# US 7,612,243 B2 · Cyclopenta[b]naphthalene derivatives

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- Number: US 7,612,243 B2
- Document ID: US7612243B2
- Status: Granted
- Kind: B2
- Application number: 11/931,711
- Filed: 2007-10-31
- Published: 2008-03-06
- Granted: 2009-11-03
- Earliest claimed: 2002-08-26
- Assignees: Merck Patent GmbH
- Inventors: Lars Lietzau; Matthias Bremer; Melanie Klasen-Memmer; Michael Heckmeier
- Web page: https://patentgrep.com/patent/US7612243B2

## CPC

- C09K 19/3402: {having oxygen as hetero atom (sugars C09K19/0422)}
- C07C 17/093: by replacement by halogens
- C07C 17/25: by splitting-off hydrogen halides from halogenated hydrocarbons
- C07C 17/35: by reactions not affecting the number of carbon or of halogen atoms in the reaction
- C07C 17/354: by hydrogenation
- C07C 22/08: containing fluorine
- C07C 25/22: with condensed rings
- C07C 25/24: Halogenated aromatic hydrocarbons with unsaturated side chains
- C07C 45/46: Friedel-Crafts reactions
- C07C 45/64: by introduction of functional groups containing oxygen only in singly bound form
- C07C 49/697: containing six-membered aromatic rings
- C07C 255/52: to carbon atoms of six-membered aromatic rings being part of condensed ring systems
- C09K 19/32: containing condensed ring systems, i.e. fused, bridged or spiro ring systems
- C07C 2601/14: The ring being saturated
- C07C 2603/14: Benz[f]indenes; Hydrogenated benz[f]indenes
- C09K 19/3491: {having sulfur as hetero atom}
- C09K 2019/3422: {the heterocyclic ring being a six-membered ring}
- C09K 2323/00: Functional layers of liquid crystal optical display excluding electroactive liquid crystal layer characterised by chemical composition
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS

## Abstract

The present invention relates to cyclopenta[b]naphthalene derivatives to the use thereof in liquid-crystalline or mesogenic media, to liquid-crystalline or mesogenic media comprising at least one of these cyclopenta[b]naphthalene derivatives, and to electro-optical display elements containing these liquid-crystalline or mesogenic media.

## Claims

### Claim 1

Cyclopenta[b]naphthalene derivatives of formula (VII) to (XI)
wherein
Z is in each case, independently of one another, a single bond, a double bond, —CF2O—, —OCF2—, —CH2CH2—, —CF2CF2—, —C(O)O—, —OC(O)—, —CH2O—, —OCH2—, —CF═CH—, —CH═CF—, —CF═CF—, —CH═CH— or —C≡C—,
A is in each case, independently of one another, 1,4-phenylene, in which ═CH— may be replaced once or twice by ═N—, and which may be monosubstituted to tetrasubstituted, independently of one another, by halogen (—F, —Cl, —Br, —I), —CN, —CH3, —CH2F, —CHF2, —CF3, —OCH3, —OCH2F, —OCHF2 or —OCF3, 1,4-cyclohexylene, 1,4-cyclohexenylene or 1,4-cyclohexadienylene, in which —CH2— may be replaced once or twice, independently of one another, by —O— or —S— in such a way that heteroatoms are not directly adjacent, and which may be monosubstituted or polysubstituted by halogen, or is 1,3-cyclobutylene or bicyclo[2.2.2]octane,
R is hydrogen, an alkyl, alkoxy, alkenyl or alkynyl radical having from 1 to 15 or 2 to 15 carbon atoms respectively which is unsubstituted, monosubstituted by —CF3 or at least monosubstituted by halogen, where, in addition, one or more CH2 groups in these radicals may each, independently of one another, be replaced by —O—, —S—, —CO—, —COO—, —OCO— or —OCO—O— in such a way that heteroatoms are not directly adjacent, halogen, —CN, —SCN, —NCS, —SF5, —CF3, —OCF3, —OCHF2 or —OCH2F,
n is 0, 1, 2 or 3, and
L1-L8 are each, independently of one another, hydrogen, an alkyl, alkoxy, alkenyl or alkynyl radical having from 1 to 15 or 2 to 15 carbon atoms respectively which is unsubstituted or at least monosubstituted by halogen, where, in addition, one or more CH2 groups in these radicals may each, independently of one another, be replaced by —O—, —S—, —CO—, —COO—, —OCO— or —OCO—O— in such a way that heteroatoms are not directly adjacent, halogen, —CN, —SCN, —NCS, —SF5, —CF3, —OCF3, —OCHF2, —OCH2F or -(Z-A-)n—R.

### Claim 2 (depends on 1)

Cyclopenta[b]naphthalene derivatives according to claim 1, wherein

### Claim 3 (depends on 1)

Cyclopenta[b]naphthalene derivatives according to claim 1, wherein A is

### Claim 4 (depends on 1)

Cyclopenta[b]naphthalene derivatives according to claim 1, wherein L2 and L3, independently of one another, are identical or different and are hydrogen, halogen, —CN, —SCN, —NCS, —SF5, —CF3, —CHF2, —OCF3 or —OCHF2.

### Claim 5 (depends on 1)

Cyclopenta[b]naphthalene derivatives according to claim 1, wherein L1 and L4, independently of one another, are identical or different and are hydrogen or fluorine.

### Claim 6 (depends on 1)

Cyclopenta[b]naphthalene derivatives according to at least claim 1, wherein L5 and L6 are hydrogen.

### Claim 7 (depends on 1)

Cyclopenta[b]naphthalene derivatives according to claim 1, wherein L1, L2, L3 and L4 are fluorine and L5 and L6 are hydrogen.

### Claim 8

Cyclopenta[b]naphthalene derivatives of formula (VII) to (XI)
wherein
Z is in each case, independently of one another, a single bond, a double bond, —CF2O—, —OCF2—, —CH2CH2—, —CF2CF2—, —C(O)O—, —OC(O)—, —CH2O—, —OCH2—, —CF═CH—, —CH═CF—, —CF═CF—, —CH═CH— or —C≡C—,
A is in each case, independently of one another, 1,4-phenylene, in which ═CH— may be replaced once or twice by ═N—, and which may be monosubstituted to tetrasubstituted, independently of one another, by halogen (—F, —Cl, —Br, —I), —CN, —CH3,—CH2F, —CHF2, —CF3, —OCH3, —OCH2F, —OCHF2 or —OCF3, 1,4-cyclohexylene, 1,4-cyclohexenylene or 1,4-cyclohexadienylene, in which —CH2— may be replaced once or twice, independently of one another, by —O— or —S— in such a way that heteroatoms are not directly adjacent, and which may be monosubstituted or polysubstituted by halogen, or is 1,3-cyclobutylene or bicyclo[2.2.2]octane,
R is hydrogen, an alkyl, alkoxy, alkenyl or alkynyl radical having from 1 to 15 or 2 to 15 carbon atoms respectively which is unsubstituted, monosubstituted by —CF3 or at least monosubstituted by halogen, where, in addition, one or more CH2 groups in these radicals may each, independently of one another, be replaced by —O—, —S—, —CO—, —COO—, —OCO— or —OCO—O— in such a way that heteroatoms are not directly adjacent, halogen, —CN, —SCN, —NCS, —SF5, —CF3, —OCF3, —OCHF2 or —OCH2F,
n is 0, 1, 2 or 3, and
L1-L6 and L8 are each, independently of one another, hydrogen, an alkyl, alkoxy, alkenyl or alkynyl radical having from 1 to 15 or 2 to 15 carbon atoms respectively which is unsubstituted or at least monosubstituted by halogen, where, in addition, one or more CH2 groups in these radicals may each, independently of one another, be replaced by —O—, —S—, —CO—, —COO—, —OCO— or —OCO—O— in such a way that heteroatoms are not directly adjacent, halogen, —CN, —SCN, —NCS, —SF5, —CF3, —OCF3, —OCHF2, —OCH2F or -(Z-A-)n—R,
and L7's are F.

### Claim 9

Cyclopental[b]naphthalene derivatives of formula (VII) to (XI)
wherein
Z is in each case, independently of one another, a single bond, a double bond, —CF2O—, —OCF2—, —CH2CH2—, —CF2CF2—, —C(O)O—, —OC(O)—, —CH2O—, —OCH2—, —CF═CH—, —CH═CF—, —CF═CF—, —CH═CH— or —c≡C—,
A is in each case, independently of one another, 1,4-phenylene, in which ═CH— may be replaced once or twice by ═N—, and which may be monosubstituted to tetrasubstituted, independently of one another, by halogen (—F, —Cl —Br, —I), —CN, —CH3, —CH2F, —CHF2, —CF3, —OCH3, —OCH2F, —OCHF2 or —OCF3, 1,4-cyclohexylene, 1,4-cyclohexenylene or 1,4-cyclohexadienylene, in which —CH2— may be replaced once or twice, independently of one another, by —O— or —S— in such a way that heteroatoms are not directly adjacent, and which may be monosubstituted or polysubstituted by halogen, or is 1,3-cyclobutylene or bicyclo[2.2.2]octane,
R is hydrogen, an alkyl, alkoxy, alkenyl or alkynyl radical having from 1 to 15 or 2 to 15 carbon atoms respectively which is unsubstituted, monosubstituted by —CF3 or at least monosubstituted by halogen, where, in addition, one or more CH2 groups in these radicals may each, independently of one another, be replaced by —O—, —S—, —CO—, —COO—, —OCO— or —OCO—O— in such a way that heteroatoms are not directly adjacent, halogen, —CN, —SCN, —NCS, —SF5, —CF3, —OCF3, —OCHF2 or —OCH2F,
n is 0, 1, 2 or 3, and
L1-L8 are each, independently of one another, hydrogen, an alkyl, alkoxy, alkenyl or alkynyl radical having from 1 to 15 or 2 to 15 carbon atoms respectively which is unsubstituted or at least monosubstituted by halogen, where, in addition, one or more CH2 groups in these radicals may each, independently of one another, be replaced by —O—, —S—, —CO—, —COO—, —OCO— or —OCO—O— in such a way that heteroatoms are not directly adjacent, halogen, —CN, —SCN, —NCS, —SF5, —CF3, —OCF3, —OCHF2, —OCH2F or -(Z-A-)n—R
wherein at least L8 is F.

### Claim 10 (depends on 9)

Cyclopenta (b) napathalene derivatives according to claim 9, wherein both L8 are F.

### Claim 11 (depends on 1)

Cyclopenta (b) napathalene derivatives according to claim 1, wherein

### Claim 12 (depends on 1)

Cyclopenta (b) napathalene derivatives according to claim 1, wherein

### Claim 13 (depends on 1)

Cyclopenta (b) napathalene derivatives according to claim 1, wherein

### Claim 14 (depends on 1)

Cyclopenta (b) napathalene derivatives according to claim 1, wherein