F;
wherein
D is a chain having from about 5 to about 20 chain atoms, and wherein D is a moiety of the formula:
R1—[X]a—
wherein
a is 0 or 1;
X is O, S, C(═W),-Z-C(═W)—; —C(═W)-Z-,—C≡C—, or NR2;
W is O or S;
Z is O, S or NR9;
R1 is selected from the group consisting of alkyl, haloalkyl, heteroalkyl, alkenyl, alkynyl, heteroalkenyl, and heteroalkynyl; and
each of R2 and R9 is independently hydrogen, alkyl, or a nitrogen protecting group;
E is a core moiety having two, three, or four ring moieties, wherein each ring moiety is connected to the other ring moiety by a linker, and wherein each linker is independently comprised of from 0 to about 5 chain atoms;
F is a moiety of the formula:
—[Y]b—R3—[Si(R4)2]c—R5—GeR6R7R8
wherein each of b and c is independently 0 or 1;
Y is O, S, C(═W), -Z-C(═W)—;—C(═W)-Z-,—C≡C—, or NR2;
W is O or S;
Z is O, S or NR9;
each of R2 and R9 is independently hydrogen, alkyl, or a nitrogen protecting group;
each of R3 and R5 is independently selected from the group consisting of alkylene, haloalkylene, heteroalkylene, alkenylene, alkynylene, heteroalkenylene, and heteroalkynylene;
each R4 is independently selected from the group consisting of hydrogen or C1-4 alkyl; and
each of R6, R7, and R8 is independently C1-4 alkyl.